| Pomperaug 2022-23 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 647 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Tue., 8/23 | V Boys Golf | Immaculate | Away - Immaculate HS-Richter Park [Directions] | 3:00 p.m. | Pomperaug 170 Immaculate 175 | |
| Wed., 8/24 | V Boys Golf | Weston | Home - Pomperaug HS-Highfield Country Club [Directions] | 2:00 p.m. | Pomperaug 165 Weston 189 | |
| Mon., 8/29 | V Boys Golf | Stratford | Home - Pomperaug HS-Highfield Country Club [Directions] | 3:00 p.m. | Pomperaug 160 Stratford 234 | |
| Wed., 9/7 | V Boys Golf | New Fairfield | Home - Pomperaug HS-Highfield Country Club [Directions] | 3:00 p.m. | Pomperaug 157 New Fairfield 196 | |
| Thu., 9/8 | V Boys Golf | Bethel | Away - Bethel HS-Connecticut Country Club [Directions] | 3:00 p.m. | Pomperaug 168 Bethel 186 | |
| Thu., 9/8 | V Boys Soccer | Abbott Tech | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | W 5-0 | |
| Thu., 9/8 | JV Boys Soccer | Abbott Tech | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Thu., 9/8 | V Field Hockey | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 7:00 p.m. | T 2-2 | |
| Thu., 9/8 | JV Field Hockey | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 5:30 p.m. | ||
| Thu., 9/8 | V Girls Volleyball | Nonnewaug | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | L 1-3 | |
| Thu., 9/8 | JV Girls Volleyball | Nonnewaug | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 9/8 | FR Girls Volleyball | Nonnewaug | Home - Pomperaug HS-Auxiliary Gym [Directions] | Canceled | Cancelled | |
| Fri., 9/9 | V Football | Fairfield Warde | Home - Pomperaug HS-Stadium [Directions] | 6:30 p.m. | L 15-29 | |
| Sat., 9/10 | V Girls Soccer | Mercy | Home - Pomperaug HS-Stadium [Directions] | 12:00 p.m. | L 0-2 | |
| Sat., 9/10 | JV Girls Soccer | Mercy | Home - Pomperaug HS-Stadium [Directions] | 10:15 a.m. | ||
| Sat., 9/10 | V Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 11:30 a.m. | L 0-3 | |
| Sat., 9/10 | JV Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 10:00 a.m. | ||
| Mon., 9/12 | V Boys Golf | Notre Dame-Fairfield | Away - Fairchild Wheeler Golf Course [Directions] | 3:00 p.m. | Pomperaug 161 Notre Dame 191 | |
| Mon., 9/12 | V Field Hockey | Farmington | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | L 1-2 | |
| Mon., 9/12 | JV Field Hockey | Farmington | Home - Pomperaug HS-Stadium [Directions] | 5:30 p.m. | ||
| Mon., 9/12 | V Girls Volleyball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 6:00 p.m. | W 3-2 | |
| Mon., 9/12 | JV Girls Volleyball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 4:45 p.m. | ||
| Mon., 9/12 | FR Girls Volleyball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 3:15 p.m. | ||
| Tue., 9/13 | V Boys Soccer | New Milford | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | W 3-1 | |
| Tue., 9/13 | JV Boys Soccer | New Milford | Home - Pomperaug HS-Stadium [Directions] | Postponed | ||
| Tue., 9/13 | V Girls Soccer | New Milford | Away - New Milford HS-Joe Wiser Stadium - NMHS [Directions] | 6:15 p.m. | W 3-0 | |
| Tue., 9/13 | JV Girls Soccer | New Milford | Away - New Milford HS-Joe Wiser Stadium - NMHS [Directions] | Postponed | ||
| Tue., 9/13 | V Girls Swimming and Diving | Joel Barlow | Home - Pomperaug HS-PHS Pool [Directions] | 4:00 p.m. | 94-63 Pomperaug | |
| Tue., 9/13 | FR Girls Volleyball | Bethel | Home - Pomperaug HS-Auxiliary Gym [Directions] | 4:00 p.m. | ||
| Wed., 9/14 | V Boys Cross Country | Immaculate, Notre Dame-Fairfield | Home - Pomperaug HS-Cross Country Course [Directions] | 5:00 p.m. | PHS 15 IHS 48 PHS 15 NDHS 44 | |
| Wed., 9/14 | FR Boys Soccer | Bethel | Away - Bethel HS-Rockwell Field [Directions] | 4:00 p.m. | ||
| Wed., 9/14 | V Girls Cross Country | Immaculate, Notre Dame-Fairfield | Home - Pomperaug HS-Cross Country Course [Directions] | 4:30 p.m. | PHS 15 IHS 50 PHS 15 NDHS 50 | |
| Wed., 9/14 | V Girls Volleyball | Seymour | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | L 0-3 | |
| Wed., 9/14 | JV Girls Volleyball | Seymour | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 9/15 | FR Football | New Fairfield | Away - New Fairfield HS-Stadium Field [Directions] | 5:15 p.m. | ||
| Thu., 9/15 | V Boys Golf | Bunnell | Away - Bunnell HS-Oronoque C.C. [Directions] | 3:00 p.m. | Pomperaug 170 | |
| Thu., 9/15 | V Boys Soccer | Brookfield | Away - Brookfield HS-BHS Stadium Field [Directions] | 7:00 p.m. | T 0-0 | |
| Thu., 9/15 | JV Boys Soccer | Brookfield | Away - Brookfield HS-BHS Stadium Field [Directions] | 5:00 p.m. | ||
| Thu., 9/15 | V Girls Soccer | Brookfield | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | T 0-0 | |
| Thu., 9/15 | JV Girls Soccer | Brookfield | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Fri., 9/16 | V Football | New Fairfield | Home - Pomperaug HS-Stadium [Directions] | 6:30 p.m. | L 14-34 | |
| Fri., 9/16 | FR Boys Soccer | New Milford | Away - New Milford HS-Middle Soccer Field - NMHS [Directions] | 4:00 p.m. | ||
| Fri., 9/16 | V Girls Volleyball | Masuk | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Fri., 9/16 | JV Girls Volleyball | Masuk | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/16 | FR Girls Volleyball | Masuk | Home - Pomperaug HS-Auxiliary Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/17 | V Boys Cross Country | Wilton | Away - Allen's Meadow-XC Course [Directions] | TBA | ||
| Sat., 9/17 | V Boys Soccer | Woodland | Home - Pomperaug HS-Stadium [Directions] | 12:00 p.m. | W 4-1 | |
| Sat., 9/17 | JV Boys Soccer | Woodland | Home - Pomperaug HS-Stadium [Directions] | Canceled | Cancelled | |
| Sat., 9/17 | V Girls Cross Country | Wilton | Away - Allen's Meadow-XC Course [Directions] | TBA | ||
| Sat., 9/17 | V Field Hockey | Granby Memorial | Away - Granby Memorial HS-Stadium Field [Directions] | 1:00 p.m. | L 2-1 | |
| Sat., 9/17 | JV Field Hockey | Granby Memorial | Away - Granby Memorial HS-Stadium Field [Directions] | 2:30 p.m. | ||
| Sat., 9/17 | V Girls Soccer | Woodland | Away - Woodland HS-Woodland Soccer Field [Directions] | 11:00 a.m. | W 1-0 | |
| Mon., 9/19 | V Boys Golf | Weston | Away - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | Pomperaug 171-189 | |
| Mon., 9/19 | V Field Hockey | Joel Barlow | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | W 2-0 | |
| Mon., 9/19 | JV Field Hockey | Joel Barlow | Home - Pomperaug HS-Stadium [Directions] | 5:30 p.m. | ||
| Mon., 9/19 | JV Girls Soccer | Woodland | Away - Woodland HS-Woodland Soccer Field [Directions] | 4:30 p.m. | ||
