| Pomperaug 2015-16 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 1668 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| TBA | JV Baseball | Notre Dame-Fairfield | Home - PHS Baseball Field [Directions] | 10:00 a.m. | ||
| TBA | JV Baseball | Stratford | Away - Penders Field [Directions] | TBA | 2:15 | |
| TBA | JV Baseball | Notre Dame-Fairfield | Away - Fabbri Field at Notre Dame [Directions] | TBA | 2:15 | |
| TBA | FR Boys Soccer | Amity | Away - Amity HS - Field # 2 [Directions] | 10:00 a.m. | 9:00 am | |
| TBA | V Co-ed Alpine Skiing | CISL Meet | Away | 3:30 p.m. | 2:20 pm | @ Mt. Southington |
| TBA | FR Girls Basketball | Weston | Away - WHS Gymnasium [Directions] | 3:30 p.m. | ||
| TBA | FR Girls Basketball | Notre Dame-Fairfield | Home - PHS Main Gym [Directions] | TBA | ||
| TBA | V Girls Soccer | Amity (Scrim.) | Away - Amity HS - Field # 3 [Directions] | Cancelled | ||
| TBA | FR Girls Soccer | Naugatuck | Home - PHS Soccer Field [Directions] | 3:45 p.m. | ||
| TBA | FR Girls Soccer | Amity | Away - Center Field - Woodbridge [Directions] | 4:00 p.m. | 3:00 pm | |
| TBA | JV Softball | Notre Dame-Fairfield | Home - PHS Softball Field [Directions] | 10:00 a.m. | ||
| TBA | JV Softball | Stratford | Away - King Street Field [Directions] | TBA | 2:15, share bus with JV Baseball | |
| TBA | JV Softball | Brookfield | Away - PTAK Softball Field [Directions] | Cancelled | ||
| Wed., 7/1 | Miscellaneous Events | Middlebury Park & Rec Swim Lessons | - PHS Pool | 11:30 a.m. | 11:30 - 2:15 pm | |
| Wed., 7/1 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 - 8:30 am | |
| Thu., 7/2 | Miscellaneous Events | Middlebury Park & Rec Swim Lessons | - PHS Pool | 11:30 a.m. | 11:30 - 2:15 pm | |
| Thu., 7/2 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 - 8:30 am | |
| Mon., 7/6 | Miscellaneous Events | Middlebury Park & Rec Swim Lessons | - PHS Pool | 11:30 a.m. | 11:30 - 2:15 pm | |
| Mon., 7/6 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 - 8:30 am | |
| Mon., 7/6 | Miscellaneous Events | Triple Threat Basketball Camp | - PHS Main Gym | 8:00 a.m. | 8:00 am - 2:00 pm | |
| Tue., 7/7 | Miscellaneous Events | Middlebury Park & Rec Swim Lessons | - PHS Pool | 11:30 a.m. | 11:30 - 2:15 pm | |
| Tue., 7/7 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 - 8:30 am | |
| Tue., 7/7 | Miscellaneous Events | Triple Threat Basketball Camp | - PHS Main Gym | 8:00 a.m. | 8:00 am - 2:00 pm | |
| Wed., 7/8 | Miscellaneous Events | Middlebury Park & Rec Swim Lessons | - PHS Pool | 11:30 a.m. | 11:30 - 2:15 pm | |
| Wed., 7/8 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 - 8:30 am | |
| Wed., 7/8 | Miscellaneous Events | Triple Threat Basketball Camp | - PHS Main Gym | 8:00 a.m. | 8:00 am - 2:00 pm | |
| Wed., 7/8 | Miscellaneous Events | Triple Threat Basketball Camp | - PHS Main Gym | 8:00 a.m. | 8:00 am - 2:00 pm | |
| Thu., 7/9 | Miscellaneous Events | Middlebury Park & Rec Swim Lessons | - PHS Pool | 11:30 a.m. | 11:30 - 2:15 pm | |
| Thu., 7/9 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 - 8:30 am | |
| Thu., 7/9 | Miscellaneous Events | Triple Threat Basketball Camp | - PHS Main Gym | 8:00 a.m. | 8:00 am - 2:00 pm | |
| Fri., 7/10 | Miscellaneous Events | Triple Threat Basketball Camp | - PHS Main Gym | 8:00 a.m. | 8:00 am - 2:00 pm | |
| Fri., 7/10 | Miscellaneous Events | Nutmeg Games Gymnastic Set-Up | - PHS Main Gym | 4:00 p.m. | 4:00 pm - 8:00 pm | |
| Sat., 7/11 | Miscellaneous Events | Nutmeg Games Gymnastic Meet | - PHS Main Gym | 10:00 a.m. | 10:00 am - 6:00 pm | |
| Sun., 7/12 | Miscellaneous Events | Nutmeg Games Gymnastic Meet | - PHS Main Gym | 10:00 a.m. | 10:00 am - 6:00 pm | |
| Mon., 7/13 | Miscellaneous Events | Middlebury Park & Rec Swim Lessons | - PHS Pool | 11:30 a.m. | 11:30 - 2:15 pm | |
| Mon., 7/13 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 - 8:30 am | |
| Tue., 7/14 | Miscellaneous Events | Middlebury Park & Rec Swim Lessons | - PHS Pool | 11:30 a.m. | 11:30 - 2:15 pm | |
| Tue., 7/14 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 - 8:30 am | |
| Wed., 7/15 | Miscellaneous Events | Middlebury Park & Rec Swim Lessons | - PHS Pool | 11:30 a.m. | 11:30 - 2:15 pm | |
| Wed., 7/15 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 - 8:30 am | |
| Thu., 7/16 | Miscellaneous Events | Middlebury Park & Rec Swim Lessons | - PHS Pool | 11:30 a.m. | 11:30 - 2:15 pm | |
| Thu., 7/16 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 - 8:30 am | |
| Mon., 7/20 | Miscellaneous Events | Middlebury Park & Rec Swim Lessons | - PHS Pool | 11:30 a.m. | 11:30 - 2:15 pm | |
| Mon., 7/20 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 - 8:30 am | |
| Mon., 7/20 | Miscellaneous Events | Panther Basketball Camp | - PHS Main Gym | 9:00 a.m. | 9:00 am - 2:15 pm | |
| Tue., 7/21 | Miscellaneous Events | Middlebury Park & Rec Swim Lessons | - PHS Pool | 11:30 a.m. | 11:30 - 2:15 pm | |
| Tue., 7/21 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 - 8:30 am | |
| Tue., 7/21 | Miscellaneous Events | Panther Basketball Camp | - PHS Main Gym | 9:00 a.m. | 9:00 am - 2:15 pm | |
| Wed., 7/22 | Miscellaneous Events | Middlebury Park & Rec Swim Lessons | - PHS Pool | 11:30 a.m. | 11:30 - 2:15 pm | |
| Wed., 7/22 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 - 8:30 am | |
| Wed., 7/22 | Miscellaneous Events | Panther Basketball Camp | - PHS Main Gym | 9:00 a.m. | 9:00 am - 2:15 pm | |
| Thu., 7/23 | Miscellaneous Events | Middlebury Park & Rec Swim Lessons | - PHS Pool | 11:30 a.m. | 11:30 - 2:15 pm | |
| Thu., 7/23 | Miscellaneous Events | Panther Basketball Camp | - PHS Main Gym | 9:00 a.m. | 9:00 am - 2:15 pm | |
| Mon., 8/17 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 4:00 p.m. | 4:00 - 6:00 pm | |
| Mon., 8/17 | Miscellaneous Events | Girls Soccer Camp | - PHS Soccer Field | 5:00 p.m. | 5:00 - 7:00 pm | |
| Tue., 8/18 | Miscellaneous Events | Link Crew Training | - Auxiliary Gym | 8:00 a.m. | ||
| Tue., 8/18 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 4:00 p.m. | 4:00 - 6:00 pm | |
| Tue., 8/18 | Miscellaneous Events | Girls Soccer Camp | - PHS Soccer Field | 5:00 p.m. | 5:00 - 7:00 pm | |
| Wed., 8/19 | Miscellaneous Events | Link Crew Training | - Auxiliary Gym | 8:00 a.m. | ||
| Wed., 8/19 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 4:00 p.m. | 4:00 - 6:00 pm | |
| Wed., 8/19 | Miscellaneous Events | Girls Soccer Camp | - PHS Soccer Field | 5:00 p.m. | 5:00 - 7:00 pm | |
| Thu., 8/20 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 4:00 p.m. | 4:00 - 6:00 pm | |
| Thu., 8/20 | Miscellaneous Events | Girls Soccer Camp | - PHS Soccer Field | 5:00 p.m. | 5:00 - 7:00 pm | |
| Fri., 8/21 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 4:00 p.m. | 4:00 - 6:00 pm | |
| Fri., 8/21 | Miscellaneous Events | Girls Soccer Camp | - PHS Soccer Field | 5:00 p.m. | 5:00 - 7:00 pm | |
| Sat., 8/22 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 9:00 a.m. | 9:00 - 11:00 am | |
| Sun., 8/23 | Miscellaneous Events | Pop Warner Cheer Clinic | - PHS Main Gym | 6:30 a.m. | 6:30 am - 6:30 pm | |
| Sun., 8/23 | Miscellaneous Events | Pop Warner Cheer Clinic | - Health Classroom - Room 201 | 6:30 a.m. | 6:30 am - 6:30 pm | |
| Mon., 8/24 | Miscellaneous Events | Freshmen Orientation | - PHS Main Gym | 8:00 a.m. | 8:00 am - 1:30 pm | |
| Mon., 8/24 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 4:00 p.m. | 4:00 - 6:00 pm | |
| Mon., 8/24 | Miscellaneous Events | Freshmen Dance | - PHS Main Gym | 6:00 p.m. | 6:00 - 9:00 pm | |
| Tue., 8/25 | Miscellaneous Events | CPR class for coaches | - Health Classroom - Room 201 | 4:00 p.m. | 4:00 to 7:00 pm | |
| Tue., 8/25 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 4:00 p.m. | 4:00 - 6:00 pm | |
| Tue., 8/25 | Miscellaneous Events | SWC Fall Coaches Pre-Season Meeting | 7:30 p.m. | @ Masuk | ||
| Wed., 8/26 | V Football | Fairfield Ludlowe (Scrim.) | Away - Tomlinson MS [Directions] | 4:00 p.m. | 2:30 pm, 2 buses | |
| Wed., 8/26 | FR Football | Fairfield Ludlowe (Scrim.) | Away [Directions] | 4:00 p.m. | 2:30 pm | |
| Wed., 8/26 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 5:00 p.m. | 5:00 - 6:00 pm | |
| Thu., 8/27 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 2:00 p.m. | 2:00 - 6:30 pm | |
| Thu., 8/27 | School Holidays and Closings | Teacher Convocation Day | ||||
| Fri., 8/28 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 3:00 p.m. | 3:00 - 6:00 pm | |
| Fri., 8/28 | School Holidays and Closings | In Service Day for Teachers | ||||
| Sat., 8/29 | V Football | Bay Shore High School | Away | 5:00 p.m. | 1:30 pm, 2 buses | |
| Sat., 8/29 | Miscellaneous Events | Post University Baseball | - PHS Baseball Field | 10:00 a.m. | 10:00 - 1:00 | |
| Sat., 8/29 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 8:00 a.m. | 8:00 am - 2:00 pm | |
| Mon., 8/31 | V Boys Soccer | South Kent (Scrim.) | Away | 4:00 p.m. | 2:15 pm | |
| Mon., 8/31 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 3:00 p.m. | 3:00 - 6:00 pm | |
| Tue., 9/1 | V Field Hockey | Cheshire (Scrim.) | Away - Cheshire HS Field Hockey Field [Directions] | 4:00 p.m. | 2:15 pm | |
| Tue., 9/1 | V Girls Soccer | Shelton (Scrim.) | Away - Shelton HS - Upper Field [Directions] | 6:00 p.m. | 4:30 pm | |
| Tue., 9/1 | V Girls Volleyball | Holy Cross (Scrim.) | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Tue., 9/1 | JV Girls Volleyball | Holy Cross (Scrim.) | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Tue., 9/1 | Miscellaneous Events | Athletic Trainer | 2:30 p.m. | 2:30 - 6:30 | ||
| Tue., 9/1 | School Holidays and Closings | Students First Day of School | ||||
| Wed., 9/2 | V Boys Soccer | Seymour (Scrim.) | Home - Sports Complex & Track [Directions] | 7:00 p.m. | ||
| Wed., 9/2 | Miscellaneous Events | Athletic Trainer | 4:00 p.m. | 4:00 - 9:00 pm | ||
| Wed., 9/2 | Miscellaneous Events | Pop Warner Cheerleader Practicing | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30 pm | |
| Thu., 9/3 | V Football | Ridgefield (Scrim.) | Away - Tiger Hollow Stadium [Directions] | 5:00 p.m. | 2:30 pm, 2 buses | |
| Thu., 9/3 | V Girls Volleyball | Terryville (Scrim.) | Away [Directions] | 3:30 p.m. | 2:15 pm share w/jv | |
| Thu., 9/3 | JV Girls Volleyball | Terryville (Scrim.) | Away [Directions] | 3:30 p.m. | 2:15 pm share w/varsity | |
| Thu., 9/3 | Miscellaneous Events | Athletic Trainer | 2:30 p.m. | 2:30 - 6:00 pm | ||
| Fri., 9/4 | V Boys Cross Country | Danbury (Scrim.) | Away [Directions] | 7:40 p.m. | 5:30 pm | |
| Fri., 9/4 | FR Football | Ridgefield (Scrim.) | Away - Tiger Hollow Turf Field II [Directions] | 5:00 p.m. | 3:00 pm | |
| Fri., 9/4 | V Boys Soccer | Bullard Havens Tech (Scrim.) | Home - Sports Complex & Track [Directions] | 4:00 p.m. | ||
| Fri., 9/4 | V Girls Cross Country | Danbury (Scrim.) | Away [Directions] | 7:40 p.m. | 5:30 pm | |
| Fri., 9/4 | JV Field Hockey | New Fairfield JV Jamboree | Away | 3:30 p.m. | 2:15 pm | |
| Fri., 9/4 | JV Field Hockey | New Fairfield JV Jamboree | Away | 3:30 p.m. | ||
| Fri., 9/4 | V Girls Soccer | Woodland (Scrim.) | Away - Woodland Soccer Field [Directions] | 3:30 p.m. | 2:15 | |
| Fri., 9/4 | Miscellaneous Events | Athletic Trainer | 3:00 p.m. | 3:00 - 6:00 pm | ||
| Sat., 9/5 | V Boys Soccer | Cheshire (Scrim.) | Away - Cheshire High Main Game field [Directions] | 6:00 p.m. | 4:15 pm | |
| Sat., 9/5 | JV Boys Soccer | Cheshire (Scrim.) | Away - Cheshire HS soccer field [Directions] | 4:30 p.m. | 3:30 pm | |
| Sat., 9/5 | V Field Hockey | New Fairfield Jamboree | Away [Directions] | 8:30 a.m. | 7:30 am | |
| Sat., 9/5 | Miscellaneous Events | Athletic Trainer | 9:00 a.m. | 9:00 am - 1:00 pm | ||
| Mon., 9/7 | V Boys Soccer | Nonnewaug (Scrim.) | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Mon., 9/7 | V Field Hockey | Pomperaug Jamboree | Home - Sports Complex & Track [Directions] | 9:00 a.m. | Hall HS and Danbury HS | |
| Mon., 9/7 | Miscellaneous Events | Athletic Trainer | 9:00 a.m. | 9:00 am - 12:00 pm | ||
| Mon., 9/7 | School Holidays and Closings | Labor Day - No School | ||||
| Tue., 9/8 | V Girls Volleyball | Oxford (Scrim.) | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Tue., 9/8 | JV Girls Volleyball | Oxford (Scrim.) | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Tue., 9/8 | Miscellaneous Events | Athletic Trainer | 2:30 p.m. | 2:30 - 6:30 pm | ||
| Wed., 9/9 | V Field Hockey | Nonnewaug (Scrim.) | Home - Sports Complex & Track [Directions] | Cancelled | $5 Adults, $3 Students | |
| Wed., 9/9 | V Girls Volleyball | Seymour (Scrim.) | Home - PHS Main Gym [Directions] | 3:15 p.m. | ||
| Wed., 9/9 | JV Girls Volleyball | Seymour (Scrim.) | Home - PHS Main Gym [Directions] | 3:15 p.m. | ||
| Wed., 9/9 | Miscellaneous Events | Athletic Trainer | 2:30 p.m. | 2:30 - 9:00 pm | ||
| Wed., 9/9 | Miscellaneous Events | PAC Swim Clinic | - PHS Pool | 6:00 p.m. | 6:00 - 7:30 pm | |
| Wed., 9/9 | School Holidays and Closings | PHS Open House | ||||
| Thu., 9/10 | V Girls Soccer | Staples (Scrim.) | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Thu., 9/10 | JV Girls Soccer | Staples (Scrim.) | Home - PHS Soccer Field [Directions] | 5:00 p.m. | ||
| Thu., 9/10 | Miscellaneous Events | Athletic Trainer | 2:30 p.m. | 2:30 - 7:00 pm | ||
| Fri., 9/11 | V Football | Newtown | Home - Sports Complex & Track [Directions] | L 0-42 | $5 Adults, $3 Students | |
| Fri., 9/11 | V Boys Soccer | Bethel | Away - Rourke Field [Directions] | L 0-1 | 2:30 pm, share bus with JVs | |
| Fri., 9/11 | JV Boys Soccer | Bethel | Away - MS Field [Directions] | 3:45 p.m. | 2:30 pm, share bus with varsity | |
| Fri., 9/11 | V Girls Volleyball | Stratford | Away - Needham Memorial Gymnasium [Directions] | W 3-0 | 3:15, share bus with JVs | Non-league game |
| Fri., 9/11 | JV Girls Volleyball | Stratford | Away - Needham Memorial Gymnasium [Directions] | 5:00 p.m. | 3:15, share bus with JVs | |
| Fri., 9/11 | FR Girls Volleyball | New Milford | Home - Auxiliary Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/11 | Miscellaneous Events | Freshmen Picnic on The Baseball Field | - PHS Baseball Field | 3:30 p.m. | 3:30 to 5:30 | |
| Fri., 9/11 | Miscellaneous Events | Athletic Trainer | 5:00 p.m. | 5:00 - 9:00 pm | ||
| Fri., 9/11 | Miscellaneous Events | PAC Swim Clinic | - PHS Pool | 6:00 p.m. | 6:00 - 7:30 pm | |
| Sat., 9/12 | JV Football | Newtown | Away - Blue and Gold Stadium [Directions] | 10:00 a.m. | 8:00 am | |
| Sat., 9/12 | FR Football | Newtown | Home - Sports Complex & Track [Directions] | 10:00 a.m. | ||
| Sat., 9/12 | FR Boys Soccer | Masuk | Home - PHS Soccer Field [Directions] | 3:45 p.m. | ||
| Sat., 9/12 | FR Field Hockey | Newtown | Away - Treadwell Town Park [Directions] | 9:00 a.m. | 8:00 am | |
| Sat., 9/12 | V Girls Soccer | Bethel | Home - Sports Complex & Track [Directions] | L 1-2 | ||
| Sat., 9/12 | JV Girls Soccer | Bethel | Home - Sports Complex & Track [Directions] | W 3-1 | ||
| Sat., 9/12 | FR Girls Soccer | Masuk | Away - Masuk Middle Field [Directions] | 8:00 a.m. | 6:30 am | |
| Sat., 9/12 | Miscellaneous Events | Athletic Trainer | 10:00 a.m. | 10:00 am - 12:00 pm | ||
| Sat., 9/12 | Miscellaneous Events | Athletic Trainer | 5:00 p.m. | 5:00 - 9:00 pm | ||
| Sun., 9/13 | Miscellaneous Events | Post University Baseball | - PHS Baseball Field | 10:00 a.m. | 10:00 - 1:00 | |
| Mon., 9/14 | Miscellaneous Events | Athletic Trainer | 11:00 a.m. | 11:00 - 1:00 pm | ||
| Mon., 9/14 | Miscellaneous Events | Pop Warner Cheerleader Practicing | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30 pm | |
| Mon., 9/14 | School Holidays and Closings | Rosh Hashanah - No School | ||||
| Tue., 9/15 | V Boys Cross Country | Bunnell, Kolbe Cathedral | Away - Roosevelt Forest [Directions] | PHS 20 Bunnell 42 PHS 15 Kolbe 50 | 2:15 pm | |
| Tue., 9/15 | V Boys Soccer | New Milford | Home - Sports Complex & Track [Directions] | L 0-2 | $5 Adults, $3 Students | |
| Tue., 9/15 | JV Boys Soccer | New Milford | Home - Sports Complex & Track [Directions] | 5:15 p.m. | ||
| Tue., 9/15 | V Girls Cross Country | Bunnell, Kolbe Cathedral | Away - Roosevelt Forest [Directions] | PHS 15 Bunnell 50 PHS 15 Kolbe 50 | 2:15 pm | |
| Tue., 9/15 | V Field Hockey | New Fairfield | Away - Rebel Turf [Directions] | W 2-1 | 2:30, share bus with JVs | Non-league game |
| Tue., 9/15 | JV Field Hockey | New Fairfield | Away - Rebel Turf [Directions] | 3:45 p.m. | 2:30, share bus with varsity | |
| Tue., 9/15 | V Girls Soccer | New Milford | Away - New Milford HS [Directions] | T 4-4 | 2:30 pm | |
| Tue., 9/15 | JV Girls Soccer | New Milford | Away - New Milford HS [Directions] | L 3-1 | 2:30 pm | |
| Tue., 9/15 | V Girls Swimming and Diving | Masuk | Home - PHS Pool [Directions] | Pomperaug 93- Masuk 85 | $5 Adults, $3 Students | |
| Tue., 9/15 | Miscellaneous Events | PAC Swim Clinic | - PHS Pool | 2:00 p.m. | 2:00 - 4:00 pm | |
| Tue., 9/15 | Miscellaneous Events | Athletic Trainer | 5:00 p.m. | 5:00 - 9:00 pm | ||
| Wed., 9/16 | FR Football | New Fairfield | Home - Sports Complex & Track [Directions] | 4:00 p.m. | ||
| Wed., 9/16 | FR Boys Soccer | New Milford | Away - New Milford HS [Directions] | 3:45 p.m. | 2:30 | |
| Wed., 9/16 | FR Field Hockey | New Milford | Home - PHS Baseball Field [Directions] | 4:30 p.m. | ||
| Wed., 9/16 | V Girls Volleyball | Masuk | Home - PHS Main Gym [Directions] | W 3-0 | Non-league game | |
| Wed., 9/16 | JV Girls Volleyball | Masuk | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Wed., 9/16 | FR Girls Volleyball | Masuk | Home - Auxiliary Gym [Directions] | 3:45 p.m. | ||
| Wed., 9/16 | Miscellaneous Events | Athletic Trainer | 3:30 p.m. | 3:30 - 7:00 pm | ||
| Wed., 9/16 | Miscellaneous Events | Pop Warner Cheerleader Practicing | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30 pm | |
| Wed., 9/16 | Miscellaneous Events | PAC Swim Clinic | - PHS Pool | 7:00 p.m. | 7:00 - 9:00 pm | |
| Thu., 9/17 | V Boys Soccer | Brookfield | Away - BHS Stadium Field [Directions] | W 2-0 | 5:00 pm | |
| Thu., 9/17 | JV Boys Soccer | Brookfield | Away - BHS Stadium Field [Directions] | 5:00 p.m. | 3:15 pm | |
| Thu., 9/17 | V Field Hockey | New Milford | Home - Sports Complex & Track [Directions] | L 0-1 | Non-league game, $5 Adults, $3 Students | |
| Thu., 9/17 | JV Field Hockey | New Milford | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Thu., 9/17 | Miscellaneous Events | Athletic Trainer | 3:00 p.m. | 3:00 -8:30 pm | ||
| Thu., 9/17 | Miscellaneous Events | PAC Swim Clinic | - PHS Pool | 7:00 p.m. | 7:00 - 9:00 pm | |
| Fri., 9/18 | V Football | New Fairfield | Away - Rebel Stadium [Directions] | L 0-39 | 4:45 pm, 2 buses | |
| Fri., 9/18 | FR Field Hockey | Joel Barlow | Home - PHS Baseball Field [Directions] | 4:30 p.m. | ||
| Fri., 9/18 | V Girls Soccer | Brookfield | Home - Sports Complex & Track [Directions] | T 0-0 | ||
| Fri., 9/18 | FR Girls Soccer | New Milford | Home - Sports Complex & Track [Directions] | 5:15 p.m. | ||
| Fri., 9/18 | V Girls Swimming and Diving | New Fairfield | Home - PHS Pool [Directions] | Pomperaug 98- New Fairfield 80 | $5 Adults, $3 Students | |
| Fri., 9/18 | V Girls Volleyball | Brookfield | Home - PHS Main Gym [Directions] | W 3-1 | Non-league game | |
| Fri., 9/18 | JV Girls Volleyball | Brookfield | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 9/18 | FR Girls Volleyball | Brookfield | Away - BHS Big Gym [Directions] | 3:30 p.m. | 2:15 pm | |
| Fri., 9/18 | Miscellaneous Events | PAC Swim Clinic | - PHS Pool | 2:00 p.m. | 2:00 - 4:00 pm | |
| Fri., 9/18 | Miscellaneous Events | Athletic Trainer | 3:00 p.m. | 3:00 -9:00 pm | ||
| Sat., 9/19 | V Boys Cross Country | Amherst Invitational | Away | 10:00 a.m. | 6:30 am, share bus with girls cc | |
| Sat., 9/19 | JV Football | New Fairfield | Home - Sports Complex & Track [Directions] | 10:00 a.m. | ||
| Sat., 9/19 | FR Boys Soccer | Newtown | Home - PHS Soccer Field [Directions] | 9:00 a.m. | ||
| Sat., 9/19 | JV Competitive Cheerleading | New Fairfield | Home - Sports Complex & Track [Directions] | 10:00 a.m. | ||
| Sat., 9/19 | V Girls Cross Country | Amherst Invitational | Away | 10:00 a.m. | 6:30, share bus with boys cc | |
| Sat., 9/19 | V Field Hockey | Watertown | Home - Sports Complex & Track [Directions] | W 3-0 | Non-league game, $5 Adults, $3 Students | |
| Sat., 9/19 | JV Field Hockey | Watertown | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Sat., 9/19 | FR Field Hockey | Amity | Away - Amity HS [Directions] | 10:00 a.m. | 9:00 am | |
| Sat., 9/19 | JV Girls Soccer | Brookfield | Home - Sports Complex & Track [Directions] | T 1-1 | ||
| Sat., 9/19 | FR Girls Soccer | Newtown | Away - Newtown HS Practice Field [Directions] | 9:00 a.m. | 8:00 am | |
| Sat., 9/19 | Miscellaneous Events | Post University Baseball | - PHS Baseball Field | 10:00 a.m. | 10:00 - 1:00 | |
| Sat., 9/19 | Miscellaneous Events | Athletic Trainer | 11:00 a.m. | 11:00 - 1:00 pm | ||
| Sun., 9/20 | Miscellaneous Events | Post University Baseball | - PHS Baseball Field | 10:00 a.m. | 10:00 - 1:00 | |
| Sun., 9/20 | Miscellaneous Events | Pop Warner Football | - Sports Complex & Track | 9:30 a.m. | 9:30 - 6:00 pm | |
| Mon., 9/21 | V Boys Soccer | Masuk | Home - Sports Complex & Track [Directions] | T 2-2 | ||
| Mon., 9/21 | JV Boys Soccer | Masuk | Home - Sports Complex & Track [Directions] | 3:45 p.m. | ||
| Mon., 9/21 | FR Boys Soccer | Naugatuck | Away - Breen Field [Directions] | 3:45 p.m. | 2:15 pm | |
| Mon., 9/21 | FR Field Hockey | Masuk | Away - Masuk Middle Field [Directions] | 4:30 p.m. | 3:15 pm | |
| Mon., 9/21 | V Girls Soccer | Masuk | Away - Benedict Stadium Field @ Masuk HS [Directions] | L 0-3 | 5:15 pm | |
| Mon., 9/21 | JV Girls Soccer | Masuk | Away - Benedict Stadium Field @ Masuk HS [Directions] | L 0-3 | 4:00 pm | |
| Mon., 9/21 | V Girls Volleyball | Stratford | Home - PHS Main Gym [Directions] | W 3-0 | ||
| Mon., 9/21 | JV Girls Volleyball | Stratford | Home - PHS Main Gym [Directions] | 5:00 p.m. | ||
| Mon., 9/21 | FR Girls Volleyball | Weston | Away - WHS Gymnasium [Directions] | 4:00 p.m. | 2:15 pm | |
| Mon., 9/21 | Miscellaneous Events | PAC Swim Clinic | - PHS Pool | 2:00 p.m. | 2:00 - 4:00 pm | |
| Mon., 9/21 | Miscellaneous Events | PAC Swim Clinic | - PHS Pool | 2:00 p.m. | 2:00 - 4:00 pm | |
| Mon., 9/21 | Miscellaneous Events | Athletic Trainer | 3:30 p.m. | 3:30 - 7:00 pm | ||
| Mon., 9/21 | Miscellaneous Events | Pop Warner Cheerleader Practicing | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30 pm | |
