| Pomperaug 2021-22 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 801 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Mon., 7/12 | Miscellaneous Events | MP&R Swim Lessons | Home - Pomperaug HS-PHS Pool [Directions] | 10:15 a.m. | ||
| Mon., 7/12 | Miscellaneous Events | SP&R Panther Basketball Camp | Home - Pomperaug HS-Main Gym [Directions] | 9:00 a.m. | ||
| Tue., 7/13 | Miscellaneous Events | MP&R Swim Lessons | Home - Pomperaug HS-PHS Pool [Directions] | 10:15 a.m. | ||
| Tue., 7/13 | Miscellaneous Events | SP&R Panther Basketball Camp | Home - Pomperaug HS-Main Gym [Directions] | 9:00 a.m. | ||
| Wed., 7/14 | Miscellaneous Events | MP&R Swim Lessons | Home - Pomperaug HS-PHS Pool [Directions] | 10:15 a.m. | ||
| Wed., 7/14 | Miscellaneous Events | SP&R Panther Basketball Camp | Home - Pomperaug HS-Main Gym [Directions] | 9:00 a.m. | ||
| Thu., 7/15 | Miscellaneous Events | MP&R Swim Lessons | Home - Pomperaug HS-PHS Pool [Directions] | 10:15 a.m. | ||
| Thu., 7/15 | Miscellaneous Events | SP&R Panther Basketball Camp | Home - Pomperaug HS-Main Gym [Directions] | 9:00 a.m. | ||
| Sat., 7/17 | Miscellaneous Events | Pomperaug Youth Baseball | Home - Pomperaug HS-Baseball Field [Directions] | 7:00 a.m. | ||
| Sun., 7/18 | Miscellaneous Events | Pomperaug Youth Baseball | Home - Pomperaug HS-Baseball Field [Directions] | 7:00 a.m. | ||
| Mon., 7/19 | Miscellaneous Events | MP&R Swim Lessons | Home - Pomperaug HS-PHS Pool [Directions] | 10:15 a.m. | ||
| Tue., 7/20 | Miscellaneous Events | MP&R Swim Lessons | Home - Pomperaug HS-PHS Pool [Directions] | 10:15 a.m. | ||
| Wed., 7/21 | Miscellaneous Events | MP&R Swim Lessons | Home - Pomperaug HS-PHS Pool [Directions] | 10:15 a.m. | ||
| Thu., 7/22 | Miscellaneous Events | MP&R Swim Lessons | Home - Pomperaug HS-PHS Pool [Directions] | 10:15 a.m. | ||
| Mon., 7/26 | Miscellaneous Events | MP&R Swim Lessons | Home - Pomperaug HS-PHS Pool [Directions] | 10:15 a.m. | ||
| Tue., 7/27 | Miscellaneous Events | MP&R Swim Lessons | Home - Pomperaug HS-PHS Pool [Directions] | 10:15 a.m. | ||
| Wed., 7/28 | Miscellaneous Events | MP&R Swim Lessons | Home - Pomperaug HS-PHS Pool [Directions] | 10:15 a.m. | ||
| Thu., 7/29 | Miscellaneous Events | MP&R Swim Lessons | Home - Pomperaug HS-PHS Pool [Directions] | 10:15 a.m. | ||
| Mon., 8/2 | Miscellaneous Events | MP&R Swim Lessons | Home - Pomperaug HS-PHS Pool [Directions] | 10:15 a.m. | ||
| Tue., 8/3 | Miscellaneous Events | MP&R Swim Lessons | Home - Pomperaug HS-PHS Pool [Directions] | 10:15 a.m. | ||
| Wed., 8/4 | Miscellaneous Events | MP&R Swim Lessons | Home - Pomperaug HS-PHS Pool [Directions] | 10:15 a.m. | ||
| Thu., 8/5 | Miscellaneous Events | MP&R Swim Lessons | Home - Pomperaug HS-PHS Pool [Directions] | 10:15 a.m. | ||
| Sun., 8/22 | Miscellaneous Events | Soccer Pre Season Camp | Home - Pomperaug HS-PHS Soccer Field [Directions] | 5:00 p.m. | ||
| Mon., 8/23 | Miscellaneous Events | Soccer Pre Season Camp | Home - Pomperaug HS-PHS Soccer Field [Directions] | 5:00 p.m. | ||
| Tue., 8/24 | Miscellaneous Events | Soccer Pre Season Camp | Home - Pomperaug HS-PHS Soccer Field [Directions] | 5:00 p.m. | ||
| Wed., 8/25 | V Football | Woodland (Scrim.) | Away - Woodland HS-Woodland Football Field [Directions] | 3:30 p.m. | ||
| Wed., 8/25 | Miscellaneous Events | Soccer Pre Season Camp | Home - Pomperaug HS-PHS Soccer Field [Directions] | 5:00 p.m. | ||
| Sat., 8/28 | V Football | Immaculate (Scrim.) | Away - Immaculate HS-Immaculate HS [Directions] | 10:00 a.m. | ||
| Sat., 8/28 | V Football | ATI, Amity, Bullard/Kolbe, Masuk, New Fairfield, Weston | Away - Immaculate HS-Mustang Valley | 9:30 a.m. | ||
| Sun., 8/29 | V Boys Soccer | TBA | Home - Pomperaug HS-Stadium [Directions] | 6:00 p.m. | ||
| Tue., 8/31 | V Boys Golf | Joel Barlow | Away - Redding Country Club [Directions] | 3:00 p.m. | Pomperaug 158 Barlow. 192 | |
| Tue., 8/31 | V Boys Soccer | Nonnewaug (Scrim.) | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | ||
| Tue., 8/31 | V Field Hockey | Cheshire (Scrim.) | Home - Pomperaug HS-Stadium [Directions] | 4:30 p.m. | ||
| Tue., 8/31 | V Girls Soccer | Cheshire (Scrim.) | Away - Cheshire High Main Game field [Directions] | 6:00 p.m. | ||
| Thu., 9/2 | V Football | Watertown (Scrim.) | Home - Pomperaug HS-Stadium [Directions] | 6:30 p.m. | ||
| Thu., 9/2 | V Boys Soccer | Avon (Scrim.) | Away - Avon HS-Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 9/2 | JV Boys Soccer | Avon (Scrim.) | Away - Fisher Meadow Soccer Fields-Fisher Meadows- Field 5 [Directions] | Canceled | Cancelled | |
| Fri., 9/3 | V Boys Cross Country | Danbury (Scrim.) | Home - Pomperaug HS-Cross Country Course [Directions] | 6:00 p.m. | ||
| Fri., 9/3 | V Girls Cross Country | Danbury (Scrim.) | Home - Pomperaug HS-Cross Country Course [Directions] | 6:00 p.m. | ||
| Fri., 9/3 | V Girls Soccer | St. Joseph (Scrim.) | Away - St. Joseph HS-Lower Turf [Directions] | 4:30 p.m. | ||
| Fri., 9/3 | V Girls Volleyball | Seymour (Scrim.) | Home - Pomperaug HS-Main Gym [Directions] | 3:30 p.m. | W 3-1 | |
| Fri., 9/3 | JV Girls Volleyball | Seymour | Home - Pomperaug HS-Auxiliary Gym [Directions] | 3:30 p.m. | ||
| Sat., 9/4 | FR Football | Watertown (Scrim.) | Home - Pomperaug HS-Stadium [Directions] | 10:00 a.m. | ||
| Sat., 9/4 | V Boys Soccer | Cheshire (Scrim.) | Away - Cheshire High Main Game field [Directions] | 6:00 p.m. | ||
| Sat., 9/4 | JV Boys Soccer | Cheshire (Scrim.) | Away - Cheshire HS-Cheshire High School Main Game field [Directions] | 4:00 p.m. | ||
| Sun., 9/5 | V Girls Soccer | Staples (Scrim.) | Home - Treadwell Park-Newtown Treadwell Park [Directions] | 10:20 a.m. | ||
| Sun., 9/5 | V Girls Soccer | Naugatuck (Scrim.) | Away - Treadwell Park-Newtown Treadwell Park [Directions] | 11:00 a.m. | ||
| Sun., 9/5 | V Girls Soccer | Newtown (Scrim.) | Away - Treadwell Park-Newtown Treadwell Park [Directions] | 11:45 a.m. | ||
| Sun., 9/5 | V Girls Soccer | Fairfield Warde (Scrim.) | Home - Treadwell Park-Treadwell Town Park--Tilson Field [Directions] | 1:00 p.m. | ||
| Mon., 9/6 | V Field Hockey | Amity, Danbury (Scrim.) | Home - Pomperaug HS-Stadium [Directions] | 9:00 a.m. | ||
| Tue., 9/7 | V Boys Golf | Masuk | Away - Whitney Farms Golf Course [Directions] | 2:30 p.m. | Cancelled | |
| Tue., 9/7 | V Field Hockey | Watertown (Scrim.) | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 6:00 p.m. | ||
| Wed., 9/8 | V Boys Golf | Notre Dame-Fairfield | Home - Pomperaug HS-Highfield Country Club [Directions] | 3:00 p.m. | Pomperaug 163 | |
| Wed., 9/8 | V Girls Volleyball | Holy Cross (Scrim.) | Home - Pomperaug HS-Main Gym [Directions] | 3:30 p.m. | W 3-0 | |
| Wed., 9/8 | JV Girls Volleyball | Holy Cross | Home - Pomperaug HS-Auxiliary Gym [Directions] | 3:30 p.m. | ||
| Thu., 9/9 | FR Football | New Fairfield | Home - Pomperaug HS-Stadium [Directions] | 3:45 p.m. | ||
| Thu., 9/9 | V Girls Soccer | Woodland | Home - Pomperaug HS-Stadium [Directions] | 6:30 p.m. | T 1-1 | |
| Fri., 9/10 | V Football | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 7:00 p.m. | L 17-42 | |
| Fri., 9/10 | V Boys Golf | Masuk, Stratford | Away - Whitney Farms Golf Course [Directions] | 3:00 p.m. | ||
| Sat., 9/11 | JV Football | Newtown | Home - Pomperaug HS-Stadium [Directions] | 10:30 a.m. | ||
| Sat., 9/11 | V Field Hockey | New Fairfield | Home - Pomperaug HS-Stadium [Directions] | 3:30 p.m. | W 6-2 | |
| Sat., 9/11 | JV Field Hockey | New Fairfield | Home - Pomperaug HS-Stadium [Directions] | 2:00 p.m. | ||
| Sat., 9/11 | V Girls Volleyball | Westhill | Home - Pomperaug HS-Main Gym [Directions] | 11:30 a.m. | W 3-0 | |
| Sat., 9/11 | JV Girls Volleyball | Westhill | Home - Pomperaug HS-Main Gym [Directions] | 10:00 a.m. | ||
| Mon., 9/13 | V Boys Golf | New Milford | Away - Candlewood Valley Country Club [Directions] | 3:00 p.m. | Pomperaug 165 New Milford 180 | |
| Mon., 9/13 | V Field Hockey | Shelton | Away - Shelton HS-Finn Stadium [Directions] | 7:00 p.m. | W 4-1 | |
| Mon., 9/13 | JV Field Hockey | Shelton | Away - Shelton HS-Finn Stadium [Directions] | 5:15 p.m. | ||
| Mon., 9/13 | V Girls Volleyball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Mon., 9/13 | JV Girls Volleyball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 4:00 p.m. | ||
| Tue., 9/14 | V Boys Cross Country | New Fairfield, Bethel, Kolbe Cathedral | Away - New Fairfield HS-Track & Field, Cross Country [Directions] | 4:30 p.m. | PHS 17 Kolbe 46 PHS 15 NFHS 50 PHS 17-46 | |
| Tue., 9/14 | V Boys Golf | Bunnell | Home - Pomperaug HS-Highfield Country Club [Directions] | 3:00 p.m. | Pomperaug 158 Bunnell 268 | |
| Tue., 9/14 | V Boys Soccer | New Milford | Away - New Milford HS-North Turf Field - NMHS [Directions] | 6:00 p.m. | L 1-0 | |
| Tue., 9/14 | JV Boys Soccer | New Milford | Away - New Milford HS-North Turf Field - NMHS [Directions] | 4:00 p.m. | ||
| Tue., 9/14 | V Girls Cross Country | New Fairfield, Bethel, Kolbe Cathedral | Away - New Fairfield HS-Track & Field, Cross Country [Directions] | 5:00 p.m. | PHS 27 NFHS 28 PHS 15 Kolbe 50 Bethel 22 PHS 33 | |
| Tue., 9/14 | V Girls Soccer | New Milford | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | W 5-0 | |
| Tue., 9/14 | JV Girls Soccer | New Milford | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Tue., 9/14 | V Girls Swimming and Diving | Joel Barlow | Home - Pomperaug HS-PHS Pool [Directions] | 4:00 p.m. | 102-59 pomp | |
| Tue., 9/14 | V Girls Volleyball | Bethel | Away - Bethel HS-BHS gym [Directions] | 5:30 p.m. | W 3-0 | |
| Tue., 9/14 | JV Girls Volleyball | Bethel | Away - Bethel HS-BHS gym [Directions] | 4:00 p.m. | ||
| Wed., 9/15 | V Boys Golf | Newtown | Home - Pomperaug HS-Highfield Country Club [Directions] | 3:00 p.m. | Pomperaug 156 Newtown 180 | |
| Wed., 9/15 | FR Boys Soccer | Newtown | Away - Newtown HS-NHS Practice Fields [Directions] | 3:30 p.m. | ||
| Wed., 9/15 | FR Field Hockey | Bethel | Away - Bethel HS-Hunt Field at Bethel HS [Directions] | Canceled | Cancelled | |
| Fri., 9/17 | V Football | Bunnell | Home - Pomperaug HS-Stadium [Directions] | 6:30 p.m. | L 7-20 | |
| Sat., 9/18 | V Boys Cross Country | Bethel | Away - Bethel HS-BHS track [Directions] | 9:30 a.m. | ||
| Sat., 9/18 | FR Football | Bunnell | Away - Bunnell HS-Bunnell Turf Field [Directions] | 11:00 a.m. | ||
| Sat., 9/18 | FM Football | Bunnell | Away - Bunnell HS-Mastroni Field [Directions] | 11:00 a.m. | ||
| Sat., 9/18 | V Boys Soccer | Brookfield | Home - Pomperaug HS-Stadium [Directions] | 12:00 p.m. | L 3-1 | |
| Sat., 9/18 | JV Boys Soccer | Brookfield | Home - Pomperaug HS-Stadium [Directions] | 10:00 a.m. | ||
| Sat., 9/18 | FR Boys Soccer | Wilton | Away - Wilton HS-Lilly Field [Directions] | 12:00 p.m. | ||
| Sat., 9/18 | V Girls Cross Country | Bethel | Away - Bethel HS-BHS track [Directions] | 9:30 a.m. | ||
| Sat., 9/18 | FR Field Hockey | Brookfield | Home - Pomperaug HS-Baseball Field [Directions] | Canceled | Cancelled | |
| Sat., 9/18 | V Girls Soccer | Brookfield | Away - Brookfield HS-BHS Stadium Field [Directions] | 9:00 a.m. | W 4-1 | |
| Sat., 9/18 | JV Girls Soccer | Brookfield | Away - Brookfield HS-BHS Back Turf [Directions] | Canceled | Cancelled | |
| Mon., 9/20 | V Boys Golf | Bethel | Home - Pomperaug HS-Highfield Country Club [Directions] | 3:00 p.m. | Pomperaug 172 Bethel 179 | |
| Mon., 9/20 | V Field Hockey | Bethel | Home - Pomperaug HS-Stadium [Directions] | 6:30 p.m. | W 2-0 | |
| Mon., 9/20 | JV Field Hockey | Bethel | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Mon., 9/20 | V Girls Volleyball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 6:00 p.m. | W 3-1 | |
| Mon., 9/20 | JV Girls Volleyball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 4:45 p.m. | ||
| Mon., 9/20 | FR Girls Volleyball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 3:30 p.m. | ||
| Tue., 9/21 | V Boys Cross Country | Brookfield, Stratford | Home - Pomperaug HS-Cross Country Course [Directions] | 4:30 p.m. | PHS 18 Brookfield 45 PHS 18 Stratford 46 | |