| Mon., 9/19 | V Girls Volleyball | Woodland | Away - Woodland HS-Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Mon., 9/19 | JV Girls Volleyball | Woodland | Away - Woodland HS-Gym [Directions] | 4:30 p.m. | ||
| Tue., 9/20 | V Boys Cross Country | Brookfield, Masuk, Stratford | Away - Brookfield HS-BHS Track [Directions] | 5:00 p.m. | PHS 23 Brookfield 36 PHS 20 Stratford 41 PHS 15 Masuk 50 | |
| Tue., 9/20 | V Boys Soccer | Masuk | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | T 1-1 | |
| Tue., 9/20 | JV Boys Soccer | Masuk | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Tue., 9/20 | V Girls Cross Country | Brookfield, Masuk, Stratford | Away - Brookfield HS-BHS Track [Directions] | 4:30 p.m. | PHS 15 Stratford 50 PHS 23 Brookfield 35 PHS 16 Masuk 47 | |
| Tue., 9/20 | V Girls Soccer | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 7:00 p.m. | T 0-0 | |
| Tue., 9/20 | JV Girls Soccer | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 5:00 p.m. | ||
| Tue., 9/20 | V Girls Swimming and Diving | Masuk | Home - Pomperaug HS-PHS Pool [Directions] | 5:30 p.m. | 92/84 Pomperaug | |
| Tue., 9/20 | FR Girls Volleyball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 4:00 p.m. | ||
| Wed., 9/21 | V Boys Golf | Immaculate | Home - Pomperaug HS-Highfield Country Club [Directions] | 3:00 p.m. | Pomperaug 161 Immaculate 171 | |
| Wed., 9/21 | FR Boys Soccer | Newtown | Home - Pomperaug HS-PHS Soccer Field [Directions] | 3:30 p.m. | ||
| Wed., 9/21 | V Field Hockey | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 6:45 p.m. | L 2-0 | |
| Wed., 9/21 | JV Field Hockey | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 5:15 p.m. | ||
| Wed., 9/21 | V Girls Volleyball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Wed., 9/21 | JV Girls Volleyball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 4:30 p.m. | ||
| Thu., 9/22 | V Boys Soccer | Joel Barlow | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | W 4-1 | |
| Thu., 9/22 | JV Boys Soccer | Joel Barlow | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Fri., 9/23 | V Football | Farmington | Home - Pomperaug HS-Stadium [Directions] | 6:30 p.m. | L 21-39 | |
| Fri., 9/23 | V Girls Volleyball | Weston | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Fri., 9/23 | JV Girls Volleyball | Weston | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/23 | FR Girls Volleyball | Weston | Home - Pomperaug HS-Auxiliary Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/24 | FR Football | Farmington | Home - Pomperaug HS-Stadium [Directions] | 10:00 a.m. | ||
| Sat., 9/24 | FR Boys Soccer | Masuk | Home - Pomperaug HS-PHS Soccer Field [Directions] | 10:30 a.m. | ||
| Sat., 9/24 | FR Girls Volleyball | Danbury | Away - Danbury HS-New Gym [Directions] | 11:00 a.m. | ||
| Tue., 9/27 | V Boys Golf | New Milford | Home - Pomperaug HS-Highfield Country Club [Directions] | 3:00 p.m. | Pomperaug 164 New Milford 171 | |
| Tue., 9/27 | V Boys Soccer | Kolbe Cathedral | Away - Veterans Memorial Park CT [Directions] | 4:15 p.m. | W 4-0 | |
| Tue., 9/27 | V Girls Soccer | Kolbe Cathedral | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | W 8-0 | |
| Wed., 9/28 | V Boys Cross Country | Joel Barlow, Kolbe Cathedral | Away - Joel Barlow HS-Cross Country Course [Directions] | 5:00 p.m. | JBHS 24 PHS 33 PHS 20 Kolbe 43 | |
| Wed., 9/28 | FR Football | Newtown | Home - Pomperaug HS-Stadium [Directions] | 3:30 p.m. | ||
| Wed., 9/28 | V Boys Golf | Joel Barlow | Home - Pomperaug HS-Highfield Country Club [Directions] | 3:00 p.m. | Pomperaug 158 Barlow184 | |
| Wed., 9/28 | V Girls Cross Country | Joel Barlow, Kolbe Cathedral | Away - Joel Barlow HS-Cross Country Course [Directions] | 4:30 p.m. | PHS 17 Joel Barlow 46 PHS 15 Kolbe 50 | |
| Wed., 9/28 | V Field Hockey | New Fairfield | Home - Pomperaug HS-Stadium [Directions] | 5:45 p.m. | W 1-0 | |
| Wed., 9/28 | JV Field Hockey | New Fairfield | Home - Pomperaug HS-Stadium [Directions] | 7:15 p.m. | ||
| Wed., 9/28 | V Girls Volleyball | Immaculate | Home - Pomperaug HS-Main Gym [Directions] | 6:30 p.m. | W 3-2 | |
| Wed., 9/28 | JV Girls Volleyball | Immaculate | Home - Pomperaug HS-Main Gym [Directions] | 5:00 p.m. | ||
| Wed., 9/28 | FR Girls Volleyball | Immaculate | Home - Pomperaug HS-Auxiliary Gym [Directions] | 5:00 p.m. | ||
| Thu., 9/29 | JV Boys Golf | vs Bethel High School at Connecticut Country Club-Easton, CT | Away - Not Listed | 3:00 p.m. | ||
| Thu., 9/29 | V Boys Soccer | Weston | Away - Weston HS-WHS Stadium Field [Directions] | 6:00 p.m. | L 1-0 | |
| Thu., 9/29 | JV Boys Soccer | Weston | Away - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 9/29 | V Girls Soccer | Weston | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | W 1-0 | |
| Thu., 9/29 | JV Girls Soccer | Weston | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Thu., 9/29 | V Girls Swimming and Diving | Bunnell | Home - Pomperaug HS-PHS Pool [Directions] | 5:30 p.m. | 90/71 Pomperaug | |
| Fri., 9/30 | V Football | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 7:00 p.m. | L 0-49 | |
| Fri., 9/30 | V Field Hockey | New Milford | Away - New Milford HS-North Turf Field - NMHS [Directions] | 5:30 p.m. | W 1-0 | |
| Fri., 9/30 | JV Field Hockey | New Milford | Away - New Milford HS-North Turf Field - NMHS [Directions] | 4:00 p.m. | ||
| Fri., 9/30 | V Girls Volleyball | Newtown | Away - Newtown HS-Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Fri., 9/30 | JV Girls Volleyball | Newtown | Away - Newtown HS-Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/30 | FR Girls Volleyball | Newtown | Home - Pomperaug HS-Auxiliary Gym [Directions] | 5:00 p.m. | ||
| Sat., 10/1 | V Boys Cross Country | Brewster Invitational | Away - Not Listed | TBA | ||
| Sat., 10/1 | V Girls Cross Country | Brewster Invitational | Away - TBA | TBA | ||
| Mon., 10/3 | V Boys Cross Country | Bunnell, New Fairfield, Weston | Home - Pomperaug HS-Cross Country Course [Directions] | 5:00 p.m. | PHS 20 Weston 43 PHS 21 NFHS 40 PHS 15 Bunnell 50 NFHS 25 Weston 32 Weston 27 Bunnell 28 NFHS 20 Bunnell 39 | |
| Mon., 10/3 | V Boys Golf | Brookfield | Away - Sunset Hill Golf Course [Directions] | 3:00 p.m. | Pomperaug 174 Brookfield 164 | |
| Mon., 10/3 | JV Boys Golf | JV Invitational at Stanley Golf Course- New Britain | Away - Not Listed | 12:00 p.m. | ||
| Mon., 10/3 | V Girls Cross Country | Bunnell, New Fairfield, Weston | Home - Pomperaug HS-Cross Country Course [Directions] | 4:30 p.m. | PHS 15 Weston 48 PHS 15 Bunnell 50 NFHS 23 PHS 32 NFHS 15 Weston 40 NFHS 15 Bunnell 42 Bunnell 22 Weston 33 | |