| Mon., 9/21 | Miscellaneous Events | PAC Swim Team | - PHS Pool | 5:45 p.m. | 6:00 - 8:30 pm | |
| Tue., 9/22 | V Boys Cross Country | Masuk, New Fairfield, New Milford | Away - Great Hollow Lake Fields at Wolfe Park [Directions] | PHS 15 Masuk 50 NMHS 23 PHS 36 PHS 20 NFHS 40 | 2:15 pm | |
| Tue., 9/22 | V Girls Cross Country | Masuk, New Fairfield, New Milford | Away - Great Hollow Lake Fields at Wolfe Park [Directions] | PHS 16 NMHS 47 PHS 17 NFHS 46 PHS 15 Masuk 50 | 2:15 pm | |
| Tue., 9/22 | Miscellaneous Events | Athletic Trainer | 2:30 p.m. | 2:30 - 6:00 pm | ||
| Tue., 9/22 | Miscellaneous Events | PAC Swim Team | - PHS Pool | 5:45 p.m. | 6:00 - 8:30 pm | |
| Tue., 9/22 | Miscellaneous Events | PAC Swim Clinic | - PHS Pool | 7:00 p.m. | 7:00 - 9:00 pm | |
| Tue., 9/22 | School Holidays and Closings | In Service - Half Day | ||||
| Wed., 9/23 | Miscellaneous Events | Athletic Trainer | 8:00 a.m. | 8:00 - 12:00 noon | ||
| Wed., 9/23 | Miscellaneous Events | PAC Swim Team | - PHS Pool | 5:45 p.m. | 6:00 - 8:30 pm | |
| Wed., 9/23 | Miscellaneous Events | PAC Swim Clinic | - PHS Pool | 7:00 p.m. | 7:00 - 9:00 pm | |
| Wed., 9/23 | School Holidays and Closings | Yom Kippur - No School | ||||
| Thu., 9/24 | FR Football | Bethel | Away - DeSantis Field at Bethel HS [Directions] | 4:00 p.m. | 2:30 pm | |
| Thu., 9/24 | V Boys Soccer | Weston | Away - WHS Turf Field [Directions] | L 3-1 | 5:00 pm | |
| Thu., 9/24 | JV Boys Soccer | Weston | Away - WHS Turf Field [Directions] | 5:00 p.m. | 3:00 pm | |
| Thu., 9/24 | V Field Hockey | Immaculate | Home - Sports Complex & Track [Directions] | L 0-2 | ||
| Thu., 9/24 | JV Field Hockey | Immaculate | Home - Sports Complex & Track [Directions] | 3:30 p.m. | ||
| Thu., 9/24 | V Girls Soccer | Weston | Home - Sports Complex & Track [Directions] | L 0-3 | ||
| Thu., 9/24 | JV Girls Soccer | Weston | Home - PHS Soccer Field [Directions] | T 1-1 | ||
| Thu., 9/24 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 2:15 p.m. | ||
| Thu., 9/24 | Miscellaneous Events | Freshmen Class Meeting | - Health Classroom - Room 201 | 2:15 p.m. | 2:15 - 3:30 pm | |
| Thu., 9/24 | Miscellaneous Events | Athletic Trainer | 3:00 p.m. | 3:00 - 9:00 pm | ||
| Thu., 9/24 | Miscellaneous Events | PAC Swim Team | - PHS Pool | 5:45 p.m. | 6:00 - 8:30 pm | |
| Thu., 9/24 | Miscellaneous Events | PAC Swim Clinic | - PHS Pool | 7:00 p.m. | 7:00 - 9:00 pm | |
| Fri., 9/25 | V Football | Bethel | Home - Sports Complex & Track [Directions] | L 14-33 | $5 Adults, $3 Students | |
| Fri., 9/25 | V Girls Volleyball | Joel Barlow | Away - Lower Gym [Directions] | L 3-0 | 2:15, share bus with JVs | |
| Fri., 9/25 | JV Girls Volleyball | Joel Barlow | Away - Lower Gym [Directions] | 3:30 p.m. | 2:15, share bus with Varsity | |
| Fri., 9/25 | FR Girls Volleyball | SWC Freshmen Jamboree | Home - Auxiliary Gym [Directions] | 3:30 p.m. | ||
| Fri., 9/25 | Miscellaneous Events | PAC Swim Clinic | - PHS Pool | 2:00 p.m. | 2:00 - 4:00 pm | |
| Fri., 9/25 | Miscellaneous Events | Athletic Trainer | 3:30 p.m. | 3:30 - 9:00 pm | ||
| Fri., 9/25 | Miscellaneous Events | PAC Swim Team | - PHS Pool | 5:45 p.m. | 6:00 - 8:30 pm | |
| Fri., 9/25 | Miscellaneous Events | Pop Warner Cheerleading | - Auxiliary Gym | 6:30 p.m. | 6:30 - 9:00 pm | |
| Sat., 9/26 | JV Football | Bethel | Away - DeSantis Field at Bethel HS [Directions] | 3:00 p.m. | 1:00 pm | |
| Sat., 9/26 | FR Boys Soccer | Joel Barlow | Away - Field I (Stadium) [Directions] | 10:00 a.m. | 8:30 am | |
| Sat., 9/26 | FR Field Hockey | Immaculate | Home - PHS Baseball Field [Directions] | Cancelled | ||
| Sat., 9/26 | V Girls Volleyball | Lauralton Hall | Home - PHS Main Gym [Directions] | W 3-1 | ||
| Sat., 9/26 | JV Girls Volleyball | Lauralton Hall | Home - PHS Main Gym [Directions] | 12:00 p.m. | ||
| Sat., 9/26 | FR Girls Volleyball | Immaculate | Home - PHS Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 9/26 | Miscellaneous Events | Post University Baseball | - PHS Baseball Field | 10:00 a.m. | 10:00 - 1:00 | |
| Sat., 9/26 | Miscellaneous Events | Athletic Trainer | 12:00 p.m. | 12:00 - 3:00 pm | ||
| Sun., 9/27 | Miscellaneous Events | Pop Warner Football | - Sports Complex & Track | 9:30 a.m. | 9:30 - 6:00 pm | |
| Mon., 9/28 | JV Field Hockey | Masuk | Home - Sports Complex & Track [Directions] | 3:45 p.m. | ||
| Mon., 9/28 | FR Field Hockey | New Fairfield | Away - Rebel Turf [Directions] | 4:30 p.m. | 3:15 pm | |
| Mon., 9/28 | V Girls Volleyball | Weston | Home - PHS Main Gym [Directions] | W 3-2 | ||
| Mon., 9/28 | JV Girls Volleyball | Weston | Home - PHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 9/28 | FR Girls Volleyball | Weston | Home - Auxiliary Gym [Directions] | 4:00 p.m. | ||
| Mon., 9/28 | Miscellaneous Events | PAC Swim Clinic | - PHS Pool | 2:00 p.m. | 2:00 - 4:00 pm | |
| Mon., 9/28 | Miscellaneous Events | Athletic Trainer | 3:30 p.m. | 3:30 - 7:00 pm | ||
| Mon., 9/28 | Miscellaneous Events | Pop Warner Cheerleader Practicing | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30 pm | |
| Tue., 9/29 | V Boys Cross Country | Immaculate, Bethel, Joel Barlow | Home - Pomperaug HS [Directions] | PHS 22 Barlow 38 PHS 15 Bethel 48 PHS 17 Immaculate 46 | ||
| Tue., 9/29 | V Boys Soccer | Newtown | Away - Treadwell Town Park [Directions] | T 1-1 | 2:30 pm, share bus with JVs | |
| Tue., 9/29 | JV Boys Soccer | Newtown | Away - Treadwell Town Park--Tilson Field [Directions] | 3:45 p.m. | 2:15 pm, share bus with varsity | |
| Tue., 9/29 | V Girls Cross Country | Immaculate, Bethel, Joel Barlow | Home - Pomperaug HS [Directions] | IHS 28 PHS 29 PHS 15 Barlow 50 PHS 15 Bethel 50 | ||
| Tue., 9/29 | V Field Hockey | Masuk | Home - Sports Complex & Track [Directions] | W 3-0 | ||
| Tue., 9/29 | V Girls Soccer | Newtown | Home - Sports Complex & Track [Directions] | W 2-0 | ||
| Tue., 9/29 | V Girls Swimming and Diving | Brookfield | Home - PHS Pool [Directions] | Pomperaug 97- Brookfield 84 | $5 Adults, $3 Students | |
| Tue., 9/29 | Miscellaneous Events | PAC Swim Clinic | - PHS Pool | 2:00 p.m. | 2:00 - 4:00 pm | |
| Tue., 9/29 | Miscellaneous Events | Athletic Trainer | 4:00 p.m. | 4:00 - 9:00 pm | ||
| Wed., 9/30 | JV Girls Soccer | Newtown | Home - Sports Complex & Track [Directions] | L 0-1 | ||
| Wed., 9/30 | V Girls Volleyball | Bunnell | Home - PHS Main Gym [Directions] | W 3-1 | ||
| Wed., 9/30 | JV Girls Volleyball | Bunnell | Home - PHS Main Gym [Directions] | 4:30 p.m. | ||
| Wed., 9/30 | FR Girls Volleyball | Amity | Home - Auxiliary Gym [Directions] | 4:00 p.m. | ||
| Wed., 9/30 | Miscellaneous Events | Athletic Trainer | 3:00 p.m. | 3:00 - 7:00 pm | ||
| Wed., 9/30 | Miscellaneous Events | Pop Warner Cheerleader Practicing | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30 pm | |
| Wed., 9/30 | Miscellaneous Events | PAC Swim Clinic | - PHS Pool | 7:00 p.m. | 7:00 - 9:00 pm | |
| Thu., 10/1 | FR Football | Stratford | Home - Sports Complex & Track [Directions] | 4:00 p.m. | ||
| Thu., 10/1 | JV Boys Soccer | Immaculate | Home - PHS Soccer Field [Directions] | 3:45 p.m. | ||
| Thu., 10/1 | FR Boys Soccer | Holy Cross | Away - Upper Murray Park [Directions] | 3:45 p.m. | 2:30 pm | |
| Thu., 10/1 | V Field Hockey | New Milford | Away - New Milford HS [Directions] | L 0-1 | 2:15, share bus with JVs | |
| Thu., 10/1 | JV Field Hockey | New Milford | Away - New Milford HS [Directions] | 5:30 p.m. | 2:15, share bus with JVs | |
| Thu., 10/1 | FR Field Hockey | Brookfield | Home - PHS Baseball Field [Directions] | Cancelled | ||
| Thu., 10/1 | V Girls Soccer | Immaculate | Away - Mustang Valley [Directions] | L 0-2 | 2:45 pm | |
| Thu., 10/1 | V Girls Swimming and Diving | Joel Barlow | Away - Western CT State University - O'Neill Center [Directions] | Pomperaug 96- Joel Barlow 82 | 2:15 pm | |
| Thu., 10/1 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 2:15 p.m. | ||
| Thu., 10/1 | Miscellaneous Events | Athletic Trainer | 3:00 p.m. | 3:00 - 9:00 pm | ||
| Fri., 10/2 | V Boys Cross Country | Nonnewaug Invitational | Away | 4:00 p.m. | 2:15 pm | |
| Fri., 10/2 | V Girls Cross Country | Nonnewaug Invitational | Away | 4:00 p.m. | 2:15 | |
| Fri., 10/2 | V Girls Volleyball | Bethel | Away - Bethel HS [Directions] | W 3-0 | 2:15, share bus with JVs | |
| Fri., 10/2 | JV Girls Volleyball | Bethel | Away - Bethel HS [Directions] | 3:30 p.m. | 2:15, share bus with varsity | |
| Fri., 10/2 | FR Girls Volleyball | Newtown | Away - Newtown HS Gymnasium [Directions] | 3:30 p.m. | 2:15 pm | |
| Fri., 10/2 | Miscellaneous Events | Pop Warner Cheerleading | - Auxiliary Gym | 6:30 p.m. | 6:30 - 9:00 pm | |
| Sat., 10/3 | V Football | Stratford | Away - Penders Field [Directions] | L 5-31 | 1:45 pm, 2 buses | |
| Sat., 10/3 | V Boys Soccer | Naugatuck | Home - Sports Complex & Track [Directions] | T 1-1 | ||
| Sat., 10/3 | V Field Hockey | Weston | Away - WHS Turf Field [Directions] | W 4-1 | 3:00 pm, share bus with varsity | |
| Sat., 10/3 | JV Field Hockey | Weston | Away - WHS Turf Field [Directions] | 5:00 p.m. | 3:00 pm, share bus with varsity | |
| Sat., 10/3 | V Girls Soccer | Naugatuck | Home - Sports Complex & Track [Directions] | W 4-0 | ||
| Sat., 10/3 | Miscellaneous Events | Post University Baseball | - PHS Baseball Field | 10:00 a.m. | 10:00 - 1:00 pm | |
| Sat., 10/3 | Miscellaneous Events | Athletic Trainer | 10:00 a.m. | 10:00 am - 7:00 pm | ||
| Sun., 10/4 | Miscellaneous Events | Post University Baseball | - PHS Baseball Field | 10:00 a.m. | 10:00 - 1:00 pm | |
| Sun., 10/4 | Miscellaneous Events | Pop Warner Football | - Sports Complex & Track | 9:30 a.m. | 9:30 - 6:00 pm | |
| Mon., 10/5 | JV Football | Stratford | Away - Sports Complex & Track [Directions] | 4:00 p.m. | 2:15 | |
| Mon., 10/5 | V Boys Soccer | Watertown | Away - John J. Mills Complex @ Watertown HS [Directions] | W 2-0 | 4:45 pm | |
| Mon., 10/5 | JV Boys Soccer | Watertown | Away - John J. Mills Complex @ Watertown HS [Directions] | 3:45 p.m. | 2:15 pm | |
| Mon., 10/5 | FR Boys Soccer | Masuk | Away - Great Hollow Lake Fields at Wolfe Park [Directions] | 4:00 p.m. | 2:45 pm | |
| Mon., 10/5 | FR Girls Soccer | Masuk | Home - Long Meadow Elementary School [Directions] | 3:45 p.m. | 3:00 one way shuttle | |
| Mon., 10/5 | V Girls Volleyball | Immaculate | Home - PHS Main Gym [Directions] | W 3-0 | ||
| Mon., 10/5 | JV Girls Volleyball | Immaculate | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Mon., 10/5 | Miscellaneous Events | Athletic Trainer | 3:00 p.m. | 3:00 - 7:00 pm | ||
| Mon., 10/5 | Miscellaneous Events | Pop Warner Cheerleading | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30 pm | |
| Mon., 10/5 | Miscellaneous Events | Stby PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:45 pm | |
| Tue., 10/6 | V Boys Cross Country | Newtown, Brookfield | Away [Directions] | PHS 27 Newtown 30 Brookfield 25 PHS 31 | 2:15 | |
| Tue., 10/6 | V Boys Soccer | Kolbe Cathedral | Away - Seaside Park Field #1 [Directions] | W 4-1 | 2:15 pm, share bus with JVs | |
| Tue., 10/6 | JV Boys Soccer | Kolbe Cathedral | Away [Directions] | Cancelled | ||
| Tue., 10/6 | V Girls Cross Country | Newtown, Brookfield | Away - Reed School [Directions] | PHS 15 Brookfield 50 Newtown 25 PHS 33 | 2:15 pm | |
| Tue., 10/6 | V Girls Soccer | Kolbe Cathedral | Home - PHS Soccer Field [Directions] | W 8-0 | ||
| Tue., 10/6 | JV Girls Soccer | Kolbe Cathedral | Home - Sports Complex & Track [Directions] | Cancelled | ||
| Tue., 10/6 | V Girls Swimming and Diving | Newtown | Away - Newtown HS Pool [Directions] | Pomperaug 92- Newtown 89 | 5:15 pm | |
| Tue., 10/6 | Miscellaneous Events | Athletic Trainer | 3:00 p.m. | 3:00 - 7:00 pm | ||
| Tue., 10/6 | Miscellaneous Events | Stby PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:45 pm | |
| Wed., 10/7 | JV Boys Soccer | Naugatuck | Away [Directions] | Cancelled | 2:15 | |
| Wed., 10/7 | V Field Hockey | Joel Barlow | Home - PHS Baseball Field [Directions] | L 0-1 | ||
| Wed., 10/7 | JV Field Hockey | Joel Barlow | Home - PHS Baseball Field [Directions] | 5:15 p.m. | ||
| Wed., 10/7 | FR Girls Soccer | New Milford | Away - New Milford HS [Directions] | 4:15 p.m. | 3:15 | |
| Wed., 10/7 | V Girls Volleyball | Newtown | Away - Newtown HS Gymnasium [Directions] | L 2-3 | 3:45, share bus with JVs | |
| Wed., 10/7 | JV Girls Volleyball | Newtown | Away - Newtown HS Gymnasium [Directions] | 5:00 p.m. | 3:45, share bus with JVs | |
| Wed., 10/7 | FR Girls Volleyball | Shelton | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Wed., 10/7 | Miscellaneous Events | Athletic Trainer | 3:00 p.m. | 3:00 - 7:00 pm | ||
| Wed., 10/7 | Miscellaneous Events | Pop Warner Cheerleading | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30 pm | |
| Wed., 10/7 | Miscellaneous Events | Stby PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:45 pm | |
| Thu., 10/8 | V Boys Soccer | Joel Barlow | Home - PHS Soccer Field [Directions] | L 2-0 | ||
| Thu., 10/8 | JV Boys Soccer | Joel Barlow | Home - Long Meadow Elementary School [Directions] | 3:45 p.m. | 3:00 pm, one way shuttle to LMES | |
| Thu., 10/8 | FR Boys Soccer | New Milford | Away - New Milford HS [Directions] | 3:45 p.m. | 2:15 pm | |
| Thu., 10/8 | FR Girls Volleyball | Amity | Away - Amity HS [Directions] | 4:00 p.m. | 3:00 pm | |
| Thu., 10/8 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 2:15 p.m. | ||
| Thu., 10/8 | Miscellaneous Events | Athletic Trainer | 3:00 p.m. | 3:00 - 7:00 pm | ||
| Thu., 10/8 | Miscellaneous Events | Stby PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:45 pm | |
| Fri., 10/9 | V Football | Weston | Away - WHS Stadium Field [Directions] | L 14-20 | 5:00 pm, 2 buses | |
| Fri., 10/9 | JV Boys Soccer | Naugatuck | Away - Breen Field [Directions] | 3:45 p.m. | 2:15 pm | @ Breen Field |
| Fri., 10/9 | V Field Hockey | New Fairfield | Away - Rebel Turf [Directions] | W 2-0 | 3:30, share bus with JVs | |
| Fri., 10/9 | JV Field Hockey | New Fairfield | Away - New Fairfield Turf [Directions] | 6:00 p.m. | 4:45 Share bus with varsity | |
| Fri., 10/9 | V Girls Swimming and Diving | Weston | Home - PHS Pool [Directions] | Pomperaug 90- Weston 94 | $5 Adults, $3 Students | |
| Fri., 10/9 | V Girls Volleyball | Kolbe Cathedral | Home - PHS Main Gym [Directions] | W 3-0 | ||
| Fri., 10/9 | JV Girls Volleyball | Kolbe Cathedral | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 10/9 | FR Girls Volleyball | New Milford | Away - New Milford HS [Directions] | 4:00 p.m. | 2:45 pm | |
| Fri., 10/9 | Miscellaneous Events | Athletic Trainer | 3:00 p.m. | 3:00 - 8:00 pm | ||
| Fri., 10/9 | Miscellaneous Events | Stby PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:45 pm | |
| Fri., 10/9 | Miscellaneous Events | Pop Warner Cheerleading | - Auxiliary Gym | 6:30 p.m. | 6:30 - 9:00 pm | |
| Fri., 10/9 | School Holidays and Closings | Prof Development - Half Day | ||||
| Sat., 10/10 | V Boys Cross Country | Manhattan College Invitational | Away | TBA | 10:00 am, share bus with girls cc | |
| Sat., 10/10 | JV Football | Weston | Away - WHS Stadium Field [Directions] | 10:00 a.m. | 8:00 am | |
| Sat., 10/10 | FR Boys Soccer | Amity | Home - PHS Soccer Field [Directions] | 10:00 a.m. | ||
| Sat., 10/10 | JV Competitive Cheerleading | Weston | Home - Sports Complex & Track [Directions] | 10:00 a.m. | ||
| Sat., 10/10 | V Girls Cross Country | Manhattan invitational | Away | TBA | 10:00 am, Share bus with boys cc | |
| Sat., 10/10 | FR Field Hockey | Amity | Home - PHS Baseball Field [Directions] | 10:00 a.m. | ||
| Sat., 10/10 | Miscellaneous Events | Post University Baseball | - PHS Baseball Field | 10:00 a.m. | 10:00 - 1:00 pm | |
| Sat., 10/10 | Miscellaneous Events | Pop Warner Cheerleaders Practice | - Auxiliary Gym | 11:00 a.m. | 11:00 - 1:00 pm | |
| Sat., 10/10 | Miscellaneous Events | Athletic Trainer | 8:30 a.m. | 8:30 am - 12:00 pm | ||
| Sun., 10/11 | Miscellaneous Events | Post University Baseball | - PHS Baseball Field | 10:00 a.m. | 10:00 - 1:00 pm | |
| Mon., 10/12 | V Field Hockey | Greenwich | Home - Taft Field [Directions] | W 2-1 | ||
| Mon., 10/12 | Miscellaneous Events | Brookfield HS Girls Swim Practice | - PHS Pool | 8:00 a.m. | 8:00 - 11:00 am | |
| Mon., 10/12 | Miscellaneous Events | Athletic Trainer | 4:00 p.m. | 4:00 - 6:00 pm | ||
| Mon., 10/12 | School Holidays and Closings | Columbus Day - No School | ||||
| Tue., 10/13 | V Boys Cross Country | Stratford, Weston, Notre Dame-Fairfield | Home - Pomperaug HS [Directions] | PHS 15 NDHS 50 PHS 19 Stratford 44 PHS 17 Weston 43 | ||
| Tue., 10/13 | V Boys Soccer | Notre Dame-Fairfield | Away - Veteran's Park - Bridgeport [Directions] | L 1-3 | 2:15 pm | |
| Tue., 10/13 | V Girls Cross Country | Stratford, Weston, Notre Dame-Fairfield | Home - Pomperaug HS [Directions] | PHS 15 Stratford 50 PHS 15 NDHS 50 PHS 15 Weston 50 | ||
| Tue., 10/13 | V Field Hockey | Bethel | Away - Hunt Field at Bethel HS [Directions] | L 0-1 | 4:25, share bus with JVs | |
| Tue., 10/13 | JV Field Hockey | Bethel | Away - Hunt Field at Bethel HS [Directions] | 5:15 p.m. | 4:25, share bus with varsity | |
| Tue., 10/13 | FR Field Hockey | Bethel | Away - Hunt Field at Bethel HS [Directions] | 3:45 p.m. | 2:30 pm | |
| Tue., 10/13 | V Girls Swimming and Diving | Bunnell | Home - PHS Pool [Directions] | Pomperaug 83- Bunnell 74 | $5 Adults, $3 Students | |
| Tue., 10/13 | V Girls Volleyball | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | W 3-1 | 3:00 pm share bus w/jv | |
| Tue., 10/13 | JV Girls Volleyball | Nonnewaug | Away - Nonnewaug HS Gym [Directions] | 4:00 p.m. | 3:00 pm share bus with varsity | |
| Tue., 10/13 | Miscellaneous Events | Athletic Trainer | 3:00 p.m. | 3:00 - 9:00 pm | ||
| Tue., 10/13 | Miscellaneous Events | Stby PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:45 pm | |
| Tue., 10/13 | Miscellaneous Events | Stby Park & Rec Open Basketball Gym | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 10/14 | JV Girls Soccer | Notre Dame-Fairfield | Home - Sports Complex & Track [Directions] | Cancelled | ||
| Wed., 10/14 | V Girls Volleyball | Notre Dame-Fairfield | Away - Sister Marion Rielly Auditorium at Notre Dame [Directions] | L 0-3 | 2:15, share bus with JVs | |
| Wed., 10/14 | JV Girls Volleyball | Notre Dame-Fairfield | Away - Sister Marion Rielly Auditorium at Notre Dame [Directions] | 3:30 p.m. | 2:15, share bus with JVs | |
| Wed., 10/14 | FR Girls Volleyball | Brookfield | Home - Auxiliary Gym [Directions] | 3:00 p.m. | ||
| Wed., 10/14 | Miscellaneous Events | PSAT Testing | - Health Classroom - Room 201 | 7:00 a.m. | 7:00 am - 3:00 pm | |
| Wed., 10/14 | Miscellaneous Events | PSAT Testing | - PHS Main Gym | 7:00 a.m. | 7:00 am - 12:00pm | |
| Wed., 10/14 | Miscellaneous Events | Athletic Trainer | 3:00 p.m. | 3:00 - 6:00 pm | ||
| Wed., 10/14 | Miscellaneous Events | Pop Warner Cheerleading | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30 pm | |
| Wed., 10/14 | Miscellaneous Events | Stby PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:45 pm | |
| Thu., 10/15 | V Boys Soccer | Stratford | Home - PHS Soccer Field [Directions] | W 5-2 | ||
| Thu., 10/15 | JV Boys Soccer | Stratford | Home - Long Meadow Elementary School [Directions] | 4:30 p.m. | 3:30, one way bus to LMES | |
| Thu., 10/15 | V Girls Soccer | Stratford | Away - Penders Field [Directions] | W 4-1 | 5:00 pm | |
| Thu., 10/15 | JV Girls Soccer | Stratford | Away - Penders Field [Directions] | W 6-1 | 3:30 pm | |
| Thu., 10/15 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 2:15 p.m. | ||
| Thu., 10/15 | Miscellaneous Events | Athletic Trainer | 3:00 p.m. | 3:00 - 9:00 pm | ||
| Thu., 10/15 | Miscellaneous Events | Stby PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:45 pm | |
| Thu., 10/15 | Miscellaneous Events | Stby Park & Rec Open Basketball Gym | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 10/16 | FR Boys Soccer | Newtown | Away - Newtown HS Practice Field [Directions] | 3:45 p.m. | 2:45 pm | |
| Fri., 10/16 | V Field Hockey | Newtown | Away - Blue and Gold Stadium [Directions] | W 3-1 | 3:00, share bus with JVs | |
| Fri., 10/16 | JV Field Hockey | Newtown | Away - Blue and Gold Stadium [Directions] | 5:45 p.m. | 3:00, share bus with varsity | |
| Fri., 10/16 | FR Girls Soccer | Newtown | Home - PHS Soccer Field [Directions] | 3:45 p.m. | ||
| Fri., 10/16 | V Girls Volleyball | New Fairfield | Home - PHS Main Gym [Directions] | W 3-0 | ||
| Fri., 10/16 | JV Girls Volleyball | New Fairfield | Home - PHS Main Gym [Directions] | 4:30 p.m. | ||
| Fri., 10/16 | FR Girls Volleyball | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | 4:00 p.m. | 2:30 pm | |
| Fri., 10/16 | Miscellaneous Events | Athletic Trainer | 3:00 p.m. | 3:00 - 8:00 pm | ||
| Fri., 10/16 | Miscellaneous Events | Stby PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:45 pm | |
| Fri., 10/16 | Miscellaneous Events | Pop Warner Cheerleading | - Auxiliary Gym | 6:30 p.m. | 6:30 - 9:00 pm | |
| Sat., 10/17 | V Boys Soccer | Immaculate | Home - PHS Soccer Field [Directions] | W 5-2 | ||
| Sat., 10/17 | FR Boys Soccer | Naugatuck | Home - PHS Soccer Field [Directions] | 9:00 a.m. | ||
| Sat., 10/17 | V Girls Soccer | Joel Barlow | Away - Field I (Stadium) [Directions] | L 0-1 | 5:00 pm | |
| Sat., 10/17 | JV Girls Soccer | Joel Barlow | Away - Field I (Stadium) [Directions] | W 1-0 | 3:30 pm | |
| Sat., 10/17 | FR Girls Soccer | Naugatuck | Away - Naugatuck HS [Directions] | 9:00 a.m. | 8:00 am | |
| Sat., 10/17 | Miscellaneous Events | Athletic Trainer | 9:00 a.m. | 9:00 - 10:30 pm | ||
| Mon., 10/19 | FR Field Hockey | Newtown | Home - PHS Baseball Field [Directions] | 4:30 p.m. | ||
| Mon., 10/19 | V Girls Volleyball | New Milford | Away - New Milford HS [Directions] | W 3-0 | 2:15, share bus with JVs | |
| Mon., 10/19 | JV Girls Volleyball | New Milford | Away - New Milford HS [Directions] | 3:30 p.m. | 2:15 pm, share bus with Varsity | |
| Mon., 10/19 | Miscellaneous Events | Athletic Trainer | 3:00 p.m. | 3:00 - 9:00 pm | ||
| Mon., 10/19 | Miscellaneous Events | Pop Warner Cheerleading | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30 pm | |
| Mon., 10/19 | Miscellaneous Events | Stby PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:45 pm | |
| Mon., 10/19 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:15 p.m. | 8:15 - 10:00 pm | |
| Tue., 10/20 | V Boys Soccer | New Fairfield | Home - Sports Complex & Track [Directions] | L 2-1 | $5 Adults, $3 Students | |