| Tue., 9/21 | V Boys Golf | Weston | Home - Pomperaug HS-Highfield Country Club [Directions] | 3:00 p.m. | Pomperaug 160 Weston 193 | |
| Tue., 9/21 | V Boys Soccer | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 7:00 p.m. | T 1-1 | |
| Tue., 9/21 | JV Boys Soccer | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 5:15 p.m. | ||
| Tue., 9/21 | V Girls Cross Country | Brookfield, Stratford | Home - Pomperaug HS-Cross Country Course [Directions] | 5:00 p.m. | Brookfield 27 PHS 28 PHS 15 Stratford 50 | |
| Tue., 9/21 | FR Field Hockey | Bethel | Home - Pomperaug HS-Baseball Field [Directions] | Canceled | Cancelled | |
| Tue., 9/21 | V Girls Soccer | Masuk | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | T 0-0 | |
| Tue., 9/21 | JV Girls Soccer | Masuk | Home - Pomperaug HS-PHS Soccer Field [Directions] | 5:00 p.m. | ||
| Tue., 9/21 | V Girls Swimming and Diving | Masuk | Away - Masuk HS-Pool [Directions] | 4:00 p.m. | 103-72 Pomp | |
| Wed., 9/22 | V Boys Golf | New Fairfield | Away - Club River Oaks [Directions] | 3:00 p.m. | Pomperaug 163 New Fairfield 229 | |
| Wed., 9/22 | FR Boys Soccer | Masuk | Home - Pomperaug HS-PHS Soccer Field [Directions] | 5:00 p.m. | ||
| Wed., 9/22 | V Field Hockey | Joel Barlow | Away - Joel Barlow HS-Field I (Stadium) [Directions] | 6:45 p.m. | W 1-0 | |
| Wed., 9/22 | JV Field Hockey | Joel Barlow | Away - Joel Barlow HS-Field I (Stadium) [Directions] | 5:30 p.m. | ||
| Wed., 9/22 | V Girls Volleyball | Joel Barlow | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | W 3-2 | |
| Wed., 9/22 | JV Girls Volleyball | Joel Barlow | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 9/23 | V Boys Golf | Immaculate, Masuk | Away - Immaculate HS-Ridgewood CC [Directions] | 3:00 p.m. | Pomperaug 165 Masuk 173 Immaculate 190 | |
| Thu., 9/23 | V Boys Soccer | Joel Barlow | Away - Joel Barlow HS-Field J (Competition Field) [Directions] | 4:30 p.m. | L 2-0 | |
| Thu., 9/23 | V Girls Soccer | Joel Barlow | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | W 4-1 | |
| Thu., 9/23 | JV Girls Soccer | Joel Barlow | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Fri., 9/24 | V Football | Guilford | Home - Pomperaug HS-Stadium [Directions] | 6:30 p.m. | L 0-21 | |
| Fri., 9/24 | V Boys Golf | Avon Invitational | Away - Blue Fox Run Golf Course | 11:30 a.m. | Pomperaug 160 | |
| Pending change awaiting acceptance by one or more parties involved: Facility to Tunxis Country Club | ||||||
| Fri., 9/24 | V Girls Swimming and Diving | Brookfield | Home - Pomperaug HS-PHS Pool [Directions] | 6:00 p.m. | 103/63 | |
| Fri., 9/24 | V Girls Volleyball | Weston | Away - Weston HS-Gym (New) [Directions] | 5:30 p.m. | L 2-3 | |
| Fri., 9/24 | JV Girls Volleyball | Weston | Away - Weston HS-Gym (New) [Directions] | 4:00 p.m. | ||
| Fri., 9/24 | FR Girls Volleyball | Weston | Away - Weston HS-Gym (Old) [Directions] | 4:00 p.m. | ||
| Sat., 9/25 | JV Football | Guilford | Away - Guilford HS-New Turf field at GHS [Directions] | Postponed | ||
| Sat., 9/25 | JV Boys Soccer | Joel Barlow | Away - Joel Barlow HS-Field E (Softball) [Directions] | Postponed | ||
| Sat., 9/25 | FR Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 9:00 a.m. | ||
| Sat., 9/25 | V Field Hockey | Masuk | Home - Pomperaug HS-Stadium [Directions] | 12:00 p.m. | OT-L 2-3 | |
| Sat., 9/25 | JV Field Hockey | Masuk | Home - Pomperaug HS-Stadium [Directions] | 10:30 a.m. | ||
| Sat., 9/25 | FR Field Hockey | New Milford | Away - New Milford HS-North Turf Field - NMHS [Directions] | Canceled | Cancelled | |
| Mon., 9/27 | V Field Hockey | New Fairfield | Away - New Fairfield HS-Marty Morgan Field [Directions] | 5:30 p.m. | W 3-2 | |
| Mon., 9/27 | JV Field Hockey | New Fairfield | Away - New Fairfield HS-Marty Morgan Field [Directions] | 7:00 p.m. | ||
| Tue., 9/28 | V Boys Cross Country | Newtown, Joel Barlow, Notre Dame-Fairfield | Away - Reed Intermediate School-Reed Intermediate School XC Trail [Directions] | 5:00 p.m. | JBHS 23 PHS 33 PHS 15 NDHS 50 PHS 17 Newtown 46 | |
| Pending change awaiting acceptance by one or more parties involved: Time to 4:30 p.m. | ||||||
| Tue., 9/28 | V Boys Soccer | Kolbe Cathedral | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | W 7-0 | |
| Tue., 9/28 | V Girls Cross Country | Newtown, Joel Barlow, Notre Dame-Fairfield | Away - Reed Intermediate School-Reed Intermediate School XC Trail [Directions] | 4:30 p.m. | PHS 18 JBHS 39 PHS 25 Newtown 31 PHS 15 NDHS 50 | |
| Pending change awaiting acceptance by one or more parties involved: Time to 5:00 p.m. | ||||||
| Tue., 9/28 | V Girls Swimming and Diving | Woodland | Away - Woodland HS-pool [Directions] | Postponed | ||
| Wed., 9/29 | V Boys Golf | Masuk | Home - Pomperaug HS-Highfield Country Club [Directions] | 3:00 p.m. | Cancelled | |
| Wed., 9/29 | FR Boys Soccer | New Milford | Away - New Milford HS-Middle Soccer Field - NMHS [Directions] | 4:00 p.m. | ||
| Wed., 9/29 | V Field Hockey | New Milford | Home - Pomperaug HS-Stadium [Directions] | 5:30 p.m. | W 3-1 | |
| Wed., 9/29 | JV Field Hockey | New Milford | Home - Pomperaug HS-Stadium [Directions] | 4:00 p.m. | ||
| Wed., 9/29 | V Girls Volleyball | Immaculate | Away - Immaculate HS-Immaculate Gym [Directions] | 7:00 p.m. | W 3-0 | |
| Wed., 9/29 | JV Girls Volleyball | Immaculate | Away - Immaculate HS-Immaculate Gym [Directions] | 5:30 p.m. | ||
| Wed., 9/29 | FR Girls Volleyball | Immaculate | Away - Immaculate HS-Immaculate Gym [Directions] | 4:00 p.m. | ||
| Thu., 9/30 | FR Football | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 5:45 p.m. | ||
| Thu., 9/30 | V Boys Golf | Stratford, Joel Barlow | Away - Mill River Country Club [Directions] | 3:00 p.m. | Stratford 240 Barlow 176 Pomperaug 167 | |
| Thu., 9/30 | V Boys Soccer | Weston | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | L 2-0 | |
| Thu., 9/30 | JV Boys Soccer | Weston | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Thu., 9/30 | V Girls Soccer | Weston | Away - Weston HS-WHS Stadium Field [Directions] | 7:00 p.m. | T 0-0 | |
| Thu., 9/30 | JV Girls Soccer | Weston | Away - Weston HS-WHS Lower Turf Field [Directions] | 7:00 p.m. | ||
| Fri., 10/1 | V Football | Fairfield Ludlowe | Home - Pomperaug HS-Stadium [Directions] | 6:30 p.m. | L 0-34 | |
| Fri., 10/1 | V Girls Swimming and Diving | Bunnell | Away - Bunnell HS-Flood M.S. Pool [Directions] | 6:30 p.m. | 88/69 pomp | |
| Fri., 10/1 | V Girls Volleyball | Newtown | Home - Pomperaug HS-Main Gym [Directions] | 6:30 p.m. | L 2-3 | |
| Fri., 10/1 | JV Girls Volleyball | Newtown | Home - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 10/1 | FR Girls Volleyball | Newtown | Home - Pomperaug HS-Auxiliary Gym [Directions] | 5:15 p.m. | ||
| Sat., 10/2 | V Boys Cross Country | Brewster Invitational | Away - Not Listed-TBA | 10:00 a.m. | ||
| Sat., 10/2 | JV Football | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 10:00 a.m. | ||
| Sat., 10/2 | FR Boys Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | 10:00 a.m. | ||
| Sat., 10/2 | V Girls Cross Country | Brewster Invitational | Away - Not Listed | 10:00 a.m. | ||
| Mon., 10/4 | V Boys Golf | Brookfield | Home - Pomperaug HS-Highfield Country Club [Directions] | 3:00 p.m. | Pomperaug 162 Brookfield 196 | |
| Mon., 10/4 | V Boys Soccer | Abbott Tech | Away - Broadview MS-Stephen A. Kaplanis Turf Field [Directions] | 3:30 p.m. | W 3-1 | |
| Tue., 10/5 | V Boys Cross Country | Bunnell, Masuk | Home - Pomperaug HS-Cross Country Course [Directions] | 4:30 p.m. | PHS 15 Masuk 50 PHS 15 Bunnell 50 | |
| Tue., 10/5 | V Boys Golf | Immaculate | Home - Pomperaug HS-Highfield Country Club [Directions] | 3:00 p.m. | Pomperaug 154 Immaculate 179 | |
| Tue., 10/5 | V Boys Soccer | Bethel | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | L 3-1 | |
| Tue., 10/5 | JV Boys Soccer | Bethel | Home - Pomperaug HS-PHS Soccer Field [Directions] | 5:00 p.m. | ||
| Tue., 10/5 | V Girls Cross Country | Bunnell, Masuk | Home - Pomperaug HS-Cross Country Course [Directions] | 5:00 p.m. | PHS 19 Bunnell 40 PHS 16 Masuk 43 | |
| Tue., 10/5 | V Girls Soccer | Bethel | Away - Bethel HS-DeSantis Field at Bethel High [Directions] | 4:15 p.m. | W 2-1 | |
| Tue., 10/5 | JV Girls Soccer | Bethel | Away - Bethel MS-Middle School soccer field [Directions] | 4:15 p.m. | ||
| Tue., 10/5 | V Girls Swimming and Diving | Newtown | Home - Pomperaug HS-PHS Pool [Directions] | 6:00 p.m. | 101/85 Pomp | |
| Tue., 10/5 | V Girls Volleyball | Kolbe Cathedral | Away - Kolbe Cathedral HS-Gym [Directions] | 7:00 p.m. | W 3-0 | |
| Tue., 10/5 | JV Girls Volleyball | Kolbe Cathedral | Away - Kolbe Cathedral HS-Gym [Directions] | 5:30 p.m. | ||
| Wed., 10/6 | FR Boys Soccer | New Milford | Home - Pomperaug HS-PHS Soccer Field [Directions] | 4:00 p.m. | ||
| Wed., 10/6 | V Field Hockey | Bethel | Away - Bethel HS-Hunt Field at Bethel HS [Directions] | 7:00 p.m. | W 1-0 | |
| Wed., 10/6 | JV Field Hockey | Bethel | Away - Bethel HS-Hunt Field at Bethel HS [Directions] | 5:30 p.m. | ||
| Wed., 10/6 | V Girls Volleyball | Notre Dame-Fairfield | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 10/6 | JV Girls Volleyball | Notre Dame-Fairfield | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/7 | V Boys Golf | CHAPPA- at Long Shore Country Club- Westport | Away - Not Listed | 11:00 a.m. | ||
| Fri., 10/8 | V Boys Soccer | Stratford | Away - Penders Field-Penders Field - Stratford [Directions] | 7:00 p.m. | T 1-1 | |
| Fri., 10/8 | JV Boys Soccer | Stratford | Away - Penders Field-Penders Field - Stratford [Directions] | 5:45 p.m. | ||
| Fri., 10/8 | V Girls Soccer | Stratford | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | W 3-0 | |
| Fri., 10/8 | JV Girls Soccer | Stratford | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Fri., 10/8 | V Girls Swimming and Diving | Stratford | Home - Pomperaug HS-PHS Pool [Directions] | 5:00 p.m. | 98/72 pomp | |
| Fri., 10/8 | V Girls Volleyball | Masuk | Home - Pomperaug HS-Main Gym [Directions] | 6:30 p.m. | W 3-0 | |
| Fri., 10/8 | JV Girls Volleyball | Masuk | Home - Pomperaug HS-Main Gym [Directions] | 5:00 p.m. | ||
| Fri., 10/8 | FR Girls Volleyball | Masuk | Home - Pomperaug HS-Auxiliary Gym [Directions] | 5:00 p.m. | ||
| Sat., 10/9 | FR Boys Soccer | Fairfield Warde | Home - Pomperaug HS-PHS Soccer Field [Directions] | 10:30 a.m. | ||
| Sat., 10/9 | V Field Hockey | Granby Memorial | Home - Pomperaug HS-Stadium [Directions] | 11:45 a.m. | OT-L 1-2 | |
| Sat., 10/9 | JV Field Hockey | Granby Memorial | Home - Pomperaug HS-Stadium [Directions] | 10:00 a.m. | ||
| Mon., 10/11 | V Boys Golf | Weston | Away - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | Pomperaug 172 Weston 201 | |
| Mon., 10/11 | V Boys Soccer | Watertown | Home - Pomperaug HS-Stadium [Directions] | 6:15 p.m. | L 1-0 | |
| Mon., 10/11 | V Field Hockey | Watertown | Home - Pomperaug HS-Stadium [Directions] | 12:15 p.m. | W 2-0 | |
| Mon., 10/11 | JV Field Hockey | Watertown | Home - Pomperaug HS-Stadium [Directions] | Canceled | Cancelled | |
| Mon., 10/11 | V Girls Soccer | Watertown | Home - Pomperaug HS-Stadium [Directions] | 4:00 p.m. | L 0-1 | |
| Tue., 10/12 | V Boys Cross Country | Immaculate, New Milford, Weston | Away - Immaculate HS-Tarrywile [Directions] | 4:30 p.m. | PHS 20 Weston 39 NMHS 15 PHS 42 PHS 21 Immaculate 38 | |
| Tue., 10/12 | V Boys Golf | SWC Championship at Fairchild Wheeler- Black | Home - Pomperaug HS-Fairchild Wheeler Golf Course [Directions] | 8:30 a.m. | ||
| Tue., 10/12 | V Boys Soccer | Notre Dame-Fairfield | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | W 1-0 | |
| Tue., 10/12 | V Girls Cross Country | Immaculate, New Milford, Weston | Away - Immaculate HS-Tarrywile [Directions] | 5:00 p.m. | NMHS 17 PHS 43 PHS 18 Weston 41 PHS 27 Immaculate 30 | |
| Tue., 10/12 | V Girls Soccer | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Park Ave Field [Directions] | 4:30 p.m. | T 0-0 | |
| Tue., 10/12 | V Girls Swimming and Diving | Weston | Away - Weston HS-Weston MS Pool [Directions] | 4:00 p.m. | 101/74 weston | |