| Mon., 10/3 | V Field Hockey | Newtown | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | W 1-0(OT) | |
| Mon., 10/3 | JV Field Hockey | Newtown | Home - Pomperaug HS-Stadium [Directions] | 5:30 p.m. | ||
| Mon., 10/3 | V Girls Volleyball | Kolbe Cathedral | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Mon., 10/3 | JV Girls Volleyball | Kolbe Cathedral | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 10/3 | FR Girls Volleyball | Weston | Away - Weston HS-Gym (Old) [Directions] | 4:00 p.m. | ||
| Tue., 10/4 | V Boys Golf | Avon Invitational | Away - Hop Meadow Country Club | 10:30 a.m. | Pomperaug 168 | |
| Tue., 10/4 | V Girls Soccer | Bethel | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | T 0-0 | |
| Tue., 10/4 | JV Girls Soccer | Bethel | Home - Pomperaug HS-Stadium [Directions] | 5:30 p.m. | ||
| Tue., 10/4 | V Girls Swimming and Diving | Brookfield | Home - Pomperaug HS-PHS Pool [Directions] | 4:30 p.m. | 94/84 Pomperaug | |
| Thu., 10/6 | V Boys Golf | CHAPPA- at Long Shore Country Club- Westport | Away - Not Listed | TBA | ||
| Thu., 10/6 | V Boys Soccer | Stratford | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | W 2-0 | |
| Thu., 10/6 | JV Boys Soccer | Stratford | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Thu., 10/6 | V Girls Soccer | Stratford | Away - Penders Field-Penders Field - Stratford [Directions] | 7:00 p.m. | W 2-0 | |
| Thu., 10/6 | JV Girls Soccer | Stratford | Away - Penders Field-Penders Field - Stratford [Directions] | 5:00 p.m. | ||
| Thu., 10/6 | FR Girls Volleyball | Brookfield | Home - Pomperaug HS-Auxiliary Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/7 | FR Boys Soccer | Naugatuck | Home - Pomperaug HS-PHS Soccer Field [Directions] | 3:30 p.m. | ||
| Fri., 10/7 | V Field Hockey | Bethel | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | W 4-0 | |
| Fri., 10/7 | JV Field Hockey | Bethel | Home - Pomperaug HS-Stadium [Directions] | 5:30 p.m. | ||
| Fri., 10/7 | V Girls Volleyball | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Sister Marion Reilly Auditorium [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 10/7 | JV Girls Volleyball | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Sister Marion Reilly Auditorium [Directions] | 4:30 p.m. | ||
| Sat., 10/8 | FR Boys Soccer | Masuk | Away - Masuk HS-Masuk High School Middle Field [Directions] | 10:30 a.m. | ||
| Sat., 10/8 | FR Girls Volleyball | Newtown | Home - Pomperaug HS-Main Gym [Directions] | 10:30 a.m. | ||
| Mon., 10/10 | V Boys Soccer | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 3:00 p.m. | W 5-0 | |
| Mon., 10/10 | V Field Hockey | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 10:00 a.m. | W 1-0 | |
| Mon., 10/10 | V Girls Soccer | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 1:00 p.m. | T 0-0 | |
| Tue., 10/11 | V Boys Cross Country | Bethel, New Milford, Newtown | Away - Bethel HS-BHS track [Directions] | 5:00 p.m. | NMHS 15 PHS 45 Bethel 26 PHS 29 PHS 28 Newtoqn 28 , NHS wins on tiebreaker | |
| Tue., 10/11 | V Boys Golf | Newtown | Away - Rock Ridge Country Club [Directions] | 3:00 p.m. | pomp 165 newtown 183 | |
| Tue., 10/11 | V Boys Soccer | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Park Ave Field [Directions] | 4:00 p.m. | T 1-1 | |
| Tue., 10/11 | V Girls Cross Country | Bethel, New Milford, Newtown | Away - Bethel HS-BHS track [Directions] | 4:30 p.m. | NMHS 19 PHS 36 PHS 26 Newtown 29 PHS 23 Bethel 38 | |
| Tue., 10/11 | V Girls Soccer | Notre Dame-Fairfield | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | L 0-1 | |
| Tue., 10/11 | JV Girls Soccer | Woodland | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Tue., 10/11 | V Girls Swimming and Diving | Stratford | Away - Flood MS-Flood MS Pool [Directions] | 4:30 p.m. | 94/71 Pomperaug | |
| Tue., 10/11 | V Girls Volleyball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 6:30 p.m. | W 3-1 | |
| Tue., 10/11 | JV Girls Volleyball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 5:00 p.m. | ||
| Tue., 10/11 | FR Girls Volleyball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 3:45 p.m. | ||
| Wed., 10/12 | FR Football | Stratford | Away - Penders Field-Penders Field - Stratford [Directions] | 4:00 p.m. | ||
| Wed., 10/12 | V Boys Golf | Masuk | Home - Pomperaug HS-Highfield Country Club [Directions] | 3:00 p.m. | pomp 167 masuk 183 | |
| Wed., 10/12 | FR Boys Soccer | New Milford | Home - Pomperaug HS-PHS Soccer Field [Directions] | 4:00 p.m. | ||
| Wed., 10/12 | V Field Hockey | Weston | Away - Weston HS-WHS Lower Turf Field [Directions] | 5:30 p.m. | W 1-0 | |
| Wed., 10/12 | JV Field Hockey | Weston | Away - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 10/13 | V Boys Soccer | Bunnell | Home - Pomperaug HS-Stadium [Directions] | 4:00 p.m. | W 5-0 | |
| Thu., 10/13 | JV Boys Soccer | Bunnell | Home - Pomperaug HS-Stadium [Directions] | Canceled | Cancelled | |
| Thu., 10/13 | V Girls Soccer | Bunnell | Away - Bunnell HS-Mastroni Field [Directions] | 4:00 p.m. | W 5-2 | |
| Thu., 10/13 | JV Girls Soccer | Bunnell | Away - Bunnell HS-Mastroni Field [Directions] | Canceled | Cancelled | |
| Thu., 10/13 | V Girls Volleyball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Thu., 10/13 | JV Girls Volleyball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/14 | V Football | Stratford | Home - Pomperaug HS-Stadium [Directions] | 6:30 p.m. | W 20-0 | |
| Fri., 10/14 | V Field Hockey | Southington | Away - Southington HS-3 TURF FIELD [Directions] | 6:00 p.m. | L 0-2 | |
| Fri., 10/14 | JV Field Hockey | Southington | Away - Southington HS-2 Field Hockey/Boys Lacrosse [Directions] | 4:30 p.m. | ||
| Fri., 10/14 | V Girls Swimming and Diving | Weston | Home - Pomperaug HS-PHS Pool [Directions] | 4:30 p.m. | 88/96 Weston | |
| Sat., 10/15 | V Field Hockey | New Milford | Home - Pomperaug HS-Stadium [Directions] | 10:30 a.m. | L 0-2 | |
| Sat., 10/15 | JV Field Hockey | New Milford | Home - Pomperaug HS-Stadium [Directions] | 12:00 p.m. | ||
| Sat., 10/15 | V Girls Soccer | Joel Barlow | Away - Joel Barlow HS-Field I (Stadium) [Directions] | 10:00 a.m. | W 1-0 | |
| Sat., 10/15 | JV Girls Soccer | Joel Barlow | Away - Joel Barlow HS-Field E (Softball) [Directions] | 10:00 a.m. | ||
| Sat., 10/15 | V Girls Volleyball | New Fairfield | Home - Pomperaug HS-Main Gym [Directions] | 12:00 p.m. | W 3-0 | |
| Sat., 10/15 | JV Girls Volleyball | New Fairfield | Home - Pomperaug HS-Main Gym [Directions] | 10:30 a.m. | ||
