| Pomperaug 2014-15 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 1693 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| TBA | FR Baseball | Bunnell | Away - Bunnell Baseball Field [Directions] | TBA | 2:15 pm | |
| TBA | FR Football | Masuk | Home - Sports Complex & Track [Directions] | 4:00 p.m. | ||
| TBA | JV Boys Lacrosse | Notre Dame-Fairfield | Home - Sports Complex & Track [Directions] | TBA | ||
| TBA | JV Boys Lacrosse | Holy Cross | Home - Sports Complex & Track [Directions] | TBA | ||
| TBA | JV Boys Soccer | Joel Barlow | Away - Field E (Softball) [Directions] | 2:00 p.m. | 12:30 pm | |
| TBA | FR Girls Basketball | Holy Cross | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| TBA | FR Girls Basketball | Masuk | Home - PHS Main Gym [Directions] | TBA | ||
| TBA | FR Field Hockey | New Fairfield | Away - Rebel Turf [Directions] | TBA | ||
| TBA | JV Girls Soccer | Bunnell | Home - Sports Complex & Track [Directions] | TBA | ||
| TBA | JV Softball | Joel Barlow | Away - Field E (Softball) [Directions] | TBA | 2:15 | |
| TBA | FR Girls Volleyball | Masuk | Home - PHS Main Gym [Directions] | 6:30 p.m. | ||
| TBA | FR Girls Volleyball | Shelton | Home - Auxiliary Gym [Directions] | TBA | ||
| Tue., 7/1 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:30 a.m. | 6:30 - 9:30 am | |
| Wed., 7/2 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:30 a.m. | 6:30 - 9:30 am | |
| Thu., 7/3 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:30 a.m. | 6:30 - 9:30 am | |
| Fri., 7/4 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Sat., 7/5 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 8:00 a.m. | 8:00 am - 9:00 pm | |
| Sun., 7/6 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 8:00 a.m. | 8:00 am - 9:00 pm | |
| Mon., 7/7 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:30 a.m. | 6:30 - 9:30 am | |
| Mon., 7/7 | Miscellaneous Events | Triple Threat Basketball Camp (Mdby Park & Rec) | - PHS Main Gym | 8:00 a.m. | 8:00 am - 2:00 pm | |
| Mon., 7/7 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Tue., 7/8 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:30 a.m. | 6:30 - 9:30 am | |
| Tue., 7/8 | Miscellaneous Events | Triple Threat Basketball Camp (Mdby Park & Rec) | - PHS Main Gym | 8:00 a.m. | 8:00 am - 2:00 pm | |
| Tue., 7/8 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Wed., 7/9 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:30 a.m. | 6:30 - 9:30 am | |
| Wed., 7/9 | Miscellaneous Events | Triple Threat Basketball Camp (Mdby Park & Rec) | - PHS Main Gym | 8:00 a.m. | 8:00 am - 2:00 pm | |
| Wed., 7/9 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Wed., 7/9 | Miscellaneous Events | CT Seahawks Softball | - PHS Softball Field | 5:45 p.m. | 5:45 - 7:45 pm | |
| Thu., 7/10 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:30 a.m. | 6:30 - 9:30 am | |
| Thu., 7/10 | Miscellaneous Events | Triple Threat Basketball Camp (Mdby Park & Rec) | - PHS Main Gym | 8:00 a.m. | 8:00 am - 2:00 pm | |
| Thu., 7/10 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Fri., 7/11 | Miscellaneous Events | Triple Threat Basketball Camp (Mdby Park & Rec) | - PHS Main Gym | 8:00 a.m. | 8:00 am - 2:00 pm | |
| Fri., 7/11 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Fri., 7/11 | Miscellaneous Events | Nutmeg Games Gymnastic Meet | - PHS Main Gym | TBA | ||
| Sat., 7/12 | Miscellaneous Events | Nutmeg Games Gymnastic Meet | - PHS Main Gym | 7:00 a.m. | 7:00 am - 10:00 pm | |
| Sat., 7/12 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 8:00 a.m. | 8:00 am - 9:00 pm | |
| Sun., 7/13 | Miscellaneous Events | Nutmeg Games Gymnastic Meet | - PHS Main Gym | 7:00 a.m. | 7:00 am - 6:00 pm | |
| Sun., 7/13 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 8:00 a.m. | 8:00 am - 9:00 pm | |
| Mon., 7/14 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:30 a.m. | 6:30 - 9:30 am | |
| Mon., 7/14 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Tue., 7/15 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:30 a.m. | 6:30 - 9:30 am | |
| Tue., 7/15 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Wed., 7/16 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:30 a.m. | 6:30 - 9:30 am | |
| Wed., 7/16 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Wed., 7/16 | Miscellaneous Events | CT Seahawks Softball | - PHS Softball Field | 5:45 p.m. | 5:45 - 7:45 pm | |
| Thu., 7/17 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:30 a.m. | 6:30 - 9:30 am | |
| Thu., 7/17 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Fri., 7/18 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Sat., 7/19 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 8:00 a.m. | 8:00 am - 9:00 pm | |
| Sun., 7/20 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 8:00 a.m. | 8:00 am - 9:00 pm | |
| Mon., 7/21 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:30 a.m. | 6:30 - 9:30 am | |
| Mon., 7/21 | Miscellaneous Events | Southbury Parks & Rec Basketball Camp | - PHS Main Gym | 9:00 a.m. | 9:00 am - 2:00 pm | |
| Mon., 7/21 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Tue., 7/22 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:30 a.m. | 6:30 - 9:30 am | |
| Tue., 7/22 | Miscellaneous Events | Southbury Parks & Rec Basketball Camp | - PHS Main Gym | 9:00 a.m. | 9:00 am - 2:00 pm | |
| Tue., 7/22 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Wed., 7/23 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:30 a.m. | 6:30 - 9:30 am | |
| Wed., 7/23 | Miscellaneous Events | Southbury Parks & Rec Basketball Camp | - PHS Main Gym | 9:00 a.m. | 9:00 am - 2:00 pm | |
| Wed., 7/23 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Wed., 7/23 | Miscellaneous Events | CT Seahawks Softball | - PHS Softball Field | 5:45 p.m. | 5:45 - 7:45 pm | |
| Thu., 7/24 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:30 a.m. | 6:30 - 9:30 am | |
| Thu., 7/24 | Miscellaneous Events | Southbury Parks & Rec Basketball Camp | - PHS Main Gym | 9:00 a.m. | 9:00 am - 2:00 pm | |
| Thu., 7/24 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Fri., 7/25 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Sat., 7/26 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 8:00 a.m. | 8:00 am - 9:00 pm | |
| Sun., 7/27 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 8:00 a.m. | 8:00 am - 9:00 pm | |
| Mon., 7/28 | Miscellaneous Events | Southbury Park & Rec Basketball Camp | - PHS Main Gym | 9:00 a.m. | 9:00 am - 2:00 pm | |
| Mon., 7/28 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Tue., 7/29 | Miscellaneous Events | Southbury Park & Rec Basketball Camp | - PHS Main Gym | 9:00 a.m. | 9:00 am - 2:00 pm | |
| Tue., 7/29 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Wed., 7/30 | Miscellaneous Events | Southbury Park & Rec Basketball Camp | - PHS Main Gym | 9:00 a.m. | 9:00 am - 2:00 pm | |
| Wed., 7/30 | Miscellaneous Events | Southbury Youth Baseball | - PHS Baseball Field | 5:00 p.m. | 5:00 - 9:00 pm | |
| Wed., 7/30 | Miscellaneous Events | CT Seahawks Softball | - PHS Softball Field | 5:45 p.m. | 5:45 - 7:45 pm | |
| Thu., 7/31 | Miscellaneous Events | Stby Parks & Rec Youth Swim Meet | - PHS Pool | 6:30 a.m. | 6:30 am - 4:00 pm | |
| Thu., 7/31 | Miscellaneous Events | Southbury Park & Rec Basketball Camp | - PHS Main Gym | 9:00 a.m. | 9:00 am - 2:00 pm | |
| Fri., 8/1 | Miscellaneous Events | Stby Parks & Rec Youth Swim Meet | - PHS Pool | 6:30 a.m. | 6:30 am - 4:00 pm | |
| Mon., 8/18 | Miscellaneous Events | Freshmen Orientation | - PHS Main Gym | 8:00 a.m. | ||
| Mon., 8/18 | Miscellaneous Events | Soccer Camp | - PHS Soccer Field | 5:00 p.m. | 5:00 to 7:30 pm | |
| Mon., 8/18 | Miscellaneous Events | Freshmen School Dance | - PHS Main Gym | 6:00 p.m. | 6:00 - 10:00 pm | |
| Tue., 8/19 | Miscellaneous Events | Soccer Camp | - PHS Soccer Field | 5:00 p.m. | 5:00 to 7:30 pm | |
| Wed., 8/20 | Miscellaneous Events | Soccer Camp | - PHS Soccer Field | 5:00 p.m. | 5:00 to 7:30 pm | |
| Thu., 8/21 | Miscellaneous Events | Soccer Camp | - PHS Soccer Field | 5:00 p.m. | 5:00 to 7:30 pm | |
| Thu., 8/21 | School Holidays and Closings | Teacher Work Day and Convocation | ||||
| Fri., 8/22 | Miscellaneous Events | Soccer Camp | - PHS Soccer Field | 5:00 p.m. | 5:00 to 7:30 pm | |
| Fri., 8/22 | School Holidays and Closings | In-Service Day | ||||
| Sun., 8/24 | V Boys Soccer | Alumni Scrimmage | Home - Sports Complex & Track [Directions] | 7:00 p.m. | ||
| Mon., 8/25 | Miscellaneous Events | CPR and First Aid Class For Coaches | - Health Classroom - Room 201 | 6:00 p.m. | ||
| Mon., 8/25 | School Holidays and Closings | In-Service Day | ||||
| Tue., 8/26 | School Holidays and Closings | First Day of School | ||||
| Wed., 8/27 | V Boys Soccer | Nonnewaug (Scrim.) | Home - Sports Complex & Track [Directions] | 7:00 p.m. | ||
| Thu., 8/28 | V Field Hockey | Cheshire (Scrim.) | Home - Sports Complex & Track [Directions] | 7:00 p.m. | ||
| Thu., 8/28 | V Girls Soccer | Staples (Scrim.) | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Thu., 8/28 | JV Girls Soccer | Staples (Scrim.) | Home - PHS Soccer Field [Directions] | 5:00 p.m. | ||
| Thu., 8/28 | V Girls Volleyball | Seymour (Scrim.) | Home - PHS Main Gym [Directions] | 3:30 p.m. | Varsity and JV on both nets in the Main gym | |
| Thu., 8/28 | JV Girls Volleyball | Seymour (Scrim.) | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 8/29 | V Boys Cross Country | Danbury (Scrim.) | Away [Directions] | 7:15 p.m. | 5:45 | |
| Fri., 8/29 | V Girls Cross Country | Danbury (Scrim.) | Away [Directions] | 7:15 p.m. | 5:45 | |
| Sat., 8/30 | V Football | Amity (Scrim.) | Away - William Johnson Football Field @ Amity HS [Directions] | 10:00 a.m. | 8:15 am, 2 buses | |
| Sat., 8/30 | FR Football | Amity (Scrim.) | Away [Directions] | 10:00 a.m. | 8:30 am | |
| Sat., 8/30 | V Boys Soccer | Cheshire (Scrim.) | Home - Sports Complex & Track [Directions] | 6:00 p.m. | ||
| Sat., 8/30 | JV Boys Soccer | Cheshire (Scrim.) | Home - Sports Complex & Track [Directions] | 4:30 p.m. | ||
| Sun., 8/31 | Miscellaneous Events | Pop Warner Football | - Sports Complex & Track | 11:00 a.m. | 11:00 am to 8:00 pm | |
| Mon., 9/1 | V Field Hockey | Pomperaug Play Day | Home - Sports Complex & Track [Directions] | 9:00 a.m. | Danbury and Hall HS. | |
| Mon., 9/1 | School Holidays and Closings | Labor Day - No School | ||||
| Wed., 9/3 | V Boys Soccer | Seymour (Scrim.) | Away - Seymour High Main Field [Directions] | 3:30 p.m. | 2:15 pm | |
| Wed., 9/3 | V Girls Soccer | Woodland (Scrim.) | Away - Woodland Soccer Field [Directions] | 3:30 p.m. | 2:15 | |
| Wed., 9/3 | V Girls Volleyball | Terryville (Scrim.) | Home - PHS Main Gym [Directions] | 3:45 p.m. | ||
| Wed., 9/3 | JV Girls Volleyball | Terryville (Scrim.) | Home - PHS Main Gym [Directions] | 3:45 p.m. | ||
| Wed., 9/3 | Miscellaneous Events | Pomperaug Pop Warner Cheerleading Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30pm | |
| Thu., 9/4 | V Football | Ridgefield (Scrim.) | Away - Tiger Hollow Stadium [Directions] | 5:00 p.m. | 3:00 pm, 2 buses | |
| Thu., 9/4 | V Field Hockey | Nonnewaug (Scrim.) | Home - Sports Complex & Track [Directions] | 7:00 p.m. | ||
| Thu., 9/4 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 2:15 p.m. | ||
| Fri., 9/5 | FR Football | Ridgefield (Scrim.) | Away - Tiger Hollow Turf Field II [Directions] | 4:00 p.m. | 2:30 pm | |
| Fri., 9/5 | V Boys Soccer | Bullard Havens Tech (Scrim.) | Home - Sports Complex & Track [Directions] | 4:00 p.m. | ||
| Fri., 9/5 | JV Field Hockey | New Fairfield (Scrim.) | Away [Directions] | 4:00 p.m. | 2:30 | New Fairfield JV Jamboree |
| Fri., 9/5 | Miscellaneous Events | Pop Warner Cheer Practice | 6:30 p.m. | 6:30 - 9:00 pm | ||
| Sat., 9/6 | V Boys Soccer | Amity (Scrim.) | Away [Directions] | 10:00 a.m. | 9:00 am | |
| Sat., 9/6 | V Field Hockey | New Fairfield (Scrim.) | Away [Directions] | 9:00 a.m. | 7:30 am | New Fairfield Jamboree |
| Sun., 9/7 | Miscellaneous Events | Pop Warner Football | - Sports Complex & Track | 1:00 p.m. | 1:00 pm to 3:00 pm | |
| Mon., 9/8 | V Girls Volleyball | Holy Cross (Scrim.) | Home - PHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 9/8 | JV Girls Volleyball | Holy Cross (Scrim.) | Home - PHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 9/8 | Miscellaneous Events | Pomperaug Pop Warner Cheerleading Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30pm | |
| Mon., 9/8 | Miscellaneous Events | PAC Swim Clinic | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Tue., 9/9 | V Boys Cross Country | Weston, Notre Dame-Fairfield | Away - WHS Track [Directions] | PHS 19 Weston 40 PHS 15 Notre Dame 48 | 2:15 pm | |
| Tue., 9/9 | V Girls Cross Country | Weston, Notre Dame-Fairfield | Away - WHS Track [Directions] | PHS 21 Weston 38 PHS 15 Notre Dame 50 | 2:30 pm | |
| Tue., 9/9 | V Girls Swimming and Diving | Immaculate | Home - PHS Pool [Directions] | Pomperaug 92- Immaculate/Bethel 70 | ||
| Wed., 9/10 | Miscellaneous Events | Pomperaug Pop Warner Cheerleading Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30pm | |
| Wed., 9/10 | Miscellaneous Events | PAC Swim Clinic | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Thu., 9/11 | FR Football | Bunnell | Home - Sports Complex & Track [Directions] | 4:00 p.m. | ||
| Thu., 9/11 | V Girls Volleyball | Griswold | Away - Gymnasium [Directions] | W 3-2 | 2:15 share bus with JVs | |
| Thu., 9/11 | JV Girls Volleyball | Griswold | Away - Gymnasium [Directions] | 4:30 p.m. | 2:15 share bus with varsity | |
| Thu., 9/11 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 2:15 p.m. | ||
| Fri., 9/12 | V Football | Bunnell | Away - Bunnell Turf Field [Directions] | W 14-6 | 4:30 pm, 2 buses | |
| Fri., 9/12 | V Competitive Cheerleading | Bunnell | Away [Directions] | 7:00 p.m. | 5:30 | |
| Fri., 9/12 | V Field Hockey | Immaculate | Home - Sports Complex & Track [Directions] | W 1-0 | non-league game | |
| Fri., 9/12 | JV Field Hockey | Immaculate | Home - Sports Complex & Track [Directions] | 3:30 p.m. | ||
| Fri., 9/12 | V Girls Swimming and Diving | Masuk | Away - Masuk Pool [Directions] | Pomperaug 101- Masuk 79 | 2:15 pm | |
| Fri., 9/12 | Miscellaneous Events | PAC Swim Clinic | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Fri., 9/12 | Miscellaneous Events | Pop Warner Cheer Practice | 6:30 p.m. | 6:30 - 9:00 pm | ||
| Sat., 9/13 | V Boys Cross Country | Wilton Invitational | Away | TBA | 7:15, share bus with girls cross country | |
| Sat., 9/13 | JV Football | Bunnell | Home - Sports Complex & Track [Directions] | 10:00 a.m. | ||
| Sat., 9/13 | V Boys Soccer | Naugatuck | Home - Sports Complex & Track [Directions] | L 1-3 | ||
| Sat., 9/13 | JV Boys Soccer | Naugatuck | Home - Sports Complex & Track [Directions] | 3:00 p.m. | ||
| Sat., 9/13 | FR Boys Soccer | Amity | Home - PHS Soccer Field [Directions] | 10:00 a.m. | ||
| Sat., 9/13 | JV Competitive Cheerleading | Bunnell | Home [Directions] | 10:00 a.m. | ||
| Sat., 9/13 | V Girls Cross Country | Wilton Invitational | Away | TBA | 7:15, share bus with boys cross country | |
| Sat., 9/13 | V Girls Soccer | Naugatuck | Away - Naugatuck High School [Directions] | W 5-1 | 11:45 am | |
| Sat., 9/13 | V Girls Volleyball | Norwich Free Academy | Home - PHS Main Gym [Directions] | L 0-3 | ||
| Sat., 9/13 | JV Girls Volleyball | Norwich Free Academy | Home - PHS Main Gym [Directions] | 11:00 a.m. | ||
| Mon., 9/15 | V Girls Volleyball | Brookfield | Away - BHS Big Gym [Directions] | L 2-3 | 2:15 Share bus with JVs | non-league game |
| Mon., 9/15 | JV Girls Volleyball | Brookfield | Away - BHS Big Gym [Directions] | 3:30 p.m. | 2:15, Share bus with varsity | |
| Mon., 9/15 | Miscellaneous Events | Pomperaug Pop Warner Cheerleading Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30pm | |
| Mon., 9/15 | Miscellaneous Events | PAC Swim Team Clinic | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Mon., 9/15 | Miscellaneous Events | PAC Swim Clinic | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Tue., 9/16 | V Boys Cross Country | Newtown, Brookfield, New Milford | Home - Pomperaug High School [Directions] | PHS 27 Brookfield 28 PHS 27 Newtown 29 NMHS 22 PHS 36 | ||
| Tue., 9/16 | V Boys Soccer | Bunnell | Away - Bunnell Turf Field [Directions] | W 3-0 | 5:00 pm | |
| Tue., 9/16 | JV Boys Soccer | Bunnell | Away - Bunnell Turf Field [Directions] | 5:00 p.m. | 3:15 pm | |
| Tue., 9/16 | V Girls Cross Country | Newtown, Brookfield, New Milford | Home - Pomperaug High School [Directions] | PHS 15 Brookfield 50 PHS 23 newtown 32 PHS 25 NMHS 33 | ||
| Tue., 9/16 | V Field Hockey | New Milford | Away - New Milford High School [Directions] | L 1-2 | 2:15, share bus with JVs | non-league game |
| Tue., 9/16 | JV Field Hockey | New Milford | Away - New Milford High School [Directions] | 5:30 p.m. | 2:15, share bus with Varsity | |
| Tue., 9/16 | V Girls Soccer | Bunnell | Home - Sports Complex & Track [Directions] | L 1-2 | ||
| Tue., 9/16 | V Girls Swimming and Diving | New Fairfield | Away - New Fairfield HS [Directions] | Pomperaug 95- New Fairfield 83 | 2:15 pm | |
| Tue., 9/16 | Miscellaneous Events | PAC Swim Team Clinic | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Wed., 9/17 | FR Boys Soccer | Masuk | Home - PHS Soccer Field [Directions] | 3:45 p.m. | ||
| Wed., 9/17 | FR Field Hockey | Newtown | Away - Treadwell Town Park [Directions] | 3:45 p.m. | 2:15 | |
| Wed., 9/17 | FR Girls Soccer | Masuk | Away - Masuk Middle Field [Directions] | 3:45 p.m. | 2:15 pm | |
| Wed., 9/17 | V Girls Volleyball | Stratford | Home - PHS Main Gym [Directions] | W 3-0 | non-league game | |
| Wed., 9/17 | JV Girls Volleyball | Stratford | Home - PHS Main Gym [Directions] | 5:00 p.m. | ||
| Wed., 9/17 | FR Girls Volleyball | New Milford | Away - New Milford High School [Directions] | 6:30 p.m. | 5:00 pm | |
| Wed., 9/17 | Miscellaneous Events | Pomperaug Pop Warner Cheerleading Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30pm | |
| Wed., 9/17 | Miscellaneous Events | PAC Swim Team Clinic | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Wed., 9/17 | Miscellaneous Events | PAC Swim Clinic | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Thu., 9/18 | V Boys Soccer | Bethel | Home - Sports Complex & Track [Directions] | W 2-0 | ||
| Thu., 9/18 | JV Boys Soccer | Bethel | Home - Sports Complex & Track [Directions] | 3:45 p.m. | ||
| Thu., 9/18 | V Field Hockey | Watertown | Away - John J. Mills Complex @ Watertown High School [Directions] | W 6-0 | 3:45, share bus with JVs | non-league game |
| Thu., 9/18 | JV Field Hockey | Watertown | Away - Swift Middle School [Directions] | 5:00 p.m. | 3:45, share bus with Varsity | |
| Thu., 9/18 | V Girls Soccer | Bethel | Away - Rourke Field [Directions] | W 3-1 | 2:15 pm | |
| Thu., 9/18 | JV Girls Soccer | Bethel | Away - Middle School Field [Directions] | 3:45 p.m. | 2:15 pm | |
| Thu., 9/18 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 2:15 p.m. | ||
| Thu., 9/18 | Miscellaneous Events | PAC Swim Team Clinic | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Fri., 9/19 | V Football | Weston | Home - Sports Complex & Track [Directions] | W 21-13 | ||
| Fri., 9/19 | JV Boys Soccer | New Milford | Away - New Milford High School [Directions] | 4:00 p.m. | 2:30 pm, Share bus Freshmen | |
| Fri., 9/19 | FR Boys Soccer | New Milford | Away - New Milford High School [Directions] | 3:45 p.m. | 2:30 Share bus with JVs | |
| Fri., 9/19 | V Competitive Cheerleading | Weston | Home - Sports Complex & Track [Directions] | 7:00 p.m. | ||
| Fri., 9/19 | V Girls Swimming and Diving | New Milford | Home - PHS Pool [Directions] | Pomperaug 96- New Milford 61 | ||
| Fri., 9/19 | V Girls Volleyball | Masuk | Away - David Strong Gymnasium @ Masuk High School [Directions] | L 0-3 | 2:15, share bus with JVs | non-league game |
| Fri., 9/19 | JV Girls Volleyball | Masuk | Away - David Strong Gymnasium @ Masuk High School [Directions] | 3:30 p.m. | 2:15, share bus with Varsity | |
| Fri., 9/19 | FR Girls Volleyball | Weston | Home - PHS Main Gym [Directions] | 4:15 p.m. | ||
| Fri., 9/19 | Miscellaneous Events | PAC Swim Team Clinic | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Fri., 9/19 | Miscellaneous Events | PAC Swim Clinic | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Fri., 9/19 | Miscellaneous Events | Pop Warner Cheer Practice | 6:30 p.m. | 6:30 - 9:00 pm | ||
| Sat., 9/20 | V Boys Cross Country | Amherst Invitational | Away | 10:00 a.m. | 7:30, Share bus with girls cross country | |
| Sat., 9/20 | JV Football | Weston | Away - WHS Stadium Field [Directions] | 10:00 a.m. | 8:00 am | |
| Sat., 9/20 | V Boys Soccer | New Milford | Away - New Milford High School [Directions] | L 1-2 | 2:15 pm | |
| Sat., 9/20 | V Girls Cross Country | Amherst Invitational | Away | 10:00 a.m. | 7:30, Share bus with boys | |
| Sat., 9/20 | V Field Hockey | Watertown | Home - Sports Complex & Track [Directions] | W 5-0 | ||
| Sat., 9/20 | JV Field Hockey | Watertown | Home - Sports Complex & Track [Directions] | 12:00 p.m. | ||
| Sat., 9/20 | FR Field Hockey | New Milford | Home - PHS Baseball Field [Directions] | 9:00 a.m. | ||
| Sat., 9/20 | V Girls Soccer | New Milford | Home - Sports Complex & Track [Directions] | W 1-0 | ||
| Sat., 9/20 | JV Girls Soccer | New Milford | Home - Sports Complex & Track [Directions] | 4:00 p.m. | ||
| Sat., 9/20 | FR Girls Soccer | New Milford | Home - PHS Soccer Field [Directions] | 9:00 a.m. | ||
| Sun., 9/21 | Miscellaneous Events | Pop Warner Football | - Sports Complex & Track | 5:00 p.m. | 5:00 pm to 7:00 pm | |
| Mon., 9/22 | V Girls Volleyball | Brookfield | Home - PHS Main Gym [Directions] | L 0-3 | ||
| Mon., 9/22 | JV Girls Volleyball | Brookfield | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Mon., 9/22 | FR Girls Volleyball | Newtown | Home - PHS Main Gym [Directions] | 6:30 p.m. | ||
| Mon., 9/22 | Miscellaneous Events | Pomperaug Pop Warner Cheerleading Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30pm | |
