| Pomperaug 2016-17 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 1907 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| TBA | JV Baseball | Danbury | Away - Westerner Baseball Field, Rogers Park [Directions] | TBA | ||
| TBA | JV Baseball | Bunnell | Away - Bunnell Baseball Field [Directions] | TBA | ||
| TBA | FR Baseball | Masuk | Home - PHS Baseball Field [Directions] | 3:45 p.m. | ||
| TBA | FR Baseball | Stratford | Away - Penders Field [Directions] | TBA | ||
| TBA | FR Baseball | Bunnell | Away - Bunnell Baseball Field [Directions] | TBA | ||
| TBA | FR Boys Basketball | New Fairfield | Home - PHS Main Gym [Directions] | TBA | ||
| TBA | JV Boys Soccer | Masuk | Away - Great Hollow Lake Fields at Wolfe Park [Directions] | 4:00 p.m. | ||
| TBA | JV Girls Basketball | Newtown | Home - PHS Main Gym [Directions] | TBA | ||
| TBA | FR Girls Basketball | Newtown | Home - PHS Main Gym [Directions] | TBA | ||
| TBA | JV Girls Lacrosse | Immaculate | Home - Sports Complex & Track [Directions] | TBA | ||
| TBA | JV Girls Soccer | Naugatuck | Home - Sports Complex & Track [Directions] | TBA | ||
| TBA | JV Girls Soccer | Stratford | Home - Sports Complex & Track [Directions] | TBA | ||
| TBA | V Softball | CIAC Tournament Game | Home - PHS Softball Field [Directions] | TBA | ||
| TBA | JV Softball | Lewis Mills | Away - Lewis Mills JV Softball Field [Directions] | 4:00 p.m. | ||
| TBA | JV Softball | Brookfield | Home - Community Softball Field [Directions] | TBA | ||
| TBA | V Girls Tennis | Fairfield Ludlowe | Home - PHS Tennis Courts [Directions] | Cancelled | Cancelled | |
| Sat., 7/2 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 8:00 a.m. | 8:00 - 10:30 am | |
| Sat., 7/2 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 8:00 a.m. | 8:00 - 10:30 am | |
| Tue., 7/5 | Miscellaneous Events | Mdby Park & Rec Swim Lessons | - PHS Pool | 11:15 a.m. | 11:15 am - 2:30 pm | |
| Tue., 7/5 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 - 10:00 am | |
| Tue., 7/5 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 7:30 pm | |
| Tue., 7/5 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 7:30 pm | |
| Wed., 7/6 | Miscellaneous Events | Mdby Park & Rec Swim Lessons | - PHS Pool | 11:15 a.m. | 11:15 am - 2:30 pm | |
| Wed., 7/6 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 - 10:00 am | |
| Wed., 7/6 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 7:30 pm | |
| Wed., 7/6 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 7:30 pm | |
| Thu., 7/7 | Miscellaneous Events | Mdby Park & Rec Swim Lessons | - PHS Pool | 11:15 a.m. | 11:15 am - 2:30 pm | |
| Thu., 7/7 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 7:30 pm | |
| Thu., 7/7 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 7:30 pm | |
| Fri., 7/8 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 - 10:00 am | |
| Fri., 7/8 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 7:30 pm | |
| Fri., 7/8 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 7:30 pm | |
| Fri., 7/8 | Miscellaneous Events | Southbury Youth Soccer | - Sports Complex & Track | 6:00 p.m. | 6:00 - 8:00 pm | |
| Sat., 7/9 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 10:00 a.m. | 10:00 - 12:30 pm | |
| Sat., 7/9 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 10:00 a.m. | 10:00 - 12:30 pm | |
| Mon., 7/11 | Miscellaneous Events | Mdby Park & Rec Swim Lessons | - PHS Pool | 11:15 a.m. | 11:15 am - 2:30 pm | |
| Mon., 7/11 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 - 10:00 am | |
| Mon., 7/11 | Miscellaneous Events | Triple Threat Basketball Camp | - PHS Main Gym | 8:00 a.m. | 8:00 am - 2:00 pm | |
| Tue., 7/12 | Miscellaneous Events | Mdby Park & Rec Swim Lessons | - PHS Pool | 11:15 a.m. | 11:15 am - 2:30 pm | |
| Tue., 7/12 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 - 10:00 am | |
| Tue., 7/12 | Miscellaneous Events | Triple Threat Basketball Camp | - PHS Main Gym | 8:00 a.m. | 8:00 am - 2:00 pm | |
| Tue., 7/12 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 7:30 pm | |
| Tue., 7/12 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 7:30 pm | |
| Wed., 7/13 | Miscellaneous Events | Mdby Park & Rec Swim Lessons | - PHS Pool | 11:15 a.m. | 11:15 am - 2:30 pm | |
| Wed., 7/13 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 - 10:00 am | |
| Wed., 7/13 | Miscellaneous Events | Triple Threat Basketball Camp | - PHS Main Gym | 8:00 a.m. | 8:00 am - 2:00 pm | |
| Wed., 7/13 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 7:30 pm | |
| Wed., 7/13 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 7:30 pm | |
| Thu., 7/14 | Miscellaneous Events | Mdby Park & Rec Swim Lessons | - PHS Pool | 11:15 a.m. | 11:15 am - 2:30 pm | |
| Thu., 7/14 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 - 10:00 am | |
| Thu., 7/14 | Miscellaneous Events | Triple Threat Basketball Camp | - PHS Main Gym | 8:00 a.m. | 8:00 am - 2:00 pm | |
| Thu., 7/14 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 7:30 pm | |
| Thu., 7/14 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 7:30 pm | |
| Fri., 7/15 | Miscellaneous Events | Nutmeg Games Gymnastic Set-Up | - PHS Main Gym | TBA | Three Hours | |
| Sat., 7/16 | Miscellaneous Events | Nutmeg Games Gymnastics | - PHS Main Gym | 7:00 a.m. | 7:00 am - 5:00 pm | |
| Sat., 7/16 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 8:00 a.m. | 8:00 - 10:30 am | |
| Sat., 7/16 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 8:00 a.m. | 8:00 - 10:30 am | |
| Sun., 7/17 | Miscellaneous Events | Nutmeg Games Gymnastics Breakdown | - PHS Main Gym | TBA | Three Hours | |
| Mon., 7/18 | Miscellaneous Events | Mdby Park & Rec Swim Lessons | - PHS Pool | 11:15 a.m. | 11:15 am - 2:30 pm | |
| Mon., 7/18 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 - 10:00 am | |
| Tue., 7/19 | Miscellaneous Events | Mdby Park & Rec Swim Lessons | - PHS Pool | 11:15 a.m. | 11:15 am - 2:30 pm | |
| Tue., 7/19 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 - 10:00 am | |
| Wed., 7/20 | Miscellaneous Events | Mdby Park & Rec Swim Lessons | - PHS Pool | 11:15 a.m. | 11:15 am - 2:30 pm | |
| Wed., 7/20 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 - 10:00 am | |
| Wed., 7/20 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 7:30 pm | |
| Wed., 7/20 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 7:30 pm | |
| Thu., 7/21 | Miscellaneous Events | Mdby Park & Rec Swim Lessons | - PHS Pool | 11:15 a.m. | 11:15 am - 2:30 pm | |
| Thu., 7/21 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 - 10:00 am | |
| Wed., 7/27 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 7:30 pm | |
| Wed., 7/27 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 7:30 pm | |
| Thu., 7/28 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 7:30 pm | |
| Thu., 7/28 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 7:30 pm | |
| Mon., 8/15 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 4:00 p.m. | ||
| Mon., 8/15 | Miscellaneous Events | PHS Soccer Camp | - PHS Soccer Field | 4:30 p.m. | ||
| Tue., 8/16 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 4:00 p.m. | ||
| Tue., 8/16 | Miscellaneous Events | PHS Soccer Camp | - PHS Soccer Field | 4:30 p.m. | ||
| Wed., 8/17 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 4:00 p.m. | ||
| Wed., 8/17 | Miscellaneous Events | PHS Soccer Camp | - PHS Soccer Field | 4:30 p.m. | ||
| Thu., 8/18 | Miscellaneous Events | Link Crew | - PHS Main Gym | 7:00 a.m. | 7:00 am - 3:00 pm | |
| Thu., 8/18 | Miscellaneous Events | Link Crew | - Auxiliary Gym | 7:00 a.m. | 7:00 am - 3:00 pm | |
| Thu., 8/18 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 4:00 p.m. | ||
| Thu., 8/18 | Miscellaneous Events | PHS Soccer Camp | - PHS Soccer Field | 4:30 p.m. | ||
| Fri., 8/19 | Miscellaneous Events | Link Crew | - Auxiliary Gym | 7:00 a.m. | 7:00 am - 3:00 pm | |
| Fri., 8/19 | Miscellaneous Events | Link Crew | - PHS Main Gym | 7:00 a.m. | 7:00 am - 3:00 pm | |
| Fri., 8/19 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 4:00 p.m. | ||
| Fri., 8/19 | Miscellaneous Events | PHS Soccer Camp | - PHS Soccer Field | 4:30 p.m. | ||
| Sat., 8/20 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:00 p.m. | ||
| Mon., 8/22 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 8:00 a.m. | ||
| Mon., 8/22 | Miscellaneous Events | Freshmen Orientation | - PHS Main Gym | 8:00 a.m. | 8:00 am - 2:00 pm | |
| Mon., 8/22 | Miscellaneous Events | Freshmen Orientation | - Auxiliary Gym | 8:00 a.m. | 8:00 am - 2:00 pm | |
| Mon., 8/22 | Miscellaneous Events | Freshmen Dance | - PHS Main Gym | 6:00 p.m. | 6:00 - 9:00 pm | |
| Tue., 8/23 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 8:00 a.m. | ||
| Tue., 8/23 | Miscellaneous Events | CPR and First Aid Class For Coaches | - Health Classroom - Room 201 | 4:00 p.m. | ||
| Wed., 8/24 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 8:00 a.m. | ||
| Thu., 8/25 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Thu., 8/25 | School Holidays and Closings | Teacher Convocation & Meetings | ||||
| Fri., 8/26 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Fri., 8/26 | School Holidays and Closings | Full Day Inservice | ||||
| Sat., 8/27 | V Football | Seymour (Scrim.) | Away [Directions] | 10:00 a.m. | ||
| Sat., 8/27 | FR Football | Seymour (Scrim.) | Away [Directions] | 10:00 a.m. | ||
| Sat., 8/27 | V Boys Soccer | Alumni Game | Home - Sports Complex & Track [Directions] | 4:00 p.m. | ||
| Sat., 8/27 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 9:00 a.m. | ||
| Mon., 8/29 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Mon., 8/29 | School Holidays and Closings | Teacher Work Day | ||||
| Tue., 8/30 | V Boys Soccer | Seymour (Scrim.) | Away - Seymour HS [Directions] | 7:00 p.m. | ||
| Tue., 8/30 | V Field Hockey | Cheshire (Scrim.) | Home - Sports Complex & Track [Directions] | 4:00 p.m. | vs. Chesire and Hand | |
| Tue., 8/30 | V Girls Volleyball | Holy Cross (Scrim.) | Home - PHS Main Gym [Directions] | 3:15 p.m. | ||
| Tue., 8/30 | JV Girls Volleyball | Holy Cross (Scrim.) | Home - PHS Main Gym [Directions] | 3:15 p.m. | ||
| Tue., 8/30 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Tue., 8/30 | School Holidays and Closings | First Day of School | ||||
| Wed., 8/31 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Wed., 8/31 | Miscellaneous Events | Girls Swim Team Parents Meeting | - Health Classroom - Room 201 | 6:15 p.m. | ||
| Thu., 9/1 | V Football | Ridgefield (Scrim.) | Home - Sports Complex & Track [Directions] | 7:00 p.m. | ||
| Thu., 9/1 | V Boys Soccer | Hopkins School (Scrim.) | Away | 3:00 p.m. | ||
| Thu., 9/1 | V Field Hockey | Nonnewaug (Scrim.) | Away - Nonnewaug HS Field [Directions] | 3:45 p.m. | ||
| Thu., 9/1 | V Girls Soccer | Shelton (Scrim.) | Home - Sports Complex & Track [Directions] | 3:30 p.m. | ||
| Thu., 9/1 | JV Girls Soccer | Shelton (Scrim.) | Home - PHS Soccer Field [Directions] | 3:00 p.m. | ||
| Thu., 9/1 | V Girls Volleyball | Seymour (Scrim.) | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Thu., 9/1 | JV Girls Volleyball | Seymour (Scrim.) | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Thu., 9/1 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Thu., 9/1 | Miscellaneous Events | Team Pictures | - PHS Main Gym | 2:00to5:00 p.m. | ||
| Thu., 9/1 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 2:15to3:15 p.m. | ||
| Fri., 9/2 | V Boys Cross Country | Danbury (Scrim.) | Away [Directions] | 7:30 p.m. | @ Danbury High School | |
| Fri., 9/2 | V Girls Cross Country | Danbury (Scrim.) | Away [Directions] | 7:30 p.m. | @ Danbury High School | |
| Fri., 9/2 | JV Field Hockey | New Fair Field Field Hockey Play Day | Away | 5:30 p.m. | ||
| Fri., 9/2 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Fri., 9/2 | Miscellaneous Events | Team Pictures | - Auxiliary Gym | 2:00to5:00 p.m. | ||
| Fri., 9/2 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30 pm | |
| Sat., 9/3 | V Boys Soccer | Cheshire (Scrim.) | Home - Sports Complex & Track [Directions] | 6:00 p.m. | $4 Adults, $3 Students | |
| Sat., 9/3 | JV Boys Soccer | Cheshire (Scrim.) | Home - Sports Complex & Track [Directions] | 4:00 p.m. | ||
| Sat., 9/3 | V Field Hockey | New Fairfield Field Hockey Play Day | Away | TBA | ||
| Sat., 9/3 | V Girls Soccer | Woodland (Scrim.) | Home - Sports Complex & Track [Directions] | 11:00 a.m. | ||
| Sat., 9/3 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 9:00 a.m. | ||
| Mon., 9/5 | V Boys Soccer | Nonnewaug (Scrim.) | Home - Sports Complex & Track [Directions] | 7:00 p.m. | $4 Adults, $3 Students | |
| Mon., 9/5 | V Field Hockey | Pomperaug Field Hockey Play Day | Home - Sports Complex & Track [Directions] | 9:00 a.m. | vs. Amity and Danbury | |
| Mon., 9/5 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Mon., 9/5 | School Holidays and Closings | Labor Day | ||||
| Tue., 9/6 | V Girls Volleyball | Woodland (Scrim.) | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Tue., 9/6 | JV Girls Volleyball | Woodland (Scrim.) | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Tue., 9/6 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Tue., 9/6 | Miscellaneous Events | PAC Swim Practice | Home - PHS Pool [Directions] | 5:30 p.m. | 5:30 - 7:30 pm | |
| Tue., 9/6 | Miscellaneous Events | PAC Swim Practice | Home - PHS Pool [Directions] | 7:15 p.m. | 7:15 - 8:45 pm | |
| Wed., 9/7 | V Boys Cross Country | Watermelon Run | Home - Sports Complex & Track [Directions] | 3:00 p.m. | ||
| Wed., 9/7 | V Boys Soccer | Bullard Havens Tech (Scrim.) | Home - Sports Complex & Track [Directions] | 4:30 p.m. | ||
| Wed., 9/7 | V Girls Cross Country | Watermelon Run | Home - Sports Complex & Track [Directions] | 3:00 p.m. | ||
| Wed., 9/7 | V Girls Soccer | Staples (Scrim.) | Away - Loeffler Field - Staples HS [Directions] | 5:00 p.m. | ||
| Wed., 9/7 | JV Girls Soccer | Staples (Scrim.) | Away - Wakeman Field E (grass) [Directions] | 5:00 p.m. | ||
| Wed., 9/7 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Wed., 9/7 | Miscellaneous Events | PAC Swim Practice | Home - PHS Pool [Directions] | 5:30 p.m. | 5:30 - 7:30 pm | |
| Wed., 9/7 | Miscellaneous Events | PAC Swim Practice | Home - PHS Pool [Directions] | 7:15 p.m. | 7:15 - 8:45 pm | |
| Thu., 9/8 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Thu., 9/8 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 2:15to3:15 p.m. | ||
| Thu., 9/8 | Miscellaneous Events | PAC Swim Practice | Home - PHS Pool [Directions] | 7:15 p.m. | 7:15 - 8:45 pm | |
| Fri., 9/9 | V Football | Joel Barlow | Home - Sports Complex & Track [Directions] | 6:00 p.m. | W 18-13 | $5 Adults, $3 Students |
| Fri., 9/9 | V Boys Soccer | New Fairfield | Away - Rebel Turf [Directions] | 6:00 p.m. | W 1-0 | |
| Fri., 9/9 | JV Boys Soccer | New Fairfield | Away - Rebel Turf [Directions] | 4:00 p.m. | ||
| Fri., 9/9 | FR Girls Soccer | Naugatuck | Away - Breen Field [Directions] | 3:45 p.m. | ||
| Fri., 9/9 | V Girls Volleyball | Nonnewaug | Home - PHS Main Gym [Directions] | 5:00 p.m. | W 3-1 | Non League Game |
| Fri., 9/9 | JV Girls Volleyball | Nonnewaug | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 9/9 | FR Girls Volleyball | Brookfield | Home - PHS Main Gym [Directions] | 3:45 p.m. | ||
| Fri., 9/9 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Fri., 9/9 | Miscellaneous Events | Sophomore Class Meeting | - Health Classroom - Room 201 | 2:15 p.m. | 2:15 - 3:00 | |
| Fri., 9/9 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30 pm | |
| Fri., 9/9 | Miscellaneous Events | PAC Swim Practice | Home - PHS Pool [Directions] | 5:30 p.m. | 5:30 - 7:30 pm | |
| Fri., 9/9 | Miscellaneous Events | PAC Swim Practice | Home - PHS Pool [Directions] | 7:15 p.m. | 7:15 - 8:45 pm | |
| Sat., 9/10 | FR Football | Brookfield | Away - BHS Stadium Field [Directions] | 10:00 a.m. | ||
| Sat., 9/10 | FR Boys Soccer | Naugatuck | Home - PHS Soccer Field [Directions] | 9:00 a.m. | ||
| Sat., 9/10 | V Girls Soccer | New Fairfield | Home - Sports Complex & Track [Directions] | 3:00 p.m. | W 7-2 | |
| Sat., 9/10 | JV Girls Soccer | New Fairfield | Home - Sports Complex & Track [Directions] | 9:00 a.m. | W 6-1 | |
| Sat., 9/10 | FR Girls Volleyball | Amity | Home - PHS Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 9/10 | Miscellaneous Events | PAC Swim Practice | Home - PHS Pool [Directions] | 11:30 a.m. | 11:30 am - 1:00 pm | |
| Sat., 9/10 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 9:00 a.m. | ||
| Sun., 9/11 | Miscellaneous Events | Pop Warner Football Games | - Sports Complex & Track | 8:00 a.m. | 8:00 am - 5:00 pm | |
| Mon., 9/12 | FR Boys Soccer | Holy Cross | Away - Lower Murray Park [Directions] | 3:45 p.m. | ||
| Mon., 9/12 | FR Girls Soccer | Weston | Home - PHS Soccer Field [Directions] | 4:15 p.m. | ||
| Mon., 9/12 | FR Girls Volleyball | Weston | Home - Auxiliary Gym [Directions] | 4:00 p.m. | ||
| Mon., 9/12 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Mon., 9/12 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30 pm | |
| Mon., 9/12 | Miscellaneous Events | PAC Swim Practice | Home - PHS Pool [Directions] | 7:15 p.m. | 7:15 - 8:45 pm | |
| Tue., 9/13 | V Boys Cross Country | Newtown, Bethel, Kolbe Cathedral | Home - Pomperaug HS [Directions] | 4:30 p.m. | PHS 15 KHS 50, PHS 15 BHS 50, PHS 25 NHS 30 | |
| Tue., 9/13 | V Boys Soccer | Bunnell | Away - Bunnell Turf Field [Directions] | 7:00 p.m. | W 3-0 | |
| Tue., 9/13 | JV Boys Soccer | Bunnell | Away - Bunnell Turf Field [Directions] | 5:00 p.m. | ||
| Tue., 9/13 | V Girls Cross Country | Newtown, Bethel, Kolbe Cathedral | Home - Pomperaug HS [Directions] | 4:30 p.m. | ||
| Tue., 9/13 | V Field Hockey | Bethel | Away - Hunt Field at Bethel HS [Directions] | 3:45 p.m. | L 0-1 | Non League Game |
| Tue., 9/13 | JV Field Hockey | Bethel | Away - Hunt Field at Bethel HS [Directions] | 5:15 p.m. | ||
| Tue., 9/13 | V Girls Soccer | Bunnell | Home - Sports Complex & Track [Directions] | 7:00 p.m. | W 8-1 | $4 Adults, $3 Students |
| Tue., 9/13 | JV Girls Soccer | Bunnell | Home - PHS Soccer Field [Directions] | 5:00 p.m. | W 7-0 | |
| Tue., 9/13 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Tue., 9/13 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 2:15to3:15 p.m. | ||
| Tue., 9/13 | Miscellaneous Events | PAC Swim Practice | Home - PHS Pool [Directions] | 7:15 p.m. | 7:15 - 8:45 pm | |
| Wed., 9/14 | FR Field Hockey | Masuk | Home - PHS Field Hockey Field [Directions] | 4:30 p.m. | ||
| Wed., 9/14 | FR Girls Soccer | Masuk | Home - PHS Soccer Field [Directions] | 4:00 p.m. | ||
| Wed., 9/14 | FR Girls Volleyball | Weston | Away - WHS Old Gymnasium [Directions] | 3:45 p.m. | ||
| Wed., 9/14 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Wed., 9/14 | Miscellaneous Events | PAC Swim Practice | Home - PHS Pool [Directions] | 7:15 p.m. | 7:15 - 8:45 pm | |
| Thu., 9/15 | FR Football | Masuk | Home - Sports Complex & Track [Directions] | 4:00 p.m. | ||
| Thu., 9/15 | V Boys Soccer | Bethel | Home - Sports Complex & Track [Directions] | 7:00 p.m. | W 2-1 | $5 Adults, $3 Students |
| Thu., 9/15 | JV Boys Soccer | Bethel | Home - PHS Soccer Field [Directions] | 4:00 p.m. | ||
| Thu., 9/15 | V Field Hockey | New Milford | Away - New Milford HS [Directions] | 5:30 p.m. | L 0-1 | Non League Game |
| Thu., 9/15 | JV Field Hockey | New Milford | Away - New Milford HS [Directions] | 3:45 p.m. | ||
| Thu., 9/15 | V Girls Soccer | Bethel | Away - Rourke Field [Directions] | 4:00 p.m. | W 2-1 | |
| Thu., 9/15 | JV Girls Soccer | Bethel | Away - MS Field [Directions] | 4:00 p.m. | W 5-0 | |
| Thu., 9/15 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Thu., 9/15 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 2:15to3:15 p.m. | ||
| Thu., 9/15 | Miscellaneous Events | PAC Swim Practice | Home - PHS Pool [Directions] | 7:15 p.m. | 7:15 - 8:45 pm | |
| Fri., 9/16 | V Football | Masuk | Away - Bunnell HS, Stratford [Directions] | 7:00 p.m. | L 8-48 | |
| Fri., 9/16 | FR Girls Soccer | Amity | Home - PHS Soccer Field [Directions] | 4:00 p.m. | ||
| Fri., 9/16 | V Girls Swimming and Diving | Masuk | Away - Masuk Pool [Directions] | 4:00 p.m. | PHS 93- Mask 85 | |
| Fri., 9/16 | V Girls Volleyball | Masuk | Home - PHS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 9/16 | JV Girls Volleyball | Masuk | Home - PHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/16 | FR Girls Volleyball | Masuk | Home - Auxiliary Gym [Directions] | 3:45 p.m. | ||
| Fri., 9/16 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Fri., 9/16 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30 pm | |
| Fri., 9/16 | Miscellaneous Events | PAC Swim Practice | Home - PHS Pool [Directions] | 7:15 p.m. | 7:15 - 8:45 pm | |
| Sat., 9/17 | V Boys Cross Country | Wilton Invitational | Away | 9:00 a.m. | @ Wilton High School | |
| Sat., 9/17 | JV Football | Masuk | Home - Sports Complex & Track [Directions] | 10:00 a.m. | ||
| Sat., 9/17 | FR Boys Soccer | Masuk | Home - PHS Soccer Field [Directions] | 9:00 a.m. | ||
| Sat., 9/17 | V Girls Cross Country | Wilton Invitational | Away | 9:00 a.m. | @ Wilton High School | |
| Sat., 9/17 | V Field Hockey | Joel Barlow | Home - Sports Complex & Track [Directions] | 2:00 p.m. | L 0-1 | Non League Game |
| Sat., 9/17 | JV Field Hockey | Joel Barlow | Home - Sports Complex & Track [Directions] | 12:15 p.m. | ||
| Sat., 9/17 | FR Field Hockey | Immaculate | Away - Mustang Valley [Directions] | Cancelled | Cancelled | |
| Sat., 9/17 | V Girls Soccer | New Milford | Away - New Milford HS [Directions] | 2:00 p.m. | W 2-0 | Non-League Game |
| Sat., 9/17 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 9:00 a.m. | ||
| Sun., 9/18 | Miscellaneous Events | Pop Warner Football Games | - Sports Complex & Track | 8:00 a.m. | 8:00 am - 5:00 pm | |
| Mon., 9/19 | FR Boys Soccer | New Milford | Away [Directions] | 3:45 p.m. | ||
| Mon., 9/19 | FR Field Hockey | New Fairfield | Home - PHS Field Hockey Field [Directions] | 5:00 p.m. | ||
| Mon., 9/19 | V Girls Volleyball | Brookfield | Home - PHS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Mon., 9/19 | JV Girls Volleyball | Brookfield | Home - PHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 9/19 | FR Girls Volleyball | New Fairfield | Away - NFHS Gym [Directions] | 4:45 p.m. | ||
| Mon., 9/19 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Mon., 9/19 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30 pm | |
| Mon., 9/19 | Miscellaneous Events | PAC Swim Practice | Home - PHS Pool [Directions] | 7:15 p.m. | 7:15 - 8:45 pm | |
| Tue., 9/20 | V Boys Cross Country | Masuk, Stratford | Away [Directions] | 4:30 p.m. | PHS 20 Masuk 43, PHS 15 Stratford 50 | @ Masuk High School |
| Tue., 9/20 | V Boys Soccer | New Milford | Away - New Milford HS [Directions] | 6:00 p.m. | L 0-1 | |
| Tue., 9/20 | JV Boys Soccer | New Milford | Away [Directions] | 4:00 p.m. | ||
| Tue., 9/20 | V Girls Cross Country | Masuk, Stratford | Away [Directions] | 4:30 p.m. | PHS 15 Stratford 50 , PHS 18 PHS 45 | @ Masuk High School |
| Tue., 9/20 | V Girls Soccer | New Milford | Home - Sports Complex & Track [Directions] | 7:00 p.m. | W 7-0 | $4 Adults, $3 Students |
| Tue., 9/20 | JV Girls Soccer | New Milford | Home - Sports Complex & Track [Directions] | 5:00 p.m. | W 4-0 | |
| Tue., 9/20 | V Girls Swimming and Diving | Joel Barlow | Home - PHS Pool [Directions] | 6:00 p.m. | PHS 100- JBHS 72 | $5 Adults, $3 Students |
| Tue., 9/20 | FR Girls Volleyball | Newtown | Away - Newtown HS Gymnasium [Directions] | 5:00 p.m. | ||
| Tue., 9/20 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Tue., 9/20 | Miscellaneous Events | PAC Swim Practice | Home - PHS Pool [Directions] | 7:15 p.m. | 7:15 - 8:45 pm | |