| Tue., 10/12 | V Girls Volleyball | Brookfield | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Tue., 10/12 | JV Girls Volleyball | Brookfield | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/12 | FR Girls Volleyball | Brookfield | Home - Pomperaug HS-Auxiliary Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/13 | FR Football | Stratford | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | ||
| Wed., 10/13 | FR Boys Soccer | Masuk | Away - Great Hollow Lake Field-Soccer Field [Directions] | 3:45 p.m. | ||
| Wed., 10/13 | V Field Hockey | Weston | Home - Pomperaug HS-Stadium [Directions] | 5:30 p.m. | W 1-0 | |
| Wed., 10/13 | JV Field Hockey | Weston | Home - Pomperaug HS-Stadium [Directions] | 4:00 p.m. | ||
| Thu., 10/14 | V Boys Soccer | Bunnell | Away - Bunnell HS-Mastroni Field [Directions] | 7:00 p.m. | T 1-1 | |
| Thu., 10/14 | JV Boys Soccer | Bunnell | Away - Bunnell HS-Mastroni Field [Directions] | 5:30 p.m. | ||
| Thu., 10/14 | V Girls Soccer | Bunnell | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | W 6-0 | |
| Thu., 10/14 | JV Girls Soccer | Bunnell | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | ||
| Thu., 10/14 | V Girls Swimming and Diving | New Fairfield | Away - New Fairfield HS-Pool [Directions] | 4:00 p.m. | 105/70 Pomp | |
| Thu., 10/14 | V Girls Volleyball | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | 7:00 p.m. | W 3-0 | |
| Thu., 10/14 | JV Girls Volleyball | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | 5:30 p.m. | ||
| Thu., 10/14 | FR Girls Volleyball | New Fairfield | Away - New Fairfield HS-MS Gym [Directions] | 5:30 p.m. | ||
| Fri., 10/15 | V Football | Stratford | Away - Penders Field-Penders Field - Stratford [Directions] | 7:00 p.m. | L 6-27 | |
| Fri., 10/15 | V Field Hockey | Farmington | Away - Farmington HS-Turf Field [Directions] | 7:00 p.m. | L 0-2 | |
| Fri., 10/15 | JV Field Hockey | Farmington | Away - Farmington HS-Turf Field [Directions] | 5:30 p.m. | ||
| Sat., 10/16 | JV Football | Stratford | Home - Pomperaug HS-Stadium [Directions] | Canceled | Cancelled | |
| Sat., 10/16 | V Boys Soccer | Naugatuck | Home - Pomperaug HS-Stadium [Directions] | 1:15 p.m. | W 2-0 | |
| Sat., 10/16 | FR Boys Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 1:00 p.m. | ||
| Sat., 10/16 | FR Field Hockey | Joel Barlow | Away - Joel Barlow High-Field D [Directions] | Canceled | Cancelled | |
| Sat., 10/16 | V Girls Volleyball | New Milford | Home - Pomperaug HS-Main Gym [Directions] | 12:00 p.m. | W 3-1 | |
| Sat., 10/16 | JV Girls Volleyball | New Milford | Home - Pomperaug HS-Main Gym [Directions] | 10:45 a.m. | ||
| Sat., 10/16 | FR Girls Volleyball | New Milford | Home - Pomperaug HS-Auxiliary Gym [Directions] | 9:30 a.m. | ||
| Mon., 10/18 | V Boys Golf | CIAC Fall Division II Boys Golf Championship | Away - Silo Point GC | 8:30 a.m. | ||
| Mon., 10/18 | V Field Hockey | Brookfield | Away - Brookfield HS-BHS Stadium Field [Directions] | 5:30 p.m. | W 2-0 | |
| Mon., 10/18 | JV Field Hockey | Brookfield | Away - Brookfield HS-BHS Stadium Field [Directions] | 7:00 p.m. | ||
| Mon., 10/18 | V Girls Volleyball | Woodland | Home - Pomperaug HS-Main Gym [Directions] | 5:00 p.m. | W 3-0 | |
| Mon., 10/18 | JV Girls Volleyball | Woodland | Home - Pomperaug HS-Main Gym [Directions] | 3:30 p.m. | ||
| Mon., 10/18 | FR Girls Volleyball | Woodland | Home - Pomperaug HS-Auxiliary Gym [Directions] | 3:30 p.m. | ||
| Tue., 10/19 | JV Boys Soccer | Immaculate | Away - Immaculate HS-Baseball Diamond [Directions] | Canceled | Cancelled | |
| Tue., 10/19 | V Girls Soccer | Immaculate | Home - Pomperaug HS-Stadium [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 10/19 | V Girls Swimming and Diving | New Milford | Home - Pomperaug HS-PHS Pool [Directions] | 4:00 p.m. | 102/75 Pomp | |
| Tue., 10/19 | V Girls Volleyball | Stratford | Away - Stratford HS-Gym [Directions] | 6:45 p.m. | W 3-0 | |
| Tue., 10/19 | JV Girls Volleyball | Stratford | Away - Stratford HS-Gym [Directions] | 5:45 p.m. | ||
| Tue., 10/19 | FR Girls Volleyball | Stratford | Away - Stratford HS-Gym [Directions] | Postponed | ||
| Wed., 10/20 | V Boys Cross Country | SWC Championship | Away - Bethel HS-BHS track | 3:30 p.m. | ||
| Wed., 10/20 | FR Boys Soccer | Newtown | Home - Pomperaug HS-PHS Soccer Field [Directions] | 4:00 p.m. | ||
| Wed., 10/20 | V Girls Cross Country | SWC Championship | Away - Bethel HS-BHS track | 3:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 4:00 p.m. | ||||||
| Wed., 10/20 | V Field Hockey | Immaculate | Home - Pomperaug HS-Stadium [Directions] | 5:30 p.m. | W 2-0 | |
| Wed., 10/20 | JV Field Hockey | Immaculate | Home - Pomperaug HS-Stadium [Directions] | Canceled | Cancelled | |
| Thu., 10/21 | FR Football | Bethel | Away - Bethel HS-DeSantis Field at Bethel High [Directions] | 4:00 p.m. | ||
| Thu., 10/21 | V Boys Soccer | New Fairfield | Away - New Fairfield HS-Marty Morgan Field [Directions] | 7:15 p.m. | T 1-1 | |
| Thu., 10/21 | JV Boys Soccer | New Fairfield | Away - New Fairfield HS-Marty Morgan Field [Directions] | 5:30 p.m. | ||
| Thu., 10/21 | V Girls Soccer | New Fairfield | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | W 3-0 | |
| Thu., 10/21 | JV Girls Soccer | New Fairfield | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Thu., 10/21 | V Girls Volleyball | Bunnell | Away - Bunnell HS-David Johnson Gymnasium [Directions] | 5:30 p.m. | W 3-0 | |
| Thu., 10/21 | JV Girls Volleyball | Bunnell | Away - Bunnell HS-David Johnson Gymnasium [Directions] | 6:30 p.m. | ||
| Fri., 10/22 | V Field Hockey | Thomaston | Home - Pomperaug HS-Stadium [Directions] | 5:15 p.m. | W 2-0 | |
| Fri., 10/22 | JV Field Hockey | Thomaston | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | ||
| Sat., 10/23 | V Boys Soccer | Immaculate | Away - Immaculate HS-Mustang Valley [Directions] | 1:30 p.m. | L 1-2 | |
| Sat., 10/23 | FR Field Hockey | Masuk | Home - Pomperaug HS-Baseball Field [Directions] | Canceled | Cancelled | |
| Sat., 10/23 | V Girls Soccer | Ridgefield | Away - Scotts Ridge MS-SRMS Turf [Directions] | 1:00 p.m. | L 0-1 | |
| Mon., 10/25 | V Boys Soccer | Newtown | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | T 0-0 | |
| Mon., 10/25 | JV Boys Soccer | Newtown | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Mon., 10/25 | V Field Hockey | Newtown | Away - Treadwell Park-Newtown Treadwell Park [Directions] | 4:00 p.m. | L 0-3 | |
| Mon., 10/25 | JV Field Hockey | Newtown | Away - Treadwell Park-Newtown Treadwell Park [Directions] | 5:45 p.m. | ||
| Mon., 10/25 | V Girls Soccer | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 6:00 p.m. | L 0-1 | |
| Mon., 10/25 | V Girls Volleyball | Bethel | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | W 3-1 | |
| Mon., 10/25 | JV Girls Volleyball | Bethel | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 10/25 | FR Girls Volleyball | Bethel | Home - Pomperaug HS-Auxiliary Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/27 | V Girls Soccer | Kolbe Cathedral | Away - Veterans Memorial Park CT [Directions] | 4:30 p.m. | W 8-1 | |
| Wed., 10/27 | JV Girls Soccer | Newtown | Away - Treadwell Park-Treadwell Town Park--Tilson Field [Directions] | 5:30 p.m. | ||
| Wed., 10/27 | V Girls Swimming and Diving | Bethel/Immaculate, Immaculate | Home - Pomperaug HS-PHS Pool [Directions] | 7:00 p.m. | 99/76 | |
| Wed., 10/27 | V Girls Volleyball | Immaculate | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 10/27 | JV Girls Volleyball | Immaculate | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/27 | FR Girls Volleyball | Immaculate | Home - Pomperaug HS-Auxiliary Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/28 | FR Football | North Haven | Home - Pomperaug HS-Stadium [Directions] | 4:00 p.m. | ||
| Thu., 10/28 | V Field Hockey | Bethel | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | W 3-0 | |
| Thu., 10/28 | V Girls Volleyball | Naugatuck | Home - Pomperaug HS-Main Gym [Directions] | 6:15 p.m. | W 3-1 | |
| Thu., 10/28 | JV Girls Volleyball | Naugatuck | Home - Pomperaug HS-Main Gym [Directions] | 5:00 p.m. | ||
| Thu., 10/28 | FR Girls Volleyball | Naugatuck | Home - Pomperaug HS-Auxiliary Gym [Directions] | 5:00 p.m. | ||
| Fri., 10/29 | V Football | North Haven | Away - North Haven MS-Vanacore Field [Directions] | 7:00 p.m. | L 7-40 | |
| Fri., 10/29 | V Girls Soccer | Brookfield | Home - Pomperaug HS-Stadium [Directions] | 5:30 p.m. | L 0-1 | |
| Fri., 10/29 | JV Girls Soccer | Ridgefield | Away - Ridgefield HS-RHS Lower Grass Field [Directions] | 6:30 p.m. | ||
| Sat., 10/30 | JV Football | North Haven | Home - Pomperaug HS-Stadium [Directions] | Canceled | Cancelled | |
| Mon., 11/1 | V Boys Cross Country | CIAC Boys Cross Country Class L Championship | Away - Wickham Park | 11:25 a.m. | ||
| Mon., 11/1 | V Girls Cross Country | CIAC Girls Cross Country Class L Championship | Away - Wickham Park | 11:55 a.m. | ||
| Mon., 11/1 | V Girls Volleyball | Brookfield | Home - Pomperaug HS-Main Gym [Directions] | 6:00 p.m. | W 3-1 | |
| Tue., 11/2 | V Field Hockey | Joel Barlow | Home - Pomperaug HS-Stadium [Directions] | 6:00 p.m. | ||
| Wed., 11/3 | V Girls Swimming and Diving | SWC Diving Championship Meet | Away - Weston HS-Weston MS Pool | 5:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 5:30 p.m. | ||||||
| Wed., 11/3 | V Girls Volleyball | Newtown | Away - Newtown HS-Gym [Directions] | 6:00 p.m. | L 1-3 | |
| Thu., 11/4 | FR Football | New Milford | Away - New Milford HS-North Turf Field - NMHS [Directions] | 6:00 p.m. | ||
| Thu., 11/4 | V Boys Soccer | Torrington (Scrim.) | Away - Torrington HS-Robert Frost Sports Complex [Directions] | 6:00 p.m. | ||
| Thu., 11/4 | V Girls Soccer | Danbury (Scrim.) | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | ||
| Fri., 11/5 | V Boys Cross Country | CIAC Boys Cross Country Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Fri., 11/5 | V Football | New Milford | Home - Pomperaug HS-Stadium [Directions] | 6:30 p.m. | L 3-14 | |
| Fri., 11/5 | V Girls Cross Country | CIAC Girls Cross Country Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Sat., 11/6 | V Girls Swimming and Diving | SWC Girls Swimming Championship Meet | Away - Masuk HS-Pool | 3:30 p.m. | ||
| Mon., 11/8 | V Girls Soccer | Windsor | Home - Pomperaug HS-Stadium [Directions] | 6:15 p.m. | W 2-1 | |
| Tue., 11/9 | V Boys Soccer | Daniel Hand | Away - Madison Surf Club-Strong Field [Directions] | 5:00 p.m. | ||
| Tue., 11/9 | V Field Hockey | Bethel | Home - Pomperaug HS-Stadium [Directions] | 5:30 p.m. | ||
| Wed., 11/10 | V Girls Soccer | Branford | Away - Branford HS-Athletic Turf Field [Directions] | 6:00 p.m. | L 0-1 | |
| Wed., 11/10 | V Girls Swimming and Diving | CIAC Class L Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Thu., 11/11 | V Field Hockey | Simsbury | Home - Pomperaug HS-Stadium [Directions] | 5:30 p.m. | ||
| Thu., 11/11 | V Girls Volleyball | St. Joseph | Home - Pomperaug HS-Main Gym [Directions] | 6:00 p.m. | ||
| Fri., 11/12 | FR Football | Joel Barlow | Home - Pomperaug HS-Stadium [Directions] | 4:00 p.m. | ||
| Sat., 11/13 | V Football | Joel Barlow | Away - Joel Barlow HS-Field I (Stadium) [Directions] | 1:00 p.m. | L 3-41 | |
| Sat., 11/13 | V Girls Swimming and Diving | CIAC Class L Qualifying Meet | Away - Cornerstone Pool | 3:15 p.m. | ||
| Tue., 11/16 | V Field Hockey | Guilford | Away - Amity Regional HS-Field Hockey Field [Directions] | 6:00 p.m. | ||
| Tue., 11/16 | V Girls Swimming and Diving | CIAC Class L Swimming Championships | Away - SCSU | 6:00 p.m. | ||
| Thu., 11/18 | FR Football | Wilton | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Thu., 11/18 | V Girls Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Fri., 11/19 | V Football | Wilton | Away - Wilton HS-Fujitani Field - Turf [Directions] | 7:00 p.m. | L 0-43 | |
| Sat., 11/20 | JV Football | Wilton | Home - Pomperaug HS-Stadium [Directions] | Canceled | Cancelled | |