| Mon., 9/22 | Miscellaneous Events | PAC Swim Clinic | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Tue., 9/23 | V Boys Cross Country | Immaculate, Kolbe Cathedral, Bethel | Away [Directions] | PHS 15 Kolbe 50 PHS 19 Bethel 44 PHS 16 Immaculate 47 | 2:15 pm, share bus with girls cross country | |
| Tue., 9/23 | V Boys Soccer | Brookfield | Home - Sports Complex & Track [Directions] | L 0-1 | ||
| Tue., 9/23 | JV Boys Soccer | Brookfield | Home - Sports Complex & Track [Directions] | 3:45 p.m. | ||
| Tue., 9/23 | FR Boys Soccer | Newtown | Home - PHS Soccer Field [Directions] | 3:45 p.m. | ||
| Tue., 9/23 | V Girls Cross Country | Immaculate, Kolbe Cathedral, Bethel | Away [Directions] | PHS 15 Kolbe 50 PHS 17 Bethel 40 Immaculate 24 PHS 31 | 2:30, share bus with boys cross country | |
| Tue., 9/23 | FR Field Hockey | Ridgefield | Home - PHS Baseball Field [Directions] | 4:15 p.m. | ||
| Tue., 9/23 | V Girls Soccer | Brookfield | Away - BHS Stadium Field [Directions] | W 6-2 | 2:15 pm, share bus with JVs | |
| Tue., 9/23 | JV Girls Soccer | Brookfield | Away - BHS Back Turf [Directions] | 3:45 p.m. | 2:15 pm, share bus with varsity | |
| Tue., 9/23 | FR Girls Soccer | Newtown | Away - Treadwell Town Park [Directions] | 3:45 p.m. | 2:30 pm | |
| Tue., 9/23 | V Girls Swimming and Diving | Brookfield | Home - Pomperaug Pool [Directions] | Pomperaug 97- Brookfield 84 | ||
| Tue., 9/23 | V Girls Volleyball | Stratford | Away - Needham Memorial Gymnasium [Directions] | W 3-0 | 3:30, share bus with JVs | Admission Fee will be charged |
| Tue., 9/23 | JV Girls Volleyball | Stratford | Away - Needham Memorial Gymnasium [Directions] | 5:00 p.m. | 3:30, share bus with Varsity | Admission Fee will be charged |
| Tue., 9/23 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 2:15 p.m. | 2:15 to 3:00 | |
| Wed., 9/24 | FR Football | Newtown | Home - Sports Complex & Track [Directions] | 4:00 p.m. | ||
| Wed., 9/24 | FR Girls Volleyball | Masuk | Away - David Strong Gymnasium @ Masuk High School [Directions] | 3:30 p.m. | 2:30 pm | |
| Wed., 9/24 | Miscellaneous Events | Pomperaug Pop Warner Cheerleading Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30pm | |
| Wed., 9/24 | Miscellaneous Events | PAC Swim Clinic | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Wed., 9/24 | School Holidays and Closings | Professional Development Day - Half Day | ||||
| Wed., 9/24 | School Holidays and Closings | Rosh Hashanah begins at sundown | ||||
| Thu., 9/25 | School Holidays and Closings | Rosh Hashanah - No School | ||||
| Fri., 9/26 | V Football | Newtown | Away - Blue and Gold Stadium [Directions] | L 3-49 | 4:30 pm, 2 buses | |
| Fri., 9/26 | V Competitive Cheerleading | Newtown | Away [Directions] | 7:00 p.m. | 5:45 | |
| Fri., 9/26 | V Field Hockey | Immaculate | Away - Mustang Valley [Directions] | W 3-1 | 2:30, share bus with JVs | |
| Fri., 9/26 | JV Field Hockey | Immaculate | Away - Mustang Valley [Directions] | 5:45 p.m. | 2:30, share bus with varsity | |
| Fri., 9/26 | V Girls Volleyball | Joel Barlow | Home - PHS Main Gym [Directions] | L 0-3 | ||
| Fri., 9/26 | JV Girls Volleyball | Joel Barlow | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 9/26 | FR Girls Volleyball | Weston | Away - WHS Gymnasium [Directions] | 4:00 p.m. | 3:00 pm | |
| Fri., 9/26 | Miscellaneous Events | PAC Swim Clinic | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Fri., 9/26 | Miscellaneous Events | Pop Warner Cheer Practice | 6:30 p.m. | 6:30 - 9:00 pm | ||
| Sat., 9/27 | JV Football | Newtown | Home - Sports Complex & Track [Directions] | 10:00 a.m. | ||
| Sat., 9/27 | V Boys Soccer | Masuk | Away - Masuk Stadium Field [Directions] | W 3-0 | 12:00 pm Share bus with varsity | |
| Sat., 9/27 | JV Boys Soccer | Masuk | Away - Masuk Middle Field [Directions] | 1:30 p.m. | 12:00 Share bus with Varsity | |
| Sat., 9/27 | FR Boys Soccer | Naugatuck | Away - Naugatuck High School [Directions] | 9:00 a.m. | 7:45 am | |
| Sat., 9/27 | JV Competitive Cheerleading | Newtown | Home - Sports Complex & Track [Directions] | 10:00 a.m. | ||
| Sat., 9/27 | FR Field Hockey | Masuk | Away - Masuk Middle Field [Directions] | 11:00 a.m. | 9:45 am | |
| Sat., 9/27 | V Girls Soccer | Masuk | Home - Sports Complex & Track [Directions] | L 1-3 | ||
| Sat., 9/27 | JV Girls Soccer | Masuk | Home - Sports Complex & Track [Directions] | 2:45 p.m. | ||
| Sat., 9/27 | FR Girls Soccer | Naugatuck | Home - PHS Soccer Field [Directions] | 9:00 a.m. | ||
| Sun., 9/28 | Miscellaneous Events | Pop Warner Football | - Sports Complex & Track | 11:00 a.m. | 11:00 am to 8:00 pm | |
| Mon., 9/29 | V Girls Soccer | Weston | Away - WHS Turf Field [Directions] | L 3-4 | 5:00 pm | |
| Mon., 9/29 | JV Girls Soccer | Weston | Away - WHS Turf Field [Directions] | 5:00 p.m. | 3:00 pm | |
| Mon., 9/29 | V Girls Volleyball | Weston | Away - WHS Gymnasium [Directions] | L 0-3 | 2:15, share bus with JVs | |
| Mon., 9/29 | JV Girls Volleyball | Weston | Away - WHS Gymnasium [Directions] | 4:00 p.m. | 2:15, share bus with Varsity | |
| Mon., 9/29 | Miscellaneous Events | Pomperaug Pop Warner Cheerleading Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30pm | |
| Mon., 9/29 | Miscellaneous Events | PAC Swim Clinic | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Tue., 9/30 | V Boys Cross Country | Stratford, Bunnell, New Fairfield | Home - Pomperaug High School [Directions] | PHS 19 SHS 44 PHS 21 Bunnell 37 BHS 21 NFHS 36 | ||
| Tue., 9/30 | V Boys Soccer | Weston | Home - Sports Complex & Track [Directions] | L 1-2 | ||
| Tue., 9/30 | V Girls Cross Country | Stratford, Bunnell, New Fairfield | Home - Pomperaug High School [Directions] | PHS 15 SHS 50 PHS 15 Bunnell 50 NFHS 25 PHS 30 | ||
| Tue., 9/30 | V Field Hockey | Masuk | Away - Masuk Middle Field [Directions] | W 7-1 | 2:15, share bus with JVs | |
| Tue., 9/30 | JV Field Hockey | Masuk | Away - Masuk Middle Field [Directions] | 5:15 p.m. | 2:15, share bus with Varsity | |
| Tue., 9/30 | FR Field Hockey | Immaculate | Home - PHS Baseball Field [Directions] | Cancelled | ||
| Tue., 9/30 | V Girls Swimming and Diving | Joel Barlow | Home - PHS Pool [Directions] | Pomperaug 91- Joel Barlow 84 | ||
| Tue., 9/30 | FR Girls Volleyball | SWC Freshmen Jamboree | Home - Auxiliary Gym [Directions] | 4:00 p.m. | 4:00 - 6:30 pm | |
| Tue., 9/30 | FR Girls Volleyball | SWC Freshmen Jamboree | Home - PHS Main Gym [Directions] | 4:00 p.m. | 4:00 - 6:30 | |
| Wed., 10/1 | FR Football | New Milford | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Wed., 10/1 | V Girls Volleyball | Bunnell | Away - Bunnell [Directions] | L 0-3 | 3:30, share bus with JVs | Admission fee will be charged |
| Wed., 10/1 | JV Girls Volleyball | Bunnell | Away - Bunnell [Directions] | 5:15 p.m. | 3:30, Share bus with Varsity | Admission Fee will be charged |
| Wed., 10/1 | Miscellaneous Events | Pomperaug Pop Warner Cheerleading Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30pm | |
| Wed., 10/1 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Thu., 10/2 | V Football | New Milford | Away - New Milford High School [Directions] | L 2-46 | 4:30 pm, 2 buses | |
| Thu., 10/2 | V Boys Soccer | Newtown | Home - Sports Complex & Track [Directions] | L 1-2 | ||
| Thu., 10/2 | FR Boys Soccer | Amity | Away - Amity High School - Field # 2 [Directions] | 3:45 p.m. | 2:15 | |
| Thu., 10/2 | V Competitive Cheerleading | New Milford | Away [Directions] | 7:00 p.m. | 5:30 | |
| Thu., 10/2 | V Field Hockey | New Milford | Home - Sports Complex & Track [Directions] | T 0-0 | ||
| Thu., 10/2 | JV Field Hockey | New Milford | Home - Sports Complex & Track [Directions] | 3:30 p.m. | ||
| Thu., 10/2 | FR Girls Soccer | Amity | Home - PHS Soccer Field [Directions] | 4:00 p.m. | ||
| Thu., 10/2 | V Girls Swimming and Diving | Newtown | Home - PHS Pool [Directions] | Pomperaug 101- Newtown 85 | $5 Adults $3 Students | |
| Thu., 10/2 | FR Girls Volleyball | Brookfield | Home - PHS Main Gym [Directions] | 6:30 p.m. | ||
| Thu., 10/2 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 2:15 p.m. | ||
| Thu., 10/2 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 2:15 p.m. | ||
| Thu., 10/2 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Fri., 10/3 | V Boys Cross Country | Nonnewaug Invitational | Away | 3:30 p.m. | 2:15 | |
| Fri., 10/3 | JV Football | New Milford | Home - Sports Complex & Track [Directions] | 3:30 p.m. | ||
| Fri., 10/3 | JV Boys Soccer | Newtown | Home - PHS Soccer Field [Directions] | 3:30 p.m. | ||
| Fri., 10/3 | JV Competitive Cheerleading | New Milford | Home [Directions] | 3:30 p.m. | ||
| Fri., 10/3 | V Girls Cross Country | Nonnewaug Invitational | Away | 3:30 p.m. | 2:15 | |
| Fri., 10/3 | V Girls Soccer | Newtown | Away - Blue and Gold Stadium [Directions] | T 2-2 | 2:15 pm | |
| Fri., 10/3 | JV Girls Soccer | Newtown | Away - Treadwell Town Park--Tilson Field [Directions] | 3:45 p.m. | 2:30 pm | |
| Fri., 10/3 | V Girls Volleyball | Bethel | Home - PHS Main Gym [Directions] | W 3-0 | ||
| Fri., 10/3 | JV Girls Volleyball | Bethel | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 10/3 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Fri., 10/3 | Miscellaneous Events | Pop Warner Cheer Practice | 6:30 p.m. | 6:30 - 9:00 pm | ||
| Fri., 10/3 | School Holidays and Closings | Yom Kippur Begins at Sundown | ||||
| Sat., 10/4 | School Holidays and Closings | Yom Kippur | ||||
| Sun., 10/5 | Miscellaneous Events | Pop Warner Football | - Sports Complex & Track | 11:00 a.m. | 11:00 am to 8:00 pm | |
| Mon., 10/6 | V Boys Soccer | Immaculate | Away - Mustang Valley [Directions] | W 4-3 | 2:45 pm | |
| Mon., 10/6 | JV Boys Soccer | Immaculate | Away - Mustang Valley [Directions] | 4:15 p.m. | ||
| Mon., 10/6 | V Girls Soccer | Immaculate | Home - Sports Complex & Track [Directions] | L 0-2 | ||
| Mon., 10/6 | JV Girls Soccer | Immaculate | Home - Sports Complex & Track [Directions] | Cancelled | ||
| Mon., 10/6 | V Girls Volleyball | Immaculate | Away - Immaculate High School [Directions] | W 3-0 | 2:15, Share bus with JVs | |
| Mon., 10/6 | JV Girls Volleyball | Immaculate | Away - Immaculate High School [Directions] | 3:30 p.m. | 2:15, share bus with Varsity | |
| Mon., 10/6 | FR Girls Volleyball | Amity | Away - Amity High School [Directions] | 4:00 p.m. | 3:00 pm | |
| Mon., 10/6 | Miscellaneous Events | Stby Park & Rec PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 3:30 pm | |
| Mon., 10/6 | Miscellaneous Events | Pomperaug Pop Warner Cheerleading Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30pm | |
| Mon., 10/6 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Tue., 10/7 | V Boys Cross Country | Joel Barlow, Masuk | Away [Directions] | PHS 20 JBHS 41 PHS 16 Masuk 47 | 2:15 pm | |
| Tue., 10/7 | FR Boys Soccer | Holy Cross | Away - Lower Murray Park [Directions] | 3:45 p.m. | 2:15 pm | |
| Tue., 10/7 | V Girls Cross Country | Joel Barlow, Masuk | Away [Directions] | PHS 21 JBHS 36 PHS 15 Masuk 50 | 2:15 pm | |
| Tue., 10/7 | V Field Hockey | Joel Barlow | Away - Field I (Stadium) [Directions] | W 5-2 | 3:45, share bus with JVs | |
| Tue., 10/7 | JV Field Hockey | Joel Barlow | Away - Field I (Stadium) [Directions] | 5:30 p.m. | 3:45, share bus with varsity | |
| Tue., 10/7 | FR Field Hockey | Brookfield | Home - PHS Baseball Field [Directions] | 4:30 p.m. | ||
| Tue., 10/7 | FR Girls Soccer | Holy Cross | Home - PHS Soccer Field [Directions] | 3:45 p.m. | ||
| Tue., 10/7 | V Girls Swimming and Diving | Weston | Away - Weston Middle School Pool [Directions] | Pomperaug 96- Weston 88 | 2:15 pm | |
| Tue., 10/7 | FR Girls Volleyball | New Milford | Home - PHS Main Gym [Directions] | 6:00 p.m. | ||
| Tue., 10/7 | Miscellaneous Events | Stby Park & Rec PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 4:15 pm | |
| Tue., 10/7 | Miscellaneous Events | Stby Park & Rec PAC Swim Practice | - PHS Pool | 4:30 p.m. | 4:30 - 7:00 pm | |
| Tue., 10/7 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Wed., 10/8 | FR Field Hockey | Amity | Away - Amity High School [Directions] | 4:00 p.m. | 2:30 pm | |
| Wed., 10/8 | FR Girls Soccer | Masuk | Home - PHS Soccer Field [Directions] | 4:00 p.m. | ||
| Wed., 10/8 | V Girls Volleyball | Newtown | Home - PHS Main Gym [Directions] | L 3-1 | ||
| Wed., 10/8 | JV Girls Volleyball | Newtown | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Wed., 10/8 | FR Girls Volleyball | Amity | Home - PHS Main Gym [Directions] | 7:00 p.m. | ||
| Wed., 10/8 | Miscellaneous Events | Westover School CC Practice | - Sports Complex & Track | 1:30 p.m. | 1:30 to 3:00 | |
| Wed., 10/8 | Miscellaneous Events | Pomperaug Pop Warner Cheerleading Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30pm | |
| Wed., 10/8 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Thu., 10/9 | FR Football | Stratford | Away [Directions] | 4:00 p.m. | 2:15 pm | |
| Thu., 10/9 | V Boys Soccer | Kolbe Cathedral | Home - Sports Complex & Track [Directions] | W 4-0 | ||
| Thu., 10/9 | FR Boys Soccer | New Milford | Home - PHS Soccer Field [Directions] | 3:45 p.m. | ||
| Thu., 10/9 | V Field Hockey | Weston | Home - Sports Complex & Track [Directions] | W 3-0 | ||
| Thu., 10/9 | JV Field Hockey | Weston | Home - Sports Complex & Track [Directions] | 5:15 p.m. | ||
| Thu., 10/9 | FR Field Hockey | Bethel | Away - Hunt Field at Bethel High School [Directions] | 4:30 p.m. | 3:00 pm | |
| Thu., 10/9 | V Girls Soccer | Kolbe Cathedral | Away - Seaside Park [Directions] | W 7-0 | 2:15 pm | |
| Thu., 10/9 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 2:15 p.m. | ||
| Thu., 10/9 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Thu., 10/9 | School Holidays and Closings | PHS Open House | ||||
| Fri., 10/10 | V Football | Stratford | Home - Sports Complex & Track [Directions] | L 7-27 | ||
| Fri., 10/10 | V Boys Soccer | Joel Barlow | Away - Field I (Stadium) [Directions] | T 0-0 | 5:00 pm | |
| Fri., 10/10 | JV Boys Soccer | Weston | Home - PHS Soccer Field [Directions] | 4:15 p.m. | ||
| Fri., 10/10 | FR Boys Soccer | Masuk | Away - Masuk Middle Field [Directions] | 4:15 p.m. | 2:15 pm | |
| Fri., 10/10 | V Competitive Cheerleading | Stratford | Home - Sports Complex & Track [Directions] | 7:00 p.m. | ||
| Fri., 10/10 | V Girls Swimming and Diving | Bunnell | Away - Flood Pool [Directions] | Pomperaug 91- Bunnell 68 | 5:00 pm | @ Flood Pool |
| Fri., 10/10 | V Girls Volleyball | Kolbe Cathedral | Away - KOLBE CATHEDRAL GYM [Directions] | L 3-0 | 2:15, Share bus with JVs | |
| Fri., 10/10 | JV Girls Volleyball | Kolbe Cathedral | Away - KOLBE CATHEDRAL GYM [Directions] | 3:30 p.m. | 2:15, share bus with varsity | |
| Fri., 10/10 | Miscellaneous Events | Stby Park & Rec PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 4:15 pm | |
| Fri., 10/10 | Miscellaneous Events | Freshmen Tail Gate | - PHS Baseball Field | 5:00 p.m. | 5:00 to 6:30 pm | |
| Fri., 10/10 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Fri., 10/10 | Miscellaneous Events | Pop Warner Cheer Practice | 6:30 p.m. | 6:30 - 9:00 pm | ||
| Fri., 10/10 | School Holidays and Closings | In Service Half Day | ||||
| Sat., 10/11 | V Boys Cross Country | Bethel (Scrim.) | Away [Directions] | TBA | 8:00 am, share bus with girls cc | |
| Sat., 10/11 | JV Football | Stratford | Away - Penders Field [Directions] | 10:00 a.m. | 8:00 am | |
| Sat., 10/11 | V Girls Cross Country | Bethel (Scrim.) | Away [Directions] | TBA | 8:00 am, share bus with boys cross country | |
| Sat., 10/11 | V Field Hockey | New Fairfield | Away - Rebel Turf [Directions] | W 3-0 | 2:15 pm, share bus with JVs | |
| Sat., 10/11 | JV Field Hockey | New Fairfield | Away - Rebel Turf [Directions] | 5:00 p.m. | 2:15 share bus with varsity | |
| Sat., 10/11 | V Girls Soccer | Joel Barlow | Home - Sports Complex & Track [Directions] | T 1-1 | ||
| Sat., 10/11 | JV Girls Soccer | Joel Barlow | Home - PHS Soccer Field [Directions] | 3:00 p.m. | ||
| Sat., 10/11 | FR Girls Soccer | New Milford | Away - New Milford High School [Directions] | 9:00 a.m. | 7:45 am | |
| Sun., 10/12 | Miscellaneous Events | Pop Warner Football | - Sports Complex & Track | 11:00 a.m. | 11:00 am to 8:00 pm | |
| Mon., 10/13 | V Boys Soccer | Watertown | Away - John J. Mills Complex @ Watertown High School [Directions] | W 4-1 | 3:45 pm | |
| Mon., 10/13 | V Field Hockey | Greenwich | Away - Cardinal Stadium [Directions] | L 0-1 | 9:45 am | |
| Mon., 10/13 | V Girls Soccer | Notre Dame-Fairfield | Away - Sacred Heart University [Directions] | L 0-2 | 3:30 pm | |
| Mon., 10/13 | School Holidays and Closings | Columbus Day - No School | ||||
| Tue., 10/14 | V Boys Soccer | Notre Dame-Fairfield | Home - Sports Complex & Track [Directions] | T 1-1 | ||
| Tue., 10/14 | FR Boys Soccer | Newtown | Away - Newtown High School Practice Field [Directions] | 3:45 p.m. | 2:45 pm | |
| Tue., 10/14 | V Field Hockey | Bethel | Home - Sports Complex & Track [Directions] | W 2-1 | ||
| Tue., 10/14 | JV Field Hockey | Bethel | Home - Sports Complex & Track [Directions] | 5:30 p.m. | ||
| Tue., 10/14 | FR Field Hockey | Newtown | Home - PHS Baseball Field [Directions] | 4:30 p.m. | ||
| Tue., 10/14 | FR Girls Soccer | Newtown | Home - PHS Soccer Field [Directions] | 3:45 p.m. | ||
| Tue., 10/14 | V Girls Swimming and Diving | Stratford | Home - PHS Pool [Directions] | Pomperaug 85- Stratford 75 | $5 Adults, $3 students | |
| Tue., 10/14 | V Girls Volleyball | Notre Dame-Fairfield | Home - PHS Main Gym [Directions] | W 3-1 | ||
| Tue., 10/14 | JV Girls Volleyball | Notre Dame-Fairfield | Home - PHS Main Gym [Directions] | 4:15 p.m. | ||
| Tue., 10/14 | Miscellaneous Events | Stby Park & Rec PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 4:15 pm | |
| Tue., 10/14 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Tue., 10/14 | Miscellaneous Events | Stby Park & Rec Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 10/15 | FR Football | Holy Cross | Home - Sports Complex & Track [Directions] | 7:00 p.m. | ||
| Wed., 10/15 | V Girls Volleyball | New Fairfield | Away - NFHS Gym [Directions] | W 3-1 | 2:15, Share bus with JVs | |
| Wed., 10/15 | JV Girls Volleyball | New Fairfield | Away - NFHS Gym [Directions] | 3:30 p.m. | 2:15, share bus with Varsity | |
| Wed., 10/15 | FR Girls Volleyball | Newtown | Away - Newtown High School Gymnasium [Directions] | 3:30 p.m. | 3:00 pm | |
| Wed., 10/15 | Miscellaneous Events | PSATs | - PHS Main Gym | 7:00 a.m. | 7:00 am to 12:00pm | |
| Wed., 10/15 | Miscellaneous Events | PSATs | - Health Classroom - Room 201 | 7:00 a.m. | 7:00 am to 3:00pm | |
| Wed., 10/15 | Miscellaneous Events | Westover School CC Practice | - Sports Complex & Track | 1:30 p.m. | 1:30 to 3:00 | |
| Wed., 10/15 | Miscellaneous Events | Pomperaug Pop Warner Cheerleading Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30pm | |
| Wed., 10/15 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Thu., 10/16 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 2:15 p.m. | ||
| Thu., 10/16 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Thu., 10/16 | Miscellaneous Events | Stby Park & Rec Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 10/17 | V Boys Cross Country | SWC Championships | Away [Directions] | 3:30 p.m. | 1:30, share bus with girls cross country | @ Bethel High School, $10 Adults, $5 Students |
| Fri., 10/17 | V Football | Holy Cross | Away - Municipal Stadium (Wtby) [Directions] | W 29-28 | 5:00 pm, 2 buses | |
| Fri., 10/17 | V Boys Soccer | Stratford | Away - Penders Field [Directions] | W 2-1 | 5:00 pm | |
| Fri., 10/17 | JV Boys Soccer | Stratford | Away - Penders Field [Directions] | 5:00 p.m. | 2:30, share bus with freshmen girls soccer | |
| Fri., 10/17 | V Competitive Cheerleading | Holy Cross | Away [Directions] | 7:00 p.m. | 5:30 | @ Municipal Stadium |
| Fri., 10/17 | V Girls Cross Country | SWC Championships | Away [Directions] | 4:00 p.m. | 1:30 pm, share with boys cc | @ Bethel High School, $10 adults, $5 Students |
| Fri., 10/17 | V Field Hockey | Newtown | Away - Treadwell Town Park [Directions] | W 2-0 | 2:30, Share bus with JVs | |
| Fri., 10/17 | JV Field Hockey | Newtown | Away - Treadwell Town Park [Directions] | 5:30 p.m. | 2:30, Share bus with Varsity | |
| Fri., 10/17 | FR Field Hockey | New Milford | Away - New Milford High School [Directions] | 4:30 p.m. | 3:00 pm | |
| Fri., 10/17 | V Girls Soccer | Stratford | Home - Sports Complex & Track [Directions] | W 5-2 | ||
| Fri., 10/17 | JV Girls Soccer | Stratford | Home - Sports Complex & Track [Directions] | 3:45 p.m. | ||
| Fri., 10/17 | FR Girls Soccer | Naugatuck | Away - Breen Field [Directions] | 3:45 p.m. | 2:30 pm, Share bus with JV boys Soccer team | |
| Fri., 10/17 | V Girls Volleyball | New Milford | Home - PHS Main Gym [Directions] | L 2-3 | ||
| Fri., 10/17 | JV Girls Volleyball | New Milford | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 10/17 | Miscellaneous Events | Stby Park & Rec PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 3:30 pm | |
| Fri., 10/17 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Fri., 10/17 | Miscellaneous Events | Pop Warner Cheer Practice | 6:30 p.m. | 6:30 - 9:00 pm | ||
| Sat., 10/18 | JV Football | Holy Cross | Home - Sports Complex & Track [Directions] | 10:00 a.m. | ||
| Sat., 10/18 | FR Boys Soccer | Naugatuck | Home - PHS Soccer Field [Directions] | 9:00 a.m. | ||
| Sat., 10/18 | JV Competitive Cheerleading | Holy Cross | Home - Sports Complex & Track [Directions] | 10:00 a.m. | ||
| Sat., 10/18 | FR Field Hockey | Amity | Home - PHS Baseball Field [Directions] | 10:00 a.m. | ||
| Sat., 10/18 | FR Girls Soccer | Amity | Away - Amity High School - Field # 2 [Directions] | Cancelled | ||
| Sun., 10/19 | Miscellaneous Events | Pop Warner - Northern CT Cheer Competition | - PHS Main Gym | 6:00 a.m. | 6:00 am - 5:00 pm | |
| Sun., 10/19 | Miscellaneous Events | Pop Warner - Northern CT Cheer Competition | - Auxiliary Gym | 6:00 a.m. | 6:00 am - 5:00 pm | |
| Sun., 10/19 | Miscellaneous Events | Pop Warner - Northern CT Cheer Competition | - Health Classroom - Room 201 | 6:00 a.m. | 6:00 am - 5:00 pm | |
| Sun., 10/19 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 12:30 p.m. | 12:30 - 4:00 pm | |
| Sun., 10/19 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:30 pm | |