| Wed., 9/21 | V Field Hockey | Masuk | Away - Masuk Middle Field [Directions] | 4:00 p.m. | W 5-0 | |
| Wed., 9/21 | JV Field Hockey | Masuk | Away - Masuk Middle Field [Directions] | 5:30 p.m. | ||
| Wed., 9/21 | V Girls Volleyball | Stratford | Away - Needham Memorial Gymnasium [Directions] | 6:00 p.m. | W 3-0 | |
| Wed., 9/21 | JV Girls Volleyball | Stratford | Away - Needham Memorial Gymnasium [Directions] | 5:00 p.m. | ||
| Wed., 9/21 | FR Girls Volleyball | Newtown | Home - PHS Main Gym [Directions] | 3:45 p.m. | ||
| Wed., 9/21 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Wed., 9/21 | Miscellaneous Events | PAC Swim Practice | Home - PHS Pool [Directions] | 7:15 p.m. | 7:15 - 8:45 pm | |
| Thu., 9/22 | FR Football | New Milford | Home - Sports Complex & Track [Directions] | 4:00 p.m. | ||
| Thu., 9/22 | V Boys Soccer | Brookfield | Home - Sports Complex & Track [Directions] | 7:00 p.m. | L 1-2 | $5 Adults, $3 Students |
| Thu., 9/22 | JV Boys Soccer | Brookfield | Home - PHS Soccer Field [Directions] | 4:00 p.m. | ||
| Thu., 9/22 | FR Field Hockey | Brookfield | Away - BHS Field Hockey Field [Directions] | 4:30 p.m. | ||
| Thu., 9/22 | V Girls Soccer | Brookfield | Away - BHS Stadium Field [Directions] | 6:00 p.m. | W 2-0 | |
| Thu., 9/22 | JV Girls Soccer | Brookfield | Away - BHS Back Turf [Directions] | 4:00 p.m. | T 1-1 | |
| Thu., 9/22 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Thu., 9/22 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 2:15to3:15 p.m. | ||
| Thu., 9/22 | Miscellaneous Events | PAC Swim Practice | Home - PHS Pool [Directions] | 7:15 p.m. | 7:15 - 8:45 pm | |
| Fri., 9/23 | V Football | New Milford | Away - New Milford HS [Directions] | 7:00 p.m. | L 19-28 | |
| Fri., 9/23 | V Field Hockey | New Milford | Home - Sports Complex & Track [Directions] | 5:30 p.m. | T 0-0 | |
| Fri., 9/23 | JV Field Hockey | New Milford | Home - Sports Complex & Track [Directions] | 3:45 p.m. | ||
| Fri., 9/23 | V Girls Swimming and Diving | New Fairfield | Home - PHS Pool [Directions] | 4:00 p.m. | PHS 99- NFHS 80 | |
| Fri., 9/23 | V Girls Volleyball | Joel Barlow | Home - PHS Main Gym [Directions] | 5:30 p.m. | L 3-1 | |
| Fri., 9/23 | JV Girls Volleyball | Joel Barlow | Home - PHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/23 | FR Girls Volleyball | Immaculate | Away - Immaculate HS [Directions] | 3:45 p.m. | ||
| Fri., 9/23 | Miscellaneous Events | PHS Field Day | - Pomperaug HS | 11:30 a.m. | ||
| Fri., 9/23 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Fri., 9/23 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30 pm | |
| Fri., 9/23 | Miscellaneous Events | PAC Swim Practice | Home - PHS Pool [Directions] | 7:15 p.m. | 7:15 - 8:45 pm | |
| Fri., 9/23 | School Holidays and Closings | Early Dismissal - In Service | ||||
| Sat., 9/24 | JV Football | New Milford | Home - Sports Complex & Track [Directions] | 10:00 a.m. | ||
| Sat., 9/24 | V Boys Soccer | Naugatuck | Away - Naugatuck HS [Directions] | 6:00 p.m. | T 1-1 | |
| Sat., 9/24 | JV Boys Soccer | Naugatuck | Home - Sports Complex & Track [Directions] | 3:00 p.m. | ||
| Sat., 9/24 | FR Boys Soccer | Newtown | Home - PHS Soccer Field [Directions] | 9:00 a.m. | ||
| Sat., 9/24 | FR Field Hockey | Amity | Home - PHS Baseball Field [Directions] | 10:00 a.m. | ||
| Sat., 9/24 | V Girls Soccer | Naugatuck | Away - Naugatuck HS [Directions] | 3:45 p.m. | W 6-1 | |
| Sat., 9/24 | FR Girls Soccer | Newtown | Away - Blue and Gold Stadium [Directions] | 9:00 a.m. | ||
| Sat., 9/24 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 9:00 a.m. | ||
| Mon., 9/26 | FR Boys Soccer | Naugatuck | Away - Breen Field [Directions] | 3:45 p.m. | ||
| Mon., 9/26 | FR Field Hockey | Bethel | Home - PHS Field Hockey Field [Directions] | 4:30 p.m. | ||
| Mon., 9/26 | FR Girls Soccer | Naugatuck | Home - PHS Soccer Field [Directions] | 3:45 p.m. | ||
| Mon., 9/26 | V Girls Volleyball | Weston | Away - WHS Gymnasium [Directions] | 5:30 p.m. | L 1-3 | |
| Mon., 9/26 | JV Girls Volleyball | Weston | Away - WHS Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 9/26 | FR Girls Volleyball | Immaculate | Home - PHS Main Gym [Directions] | 5:00 p.m. | ||
| Mon., 9/26 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Mon., 9/26 | Miscellaneous Events | Sophomore Class Meeting | - Health Classroom - Room 201 | 2:15 p.m. | 2:15 - 3:00 pm | |
| Mon., 9/26 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30 pm | |
| Mon., 9/26 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:45 pm | |
| Tue., 9/27 | V Boys Cross Country | New Fairfield, Brookfield, Weston | Away [Directions] | 4:30 p.m. | PHS 17 NFHS 44 , PHS 21 Weston 38 , PHS 18 Brookfield 41 | @ New Fairfield High School |
| Tue., 9/27 | V Boys Soccer | Masuk | Away - Great Hollow Lake Fields at Wolfe Park [Directions] | 4:00 p.m. | L 1-0 | |
| Tue., 9/27 | V Girls Cross Country | New Fairfield, Brookfield, Weston | Away - Rebel Stadium [Directions] | 4:30 p.m. | PHS 15 Brookfield 48 , PHS 15 Weston 48 , PHS 15 NFHS 50 | @ New Fairfield High School |
| Tue., 9/27 | V Field Hockey | Weston | Home - Sports Complex & Track [Directions] | 7:30 p.m. | L 0-2 | |
| Tue., 9/27 | JV Field Hockey | Weston | Home - Sports Complex & Track [Directions] | 6:00 p.m. | ||
| Tue., 9/27 | V Girls Soccer | Masuk | Home - Sports Complex & Track [Directions] | 3:30 p.m. | W 1-0 | |
| Tue., 9/27 | JV Girls Soccer | Masuk | Home - PHS Soccer Field [Directions] | 5:00 p.m. | W 4-0 | |
| Tue., 9/27 | V Girls Swimming and Diving | New Milford | Home - PHS Pool [Directions] | 6:00 p.m. | PHS 90- NMHS 67 | $5 Adults, $3 Students |
| Tue., 9/27 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Tue., 9/27 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 2:15to3:15 p.m. | ||
| Tue., 9/27 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 4:00 pm | |
| Wed., 9/28 | V Girls Volleyball | Bunnell | Away - Bunnell [Directions] | 6:15 p.m. | L 2-3 | |
| Wed., 9/28 | JV Girls Volleyball | Bunnell | Away - Bunnell [Directions] | 5:00 p.m. | ||
| Wed., 9/28 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Wed., 9/28 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:45 pm | |
| Thu., 9/29 | FR Football | Bunnell | Home - Sports Complex & Track [Directions] | 4:00 p.m. | ||
| Thu., 9/29 | V Boys Soccer | Weston | Home - Sports Complex & Track [Directions] | 7:00 p.m. | L 0-1 | $5 Adults, $3 Students |
| Thu., 9/29 | JV Boys Soccer | Weston | Home - PHS Soccer Field [Directions] | 5:00 p.m. | ||
| Thu., 9/29 | V Field Hockey | Joel Barlow | Away - Field I (Stadium) [Directions] | 6:45 p.m. | L 2-3 | |
| Thu., 9/29 | JV Field Hockey | Joel Barlow | Away - Field I (Stadium) [Directions] | 5:15 p.m. | ||
| Thu., 9/29 | V Girls Soccer | Weston | Away - WHS Turf Field [Directions] | 7:15 p.m. | W 1-0 | |
| Thu., 9/29 | JV Girls Soccer | Weston | Away - WHS Stadium Field [Directions] | 5:30 p.m. | W 3-0 | |
| Thu., 9/29 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Thu., 9/29 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 2:15to3:15 p.m. | ||
| Thu., 9/29 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:45 pm | |
| Fri., 9/30 | V Football | Bunnell | Away - Bunnell Turf Field [Directions] | 7:00 p.m. | L 14-20 | |
| Fri., 9/30 | V Girls Swimming and Diving | Brookfield | Home - PHS Pool [Directions] | 6:00 p.m. | PHS 95- BHS 89 | $5 Adults, $3 Students |
| Fri., 9/30 | V Girls Volleyball | Bethel | Home - PHS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 9/30 | JV Girls Volleyball | Bethel | Home - PHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/30 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Fri., 9/30 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30 pm | |
| Fri., 9/30 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:45 pm | |
| Sat., 10/1 | JV Football | Bunnell | Home - Sports Complex & Track [Directions] | 10:00 a.m. | ||
| Sat., 10/1 | FR Boys Soccer | Holy Cross | Home - PHS Soccer Field [Directions] | 9:00 a.m. | ||
| Sat., 10/1 | FR Field Hockey | Amity | Away - Amity HS [Directions] | 10:00 a.m. | ||
| Sat., 10/1 | FR Girls Soccer | Weston | Away - WHS Turf Field [Directions] | 9:00 a.m. | ||
| Sat., 10/1 | FR Girls Volleyball | Brookfield | Away - BHS Big Gym [Directions] | 10:00 a.m. | ||
| Sat., 10/1 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 8:30 a.m. | 9:00 - 11:00 am | |
| Sat., 10/1 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 3:00 p.m. | 3:00 - 6:00 pm | |
| Sat., 10/1 | School Holidays and Closings | Senior Semi-Formal Dance | 7:00 pm | |||
| Sun., 10/2 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 10:00 a.m. | 10:00 - 11:30 am | |
| Mon., 10/3 | School Holidays and Closings | Rosh Hashanah - No School | ||||
| Tue., 10/4 | V Boys Cross Country | Joel Barlow, Bunnell, Immaculate | Away - Cross Country Loop [Directions] | 4:30 p.m. | PHS 25 JBHS 36, PHS 21 IHS 39 , PHS 16 Bunnell 47 | @ Joel Barlow |
| Tue., 10/4 | V Girls Cross Country | Joel Barlow, Bunnell, Immaculate | Away - Cross Country Loop [Directions] | 4:30 p.m. | PHS 26 IHS 31 , PHS 15 JBHS 49 , PHS 15 Bunnell 50 | @ Joel Barlow High School |
| Tue., 10/4 | V Field Hockey | Bethel | Home - Sports Complex & Track [Directions] | 5:30 p.m. | W 2-1 | |
| Tue., 10/4 | JV Field Hockey | Bethel | Home - Sports Complex & Track [Directions] | 3:30 p.m. | ||
| Tue., 10/4 | V Girls Soccer | Newtown | Away - Blue and Gold Stadium [Directions] | 7:00 p.m. | W 1-0 | |
| Tue., 10/4 | JV Girls Soccer | Newtown | Away - Blue and Gold Stadium [Directions] | 5:00 p.m. | W 8-0 | |
| Tue., 10/4 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Tue., 10/4 | Miscellaneous Events | Unified Sports Practice | 2:15 p.m. | |||
| Tue., 10/4 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 2:30-3:30 p.m. | ||
| Wed., 10/5 | V Boys Soccer | Newtown | Home - Sports Complex & Track [Directions] | 7:00 p.m. | W 1-0 | $5 Adults, $3 Students |
| Wed., 10/5 | JV Boys Soccer | Newtown | Home - Sports Complex & Track [Directions] | 5:15 p.m. | ||
| Wed., 10/5 | V Girls Volleyball | Immaculate | Away - Immaculate HS [Directions] | 6:30 p.m. | W 3-1 | |
| Wed., 10/5 | JV Girls Volleyball | Immaculate | Away - Immaculate HS [Directions] | 5:00 p.m. | ||
| Wed., 10/5 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Wed., 10/5 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 2:30-3:30 p.m. | ||
| Wed., 10/5 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30 pm | |
| Wed., 10/5 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:45 pm | |
| Wed., 10/5 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 6:00-7:30 p.m. | ||
| Thu., 10/6 | FR Boys Soccer | Masuk | Away - Great Hollow Lake Fields at Wolfe Park [Directions] | 3:45 p.m. | ||
| Thu., 10/6 | V Field Hockey | New Fairfield | Away - Rebel Turf [Directions] | 5:30 p.m. | L 1-2 | |
| Thu., 10/6 | JV Field Hockey | New Fairfield | Away - Rebel Turf [Directions] | 4:00 p.m. | ||
| Thu., 10/6 | FR Field Hockey | Newtown | Away - Treadwell Town Park [Directions] | 4:30 p.m. | ||
| Thu., 10/6 | FR Girls Soccer | Masuk | Home - PHS Soccer Field [Directions] | 3:45 p.m. | ||
| Thu., 10/6 | FR Girls Volleyball | New Fairfield | Home - PHS Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 10/6 | Miscellaneous Events | Sophomore Class Meeting | - Health Classroom - Room 201 | 2:15 p.m. | 2:15 - 3:00 pm | |
| Thu., 10/6 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 2:15to3:15 p.m. | ||
| Thu., 10/6 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 2:30-3:30 p.m. | ||
| Thu., 10/6 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:45 pm | |
| Fri., 10/7 | V Boys Soccer | Immaculate | Away - Mustang Valley [Directions] | 3:45 p.m. | W 1-0 | |
| Fri., 10/7 | JV Boys Soccer | Immaculate | Away - Immaculate HS [Directions] | 4:00 p.m. | ||
| Fri., 10/7 | V Field Hockey | Newtown | Away - Treadwell Town Park [Directions] | 3:45 p.m. | W 3-1 | |
| Fri., 10/7 | JV Field Hockey | Newtown | Away - Treadwell Town Park [Directions] | 5:30 p.m. | ||
| Fri., 10/7 | V Girls Soccer | Immaculate | Home - Sports Complex & Track [Directions] | 7:00 p.m. | T 0-0 | $4 Adults, $3 Students |
| Fri., 10/7 | JV Girls Soccer | Immaculate | Home - Sports Complex & Track [Directions] | 4:00 p.m. | W 8-0 | |
| Fri., 10/7 | V Girls Swimming and Diving | Newtown | Home - PHS Pool [Directions] | 6:00 p.m. | PHS 98- NHS 80 | $5 Adults, $3 Students |
| Fri., 10/7 | V Girls Volleyball | Newtown | Home - PHS Main Gym [Directions] | 5:30 p.m. | W 3-1 | |
| Fri., 10/7 | JV Girls Volleyball | Newtown | Home - PHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/7 | FR Girls Volleyball | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | 4:15 p.m. | ||
| Fri., 10/7 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 9:00 a.m. | 9:00 - 12:00 | |
| Fri., 10/7 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 2:30-3:30 p.m. | ||
| Fri., 10/7 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 3:30 p.m. | ||
| Fri., 10/7 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30 pm | |
| Fri., 10/7 | School Holidays and Closings | Professional Development - No Classes | ||||
| Sat., 10/8 | V Boys Cross Country | Wickham Invitational | Away | 11:00 a.m. | Selected squad | |
| Sat., 10/8 | V Girls Cross Country | Wickham Invitational | Away | 11:00 a.m. | Selected squad | |
| Sat., 10/8 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 8:30 a.m. | 9:00 - 12:30 pm | |
| Sun., 10/9 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 9:00 a.m. | 9:00 - 11:00 am | |
| Mon., 10/10 | V Boys Soccer | Kolbe Cathedral | Home - Sports Complex & Track [Directions] | 4:00 p.m. | W 2-0 | |
| Mon., 10/10 | V Field Hockey | Greenwich | Away - Cardinal Stadium [Directions] | 4:00 p.m. | L 2-4 | |
| Mon., 10/10 | V Girls Soccer | Kolbe Cathedral | Away - Seaside Park [Directions] | 4:00 p.m. | W 7-0 | |
| Mon., 10/10 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Tue., 10/11 | V Boys Cross Country | Notre Dame-Fairfield, New Milford | Home - Pomperaug HS [Directions] | 4:30 p.m. | PHS 15 NDHS 50 , NMHS 19 PHS 36 | |
| Tue., 10/11 | V Girls Cross Country | Notre Dame-Fairfield, New Milford | Home - Pomperaug HS [Directions] | 4:30 p.m. | PHS 15 NDHS 50 , PHS 15 NMHS 50 | |
| Tue., 10/11 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 3:00 p.m. | ||
| Tue., 10/11 | School Holidays and Closings | No School | ||||
| Wed., 10/12 | School Holidays and Closings | Yom Kippur - No School | ||||
| Thu., 10/13 | FR Football | Stratford | Away - Penders Field [Directions] | 4:00 p.m. | ||
| Thu., 10/13 | V Boys Soccer | Joel Barlow | Away - Field J (competition field) [Directions] | 4:00 p.m. | W 2-1 | |
| Thu., 10/13 | JV Boys Soccer | Joel Barlow | Away - Field E (Softball) [Directions] | 4:00 p.m. | ||
| Thu., 10/13 | V Field Hockey | Brookfield | Home - Sports Complex & Track [Directions] | 3:45 p.m. | W 4-3(OT) | |
| Thu., 10/13 | JV Field Hockey | Brookfield | Home - PHS Baseball Field [Directions] | 5:15 p.m. | ||
| Thu., 10/13 | V Girls Soccer | Joel Barlow | Home - Sports Complex & Track [Directions] | 7:15 p.m. | W 3-2 | $4 Adults, $3 Students |
| Thu., 10/13 | JV Girls Soccer | Joel Barlow | Home - Sports Complex & Track [Directions] | 5:15 p.m. | W 2-0 | |
| Thu., 10/13 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Thu., 10/13 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 2:15to3:15 p.m. | ||
| Thu., 10/13 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 2:30-3:30 p.m. | ||
| Thu., 10/13 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 9:00 pm | |
| Fri., 10/14 | V Football | Stratford | Home - Sports Complex & Track [Directions] | 6:00 p.m. | L 12-21 | $5 Adults, $3 Students |
| Fri., 10/14 | FR Boys Soccer | New Milford | Home - PHS Soccer Field [Directions] | 3:45 p.m. | ||
| Fri., 10/14 | FR Field Hockey | New Milford | Home - PHS Field Hockey Field [Directions] | 4:30 p.m. | ||
| Fri., 10/14 | V Girls Swimming and Diving | Weston | Away - Weston MS Pool [Directions] | 4:00 p.m. | PHS 88- WHS 96 | |
| Fri., 10/14 | V Girls Volleyball | Kolbe Cathedral | Away [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 10/14 | JV Girls Volleyball | Kolbe Cathedral | Away [Directions] | 4:00 p.m. | ||
| Fri., 10/14 | FR Girls Volleyball | Freshmen Volleyball Jamboree | Home - PHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/14 | FR Girls Volleyball | Freshmen Volleyball Jamboree | Home - Auxiliary Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/14 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Fri., 10/14 | Miscellaneous Events | Band Practice | - PHS Soccer Field | 2:15 p.m. | 2:15 to 3:00 | |
| Fri., 10/14 | Miscellaneous Events | Sophomore Class Meeting | - Health Classroom - Room 201 | 2:15 p.m. | 2:15 - 3:00 pm | |
| Fri., 10/14 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 7:30 pm | |
| Fri., 10/14 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 2:30-3:30 p.m. | ||
| Fri., 10/14 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30 pm | |
| Fri., 10/14 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 6:00-7:00 p.m. | ||
| Sat., 10/15 | V Boys Cross Country | Bethel (Scrim.) | Away [Directions] | 9:00 a.m. | Selected Athletes | |
| Sat., 10/15 | JV Football | Stratford | Away - Penders Field [Directions] | 10:00 a.m. | ||
| Sat., 10/15 | V Boys Soccer | Watertown | Home - Sports Complex & Track [Directions] | 7:00 p.m. | W 1-0 | $5 Adults, $3 Students |
| Sat., 10/15 | JV Boys Soccer | Watertown | Home - Sports Complex & Track [Directions] | 5:15 p.m. | ||
| Sat., 10/15 | V Girls Cross Country | Bethel (Scrim.) | Away [Directions] | 9:00 a.m. | Selected Athletes | |
| Sat., 10/15 | V Field Hockey | Watertown | Home - Sports Complex & Track [Directions] | 10:00 a.m. | W 3-0 | |
| Sat., 10/15 | JV Field Hockey | Watertown | Home - Sports Complex & Track [Directions] | 11:45 a.m. | ||
| Sat., 10/15 | V Girls Soccer | Shelton | Away - Shelton HS Finn Stadium [Directions] | 7:15 p.m. | L 1-5 | |
| Sat., 10/15 | JV Girls Soccer | Shelton | Away - Shelton HS Finn Stadium [Directions] | 5:30 p.m. | L 4-0 | |
| Sat., 10/15 | V Girls Volleyball | Lauralton Hall | Away - Lauralton Hall Gymnasium [Directions] | 12:00 p.m. | W 3-1 | non league |
| Sat., 10/15 | JV Girls Volleyball | Lauralton Hall | Away - Lauralton Hall Gymnasium [Directions] | 10:30 a.m. | ||
| Sat., 10/15 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 9:30 a.m. | ||
| Sun., 10/16 | Miscellaneous Events | Pop Warner Football Games | - Sports Complex & Track | 8:00 a.m. | 8:00 am - 5:00 pm | |
| Sun., 10/16 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 9:00 a.m. | 9:00 - 11:00 am | |
| Mon., 10/17 | FR Boys Soccer | Newtown | Away - Treadwell Town Park--Tilson Field [Directions] | 3:45 p.m. | ||
| Mon., 10/17 | FR Field Hockey | Joel Barlow | Home - PHS Field Hockey Field [Directions] | 4:30 p.m. | ||
| Mon., 10/17 | FR Girls Soccer | Newtown | Home - PHS Soccer Field [Directions] | 3:45 p.m. | ||
| Mon., 10/17 | V Girls Volleyball | Notre Dame-Fairfield | Home - PHS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Mon., 10/17 | JV Girls Volleyball | Notre Dame-Fairfield | Home - PHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 10/17 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Mon., 10/17 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 2:30-3:30 p.m. | ||
| Mon., 10/17 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30 pm | |
| Mon., 10/17 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 9:00 pm | |
| Mon., 10/17 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 6:00-7:00 p.m. | ||
| Tue., 10/18 | V Boys Soccer | Notre Dame-Fairfield | Home - Sports Complex & Track [Directions] | 7:00 p.m. | L 3-1 | |
| Tue., 10/18 | JV Boys Soccer | Notre Dame-Fairfield | Home - Sports Complex & Track [Directions] | 4:00 p.m. | ||
| Tue., 10/18 | V Girls Soccer | Notre Dame-Fairfield | Away - Veteran's Park - Bridgeport [Directions] | 4:15 p.m. | L 1-2 | |
| Tue., 10/18 | V Girls Swimming and Diving | Bunnell | Away - Flood Pool [Directions] | 6:00 p.m. | PHS 89- BHS 71 | @ Flood School |
| Tue., 10/18 | FR Girls Volleyball | New Milford | Away - New Milford HS [Directions] | 5:00 p.m. | ||
| Tue., 10/18 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Tue., 10/18 | Miscellaneous Events | Unified Sports Practice | 2:15 p.m. | |||
| Tue., 10/18 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 2:15 p.m. | ||
| Tue., 10/18 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 2:30-3:30 p.m. | ||
| Tue., 10/18 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 9:00 pm | |
| Wed., 10/19 | V Boys Cross Country | South-West Conference Championships | Away [Directions] | 4:30 p.m. | @ Bethel High School | |
| Wed., 10/19 | V Girls Cross Country | South-West Conference Championships | Away [Directions] | 4:00 p.m. | ||
| Wed., 10/19 | V Girls Volleyball | New Fairfield | Away - NFHS Gym [Directions] | 5:30 p.m. | W 3-1 | |
| Wed., 10/19 | JV Girls Volleyball | New Fairfield | Away - NFHS Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/19 | Miscellaneous Events | PSAT Extended Time | - Health Classroom - Room 201 | 7:30 a.m. | ||
| Wed., 10/19 | Miscellaneous Events | PSAT Testing | - PHS Main Gym | 8:00 a.m. | 8:00 am - 1:00 pm | |
| Wed., 10/19 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Wed., 10/19 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 2:30-3:30 p.m. | ||
| Wed., 10/19 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30 pm | |
| Wed., 10/19 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 9:00 pm | |
| Wed., 10/19 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 6:00-7:00 p.m. | ||
| Thu., 10/20 | FR Football | Watertown | Away - John J. Mills Complex @ Watertown HS [Directions] | 3:30 p.m. | ||
| Thu., 10/20 | V Boys Soccer | Stratford | Away - Penders Field [Directions] | 7:00 p.m. | W 2-1 | |
| Thu., 10/20 | JV Boys Soccer | Stratford | Away - Penders Field [Directions] | 5:15 p.m. | ||
| Thu., 10/20 | FR Field Hockey | Masuk | Away - Masuk Middle Field [Directions] | 4:30 p.m. | ||
| Thu., 10/20 | V Girls Soccer | Stratford | Home - Sports Complex & Track [Directions] | 7:00 p.m. | W 8-0 | $4 Adults, $3 Students |
| Thu., 10/20 | V Girls Swimming and Diving | Stratford | Home - PHS Pool [Directions] | 6:00 p.m. | PHS 90- SHS 79 | $5 Adults, $3 Students |
| Thu., 10/20 | FR Girls Volleyball | Amity | Away - Paul D. Mengold Gymnasium at Amity Regional HS [Directions] | 4:00 p.m. | ||
| Thu., 10/20 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Thu., 10/20 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 2:15to3:15 p.m. | ||
| Thu., 10/20 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 2:30-3:30 p.m. | ||
| Thu., 10/20 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 9:00 pm | |
| Thu., 10/20 | Miscellaneous Events | Southbury Park & Rec Adult Open BB | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 10/20 | Miscellaneous Events | Stby Park & Rec Adult Open Bball | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 10/21 | V Football | Weston | Home - Sports Complex & Track [Directions] | 6:00 p.m. | W 21-14 | Homecoming Game, $5 Adults, $3 Students |
| Fri., 10/21 | V Field Hockey | Immaculate | Away - Mustang Valley [Directions] | 3:45 p.m. | W 1-0 | |
| Fri., 10/21 | V Girls Volleyball | New Milford | Home - PHS Main Gym [Directions] | 4:45 p.m. | W 3-0 | |
| Fri., 10/21 | JV Girls Volleyball | New Milford | Home - PHS Main Gym [Directions] | 3:15 p.m. | ||
| Fri., 10/21 | FR Girls Volleyball | New Milford | Home - Auxiliary Gym [Directions] | 5:30 p.m. | ||
| Fri., 10/21 | Miscellaneous Events | Pep Rally | - PHS Main Gym | 1:00 p.m. | 1:00 - 2:00 pm | |