| Tue., 10/20 | JV Boys Soccer | New Fairfield | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Tue., 10/20 | V Field Hockey | Brookfield | Away - BHS Stadium Field [Directions] | W 1-0 | 2:15, share bus with JVs | |
| Tue., 10/20 | JV Field Hockey | Brookfield | Away - BHS Back Turf [Directions] | 5:30 p.m. | 2:15, share bus with varsity | |
| Tue., 10/20 | V Girls Soccer | New Fairfield | Away - Rebel Turf [Directions] | W 4-1 | 2:30 pm, share bus with JVs | |
| Tue., 10/20 | JV Girls Soccer | New Fairfield | Away - NFHS Komlo Field [Directions] | W 3-2 | 2:30 pm, share bus with varsity | |
| Tue., 10/20 | V Girls Swimming and Diving | Stratford | Away - Flood MS Pool [Directions] | Pomperaug 94- Stratford 68 | 2:15 pm | |
| Tue., 10/20 | FR Girls Volleyball | Immaculate | Away [Directions] | 6:00 p.m. | 4:30 pm | |
| Tue., 10/20 | Miscellaneous Events | Athletic Trainer | 3:00 p.m. | 3:00 - 9:00 pm | ||
| Tue., 10/20 | Miscellaneous Events | Stby PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:45 pm | |
| Tue., 10/20 | Miscellaneous Events | Stby Park & Rec Youth Basketball | - PHS Main Gym | 7:30 p.m. | 7:30 - 9:30 pm | |
| Tue., 10/20 | Miscellaneous Events | Stby Park & Rec Open Basketball Gym | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 10/21 | V Boys Cross Country | SWC Championships | Away [Directions] | 3:30 p.m. | 1:45 pm | boys jv @ 4:30 |
| Wed., 10/21 | V Girls Cross Country | SWC Championships | Away [Directions] | 4:00 p.m. | 1:45 pm | girls jv @ 5:00 pm |
| Wed., 10/21 | V Girls Volleyball | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | W 3-0 | 2:15, share bus with JVs | |
| Wed., 10/21 | JV Girls Volleyball | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | 3:30 p.m. | 2:15, share bus with varsity | |
| Wed., 10/21 | FR Girls Volleyball | Newtown | Home - Auxiliary Gym [Directions] | 3:30 p.m. | ||
| Wed., 10/21 | Miscellaneous Events | Athletic Trainer | 3:00 p.m. | 3:00 - 6:00 pm | ||
| Wed., 10/21 | Miscellaneous Events | Pop Warner Cheerleading | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30 pm | |
| Wed., 10/21 | Miscellaneous Events | Stby PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:45 pm | |
| Wed., 10/21 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:15 p.m. | 8:15 - 10:00 pm | |
| Thu., 10/22 | FR Football | New Milford | Away - New Milford HS [Directions] | 4:00 p.m. | 2:30 pm | |
| Thu., 10/22 | V Boys Soccer | Bunnell | Home - Sports Complex & Track [Directions] | W 4-0 | $5 Adults, $3 Students | |
| Thu., 10/22 | JV Boys Soccer | Bunnell | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Thu., 10/22 | FR Field Hockey | New Milford | Away - New Milford HS [Directions] | 4:30 p.m. | 3:15 pm | |
| Thu., 10/22 | V Girls Soccer | Bunnell | Away - Bunnell Turf Field [Directions] | W 3-1 | 5:15 pm | |
| Thu., 10/22 | JV Girls Soccer | Bunnell | Away - Bunnell Turf Field [Directions] | 5:00 p.m. | 3:15 pm | |
| Thu., 10/22 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 2:15 p.m. | ||
| Thu., 10/22 | Miscellaneous Events | Athletic Trainer | 3:00 p.m. | 3:00 - 9:00 pm | ||
| Thu., 10/22 | Miscellaneous Events | Stby PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:45 pm | |
| Thu., 10/22 | Miscellaneous Events | Stby Park & Rec Youth Basketball | - PHS Main Gym | 7:30 p.m. | 7:30 - 9:30 pm | |
| Thu., 10/22 | Miscellaneous Events | Stby Park & Rec Open Basketball Gym | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 10/23 | V Football | New Milford | Home - Sports Complex & Track [Directions] | L 14-45 | $5 Adults, $3 Students | |
| Fri., 10/23 | V Field Hockey | Watertown | Away - John J. Mills Complex @ Watertown HS [Directions] | W 2-1 | 2:30, share bus with JVs | |
| Fri., 10/23 | JV Field Hockey | Watertown | Away - John J. Mills Complex @ Watertown HS [Directions] | 3:45 p.m. | 2:30, share bus with varsity | |
| Fri., 10/23 | V Girls Volleyball | Brookfield | Away - BHS Big Gym [Directions] | L 3-2 | 4:00, share bus with JVs | |
| Fri., 10/23 | JV Girls Volleyball | Brookfield | Away - BHS Big Gym [Directions] | 5:30 p.m. | 4:00, share bus with varsity | |
| Fri., 10/23 | FR Girls Volleyball | SWC Freshmen Jamboree | Away | 3:30 p.m. | 2:15 pm | @ Masuk High School |
| Fri., 10/23 | Miscellaneous Events | Freshmen Student Council | - Health Classroom - Room 201 | 2:15 p.m. | 2:15 - 3:00 | |
| Fri., 10/23 | Miscellaneous Events | Athletic Trainer | 4:00 p.m. | 4:00 - 9:30 pm | ||
| Fri., 10/23 | Miscellaneous Events | Stby PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:45 pm | |
| Fri., 10/23 | Miscellaneous Events | Pop Warner Cheerleading | - Auxiliary Gym | 6:30 p.m. | 6:30 - 9:00 pm | |
| Sat., 10/24 | JV Football | New Milford | Away - New Milford HS [Directions] | 10:00 a.m. | 8:30 am | |
| Sat., 10/24 | FR Field Hockey | Joel Barlow | Away - Field I (Stadium) [Directions] | 9:00 a.m. | 7:30 am | |
| Sat., 10/24 | FR Girls Soccer | Amity | Home - PHS Soccer Field [Directions] | 10:00 a.m. | ||
| Sat., 10/24 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 11:00 a.m. | 11:00 - 12:45 pm | |
| Sat., 10/24 | Miscellaneous Events | Run for the Rams Road Race | 8:00 a.m. | |||
| Sat., 10/24 | Miscellaneous Events | Pop Warner Cheerleaders Practice | - Auxiliary Gym | 1:00 p.m. | 1:00 - 3:00 pm | |
| Sat., 10/24 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sat., 10/24 | Miscellaneous Events | Gunnery Field Hockey Game | - Sports Complex & Track | 2:00 p.m. | 2:00 - 4:30 pm | |
| Sat., 10/24 | Miscellaneous Events | Basketball Clinic | - Auxiliary Gym | 5:00 p.m. | 5:00 to 8:00 pm | |
| Sat., 10/24 | Miscellaneous Events | Basketball Clinic | - PHS Main Gym | 5:00 p.m. | 5:00 to 8:00 pm | |
| Sun., 10/25 | V Girls Soccer | Notre Dame-Fairfield | Home - Sports Complex & Track [Directions] | L 0-1 | ||
| Sun., 10/25 | Miscellaneous Events | Boys Basketball Clinic | - Auxiliary Gym | 9:00 a.m. | 8:30 am set up 9:00 - 12:00 Clinic | |
| Sun., 10/25 | Miscellaneous Events | Boys Basketball Clinic | - PHS Main Gym | 9:00 a.m. | 8:30 am set up 9:00 - 12:00 Clinic | |
| Sun., 10/25 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 10/25 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 to 4:00 pm | |
| Mon., 10/26 | FR Field Hockey | Masuk | Home - PHS Baseball Field [Directions] | 4:30 p.m. | ||
| Mon., 10/26 | V Girls Volleyball | New Fairfield | Away - NFHS Gym [Directions] | W 3-0 | 3:00, share bus with JVs | Non-league game |
| Mon., 10/26 | JV Girls Volleyball | New Fairfield | Away - NFHS Gym [Directions] | 4:30 p.m. | 3:00 pm, share bus with varsity | |
| Mon., 10/26 | FR Girls Volleyball | Shelton | Away - Shelton HS Gym [Directions] | 3:30 p.m. | 2:15 pm | |
| Mon., 10/26 | Miscellaneous Events | Athletic Trainer | 3:00 p.m. | 3:00 - 6:00 pm | ||
| Mon., 10/26 | Miscellaneous Events | Pop Warner Cheerleading | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30 pm | |
| Mon., 10/26 | Miscellaneous Events | Stby PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:45 pm | |
| Mon., 10/26 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:15 p.m. | 8:15 - 10:00 pm | |
| Tue., 10/27 | V Boys Soccer | New Milford | Away - New Milford HS [Directions] | W 2-1 | 4:15 pm | Non-league game |
| Tue., 10/27 | JV Boys Soccer | New Milford | Away - New Milford HS [Directions] | 4:00 p.m. | 2:30 pm | |
| Tue., 10/27 | JV Girls Soccer | Newtown | Away - Treadwell Town Park [Directions] | 3:45 p.m. | 2:45 pm | |
| Tue., 10/27 | V Girls Swimming and Diving | Immaculate | Away - The Dive Shop/Brookfield [Directions] | 7:00 p.m. | 5:15 pm | |
| Tue., 10/27 | Miscellaneous Events | Athletic Trainer | 3:00 p.m. | 3:00 - 6:00 pm | ||
| Tue., 10/27 | Miscellaneous Events | Stby PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:45 pm | |
| Tue., 10/27 | Miscellaneous Events | Stby Park & Rec Youth Basketball | - PHS Main Gym | 7:30 p.m. | 7:30 - 9:30 pm | |
| Tue., 10/27 | Miscellaneous Events | Stby Park & Rec Open Basketball Gym | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 10/28 | Miscellaneous Events | Red Cross Blood Drive | - Auxiliary Gym | 6:00 a.m. | 6:00 am - 2:30 pm | |
| Wed., 10/28 | Miscellaneous Events | Athletic Trainer | 3:00 p.m. | 3:00 - 6:00 pm | ||
| Wed., 10/28 | Miscellaneous Events | Pop Warner Cheerleading | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30 pm | |
| Wed., 10/28 | Miscellaneous Events | Stby PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:45 pm | |
| Wed., 10/28 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:15 p.m. | 8:15 - 10:00 pm | |
| Thu., 10/29 | V Boys Cross Country | The Freshmen Race | Away | 4:00 p.m. | 2:30, share bus with girls CC | Tarrywile park in Danbury |
| Thu., 10/29 | FR Football | Masuk | Away - Benedict Stadium Field @ Masuk HS [Directions] | 4:00 p.m. | 2:30 pm | |
| Thu., 10/29 | V Girls Cross Country | The Freshmen Race | Away | 4:00 p.m. | 2:30, Share bus with boys CC | Tarrywile park in Danbury |
| Thu., 10/29 | V Field Hockey | Lewis Mills | Home - Sports Complex & Track [Directions] | L 0-1 | ||
| Thu., 10/29 | JV Field Hockey | Lewis Mills | Home - Sports Complex & Track [Directions] | 4:30 p.m. | ||
| Thu., 10/29 | FR Field Hockey | Immaculate | Away - Mustang Valley [Directions] | Cancelled | ||
| Thu., 10/29 | V Girls Swimming and Diving | New Milford | Home - PHS Pool [Directions] | 4:00 p.m. | ||
| Thu., 10/29 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 2:15 p.m. | ||
| Thu., 10/29 | Miscellaneous Events | Athletic Trainer | 3:00 p.m. | 3:00 - 7:00 pm | ||
| Thu., 10/29 | Miscellaneous Events | Stby PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:45 pm | |
| Thu., 10/29 | Miscellaneous Events | Stby Park & Rec Youth Basketball | - PHS Main Gym | 7:30 p.m. | 7:30 - 9:30 pm | |
| Thu., 10/29 | Miscellaneous Events | Stby Park & Rec Open Basketball Gym | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 10/30 | V Football | Masuk | Home - Sports Complex & Track [Directions] | L 17-26 | $5 Adults, $3 Students | |
| Fri., 10/30 | V Boys Soccer | SWC Quarter-Finals | Home - Sports Complex & Track [Directions] | Cancelled | $8 Adults, $5 Students | |
| Fri., 10/30 | V Boys Soccer | New Milford | Away - New Milford HS [Directions] | 3:00 p.m. | 1:30 pm | SWC Quarter Final Game, $8 Adults $5 Students |
| Fri., 10/30 | V Field Hockey | SWC Quarter-Finals | Away - Sports Complex & Track | 5:00 p.m. | 3:00 pm | vs. New Milford @ Barlow. $8 Adults, $5 Students |
| Fri., 10/30 | V Girls Soccer | Immaculate | Away - Sports Complex & Track [Directions] | L 0-1 | 1:45 pm | SWC Tournament Game, $8 Adults, $5 Students |
| Fri., 10/30 | V Girls Volleyball | Brookfield (Scrim.) | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 10/30 | Miscellaneous Events | Freshmen Student Council | - Health Classroom - Room 201 | 2:30 p.m. | 2:30 - 3:00 pm | |
| Fri., 10/30 | Miscellaneous Events | Athletic Trainer | 3:00 p.m. | 3:00 - 9:30 pm | ||
| Fri., 10/30 | Miscellaneous Events | Stby PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:45 pm | |
| Fri., 10/30 | Miscellaneous Events | Pop Warner Cheerleading | - Auxiliary Gym | 6:30 p.m. | 6:30 - 9:00 pm | |
| Sat., 10/31 | V Boys Cross Country | CIAC Class Meet | Away | 9:50 a.m. | 6:30 am, share bus with girls cc | |
| Sat., 10/31 | JV Football | Masuk | Away - Benedict Stadium Field @ Masuk HS [Directions] | 10:00 a.m. | 8:30 am | |
| Sat., 10/31 | V Girls Cross Country | CIAC Class Meet | Away | 9:15 a.m. | 6:30 am, share bus with boys cc | |
| Sat., 10/31 | Miscellaneous Events | Pop Warner Cheerleading | - Auxiliary Gym | 11:00 a.m. | 11:00 am to 1:00 pm | |
| Sat., 10/31 | Miscellaneous Events | Pop Warner Cheerleading Practice | - Auxiliary Gym | 11:00 a.m. | 11:00 - 1:00 pm | |
| Sat., 10/31 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sat., 10/31 | School Holidays and Closings | Halloween | ||||
| Sun., 11/1 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 11/1 | Miscellaneous Events | Pop Warner Football | - Sports Complex & Track | 4:00 p.m. | ||
| Mon., 11/2 | V Boys Soccer | SWC Semi-Finals | Away [Directions] | Cancelled | $8 Adults, $5 Students | |
| Mon., 11/2 | V Field Hockey | SWC Semi-Finals | Away [Directions] | 7:30 p.m. | 5:30 pm | Adults $8, Students $5 |
| Mon., 11/2 | V Girls Volleyball | SWC Quarter-Finals | Away [Directions] | 5:00 p.m. | 3:30 pm, $8 Adults, $5 Students | |
| Mon., 11/2 | Miscellaneous Events | Band Practice | - Auxiliary Gym | 2:15 p.m. | 2:15 to 3:30 | |
| Mon., 11/2 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 3:00 p.m. | 3:00 - 7:00 pm | |
| Mon., 11/2 | Miscellaneous Events | CPR and First Aid Class For Coaches | - Health Classroom - Room 201 | 5:00 p.m. | ||
| Mon., 11/2 | Miscellaneous Events | Pop Warner Cheerleading | - Auxiliary Gym | 5:30 p.m. | 5:30 - 8:00 pm | |
| Mon., 11/2 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Mon., 11/2 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 8:15 p.m. | 8:15 - 10:00 pm | |
| Mon., 11/2 | Miscellaneous Events | Mdby Park & Rec Basketball Over 30 | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 11/3 | V Girls Soccer | SWC Semi-Finals | Away [Directions] | Cancelled | ||
| Tue., 11/3 | V Girls Volleyball | SWC Semi-Finals | Home - PHS Main Gym [Directions] | 5:00 p.m. | Two games - 5:00 and 7:00 pm | |
| Tue., 11/3 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 3:00 p.m. | 3:00 - 9:00 pm | |
| Tue., 11/3 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Tue., 11/3 | Miscellaneous Events | Stby Park & Rec Open Basketball Gym | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 11/4 | V Boys Soccer | Watertown (Scrim.) | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Wed., 11/4 | V Boys Soccer | SWC Championship Game | Away | Cancelled | $10 Adults, $5 Students | |
| Wed., 11/4 | V Field Hockey | Amity (Scrim.) | Home - Sports Complex & Track [Directions] | 3:00 p.m. | ||
| Wed., 11/4 | V Girls Swimming and Diving | SWC Diving Championships | Away [Directions] | 5:30 p.m. | 2:45 pm | @ New Fairfield, $10 Adults, $5 Students |
| Wed., 11/4 | Miscellaneous Events | Band Practice | - Auxiliary Gym | 2:15 p.m. | 2:15 to 3:30 | |
| Wed., 11/4 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 3:00 p.m. | 3:00 - 5:00 pm | |
| Wed., 11/4 | Miscellaneous Events | Pop Warner Cheerleading | - Auxiliary Gym | 5:30 p.m. | 5:30 - 8:00 pm | |
| Wed., 11/4 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Wed., 11/4 | Miscellaneous Events | Mdby Park & Rec Basketball | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Wed., 11/4 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 8:15 p.m. | 8:15 - 10:00 pm | |
| Thu., 11/5 | FR Football | Bunnell | Away - Bunnell Turf Field [Directions] | 6:00 p.m. | 4:00 pm | |
| Thu., 11/5 | V Girls Soccer | Bunnell (Scrim.) | Home - Sports Complex & Track [Directions] | 6:30 p.m. | ||
| Thu., 11/5 | V Girls Volleyball | Naugatuck (Scrim.) | Home - PHS Main Gym [Directions] | 3:15 p.m. | ||
| Thu., 11/5 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 2:15 p.m. | ||
| Thu., 11/5 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 3:00 p.m. | 3:00 - 5:00 pm | |
| Thu., 11/5 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Thu., 11/5 | Miscellaneous Events | Stby Park & Rec Youth Basketball | - PHS Main Gym | 7:30 p.m. | 7:30 - 9:30 pm | |
| Thu., 11/5 | Miscellaneous Events | Stby Park & Rec Open Basketball Gym | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 11/6 | V Boys Cross Country | CIAC State Open | Away | 2:45 p.m. | 11:30 am, share bus with girls cc | |
| Fri., 11/6 | V Football | Bunnell | Home - Sports Complex & Track [Directions] | L 30-33 | $5 Adults, $3 Students | |
| Fri., 11/6 | V Girls Cross Country | CIAC State Open | Away | 2:00 p.m. | 11:30 am, share bus with boys cc | |
| Fri., 11/6 | Miscellaneous Events | Drumline Practice | - PHS Main Gym | 11:30 a.m. | ||
| Fri., 11/6 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 5:00 p.m. | 5:00 - 10:00 pm | |
| Fri., 11/6 | Miscellaneous Events | Pop Warner Cheerleading | - Auxiliary Gym | 5:30 p.m. | 5:30 - 8:00 pm | |
| Fri., 11/6 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 9:00 pm | |
| Fri., 11/6 | Miscellaneous Events | Homecoming Dance | - PHS Main Gym | 6:30 p.m. | Dance Begins: 8:00 pm Ends: 11:00 pm | |
| Sat., 11/7 | JV Football | Bunnell | Away - Bunnell Turf Field [Directions] | 3:30 p.m. | 1:30 pm | |
| Sat., 11/7 | V Girls Swimming and Diving | SWC Championship Meet | Away [Directions] | 4:00 p.m. | 12:45 pm | $10 Adults, $5 Students |
| Sat., 11/7 | Miscellaneous Events | Stby Park & Rec Youth BB Travel Practice | - PHS Main Gym | 11:30 a.m. | 11:30 - 9:00 pm | |
| Sat., 11/7 | Miscellaneous Events | Turkey Tumble Gymnastics | - PHS Main Gym | 6:00 a.m. | 6:00 am - 8:00 pm | |
| Sat., 11/7 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 to 4:00 pm | |
| Sat., 11/7 | School Holidays and Closings | Junior Ring Dance | ||||
| Sun., 11/8 | Miscellaneous Events | Turkey Tumble Gymnastics | - PHS Main Gym | 6:00 a.m. | 6:00 am - 8:00 pm | |
| Sun., 11/8 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 to 4:00 pm | |
| Mon., 11/9 | V Girls Soccer | Ledyard | Away - Blonders Park [Directions] | W 3-1 | 1:30 pm | |
| Mon., 11/9 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 3:00 p.m. | 3:00 - 7:00 pm | |
| Mon., 11/9 | Miscellaneous Events | Pop Warner Cheerleading | - Auxiliary Gym | 5:30 p.m. | 5:30 - 8:00 pm | |
| Mon., 11/9 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Mon., 11/9 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 8:15 p.m. | 8:15 - 10:00 pm | |
| Mon., 11/9 | Miscellaneous Events | Mdby Park & Rec Basketball Over 30 | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 11/10 | V Boys Soccer | East Lyme | Away - ELHS Turf Field [Directions] | 4:00 p.m. | 1:00 pm | |
| Tue., 11/10 | V Field Hockey | Farmington | Away [Directions] | 4:00 p.m. | 1:45 pm | |
| Tue., 11/10 | V Girls Volleyball | Brien McMahon (Scrim.) | Away [Directions] | 3:45 p.m. | 2:15 pm | |
| Tue., 11/10 | Miscellaneous Events | Ultimate Frisbee Club Tournament | - PHS Soccer Field | 2:30 p.m. | 2:30 - 5:00 pm | |
| Tue., 11/10 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 3:00 p.m. | 3:00 - 7:00 pm | |
| Tue., 11/10 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Tue., 11/10 | Miscellaneous Events | Stby Park & Rec Youth Basketball | - PHS Main Gym | 7:30 p.m. | 7:30 - 9:30 pm | |
| Wed., 11/11 | V Girls Soccer | RHAM | Home - Sports Complex & Track [Directions] | W 3-1 | $8 Adults, $5 Students | |
| Wed., 11/11 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 3:00 p.m. | 3:00 - 5:00 pm | |
| Wed., 11/11 | Miscellaneous Events | Pop Warner Cheerleading | - Auxiliary Gym | 5:30 p.m. | 5:30 - 8:00 pm | |
| Wed., 11/11 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Wed., 11/11 | Miscellaneous Events | Mdby Park & Rec Basketball | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Wed., 11/11 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 8:15 p.m. | 8:15 - 10:00 pm | |
| Thu., 11/12 | FR Football | Joel Barlow | Home - Sports Complex & Track [Directions] | 4:00 p.m. | ||
| Thu., 11/12 | V Boys Soccer | Wethersfield | Away - Cottone Field at WHS [Directions] | 6:00 p.m. | 3:45 pm | $5 Adults, $3 Students |
| Thu., 11/12 | V Girls Swimming and Diving | CIAC Class L Diving Trials/Finals | Away - Middletown HS [Directions] | 5:30 p.m. | ||
| Thu., 11/12 | V Girls Volleyball | Guilford | Away - Main Gym at GHS [Directions] | 6:00 p.m. | 3:30 pm | |
| Thu., 11/12 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 3:00 p.m. | 3:00 - 7:00 pm | |
| Thu., 11/12 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Thu., 11/12 | Miscellaneous Events | Stby Park & Rec Youth Basketball | - PHS Main Gym | 7:30 p.m. | 7:30 - 9:30 pm | |
| Thu., 11/12 | Miscellaneous Events | Stby Park & Rec Open Basketball Gym | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 11/13 | V Girls Soccer | East Lyme | Away - ELHS Turf Field [Directions] | W 3-2 | 3:15 | |
| Fri., 11/13 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 3:00 p.m. | 3:00 - 5:00 pm | |
| Fri., 11/13 | Miscellaneous Events | Pop Warner Cheerleading | - PHS Main Gym | 5:30 p.m. | 5:30 - 8:00 pm | |
| Fri., 11/13 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 9:00 pm | |
| Fri., 11/13 | Miscellaneous Events | Pomperaug Youth Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 9:30 pm | |
| Sat., 11/14 | V Football | Joel Barlow | Away - Field I (Stadium) [Directions] | L 8-40 | 10:00 am, 2 buses | |
| Sat., 11/14 | V Girls Swimming and Diving | CIAC Class L Qualifying | Away - ast Hartford [Directions] | 6:00 p.m. | 2:30 pm | |
| Sat., 11/14 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 to 4:00 pm | |
| Sat., 11/14 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 11/15 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 to 4:00 pm | |
| Sun., 11/15 | Miscellaneous Events | Southbury Park and Rec Basketball | - Auxiliary Gym | 1:00to9:30 p.m. | ||
| Mon., 11/16 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 3:00 p.m. | 3:00 - 5:00 pm | |
| Mon., 11/16 | Miscellaneous Events | Pop Warner Cheerleading | - Auxiliary Gym | 5:30 p.m. | 5:30 - 8:00 pm | |
| Mon., 11/16 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Mon., 11/16 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 8:15 p.m. | 8:15 - 10:00 pm | |
| Mon., 11/16 | Miscellaneous Events | Mdby Park & Rec Basketball Over 30 | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 11/17 | V Girls Soccer | CIAC Semi Final | Away | 6:30 p.m. | 5:00 pm | @ Newtown High School, $8 Adults, $5 Students |
| Tue., 11/17 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 3:00 p.m. | 3:00 - 5:00 pm | |
| Tue., 11/17 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Tue., 11/17 | Miscellaneous Events | Stby Park & Rec Youth Basketball | - PHS Main Gym | 7:30 p.m. | 7:30 - 9:30 pm | |
| Tue., 11/17 | Miscellaneous Events | Stby Park & Rec Open Basketball Gym | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 11/18 | V Girls Swimming and Diving | CIAC Class L Finals | Away - Wesleyan Univ. [Directions] | 7:00 p.m. | 4:00 pm | |
| Wed., 11/18 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 3:00 p.m. | 3:00 - 5:00 pm | |
| Wed., 11/18 | Miscellaneous Events | Pop Warner Cheerleading | - Auxiliary Gym | 5:30 p.m. | 5:30 - 8:00 pm | |
| Wed., 11/18 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Wed., 11/18 | Miscellaneous Events | Mdby Park & Rec Basketball | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Wed., 11/18 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 8:15 p.m. | 8:15 - 10:00 pm | |