| Mon., 10/20 | V Boys Soccer | New Fairfield | Away - Rebel Turf [Directions] | T 1-1 | 5:00 pm | |
| Mon., 10/20 | JV Boys Soccer | New Fairfield | Away - Rebel Turf [Directions] | 4:30 p.m. | 3:00 pm | |
| Mon., 10/20 | V Field Hockey | Brookfield | Home - Sports Complex & Track [Directions] | W 2-1(OT) | ||
| Mon., 10/20 | JV Field Hockey | Brookfield | Home - PHS Baseball Field [Directions] | Cancelled | ||
| Mon., 10/20 | V Girls Soccer | New Fairfield | Home - Sports Complex & Track [Directions] | W 4-1 | ||
| Mon., 10/20 | JV Girls Soccer | New Fairfield | Home - Sports Complex & Track [Directions] | 5:15 p.m. | ||
| Mon., 10/20 | V Girls Volleyball | Masuk | Home - PHS Main Gym [Directions] | L 3-0 | ||
| Mon., 10/20 | JV Girls Volleyball | Masuk | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Mon., 10/20 | FR Girls Volleyball | Brookfield | Away - BHS Big Gym [Directions] | 4:00 p.m. | 3:00 pm | |
| Mon., 10/20 | Miscellaneous Events | Stby Park & Rec PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 3:30 pm | |
| Mon., 10/20 | Miscellaneous Events | Pomperaug Pop Warner Cheerleading Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30pm | |
| Mon., 10/20 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Mon., 10/20 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Mon., 10/20 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 | |
| Tue., 10/21 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Tue., 10/21 | Miscellaneous Events | Stby Park & Rec Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 10/22 | V Boys Soccer | New Milford | Home - Sports Complex & Track [Directions] | T 0-0 | non-league game | |
| Wed., 10/22 | JV Boys Soccer | New Milford | Home - Sports Complex & Track [Directions] | 3:30 p.m. | ||
| Wed., 10/22 | V Girls Soccer | Newtown | Home - Sports Complex & Track [Directions] | W 3-0 | non-league game | |
| Wed., 10/22 | JV Girls Soccer | Newtown | Home - PHS Soccer Field [Directions] | 3:45 p.m. | ||
| Wed., 10/22 | V Girls Volleyball | New Fairfield | Home - PHS Main Gym [Directions] | W 3-0 | non-league game | |
| Wed., 10/22 | JV Girls Volleyball | New Fairfield | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Wed., 10/22 | FR Girls Volleyball | SWC Freshmen Jamboree | Away [Directions] | 4:00 p.m. | 2:30 pm | @ Masuk |
| Wed., 10/22 | Miscellaneous Events | Westover School CC Practice | - Sports Complex & Track | 1:30 p.m. | 1:30 to 3:00 | |
| Wed., 10/22 | Miscellaneous Events | Pomperaug Pop Warner Cheerleading Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30pm | |
| Wed., 10/22 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Wed., 10/22 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 10/22 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 | |
| Thu., 10/23 | V Boys Cross Country | Danbury Freshmen Meet | Away | TBA | 2:15, Share bus with girls cc | |
| Thu., 10/23 | FR Football | Bethel | Home - Sports Complex & Track [Directions] | 3:30 p.m. | ||
| Thu., 10/23 | V Girls Cross Country | Danbury Freshmen Meet | Away | TBA | 2:15, Share bus with boys cc | |
| Thu., 10/23 | V Field Hockey | New Fairfield | Home - Sports Complex & Track [Directions] | W 2-1 | non-league game | |
| Thu., 10/23 | JV Field Hockey | New Fairfield | Home - Sports Complex & Track [Directions] | 5:45 p.m. | ||
| Thu., 10/23 | FR Field Hockey | Masuk | Home - PHS Baseball Field [Directions] | 4:30 p.m. | ||
| Thu., 10/23 | V Girls Swimming and Diving | Shelton | Home - PHS Pool [Directions] | 4:00 p.m. | ||
| Thu., 10/23 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 2:15 p.m. | ||
| Thu., 10/23 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Thu., 10/23 | Miscellaneous Events | Stby Park & Rec Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 10/24 | V Football | Bethel | Away - DeSantis Field at Bethel High School [Directions] | L 6-48 | 5:00 pm, 2 buses | |
| Fri., 10/24 | V Competitive Cheerleading | Bethel | Away [Directions] | 7:00 p.m. | 5:30 | |
| Fri., 10/24 | V Girls Volleyball | Nonnewaug | Home - PHS Main Gym [Directions] | W 3-1 | ||
| Fri., 10/24 | JV Girls Volleyball | Nonnewaug | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 10/24 | Miscellaneous Events | Stby Park & Rec PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 3:30 pm | |
| Fri., 10/24 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Fri., 10/24 | Miscellaneous Events | Pop Warner Cheer Practice | 6:30 p.m. | 6:30 - 9:00 pm | ||
| Sat., 10/25 | V Boys Cross Country | CIAC Class L Championship | Away - Wickham Park - East Hartford [Directions] | 12:00 p.m. | 8:00 am, share bus with girls cc | |
| Sat., 10/25 | JV Football | Bethel | Home - Sports Complex & Track [Directions] | 10:00 a.m. | ||
| Sat., 10/25 | V Boys Soccer | Brookfield | Away - BHS Stadium Field [Directions] | L 3-1 | 12:30 | |
| Sat., 10/25 | FR Boys Soccer | Holy Cross | Home - PHS Soccer Field [Directions] | 9:00 a.m. | ||
| Sat., 10/25 | JV Competitive Cheerleading | Bethel | Home - Sports Complex & Track [Directions] | 10:00 a.m. | ||
| Sat., 10/25 | V Girls Cross Country | CIAC Class L Championship | Away - Wickham Park - East Hartford [Directions] | 11:25 a.m. | 8:00 am, share bus with boys cc | |
| Sat., 10/25 | V Field Hockey | Adults $8, Students $5, SWC Quarter-Final Tournament | Home - Sports Complex & Track [Directions] | 2:00 p.m. | ||
| Sat., 10/25 | FR Field Hockey | Immaculate | Away [Directions] | Cancelled | ||
| Sat., 10/25 | V Girls Soccer | Weston | Away - WHS Turf Field [Directions] | L 0-1 | 2:00 pm | |
| Sat., 10/25 | FR Girls Soccer | Holy Cross | Away - Upper Murray Park [Directions] | 9:00 a.m. | 7:45 am | |
| Sat., 10/25 | Miscellaneous Events | RMS 5K at PHS | 8:00 a.m. | |||
| Sat., 10/25 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 12:30 p.m. | 12:30 - 4:00 pm | |
| Sat., 10/25 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:30 pm | |
| Sun., 10/26 | Miscellaneous Events | Pop Warner Football | - Sports Complex & Track | 10:30 a.m. | Game 12 - 2:00 pm | |
| Sun., 10/26 | Miscellaneous Events | Stby Park & Rec Masters Swim Program | - PHS Pool | 9:30 a.m. | 9:30 - 11:30 am | |
| Sun., 10/26 | Miscellaneous Events | Pop Warner Football | - Sports Complex & Track | 12:00 p.m. | ||
| Sun., 10/26 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 12:30 p.m. | 12:30 - 4:00 pm | |
| Sun., 10/26 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:30 pm | |
| Mon., 10/27 | FR Field Hockey | Bethel | Home [Directions] | 3:30 p.m. | ||
| Mon., 10/27 | V Girls Soccer | SWC Semi-Final Championship | Away [Directions] | Cancelled | 3:15 pm | @ New Fairfield, $8 adults $5 students |
| Mon., 10/27 | V Girls Volleyball | SWC Quarter-Final Tournament | Away | Cancelled | ||
| Mon., 10/27 | Miscellaneous Events | Stby Park & Rec PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 3:30 pm | |
| Mon., 10/27 | Miscellaneous Events | Pomperaug Pop Warner Cheerleading Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30pm | |
| Mon., 10/27 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Mon., 10/27 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 10/28 | V Boys Soccer | SWC Semi-Final Tournament | Away [Directions] | Cancelled | 3:15 pm | Penders Field, $8 adults $5 students |
| Tue., 10/28 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Tue., 10/28 | Miscellaneous Events | Stby Park & Rec Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 10/29 | V Boys Soccer | Weston (Scrim.) | Away [Directions] | 4:00 p.m. | 2:30 | |
| Wed., 10/29 | V Field Hockey | SWC Semi-Final Tournament | Away [Directions] | 7:30 p.m. | 4:00 pm | @ Joel Barlow, $8 Adults, $5 students |
| Wed., 10/29 | V Girls Soccer | SWC Championship Game | Away | Cancelled | TBA | |
| Wed., 10/29 | V Girls Swimming and Diving | SWC Diving Championships | Home - PHS Pool [Directions] | 5:30 p.m. | Warm-Ups @ 4:00 pm | |
| Wed., 10/29 | V Girls Swimming and Diving | SWC Diving Championship | Home [Directions] | 5:30 p.m. | 4:00 warm - up, $8 Adults, $5 students | |
| Wed., 10/29 | V Girls Volleyball | SWC Semi-Final Tournament | Away | Cancelled | ||
| Wed., 10/29 | Miscellaneous Events | Blood Drive | - Auxiliary Gym | 6:00 a.m. | 6:00 am to 2:15 pm | |
| Wed., 10/29 | Miscellaneous Events | Westover School CC Practice | - Sports Complex & Track | 1:30 p.m. | 1:30 to 3:00 | |
| Wed., 10/29 | Miscellaneous Events | Pomperaug Pop Warner Cheerleading Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30pm | |
| Wed., 10/29 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Wed., 10/29 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 10/30 | FR Football | Brookfield | Away - BHS Stadium Field [Directions] | 4:00 p.m. | 2:15 pm | |
| Thu., 10/30 | V Boys Soccer | SWC Championship Game | Away | Cancelled | TBA | |
| Thu., 10/30 | V Girls Volleyball | Naugatuck (Scrim.) | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Thu., 10/30 | Miscellaneous Events | Stby Park & Rec PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 3:30 pm | |
| Thu., 10/30 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 2:15 p.m. | ||
| Thu., 10/30 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Thu., 10/30 | Miscellaneous Events | Stby Park & Rec Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 10/31 | V Boys Cross Country | CIAC Open Championship | Away - Wickham Park - East Hartford [Directions] | 2:45 p.m. | 11:45, share bus with girls cc | |
| Fri., 10/31 | V Football | Brookfield | Home - Sports Complex & Track [Directions] | L 22-45 | ||
| Fri., 10/31 | V Competitive Cheerleading | Brookfield | Home [Directions] | 7:00 p.m. | ||
| Fri., 10/31 | V Girls Cross Country | CIAC Open Championship | Away - Wickham Park - East Hartford [Directions] | 2:00 p.m. | 11:45 am, share bus with boys cc | |
| Fri., 10/31 | V Field Hockey | SWC Championship Game | Away [Directions] | 5:00 p.m. | 5:00 pm | @ Brookfield HS, $10 adults, $5 students |
| Fri., 10/31 | Miscellaneous Events | PAC Swim Team Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Fri., 10/31 | Miscellaneous Events | Pop Warner Cheer Practice | 6:30 p.m. | 6:30 - 9:00 pm | ||
| Sat., 11/1 | JV Football | Brookfield | Away - BHS Stadium Field [Directions] | 10:00 a.m. | 8:15 am | |
| Sat., 11/1 | V Girls Swimming and Diving | SWC Swim Championships | Away | Cancelled | ||
| Sat., 11/1 | V Girls Swimming and Diving | SWC Championship | Away | 1:00 p.m. | 10:00 | @ Masuk, $10 Adults, $5 students |
| Sat., 11/1 | Miscellaneous Events | Stby Park & Rec Travel Basketball Practice | - PHS Main Gym | 10:00 a.m. | 10:00 am - 9:00 pm | |
| Sat., 11/1 | Miscellaneous Events | Stby Park & Rec Travel Basketball Practice | - PHS Main Gym | 12:30 p.m. | 1:00 - 5:30 pm | |
| Sat., 11/1 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 12:30 p.m. | 12:30 - 4:00 pm | |
| Sat., 11/1 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:30 pm | |
| Sat., 11/1 | Miscellaneous Events | Stby Park & Rec Travel Basketball Practice | - Auxiliary Gym | 5:30 p.m. | 5:30 - 9:00 pm | |
| Sat., 11/1 | Miscellaneous Events | Student Council Spirit Dance | - PHS Main Gym | 6:30 p.m. | 5:30 set-up, 6:30 - 10:30 pm dance | |
| Sun., 11/2 | Miscellaneous Events | Stby Park & Rec Travel Basketball Practice | - PHS Main Gym | 10:00 a.m. | 10:00 am - 3:30 pm | |
| Sun., 11/2 | Miscellaneous Events | Pop Warner Football | - Sports Complex & Track | 8:30 a.m. | 8:30 am to 1:00 pm | |
| Sun., 11/2 | Miscellaneous Events | Stby Park & Rec Masters Swim Program | - PHS Pool | 9:30 a.m. | 9:30 - 11:30 am | |
| Sun., 11/2 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 12:30 p.m. | 12:30 - 4:00 pm | |
| Sun., 11/2 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:30 pm | |
| Sun., 11/2 | Miscellaneous Events | Revolution Soccer | - Sports Complex & Track | 1:15 p.m. | 1:15 pm to 4:00 pm | |
| Mon., 11/3 | V Boys Soccer | Wethersfield | Away - Cottone Field at WHS [Directions] | 6:00 p.m. | 4:00 pm | |
| Mon., 11/3 | V Girls Volleyball | Mercy | Away - Mercy [Directions] | 6:00 p.m. | 4:00 pm | $5.00 adults and $3.00 for students. |
| Mon., 11/3 | Miscellaneous Events | Pomperaug Pop Warner Cheerleading Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30pm | |
| Mon., 11/3 | Miscellaneous Events | Stby Park & Rec Basketball | - PHS Main Gym | 6:45 p.m. | 7:00 - 8:30 pm | |
| Mon., 11/3 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Mon., 11/3 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 | |
| Mon., 11/3 | Miscellaneous Events | Mdby Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 11/4 | V Field Hockey | Brookfield | Home - Sports Complex & Track [Directions] | 3:30 p.m. | $8 Adults, $5 Students | |
| Tue., 11/4 | V Girls Soccer | Naugatuck | Home - Sports Complex & Track [Directions] | 6:00 p.m. | $8 Adults, $5 students | |
| Tue., 11/4 | Miscellaneous Events | Stby Park & Rec Basketball | - PHS Main Gym | 6:45 p.m. | 6:00 - 8:30 pm | |
| Tue., 11/4 | Miscellaneous Events | Stby Park & Rec Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 11/5 | V Girls Swimming and Diving | CIAC Class L Diving Trials/Finals | Away - Middletown HS [Directions] | 5:30 p.m. | ||
| Wed., 11/5 | Miscellaneous Events | Westover School CC Practice | - Sports Complex & Track | 1:30 p.m. | 1:30 to 3:00 | |
| Wed., 11/5 | Miscellaneous Events | Pomperaug Pop Warner Cheerleading Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30pm | |
| Wed., 11/5 | Miscellaneous Events | Middlebury Park & Rec Basketball Practice | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Wed., 11/5 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 11/5 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 | |
| Thu., 11/6 | V Field Hockey | Lauralton Hall | Away [Directions] | 2:00 p.m. | 12:30 | @ Watertown High School, $8 Adults, $5 Students |
| Thu., 11/6 | V Girls Soccer | Masuk | Away - Trumbull HS [Directions] | 7:00 p.m. | 5:15 | @ Trumbull High School, $8 Adults, $5 Students |
| Fri., 11/7 | V Football | Masuk | Away - Masuk Stadium Field [Directions] | L 13-25 | 5:00 pm, 2 buses | |
| Fri., 11/7 | V Competitive Cheerleading | Masuk | Away [Directions] | 7:00 p.m. | 5:30 | |
| Fri., 11/7 | Miscellaneous Events | Turkey Tumble Set up | 5:00 p.m. | |||
| Fri., 11/7 | Miscellaneous Events | Pop Warner Cheer Practice | 6:30 p.m. | 6:30 - 9:00 pm | ||
| Sat., 11/8 | V Boys Cross Country | New England Championship | Away - Wickham Park - East Hartford [Directions] | TBA | 8:30 am, share bus with girls cc | |
| Sat., 11/8 | JV Football | Masuk | Home - Sports Complex & Track [Directions] | 10:00 a.m. | ||
| Sat., 11/8 | JV Competitive Cheerleading | Masuk | Home - Sports Complex & Track [Directions] | 10:00 a.m. | ||
| Sat., 11/8 | V Girls Cross Country | New England Championship | Away - Wickham Park - East Hartford [Directions] | TBA | 8:30 am, share bus with boys cc | |
| Sat., 11/8 | V Girls Soccer | Wethersfield | Away - Cottone Field at WHS [Directions] | 4:00 p.m. | 2:15 pm | $8 Adults, $5 Students |
| Sat., 11/8 | V Girls Swimming and Diving | CIAC Class L Qualifying | Away - Cornerstone Pool [Directions] | 6:15 p.m. | 3:00 pm | Admission will be charged |
| Sat., 11/8 | Miscellaneous Events | Turkey Tumble | - PHS Main Gym | 9:00 a.m. | ||
| Sat., 11/8 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 12:30 p.m. | 12:30 - 4:00 pm | |
| Sat., 11/8 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:30 pm | |
| Sun., 11/9 | Miscellaneous Events | Pomperaug Youth Lacrosse Jamboree | - Sports Complex & Track | 8:30 a.m. | 8:30 am - 4:00 pm | |
| Sun., 11/9 | Miscellaneous Events | Pomperaug Youth Lacrosse Jamboree | - PHS Soccer Field | 8:30 a.m. | 8:30 am - 4:00 pm | |
| Sun., 11/9 | Miscellaneous Events | Pomperaug Youth Lacrosse Jamboree | - PHS Softball Field | 8:30 a.m. | 8:30 am - 4:00 pm | |
| Sun., 11/9 | Miscellaneous Events | Turkey Tumble | - PHS Main Gym | 9:00 a.m. | ||
| Sun., 11/9 | Miscellaneous Events | Stby Park & Rec Masters Swim Program | - PHS Pool | 9:30 a.m. | 9:30 - 11:30 am | |
| Sun., 11/9 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 12:30 p.m. | 12:30 - 4:00 pm | |
| Sun., 11/9 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:30 pm | |
| Mon., 11/10 | Miscellaneous Events | Pomperaug Pop Warner Cheerleading Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30pm | |
| Mon., 11/10 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Mon., 11/10 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 | |
| Mon., 11/10 | Miscellaneous Events | Mdby Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 11/11 | Miscellaneous Events | Stby Park & Rec Basketball | - PHS Main Gym | 6:45 p.m. | 7:00 - 8:30 pm | |
| Tue., 11/11 | Miscellaneous Events | Stby Park & Rec Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 11/12 | V Girls Swimming and Diving | CIAC Class L Finals | Away - SCSU [Directions] | 6:00 p.m. | 3:00 pm | Admission will be charged |
| Wed., 11/12 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 4:30 pm | |
| Wed., 11/12 | Miscellaneous Events | Pomperaug Pop Warner Cheerleading Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30pm | |
| Wed., 11/12 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 11/13 | FR Football | Joel Barlow | Away - Field I (Stadium) [Directions] | 4:00 p.m. | 2:15 pm | |
| Thu., 11/13 | V Girls Swimming and Diving | CIAC Open Diving | Away - Middletown HS [Directions] | 5:30 p.m. | 2:15 pm | |
| Thu., 11/13 | Miscellaneous Events | Band Practice | - Sports Complex & Track | 2:15 p.m. | ||
| Thu., 11/13 | Miscellaneous Events | Stby Park & Rec Basketball | - PHS Main Gym | 6:45 p.m. | 7:00 - 8:30 pm | |
| Thu., 11/13 | Miscellaneous Events | Stby Park & Rec Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 11/14 | V Football | Joel Barlow | Home - Sports Complex & Track [Directions] | W 27-14 | ||
| Fri., 11/14 | V Competitive Cheerleading | Joel Barlow | Home - Sports Complex & Track [Directions] | 7:00 p.m. | ||
| Fri., 11/14 | Miscellaneous Events | Stby Park & Rec Basketball | - Auxiliary Gym | 6:45 p.m. | 6:00 - 8:30 pm | |
| Fri., 11/14 | Miscellaneous Events | Middlebury Park & Rec Basketball Practice | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Sat., 11/15 | JV Football | Joel Barlow | Away - Field I (Stadium) [Directions] | 10:00 a.m. | 8:00 am | |
| Sat., 11/15 | V Girls Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 7:30 p.m. | 4:00 pm | Admission Fee will be charged |
| Sat., 11/15 | Miscellaneous Events | Stby Park & Rec Travel Basketball Practice | - PHS Main Gym | 10:00 a.m. | 10:00 am - 9:00 pm | |
| Sat., 11/15 | Miscellaneous Events | Stby Park & Rec Travel Basketball Practice | - PHS Main Gym | 12:30 p.m. | 1:00 - 5:30 pm | |
| Sat., 11/15 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 12:30 p.m. | 12:30 - 4:00 pm | |
| Sat., 11/15 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:30 pm | |
| Sun., 11/16 | Miscellaneous Events | Stby Park & Rec Travel Basketball Practice | - PHS Main Gym | 10:00 a.m. | 10:00 am - 9:00 pm | |
| Sun., 11/16 | Miscellaneous Events | Pop Warner Football | - Sports Complex & Track | 8:00 a.m. | 8:00 am to 8:00 pm | |
| Sun., 11/16 | Miscellaneous Events | Stby Park & Rec Masters Swim Program | - PHS Pool | 9:30 a.m. | 9:30 - 11:30 am | |
| Sun., 11/16 | Miscellaneous Events | Stby Park & Rec Travel Basketball Practice | - PHS Main Gym | 12:30 p.m. | 1:00 - 5:30 pm | |
| Sun., 11/16 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 12:30 p.m. | 12:30 - 4:00 pm | |
| Sun., 11/16 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:30 pm | |
| Mon., 11/17 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:30 - 4:45 pm | |
| Mon., 11/17 | Miscellaneous Events | Pomperaug Pop Warner Cheerleading Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30pm | |
| Mon., 11/17 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 pm - 8:00 pm | |
| Mon., 11/17 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Mon., 11/17 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 | |
| Mon., 11/17 | Miscellaneous Events | Mdby Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 11/18 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:30 - 4:45 pm | |
| Tue., 11/18 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 pm - 8:00 pm | |
| Wed., 11/19 | FR Football | Notre Dame-Fairfield | Away - McCarty Stadium at Notre Dame [Directions] | 3:30 p.m. | 2:15 pm | |
| Wed., 11/19 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:30 - 4:45 pm | |
| Wed., 11/19 | Miscellaneous Events | Pomperaug Pop Warner Cheerleading Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30pm | |
| Wed., 11/19 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Wed., 11/19 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 pm - 8:00 pm | |
| Wed., 11/19 | Miscellaneous Events | Middlebury Park & Rec Basketball Practice | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Wed., 11/19 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 11/20 | V Football | SWC Championship Game | Away [Directions] | Cancelled | ||
| Thu., 11/20 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:30 - 4:45 pm | |
| Thu., 11/20 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Thu., 11/20 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 pm - 8:00 pm | |
| Thu., 11/20 | Miscellaneous Events | Stby Park & Rec Basketball | - PHS Main Gym | 6:45 p.m. | ||
| Thu., 11/20 | Miscellaneous Events | SWC Football Championship | - Sports Complex & Track | 7:00 p.m. | ||
| Thu., 11/20 | Miscellaneous Events | Stby Park & Rec Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 11/21 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:30 - 4:45 pm | |
| Fri., 11/21 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 p.m. | 6:00 - 8:30 pm | |
| Fri., 11/21 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 pm - 8:00 pm | |
| Fri., 11/21 | Miscellaneous Events | Middlebury Park & Rec Basketball Practice | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Sat., 11/22 | Miscellaneous Events | CT Assoc. of Schools Student Leaders Conference | - PHS Main Gym | 8:00 a.m. | 8:00 - 3:00 pm | |