| Fri., 10/21 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Fri., 10/21 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 4:00 pm | |
| Fri., 10/21 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 2:30-3:30 p.m. | ||
| Fri., 10/21 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30 pm | |
| Fri., 10/21 | Miscellaneous Events | Homecoming Dance | - PHS Main Gym | 8:00 p.m. | 8:00 - 11:00 pm | |
| Fri., 10/21 | School Holidays and Closings | Homecoming Day | ||||
| Sat., 10/22 | JV Football | Weston | Away - WHS Stadium Field [Directions] | 10:00 a.m. | Will be played as a Froshmore Game | |
| Sat., 10/22 | FR Boys Soccer | Naugatuck | Home - PHS Soccer Field [Directions] | 9:00 a.m. | ||
| Sat., 10/22 | JV Field Hockey | Immaculate | Home - Sports Complex & Track [Directions] | Cancelled | Cancelled | |
| Sat., 10/22 | FR Field Hockey | Immaculate | Home - PHS Baseball Field [Directions] | Cancelled | Cancelled | |
| Sat., 10/22 | FR Girls Soccer | Naugatuck | Away - Naugatuck HS [Directions] | Cancelled | Cancelled | |
| Sat., 10/22 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 8:30 a.m. | ||
| Sat., 10/22 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 8:30 a.m. | 9:00 - 12:30 pm | |
| Sat., 10/22 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 10/23 | Miscellaneous Events | Pop Warner Football Games | - Sports Complex & Track | 8:00 a.m. | 8:00 am - 5:00 pm | |
| Sun., 10/23 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Mon., 10/24 | V Boys Soccer | Masuk | Home - Sports Complex & Track [Directions] | 7:00 p.m. | W 1-0 | Non League Game, $5 Adults, $3 Students |
| Mon., 10/24 | JV Boys Soccer | Masuk | Home - Sports Complex & Track [Directions] | 4:00 p.m. | ||
| Mon., 10/24 | V Field Hockey | Brookfield | Away - BHS Stadium Field [Directions] | 4:00 p.m. | W 3-0 | Non League Game |
| Mon., 10/24 | JV Field Hockey | Brookfield | Away - BHS Back Turf [Directions] | 5:30 p.m. | ||
| Mon., 10/24 | V Girls Volleyball | Bethel | Away - Bethel HS [Directions] | 5:30 p.m. | W 3-0 | Non League Game |
| Mon., 10/24 | JV Girls Volleyball | Bethel | Away - Bethel HS [Directions] | 4:00 p.m. | ||
| Mon., 10/24 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Mon., 10/24 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 2:30-3:30 p.m. | ||
| Mon., 10/24 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 2:30-3:30 p.m. | ||
| Mon., 10/24 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30 pm | |
| Mon., 10/24 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 9:00 pm | |
| Mon., 10/24 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 6:00-7:00 p.m. | ||
| Tue., 10/25 | FR Field Hockey | Newtown | Home - PHS Field Hockey Field [Directions] | 4:30 p.m. | ||
| Tue., 10/25 | FR Girls Soccer | Weston | Home - PHS Soccer Field [Directions] | 4:00 p.m. | ||
| Tue., 10/25 | V Girls Swimming and Diving | Immaculate | Home - PHS Pool [Directions] | 6:00 p.m. | PHS 100- IBHS 76 | $5 Adults, $3 Students |
| Tue., 10/25 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Tue., 10/25 | Miscellaneous Events | Unified Sports Practice | 2:15 p.m. | |||
| Tue., 10/25 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 4:00 pm | |
| Tue., 10/25 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 2:30-3:30 p.m. | ||
| Tue., 10/25 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 9:00 pm | |
| Tue., 10/25 | Miscellaneous Events | Southbury Park & Rec Adult Open BB | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 10/25 | Miscellaneous Events | Southbury Park & Rec Adult Open BB | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 10/25 | Miscellaneous Events | Stby Park & Rec Adult Open Bball | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 10/26 | V Field Hockey | Haddam-Killingworth | Home - Sports Complex & Track [Directions] | 7:00 p.m. | L 0-1 | |
| Wed., 10/26 | JV Field Hockey | Haddam-Killingworth | Home - Sports Complex & Track [Directions] | 5:15 p.m. | ||
| Wed., 10/26 | V Girls Volleyball | Southington | Home - PHS Main Gym [Directions] | 6:30 p.m. | L 3-1 | non league |
| Wed., 10/26 | JV Girls Volleyball | Southington | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 10/26 | FR Girls Volleyball | Southington | Home - PHS Main Gym [Directions] | 5:00 p.m. | ||
| Wed., 10/26 | Miscellaneous Events | Red Cross Blood Drive | - Auxiliary Gym | 6:00 a.m. | 6:00 am - 3:00 pm | |
| Wed., 10/26 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Wed., 10/26 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 2:30-3:30 p.m. | ||
| Wed., 10/26 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30 pm | |
| Wed., 10/26 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 9:00 pm | |
| Wed., 10/26 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 6:00-7:00 p.m. | ||
| Wed., 10/26 | Miscellaneous Events | Volleyball Team Senior Party | - Health Classroom - Room 201 | 6:00to9:00 p.m. | ||
| Thu., 10/27 | FR Football | Newtown | Home - Sports Complex & Track [Directions] | Cancelled | Cancelled | |
| Thu., 10/27 | V Girls Cross Country | Danbury | Away [Directions] | Cancelled | Cancelled | |
| Thu., 10/27 | V Girls Cross Country | Danbury | Away [Directions] | 4:00 p.m. | ||
| Thu., 10/27 | FR Field Hockey | New Milford | Away - New Milford HS [Directions] | Cancelled | Cancelled | |
| Thu., 10/27 | V Girls Volleyball | Bunnell | Home - PHS Main Gym [Directions] | 6:00 p.m. | SWC Quarterfinal, $8 Adults, $5 Students | |
| Thu., 10/27 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Thu., 10/27 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 2:30-3:30 p.m. | ||
| Thu., 10/27 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 9:00 pm | |
| Thu., 10/27 | Miscellaneous Events | Stby Park & Rec Adult Open Bball | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 10/28 | V Football | Newtown | Away - Blue and Gold Stadium [Directions] | 7:00 p.m. | L 8-28 | |
| Fri., 10/28 | V Boys Soccer | Weston | Home - Sports Complex & Track [Directions] | 4:00 p.m. | SWC Quarter Finals, $8 Adults, $5 Students | |
| Fri., 10/28 | V Girls Soccer | Bunnell | Home - Sports Complex & Track [Directions] | 6:00 p.m. | W 4-0 | SWC Quarter-Finals, $8 Adults, $5 Students |
| Fri., 10/28 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Fri., 10/28 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30 pm | |
| Fri., 10/28 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 9:00 pm | |
| Sat., 10/29 | V Boys Cross Country | CIAC Class L State Meet | Away | 2:05 p.m. | ||
| Sat., 10/29 | JV Football | Newtown | Home - Sports Complex & Track [Directions] | 10:00 a.m. | ||
| Sat., 10/29 | V Girls Cross Country | CIAC Class L State Meet | Away | 2:35 p.m. | ||
| Sat., 10/29 | V Field Hockey | SWC Quarter-Finals | Away | 12:00 p.m. | vs. New Fairfield, @ Brookfield, $8 Adults, $5 Students | |
| Sat., 10/29 | FR Girls Soccer | Amity | Away - Center Field - Woodbridge [Directions] | 10:30 a.m. | ||
| Sat., 10/29 | FR Girls Volleyball | New Fairfield (Scrim.) | Away [Directions] | 9:00 a.m. | ||
| Sat., 10/29 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 8:30 a.m. | 9:00 - 12:30 pm | |
| Sat., 10/29 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sat., 10/29 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | TBA | ||
| Sun., 10/30 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 10/30 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 4:00 pm | 4:00 - 5:00 pm | |
| Mon., 10/31 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | ||
| Mon., 10/31 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 2:30-3:30 p.m. | ||
| Mon., 10/31 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30 pm | |
| Mon., 10/31 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 9:00 pm | |
| Mon., 10/31 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 6:00-7:00 p.m. | ||
| Tue., 11/1 | V Boys Cross Country | Danbury (Scrim.) | Away [Directions] | 4:45 p.m. | ||
| Tue., 11/1 | V Boys Soccer | SWC Semi-Finals | Away [Directions] | 7:00 p.m. | @ Barlow, $8 adults, $5 students | |
| Tue., 11/1 | FR Boys Soccer | Masuk | Home - PHS Soccer Field [Directions] | 3:30 p.m. | ||
| Tue., 11/1 | V Girls Cross Country | Danbury Freshmen Invitational | Away | 4:15 p.m. | ||
| Tue., 11/1 | V Girls Soccer | Joel Barlow | Home - Sports Complex & Track [Directions] | TBA | L 1-2 | |
| Tue., 11/1 | Miscellaneous Events | Unified Sports Practice | 2:15 p.m. | |||
| Tue., 11/1 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 2:30-3:30 p.m. | ||
| Tue., 11/1 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 11/1 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 9:30 pm | |
| Tue., 11/1 | Miscellaneous Events | Southbury Park & Rec Adult Open BB | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 11/1 | Miscellaneous Events | Stby Park & Rec Adult Open Bball | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 11/2 | V Field Hockey | SWC Semi-Finals | Away [Directions] | 5:00 p.m. | @ New Milford, $8 Adults, $5 Students | |
| Wed., 11/2 | FR Girls Soccer | Masuk | Away - Benedict Stadium Field @ Masuk HS [Directions] | 3:45 p.m. | ||
| Wed., 11/2 | V Girls Swimming and Diving | SWC Diving Championships | Away [Directions] | 5:30 p.m. | @ Weston, warm-ups @ 4:00 pm | |
| Wed., 11/2 | V Girls Volleyball | SWC Semi-Finals | Away [Directions] | 7:00 p.m. | @ Masuk HS | |
| Wed., 11/2 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 2:30-3:30 p.m. | ||
| Wed., 11/2 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30 pm | |
| Wed., 11/2 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 11/2 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 9:30 pm | |
| Wed., 11/2 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 6:00-7:00 p.m. | ||
| Wed., 11/2 | Miscellaneous Events | Mdby Park & Rec Basketball | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Wed., 11/2 | Miscellaneous Events | Mdby Park & Rec Basketball | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Thu., 11/3 | FR Football | New Fairfield | Away - Rebel Stadium [Directions] | 4:00 p.m. | ||
| Thu., 11/3 | V Boys Soccer | SWC Championship Game | Away | Cancelled | Cancelled | |
| Thu., 11/3 | V Girls Soccer | SWC Championship Game | Away | Cancelled | Cancelled | |
| Thu., 11/3 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 2:30-3:30 p.m. | ||
| Thu., 11/3 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 11/3 | Miscellaneous Events | SWC Boys Soccer Championship Game | - Sports Complex & Track | 6:00 p.m. | 6:00 pm (Game Time 7:00 pm) | |
| Thu., 11/3 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 9:30 pm | |
| Thu., 11/3 | Miscellaneous Events | Stby Park & Rec Adult Open Bball | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 11/4 | V Boys Cross Country | CIAC State Open Championships | Away | 2:00 p.m. | ||
| Fri., 11/4 | V Football | New Fairfield | Home - Sports Complex & Track [Directions] | 7:00 p.m. | L 16-17 | Senior Night, $5 Adults, $3 Students |
| Fri., 11/4 | V Girls Cross Country | CIAC State Open Championships | Away | 2:45 p.m. | ||
| Fri., 11/4 | V Field Hockey | SWC Championship Game | Away | 7:00 p.m. | $10 Adults, $5 Students | |
| Fri., 11/4 | V Girls Volleyball | SWC Championship Game | Away | Cancelled | Cancelled | |
| Fri., 11/4 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30 pm | |
| Fri., 11/4 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Fri., 11/4 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 9:30 pm | |
| Sat., 11/5 | JV Football | New Fairfield | Away - NFHS Gym [Directions] | 3:00 p.m. | ||
| Sat., 11/5 | V Boys Soccer | Woodland (Scrim.) | Home - Sports Complex & Track [Directions] | 1:00 p.m. | ||
| Sat., 11/5 | V Girls Swimming and Diving | SWC Swim Championships | Away [Directions] | 4:00 p.m. | @ Masuk, $10 Adults, $5 Students, warm-ups @ 2:30 pm | |
| Sat., 11/5 | Miscellaneous Events | Stby Park & Rec Youth Bball Practice | - Auxiliary Gym | 1:00 p.m. | 1:00 - 9:00 pm | |
| Sat., 11/5 | Miscellaneous Events | Southbury Park & Rec Youth Bball Travel Practice | - Auxiliary Gym | 1:00 p.m. | 1:00 - 9:00 pm | |
| Sat., 11/5 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 11/6 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Mon., 11/7 | Miscellaneous Events | Sophomore Class Meeting | - Health Classroom - Room 201 | 2:15 p.m. | 2:15 - 3:00 pm | |
| Mon., 11/7 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 2:30-3:30 p.m. | ||
| Mon., 11/7 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30 pm | |
| Mon., 11/7 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Mon., 11/7 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 6:00-7:00 p.m. | ||
| Mon., 11/7 | Miscellaneous Events | Southbury Park & Rec Youth Bball | - PHS Main Gym | 7:00 p.m. | 7:00 - 8:30 pm | |
| Mon., 11/7 | Miscellaneous Events | Mdby Park & Rec Over 30 BB | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 11/8 | V Boys Soccer | CIAC Tournament Game | Home - Sports Complex & Track [Directions] | 4:00 p.m. | $8 Adults, $5 Students | |
| Tue., 11/8 | V Field Hockey | Branford | Away [Directions] | 6:30 p.m. | ||
| Tue., 11/8 | Miscellaneous Events | Unified Sports Practice | 2:15 p.m. | |||
| Tue., 11/8 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 2:30-3:30 p.m. | ||
| Tue., 11/8 | School Holidays and Closings | Professional Development Day - No Classes | ||||
| Wed., 11/9 | V Girls Swimming and Diving | CIAC Class L Diving Trials/Finals | Away - Middletown HS [Directions] | 5:30 p.m. | @ Middletown HS | |
| Wed., 11/9 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 2:30-3:30 p.m. | ||
| Wed., 11/9 | Miscellaneous Events | Pop Warner Cheer Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30 pm | |
| Wed., 11/9 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 11/9 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 6:00-7:00 p.m. | ||
| Wed., 11/9 | Miscellaneous Events | Mdby Park & Rec Basketball | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Thu., 11/10 | FR Football | Bethel | Home - Sports Complex & Track [Directions] | 4:00 p.m. | ||
| Thu., 11/10 | V Girls Volleyball | CIAC Tournament Game | Home [Directions] | 6:00 p.m. | $8 Adults, $5 Students | |
| Thu., 11/10 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 2:30-3:30 p.m. | ||
| Thu., 11/10 | Miscellaneous Events | Pomperaug Pop Warner Cheerleaders | - Health Classroom - Room 201 | 6:00 p.m. | Meeting - 6:00 - 7:30 pm | |
| Thu., 11/10 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 11/10 | Miscellaneous Events | Stby Park & Rec Adult Open Bball | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 11/11 | V Football | Bethel | Away - DeSantis Field at Bethel HS [Directions] | 7:00 p.m. | W 36-7 | |
| Fri., 11/11 | V Girls Soccer | Avon | Home - Sports Complex & Track [Directions] | 4:00 p.m. | W 4-1 | $8 Adults, $5 Students |
| Fri., 11/11 | Miscellaneous Events | Gymnastics Set up for Turkey Tumble | - PHS Main Gym | 5:00 p.m. | ||
| Fri., 11/11 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Sat., 11/12 | V Girls Cross Country | New England Championships | Away | 12:30 p.m. | North Scituate , Rhode Island | |
| Sat., 11/12 | V Girls Swimming and Diving | CIAC Class L Qualifying | Away - ast Hartford [Directions] | 11:30 a.m. | ||
| Sat., 11/12 | V Girls Volleyball | Daniel Hand | Away - DHHS Gym [Directions] | 6:00 p.m. | $10 Adults, $5 Students | |
| Sat., 11/12 | Miscellaneous Events | Turkey Tumble Gymnastics | - PHS Main Gym | 7:00 a.m. | 7:00 am - 8:00 pm | |
| Sat., 11/12 | Miscellaneous Events | Stby Park & Rec Youth Bball Practice | - Auxiliary Gym | 1:00 p.m. | 1:00 - 9:00 pm | |
| Sat., 11/12 | Miscellaneous Events | Southbury Park & Rec Youth Bball Travel Practice | - Auxiliary Gym | 1:00 p.m. | 1:00 - 9:00 pm | |
| Sat., 11/12 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 11/13 | Miscellaneous Events | Turkey Tumble Gymnastics | - PHS Main Gym | 7:00 a.m. | 7:00 am - 8:00 pm | |
| Sun., 11/13 | Miscellaneous Events | Pop Warner Football Games | - Sports Complex & Track | 8:00 a.m. | 8:00 am - 5:00 pm | |
| Sun., 11/13 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Mon., 11/14 | V Girls Soccer | St. Joseph | Away - St. Joseph HS [Directions] | 2:00 p.m. | L 0-4 | $8 Adults, $5 Students |
| Mon., 11/14 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 2:30-3:30 p.m. | ||
| Mon., 11/14 | Miscellaneous Events | CPR Class For Coaches | 5:00 p.m. | |||
| Mon., 11/14 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Mon., 11/14 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 6:00-7:00 p.m. | ||
| Mon., 11/14 | Miscellaneous Events | Southbury Park & Rec Youth Bball | - PHS Main Gym | 7:00 p.m. | 7:00 - 8:30 pm | |
| Mon., 11/14 | Miscellaneous Events | Mdby Park & Rec Over 30 BB | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 11/15 | V Girls Swimming and Diving | CIAC Class L Finals | Away - SCSU [Directions] | 6:00 p.m. | ||
| Tue., 11/15 | Miscellaneous Events | Unified Sports Practice | 2:15 p.m. | |||
| Tue., 11/15 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 2:30-3:30 p.m. | ||
| Tue., 11/15 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 11/15 | Miscellaneous Events | Southbury Parks & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 11/15 | Miscellaneous Events | Stby Park & Rec Adult Open Bball | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 11/15 | Miscellaneous Events | Southbury Park & Rec Open Bball | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 11/16 | V Girls Volleyball | State Semifinals vs. Farmington | Away [Directions] | 6:00 p.m. | @ Wolcott HS, $10 Adults, $5 Students | |
| Wed., 11/16 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 2:30-3:30 p.m. | ||
| Wed., 11/16 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 11/16 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 6:00-7:00 p.m. | ||
| Wed., 11/16 | Miscellaneous Events | Mdby Park & Rec Basketball | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Thu., 11/17 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 2:30-3:30 p.m. | ||
| Thu., 11/17 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 11/17 | Miscellaneous Events | Southbury Parks & Rec Youth Bball | - PHS Main Gym | 7:00 p.m. | 7:00 - 8:30 pm | |
| Thu., 11/17 | Miscellaneous Events | Southbury Park & Rec Open Bball | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 11/17 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 11/17 | Miscellaneous Events | Southbury Parks & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 11/17 | Miscellaneous Events | Stby Park & Rec Adult Open Bball | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 11/18 | V Girls Swimming and Diving | CIAC Open Diving | Away - Bulkeley HS [Directions] | Cancelled | Cancelled | |
| Fri., 11/18 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 2:30 p.m. | 2:30 - 3:30 pm | |
| Fri., 11/18 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Fri., 11/18 | Miscellaneous Events | Nonnewaug Football Game | - Sports Complex & Track | 7:00 p.m. | ||
| Sat., 11/19 | FR Football | Notre Dame-Fairfield | Away - McCarty Stadium at Notre Dame [Directions] | 10:30 a.m. | Sophomore/Freshmen Game | |
| Sat., 11/19 | V Girls Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 12:00 p.m. | ||
| Sat., 11/19 | Miscellaneous Events | Stby Park & Rec Youth Bball Practice | - Auxiliary Gym | 1:00 p.m. | 1:00 - 9:00 pm | |
| Sat., 11/19 | Miscellaneous Events | Southbury Park & Rec Youth Bball Travel Practice | - Auxiliary Gym | 1:00 p.m. | 1:00 - 9:00 pm | |
| Sat., 11/19 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sat., 11/19 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 11/20 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 11/20 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Mon., 11/21 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 3:30 p.m. | 3:30 - 8:30 pm | |
| Mon., 11/21 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Mon., 11/21 | Miscellaneous Events | Southbury Park & Rec Youth Bball | - PHS Main Gym | 7:00 p.m. | 7:00 - 8:30 pm | |
| Mon., 11/21 | Miscellaneous Events | Mdby Park & Rec Over 30 BB | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 11/22 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 3:30 p.m. | 3:30 - 8:30 pm | |
| Tue., 11/22 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 11/22 | Miscellaneous Events | Southbury Park & Rec Open Bball | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 11/22 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 11/22 | Miscellaneous Events | Southbury Parks & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 11/22 | Miscellaneous Events | Stby Park & Rec Adult Open Bball | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 11/23 | V Football | Notre Dame-Fairfield | Home - Sports Complex & Track [Directions] | 6:00 p.m. | L 8-27 | $5 Adults, $3 Students |
| Wed., 11/23 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 11:30 a.m. | 11:30 am - 3:00 pm | |
| Wed., 11/23 | School Holidays and Closings | Early Dismissal - Half Day Thanksgiving | ||||
| Thu., 11/24 | School Holidays and Closings | Thanksgiving Day | ||||
| Fri., 11/25 | School Holidays and Closings | Thanksgiving Recess - No School | ||||
| Mon., 11/28 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 2:30-3:30 p.m. | ||
| Mon., 11/28 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 3:30 p.m. | 3:30 - 8:30 pm | |
| Mon., 11/28 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Mon., 11/28 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 6:00-7:00 p.m. | ||
| Mon., 11/28 | Miscellaneous Events | Southbury Park & Rec Youth Bball | - PHS Main Gym | 7:00 p.m. | 7:00 - 8:30 pm | |
| Mon., 11/28 | Miscellaneous Events | Mdby Park & Rec Over 30 BB | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 11/29 | Miscellaneous Events | Sophomore Class Meeting | - Health Classroom - Room 201 | 2:15 p.m. | 2:15 - 3:00 pm | |
| Tue., 11/29 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 2:30-3:30 p.m. | ||
| Tue., 11/29 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 3:30 p.m. | 3:30 - 8:30 pm | |
| Tue., 11/29 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 11/29 | Miscellaneous Events | Southbury Park & Rec Open Bball | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 11/29 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 11/29 | Miscellaneous Events | Southbury Parks & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 11/29 | Miscellaneous Events | Stby Park & Rec Adult Open Bball | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 11/30 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 2:30-3:30 p.m. | ||
| Wed., 11/30 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 3:30 p.m. | 3:30 - 8:30 pm | |
| Wed., 11/30 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 11/30 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 6:00-7:00 p.m. | ||
| Wed., 11/30 | Miscellaneous Events | Mdby Park & Rec Basketball | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Thu., 12/1 | V Girls Basketball | Career Magnet (Scrim.) | Home - PHS Main Gym [Directions] | 5:00 p.m. | ||
| Thu., 12/1 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 2:30-3:30 p.m. | ||
| Thu., 12/1 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 3:30 p.m. | 3:30 - 8:30 pm | |
| Thu., 12/1 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 5:00 p.m. | 5:00 - 7:00 pm | |
| Thu., 12/1 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 12/1 | Miscellaneous Events | Southbury Parks & Rec Youth Bball | - PHS Main Gym | 7:00 p.m. | 7:00 - 8:30 pm | |