| Thu., 11/19 | FR Football | Notre Dame-Fairfield | Home - Sports Complex & Track [Directions] | 4:00 p.m. | ||
| Thu., 11/19 | V Girls Swimming and Diving | CIAC Open Diving | Away - Middletown HS [Directions] | 5:30 p.m. | No bus | |
| Thu., 11/19 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 3:00 p.m. | 3:00 - 7:00 pm | |
| Thu., 11/19 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Thu., 11/19 | Miscellaneous Events | Stby Park & Rec Youth Basketball | - PHS Main Gym | 7:30 p.m. | 7:30 - 9:30 pm | |
| Thu., 11/19 | Miscellaneous Events | Southbury Soocer Club Game | - Sports Complex & Track | 8:00 p.m. | 8:00 - 9:00 pm | |
| Thu., 11/19 | Miscellaneous Events | Stby Park & Rec Open Basketball Gym | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 11/20 | Miscellaneous Events | Speedball | - PHS Main Gym | 2:15 p.m. | 2:15 to 3:00 pm | |
| Fri., 11/20 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 3:00 p.m. | 3:00 - 5:00 pm | |
| Fri., 11/20 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 9:00 pm | |
| Fri., 11/20 | Miscellaneous Events | Mdby Park & Rec Basketball | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Fri., 11/20 | Miscellaneous Events | Pomperaug Youth Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 9:30 pm | |
| Sat., 11/21 | V Girls Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 12:00 p.m. | 8:30 am | |
| Sat., 11/21 | Miscellaneous Events | Stby Park & Rec Youth Basketball Travel Practice | - PHS Main Gym | 12:00 p.m. | 11:30 enter - 12:00 - 9:00 pm | |
| Sat., 11/21 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 to 4:00 pm | |
| Sat., 11/21 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 11/22 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 to 4:00 pm | |
| Mon., 11/23 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 3:00 p.m. | 3:00 - 5:00 pm | |
| Mon., 11/23 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Mon., 11/23 | Miscellaneous Events | Southbury Park & Rec Open Swim | - PHS Pool | 8:15 p.m. | 8:15 - 10:00 pm | |
| Mon., 11/23 | Miscellaneous Events | Mdby Park & Rec Basketball Over 30 | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 11/24 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 3:00 p.m. | 3:00 - 5:00 pm | |
| Tue., 11/24 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Tue., 11/24 | Miscellaneous Events | Southbury Park and Rec Basketball | - PHS Main Gym | 7:30 p.m. | 7:30 to 9:00 | |
| Tue., 11/24 | Miscellaneous Events | Stby Park & Rec Open Basketball Gym | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 11/25 | School Holidays and Closings | Thanksgiving Eve - Half Day | ||||
| Thu., 11/26 | V Football | Notre Dame-Fairfield | Away - McCarty Stadium at Notre Dame [Directions] | L 27-34 | 7:30 am, 2 buses | |
| Thu., 11/26 | School Holidays and Closings | Thanksgiving Day | ||||
| Fri., 11/27 | School Holidays and Closings | Thanksgiving Recess - No School | ||||
| Mon., 11/30 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 3:00 p.m. | 3:00 - 7:00 pm | |
| Mon., 11/30 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Mon., 11/30 | Miscellaneous Events | Mdby Park & Rec Basketball Over 30 | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 12/1 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Tue., 12/1 | Miscellaneous Events | Pomp Youth Wrestling | - Wrestling Room | 6:30 p.m. | 6:30 - 8:30 pm | |
| Tue., 12/1 | Miscellaneous Events | Stby Park & Rec Open Basketball Gym | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 12/2 | Miscellaneous Events | Pop Warner Cheerleading | - Auxiliary Gym | 5:30 p.m. | 5:30 - 8:00 pm | |
| Wed., 12/2 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Wed., 12/2 | Miscellaneous Events | Mdby Park & Rec Basketball | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Thu., 12/3 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Thu., 12/3 | Miscellaneous Events | Pomp Youth Wrestling | - Wrestling Room | 6:30 p.m. | 6:30 - 8:30 pm | |
| Thu., 12/3 | Miscellaneous Events | Stby Park & Rec Open Basketball Gym | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 12/4 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Fri., 12/4 | Miscellaneous Events | Pomp Youth Wrestling | - Wrestling Room | 6:30 p.m. | 6:30 - 8:30 pm | |
| Fri., 12/4 | Miscellaneous Events | Mdby Park & Rec Basketball | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Sat., 12/5 | V Girls Basketball | Trumbull (Scrim.) | Home - PHS Main Gym [Directions] | 1:00 p.m. | Tri-scrimmage vs Northwest and Trumbull | |
| Sat., 12/5 | V Girls Basketball | Northwest Catholic (Scrim.) | Home - PHS Main Gym [Directions] | 1:00 p.m. | Tri-scrimmage vs Northwest and Trumbull | |
| Sat., 12/5 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 12/6 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Mon., 12/7 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Mon., 12/7 | Miscellaneous Events | Mdby Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | ||
| Tue., 12/8 | V Boys Basketball | Wilby (Scrim.) | Home - PHS Main Gym [Directions] | 6:30 p.m. | ||
| Tue., 12/8 | V Girls Basketball | Farmington (Scrim.) | Away [Directions] | 5:00 p.m. | 4:00 pm | Tri scrimmage at Thomaston, also vs. Farmington |
| Tue., 12/8 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Tue., 12/8 | Miscellaneous Events | Pomp Youth Wrestling | - Wrestling Room | 6:30 p.m. | 6:30 - 8:30 pm | |
| Tue., 12/8 | Miscellaneous Events | Stby Park & Rec Open Basketball Gym | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 12/9 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Wed., 12/9 | Miscellaneous Events | Stby Park & Rec Youth BB Games | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:30 pm | |
| Wed., 12/9 | Miscellaneous Events | Mdby Park & Rec Basketball | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Thu., 12/10 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Thu., 12/10 | Miscellaneous Events | Pomp Youth Wrestling | - Wrestling Room | 6:30 p.m. | 6:30 - 8:30 pm | |
| Thu., 12/10 | Miscellaneous Events | Stby Park & Rec Youth BB Games | - Auxiliary Gym | 7:00 p.m. | 7:00 - 8:00 pm | |
| Thu., 12/10 | Miscellaneous Events | Stby Park & Rec Open Basketball Gym | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 12/11 | V Boys Basketball | Nonnewaug (Scrim.) | Away - Nonnewaug HS Gym [Directions] | 3:30 p.m. | 2:15 pm | |
| Fri., 12/11 | V Girls Basketball | Career Magnet (Scrim.) | Away - Career HS [Directions] | 5:00 p.m. | 3:30 pm | |
| Fri., 12/11 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Fri., 12/11 | Miscellaneous Events | Pomp Youth Wrestling | - Wrestling Room | 6:30 p.m. | 6:30 - 8:30 pm | |
| Fri., 12/11 | Miscellaneous Events | Mdby Park & Rec Basketball | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Sat., 12/12 | V Boys Basketball | Wolcott (Scrim.) | Away [Directions] | 10:00 p.m. | 9:00 am | |
| Sat., 12/12 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 12/13 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Mon., 12/14 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Mon., 12/14 | Miscellaneous Events | Mdby Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | ||
| Tue., 12/15 | V Girls Basketball | St. Joseph | Away - Newtown HS [Directions] | W 41-34 | 4:00 pm | @ Newtown High School, vs. St. Joseph's HS |
| Tue., 12/15 | FR Girls Basketball | Masuk | Home - PHS Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 12/15 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Tue., 12/15 | Miscellaneous Events | Pomp Youth Wrestling | - Wrestling Room | 6:30 p.m. | 6:30 - 8:30 pm | |
| Tue., 12/15 | Miscellaneous Events | Stby Park & Rec Open Basketball Gym | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 12/16 | V Boys Basketball | Holy Cross (Scrim.) | Away [Directions] | 4:15 p.m. | 3:15 pm | |
| Wed., 12/16 | V Wrestling | Newtown | Away - Newtown HS Gymnasium [Directions] | 7:00 p.m. | 5:30 pm | |
| Wed., 12/16 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Wed., 12/16 | Miscellaneous Events | Mdby Park & Rec Basketball | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Thu., 12/17 | V Girls Basketball | Danbury | Away - Newtown HS [Directions] | W 59-39 | 3:30 pm | @ Newtown HS, vs. Danbury |
| Thu., 12/17 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Thu., 12/17 | Miscellaneous Events | Pomp Youth Wrestling | - Wrestling Room | 6:30 p.m. | 6:30 - 8:30 pm | |
| Thu., 12/17 | Miscellaneous Events | Stby Park & Rec Youth Basketball | - PHS Main Gym | 7:00 p.m. | 7:00 - 8:30 pm | |
| Thu., 12/17 | Miscellaneous Events | Stby Park & Rec Open Basketball Gym | - Auxiliary Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 12/18 | FR Girls Basketball | Ridgefield | Home - PHS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 12/18 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Fri., 12/18 | Miscellaneous Events | Pomp Youth Wrestling | - Wrestling Room | 6:30 p.m. | 6:30 - 8:30 pm | |
| Fri., 12/18 | Miscellaneous Events | Mdby Park & Rec Basketball | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Sat., 12/19 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland Of Ice [Directions] | L 1-3 | ||
| Sat., 12/19 | V Boys Indoor Track | New Haven Invitational | Away | 9:00 a.m. | 7:30 am, share bus with girls Indoor Track | |
| Sat., 12/19 | V Wrestling | Pomperaug Holiday Invitational | Home - PHS Main Gym [Directions] | 9:00 a.m. | $5 Adults, $4 Students | |
| Sat., 12/19 | V Girls Indoor Track | New Haven Invitational | Away | 9:00 a.m. | 7:30 am, share bus to boys indoor track | |
| Sat., 12/19 | Miscellaneous Events | Wrestling Tournament | - Health Classroom - Room 201 | 7:00 a.m. | 7:00 am to 7:00 pm | |
| Sat., 12/19 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 12/20 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Mon., 12/21 | V Boys Basketball | Wilton | Home - PHS Main Gym [Directions] | W 71 - 58 | $5 Adults, $4 Students | |
| Mon., 12/21 | JV Boys Basketball | Wilton | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 12/21 | FR Boys Basketball | Wilton | Home - PHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 12/21 | V Boys Ice Hockey | Westhill-Stamford | Home - Taft-Mays Rink [Directions] | L 0-5 | ||
| Mon., 12/21 | V Boys Swimming and Diving | Barlow/Bethel | Away - Western CT State University - O'Neill Center [Directions] | 4:00 p.m. | 2:15 pm | |
| Mon., 12/21 | V Girls Basketball | Cromwell | Away [Directions] | L 50-48 | 3:45 pm | vs. Cromwell |
| Mon., 12/21 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Tue., 12/22 | V Girls Basketball | Hillhouse | Away [Directions] | W 53-40 | TBA | 5:00 Consolation Game, 7:00 championship game |
| Tue., 12/22 | FR Girls Basketball | Newtown | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Tue., 12/22 | V Girls Gymnastics | Nonnewaug, Joel Barlow, Foran | Home - Auxiliary Gym [Directions] | 127.4 | ||
| Tue., 12/22 | Miscellaneous Events | Lacrosse Booster Alumni Game | - Sports Complex & Track | 5:00 p.m. | 5:00 - 6:00 pm | |
| Tue., 12/22 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Tue., 12/22 | Miscellaneous Events | Pomp Youth Wrestling | - Wrestling Room | 6:30 p.m. | 6:30 - 8:30 pm | |
| Wed., 12/23 | V Boys Basketball | New Milford | Away - New Milford HS [Directions] | W 82 - 67 | 4:00 share w/jv boys bb | |
| Wed., 12/23 | JV Boys Basketball | New Milford | Away - New Milford HS [Directions] | 5:15 p.m. | 4:00, share bus with varsity | |
| Wed., 12/23 | FR Boys Basketball | New Milford | Away - New Milford HS [Directions] | 3:30 p.m. | 2:15 pm | |
| Wed., 12/23 | V Boys Ice Hockey | Trumbull | Away - Shelton Rinks [Directions] | T 5-5 | 5:30 PM | |
| Wed., 12/23 | V Boys Swimming and Diving | Alumni Meet | Home - PHS Pool [Directions] | 7:00 p.m. | ||
| Wed., 12/23 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Wed., 12/23 | Miscellaneous Events | Mdby Park & Rec Basketball | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Thu., 12/24 | School Holidays and Closings | Christmas Eve - Winter Vacation Begins | ||||
| Fri., 12/25 | School Holidays and Closings | Christmas Day | ||||
| Mon., 12/28 | V Wrestling | Frank Chaves Farmington Valley Invitational | Away [Directions] | 9:00 a.m. | 6:30 am | |
| Mon., 12/28 | V Girls Basketball | St. Paul Catholic | Away [Directions] | L 63-53 | 1:00 pm | vs. ST Paul, $6 Adult $3 Student $2 Senior citizens |
| Mon., 12/28 | School Holidays and Closings | Winter Vacation | ||||
| Tue., 12/29 | V Boys Basketball | Bristol Eastern | Away [Directions] | W 79 - 58 | 4:45 pm | vs Bristol Eastern, @ Nonnewaug |
| Tue., 12/29 | V Girls Basketball | Plainville | Away - Wood Gymnasium [Directions] | W 69-28 | TBA | 3:00 Consolation Game, 6:15 Championship Game, $6 Adult $3 Student $2 Senior citizens |
| Tue., 12/29 | FR Girls Basketball | Danbury | Home - PHS Main Gym [Directions] | 12:00 p.m. | ||
| Tue., 12/29 | School Holidays and Closings | Winter Vacation | ||||
| Wed., 12/30 | V Boys Basketball | Watertown | Away - Nonnewaug HS Gym [Directions] | W 67 - 53 | TBA | 6:00 Consolation Game, 7:30 Championship |
| Wed., 12/30 | FR Boys Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 12:00 p.m. | 10:15 am | |
| Wed., 12/30 | V Boys Ice Hockey | Wilton | Home - Taft-Mays Rink [Directions] | W 3-0 | ||
| Wed., 12/30 | V Wrestling | New Milford | Away - New Milford HS [Directions] | 6:00 p.m. | 4:15 pm | |
| Wed., 12/30 | School Holidays and Closings | Winter Vacation | ||||
| Thu., 12/31 | School Holidays and Closings | Winter Vacation | ||||
| Fri., 1/1 | School Holidays and Closings | New Years Day | ||||
| Sat., 1/2 | V Boys Indoor Track | SWC Developmental at Wilton HS | Away | 2:00 p.m. | 12:15 share bus with girls | |
| Sat., 1/2 | V Wrestling | Trumbull Tournament | Away | 9:00 a.m. | 7:00 am | |
| Sat., 1/2 | V Girls Basketball | Kolbe Cathedral | Away - Shehan Center [Directions] | W 50-38 | 4:00 pm share w/jv girls bb | Non-league game |
| Sat., 1/2 | JV Girls Basketball | Kolbe Cathedral | Away - Shehan Center [Directions] | 5:15 p.m. | 4:00, share bus with varsity | |
| Sat., 1/2 | V Girls Indoor Track | Devlopmental Meet @ Wilton | Away | 2:00 p.m. | 12:15 share bus w/boys | |
| Mon., 1/4 | V Boys Basketball | Northwestern | Away - NWR-7 Gym [Directions] | L 62 - 72 | 4:00, share bus with JVs | |
| Mon., 1/4 | JV Boys Basketball | Northwestern | Away - NWR-7 Gym [Directions] | 5:30 p.m. | 4:00, share bus with varsity | |
| Mon., 1/4 | Miscellaneous Events | PAC Swim Team | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Mon., 1/4 | Miscellaneous Events | Mdby Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 1/5 | V Boys Swimming and Diving | Bethel | Home - PHS Pool [Directions] | 4:00 p.m. | ||
| Tue., 1/5 | V Girls Basketball | Stratford | Home - PHS Main Gym [Directions] | W 55-32 | $5 Adults, $4 Students | |
| Tue., 1/5 | JV Girls Basketball | Stratford | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/5 | Miscellaneous Events | PAC Swim Team | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Tue., 1/5 | Miscellaneous Events | Pomp Youth Wrestling | - Wrestling Room | 6:30 p.m. | 6:30 - 8:30 pm | |
| Tue., 1/5 | Miscellaneous Events | Southbury Park and Rec Adult Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 to 10:00 pm | |
| Wed., 1/6 | V Boys Basketball | Bethel | Home - PHS Main Gym [Directions] | W 55 - 31 | 4:00 share w/jv boys bb | $5 Adults, $4 Students |
| Wed., 1/6 | JV Boys Basketball | Bethel | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 1/6 | FR Boys Basketball | Bethel | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Wed., 1/6 | V Boys Ice Hockey | Cheshire | Away - Wesleyan University Ice Rink [Directions] | L 1-6 | 4:45 p.m. | |
| Wed., 1/6 | V Boys Indoor Track | SWC JV Developmental Meet | Away | 3:00 p.m. | 2:15 pm | @ Danbury Sports Dome |
| Wed., 1/6 | V Wrestling | Bunnell | Home - Auxiliary Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/6 | V Girls Indoor Track | SWC JV Developmental Meet | Away | 3:00 p.m. | 2:15 pm | @Danbury Sports Dome |
| Wed., 1/6 | Miscellaneous Events | PAC Swim Team | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Thu., 1/7 | V Girls Gymnastics | Jonathan Law, Daniel Hand, Joel Barlow, Nonnewaug | Away - Jonathan Law HS Old Gym [Directions] | 110.6 | ||
| Thu., 1/7 | Miscellaneous Events | PAC Swim Team | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Thu., 1/7 | Miscellaneous Events | Pomp Youth Wrestling | - Wrestling Room | 6:30 p.m. | 6:30 - 8:30 pm | |
| Thu., 1/7 | Miscellaneous Events | Southbury Park and Rec Adult Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 to 10:00 pm | |
| Fri., 1/8 | V Boys Basketball | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | W 50 - 46 | 4:00 share w/jv boys bb | Non-league game |
| Fri., 1/8 | JV Boys Basketball | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | 5:15 p.m. | 4:00, share bus with varsity | |
| Fri., 1/8 | FR Boys Basketball | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | 3:30 p.m. | 2:15 pm | |
| Fri., 1/8 | V Wrestling | Waterford Quad | Away | 6:00 p.m. | 3:00 pm | |
| Fri., 1/8 | V Competitive Cheerleading | Immaculate | Home - PHS Main Gym [Directions] | 7:00 p.m. | ||
| Fri., 1/8 | V Girls Basketball | Immaculate | Home - PHS Main Gym [Directions] | W 63-34 | $5 Adults, $4 Students | |
| Fri., 1/8 | JV Girls Basketball | Immaculate | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/8 | FR Girls Basketball | Immaculate | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 1/8 | Miscellaneous Events | PAC Swim Team | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Fri., 1/8 | Miscellaneous Events | Pomp Youth Wrestling | - Wrestling Room | 6:30 p.m. | 6:30 - 8:30 pm | |
| Fri., 1/8 | Miscellaneous Events | Mdby Park & Rec Basketball | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Sat., 1/9 | V Boys Ice Hockey | Milford Coop | Away - Milford Ice Pavilion [Directions] | W 7-1 | ||
| Sat., 1/9 | V Boys Indoor Track | SWC Developmental Meet | Away | 9:00 a.m. | 6:45 am | @ Wesleyan University |
| Sat., 1/9 | V Girls Gymnastics | Pomperaug Invitational | Home - PHS Main Gym [Directions] | 122.2 | $5 Adults, $4 Students | |
| Sat., 1/9 | V Girls Indoor Track | SWC Developmental Meet | Away | 9:00 a.m. | 6:45 am | @ Wesleyan University |
| Sat., 1/9 | Miscellaneous Events | Stby Park & Rec Basketball | - Auxiliary Gym | 12:00 p.m. | 11:30 - 9:00 pm | |
| Sat., 1/9 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 1/10 | Miscellaneous Events | Pomperaug Youth Softball | - Auxiliary Gym | 8:00 a.m. | 8:00 - 11:00 am | |
| Sun., 1/10 | Miscellaneous Events | Stby Park & Rec Youth Basketball | - PHS Main Gym | 1:00 p.m. | 1:00 - 9:00 pm | |
| Sun., 1/10 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Mon., 1/11 | Miscellaneous Events | PAC Swim Team | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Mon., 1/11 | Miscellaneous Events | Mdby Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 1/12 | Miscellaneous Events | Freshmen Class Meeting | - Health Classroom - Room 201 | 2:15 p.m. | 2:15 - 3:00 pm | |
| Tue., 1/12 | Miscellaneous Events | PAC Swim Team | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Tue., 1/12 | Miscellaneous Events | Pomp Youth Wrestling | - Wrestling Room | 6:30 p.m. | 6:30 - 8:30 pm | |
| Tue., 1/12 | Miscellaneous Events | Pomp Softball Assoc Clinic | - Auxiliary Gym | 8:15 p.m. | 8:15 - 10:00 pm | |
| Tue., 1/12 | Miscellaneous Events | Southbury Park and Rec Adult Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 to 10:00 pm | |
| Wed., 1/13 | V Boys Basketball | Trinity Catholic | Away - Walsh Court | L 54 - 62 | 3:30, share bus with JVs | |
| Wed., 1/13 | JV Boys Basketball | Trinity Catholic | Away - Walsh Court | 5:30 p.m. | 3:30, share bus with varsity | |
| Wed., 1/13 | FR Boys Basketball | Trinity Catholic | Away - Walsh Court | 4:00 p.m. | 2:15 pm | |
| Wed., 1/13 | V Boys Indoor Track | SWC JV Developmental Meet | Away | 3:00 p.m. | 2:15 pm | @ Danbury Sports Dome |
| Wed., 1/13 | V Boys Swimming and Diving | Bunnell/Stratford | Home - PHS Pool [Directions] | 5:00 p.m. | ||
| Wed., 1/13 | V Wrestling | Stratford | Away - Needham Memorial Gymnasium [Directions] | 6:00 p.m. | 4:00 pm | |
| Wed., 1/13 | V Girls Indoor Track | SWC JV Developmental Meet | Away | 3:00 p.m. | 2:15 pm | @ Danbury Sports Dome |
| Wed., 1/13 | Miscellaneous Events | PAC Swim Team | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Wed., 1/13 | Miscellaneous Events | Mdby Park & Rec Basketball | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Thu., 1/14 | V Girls Basketball | New Milford | Home - PHS Main Gym [Directions] | W 71-19 | $5 Adults, $4 Students | |
| Thu., 1/14 | JV Girls Basketball | New Milford | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Thu., 1/14 | FR Girls Basketball | New Milford | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Thu., 1/14 | Miscellaneous Events | PAC Swim Team | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Thu., 1/14 | Miscellaneous Events | Pomp Youth Wrestling | - Wrestling Room | 6:30 p.m. | 6:30 - 8:30 pm | |
| Thu., 1/14 | Miscellaneous Events | Southbury Park and Rec Adult Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 to 10:00 pm | |
| Fri., 1/15 | V Boys Basketball | Bunnell | Home - PHS Main Gym [Directions] | W 65 - 62 | $5 Adults, $4 Students | |
| Fri., 1/15 | JV Boys Basketball | Bunnell | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/15 | FR Boys Basketball | Bunnell | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 1/15 | V Boys Swimming and Diving | Brookfield | Home - PHS Pool [Directions] | 7:00 p.m. | $5 Adults, $4 Students | |
| Fri., 1/15 | V Wrestling | JV Scrimmage Night | Home - Auxiliary Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/15 | V Competitive Cheerleading | Bunnell | Home - PHS Main Gym [Directions] | 7:00 p.m. | ||
| Fri., 1/15 | V Girls Basketball | Bunnell | Away - Bunnell [Directions] | W 70-21 | 4:00 pm share w/jv girls bb | |
| Fri., 1/15 | JV Girls Basketball | Bunnell | Away - Bunnell [Directions] | 5:15 p.m. | 4:00, share bus with varsity | |
| Fri., 1/15 | FR Girls Basketball | Bunnell | Away - Bunnell [Directions] | 3:30 p.m. | 2:15 pm | |
| Fri., 1/15 | Miscellaneous Events | PAC Swim Team | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Fri., 1/15 | Miscellaneous Events | Pomp Youth Wrestling | - Wrestling Room | 6:30 p.m. | 6:30 - 8:30 pm | |