| Sat., 10/15 | FR Girls Volleyball | New Fairfield | Home - Pomperaug HS-Auxiliary Gym [Directions] | 10:30 a.m. | ||
| Mon., 10/17 | V Field Hockey | Brookfield | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | T 0-0 | |
| Mon., 10/17 | JV Field Hockey | Brookfield | Home - Pomperaug HS-Stadium [Directions] | 5:30 p.m. | ||
| Mon., 10/17 | V Girls Swimming and Diving | Newtown | Away - Newtown HS-pool [Directions] | 4:00 p.m. | 99.5/86.5 Pomperaug | |
| Mon., 10/17 | V Girls Volleyball | New Milford | Away - New Milford HS-Main Gym - NMHS [Directions] | 7:00 p.m. | W 3-1 | |
| Mon., 10/17 | JV Girls Volleyball | New Milford | Away - New Milford HS-Main Gym - NMHS [Directions] | 5:30 p.m. | ||
| Mon., 10/17 | FR Girls Volleyball | New Milford | Away - New Milford HS-Small Gym - NMHS [Directions] | 5:30 p.m. | ||
| Tue., 10/18 | V Boys Soccer | Immaculate | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | L 2-0 | |
| Tue., 10/18 | JV Boys Soccer | Immaculate | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Tue., 10/18 | FR Boys Soccer | Newtown | Away - Treadwell Park-Treadwell Town Park--Tilson Field [Directions] | 4:00 p.m. | ||
| Tue., 10/18 | V Girls Soccer | Immaculate | Away - Immaculate HS-Mustang Valley [Directions] | 4:00 p.m. | W 3-1 | |
| Tue., 10/18 | V Girls Swimming and Diving | New Fairfield | Home - Pomperaug HS-PHS Pool [Directions] | 4:00 p.m. | 90/85 Pomperaug | |
| Tue., 10/18 | V Girls Volleyball | Naugatuck | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | W 3-1 | |
| Tue., 10/18 | JV Girls Volleyball | Naugatuck | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/19 | V Boys Cross Country | SWC cross country championships | Away - Bethel HS-BHS track | 4:00 p.m. | ||
| Wed., 10/19 | FR Football | New Milford | Home - Pomperaug HS-Stadium [Directions] | 4:30 p.m. | ||
| Wed., 10/19 | V Girls Cross Country | SWC cross country championships | Away - Bethel HS-BHS track | 3:30 p.m. | ||
| Thu., 10/20 | V Boys Soccer | New Fairfield | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | W 5-0 | |
| Thu., 10/20 | JV Boys Soccer | New Fairfield | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Thu., 10/20 | V Field Hockey | Immaculate | Away - Immaculate HS-Mustang Valley [Directions] | 4:00 p.m. | T 2-2 | |
| Thu., 10/20 | JV Field Hockey | Immaculate | Away - Immaculate HS-Mustang Valley [Directions] | 5:30 p.m. | ||
| Thu., 10/20 | V Girls Soccer | New Fairfield | Away - New Fairfield HS-Marty Morgan Field [Directions] | 7:00 p.m. | T 0-0 | |
| Thu., 10/20 | JV Girls Soccer | New Fairfield | Away - New Fairfield HS-Marty Morgan Field [Directions] | 5:00 p.m. | ||
| Thu., 10/20 | V Girls Volleyball | Stratford | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Thu., 10/20 | JV Girls Volleyball | Stratford | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/20 | FR Girls Volleyball | Stratford | Home - Pomperaug HS-Auxiliary Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/21 | V Football | New Milford | Away - New Milford HS-Joe Wiser Stadium - NMHS [Directions] | 7:00 p.m. | L 0-35 | |
| Fri., 10/21 | V Girls Swimming and Diving | New Milford | Away - Canterbury School-Higgins Aquatic Center [Directions] | 6:00 p.m. | 101-77 Pomperaug | |
| Sat., 10/22 | V Boys Soccer | Bethel | Away - Bethel HS-MS Turf Soccer Field [Directions] | 3:00 p.m. | T 2-2 | |
| Sat., 10/22 | JV Boys Soccer | Bethel | Away - Bethel HS-Rockwell Field [Directions] | 1:00 p.m. | ||
| Sat., 10/22 | FR Boys Soccer | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | 10:30 a.m. | ||
| Sat., 10/22 | V Field Hockey | Fairfield Ludlowe | Home - Pomperaug HS-Stadium [Directions] | 12:00 p.m. | L 1-0 | |
| Sat., 10/22 | JV Field Hockey | Fairfield Ludlowe | Home - Pomperaug HS-Stadium [Directions] | 10:30 a.m. | ||
| Sat., 10/22 | FR Girls Volleyball | Naugatuck | Home - Pomperaug HS-Auxiliary Gym [Directions] | 9:00 a.m. | ||
| Mon., 10/24 | V Girls Soccer | Newtown | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | W 3-1 | |
| Mon., 10/24 | JV Girls Soccer | Newtown | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Tue., 10/25 | V Boys Soccer | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 6:00 p.m. | L 2-0 | |
| Tue., 10/25 | JV Boys Soccer | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 4:00 p.m. | ||
| Tue., 10/25 | FR Boys Soccer | Bethel | Away - Bethel HS-MS Turf Soccer Field [Directions] | 3:30 p.m. | ||
| Tue., 10/25 | V Girls Swimming and Diving | Bethel/Immaculate | Away - Bethel HS-Brookfield YMCA [Directions] | 5:30 p.m. | ||
| Tue., 10/25 | V Girls Volleyball | Bethel | Away - Bethel HS-BHS gym [Directions] | 5:00 p.m. | W 3-0 | |
| Tue., 10/25 | JV Girls Volleyball | Bethel | Away - Bethel HS-BHS gym [Directions] | 3:30 p.m. | ||
| Thu., 10/27 | FR Football | Bethel | Home - Pomperaug HS-Stadium [Directions] | 4:00 p.m. | ||
| Thu., 10/27 | V Girls Volleyball | Bunnell | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | W 3-1 | |
| Thu., 10/27 | JV Girls Volleyball | Bunnell | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 10/27 | FR Girls Volleyball | Bethel | Away - Bethel HS-BHS gym [Directions] | 3:30 p.m. | ||
| Fri., 10/28 | V Football | Bethel | Away - Bethel HS-DeSantis Field at Bethel High [Directions] | 7:00 p.m. | W 41-3 | |
| Mon., 10/31 | Unified Sports Soccer | Bethel | Home - Pomperaug HS-PHS Soccer Field [Directions] | 3:00 p.m. | ||
| Thu., 11/3 | FR Football | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | Canceled | Cancelled | |
| Fri., 11/4 | V Football | Masuk | Home - Pomperaug HS-Stadium [Directions] | 6:30 p.m. | L 12-46 | |
| Thu., 11/10 | FR Football | Bunnell | Home - Pomperaug HS-Stadium [Directions] | 4:00 p.m. | ||
| Thu., 11/10 | V Girls Volleyball | Berlin | Away - Berlin HS-Gibney Gymnasium [Directions] | 5:00 p.m. | W 3-2 | |
| Sat., 11/12 | V Football | Bunnell | Away - Bunnell HS-Mastroni Field [Directions] | 3:30 p.m. | L 0-49 | |
| Thu., 11/17 | FR Football | Notre Dame-Fairfield | Home - Pomperaug HS-Stadium [Directions] | 4:00 p.m. | ||
| Tue., 11/22 | V Football | Notre Dame-Fairfield | Away - Sacred Heart University-Campus Field [Directions] | 6:30 p.m. | L 16-22 | |
| Tue., 12/13 | V Girls Basketball | Cheshire | Away - Cheshire HS-Gym West [Directions] | 7:00 p.m. | W 57-42 | |
| Tue., 12/13 | JV Girls Basketball | Cheshire | Away - Cheshire HS-Gym West [Directions] | 5:15 p.m. | ||
| Tue., 12/13 | FR Girls Basketball | Cheshire | Away - Cheshire HS-Gym West [Directions] | 3:45 p.m. | ||