| Sun., 11/21 | V Girls Swimming and Diving | CIAC State Open Swimming Championships | Away - Cornerstone Pool | 2:00 p.m. | ||
| Wed., 11/24 | V Football | Notre Dame-Fairfield | Home - Pomperaug HS-Stadium [Directions] | 6:30 p.m. | L 0-46 | |
| Sat., 12/4 | V Boys Ice Hockey | Milford Coop (Scrim.) | Away - Milford Ice Pavillion-Ice Rink [Directions] | 5:30 p.m. | ||
| Tue., 12/7 | V Boys Basketball | Wilby (Scrim.) | Home - Pomperaug HS-Main Gym [Directions] | 5:00 p.m. | ||
| Wed., 12/8 | V Boys Ice Hockey | Tri-Town (Scrim.) | Away - Enfield Twin Rinks-Rink 2 [Directions] | 3:50 p.m. | ||
| Wed., 12/8 | V Girls Basketball | Ridgefield (Scrim.) | Away - Ridgefield HS-Main Gym [Directions] | 4:30 p.m. | ||
| Thu., 12/9 | V Boys Basketball | Holy Cross (Scrim.) | Away - Holy Cross-gym [Directions] | 5:00 p.m. | ||
| Fri., 12/10 | V Girls Basketball | Trumbull (Scrim.) | Away - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | ||
| Sat., 12/11 | V Girls Basketball | Norwich Free Academy (Scrim.) | Away - Norwich Free Academy-Alumni Gym [Directions] | 3:00 p.m. | ||
| Mon., 12/13 | V Boys Basketball | Nonnewaug (Scrim.) | Home - Pomperaug HS-Auxiliary Gym [Directions] | 4:00 p.m. | ||
| Mon., 12/13 | V Girls Basketball | Cheshire | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | W 55-40 | |
| Mon., 12/13 | JV Girls Basketball | Cheshire | Home - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 12/13 | FR Girls Basketball | Cheshire | Home - Pomperaug HS-Main Gym [Directions] | 3:30 p.m. | ||
| Wed., 12/15 | V Boys Ice Hockey | Trumbull | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | 8:30 p.m. | L 4-5 | |
| Wed., 12/15 | V Wrestling | Weston | Home - Pomperaug HS-Auxiliary Gym [Directions] | 6:00 p.m. | Weston 39 Pomperaug 33 | |
| Thu., 12/16 | V Boys Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 7:00 p.m. | L 61-65 | |
| Thu., 12/16 | JV Boys Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 12/16 | FR Boys Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 12/18 | V Boys Basketball | Branford | Away - Branford HS-Gym [Directions] | 5:15 p.m. | L 57-61 | |
| Sat., 12/18 | JV Boys Basketball | Branford | Away - Branford HS-Gym [Directions] | 3:30 p.m. | ||
| Sat., 12/18 | FR Boys Basketball | Branford | Away - Branford HS-Gym [Directions] | 2:00 p.m. | ||
| Sat., 12/18 | V Boys Ice Hockey | Daniel Hand | Home - Taft School-Mays [Directions] | 7:30 p.m. | W 3-0 | |
| Sat., 12/18 | V Wrestling | Pomperaug Quads (2 mats) | Home - Pomperaug HS-Auxiliary Gym [Directions] | 10:00 a.m. | Pomperaug 59 Terryville 12 Pomperaug 48 bacon academy 24 Pomperaug 48 nonnewaug 21 Pomperaug 45 new Canaan 30 Pomperaug 48 Portland 18 | |
| Sat., 12/18 | V Girls Basketball | Stamford | Home - Pomperaug HS-Main Gym [Directions] | 1:15 p.m. | L 60-51 | |
| Sat., 12/18 | JV Girls Basketball | Stamford | Home - Pomperaug HS-Main Gym [Directions] | 11:30 a.m. | ||
| Sat., 12/18 | FR Girls Basketball | Stamford | Home - Pomperaug HS-Main Gym [Directions] | 10:00 a.m. | ||
| Mon., 12/20 | V Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena-Patriot Rink [Directions] | 8:00 p.m. | W 5-0 | |
| Tue., 12/21 | V Boys Swimming and Diving | Masuk | Away - Masuk HS-Pool [Directions] | 6:00 p.m. | Pomperaug- 95 Masuk- 80 | |
| Tue., 12/21 | V Girls Basketball | East Lyme | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | W 40-30 | |
| Tue., 12/21 | JV Girls Basketball | East Lyme | Home - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 12/21 | FR Girls Basketball | Foran | Home - Pomperaug HS-Main Gym [Directions] | 3:30 p.m. | ||
| Wed., 12/22 | V Boys Basketball | Shelton | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | W 64-61 | |
| Wed., 12/22 | JV Boys Basketball | Shelton | Home - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 12/22 | FR Boys Basketball | Shelton | Home - Pomperaug HS-Main Gym [Directions] | 3:30 p.m. | ||
| Wed., 12/22 | V Boys Ice Hockey | Sheehan | Home - Taft School-Mays [Directions] | 7:30 p.m. | L 1-8 | |
| Wed., 12/22 | V Wrestling | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 6:00 p.m. | Pomperaug 36 Masuk 15 | |
| Thu., 12/23 | V Girls Basketball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 7:00 p.m. | L 35-54 | |
| Thu., 12/23 | JV Girls Basketball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 12/27 | V Boys Basketball | E.O. Smith | Home - Pomperaug HS-Main Gym [Directions] | 6:00 p.m. | L 62-63 | |
| Tue., 12/28 | V Boys Ice Hockey | Cheshire | Away - Hamden-Lou Astorino Ice Rink [Directions] | 1:30 p.m. | L 1-5 | |
| Wed., 12/29 | V Boys Basketball | Staples | Away - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | L 50-75 | |
| Wed., 12/29 | V Girls Basketball | Coginchaug | Away - North Haven HS-Fred Kelly Gymnasium [Directions] | 3:00 p.m. | W 53-42 | |
| Thu., 12/30 | V Wrestling | Trumbull Duals | Away - Trumbull HS-THS Main Gym | 9:00 a.m. | Cancelled | |
| Thu., 12/30 | V Girls Basketball | North Haven | Away - North Haven HS-Fred Kelly Gymnasium [Directions] | 5:00 p.m. | W 54-36 | |
| Mon., 1/3 | V Girls Basketball | Naugatuck | Home - Pomperaug HS-Main Gym [Directions] | 6:00 p.m. | W 56-26 | |
| Mon., 1/3 | JV Girls Basketball | Naugatuck | Home - Pomperaug HS-Main Gym [Directions] | Postponed | ||
| Wed., 1/5 | V Boys Ice Hockey | Farmington Valley Generals | Away - Avon Old Farms-Jennings Rink [Directions] | 8:00 p.m. | L 1-4 | |
| Thu., 1/6 | V Boys Basketball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 7:00 p.m. | L 60-71 | |
| Thu., 1/6 | JV Boys Basketball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 5:15 p.m. | ||
| Thu., 1/6 | FR Boys Basketball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 3:30 p.m. | ||
| Thu., 1/6 | V Boys Indoor Track | SWC Varsity Indoor Meet | Away - Bethel HS | 4:00 p.m. | ||
| Thu., 1/6 | V Wrestling | Haddam-Killingworth, Middletown, Nonnewaug (2 mats) | Away - Haddam Killingworth HS (HK)-Patsy Kamercia Field House [Directions] | 5:30 p.m. | Pomperaug 39 Middletown 27 Pomperaug 36 Haddam-killingworth 30 | |
| Thu., 1/6 | V Girls Basketball | Weston | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | W 62-25 | |
| Thu., 1/6 | JV Girls Basketball | Weston | Home - Pomperaug HS-Main Gym [Directions] | 5:45 p.m. | ||
| Thu., 1/6 | V Girls Indoor Track | SWC Indoor Track Meet | Away - Bethel HS-Track and Field Training Center | 4:00 p.m. | ||
| Thu., 1/6 | V Girls Indoor Track | SWC Varsity Indoor Meet | Away - Bethel HS | 4:00 p.m. | ||
| Sat., 1/8 | V Boys Ice Hockey | Immaculate | Home - Taft School-Mays [Directions] | 8:00 p.m. | L 4-6 | |
| Sat., 1/8 | V Boys Indoor Track | SWC JV Developmental | Away - Bethel HS-Track and Field Training Center | 3:00 p.m. | ||
| Pending changes awaiting acceptance by one or more parties involved: Date to 1/17, Time to 2:00 p.m. | ||||||
| Sat., 1/8 | V Wrestling | Bristol Central Invitational (4 mats) | Away - Bristol Central HS-Charles C. Marsh Gymnasium | 8:00 a.m. | Mike carpenter 1st Zach Hartman 1st Julianna Morris 4th Noen Jian 5th Alex Lee 5th Emin ismaili 5th Steve Purcell 6th Blake Dawson 6th | |
| Sat., 1/8 | V Girls Basketball | Immaculate | Home - Pomperaug HS-Main Gym [Directions] | 12:30 p.m. | W 51-49 | |
| Sat., 1/8 | JV Girls Basketball | Immaculate | Home - Pomperaug HS-Main Gym [Directions] | 11:15 a.m. | ||
| Sat., 1/8 | FR Girls Basketball | Immaculate | Home - Pomperaug HS-Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 1/8 | V Girls Indoor Track | JV Developmental Meet | Away - Bethel HS-Track and Field Training Center | 3:00 p.m. | ||
| Pending changes awaiting acceptance by one or more parties involved: Date to 1/17, Time to 2:00 p.m. | ||||||
| Mon., 1/10 | V Boys Basketball | Kolbe Cathedral | Away - Cardinal Sheehan Center Bridgeport [Directions] | 7:00 p.m. | L 53-62 | |
| Mon., 1/10 | JV Boys Basketball | Kolbe Cathedral | Away - Cardinal Sheehan Center Bridgeport [Directions] | 5:15 p.m. | ||
| Mon., 1/10 | V Wrestling | Brookfield/Shepaug | Away - Brookfield HS-BHS Small Gym [Directions] | 6:00 p.m. | Pomperaug 63 Brookfield 4 | |
| Mon., 1/10 | V Girls Basketball | Kolbe Cathedral | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | L 45-46 | |
| Mon., 1/10 | JV Girls Basketball | Kolbe Cathedral | Home - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/11 | V Boys Swimming and Diving | Newtown | Home - Pomperaug HS-PHS Pool [Directions] | 7:00 p.m. | PHS- 99 NHS- 81 | |
| Wed., 1/12 | V Boys Indoor Track | SWC JV Developmental | Away - Bethel HS-Track and Field Training Center | 4:00 p.m. | ||
| Wed., 1/12 | V Wrestling | Stratford | Home - Pomperaug HS-Auxiliary Gym [Directions] | 6:00 p.m. | Pomperaug 47 Stratford 24 | |
| Wed., 1/12 | V Girls Indoor Track | JV Developmental Meet | Away - Bethel HS-Track and Field Training Center | 4:00 p.m. | ||
| Thu., 1/13 | V Boys Basketball | Bunnell | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | W 62-45 | |
| Thu., 1/13 | JV Boys Basketball | Bunnell | Home - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | ||
| Thu., 1/13 | FR Boys Basketball | Bunnell | Home - Pomperaug HS-Main Gym [Directions] | 3:45 p.m. | ||
| Thu., 1/13 | V Girls Basketball | Bunnell | Away - Bunnell HS-David Johnson Gymnasium [Directions] | 7:00 p.m. | W 57-28 | |
| Thu., 1/13 | JV Girls Basketball | Bunnell | Away - Bunnell HS-David Johnson Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/14 | V Boys Swimming and Diving | Weston | Home - Pomperaug HS-PHS Pool [Directions] | 5:00 p.m. | PHS- 90 Weston- 83 | |
| Sat., 1/15 | V Boys Ice Hockey | Lyman Hall | Home - Taft School-Mays [Directions] | 7:30 p.m. | L 2-4 | |
| Sat., 1/15 | V Wrestling | Berlin, Avon, Bethel, Branford, Portland, Terryville/Thomaston (3 mats) | Away - Berlin HS-Jim Day Gymnasium | 10:00 a.m. | Pomperaug 18 Branford 46 Pomperaug 54 Berlin 15 Pomperaug 45 Bethel 24 Pomperaug 22 Avon 60 | |
| Mon., 1/17 | V Boys Ice Hockey | North Haven | Home - Taft School-Mays [Directions] | 7:30 p.m. | L 3-5 | |
| Mon., 1/17 | V Boys Indoor Track | Varsity Developmental Race | Away - TBA | Postponed | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 9:00 a.m. | ||||||
| Mon., 1/17 | V Boys Indoor Track | Bethel, Brookfield, Bunnell, Immaculate, Joel Barlow, Kolbe Cathedral, Masuk, New Fairfield, New Milford, Newtown, Notre Dame-Fairfield, Stratford, Weston | Away - Bethel HS-Track and Field Training Center | 2:00 p.m. | ||
| Mon., 1/17 | V Girls Indoor Track | Varsity Developmental Meet | Away - TBA-connell memorial rink | Postponed | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 9:00 a.m. | ||||||
| Mon., 1/17 | V Girls Indoor Track | Bethel, Brookfield, Bunnell, Immaculate, Joel Barlow, Kolbe Cathedral, Masuk, New Fairfield, New Milford, Newtown, Notre Dame-Fairfield, Stratford, Weston | Away - Bethel HS-Track and Field Training Center | 2:00 p.m. | ||
| Tue., 1/18 | V Boys Basketball | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Sister Marion Reilly Auditorium [Directions] | 7:00 p.m. | L 52-91 | |
| Tue., 1/18 | JV Boys Basketball | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Sister Marion Reilly Auditorium [Directions] | 5:15 p.m. | ||
| Tue., 1/18 | FR Boys Basketball | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Sister Marion Reilly Auditorium [Directions] | 3:30 p.m. | ||
| Tue., 1/18 | V Boys Swimming and Diving | New Fairfield | Away - New Fairfield HS-Pool [Directions] | 6:00 p.m. | PHS- 93 NFHS-65 | |
| Tue., 1/18 | V Girls Basketball | Notre Dame-Fairfield | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | L 27-56 | |
| Tue., 1/18 | JV Girls Basketball | Notre Dame-Fairfield | Home - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/18 | FR Girls Basketball | Notre Dame-Fairfield | Home - Pomperaug HS-Main Gym [Directions] | Canceled | Cancelled | |
| Wed., 1/19 | V Boys Ice Hockey | Masuk | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 8:00 p.m. | W 5-2 | |
| Wed., 1/19 | V Boys Indoor Track | Brookfield, Bethel, Bunnell, Immaculate, Joel Barlow, Kolbe Cathedral, Masuk, New Fairfield, New Milford, Newtown, Notre Dame-Fairfield, Stratford, Weston | Away - Floyd Little Athletic Center-Field House | 5:15 p.m. | ||