| Sat., 11/22 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 12:30 p.m. | 12:30 - 4:00 pm | |
| Sun., 11/23 | Miscellaneous Events | Stby Park & Rec Travel Basketball Practice | - PHS Main Gym | 10:00 a.m. | 10:00 am - 9:00 pm | |
| Sun., 11/23 | Miscellaneous Events | Stby Park & Rec Masters Swim Program | - PHS Pool | 9:30 a.m. | 9:30 - 11:30 am | |
| Sun., 11/23 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:30 pm | |
| Mon., 11/24 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:30 - 7:45 pm | |
| Mon., 11/24 | Miscellaneous Events | CPR class for Coaches | - Health Classroom - Room 201 | 5:00 p.m. | ||
| Mon., 11/24 | Miscellaneous Events | Pomperaug Pop Warner Cheerleading Practice | - Auxiliary Gym | 5:00 p.m. | 5:00 - 8:30pm | |
| Mon., 11/24 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 pm - 8:00 pm | |
| Mon., 11/24 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Mon., 11/24 | Miscellaneous Events | Mdby Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 11/25 | V Football | Notre Dame-Fairfield | Home - Sports Complex & Track [Directions] | W 35-7 | ||
| Tue., 11/25 | V Competitive Cheerleading | Notre Dame-Fairfield | Home - Sports Complex & Track [Directions] | 7:00 p.m. | ||
| Tue., 11/25 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:30 - 7:45 pm | |
| Tue., 11/25 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 pm - 8:00 pm | |
| Tue., 11/25 | Miscellaneous Events | Stby Park & Rec Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 11/26 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 11:30 p.m. | 11:30 - 2:45 pm | |
| Wed., 11/26 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Sun., 11/30 | V Girls Basketball | Trumbull (Scrim.) | Away [Directions] | 10:30 a.m. | 9:00 am | |
| Sun., 11/30 | JV Girls Basketball | Trumbull (Scrim.) | Away [Directions] | 10:30 a.m. | 9:00 am (share bus w/varsity) | |
| Sun., 11/30 | Miscellaneous Events | Stby Park & Rec Masters Swim Program | - PHS Pool | 9:30 a.m. | 9:30 - 11:30 am | |
| Mon., 12/1 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Mon., 12/1 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 pm - 8:00 pm | |
| Mon., 12/1 | Miscellaneous Events | Mdby Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 12/2 | V Girls Basketball | Farmington (Scrim.) | Away - Farmington High School [Directions] | 5:00 p.m. | 3:45 | |
| Tue., 12/2 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Tue., 12/2 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 pm - 8:00 pm | |
| Tue., 12/2 | Miscellaneous Events | Stby Park & Rec Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 12/3 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Wed., 12/3 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 pm - 8:00 pm | |
| Wed., 12/3 | Miscellaneous Events | Middlebury Park & Rec Basketball Practice | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Thu., 12/4 | V Boys Basketball | Wilby (Scrim.) | Away - Wilby H.S. [Directions] | 6:30 p.m. | 5:30 pm | |
| Thu., 12/4 | V Girls Basketball | St. Joseph (Scrim.) | Away - St. Joseph High School [Directions] | 6:00 p.m. | 4:30 pm | |
| Thu., 12/4 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Thu., 12/4 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 pm - 8:00 pm | |
| Thu., 12/4 | Miscellaneous Events | Stby Park & Rec Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 12/5 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:00 p.m. | 5:00 - 8:30 pm | |
| Fri., 12/5 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 pm - 8:00 pm | |
| Fri., 12/5 | Miscellaneous Events | Middlebury Park & Rec Basketball Practice | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Sat., 12/6 | V Boys Ice Hockey | Rumsey Hall (Scrim.) | Away - The Forman School | 5:30 p.m. | 3:45 p.m. | |
| Sat., 12/6 | V Girls Basketball | Career Magnet (Scrim.) | Home - PHS Main Gym [Directions] | 11:00 a.m. | ||
| Sat., 12/6 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 12:30 p.m. | 12:30 - 4:00 pm | |
| Sat., 12/6 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:30 pm | |
| Sun., 12/7 | Miscellaneous Events | Stby Park & Rec Masters Swim Program | - PHS Pool | 9:30 a.m. | 9:30 - 11:30 am | |
| Sun., 12/7 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 12:30 p.m. | 12:30 - 4:00 pm | |
| Sun., 12/7 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:30 pm | |
| Mon., 12/8 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Mon., 12/8 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 pm - 8:00 pm | |
| Mon., 12/8 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Mon., 12/8 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 | |
| Mon., 12/8 | Miscellaneous Events | Mdby Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 12/9 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Tue., 12/9 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 pm - 8:00 pm | |
| Tue., 12/9 | Miscellaneous Events | Stby Park & Rec High School Basketball | - PHS Main Gym | 7:00 p.m. | 7:00 - 8:30 pm | |
| Tue., 12/9 | Miscellaneous Events | Stby Park & Rec Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 12/10 | V Boys Basketball | Holy Cross (Scrim.) | Home - PHS Main Gym [Directions] | 2:30 p.m. | ||
| Wed., 12/10 | V Boys Ice Hockey | Shepaug Jamboree | Away - Shepaug Jamboree | 7:15 p.m. | 5:45 p.m. | |
| Wed., 12/10 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Wed., 12/10 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 pm - 8:00 pm | |
| Wed., 12/10 | Miscellaneous Events | Stby Park & Rec High School Basketball | - Auxiliary Gym | 6:00 p.m. | 6:00 - 7:00 pm | |
| Wed., 12/10 | Miscellaneous Events | Middlebury Park & Rec Basketball Practice | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Wed., 12/10 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 12/10 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 | |
| Thu., 12/11 | V Girls Basketball | Norwich Free Academy | Away - Masuk High School [Directions] | L 70-41 | 3:30 pm | @ Masuk High School |
| Thu., 12/11 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Thu., 12/11 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 pm - 8:00 pm | |
| Thu., 12/11 | Miscellaneous Events | Stby Park & Rec Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 12/12 | V Boys Indoor Track | Weslyan Developmental | Away | 3:00 p.m. | 3:00, share bus with girls IT | |
| Fri., 12/12 | V Girls Basketball | Brookfield | Away [Directions] | W 81-27 | 3:30 pm | |
| Fri., 12/12 | FR Girls Basketball | Ridgefield | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 12/12 | V Girls Indoor Track | Weslyan | Away | TBA | 3:00, share bus with boys IT | |
| Fri., 12/12 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Fri., 12/12 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Fri., 12/12 | Miscellaneous Events | Middlebury Park & Rec Basketball Practice | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Sat., 12/13 | V Boys Basketball | Wolcott (Scrim.) | Away [Directions] | 10:00 a.m. | 9:00 am | |
| Sat., 12/13 | V Boys Ice Hockey | Shelton Jamboree | Away | 6:00 p.m. | 4:00 p.m. | |
| Sat., 12/13 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 12:30 p.m. | 12:30 - 4:00 pm | |
| Sat., 12/13 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:00 p.m. | 1:00 - 4:30 pm | |
| Sun., 12/14 | Miscellaneous Events | Stby Park & Rec Masters Swim Program | - PHS Pool | 9:30 a.m. | 9:30 - 11:30 am | |
| Sun., 12/14 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 12:30 p.m. | 12:30 - 4:00 pm | |
| Sun., 12/14 | Miscellaneous Events | Stby Park & Rec Open Swimming | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Mon., 12/15 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Mon., 12/15 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Mon., 12/15 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Mon., 12/15 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 | |
| Mon., 12/15 | Miscellaneous Events | Mdby Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 12/16 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Tue., 12/16 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 12/16 | Miscellaneous Events | Stby Park & Rec Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 12/17 | V Boys Basketball | New Milford | Away - New Milford High School [Directions] | L 58-65 | 4:00 pm, Share bus with JVs | |
| Wed., 12/17 | JV Boys Basketball | New Milford | Away - New Milford High School [Directions] | 5:15 p.m. | 4:00 pm, Share bus with Varsity | |
| Wed., 12/17 | FR Boys Basketball | New Milford | Away - New Milford High School [Directions] | 3:30 p.m. | 2:15 | |
| Wed., 12/17 | V Boys Ice Hockey | Trumbull | Home - Taft-Mays Rink [Directions] | L 0-4 | ||
| Wed., 12/17 | V Boys Swimming and Diving | Newtown | Away - Newtown High School Pool [Directions] | 4:00 p.m. | 2:30 | |
| Wed., 12/17 | V Wrestling | Masuk | Away - David Strong Gymnasium @ Masuk High School [Directions] | 7:00 p.m. | 5:15 pm | |
| Wed., 12/17 | FR Girls Basketball | Naugatuck | Away - Naugatuck High School [Directions] | 3:30 p.m. | 2:45 | |
| Wed., 12/17 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Wed., 12/17 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 12/17 | Miscellaneous Events | Middlebury Park & Rec Basketball Practice | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Wed., 12/17 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 12/17 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 | |
| Thu., 12/18 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Thu., 12/18 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 12/18 | Miscellaneous Events | Stby Park & Rec Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 12/19 | V Boys Indoor Track | New Haven Invitational | Away | 4:00 p.m. | 2:30, Share bus with Girls IT | @ Floyd Little Athletic Center |
| Fri., 12/19 | V Boys Swimming and Diving | Alumni Meet | Home - PHS Pool [Directions] | 7:30 p.m. | ||
| Fri., 12/19 | V Girls Basketball | Hillhouse | Away [Directions] | W 58-55 | 3:30 | vs. Hillhouse |
| Fri., 12/19 | V Girls Indoor Track | New Haven Invitational | Away | 4:00 p.m. | 2:30, Share bus with Boys IT | @ Floyd Little Athletic Center |
| Fri., 12/19 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Fri., 12/19 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Fri., 12/19 | Miscellaneous Events | Youth Wrestling Match | - Auxiliary Gym | 6:30 p.m. | 6:30 - 8:30 pm | |
| Fri., 12/19 | Miscellaneous Events | Middlebury Park & Rec Basketball Practice | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Sat., 12/20 | V Boys Ice Hockey | Wilton | Away - Winter Garden Rink-Ridgefield [Directions] | L 1-2 | 6:45 p.m. | |
| Sat., 12/20 | V Boys Indoor Track | New Haven Invitational | Away | 9:00 a.m. | 7:45 Share bus with Girls IT | |
| Sat., 12/20 | V Wrestling | Pomperaug Holiday Invitational Tournament | Home - PHS Main Gym [Directions] | 9:00 a.m. | ||
| Sat., 12/20 | V Girls Basketball | Cromwell | Away [Directions] | W 63-61 | TBA | 1:00 consolation, 3:00 championship |
| Sat., 12/20 | V Girls Indoor Track | New Haven Invitational | Away | 9:00 a.m. | 7:45 am share bus with Boys IT | |
| Sat., 12/20 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 12:30 p.m. | 12:30 - 4:00 pm | |
| Sat., 12/20 | Miscellaneous Events | Stby Park & Rec Open Swimming | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 12/21 | Miscellaneous Events | Stby Park & Rec Masters Swim Program | - PHS Pool | 9:30 a.m. | 9:30 - 11:30 am | |
| Sun., 12/21 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 12:30 p.m. | 12:30 - 4:00 pm | |
| Sun., 12/21 | Miscellaneous Events | Stby Park & Rec Open Swimming | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Mon., 12/22 | V Boys Basketball | Joel Barlow | Home - PHS Main Gym [Directions] | L 55-61 | non league game, $5 Adults, $3 Students | |
| Mon., 12/22 | JV Boys Basketball | Joel Barlow | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 12/22 | FR Boys Basketball | Joel Barlow | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Mon., 12/22 | V Boys Ice Hockey | EnricoFermi | Home [Directions] | L 3-4 | ||
| Mon., 12/22 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Mon., 12/22 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Mon., 12/22 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Mon., 12/22 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 | |
| Mon., 12/22 | Miscellaneous Events | Mdby Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 12/23 | V Girls Basketball | Kolbe Cathedral | Away - Sheehan Center [Directions] | W 74-53 | $5 Adults, $3 Students | |
| Tue., 12/23 | JV Girls Basketball | Kolbe Cathedral | Home - PHS Main Gym [Directions] | Cancelled | ||
| Tue., 12/23 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Tue., 12/23 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 12/23 | Miscellaneous Events | Stby Park & Rec Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Sat., 12/27 | V Boys Basketball | Northwestern | Home - PHS Main Gym [Directions] | W 71-59 | $5 Adults, $3 Students | |
| Sat., 12/27 | JV Boys Basketball | Northwestern | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Sat., 12/27 | FR Boys Basketball | WCA | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Sat., 12/27 | V Boys Ice Hockey | Trinity Catholic | Home - Taft-Mays Rink [Directions] | W 7-2 | ||
| Sat., 12/27 | V Boys Indoor Track | Wesleyan Invitational | Away | Cancelled | ||
| Sat., 12/27 | V Wrestling | Frank Chaves Farmington Valley Invitational | Away [Directions] | 9:00 a.m. | 6:30 am | |
| Sat., 12/27 | V Competitive Cheerleading | Northwestern | Home - PHS Main Gym [Directions] | 7:00 p.m. | ||
| Sat., 12/27 | V Girls Basketball | Sacred Heart Academy | Away [Directions] | W 56-49 | 1:00 pm | vs. SHA |
| Sat., 12/27 | FR Girls Basketball | Danbury | Home - PHS Main Gym [Directions] | 1:00 p.m. | ||
| Sat., 12/27 | V Girls Indoor Track | Wesleyan Invitational | Away | Cancelled | ||
| Sun., 12/28 | Miscellaneous Events | Stby Park & Rec Masters Swim | - PHS Pool | 8:00 a.m. | 8:00 am - 12:00 noon | |
| Mon., 12/29 | V Boys Ice Hockey | Stamford | Away - Terry Conners Ice Rink [Directions] | W 3-2 | 12:30 p.m. | |
| Mon., 12/29 | V Girls Basketball | Plainville | Away - Wood Gymnasium [Directions] | W 54-28 | 3:45 | 3:00 Consolation or 6:15 Championship |
| Mon., 12/29 | Miscellaneous Events | PAC Team Swim Practice | - PHS Pool | 11:00 a.m. | 11:00 - 1:45 pm | |
| Tue., 12/30 | V Boys Basketball | Middletown | Home - PHS Main Gym [Directions] | L 50-61 | $5 Adults, $3 Students | |
| Tue., 12/30 | JV Boys Basketball | Middletown | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 12/30 | FR Boys Basketball | Middletown | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Tue., 12/30 | V Boys Indoor Track | SWC Developmental | Away | 2:00 p.m. | 12:30 pm, share bus with girls track | @ Wilton High School |
| Tue., 12/30 | V Girls Indoor Track | SWC Developmental | Away [Directions] | 2:00 p.m. | 12:30 pm, share bus with boys track | @ Wilton HS |
| Tue., 12/30 | Miscellaneous Events | PAC Team Swim Practice | - PHS Pool | 11:00 a.m. | 11:00 - 1:45 pm | |
| Fri., 1/2 | V Girls Basketball | Wilton (Scrim.) | Away [Directions] | 11:00 a.m. | 9:30 am | |
| Fri., 1/2 | FR Girls Soccer | Wilton (Scrim.) | Away [Directions] | Cancelled | ||
| Fri., 1/2 | Miscellaneous Events | PAC Team Swim Practice | - PHS Pool | 11:00 a.m. | 11:00 - 1:45 pm | |
| Sat., 1/3 | V Boys Basketball | Nonnewaug | Away - Nonnewaug High School [Directions] | W 52-51 | 2:30, share bus with JVs | |
| Sat., 1/3 | JV Boys Basketball | Nonnewaug | Away - Nonnewaug High School [Directions] | 1:30 p.m. | 2:30 share bus w/varsity | |
| Sat., 1/3 | V Boys Ice Hockey | Cheshire | Home - Taft-Mays Rink [Directions] | L 1-5 | ||
| Sat., 1/3 | V Boys Indoor Track | SWC Developmental Meet | Away | 9:00 a.m. | 7:15 am | @ Wesleyan University |
| Sat., 1/3 | V Wrestling | Trumball Duals | Away | 9:00 a.m. | 7:00 am | |
| Sat., 1/3 | V Girls Gymnastics | Pomperaug Invitational | Home - PHS Main Gym [Directions] | 120.85 | ||
| Sat., 1/3 | V Girls Indoor Track | SWC Developmental Meet | Away | 9:00 a.m. | 7:15 am | @ Wesleyan University |
| Sat., 1/3 | Miscellaneous Events | Stby Park & Rec High School Basketball | - Auxiliary Gym | 12:00 p.m. | 12:00 - 9:30 pm | |
| Sun., 1/4 | Miscellaneous Events | Stby Park & Rec Masters Swim | - PHS Pool | 8:00 a.m. | 8:00 am - 12:00 noon | |
| Sun., 1/4 | Miscellaneous Events | Southbury Softball | - Auxiliary Gym | 8:00 a.m. | 8:00 to 11:00 am | |
| Sun., 1/4 | Miscellaneous Events | Stby Park & Rec High School Basketball | - PHS Main Gym | 1:15 p.m. | 1:15 - 9:00 pm | |
| Mon., 1/5 | Miscellaneous Events | PAC Team Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Mon., 1/5 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Mon., 1/5 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Mon., 1/5 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 | |
| Mon., 1/5 | Miscellaneous Events | Mdby Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 1/6 | V Boys Basketball | Bethel | Away - Bethel High School [Directions] | W 65-62 | 4:00 pm, Share bus with JVs | |
| Tue., 1/6 | JV Boys Basketball | Bethel | Away - Bethel High School [Directions] | 5:15 p.m. | 4:00 pm, Share bus with Varsity | |
| Tue., 1/6 | FR Boys Basketball | Bethel | Away - Bethel High School [Directions] | 3:30 p.m. | 2:15 | |
| Tue., 1/6 | V Boys Swimming and Diving | Bethel | Home - PHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/6 | V Girls Basketball | Bethel | Home - PHS Main Gym [Directions] | W 43-37 | $5 Adults, $3 Students | |
| Tue., 1/6 | JV Girls Basketball | Bethel | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/6 | Miscellaneous Events | PAC Team Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Tue., 1/6 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 1/6 | Miscellaneous Events | Stby Softball Parents Clinic | - Auxiliary Gym | 7:00 p.m. | 7 - 9:00 pm | |
| Tue., 1/6 | Miscellaneous Events | Stby Park & Rec Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 1/7 | V Boys Ice Hockey | Farmington Valley Generals | Away - Avon Old Farms [Directions] | W 4-1 | 6:00 p.m. | |
| Wed., 1/7 | V Boys Indoor Track | SWC JV Developmental Meet | Away | 3:00 p.m. | 2:15 pm | @ Danbury Sports Dome |
| Wed., 1/7 | V Wrestling | New Milford | Home - Auxiliary Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/7 | V Co-ed Alpine Skiing | League Ski Race | Away - Mt. Southington | 3:00 p.m. | 2:15 pm | |
| Wed., 1/7 | V Girls Indoor Track | SWC JV Developmental Meet | Away | 3:00 p.m. | 2:15 | @ Danbury Sports Dome |
| Wed., 1/7 | Miscellaneous Events | PAC Team Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Wed., 1/7 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 1/7 | Miscellaneous Events | Middlebury Park & Rec Basketball Practice | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Wed., 1/7 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 1/8 | V Boys Swimming and Diving | Joel Barlow-Bethel Swim | Home [Directions] | 4:30 p.m. | ||
| Thu., 1/8 | Miscellaneous Events | PAC Team Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Thu., 1/8 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 1/8 | Miscellaneous Events | Stby Park & Rec Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 1/9 | V Girls Gymnastics | Oxford | Away [Directions] | 132.95 | @ Kinetic Kids | |
| Fri., 1/9 | Miscellaneous Events | PAC Team Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Fri., 1/9 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Fri., 1/9 | Miscellaneous Events | Middlebury Park & Rec Basketball Practice | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Sat., 1/10 | V Boys Basketball | Masuk | Home - PHS Main Gym [Directions] | L 55-65 | $5 Adults, $3 Students | |
| Sat., 1/10 | JV Boys Basketball | Masuk | Home - PHS Main Gym [Directions] | 12:15 p.m. | ||
| Sat., 1/10 | FR Boys Basketball | Masuk | Home - PHS Main Gym [Directions] | 10:30 a.m. | ||
| Sat., 1/10 | V Boys Ice Hockey | Milford Coop | Home - Taft-Mays Rink [Directions] | L 3-5 | ||
| Sat., 1/10 | V Wrestling | Xavier Duals | Away [Directions] | 9:00 a.m. | 7:00 am | |
| Sat., 1/10 | Miscellaneous Events | Stby Park & Rec High School Basketball | - PHS Main Gym | 12:00 p.m. | 12:00 - 9:30 pm | |
| Sat., 1/10 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 12:30 p.m. | 12:30 - 4:00 pm | |
| Sat., 1/10 | Miscellaneous Events | Stby Park & Rec Open Swimming | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 1/11 | Miscellaneous Events | Southbury Softball | - Auxiliary Gym | 8:00 a.m. | 8:00 to 11:00 am | |
| Sun., 1/11 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 12:30 p.m. | 12:30 - 4:00 pm | |
| Sun., 1/11 | Miscellaneous Events | Stby Park & Rec Open Swimming | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 1/11 | Miscellaneous Events | Stby Park & Rec High School Basketball | - PHS Main Gym | 1:15 p.m. | 1:15 - 9:00 pm | |
| Mon., 1/12 | Miscellaneous Events | PAC Team Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Mon., 1/12 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Mon., 1/12 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Mon., 1/12 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 | |
| Mon., 1/12 | Miscellaneous Events | Mdby Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 1/13 | V Boys Basketball | Immaculate | Home - PHS Main Gym [Directions] | L 50-62 | $5 Adults, $3 Students | |
| Tue., 1/13 | JV Boys Basketball | Immaculate | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/13 | FR Boys Basketball | Immaculate | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Tue., 1/13 | V Boys Swimming and Diving | Bunnell-Stratford | Away - Flood Pool [Directions] | 6:00 p.m. | 4:00 pm | @ Flood Jr. High |
| Tue., 1/13 | V Girls Basketball | Immaculate | Away - Immaculate High School [Directions] | W 62-48 | 4:00 pm, Share bus with JVs | |
| Tue., 1/13 | JV Girls Basketball | Immaculate | Away - Immaculate High School [Directions] | 5:15 p.m. | 4:00 pm, Share bus with Varsity | |