| Fri., 1/15 | Miscellaneous Events | Mdby Park & Rec Basketball | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Sat., 1/16 | V Boys Ice Hockey | Farmington Valley | Home - Taft-Mays Rink [Directions] | L 2-4 | ||
| Sat., 1/16 | V Wrestling | Colter Abely Mid Season Classic | Away | 9:00 a.m. | 6:30 am | |
| Sat., 1/16 | V Competitive Cheerleading | Seymour Competition | Away | TBA | 8:00 am | @ Seymour Middle School |
| Sat., 1/16 | Miscellaneous Events | Stby Park & Rec Basketball | - Auxiliary Gym | 12:00 p.m. | 11:30 - 9:00 pm | |
| Sat., 1/16 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 1/17 | Miscellaneous Events | Pomperaug Youth Softball | - Auxiliary Gym | 8:00 a.m. | 8:00 - 11:00 am | |
| Sun., 1/17 | Miscellaneous Events | Stby Park & Rec Youth Basketball | - PHS Main Gym | 1:00 p.m. | 1:00 - 9:00 pm | |
| Sun., 1/17 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Mon., 1/18 | V Boys Ice Hockey | Daniel Hand | Away - Northford Ice Pavilion [Directions] | L 0-1 | ||
| Mon., 1/18 | V Boys Indoor Track | SWC Developmental Meet | Away | 9:00 a.m. | 7:00 am | @ Wesleyan University |
| Mon., 1/18 | V Girls Indoor Track | SWC Developmental Meet | Away | 9:00 a.m. | 7:00 am | @ Wesleyan University |
| Mon., 1/18 | Miscellaneous Events | Mdby Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Mon., 1/18 | School Holidays and Closings | Martin Luther King Day - No School, Inservice Day | ||||
| Tue., 1/19 | V Boys Basketball | New Fairfield | Home - PHS Main Gym [Directions] | W 57 - 39 | $5 Adults, $4 Students | |
| Tue., 1/19 | JV Boys Basketball | New Fairfield | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/19 | FR Boys Basketball | New Fairfield | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Tue., 1/19 | V Boys Swimming and Diving | Masuk | Away - Masuk Pool [Directions] | 4:00 p.m. | 2:15 pm | |
| Tue., 1/19 | V Girls Basketball | New Fairfield | Away - NFHS Gym [Directions] | L 62-49 | 4:00 pm share w/jv girls bb | |
| Tue., 1/19 | JV Girls Basketball | New Fairfield | Away - NFHS Gym [Directions] | 5:15 p.m. | 4:00, share bus with varsity | |
| Tue., 1/19 | FR Girls Basketball | New Fairfield | Away - NFHS Gym [Directions] | 3:30 p.m. | 2:15 pm | |
| Tue., 1/19 | V Girls Gymnastics | New Milford, Hamden, Newtown, Oxford | Away - New Milford [Directions] | 120.65 | ||
| Tue., 1/19 | Miscellaneous Events | PAC Swim Team | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Tue., 1/19 | Miscellaneous Events | Pomp Youth Wrestling | - Wrestling Room | 6:30 p.m. | 6:30 - 8:30 pm | |
| Tue., 1/19 | Miscellaneous Events | Pomp Softball Assoc Clinic | - Auxiliary Gym | 8:15 p.m. | 8:15 - 10:00 pm | |
| Tue., 1/19 | Miscellaneous Events | Southbury Park and Rec Adult Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 to 10:00 pm | |
| Wed., 1/20 | V Boys Ice Hockey | Masuk | Away - The Rinks at Shelton [Directions] | W 7-1 | 6:00 PM | |
| Wed., 1/20 | V Wrestling | Masuk | Home - Auxiliary Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/20 | Miscellaneous Events | PAC Swim Team | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Wed., 1/20 | Miscellaneous Events | Mdby Park & Rec Basketball | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Thu., 1/21 | Miscellaneous Events | PAC Swim Team | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Thu., 1/21 | Miscellaneous Events | Pomp Youth Wrestling | - Wrestling Room | 6:30 p.m. | 6:30 - 8:30 pm | |
| Thu., 1/21 | Miscellaneous Events | Southbury Park and Rec Adult Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 to 10:00 pm | |
| Thu., 1/21 | School Holidays and Closings | Mid-Year Exams, Early Dismissal | ||||
| Fri., 1/22 | V Boys Basketball | Brookfield | Home - PHS Main Gym [Directions] | W 84 - 61 | $5 Adults, $4 Students | |
| Fri., 1/22 | JV Boys Basketball | Brookfield | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/22 | FR Boys Basketball | Brookfield | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 1/22 | V Boys Swimming and Diving | Naugatuck | Away [Directions] | 4:00 p.m. | 2:30 pm | |
| Fri., 1/22 | V Wrestling | JV Scrimmage Night | Home - Auxiliary Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/22 | V Competitive Cheerleading | Brookfield | Home - PHS Main Gym [Directions] | 7:00 p.m. | ||
| Fri., 1/22 | V Girls Basketball | Brookfield | Away - BHS Big Gym [Directions] | W 61-37 | 3:00 pm share w/jv girls bb | |
| Fri., 1/22 | JV Girls Basketball | Brookfield | Away - BHS Big Gym [Directions] | 4:15 p.m. | 3:00, share bus with varsity | |
| Fri., 1/22 | Miscellaneous Events | PAC Swim Team | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Fri., 1/22 | Miscellaneous Events | Pomp Youth Wrestling | - Wrestling Room | 6:30 p.m. | 6:30 - 8:30 pm | |
| Fri., 1/22 | Miscellaneous Events | Mdby Park & Rec Basketball | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Fri., 1/22 | Miscellaneous Events | Kinetic Kids Gymnastics | - PHS Main Gym | 8:30 p.m. | Set-up 8:30 - 10:00 | |
| Fri., 1/22 | School Holidays and Closings | Mid-Year Exams, Early Dismissal | ||||
| Sat., 1/23 | V Wrestling | Rodney Smith Invitational | Away [Directions] | Cancelled | ||
| Sat., 1/23 | Miscellaneous Events | Kinetic Kids Gymnastics | - PHS Main Gym | 7:00 a.m. | 7:00 am - 10:00 pm | |
| Sat., 1/23 | Miscellaneous Events | Stby Park & Rec Basketball | - Auxiliary Gym | 12:00 p.m. | 11:30 - 9:00 pm | |
| Sat., 1/23 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 1/24 | Miscellaneous Events | Kinetic Kids Gymnastics | - PHS Main Gym | 7:00 a.m. | 7:00 am - 9:00 pm | |
| Sun., 1/24 | Miscellaneous Events | Stby Park & Rec Youth Basketball | - Auxiliary Gym | 1:00 p.m. | 1:00 - 9:00 pm | |
| Sun., 1/24 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Mon., 1/25 | V Boys Ice Hockey | Guilford | Home - Taft-Mays Rink [Directions] | L 2-3 | ||
| Mon., 1/25 | Miscellaneous Events | PAC Swim Team | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Mon., 1/25 | Miscellaneous Events | Mdby Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Mon., 1/25 | School Holidays and Closings | Mid-Year Exams, Early Dismissal | ||||
| Tue., 1/26 | V Boys Basketball | Joel Barlow | Home - PHS Main Gym [Directions] | W 63 - 53 | $5 Adults, $4 Students | |
| Tue., 1/26 | JV Boys Basketball | Joel Barlow | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/26 | FR Boys Basketball | Joel Barlow | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Tue., 1/26 | V Boys Swimming and Diving | Weston | Home - PHS Pool [Directions] | 6:00 p.m. | $5 Adults, $4 Students | |
| Tue., 1/26 | V Girls Basketball | Joel Barlow | Away - Lower Gym [Directions] | L 35-37(OT) | 4:00 pm share w/jv girls bb | |
| Tue., 1/26 | JV Girls Basketball | Joel Barlow | Away - Lower Gym [Directions] | 5:15 p.m. | 4:00, share bus with varsity | |
| Tue., 1/26 | FR Girls Basketball | Joel Barlow | Away - Lower Gym [Directions] | 3:30 p.m. | 2:15 pm | |
| Tue., 1/26 | V Girls Gymnastics | Newtown, Nonnewaug, Oxford | Home - Auxiliary Gym [Directions] | 120.70 | ||
| Tue., 1/26 | Miscellaneous Events | PAC Swim Team | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Tue., 1/26 | Miscellaneous Events | Pomp Youth Wrestling | - Wrestling Room | 6:30 p.m. | 6:30 - 8:30 pm | |
| Tue., 1/26 | Miscellaneous Events | Southbury Park and Rec Basketball | - PHS Main Gym | 8:30 p.m. | ||
| Tue., 1/26 | School Holidays and Closings | Mid-Year Exams, Early Dismissal | ||||
| Wed., 1/27 | V Boys Ice Hockey | E.Haven Coop | Home - Taft-Mays Rink [Directions] | L 3-4 | ||
| Wed., 1/27 | V Boys Indoor Track | SWC JV Developmental Meet | Away | 3:00 p.m. | 2:15 pm | @ Danbury Sports Dome |
| Wed., 1/27 | V Wrestling | Joel Barlow | Home - Auxiliary Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/27 | V Girls Indoor Track | SWC JV Development Meet | Away | 3:00 p.m. | 2:15 pm | @ Danbury Sports Dome |
| Wed., 1/27 | Miscellaneous Events | PAC Swim Team | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Wed., 1/27 | Miscellaneous Events | Pomperaug Youth Wrestling Match | - Auxiliary Gym | 6:30 p.m. | 6:30 - 9:30 pm | |
| Wed., 1/27 | Miscellaneous Events | Mdby Park & Rec Basketball | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Thu., 1/28 | Miscellaneous Events | PAC Swim Team | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Thu., 1/28 | Miscellaneous Events | Pomp Youth Wrestling | - Wrestling Room | 6:30 p.m. | 6:30 - 8:30 pm | |
| Thu., 1/28 | Miscellaneous Events | Southbury Park and Rec Adult Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 to 10:00 pm | |
| Fri., 1/29 | V Boys Basketball | Weston | Away - WHS Gymnasium [Directions] | W 73 - 55 | 4:00 pm share w/jv boys bb | |
| Fri., 1/29 | JV Boys Basketball | Weston | Away - WHS Gymnasium [Directions] | 5:15 p.m. | 4:00, share bus with varsity | |
| Fri., 1/29 | FR Boys Basketball | Weston | Away - WHS Gymnasium [Directions] | 3:30 p.m. | 2:15 pm | |
| Fri., 1/29 | V Wrestling | JV Scrimmage Night | Home - Auxiliary Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/29 | V Competitive Cheerleading | Weston | Home - PHS Main Gym [Directions] | 7:00 p.m. | ||
| Fri., 1/29 | V Girls Basketball | Weston | Home - PHS Main Gym [Directions] | W 47-30 | $5 Adults, All Region 15 Students are free! | |
| Fri., 1/29 | JV Girls Basketball | Weston | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/29 | Miscellaneous Events | PAC Swim Team | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Fri., 1/29 | Miscellaneous Events | Pomp Youth Wrestling | - Wrestling Room | 6:30 p.m. | 6:30 - 8:30 pm | |
| Fri., 1/29 | Miscellaneous Events | Mdby Park & Rec Basketball | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Sat., 1/30 | V Boys Ice Hockey | New Milford | Home - Taft-Mays Rink [Directions] | L 0-5 | ||
| Sat., 1/30 | V Wrestling | Portland Tournament | Away [Directions] | 8:00 a.m. | 6:30 am | |
| Sat., 1/30 | V Competitive Cheerleading | Wolcott Competition | Away | TBA | 11:15 am | @ Wolcott HS |
| Sat., 1/30 | FR Girls Basketball | Holy Cross | Away - Holy Cross HS [Directions] | 10:00 a.m. | 9:00 am | |
| Sat., 1/30 | Miscellaneous Events | Stby Park & Rec Basketball | - PHS Main Gym | 1:00 p.m. | 1:00 - 9:00 pm | |
| Sat., 1/30 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 1/31 | Miscellaneous Events | Pomperaug Youth Softball | - Auxiliary Gym | 8:00 a.m. | 8:00 - 11:00 am | |
| Sun., 1/31 | Miscellaneous Events | Stby Park & Rec Youth Basketball | - PHS Main Gym | 1:00 p.m. | 1:00 - 9:00 pm | |
| Sun., 1/31 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 1/31 | Miscellaneous Events | Pomperaug Softball Association Middle School Clinic | - Auxiliary Gym | 4:00 p.m. | 3:30 enter 4:00 - 6:00 pm clinic | |
| Mon., 2/1 | Miscellaneous Events | Mdby Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 2/2 | V Boys Basketball | Notre Dame-Fairfield | Away - Sister Marion Rielly Auditorium at Notre Dame [Directions] | L 50 - 66 | 4:00, share bus with JVs | |
| Tue., 2/2 | JV Boys Basketball | Notre Dame-Fairfield | Away - Sister Marion Rielly Auditorium at Notre Dame [Directions] | 5:15 p.m. | 4:00, share bus with varsity | |
| Tue., 2/2 | FR Boys Basketball | Notre Dame-Fairfield | Away - Sister Marion Rielly Auditorium at Notre Dame [Directions] | 3:30 p.m. | 2:15 pm | |
| Tue., 2/2 | V Boys Swimming and Diving | New Fairfield | Away - New Fairfield HS [Directions] | 4:00 p.m. | 2:15 pm | |
| Tue., 2/2 | V Girls Basketball | Notre Dame-Fairfield | Home - PHS Main Gym [Directions] | W 42-41 | $5 Adults, $4 Students | |
| Tue., 2/2 | JV Girls Basketball | Notre Dame-Fairfield | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/2 | V Girls Gymnastics | Jonathan Law, Nonnewaug, New Milford | Home - Auxiliary Gym [Directions] | 122.15 | ||
| Tue., 2/2 | Miscellaneous Events | Pomp Youth Wrestling | - Wrestling Room | 6:30 p.m. | 6:30 - 8:30 pm | |
| Tue., 2/2 | Miscellaneous Events | Southbury Park and Rec Basketball | - PHS Main Gym | 8:30 pm | 8:30 to 10:00 pm | |
| Wed., 2/3 | V Wrestling | Weston | Away - WHS Gymnasium [Directions] | 7:15 p.m. | 5:00 pm | |
| Wed., 2/3 | Miscellaneous Events | Mdby Park & Rec Basketball | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Wed., 2/3 | Miscellaneous Events | Stby Softball Assn High School Clinic | - Auxiliary Gym | 7:00 p.m. | 6:30 pm - 9:00 pm | |
| Thu., 2/4 | V Co-ed Alpine Skiing | CISL Race | Away | 3:30 p.m. | 2:20 pm | @ Mt. Southington |
| Thu., 2/4 | Miscellaneous Events | Stby Winter Swim Team (PAC) | - PHS Pool | 5:30 p.m. | 5:30 - 8:45 PM | |
| Thu., 2/4 | Miscellaneous Events | Pomp Youth Wrestling | - Wrestling Room | 6:30 p.m. | 6:30 - 8:30 pm | |
| Thu., 2/4 | Miscellaneous Events | Southbury Park and Rec Adult Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 to 10:00 pm | |
| Fri., 2/5 | Miscellaneous Events | Pomp Youth Wrestling | - Wrestling Room | 6:30 p.m. | 6:30 - 8:30 pm | |
| Fri., 2/5 | Miscellaneous Events | Mdby Park & Rec Basketball | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Sat., 2/6 | V Boys Basketball | Masuk | Home - PHS Main Gym [Directions] | W 65 - 56 OT | $5 Adults, $4 Students | |
| Sat., 2/6 | JV Boys Basketball | Masuk | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Sat., 2/6 | FR Boys Basketball | Masuk | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Sat., 2/6 | V Boys Ice Hockey | North Branford | Home - Taft-Mays Rink [Directions] | L 2-6 | ||
| Sat., 2/6 | V Boys Indoor Track | SWC Championship Meet | Away | 4:30 p.m. | 2:45 pm | @ Floyd Little Athletic Center in New Haven |
| Sat., 2/6 | V Boys Swimming and Diving | Inter-Squad Meet | Home - PHS Pool [Directions] | 5:00 p.m. | ||
| Sat., 2/6 | V Wrestling | Branford, Maloney, Farmington, Seymour | Away [Directions] | 10:00 a.m. | 6:30 am | @ Branford |
| Sat., 2/6 | V Wrestling | Maloney, Farmington, Branford, Seymour | Away [Directions] | Cancelled | ||
| Sat., 2/6 | V Competitive Cheerleading | SWC Competition | Away [Directions] | 4:00 p.m. | 1:30 pm | @ Newtown HS, $10 Adults, $5 Students |
| Sat., 2/6 | FR Girls Basketball | Holy Cross | Home - PHS Main Gym [Directions] | 9:00 a.m. | ||
| Sat., 2/6 | V Girls Indoor Track | SWC Championship Meet | Away | 4:30 p.m. | 2:45 pm, share bus with boys indoor track | @ Floyd Little Athletic Center in New Haven |
| Sat., 2/6 | Miscellaneous Events | Stby Park & Rec Basketball | - Auxiliary Gym | 12:00 p.m. | 11:30 - 9:00 pm | |
| Sat., 2/6 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 2/7 | Miscellaneous Events | Stby Park & Rec Youth Basketball Games | - Auxiliary Gym | 11:30 a.m. | 11:30 - 3:30 pm | |
| Sun., 2/7 | Miscellaneous Events | Southbury Youth Softball Clinic | - Auxiliary Gym | 8:00 a.m. | 8:00 - 11:00 am | |
| Sun., 2/7 | Miscellaneous Events | Stby Park & Rec Youth Basketball | - PHS Main Gym | 1:00 p.m. | 1:00 - 9:00 pm | |
| Sun., 2/7 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 2/7 | Miscellaneous Events | Stby Softball Assn Middle School Clinic | - Auxiliary Gym | 3:30 p.m. | 4:00 - 6:00 pm | |
| Mon., 2/8 | Miscellaneous Events | Stby Winter Swim Team (PAC) | - PHS Pool | 5:30 p.m. | 5:30 - 8:45 PM | |
| Mon., 2/8 | Miscellaneous Events | Mdby Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 2/9 | V Boys Basketball | Kolbe Cathedral | Away - Shehan Center [Directions] | W 81 - 68 | 4:00 pm share bus w/jv boys bb | |
| Tue., 2/9 | JV Boys Basketball | Kolbe Cathedral | Away - Shehan Center [Directions] | 5:15 p.m. | 4:00, share bus with varsity | |
| Tue., 2/9 | V Boys Swimming and Diving | New Milford | Home - PHS Pool [Directions] | 4:30 p.m. | ||
| Tue., 2/9 | V Wrestling | Ridgefield | Home - Auxiliary Gym [Directions] | 6:00 p.m. | ||
| Tue., 2/9 | V Wrestling | Brookfield/Shepaug | Home - Auxiliary Gym [Directions] | Cancelled | ||
| Tue., 2/9 | V Girls Basketball | Kolbe Cathedral | Home - PHS Main Gym [Directions] | W 59-50 | $5 Adults, $4 Students | |
| Tue., 2/9 | JV Girls Basketball | Kolbe Cathedral | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/9 | FR Girls Basketball | Bunnell | Away - Bunnell [Directions] | 3:30 p.m. | 2:15 pm | |
| Tue., 2/9 | Miscellaneous Events | Stby Winter Swim Team (PAC) | - PHS Pool | 5:30 p.m. | 5:30 - 8:45 PM | |
| Tue., 2/9 | Miscellaneous Events | Stby Softball Assn High School Clinic | - Auxiliary Gym | 7:00 p.m. | 6:30 pm - 9:00 pm | |
| Tue., 2/9 | Miscellaneous Events | Southbury Park and Rec Adult Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 to 10:00 pm | |
| Wed., 2/10 | V Boys Ice Hockey | North Haven | Away - Northford Ice Pavilion [Directions] | L 0-3 | 6:00 PM | |
| Wed., 2/10 | Miscellaneous Events | Stby Winter Swim Team (PAC) | - PHS Pool | 5:30 p.m. | 5:30 - 8:45 PM | |
| Wed., 2/10 | Miscellaneous Events | Mdby Park & Rec Basketball | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Wed., 2/10 | Miscellaneous Events | Stby Softball Assn High School Clinic | - Auxiliary Gym | 7:00 p.m. | 6:30 pm - 9:00 pm | |
| Thu., 2/11 | V Girls Basketball | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | W 59-34 | 4:00 pm share w/jv girls bb | |
| Thu., 2/11 | JV Girls Basketball | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | 5:15 p.m. | 4:00, share bus with varsity | |
| Thu., 2/11 | FR Girls Basketball | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | 3:45 p.m. | 2:15 pm | |
| Thu., 2/11 | V Girls Gymnastics | SWC Championships | Away [Directions] | 127.65 | ||
| Thu., 2/11 | Miscellaneous Events | Stby Winter Swim Team (PAC) | - PHS Pool | 5:30 p.m. | 5:30 - 8:45 PM | |
| Thu., 2/11 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:30 p.m. | 6:30 - 8:30 pm | |
| Thu., 2/11 | Miscellaneous Events | Southbury Park and Rec Adult Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 to 10:00 pm | |
| Thu., 2/11 | School Holidays and Closings | Prof Development - Half Day | ||||
| Fri., 2/12 | V Boys Basketball | Newtown | Away - Newtown HS Gymnasium [Directions] | W 72 - 66 | 4:00 pm share bus w/jv boys bb | |
| Fri., 2/12 | JV Boys Basketball | Newtown | Away - Newtown HS Gymnasium [Directions] | 5:15 p.m. | 4:00, share bus with varsity | |
| Fri., 2/12 | FR Boys Basketball | Newtown | Away - Newtown HS Gymnasium [Directions] | 3:30 p.m. | 2:15 pm | |
| Fri., 2/12 | V Boys Indoor Track | Class L State Meet | Away | Cancelled | @ Floyd Little Athletic Center in New Haven | |
| Fri., 2/12 | V Competitive Cheerleading | Newtown | Home - PHS Main Gym [Directions] | 7:00 p.m. | ||
| Fri., 2/12 | V Girls Basketball | Newtown | Home - PHS Main Gym [Directions] | W 37-34 | $5 Adults, $4 Students, The actual start time may vary. | |
| Fri., 2/12 | JV Girls Basketball | Newtown | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/12 | FR Girls Basketball | Newtown | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 2/12 | V Girls Indoor Track | Class L State Meet | Away | Cancelled | @Floyd Little Athletic Center in New Haven | |
| Fri., 2/12 | School Holidays and Closings | Presidents' Weekend - No School | ||||
| Sat., 2/13 | V Boys Ice Hockey | Branford | Home - Taft-Mays Rink [Directions] | W 6-2 | ||
| Sat., 2/13 | V Boys Indoor Track | Class L State Meet | Away | 10:00 a.m. | 8:00 am | @ Floyd Little Athletic Center in New Haven |
| Sat., 2/13 | V Wrestling | SWC Championship | Away [Directions] | 9:00 a.m. | 6:15 am | weigh-in 7:00 - 8:00 am |
| Sat., 2/13 | V Girls Indoor Track | Class L State Meet | Away | 10:00 a.m. | 8:00 am | @ Floyd Little Athletic Center in New Haven |
| Sat., 2/13 | Miscellaneous Events | Stby Park & Rec Basketball | - Auxiliary Gym | 12:00 p.m. | 11:30 - 9:00 pm | |
| Sun., 2/14 | Miscellaneous Events | Southbury Youth Softball Clinic | - Auxiliary Gym | 8:00 a.m. | 8:00 - 11:00 am | |
| Sun., 2/14 | Miscellaneous Events | Stby Park & Rec Youth Basketball | - PHS Main Gym | 1:00 p.m. | 1:00 - 9:00 pm | |
| Sun., 2/14 | Miscellaneous Events | Stby Softball Assn Middle School Clinic | - Auxiliary Gym | 3:30 p.m. | 4:00 - 6:00 pm | |
| Mon., 2/15 | V Wrestling | Pomperaug JV Tournament | Home - PHS Main Gym [Directions] | 9:00 a.m. | ||
| Mon., 2/15 | V Girls Gymnastics | Newtown, Oxford, Nonnewaug | Away - Kinetic Kids - Oxford [Directions] | 129.00 | @ Kinetic Kids | |
| Mon., 2/15 | School Holidays and Closings | Washingtons Birthday - No School | ||||
| Tue., 2/16 | Miscellaneous Events | Stby Winter Swim Team (PAC) | - PHS Pool | 5:30 p.m. | 5:30 - 8:45 PM | |
| Tue., 2/16 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:30 p.m. | 6:30 - 8:30 pm | |
| Tue., 2/16 | Miscellaneous Events | Stby Softball Assn High School Clinic | - Auxiliary Gym | 7:00 p.m. | 6:30 pm - 9:00 pm | |
| Tue., 2/16 | Miscellaneous Events | Southbury Park and Rec Adult Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 to 10:00 pm | |
| Wed., 2/17 | V Boys Basketball | Bethel | Home - PHS Main Gym [Directions] | W 85 - 61 | $5 Adults, $4 Students, The actual start time may vary. | |
| Wed., 2/17 | JV Boys Basketball | Bethel | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 2/17 | FR Boys Basketball | Bethel | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Wed., 2/17 | V Boys Ice Hockey | EnricoFermi | Away - Enfield Twin Rinks | W 3-2 | 1:45 PM | |
| Wed., 2/17 | V Co-ed Alpine Skiing | CISL Race | Away | 3:30 p.m. | 2:20 pm | @ Mt Southington |
| Wed., 2/17 | V Girls Basketball | Bethel | Away - Bethel HS [Directions] | W 56-52 | 4:00 pm share w/jv girls bb | |
| Wed., 2/17 | JV Girls Basketball | Bethel | Away - Bethel HS [Directions] | 5:15 p.m. | 4:00, share bus with varsity | |
| Wed., 2/17 | FR Girls Basketball | Bethel | Away - @ Bethel HS [Directions] | Cancelled | ||
| Wed., 2/17 | FR Girls Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | 2:15 pm | |
| Wed., 2/17 | V Girls Gymnastics | Daniel Hand, Nonnewaug | Away - Polson Gymnastics Gym/DHHS Campus [Directions] | 117.6 | ||
| Wed., 2/17 | Miscellaneous Events | Stby Winter Swim Team (PAC) | - PHS Pool | 5:30 p.m. | 5:30 - 8:45 PM | |
| Wed., 2/17 | Miscellaneous Events | Mdby Park & Rec Basketball | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Wed., 2/17 | Miscellaneous Events | Stby Softball Assn High School Clinic | - Auxiliary Gym | 7:00 p.m. | 6:30 pm - 9:00 pm | |
| Thu., 2/18 | V Boys Basketball | Stratford | Away - Needham Memorial Gymnasium [Directions] | L 65 - 71 | 4:00 pm share w/ jv boys bb | |
| Thu., 2/18 | JV Boys Basketball | Stratford | Away - Needham Memorial Gymnasium [Directions] | 5:15 p.m. | 4:00, share bus with varsity | |