| Thu., 12/1 | Miscellaneous Events | Southbury Park & Rec Open Bball | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 12/1 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 12/1 | Miscellaneous Events | Southbury Parks & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 12/1 | Miscellaneous Events | Stby Park & Rec Adult Open Bball | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 12/2 | V Girls Basketball | Nonnewaug (Scrim.) | Away - Nonnewaug HS Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 12/2 | JV Girls Basketball | Nonnewaug (Scrim.) | Away - Nonnewaug HS Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 12/2 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 3:30 p.m. | 3:30 - 8:30 pm | |
| Fri., 12/2 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 4:30 p.m. | 4:30 - 6:30 pm | |
| Fri., 12/2 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Sat., 12/3 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 8:00 a.m. | 8:00 am - 12:00 pm | |
| Sat., 12/3 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sat., 12/3 | Miscellaneous Events | Southbury Park & Rec Olympic Swim Clinic | - PHS Pool | 1:30 p.m. | 1:30 - 7:00 pm | |
| Sun., 12/4 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 12/4 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 12/4 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 4:00 p.m. | 4:00 - 5:00 pm | |
| Mon., 12/5 | JV Girls Basketball | Berlin (Scrim.) | Home - PHS Main Gym [Directions] | 4:30 p.m. | $4 Adults, $3 Students | |
| Mon., 12/5 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | 1:45 - 6:45pm | |
| Mon., 12/5 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 2:30-3:30 p.m. | ||
| Mon., 12/5 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Mon., 12/5 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Mon., 12/5 | Miscellaneous Events | Conditioning By Thrive | - Weight Room | 6:00-7:00 p.m. | ||
| Mon., 12/5 | Miscellaneous Events | Southbury Park & Rec Youth Bball | - PHS Main Gym | 7:00 p.m. | 7:00 - 8:30 pm | |
| Mon., 12/5 | Miscellaneous Events | Mdby Park & Rec Over 30 BB | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 12/6 | V Boys Basketball | Wilby (Scrim.) | Away - Reggie O'Brien Gymnasium [Directions] | 6:30 p.m. | ||
| Tue., 12/6 | V Girls Basketball | Thomaston (Scrim.) | Away - Thomaston H.S. Gymnasium [Directions] | 5:00 p.m. | ||
| Tue., 12/6 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | 1:45 - 6:45pm | |
| Tue., 12/6 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 2:30-3:30 p.m. | ||
| Tue., 12/6 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Tue., 12/6 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 12/6 | Miscellaneous Events | Southbury Park & Rec Open Bball | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 12/6 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 12/6 | Miscellaneous Events | Southbury Parks & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 12/6 | Miscellaneous Events | Stby Park & Rec Adult Open Bball | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 12/7 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | 1:45 - 6:45pm | |
| Wed., 12/7 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 2:30-3:30 p.m. | ||
| Wed., 12/7 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Wed., 12/7 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 12/7 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 6:00-7:00 p.m. | ||
| Wed., 12/7 | Miscellaneous Events | Mdby Park & Rec Basketball | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Thu., 12/8 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | 1:45 - 6:45pm | |
| Thu., 12/8 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 2:30-3:30 p.m. | ||
| Thu., 12/8 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Thu., 12/8 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 12/8 | Miscellaneous Events | Southbury Parks & Rec Youth Bball | - PHS Main Gym | 7:00 p.m. | 7:00 - 8:30 pm | |
| Thu., 12/8 | Miscellaneous Events | Southbury Park & Rec Open Bball | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 12/8 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 12/8 | Miscellaneous Events | Southbury Parks & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 12/8 | Miscellaneous Events | Stby Park & Rec Adult Open Bball | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 12/9 | V Boys Ice Hockey | Northeastern Shamrocks (Scrim.) | Away - Bolton Ice Palace [Directions] | 8:10 p.m. | ||
| Fri., 12/9 | V Girls Basketball | Trumbull (Scrim.) | Away [Directions] | 4:00 p.m. | ||
| Fri., 12/9 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 2:30 p.m. | 2:30 - 6:30 pm | |
| Fri., 12/9 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Fri., 12/9 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Fri., 12/9 | School Holidays and Closings | Professional Development Day - No Classes | ||||
| Sat., 12/10 | V Boys Basketball | Wolcott (Scrim.) | Away [Directions] | 10:00 a.m. | ||
| Sat., 12/10 | V Boys Ice Hockey | Jamboree | Away - Shelton Rinks | 6:00 p.m. | ||
| Sat., 12/10 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sat., 12/10 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sat., 12/10 | Miscellaneous Events | Southbury Girls Softball | - Auxiliary Gym | 4:30 p.m. | 4:30 - 9:00 pm | |
| Sun., 12/11 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 12/11 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 12/11 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 4:00 p.m. | 4:00 - 5:00 pm | |
| Mon., 12/12 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | 1:45 - 6:45 pm | |
| Mon., 12/12 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 2:30-3:30 p.m. | ||
| Mon., 12/12 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Mon., 12/12 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 6:00-7:00 p.m. | ||
| Mon., 12/12 | Miscellaneous Events | Southbury Park & Rec Youth Bball | - PHS Main Gym | 7:00 p.m. | 7:00 - 8:30 pm | |
| Mon., 12/12 | Miscellaneous Events | Mdby Park & Rec Over 30 BB | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 12/13 | V Boys Basketball | Holy Cross (Scrim.) | Home - PHS Main Gym [Directions] | 3:00 p.m. | ||
| Tue., 12/13 | V Girls Basketball | St. Joseph | Away [Directions] | 5:00 p.m. | L 41-42 | @ Danbury High School |
| Tue., 12/13 | FR Girls Basketball | Ridgefield | Home - PHS Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 12/13 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | 1:45 - 6:45 pm | |
| Tue., 12/13 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 2:30-3:30 p.m. | ||
| Tue., 12/13 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Tue., 12/13 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 12/13 | Miscellaneous Events | Southbury Park & Rec Open Bball | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 12/13 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 12/13 | Miscellaneous Events | Southbury Parks & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 12/13 | Miscellaneous Events | Stby Park & Rec Adult Open Bball | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 12/14 | V Boys Ice Hockey | Northwest Catholic (Scrim.) | Home - Taft-Mays Rink [Directions] | 7:30 p.m. | ||
| Wed., 12/14 | V Wrestling | Brookfield/Shepaug | Away - BHS Small Gym [Directions] | 4:00 p.m. | Pomperaug: 54 Brookfield: 27 | |
| Wed., 12/14 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | 1:45 - 6:45 pm | |
| Wed., 12/14 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 2:30-3:30 p.m. | ||
| Wed., 12/14 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Wed., 12/14 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 12/14 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 6:00-7:00 p.m. | ||
| Wed., 12/14 | Miscellaneous Events | Mdby Park & Rec Basketball | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Thu., 12/15 | V Girls Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 7:00 p.m. | W 65-58 | @ Danbury High School |
| Thu., 12/15 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | 1:45 - 6:45 pm | |
| Thu., 12/15 | Miscellaneous Events | Conditioning by Thrive | - Weight Room | 2:30-3:30 p.m. | ||
| Thu., 12/15 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Thu., 12/15 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 12/15 | Miscellaneous Events | Southbury Parks & Rec Youth Bball | - PHS Main Gym | 7:00 p.m. | 7:00 - 8:30 pm | |
| Thu., 12/15 | Miscellaneous Events | Southbury Park & Rec Open Bball | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 12/15 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 12/15 | Miscellaneous Events | Southbury Parks & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 12/15 | Miscellaneous Events | Stby Park & Rec Adult Open Bball | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 12/16 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | 1:45 - 6:45 pm | |
| Fri., 12/16 | Miscellaneous Events | Wrestling Parents Refreshments Set Up | - Health Classroom - Room 201 | 5:30 p.m. | 5:30 - 8:30 pm | |
| Fri., 12/16 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Fri., 12/16 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Sat., 12/17 | V Boys Ice Hockey | Trumbull | Home - Taft-Mays Rink [Directions] | 7:30 p.m. | L 2-5 | |
| Sat., 12/17 | V Boys Indoor Track | Hillhouse Invitational | Away | 12:00 p.m. | ||
| Sat., 12/17 | V Wrestling | Pomperaug - Mike O'Keefe Invitational Tournament | Home - PHS Main Gym [Directions] | Cancelled | Cancelled | |
| Sat., 12/17 | V Girls Indoor Track | Hillhouse Invitational | Away | 12:00 p.m. | ||
| Sat., 12/17 | Miscellaneous Events | Wrestling Parents Refreshments for Tournament | - Health Classroom - Room 201 | 6:30 a.m. | 6:30 am - 5:00 pm | |
| Sat., 12/17 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 8:00 a.m. | 8:00 - 6:00 pm | |
| Sat., 12/17 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sat., 12/17 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 12/18 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 12/18 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 12/18 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 4:00 p.m. | 4:00 - 5:00 pm | |
| Mon., 12/19 | V Boys Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 7:00 p.m. | L 46 - 77 | |
| Mon., 12/19 | JV Boys Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 5:15 p.m. | ||
| Mon., 12/19 | FR Boys Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | ||
| Mon., 12/19 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | 1:45 - 6:45 pm | |
| Mon., 12/19 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Mon., 12/19 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Mon., 12/19 | Miscellaneous Events | Southbury Park & Rec Youth Bball | - PHS Main Gym | 7:00 p.m. | 7:00 - 8:30 pm | |
| Mon., 12/19 | Miscellaneous Events | Mdby Park & Rec Over 30 BB | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 12/20 | V Boys Swimming and Diving | Newtown | Away - Newtown HS Pool [Directions] | 4:00 p.m. | ||
| Tue., 12/20 | V Girls Basketball | New Fairfield | Away - NFHS Gym [Directions] | 7:00 p.m. | L 53-41 | @ New Fairfield HS |
| Tue., 12/20 | JV Girls Basketball | New Fairfield | Away - NFHS Gym [Directions] | 5:15 p.m. | ||
| Tue., 12/20 | FR Girls Basketball | New Fairfield | Away - New Fairfield HS [Directions] | 3:30 p.m. | ||
| Tue., 12/20 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | 1:45 - 6:45 pm | |
| Tue., 12/20 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Tue., 12/20 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 12/20 | Miscellaneous Events | Southbury Park and Rec Basketball | - PHS Main Gym | 7:00 p.m. | ||
| Tue., 12/20 | Miscellaneous Events | Southbury Park & Rec Open Bball | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 12/20 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 12/20 | Miscellaneous Events | Southbury Parks & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 12/20 | Miscellaneous Events | Stby Park & Rec Adult Open Bball | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 12/21 | V Boys Basketball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 7:00 p.m. | L 63 - 67 | |
| Wed., 12/21 | JV Boys Basketball | Wilton | Away [Directions] | 5:15 p.m. | ||
| Wed., 12/21 | FR Boys Basketball | Wilton | Away [Directions] | 3:45 p.m. | ||
| Wed., 12/21 | V Wrestling | Newtown | Home - Auxiliary Gym [Directions] | 6:00 p.m. | Pomperaug:6, Newtown: 76 | |
| Wed., 12/21 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | 1:45 - 7:45 pm | |
| Wed., 12/21 | Miscellaneous Events | Unified Sports Basketball Team Try-Outs | - PHS Main Gym | 2:15 p.m. | 2:15 - 3:30 pm | |
| Wed., 12/21 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Wed., 12/21 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 12/21 | Miscellaneous Events | Mdby Park & Rec BB | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Thu., 12/22 | V Girls Basketball | Hillhouse | Away [Directions] | TBA | W 63-58 | 5:00 game time, Vs. Hillhouse @ Newtown HS |
| Thu., 12/22 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | 1:45 - 6:45 pm | |
| Thu., 12/22 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Thu., 12/22 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 12/22 | Miscellaneous Events | Southbury Park & Rec Open Bball | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 12/22 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 12/22 | Miscellaneous Events | Southbury Parks & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 12/22 | Miscellaneous Events | Stby Park & Rec Adult Open Bball | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 12/23 | V Boys Ice Hockey | Enfield/East Granby/Stafford | Home - Taft-Mays Rink [Directions] | 7:30 p.m. | W 2-1 | |
| Fri., 12/23 | V Boys Swimming and Diving | Alumni Meet | Home - PHS Pool [Directions] | 6:00 p.m. | ||
| Fri., 12/23 | V Boys Swimming and Diving | Alumni Meet | Home - PHS Pool [Directions] | 6:00 p.m. | ||
| Fri., 12/23 | V Girls Basketball | Cromwell | Away [Directions] | 7:00 p.m. | W 73-72 OT | @ Newtown HS |
| Fri., 12/23 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | 1:45 - 6:45 pm | |
| Sun., 12/25 | School Holidays and Closings | Christmas | ||||
| Mon., 12/26 | V Boys Ice Hockey | Brookfield | Away - Danbury Ice Arena [Directions] | 3:30 p.m. | W 7-3 | |
| Mon., 12/26 | School Holidays and Closings | Winter Recess | ||||
| Tue., 12/27 | V Wrestling | Frank Chavez Tournament | Away | 9:00 a.m. | @ Simsbury HS | |
| Tue., 12/27 | FR Girls Basketball | Holy Cross | Away - Holy Cross HS [Directions] | 10:00 a.m. | ||
| Tue., 12/27 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 8:00 a.m. | 8:00 am - 12:00 pm | |
| Tue., 12/27 | Miscellaneous Events | RMS Girls Basketball Practice | - Auxiliary Gym | 12:00 p.m. | 12:00 to 2:00 pm | |
| Tue., 12/27 | School Holidays and Closings | Winter Recess | ||||
| Wed., 12/28 | V Boys Basketball | Bristol Eastern | Away - Nonnewaug HS Gymnasium [Directions] | 5:00 p.m. | W 50 - 48 | Nonnewaug Tournament |
| Wed., 12/28 | V Boys Ice Hockey | Westhill/Stamford | Away - Terry Connors [Directions] | 6:20 p.m. | W 4-1 | |
| Wed., 12/28 | V Boys Indoor Track | SWC Developmental | Away | Cancelled | Cancelled | @ Wilton High School |
| Wed., 12/28 | V Girls Indoor Track | SWC Developmental | Away | Cancelled | Cancelled | |
| Wed., 12/28 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 8:00 a.m. | 8:00 am - 12:00 pm | |
| Wed., 12/28 | School Holidays and Closings | Winter Recess | ||||
| Thu., 12/29 | V Boys Basketball | Nonnewaug | Away - Nonnewaug HS Gymnasium [Directions] | 7:00 p.m. | W 79 - 52 | 7:00 start |
| Thu., 12/29 | School Holidays and Closings | Winter Recess | ||||
| Fri., 12/30 | V Boys Ice Hockey | Daniel Hand | Home - Taft-Mays Rink [Directions] | 7:30 p.m. | W 5-2 | |
| Fri., 12/30 | V Wrestling | Trumbull Tournament | Away | 9:00 a.m. | ||
| Fri., 12/30 | V Girls Basketball | SMSA | Away [Directions] | 2:30 p.m. | W 59-48 | |
| Fri., 12/30 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 8:00 a.m. | 8:00 am - 12:00 pm | |
| Fri., 12/30 | School Holidays and Closings | Winter Recess | ||||
| Sun., 1/1 | School Holidays and Closings | New Years Day | ||||
| Mon., 1/2 | School Holidays and Closings | Winter Recess | ||||
| Tue., 1/3 | V Boys Swimming and Diving | Joel Barlow-Bethel Swim | Home - PHS Pool [Directions] | 4:00 p.m. | ||
| Tue., 1/3 | V Girls Basketball | Notre Dame-Fairfield | Away - Sister Marion Rielly Auditorium at Notre Dame [Directions] | 7:00 p.m. | L 57-39 | |
| Tue., 1/3 | JV Girls Basketball | Notre Dame-Fairfield | Away - Sister Marion Rielly Auditorium at Notre Dame [Directions] | 5:15 p.m. | ||
| Tue., 1/3 | FR Girls Basketball | Notre Dame-Fairfield | Away - Sister Marion Rielly Auditorium at Notre Dame [Directions] | 3:30 p.m. | ||
| Tue., 1/3 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | 1:45 - 9:00 pm | |
| Tue., 1/3 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Tue., 1/3 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 1/3 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 1/3 | Miscellaneous Events | Southbury Park & Rec Adult Open BB | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 1/3 | Miscellaneous Events | Southbury Parks & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 1/3 | Miscellaneous Events | Stby Park & Rec Adult Open Bball | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 1/4 | V Boys Basketball | New Fairfield | Home - PHS Main Gym [Directions] | 7:00 p.m. | W 51 - 29 | $4 Adults, $3 Students |
| Wed., 1/4 | JV Boys Basketball | New Fairfield | Home - PHS Main Gym [Directions] | 5:15 p.m. | $4 Adults, $3 Students | |
| Wed., 1/4 | V Boys Ice Hockey | Cheshire | Home - Taft-Mays Rink [Directions] | 8:00 p.m. | L 1-2 | |
| Wed., 1/4 | V Boys Indoor Track | SWC JV Developmental | Away | 3:00 p.m. | @ Danbury Dome | |
| Wed., 1/4 | V Wrestling | Joel Barlow | Home - Auxiliary Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/4 | V Girls Indoor Track | SWC JV Developmental | Away | 3:00 p.m. | @ Danbury Dome | |
| Wed., 1/4 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | 1:45 - 9:00 pm | |
| Wed., 1/4 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Wed., 1/4 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 1/5 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | 1:45 - 6:30 pm | |
| Thu., 1/5 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Thu., 1/5 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 1/5 | Miscellaneous Events | Southbury Parks & Rec Youth Bball | - PHS Main Gym | 7:00 p.m. | 7:00 - 8:30 pm | |
| Thu., 1/5 | Miscellaneous Events | Pomperaug Parents Softball Clinic | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Thu., 1/5 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 1/5 | Miscellaneous Events | Southbury Park & Rec Adult Open BB | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 1/5 | Miscellaneous Events | Southbury Parks & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 1/5 | Miscellaneous Events | Stby Park & Rec Adult Open Bball | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 1/6 | V Boys Basketball | New Milford | Away - New Milford HS [Directions] | 7:00 p.m. | W 76 - 56 | |
| Fri., 1/6 | JV Boys Basketball | New Milford | Away - New Milford HS [Directions] | 5:15 p.m. | ||
| Fri., 1/6 | FR Boys Basketball | New Milford | Away - New Milford HS [Directions] | 3:30 p.m. | ||
| Fri., 1/6 | V Competitive Cheerleading | Bethel | Home - PHS Main Gym [Directions] | 6:00 p.m. | Varsity Girls Basketball Game | |
| Fri., 1/6 | V Girls Basketball | Bethel | Home - PHS Main Gym [Directions] | 6:00 p.m. | L 58-33 | $4 Adults, $3 Students |
| Fri., 1/6 | JV Girls Basketball | Bethel | Home - PHS Main Gym [Directions] | 4:15 p.m. | $4 Adults, $3 Students | |
| Fri., 1/6 | FR Girls Basketball | Masuk | Home - PHS Main Gym [Directions] | 3:00 p.m. | ||
| Fri., 1/6 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | 1:45 - 9:00 pm | |
| Fri., 1/6 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Fri., 1/6 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Sat., 1/7 | Miscellaneous Events | Southbury Park & Rec Youth Bball Travel Practice | - Auxiliary Gym | 11:30 a.m. | 11:30 am - 9:00 pm | |
| Sat., 1/7 | Miscellaneous Events | Stby Park & Rec Youth Bball Practice | - Auxiliary Gym | 12:00 p.m. | 12:00 - 9:00 pm | |
| Sat., 1/7 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sat., 1/7 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 1/8 | Miscellaneous Events | Southbury Girls Softball | - Auxiliary Gym | 8:00 a.m. | 8:00 - 11:00 am | |
| Sun., 1/8 | Miscellaneous Events | Stby Park & Rec Youth Bball Practice | - PHS Main Gym | 1:00 p.m. | 1:00 - 9:00 pm | |
| Sun., 1/8 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 1/8 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 4:00 p.m. | 4:00 - 4:30 pm | |
| Mon., 1/9 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | 1:45 - 5:00 pm | |
| Mon., 1/9 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Mon., 1/9 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Mon., 1/9 | Miscellaneous Events | Southbury Park & Rec Youth Bball | - PHS Main Gym | 7:00 p.m. | 7:00 - 8:30 pm | |
| Mon., 1/9 | Miscellaneous Events | Pomperaug Parents Softball Clinic | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Mon., 1/9 | Miscellaneous Events | Mdby Park & Rec Over 30 BB | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 1/10 | V Co-ed Alpine Skiing | Ski Race | Away | Cancelled | Cancelled | |
| Tue., 1/10 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | 1:45 - 9:00 pm | |
| Tue., 1/10 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Tue., 1/10 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 1/10 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 1/10 | Miscellaneous Events | Southbury Park & Rec Adult Open BB | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 1/10 | Miscellaneous Events | Southbury Parks & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 1/10 | Miscellaneous Events | Stby Park & Rec Adult Open Bball | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 1/11 | V Boys Basketball | Bunnell | Away - Bunnell [Directions] | 7:00 p.m. | L 65 - 67 OT | |
| Wed., 1/11 | JV Boys Basketball | Bunnell | Away - Bunnell [Directions] | 5:15 p.m. | ||
| Wed., 1/11 | FR Boys Basketball | Bunnell | Away - Bunnell [Directions] | 3:30 p.m. | ||
| Wed., 1/11 | V Boys Ice Hockey | Farmington Valley Generals | Away - Avon Old Farms Rink [Directions] | 8:00 p.m. | W 4-0 | |
| Wed., 1/11 | V Boys Indoor Track | SWC JV Developmental | Away | 3:00 p.m. | @ Danbury Dome | |
| Wed., 1/11 | V Boys Swimming and Diving | Bethel | Home - PHS Pool [Directions] | 6:00 p.m. | ||
| Wed., 1/11 | V Wrestling | Bunnell | Away - Bunnell [Directions] | 6:00 p.m. | ||
| Wed., 1/11 | V Girls Basketball | Bunnell | Home - PHS Main Gym [Directions] | 7:00 p.m. | W 72-27 | $4 Adults, $3 Students |
| Wed., 1/11 | JV Girls Basketball | Bunnell | Home - PHS Main Gym [Directions] | 5:30 p.m. | $4 Adults, $3 Students | |
| Wed., 1/11 | FR Girls Basketball | Trumbull | Home - PHS Main Gym [Directions] | 3:45 p.m. | ||
| Wed., 1/11 | V Girls Indoor Track | SWC JV Developmental | Away | 3:00 p.m. | @ Danbury Dome | |
| Wed., 1/11 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | 1:45 - 6:30 pm | |
| Wed., 1/11 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Wed., 1/11 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 1/11 | Miscellaneous Events | Mdby Park & Rec BB | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Thu., 1/12 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | 1:45 - 5:00 pm | |