| Tue., 1/13 | FR Girls Basketball | Immaculate | Away - Immaculate High School [Directions] | 3:30 p.m. | 2:15 pm | |
| Tue., 1/13 | V Girls Gymnastics | Weston, Joel Barlow, Nonnewaug | Home - Auxiliary Gym [Directions] | 127.30 | ||
| Tue., 1/13 | Miscellaneous Events | PAC Team Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Tue., 1/13 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 1/13 | Miscellaneous Events | Stby Park & Rec Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 1/14 | V Boys Indoor Track | JV Developmental Meet | Away | 3:00 p.m. | 2:15 pm | @ Danbury Sports Dome |
| Wed., 1/14 | V Wrestling | Bunnell | Away - Bunnell [Directions] | 7:00 p.m. | 5:00 pm | |
| Wed., 1/14 | V Girls Indoor Track | JV Developmental Meet | Away | 3:00 p.m. | 2:15 pm | @ Danbury Sports Dome |
| Wed., 1/14 | Miscellaneous Events | PAC Team Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Wed., 1/14 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 1/14 | Miscellaneous Events | Middlebury Park & Rec Basketball Practice | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Wed., 1/14 | Miscellaneous Events | Stby Softball Parents Clinic | - Auxiliary Gym | 7:00 p.m. | 7 - 9:00 pm | |
| Wed., 1/14 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 1/14 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 | |
| Thu., 1/15 | Miscellaneous Events | PAC Team Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Thu., 1/15 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 1/15 | Miscellaneous Events | Stby Park & Rec Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 1/16 | V Boys Basketball | Bunnell | Away - Bunnell [Directions] | L 40-61 | 4:00 pm, Share bus with JVs | |
| Fri., 1/16 | JV Boys Basketball | Bunnell | Away - Bunnell [Directions] | 5:15 p.m. | 4:00 pm, Share bus with Varsity | |
| Fri., 1/16 | FR Boys Basketball | Bunnell | Away - Bunnell [Directions] | 3:30 p.m. | 2:15 | |
| Fri., 1/16 | V Boys Ice Hockey | Masuk | Home - Taft-Mays Rink [Directions] | L 0-5 | ||
| Fri., 1/16 | V Boys Swimming and Diving | Brookfield | Home - PHS Pool [Directions] | 6:00 p.m. | ||
| Fri., 1/16 | JV Wrestling | JV Wrestling Night | Home - Auxiliary Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/16 | V Competitive Cheerleading | Bunnell | Home - PHS Main Gym [Directions] | 7:00 p.m. | ||
| Fri., 1/16 | V Girls Basketball | Bunnell | Home - PHS Main Gym [Directions] | W 76-22 | $5 Adults, $3 Students | |
| Fri., 1/16 | JV Girls Basketball | Bunnell | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/16 | FR Girls Basketball | Bunnell | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 1/16 | Miscellaneous Events | PAC Team Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Fri., 1/16 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Fri., 1/16 | Miscellaneous Events | Middlebury Park & Rec Basketball Practice | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Sat., 1/17 | V Wrestling | Lyman Memorial/Windham Tech | Away [Directions] | 10:00 a.m. | 7:00 am | |
| Sat., 1/17 | V Competitive Cheerleading | Seymour Competition | Away | TBA | 8:15 am | |
| Sat., 1/17 | V Girls Basketball | Stratford | Away - Needham Memorial Gymnasium [Directions] | W 60-40 | 10:00 am, Share bus with JVs | |
| Sat., 1/17 | JV Girls Basketball | Stratford | Away - Needham Memorial Gymnasium [Directions] | 11:30 a.m. | 10:00 am, Share bus with Varsity | |
| Sat., 1/17 | FR Girls Basketball | Stratford | Away - Needham Memorial Gymnasium [Directions] | 10:00 a.m. | 8:30 am | |
| Sat., 1/17 | Miscellaneous Events | Stby Park & Rec High School Basketball | - PHS Main Gym | 12:00 p.m. | 12:00 - 9:30 pm | |
| Sat., 1/17 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 12:30 p.m. | 12:30 - 4:00 pm | |
| Sat., 1/17 | Miscellaneous Events | Stby Park & Rec Open Swimming | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 1/18 | Miscellaneous Events | Southbury Softball | - Auxiliary Gym | 8:00 a.m. | 8:00 to 11:00 am | |
| Sun., 1/18 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 12:30 p.m. | 12:30 - 4:00 pm | |
| Sun., 1/18 | Miscellaneous Events | Stby Park & Rec Open Swimming | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 1/18 | Miscellaneous Events | Stby Park & Rec High School Basketball | - PHS Main Gym | 1:15 p.m. | 1:15 - 9:00 pm | |
| Mon., 1/19 | V Boys Indoor Track | SWC Developmental Meet | Away | 9:00 a.m. | 7:15 am | @ Wesleyan University |
| Mon., 1/19 | V Girls Indoor Track | SWC Developmental Meet | Away | 9:00 a.m. | 7:30 am | @ Wesleyan University |
| Tue., 1/20 | V Boys Basketball | New Milford | Home - PHS Main Gym [Directions] | W 63-52 | $5 Adults, $3 Students | |
| Tue., 1/20 | JV Boys Basketball | New Milford | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/20 | FR Boys Basketball | New Milford | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Tue., 1/20 | V Boys Swimming and Diving | Masuk | Home - PHS Pool [Directions] | 4:00 p.m. | ||
| Tue., 1/20 | V Girls Basketball | New Milford | Away - New Milford High School [Directions] | W 39-38 | 4:00 pm, Share bus with JVs | |
| Tue., 1/20 | JV Girls Basketball | New Milford | Away - New Milford High School [Directions] | 5:15 p.m. | 4:00 pm, Share bus with Varsity | |
| Tue., 1/20 | FR Girls Basketball | New Milford | Away - New Milford High School [Directions] | 3:30 p.m. | 2:15 pm | |
| Tue., 1/20 | V Girls Gymnastics | New Milford, Nonnewaug, Jonathan Law | Home - Auxiliary Gym [Directions] | 122.05 | ||
| Tue., 1/20 | Miscellaneous Events | PAC Team Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Tue., 1/20 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 1/21 | V Wrestling | Stratford | Home - Auxiliary Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/21 | V Co-ed Alpine Skiing | League Ski Race | Away - Mt. Southington | 3:00 p.m. | 2:15 pm | |
| Wed., 1/21 | Miscellaneous Events | PAC Team Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Wed., 1/21 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 1/21 | Miscellaneous Events | Middlebury Park & Rec Basketball Practice | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Wed., 1/21 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 1/21 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 | |
| Wed., 1/21 | School Holidays and Closings | Mid Term Exams | ||||
| Thu., 1/22 | Miscellaneous Events | PAC Team Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Thu., 1/22 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 1/22 | Miscellaneous Events | Stby Park & Rec Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 1/22 | School Holidays and Closings | Mid Term Exams | ||||
| Fri., 1/23 | V Boys Basketball | New Fairfield | Away - NFHS Gym [Directions] | L 36-52 | 4:00 pm, Share bus with JVs | |
| Fri., 1/23 | JV Boys Basketball | New Fairfield | Away - New Fairfield HS [Directions] | 5:15 p.m. | 4:00 pm, Share bus with Varsity | |
| Fri., 1/23 | FR Boys Basketball | New Fairfield | Away - NFHS Gym [Directions] | 3:30 p.m. | 2:15 | |
| Fri., 1/23 | V Boys Ice Hockey | Shepaug Valley Ice Hockey | Home - Taft-Mays Rink [Directions] | W 3-0 | ||
| Fri., 1/23 | V Boys Swimming and Diving | Naugatuck, Conard | Away - Naugatuck High School [Directions] | 4:00 p.m. | 2:30 pm | |
| Fri., 1/23 | JV Wrestling | JV Wrestling Night | Home - Auxiliary Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/23 | V Competitive Cheerleading | New Fairfield | Home - PHS Main Gym [Directions] | 7:00 p.m. | ||
| Fri., 1/23 | V Girls Basketball | New Fairfield | Home - PHS Main Gym [Directions] | L 58-60 | $5 Adults, $3 Students | |
| Fri., 1/23 | JV Girls Basketball | New Fairfield | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/23 | Miscellaneous Events | PAC Team Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Fri., 1/23 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Fri., 1/23 | Miscellaneous Events | Mid-Year Exams | 7:00 p.m. | |||
| Fri., 1/23 | Miscellaneous Events | Middlebury Park & Rec Basketball Practice | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Fri., 1/23 | School Holidays and Closings | Mid Term Exams | ||||
| Sat., 1/24 | V Wrestling | Rodney Smith Invitational | Away [Directions] | Cancelled | ||
| Sat., 1/24 | Miscellaneous Events | Kinetic Kids Gymnastic Invitational | - PHS Main Gym | 7:00 a.m. | 7:00 am - 10:00 pm | |
| Sat., 1/24 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 12:30 p.m. | 12:30 - 4:00 pm | |
| Sat., 1/24 | Miscellaneous Events | Stby Park & Rec Open Swimming | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 1/25 | V Competitive Cheerleading | Wolcott Competition | Away [Directions] | TBA | 10:00 am | |
| Sun., 1/25 | Miscellaneous Events | Kinetic Kids Gymnastic Invitational | - PHS Main Gym | 7:00 a.m. | 7:00 am - 10:00 pm | |
| Sun., 1/25 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 12:30 p.m. | 12:30 - 4:00 pm | |
| Sun., 1/25 | Miscellaneous Events | Stby Park & Rec Open Swimming | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Mon., 1/26 | Miscellaneous Events | PAC Team Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Mon., 1/26 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Mon., 1/26 | Miscellaneous Events | Mid-Year Exams | 7:00 p.m. | |||
| Mon., 1/26 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Mon., 1/26 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 | |
| Mon., 1/26 | Miscellaneous Events | Mdby Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Mon., 1/26 | School Holidays and Closings | Mid Term Exams | ||||
| Tue., 1/27 | Miscellaneous Events | PAC Team Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Tue., 1/27 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 1/27 | Miscellaneous Events | Stby Park & Rec Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 1/28 | V Boys Ice Hockey | New Milford | Away - Canterbury School [Directions] | L 1-3 | 6:00 p.m. | |
| Wed., 1/28 | V Boys Swimming and Diving | Weston | Away - Weston Middle School Pool [Directions] | 4:30 p.m. | 2:15 pm | |
| Wed., 1/28 | V Wrestling | Notre Dame-Fairfield | Home - Auxiliary Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/28 | Miscellaneous Events | PAC Team Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Wed., 1/28 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 1/28 | Miscellaneous Events | Middlebury Park & Rec Basketball Practice | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Wed., 1/28 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 1/28 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 | |
| Thu., 1/29 | V Boys Basketball | Brookfield | Away - BHS Big Gym [Directions] | L 51-53 | 4:00 pm, Share bus with JVs | |
| Thu., 1/29 | JV Boys Basketball | Brookfield | Away - BHS Big Gym [Directions] | 5:15 p.m. | 4:00 pm, Share bus with Varsity | |
| Thu., 1/29 | FR Boys Basketball | Brookfield | Away - BHS Big Gym [Directions] | 3:30 p.m. | 2:15 | |
| Thu., 1/29 | V Co-ed Alpine Skiing | League Ski Race | Away - Mt. Southington | 3:00 p.m. | 2:15 pm | |
| Thu., 1/29 | V Girls Basketball | Brookfield | Home - PHS Main Gym [Directions] | W 63-22 | $5 Adults, $3 Students | |
| Thu., 1/29 | JV Girls Basketball | Brookfield | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Thu., 1/29 | FR Girls Basketball | Brookfield | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Thu., 1/29 | V Girls Gymnastics | Newtown, Oxford, Nonnewaug | Home - Auxiliary Gym [Directions] | 128.05 | ||
| Thu., 1/29 | Miscellaneous Events | PAC Team Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Thu., 1/29 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 1/29 | Miscellaneous Events | Stby Park & Rec Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 1/30 | V Boys Basketball | Joel Barlow | Away - Lower Gym [Directions] | W 58-35 | 4:00 pm, Share bus with JVs | |
| Fri., 1/30 | JV Boys Basketball | Joel Barlow | Away - Lower Gym [Directions] | 5:15 p.m. | 4:00 share bus w/varsity | |
| Fri., 1/30 | FR Boys Basketball | Joel Barlow | Away - Lower Gym [Directions] | 3:30 p.m. | 2:15 | |
| Fri., 1/30 | V Boys Swimming and Diving | Watertown | Away - Frank M. Reinhold Pool @ Watertown High School [Directions] | 6:00 p.m. | 4:15 | |
| Fri., 1/30 | JV Wrestling | JV Wrestling Night | Home - Auxiliary Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/30 | V Competitive Cheerleading | Joel Barlow | Home - PHS Main Gym [Directions] | 7:00 p.m. | ||
| Fri., 1/30 | V Girls Basketball | Joel Barlow | Home - PHS Main Gym [Directions] | W 57-40 | $5 Adults, $3 Students, Park and Rec Basketball Night | |
| Fri., 1/30 | JV Girls Basketball | Joel Barlow | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/30 | FR Girls Basketball | Joel Barlow | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 1/30 | Miscellaneous Events | PAC Team Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Fri., 1/30 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Fri., 1/30 | Miscellaneous Events | Middlebury Park & Rec Basketball Practice | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Sat., 1/31 | V Boys Ice Hockey | Danbury | Home - Taft-Mays Rink [Directions] | W 3-1 | ||
| Sat., 1/31 | V Wrestling | Portland Duals | Away | 8:00 a.m. | 6:30 am | |
| Sat., 1/31 | Miscellaneous Events | Stby Park & Rec High School Basketball | - PHS Main Gym | 12:00 p.m. | 12:00 - 9:30 pm | |
| Sat., 1/31 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 12:30 p.m. | 12:30 - 4:00 pm | |
| Sun., 2/1 | Miscellaneous Events | Southbury Softball | - Auxiliary Gym | 8:00 a.m. | 8:00 to 11:00 am | |
| Sun., 2/1 | Miscellaneous Events | Stby Park & Rec High School Basketball | - PHS Main Gym | 1:15 p.m. | 1:15 - 9:00 pm | |
| Sun., 2/1 | Miscellaneous Events | Southbury Park and Rec Basketball | - Auxiliary Gym | 4:00 p.m. | ||
| Mon., 2/2 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Mon., 2/2 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Mon., 2/2 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Mon., 2/2 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 | |
| Mon., 2/2 | Miscellaneous Events | Mdby Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 2/3 | V Girls Gymnastics | Nonnewaug, Staples | Home - Auxiliary Gym [Directions] | 129 | ||
| Tue., 2/3 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Tue., 2/3 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 2/3 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 2/3 | Miscellaneous Events | Stby Park & Rec Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 2/4 | V Boys Ice Hockey | North Branford | Away - Northford Ice Pavilion [Directions] | L 1-4 | 6:30 p.m. | |
| Wed., 2/4 | V Boys Indoor Track | SWC JV Developmental Meet | Away | 3:00 a.m. | 2:15 pm | @ Danbury Sports Dome |
| Wed., 2/4 | V Boys Swimming and Diving | New Fairfield | Home [Directions] | 6:30 p.m. | $5 Adults, $3 Students | |
| Wed., 2/4 | V Wrestling | New Fairfield | Away - NFHS Gym [Directions] | 6:00 p.m. | 4:15 pm | |
| Wed., 2/4 | V Girls Indoor Track | SWC JV Developmental Meet | Away | 3:00 p.m. | 2:15 pm | @ Danbury Sports Dome |
| Wed., 2/4 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Wed., 2/4 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 2/4 | Miscellaneous Events | Middlebury Park & Rec Basketball Practice | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Wed., 2/4 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 2/5 | V Boys Basketball | Weston | Home - PHS Main Gym [Directions] | L 41-56 | $5 Adults, $3 Students | |
| Thu., 2/5 | JV Boys Basketball | Weston | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Thu., 2/5 | FR Boys Basketball | Weston | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Thu., 2/5 | V Co-ed Alpine Skiing | League Ski Race | Away - Mt. Southington | 3:00 p.m. | 2:15 pm | |
| Thu., 2/5 | V Bowling | Lakewood Lanes | Away | 3:00 p.m. | 2:15 | |
| Thu., 2/5 | V Girls Basketball | Weston | Away - WHS Gymnasium [Directions] | W 63-37 | 4:00 pm, Share bus with JVs | |
| Thu., 2/5 | JV Girls Basketball | Weston | Away - WHS Gymnasium [Directions] | 5:15 p.m. | 4:00 pm, Share bus with Varsity | |
| Thu., 2/5 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Thu., 2/5 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 2/5 | Miscellaneous Events | Stby Park & Rec Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 2/6 | V Boys Basketball | Notre Dame-Fairfield | Home - PHS Main Gym [Directions] | L 46-55 | $5 Adults, $3 Students | |
| Fri., 2/6 | JV Boys Basketball | Notre Dame-Fairfield | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/6 | FR Boys Basketball | Notre Dame-Fairfield | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 2/6 | V Competitive Cheerleading | Notre Dame-Fairfield | Home - PHS Main Gym [Directions] | 7:00 p.m. | ||
| Fri., 2/6 | V Girls Basketball | Notre Dame-Fairfield | Away - Sister Marion Rielly Auditorium at Notre Dame [Directions] | L 57-66 | 4:00 pm, Share bus with JVs | |
| Fri., 2/6 | JV Girls Basketball | Notre Dame-Fairfield | Away - Sister Marion Rielly Auditorium at Notre Dame [Directions] | 5:15 p.m. | 4:00 pm, Share bus with Varsity | |
| Fri., 2/6 | FR Girls Basketball | Notre Dame-Fairfield | Away - Sister Marion Rielly Auditorium at Notre Dame [Directions] | 3:30 p.m. | 2:15 pm | |
| Fri., 2/6 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Fri., 2/6 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Fri., 2/6 | Miscellaneous Events | Middlebury Park & Rec Basketball Practice | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Sat., 2/7 | V Boys Indoor Track | South-West Championship Meet | Away | 5:00 p.m. | 3:30 pm | @ Floyd Little Athletic Center, New Haven |
| Sat., 2/7 | V Wrestling | Farmington, Branford, Seymour, Maloney | Home - PHS Main Gym [Directions] | Cancelled | ||
| Sat., 2/7 | V Wrestling | Farmington, Seymour, Branford, Maloney | Away [Directions] | 9:00 a.m. | 7:00 am | @ Farmington HS |
| Sat., 2/7 | V Competitive Cheerleading | SWC Championship | Away [Directions] | 4:00 p.m. | 12:00 pm | |
| Sat., 2/7 | FR Girls Basketball | Holy Cross | Away - Holy Cross HS [Directions] | 11:00 a.m. | 10:00 am | |
| Sat., 2/7 | V Girls Indoor Track | SWC Championship Meet | Away | 5:00 p.m. | 3:30 pm | @ Floyd Little Athletic Center in New Haven |
| Sat., 2/7 | Miscellaneous Events | Stby Park & Rec High School Basketball | - Auxiliary Gym | 12:00 p.m. | 12:00 - 9:30 pm | |
| Sat., 2/7 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 12:30 p.m. | 12:30 - 4:00 pm | |
| Sat., 2/7 | Miscellaneous Events | Stby Park & Rec Open Swimming | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 2/8 | Miscellaneous Events | Southbury Softball | - Auxiliary Gym | 8:00 a.m. | 8:00 to 11:00 am | |
| Sun., 2/8 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 12:30 p.m. | 12:30 - 4:00 pm | |
| Sun., 2/8 | Miscellaneous Events | Stby Park & Rec Open Swimming | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 2/8 | Miscellaneous Events | Stby Park & Rec High School Basketball | - PHS Main Gym | 1:15 p.m. | 1:15 - 9:00 pm | |
| Mon., 2/9 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Mon., 2/9 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Mon., 2/9 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Mon., 2/9 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 | |
| Mon., 2/9 | Miscellaneous Events | Mdby Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 2/10 | V Boys Basketball | Masuk | Away - David Strong Gymnasium @ Masuk High School [Directions] | L 54-64 | 4:00 pm, Share bus with JVs | |
| Tue., 2/10 | JV Boys Basketball | Masuk | Away - David Strong Gymnasium @ Masuk High School [Directions] | 5:15 p.m. | 4:00 pm, Share bus with Varsity | |
| Tue., 2/10 | FR Boys Basketball | Masuk | Away - David Strong Gymnasium @ Masuk High School [Directions] | 3:30 p.m. | 2:15 | |
| Tue., 2/10 | V Boys Swimming and Diving | New Milford | Home [Directions] | 6:00 p.m. | ||
| Tue., 2/10 | V Wrestling | Bethel | Home - Auxiliary Gym [Directions] | 6:00 p.m. | ||
| Tue., 2/10 | V Girls Basketball | Masuk | Home - PHS Main Gym [Directions] | W 60-42 | $5 Adults, $3 Students | |
| Tue., 2/10 | JV Girls Basketball | Masuk | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/10 | FR Girls Basketball | Masuk | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Tue., 2/10 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Tue., 2/10 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 2/10 | Miscellaneous Events | Stby Park & Rec Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 2/11 | V Boys Ice Hockey | Branford | Away - NORTHFORD ICE PAVILION [Directions] | L 0-5 | 2:00 p.m. | |
| Wed., 2/11 | V Boys Swimming and Diving | Florida Trip | Away | TBA | 4:15 am leave PHS | |
| Wed., 2/11 | V Co-ed Alpine Skiing | League Ski Race | Away - Mt. Southington | 3:00 p.m. | 2:15 pm | |
| Wed., 2/11 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Wed., 2/11 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 2/11 | Miscellaneous Events | Middlebury Park & Rec Basketball Practice | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Wed., 2/11 | Miscellaneous Events | Stby Softball Parents Clinic | - Auxiliary Gym | 7:00 p.m. | 7 - 9:00 pm | |
| Wed., 2/11 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 2/11 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 | |
| Thu., 2/12 | V Bowling | Lakewood Lanes | Away | 3:00 p.m. | 2:30 | |
| Thu., 2/12 | V Girls Gymnastics | SWC Championships | Away [Directions] | 133.2 | ||
| Thu., 2/12 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 2/12 | Miscellaneous Events | Mdby Fire Dept. | - PHS Pool | 8:00 p.m. | ||
| Thu., 2/12 | Miscellaneous Events | Stby Park & Rec Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 2/13 | V Boys Basketball | Kolbe Cathedral | Home - PHS Main Gym [Directions] | W 51-35 | $5 Adults, $3 Students | |
| Fri., 2/13 | JV Boys Basketball | Kolbe Cathedral | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/13 | V Boys Indoor Track | Class L State Meet | Away | 4:00 p.m. | 2:15 Share Bus with Girls Track | Floyd Little Athletic Center, New Haven |
| Fri., 2/13 | V Competitive Cheerleading | Kolbe Cathedral | Home - PHS Main Gym [Directions] | 7:00 p.m. | ||