| Thu., 2/18 | FR Boys Basketball | Stratford | Away - Needham Memorial Gymnasium [Directions] | 3:30 p.m. | 2:15 pm | |
| Thu., 2/18 | Miscellaneous Events | Stby Winter Swim Team (PAC) | - PHS Pool | 5:30 p.m. | 5:30 - 8:45 PM | |
| Thu., 2/18 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:30 p.m. | 6:30 - 8:30 pm | |
| Thu., 2/18 | Miscellaneous Events | Southbury Park and Rec Adult Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 to 10:00 pm | |
| Fri., 2/19 | V Wrestling | CIAC Class Meet | Away | TBA | 1:15 pm | |
| Fri., 2/19 | V Competitive Cheerleading | Girls SWC Quarter-Finals | Home - PHS Main Gym [Directions] | TBA | ||
| Fri., 2/19 | V Girls Basketball | SWC Quarter-Finals | Home - PHS Main Gym [Directions] | 7:00 p.m. | $8 Adults, $5 Students | |
| Fri., 2/19 | Miscellaneous Events | Stby Winter Swim Team (PAC) | - PHS Pool | 5:30 p.m. | 5:30 - 8:45 PM | |
| Fri., 2/19 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:30 p.m. | 6:30 - 8:30 pm | |
| Fri., 2/19 | Miscellaneous Events | Mdby Park & Rec Basketball | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Sat., 2/20 | FR Boys Basketball | Masuk | Home - PHS Main Gym [Directions] | 9:00 a.m. | ||
| Sat., 2/20 | V Boys Ice Hockey | New Fairfield | Home - Taft-Mays Rink [Directions] | L 0-2 | ||
| Sat., 2/20 | V Boys Indoor Track | State Open | Away | 12:00 p.m. | 10:00 am | @ Floyd Little Athletic Center in New Haven |
| Sat., 2/20 | V Wrestling | CIAC Class Championship | Away | TBA | 6:30 am. One way bus. | @ Bristol Central |
| Sat., 2/20 | V Girls Indoor Track | State Open Meet | Away | 12:00 p.m. | 10:00 am | @ Floyd Little Athletic Center in New Haven |
| Sat., 2/20 | Miscellaneous Events | Stby Park & Rec Basketball | - Auxiliary Gym | 12:00 p.m. | 11:30 - 9:00 pm | |
| Sat., 2/20 | Miscellaneous Events | Baseball Clinic | - PHS Main Gym | 12:00 p.m. | 12:00 to 2:00 pm | |
| Sat., 2/20 | Miscellaneous Events | Baseball Clinic | - Auxiliary Gym | 12:00 p.m. | 12:00 to 2:00 pm | |
| Sat., 2/20 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sat., 2/20 | School Holidays and Closings | Senior Semi-Formal | ||||
| Sun., 2/21 | Miscellaneous Events | Southbury Youth Softball Clinic | - Auxiliary Gym | 8:00 a.m. | 8:00 - 11:00 am | |
| Sun., 2/21 | Miscellaneous Events | Stby Park & Rec Youth Basketball | - PHS Main Gym | 1:00 p.m. | 1:00 - 9:00 pm | |
| Sun., 2/21 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 2/21 | Miscellaneous Events | Stby Softball Assn Middle School Clinic | - Auxiliary Gym | 3:30 p.m. | 4:00 - 6:00 pm | |
| Mon., 2/22 | V Boys Ice Hockey | New Milford | Away - Canterbury School [Directions] | L 2-3(OT) | 5:30 PM | |
| Mon., 2/22 | V Girls Basketball | SWC Semi-Finals | Away [Directions] | 5:15 p.m. | 3:30 pm | $8 Adults, $5 Students |
| Mon., 2/22 | Miscellaneous Events | Stby Winter Swim Team (PAC) | - PHS Pool | 5:30 p.m. | 5:30 - 8:45 PM | |
| Mon., 2/22 | Miscellaneous Events | Middlebury Baseball Practice | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Mon., 2/22 | Miscellaneous Events | Mdby Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 2/23 | Miscellaneous Events | Stby Winter Swim Team (PAC) | - PHS Pool | 5:30 p.m. | 5:30 - 8:45 PM | |
| Tue., 2/23 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:30 p.m. | 6:30 - 8:30 pm | |
| Tue., 2/23 | Miscellaneous Events | Southbury Park and Rec Adult Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 to 10:00 pm | |
| Wed., 2/24 | V Boys Basketball | Immaculate | Away - Immaculate HS [Directions] | W 82 - 78(2OT) | 4:00 pm share bus w/ jv boys bb | |
| Wed., 2/24 | JV Boys Basketball | Immaculate | Away - Immaculate HS [Directions] | 5:15 p.m. | 4:00, share bus with varsity | |
| Wed., 2/24 | FR Boys Basketball | Immaculate | Away - Immaculate HS [Directions] | 3:30 p.m. | 2:15 pm | |
| Wed., 2/24 | V Boys Ice Hockey | Amity | Away - Bennett Rink - West Haven [Directions] | W 2-1 | 1:45 PM | |
| Wed., 2/24 | V Boys Swimming and Diving | Newtown | Home - PHS Pool [Directions] | 6:00 p.m. | $5 Adults, $4 Students | |
| Wed., 2/24 | V Girls Basketball | SWC Championship Game | Away | Cancelled | $10 Adults, $5 Students | |
| Wed., 2/24 | Miscellaneous Events | Stby Winter Swim Team (PAC) | - PHS Pool | 5:30 p.m. | 5:30 - 8:45 PM | |
| Wed., 2/24 | Miscellaneous Events | Mdby Park & Rec Basketball | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Wed., 2/24 | Miscellaneous Events | Stby Softball Assn High School Clinic | - Auxiliary Gym | 7:00 p.m. | 6:30 pm - 9:00 pm | |
| Thu., 2/25 | Miscellaneous Events | Stby Winter Swim Team (PAC) | - PHS Pool | 5:30 p.m. | 5:30 - 8:45 PM | |
| Thu., 2/25 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:30 p.m. | 6:30 - 8:30 pm | |
| Thu., 2/25 | Miscellaneous Events | Southbury Park and Rec Adult Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 to 10:00 pm | |
| Fri., 2/26 | V Boys Basketball | Joel Barlow | Home - PHS Main Gym [Directions] | W 66 - 37 | $8 Adults, $5 Students | |
| Fri., 2/26 | V Wrestling | CIAC State Open | Away | 4:00 p.m. | 12:30 pm | @ Floyd Little Center in New Haven |
| Fri., 2/26 | V Girls Basketball | CIAC Tournament Game | Home - PHS Main Gym [Directions] | TBA | $8 Adults, $5 Students | |
| Fri., 2/26 | Miscellaneous Events | Stby Winter Swim Team (PAC) | - PHS Pool | 5:30 p.m. | 5:30 - 8:45 PM | |
| Fri., 2/26 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:30 p.m. | 6:30 - 8:30 pm | |
| Fri., 2/26 | Miscellaneous Events | Mdby Park & Rec Basketball | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Sat., 2/27 | V Boys Ice Hockey | Danbury | Home - Taft-Mays Rink [Directions] | W 4-1 | SENIOR NIGHT | |
| Sat., 2/27 | V Wrestling | CIAC State Open | Away | TBA | No Bus | |
| Sat., 2/27 | V Girls Gymnastics | CIAC State Championships | Home - PHS Main Gym [Directions] | TBA | $10 Adults, $5 Students | |
| Sat., 2/27 | Miscellaneous Events | Stby Park & Rec Basketball | - Auxiliary Gym | 12:00 p.m. | 11:30 - 9:00 pm | |
| Sat., 2/27 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sat., 2/27 | Miscellaneous Events | Kinetic Kids Gymnastics Invitational | - PHS Main Gym | 3:00 p.m. | 3:00 - 10:00 pm | |
| Sun., 2/28 | V Boys Indoor Track | New England Meet | Away | 1:00 p.m. | 9:00 am, Share bus with Girls' Indoor Track | @ Regie Lewis Center, Boston, MA |
| Sun., 2/28 | V Boys Indoor Track | New England Meet | Away | Cancelled | ||
| Sun., 2/28 | V Girls Indoor Track | New England Meet | Away | 1:00 p.m. | 9:00 am, Share bus with Boys Indoor Track | |
| Sun., 2/28 | V Girls Indoor Track | New England Meet | Away | Cancelled | ||
| Sun., 2/28 | Miscellaneous Events | Kinetic Kids Gymnastics Invitational | - PHS Main Gym | 7:00 a.m. | 7:00 am - 1:00 pm | |
| Sun., 2/28 | Miscellaneous Events | Southbury Youth Softball Clinic | - Auxiliary Gym | 8:00 a.m. | 8:00 - 11:00 am | |
| Sun., 2/28 | Miscellaneous Events | Stby Park & Rec Youth Basketball | - Auxiliary Gym | 1:00 p.m. | 1:00 - 9:00 pm | |
| Sun., 2/28 | Miscellaneous Events | Stby Softball Assn Middle School Clinic | - Auxiliary Gym | 3:30 p.m. | 4:00 - 6:00 pm | |
| Mon., 2/29 | V Boys Basketball | Notre Dame-Fairfield | Away [Directions] | L 74 - 88 | 3:00 pm | $8 Adults, $5 Students, @ Weston |
| Mon., 2/29 | V Co-ed Alpine Skiing | CISL Race | Away | 3:30 p.m. | 2:20 pm | @ Mount Southington |
| Mon., 2/29 | V Girls Basketball | Brookfield | Home - PHS Main Gym [Directions] | W 53-20 | $8 Adults, $5 Students | |
| Mon., 2/29 | Miscellaneous Events | Middlebury Baseball Practice | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Mon., 2/29 | Miscellaneous Events | Mdby Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 3/1 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:30 p.m. | 6:30 - 8:30 pm | |
| Tue., 3/1 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:30 p.m. | 6:30 - 8:30 pm | |
| Wed., 3/2 | V Boys Swimming and Diving | SWC Diving Championships | Away [Directions] | 6:00 p.m. | 3:00 pm | warm-ups @ 4:30 pm |
| Wed., 3/2 | V Co-ed Alpine Skiing | CISL Race | Away | 3:30 p.m. | 2:20 pm | @ Mount Southington |
| Wed., 3/2 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:30 p.m. | 6:30 - 8:30 pm | |
| Wed., 3/2 | Miscellaneous Events | Middlebury Youth Basketball | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Wed., 3/2 | Miscellaneous Events | Stby Softball Assn High School Clinic | - Auxiliary Gym | 7:00 p.m. | 6:30 pm - 9:00 pm | |
| Thu., 3/3 | V Boys Basketball | SWC Championship Game | Away | Cancelled | $10 Adults, $5 Students | |
| Thu., 3/3 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:30 p.m. | 6:30 - 8:30 pm | |
| Thu., 3/3 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:30 p.m. | 6:30 - 8:30 pm | |
| Fri., 3/4 | V Boys Swimming and Diving | SWC Championship Meet | Away [Directions] | 6:00 p.m. | 3:00 pm 1st bus, 4:30 pm second bus. | warm-ups @ 4:00 pm |
| Fri., 3/4 | V Girls Basketball | RHAM | Home - PHS Main Gym [Directions] | 7:00 p.m. | $8 Adults, $5 Students | |
| Fri., 3/4 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:30 p.m. | 6:30 - 8:30 pm | |
| Fri., 3/4 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:30 p.m. | 6:30 - 8:30 pm | |
| Fri., 3/4 | Miscellaneous Events | Mdby Park & Rec Basketball | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Fri., 3/4 | School Holidays and Closings | Prof Development - Half Day | ||||
| Sat., 3/5 | V Boys Swimming and Diving | Naugatuck (Scrim.) | Away [Directions] | 3:00 p.m. | 1:00 pm | JV Meet |
| Sat., 3/5 | V Bowling | CT High School Bowling Tournament | Away | 10:00 a.m. | 8:15 am | @ Bowl-O-Rama in Newington |
| Sat., 3/5 | V Competitive Cheerleading | State Cheer Competition | Away | TBA | 1:45 pm | |
| Sat., 3/5 | V Girls Gymnastics | CIAC State Open | Away | TBA | ||
| Sat., 3/5 | Miscellaneous Events | Stby Park & Rec Basketball | - Auxiliary Gym | 12:00 p.m. | 11:30 - 9:00 pm | |
| Sat., 3/5 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 3/6 | Miscellaneous Events | Southbury Youth Softball Clinic | - Auxiliary Gym | 8:00 a.m. | 8:00 - 11:00 am | |
| Sun., 3/6 | Miscellaneous Events | Stby Park & Rec Youth Basketball | - PHS Main Gym | 1:00 p.m. | 1:00 - 9:00 pm | |
| Sun., 3/6 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 3/6 | Miscellaneous Events | Stby Softball Assn Middle School Clinic | - Auxiliary Gym | 3:30 p.m. | 4:00 - 6:00 pm | |
| Mon., 3/7 | V Boys Basketball | North Haven | Home - PHS Main Gym [Directions] | W 90 - 53 | $8 Adults, $5 Students | |
| Mon., 3/7 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:30 p.m. | 6:30 - 8:30 pm | |
| Mon., 3/7 | Miscellaneous Events | Middlebury Baseball Practice | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Mon., 3/7 | Miscellaneous Events | Mdby Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 3/8 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland Of Ice [Directions] | 8:00 p.m. | 6:00 PM | |
| Tue., 3/8 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:30 p.m. | 6:30 - 8:30 pm | |
| Tue., 3/8 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:30 p.m. | 6:30 - 8:30 pm | |
| Wed., 3/9 | V Boys Basketball | Lyman Hall | Home - PHS Main Gym [Directions] | W 85 - 55 | $8 Adults, $5 Students | |
| Wed., 3/9 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:30 p.m. | 6:30 - 8:30 pm | |
| Wed., 3/9 | Miscellaneous Events | Mdby Park & Rec Basketball | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Thu., 3/10 | V Boys Swimming and Diving | CIAC Class M Diving Trials/Finals | Away - Bulkeley HS [Directions] | 5:30 p.m. | @ Buckley HS | |
| Thu., 3/10 | V Boys Swimming and Diving | CIAC Class M Diving Trials/Finals | Away - Bulkeley HS [Directions] | 5:30 p.m. | 2:30 pm, one way bus | @ Buckley HS |
| Thu., 3/10 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 3:00 p.m. | ||
| Thu., 3/10 | Miscellaneous Events | Spring Coaches Meeting | - All Purpose Room | 4:00 p.m. | ||
| Thu., 3/10 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:30 p.m. | 6:30 - 8:30 pm | |
| Thu., 3/10 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:30 p.m. | 6:30 - 8:30 pm | |
| Fri., 3/11 | V Boys Basketball | Middletown | Away [Directions] | 7:00 p.m. | 5:00 pm | |
| Fri., 3/11 | Miscellaneous Events | Rochambeau March Madness Game | - PHS Main Gym | 3:00 p.m. | Game Begins @ 6:00 pm - 9:00 pm | |
| Fri., 3/11 | Miscellaneous Events | RMS Basketball Blowout | - PHS Main Gym | 4:00 p.m. | Setu up at 4:00 pm | |
| Fri., 3/11 | Miscellaneous Events | Pomperaug Outreach Babysitting | - Auxiliary Gym | 5:30 p.m. | 5:30 - 7:00 pm | |
| Fri., 3/11 | Miscellaneous Events | Pomperaug Youth Wrestling | - Wrestling Room | 6:30 p.m. | 6:30 - 8:30 pm | |
| Fri., 3/11 | Miscellaneous Events | Mdby Park & Rec Basketball | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Sat., 3/12 | V Boys Swimming and Diving | CIAC Class M Qualifying | Away - Masuk HS [Directions] | 3:30 p.m. | @ Masuk HS, $8 Adults, $5 Students | |
| Sat., 3/12 | V Boys Swimming and Diving | CIAC Class M Qualifying | Away - Masuk HS [Directions] | 3:30 p.m. | 12:45 pm | @ Masuk HS, $8 Adults, $5 Students |
| Sat., 3/12 | Miscellaneous Events | Stby Park & Rec Basketball | - Auxiliary Gym | 12:00 p.m. | 11:30 - 9:00 pm | |
| Sat., 3/12 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 3/13 | Miscellaneous Events | Southbury Youth Softball Clinic | - Auxiliary Gym | 8:00 a.m. | 8:00 - 11:00 am | |
| Sun., 3/13 | Miscellaneous Events | Stby Park & Rec Youth Basketball | - PHS Main Gym | 1:00 p.m. | 1:00 - 9:00 pm | |
| Sun., 3/13 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Mon., 3/14 | Miscellaneous Events | Girls Lacrosse Conditioning | - Sports Complex & Track | 2:30 p.m. | 2:30 - 4:30 | |
| Mon., 3/14 | Miscellaneous Events | Girls Lacrosse Conditioning | - Sports Complex & Track | 2:30 p.m. | 2:30 - 4:30 | |
| Mon., 3/14 | Miscellaneous Events | Middlebury Baseball Practice | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Tue., 3/15 | V Boys Swimming and Diving | CIAC Class M Finals | Away - Wesleyan Univ. [Directions] | 1:30 p.m. | 11:00 am | @ Weslyan, $10 Adults, $5 Students |
| Tue., 3/15 | V Boys Swimming and Diving | CIAC Class M Finals | Away - Wesleyan Univ. [Directions] | 1:30 p.m. | 11:00 am | @ Weslyan, $10 Adults, $5 Students |
| Tue., 3/15 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 3:00 p.m. | ||
| Tue., 3/15 | Miscellaneous Events | Southbury Park & Rec HS Basketball Playoffs | - PHS Main Gym | 5:30 p.m. | 5:30 - 8:30 pm | |
| Wed., 3/16 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 6:30 pm | |
| Wed., 3/16 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 p.m. | 7:00 - 8:00 pm | |
| Wed., 3/16 | Miscellaneous Events | Mdby Park & Rec Basketball | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Thu., 3/17 | V Boys Swimming and Diving | CIAC Open Diving | Away - Bulkeley [Directions] | Cancelled | @ Buckley | |
| Thu., 3/17 | V Boys Swimming and Diving | CIAC Open Diving | Away - Bulkeley [Directions] | 5:30 p.m. | @ Buckley | |
| Thu., 3/17 | Miscellaneous Events | Southbury Park & Rec HS Basketball Playoffs | - PHS Main Gym | 5:30 p.m. | 5:30 - 8:30 pm | |
| Thu., 3/17 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 6:30 pm | |
| Thu., 3/17 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 p.m. | 7:00 - 8:00 pm | |
| Fri., 3/18 | Miscellaneous Events | Red Cross Blood Drive | - Auxiliary Gym | 6:00 a.m. | 6:00 am - 2:30 pm | |
| Fri., 3/18 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 p.m. | 7:00 - 8:00 pm | |
| Fri., 3/18 | Miscellaneous Events | Mdby Park & Rec Basketball | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Sat., 3/19 | V Boys Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | Cancelled | @ Yale, $10 Adults, $5 Students | |
| Sat., 3/19 | V Boys Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 2:30 p.m. | 11:30 am | @ Yale, $10 Adults, $5 Students |
| Sat., 3/19 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sat., 3/19 | Miscellaneous Events | CT Drama Festival | - PHS Main Gym | 6:00 p.m. | 6:00 - 10:00 pm | |
| Sun., 3/20 | Miscellaneous Events | Southbury Youth Softball Clinic | - Auxiliary Gym | 8:00 a.m. | 8:00 - 11:00 am | |
| Sun., 3/20 | Miscellaneous Events | Stby Park & Rec Youth Basketball | - PHS Main Gym | 1:00 p.m. | 1:00 - 9:00 pm | |
| Sun., 3/20 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Mon., 3/21 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 p.m. | 7:00 - 8:00 pm | |
| Mon., 3/21 | Miscellaneous Events | Mdby Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 3/22 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 6:30 pm | |
| Tue., 3/22 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 p.m. | 7:00 - 8:00 pm | |
| Wed., 3/23 | V Baseball | Bristol Central (Scrim.) | Home - PHS Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 3/23 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 p.m. | 7:00 - 8:00 pm | |
| Wed., 3/23 | Miscellaneous Events | Mdby Park & Rec Basketball | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Thu., 3/24 | V Boys Lacrosse | Shelton (Scrim.) | Away - Shelton HS Finn Stadium [Directions] | 8:00 p.m. | 5:30 pm | |
| Thu., 3/24 | V Girls Lacrosse | North Branford (Scrim.) | Away - North Branford HS [Directions] | 4:00 p.m. | 2:15 pm | |
| Thu., 3/24 | JV Girls Lacrosse | North Branford (Scrim.) | Away [Directions] | 4:00 p.m. | 2:15 pm., Share bus with varsity | |
| Thu., 3/24 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 6:30 pm | |
| Thu., 3/24 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 p.m. | 7:00 - 8:00 pm | |
| Fri., 3/25 | School Holidays and Closings | Good Friday - No School | ||||
| Sat., 3/26 | V Baseball | Weston (Scrim.) | Away [Directions] | 10:00 a.m. | 8:30 am | |
| Sat., 3/26 | V Boys Lacrosse | Hamden (Scrim.) | Away [Directions] | 10:30 a.m. | 8:30 am | Hamden Jamboree |
| Sat., 3/26 | V Girls Lacrosse | Danbury Play Date | Away | 9:00 a.m. | 8:00 am | |
| Sat., 3/26 | V Softball | Seymour (Scrim.) | Home - PHS Softball Field [Directions] | 1:00 p.m. | ||
| Sun., 3/27 | Miscellaneous Events | Southbury Youth Softball Clinic | - Auxiliary Gym | 8:00 a.m. | 8:00 - 11:00 am | |
| Sun., 3/27 | School Holidays and Closings | Easter Sunday | ||||
| Mon., 3/28 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 p.m. | 7:00 - 8:00 pm | |
| Mon., 3/28 | Miscellaneous Events | Middlebury Baseball Practice | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Mon., 3/28 | Miscellaneous Events | Mdby Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 3/29 | V Baseball | Holy Cross (Scrim.) | Home - PHS Baseball Field [Directions] | 4:00 p.m. | ||
| Tue., 3/29 | V Softball | Holy Cross (Scrim.) | Home - PHS Softball Field [Directions] | 4:00 p.m. | ||
| Tue., 3/29 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 6:30 pm | |
| Tue., 3/29 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 p.m. | 7:00 - 8:00 pm | |
| Wed., 3/30 | V Baseball | Naugatuck (Scrim.) | Away - Naugatuck HS [Directions] | 3:30 p.m. | 2:45 pm | |
| Wed., 3/30 | V Softball | Oxford (Scrim.) | Home - PHS Softball Field [Directions] | 4:00 p.m. | ||
| Wed., 3/30 | JV Softball | Oxford (Scrim.) | Home - PHS Softball Field [Directions] | 4:00 p.m. | ||
| Wed., 3/30 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 p.m. | 7:00 - 8:00 pm | |
| Wed., 3/30 | Miscellaneous Events | Mdby Park & Rec Basketball | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Thu., 3/31 | V Girls Lacrosse | Farmington (Scrim.) | Away - Farmington HS [Directions] | 4:00 p.m. | 2:15 pm | 4:00 to 7:00 pm |
| Thu., 3/31 | V Girls Tennis | Nonnewaug (Scrim.) | Home - PHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 3/31 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 6:30 pm | |
| Fri., 4/1 | Miscellaneous Events | USA Gymnastics State Championships Set-Up | - PHS Main Gym | 3:00 p.m. | 3:00 - 7:00 pm | |
| Fri., 4/1 | Miscellaneous Events | Dodgeball for Diabetes | - PHS Main Gym | 7:00 p.m. | 7:00 - 10:00 pm | |
| Sat., 4/2 | Miscellaneous Events | USA Gymnastics State Championships | - PHS Main Gym | 7:00 a.m. | 7:00 am - 9:00 pm | |
| Sun., 4/3 | Miscellaneous Events | USA Gymnastics State Championships | - PHS Main Gym | 7:00 a.m. | 7:00 am - 9:00 pm | |
| Mon., 4/4 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:30 p.m. | 6:30 - 8:00 pm | |
| Mon., 4/4 | Miscellaneous Events | Mdby Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 4/5 | V Boys Lacrosse | North Haven | Home - Sports Complex & Track [Directions] | L 3-9 | ||
| Tue., 4/5 | JV Boys Lacrosse | North Haven | Home - Sports Complex & Track [Directions] | 5:15 p.m. | ||
| Tue., 4/5 | V Girls Tennis | Bethel | Away [Directions] | W 5-2 | 2:15 pm | Non-League Game |
| Wed., 4/6 | V Boys Golf | Stratford | Home - Heritage Village C.C. [Directions] | Pomperaug 164 Stratford 224 | ||
| Wed., 4/6 | V Softball | Masuk | Away - Masuk HS Softball Field [Directions] | L 10-9 | 2:15 | Non-league game |
| Wed., 4/6 | V Girls Tennis | Brookfield | Away - BHS Tennis Courts [Directions] | W 5-2 | 2:15 pm | Non-League Game |
| Wed., 4/6 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 2:30 p.m. | 2:30 - 7:00 pm | |
| Wed., 4/6 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:30 p.m. | 6:30 - 8:00 pm | |
| Thu., 4/7 | V Boys Lacrosse | Stratford | Home - Sports Complex & Track [Directions] | W 14-8 | Division Game | |
| Thu., 4/7 | JV Boys Lacrosse | Stratford | Home - Sports Complex & Track [Directions] | 5:15 p.m. | ||
| Thu., 4/7 | V Girls Lacrosse | Stratford/Bunnell | Away - Penders Field [Directions] | W 16-4 | 3:45 share bus with jv | Division Game |
| Thu., 4/7 | JV Girls Lacrosse | Stratford/Bunnell | Away - Penders Field [Directions] | 5:30 p.m. | 3:45 share w/varsity | |
| Thu., 4/7 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 2:30 p.m. | 2:30 - 9:00 pm | |
| Thu., 4/7 | Miscellaneous Events | Boys Soccer Team Meeting | - Health Classroom - Room 201 | 3:30 p.m. | 3:30 - 4:00 pm | |
| Fri., 4/8 | V Baseball | Danbury | Home - Community Baseball Field [Directions] | W 1-0 | ||
| Fri., 4/8 | FR Baseball | Danbury | Away - Danbury HS Varsity Baseball Field [Directions] | 4:15 p.m. | 2:15 pm | |
| Fri., 4/8 | V Boys Tennis | Newtown | Away - Newtown HS [Directions] | W 6-1 | 2:15 pm | Non-League Game |
| Fri., 4/8 | V Softball | Danbury | Home - PHS Softball Field [Directions] | W 8 - 1 | ||
| Fri., 4/8 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 2:30 p.m. | 2:30 - 7:00 pm | |