| Wed., 12/14 | V Boys Ice Hockey | Trumbull | Home - Taft School-Mays [Directions] | 8:00 p.m. | L 3-4 | |
| Wed., 12/14 | V Wrestling | Weston | Away - Weston HS-Gym (New) [Directions] | 6:00 p.m. | Weston 48 Pomperaug 21 | |
| Fri., 12/16 | V Boys Indoor Track | Hillhouse Invitational at Floyd Little Athletic Center- New Haven | Away - Not Listed | 4:30 p.m. | ||
| Fri., 12/16 | V Girls Indoor Track | Hillhouse Invitational at Floyd Little Athletic Center- New Haven | Away - Not Listed | 4:30 p.m. | ||
| Sat., 12/17 | V Boys Basketball | Jonathan Law | Home - Pomperaug HS-Main Gym [Directions] | 1:00 p.m. | L 47-66 | |
| Sat., 12/17 | JV Boys Basketball | Jonathan Law | Home - Pomperaug HS-Main Gym [Directions] | 11:30 p.m. | ||
| Sat., 12/17 | FR Boys Basketball | Jonathan Law | Home - Pomperaug HS-Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 12/17 | V Boys Ice Hockey | Conard | Away - Veterans Memorial Ice Rink - West Hartford-Ice Rink [Directions] | 1:30 p.m. | L 1-3 | |
| Sat., 12/17 | V Boys Indoor Track | Hillhouse Invitational at Floyd Little Athletic Center- New Haven | Away - Not Listed | 10:00 a.m. | ||
| Sat., 12/17 | V Wrestling | Bacon Academy, New Canaan, Nonnewaug, Portland, Wethersfield | Home - Pomperaug HS-Auxiliary Gym [Directions] | 9:00 a.m. | ||
| Sat., 12/17 | V Girls Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 2:00 p.m. | W 36-28 | |
| Sat., 12/17 | JV Girls Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 12:30 p.m. | ||
| Sat., 12/17 | V Girls Indoor Track | Hillhouse Invitational at Floyd Little Athletic Center- New Haven | Away - Not Listed | 10:00 a.m. | ||
| Mon., 12/19 | V Girls Basketball | Immaculate | Away - Immaculate HS-Immaculate Gym [Directions] | 7:00 p.m. | L 32-47 | |
| Mon., 12/19 | JV Girls Basketball | Immaculate | Away - Immaculate HS-Immaculate Gym [Directions] | 5:15 p.m. | ||
| Mon., 12/19 | FR Girls Basketball | Immaculate | Away - Immaculate HS-Immaculate Gym [Directions] | 3:30 p.m. | ||
| Wed., 12/21 | V Boys Ice Hockey | Sheehan | Away - Choate Rosemary Hall-Ice Rink [Directions] | 6:00 p.m. | W 1-0 | |
| Wed., 12/21 | V Boys Swimming and Diving | Masuk | Home - Pomperaug HS-PHS Pool [Directions] | 6:00 p.m. | Pomperaug 95 Masuk 77 | |
| Wed., 12/21 | V Wrestling | Masuk | Home - Pomperaug HS-Auxiliary Gym [Directions] | 6:00 p.m. | Masuk 46 Pomperaug 27 | |
| Wed., 12/21 | V Girls Basketball | Cromwell | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | W 63-54 | |
| Wed., 12/21 | JV Girls Basketball | Cromwell | Home - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 12/21 | FR Girls Basketball | Danbury | Home - Pomperaug HS-Main Gym [Directions] | 3:45 p.m. | ||
| Thu., 12/22 | V Boys Basketball | Nonnewaug | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | W 78-41 | |
| Thu., 12/22 | JV Boys Basketball | Nonnewaug | Home - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 12/27 | V Boys Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 5:00 p.m. | L 38-61 | |
| Tue., 12/27 | V Girls Basketball | Naugatuck | Home - Pomperaug HS-Main Gym [Directions] | 5:00 p.m. | W 56-25 | |
| Wed., 12/28 | V Boys Ice Hockey | Cheshire | Home - Taft School-Mays [Directions] | 1:00 p.m. | W 5-3 | |
| Thu., 12/29 | V Boys Basketball | Immaculate | Away - Staples HS-Staples Gym [Directions] | 3:00 p.m. | L 52-54 | |
| Thu., 12/29 | V Girls Basketball | Wethersfield | Away - Pomperaug HS-Main Gym [Directions] | 5:00 p.m. | W 57-27 | |
| Fri., 12/30 | V Boys Ice Hockey | Brien McMahon/Norwalk | Home - Taft School-Mays [Directions] | 3:30 p.m. | W 5-3 | |
| Fri., 12/30 | V Wrestling | Trumbull, Amity, Berlin, Greenwich, Foran, Manchester, Masuk, Minnechaug (MA), TBA, Stratford | Away - Trumbull HS-Aux Gym | 8:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 9:00 a.m. | ||||||
| Tue., 1/3 | V Boys Indoor Track | Wilton Wright Invitational at Southern Connecticut State University | Away - Not Listed | 4:00 p.m. | ||
| Tue., 1/3 | V Girls Indoor Track | Wilton Wright Invitational at Southern Connecticut State University | Away - Not Listed | 4:00 p.m. | ||
| Wed., 1/4 | V Boys Ice Hockey | North Haven | Away - Northford-Red [Directions] | 8:30 p.m. | L 2-3 | |
| Wed., 1/4 | V Wrestling | Brookfield/Shepaug | Home - Pomperaug HS-Auxiliary Gym [Directions] | 6:00 p.m. | Brookfield 28 Pomperaug 24 | |
| Thu., 1/5 | V Boys Basketball | Kolbe Cathedral | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | L 42-68 | |
| Thu., 1/5 | JV Boys Basketball | Kolbe Cathedral | Home - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | ||
| Thu., 1/5 | FR Boys Basketball | Wolcott | Home - Pomperaug HS-Main Gym [Directions] | 3:45 p.m. | ||
| Thu., 1/5 | V Boys Indoor Track | SWC Split Meet Developmental at Bethel | Away - Bethel HS-Bethel Track and Field Center | 4:00 p.m. | ||
| Thu., 1/5 | V Boys Swimming and Diving | Weston | Away - Weston HS-Weston MS Pool [Directions] | 4:30 p.m. | Pomperaug 95 Weston 83 | |
| Thu., 1/5 | V Girls Basketball | Kolbe Cathedral | Away - Cardinal Sheehan Center Bridgeport [Directions] | 7:00 p.m. | W 55-54 | |
| Thu., 1/5 | JV Girls Basketball | Kolbe Cathedral | Away - Cardinal Sheehan Center Bridgeport [Directions] | 5:15 p.m. | ||
| Thu., 1/5 | V Girls Indoor Track | SWC Split Meet Developmental at Bethel | Away - Bethel HS-Bethel Track and Field Center | 4:00 p.m. | ||
| Sat., 1/7 | V Boys Ice Hockey | Westhill/Stamford | Away - Terry Conners - Stamford-Ice Rink [Directions] | 8:10 p.m. | L 3-4 | |
| Sat., 1/7 | JV Wrestling | Bristol Eastern, Avon, Berlin, Branford, Bristol Central, East Hartford, Enfield, Farmington, Guilford, Ledyard, Middletown, TBA, New Fairfield, New Milford, Wethersfield, Hall | Away - Bristol Eastern HS-Gym | TBA | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 9:30 a.m. | ||||||
| Sat., 1/7 | V Girls Basketball | East Lyme | Away - East Lyme HS-North Gym [Directions] | 2:00 p.m. | W 61-28 | |
| Sat., 1/7 | JV Girls Basketball | East Lyme | Away - East Lyme HS-North Gym [Directions] | 12:15 p.m. | ||
| Sat., 1/7 | V Girls Gymnastics | Joel Barlow, Brookfield, Oxford | Away - Gymnastics Revolution [Directions] | 4:00 p.m. | ||
| Mon., 1/9 | V Boys Basketball | Bunnell | Away - Bunnell HS-David Johnson Gymnasium [Directions] | 7:00 p.m. | L 53-58 | |
| Mon., 1/9 | JV Boys Basketball | Bunnell | Away - Bunnell HS-David Johnson Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 1/9 | FR Boys Basketball | Bunnell | Away - Bunnell HS-David Johnson Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 1/9 | V Girls Basketball | Bunnell | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | W 76-35 | |