| Fri., 2/13 | V Girls Basketball | Kolbe Cathedral | Away - Shehan Center [Directions] | W 60-42 | 4:00 pm, Share bus with JVS | |
| Fri., 2/13 | JV Girls Basketball | Kolbe Cathedral | Away - Shehan Center [Directions] | 5:15 p.m. | 4:00 pm, Share bus with Varsity | |
| Fri., 2/13 | V Girls Gymnastics | Jonathan Law | Away - Jonathan Law HS Old Gym [Directions] | 129.7 | ||
| Fri., 2/13 | V Girls Indoor Track | Class L State Meet | Away | 4:00 p.m. | 2:15, Share bus with Boys Track | @ Floyd Little Athletic Center, New Haven |
| Fri., 2/13 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 7:30 pm | |
| Sat., 2/14 | V Boys Indoor Track | Class L State Meet | Away | Cancelled | ||
| Sat., 2/14 | V Wrestling | Southwest Conference Championships | Away [Directions] | 8:00 a.m. | 6:00 am | @ Bunnell HS, 7:00 am Weigh In, $10 Adults, $5 Students |
| Sat., 2/14 | V Girls Indoor Track | Class L State Meet | Away | Cancelled | ||
| Sun., 2/15 | Miscellaneous Events | Southbury Softball | - Auxiliary Gym | 8:00 a.m. | 8:00 to 11:00 am | |
| Mon., 2/16 | V Boys Ice Hockey | North Haven | Home - Taft-Mays Rink [Directions] | L 0-1 | ||
| Mon., 2/16 | JV Wrestling | Pomperaug JV Tournament | Home - PHS Main Gym [Directions] | 9:00 a.m. | ||
| Mon., 2/16 | Miscellaneous Events | JV Wrestling Tournament Refreshments | - Health Classroom - Room 201 | 7:00 a.m. | 7:00 am to 5:00 pm | |
| Tue., 2/17 | V Boys Basketball | Newtown | Home - PHS Main Gym [Directions] | W 54-49 | $5 Adults, $3 Students | |
| Tue., 2/17 | JV Boys Basketball | Newtown | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/17 | FR Boys Basketball | Newtown | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Tue., 2/17 | V Boys Swimming and Diving | Return Trip from Florida | Away | 1:30 p.m. | 1:30 pick up at Bradley | |
| Tue., 2/17 | V Girls Basketball | Newtown | Away - Newtown High School Gymnasium [Directions] | L 54-62(OT) | 4:00 pm, Share bus with JVs | |
| Tue., 2/17 | JV Girls Basketball | Newtown | Away - Newtown High School Gymnasium [Directions] | 5:15 p.m. | 4:00 pm, Share bus with Varsity | |
| Tue., 2/17 | FR Girls Basketball | Newtown | Away - Newtown High School Gymnasium [Directions] | 3:30 p.m. | 2:15 pm | |
| Tue., 2/17 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Tue., 2/17 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 2/17 | Miscellaneous Events | Stby Softball Parents Clinic | - Auxiliary Gym | 7:00 p.m. | 7 - 9:00 pm | |
| Tue., 2/17 | Miscellaneous Events | Stby Park & Rec Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 2/18 | V Boys Ice Hockey | New Fairfield | Away [Directions] | L 0-3 | 5:30 p.m. | |
| Wed., 2/18 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Wed., 2/18 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 2/18 | Miscellaneous Events | Middlebury Park & Rec Basketball Practice | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Wed., 2/18 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 2/18 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 2/19 | V Boys Ice Hockey | Guilford | Away - East Haven Ice Rink [Directions] | L 0-5 | 5:15 p.m. | |
| Thu., 2/19 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Thu., 2/19 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 2/19 | Miscellaneous Events | Stby Park & Rec Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 2/20 | V Boys Basketball | Stratford | Home - PHS Main Gym [Directions] | L 56-66 | $5 Adults, $3 Students | |
| Fri., 2/20 | JV Boys Basketball | Stratford | Home - PHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/20 | FR Boys Basketball | Stratford | Home - PHS Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 2/20 | V Wrestling | Class L State Tournament | Away [Directions] | 6:00 p.m. | 1:30 | @ Bristol Central HS |
| Fri., 2/20 | V Competitive Cheerleading | Stratford | Home - PHS Main Gym [Directions] | 7:00 p.m. | ||
| Fri., 2/20 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Fri., 2/20 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Fri., 2/20 | Miscellaneous Events | Middlebury Park & Rec Basketball Practice | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Sat., 2/21 | V Boys Indoor Track | CIAC State Open | Away | 10:00 a.m. | 8:00 am,share bus with girls track | |
| Sat., 2/21 | V Wrestling | Class L State Tournament | Away [Directions] | 8:00 a.m. | 6:00 am | @ Bristol Central HS |
| Sat., 2/21 | V Girls Basketball | SWC Quarter-Finals | Away [Directions] | 1:00 p.m. | 11:15 am | @ New Fairfield High School, $8 Adults, $5 Students |
| Sat., 2/21 | V Girls Indoor Track | CIAC State Open | Away | 10:00 a.m. | 8:00 am, share bus with boys track | |
| Sat., 2/21 | Miscellaneous Events | Stby Park & Rec High School Basketball | - Auxiliary Gym | 12:00 p.m. | 12:00 - 9:30 pm | |
| Sat., 2/21 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 12:30 p.m. | 12:30 - 4:00 pm | |
| Sat., 2/21 | Miscellaneous Events | Stby Park & Rec Open Swimming | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 2/22 | Miscellaneous Events | Southbury Softball | - Auxiliary Gym | 8:00 a.m. | 8:00 to 11:00 am | |
| Sun., 2/22 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 12:30 p.m. | 12:30 - 4:00 pm | |
| Sun., 2/22 | Miscellaneous Events | Stby Park & Rec Open Swimming | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 2/22 | Miscellaneous Events | Stby Park & Rec High School Basketball | - PHS Main Gym | 1:15 p.m. | 1:15 - 9:00 pm | |
| Mon., 2/23 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Mon., 2/23 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Mon., 2/23 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Mon., 2/23 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Mon., 2/23 | Miscellaneous Events | Mdby Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 2/24 | V Boys Basketball | Bethel | Away - Bethel High School [Directions] | L 46-57 | 4:15 pm, Share bus with JVs | |
| Tue., 2/24 | JV Boys Basketball | Bethel | Away - Bethel High School [Directions] | 5:15 p.m. | 4:15 pm, Share bus with Varsity | |
| Tue., 2/24 | FR Boys Basketball | Bethel | Away - Bethel High School [Directions] | 3:30 p.m. | 2:15 | |
| Tue., 2/24 | V Girls Basketball | SWC Semi-Finals | Away [Directions] | 7:30 p.m. | 5:15 pm | @ Newtown HS. $8 Adults, $5 Students |
| Tue., 2/24 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Tue., 2/24 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 2/24 | Miscellaneous Events | Stby Park & Rec Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 2/25 | V Boys Ice Hockey | East Haven Coop | Away - DiLungo Rink [Directions] | L 2-10 | 3:45 p.m. | |
| Wed., 2/25 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Wed., 2/25 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 2/25 | Miscellaneous Events | Middlebury Park & Rec Basketball Practice | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Wed., 2/25 | Miscellaneous Events | Stby Softball Parents Clinic | - Auxiliary Gym | 7:00 p.m. | 7 - 9:00 pm | |
| Wed., 2/25 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 2/25 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 2/26 | V Girls Basketball | SWC Championship Game | Away | Cancelled | ||
| Thu., 2/26 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Thu., 2/26 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 2/26 | Miscellaneous Events | Stby Park & Rec Basketball | - PHS Main Gym | 6:30 p.m. | 6:30 - 8:45 pm | |
| Thu., 2/26 | Miscellaneous Events | Stby Park & Rec Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 2/27 | V Boys Basketball | SWC Quarter-Finals | Away | Cancelled | ||
| Fri., 2/27 | V Wrestling | CIAC Open Tournament | Away | 4:15 p.m. | 12:30 pm | |
| Fri., 2/27 | V Girls Indoor Track | New England Indoor Track Championships | Away | 4:30 p.m. | 11:00 am | @ Reggie Lewis Center, Roxbury, MA |
| Fri., 2/27 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:30 p.m. | 5:30 - 8:30 pm | |
| Fri., 2/27 | Miscellaneous Events | Student Council Dance | - PHS Main Gym | 6:00 p.m. | 6:00 - 11:00 pm | |
| Fri., 2/27 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Fri., 2/27 | Miscellaneous Events | Middlebury Park & Rec Basketball Practice | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Sat., 2/28 | V Boys Ice Hockey | Amity | Home - Taft-Mays Rink [Directions] | W 4-1 | ||
| Sat., 2/28 | V Wrestling | CIAC Open Tournament | Away | 9:00 a.m. | 6:45 am | |
| Sat., 2/28 | V Bowling | Bowl-O-Rama | Away | TBA | 8:30 am | |
| Sat., 2/28 | V Girls Gymnastics | Class M State Tournament | Home - PHS Main Gym [Directions] | TBA | ||
| Sat., 2/28 | Miscellaneous Events | Stby Park & Rec High School Basketball | - Auxiliary Gym | 12:00 p.m. | 12:00 - 9:30 pm | |
| Sat., 2/28 | Miscellaneous Events | Stby Park & Rec Open Swimming | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sat., 2/28 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 1:15 p.m. | 12:30 - 4:00 pm | |
| Sun., 3/1 | Miscellaneous Events | Southbury Softball | - Auxiliary Gym | 8:00 a.m. | 8:00 to 11:00 am | |
| Sun., 3/1 | Miscellaneous Events | Stby Park & Rec High School Basketball | - PHS Main Gym | 1:15 p.m. | 1:15 - 9:00 pm | |
| Sun., 3/1 | Miscellaneous Events | Stby Park & Rec Basketball | - Auxiliary Gym | 1:30 p.m. | 1:30 - 7:30 pm | |
| Mon., 3/2 | V Girls Basketball | East Catholic | Home [Directions] | 7:00 p.m. | $8 Adults, $5 Students | |
| Mon., 3/2 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Mon., 3/2 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:15 p.m. | 6:15 - 8:30 pm | |
| Mon., 3/2 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Mon., 3/2 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Mon., 3/2 | Miscellaneous Events | Mdby Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 3/3 | V Boys Basketball | SWC Semi-Finals | Away [Directions] | Cancelled | ||
| Tue., 3/3 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 3/3 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:15 p.m. | 6:15 - 8:30 pm | |
| Tue., 3/3 | Miscellaneous Events | Stby Park & Rec Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 3/4 | V Boys Ice Hockey | Daniel Hand | Home - Taft-Mays Rink [Directions] | L 1-2 | ||
| Wed., 3/4 | V Boys Swimming and Diving | SWC Diving Championships | Away [Directions] | 4:30 p.m. | 1:45 pm | warm-ups @ 4:30 pm |
| Wed., 3/4 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 3/4 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:15 p.m. | 6:15 - 8:30 pm | |
| Wed., 3/4 | Miscellaneous Events | Middlebury Park & Rec Basketball Practice | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Wed., 3/4 | Miscellaneous Events | Stby Softball Parents Clinic | - Auxiliary Gym | 7:00 p.m. | 7 - 9:00 pm | |
| Wed., 3/4 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 3/5 | V Boys Basketball | SWC Championship Game | Away | Cancelled | ||
| Thu., 3/5 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 3/5 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:15 p.m. | 6:15 - 8:30 pm | |
| Thu., 3/5 | Miscellaneous Events | Stby Park & Rec Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 3/6 | V Boys Swimming and Diving | SWC Championships | Away [Directions] | 6:00 p.m. | 2 buses, Varsity at 3:00pm, JVs at 4:45 pm | warm-ups begin @ 4:00 pm |
| Fri., 3/6 | V Girls Basketball | Avon | Away [Directions] | 7:00 p.m. | 5:00 pm | |
| Fri., 3/6 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Fri., 3/6 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:15 p.m. | 6:15 - 8:30 pm | |
| Fri., 3/6 | Miscellaneous Events | Stby Park & Rec Basketball Games | - PHS Main Gym | 6:30 p.m. | 6:30 - 8:00 pm | |
| Fri., 3/6 | Miscellaneous Events | Middlebury Park & Rec Basketball Practice | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Sat., 3/7 | V Competitive Cheerleading | State Championships | Away | TBA | 7:30 am | |
| Sat., 3/7 | V Girls Gymnastics | CIAC State Open | Away | TBA | TBA | |
| Sat., 3/7 | Miscellaneous Events | Stby Park & Rec High School Basketball | - Auxiliary Gym | 12:00 p.m. | 12:00 - 9:30 pm | |
| Sat., 3/7 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 12:30 p.m. | 12:30 - 4:00 pm | |
| Sat., 3/7 | Miscellaneous Events | Stby Park & Rec Open Swimming | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 3/8 | Miscellaneous Events | Southbury Softball | - Auxiliary Gym | 8:00 a.m. | 8:00 to 11:00 am | |
| Sun., 3/8 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 12:30 p.m. | 12:30 - 4:00 pm | |
| Sun., 3/8 | Miscellaneous Events | Stby Park & Rec Open Swimming | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 3/8 | Miscellaneous Events | Stby Park & Rec High School Basketball | - PHS Main Gym | 1:15 p.m. | 1:15 - 9:00 pm | |
| Mon., 3/9 | V Boys Ice Hockey | Championships | Away | TBA | ||
| Mon., 3/9 | Miscellaneous Events | Coaches Workshop | - Health Classroom - Room 201 | 4:00 p.m. | 4:00 to 7:00 pm | |
| Mon., 3/9 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Mon., 3/9 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:15 p.m. | 6:15 - 8:30 pm | |
| Mon., 3/9 | Miscellaneous Events | Mdby Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Mon., 3/9 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Mon., 3/9 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 3/10 | V Boys Swimming and Diving | JV Meet | Away | 4:30 p.m. | 2:30 pm | |
| Tue., 3/10 | Miscellaneous Events | CPR class for coaches | - Health Classroom - Room 201 | 5:00 p.m. | ||
| Tue., 3/10 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 3/10 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:15 p.m. | 6:15 - 8:30 pm | |
| Tue., 3/10 | Miscellaneous Events | Stby Park & Rec Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 3/11 | V Boys Swimming and Diving | CIAC Class L Diving Trials/Finals | Away - Middletown HS [Directions] | 5:30 p.m. | 2:30 | @ Middletown High School |
| Wed., 3/11 | Miscellaneous Events | Mdby Baseball Practice | - Auxiliary Gym | 5:45 p.m. | 5:45 - 7:15 pm | |
| Wed., 3/11 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 3/11 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:15 p.m. | 6:15 - 8:30 pm | |
| Wed., 3/11 | Miscellaneous Events | Middlebury Park & Rec Basketball Practice | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Wed., 3/11 | Miscellaneous Events | Stby Softball Parents Clinic | - Auxiliary Gym | 7:00 p.m. | 7 - 9:00 pm | |
| Wed., 3/11 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 3/12 | Miscellaneous Events | Spring Coaches and Captains Meeting | - All Purpose Room | 4:00 p.m. | 4:00 to 6:00 pm | |
| Thu., 3/12 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 3/12 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:15 p.m. | 6:15 - 8:30 pm | |
| Thu., 3/12 | Miscellaneous Events | Stby Park & Rec Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 3/13 | Miscellaneous Events | Rochambeau PTO March Madness | - PHS Main Gym | 5:00 p.m. | 5:00 - 9:30 pm | |
| Fri., 3/13 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Fri., 3/13 | Miscellaneous Events | Middlebury Park & Rec Basketball Practice | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Sat., 3/14 | V Boys Swimming and Diving | CIAC Class L Qualifying | Away - Kennedy HS [Directions] | 4:30 p.m. | 1:30 pm | @ Kenedy High School |
| Sat., 3/14 | Miscellaneous Events | Southbury Park and Rec Basketball | - PHS Main Gym | 10:00 a.m. | 10:00 am to 1:00 pm | |
| Sat., 3/14 | Miscellaneous Events | Southbury Park and Rec Basketball | - Auxiliary Gym | 12:00 p.m. | 12:00 - 4:00 | |
| Sat., 3/14 | Miscellaneous Events | Stby Park & Rec High School Basketball | - PHS Main Gym | 12:00 p.m. | 1:00 - 9:30 pm | |
| Sun., 3/15 | Miscellaneous Events | Southbury Softball | - Auxiliary Gym | 8:00 a.m. | 8:00 to 11:00 am | |
| Sun., 3/15 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 12:30 p.m. | 12:30 - 4:00 pm | |
| Sun., 3/15 | Miscellaneous Events | Stby Park & Rec Open Swimming | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 3/15 | Miscellaneous Events | Stby Park & Rec High School Basketball | - PHS Main Gym | 1:15 p.m. | 1:15 - 9:00 pm | |
| Mon., 3/16 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Mon., 3/16 | Miscellaneous Events | Mdby Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Mon., 3/16 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 3/17 | V Boys Swimming and Diving | CIAC Class L Finals | Away - Wesleyan Univ. [Directions] | 1:30 p.m. | 11:15 am | @ Weslyan University, $10 Adults, $8 Students |
| Tue., 3/17 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 3/17 | Miscellaneous Events | Stby Softball Parents Clinic | - Auxiliary Gym | 7:00 p.m. | 7 - 9:00 pm | |
| Tue., 3/17 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:15 p.m. | 7:15 - 8:45 pm | |
| Tue., 3/17 | Miscellaneous Events | Stby Park & Rec Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 3/18 | Miscellaneous Events | Mdby Baseball Practice | - Auxiliary Gym | 5:45 p.m. | 5:45 - 7:15 pm | |
| Wed., 3/18 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 3/18 | Miscellaneous Events | Middlebury Park & Rec Basketball Practice | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Wed., 3/18 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 8:30 p.m. | 8:30 - 10:00 pm | |
| Thu., 3/19 | V Boys Swimming and Diving | CIAC Open Diving | Away - Middletown [Directions] | 5:30 p.m. | No bus | |
| Thu., 3/19 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:15 p.m. | 5:15 - 6:45 pm | |
| Thu., 3/19 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 3/19 | Miscellaneous Events | Stby Park & Rec Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 3/20 | Miscellaneous Events | Blood Drive | - Auxiliary Gym | 6:00 a.m. | 6:00 am - 2:00 pm | |
| Fri., 3/20 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Fri., 3/20 | Miscellaneous Events | Middlebury Park & Rec Basketball Practice | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Sat., 3/21 | V Boys Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 2:30 p.m. | 11:30 am | |
| Sat., 3/21 | Miscellaneous Events | Stby Park & Rec High School Basketball | - PHS Main Gym | 9:00 a.m. | 9:00 am - 9:30 pm | |
| Sat., 3/21 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 12:30 p.m. | 12:30 - 4:00 pm | |
| Sat., 3/21 | Miscellaneous Events | Stby Park & Rec Open Swimming | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 3/22 | Miscellaneous Events | Southbury Softball | - Auxiliary Gym | 8:00 a.m. | 8:00 to 11:00 am | |
| Sun., 3/22 | Miscellaneous Events | Stby Park & Rec Open Swim | - PHS Pool | 12:30 p.m. | 12:30 - 4:00 pm | |
| Sun., 3/22 | Miscellaneous Events | Stby Park & Rec Open Swimming | - PHS Pool | 1:00 p.m. | 1:00 - 4:00 pm | |
| Sun., 3/22 | Miscellaneous Events | Stby Park & Rec High School Basketball | - PHS Main Gym | 1:15 p.m. | 1:15 - 9:00 pm | |
| Mon., 3/23 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Mon., 3/23 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:15 p.m. | 7:15 - 8:45 pm | |
| Mon., 3/23 | Miscellaneous Events | Mdby Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 3/24 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:15 p.m. | 5:15 - 6:45 pm | |
| Tue., 3/24 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Tue., 3/24 | Miscellaneous Events | Stby Park & Rec Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Wed., 3/25 | Miscellaneous Events | Mdby Baseball Practice | - Auxiliary Gym | 5:45 p.m. | 5:45 - 7:15 pm | |
| Wed., 3/25 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Wed., 3/25 | Miscellaneous Events | Middlebury Park & Rec Basketball Practice | - PHS Main Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Wed., 3/25 | Miscellaneous Events | Stby Park & Rec Adult Swim | - PHS Pool | 8:15 p.m. | 8:30 - 10:00 pm | |
| Thu., 3/26 | V Baseball | Torrington (Scrim.) | Home - PHS Baseball Field [Directions] | TBA | ||
| Thu., 3/26 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Thu., 3/26 | Miscellaneous Events | Stby Park & Rec Adult Swim | - PHS Pool | 8:15 p.m. | 8:30 - 10:00 pm | |
| Thu., 3/26 | Miscellaneous Events | Stby Park & Rec Open Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Fri., 3/27 | Miscellaneous Events | Youth Wrestling | - Wrestling Room | 6:00 p.m. | 6:00 - 8:00 pm | |
| Fri., 3/27 | Miscellaneous Events | Middlebury Park & Rec Basketball Practice | - Auxiliary Gym | 7:00 p.m. | 7:00 - 9:00 pm | |
| Sat., 3/28 | V Boys Lacrosse | Hamden (Scrim.) | Away [Directions] | 10:00 a.m. | 8:15 am | |
| Sat., 3/28 | V Girls Lacrosse | Pomperaug Jamboree | Home - Sports Complex & Track [Directions] | 9:00 a.m. | ||
| Sun., 3/29 | V Baseball | Indoor Srimmage at Bethel Dome | Away | 5:00 p.m. | 3:30 pm | Danbury, Holy Cross, Brewster, Pomperaug |
| Sun., 3/29 | Miscellaneous Events | Revolution United Soccer Game | - Sports Complex & Track | 3:30 p.m. | 3:30 - 5:30 pm | |
| Tue., 3/31 | V Girls Tennis | Shelton (Scrim.) | Away - Shelton High School Tennis Courts [Directions] | 3:45 p.m. | 2:15 | |
| Wed., 4/1 | V Softball | Fairfield Warde (Scrim.) | Away - Fairfield Warde H.S. [Directions] | 4:15 p.m. | 2:15 | |
| Thu., 4/2 | V Baseball | Bristol Central (Scrim.) | Home - Danbury Dome [Directions] | 4:00 p.m. | 3:00 pm | @ Danbury Dome |
| Thu., 4/2 | V Girls Lacrosse | North Branford (Scrim.) | Away - North Branford High School [Directions] | 4:00 p.m. | 2:15 pm | |
| Thu., 4/2 | V Softball | Holy Cross (Scrim.) | Home - PHS Softball Field [Directions] | 4:00 p.m. | ||
| Thu., 4/2 | V Girls Tennis | Nonnewaug (Scrim.) | Home - PHS Tennis Courts [Directions] | 2:45 p.m. | ||
| Sat., 4/4 | V Baseball | Weston (Scrim.) | Away [Directions] | 10:00 a.m. | 8:30 am | |
| Sat., 4/4 | V Boys Lacrosse | Pomperaug Jamboree | Home - Sports Complex & Track [Directions] | 10:00 a.m. | 10:00 am to 3:00 pm | |
| Sat., 4/4 | V Girls Lacrosse | Hamden (Scrim.) | Away - HHS Turf Field [Directions] | 10:30 a.m. | 8:30 am | |
| Sat., 4/4 | V Girls Lacrosse | Hamden (Scrim.) | Away [Directions] | 10:30 a.m. | 8:30 am | |
| Sat., 4/4 | V Softball | Nonnewaug (Scrim.) | Home - PHS Softball Field [Directions] | 1:00 p.m. | ||