| Fri., 4/8 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:45 p.m. | 2:45 - 4:45 pm | |
| Sat., 4/9 | JV Baseball | Danbury | Away - Danbury HS Junior Varsity Baseball Field [Directions] | 10:00 a.m. | 8:15 am, share bus with JV Softball | |
| Sat., 4/9 | V Boys Lacrosse | Trumbull | Home - Sports Complex & Track [Directions] | L 5-11 | ||
| Sat., 4/9 | JV Boys Lacrosse | Trumbull | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Sat., 4/9 | V Girls Lacrosse | Amity | Away - Amity HS - Field # 3 [Directions] | W 19-10 | 12:00 pm | |
| Sat., 4/9 | JV Girls Lacrosse | Amity | Away - Amity HS - Field # 3 [Directions] | 4:00 p.m. | 2:00 pm | |
| Sat., 4/9 | JV Softball | Danbury | Away - Danbury HS Junior Varsity Softball Field [Directions] | 10:00 a.m. | 8:15, share bus with JV Baseball | |
| Sat., 4/9 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 2:30 p.m. | 2:30 - 7:00 pm | |
| Mon., 4/11 | V Boys Golf | New Milford | Home - Heritage Village C.C. [Directions] | Pomperaug 166 New Milford 178 | ||
| Mon., 4/11 | V Boys Tennis | Brookfield | Away - BHS Tennis Courts [Directions] | W 7-0 | 2:15 pm | |
| Mon., 4/11 | V Girls Lacrosse | New Milford | Home - Sports Complex & Track [Directions] | W 19-9 | Cross Over Game | |
| Mon., 4/11 | JV Girls Lacrosse | New Milford | Home - Sports Complex & Track [Directions] | 3:30 p.m. | ||
| Mon., 4/11 | V Girls Outdoor Track | Danbury | Away - Danbury HS Stadium [Directions] | DHS 100 PHS 45 | 2:00 pm | |
| Mon., 4/11 | V Softball | Brookfield | Away - BHS Softball Field [Directions] | W 7-6 | 2:15 | Non-League Game |
| Mon., 4/11 | V Girls Tennis | Brookfield | Home - PHS Tennis Courts [Directions] | W 6-1 | ||
| Mon., 4/11 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 8:30 a.m. | 8:30 - 10:00 am | |
| Mon., 4/11 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 2:30 p.m. | 2:30 - 7:00 pm | |
| Mon., 4/11 | School Holidays and Closings | Spring Recess | ||||
| Tue., 4/12 | V Boys Lacrosse | New Milford | Home - Sports Complex & Track [Directions] | W 13-6 | Cross over game | |
| Tue., 4/12 | JV Boys Lacrosse | New Milford | Home - Sports Complex & Track [Directions] | 5:15 p.m. | ||
| Tue., 4/12 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 8:30 a.m. | 8:30 - 10:00 am | |
| Tue., 4/12 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 3:00 p.m. | 3:00 - 7:00 pm | |
| Tue., 4/12 | School Holidays and Closings | Spring Recess | ||||
| Wed., 4/13 | V Baseball | Bunnell | Home - PHS Baseball Field [Directions] | W 8-3 | Non-League Game | |
| Wed., 4/13 | FR Baseball | Bunnell | Away - Bunnell Baseball Field [Directions] | 3:45 p.m. | 2:15 pm | |
| Wed., 4/13 | V Boys Tennis | Bunnell | Home - PHS Tennis Courts [Directions] | W 7-0 | ||
| Wed., 4/13 | V Softball | Bunnell | Home - PHS Softball Field [Directions] | W 3-0 | Non-League Game | |
| Wed., 4/13 | V Girls Tennis | Bunnell | Away - Bunnell Tennis Courts [Directions] | W 6-1 | 8:45 am | |
| Wed., 4/13 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 8:30 a.m. | 8:30 - 10:00 am | |
| Wed., 4/13 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 3:00 p.m. | 3:00 - 7:00 pm | |
| Wed., 4/13 | School Holidays and Closings | Spring Recess | ||||
| Thu., 4/14 | JV Baseball | Bunnell | Home - Community Baseball Field [Directions] | 3:45 p.m. | Meet at Community Field | |
| Thu., 4/14 | V Boys Lacrosse | New Fairfield | Home - Sports Complex & Track [Directions] | L 3-14 | Cross Over Game | |
| Thu., 4/14 | JV Boys Lacrosse | New Fairfield | Home - Sports Complex & Track [Directions] | 5:15 p.m. | ||
| Thu., 4/14 | V Boys Tennis | Weston | Away - WHS Tennis Courts [Directions] | L 3-4 | 8:15 am | |
| Thu., 4/14 | V Girls Lacrosse | New Fairfield | Away - Rebel Turf [Directions] | L 13-17 | 3:45 share bus w/jv | Cross Over Game |
| Thu., 4/14 | JV Girls Lacrosse | New Fairfield | Away - Rebel Turf [Directions] | 5:15 p.m. | 3:45 share w/varsity | |
| Thu., 4/14 | JV Softball | Bunnell | Home - Community Softball Field [Directions] | Cancelled | Meet at Community Field | |
| Thu., 4/14 | V Girls Tennis | Weston | Home - PHS Tennis Courts [Directions] | L 1-6 | ||
| Thu., 4/14 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 8:30 a.m. | 8:30 - 10:00 am | |
| Thu., 4/14 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 4:00 p.m. | 4:00 - 7:00 pm | |
| Thu., 4/14 | School Holidays and Closings | Spring Recess | ||||
| Fri., 4/15 | V Baseball | Weston | Away - Revson Field, Weston [Directions] | W 11-6 | 2:15 | Non-League Game |
| Fri., 4/15 | FR Baseball | Weston | Home - PHS Baseball Field [Directions] | 12:00 p.m. | ||
| Fri., 4/15 | V Softball | New Milford | Away - New Milford HS [Directions] | W 4-2 | 2:15 | Non-League Game |
| Fri., 4/15 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 10:00 a.m. | 10:00 am - 2:00 pm | |
| Fri., 4/15 | School Holidays and Closings | Spring Recess | ||||
| Sat., 4/16 | V Baseball | Nonnewaug | Away - Nonnewaug HS Field [Directions] | W 12-3 | 11:45 am | |
| Sat., 4/16 | JV Baseball | Weston | Away - Revson Field, Weston [Directions] | 10:00 a.m. | 8:00 am | |
| Sat., 4/16 | V Boys Lacrosse | Danbury | Home - Sports Complex & Track [Directions] | L 5-16 | ||
| Sat., 4/16 | JV Boys Lacrosse | Danbury | Home - Sports Complex & Track [Directions] | 12:00 p.m. | ||
| Sat., 4/16 | JV Softball | New Milford | Away - New Milford HS [Directions] | Cancelled | ||
| Sat., 4/16 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 9:00 a.m. | 9:00 am - 2:00 pm | |
| Mon., 4/18 | V Baseball | Newtown | Home - PHS Baseball Field [Directions] | L 4-2 | Non-League Game | |
| Mon., 4/18 | FR Baseball | Newtown | Away - Newtown HS Baseball Field [Directions] | 3:45 p.m. | 2:15 pm | |
| Mon., 4/18 | V Boys Golf | Brookfield | Away - Sunset Hill Golf Course [Directions] | Pomperaug 175 Brookfield 169 | 1:45 pm | |
| Mon., 4/18 | V Girls Outdoor Track | Newtown, Bethel | Home - Sports Complex & Track [Directions] | NHS 79.5 PHS 70.5 PHS 95.5 BHS 53.5 | ||
| Mon., 4/18 | V Softball | Newtown | Home - PHS Softball Field [Directions] | L 1-7 | Non-League Game | |
| Mon., 4/18 | FR Softball | Newtown | Away - Newtown HS Softball Field [Directions] | 3:45 p.m. | 2:15 | |
| Mon., 4/18 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 pm | |
| Mon., 4/18 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 2:30 p.m. | 2:30 - 7:00 pm | |
| Mon., 4/18 | Miscellaneous Events | Mdby Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 4/19 | JV Baseball | Newtown | Home - Community Baseball Field [Directions] | 3:45 p.m. | 2:15, one way bus | |
| Tue., 4/19 | V Boys Golf | Bunnell | Away - Oronoque Country Club [Directions] | Pomperaug 166 Bunnell 206 | 1:45 pm | |
| Tue., 4/19 | V Boys Lacrosse | Notre Dame-Fairfield | Away - Veteran's Park - Bridgeport [Directions] | W 18-2 | 2:15 pm | Division Game |
| Tue., 4/19 | V Boys Outdoor Track | Newtown, Bethel | Away - Blue and Gold Stadium [Directions] | Pomperaug 53 Newtown 97 Pomperaug 93 Newtown 56 | 2:15 pm | @ Newtown |
| Tue., 4/19 | V Girls Lacrosse | Notre Dame-Fairfield | Home - Sports Complex & Track [Directions] | W 15-5 | Division Game | |
| Tue., 4/19 | JV Girls Lacrosse | New Milford | Home - Sports Complex & Track [Directions] | 5:3`0 p.m. | ||
| Tue., 4/19 | JV Softball | Newtown | Home - Community Softball Field [Directions] | 3:45 p.m. | 2:15, one way bus | |
| Tue., 4/19 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 pm | |
| Tue., 4/19 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 2:30 p.m. | 2:30 - 9:00 pm | |
| Wed., 4/20 | V Baseball | Brookfield | Home - PHS Baseball Field [Directions] | W 10-4 | ||
| Wed., 4/20 | FR Baseball | Brookfield | Away - BHS Baseball Field [Directions] | 3:45 p.m. | 2:15 pm | |
| Wed., 4/20 | V Boys Tennis | Bethel | Away [Directions] | W 7-0 | 2:15 pm | |
| Wed., 4/20 | V Softball | Brookfield | Home - PHS Softball Field [Directions] | W 7 - 3 | ||
| Wed., 4/20 | V Girls Tennis | Bethel | Home - PHS Tennis Courts [Directions] | W 6-1 | ||
| Wed., 4/20 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 pm | |
| Wed., 4/20 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 2:30 p.m. | 2:30 - 7:00 pm | |
| Wed., 4/20 | Miscellaneous Events | College Night | - PHS Main Gym | 5:00 p.m. | ||
| Thu., 4/21 | V Baseball | Bunnell | Away - Bunnell Baseball Field [Directions] | W 9-6 | 2:15, share bus with softball | |
| Thu., 4/21 | JV Baseball | Brookfield | Home - Community Baseball Field [Directions] | 3:45 p.m. | 2:15, one way bus | |
| Thu., 4/21 | FR Baseball | Bunnell | Home - PHS Baseball Field [Directions] | 3:45 p.m. | ||
| Thu., 4/21 | V Boys Golf | Masuk | Home - Heritage Village C.C. [Directions] | Pomperaug 173 Masuk 174 | ||
| Thu., 4/21 | V Boys Lacrosse | Newtown | Away - Blue and Gold Stadium [Directions] | L 2-19 | 5:15 | Cross Over Game |
| Thu., 4/21 | JV Boys Lacrosse | Newtown | Away - Blue and Gold Stadium [Directions] | 5:15 p.m. | 4:00 pm | |
| Thu., 4/21 | V Boys Tennis | Stratford | Home - PHS Tennis Courts [Directions] | W 7-0 | ||
| Thu., 4/21 | V Girls Lacrosse | Newtown | Home - Sports Complex & Track [Directions] | W 16-15(OT) | Cross Over Game | |
| Thu., 4/21 | JV Girls Lacrosse | Newtown | Home - Sports Complex & Track [Directions] | 5:15 p.m. | ||
| Thu., 4/21 | V Softball | Bunnell | Away - Bunnell Softball Field [Directions] | W 2-1 | 2:15, share bus with baseball | |
| Thu., 4/21 | JV Softball | Brookfield | Home - Community Softball Field [Directions] | 3:45 p.m. | 2:15, one way bus | |
| Thu., 4/21 | V Girls Tennis | Stratford | Away - Short Beach Tennis Courts [Directions] | W 7-0 | 2:15 pm | |
| Thu., 4/21 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 pm | |
| Thu., 4/21 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 2:30 p.m. | 2:30 - 9:00 pm | |
| Fri., 4/22 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 pm | |
| Fri., 4/22 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 2:30 p.m. | 2:30 - 5:00 pm | |
| Fri., 4/22 | Miscellaneous Events | Student Council Dance | - PHS Main Gym | 6:30 p.m. | Set-Up 5:00 pm 6:30 - 10:30 pm | |
| Fri., 4/22 | School Holidays and Closings | Passover begins at sundown | ||||
| Sat., 4/23 | V Baseball | Ridgefield | Away - Governor's Park Field (aka Ciuccoli or Old HS) [Directions] | L 2-6 | 9:00 am, pick up at Ewald Park | |
| Sat., 4/23 | JV Baseball | Bunnell | Away - Bunnell Baseball Field [Directions] | 2:00 p.m. | 12:00 pm, share bus with JV softball | |
| Sat., 4/23 | V Boys Lacrosse | Bethel | Home - Sports Complex & Track [Directions] | W 7-6 | Cross Over Game | |
| Sat., 4/23 | JV Boys Lacrosse | Bethel | Home - Sports Complex & Track [Directions] | 12:00 p.m. | ||
| Sat., 4/23 | V Softball | Ridgefield | Away - RHS Upper Grass Field [Directions] | L 1-4 | 9:00 am | |
| Sat., 4/23 | JV Softball | Bunnell | Away - Bunnell Softball Field [Directions] | 2:00 p.m. | 12:00, share bus with JV Baseball | |
| Sat., 4/23 | Miscellaneous Events | Pomperaug Pop Warner Registration | - Health Classroom - Room 201 | 9:00 a.m. | 9:00 am - 2:00 pm | |
| Sat., 4/23 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 9:00 a.m. | 9:00 am - 2:00 pm | |
| Sat., 4/23 | School Holidays and Closings | First day of Passover | ||||
| Mon., 4/25 | V Baseball | Weston | Home - PHS Baseball Field [Directions] | W 8-2 | ||
| Mon., 4/25 | FR Baseball | Weston | Away - Revson Field, Weston [Directions] | 3:45 p.m. | 2:15 pm | |
| Mon., 4/25 | V Boys Golf | New Fairfield | Away [Directions] | Pomperaug 164 New Fairfield 188 | 1:45 pm | |
| Mon., 4/25 | V Boys Tennis | Newtown | Home - PHS Tennis Courts [Directions] | W 7-0 | ||
| Mon., 4/25 | V Girls Lacrosse | Lauralton Hall | Away - Lauralton Hall Field [Directions] | W 16-12 | 2:15 pm, share bus with JVs | |
| Mon., 4/25 | JV Girls Lacrosse | Lauralton Hall | Away - Lauralton Hall Field [Directions] | 5:15 p.m. | 2:15, share bus with Varsity | |
| Mon., 4/25 | V Girls Outdoor Track | Immaculate, Bunnell, New Fairfield | Away - Bunnell [Directions] | PHS 105 Bunnell 45 PHS 110 IHS 30 PHS 126 NFHS 14 | 2:15 pm | @ Bunnell HS |
| Mon., 4/25 | V Softball | Weston | Home - PHS Softball Field [Directions] | W 5-0 | ||
| Mon., 4/25 | V Girls Tennis | Newtown | Away - Newtown HS [Directions] | L 2-5 | 2:15 pm | |
| Mon., 4/25 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 pm | |
| Mon., 4/25 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 2:30 p.m. | 2:30 - 7:00 pm | |
| Mon., 4/25 | Miscellaneous Events | Mdby Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 4/26 | V Boys Outdoor Track | New Fairfield, Bunnell, Immaculate | Away - Sports Complex & Track [Directions] | Pomperaug 87 vs New Fairfield 55 Pomperaug 82 vs Immaculate 50 Pomperaug 72 vs Bunnell 78 | 2:15 pm, 2 buses | @ New Fairfield |
| Tue., 4/26 | V Girls Lacrosse | Southington | Away - Turf Field SHS [Directions] | W 18-3 | 2:15 pm share bus w/jv | |
| Tue., 4/26 | JV Girls Lacrosse | Southington | Away - Turf Field SHS [Directions] | 5:15 p.m. | 2:15 share bus w/varsity | |
| Tue., 4/26 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 pm | |
| Tue., 4/26 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 2:30 p.m. | 2:30 - 6:00 pm | |
| Wed., 4/27 | V Baseball | Kolbe Cathedral | Away - Seaside Park Field #10 [Directions] | W 23-6 | 2:15, share bus with softball | |
| Wed., 4/27 | JV Baseball | Weston | Home - Community Baseball Field [Directions] | 3:45 p.m. | 2:15, one way bus | |
| Wed., 4/27 | V Boys Golf | Newtown | Home - Heritage Village C.C. [Directions] | Pomperaug 162 Newtown 163 | ||
| Wed., 4/27 | V Softball | Kolbe Cathedral | Away - UB Softball Field at Seaside Park [Directions] | W 15-1 | 2:15 share bus with baseball | |
| Wed., 4/27 | JV Softball | Weston | Home - Community Softball Field [Directions] | 3:45 p.m. | 2:15, one way bus | |
| Wed., 4/27 | V Girls Tennis | Notre Dame-Fairfield | Home - PHS Tennis Courts [Directions] | W 7-0 | ||
| Wed., 4/27 | Miscellaneous Events | Freshmen Council Meeting | - Health Classroom - Room 201 | 2:15 p.m. | 2:15 - 3:00 pm | |
| Wed., 4/27 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 pm | |
| Wed., 4/27 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 3:00 p.m. | 3:00 - 7:00 pm | |
| Thu., 4/28 | V Baseball | Bethel | Home - PHS Baseball Field [Directions] | W 4-3 | ||
| Thu., 4/28 | V Boys Lacrosse | Weston | Away - WHS Turf Field [Directions] | L 7-9 | 4:30 | Cross Over Game |
| Thu., 4/28 | JV Boys Lacrosse | Weston | Away - WHS Turf Field [Directions] | 4:30 p.m. | 2:30 | |
| Thu., 4/28 | V Boys Tennis | New Fairfield | Home - PHS Tennis Courts [Directions] | W 7-0 | ||
| Thu., 4/28 | V Girls Lacrosse | Weston | Home - Sports Complex & Track [Directions] | W 14-10 | Cross Over Game | |
| Thu., 4/28 | JV Girls Lacrosse | Weston | Home - Sports Complex & Track [Directions] | 5:45 p.m. | ||
| Thu., 4/28 | V Softball | Bethel | Home - PHS Softball Field [Directions] | W 2-0 | ||
| Thu., 4/28 | V Girls Tennis | New Fairfield | Away [Directions] | W 5-2 | 2:15 pm | |
| Thu., 4/28 | Miscellaneous Events | Art Show Set Up | - PHS Main Gym | 8:00 a.m. | ||
| Thu., 4/28 | Miscellaneous Events | SWC Meeting | - Health Classroom - Room 201 | 8:30 a.m. | 8:30 am to 12:00 pm | |
| Thu., 4/28 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 pm | |
| Thu., 4/28 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 2:30 p.m. | 2:30 - 9:00 pm | |
| Fri., 4/29 | FR Baseball | Bethel | Away - Parloa Field [Directions] | 3:45 p.m. | 2:15 pm | |
| Fri., 4/29 | V Boys Outdoor Track | O'Grady relay | Away | 5:30 p.m. | 4:00 pm, Share bus with boys track | @ Danbury HS |
| Fri., 4/29 | V Girls Outdoor Track | O'Grady Relays | Away | 5:30 p.m. | 4:00 pm, Share bus with boys track | @ Danbury HS |
| Fri., 4/29 | Miscellaneous Events | Region 15 Art Show | - PHS Main Gym | 7:00 a.m. | 7:00 am - 10:00 pm | |
| Fri., 4/29 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 pm | |
| Fri., 4/29 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 2:30 p.m. | 2:30 - 7:00 pm | |
| Sat., 4/30 | JV Baseball | Bethel | Home - PHS Baseball Field [Directions] | 9:00 a.m. | ||
| Sat., 4/30 | V Boys Lacrosse | Stamford | Away - Stamford HS [Directions] | L 7-10 | 5:00 pm | |
| Sat., 4/30 | JV Boys Lacrosse | Stamford | Away - Stamford High Soccer Field [Directions] | 5:00 p.m. | 3:00 pm | |
| Sat., 4/30 | V Boys Outdoor Track | O'Grady Relays | Away | 9:00 a.m. | 7:45 am, share bus with girls track | @ Danbury |
| Sat., 4/30 | V Girls Outdoor Track | O'Grady Relays | Away | 9:00 a.m. | 7:45 am, share bus with boys track | @ Danbury HS |
| Sat., 4/30 | JV Softball | Bethel | Home - PHS Softball Field [Directions] | Cancelled | ||
| Sat., 4/30 | Miscellaneous Events | Region 15 Art Show | - PHS Main Gym | 7:00 a.m. | 7:00 am - 6:00 pm | |
| Sat., 4/30 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 9:00 a.m. | 9:00 am - 11:00 am | |
| Sat., 4/30 | School Holidays and Closings | Last day of Passover | ||||
| Sun., 5/1 | Miscellaneous Events | Youth Lacrosse Honor the Game Day | - Sports Complex & Track | 7:00 a.m. | 7:00 am - 6:00 pm | |
| Sun., 5/1 | Miscellaneous Events | Youth Lacrosse Honor the Game Day | - PHS Soccer Field | 7:00 a.m. | 7:00 am - 6:00 pm | |
| Sun., 5/1 | Miscellaneous Events | Youth Lacrosse Honor the Game Day | - Auxiliary Gym | 8:00 a.m. | 8:00 - 3:00 pm For photos | |
| Mon., 5/2 | V Baseball | Stratford | Away - Penders Field [Directions] | L 0-2 | 5:15 pm | |
| Mon., 5/2 | FR Baseball | Stratford | Home - PHS Baseball Field [Directions] | 3:45 p.m. | ||
| Mon., 5/2 | V Boys Golf | Immaculate | Home - Heritage Village C.C. [Directions] | Pomperaug 166 Immaculate 174 | ||
| Mon., 5/2 | V Boys Lacrosse | Lewis Mills | Away - Lewis Mills Lacrosse Field [Directions] | W 14-2 | 2:15 pm | |
| Mon., 5/2 | JV Boys Lacrosse | Lewis Mills | Away - Lewis Mills Lacrosse Field [Directions] | 5:15 p.m. | 3:15 pm | |
| Mon., 5/2 | V Girls Outdoor Track | Weston, Notre Dame-Fairfield | Away - WHS Stadium Field [Directions] | WHS 96.5 PHS 53.5 PHS 130.5 NDHS 10.5 | 3:00 pm | @ Weston |
| Mon., 5/2 | V Softball | Stratford | Away - DeLuca Field [Directions] | W 22-0 | 5:15 pm | |
| Mon., 5/2 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 2:00 p.m. | 2:00 - 6:00 pm | |
| Mon., 5/2 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 4:00 p.m. | 4:00 - 8:30 pm | |
| Tue., 5/3 | V Boys Golf | Weston | Home - Heritage Village C.C. [Directions] | Pomperaug 158 Weston 172 | ||
| Tue., 5/3 | V Boys Outdoor Track | Weston, Notre Dame-Fairfield | Home - Sports Complex & Track [Directions] | Pomperaug 78.5 Weston 71.5 Pomperaug 128 Notre Dame, Fairfield 12 | ||
| Tue., 5/3 | V Girls Lacrosse | Bethel | Away - Rockwell Field [Directions] | W 20-10 | 2:30 pm | Cross Over Game |
| Tue., 5/3 | JV Girls Lacrosse | Bethel | Away - Rockwell Field [Directions] | 5:30 p.m. | 4:00 pm | |
| Tue., 5/3 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 2:00 p.m. | 2:00 - 7:00 pm | |
| Tue., 5/3 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 3:00 p.m. | 3:00 - 7:30 pm | |
| Wed., 5/4 | FR Baseball | Newtown | Home - PHS Baseball Field [Directions] | 3:45 p.m. | ||
| Wed., 5/4 | V Boys Golf | Notre Dame-Fairfield | Away - Fairchild Wheeler Golf Course [Directions] | Pomperaug 160 Notre Dame 173 | 1:45 pm | |
| Wed., 5/4 | FR Softball | Newtown | Home - PHS Softball Field [Directions] | 3:30 p.m. | ||
| Wed., 5/4 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 2:00 p.m. | 2:00 - 7:00 pm | |
| Wed., 5/4 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 4:00 p.m. | 4:00 - 8:30 pm | |
| Thu., 5/5 | V Baseball | Notre Dame-Fairfield | Home - PHS Baseball Field [Directions] | L 0-3 | ||
| Thu., 5/5 | JV Baseball | Newtown | Away - Newtown HS Baseball Field [Directions] | 3:30 p.m. | 2:15, share bus with JV Softball | |
| Thu., 5/5 | V Boys Golf | Woodland Tournament | Away | Pomperaug 165 | 7:00 am | |
| Thu., 5/5 | V Boys Tennis | Masuk | Away - Wolfe Park Tennis Courts [Directions] | W 7-0 | 2:15 pm | |
| Thu., 5/5 | V Softball | Newtown | Away - Newtown HS Softball Field [Directions] | W 7-3 | 5:30 pm | |
| Thu., 5/5 | JV Softball | Newtown | Away - Treadwell Town Park [Directions] | 3:45 p.m. | 2:15, share bus with JV Baseball | |
| Thu., 5/5 | V Girls Tennis | Masuk | Home - PHS Tennis Courts [Directions] | W 7-0 | ||
| Thu., 5/5 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 2:00 p.m. | 2:00 - 7:00 pm | |
| Thu., 5/5 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 3:00 p.m. | 3:00 - 7:30 pm | |
| Fri., 5/6 | V Girls Lacrosse | Branford | Away - Branford HS-Turf Field [Directions] | L 11-16 | 4:30 pm | |
| Fri., 5/6 | JV Girls Lacrosse | Branford | Away - Branford HS-Turf Field [Directions] | 5:30 p.m. | 4:00 pm | |
| Fri., 5/6 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 2:00 p.m. | 2:00 - 7:00 pm | |
| Fri., 5/6 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 2:30 p.m. | 2:30 - 6:30 pm | |
| Sat., 5/7 | V Baseball | Newtown | Away - Community Field Southbury CT [Directions] | L 0-1 | 2:30 pm | |
| Sat., 5/7 | V Boys Lacrosse | Bunnell-Stratford | Away - Bunnell [Directions] | W 12-7 | 4:00 pm | Division Game |
| Sat., 5/7 | JV Boys Lacrosse | Bunnell-Stratford | Away - Bunnell Turf Field [Directions] | 4:00 p.m. | 2:00 pm | |
| Sat., 5/7 | V Girls Lacrosse | Bunnell | Home - Sports Complex & Track [Directions] | W 20-8 | Division Game | |
| Sat., 5/7 | JV Girls Lacrosse | Bunnell | Home - Sports Complex & Track [Directions] | 5:15 p.m. | ||
| Sat., 5/7 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 8:00 a.m. | 8:00 - 1:00 pm | |
| Sat., 5/7 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 5:00 p.m. | 5:00 - 9:00 pm | |
| Mon., 5/9 | V Baseball | New Fairfield | Away - NFHS Baseball Field [Directions] | W 3-1 | 2:15 share bus with softball | |
| Mon., 5/9 | V Boys Golf | Masuk | Away - Whitney Farms Golf Course [Directions] | Pomperaug 183 Masuk 177 | 1:45 pm | |
| Mon., 5/9 | V Boys Tennis | Immaculate | Away - Rogers Park [Directions] | W 7-0 | 2:15 pm | |
| Mon., 5/9 | V Girls Outdoor Track | Brookfield, Kolbe Cathedral, Stratford | Away - BHS Stadium Field [Directions] | PHS 131 SHS 10 PHS 116 KHS 25 PHS 92 Brook 58 | 2:15 pm | @ Brookfield |
| Mon., 5/9 | V Softball | New Fairfield | Away - NFHS Softball Field [Directions] | W 13-2 | 2:15 share bus with baseball | |
| Mon., 5/9 | V Girls Tennis | Immaculate | Home - PHS Tennis Courts [Directions] | W 6-1 | ||
| Mon., 5/9 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 2:00 p.m. | 2:00 - 7:00 pm | |