| Thu., 1/12 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Thu., 1/12 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 1/12 | Miscellaneous Events | Pomperaug Parents Softball Clinic | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Thu., 1/12 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 1/12 | Miscellaneous Events | Southbury Parks & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 1/12 | Miscellaneous Events | Stby Park & Rec Adult Open Bball | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 1/13 | V Boys Basketball | Immaculate | Home - PHS Main Gym [Directions] | 7:00 p.m. | W 54 - 52 | $4 Adults, $3 Students |
| Fri., 1/13 | JV Boys Basketball | Immaculate | Home - PHS Main Gym [Directions] | 5:15 p.m. | $4 Adults, $3 Students | |
| Fri., 1/13 | FR Boys Basketball | Immaculate | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 1/13 | V Boys Swimming and Diving | Brookfield | Home - PHS Pool [Directions] | 7:00 p.m. | $4 Adults, $3 Students | |
| Fri., 1/13 | V Wrestling | JV Wrestling Night | Home - Auxiliary Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/13 | V Competitive Cheerleading | Immaculate | Home - PHS Main Gym [Directions] | 7:00 p.m. | Varsity Boys Basketball Game | |
| Fri., 1/13 | V Girls Basketball | Immaculate | Away - Immaculate HS [Directions] | 7:00 p.m. | W 79-63 | |
| Fri., 1/13 | JV Girls Basketball | Immaculate | Away - Immaculate HS [Directions] | 5:15 p.m. | ||
| Fri., 1/13 | FR Girls Basketball | Immaculate | Away [Directions] | 3:30 p.m. | ||
| Fri., 1/13 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 3:00 p.m. | 3:00 - 9:00 pm | |
| Fri., 1/13 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Fri., 1/13 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Fri., 1/13 | School Holidays and Closings | Early Dismissal - Professional Development | ||||
| Sat., 1/14 | V Wrestling | Colter Abely Mid Season Tournament | Away | 9:00 a.m. | @ Mercy High School | |
| Sat., 1/14 | FR Girls Basketball | Holy Cross | Home - PHS Main Gym [Directions] | 11:30 a.m. | ||
| Sat., 1/14 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 11:00 a.m. | 11:00 - 1:00 pm | |
| Sat., 1/14 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 11:30 a.m. | 11:30 am - 1:00 pm | |
| Sat., 1/14 | Miscellaneous Events | Park and Rec Basketball | - PHS Main Gym | 1:00 p.m. | 1:00 pm to 9:00 pm | |
| Sat., 1/14 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 1/15 | Miscellaneous Events | Southbury Girls Softball | - Auxiliary Gym | 8:00 a.m. | 8:00 - 11:00 am | |
| Sun., 1/15 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Mon., 1/16 | V Boys Indoor Track | SWC Developmental | Away | 9:00 a.m. | @ Wesleyan University | |
| Mon., 1/16 | V Wrestling | Bristol Central Tournament | Away | 9:00 a.m. | ||
| Mon., 1/16 | V Girls Gymnastics | Fairfield Ludlowe, Nonnewaug | Away - Gymnastics & Cheer Academy [Directions] | 10:00 a.m. | 117.15 | |
| Mon., 1/16 | V Girls Indoor Track | SWC Developmental | Away | 9:00 a.m. | @ Wesleyan University | |
| Mon., 1/16 | School Holidays and Closings | Martin Luther King Day - no school | ||||
| Tue., 1/17 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | 1:45 - 9:00 pm | |
| Tue., 1/17 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Tue., 1/17 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 1/17 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 1/17 | Miscellaneous Events | Southbury Park & Rec Adult Open BB | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 1/17 | Miscellaneous Events | Southbury Parks & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 1/17 | Miscellaneous Events | Stby Park & Rec Adult Open Bball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 1/18 | V Boys Basketball | New Fairfield | Away - NFHS Gym [Directions] | 7:00 p.m. | L 58 - 61 | |
| Wed., 1/18 | JV Boys Basketball | New Fairfield | Away - NFHS Gym [Directions] | 5:15 p.m. | ||
| Wed., 1/18 | FR Boys Basketball | New Fairfield | Away - NFHS Gym [Directions] | 3:30 p.m. | ||
| Wed., 1/18 | V Boys Ice Hockey | North Branford | Away - Northford Ice Pavilion [Directions] | 6:15 p.m. | W 4-1 | |
| Wed., 1/18 | V Wrestling | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | 7:00 p.m. | ||
| Wed., 1/18 | V Girls Basketball | New Fairfield | Home - PHS Main Gym [Directions] | 7:00 p.m. | W 64-52 | $4 Adults, $3 Students |
| Wed., 1/18 | JV Girls Basketball | New Fairfield | Home - PHS Main Gym [Directions] | 5:15 p.m. | $4 Adults, $3 Students | |
| Wed., 1/18 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | 1:45 - 5:00 pm | |
| Wed., 1/18 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Wed., 1/18 | Miscellaneous Events | Mdby Park & Rec BB | - Auxiliary Gym | 6:00 p.m. | 6:00 - 7:30 pm | |
| Wed., 1/18 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 1/19 | V Boys Swimming and Diving | Bunnell-Stratford | Away - Flood Pool [Directions] | 6:00 p.m. | @ Flood Jr. High | |
| Thu., 1/19 | FR Girls Basketball | New Fairfield | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Thu., 1/19 | V Girls Gymnastics | New Milford, Nonnewaug | Away - New Milford HS [Directions] | 5:00 p.m. | 123.15 | |
| Thu., 1/19 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Thu., 1/19 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 1/19 | Miscellaneous Events | Southbury Parks & Rec Youth Bball | - PHS Main Gym | 7:00 p.m. | 7:00 - 8:30 pm | |
| Thu., 1/19 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 1/19 | Miscellaneous Events | Southbury Parks & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 1/19 | Miscellaneous Events | Stby Park & Rec Adult Open Bball | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 1/19 | School Holidays and Closings | Mid-terms (tentative) | ||||
| Fri., 1/20 | V Boys Basketball | Stratford | Home - PHS Main Gym [Directions] | 7:00 p.m. | W 77 - 54 | $4 Adults, $3 Students |
| Fri., 1/20 | JV Boys Basketball | Stratford | Home - PHS Main Gym [Directions] | 5:15 p.m. | $4 Adults, $3 Students | |
| Fri., 1/20 | FR Boys Basketball | Stratford | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 1/20 | V Boys Indoor Track | SWC Developmental | Away | 3:00 p.m. | ||
| Fri., 1/20 | V Boys Swimming and Diving | Naugatuck | Away - Naugatuck HS [Directions] | 4:00 p.m. | ||
| Fri., 1/20 | V Wrestling | JV Wrestling Night | Home - Auxiliary Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/20 | V Competitive Cheerleading | Stratford | Home - PHS Main Gym [Directions] | 7:00 p.m. | Varsity Boys Basketball Game | |
| Fri., 1/20 | V Girls Basketball | Stratford | Away - Needham Memorial Gymnasium [Directions] | 7:00 p.m. | W 70-27 | |
| Fri., 1/20 | JV Girls Basketball | Stratford | Away - Needham Memorial Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/20 | V Girls Indoor Track | SWC Developmental | Away | 3:00 p.m. | @ Weslyan University | |
| Fri., 1/20 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 3:00 p.m. | 3:00 - 9:00 pm | |
| Fri., 1/20 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Fri., 1/20 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Fri., 1/20 | Miscellaneous Events | Kinetic Kids Gymnastics Set-Up | Home - PHS Main Gym [Directions] | 8:00 p.m. | ||
| Fri., 1/20 | School Holidays and Closings | Mid-terms (tentative) | ||||
| Sat., 1/21 | V Boys Ice Hockey | Masuk | Home - Taft-Mays Rink [Directions] | 7:30 p.m. | W 5-0 | |
| Sat., 1/21 | V Wrestling | Granby Memorial | Away [Directions] | 10:00 a.m. | 9:00 Weigh In | |
| Sat., 1/21 | Miscellaneous Events | Southbury Park & Rec Youth Bball Travel Practice | - Auxiliary Gym | 11:30 a.m. | 11:30 am - 9:00 pm | |
| Sat., 1/21 | Miscellaneous Events | Kinetic Kids Gymnastics Invitational | Home - PHS Main Gym [Directions] | 7:00 a.m. | 7:00 am - 9:00 pm | |
| Sat., 1/21 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sat., 1/21 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 1/22 | Miscellaneous Events | Kinetic Kids Gymnastics Invitational | Home - PHS Main Gym [Directions] | 7:00 a.m. | 7:00 am - 9:00 pm | |
| Sun., 1/22 | Miscellaneous Events | Stby Park & Rec Youth Bball Practice | - Auxiliary Gym | 1:00 p.m. | 1:00 - 9:00 pm | |
| Sun., 1/22 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 1/22 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 4:00 p.m. | 4:00 - 4:30 pm | |
| Mon., 1/23 | V Girls Gymnastics | Pomperaug Invitational | Home - PHS Main Gym [Directions] | Cancelled | Cancelled | |
| Mon., 1/23 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Mon., 1/23 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Mon., 1/23 | School Holidays and Closings | Mid-terms (tentative) | ||||
| Tue., 1/24 | School Holidays and Closings | Mid-terms (tentative) | ||||
| Wed., 1/25 | V Boys Basketball | Joel Barlow | Away - Lower Gym [Directions] | 7:00 p.m. | W 72 - 50 | |
| Wed., 1/25 | JV Boys Basketball | Joel Barlow | Away - Lower Gym [Directions] | 5:15 p.m. | ||
| Wed., 1/25 | FR Boys Basketball | Joel Barlow | Away - Lower Gym [Directions] | 3:30 p.m. | ||
| Wed., 1/25 | V Boys Ice Hockey | East Haven Coop | Away - DiLungo Rink [Directions] | 7:00 p.m. | L 1-4 | |
| Wed., 1/25 | V Boys Indoor Track | SWC JV Developmental | Away | 3:00 p.m. | @ Danbury Dome | |
| Wed., 1/25 | V Boys Swimming and Diving | Masuk | Home - PHS Pool [Directions] | 7:00 p.m. | $4 Adults, $3 Students | |
| Wed., 1/25 | V Wrestling | New Milford | Home - Auxiliary Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/25 | V Girls Indoor Track | SWC JV Developmental | Away | 3:00 p.m. | @ Danbury Dome | |
| Wed., 1/25 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | 1:45 - 9:00 pm | |
| Wed., 1/25 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Wed., 1/25 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 1/25 | Miscellaneous Events | Mdby Park & Rec BB | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Thu., 1/26 | V Co-ed Alpine Skiing | Ski Race | Away | 4:00 p.m. | ||
| Thu., 1/26 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | 1:45 - 5:00 pm | |
| Thu., 1/26 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Thu., 1/26 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 1/26 | Miscellaneous Events | Southbury Parks & Rec Youth Bball | - PHS Main Gym | 7:00 p.m. | 7:00 - 8:30 pm | |
| Thu., 1/26 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 1/26 | Miscellaneous Events | Southbury Parks & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 1/26 | Miscellaneous Events | Stby Park & Rec Adult Open Bball | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 1/27 | V Boys Basketball | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | 7:00 p.m. | W 92 - 60 | |
| Fri., 1/27 | JV Boys Basketball | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | 5:15 p.m. | ||
| Fri., 1/27 | FR Boys Basketball | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | 3:30 p.m. | ||
| Fri., 1/27 | V Wrestling | JV Wrestling Night | Home - Auxiliary Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/27 | V Competitive Cheerleading | Masuk | Home - PHS Main Gym [Directions] | 7:00 p.m. | Varsity Girls Basketball Game | |
| Fri., 1/27 | V Girls Basketball | Masuk | Home - PHS Main Gym [Directions] | 7:00 p.m. | W 59-43 | $4 Adults, $3 Students |
| Fri., 1/27 | JV Girls Basketball | Masuk | Home - PHS Main Gym [Directions] | 5:15 p.m. | $4 Adults, $3 Students | |
| Fri., 1/27 | FR Girls Basketball | Masuk | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 1/27 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | 1:45 - 9:00 pm | |
| Fri., 1/27 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Fri., 1/27 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Sat., 1/28 | V Wrestling | Portland Tournament | Away | 8:00 a.m. | @ Portland High School | |
| Sat., 1/28 | V Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 6:00 p.m. | W 59-55 | |
| Sat., 1/28 | JV Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 4:30 p.m. | ||
| Sat., 1/28 | FR Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 3:00 p.m. | ||
| Sat., 1/28 | V Girls Gymnastics | Daniel Hand, Hamden, New Milford | Away - Polson Gymnastics Gym/DHHS Campus [Directions] | 10:30 a.m. | 114.55 | |
| Sat., 1/28 | Miscellaneous Events | Southbury Park & Rec Youth Bball Travel Practice | - Auxiliary Gym | 11:30 a.m. | 11:30 am - 9:00 pm | |
| Sat., 1/28 | Miscellaneous Events | Stby Park & Rec Youth Bball Practice | - Auxiliary Gym | 12:00 p.m. | 12:00 - 9:00 pm | |
| Sat., 1/28 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 1/29 | Miscellaneous Events | Southbury Girls Softball | - Auxiliary Gym | 8:00 a.m. | 8:00 - 11:00 am | |
| Sun., 1/29 | Miscellaneous Events | Stby Park & Rec Youth Bball Practice | - Auxiliary Gym | 1:00 p.m. | 1:00 - 9:00 pm | |
| Sun., 1/29 | Miscellaneous Events | Stby Parks & Rec Youth Bball | - PHS Main Gym | 1:00 p.m. | 1:00 pm - 9:00 pm | |
| Sun., 1/29 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 1/29 | Miscellaneous Events | Pomperaug Parents Softball Clinic | - Auxiliary Gym | 3:00 p.m. | 3:00 - 5:00 pm | |
| Sun., 1/29 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 4:00 p.m. | 4:00 - 4:30 pm | |
| Mon., 1/30 | V Boys Ice Hockey | New Milford | Away - Canterbury School [Directions] | 8:00 p.m. | W 5-1 | |
| Mon., 1/30 | V Girls Basketball | Joel Barlow | Home - PHS Main Gym [Directions] | 7:00 p.m. | W 45-38 | $4 Adults, $3 Students |
| Mon., 1/30 | JV Girls Basketball | Joel Barlow | Home - PHS Main Gym [Directions] | 5:15 p.m. | $4 Adults, $3 Students | |
| Mon., 1/30 | FR Girls Basketball | Joel Barlow | Home - PHS Main Gym [Directions] | Cancelled | Cancelled | |
| Mon., 1/30 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | 1:45 - 5:00 pm | |
| Mon., 1/30 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Mon., 1/30 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Mon., 1/30 | Miscellaneous Events | Pomperaug Parents Softball Clinic | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Mon., 1/30 | Miscellaneous Events | Southbury Park & Rec Youth Bball | - PHS Main Gym | 7:00 p.m. | 7:00 - 8:30 pm | |
| Mon., 1/30 | Miscellaneous Events | Mdby Park & Rec Over 30 BB | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 1/31 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 1:45 p.m. | 1:45 - 9:00 pm | |
| Tue., 1/31 | Miscellaneous Events | Unified Arts Basketball Practice | - PHS Main Gym | 2:15 p.m. | 2:15 - 3:00 pm | |
| Tue., 1/31 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Tue., 1/31 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 1/31 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 1/31 | Miscellaneous Events | Southbury Parks & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 2/1 | V Boys Swimming and Diving | Weston | Away - Weston MS Pool [Directions] | 4:30 p.m. | ||
| Wed., 2/1 | V Wrestling | Weston | Home - PHS Main Gym [Directions] | 7:00 p.m. | ||
| Wed., 2/1 | V Girls Gymnastics | New Milford, Joel Barlow, Nonnewaug | Home - Auxiliary Gym [Directions] | 5:00 p.m. | 128.2 | |
| Wed., 2/1 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Wed., 2/1 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 2/2 | V Co-ed Alpine Skiing | Ski Race | Away | 4:00 p.m. | ||
| Thu., 2/2 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Thu., 2/2 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 2/2 | Miscellaneous Events | Southbury Parks & Rec Youth Bball | - PHS Main Gym | 7:00 p.m. | 7:00 - 8:30 pm | |
| Thu., 2/2 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 2/2 | Miscellaneous Events | Southbury Parks & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 2/2 | Miscellaneous Events | Stby Park & Rec Adult Open Bball | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 2/3 | V Boys Basketball | Brookfield | Away - Brookfield Gym [Directions] | 7:00 p.m. | L 69 - 82 | |
| Fri., 2/3 | JV Boys Basketball | Brookfield | Away - Brookfield Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/3 | FR Boys Basketball | Brookfield | Away - Brookfield Gym [Directions] | 3:30 p.m. | ||
| Fri., 2/3 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Home - Taft-Mays Rink [Directions] | 7:30 p.m. | W 3-1 | |
| Fri., 2/3 | V Wrestling | Farmington, Branford, Seymour, Maloney | Home - Auxiliary Gym [Directions] | 5:00 p.m. | ||
| Fri., 2/3 | V Competitive Cheerleading | Brookfield | Home - PHS Main Gym [Directions] | 7:00 p.m. | Varsity Girls Basketball Game | |
| Fri., 2/3 | V Girls Basketball | Brookfield | Home - PHS Main Gym [Directions] | 7:00 p.m. | W 66-48 | $4 Adults, $3 Students |
| Fri., 2/3 | JV Girls Basketball | Brookfield | Home - PHS Main Gym [Directions] | 5:15 p.m. | $4 Adults, $3 Students | |
| Fri., 2/3 | V Girls Gymnastics | Oxford | Away [Directions] | 7:00 p.m. | 119.45 | @ Kinetic Kids |
| Fri., 2/3 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Fri., 2/3 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Sat., 2/4 | V Boys Indoor Track | SWC Championships | Away | 5:00 p.m. | FL Athletic Center in New Haven | |
| Sat., 2/4 | V Competitive Cheerleading | SWC Cheer Championships | Away [Directions] | Cancelled | Cancelled | |
| Sat., 2/4 | FR Girls Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 10:30 a.m. | ||
| Sat., 2/4 | V Girls Gymnastics | Joel Barlow, New Milford | Away [Directions] | Cancelled | Cancelled | @ Gymnastics and Cheer Academy of CT, Fairfield, Ct |
| Sat., 2/4 | V Girls Indoor Track | SWC Championships | Away | 5:00 p.m. | FL Athletic Center in New Haven | |
| Sat., 2/4 | Miscellaneous Events | Stby Park & Rec Youth Bball Practice | - Auxiliary Gym | 12:00 p.m. | 12:00 - 9:00 pm | |
| Sat., 2/4 | Miscellaneous Events | Stby Park & Rec Youth Bball Games | - PHS Main Gym | 1:00 p.m. | 1:00 - 8:30 pm | |
| Sat., 2/4 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sat., 2/4 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 2/5 | Miscellaneous Events | Southbury Girls Softball | - Auxiliary Gym | 8:00 a.m. | 8:00 - 11:00 am | |
| Sun., 2/5 | Miscellaneous Events | Stby Park & Rec Youth Bball Practice | - PHS Main Gym | 1:00 p.m. | 1:00 - 9:00 pm | |
| Sun., 2/5 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 2/5 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 2/5 | Miscellaneous Events | Pomperaug Parents Softball Clinic | - Auxiliary Gym | 3:00 p.m. | 3:00 - 5:00 pm | |
| Sun., 2/5 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 4:00 p.m. | 4:00 - 4:30 pm | |
| Mon., 2/6 | V Boys Basketball | Weston | Home - PHS Main Gym [Directions] | 7:00 p.m. | W 71 - 65 | $4 Adults, $3 Students |
| Mon., 2/6 | JV Boys Basketball | Weston | Home - PHS Main Gym [Directions] | 5:15 p.m. | $4 Adults, $3 Students | |
| Mon., 2/6 | FR Boys Basketball | Weston | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Mon., 2/6 | V Wrestling | Notre Dame-Fairfield | Away - Sister Marion Rielly Auditorium at Notre Dame [Directions] | 7:00 p.m. | ||
| Mon., 2/6 | V Girls Basketball | Weston | Away - WHS Gymnasium [Directions] | 7:00 p.m. | W 70-50 | |
| Mon., 2/6 | JV Girls Basketball | Weston | Away - WHS Gymnasium [Directions] | 5:15 p.m. | ||
| Mon., 2/6 | FR Girls Basketball | Weston | Away - WHS Gymnasium [Directions] | 3:30 p.m. | ||
| Mon., 2/6 | Miscellaneous Events | Unified Sports Basketball Practice | - Auxiliary Gym | 2:15 p.m. | 2:15 - 3:00 pm | |
| Mon., 2/6 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Mon., 2/6 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Mon., 2/6 | Miscellaneous Events | Pomperaug Parents Softball Clinic | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Mon., 2/6 | Miscellaneous Events | Southbury Park & Rec Youth Bball | - PHS Main Gym | 7:00 p.m. | 7:00 - 8:30 pm | |
| Mon., 2/6 | Miscellaneous Events | Mdby Park & Rec Over 30 BB | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 2/7 | V Girls Gymnastics | Fairfield Ludlowe, Daniel Hand | Away [Directions] | 6:00 p.m. | ||
| Tue., 2/7 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Tue., 2/7 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 2/7 | Miscellaneous Events | Southbury Park and Rec Youth BB | - PHS Main Gym | 7:00 p.m. | 7:00 to 8:30 pm | |
| Tue., 2/7 | Miscellaneous Events | Stby Park & Rec Youth Basketball | - PHS Main Gym | 7:00 p.m. | ||
| Tue., 2/7 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 2/7 | Miscellaneous Events | Southbury Parks & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 2/7 | Miscellaneous Events | Stby Park & Rec Adult Open Bball | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 2/8 | V Boys Basketball | Northwestern | Home - PHS Main Gym [Directions] | 7:00 p.m. | W 81 - 49 | $4 Adults, $3 Students |
| Wed., 2/8 | JV Boys Basketball | Northwestern | Home - PHS Main Gym [Directions] | 5:15 p.m. | $4 Adults, $3 Students | |
| Wed., 2/8 | V Boys Ice Hockey | Guilford | Away - East Haven Ice Rink [Directions] | 7:10 p.m. | W 3-2 | |
| Wed., 2/8 | V Boys Swimming and Diving | New Fairfield | Home - PHS Pool [Directions] | 4:30 p.m. | ||
| Wed., 2/8 | Miscellaneous Events | Unified Sports Basketball Practice | - PHS Main Gym | 2:15 p.m. | 2:15 - 3:00 pm | |
| Wed., 2/8 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Wed., 2/8 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 2/8 | Miscellaneous Events | Southbury Park and Rec Youth BB | - Auxiliary Gym | 7:00 p.m. | 7:00 to 8:30 pm | |
| Wed., 2/8 | Miscellaneous Events | Stby Park & Rec Youth Basketball | - Auxiliary Gym | 7:00 p.m. | ||
| Thu., 2/9 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Thu., 2/9 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 2/9 | Miscellaneous Events | Southbury Parks & Rec Youth Bball | - PHS Main Gym | 7:00 p.m. | 7:00 - 8:30 pm | |
| Thu., 2/9 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 2/9 | Miscellaneous Events | Southbury Parks & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 2/9 | Miscellaneous Events | Stby Park & Rec Adult Open Bball | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 2/10 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Fri., 2/10 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Fri., 2/10 | Miscellaneous Events | Softball Clinic | - Auxiliary Gym | 7:00 p.m. | ||
| Sat., 2/11 | V Boys Basketball | Kolbe Cathedral | Home - PHS Main Gym [Directions] | 5:15 p.m. | W 75 - 62 | $4 Adults, $3 Students |
| Sat., 2/11 | JV Boys Basketball | Kolbe Cathedral | Home - PHS Main Gym [Directions] | 3:30 p.m. | $4 Adults, $3 Students | |
| Sat., 2/11 | V Boys Ice Hockey | North Haven | Home - Taft-Mays Rink [Directions] | 7:30 p.m. | W 4-0 | |
| Sat., 2/11 | V Boys Indoor Track | CIAC Class Meet | Away | 4:00 p.m. | FL Athletic Center in New Haven | |
| Sat., 2/11 | V Boys Swimming and Diving | Intersquad Scrimmage | Home - PHS Pool [Directions] | Cancelled | Cancelled | |
| Sat., 2/11 | V Wrestling | SWC Championships | Away [Directions] | 9:30 a.m. | ||
| Sat., 2/11 | V Girls Basketball | Newtown | Away - Newtown HS Gymnasium [Directions] | 7:00 p.m. | L 45-47 | |
| Sat., 2/11 | JV Girls Basketball | Newtown | Away - Newtown HS Gymnasium [Directions] | 5:15 p.m. | ||
| Sat., 2/11 | FR Girls Basketball | Newtown | Away - Newtown HS Gymnasium [Directions] | 3:30 p.m. | ||
| Sat., 2/11 | V Girls Indoor Track | CIAC Class Meet | Away | TBA | FL Athletic Center in New Haven | |
| Sat., 2/11 | Miscellaneous Events | Southbury Park & Rec Youth Bball Travel Practice | - Auxiliary Gym | 11:30 a.m. | 11:30 am - 9:00 pm | |
| Sat., 2/11 | Miscellaneous Events | Stby Park & Rec Youth Bball Practice | - Auxiliary Gym | 12:00 p.m. | 12:00 - 9:00 pm | |
| Sat., 2/11 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sat., 2/11 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 2/12 | Miscellaneous Events | Southbury Girls Softball | - Auxiliary Gym | 8:00 a.m. | 8:00 - 11:00 am | |