| Wed., 1/19 | V Wrestling | Bunnell | Away - Bunnell HS-David Johnson Gymnasium [Directions] | 6:00 p.m. | Pomperaug 42 Bunnell 39 | |
| Wed., 1/19 | V Girls Indoor Track | Brookfield, Bethel, Bunnell, Immaculate, Joel Barlow, Kolbe Cathedral, Masuk, New Fairfield, New Milford, Newtown, Notre Dame-Fairfield, Stratford, Weston | Away - Floyd Little Athletic Center-Field House | 5:15 p.m. | ||
| Fri., 1/21 | V Boys Basketball | Stratford | Away - Stratford HS-Gym [Directions] | 7:00 p.m. | L 57-64 | |
| Fri., 1/21 | JV Boys Basketball | Stratford | Away - Stratford HS-Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/21 | FR Boys Basketball | Stratford | Away - Stratford HS-Gym [Directions] | 3:30 p.m. | ||
| Fri., 1/21 | V Girls Basketball | Stratford | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | W 52-27 | |
| Fri., 1/21 | JV Girls Basketball | Stratford | Home - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | ||
| Sat., 1/22 | V Boys Ice Hockey | Branford | Away - Northford Ice Pavilion-Red [Directions] | 5:00 p.m. | L 4-5 | |
| Sat., 1/22 | V Wrestling | Xavier, Bristol Central, Bristol Eastern, Burlington (MA), Cheshire, Fitch, Guilford, Joel Barlow, TBA, Ridgefield, Simsbury, Trumbull, Hall, Xaverian Brothers (MA) | Away - Xavier HS-Gym | 9:00 a.m. | ||
| Sat., 1/22 | FR Girls Basketball | Foran | Away - Foran HS -Edna L. Fraser Gymnasium [Directions] | 10:00 a.m. | ||
| Tue., 1/25 | V Boys Basketball | Masuk | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | L 41-46 | |
| Tue., 1/25 | JV Boys Basketball | Masuk | Home - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/25 | FR Boys Basketball | Masuk | Home - Pomperaug HS-Main Gym [Directions] | 3:45 p.m. | ||
| Tue., 1/25 | V Boys Swimming and Diving | New Milford | Home - Pomperaug HS-PHS Pool [Directions] | 6:00 p.m. | PHS- 97 NMHS- 80 | |
| Tue., 1/25 | V Girls Basketball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 7:00 p.m. | W 58-38 | |
| Tue., 1/25 | JV Girls Basketball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 5:15 p.m. | ||
| Tue., 1/25 | FR Girls Basketball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | Canceled | Cancelled | |
| Wed., 1/26 | V Boys Ice Hockey | Staples | Away - Milford Ice Pavillion-Ice Rink [Directions] | 5:25 p.m. | W 5-4 | |
| Wed., 1/26 | V Boys Indoor Track | SWC JV Developmental | Away - Bethel HS-Track and Field Training Center | 4:00 p.m. | ||
| Wed., 1/26 | V Wrestling | Newtown | Home - Pomperaug HS-Auxiliary Gym [Directions] | 6:00 p.m. | Newtown 38 Pomperaug 36 | |
| Wed., 1/26 | V Girls Indoor Track | JV Developmental Meet | Away - Bethel HS-Track and Field Training Center | 4:00 p.m. | ||
| Fri., 1/28 | V Boys Basketball | Brookfield | Home - Pomperaug HS-Main Gym [Directions] | 6:00 p.m. | W 52-49 | |
| Fri., 1/28 | JV Boys Basketball | Brookfield | Home - Pomperaug HS-Main Gym [Directions] | 4:30 p.m. | ||
| Fri., 1/28 | FR Boys Basketball | Brookfield | Home - Pomperaug HS-Main Gym [Directions] | 3:15 p.m. | ||
| Fri., 1/28 | V Girls Basketball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 6:00 p.m. | L 52-59 | |
| Fri., 1/28 | JV Girls Basketball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 4:30 p.m. | ||
| Fri., 1/28 | FR Girls Basketball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 3:15 p.m. | ||
| Sat., 1/29 | V Wrestling | Brookfield, Bethel, Canton, Danbury, Darien, Joel Barlow, Montville, New Canaan, Newtown, Stratford, Harding, Wilton | Away - Brookfield HS-BHS Small & Big Gym | Canceled | Cancelled | |
| Pending changes awaiting acceptance by one or more parties involved: Date to 1/30, Time to 11:00 a.m. | ||||||
| Mon., 1/31 | V Boys Basketball | Bethel | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | L 55-60 | |
| Mon., 1/31 | JV Boys Basketball | Bethel | Home - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 1/31 | FR Boys Basketball | Bethel | Home - Pomperaug HS-Main Gym [Directions] | 3:45 p.m. | ||
| Mon., 1/31 | V Girls Basketball | Bethel | Away - Bethel HS-BHS gym [Directions] | 6:00 p.m. | W 67-44 | |
| Mon., 1/31 | JV Girls Basketball | Bethel | Away - Bethel HS-BHS gym [Directions] | 4:15 p.m. | ||
| Tue., 2/1 | V Boys Indoor Track | Last Chance Meet | Away - Bethel HS-BHS gym | 4:00 p.m. | ||
| Tue., 2/1 | V Girls Indoor Track | Last Chance Meet | Away - Bethel HS-Track and Field Training Center | 4:00 p.m. | ||
| Wed., 2/2 | V Boys Ice Hockey | Conard | Home - Taft School-Mays [Directions] | 7:30 p.m. | W 5-1 | |
| Wed., 2/2 | V Wrestling | New Milford | Home - Pomperaug HS-Auxiliary Gym [Directions] | 6:00 p.m. | New milford 48 Pomperaug 26 | |
| Thu., 2/3 | V Boys Basketball | New Milford | Away - New Milford HS-Main Gym - NMHS [Directions] | 7:00 p.m. | L 47-65 | |
| Thu., 2/3 | JV Boys Basketball | New Milford | Away - New Milford HS-Main Gym - NMHS [Directions] | 5:15 p.m. | ||
| Thu., 2/3 | FR Boys Basketball | New Milford | Away - New Milford HS-Main Gym - NMHS [Directions] | 3:45 p.m. | ||
| Thu., 2/3 | V Girls Basketball | New Milford | Home - Pomperaug HS-Main Gym [Directions] | 6:00 p.m. | W 53-36 | |
| Thu., 2/3 | JV Girls Basketball | New Milford | Home - Pomperaug HS-Main Gym [Directions] | 4:30 p.m. | ||
| Thu., 2/3 | FR Girls Basketball | New Milford | Home - Pomperaug HS-Main Gym [Directions] | Canceled | Cancelled | |
| Fri., 2/4 | V Wrestling | Farmington, Maloney, TBA, New Milford | Home - Pomperaug HS-Auxiliary Gym [Directions] | 4:30 p.m. | Cancelled | |
| Sat., 2/5 | V Boys Basketball | Jonathan Law | Away - Jonathan Law HS-James L. Richetelli Memorial Gymnasium [Directions] | 7:00 p.m. | L 57-65 | |
| Sat., 2/5 | JV Boys Basketball | Jonathan Law | Away - Jonathan Law HS-James L. Richetelli Memorial Gymnasium [Directions] | 5:15 p.m. | ||
| Sat., 2/5 | FR Boys Basketball | Jonathan Law | Away - Jonathan Law HS-James L. Richetelli Memorial Gymnasium [Directions] | 3:45 p.m. | ||
| Sat., 2/5 | V Boys Ice Hockey | North Branford | Home - Taft School-Mays [Directions] | 7:30 p.m. | W 5-3 | |
| Sat., 2/5 | V Boys Indoor Track | SWC Indoor Track Championships | Away - Floyd Little Athletic Center-Field House | 5:00 p.m. | ||
| Sat., 2/5 | V Boys Swimming and Diving | Brookfield | Home - Pomperaug HS-PHS Pool [Directions] | 5:00 p.m. | PHS-99 BHS-77 | |
| Sat., 2/5 | V Wrestling | Farmington, Maloney | Home - Pomperaug HS-Auxiliary Gym [Directions] | 11:00 a.m. | Pomperaug 42 Farmington 26 Pomperaug 42 Maloney 36 | |
| Sat., 2/5 | V Girls Indoor Track | SWC Indoor Track Championship | Away - Floyd Little Athletic Center-Field House | 5:00 p.m. | ||
| Mon., 2/7 | V Boys Basketball | Newtown | Away - Newtown HS-Gym [Directions] | 7:00 p.m. | L 44-63 | |
| Mon., 2/7 | JV Boys Basketball | Newtown | Away - Newtown HS-Gym [Directions] | 5:15 p.m. | ||
| Mon., 2/7 | FR Boys Basketball | Newtown | Away - Newtown HS-Gym [Directions] | 3:45 p.m. | ||
| Mon., 2/7 | V Girls Basketball | Newtown | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | W 43-33 | |
| Mon., 2/7 | JV Girls Basketball | Newtown | Home - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 2/7 | Unified Sports Basketball | Newtown | Home - Pomperaug HS-Main Gym [Directions] | 4:30 p.m. | ||
| Tue., 2/8 | V Boys Swimming and Diving | Joel Barlow-Bethel Swim | Home - Pomperaug HS-PHS Pool [Directions] | 5:00 p.m. | Phs-98 B&B-79 | |
| Wed., 2/9 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland of Ice-Stadium [Directions] | 4:15 p.m. | L 1-4 | |
| Thu., 2/10 | V Boys Basketball | New Fairfield | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | W 49-47 | |
| Thu., 2/10 | JV Boys Basketball | New Fairfield | Home - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | ||
| Thu., 2/10 | FR Boys Basketball | New Fairfield | Home - Pomperaug HS-Main Gym [Directions] | 3:45 p.m. | ||
| Thu., 2/10 | V Girls Basketball | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | 7:00 p.m. | W 53-49 | |
| Thu., 2/10 | JV Girls Basketball | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | 5:15 p.m. | ||
| Thu., 2/10 | FR Girls Basketball | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | 3:45 p.m. | ||
| Sat., 2/12 | V Boys Ice Hockey | Guilford | Home - Taft School-Mays [Directions] | 8:00 p.m. | T 4-4(OT) | |
| Sat., 2/12 | V Boys Indoor Track | Class L Championship | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Sat., 2/12 | V Wrestling | New Milford, Brookfield, Bunnell, Joel Barlow, Masuk, SWC Tournament, New Fairfield, Newtown, Stratford, Weston | Away - New Milford HS-Main Gym - NMHS | 8:30 a.m. | ||
| Sat., 2/12 | V Girls Indoor Track | Class L Championship | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Tue., 2/15 | V Boys Basketball | Joel Barlow | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | L 44-58 | |
| Tue., 2/15 | JV Boys Basketball | Joel Barlow | Home - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/15 | FR Boys Basketball | Joel Barlow | Home - Pomperaug HS-Main Gym [Directions] | 3:45 p.m. | ||
| Tue., 2/15 | V Boys Swimming and Diving | Oxford | Home - Pomperaug HS-PHS Pool [Directions] | 6:00 p.m. | PHS- 96 OHS-79 | |
| Tue., 2/15 | V Girls Basketball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 7:00 p.m. | W 65-26 | |
| Tue., 2/15 | JV Girls Basketball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/15 | FR Girls Basketball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/16 | V Boys Ice Hockey | Brien McMahon/Norwalk | Away - Sono Ice House-Main Rink [Directions] | 8:30 p.m. | W 3-1 | |
| Fri., 2/18 | V Boys Basketball | Weston | Away - Weston HS-Gym (New) [Directions] | 7:00 p.m. | W 63-60 | |
| Fri., 2/18 | JV Boys Basketball | Weston | Away - Weston HS-Gym (New) [Directions] | 5:15 p.m. | ||
| Fri., 2/18 | FR Boys Basketball | Weston | Away - Weston HS-Gym (New) [Directions] | 3:45 p.m. | ||
| Fri., 2/18 | V Wrestling | Class L Championship - Day 1 | Away - Wilton | 3:00 p.m. | ||
| Sat., 2/19 | V Boys Ice Hockey | Amity | Away - West Haven HS-Bennett Rink [Directions] | 1:00 p.m. | W 3-1 | |
| Sat., 2/19 | V Boys Indoor Track | State Open | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/19 | V Wrestling | Class L Championship - Day 2 | Away - Wilton | 9:00 a.m. | ||
| Sat., 2/19 | V Girls Basketball | Kolbe Cathedral | Home - Pomperaug HS-Main Gym [Directions] | 1:00 p.m. | ||
| Sat., 2/19 | FR Girls Basketball | Newtown | Home - Pomperaug HS-Main Gym [Directions] | 10:30 a.m. | ||
| Sat., 2/19 | V Girls Indoor Track | State Open | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Mon., 2/21 | V Girls Basketball | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Sister Marion Reilly Auditorium [Directions] | 6:00 p.m. | ||
| Tue., 2/22 | V Boys Basketball | Immaculate | Away - Immaculate HS-Immaculate Gym [Directions] | 7:00 p.m. | L 36-64 | |
| Tue., 2/22 | JV Boys Basketball | Immaculate | Away - Immaculate HS-Immaculate Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/22 | FR Boys Basketball | Immaculate | Away - Immaculate HS-Immaculate Gym [Directions] | 3:45 p.m. | ||
| Tue., 2/22 | V Boys Swimming and Diving | Bunnell-Stratford | Home - Pomperaug HS-PHS Pool [Directions] | 4:30 p.m. | PHS- 97 B/S- 64 | |
| Wed., 2/23 | V Boys Ice Hockey | Westhill/Stamford | Home - Taft School-Mays [Directions] | 7:30 p.m. | W 2-1 | |
| Thu., 2/24 | V Boys Swimming and Diving | Naugatuck | Home - Pomperaug HS-PHS Pool [Directions] | 5:00 p.m. | ||
| Sat., 2/26 | V Wrestling | State Open - Day 1 | Away - Floyd Little Athletic Center | 12:45 p.m. | ||
| Sat., 2/26 | V Girls Basketball | Trumbull (Scrim.) | Home - Pomperaug HS-Main Gym [Directions] | 10:00 a.m. | ||
| Sun., 2/27 | V Wrestling | State Open - Day 2 | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Mon., 2/28 | V Boys Ice Hockey | East Haven Coop | Home - Taft School-Mays [Directions] | 7:30 p.m. | W 4-3(OT) | |
| Tue., 3/1 | V Girls Basketball | Rockville | Home - Pomperaug HS-Main Gym [Directions] | 6:30 p.m. | ||