| Mon., 4/6 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 3:45 p.m. | 3:45 - 8:15 pm | |
| Mon., 4/6 | Miscellaneous Events | Stby Park & Rec Adult Swim | - PHS Pool | 8:15 p.m. | 8:30 - 10:00 pm | |
| Mon., 4/6 | Miscellaneous Events | Mdby Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 4/7 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:45 p.m. | 5:45 - 8:15 pm | |
| Wed., 4/8 | V Baseball | Ridgefield | Home - Community Baseball Field [Directions] | L 1-8 | ||
| Wed., 4/8 | JV Baseball | Ridgefield | Away - Governor's Park Field (aka Ciuccoli or Old High School) [Directions] | 4:15 p.m. | 2:15, share bus with JV softball | |
| Wed., 4/8 | V Boys Lacrosse | Foran | Home - Sports Complex & Track [Directions] | W 15-3 | ||
| Wed., 4/8 | JV Boys Lacrosse | Foran | Home - Sports Complex & Track [Directions] | 5:15 p.m. | ||
| Wed., 4/8 | V Girls Lacrosse | Sheehan | Away - Sheehan HS Riccitelli Field [Directions] | W 17-6 | 4:30 | |
| Wed., 4/8 | JV Girls Lacrosse | Sheehan | Away - Sheehan HS Riccitelli Field [Directions] | 5:00 p.m. | 3:15 pm | |
| Wed., 4/8 | V Softball | Ridgefield | Home - PHS Softball Field [Directions] | W 3-1 | ||
| Wed., 4/8 | JV Softball | Ridgefield | Away - RHS Upper Grass Field [Directions] | W 11-4 | 2:15, share bus with JV Baseball | |
| Wed., 4/8 | V Girls Tennis | Bethel | Home - PHS Tennis Courts [Directions] | L 1-6 | Non League Game | |
| Wed., 4/8 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 3:45 p.m. | 3:45 - 8:15 pm | |
| Wed., 4/8 | Miscellaneous Events | Stby Park & Rec Adult Swim | - PHS Pool | 8:15 p.m. | 8:30 - 10:00 pm | |
| Thu., 4/9 | V Baseball | Masuk | Home - PHS Baseball Field [Directions] | W 5-4(9) | Non league game | |
| Thu., 4/9 | V Boys Tennis | Newtown | Home - PHS Tennis Courts [Directions] | W 5-2 | Non League Game | |
| Thu., 4/9 | Miscellaneous Events | College Fair | - PHS Main Gym | 2:15 p.m. | 2:15 Set-Up 6:00- 9:00 Fair | |
| Thu., 4/9 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 5:45 p.m. | 5:45 - 8:15 pm | |
| Thu., 4/9 | Miscellaneous Events | Stby Park & Rec Adult Swim | - PHS Pool | 8:15 p.m. | 8:30 - 10:00 pm | |
| Fri., 4/10 | Miscellaneous Events | Kinetic Kids -USA Gymnastics State Championships | - PHS Main Gym | 2:30 p.m. | Set Up 2:30 - 7:00 pm | |
| Fri., 4/10 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 3:45 p.m. | 3:45 - 8:15 pm | |
| Sat., 4/11 | V Baseball | New Fairfield | Home - Community Baseball Field [Directions] | L 15-7 | Non Leauge | |
| Sat., 4/11 | V Boys Lacrosse | Holy Cross | Home - Sports Complex & Track [Directions] | W 19-1 | ||
| Sat., 4/11 | Miscellaneous Events | Kinetic Kids -USA Gymnastics State Championships | - PHS Main Gym | 7:00 a.m. | 7:00 am - 9:00 pm | |
| Sun., 4/12 | Miscellaneous Events | Kinetic Kids -USA Gymnastics State Championships | - PHS Main Gym | 7:00 a.m. | 7:00 am - 9:00 pm | |
| Sun., 4/12 | Miscellaneous Events | Revolution United Soccer Game | - Sports Complex & Track | 3:30 p.m. | 3:30 - 5:30 pm | |
| Mon., 4/13 | V Baseball | Bunnell | Away - Bunnell Baseball Field [Directions] | L 6-0 | 2:30 pm | Non League Game |
| Mon., 4/13 | FR Baseball | Bunnell | Home - PHS Baseball Field [Directions] | 3:45 p.m. | ||
| Mon., 4/13 | V Boys Golf | Immaculate | Away [Directions] | Pomperaug 163 Immaculate 197 | 1:45 pm | |
| Mon., 4/13 | V Boys Tennis | Brookfield | Home - PHS Tennis Courts [Directions] | W 6-1 | ||
| Mon., 4/13 | V Girls Outdoor Track | Danbury | Away - Danbury High School Stadium [Directions] | 4:00 p.m. | 2:30 | |
| Mon., 4/13 | V Softball | Bunnell | Away - Bunnell Softball Field [Directions] | L 4-2 | 2:15 | Non League Game |
| Mon., 4/13 | V Girls Tennis | Brookfield | Away - BHS Tennis Courts [Directions] | W 5-2 | 2:15 pm | |
| Mon., 4/13 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:45 p.m. | 2:45 - 8:15 pm | |
| Mon., 4/13 | Miscellaneous Events | Stby Park & Rec Adult Swim | - PHS Pool | 8:15 p.m. | 8:30 - 10:00 pm | |
| Mon., 4/13 | Miscellaneous Events | Mdby Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 4/14 | JV Baseball | Bunnell | Home - Community Baseball Field [Directions] | 4:15 p.m. | ||
| Tue., 4/14 | V Boys Golf | New Milford | Away - Candlewood Valley [Directions] | Pomperaug 164 New Milford 167 | 2:15 pm | |
| Tue., 4/14 | V Boys Lacrosse | Bethel | Away - DeSantis Field at Bethel High School [Directions] | L 10-13 | 3:15 pm | |
| Tue., 4/14 | JV Boys Lacrosse | Bethel | Away - DeSantis Field at Bethel High School [Directions] | 6:30 p.m. | 4:30 pm | |
| Tue., 4/14 | V Girls Lacrosse | Bethel | Home - Sports Complex & Track [Directions] | L 8-12 | ||
| Tue., 4/14 | JV Girls Lacrosse | Bethel | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Tue., 4/14 | JV Softball | Bunnell | Home - Community Softball Field [Directions] | W 12-6 | ||
| Tue., 4/14 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:45 p.m. | 2:45 - 8:15 pm | |
| Wed., 4/15 | V Baseball | Weston | Home - PHS Baseball Field [Directions] | L 5-0 | Non League Game | |
| Wed., 4/15 | FR Baseball | Weston | Away - Revson Field, Weston [Directions] | 3:45 p.m. | 2:15 pm | |
| Wed., 4/15 | V Boys Tennis | Bunnell | Away - Bunnell Tennis Courts [Directions] | W 6-1 | 2:15 pm | |
| Wed., 4/15 | V Softball | Masuk | Home - PHS Softball Field [Directions] | L 2-8 | non leauge game | |
| Wed., 4/15 | V Girls Tennis | Bunnell | Home - PHS Tennis Courts [Directions] | W 6-1 | ||
| Wed., 4/15 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:45 p.m. | 2:45 - 8:15 pm | |
| Wed., 4/15 | Miscellaneous Events | Stby Park & Rec Adult Swim | - PHS Pool | 8:15 p.m. | 8:30 - 10:00 pm | |
| Thu., 4/16 | JV Baseball | Weston | Away - Revson Field, Weston [Directions] | 4:15 p.m. | 2:15 | |
| Thu., 4/16 | V Boys Lacrosse | Stratford | Away - Penders Field [Directions] | W 17-4 | 5:00 pm | |
| Thu., 4/16 | JV Boys Lacrosse | Stratford | Away - Penders Field [Directions] | 5:30 p.m. | 3:45 pm | |
| Thu., 4/16 | V Boys Tennis | Weston | Home - PHS Tennis Courts [Directions] | L 2-5 | ||
| Thu., 4/16 | V Girls Lacrosse | Stratford/Bunnell | Home - Sports Complex & Track [Directions] | W 22-5 | ||
| Thu., 4/16 | JV Girls Lacrosse | Stratford/Bunnell | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Thu., 4/16 | V Softball | New Milford | Home - PHS Softball Field [Directions] | W 3-2 | Non League Game | |
| Thu., 4/16 | JV Softball | New Milford | Away - New Milford High School [Directions] | L 9-1 | 2:15 | |
| Thu., 4/16 | V Girls Tennis | Weston | Away - WHS Tennis Courts [Directions] | L 2-5 | 2:15 pm | |
| Thu., 4/16 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:45 p.m. | 2:45 - 8:15 pm | |
| Thu., 4/16 | Miscellaneous Events | Stby Park & Rec Adult Swim | - PHS Pool | 8:15 p.m. | 8:30 - 10:00 pm | |
| Fri., 4/17 | JV Baseball | Joel Barlow | Home - Community Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 4/17 | FR Baseball | Newtown | Home - PHS Baseball Field [Directions] | 3:45 p.m. | ||
| Fri., 4/17 | V Softball | Newtown | Away - Newtown High School Softball Field [Directions] | L 4-5 | 2:15 | Non League Game |
| Fri., 4/17 | V Girls Tennis | Brookfield | Home - PHS Tennis Courts [Directions] | W 7-0 | Non League Game | |
| Fri., 4/17 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:45 p.m. | 2:45 - 8:15 pm | |
| Fri., 4/17 | Miscellaneous Events | Outreach Club Babysitting | - Auxiliary Gym | 4:00 p.m. | 4:00 - 8:00 pm | |
| Fri., 4/17 | Miscellaneous Events | Dodgeball for Diabetes | - PHS Main Gym | 7:00 p.m. | ||
| Sat., 4/18 | V Baseball | Newtown | Home - PHS Baseball Field [Directions] | W 3-0 | SWC Game | |
| Sat., 4/18 | V Baseball | Newtown | Home - PHS Baseball Field [Directions] | L 14-8 | Non League Game | |
| Sat., 4/18 | JV Baseball | Newtown | Home - Pomperaug High School [Directions] | 9:00 a.m. | ||
| Sat., 4/18 | JV Softball | Newtown | Home - PHS Softball Field [Directions] | L 12-5 | ||
| Sun., 4/19 | Miscellaneous Events | Revolution United Soccer Game | - Sports Complex & Track | 2:00 p.m. | 2:00 - 6:00 pm | |
| Mon., 4/20 | V Boys Lacrosse | Notre Dame-Fairfield | Home - Sports Complex & Track [Directions] | W 18-0 | ||
| Mon., 4/20 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:45 p.m. | 2:45 - 8:15 pm | |
| Mon., 4/20 | Miscellaneous Events | Stby Park & Rec Adult Swim | - PHS Pool | 8:15 p.m. | 8:30 - 10:00 pm | |
| Mon., 4/20 | Miscellaneous Events | Mdby Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 4/21 | JV Baseball | Brookfield | Home - Community Baseball Field [Directions] | 4:15 p.m. | ||
| Tue., 4/21 | V Boys Golf | Joel Barlow | Away - Redding Country Club [Directions] | Pomperaug 166 Barlow 182 | 1:45 pm | |
| Tue., 4/21 | V Girls Outdoor Track | Newtown, Kolbe Cathedral | Home - Sports Complex & Track [Directions] | Newtown 102 PHS 48 PHS 141 Kolbe 9 Newtown 150 Kolbe 0 | ||
| Tue., 4/21 | JV Softball | Brookfield | Home - Community Softball Field [Directions] | W 4-3 | ||
| Tue., 4/21 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:45 p.m. | 2:45 - 8:15 pm | |
| Wed., 4/22 | V Girls Lacrosse | New Milford | Home - Sports Complex & Track [Directions] | L 12 - 13 | ||
| Wed., 4/22 | JV Girls Lacrosse | New Milford | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Wed., 4/22 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:45 p.m. | 2:45 - 8:15 pm | |
| Wed., 4/22 | Miscellaneous Events | Stby Park & Rec Adult Swim | - PHS Pool | 8:15 p.m. | 8:30 - 10:00 pm | |
| Thu., 4/23 | V Baseball | Bunnell | Home - PHS Baseball Field [Directions] | L 8-0 | ||
| Thu., 4/23 | JV Baseball | Bunnell | Away - Bunnell [Directions] | 4:15 p.m. | 2:15 | |
| Thu., 4/23 | V Boys Golf | Brookfield | Home - Heritage Village CC [Directions] | Pomperaug 164 Brookfield 203 | ||
| Thu., 4/23 | V Boys Lacrosse | Stamford | Home - Sports Complex & Track [Directions] | W 14-5 | ||
| Thu., 4/23 | JV Boys Lacrosse | Stamford | Home - Sports Complex & Track [Directions] | 5:45 p.m. | ||
| Thu., 4/23 | V Boys Outdoor Track | Newtown, Kolbe Cathedral | Away - Blue and Gold Stadium [Directions] | N 54 - p 92 K 4 - p 141 | 1 bus at 2:15, 2nd bus at 2:45 | @ Newtown |
| Thu., 4/23 | V Boys Tennis | Stratford | Away - Short Beach Tennis Courts [Directions] | W 7-0 | 2:15 pm | |
| Thu., 4/23 | JV Softball | Bunnell | Away - Wigwam Lane Field [Directions] | W 7-3 | 2:15 | |
| Thu., 4/23 | V Girls Tennis | Stratford | Home - PHS Tennis Courts [Directions] | W 7-0 | ||
| Thu., 4/23 | Miscellaneous Events | Region 15 Art Show Set-Up | - PHS Main Gym | 7:30 a.m. | 7:30 am - 7:00 pm | |
| Thu., 4/23 | Miscellaneous Events | Region 15 Art Show Set-Up | - Health Classroom - Room 201 | 7:30 a.m. | 7:30 am - 7:00 pm | |
| Thu., 4/23 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:45 p.m. | 2:45 - 8:15 pm | |
| Thu., 4/23 | Miscellaneous Events | Stby Park & Rec Adult Swim | - PHS Pool | 8:15 p.m. | 8:30 - 10:00 pm | |
| Fri., 4/24 | V Baseball | Weston | Away - Revson Field, Weston [Directions] | W 2-1 | 2:15 | |
| Fri., 4/24 | FR Baseball | Weston | Home - Community Baseball Field [Directions] | 3:45 p.m. | ||
| Fri., 4/24 | V Boys Golf | Bunnell | Home - Heritage Village CC [Directions] | Pomperaug 164 Bunnell 198 | ||
| Fri., 4/24 | V Boys Outdoor Track | O'Grady Relays | Away | 6:00 p.m. | 4:00 pm, share bus with girls track | |
| Fri., 4/24 | V Girls Lacrosse | Watertown | Home - Sports Complex & Track [Directions] | W 17-4 | ||
| Fri., 4/24 | JV Girls Lacrosse | Watertown | Home - Sports Complex & Track [Directions] | 5:15 p.m. | ||
| Fri., 4/24 | V Girls Outdoor Track | O'Grady Relays | Away | 6:00 p.m. | 4:00 pm, share bus with boys track | |
| Fri., 4/24 | V Softball | Weston | Away - Hurlbutt El. School, Weston [Directions] | W 15-1 | 2:15 | |
| Fri., 4/24 | Miscellaneous Events | Region 15 Art Show | - Health Classroom - Room 201 | 7:30 a.m. | 7:30 am - 9:30 pm | |
| Fri., 4/24 | Miscellaneous Events | Region 15 Art Show | - PHS Main Gym | 7:30 a.m. | 7:30 am - 9:30 pm | |
| Fri., 4/24 | Miscellaneous Events | Art Show - History Exhibit | - Health Classroom - Room 201 | 2:30 p.m. | 2:30 - 11:00 pm | |
| Fri., 4/24 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:45 p.m. | 2:45 - 8:15 pm | |
| Sat., 4/25 | V Baseball | Brookfield | Away - BHS Baseball Field [Directions] | W 6-2 | 12:30 | |
| Sat., 4/25 | JV Baseball | Weston | Home - PHS Baseball Field [Directions] | 12:30 p.m. | ||
| Sat., 4/25 | FR Baseball | Brookfield | Home - PHS Baseball Field [Directions] | 10:00 a.m. | ||
| Sat., 4/25 | V Boys Outdoor Track | O'Grady Relays | Away | 9:00 a.m. | 7:30 am, share bus with girls track | |
| Sat., 4/25 | V Girls Outdoor Track | O'Grady Relays | Away | 9:00 a.m. | 7:30 am, share bus with boys track | |
| Sat., 4/25 | V Softball | Greenwich | Home - PHS Softball Field [Directions] | W 8 - 0 | ||
| Sat., 4/25 | JV Softball | Weston | Home - PHS Softball Field [Directions] | W 14-4 | ||
| Sat., 4/25 | Miscellaneous Events | Art Show - History Exhibit | - Health Classroom - Room 201 | 8:00 a.m. | 8:00 - 8:00 pm | |
| Sat., 4/25 | Miscellaneous Events | Region 15 Art Show | - PHS Main Gym | 9:00 a.m. | 9:00 - 3:00 pm | |
| Sat., 4/25 | Miscellaneous Events | Region 15 Art Show | - Health Classroom - Room 201 | 9:00 a.m. | 9:00 - 3:00 pm | |
| Sat., 4/25 | Miscellaneous Events | Revolution United Soccer Game | - Sports Complex & Track | 3:00 p.m. | 3:00 - 7:00 pm | |
| Sun., 4/26 | Miscellaneous Events | Edgewood Bath & Tennis Life Guard Review | - PHS Pool | 9:00 a.m. | 9:00 - 10:30 am | |
| Mon., 4/27 | V Baseball | Kolbe Cathedral | Home - PHS Baseball Field [Directions] | W 12-3 | ||
| Mon., 4/27 | FR Baseball | Kolbe Cathedral | Away [Directions] | Cancelled | Cancelled | |
| Mon., 4/27 | V Boys Golf | Newtown | Home - Heritage Village CC [Directions] | Pomperaug 164 Newtown 175 | ||
| Mon., 4/27 | V Boys Outdoor Track | New Milford, Bunnell, Immaculate | Home - Sports Complex & Track [Directions] | I 41 - p 108 B 55 - p 95 Nam 40. P 109 | ||
| Mon., 4/27 | V Boys Tennis | Newtown | Away - Newtown High School [Directions] | W 4-3 | 2:15 pm | |
| Mon., 4/27 | V Girls Lacrosse | Notre Dame-Fairfield | Away - Park Avenue Field at Notre Dame [Directions] | W 21-5 | 2:15 pm | |
| Mon., 4/27 | JV Girls Lacrosse | Notre Dame-Fairfield | Away - Park Avenue Field at Notre Dame [Directions] | 5:30 p.m. | 3:30 | |
| Mon., 4/27 | V Softball | Kolbe Cathedral | Home - PHS Softball Field [Directions] | W 6-0 | ||
| Mon., 4/27 | V Girls Tennis | Newtown | Home - PHS Tennis Courts [Directions] | L 3-4 | ||
| Mon., 4/27 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:45 p.m. | 2:45 - 8:15 pm | |
| Mon., 4/27 | Miscellaneous Events | Stby Park & Rec Adult Swim | - PHS Pool | 8:15 p.m. | 8:30 - 10:00 pm | |
| Mon., 4/27 | Miscellaneous Events | Mdby Park & Rec Over 30 Basketball | - PHS Main Gym | 8:30 p.m. | 8:30 - 10:00 pm | |
| Tue., 4/28 | V Boys Lacrosse | Masuk | Home - Sports Complex & Track [Directions] | W 14-5 | ||
| Tue., 4/28 | JV Boys Lacrosse | Masuk | Home - Sports Complex & Track [Directions] | 5:15 p.m. | ||
| Tue., 4/28 | V Boys Tennis | Bethel | Home - PHS Tennis Courts [Directions] | W 7-0 | ||
| Tue., 4/28 | V Girls Lacrosse | Masuk | Away - Masuk Stadium Field [Directions] | W 15-9 | 4:00 pm, share bus with JVs | |
| Tue., 4/28 | JV Girls Lacrosse | Masuk | Away - Masuk Stadium Field [Directions] | 5:30 p.m. | 4:00 pm, Share bus with varsity | |
| Tue., 4/28 | V Girls Outdoor Track | Bunnell, New Milford, Immaculate | Away - Bunnell Track [Directions] | PHS 78 Bunnell 72 PHS 124 Immaculate 22 NMHS 80 PHS 70 | 2:15 pm | @ New Milford |
| Tue., 4/28 | V Softball | Brookfield | Away - BHS Softball Field [Directions] | L 2-0 | 2:15 | |
| Tue., 4/28 | JV Softball | Kolbe Cathedral | Away [Directions] | Cancelled | 2:30 pm | |
| Tue., 4/28 | V Girls Tennis | Bethel | Away - TBA [Directions] | W 5-2 | 2:15 pm | |
| Tue., 4/28 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:45 p.m. | 2:45 - 8:15 pm | |
| Wed., 4/29 | V Baseball | Bethel | Away - Hunt Field at Bethel High School [Directions] | W 4-2 | 2:15 | |
| Wed., 4/29 | FR Baseball | Bethel | Home - Community Baseball Field [Directions] | 3:45 p.m. | ||
| Wed., 4/29 | V Boys Golf | New Fairfield | Home - Heritage Village CC [Directions] | Pomperaug 157 New Fairfield 209 | ||
| Wed., 4/29 | V Softball | Bethel | Away - Kasack Field at Johnson School [Directions] | W 13-2 | 2:15 | |
| Wed., 4/29 | FR Softball | Newtown | Away - Newtown High School Softball Field [Directions] | L 11-3 | 2:15 | |
| Wed., 4/29 | V Girls Tennis | Notre Dame-Fairfield | Away - Sacred Heart University [Directions] | W 6-1 | 2:15 pm | |
| Wed., 4/29 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:45 p.m. | 2:45 - 8:15 pm | |
| Wed., 4/29 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:45 p.m. | 2:45 - 8:15 pm | |
| Wed., 4/29 | Miscellaneous Events | Stby Park & Rec Adult Swim | - PHS Pool | 8:15 p.m. | 8:30 - 10:00 pm | |
| Thu., 4/30 | JV Baseball | Bethel | Home - Community Baseball Field [Directions] | 4:15 p.m. | 2:15, one way bus | |
| Thu., 4/30 | V Boys Golf | New Milford | Home - Heritage Village CC [Directions] | Pomperaug 162 New Milford 186 | Non League Game | |
| Thu., 4/30 | V Boys Tennis | New Fairfield | Away - New Fairfield HS [Directions] | W 6-1 | 2:15 pm | |
| Thu., 4/30 | V Girls Lacrosse | Branford | Home - Sports Complex & Track [Directions] | L 9-10 | ||
| Thu., 4/30 | JV Girls Lacrosse | Branford | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Thu., 4/30 | FR Softball | Amity | Away - Center Field - Woodbridge [Directions] | L 13-3 | 2:15 | |
| Thu., 4/30 | V Girls Tennis | New Fairfield | Home - PHS Tennis Courts [Directions] | L 3-4 | ||
| Thu., 4/30 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:45 p.m. | 2:45 - 8:15 pm | |
| Thu., 4/30 | Miscellaneous Events | Stby Park & Rec Adult Swim | - PHS Pool | 8:15 p.m. | 8:30 - 10:00 pm | |
| Fri., 5/1 | V Baseball | Stratford | Home - PHS Baseball Field [Directions] | W 6-5 | ||
| Fri., 5/1 | FR Baseball | Stratford | Away - Penders Field [Directions] | 3:45 p.m. | 2:15 pm | |
| Fri., 5/1 | V Boys Lacrosse | Southington | Away - SHS TURF FIELD [Directions] | W 7-12 | 5:00 pm | |
| Fri., 5/1 | JV Boys Lacrosse | Southington | Away - Southington High School [Directions] | 5:00 p.m. | 3:45 pm | |
| Fri., 5/1 | V Softball | Stratford | Home - PHS Softball Field [Directions] | W 14-0 | ||
| Fri., 5/1 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 8:30 pm | |
| Sat., 5/2 | JV Baseball | Stratford | Away - Penders Field [Directions] | 3:00 p.m. | 1:30 pm | |
| Sat., 5/2 | V Girls Lacrosse | Weston | Home - Sports Complex & Track [Directions] | L 7-10 | Non League game | |
| Sat., 5/2 | JV Girls Lacrosse | Weston | Home - Sports Complex & Track [Directions] | 3:30 p.m. | ||
| Sat., 5/2 | JV Softball | Stratford | Away [Directions] | W 5-0 | 2:15 | |
| Sun., 5/3 | Miscellaneous Events | Lacrosse - Honor the Game Day | - Sports Complex & Track | 7:00 a.m. | 7:00 am to 6:00 pm | |
| Sun., 5/3 | Miscellaneous Events | Lacrosse - Honor the Game Day | - Auxiliary Gym | 7:00 a.m. | 7:00 am to 6:00 pm | |
| Sun., 5/3 | Miscellaneous Events | Lacrosse - Honor the Game Day | - PHS Soccer Field | 7:00 a.m. | 7:00 am to 6:00 pm | |
| Mon., 5/4 | V Boys Golf | Weston | Away - Aspetuck Valley Country Club [Directions] | Pomperaug 160 Weston 180 | 1:45 pm | |
| Mon., 5/4 | V Boys Lacrosse | Bunnell-Stratford | Home - Sports Complex & Track [Directions] | W 3-11 | ||
| Mon., 5/4 | JV Boys Lacrosse | Bunnell-Stratford | Home - Sports Complex & Track [Directions] | 5:15 p.m. | ||
| Mon., 5/4 | V Boys Outdoor Track | Bethel, Stratford, Masuk | Away - DeSantis Field at Bethel High School [Directions] | B 71. - p 79 S 53 - p 96 M 76 - p 74 | 2:15 pm, 2 buses | @ Bethel |
| Mon., 5/4 | V Boys Tennis | New Milford | Home - PHS Tennis Courts [Directions] | W 7-0 | ||
| Mon., 5/4 | V Girls Lacrosse | Bunnell | Away - Bunnell Turf Field [Directions] | W 17-5 | 5:00 pm | |
| Mon., 5/4 | V Softball | Newtown | Home - PHS Softball Field [Directions] | W 3-2 | ||
| Mon., 5/4 | V Girls Tennis | New Milford | Away - New Milford High School [Directions] | W 7-0 | 2:15 pm | |
| Mon., 5/4 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 8:30 pm | |
| Mon., 5/4 | Miscellaneous Events | Stby Park & Rec Adult Swim | - PHS Pool | 8:15 p.m. | 8:30 - 10:00 pm | |
| Tue., 5/5 | JV Baseball | Newtown | Home - Community Baseball Field [Directions] | 3:45 p.m. | 2:15, one way bus | |
| Tue., 5/5 | V Boys Golf | Bethel | Away - Redding Country Club [Directions] | Pomperaug 162 Bethel 174 | 1:45 pm | |
| Tue., 5/5 | V Girls Lacrosse | St. Joseph | Away - St. Joseph High School [Directions] | W 20-12 | 2:30, share bus with JVs | |
| Tue., 5/5 | JV Girls Lacrosse | St. Joseph | Away - St Joes upper back field [Directions] | 4:15 p.m. | 2:30, share bus with varsity | |
| Tue., 5/5 | V Girls Outdoor Track | Bethel, Stratford, Masuk | Home - Sports Complex & Track [Directions] | PHS 134 Stratford 12 PHS 89 Bethel 61 PHS 108 1/2 Masuk 37 1/2 | ||
| Tue., 5/5 | JV Softball | Newtown | Away - Newtown High School Softball Field [Directions] | L 10-3 | 2:15 | |
| Tue., 5/5 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 8:30 pm | |
| Wed., 5/6 | V Baseball | Notre Dame-Fairfield | Away - Fabbri Field at Notre Dame [Directions] | W 3-0 | 2:15 | |
| Wed., 5/6 | V Boys Golf | Weston | Home - Heritage Village CC [Directions] | Pomperaug 161 Weston 176 | Non League Game | |
| Wed., 5/6 | V Boys Tennis | Joel Barlow | Away - Tennis Courts [Directions] | W 5-2 | 2:15 pm | |
| Wed., 5/6 | V Softball | Notre Dame-Fairfield | Away - Park Avenue Field at Notre Dame [Directions] | W 6-2 | 2:15 | |
| Wed., 5/6 | FR Softball | Newtown | Home - PHS Softball Field [Directions] | L 10-4 | ||
| Wed., 5/6 | V Girls Tennis | Joel Barlow | Home - PHS Tennis Courts [Directions] | L 1-6 | ||
| Wed., 5/6 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 8:30 pm | |
| Wed., 5/6 | Miscellaneous Events | Stby Park & Rec Adult Swim | - PHS Pool | 8:15 p.m. | 8:30 - 10:00 pm | |