| Sun., 2/12 | Miscellaneous Events | Stby Parks & Rec Youth Bball | - PHS Main Gym | 1:00 p.m. | 1:00 pm - 9:00 pm | |
| Sun., 2/12 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 2/12 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 2/12 | Miscellaneous Events | Pomperaug Parents Softball Clinic | - Auxiliary Gym | 3:00 p.m. | 3:00 - 5:00 pm | |
| Mon., 2/13 | V Boys Basketball | Newtown | Home - PHS Main Gym [Directions] | 7:00 p.m. | W 69 - 56 | $4 Adults, $3 Students |
| Mon., 2/13 | JV Boys Basketball | Newtown | Home - PHS Main Gym [Directions] | 5:15 p.m. | $4 Adults, $3 Students | |
| Mon., 2/13 | FR Boys Basketball | Newtown | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Mon., 2/13 | V Competitive Cheerleading | Newtown | Home - PHS Main Gym [Directions] | 7:00 p.m. | Varsity Boys Basketball Game | |
| Mon., 2/13 | V Girls Basketball | Kolbe Cathedral | Away - Shehan Center [Directions] | 7:00 p.m. | W 65-54 | @ The Sheehan Center |
| Mon., 2/13 | JV Girls Basketball | Kolbe Cathedral | Away - Shehan Center [Directions] | 5:15 p.m. | ||
| Mon., 2/13 | V Girls Gymnastics | SWC Championship Meet | Away [Directions] | 5:00 p.m. | 128.05 | @ New Milford |
| Mon., 2/13 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Mon., 2/13 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Mon., 2/13 | Miscellaneous Events | Pomperaug Parents Softball Clinic | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Mon., 2/13 | Miscellaneous Events | Southbury Park & Rec Youth Bball | - PHS Main Gym | 7:00 p.m. | 7:00 - 8:30 pm | |
| Mon., 2/13 | Miscellaneous Events | Mdby Park & Rec Over 30 BB | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 2/14 | V Boys Basketball | New Milford | Home - PHS Main Gym [Directions] | 7:00 p.m. | W 83 - 56 | $4 Adults, $3 Students |
| Tue., 2/14 | JV Boys Basketball | New Milford | Home - PHS Main Gym [Directions] | 5:15 p.m. | $4 Adults, $3 Students | |
| Tue., 2/14 | FR Boys Basketball | New Milford | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Tue., 2/14 | V Boys Swimming and Diving | New Milford | Home - Pomperaug HS [Directions] | 6:00 p.m. | ||
| Tue., 2/14 | V Girls Basketball | New Milford | Away - New Milford HS [Directions] | 7:00 p.m. | W 69-37 | |
| Tue., 2/14 | JV Girls Basketball | New Milford | Away - New Milford HS [Directions] | 5:15 p.m. | ||
| Tue., 2/14 | FR Girls Basketball | New Milford | Away - New Milford HS [Directions] | 3:30 p.m. | ||
| Tue., 2/14 | V Girls Gymnastics | New Milford, Staples | Away - New Milford HS [Directions] | 5:00 p.m. | 125.6 | @ New Milford |
| Tue., 2/14 | Miscellaneous Events | Unified Sports Basketball Practice | - Auxiliary Gym | 2:15 p.m. | 2:15 - 3:00 pm | |
| Tue., 2/14 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Tue., 2/14 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 2/14 | Miscellaneous Events | Stby Park & Rec Adult Open Bball | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 2/14 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 2/14 | Miscellaneous Events | Southbury Parks & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 2/15 | V Boys Ice Hockey | Hall | Home - Taft-Mays Rink [Directions] | 8:00 p.m. | W 4-0 | |
| Wed., 2/15 | V Co-ed Alpine Skiing | Ski Meet | Away | Cancelled | Cancelled | |
| Wed., 2/15 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Wed., 2/15 | Miscellaneous Events | Southbury Park & Rec Youth Basketball | - Auxiliary Gym | 6:00 p.m. | 6:00 - 9:00 pm | |
| Wed., 2/15 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 2/15 | Miscellaneous Events | Mdby Park & Rec BB | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Thu., 2/16 | V Boys Basketball | Notre Dame-Fairfield | Home - PHS Main Gym [Directions] | 7:00 p.m. | L 61 - 73 | $4 Adults, $3 Students |
| Thu., 2/16 | JV Boys Basketball | Notre Dame-Fairfield | Home - PHS Main Gym [Directions] | 5:15 p.m. | $4 Adults, $3 Students | |
| Thu., 2/16 | FR Boys Basketball | Notre Dame-Fairfield | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Thu., 2/16 | Miscellaneous Events | Unified Sports Basketball Practice | - Auxiliary Gym | 2:15 p.m. | 2:15 - 3:00 pm | |
| Thu., 2/16 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Thu., 2/16 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 2/16 | Miscellaneous Events | Stby Park & Rec Adult Open Bball | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 2/16 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 2/16 | Miscellaneous Events | Southbury Parks & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 2/17 | V Wrestling | CIAC Class L Championships | Away - Bristol Central HS [Directions] | 4:00 p.m. | ||
| Fri., 2/17 | V Girls Basketball | SWC Quarter-Finals | Home - PHS Main Gym [Directions] | 7:00 p.m. | $8 Adults, $5 Students | |
| Fri., 2/17 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Fri., 2/17 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Fri., 2/17 | Miscellaneous Events | Middlebury Baseball Workouts | - Auxiliary Gym | 6:30 p.m. | 6:30 - 8:30pm | |
| Sat., 2/18 | V Boys Ice Hockey | Amity | Home - Taft-Mays Rink [Directions] | 8:00 p.m. | W 3-1 | |
| Sat., 2/18 | V Wrestling | CIAC Class L Championships | Away - Bristol Central HS [Directions] | 9:00 a.m. | ||
| Sat., 2/18 | V Competitive Cheerleading | St. Joseph's Competition | Away | Cancelled | Cancelled | |
| Sat., 2/18 | V Girls Gymnastics | Fairfield Ludlowe | Away [Directions] | 10:00 a.m. | 120.7 | |
| Sat., 2/18 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 10:30 a.m. | 10:30 am to 12:00 pm | |
| Sun., 2/19 | Miscellaneous Events | Southbury Girls Softball | - Auxiliary Gym | 8:00 a.m. | 8:00 - 11:00 am | |
| Sun., 2/19 | Miscellaneous Events | Pomperaug Parents Softball Clinic | - Auxiliary Gym | 3:00 p.m. | 3:00 - 5:00 pm | |
| Mon., 2/20 | V Boys Basketball | Bethel | Away - Bethel HS [Directions] | 4:30 p.m. | W 57 - 52 | |
| Mon., 2/20 | JV Boys Basketball | Bethel | Away - Bethel HS [Directions] | 2:45 p.m. | ||
| Mon., 2/20 | FR Boys Basketball | Bethel | Away - Bethel HS [Directions] | 1:00 p.m. | ||
| Mon., 2/20 | V Boys Ice Hockey | Guilford | Home - Taft-Mays Rink [Directions] | 8:00 p.m. | W 4-1 | |
| Mon., 2/20 | V Boys Indoor Track | State Indoor Track Open | Away | 4:00 p.m. | FL Athletic Center in New Haven | |
| Mon., 2/20 | V Wrestling | Pomperaug JV Wrestling Tournament | Home - PHS Main Gym [Directions] | 9:00 a.m. | ||
| Mon., 2/20 | V Girls Basketball | SWC Semi-Finals | Away | Cancelled | Cancelled | $8 Adults, $5 Students |
| Mon., 2/20 | V Girls Gymnastics | Newtown, Oxford, Nonnewaug | Home - Auxiliary Gym [Directions] | 3:00 p.m. | 131.4 | |
| Mon., 2/20 | V Girls Indoor Track | State Indoor Track Open | Away | 4:00 p.m. | FL Athletic Center in New Haven | |
| Mon., 2/20 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 10:30 a.m. | 10:30 am to 1:00 pm | |
| Mon., 2/20 | Miscellaneous Events | Wrestling Parents Refreshments | - Health Classroom - Room 201 | 6:00 a.m. | 6:00 am - 5:00 pm | |
| Mon., 2/20 | School Holidays and Closings | Presidents Day - No School | ||||
| Tue., 2/21 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 2/21 | School Holidays and Closings | Winter Recess | ||||
| Wed., 2/22 | V Boys Ice Hockey | New Fairfield | Away - Danbury Ice Arena [Directions] | 7:40 p.m. | L 0-3 | |
| Wed., 2/22 | FR Girls Basketball | St. Joseph | Home - PHS Main Gym [Directions] | 5:00 p.m. | ||
| Wed., 2/22 | Miscellaneous Events | Unified Sports Basketball Practice | - PHS Main Gym | 2:15 p.m. | 2:15 - 3:00 pm | |
| Wed., 2/22 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Wed., 2/22 | Miscellaneous Events | Stby Park & Rec Basketball | - Auxiliary Gym | 6:00 p.m. | 6:00 - 9:00 pm | |
| Wed., 2/22 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 2/22 | Miscellaneous Events | Mdby Park & Rec BB | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Thu., 2/23 | V Boys Ice Hockey | Milford Coop | Home - Taft-Mays Rink [Directions] | 7:30 p.m. | W 5-0 | |
| Thu., 2/23 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Thu., 2/23 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 2/23 | Miscellaneous Events | Southbury Parks & Rec Youth Bball | - PHS Main Gym | 7:00 p.m. | 7:00 - 8:30 pm | |
| Thu., 2/23 | Miscellaneous Events | Stby Park & Rec Adult Open Bball | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 2/23 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 2/23 | Miscellaneous Events | Southbury Parks & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 2/24 | V Boys Basketball | Weston | Home - PHS Main Gym [Directions] | 7:00 p.m. | W 82 - 50 | $8 Adults, $5 Students |
| Fri., 2/24 | V Boys Indoor Track | New England Indoor Track Meet | Away | Cancelled | Cancelled | |
| Fri., 2/24 | V Wrestling | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | ||
| Fri., 2/24 | V Girls Indoor Track | New England Indoor Track Meet | Away | Cancelled | Cancelled | |
| Fri., 2/24 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Fri., 2/24 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Fri., 2/24 | Miscellaneous Events | Middlebury Baseball Workouts | - Auxiliary Gym | 6:30 p.m. | 6:30 - 8:30pm | |
| Sat., 2/25 | V Wrestling | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 9:00 a.m. | No Bus | |
| Sat., 2/25 | V Girls Gymnastics | CIAC Class Meet | Home - PHS Main Gym [Directions] | TBA | ||
| Sat., 2/25 | Miscellaneous Events | Stby Parks & Rec Youth Bball | - Auxiliary Gym | 11:30 a.m. | 11:30 am - 9:00 pm | |
| Sat., 2/25 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sat., 2/25 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 2/26 | Miscellaneous Events | Mdby Park & Rec Dive Team Training | - PHS Pool | 10:00 a.m. | 10:00 am - 1:00 pm | |
| Sun., 2/26 | Miscellaneous Events | Southbury Girls Softball | - Auxiliary Gym | 8:00 a.m. | 8:00 - 11:00 am | |
| Sun., 2/26 | Miscellaneous Events | Stby Park & Rec Youth Bball Practice | - PHS Main Gym | 1:00 p.m. | 1:00 - 9:00 pm | |
| Sun., 2/26 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 2/26 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 2/26 | Miscellaneous Events | Pomperaug Parents Softball Clinic | - Auxiliary Gym | 3:00 p.m. | 3:00 - 5:00 pm | |
| Mon., 2/27 | V Boys Basketball | Bunnell | Away - Bunnell [Directions] | 7:00 p.m. | @ Bunnell High School, $8 Adults, $5 Students | |
| Mon., 2/27 | V Boys Ice Hockey | Branford | Away - NORTHFORD ICE PAVILION [Directions] | 8:00 p.m. | T 1-1(OT) | |
| Mon., 2/27 | V Co-ed Alpine Skiing | Ski Meet | Away | 3:00 p.m. | @ Mount Southington | |
| Mon., 2/27 | V Girls Basketball | Tournament Game - Opponent Not Known | Home - PHS Main Gym [Directions] | 7:00 p.m. | $8 Adults, $5 Students, CIAC Tournament game | |
| Mon., 2/27 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Mon., 2/27 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Mon., 2/27 | Miscellaneous Events | Pomperaug Parents Softball Clinic | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Mon., 2/27 | Miscellaneous Events | Southbury Park & Rec Youth Bball | - PHS Main Gym | 7:00 p.m. | 7:00 - 8:30 pm | |
| Mon., 2/27 | Miscellaneous Events | Mdby Park & Rec Over 30 BB | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 2/28 | Miscellaneous Events | Unified Sports Basketball Practice | - PHS Main Gym | 2:15 p.m. | 2:15 - 3:30 pm | |
| Tue., 2/28 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Tue., 2/28 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 2/28 | Miscellaneous Events | Stby Park & Rec Adult Open Bball | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 2/28 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 2/28 | Miscellaneous Events | Southbury Parks & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 3/1 | V Boys Swimming and Diving | SWC Diving Championship | Home - PHS Pool [Directions] | 6:00 p.m. | 4:15 warm up, @ Pomperaug High School | |
| Wed., 3/1 | Miscellaneous Events | Unified Sports Basketball Practice | - Auxiliary Gym | 2:15 p.m. | 2:15 - 3:30 pm | |
| Wed., 3/1 | Miscellaneous Events | Athletic Trainer | 2:30 p.m. | 2:30 - 9:00 pm | ||
| Wed., 3/1 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 3/1 | Miscellaneous Events | Mdby Park & Rec BB | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Thu., 3/2 | V Boys Basketball | SWC Championship Game | Away | Cancelled | Cancelled | $10 Adults, $5 Students |
| Thu., 3/2 | V Girls Basketball | CIAC Tournament Game | Home - PHS Main Gym [Directions] | 7:00 p.m. | $8 Adults, $5 students | |
| Thu., 3/2 | Miscellaneous Events | Athletic Trainer | 2:30 p.m. | 2:30 - TBA | ||
| Thu., 3/2 | Miscellaneous Events | PAC Swimming | - PHS Pool | 5:30 p.m. | 5:30 - 7:30 pm | |
| Thu., 3/2 | Miscellaneous Events | Southbury Park and Rec Basketball | - Auxiliary Gym | 6:00 p.m. | 6:00 to 9:00 pm | |
| Thu., 3/2 | Miscellaneous Events | Stby Park & Rec Basketball | - Auxiliary Gym | 6:00 p.m. | 6:00 - 9:00 pm | |
| Thu., 3/2 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 3/2 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 3/2 | Miscellaneous Events | Stby Park & Rec Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 9:30 pm | |
| Thu., 3/2 | Miscellaneous Events | Southbury Parks & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 3/3 | V Boys Ice Hockey | East Haven Coop | Away - DiLungo Rink [Directions] | 4:00 p.m. | ||
| Fri., 3/3 | V Boys Swimming and Diving | SWC Swim Championship, 3:30 Warm-ups | Away [Directions] | 5:00 p.m. | @ Masuk High School, $10 Adults, $5 Students | |
| Fri., 3/3 | V Wrestling | New England Championships | Away - Providence Career and Technical Center [Directions] | 4:00 p.m. | ||
| Fri., 3/3 | Miscellaneous Events | Athletic Trainer | 2:30 p.m. | 2:30 - 6:30 pm | ||
| Fri., 3/3 | Miscellaneous Events | PAC Swimming | - PHS Pool | 5:30 p.m. | 5:30 - 7:30 pm | |
| Fri., 3/3 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Fri., 3/3 | Miscellaneous Events | Middlebury Baseball Workouts | - Auxiliary Gym | 6:30 p.m. | 6:30 - 8:30 pm | |
| Fri., 3/3 | Miscellaneous Events | Stby Park & Rec Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 9:30 pm | |
| Sat., 3/4 | V Boys Swimming and Diving | Naugatuck (Scrim.) | Away [Directions] | 2:00 p.m. | JV Meet at Naugatuck High School | |
| Sat., 3/4 | V Wrestling | New England Championships | Away - Providence Career and Technical Center [Directions] | 9:00 a.m. | ||
| Sat., 3/4 | V Competitive Cheerleading | State Competition | Away | Cancelled | Cancelled | @ Hillhouse High School |
| Sat., 3/4 | V Girls Gymnastics | CIAC Opens | Away | TBA | TBA | |
| Sat., 3/4 | Miscellaneous Events | Stby Park & Rec Youth Bball Practice | - Auxiliary Gym | 12:00 p.m. | 12:00 - 9:00 pm | |
| Sat., 3/4 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sat., 3/4 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 3/5 | Miscellaneous Events | Southbury Girls Softball | - Auxiliary Gym | 8:00 a.m. | 8:00 - 11:00 am | |
| Sun., 3/5 | Miscellaneous Events | Stby Park & Rec Youth Bball Practice | - PHS Main Gym | 1:00 p.m. | 1:00 - 9:00 pm | |
| Sun., 3/5 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 3/5 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 3/5 | Miscellaneous Events | Pomperaug Parents Softball Clinic | - Auxiliary Gym | 3:00 p.m. | 3:00 - 5:00 pm | |
| Mon., 3/6 | Miscellaneous Events | Junior Class Government Meeting | - Health Classroom - Room 201 | 2:15 p.m. | 2:15 - 3:00 pm | |
| Mon., 3/6 | Miscellaneous Events | Athletic Trainer | 2:30 p.m. | 2:30 - 6:30 pm | ||
| Mon., 3/6 | Miscellaneous Events | CPR Class For Coaches | - Health Classroom - Room 201 | 5:00 p.m. | ||
| Mon., 3/6 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Mon., 3/6 | Miscellaneous Events | Mdby Park & Rec Over 30 BB | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 3/7 | V Boys Basketball | CIAC Tournament Game | Home - PHS Main Gym [Directions] | 6:00 p.m. | $8 Adults, $5 Students | |
| Tue., 3/7 | V Girls Basketball | CIAC Tournament Game | Home - PHS Main Gym [Directions] | 8:00 p.m. | $8 Adults, $5 Students | |
| Tue., 3/7 | Miscellaneous Events | Unified Sports Basketball Practice | - Auxiliary Gym | 2:15 p.m. | 2:15 - 3:30 pm | |
| Tue., 3/7 | Miscellaneous Events | Athletic Trainer | 2:30 p.m. | 2:30 - 9:00 pm | ||
| Tue., 3/7 | Miscellaneous Events | PAC Swimming | - PHS Pool | 5:30 p.m. | 5:30 - 7:30 pm | |
| Tue., 3/7 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 3/7 | Miscellaneous Events | Civil Air Patrol | - PHS Pool | 6:15 p.m. | Water Survival Training, 6:30 - 8:30 | |
| Tue., 3/7 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 3/7 | Miscellaneous Events | Southbury Parks & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 3/8 | V Boys Swimming and Diving | CIAC Class L Diving Trials/Finals | Away - Middletown HS [Directions] | 5:30 p.m. | ||
| Wed., 3/8 | Miscellaneous Events | Unified Sports Basketball Scrimmage | - Auxiliary Gym | 2:15 p.m. | 2:15 - 3:30 pm | |
| Wed., 3/8 | Miscellaneous Events | Athletic Trainer | 2:30 p.m. | 2:30 - 6:30 pm | ||
| Wed., 3/8 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 3/8 | Miscellaneous Events | PAC Swimming | - PHS Pool | 6:30 p.m. | 6:30 - 8:30 pm | |
| Wed., 3/8 | Miscellaneous Events | Mdby Park & Rec BB | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Thu., 3/9 | Miscellaneous Events | Athletic Trainer | 2:30 p.m. | 2:30 - 6:30 pm | ||
| Thu., 3/9 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 3/9 | Miscellaneous Events | Middlebury Baseball Workouts | - Auxiliary Gym | 6:30 p.m. | 6:30 - 8:30 pm | |
| Thu., 3/9 | Miscellaneous Events | PAC Swimming | - PHS Pool | 6:30 p.m. | 6:30 - 8:30 pm | |
| Thu., 3/9 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 3/9 | Miscellaneous Events | Southbury Parks & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 3/10 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Fri., 3/10 | Miscellaneous Events | Middlebury Baseball Workouts | - Auxiliary Gym | 6:30 p.m. | 6:30 - 8:30 pm | |
| Fri., 3/10 | Miscellaneous Events | PAC Swimming | - PHS Pool | 6:30 p.m. | 6:30 - 8:30 pm | |
| Fri., 3/10 | Miscellaneous Events | Athletic Trainer | TBA | |||
| Fri., 3/10 | School Holidays and Closings | Early Dismissal - Professional Development | ||||
| Sat., 3/11 | V Boys Ice Hockey | Branford | Away - Bennett Rink - West Haven [Directions] | 4:00 p.m. | ||
| Sat., 3/11 | V Boys Swimming and Diving | CIAC Class L Qualifying | Away - Kennedy HS [Directions] | 4:30 p.m. | ||
| Sat., 3/11 | V Girls Basketball | CIAC Tournament Game | Away | 5:00 p.m. | @ Sheehan HS, $8 Adults, $5 Students | |
| Sat., 3/11 | V Girls Gymnastics | New England Championships | Away | TBA | TBA | |
| Sat., 3/11 | Miscellaneous Events | Stby Park & Rec Youth Bball Practice | - Auxiliary Gym | 12:00 p.m. | 12:00 - 9:00 pm | |
| Sat., 3/11 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sat., 3/11 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 3/12 | Miscellaneous Events | Mdby Park & Rec Dive Team Training | - PHS Pool | 10:00 a.m. | 10:00 am - 1:00 pm | |
| Sun., 3/12 | Miscellaneous Events | PHS Baseball Clinic | - Auxiliary Gym | 10:30 a.m. | 10:30 - 1:00 pm | |
| Sun., 3/12 | Miscellaneous Events | PHS Baseball Clinic | - PHS Main Gym | 10:30 a.m. | 10:30 - 1:00 pm | |
| Sun., 3/12 | Miscellaneous Events | Southbury Girls Softball | - Auxiliary Gym | 8:00 a.m. | 8:00 - 11:00 am | |
| Sun., 3/12 | Miscellaneous Events | Stby Park & Rec Youth Bball Practice | - PHS Main Gym | 1:00 p.m. | 1:00 - 9:00 pm | |
| Sun., 3/12 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 3/12 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Mon., 3/13 | V Boys Swimming and Diving | CIAC Class L Finals | Away - Wesleyan Univ. [Directions] | 1:30 p.m. | @ Weslyan, $10 Adults, $5 Students | |
| Mon., 3/13 | Miscellaneous Events | Unified Sports Basketball Practice | - Auxiliary Gym | 2:15 p.m. | 2:15 - 3:30 pm | |
| Mon., 3/13 | Miscellaneous Events | Athletic Trainer | 2:30 p.m. | |||
| Mon., 3/13 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Mon., 3/13 | Miscellaneous Events | PAC Swimming | - PHS Pool | 6:30 p.m. | 6:30 - 8:30 pm | |
| Mon., 3/13 | Miscellaneous Events | Mdby Park & Rec Over 30 BB | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 3/14 | Miscellaneous Events | Athletic Trainer | 2:30 p.m. | |||
| Tue., 3/14 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 3/14 | Miscellaneous Events | PAC Swimming | - PHS Pool | 6:30 p.m. | 6:30 - 8:30 pm | |
| Tue., 3/14 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 3/14 | Miscellaneous Events | Southbury Parks & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 3/15 | Miscellaneous Events | Athletic Trainer | 2:30 p.m. | |||
| Wed., 3/15 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 3/15 | Miscellaneous Events | PAC Swimming | - PHS Pool | 6:30 p.m. | 6:30 - 8:30 pm | |
| Wed., 3/15 | Miscellaneous Events | Mdby Park & Rec BB | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Thu., 3/16 | V Boys Swimming and Diving | CIAC Open Diving | Away - Buckley HS | 5:30 p.m. | @ Buckley High School | |
| Thu., 3/16 | Miscellaneous Events | Athletic Trainer | 2:30 p.m. | |||
| Thu., 3/16 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 3/16 | Miscellaneous Events | Middlebury Baseball Workouts | - Auxiliary Gym | 6:30 p.m. | 6:30 - 8:30 pm | |
| Thu., 3/16 | Miscellaneous Events | PAC Swimming | - PHS Pool | 6:30 p.m. | 6:30 - 8:30 pm | |
| Thu., 3/16 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 3/16 | Miscellaneous Events | Southbury Parks & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 3/17 | Miscellaneous Events | Athletic Trainer | 2:30 p.m. | |||
| Fri., 3/17 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Fri., 3/17 | Miscellaneous Events | Middlebury Baseball Workouts | - Auxiliary Gym | 6:30 p.m. | 6:30 - 8:30 pm | |
| Fri., 3/17 | Miscellaneous Events | PAC Swimming | - PHS Pool | 6:30 p.m. | 6:30 - 8:30 pm | |
| Sat., 3/18 | V Boys Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 2:30 p.m. | ||
| Sat., 3/18 | Miscellaneous Events | Athletic Trainer | 8:00 a.m. | 8:00 am - 6:30 pm | ||
| Sat., 3/18 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sat., 3/18 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 3/19 | Miscellaneous Events | Southbury Girls Softball | - Auxiliary Gym | 8:00 a.m. | 8:00 - 11:00 am | |
| Sun., 3/19 | Miscellaneous Events | Stby Park & Rec Youth Bball Practice | - Auxiliary Gym | 1:00 p.m. | 1:00 - 9:00 pm | |
| Sun., 3/19 | Miscellaneous Events | Stby Parks & Rec Youth Bball | - Auxiliary Gym | 1:00 p.m. | 1:00 pm - 9:00 pm | |
| Sun., 3/19 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 3/19 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Mon., 3/20 | Miscellaneous Events | Athletic Trainer | 1:45 p.m. | 1:45 - 8:30 pm | ||
| Mon., 3/20 | Miscellaneous Events | Sophomore Class Meeting | - Health Classroom - Room 201 | 2:15 p.m. | 2:15 - 2:45 pm | |
| Mon., 3/20 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 4:00 pm | |
| Mon., 3/20 | Miscellaneous Events | Southbury Park and Rec High School Basketball | - Auxiliary Gym | 7:00 p.m. | 7:00 to 8:30 pm | |
| Mon., 3/20 | Miscellaneous Events | Mdby Park & Rec Over 30 BB | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 3/21 | Miscellaneous Events | Athletic Trainer | 1:45 p.m. | 1:45 - 8:30 pm | ||
| Tue., 3/21 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 4:00 pm | |
| Tue., 3/21 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 3/22 | Miscellaneous Events | Athletic Trainer | 1:45 p.m. | 1:45 - 8:30 pm | ||