| Tue., 3/1 | Unified Sports Basketball | Bethel | Home - Pomperaug HS-Main Gym [Directions] | 3:00 p.m. | ||
| Wed., 3/2 | V Boys Swimming and Diving | SWC Diving Championship | Away - New Fairfield HS-Pool | 6:00 p.m. | ||
| Fri., 3/4 | V Boys Swimming and Diving | SWC Boys Swimming Championship | Away - Masuk HS-Pool | 5:00 p.m. | ||
| Fri., 3/4 | V Girls Basketball | Windsor | Home - Pomperaug HS-Main Gym [Directions] | 6:30 p.m. | ||
| Sat., 3/5 | V Boys Swimming and Diving | JV Invitational | Home - Pomperaug HS-PHS Pool [Directions] | 4:00 p.m. | ||
| Mon., 3/7 | V Boys Ice Hockey | South Windsor | Away - South Windsor Arena-Ice Rink [Directions] | 5:30 p.m. | ||
| Tue., 3/8 | V Girls Basketball | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Sister Marion Reilly Auditorium [Directions] | 7:00 p.m. | ||
| Thu., 3/10 | V Boys Swimming and Diving | CIAC Class M Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Fri., 3/11 | V Boys Ice Hockey | Wethersfield | Away - Koeppel Community Sports Center - Trinity College-Albert Creighton Williams '64 Rink [Directions] | 8:00 p.m. | ||
| Sun., 3/13 | V Boys Swimming and Diving | CIAC Class M Qualifying Meet | Away - Cornerstone Pool | 1:00 p.m. | ||
| Wed., 3/16 | V Boys Swimming and Diving | CIAC Class M Swimming Championships | Away - Cornerstone Pool | 6:00 p.m. | ||
| Thu., 3/17 | V Boys Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/19 | V Boys Swimming and Diving | CIAC State Open Swimming Championships | Away - Cornerstone Pool | 3:15 p.m. | ||
| Thu., 3/24 | V Girls Lacrosse | Daniel Hand (Scrim.) | Home - Pomperaug HS-Stadium [Directions] | 6:00 p.m. | ||
| Fri., 3/25 | V Boys Tennis | Nonnewaug (Scrim.) | Away - Nonnewaug HS-Tennis Courts [Directions] | 3:45 p.m. | [Detailed Results] | |
| Fri., 3/25 | V Boys Volleyball | Ridgefield (Scrim.) | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 3/25 | JV Boys Volleyball | Ridgefield (Scrim.) | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 3/26 | V Boys Lacrosse | Watertown (Scrim.) | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 11:00 a.m. | ||
| Sat., 3/26 | V Girls Lacrosse | Cheshire (Scrim.) | Home - Pomperaug HS-Stadium [Directions] | 10:00 a.m. | ||
| Sat., 3/26 | JV Girls Lacrosse | Cheshire (Scrim.) | Home - Pomperaug HS-Stadium [Directions] | 11:30 a.m. | ||
| Mon., 3/28 | V Baseball | Holy Cross (Scrim.) | Home - Pomperaug HS-Baseball Field [Directions] | Canceled | Cancelled | |
| Tue., 3/29 | V Baseball | Watertown (Scrim.) | Away - Deland Field-Deland field [Directions] | Canceled | Cancelled | |
| Tue., 3/29 | V Boys Volleyball | St. Joseph (Scrim.) | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 3/29 | JV Boys Volleyball | St. Joseph (Scrim.) | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 3/29 | V Softball | Naugatuck (Scrim.) | Away - Naugatuck HS-Softball Diamond [Directions] | Postponed | ||
| Wed., 3/30 | V Girls Lacrosse | Jonathan Law (Scrim.) | Away - Jonathan Law HS-Lawmen Stadium [Directions] | 4:30 p.m. | ||
| Wed., 3/30 | V Softball | Seymour (Scrim.) | Away - Seymour HS-Softball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 3/30 | V Girls Tennis | Naugatuck (Scrim.) | Home - Edgewood Bath and Tennis Club [Directions] | 3:00 p.m. | ||
| Thu., 3/31 | V Boys Tennis | Naugatuck (Scrim.) | Away - Naugatuck HS-Tennis Courts [Directions] | 3:00 p.m. | [Detailed Results] | |
| Fri., 4/1 | V Girls Tennis | Nonnewaug (Scrim.) | Home - Edgewood Bath and Tennis Club [Directions] | 3:30 p.m. | ||
| Sat., 4/2 | V Baseball | Oxford | Away - Oxford HS-Baseball Field [Directions] | 12:00 p.m. | L 3-18 | |
| Sat., 4/2 | V Boys Lacrosse | Amity | Away - Amity Regional HS-William Johnson Stadium Field [Directions] | 12:00 p.m. | L 16-10 | |
| Sat., 4/2 | JV Boys Lacrosse | Amity | Away - Amity Regional HS-William Johnson Stadium Field [Directions] | 1:30 p.m. | ||
| Sat., 4/2 | V Boys Volleyball | Wolcott Tech | Away - Oliver Wolcott Technical HS-Gym [Directions] | 11:30 a.m. | W 3-2 | |
| Sat., 4/2 | JV Boys Volleyball | Wolcott Tech | Away - Oliver Wolcott Technical HS-Gym [Directions] | 10:30 a.m. | ||
| Sat., 4/2 | V Girls Lacrosse | Brookfield | Home - Pomperaug HS-Stadium [Directions] | 10:00 a.m. | T 5-5 | |
| Sat., 4/2 | JV Girls Lacrosse | Brookfield | Home - Pomperaug HS-Stadium [Directions] | 12:00 p.m. | W 11-2 | |
| Sat., 4/2 | V Softball | Oxford | Home - Community House Park-Softball Field [Directions] | 11:00 a.m. | L 16-1 | |
| Mon., 4/4 | V Baseball | Abbott Tech | Home - Community House Park-Baseball Field [Directions] | 4:15 p.m. | W 1-0 | |
| Mon., 4/4 | V Boys Lacrosse | Wolcott | Home - Pomperaug HS-Stadium [Directions] | 6:00 p.m. | W 17-2 | |
| Mon., 4/4 | V Girls Lacrosse | Sacred Heart Academy | Away - Sacred Heart Academy-Lacrosse Field [Directions] | 3:45 p.m. | L 14-5 | |
| Mon., 4/4 | JV Girls Lacrosse | Sacred Heart Academy | Away - Sacred Heart Academy-Lacrosse Field [Directions] | 5:15 p.m. | W 7-5 | |
| Mon., 4/4 | V Softball | Trumbull | Home - Community House Park-Softball Field [Directions] | 4:15 p.m. | L 6-5 | |
| Tue., 4/5 | V Boys Volleyball | Shelton | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | W 3-2 | |
| Tue., 4/5 | JV Boys Volleyball | Shelton | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 4/5 | V Girls Golf | Bunnell, Weston | Away - Bunnell HS-Oronoque C.C. [Directions] | 3:00 p.m. | Pomperaug - 249 Weston - 285 Bunnell - 321 | |
| Tue., 4/5 | V Girls Golf | Weston | Away - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | ||
| Tue., 4/5 | JV Softball | Bunnell | Away - Bunnell HS-Bunnell Softball FIeld [Directions] | 5:00 p.m. | ||
| Wed., 4/6 | FR Baseball | Joel Barlow | Home - Pomperaug HS-Baseball Field [Directions] | Canceled | Cancelled | |
| Wed., 4/6 | V Boys Lacrosse | Brookfield | Away - Brookfield HS-BHS Stadium Field [Directions] | 4:00 p.m. | L 2-8 | |
| Wed., 4/6 | JV Boys Lacrosse | Brookfield | Away - Brookfield HS-BHS Back Turf [Directions] | 6:00 p.m. | ||
| Wed., 4/6 | V Boys Volleyball | Xavier | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Wed., 4/6 | JV Boys Volleyball | Xavier | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 4/6 | V Girls Golf | Joel Barlow | Away - Redding Country Club [Directions] | 3:00 p.m. | Joel Barlow - 226 Pomperaug 272 | |
| Thu., 4/7 | V Boys Lacrosse | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 5:45 p.m. | L 6-8 | |
| Thu., 4/7 | JV Boys Lacrosse | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | Canceled | Cancelled | |
| Thu., 4/7 | V Girls Lacrosse | Masuk | Home - Pomperaug HS-Stadium [Directions] | 5:30 p.m. | L 11-6 | |
| Thu., 4/7 | JV Girls Lacrosse | Masuk | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | Cancelled | |
| Fri., 4/8 | V Boys Tennis | Holy Cross | Away - Holy Cross-Tennis Courts [Directions] | 3:30 p.m. | W 5-0 [Detailed Results] | |
| Fri., 4/8 | V Boys Volleyball | Kolbe Cathedral | Away - Kolbe Cathedral HS-Gym [Directions] | 5:45 p.m. | W 3-0 | |
| Fri., 4/8 | JV Boys Volleyball | Kolbe Cathedral | Away - Kolbe Cathedral HS-Gym [Directions] | 4:15 p.m. | ||
| Fri., 4/8 | JV Softball | Seymour | Away - Seymour HS-Bungay Field [Directions] | Canceled | Cancelled | |
| Sat., 4/9 | V Baseball | Wilton | Home - Community House Park-Baseball Field [Directions] | 11:00 a.m. | L 1-13 | |
| Sat., 4/9 | FR Baseball | Wilton | Home - Community House Park-Baseball Field [Directions] | Canceled | Cancelled | |
| Sat., 4/9 | V Boys Lacrosse | Southington | Away - Southington HS-TURF FIELD [Directions] | 12:00 p.m. | L 7-18 | |
| Sat., 4/9 | JV Boys Lacrosse | Southington | Away - Southington HS-TURF FIELD [Directions] | 10:00 a.m. | ||
| Sat., 4/9 | V Girls Lacrosse | Southington | Away - Southington HS-TURF FIELD [Directions] | 2:30 p.m. | L 10-4 | |
| Sat., 4/9 | JV Girls Lacrosse | Southington | Away - Southington HS-TURF FIELD [Directions] | 4:30 p.m. | W 7-5 | |
| Mon., 4/11 | V Baseball | Weston | Home - Community House Park-Baseball Field [Directions] | 4:15 p.m. | W 2-1 | |
| Mon., 4/11 | V Boys Tennis | Brookfield | Home - Pomperaug HS-Edgewood Bath & Tennis Club [Directions] | 3:45 p.m. | L 1-6 [Detailed Results] | |
| Mon., 4/11 | V Softball | Weston | Away - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 4:15 p.m. | W 6-3 | |
| Mon., 4/11 | V Girls Tennis | Brookfield | Away - Brookfield HS-BHS Tennis Courts [Directions] | 3:45 p.m. | W 5-2 | |
| Tue., 4/12 | JV Baseball | Weston | Away - Weston HS-Revson #2 (JV) [Directions] | 4:15 p.m. | L 9-6 | |
| Tue., 4/12 | V Boys Lacrosse | Immaculate | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | W 13-6 | |
| Tue., 4/12 | V Girls Lacrosse | Immaculate | Away - Immaculate HS-Mustang Valley [Directions] | 4:00 p.m. | W 15-5 | |
| Tue., 4/12 | V Softball | Bunnell | Home - Community House Park-Softball Field [Directions] | 4:15 p.m. | L 7-2 | |
| Wed., 4/13 | V Baseball | Bethel | Home - Pomperaug HS-Baseball Field [Directions] | 4:15 p.m. | L 2-10 | |
| Wed., 4/13 | FR Baseball | New Milford | Away - New Milford HS-Baseball Sub Varsity Field - NMHS [Directions] | 4:00 p.m. | L 10-3 | |
| Wed., 4/13 | V Boys Tennis | Weston | Away - Weston HS-WHS Tennis Courts [Directions] | 11:00 a.m. | L 0-7 [Detailed Results] | |
| Wed., 4/13 | V Boys Volleyball | Newtown | Home - Pomperaug HS-Main Gym [Directions] | 11:30 a.m. | L 3-0 | |
| Wed., 4/13 | JV Boys Volleyball | Newtown | Home - Pomperaug HS-Main Gym [Directions] | 10:00 a.m. | ||
| Wed., 4/13 | V Softball | Bethel | Home - Pomperaug HS-Softball Field [Directions] | 4:15 p.m. | W 9-2 | |
| Wed., 4/13 | V Girls Tennis | Maloney | Home - Pomperaug HS-Edgewood Bath & Tennis Club [Directions] | 11:00 a.m. | W 5-2 | |
| Thu., 4/14 | JV Baseball | Bethel | Away - Bethel HS-Hunt Field at Bethel HS [Directions] | 4:00 p.m. | ||
| Thu., 4/14 | JV Softball | Bethel | Away - Bethel HS-Kisling Field [Directions] | Postponed | ||
| Fri., 4/15 | V Baseball | Bunnell | Home - Pomperaug HS-Baseball Field [Directions] | 11:00 a.m. | W 10-5 | |
| Sat., 4/16 | JV Baseball | Bunnell | Away - Bunnell HS-Bunnell Baseball Field [Directions] | 11:00 a.m. | W 14-4 | |
| Mon., 4/18 | V Baseball | Newtown | Home - Pomperaug HS-Baseball Field [Directions] | 4:15 p.m. | L 1-7 | |
| Mon., 4/18 | FR Baseball | Masuk | Home - Community House Park-Baseball Field [Directions] | 4:15 p.m. | L 11-7 | |
| Mon., 4/18 | V Boys Tennis | Bethel | Home - Pomperaug HS-Edgewood Bath & Tennis Club [Directions] | 3:45 p.m. | L 3-4 [Detailed Results] | |
| Mon., 4/18 | V Boys Volleyball | Amity | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | W 3-1 | |
| Mon., 4/18 | JV Boys Volleyball | Amity | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 4/18 | V Girls Golf | Joel Barlow | Home - Pomperaug HS-Pomperaug Golf Course [Directions] | 3:00 p.m. | Joel Barlow 218 Pomperaug 255 | |
| Mon., 4/18 | V Girls Outdoor Track | Brookfield, Notre Dame-Fairfield | Home - Pomperaug HS-Stadium [Directions] | 4:00 p.m. | PHS 92 Brookfield 51 PHS 118 NDHS 2 | |
| Mon., 4/18 | V Softball | Newtown | Home - Pomperaug HS-Softball Field [Directions] | 4:15 p.m. | L 4-0 | |
| Mon., 4/18 | V Girls Tennis | Bethel | Away - Bethel HS-BHS Tennis Courts [Directions] | 3:45 p.m. | L 3-4 | |
| Tue., 4/19 | JV Baseball | Newtown | Away - Fairfield Hills-Baseball Field [Directions] | 3:45 p.m. | W 5-3 | |
| Tue., 4/19 | V Boys Lacrosse | Weston | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | L 20-6 | |
| Tue., 4/19 | JV Boys Lacrosse | Weston | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Tue., 4/19 | V Boys Outdoor Track | Brookfield, Notre Dame-Fairfield | Away - Brookfield HS-BHS Track [Directions] | 4:00 p.m. | PHS 78 - BHS 69 PHS 133 - ND 14 | |
| Tue., 4/19 | V Girls Golf | Weston | Home - Pomperaug HS-Pomperaug Golf Course [Directions] | 3:00 p.m. | Pomperaug 231 Weston 241 | |
| Tue., 4/19 | V Girls Lacrosse | Weston | Away - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | L 12-6 | |