| Mon., 1/9 | JV Girls Basketball | Bunnell | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/10 | V Boys Swimming and Diving | Newtown | Away - Newtown HS-pool [Directions] | 4:00 p.m. | Pomperaug 93.5 Newtown 84.5 | |
| Tue., 1/10 | V Girls Gymnastics | New Milford, Brookfield, Oxford | Away - New Milford HS-Small Gym - NMHS [Directions] | 6:15 p.m. | ||
| Wed., 1/11 | V Boys Ice Hockey | Branford | Home - Taft School-Mays [Directions] | 8:00 p.m. | W 4-2 | |
| Wed., 1/11 | V Boys Indoor Track | Developmental Meet | Away - Bethel HS-Track and Field Training Center | 4:00 p.m. | ||
| Wed., 1/11 | V Wrestling | Stratford | Away - Stratford HS-Gym [Directions] | 6:00 p.m. | Stratford 54 Pomperaug 18 | |
| Wed., 1/11 | V Girls Indoor Track | SWC Developmental | Away - Bethel HS-Track and Field Training Center | 4:00 p.m. | ||
| Thu., 1/12 | V Boys Basketball | Notre Dame-Fairfield | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | L 52-58 | |
| Thu., 1/12 | JV Boys Basketball | Notre Dame-Fairfield | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 1/12 | FR Boys Basketball | Notre Dame-Fairfield | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 1/12 | V Girls Basketball | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Sister Marion Reilly Auditorium [Directions] | 7:00 p.m. | L 32-43 | |
| Thu., 1/12 | JV Girls Basketball | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Sister Marion Reilly Auditorium [Directions] | 5:30 p.m. | ||
| Sat., 1/14 | V Boys Ice Hockey | Lyman Hall | Away - Northford-Red [Directions] | 5:00 p.m. | W 5-2 | |
| Sat., 1/14 | V Wrestling | Art Powers Duals | Away - Berlin HS-Jim Day Gymnasium | 9:00 a.m. | ||
| Sat., 1/14 | FR Girls Basketball | St. Paul Catholic | Away - St. Paul Catholic HS -Rev. Brian Monnerat Gymnasium [Directions] | 11:00 a.m. | ||
| Tue., 1/17 | V Boys Basketball | Stratford | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | W 56-45 | |
| Tue., 1/17 | JV Boys Basketball | Stratford | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/17 | FR Boys Basketball | Stratford | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/17 | V Boys Swimming and Diving | New Fairfield | Home - Pomperaug HS-PHS Pool [Directions] | 5:00 p.m. | Pomperaug 83 New Fairfield 52 | |
| Tue., 1/17 | V Girls Basketball | Stratford | Away - Stratford HS-Gym [Directions] | 7:00 p.m. | W 78-50 | |
| Tue., 1/17 | JV Girls Basketball | Stratford | Away - Stratford HS-Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/18 | V Boys Basketball | Foran | Away - Foran HS -Edna L. Fraser Gymnasium [Directions] | 4:00 p.m. | L 39-41 | |
| Wed., 1/18 | JV Boys Basketball | Foran | Away - Foran HS -Edna L. Fraser Gymnasium [Directions] | 5:45 p.m. | ||
| Wed., 1/18 | FR Boys Basketball | Foran | Home - Pomperaug HS-Main Gym [Directions] | 3:30 p.m. | ||
| Wed., 1/18 | V Boys Indoor Track | Developmental Meet | Away - Bethel HS-Track and Field Training Center | 4:00 p.m. | ||
| Wed., 1/18 | V Wrestling | Bunnell | Home - Pomperaug HS-Auxiliary Gym [Directions] | 6:00 p.m. | Bunnell 45 Pomperaug 19 | |
| Wed., 1/18 | V Girls Indoor Track | Developmental Meet | Away - Bethel HS-Track and Field Training Center | 4:00 p.m. | ||
| Fri., 1/20 | V Boys Basketball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 7:00 p.m. | W 58-52 | |
| Fri., 1/20 | JV Boys Basketball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 5:30 p.m. | ||
| Fri., 1/20 | FR Boys Basketball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 4:00 p.m. | ||
| Fri., 1/20 | V Boys Ice Hockey | South Windsor | Away - South Windsor Arena-Ice Rink [Directions] | 8:00 p.m. | L 0-2 | |
| Fri., 1/20 | V Girls Basketball | Masuk | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | W 57-32 | |
| Fri., 1/20 | JV Girls Basketball | Masuk | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/20 | V Girls Gymnastics | New Milford, Brookfield, Joel Barlow, Oxford | Away - New Milford HS-Small Gym - NMHS [Directions] | 6:15 p.m. | ||
| Sat., 1/21 | V Boys Basketball | Northwestern | Home - Pomperaug HS-Main Gym [Directions] | 1:45 p.m. | L 55-70 | |
| Sat., 1/21 | JV Boys Basketball | Northwestern | Home - Pomperaug HS-Main Gym [Directions] | 11:45 a.m. | ||
| Sat., 1/21 | FR Boys Basketball | Northwestern | Home - Pomperaug HS-Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 1/21 | V Boys Ice Hockey | Newtown/New Fairfield | Home - Taft School-Mays [Directions] | 7:30 p.m. | W 4-1 | |
| Sat., 1/21 | V Wrestling | Colter Abely Wrestling Tournament | Away - Mercy HS-Gym | 8:00 a.m. | ||
| Sat., 1/21 | FR Girls Basketball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 9:00 a.m. | ||
| Tue., 1/24 | V Boys Basketball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 7:00 p.m. | L 77-100 | |
| Tue., 1/24 | JV Boys Basketball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/24 | FR Boys Basketball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 3:30 p.m. | ||
| Tue., 1/24 | V Boys Indoor Track | Varsity Developmental Meet | Away - Southern Connecticut State University-indoor track | 4:00 p.m. | ||
| Tue., 1/24 | V Girls Basketball | Brookfield | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | W 47-37 | |
| Tue., 1/24 | JV Girls Basketball | Brookfield | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/24 | FR Girls Basketball | Brookfield | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/24 | V Girls Gymnastics | Jonathan Law, Oxford | Away - Jonathan Law HS-North Gymnasium [Directions] | 6:00 p.m. | ||
| Tue., 1/24 | V Girls Indoor Track | Varsity Developmental Meet | Away - Southern Connecticut State University-indoor track | 4:00 p.m. | ||
| Thu., 1/26 | V Wrestling | Newtown | Away - Newtown HS-Gym [Directions] | 7:00 p.m. | ||
| Fri., 1/27 | V Boys Basketball | Bethel | Away - Bethel HS-BHS gym [Directions] | 7:00 p.m. | W 69-45 | |
| Fri., 1/27 | JV Boys Basketball | Bethel | Away - Bethel HS-BHS gym [Directions] | 5:15 p.m. | ||
| Fri., 1/27 | FR Boys Basketball | Bethel | Away - Bethel HS-BHS gym [Directions] | 3:45 p.m. | ||
| Fri., 1/27 | V Girls Basketball | Bethel | Home - Pomperaug HS-Main Gym [Directions] | 6:30 p.m. | W 56-50 | |
| Fri., 1/27 | JV Girls Basketball | Bethel | Home - Pomperaug HS-Main Gym [Directions] | 4:45 p.m. | ||
| Sat., 1/28 | V Boys Ice Hockey | Farmington Valley Generals | Home - Taft School-Mays [Directions] | 7:30 p.m. | L 2-3 | |