| Wed., 3/22 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 4:00 pm | |
| Wed., 3/22 | Miscellaneous Events | Mdby Park & Rec BB | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Thu., 3/23 | Miscellaneous Events | Athletic Trainer | 1:45 p.m. | 1:45 - 8:30 pm | ||
| Thu., 3/23 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 4:00 pm | |
| Thu., 3/23 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 3/24 | V Girls Lacrosse | Lakeland/Panas (NY) (Scrim.) | Away - Cheshire Academy | 3:30 p.m. | ||
| Fri., 3/24 | JV Girls Lacrosse | Lakeland/Panas (NY) (Scrim.) | Away - Cheshire Academy | 3:30 p.m. | At Cheshire Academy | |
| Fri., 3/24 | Miscellaneous Events | Athletic Trainer | 1:45 p.m. | 1:45 - 8:30 pm | ||
| Fri., 3/24 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 4:00 pm | |
| Fri., 3/24 | Miscellaneous Events | Rochambeau March Madness | - PHS Main Gym | 7:00 p.m. | ||
| Fri., 3/24 | Miscellaneous Events | USA Gymnastics State Set Up and Rehearsal | - PHS Main Gym | 9:00 p.m. | ||
| Sat., 3/25 | V Boys Lacrosse | Hamden (Scrim.) | Away [Directions] | 9:00 a.m. | ||
| Sat., 3/25 | V Girls Lacrosse | Danbury (Scrim.) | Away [Directions] | 9:00 a.m. | ||
| Sat., 3/25 | V Girls Tennis | Guilford (Scrim.) | Away [Directions] | 12:00 p.m. | ||
| Sat., 3/25 | Miscellaneous Events | USA Gymnastics State Championships | - PHS Main Gym | 7:00 a.m. | 7:00 am - 10:00 pm | |
| Sat., 3/25 | Miscellaneous Events | Athletic Trainer | 8:00 a.m. | |||
| Sat., 3/25 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 3/26 | Miscellaneous Events | USA Gymnastics State Championships | - PHS Main Gym | 7:00 a.m. | 7:00 am - 10:00 pm | |
| Sun., 3/26 | Miscellaneous Events | Southbury Girls Softball | - Auxiliary Gym | 8:00 a.m. | 8:00 - 11:00 am | |
| Sun., 3/26 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Mon., 3/27 | Miscellaneous Events | Athletic Trainer | 1:45 p.m. | 1:45 - 8:30 pm | ||
| Mon., 3/27 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 4:00 pm | |
| Mon., 3/27 | Miscellaneous Events | Mdby Park & Rec Over 30 BB | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 3/28 | Miscellaneous Events | Athletic Trainer | 1:45 p.m. | 1:45 - 8:30 pm | ||
| Tue., 3/28 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 4:00 pm | |
| Tue., 3/28 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 3/29 | V Boys Tennis | Nonnewaug (Scrim.) | Home - Edgewood [Directions] | 3:00 p.m. | ||
| Wed., 3/29 | V Boys Tennis | Nonnewaug (Scrim.) | Home - PHS Tennis Courts [Directions] | 3:00 p.m. | ||
| Wed., 3/29 | V Girls Lacrosse | Daniel Hand (Scrim.) | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Wed., 3/29 | JV Girls Lacrosse | Daniel Hand (Scrim.) | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Wed., 3/29 | Miscellaneous Events | Athletic Trainer | 1:45 p.m. | 1:45 - 8:30 pm | ||
| Wed., 3/29 | Miscellaneous Events | Mdby Park & Rec BB | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Thu., 3/30 | V Baseball | Bristol Central (Scrim.) | Home - Community Baseball Field [Directions] | 4:00 p.m. | ||
| Thu., 3/30 | V Boys Lacrosse | North Haven (Scrim.) | Away - North Haven Athletic Complex [Directions] | 3:30 p.m. | ||
| Thu., 3/30 | V Girls Tennis | Nonnewaug (Scrim.) | Home [Directions] | 3:30 p.m. | ||
| Thu., 3/30 | Miscellaneous Events | Athletic Trainer | 1:45 p.m. | 1:45 - 8:30 pm | ||
| Thu., 3/30 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 3/31 | V Softball | Holy Cross (Scrim.) | Home - PHS Softball Field [Directions] | TBA | ||
| Fri., 3/31 | Miscellaneous Events | Athletic Trainer | 1:45 p.m. | 1:45 - 8:30 pm | ||
| Sat., 4/1 | V Boys Lacrosse | New Milford | Away - New Milford HS [Directions] | 12:00 p.m. | L 6-8 | |
| Sat., 4/1 | JV Boys Lacrosse | New Milford | Away - New Milford HS [Directions] | 10:15 a.m. | ||
| Sat., 4/1 | Miscellaneous Events | Athletic Trainer | 8:00 a.m. | 8:00 am - 3:00 pm | ||
| Mon., 4/3 | Miscellaneous Events | Athletic Trainer | 1:45 p.m. | 1:45 - 8:30 pm | ||
| Mon., 4/3 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:30 p.m. | 6:30 - 7:30 pm | |
| Mon., 4/3 | Miscellaneous Events | Mdby Park & Rec Over 30 BB | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 4/4 | V Boys Lacrosse | Brookfield | Home - Sports Complex & Track [Directions] | 7:00 p.m. | L 13-8 | |
| Tue., 4/4 | JV Boys Lacrosse | Brookfield | Home - Sports Complex & Track [Directions] | 5:15 p.m. | ||
| Tue., 4/4 | V Girls Lacrosse | Brookfield | Away - BHS Stadium Field [Directions] | 5:30 p.m. | W 10-9 | |
| Tue., 4/4 | JV Girls Lacrosse | Brookfield | Away - BHS Back Turf [Directions] | 4:00 p.m. | ||
| Tue., 4/4 | Miscellaneous Events | Athletic Trainer | 1:45 p.m. | 1:45 - 8:30 pm | ||
| Wed., 4/5 | V Baseball | Oxford | Away - OHS Baseball Field [Directions] | 4:30 p.m. | L 5-6 | |
| Wed., 4/5 | V Boys Golf | Stratford | Away - Mill River C.C. [Directions] | 3:00 p.m. | Pomperaug 179 | |
| Wed., 4/5 | V Boys Tennis | Joel Barlow | Home - PHS Tennis Courts [Directions] | 3:45 p.m. | L 2-5 | non-league |
| Wed., 4/5 | Miscellaneous Events | SAT Testing in the Main Gym | - PHS Main Gym | 7:00 a.m. | ||
| Wed., 4/5 | Miscellaneous Events | Athletic Trainer | 1:45 p.m. | 1:45 - 8:30 pm | ||
| Wed., 4/5 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:30 p.m. | 6:30 - 7:30 pm | |
| Thu., 4/6 | Miscellaneous Events | Athletic Trainer | 1:45 p.m. | 1:45 - 8:30 pm | ||
| Fri., 4/7 | V Boys Lacrosse | Masuk | Home - Sports Complex & Track [Directions] | 5:45 p.m. | W 13-7 | |
| Fri., 4/7 | JV Boys Lacrosse | Masuk | Home - Sports Complex & Track [Directions] | 4:00 p.m. | ||
| Fri., 4/7 | V Boys Tennis | Newtown | Home - PHS Tennis Courts [Directions] | 3:45 p.m. | L 1-6 | non-league |
| Fri., 4/7 | V Girls Lacrosse | Masuk | Away - Benedict Stadium Field @ Masuk HS [Directions] | 5:30 p.m. | W 16-6 | |
| Fri., 4/7 | JV Girls Lacrosse | Masuk | Away - Benedict Stadium Field @ Masuk HS [Directions] | 4:00 p.m. | ||
| Fri., 4/7 | V Softball | Trumbull | Home - PHS Softball Field [Directions] | 4:15 p.m. | W 10-8 | |
| Fri., 4/7 | Miscellaneous Events | Athletic Trainer | 1:45 p.m. | 1:45 - 8:30 pm | ||
| Fri., 4/7 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 3:30 p.m. | 3:30 - 4:30 pm | |
| Sat., 4/8 | V Boys Outdoor Track | Bloomfield Invitational | Away | 9:00 a.m. | ||
| Sat., 4/8 | JV Girls Lacrosse | Weston | Home - Sports Complex & Track [Directions] | 4:00 p.m. | ||
| Sat., 4/8 | JV Girls Lacrosse | Weston | Home - Sports Complex & Track [Directions] | 4:00 p.m. | ||
| Sat., 4/8 | V Girls Outdoor Track | Bloomfield Invitational | Away | 9:00 a.m. | ||
| Sat., 4/8 | V Softball | Fitch | Home - PHS Softball Field [Directions] | 1:00 p.m. | W 16-3 | |
| Sat., 4/8 | JV Softball | Fitch | Home - PHS Softball Field [Directions] | 10:30 a.m. | ||
| Sat., 4/8 | V Girls Tennis | New Fairfield | Away [Directions] | 3:30 p.m. | L 2-5 | non-league |
| Sat., 4/8 | Miscellaneous Events | Athletic Trainer | 10:00 a.m. | 10:00 am - 4:00 pm | ||
| Mon., 4/10 | FR Baseball | Brookfield | Home - PHS Baseball Field [Directions] | 3:45 p.m. | ||
| Mon., 4/10 | V Boys Lacrosse | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 2:30 p.m. | W 13-8 | |
| Mon., 4/10 | JV Boys Lacrosse | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 4/10 | V Boys Tennis | Masuk | Home - PHS Tennis Courts [Directions] | 11:00 a.m. | W 6-1 | |
| Mon., 4/10 | V Softball | Joel Barlow | Away - Field E (Softball) [Directions] | 3:45 p.m. | L 3-16 | non-league |
| Mon., 4/10 | JV Softball | Trumbull | Home - PHS Softball Field [Directions] | 12:00 p.m. | ||
| Mon., 4/10 | V Girls Tennis | Masuk | Home - PHS Tennis Courts [Directions] | 2:00 p.m. | W 4-3 | |
| Mon., 4/10 | Miscellaneous Events | Athletic Trainer | 10:00 a.m. | 10:00 am - 5:00 pm | ||
| Mon., 4/10 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Mon., 4/10 | School Holidays and Closings | Spring Recess | ||||
| Tue., 4/11 | V Baseball | Holy Cross | Home - PHS Baseball Field [Directions] | 11:00 a.m. | L 9-3 | |
| Tue., 4/11 | V Baseball | Danbury | Away - Danbury HS Varsity Baseball Field [Directions] | 3:00 p.m. | L 9-8 | |
| Tue., 4/11 | V Boys Golf | New Milford | Away - Candlewood Valley [Directions] | 10:00 a.m. | Pomperaug 173 New Milford 203 | |
| Tue., 4/11 | V Boys Tennis | New Milford | Home - PHS Tennis Courts [Directions] | 11:00 a.m. | W 6-1 | |
| Tue., 4/11 | V Girls Lacrosse | New Fairfield | Home - Sports Complex & Track [Directions] | 7:00 p.m. | W 14-10 | |
| Tue., 4/11 | JV Girls Lacrosse | New Fairfield | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Tue., 4/11 | V Girls Outdoor Track | Bloomfield Invitational | Away | Cancelled | Cancelled | |
| Tue., 4/11 | Miscellaneous Events | Athletic Trainer | 10:00 a.m. | 10:00 am - 9:00 pm | ||
| Tue., 4/11 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 4/11 | School Holidays and Closings | Spring Recess | ||||
| Wed., 4/12 | V Baseball | Masuk | Home - PHS Baseball Field [Directions] | 12:00 p.m. | L 2-7 | non-league |
| Wed., 4/12 | FR Baseball | Masuk | Away - John Giampaolo Baseball Field @ Masuk HS [Directions] | 3:45 p.m. | ||
| Wed., 4/12 | V Softball | Masuk | Home - PHS Softball Field [Directions] | 3:45 p.m. | L 1-8 | non-league |
| Wed., 4/12 | Miscellaneous Events | Athletic Trainer | 10:00 a.m. | 10:00 am - 6:00 pm | ||
| Wed., 4/12 | Miscellaneous Events | Middlebury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 3:00 pm | |
| Wed., 4/12 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 4/12 | School Holidays and Closings | Spring Recess | ||||
| Thu., 4/13 | V Baseball | New Milford | Home - PHS Baseball Field [Directions] | 3:45 p.m. | L 3-15 | non-league |
| Thu., 4/13 | FR Baseball | New Milford | Away - New Milford HS [Directions] | 3:45 p.m. | ||
| Thu., 4/13 | V Boys Lacrosse | Avon | Home - Sports Complex & Track [Directions] | 7:00 p.m. | W 9-8 | |
| Thu., 4/13 | JV Boys Lacrosse | Avon | Home - Sports Complex & Track [Directions] | 5:15 p.m. | ||
| Thu., 4/13 | V Girls Lacrosse | Newtown | Away - Treadwell Town Park [Directions] | 3:30 p.m. | L 15-6 | |
| Thu., 4/13 | JV Girls Lacrosse | Newtown | Away - Treadwell Town Park [Directions] | 5:00 p.m. | ||
| Thu., 4/13 | V Softball | Brookfield | Home - PHS Softball Field [Directions] | 3:45 p.m. | W 13 -3 | non-league |
| Thu., 4/13 | JV Softball | Masuk | Away - Masuk HS Softball Field [Directions] | 10:30 a.m. | ||
| Thu., 4/13 | Miscellaneous Events | Athletic Trainer | 10:00 a.m. | 10:00 am - 9:00 pm | ||
| Thu., 4/13 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 4/13 | School Holidays and Closings | Spring Recess | ||||
| Fri., 4/14 | Miscellaneous Events | Athletic Trainer | 10:00 a.m. | 10:00 am - 6:00 pm | ||
| Fri., 4/14 | School Holidays and Closings | Spring Recess - Good Friday | ||||
| Sat., 4/15 | JV Baseball | New Milford | Away - New Milford HS [Directions] | 10:00 a.m. | ||
| Sat., 4/15 | V Boys Lacrosse | Southington | Away - Turf Field SHS [Directions] | 12:00 p.m. | W 10-4 | |
| Sat., 4/15 | JV Boys Lacrosse | Southington | Away - SubVarsity Lacrosse/Soccer [Directions] | 12:00 p.m. | ||
| Sat., 4/15 | V Softball | Lewis Mills | Away - Lewis Mills Softball Field [Directions] | 12:00 p.m. | W 4-1 | |
| Sat., 4/15 | JV Softball | Brookfield | Away - BHS Softball Field [Directions] | 10:00 a.m. | ||
| Sat., 4/15 | Miscellaneous Events | Athletic Trainer | 8:00 a.m. | 8:00 am - 1:00 pm | ||
| Mon., 4/17 | V Baseball | Newtown | Away - Newtown HS Baseball Field [Directions] | 4:00 p.m. | W 5-0 | non-league |
| Mon., 4/17 | FR Baseball | Newtown | Home - PHS Baseball Field [Directions] | 3:30 p.m. | ||
| Mon., 4/17 | V Boys Golf | Brookfield | Home - Heritage Village C.C. [Directions] | 3:00 p.m. | Pomperaug 167 Brookfield 177 | |
| Mon., 4/17 | V Boys Outdoor Track | Bethel, Immaculate | Home - Sports Complex & Track [Directions] | 4:00 p.m. | Pomperaug 88 Bethel 62 Pomperaug 86 Immaculate 55 | |
| Mon., 4/17 | V Boys Tennis | Bunnell | Away [Directions] | 3:45 p.m. | W 7-0 | |
| Mon., 4/17 | V Softball | Newtown | Away - Newtown HS Softball Field [Directions] | 4:15 p.m. | W 9 - 5 | non-league |
| Mon., 4/17 | V Girls Tennis | Bunnell | Home - PHS Tennis Courts [Directions] | 3:45 p.m. | W 5-2 | |
| Mon., 4/17 | Miscellaneous Events | Athletic Trainer | 1:45 p.m. | 1:45 - 7:00 pm | ||
| Mon., 4/17 | Miscellaneous Events | Mdby Park & Rec Over 30 BB | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 4/18 | V Baseball | New Milford | Away - New Milford HS [Directions] | 4:00 p.m. | L 13-2 | |
| Tue., 4/18 | JV Baseball | Newtown | Home - Community Baseball Field [Directions] | 3:30 p.m. | ||
| Tue., 4/18 | V Boys Golf | Bunnell | Home - Heritage Village C.C. [Directions] | 3:00 p.m. | Pomperaug 166 Bunnell 235 Nonnewaug 200 | |
| Tue., 4/18 | V Girls Lacrosse | Weston | Away - WHS Turf Field [Directions] | 5:30 p.m. | L 21-15 | |
| Tue., 4/18 | JV Girls Lacrosse | Weston | Away - WHS Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 4/18 | V Girls Outdoor Track | Bethel, Immaculate | Away - Bethel HS [Directions] | 4:00 p.m. | PHS 106 Bethel 42 PHS 94.5 IHS 47.5 | |
| Tue., 4/18 | V Softball | Naugatuck (Scrim.) | Home - PHS Softball Field [Directions] | Cancelled | Cancelled | |
| Tue., 4/18 | V Softball | New Milford | Away - New Milford HS [Directions] | 4:00 p.m. | W 14-9 | |
| Tue., 4/18 | JV Softball | Newtown | Home - Community Softball Field [Directions] | 4:15 p.m. | ||
| Tue., 4/18 | Miscellaneous Events | Athletic Trainer | 1:45 p.m. | 1:45 - 5:30 pm | ||
| Wed., 4/19 | FR Baseball | New Milford | Home - Community Baseball Field [Directions] | 3:45 p.m. | ||
| Wed., 4/19 | V Girls Tennis | Weston | Away - WHS Tennis Courts [Directions] | 3:45 p.m. | L 0-4 | |
| Wed., 4/19 | Miscellaneous Events | Athletic Trainer | 1:45 p.m. | 1:45 - 8:30 pm | ||
| Thu., 4/20 | JV Baseball | New Milford | Home - Community Baseball Field [Directions] | 4:00 p.m. | ||
| Thu., 4/20 | V Boys Lacrosse | Stamford | Away - Stamford HS [Directions] | 7:00 p.m. | W 10-2 | |
| Thu., 4/20 | JV Boys Lacrosse | Stamford | Away - Stamford High Soccer Field [Directions] | 4:30 p.m. | ||
| Thu., 4/20 | V Boys Tennis | Brookfield | Away - BHS Tennis Courts [Directions] | 3:45 p.m. | L 2-5 | non-league |
| Thu., 4/20 | V Boys Tennis | Brookfield | Away - Brookfield HS [Directions] | 5:30 p.m. | W 4-3 | |
| Thu., 4/20 | JV Softball | New Milford | Home - Community Softball Field [Directions] | 4:15 p.m. | ||
| Thu., 4/20 | Miscellaneous Events | Athletic Trainer | 1:45 p.m. | 1:45 - 5:30 pm | ||
| Fri., 4/21 | V Boys Golf | Masuk | Away - Whitney Farms Golf Course [Directions] | 3:00 p.m. | Pomperaug 183 Masuk 168 | non-league |
| Fri., 4/21 | Miscellaneous Events | Character Breakfast | 5:00 a.m. | 5:00 am to 7:30 am | ||
| Fri., 4/21 | Miscellaneous Events | Athletic Trainer | 1:45 p.m. | 1:45 - 8:30 pm | ||
| Fri., 4/21 | Miscellaneous Events | Girls Soccer Team Meeting | - Health Classroom - Room 201 | 3:30 p.m. | ||
| Fri., 4/21 | Miscellaneous Events | Raindate for Dodgeball for Diabetes | - PHS Main Gym | 6:00 p.m. | ||
| Sat., 4/22 | JV Baseball | Masuk | Home - PHS Baseball Field [Directions] | 10:00 a.m. | ||
| Sat., 4/22 | V Boys Lacrosse | Amity | Home - Sports Complex & Track [Directions] | 10:00 a.m. | W 10-5 | |
| Sat., 4/22 | JV Boys Lacrosse | Amity | Home - Sports Complex & Track [Directions] | 12:00 p.m. | ||
| Sat., 4/22 | V Girls Lacrosse | Bacon Academy | Home - Sports Complex & Track [Directions] | 5:30 p.m. | W 18-6 | |
| Sat., 4/22 | JV Girls Lacrosse | Bacon Academy | Home - Sports Complex & Track [Directions] | 4:00 p.m. | ||
| Sat., 4/22 | JV Softball | Masuk | Home - PHS Softball Field [Directions] | 10:00 a.m. | ||
| Sat., 4/22 | Miscellaneous Events | Athletic Trainer | 8:00 a.m. | 8:00 am - 6:00 pm | ||
| Mon., 4/24 | FR Baseball | Brookfield | Home - Community Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/24 | V Boys Golf | New Fairfield | Home - Heritage Village C.C. [Directions] | 3:00 p.m. | Pomperaug 162 New Fairfield 206 | |
| Mon., 4/24 | V Boys Outdoor Track | Masuk, Newtown, Stratford | Away [Directions] | 4:00 p.m. | Pomperaug 35 Masuk 115 Pomperaug 51 Newtown 99 Pomperaug 117 Stratford 32 | @ Masuk |
| Mon., 4/24 | V Boys Tennis | Bethel | Away - Bethel HS [Directions] | 5:00 p.m. | W 6-1 | |
| Mon., 4/24 | V Girls Lacrosse | Bethel | Home - Sports Complex & Track [Directions] | 7:00 p.m. | W 18-9 | |
| Mon., 4/24 | JV Girls Lacrosse | Bethel | Home - Sports Complex & Track [Directions] | 5:30 p.m. | ||
| Mon., 4/24 | V Softball | Brookfield | Away - BHS Softball Field [Directions] | 4:15 p.m. | W 6 - 1 | |
| Mon., 4/24 | V Girls Tennis | Bethel | Away - Bethel HS [Directions] | 2:30 p.m. | W 5-2 | |
| Mon., 4/24 | Miscellaneous Events | Athletic Trainer | 1:45 p.m. | 1:45 - 8:30 pm | ||
| Mon., 4/24 | Miscellaneous Events | Mdby Park & Rec Over 30 BB | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 4/25 | Miscellaneous Events | Athletic Trainer | 1:45 p.m. | 1:45 - 7:00 pm | ||
| Tue., 4/25 | Miscellaneous Events | PHS College Fair | - PHS Main Gym | 2:30 p.m. | set-up 2:30 - 5:00 pm, Fair 6:00 - 10:00 pm | |
| Wed., 4/26 | V Baseball | Bunnell | Home - Community Baseball Field [Directions] | 3:45 p.m. | L 3-5 | |
| Wed., 4/26 | V Boys Golf | Newtown | Away - Rock Ridge CC [Directions] | 3:00 p.m. | Pomperaug 180 Newtown 169 | |
| Wed., 4/26 | V Boys Tennis | Stratford | Away - Flood MS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Wed., 4/26 | V Girls Lacrosse | Stratford/Bunnell | Away - Penders Field [Directions] | 7:00 p.m. | W 17-3 | |
| Wed., 4/26 | V Girls Outdoor Track | Masuk, Newtown, Stratford | Home - Sports Complex & Track [Directions] | 4:00 p.m. | NHS 104.5 PHS 45.5 PHS 107.5 Masuk 37.5 PHS 117 SHS 27 | |
| Wed., 4/26 | V Softball | Bunnell | Home - Community Softball Field [Directions] | 4:15 p.m. | W 9-0 | |
| Wed., 4/26 | V Girls Tennis | Stratford | Home - Edgewood Tennis Club, Middlebury [Directions] | 3:45 p.m. | W 7-0 | |
| Wed., 4/26 | Miscellaneous Events | Athletic Trainer | 1:45 p.m. | 1:45 - 7:00 pm | ||
| Wed., 4/26 | Miscellaneous Events | Volleyball Club | - PHS Main Gym | 2:30 p.m. | 2:30 to 4:15 pm | |
| Thu., 4/27 | V Baseball | Masuk | Away - John Giampaolo Baseball Field @ Masuk HS [Directions] | 4:15 p.m. | L 14-0 | |
| Thu., 4/27 | V Boys Tennis | Newtown | Away [Directions] | 3:45 p.m. | L 2-5 | |
| Thu., 4/27 | V Softball | Masuk | Away - Masuk HS Softball Field [Directions] | 4:15 p.m. | W 4-0 | |
| Thu., 4/27 | JV Softball | Bunnell | Away - Wigwam Lane Field [Directions] | 4:15 p.m. | ||
| Thu., 4/27 | V Girls Tennis | Newtown | Away - PHS Tennis Courts [Directions] | 3:45 p.m. | W 4-3 | |
| Thu., 4/27 | Miscellaneous Events | Region 15 Art Show Set Up | - PHS Main Gym | 8:00 a.m. | 8:00 - 5:00 pm | |
| Thu., 4/27 | Miscellaneous Events | Athletic Trainer | 1:45 p.m. | 1:45 - 8:30 pm | ||
| Fri., 4/28 | V Baseball | Weston | Away - Revson Field, Weston [Directions] | 4:15 p.m. | L 2-10 | |
| Fri., 4/28 | JV Baseball | Weston | Away - Revson Field, Weston [Directions] | 4:00 p.m. | ||
| Fri., 4/28 | FR Baseball | Weston | Home - PHS Baseball Field [Directions] | 4:15 p.m. | ||
| Fri., 4/28 | V Boys Outdoor Track | O'Grady Relays | Away | Cancelled | Cancelled | |
| Fri., 4/28 | V Girls Outdoor Track | O'Grady Relays | Away | Cancelled | Cancelled | |
| Fri., 4/28 | V Softball | Weston | Away - Hurlbutt El. School, Weston [Directions] | 4:15 p.m. | W 5-0 | |
| Fri., 4/28 | Miscellaneous Events | Region 15 Art Show | - PHS Main Gym | 8:00 a.m. | 8:00 am - 10:00 pm | |
| Fri., 4/28 | Miscellaneous Events | Region 15 Art Show | - Health Classroom - Room 201 | 8:00 a.m. | 8:00 am - 10:00 pm | |
| Fri., 4/28 | Miscellaneous Events | Athletic Trainer | 1:45 p.m. | 1:45 - 8:30 pm | ||
| Sat., 4/29 | V Baseball | Brookfield | Away - @ Dodd Stadium in Norwich [Directions] | 12:00 p.m. | L 3-4 | |
| Sat., 4/29 | V Boys Outdoor Track | O'Grady Relays | Away | 9:00 a.m. | ||
| Sat., 4/29 | V Girls Lacrosse | Farmington | Away - Farmington HS [Directions] | 11:00 a.m. | W 19-9 | |
| Sat., 4/29 | JV Girls Lacrosse | Farmington | Away - Farmington HS [Directions] | 12:15 p.m. | ||
| Sat., 4/29 | V Girls Outdoor Track | O'Grady Relays | Away | 9:00 a.m. | ||
| Sat., 4/29 | JV Softball | Weston | Home - PHS Softball Field [Directions] | 10:00 a.m. | ||
| Sat., 4/29 | V Girls Tennis | Newtown | Away [Directions] | 1:00 p.m. | W 4-3 | non-league |
| Sat., 4/29 | Miscellaneous Events | Region 15 Art Show | - Health Classroom - Room 201 | 8:00 a.m. | 8:00 am - 5:00 pm | |
| Sat., 4/29 | Miscellaneous Events | Region 15 Art Show | - PHS Main Gym | 8:00 a.m. | 8:00 am - 5:00 pm | |
| Sat., 4/29 | Miscellaneous Events | Athletic Trainer | 9:30 a.m. | 9:30 am - 2:00 pm | ||
| Mon., 5/1 | V Baseball | Kolbe Cathedral | Home - PHS Baseball Field [Directions] | 4:15 p.m. | W 12-0 | |
| Mon., 5/1 | JV Baseball | Brookfield | Away - BHS Baseball Field [Directions] | 3:45 p.m. | ||
| Mon., 5/1 | FR Baseball | Brookfield | Away - H.H.E.S. Baseball Field [Directions] | 4:15 p.m. | ||
| Mon., 5/1 | V Boys Golf | Weston | Away - Aspetuck Valley Country Club [Directions] | 3:00 p.m. | pomperaug 190 | |
| Mon., 5/1 | V Boys Outdoor Track | Bunnell, Kolbe Cathedral, New Fairfield | Away [Directions] | 4:00 p.m. | Pomperaug 107 Bunnell 43 Pomperaug 137.5 Kolbe Cathedral 12.5 Pomperaug 133.5 New Fairfield 16.5 | @ Bunnell |
| Mon., 5/1 | V Girls Lacrosse | Bunnell | Home - Sports Complex & Track [Directions] | 7:00 p.m. | W 18-5 | |
| Mon., 5/1 | JV Girls Lacrosse | New Fairfield | Home - Sports Complex & Track [Directions] | 5:15 p.m. | ||
| Mon., 5/1 | V Softball | Kolbe Cathedral | Home - PHS Softball Field [Directions] | 4:15 p.m. | W 16-0 | |
| Mon., 5/1 | V Girls Tennis | Notre Dame-Fairfield | Away - Sacred Heart University [Directions] | 3:45 p.m. | W 7-0 | |
| Mon., 5/1 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 4:00 p.m. | 4:00 - 8:30 pm | |
| Tue., 5/2 | V Boys Lacrosse | Bunnell-Stratford | Away - Bunnell Turf Field [Directions] | 5:15 p.m. | W 16-4 | |
| Tue., 5/2 | JV Boys Lacrosse | Bunnell-Stratford | Away - Bunnell Turf Field [Directions] | 7:00 p.m. | ||
| Tue., 5/2 | V Boys Tennis | Weston | Home - PHS Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Tue., 5/2 | V Girls Outdoor Track | Bunnell, New Fairfield, Kolbe Cathedral | Home - Sports Complex & Track [Directions] | 4:00 p.m. | PHS 118.5 Kolbe 22.5 PHS 114 Bunnell 35 PHS 114 New Fairfield 19 | |
| Tue., 5/2 | JV Softball | Weston | Away - Weston MS [Directions] | 4:00 p.m. | ||
| Tue., 5/2 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 4:00 p.m. | 4:00 - 8:30 pm | |
| Wed., 5/3 | V Baseball | Bethel | Away - Hunt Field at Bethel HS [Directions] | 4:00 p.m. | W 8-1 | |
| Wed., 5/3 | FR Baseball | Bethel | Home - PHS Baseball Field [Directions] | 3:45 p.m. | ||
| Wed., 5/3 | V Boys Golf | Notre Dame-Fairfield | Home - Heritage Village C.C. [Directions] | 3:00 p.m. | Pomperaug 168 Notre Dame 179 | |
| Wed., 5/3 | V Boys Lacrosse | Watertown | Away - John J. Mills Complex @ Watertown HS [Directions] | 7:30 p.m. | W 14-4 | |
| Wed., 5/3 | JV Boys Lacrosse | Watertown | Away - John J. Mills Complex @ Watertown HS [Directions] | 6:00 p.m. | ||
| Wed., 5/3 | V Boys Tennis | New Fairfield | Away [Directions] | 3:45 p.m. | W 7-0 | |
| Wed., 5/3 | V Girls Lacrosse | Notre Dame-Fairfield | Home - Sports Complex & Track [Directions] | 7:00 p.m. | W 16-5 | |
| Wed., 5/3 | JV Girls Lacrosse | Notre Dame-Fairfield | Home - Sports Complex & Track [Directions] | Cancelled | Cancelled | |
| Wed., 5/3 | JV Girls Lacrosse | North Branford | Home - Sports Complex & Track [Directions] | 5:15 p.m. | ||