| Tue., 4/19 | JV Girls Lacrosse | Weston | Away - Weston HS-WHS Lower Turf Field [Directions] | 4:15 p.m. | W 9-7 | |
| Tue., 4/19 | JV Softball | Newtown | Away - Newtown HS-NHS Softball Field [Directions] | Postponed | ||
| Wed., 4/20 | V Baseball | New Fairfield | Away - New Fairfield HS-Baseball Field [Directions] | 4:15 p.m. | W 8-7 | |
| Wed., 4/20 | V Boys Tennis | Newtown | Home - Pomperaug HS-Edgewood Bath & Tennis Club [Directions] | 3:45 p.m. | L 2-5 [Detailed Results] | |
| Wed., 4/20 | V Boys Volleyball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 4:15 p.m. | W 3-0 | |
| Wed., 4/20 | JV Boys Volleyball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 5:45 p.m. | ||
| Wed., 4/20 | V Softball | New Fairfield | Away - New Fairfield HS-Softball Field [Directions] | 4:15 p.m. | W 8-4 | |
| Wed., 4/20 | V Girls Tennis | Newtown | Away - Newtown HS [Directions] | 3:45 p.m. | L 3-4 | |
| Thu., 4/21 | JV Baseball | New Fairfield | Home - Pomperaug HS-Baseball Field [Directions] | 4:15 p.m. | W 11-1 | |
| Thu., 4/21 | V Boys Lacrosse | Holy Cross | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | W 13-10 | |
| Thu., 4/21 | V Boys Tennis | Immaculate | Away - Immaculate HS-Rogers Park, Danbury [Directions] | 3:45 p.m. | L 2-5 [Detailed Results] | |
| Thu., 4/21 | V Boys Volleyball | Oxford | Away - Oxford HS-Main Gym [Directions] | 5:30 p.m. | W 3-2 | |
| Thu., 4/21 | JV Boys Volleyball | Oxford | Away - Oxford HS-Main Gym [Directions] | 4:15 p.m. | ||
| Thu., 4/21 | V Softball | Bristol Central | Away - Casey Field-Softball Field [Directions] | 4:15 p.m. | L 16-6 | |
| Thu., 4/21 | V Girls Tennis | Immaculate | Home - Edgewood Bath and Tennis Club [Directions] | 3:45 p.m. | W 6-1 | |
| Fri., 4/22 | V Boys Tennis | Joel Barlow | Away - Joel Barlow HS-Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | |
| Fri., 4/22 | JV Softball | Bethel | Away - Bethel HS-Kisling Field [Directions] | 4:00 p.m. | ||
| Sat., 4/23 | V Baseball | Stratford | Home - Pomperaug HS-Baseball Field [Directions] | 11:00 a.m. | W 7-4 | |
| Sat., 4/23 | FR Baseball | North Branford | Away - North Branford HS-NBHS Baseball Field [Directions] | 2:30 p.m. | L 8-7 | |
| Sat., 4/23 | V Girls Lacrosse | Stratford/Bunnell | Away - Penders Field-Penders Field - Stratford [Directions] | 10:30 a.m. | L 8-7 | |
| Sat., 4/23 | JV Girls Lacrosse | Stratford/Bunnell | Away - Penders Field-Penders Field - Stratford [Directions] | 12:00 p.m. | ||
| Sat., 4/23 | V Softball | Norwalk | Home - Pomperaug HS-Softball Field [Directions] | 11:00 a.m. | L 14-3 | |
| Mon., 4/25 | V Baseball | Kolbe Cathedral | Home - Pomperaug HS-Baseball Field [Directions] | 4:45 p.m. | W 26-1 | |
| Mon., 4/25 | FR Baseball | Newtown | Away - Fairfield Hills-Baseball Field [Directions] | 3:30 p.m. | L 13-3 | |
| Mon., 4/25 | V Boys Lacrosse | New Fairfield | Home - Pomperaug HS-Stadium [Directions] | 5:15 p.m. | L 11-12 (OT) | |
| Mon., 4/25 | JV Boys Lacrosse | New Fairfield | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | ||
| Mon., 4/25 | V Boys Tennis | New Fairfield | Home - Pomperaug HS-Edgewood Bath & Tennis Club [Directions] | 3:45 p.m. | W 4-3 [Detailed Results] | |
| Mon., 4/25 | V Boys Volleyball | Masuk | Home - Pomperaug HS-Main Gym [Directions] | 6:30 p.m. | L 0-3 | |
| Mon., 4/25 | JV Boys Volleyball | Masuk | Home - Pomperaug HS-Main Gym [Directions] | 5:00 p.m. | ||
| Mon., 4/25 | V Girls Outdoor Track | Joel Barlow, Weston | Away - Joel Barlow HS-Joel Barlow HS Stadium [Directions] | 4:00 p.m. | JBHS 79 PHS 71 WHS 101 PHS 49 | |
| Mon., 4/25 | V Softball | Kolbe Cathedral | Home - Pomperaug HS-Softball Field [Directions] | 4:45 p.m. | W 13-1 | |
| Mon., 4/25 | V Girls Tennis | New Fairfield | Away - New Fairfield HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 4/26 | V Boys Outdoor Track | Joel Barlow, Weston | Home - Pomperaug HS-Stadium [Directions] | 4:00 p.m. | PHS 63 vs Weston 87 PHS 79 vs JB 66 Weston 98 vs JB 51 | |
| Tue., 4/26 | V Boys Volleyball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Tue., 4/26 | JV Boys Volleyball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 4:00 p.m. | ||
| Tue., 4/26 | V Girls Lacrosse | New Fairfield | Away - New Fairfield HS-Marty Morgan Field [Directions] | 5:45 p.m. | L 12-6 | |
| Tue., 4/26 | JV Girls Lacrosse | New Fairfield | Away - New Fairfield HS-Marty Morgan Field [Directions] | 4:00 p.m. | T 6-6 | |
| Wed., 4/27 | V Baseball | Immaculate | Away - Immaculate HS-Rogers Park, Danbury [Directions] | 4:15 p.m. | L 2-6 | |
| Wed., 4/27 | FR Baseball | New Fairfield | Home - Pomperaug HS-Baseball Field [Directions] | 4:00 p.m. | W 16-4 | |
| Wed., 4/27 | V Boys Tennis | Joel Barlow | Home - Pomperaug HS-Edgewood Bath & Tennis Club [Directions] | 3:45 p.m. | L 0-7 [Detailed Results] | |
| Wed., 4/27 | V Girls Golf | Brookfield | Home - Pomperaug HS-Pomperaug Golf Course [Directions] | 3:00 p.m. | Pomperaug 223 Brookfield 252 | |
| Wed., 4/27 | V Softball | Immaculate | Away - Immaculate HS-Mustang Valley [Directions] | 4:15 p.m. | L 15-2 | |
| Wed., 4/27 | V Girls Tennis | Joel Barlow | Away - Joel Barlow HS-Tennis Courts [Directions] | 3:45 p.m. | L 2-5 | |
| Thu., 4/28 | V Baseball | Brookfield | Home - Pomperaug HS-Baseball Field [Directions] | 4:15 p.m. | L 10-13 | |
| Thu., 4/28 | V Boys Lacrosse | Joel Barlow | Away - Joel Barlow HS-Field J [Directions] | 4:00 p.m. | L 3-11 | |
| Thu., 4/28 | JV Boys Lacrosse | Joel Barlow | Away - Joel Barlow HS-Field J [Directions] | 5:30 p.m. | ||
| Thu., 4/28 | V Girls Golf | Immaculate, Bunnell | Away - Immaculate HS-Richter Park [Directions] | 3:00 p.m. | Immaculate 203 Pomperaug 238 Bunnell DNP | |
| Thu., 4/28 | V Girls Lacrosse | Joel Barlow | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | L 7-6 | |
| Thu., 4/28 | JV Girls Lacrosse | Joel Barlow | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | L 6-7 | |
| Thu., 4/28 | V Softball | Brookfield | Home - Pomperaug HS-Softball Field [Directions] | 4:15 p.m. | L 13-7 | |
| Thu., 4/28 | JV Softball | Naugatuck | Away - Naugatuck HS-Softball Diamond [Directions] | 5:30 p.m. | ||
| Thu., 4/28 | V Girls Tennis | Weston | Home - Edgewood Bath and Tennis Club [Directions] | 3:45 p.m. | L 0-7 | |
| Fri., 4/29 | V Boys Volleyball | Newtown | Away - Newtown HS-Gym [Directions] | 4:30 p.m. | L 0-3 | |
| Fri., 4/29 | JV Boys Volleyball | Newtown | Away - Newtown HS-Gym [Directions] | 6:00 p.m. | ||
| Fri., 4/29 | JV Softball | Brookfield | Home - Pomperaug HS-Softball Field [Directions] | 3:30 p.m. | ||
| Sat., 4/30 | V Baseball | Seymour | Away - French Park [Directions] | 11:30 a.m. | W 2-1 | |
| Sat., 4/30 | JV Baseball | Brookfield | Away - Brookfield HS-Baseball Field [Directions] | 9:00 a.m. | L 9-2 | |
| Sat., 4/30 | FR Baseball | Bethel | Away - Bethel HS-Hunt Field at Bethel HS [Directions] | 11:00 a.m. | W 9-4 | |
| Sat., 4/30 | V Girls Lacrosse | Amity | Home - Pomperaug HS-Stadium [Directions] | 10:00 a.m. | W 6-5 | |
| Sat., 4/30 | JV Girls Lacrosse | Amity | Home - Pomperaug HS-Stadium [Directions] | 11:30 a.m. | W 11-3 | |
| Sat., 4/30 | JV Girls Tennis | JV Girls Tennis Tournament | Away - Nonnewaug HS-Tennis Courts | 9:00 a.m. | ||
| Mon., 5/2 | V Baseball | Stratford | Away - Penders Field-Penders Field - Stratford [Directions] | 4:15 p.m. | L 1-9 | |
| Mon., 5/2 | FR Baseball | Bethel | Home - Pomperaug HS-Baseball Field [Directions] | 5:15 p.m. | ||
| Mon., 5/2 | V Boys Lacrosse | Bunnell-Stratford | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | W 12-9 | |
| Mon., 5/2 | JV Boys Lacrosse | Bunnell-Stratford | Home - Pomperaug HS-Stadium [Directions] | Canceled | Cancelled | |
| Tue., 5/3 | JV Baseball | Stratford | Home - Community House Park-Baseball Field [Directions] | 4:15 p.m. | W 11-1 | |
| Tue., 5/3 | V Boys Outdoor Track | Immaculate, Newtown, Stratford | Home - Pomperaug HS-Stadium [Directions] | 4:00 p.m. | Pomp 63 vs Newtown 86 Pomp 104 vs Stratford 42 Pomp 114 vs Immaculate 31 Stratford 32 vs Newtown 110 Stratford 80 vs Immaculate 54 Newtown 102 vs Immaculate 41 | |
| Tue., 5/3 | V Girls Golf | Newtown, Immaculate | Away - Newtown Country Club [Directions] | 2:30 p.m. | Newtown 179 Pomperaug 238 | |
| Tue., 5/3 | V Softball | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Park Ave Field [Directions] | 4:00 p.m. | W 11-2 | |
| Tue., 5/3 | V Girls Tennis | Litchfield | Home - Pomperaug HS-Edgewood Bath & Tennis Club [Directions] | 4:00 p.m. | W 5-2 | |
| Wed., 5/4 | V Boys Volleyball | Daniel Hand | Away - Daniel Hand HS-DHHS Gym [Directions] | 5:30 p.m. | W 3-1 | |
| Wed., 5/4 | V Girls Golf | Stratford | Home - Pomperaug HS-Pomperaug Golf Course [Directions] | 3:00 p.m. | Pomperaug - 235 Stratford - 263 | |
| Thu., 5/5 | V Boys Lacrosse | Bethel | Away - Bethel HS-DeSantis Field at Bethel High [Directions] | 5:45 p.m. | W 15-13 | |
| Thu., 5/5 | JV Boys Lacrosse | Bethel | Away - Bethel HS-DeSantis Field at Bethel High [Directions] | 7:30 p.m. | ||
| Thu., 5/5 | V Boys Tennis | Stratford | Away - Flood MS-Flood MS Tennis Courts [Directions] | 3:45 p.m. | W 4-3 [Detailed Results] | |
| Thu., 5/5 | V Boys Volleyball | Brookfield | Home - Pomperaug HS-Main Gym [Directions] | 6:45 p.m. | L 1-3 | |
| Thu., 5/5 | JV Boys Volleyball | Brookfield | Home - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | ||
| Thu., 5/5 | V Girls Lacrosse | Bethel | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | L 8-7 ot | |
| Thu., 5/5 | JV Girls Lacrosse | Bethel | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | W 12-1 | |
| Thu., 5/5 | V Girls Outdoor Track | Newtown, Immaculate, Stratford | Away - Newtown HS-Blue and Gold Stadium [Directions] | 3:30 p.m. | NHS 100 PHS 50 PHS 115 Imma. 35 PHS116 Stratford 34 | |
| Thu., 5/5 | JV Softball | Naugatuck | Away - Naugatuck HS-Softball Diamond [Directions] | 3:45 p.m. | ||
| Thu., 5/5 | V Girls Tennis | Stratford | Home - Edgewood Bath and Tennis Club [Directions] | 3:45 p.m. | W 7-0 | |
| Fri., 5/6 | JV Baseball | Notre Dame-Fairfield | Home - Community House Park-Baseball Field [Directions] | Postponed | ||
| Fri., 5/6 | V Boys Lacrosse | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 4:30 p.m. | W 19-1 | |
| Sat., 5/7 | FR Baseball | Wolcott | Home - Pomperaug HS-Baseball Field [Directions] | Postponed | ||
| Sat., 5/7 | V Boys Volleyball | Norwich Free Academy | Away - Norwich Free Academy-Alumni Gym [Directions] | 12:00 p.m. | W 3-0 | |
| Sat., 5/7 | JV Boys Volleyball | Norwich Free Academy | Away - Norwich Free Academy-Alumni Gym [Directions] | 11:00 a.m. | ||
| Sat., 5/7 | V Girls Lacrosse | Conard | Home - Pomperaug HS-Stadium [Directions] | 10:00 a.m. | W 7-6 | |
| Sat., 5/7 | JV Girls Lacrosse | Conard | Home - Pomperaug HS-Stadium [Directions] | 11:45 a.m. | W 8-4 | |
| Sat., 5/7 | JV Softball | Stratford | Home - Community House Park-Softball Field [Directions] | Postponed | ||
| Mon., 5/9 | V Baseball | New Milford | Home - Pomperaug HS-Baseball Field [Directions] | 4:15 p.m. | L 2-0 | |
| Mon., 5/9 | FR Baseball | Masuk | Away - Wolfe Park-Baseball Field [Directions] | 4:00 p.m. | W 4-1 | |
| Mon., 5/9 | V Boys Volleyball | Oxford | Home - Pomperaug HS-Main Gym [Directions] | 6:15 p.m. | W 3-2 | |
| Mon., 5/9 | JV Boys Volleyball | Oxford | Home - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 5/9 | V Girls Golf | Masuk, Newtown | Home - Pomperaug HS-Pomperaug Golf Course [Directions] | 3:00 p.m. | Newtown - 204 Masuk - 205 Pomperaug - 251 | |
| Mon., 5/9 | V Girls Outdoor Track | Bunnell, Kolbe Cathedral, New Fairfield | Home - Pomperaug HS-Stadium [Directions] | 4:00 p.m. | PHS 94 NFHS 51 PHS 121 Kolbe 14 PHS 99 Bunnell 51 | |
| Mon., 5/9 | V Softball | New Milford | Home - Pomperaug HS-Softball Field [Directions] | 4:15 p.m. | W 5-1 | |
| Mon., 5/9 | V Girls Tennis | Notre Dame-Fairfield | Home - Edgewood Bath and Tennis Club [Directions] | 3:45 p.m. | W 6-1 | |
| Tue., 5/10 | JV Baseball | New Milford | Away - New Milford HS-Baseball Sub Varsity Field - NMHS [Directions] | 4:00 p.m. | L 11-19 | |
| Tue., 5/10 | FR Baseball | New Milford | Home - Pomperaug HS-Baseball Field [Directions] | 4:15 p.m. | L 20-2 | |