| Mon., 5/9 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 4:00 p.m. | 4:00 - 8:30 pm | |
| Tue., 5/10 | JV Baseball | New Fairfield | Home - Community Softball Field [Directions] | 3:45 p.m. | ||
| Tue., 5/10 | V Boys Golf | Bethel | Home - Heritage Village C.C. [Directions] | Pomperaug 166 Bethel 177 | ||
| Tue., 5/10 | V Boys Lacrosse | Immaculate | Away - Mustang Valley [Directions] | W 16-4 | 2:30 pm | Division Game |
| Tue., 5/10 | V Boys Outdoor Track | Brookfield, Kolbe Cathedral, Stratford | Away - BHS Stadium Field [Directions] | Pomperaug 80.5 Brookfield 68.5 Pomperaug 112 Stratford 30 Pomperaug 127 Kolbe Cathedral 10 | 2:15 pm, 2 buses | @ Brookfield |
| Tue., 5/10 | V Boys Tennis | Joel Barlow | Home - PHS Tennis Courts [Directions] | W 6-1 | ||
| Tue., 5/10 | V Girls Lacrosse | Immaculate | Home - Sports Complex & Track [Directions] | W 19-6 | Division Game | |
| Tue., 5/10 | JV Girls Lacrosse | Immaculate | Home - Sports Complex & Track [Directions] | Cancelled | ||
| Tue., 5/10 | V Softball | Notre Dame-Fairfield | Home - PHS Softball Field [Directions] | W 7-3 | ||
| Tue., 5/10 | JV Softball | New Fairfield | Home - Community Baseball Field [Directions] | 3:45 p.m. | ||
| Tue., 5/10 | V Girls Tennis | Joel Barlow | Away - Tennis Courts [Directions] | L 1-6 | 2:15 pm | |
| Tue., 5/10 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 2:00 p.m. | 2:00 - 9:00 pm | |
| Tue., 5/10 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 3:00 p.m. | 3:00 - 7:30 pm | |
| Wed., 5/11 | V Baseball | New Milford | Home - PHS Baseball Field [Directions] | L 2-10 | ||
| Wed., 5/11 | FR Baseball | New Milford | Away - New Milford HS [Directions] | 3:45 p.m. | 2:15 pm | |
| Wed., 5/11 | V Boys Tennis | Joel Barlow | Away - Tennis Courts [Directions] | W 7-0 | 2:15 pm | Non-League Game |
| Wed., 5/11 | V Softball | New Milford | Home - PHS Softball Field [Directions] | W 3-2 | ||
| Wed., 5/11 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 2:00 p.m. | 2:00 - 7:00 pm | |
| Wed., 5/11 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 4:00 p.m. | 4:00 - 8:30 pm | |
| Wed., 5/11 | School Holidays and Closings | Prof Development - Half Day | ||||
| Thu., 5/12 | V Baseball | Joel Barlow | Away - Field G (Baseball) [Directions] | L 4-8 | 2:15, share bus with softball | |
| Thu., 5/12 | JV Baseball | New Milford | Home - Community Baseball Field [Directions] | 3:45 p.m. | 2:15, one way bus | |
| Thu., 5/12 | FR Baseball | New Fairfield | Home - PHS Baseball Field [Directions] | 3:45 p.m. | ||
| Thu., 5/12 | V Boys Golf | Joel Barlow | Home - Heritage Village C.C. [Directions] | Pomperaug 177 Barlow 156 | ||
| Thu., 5/12 | V Boys Lacrosse | Masuk | Away - Benedict Stadium Field @ Masuk HS [Directions] | L 6-8 | 5:00 | Division Game |
| Thu., 5/12 | JV Boys Lacrosse | Masuk | Away - Benedict Stadium Field @ Masuk HS [Directions] | 5:00 p.m. | 3:30 | |
| Thu., 5/12 | V Boys Outdoor Track | Bethel Freshmen Meet | Away | 4:00 p.m. | 2:15 share bus with girls freshmen track | |
| Thu., 5/12 | V Boys Tennis | New Milford | Away [Directions] | W 6-1 | 2:15 pm | |
| Thu., 5/12 | V Girls Lacrosse | Masuk | Home - Sports Complex & Track [Directions] | W 20-9 | Division Game | |
| Thu., 5/12 | JV Girls Lacrosse | Masuk | Home - Sports Complex & Track [Directions] | 7:00 p.m. | ||
| Thu., 5/12 | V Girls Outdoor Track | Bethel Freshmen Meet | Away [Directions] | 4:00 p.m. | 2:15 pm | @ Bethel High School |
| Thu., 5/12 | V Softball | Joel Barlow | Away - Field E (Softball) [Directions] | W 4-1 | 2:15, share bus with baseball | |
| Thu., 5/12 | JV Softball | New Milford | Home - Community Softball Field [Directions] | 3:45 p.m. | 2:15, one way bus | |
| Thu., 5/12 | V Girls Tennis | New Fairfield | Home - PHS Tennis Courts [Directions] | W 6-1 | Non-League Game | |
| Thu., 5/12 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 3:00 p.m. | 3:00 - 7:30 pm | |
| Thu., 5/12 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 4:00 p.m. | 4:00 - 9:00 pm | |
| Fri., 5/13 | FR Baseball | Joel Barlow | Home - PHS Baseball Field [Directions] | 3:45 p.m. | ||
| Fri., 5/13 | V Girls Outdoor Track | Loucks Games | Away | TBA | 12:30, Share bus with boys track | |
| Fri., 5/13 | Miscellaneous Events | CT State Robotics Championship | - PHS Main Gym | 12:45 p.m. | 12:45 - 7:00 Set up | |
| Fri., 5/13 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 2:00 p.m. | 2:00 - 7:00 pm | |
| Fri., 5/13 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 2:30 p.m. | 2:30 - 6:30 pm | |
| Sat., 5/14 | JV Baseball | Joel Barlow | Away - Field G (Baseball) [Directions] | 10:00 a.m. | 8:00 am | |
| Sat., 5/14 | V Boys Outdoor Track | Greater Hartford Open | Away [Directions] | TBA | 7:00 am, Share bus with girls track | @ Simsbury HS |
| Sat., 5/14 | V Girls Outdoor Track | Greater Hartford Invitational | Away [Directions] | TBA | 7:00 am, Share bus with boys track | @ Simsbury HS |
| Sat., 5/14 | V Girls Tennis | New Milford | Home - PHS Tennis Courts [Directions] | W 7-0 | ||
| Sat., 5/14 | Miscellaneous Events | CT State Robotics Championship | - PHS Main Gym | 8:00 a.m. | 8:00 am - 3:30 pm | |
| Sat., 5/14 | Miscellaneous Events | CT State Robotics Championship | - Auxiliary Gym | 8:00 a.m. | 8:00 am - 3:30 pm | |
| Sat., 5/14 | Miscellaneous Events | Powder Puff Football Game | - Sports Complex & Track | 4:00 p.m. | 4:00 to 9:00 pm | |
| Sat., 5/14 | Miscellaneous Events | Kinetic Kids Gymnastics Enhibition Set-Up | - PHS Main Gym | 6:00 p.m. | 6:00 - 10:00 pm | |
| Sun., 5/15 | Miscellaneous Events | Kinetic Kids Gymnastics Enhibition | - PHS Main Gym | 7:00 a.m. | 7:00 am - 5:00 pm | |
| Mon., 5/16 | V Baseball | Masuk | Home - PHS Baseball Field [Directions] | W 7-4 | ||
| Mon., 5/16 | FR Baseball | Masuk | Away - Wolfe Park [Directions] | 4:00 p.m. | 2:15 pm | |
| Mon., 5/16 | V Boys Tennis | Joel Barlow | Home - PHS Tennis Courts [Directions] | W 7-0 | SWC Team Tournament Semi-Finals | |
| Mon., 5/16 | V Girls Outdoor Track | Masuk, Joel Barlow, New Milford | Away - Masuk HS Track [Directions] | PHS 97 Masuk 49 PHS 94 Barlow 52 PHS 93 NMHS 57 | 2:15 pm | @ Masuk |
| Mon., 5/16 | V Softball | Masuk | Home - PHS Softball Field [Directions] | L 9-14 | ||
| Mon., 5/16 | V Girls Tennis | SWC Team Semi-Finals | Away | 3:30 p.m. | TBA | @ Higher Ranked Site |
| Mon., 5/16 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 2:00 p.m. | 2:00 - 9:00 pm | |
| Mon., 5/16 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 4:00 p.m. | 4:00 - 8:30 pm | |
| Tue., 5/17 | V Baseball | Immaculate | Home - PHS Baseball Field [Directions] | W 15-7 | ||
| Tue., 5/17 | JV Baseball | Masuk | Home - Community Baseball Field [Directions] | 3:45 p.m. | 2:15, one way bus | |
| Tue., 5/17 | V Boys Outdoor Track | Masuk, Joel Barlow, New Milford | Home - Sports Complex & Track [Directions] | Pomperaug 91 Joel Barlow 58 Pomperaug 63.5 New Milford 81.5 Pomperaug 45 Masuk 105 | ||
| Tue., 5/17 | V Softball | Immaculate | Home - PHS Softball Field [Directions] | W 10-1 | ||
| Tue., 5/17 | JV Softball | Masuk | Home - Community Softball Field [Directions] | 3:45 p.m. | 2:15, one way bus | |
| Tue., 5/17 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 2:00 p.m. | 2:00 - 7:00 pm | |
| Tue., 5/17 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 3:00 p.m. | 3:00 - 7:30 pm | |
| Wed., 5/18 | JV Baseball | Immaculate | Home - Community Baseball Field [Directions] | 3:45 p.m. | 2:15, one way bus to community | |
| Wed., 5/18 | JV Baseball | Immaculate | Home - Community Baseball Field [Directions] | Cancelled | ||
| Wed., 5/18 | V Boys Golf | Joel Barlow | Away - Redding Country Club [Directions] | Pomperaug 186 | 1:45 pm | |
| Wed., 5/18 | V Boys Lacrosse | Southington | Home - Sports Complex & Track [Directions] | L 9-15 | ||
| Wed., 5/18 | JV Boys Lacrosse | Southington | Home - Sports Complex & Track [Directions] | 5:15 p.m. | ||
| Wed., 5/18 | V Boys Tennis | SWC Team Championships | Away | 3:30 p.m. | 1:45 pm | @ Higher Ranked Team |
| Wed., 5/18 | JV Softball | Immaculate | Home - Community Softball Field [Directions] | Cancelled | ||
| Wed., 5/18 | V Girls Tennis | SWC Team Championship | Away | 3:30 p.m. | TBA | @ Higher Ranked Site |
| Wed., 5/18 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 2:00 p.m. | 2:00 - 9:00 pm | |
| Wed., 5/18 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 4:00 p.m. | 4:00 - 7:00 pm | |
| Wed., 5/18 | Miscellaneous Events | Mdby Park & Rec Lifeguard Testing | - PHS Pool | 7:00 p.m. | 7:00 - 8:30 pm | |
| Thu., 5/19 | V Baseball | Oxford | Home - PHS Baseball Field [Directions] | L 3-14 | ||
| Thu., 5/19 | JV Baseball | Oxford | Away - OHS Baseball Field [Directions] | 3:00 p.m. | 2:30 pm | |
| Thu., 5/19 | V Girls Lacrosse | Danbury | Home - Sports Complex & Track [Directions] | L 12-15 | ||
| Thu., 5/19 | JV Girls Lacrosse | Danbury | Home - Sports Complex & Track [Directions] | 5:15 p.m. | ||
| Thu., 5/19 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 2:00 p.m. | 2:00 - 9:00 pm | |
| Thu., 5/19 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 3:00 p.m. | 3:00 - 7:30 pm | |
| Fri., 5/20 | V Girls Lacrosse | Shelton | Home - Sports Complex & Track [Directions] | W 19-15 | ||
| Fri., 5/20 | JV Girls Lacrosse | Shelton | Home - Sports Complex & Track [Directions] | 5:15 p.m. | ||
| Fri., 5/20 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 2:00 p.m. | 2:00 - 7:00 pm | |
| Fri., 5/20 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 2:30 p.m. | 2:30 - 6:30 pm | |
| Sat., 5/21 | V Baseball | SWC Quarter Finals | Home - PHS Baseball Field [Directions] | 12:30 p.m. | $8 Adults, $5 Students | |
| Sat., 5/21 | V Softball | Bethel | Home - PHS Softball Field [Directions] | W 6-0 | $8 Adults, $5 Students | |
| Mon., 5/23 | V Baseball | SWC Semi-Finals | Away [Directions] | 7:00 p.m. | 5:15 pm | Penders Field, $8 Adults, $5 Students |
| Mon., 5/23 | JV Baseball | Ridgefield | Home - PHS Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/23 | V Boys Outdoor Track | SWC Championship Meet | Away [Directions] | 3:30 p.m. | 1:15 pm, share bus with girls track | |
| Mon., 5/23 | V Boys Tennis | SWC Individual Tournament | Away [Directions] | 3:00 p.m. | 1:45 pm | @ Rogers Park, Danbury |
| Mon., 5/23 | V Girls Outdoor Track | SWC Championship Meet | Away [Directions] | 3:30 p.m. | 1:15 pm | @ Bethel, $10 Adults, $5 Students |
| Mon., 5/23 | JV Softball | Ridgefield | Home - Community Softball Field [Directions] | 4:00 p.m. | 2:15 one way bus to community | |
| Mon., 5/23 | V Girls Tennis | SWC Individual Tournament | Away [Directions] | 3:00 p.m. | 1:45 pm | @ Joel Barlow |
| Mon., 5/23 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 2:00 p.m. | 2:00 - 7:00 pm | |
| Mon., 5/23 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 4:00 p.m. | 4:00 - 7:00 pm | |
| Mon., 5/23 | Miscellaneous Events | Lifeguard Recertifications | - Health Classroom - Room 201 | 5:00 p.m. | 5:00 - 7:00 pm | |
| Mon., 5/23 | Miscellaneous Events | Lifeguard Recertifications | - PHS Pool | 7:00 p.m. | 7:00 - 9:30 pm | |
| Tue., 5/24 | V Boys Lacrosse | SWC Div II Semi-Finals | Home - Sports Complex & Track [Directions] | 5:00 p.m. | $8 Adults, $5 Students. Double Headers Semifinals at Pomperaug. 5:00 and 7:00 pm | |
| Tue., 5/24 | V Girls Lacrosse | SWC Div II Semi-Finals | Away [Directions] | 7:00 p.m. | 5:00 pm | @ Bunnell - $8 Adults, $5 Students |
| Tue., 5/24 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 2:00 p.m. | 2:00 - 9:00 pm | |
| Tue., 5/24 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 3:00 p.m. | 3:00 - 7:00 pm | |
| Tue., 5/24 | Miscellaneous Events | Lifeguard Recertifications | - Health Classroom - Room 201 | 5:00 p.m. | 5:00 - 7:00 pm | |
| Tue., 5/24 | Miscellaneous Events | Lifeguard Recertifications | - PHS Pool | 7:00 p.m. | 7:00 - 9:30 pm | |
| Wed., 5/25 | V Baseball | SWC Championship Game | Away | Cancelled | $10 Adults, $5 Students | |
| Wed., 5/25 | V Boys Tennis | SWC Individual Tournament | Away [Directions] | 3:00 p.m. | 1:45 pm | @ Rogers Park, Danbury |
| Wed., 5/25 | V Softball | SWC Semi-Finals | Away [Directions] | 7:00 p.m. | 5:00 pm | DeLuca Field, $8 Adults, $5 Students |
| Wed., 5/25 | V Girls Tennis | SWC Individual Tournament | Away [Directions] | 3:00 p.m. | 2:30 pm | @ Joel Barlow |
| Wed., 5/25 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 6:00 a.m. | 6:00 - 7:00 am | |
| Wed., 5/25 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 2:00 p.m. | 2:00 - 7:00 pm | |
| Wed., 5/25 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 4:00 p.m. | 4:00 - 7:00 pm | |
| Wed., 5/25 | Miscellaneous Events | Lifeguard Recertifications | - Health Classroom - Room 201 | 5:00 p.m. | 5:00 - 7:00 pm | |
| Wed., 5/25 | Miscellaneous Events | Lifeguard Recertifications | - PHS Pool | 7:00 p.m. | 7:00 - 9:30 pm | |
| Thu., 5/26 | V Boys Golf | CHAPPA Tournament | Away | TBA | No Bus | |
| Thu., 5/26 | V Boys Lacrosse | SWC Championship Game Div II | Away [Directions] | 7:00 p.m. | 5:00 pm | @ Bunnell HS. $10 Adults, $5 Students |
| Thu., 5/26 | V Girls Lacrosse | SWC Div II Championship Game | Away [Directions] | 5:00 p.m. | 3:15 pm | @ Bunnell -- $10 Adults, $5 Students |
| Thu., 5/26 | V Softball | SWC Championship Game | Away [Directions] | 7:00 p.m. | 5:00 pm | DeLuca Field, $10 Adults, $5 Students |
| Thu., 5/26 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 2:00 p.m. | 2:00 - 7:00 pm | |
| Thu., 5/26 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 3:00 p.m. | 3:00 - 7:30 pm | |
| Fri., 5/27 | V Boys Golf | SWC Championship | Away | 7:30 a.m. | 6:00 am | @ Ridgewood CC, Danbury |
| Fri., 5/27 | Miscellaneous Events | Athletic Trainer | - Pomperaug HS | 2:00 p.m. | 2:00 - 7:00 pm | |
| Fri., 5/27 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 2:30 p.m. | 2:30 - 6:30 pm | |
| Sat., 5/28 | V Boys Lacrosse | Branford | Away - Branford HS-Turf Field [Directions] | 5:00 p.m. | 2:45 pm | |
| Sat., 5/28 | V Boys Tennis | State Tournament | Away [Directions] | TBA | 7:00 am | @ William Hall High School in West Hartford |
| Sat., 5/28 | V Girls Tennis | Sheehan | Home [Directions] | 10:00 a.m. | ||
| Mon., 5/30 | V Girls Tennis | Berlin | Away - Newington Tennis Center [Directions] | 11:00 a.m. | 9:15 am | @ The Newington Tennis Center |
| Mon., 5/30 | School Holidays and Closings | Memorial Day - No School | ||||
| Tue., 5/31 | V Baseball | Wethersfield | Home - PHS Baseball Field [Directions] | 3:30 p.m. | ||
| Tue., 5/31 | V Boys Outdoor Track | State Class L Tournament | Away | 3:00 p.m. | 12:00 pm, share bus with girls track | @ Middletown |
| Tue., 5/31 | V Girls Lacrosse | Bacon Academy | Away [Directions] | W 15-13 | 1:45 pm | |
| Tue., 5/31 | V Girls Outdoor Track | State Class L Championship | Away | 3:00 p.m. | 12:00 pm, Share bus with boys track | @ Middletown HS |
| Tue., 5/31 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 6:00 a.m. | 6:00 - 7:00 am | |
| Tue., 5/31 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 3:00 p.m. | 3:00 - 7:30 pm | |
| Wed., 6/1 | V Boys Golf | Newtown | Away - Rock Ridge Country Club [Directions] | 172 | 1:30 | |
| Wed., 6/1 | V Boys Lacrosse | Watertown | Away - John J. Mills Complex @ Watertown HS [Directions] | 5:30 p.m. | 4:00 pm | |
| Wed., 6/1 | V Softball | Berlin | Home [Directions] | W 8-4 | ||
| Wed., 6/1 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 PM | |
| Wed., 6/1 | Miscellaneous Events | Cross Country Team Meeting | - Health Classroom - Room 201 | 6:00 p.m. | ||
| Wed., 6/1 | Miscellaneous Events | Cross Country Team Meeting | - Health Classroom - Room 201 | 6:30 p.m. | 6:30 - 7:30 pm | |
| Thu., 6/2 | V Girls Lacrosse | Daniel Hand | Away - Surf Club [Directions] | 5:00 p.m. | 2:00 pm | |
| Thu., 6/2 | V Softball | Torrington | Away [Directions] | 4:00 p.m. | 2:15 pm | |
| Thu., 6/2 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 6:00 a.m. | 6:00 - 7:00 am | |
| Thu., 6/2 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 PM | |
| Fri., 6/3 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 PM | |
| Fri., 6/3 | Miscellaneous Events | Boys & Girls Charity Swim Meet | - PHS Pool | 5:00 p.m. | 5:00 - 9:00 pm | |
| Fri., 6/3 | Miscellaneous Events | Swim Fundraiser | - PHS Pool | 6:00 p.m. | ||
| Sun., 6/5 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 11:00 a.m. | 11:00 am - 1:30 pm | |
| Sun., 6/5 | School Holidays and Closings | Junior/Senior Prom | ||||
| Mon., 6/6 | V Boys Golf | CIAC Div. II Championship | Away - Timberlin GC - Kensington [Directions] | 7:00 a.m. | 6:15 am | |
| Mon., 6/6 | V Boys Golf | CIAC Tournament | Cancelled | 6:45 am | ||
| Mon., 6/6 | V Boys Outdoor Track | State Open Championship | Away | 1:30 p.m. | 11:15 am, Share bus with girls track | New Britain |
| Mon., 6/6 | V Girls Outdoor Track | State Open Championship | Away | 1:30 p.m. | 11:15 am, share bus with boys track | New Britain |
| Mon., 6/6 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 PM | |
| Mon., 6/6 | School Holidays and Closings | Teacher Work Day - No School | ||||
| Tue., 6/7 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 6:00 a.m. | 6:00 - 7:00 am | |
| Tue., 6/7 | Miscellaneous Events | Field Hockey Meeting | - Health Classroom - Room 201 | 2:15 p.m. | 2:15 - 3:00 pm | |
| Tue., 6/7 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 PM | |
| Tue., 6/7 | Miscellaneous Events | CPR Class for Coaches | - Health Classroom - Room 201 | 5:00 p.m. | ||
| Tue., 6/7 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 7:30 pm | |
| Wed., 6/8 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 PM | |
| Thu., 6/9 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 PM | |
| Thu., 6/9 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 7:30 pm | |
| Fri., 6/10 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:30 pm | |
| Sat., 6/11 | V Boys Outdoor Track | New England Chapmpionship | Away | TBA | New Britain | |
| Sat., 6/11 | V Girls Outdoor Track | New England Championships | Away | Cancelled | New Britain | |
| Sat., 6/11 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 10:00 a.m. | 10:00 am - 12:30 pm | |
| Sat., 6/11 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 3:00 p.m. | 3:00 - 5:30 pm | |
| Sun., 6/12 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 10:00 a.m. | 10:00 am - 12:30 pm | |
| Sun., 6/12 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 1:00 p.m. | 1:00 - 3:30 pm | |
| Mon., 6/13 | V Boys Outdoor Track | Decathlon, Hammer, Steeple Chase | Away [Directions] | Cancelled | @ Willowbrook Park in New Britain | |
| Tue., 6/14 | V Boys Outdoor Track | Decathlon, Hammer, Steeple Chase | Away | TBA | @ Willowbrook Park in New Britain | |
| Tue., 6/14 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 6:00 a.m. | 6:00 - 7:00 am | |
| Tue., 6/14 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 7:30 pm | |
| Wed., 6/15 | School Holidays and Closings | Last Day of School - Graduation | ||||
| Thu., 6/16 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 1:00 p.m. | 1:00 - 3:45 pm | |
| Thu., 6/16 | School Holidays and Closings | Teacher Work Day | ||||
| Fri., 6/17 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 1:00 p.m. | 1:00 - 3:45 pm | |
| Fri., 6/17 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 7:30 pm | |
| Sun., 6/19 | School Holidays and Closings | Fathers Day | ||||
| Mon., 6/20 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 7:00 a.m. | 7:00 - 10:00 am | |
| Tue., 6/21 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 7:00 a.m. | 7:00 - 10:00 am | |
| Tue., 6/21 | Miscellaneous Events | PHS Girls Track Camp - RAIN DATE | - Pomperaug HS | 8:00 a.m. | 8:00 - 4:00 pm | |
| Tue., 6/21 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 7:30 pm | |
| Wed., 6/22 | V Boys Golf | New England Championships | Away - Bretwood GC - Keene, NH | TBA | ||
| Wed., 6/22 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 7:00 a.m. | 7:00 - 10:00 am | |
| Wed., 6/22 | Miscellaneous Events | Cheerleading Camp | - PHS Main Gym | 12:00 p.m. | 12:00 - 6:30 pm | |
| Thu., 6/23 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 7:00 a.m. | 7:00 - 10:00 am | |
| Thu., 6/23 | Miscellaneous Events | Pop Warner Cheer Clinic | - PHS Softball Field | 8:00 a.m. | 8:00 - 11:30 am | |
| Thu., 6/23 | Miscellaneous Events | Cheerleading Camp | - PHS Main Gym | 9:00 a.m. | 9:00 am - 4:00 pm | |
| Thu., 6/23 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 7:30 pm | |
| Fri., 6/24 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 7:00 a.m. | 7:00 - 10:00 am | |
| Sat., 6/25 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 9:00 a.m. | 9:00 - 11:30 am | |
| Sun., 6/26 | Miscellaneous Events | Pop Warner Coaches Clinic | - PHS Main Gym | 6:00 a.m. | 6:00 am - 5:00 pm | |
| Sun., 6/26 | Miscellaneous Events | Pop Warner Coaches Clinic | - Auxiliary Gym | 6:00 a.m. | 6:00 am - 5:00 pm | |
| Sun., 6/26 | Miscellaneous Events | Pop Warner Coaches Clinic | - Health Classroom - Room 201 | 6:00 a.m. | 6:00 am - 5:00 pm | |
| Mon., 6/27 | Miscellaneous Events | Mdby Park & Rec Swim Lessons | - PHS Pool | 11:15 a.m. | 11:15 am - 2:30 pm | |
| Mon., 6/27 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 7:00 a.m. | 7:00 - 10:00 am | |
| Mon., 6/27 | Miscellaneous Events | Fundamental Field Hockey Camp | - Field Hockey Field | 8:30 a.m. | 8:30 am - 12:00 noon | |
| Tue., 6/28 | Miscellaneous Events | Mdby Park & Rec Swim Lessons | - PHS Pool | 11:15 a.m. | 11:15 am - 2:30 pm | |
| Tue., 6/28 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 7:00 a.m. | 7:00 - 10:00 am | |
| Tue., 6/28 | Miscellaneous Events | Fundamental Field Hockey Camp | - Field Hockey Field | 8:30 a.m. | 8:30 am - 12:00 noon | |
| Wed., 6/29 | Miscellaneous Events | Mdby Park & Rec Swim Lessons | - PHS Pool | 11:15 a.m. | 11:15 am - 2:30 pm | |
| Wed., 6/29 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 7:00 a.m. | 7:00 - 10:00 am | |
| Wed., 6/29 | Miscellaneous Events | Fundamental Field Hockey Camp | - Field Hockey Field | 8:30 a.m. | 8:30 am - 12:00 noon | |
| Wed., 6/29 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 7:30 pm | |
| Thu., 6/30 | Miscellaneous Events | Mdby Park & Rec Swim Lessons | - PHS Pool | 11:15 a.m. | 11:15 am - 2:30 pm | |
| Thu., 6/30 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 7:00 a.m. | 7:00 - 10:00 am | |
| Thu., 6/30 | Miscellaneous Events | Fundamental Field Hockey Camp | - Field Hockey Field | 8:30 a.m. | 8:30 am - 12:00 noon | |