| Thu., 5/7 | JV Baseball | Notre Dame-Fairfield | Home - Community Baseball Field [Directions] | 4:15 p.m. | 2:15, one way bus | |
| Thu., 5/7 | FR Baseball | Newtown | Away - Newtown High School Baseball Field [Directions] | 3:45 p.m. | 2:15 pm | |
| Thu., 5/7 | V Boys Golf | Woodland Invitational | Away | Pomperaug 161 | 8:45 am | |
| Thu., 5/7 | V Boys Lacrosse | Joel Barlow | Away - Field J [Directions] | L 4-18 | 2:15 | |
| Thu., 5/7 | JV Boys Lacrosse | Joel Barlow | Away - Field J [Directions] | 5:30 p.m. | 3:30 | |
| Thu., 5/7 | V Boys Tennis | Masuk | Home - PHS Tennis Courts [Directions] | W 5-2 | ||
| Thu., 5/7 | V Girls Lacrosse | Joel Barlow | Home - Sports Complex & Track [Directions] | L 5-17 | ||
| Thu., 5/7 | JV Girls Lacrosse | Joel Barlow | Home - Sports Complex & Track [Directions] | 5:00 p.m. | ||
| Thu., 5/7 | JV Softball | Notre Dame-Fairfield | Home - Community Softball Field [Directions] | W 6-1 | 2:15, one way bus | |
| Thu., 5/7 | V Girls Tennis | Masuk | Away - Wolfe Park Tennis Courts [Directions] | W 7-0 | 2:15 pm | |
| Thu., 5/7 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 8:30 pm | |
| Thu., 5/7 | Miscellaneous Events | Stby Park & Rec Adult Swim | - PHS Pool | 8:15 p.m. | 8:30 - 10:00 pm | |
| Fri., 5/8 | V Baseball | New Fairfield | Home - PHS Baseball Field [Directions] | L 10-0 | ||
| Fri., 5/8 | V Softball | New Fairfield | Home - PHS Softball Field [Directions] | W 14-2 | ||
| Fri., 5/8 | FR Softball | New Milford | Home - Community Softball Field [Directions] | L 6-3 | 2:15 | |
| Fri., 5/8 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 8:30 pm | |
| Sat., 5/9 | V Baseball | Oxford | Away - Dodd Stadium - Norwich [Directions] | W 9-8 | 3:00 pm | @ Dodd Stadium |
| Sat., 5/9 | JV Baseball | New Fairfield | Away - NFHS Baseball Field [Directions] | 9:00 a.m. | 7:30 am | |
| Sat., 5/9 | FR Baseball | New Fairfield | Away - NFHS Baseball Field [Directions] | 12:00 p.m. | 10:30 am | |
| Sat., 5/9 | V Boys Lacrosse | Hall | Away - Hall HS Stadium (Turf Field) [Directions] | L 10-15 | 8:00 am | |
| Sat., 5/9 | JV Boys Lacrosse | Hall | Away - Hall HS Boys Lacrosse Practice Field [Directions] | 10:00 a.m. | 8:00 am | |
| Sat., 5/9 | V Girls Outdoor Track | Greater Hartford Invitational | Away [Directions] | 9:00 a.m. | 7:00 am | |
| Sat., 5/9 | V Softball | Bunnell | Home - PHS Softball Field [Directions] | W 6-1 | ||
| Sat., 5/9 | JV Softball | New Fairfield | Away - NFHS Softball Field [Directions] | L 12-10 | 7:30, am, share bus with JV baseball | |
| Sun., 5/10 | Miscellaneous Events | Revolution United Soccer Game | - Sports Complex & Track | 2:00 p.m. | 2:00 and 4:00 | |
| Mon., 5/11 | V Baseball | New Milford | Away - New Milford High School [Directions] | L 3-0 | 2:15 | |
| Mon., 5/11 | FR Baseball | New Milford | Home - Community Baseball Field [Directions] | 3:45 p.m. | 2:15, one way bus | |
| Mon., 5/11 | V Boys Outdoor Track | Joel Barlow, Notre Dame-Fairfield | Home - Sports Complex & Track [Directions] | P (100) JB (48) P(119) ND (27) | ||
| Mon., 5/11 | V Boys Tennis | Immaculate | Home - PHS Tennis Courts [Directions] | W 6-1 | ||
| Mon., 5/11 | V Softball | New Milford | Away - New Milford High School [Directions] | W 3-0 | 2:15 | |
| Mon., 5/11 | V Girls Tennis | Immaculate | Away - Rogers Park [Directions] | W 4-3 | 2:15 pm | |
| Mon., 5/11 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 8:30 pm | |
| Mon., 5/11 | Miscellaneous Events | Stby Park & Rec Adult Swim | - PHS Pool | 8:15 p.m. | 8:30 - 10:00 pm | |
| Tue., 5/12 | JV Baseball | New Milford | Home - Community Baseball Field [Directions] | 4:15 p.m. | 2:15, one way bus | |
| Tue., 5/12 | V Boys Golf | Masuk | Home - Heritage Village CC [Directions] | Pomperaug 160 Masuk 172 | ||
| Tue., 5/12 | V Boys Lacrosse | Immaculate | Home - Sports Complex & Track [Directions] | W 7-14 | ||
| Tue., 5/12 | V Girls Lacrosse | Immaculate | Away - Mustang Valley [Directions] | W 10-9 OT | 2:45 pm | |
| Tue., 5/12 | JV Girls Lacrosse | Immaculate | Away - Mustang Valley [Directions] | 5:45 p.m. | 4:15 pm | |
| Tue., 5/12 | V Girls Outdoor Track | Joel Barlow, Notre Dame-Fairfield | Home - Field I (Stadium) [Directions] | Cancelled | 2:15 | @ Joel Barlow |
| Tue., 5/12 | V Girls Outdoor Track | Joel Barlow, Notre Dame-Fairfield | Away [Directions] | PHS 81 JBHS 69 PHS 143 NDHS 5 | ||
| Tue., 5/12 | JV Softball | New Milford | Home - Community Softball Field [Directions] | W 5-3 | 2:15, one way bus | |
| Tue., 5/12 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 8:30 pm | |
| Tue., 5/12 | Miscellaneous Events | Mdby Park & Rec Lifeguard Testing | - PHS Pool | 7:00 p.m. | 7:00 - 9:00 pm | |
| Wed., 5/13 | V Baseball | Joel Barlow | Home - PHS Baseball Field [Directions] | W 10-2 | ||
| Wed., 5/13 | FR Baseball | Joel Barlow | Away - Field G (Baseball) [Directions] | 3:45 p.m. | 2:15 pm | |
| Wed., 5/13 | V Boys Tennis | Joel Barlow | Home - PHS Tennis Courts [Directions] | W 5-2 | Non League Game | |
| Wed., 5/13 | V Softball | Joel Barlow | Home - PHS Softball Field [Directions] | L 5-3 | ||
| Wed., 5/13 | V Girls Tennis | New Fairfield | Away - New Fairfield HS [Directions] | L 2-5 | 2:15 pm | Non League Game |
| Wed., 5/13 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 8:30 pm | |
| Wed., 5/13 | Miscellaneous Events | Stby Park & Rec Adult Swim | - PHS Pool | 8:15 p.m. | 8:30 - 10:00 pm | |
| Thu., 5/14 | V Baseball | Masuk | Away - John Giampaolo Field @ Masuk [Directions] | L 13-5 | 2:15 | |
| Thu., 5/14 | JV Baseball | Joel Barlow | Away - Veteran's Field - Easton [Directions] | 4:15 p.m. | 2:15 | |
| Thu., 5/14 | V Boys Golf | Stratford | Away - Mill River C.C. [Directions] | Pomperaug 161 Stratford 193 | 1:45 pm | |
| Thu., 5/14 | V Boys Lacrosse | Brookfield | Away - BHS Stadium Field [Directions] | L 7-13 | 5:15 pm | |
| Thu., 5/14 | JV Boys Lacrosse | Brookfield | Away - BHS Stadium Field [Directions] | 5:00 p.m. | 3:45 pm | |
| Thu., 5/14 | V Girls Lacrosse | Brookfield | Home - Sports Complex & Track [Directions] | L 8-10 | ||
| Thu., 5/14 | JV Girls Lacrosse | Brookfield | Home - Sports Complex & Track [Directions] | 5:30 p.m. | ||
| Thu., 5/14 | V Softball | Masuk | Away - Masuk Upper Softball Field [Directions] | W 7-1 | 2:15 | |
| Thu., 5/14 | FR Softball | Amity | Home - PHS Softball Field [Directions] | L 10-5 | ||
| Thu., 5/14 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 8:30 pm | |
| Thu., 5/14 | Miscellaneous Events | Stby Park & Rec Adult Swim | - PHS Pool | 8:15 p.m. | 8:30 - 10:00 pm | |
| Fri., 5/15 | FR Baseball | Masuk | Home - Community Baseball Field [Directions] | 3:45 p.m. | 2:15, one way bus | |
| Fri., 5/15 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 a.m. | 6:00 - 7:00 am | |
| Fri., 5/15 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 8:30 pm | |
| Fri., 5/15 | Miscellaneous Events | Student Council Dance | - PHS Main Gym | 4:30 p.m. | 4:30 set-up Dance 6:00 - 10:00 | |
| Sat., 5/16 | V Boys Lacrosse | Lewis Mills | Home - Sports Complex & Track [Directions] | W 2-14 | ||
| Sat., 5/16 | JV Boys Lacrosse | Lewis Mills | Home - Sports Complex & Track [Directions] | 2:00 p.m. | ||
| Sat., 5/16 | V Girls Lacrosse | Amity | Home - Sports Complex & Track [Directions] | W 16-12 | ||
| Sat., 5/16 | JV Girls Lacrosse | Amity | Home - Sports Complex & Track [Directions] | 3:45 p.m. | ||
| Mon., 5/18 | V Baseball | Immaculate | Away - Immaculate High School [Directions] | W 7-1 | 2:15 | |
| Mon., 5/18 | V Boys Lacrosse | Trumbull | Home - Sports Complex & Track [Directions] | L 13-4 | ||
| Mon., 5/18 | JV Boys Lacrosse | Trumbull | Home - Sports Complex & Track [Directions] | 5:15 p.m. | ||
| Mon., 5/18 | V Boys Outdoor Track | New Fairfield, Brookfield, Weston | Away [Directions] | NF (84) P (66) B (62) P (88) W (92) P (58) | 2:15 pm, 2 buses | |
| Mon., 5/18 | V Boys Tennis | Newtown | Home - PHS Tennis Courts [Directions] | W 5-2 | ||
| Mon., 5/18 | V Softball | Immaculate | Away - Immaculate High School [Directions] | L 11-1 | 2:15 | |
| Mon., 5/18 | V Girls Tennis | SWC Team Semi-Finals | Away | Cancelled | ||
| Mon., 5/18 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 5:00 pm | |
| Mon., 5/18 | Miscellaneous Events | Middlebury Park and Rec Lifeguard Training | - Health Classroom - Room 201 | 5:00 p.m. | 5:00 to 7:00 pm | |
| Mon., 5/18 | Miscellaneous Events | Mdby Park & Rec Lifeguard Recertification | - PHS Pool | 7:00 p.m. | 7:00 - 9:00 pm | |
| Tue., 5/19 | JV Baseball | Immaculate | Home - Community Baseball Field [Directions] | 4:15 p.m. | 2:15, one way bus | |
| Tue., 5/19 | V Girls Outdoor Track | Weston, Brookfield, New Fairfield | Away - WHS Track [Directions] | WHS 76 PHS 74 PHS 91 Brook 59 PHS 116 NFHS 33 | 2:15 pm | @ Weston |
| Tue., 5/19 | V Softball | Brookfield | Home - PHS Softball Field [Directions] | L 5-4 | Non League Game | |
| Tue., 5/19 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 5:00 pm | |
| Tue., 5/19 | Miscellaneous Events | Middlebury Park and Rec Lifeguard Training | - Health Classroom - Room 201 | 5:00 p.m. | 5:00 to 7:00 pm | |
| Tue., 5/19 | Miscellaneous Events | Mdby Park & Rec Lifeguard Recertification | - PHS Pool | 7:00 p.m. | 7:00 - 9:00 pm | |
| Wed., 5/20 | FR Baseball | Joel Barlow | Home - Community Baseball Field [Directions] | 4:00 p.m. | 2:15, one way bus | |
| Wed., 5/20 | V Boys Golf | Notre Dame-Fairfield | Home - Heritage Village CC [Directions] | Pomperaug 170 Notre Dame 201 | ||
| Wed., 5/20 | V Boys Tennis | SWC Team Championship | Away | 3:30 p.m. | 2:15 pm | @ Weston, SWC QuarterFinals |
| Wed., 5/20 | V Girls Lacrosse | Shelton | Away - Shelton High School Finn Stadium [Directions] | W 20-10 | 4:00 pm, share bus with JVs | |
| Wed., 5/20 | JV Girls Lacrosse | Shelton | Away - Shelton High School Finn Stadium [Directions] | 5:30 p.m. | 4:00 pm, share bus with varsity | |
| Wed., 5/20 | JV Softball | Brookfield | Away - PTAK Softball Field [Directions] | L 11-3 | 2:15 | |
| Wed., 5/20 | V Girls Tennis | SWC Team Championship | Away | Cancelled | ||
| Wed., 5/20 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 5:00 pm | |
| Wed., 5/20 | Miscellaneous Events | Middlebury Park and Rec Lifeguard Training | - Health Classroom - Room 201 | 5:00 p.m. | 5:00 to 7:00 pm | |
| Wed., 5/20 | Miscellaneous Events | Mdby Park & Rec Lifeguard Recertification | - PHS Pool | 7:00 p.m. | 7:00 - 9:00 pm | |
| Thu., 5/21 | JV Baseball | Masuk | Home - Community Baseball Field [Directions] | 3:30 p.m. | 2:15, one way bus | |
| Thu., 5/21 | V Boys Lacrosse | Danbury | Away - Danbury High School Stadium [Directions] | L 8-10 | 2:45 pm | |
| Thu., 5/21 | JV Boys Lacrosse | Danbury | Away - Danbury High School Stadium [Directions] | 6:00 p.m. | 4:15 pm | |
| Thu., 5/21 | V Boys Outdoor Track | Bunnell | Away [Directions] | 4:00 p.m. | 2:15, share bus with girls track | |
| Thu., 5/21 | V Girls Outdoor Track | Bunnell | Away [Directions] | 4:00 p.m. | 2:15, Share bus with boys basketball | |
| Thu., 5/21 | JV Softball | Immaculate | Home - Community Softball Field [Directions] | Cancelled | 2:15, one way bus | |
| Thu., 5/21 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 8:30 pm | |
| Fri., 5/22 | FR Baseball | New Milford | Away - New Milford High School [Directions] | 3:45 p.m. | 2:15 pm | |
| Fri., 5/22 | FR Softball | New Milford | Away - New Milford High School [Directions] | L 2-1 | 2:15 pm | |
| Fri., 5/22 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 a.m. | 6:00 - 7:00 am | |
| Fri., 5/22 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 8:30 pm | |
| Sat., 5/23 | V Baseball | Bethel | Home - PHS Baseball Field [Directions] | 12:00 p.m. | SWC Quarter Finals, $8 Adults, $5 Students | |
| Sat., 5/23 | FR Baseball | Stratford | Away - Penders Field [Directions] | 9:00 a.m. | 7:30 am | |
| Sat., 5/23 | V Softball | Kolbe Cathedral | Home - PHS Softball Field [Directions] | W 12-0 | SWC Quarterfinals, $8 Adults, $5 Students | |
| Sat., 5/23 | Miscellaneous Events | Middle School Track Meet | - Sports Complex & Track | 9:00 a.m. | ||
| Tue., 5/26 | V Baseball | SWC Semi-Finals | Away [Directions] | 7:00 p.m. | 5:00 pm | @ Bethel HS, $8 Adults, $5 Students |
| Tue., 5/26 | V Boys Golf | Coaches Cup | Away | TBA | ||
| Tue., 5/26 | V Boys Lacrosse | SWC Tournament | Away | 7:00 p.m. | 5:00 pm | @ Bunnell. $8 Adults, $5 Students |
| Tue., 5/26 | V Boys Outdoor Track | SWC Championship Meet | Away [Directions] | 4:00 p.m. | 1:45 pm | @ Weston |
| Tue., 5/26 | V Boys Tennis | SWC Individual Tournament | Away [Directions] | 3:30 p.m. | 2:15 pm | @ Rogers Park |
| Tue., 5/26 | V Girls Lacrosse | SWC Semi Final | Home - Sports Complex & Track [Directions] | TBA | Adults $8, Students $5, 5:00 and 7:00 pm | |
| Tue., 5/26 | V Girls Outdoor Track | SWC Championship Meet | Away [Directions] | 4:00 p.m. | 1:45 pm | @ Weston HS |
| Tue., 5/26 | V Softball | SWC Semi-Finals | Away | 7:00 p.m. | 4:00 pm | @ Deluca Field, 5:00 pm or 7:00 pm |
| Tue., 5/26 | V Girls Tennis | SWC Individual Tournament | Away [Directions] | 3:30 p.m. | 2:15 pm | |
| Tue., 5/26 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 8:30 pm | |
| Wed., 5/27 | V Baseball | SWC Championship Game | Away [Directions] | 7:00 p.m. | TBA | |
| Wed., 5/27 | V Boys Golf | Joel Barlow | Home - Heritage Village CC [Directions] | Pomperaug 158 Barlow 178 | Non League Game | |
| Wed., 5/27 | V Boys Tennis | SWC Individual Tournament | Away [Directions] | 3:30 p.m. | 2:15 pm | @ Rogers Park |
| Wed., 5/27 | V Softball | SWC Championship Game | Away | 7:00 p.m. | TBA | DeLuca Field - Stratfield |
| Wed., 5/27 | V Girls Tennis | SWC Individual Tournament | Away [Directions] | 3:30 p.m. | 2:15 pm | |
| Wed., 5/27 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 8:30 pm | |
| Thu., 5/28 | V Boys Lacrosse | SWC Boy's Lacrosse Championship | Home - Sports Complex & Track [Directions] | 7:00 p.m. | $10 Adults, $5 Students | |
| Thu., 5/28 | V Girls Lacrosse | SWC Division II Championship | Home - Sports Complex & Track [Directions] | 5:00 p.m. | $10 Adults, $5 Students | |
| Thu., 5/28 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 a.m. | 6:00 - 7:00 am | |
| Thu., 5/28 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 8:30 pm | |
| Fri., 5/29 | V Boys Golf | SWC Championships | Away | 7:30 a.m. | 6:15 am | @ Ridgewood CC, Danbury |
| Fri., 5/29 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:15 p.m. | 2:15 - 8:30 pm | |
| Fri., 5/29 | Miscellaneous Events | Gymnastics Set-up | - PHS Main Gym | 3:00 p.m. | 3:00 - 6:00 pm | |
| Sat., 5/30 | V Boys Lacrosse | Brookfield | Home - Sports Complex & Track [Directions] | 11:00 a.m. | $8 Adults, $5 Students | |
| Sat., 5/30 | V Boys Tennis | CIAC Tournament | Away | 9:00 a.m. | 7:00 am | @ Yale |
| Sat., 5/30 | V Girls Lacrosse | CIAC Tournament Game | Home - Sports Complex & Track [Directions] | Cancelled | $8 Adults, $5 Students | |
| Sat., 5/30 | V Girls Lacrosse | North Haven | Home - Sports Complex & Track [Directions] | 2:00 p.m. | ||
| Sat., 5/30 | V Girls Lacrosse | TBA | Home - Sports Complex & Track [Directions] | Cancelled | $8 Adults, $5 Students | |
| Sat., 5/30 | V Girls Tennis | State Tournament | Away [Directions] | 9:00 a.m. | 7:30 am | |
| Sun., 5/31 | V Boys Tennis | CIAC Tournament | Away | 12:00 p.m. | TBA | |
| Sun., 5/31 | Miscellaneous Events | Gymnastics Exhibition | - PHS Main Gym | 7:00 a.m. | 9:00 am - 5:00 pm (7:00 pm) | |
| Mon., 6/1 | V Girls Lacrosse | East Lyme | Away [Directions] | 6:00 p.m. | 3:00 pm | |
| Mon., 6/1 | V Girls Lacrosse | CIAC Tournament Game | Away | Cancelled | ||
| Tue., 6/2 | V Boys Tennis | CIAC Tournament | Away | Cancelled | 10:30 am | If needed, @ Yale |
| Tue., 6/2 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 a.m. | 6:00 - 7:00 am | |
| Tue., 6/2 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:15 pm | |
| Wed., 6/3 | V Baseball | Torrington | Away [Directions] | 3:30 p.m. | 1:30 pm | |
| Wed., 6/3 | V Boys Lacrosse | Daniel Hand | Away [Directions] | Cancelled | ||
| Wed., 6/3 | V Boys Outdoor Track | CIAC Class L Championship | Away - Middletown HS [Directions] | 9:00 a.m. | 7:00 am, Share bus with boys track | |
| Wed., 6/3 | V Girls Outdoor Track | CIAC Class L Championship | Away - Middletown HS [Directions] | 9:00 a.m. | 7:00 am, share bus with girls track | |
| Wed., 6/3 | V Softball | Masuk | Home - PHS Softball Field [Directions] | 4:00 p.m. | ||
| Wed., 6/3 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:15 pm | |
| Thu., 6/4 | V Baseball | Daniel Hand | Home - PHS Baseball Field [Directions] | 3:30 p.m. | ||
| Thu., 6/4 | V Softball | Windsor | Away [Directions] | Cancelled | ||
| Thu., 6/4 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 a.m. | 6:00 - 7:00 am | |
| Thu., 6/4 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:15 pm | |
| Fri., 6/5 | V Baseball | CIAC Tournament Game | Home - PHS Baseball Field [Directions] | Cancelled | ||
| Fri., 6/5 | V Baseball | CIAC Tournament Game | Home - PHS Baseball Field [Directions] | Cancelled | ||
| Fri., 6/5 | Miscellaneous Events | Volleyball Team Meeting | - Health Classroom - Room 201 | 2:30 p.m. | 2:30 - 3:00 pm | |
| Fri., 6/5 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:15 pm | |
| Mon., 6/8 | V Boys Golf | CIAC Div. I Championship | Away - Timberlin GC - Kensington [Directions] | 8:40 a.m. | 6:45 am | |
| Mon., 6/8 | V Boys Outdoor Track | CIAC Open Championship | Away - Willow Brook Park [Directions] | 1:30 p.m. | 11:00 am, Share bus with Girls track | |
| Mon., 6/8 | V Girls Outdoor Track | CIAC Open Championship | Away - Willow Brook Park [Directions] | 1:30 p.m. | 11:00 am, share bus with girls track | |
| Mon., 6/8 | Miscellaneous Events | Football Team Study | - Health Classroom - Room 201 | 2:30 p.m. | 2:30 - 4:00 pm | |
| Mon., 6/8 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:15 pm | |
| Tue., 6/9 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 a.m. | 6:00 - 7:00 am | |
| Tue., 6/9 | Miscellaneous Events | Football Team Study | - Health Classroom - Room 201 | 2:30 p.m. | 2:30 - 4:00 pm | |
| Tue., 6/9 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:15 pm | |
| Tue., 6/9 | Miscellaneous Events | CPR Class For Coaches | - Health Classroom - Room 201 | 5:00 p.m. | 5:00 to 8:00 pm | |
| Tue., 6/9 | Miscellaneous Events | Southbury Youth Soccer | - Sports Complex & Track | 6:15 p.m. | 6:15 - 7:45 pm | |
| Wed., 6/10 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:15 pm | |
| Wed., 6/10 | Miscellaneous Events | Coaches CEU Workshop | - Health Classroom - Room 201 | 4:00 p.m. | ||
| Thu., 6/11 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 a.m. | 6:00 - 7:00 am | |
| Thu., 6/11 | Miscellaneous Events | Football Team Study | - Health Classroom - Room 201 | 2:30 p.m. | 2:30 - 4:00 pm | |
| Thu., 6/11 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:15 pm | |
| Fri., 6/12 | Miscellaneous Events | Football Team Study | - Health Classroom - Room 201 | 2:30 p.m. | 2:30 - 4:00 pm | |
| Fri., 6/12 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:15 pm | |
| Fri., 6/12 | Miscellaneous Events | Southbury Youth Soccer | - Sports Complex & Track | 4:45 p.m. | 4:45 - 6:00 pm | |
| Sat., 6/13 | V Boys Outdoor Track | New England Championship | Away - Thornton Academy (ME) | TBA | ||
| Sat., 6/13 | V Girls Outdoor Track | New England Championship | Away - Thornton Academy (ME) | TBA | ||
| Mon., 6/15 | Miscellaneous Events | Lifeguarding Retests & Student Make-ups | - PHS Pool | 12:30 p.m. | 12:30 - 3:00 pm | |
| Tue., 6/16 | V Boys Outdoor Track | CIAC Decathlon Champ. | Away - Willow Brook Park [Directions] | 11:00 a.m. | 9:30 am, share bus with girls track | |
| Tue., 6/16 | V Girls Outdoor Track | CIAC Heptathlon/Hammer/Steeplechase Champ. | Away - Willow Brook Park | 11:30 a.m. | 9:30 am, share bus with boys track | |
| Tue., 6/16 | Miscellaneous Events | Girls Soccer Meeting | - Health Classroom - Room 201 | 12:00 p.m. | ||
| Tue., 6/16 | Miscellaneous Events | Lifeguarding Retests & Student Make-ups | - PHS Pool | 12:30 p.m. | 12:30 - 3:00 pm | |
| Wed., 6/17 | V Boys Outdoor Track | CIAC Decathlon/Hammer/Steeplechase Champ. | Away - Willow Brook Park [Directions] | 11:00 a.m. | 9:30 am, share bus with girls track | |
| Wed., 6/17 | Miscellaneous Events | Lifeguarding Retests & Student Make-ups | - PHS Pool | 12:30 p.m. | 12:30 - 3:00 pm | |
| Thu., 6/18 | V Girls Outdoor Track | CIAC Heptathlon Champ. | Away - Willow Brook Park [Directions] | 11:00 a.m. | 9:30 am, share bus with boys track | |
| Mon., 6/22 | V Boys Golf | New England Championships | Away - Bretwood GC - Keene, NH | TBA | ||
| Mon., 6/22 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 6:00 a.m. | 6:00 - 8:30 am | |
| Mon., 6/22 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 - 8:30 am | |
| Mon., 6/22 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 2:30 p.m. | 2:30 - 8:15 pm | |
| Mon., 6/22 | Miscellaneous Events | Stby Park & Rec Field Hockey Camp | - PHS Baseball Field | 8:30 p.m. | 8:30 - 12:15 pm | |
| Tue., 6/23 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 - 8:30 am | |
| Tue., 6/23 | Miscellaneous Events | Stby Park & Rec Field Hockey Camp | - PHS Baseball Field | 8:30 p.m. | 8:30 - 12:15 pm | |
| Wed., 6/24 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 - 8:30 am | |
| Wed., 6/24 | Miscellaneous Events | Stby Park & Rec Field Hockey Camp | - PHS Baseball Field | 8:30 p.m. | 8:30 - 12:15 pm | |
| Thu., 6/25 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 - 8:30 am | |
| Thu., 6/25 | Miscellaneous Events | Stby Park & Rec Field Hockey Camp | - PHS Baseball Field | 8:30 p.m. | 8:30 - 12:15 pm | |
| Fri., 6/26 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 - 8:30 am | |
| Mon., 6/29 | Miscellaneous Events | Middlebury Park & Rec Swim Lessons | - PHS Pool | 11:30 a.m. | 11:30 - 2:15 pm | |
| Mon., 6/29 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 - 8:30 am | |
| Tue., 6/30 | Miscellaneous Events | Middlebury Park & Rec Swim Lessons | - PHS Pool | 11:30 a.m. | 11:30 - 2:15 pm | |
| Tue., 6/30 | Miscellaneous Events | PAC Swim Practice | - PHS Pool | 7:00 a.m. | 7:00 - 8:30 am | |