| Tue., 5/10 | V Boys Lacrosse | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 7:00 p.m. | W 14-11 | |
| Tue., 5/10 | JV Boys Lacrosse | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 5:30 p.m. | ||
| Tue., 5/10 | V Boys Outdoor Track | Bunnell, Kolbe Cathedral, New Fairfield | Away - Bunnell HS-Bunnell Track [Directions] | 4:00 p.m. | Pomp 116 New Fairfield 35 Pomperaug 96 Bunnell 58 Pomperaug 124 Kolbe 25 | |
| Tue., 5/10 | V Boys Tennis | Bunnell | Away - Bunnell HS [Directions] | 3:45 p.m. | W 5-1 [Detailed Results] | |
| Tue., 5/10 | V Girls Lacrosse | Newtown | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | L 9-8 | |
| Tue., 5/10 | JV Girls Lacrosse | Newtown | Home - Pomperaug HS-Stadium [Directions] | 5:30 p.m. | T 6-6 | |
| Tue., 5/10 | JV Softball | New Milford | Away - New Milford HS-Softball JV Field - NMHS [Directions] | Postponed | ||
| Wed., 5/11 | V Baseball | Masuk | Away - Masuk HS-John Giampaolo Baseball Field @ Masuk HS [Directions] | 4:30 p.m. | L 6-1 | |
| Wed., 5/11 | V Boys Tennis | New Milford | Home - Pomperaug HS-Edgewood Bath & Tennis Club [Directions] | 3:45 p.m. | L 2-5 [Detailed Results] | |
| Wed., 5/11 | V Boys Volleyball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 5:15 p.m. | L 0-3 | |
| Wed., 5/11 | JV Boys Volleyball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 4:00 p.m. | ||
| Wed., 5/11 | V Girls Golf | Bunnell | Home - Pomperaug HS-Pomperaug Golf Course [Directions] | 3:00 p.m. | Pomperaug - 241 Bunnell - 317 | |
| Wed., 5/11 | V Softball | Masuk | Away - Masuk HS-Masuk High School Softball Field [Directions] | 4:15 p.m. | L 13-0 | |
| Wed., 5/11 | V Girls Tennis | New Milford | Away - New Milford HS-Tennis Courts - NMHS [Directions] | 3:45 p.m. | W 7-0 | |
| Thu., 5/12 | V Baseball | Weston | Away - Weston HS-Revson #1 (Varsity) [Directions] | 4:15 p.m. | L 1-11 | |
| Thu., 5/12 | JV Baseball | Masuk | Home - Community House Park-Baseball Field [Directions] | 4:15 p.m. | L 0-5 | |
| Thu., 5/12 | V Boys Lacrosse | Notre Dame-Fairfield | Home - Pomperaug HS-Stadium [Directions] | 6:00 p.m. | W 15-6 | |
| Thu., 5/12 | V Girls Lacrosse | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Park Ave Field [Directions] | 6:00 p.m. | W 14-5 | |
| Thu., 5/12 | JV Girls Lacrosse | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Park Ave Field [Directions] | 4:30 p.m. | W 8-3 | |
| Thu., 5/12 | V Softball | Bristol Eastern | Away - Bristol Eastern HS-Softball Field [Directions] | 5:00 p.m. | L 7-2 | |
| Thu., 5/12 | JV Softball | Oxford | Home - Pomperaug HS-Softball Field [Directions] | 5:30 p.m. | ||
| Fri., 5/13 | FR Baseball | Newtown | Home - Pomperaug HS-Baseball Field [Directions] | 4:15 p.m. | W 3-1 | |
| Fri., 5/13 | V Boys Volleyball | Joel Barlow | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | L 0-3 | |
| Fri., 5/13 | JV Boys Volleyball | Joel Barlow | Home - Pomperaug HS-Main Gym [Directions] | Canceled | Cancelled | |
| Fri., 5/13 | V Softball | Stratford | Away - DeLuca Field-Deluca Field [Directions] | 6:30 p.m. | W 19-14 | |
| Fri., 5/13 | V Girls Tennis | Bunnell | Home - Edgewood Bath and Tennis Club [Directions] | 3:45 p.m. | W 7-0 | |
| Sat., 5/14 | V Baseball | Naugatuck | Away - Naugatuck HS-Raymond Legenza Field [Directions] | 10:00 a.m. | L 0-1 | |
| Sat., 5/14 | JV Baseball | Newtown | Away - Newtown HS-Nighthawk Ball Park [Directions] | 10:00 a.m. | W 5-3 | |
| Sat., 5/14 | FR Baseball | New Fairfield | Away - New Fairfield HS-Baseball Field [Directions] | 10:00 a.m. | L 4-1 | |
| Sat., 5/14 | V Boys Tennis | Watertown | Away - Crestbrook Park-Crestbrook Park Tennis Courts [Directions] | 10:00 a.m. | L 0-5 [Detailed Results] | |
| Sat., 5/14 | V Girls Lacrosse | Simsbury | Away - Holden Field-Turf [Directions] | 5:00 p.m. | L 9-3 | |
| Sat., 5/14 | V Softball | Granby Memorial | Away - Granby Memorial HS-Softball Diamond [Directions] | 10:30 a.m. | W 12-4 | |
| Sat., 5/14 | JV Softball | Danbury | Home - Pomperaug HS-Softball Field [Directions] | 10:00 a.m. | ||
| Sat., 5/14 | JV Softball | Danbury | Home - Pomperaug HS-Softball Field [Directions] | Canceled | Cancelled | |
| Tue., 5/17 | V Baseball | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Fabbri Field [Directions] | 4:00 p.m. | W 7-3 | |
| Tue., 5/17 | JV Baseball | Joel Barlow | Away - Joel Barlow HS-Baseball Field [Directions] | 4:15 p.m. | L 6-0 | |
| Tue., 5/17 | V Boys Lacrosse | New Milford | Away - New Milford HS-North Turf Field - NMHS [Directions] | 7:15 p.m. | L 12-5 | |
| Tue., 5/17 | JV Boys Lacrosse | New Milford | Away - New Milford HS-North Turf Field - NMHS [Directions] | 5:45 p.m. | ||
| Tue., 5/17 | V Boys Outdoor Track | Bethel, Masuk, New Milford | Away - Bethel HS-BHS track [Directions] | 4:00 p.m. | ||
| Tue., 5/17 | V Boys Tennis | Masuk | Away - Wolfe Park-Tennis Courts [Directions] | 3:45 p.m. | L 1-6 [Detailed Results] | |
| Tue., 5/17 | V Girls Lacrosse | New Milford | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | W 18-2 | |
| Tue., 5/17 | JV Girls Lacrosse | New Milford | Home - Pomperaug HS-Stadium [Directions] | 5:30 p.m. | W 13-2 | |
| Wed., 5/18 | V Baseball | Joel Barlow | Home - Pomperaug HS-Baseball Field [Directions] | 4:15 p.m. | L 0-11 | |
| Wed., 5/18 | JV Baseball | Weston | Home - Community House Park-Baseball Field [Directions] | 4:15 p.m. | W 10-0 | |
| Wed., 5/18 | V Boys Volleyball | Wolcott Tech | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | W 3-2 | |
| Wed., 5/18 | JV Boys Volleyball | Wolcott Tech | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 5/18 | V Girls Outdoor Track | New Milford, Bethel, Masuk | Away - New Milford HS-Joe Wiser Stadium - NMHS [Directions] | 3:30 p.m. | PHS 90.5 Masuk 59.5 PHS 80 NMHS 67 Bethel 94 PHS 55 | |
| Wed., 5/18 | V Softball | Joel Barlow | Home - Pomperaug HS-Softball Field [Directions] | 4:15 p.m. | W 22-10 | |
| Wed., 5/18 | V Girls Tennis | Masuk | Home - Edgewood Bath and Tennis Club [Directions] | 3:45 p.m. | W 4-3 | |
| Thu., 5/19 | FR Baseball | North Branford | Home - Community House Park-Baseball Field [Directions] | 4:15 p.m. | L 5-0 | |
| Thu., 5/19 | V Boys Lacrosse | New Fairfield | Away - New Fairfield HS-Marty Morgan Field [Directions] | 7:00 p.m. | ||
| Thu., 5/19 | V Boys Tennis | SWC Boys Tennis Championships | Away - Rogers Park (Danbury, CT)-Tennis Courts | 12:00 p.m. | ||
| Thu., 5/19 | V Softball | New Canaan | Home - Community House Park-Softball Field [Directions] | 4:30 p.m. | L 9-5 | |
| Thu., 5/19 | V Girls Tennis | SWC Girls Tennis Championships | Away - Joel Barlow HS-Tennis Courts | 2:00 p.m. | ||
| Fri., 5/20 | V Boys Outdoor Track | SWC Freshmen Invite | Away - Bethel HS-BHS track | 4:00 p.m. | ||
| Fri., 5/20 | V Boys Volleyball | Kolbe Cathedral | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 5/20 | JV Boys Volleyball | Kolbe Cathedral | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 5/20 | V Girls Outdoor Track | SWC Freshmen Invite | Away - Bethel HS-BHS track | 4:00 p.m. | ||
| Sat., 5/21 | V Softball | Immaculate | Away - Immaculate HS-Mustang Valley [Directions] | 10:00 a.m. | ||
| Sat., 5/21 | V Softball | Immaculate | Away - Immaculate HS-Softball Diamond [Directions] | 10:00 a.m. | L 10-5 | |
| Mon., 5/23 | V Boys Volleyball | Cheshire | Away - Cheshire HS-Gym West [Directions] | 6:00 p.m. | L 2-3 | |
| Mon., 5/23 | JV Boys Volleyball | Cheshire | Away - Cheshire HS-Gym West [Directions] | 5:00 p.m. | ||
| Mon., 5/23 | V Girls Golf | Brookfield | Away - Sunset Hill Golf Course [Directions] | 3:00 p.m. | Pomperaug - 220 Brookfield - 237 | |
| Mon., 5/23 | V Girls Tennis | SWC Championship Tournament | Away - Joel Barlow HS-Tennis Courts | 2:00 p.m. | ||
| Tue., 5/24 | V Boys Outdoor Track | Bunnell, Bethel, Brookfield, Immaculate, Joel Barlow, Kolbe Cathedral, Masuk, New Fairfield, New Milford, Newtown, Notre Dame-Fairfield, Stratford, Weston | Away - New Milford HS-Track | 3:00 p.m. | ||
| Tue., 5/24 | V Girls Golf | Masuk | Away - Whitney Farms Golf Course [Directions] | 3:00 p.m. | Pomperaug - 235 Masuk - 199 | |
| Tue., 5/24 | V Girls Outdoor Track | Bunnell, Bethel, Brookfield, Immaculate, Joel Barlow, Kolbe Cathedral, Masuk, New Fairfield, New Milford, Newtown, Notre Dame-Fairfield, Stratford, Weston | Away - New Milford HS-Track | 3:00 p.m. | ||
| Wed., 5/25 | V Boys Volleyball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Thu., 5/26 | V Softball | Holy Cross (Scrim.) | Home - Pomperaug HS-Softball Field [Directions] | 3:45 p.m. | ||
| Sat., 5/28 | V Boys Lacrosse | Fitch | Away - Groton MS-Groton Middle School-Turf Feld [Directions] | 12:30 p.m. | ||
| Tue., 5/31 | V Baseball | RHAM | Away - RHAM HS-Baseball Field [Directions] | 4:00 p.m. | ||
| Tue., 5/31 | V Girls Golf | SWC Girls Golf Championship Tournament @ Fairchild Wheeler Golf Course | Away - Fairchild Wheeler Golf Course | 8:00 a.m. | ||
| Tue., 5/31 | V Softball | St. Joseph | Away - St. Joseph HS-Softball Diamond [Directions] | 4:00 p.m. | L 3-0 | |
| Tue., 5/31 | V Girls Tennis | North Haven | Away - North Haven Athletic Complex-Tennis Courts [Directions] | 3:45 p.m. | ||
| Wed., 6/1 | V Baseball | Daniel Hand | Away - Daniel Hand HS-Polson Baseball Field /DHHS Campus [Directions] | 3:30 p.m. | ||
| Wed., 6/1 | V Boys Lacrosse | Wilton | Away - Wilton HS-Veterans Memorial Stadium [Directions] | 4:30 p.m. | ||
| Wed., 6/1 | V Boys Outdoor Track | CIAC Class L Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Wed., 6/1 | V Boys Volleyball | Newington | Away - Newington HS-Gym [Directions] | 5:00 p.m. | L 1-3 | |
| Wed., 6/1 | V Girls Outdoor Track | CIAC Class L Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Mon., 6/6 | V Boys Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/6 | V Boys Tennis | CIAC Individual Invitational - Opening Round, Singles and Doubles | Away - Wesleyan | 10:00 a.m. | ||
| Mon., 6/6 | V Girls Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/6 | V Girls Tennis | CIAC Individual Invitational - Opening Round, Singles and Doubles | Away - Wesleyan | 10:00 a.m. | ||
| Tue., 6/7 | V Boys Tennis | CIAC Individual Invitational - Round of 16 | Away - Wesleyan | 9:00 a.m. | ||
| Tue., 6/7 | V Girls Tennis | CIAC Individual Invitational - Round of 16 | Away - Wesleyan | 9:00 a.m. | ||
| Wed., 6/8 | V Boys Tennis | CIAC Individual Invitational - Quarterfinals | Away - Wesleyan | 3:00 p.m. | ||
| Wed., 6/8 | V Girls Golf | CIAC Division II Championship | Away - Timberlin GC | 8:30 a.m. | ||
| Wed., 6/8 | V Girls Tennis | CIAC Individual Invitational - Quarterfinals | Away - Wesleyan | 3:00 p.m. | ||
| Thu., 6/9 | V Boys Tennis | CIAC Individual Invitational - Semifinals | Away - Wesleyan | 3:00 p.m. | ||
| Thu., 6/9 | V Girls Tennis | CIAC Individual Invitational - Semifinals | Away - Wesleyan | 3:00 p.m. | ||
| Fri., 6/10 | V Boys Tennis | CIAC Individual Invitational - Finals | Away - Wesleyan | 3:00 p.m. | ||
| Fri., 6/10 | V Girls Tennis | CIAC Individual Invitational - Finals | Away - Wesleyan | 3:00 p.m. | ||
| Sat., 6/11 | V Girls Golf | CIAC Girls State Open | Away - Black Hall Club | 1:00 p.m. | ||
| Mon., 6/13 | V Boys Outdoor Track | CIAC Boys Hammer Throw Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Mon., 6/13 | V Girls Outdoor Track | CIAC Girls Hammer Throw Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Tue., 6/14 | V Boys Outdoor Track | CIAC Decathlon Championship Day 1 | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 6/14 | V Girls Outdoor Track | CIAC Heptathlon Championship Day 1 | Away - Willow Brook Park | 10:30 a.m. | ||
| Tue., 6/14 | V Girls Outdoor Track | CIAC Girls Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/15 | V Boys Outdoor Track | CIAC Decathlon Championship Day 2 | Away - Willow Brook Park | 10:00 a.m. | ||
| Wed., 6/15 | V Boys Outdoor Track | CIAC Boys Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/15 | V Girls Outdoor Track | CIAC Heptathlon Championship Day 2 | Away - Willow Brook Park | 10:00 a.m. | ||