| Wed., 5/3 | V Softball | Bethel | Away - Freebairn Field [Directions] | 7:00 p.m. | W 19 - 7 | |
| Wed., 5/3 | V Girls Tennis | New Fairfield | Home - PHS Tennis Courts [Directions] | 3:45 p.m. | W 5-2 | |
| Wed., 5/3 | Miscellaneous Events | Volleyball Club | - PHS Main Gym | 2:30 p.m. | 2:30 to 4:15 pm | |
| Wed., 5/3 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 4:00 p.m. | 4:00 - 8:30 pm | |
| Thu., 5/4 | JV Baseball | Bethel | Home - Community Baseball Field [Directions] | 3:45 p.m. | ||
| Thu., 5/4 | V Boys Golf | Woodland Tournament | Away | 8:00 a.m. | Pomperaug 165 | @ Oxford Greens |
| Thu., 5/4 | V Boys Tennis | Immaculate | Home - PHS Tennis Courts [Directions] | 3:45 p.m. | W 6-1 | |
| Thu., 5/4 | JV Softball | Bethel | Home - Community Softball Field [Directions] | Cancelled | Cancelled | |
| Thu., 5/4 | Miscellaneous Events | Volleyball Club | - PHS Main Gym | 2:30 p.m. | 2:30 to 4:15 pm | |
| Thu., 5/4 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 4:00 p.m. | 4:00 - 8:30 pm | |
| Fri., 5/5 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 6:30 pm | |
| Fri., 5/5 | Miscellaneous Events | USA State Gymnastic Championships Rehersal & Set up | - PHS Main Gym | 3:00 p.m. | 3:00 - 8:00 pm2/7/17 | |
| Sat., 5/6 | JV Baseball | Stratford | Away - Penders Field [Directions] | 3:00 p.m. | ||
| Sat., 5/6 | V Boys Lacrosse | Lewis Mills | Home - Sports Complex & Track [Directions] | 3:45 p.m. | W 15-7 | |
| Sat., 5/6 | JV Boys Lacrosse | Lewis Mills | Home - Sports Complex & Track [Directions] | 2:00 p.m. | ||
| Sat., 5/6 | V Girls Lacrosse | Amity | Home - Sports Complex & Track [Directions] | 7:30 p.m. | W 15-2 | |
| Sat., 5/6 | JV Girls Lacrosse | Amity | Home - Sports Complex & Track [Directions] | 5:45 p.m. | ||
| Sat., 5/6 | Miscellaneous Events | USA State Gymnastic Championships | - PHS Main Gym | 7:00 a.m. | 7:00 am - 10:00 pm | |
| Sun., 5/7 | Miscellaneous Events | USA State Gymnastic Championships | - PHS Main Gym | 7:00 a.m. | 7:00 am - 10:00 pm | |
| Sun., 5/7 | Miscellaneous Events | Pomperaug Lacrosse Club - Honor the Game Day | - PHS Soccer Field | 7:00 a.m. | 7:00 am - 6:00 pm | |
| Sun., 5/7 | Miscellaneous Events | Pomperaug Lacrosse Club - Honor the Game Day | - Sports Complex & Track | 7:00 a.m. | 7:00 am - 6:00 pm | |
| Sun., 5/7 | Miscellaneous Events | Youth Lacrosse Honor the Game Day | - Sports Complex & Track | TBA | ||
| Mon., 5/8 | V Baseball | Newtown | Home - Baseball Field at Fairfield Hills Complex [Directions] | 7:00 p.m. | W 5-4 | |
| Mon., 5/8 | FR Baseball | Newtown | Away - Newtown HS Baseball Field [Directions] | 4:15 p.m. | ||
| Mon., 5/8 | V Boys Golf | Joel Barlow | Away - Connecticut Golf Club [Directions] | 3:00 p.m. | Pomperaug 209 Barlow 183 | |
| Mon., 5/8 | V Boys Outdoor Track | Notre Dame-Fairfield, New Milford | Home - Sports Complex & Track [Directions] | 4:00 p.m. | Pomperaug 134 Notre Dame-Fairfield 15 Pomperaug 60 New Milford 90 | |
| Mon., 5/8 | V Boys Tennis | Joel Barlow | Away - Tennis Courts [Directions] | 3:45 p.m. | W 4-3 | |
| Mon., 5/8 | V Softball | Newtown | Home - PHS Softball Field [Directions] | 4:15 p.m. | W 11 - 0 | |
| Mon., 5/8 | V Girls Tennis | Joel Barlow | Home - PHS Tennis Courts [Directions] | 3:45 p.m. | L 3-4 | |
| Mon., 5/8 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 4:00 p.m. | 4:00 - 8:30 pm | |
| Tue., 5/9 | JV Baseball | Newtown | Away - Baseball Field at Fairfield Hills Complex [Directions] | 4:15 p.m. | ||
| Tue., 5/9 | V Boys Golf | Masuk | Home - Heritage Village C.C. [Directions] | 3:00 p.m. | Pomperaug 177 Masuk 149 | |
| Tue., 5/9 | V Boys Lacrosse | Joel Barlow | Home - Sports Complex & Track [Directions] | 7:00 p.m. | L 10-19 | |
| Tue., 5/9 | JV Boys Lacrosse | Joel Barlow | Home - Sports Complex & Track [Directions] | 5:15 p.m. | ||
| Tue., 5/9 | V Girls Lacrosse | Joel Barlow | Away - Field I (Stadium) [Directions] | 6:30 p.m. | W 17-6 | |
| Tue., 5/9 | JV Girls Lacrosse | Joel Barlow | Away - Field I (Stadium) [Directions] | 5:00 p.m. | ||
| Tue., 5/9 | V Girls Outdoor Track | New Milford, Notre Dame-Fairfield | Away - New Milford HS [Directions] | 4:00 p.m. | PHS 76 NMHS 73 PHS 126 NDHS 3 | |
| Tue., 5/9 | JV Softball | Newtown | Away - Newtown HS Softball Field [Directions] | 4:15 p.m. | ||
| Tue., 5/9 | V Girls Tennis | Bethel | Home - PHS Tennis Courts [Directions] | 3:45 p.m. | W 5-2 | non-league |
| Tue., 5/9 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 4:00 p.m. | 4:00 - 8:30 pm | |
| Wed., 5/10 | V Baseball | Notre Dame-Fairfield | Away - Fabbri Field at Notre Dame [Directions] | 4:45 p.m. | W 5-2 | |
| Wed., 5/10 | V Boys Golf | Bethel | Away - Redding Country Club [Directions] | 2:30 p.m. | Pomperaug 186 | |
| Wed., 5/10 | V Softball | Notre Dame-Fairfield | Away - Park Avenue Field at Notre Dame [Directions] | 4:15 p.m. | W 6-4 | |
| Wed., 5/10 | V Girls Tennis | Brookfield | Away - BHS Tennis Courts [Directions] | 5:00 p.m.. | W 7-0 | |
| Wed., 5/10 | Miscellaneous Events | Volleyball Club | - PHS Main Gym | 2:30 p.m. | 2:30 to 4:15 pm | |
| Wed., 5/10 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 4:00 p.m. | 4:00 - 8:30 pm | |
| Thu., 5/11 | V Baseball | Seymour | Home - PHS Baseball Field [Directions] | 4:15 p.m. | W 5-4 | |
| Thu., 5/11 | JV Baseball | Notre Dame-Fairfield | Home - Community Baseball Field [Directions] | 4:00 p.m. | ||
| Thu., 5/11 | V Boys Lacrosse | Immaculate | Away - Mustang Valley [Directions] | 4:00 p.m. | L 9-10 | |
| Thu., 5/11 | V Girls Lacrosse | Immaculate | Home - Sports Complex & Track [Directions] | 7:00 p.m. | W 19-4 | |
| Thu., 5/11 | V Girls Tennis | New Milford | Away - New Milford HS [Directions] | 3:45 p.m. | W 7-0 | |
| Thu., 5/11 | Miscellaneous Events | Volleyball Club | - PHS Main Gym | 2:30 p.m. | 2:30 to 4:15 pm | |
| Thu., 5/11 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 4:00 p.m. | 4:00 - 8:30 pm | |
| Fri., 5/12 | V Baseball | New Fairfield | Home - PHS Baseball Field [Directions] | 4:30 p.m. | W 8-7 | |
| Fri., 5/12 | FR Baseball | New Fairfield | Away [Directions] | 3:45 p.m. | ||
| Fri., 5/12 | V Boys Lacrosse | Bethel | Away - DeSantis Field at Bethel HS [Directions] | 7:00 p.m. | W 22-7 | |
| Fri., 5/12 | JV Boys Lacrosse | Bethel | Away - Bethel HS [Directions] | 5:15 p.m. | ||
| Fri., 5/12 | V Softball | New Fairfield | Home - PHS Softball Field [Directions] | 4:15 p.m. | W 10-4 | |
| Fri., 5/12 | V Girls Tennis | Immaculate | Home - Pomperaug HS [Directions] | 3:45 p.m. | W 6-1 | |
| Fri., 5/12 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 6:30 pm | |
| Sat., 5/13 | V Boys Outdoor Track | Hartford Invitational | Away [Directions] | 9:00 a.m. | @ Simsbury HS | |
| Sat., 5/13 | V Girls Lacrosse | Branford | Home - Sports Complex & Track [Directions] | 10:00 a.m. | W 13-12 OT | |
| Sat., 5/13 | JV Girls Lacrosse | Branford | Home - Sports Complex & Track [Directions] | 11:30 a.m. | ||
| Sat., 5/13 | V Girls Outdoor Track | Greater Hartford Open | Away [Directions] | 9:00 a.m. | @ Simsbury HS | |
| Mon., 5/15 | V Baseball | Joel Barlow | Home - PHS Baseball Field [Directions] | 4:15 p.m. | L 13-6 | |
| Mon., 5/15 | FR Baseball | Joel Barlow | Away - Field G (Baseball) [Directions] | 4:15 p.m. | ||
| Mon., 5/15 | V Boys Golf | Immaculate | Away - Richter Park [Directions] | 3:00 p.m. | Pomperaug 192 Immaculate 175 | |
| Mon., 5/15 | V Boys Lacrosse | Stratford | Home - Sports Complex & Track [Directions] | 7:00 p.m. | W 14-6 | |
| Mon., 5/15 | JV Boys Lacrosse | Stratford | Home - Sports Complex & Track [Directions] | 5:15 p.m. | ||
| Mon., 5/15 | V Boys Outdoor Track | Weston, Brookfield, Joel Barlow | Away [Directions] | 4:00 p.m. | Weston 97 Pomperaug 53 Pomperaug 93 Joel Barlow 56 Pomperaug 105 Brookfield 44 | @ Weston |
| Mon., 5/15 | V Boys Tennis | Newtown | Away [Directions] | 3:30 p.m. | SWC Team Semi-Finals | |
| Mon., 5/15 | V Softball | Joel Barlow | Home - PHS Softball Field [Directions] | 4:15 p.m. | W 5 - 4 | |
| Mon., 5/15 | JV Softball | Brookfield | Home - Community Softball Field [Directions] | Cancelled | Cancelled | |
| Mon., 5/15 | V Girls Tennis | SWC Team Semi-Finals | Away | 4:00 p.m. | SWC Team Semi-Finals | |
| Mon., 5/15 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 4:00 p.m. | 4:00 - 8:30 pm | |
| Mon., 5/15 | Miscellaneous Events | Middlebury Park & Rec Lifeguard Swim Test | - PHS Pool | 6:30 p.m. | 6:30 - 8:30 pm | |
| Tue., 5/16 | V Baseball | Immaculate | Away - Immaculate HS [Directions] | 4:15 p.m. | L 4-3 | |
| Tue., 5/16 | JV Baseball | Joel Barlow | Away - Veteran's Field - Easton [Directions] | 4:15 p.m. | ||
| Tue., 5/16 | V Boys Lacrosse | Notre Dame-Fairfield | Away - Park Avenue Field at Notre Dame [Directions] | 4:00 p.m. | W 12-5 | |
| Tue., 5/16 | JV Boys Lacrosse | Notre Dame-Fairfield | Away - Park Avenue Field at Notre Dame [Directions] | 6:00 p.m. | ||
| Tue., 5/16 | V Girls Lacrosse | New Milford | Home - Sports Complex & Track [Directions] | 7:00 p.m. | W 17-6 | |
| Tue., 5/16 | JV Girls Lacrosse | New Milford | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Tue., 5/16 | V Girls Outdoor Track | Brookfield, Weston, Joel Barlow | Away - BHS Track [Directions] | 3:30 p.m. | PHS 109 Weston 41 PHS 108 Barlow 42 PHS 109.5 Brookfield 38.5 | |
| Tue., 5/16 | V Softball | Immaculate | Away - Immaculate HS [Directions] | 4:15 p.m. | W 5 - 0 | |
| Tue., 5/16 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 4:00 p.m. | 4:00 - 8:30 pm | |
| Wed., 5/17 | JV Baseball | Immaculate | Home - Community Baseball Field [Directions] | 3:45 p.m. | ||
| Wed., 5/17 | V Boys Golf | Joel Barlow | Home - Heritage Village C.C. [Directions] | 3:00 p.m. | Pomperaug 174 Barlow 154 | non-league |
| Wed., 5/17 | V Boys Tennis | SWC Team Championships | Away | Cancelled | Cancelled | Site TBA |
| Wed., 5/17 | JV Softball | Immaculate | Home - Community Softball Field [Directions] | 4:15 p.m. | ||
| Wed., 5/17 | V Girls Tennis | SWC Team Championships | Away | Cancelled | Cancelled | |
| Wed., 5/17 | Miscellaneous Events | Volleyball Club | - PHS Main Gym | 2:30 p.m. | 2:30 to 4:15 pm | |
| Wed., 5/17 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 4:00 p.m. | 4:00 - 8:30 pm | |
| Thu., 5/18 | V Baseball | Stratford | Home - PHS Baseball Field [Directions] | 3:45 p.m. | W 6-5 | |
| Thu., 5/18 | JV Baseball | Masuk | Away - John Giampaolo Baseball Field @ Masuk HS [Directions] | 4:45 p.m. | ||
| Thu., 5/18 | FR Baseball | Bethel | Home - Community Baseball Field [Directions] | 3:45 p.m. | ||
| Thu., 5/18 | V Boys Outdoor Track | Bethel | Away [Directions] | 4:00 p.m. | Bethel Freshmen Meet | |
| Thu., 5/18 | V Girls Lacrosse | Masuk | Home - Sports Complex & Track [Directions] | 7:00 p.m. | W 10-9 OT | $8 Adults, $5 Students |
| Thu., 5/18 | JV Girls Lacrosse | New Milford | Away - New Milford HS [Directions] | Cancelled | Cancelled | |
| Thu., 5/18 | JV Girls Lacrosse | New Milford | Away [Directions] | Cancelled | Cancelled | |
| Thu., 5/18 | JV Girls Lacrosse | Shelton | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Thu., 5/18 | JV Girls Lacrosse | Shelton | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Thu., 5/18 | V Girls Outdoor Track | Bethel | Away [Directions] | 4:00 p.m. | Bethel Freshmen Meet | |
| Thu., 5/18 | V Softball | Stratford | Home - PHS Softball Field [Directions] | 3:45 p.m. | W 14-0 | |
| Thu., 5/18 | Miscellaneous Events | Volleyball Club | - PHS Main Gym | 2:30 p.m. | 2:30 to 4:15 pm | |
| Thu., 5/18 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 4:00 p.m. | 4:00 - 8:30 pm | |
| Fri., 5/19 | JV Softball | New Fairfield | Away - NFHS Softball Field [Directions] | 3:30 p.m. | ||
| Fri., 5/19 | V Girls Tennis | Southington | Away - Tennis Courts [Directions] | 3:45 p.m. | L 3-4 | |
| Fri., 5/19 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 6:30 pm | |
| Sat., 5/20 | V Baseball | New Milford | Away - New Milford HS [Directions] | 9:30 a.m. | $8 Adults, $5 Students | |
| Sat., 5/20 | V Softball | Bunnell | Home - PHS Softball Field [Directions] | 1:00 p.m. | W 15-0 | $8 Adults, $5 Students |
| Sat., 5/20 | FR Softball | Danbury | Away - Danbury HS Varsity Softball Field [Directions] | 10:00 a.m. | ||
| Mon., 5/22 | V Girls Lacrosse | Weston | Away - WHS Turf Field [Directions] | 7:00 p.m. | L 13-8 | @ Weston, $8 Adults, $5 Students |
| Mon., 5/22 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 4:00 p.m. | 4:00 - 8:30 pm | |
| Mon., 5/22 | Miscellaneous Events | Middlebury Park & Rec Lifeguard Recertification Class | - Health Classroom - Room 201 | 5:00 p.m. | 5:00 - 7:00 pm | |
| Mon., 5/22 | Miscellaneous Events | Middlebury Park & Rec Lifeguard Recertification Class | - PHS Pool | 7:00 p.m. | 7:00 - 9:30 pm | |
| Tue., 5/23 | V Baseball | SWC Semi-Finals | Away | 7:00 p.m. | @ Bethel, $8 Adults, $5 Students | |
| Tue., 5/23 | V Boys Lacrosse | Bunnell-Stratford | Home - Sports Complex & Track [Directions] | 7:00 p.m. | W 19-3 | SWC Tournament. $8 Adults, $5 Students |
| Tue., 5/23 | V Boys Outdoor Track | SWC Championship Meet | Away [Directions] | 3:00 p.m. | @ New Milford, $10 Adults, $5 Students | |
| Tue., 5/23 | V Boys Tennis | SWC Individual Tournament | Away [Directions] | 12:00 p.m. | @ Joel Barlow High School | |
| Tue., 5/23 | V Girls Outdoor Track | SWC Championship Meet | Away [Directions] | 3:00 p.m. | @ New Milford | |
| Tue., 5/23 | V Softball | Joel Barlow | Away [Directions] | 7:00 p.m. | W 7-2 | @ DeLuca Field (Stratford), $8 Adults, $5 Students |
| Tue., 5/23 | FR Softball | Newtown | Away - Newtown HS Softball Field [Directions] | 3:30 p.m. | ||
| Tue., 5/23 | V Girls Tennis | SWC Individual Tournament | Away [Directions] | 3:30 p.m. | @ Joel Barlow | |
| Tue., 5/23 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 4:00 p.m. | 4:00 - 8:30 pm | |
| Tue., 5/23 | Miscellaneous Events | Middlebury Park & Rec Lifeguard Recertification Class | - Health Classroom - Room 201 | 5:00 p.m. | 5:00 - 7:00 pm | |
| Tue., 5/23 | Miscellaneous Events | Middlebury Park & Rec Lifeguard Recertification Class | - PHS Pool | 7:00 p.m. | 7:00 - 9:30 pm | |
| Wed., 5/24 | V Baseball | SWC Championship Game | Away | Cancelled | Cancelled | @ Bethel or Penders Field in Stratford |
| Wed., 5/24 | JV Baseball | New Fairfield | Away - NFHS Baseball Field [Directions] | 3:45 p.m. | ||
| Wed., 5/24 | V Boys Golf | Newtown | Home - Heritage Village C.C. [Directions] | 2:30 p.m. | POmperaug | non-league |
| Wed., 5/24 | V Boys Tennis | SWC Individual Tournament | Away [Directions] | 2:00 p.m. | @ Weston | |
| Wed., 5/24 | V Girls Lacrosse | SWC Championship Game | Away | Cancelled | Cancelled | |
| Wed., 5/24 | V Softball | SWC Championship Game | Away [Directions] | 7:00 p.m. | @ DeLuca Field, $10 adults $5 Students | |
| Wed., 5/24 | FR Softball | Danbury | Home - Community Softball Field [Directions] | 3:30 p.m. | ||
| Wed., 5/24 | V Girls Tennis | SWC Individual Tournament | Away | 2:00 p.m. | @ Joel Barlow | |
| Wed., 5/24 | Miscellaneous Events | Volleyball Club | - PHS Main Gym | 2:30 p.m. | 2:30 to 4:15 pm | |
| Wed., 5/24 | Miscellaneous Events | Boys Soccer Pre Season Meeting | - Health Classroom - Room 201 | 3:30 p.m. | ||
| Wed., 5/24 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 4:00 p.m. | 4:00 - 8:30 pm | |
| Wed., 5/24 | Miscellaneous Events | Middlebury Park & Rec Lifeguard Recertification Class | - Health Classroom - Room 201 | 5:00 p.m. | 5:00 - 7:00 pm | |
| Wed., 5/24 | Miscellaneous Events | Middlebury Park & Rec Lifeguard Recertification Class | - PHS Pool | 7:00 p.m. | 7:00 - 9:30 pm | |
| Thu., 5/25 | V Boys Golf | CHAPPA Tournament | Away | TBA | No bus | |
| Thu., 5/25 | V Boys Lacrosse | Masuk | Away [Directions] | 5:00 p.m. | L 6-8 | @ Brookfield High School, $10 Adults, $5 Students |
| Thu., 5/25 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 4:00 p.m. | 4:00 - 8:30 pm | |
| Fri., 5/26 | V Boys Golf | SWC Championships | Away | 7:30 a.m. | @ Ridgewood CC, Danbury | |
| Fri., 5/26 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 6:30 pm | |
| Fri., 5/26 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 4:00 p.m. | 4:00 - 7:00 pm | |
| Fri., 5/26 | School Holidays and Closings | Early Dismissal - Professional Development | ||||
| Sat., 5/27 | V Boys Tennis | CIAC Tournament | Away | 8:30 p.m. | @ Hall High School | |
| Sat., 5/27 | V Girls Tennis | CIAC Tournament | Home [Directions] | 10:00 a.m. | at RHAM High School | |
| Mon., 5/29 | School Holidays and Closings | Memorial Day | ||||
| Tue., 5/30 | V Baseball | Westhill | Away [Directions] | 3:30 p.m. | ||
| Tue., 5/30 | V Baseball | CIAC Tournament | Away | 3:30 p.m. | ||
| Tue., 5/30 | V Boys Outdoor Track | CIAC Class Meet | Away [Directions] | TBA | @ Manchester High School | |
| Tue., 5/30 | V Girls Lacrosse | CIAC Tournament | Home - Sports Complex & Track [Directions] | 5:00 p.m. | $8 Adults, $5 Students | |
| Tue., 5/30 | V Girls Outdoor Track | CIAC Class Meet | Away [Directions] | TBA | @ Manchester HS | |
| Tue., 5/30 | V Girls Tennis | CIAC Tournament | Away | 3:00 p.m. | At Edgewo at Edgewood tennis courts in Middlebury | |
| Tue., 5/30 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 4:00 p.m. | 4:00 - 8:30 pm | |
| Tue., 5/30 | School Holidays and Closings | Senior Class Trip | ||||
| Wed., 5/31 | V Boys Lacrosse | Fitch | Home - Sports Complex & Track [Directions] | 4:30 p.m. | W 16-4 | $8 Adults, $5 Students |
| Wed., 5/31 | V Softball | CIAC Tournament Game | Home - PHS Softball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/31 | V Girls Tennis | Daniel Hand | Away [Directions] | 3:00 p.m. | ||
| Wed., 5/31 | Miscellaneous Events | Volleyball Club | - PHS Main Gym | 2:30 p.m. | 2:30 to 4:15 pm | |
| Wed., 5/31 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 4:00 p.m. | 4:00 - 8:30 pm | |
| Thu., 6/1 | V Girls Lacrosse | CIAC Tournament | Home - Sports Complex & Track [Directions] | 3:00 p.m. | $8 Adults, $5 Students | |
| Thu., 6/1 | Miscellaneous Events | Volleyball Club | - PHS Main Gym | 2:30 p.m. | 2:30 to 4:15 pm | |
| Thu., 6/1 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 7:30 pm | |
| Fri., 6/2 | V Softball | Daniel Hand | Home - PHS Softball Field [Directions] | 4:00 p.m. | $8 Adults, $5 Students | |
| Fri., 6/2 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 7:30 pm | |
| Sat., 6/3 | V Boys Lacrosse | North Haven | Away [Directions] | 3:00 p.m. | L 14-7 | $8 adults, $5 students |
| Sun., 6/4 | Miscellaneous Events | Kinetic Kids Gymnastics Exhibition | - PHS Main Gym | 7:00 a.m. | 7:00 am - 7:00 pm | |
| Sun., 6/4 | School Holidays and Closings | Prom | ||||
| Mon., 6/5 | V Boys Outdoor Track | State Open Meet | Away | 2:30 p.m. | ||
| Mon., 6/5 | V Girls Outdoor Track | State Open Meet | Away | 2:30 p.m. | ||
| Mon., 6/5 | School Holidays and Closings | Teacher Work Day - No School | ||||
| Tue., 6/6 | V Boys Golf | CIAC Div. I Championship | Away - Fairview Farms - Harwinton [Directions] | Cancelled | Cancelled | |
| Tue., 6/6 | V Girls Lacrosse | CIAC Tournament | Away [Directions] | 5:00 p.m. | $10 Adults, $5 Students, @ Guilford HS | |
| Tue., 6/6 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 3:00 p.m. | 3:00 - 7:30 pm | |
| Tue., 6/6 | Miscellaneous Events | CPR class for Coaches | - Health Classroom - Room 201 | 5:00 p.m. | ||
| Wed., 6/7 | Miscellaneous Events | Boys Track Meeting | - Health Classroom - Room 201 | 3:00 p.m. | 3:00 - 5:00 pm | |
| Wed., 6/7 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 4:00 p.m. | 4:00 pm - 8:30 pm | |
| Thu., 6/8 | V Softball | CIAC Semi Final | Away [Directions] | 7:00 p.m. | @ West Haven, $10 Adults, $5 Students | |
| Thu., 6/8 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 3:00 p.m. | 3:00 - 7:30 pm | |
| Fri., 6/9 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 pm - 6:30 pm | |
| Sat., 6/10 | V Boys Outdoor Track | New England Meet | Away | TBA | ||
| Sat., 6/10 | V Girls Lacrosse | CIAC Championship Game | Away | 3:00 p.m. | $10 Adults, $5 Students | |
| Sat., 6/10 | V Girls Outdoor Track | New England Meet | Away | TBA | ||
| Sat., 6/10 | Miscellaneous Events | Southbury Baseball/American Legion | - PHS Baseball Field | 10:00 a.m. | 10:00 am - 1:00 pm | |
| Tue., 6/13 | V Girls Outdoor Track | State Heptathlon/Hammer/Steeplechase | Away | TBA | ||
| Tue., 6/13 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 3:00 p.m. | 3:00 - 7:30 pm | |
| Tue., 6/13 | Miscellaneous Events | Southbury Baseball/American Legion | - PHS Baseball Field | 4:30 p.m. | 4:30 - 7:30 pm | |
| Wed., 6/14 | V Boys Outdoor Track | State Heptathlon/Hammer/Steeplechase | Away | TBA | ||
| Wed., 6/14 | Miscellaneous Events | Field Hockey Meeting | - Health Classroom - Room 201 | 2:15 p.m. | ||
| Wed., 6/14 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 4:00 p.m. | 4:00 pm - 8:30 pm | |
| Thu., 6/15 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 3:00 p.m. | 3:00 - 7:30 pm | |
| Thu., 6/15 | Miscellaneous Events | Southbury Baseball/American Legion | - PHS Baseball Field | 4:30 p.m. | 4:30 - 7:30 pm | |
| Fri., 6/16 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 pm - 6:30 pm | |
| Sat., 6/17 | Miscellaneous Events | Southbury Baseball/American Legion | - PHS Baseball Field | 10:00 a.m. | 10:00 am - 3:00 pm | |
| Wed., 6/21 | V Boys Golf | New England Championships | Away - Bretwood GC - Keene, NH | Cancelled | Cancelled | |
| Wed., 6/21 | Miscellaneous Events | Southbury Baseball/American Legion | - PHS Baseball Field | 4:30 p.m. | 4:30 - 7:30 pm | |
| Thu., 6/22 | Miscellaneous Events | Southbury Baseball/American Legion | - PHS Baseball Field | 4:30 p.m. | 4:30 - 7:30 pm | |
| Thu., 6/22 | School Holidays and Closings | Tentative Last Day of School | ||||
| Fri., 6/23 | School Holidays and Closings | Teacher Work Day | ||||
| Sat., 6/24 | Miscellaneous Events | Southbury Baseball/American Legion | - PHS Baseball Field | 10:00 a.m. | 10:00 am - 3:00 pm | |
| Mon., 6/26 | Miscellaneous Events | Middlebury Park & Rec Swim Lessons | - PHS Pool | 11:15 a.m. | 11:30 - 2:30 pm | |
| Mon., 6/26 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 am - 10:15 am | |
| Tue., 6/27 | Miscellaneous Events | Middlebury Park & Rec Swim Lessons | - PHS Pool | 11:15 a.m. | 11:30 - 2:30 pm | |
| Tue., 6/27 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 am - 10:15 am | |
| Tue., 6/27 | Miscellaneous Events | Southbury Baseball/American Legion | - PHS Baseball Field | 4:30 p.m. | 4:30 - 7:30 pm | |
| Wed., 6/28 | Miscellaneous Events | Middlebury Park & Rec Swim Lessons | - PHS Pool | 11:15 a.m. | 11:30 - 2:30 pm | |
| Wed., 6/28 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 am - 10:15 am | |
| Wed., 6/28 | Miscellaneous Events | Southbury Baseball/American Legion | - PHS Baseball Field | 4:30 p.m. | 4:30 - 7:30 pm | |
| Thu., 6/29 | Miscellaneous Events | Middlebury Park & Rec Swim Lessons | - PHS Pool | 11:15 a.m. | 11:30 - 2:30 pm | |
| Thu., 6/29 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 am - 10:15 am | |
| Thu., 6/29 | Miscellaneous Events | Southbury Baseball/American Legion | - PHS Baseball Field | 4:30 p.m. | 4:30 - 7:30 pm | |
| Fri., 8/25 | Miscellaneous Events | Professional Development - Phys Ed & Health | - Health Classroom - Room 201 | 8:00 a.m. | 8:00 - 3:00 pm | |
| Fri., 10/6 | Miscellaneous Events | Professional Development - Phys Ed & Health | - Health Classroom - Room 201 | 8:00 a.m. | 8:00 - 3:00 pm | |
| Fri., 11/3 | Miscellaneous Events | Southbury Park & Rec Open Bball | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 11/7 | Miscellaneous Events | Professional Development - Phys Ed & Health | - Health Classroom - Room 201 | 8:00 a.m. | 8:00 - 3:00 pm | |