| Sat., 1/28 | V Boys Swimming and Diving | Brookfield | Home - Pomperaug HS-PHS Pool [Directions] | 5:00 p.m. | Pomperaug 90 Brookfield 76 | |
| Sat., 1/28 | V Wrestling | Brookfield Wrestling Tournament | Away - Brookfield HS-BHS Small Gym | 9:30 a.m. | ||
| Mon., 1/30 | V Boys Basketball | New Milford | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | W 75-48 | |
| Mon., 1/30 | JV Boys Basketball | New Milford | Home - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 1/30 | FR Boys Basketball | New Milford | Home - Pomperaug HS-Main Gym [Directions] | 3:45 p.m. | ||
| Mon., 1/30 | V Girls Basketball | New Milford | Away - New Milford HS-Main Gym - NMHS [Directions] | 6:00 p.m. | W 62-43 | |
| Mon., 1/30 | JV Girls Basketball | New Milford | Away - New Milford HS-Main Gym - NMHS [Directions] | 4:30 p.m. | ||
| Mon., 1/30 | FR Girls Basketball | Naugatuck | Home - Pomperaug HS-Auxiliary Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/31 | V Boys Indoor Track | Senior Meet | Away - Bethel HS-Track and Field Training Center | 4:00 p.m. | ||
| Tue., 1/31 | V Girls Indoor Track | Senior Meet | Away - Bethel HS-Track and Field Training Center | 4:00 p.m. | ||
| Wed., 2/1 | V Boys Ice Hockey | JBWA | Away - Danbury Ice Arena-Patriot Rink [Directions] | 5:30 p.m. | L 1-3 | |
| Wed., 2/1 | V Boys Swimming and Diving | New Milford | Away - Canterbury School-Higgins Aquatic Center [Directions] | 7:00 p.m. | Pomperaug 94 New Milford 68 | |
| Wed., 2/1 | V Wrestling | New Milford | Away - New Milford HS-Small Gym - NMHS [Directions] | 6:00 p.m. | ||
| Wed., 2/1 | V Girls Gymnastics | Jonathan Law, Oxford | Away - Jonathan Law HS-North Gymnasium [Directions] | 6:00 p.m. | ||
| Thu., 2/2 | V Boys Basketball | Newtown | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | L 37-55 | |
| Thu., 2/2 | JV Boys Basketball | Newtown | Home - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | ||
| Thu., 2/2 | FR Boys Basketball | Newtown | Home - Pomperaug HS-Main Gym [Directions] | 3:45 p.m. | ||
| Thu., 2/2 | V Girls Basketball | Newtown | Away - Newtown HS-Gym [Directions] | 7:00 p.m. | W 48-47 | |
| Thu., 2/2 | JV Girls Basketball | Newtown | Away - Newtown HS-Gym [Directions] | 5:30 p.m. | ||
| Thu., 2/2 | FR Girls Basketball | Newtown | Away - Newtown HS-Gym [Directions] | 4:00 p.m. | ||
| Sat., 2/4 | V Boys Ice Hockey | North Branford | Away - Northford-Red [Directions] | 2:30 p.m. | T 3-3 | |
| Sat., 2/4 | V Boys Indoor Track | SWC Championship Meet | Away - Floyd Little Athletic Center-Field House | 5:00 p.m. | ||
| Sat., 2/4 | V Boys Swimming and Diving | Hall, Amity, Conard, East Lyme, Glastonbury, Southington | Away - Cornerstone Aquatics Center-Pool | 3:00 p.m. | N/A | |
| Sat., 2/4 | V Girls Indoor Track | Bethel, Brookfield, Bunnell, Immaculate, Joel Barlow, Kolbe Cathedral, Masuk, New Fairfield, New Milford, Newtown, Notre Dame-Fairfield, Stratford, Weston | Away - Floyd Little Athletic Center-Field House | 5:00 p.m. | ||
| Mon., 2/6 | V Boys Basketball | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | 7:00 p.m. | L 38-45 | |
| Mon., 2/6 | JV Boys Basketball | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/6 | FR Boys Basketball | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | 4:00 p.m. | ||
| Mon., 2/6 | V Wrestling | Notre Dame-Fairfield | Home - Pomperaug HS-Auxiliary Gym [Directions] | 6:00 p.m. | ||
| Mon., 2/6 | V Girls Basketball | New Fairfield | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | W 45-22 | |
| Mon., 2/6 | JV Girls Basketball | New Fairfield | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/6 | FR Girls Basketball | New Fairfield | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/7 | V Boys Swimming and Diving | Oxford | Away - Oxford HS-Pool [Directions] | 6:00 p.m. | Pomperaug 99 Oxford 86 | |
| Wed., 2/8 | V Boys Ice Hockey | Masuk | Home - Taft School-Mays [Directions] | 8:00 p.m. | T 1-1 | |
| Thu., 2/9 | V Boys Basketball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 7:00 p.m. | W 44-41 | |
| Thu., 2/9 | JV Boys Basketball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 5:30 p.m. | ||
| Thu., 2/9 | FR Boys Basketball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 4:00 p.m. | ||
| Thu., 2/9 | V Boys Swimming and Diving | Joel Barlow-Bethel Swim | Home - Pomperaug HS-PHS Pool [Directions] | 6:00 p.m. | Pomperaug 88 Barlow/Bethel 71 | |
| Thu., 2/9 | V Girls Basketball | Joel Barlow | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | W 55-31 | |
| Thu., 2/9 | JV Girls Basketball | Joel Barlow | Home - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | ||
| Thu., 2/9 | FR Girls Basketball | St. Paul Catholic | Home - Pomperaug HS-Main Gym [Directions] | 3:45 p.m. | ||
| Sat., 2/11 | V Boys Ice Hockey | Guilford | Away - East Haven HS-Veterans Rink [Directions] | 1:00 p.m. | L 2-4 | |
| Sat., 2/11 | V Girls Basketball | Stamford | Home - Pomperaug HS-Main Gym [Directions] | 2:00 p.m. | W 53-26 | |
| Sat., 2/11 | JV Girls Basketball | Stamford | Home - Pomperaug HS-Main Gym [Directions] | 12:30 p.m. | ||
| Sat., 2/11 | FR Girls Basketball | Stamford | Home - Pomperaug HS-Main Gym [Directions] | 11:00 a.m. | ||
| Sat., 2/11 | V Girls Gymnastics | Oxford | Away - Kinetic Kids [Directions] | 4:00 p.m. | ||
| Mon., 2/13 | V Boys Ice Hockey | St. Joseph | Home - Taft School-Mays [Directions] | 8:15 p.m. | W 1-0 | |
| Mon., 2/13 | FR Girls Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/14 | V Boys Basketball | Weston | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | L 55-56 | |
| Tue., 2/14 | JV Boys Basketball | Weston | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/14 | FR Boys Basketball | Weston | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/14 | V Boys Swimming and Diving | Naugatuck | Home - Pomperaug HS-PHS Pool [Directions] | 5:00 p.m. | Pomperaug- 95 Naugatuck-83 | |
| Tue., 2/14 | V Girls Basketball | Weston | Away - Weston HS-Gym (New) [Directions] | 7:00 p.m. | W 51-34 | |
| Tue., 2/14 | JV Girls Basketball | Weston | Away - Weston HS-Gym (New) [Directions] | 5:30 p.m. | ||
| Wed., 2/15 | V Boys Ice Hockey | East Haven Coop | Away - East Haven HS-Veterans Rink [Directions] | 7:30 p.m. | T 2-2(OT) | |
| Fri., 2/17 | V Boys Basketball | Immaculate | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | L 44-63 | |
| Fri., 2/17 | JV Boys Basketball | Immaculate | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/17 | FR Boys Basketball | Immaculate | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 2/18 | V Boys Ice Hockey | Amity | Home - Taft School-Mays [Directions] | 7:30 p.m. | W 4-0 | |
| Sat., 2/18 | V Girls Gymnastics | Oxford | Home - Kinetic Kids [Directions] | 4:00 p.m. | ||
| Mon., 2/20 | V Boys Basketball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | 7:00 p.m. | W 60-51 | |
| Mon., 2/20 | JV Boys Basketball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | 5:15 p.m. | ||
| Mon., 2/20 | FR Boys Basketball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | 3:45 p.m. | ||
| Mon., 2/20 | V Girls Gymnastics | Joel Barlow, Newtown, Nonnewaug, Oxford | Away - Gymnastics Revolution [Directions] | 5:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 10:00 a.m. | ||||||
| Wed., 2/22 | V Boys Ice Hockey | Daniel Hand | Away - Northford-Red [Directions] | 5:00 p.m. | W 6-4 | |
| Thu., 2/23 | V Boys Swimming and Diving | Bunnell-Stratford | Away - Bunnell HS-Flood M.S. Pool [Directions] | 6:00 p.m. | Pomperaug-86 Bunnell/Stratford-60 | |
| Sat., 3/4 | V Boys Swimming and Diving | Naugatuck | Home - Pomperaug HS-PHS Pool [Directions] | 11:00 a.m. | ||
| Sat., 4/1 | V Boys Lacrosse | Holy Cross | Away - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 11:30 a.m. | W 20-7 | |
| Sat., 4/1 | JV Boys Lacrosse | Holy Cross | Away - Municipal Stadium Complex (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | Canceled | Cancelled | |
| Sat., 4/1 | V Boys Volleyball | Wolcott Tech | Away - Oliver Wolcott Technical HS-Wolcott Tech Gym [Directions] | 11:30 a.m. | L 2-3 | |
| Sat., 4/1 | JV Boys Volleyball | Wolcott Tech | Away - Oliver Wolcott Technical HS-Wolcott Tech Gym [Directions] | 10:00 a.m. | ||
| Sat., 4/1 | V Girls Lacrosse | Amity | Away - Amity Regional HS-William Johnson Stadium Field [Directions] | 11:00 a.m. | L 16-9 | |
| Sat., 4/1 | JV Girls Lacrosse | Amity | Away - Amity Regional HS-William Johnson Stadium Field [Directions] | 12:45 p.m. | ||
| Sun., 4/2 | V Baseball | Oxford | Home - Pomperaug HS-Baseball Field [Directions] | 2:00 p.m. | L 2-13 | |
| Mon., 4/3 | V Baseball | Abbott Tech | Away - Abbott V-T School-Abbott Tech Baseball Field, School Campus [Directions] | 3:45 p.m. | L 1-11 | |
| Mon., 4/3 | V Boys Lacrosse | Norwalk | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | W 22-8 | |
| Mon., 4/3 | JV Boys Lacrosse | Norwalk | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Mon., 4/3 | V Boys Volleyball | St. Joseph | Home - Pomperaug HS-Main Gym [Directions] | 5:00 p.m. | W 3-0 | |
| Mon., 4/3 | JV Boys Volleyball | St. Joseph | Home - Pomperaug HS-Main Gym [Directions] | 3:30 p.m. | ||
| Mon., 4/3 | V Softball | Nonnewaug | Away - Nonnewaug HS-Varsity Field [Directions] | 3:45 p.m. | W 10-0 | |
| Mon., 4/3 | JV Softball | Bethel | Away - Bethel HS-Kisling Field [Directions] | 4:00 p.m. | ||
| Tue., 4/4 | JV Baseball | Seymour | Home - Pomperaug HS-Baseball Field [Directions] | 4:15 p.m. | W 9-9 | |
| Tue., 4/4 | V Girls Golf | Bunnell | Away - Bunnell HS-Oronoque C.C. [Directions] | 3:00 p.m. | ||
| Tue., 4/4 | V Girls Lacrosse | Conard | Away - Conard HS-McKee Stadium [Directions] | 4:00 p.m. | L 14-7 | |
| Tue., 4/4 | JV Girls Lacrosse | Conard | Away - Conard HS-McKee Stadium [Directions] | 5:15 p.m. | ||
| Tue., 4/4 | V Softball | Oxford | Away - Oxford HS-Softball Field [Directions] | 4:00 p.m. | W 2-1 | |
| Tue., 4/4 | JV Softball | Brookfield | Away - Brookfield HS-BHS Softball Field [Directions] | 4:15 p.m. | ||
| Wed., 4/5 | V Boys Tennis | Immaculate | Home - Edgewood Bath and Tennis Club [Directions] | 5:30 p.m. | W 6-1 [Detailed Results] | |
| Wed., 4/5 | V Boys Volleyball | Xavier | Away - Mercy HS-Gym [Directions] | 5:15 p.m. | W 3-1 | |
| Wed., 4/5 | JV Boys Volleyball | Xavier | Away - Mercy HS-Gym [Directions] | 4:15 p.m. | ||
| Wed., 4/5 | V Girls Golf | Joel Barlow | Away - Redding Country Club [Directions] | 3:00 p.m. | Barlow 229 - Pomperaug 248 | |
| Wed., 4/5 | V Girls Tennis | Immaculate | Away - Rogers Park (Danbury, CT)-Tennis Courts [Directions] | 3:45 p.m. | W 5-2 [Detailed Results] | |
| Thu., 4/6 | V Boys Lacrosse | Masuk | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | W 12-9 | |
| Thu., 4/6 | JV Boys Lacrosse | Masuk | Home - Pomperaug HS-Stadium [Directions] | Canceled | Cancelled | |
| Thu., 4/6 | V Girls Lacrosse | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 6:30 p.m. | L 6-7 | |
| Thu., 4/6 | JV Girls Lacrosse | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 5:00 p.m. | ||
| Thu., 4/6 | V Softball | Amity | Home - Pomperaug HS-Softball Field [Directions] | 4:15 p.m. | L 3-5 | |
| Sat., 4/8 | V Baseball | New Britain | Away - Beehive Field-Baseball Diamond [Directions] | 10:00 a.m. | W 5-0 | |
| Sat., 4/8 | V Boys Lacrosse | Wolcott | Away - Wolcott HS-Turf Field [Directions] | 11:00 a.m. | W 18-1 | |
| Mon., 4/10 | V Baseball | Weston | Home - Pomperaug HS-Baseball Field [Directions] | 4:15 p.m. | L 2-4 | |
| Mon., 4/10 | JV Baseball | Bethel | Home - Pomperaug HS-Baseball Field [Directions] | 10:30 a.m. | ||
| Mon., 4/10 | V Boys Volleyball | Kolbe Cathedral | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Mon., 4/10 | JV Boys Volleyball | Kolbe Cathedral | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 4/10 | V Softball | Weston | Home - Pomperaug HS-Softball Field [Directions] | 4:15 p.m. | W 21-2 | |
| Mon., 4/10 | JV Softball | Naugatuck | Away - Naugatuck HS-Softball Diamond [Directions] | 2:00 p.m. | ||
| Mon., 4/10 | V Girls Tennis | Brookfield | Home - Edgewood Bath and Tennis Club [Directions] | 10:00 a.m. | L 3-4 [Detailed Results] | |
| Tue., 4/11 | JV Baseball | Weston | Away - Weston HS-Revson #2 (JV) [Directions] | 4:15 p.m. | W 15-3 | |
| Tue., 4/11 | FR Baseball | Bethel | Home - Pomperaug HS-Baseball Field [Directions] | 4:15 p.m. | L 15-12 | |
| Tue., 4/11 | V Boys Lacrosse | Immaculate | Away - Immaculate HS-Mustang Valley [Directions] | 4:00 p.m. | W 20-2 | |
| Tue., 4/11 | V Boys Tennis | Brookfield | Away - Brookfield HS-BHS Tennis Courts [Directions] | 10:00 a.m. | L 6-1 [Detailed Results] | |
| Tue., 4/11 | V Girls Lacrosse | Immaculate | Home - Pomperaug HS-Stadium [Directions] | 6:00 p.m. | W 16-3 | |
| Wed., 4/12 | V Baseball | Bethel | Away - Bethel HS-Hunt Field at Bethel HS [Directions] | 4:00 p.m. | L 4-5 | |
| Wed., 4/12 | FR Baseball | New Milford | Home - Pomperaug HS-Baseball Field [Directions] | 4:15 p.m. | L 12-9 | |
| Wed., 4/12 | V Boys Tennis | Weston | Home - Edgewood Bath and Tennis Club [Directions] | 10:00 a.m. | L 7-0 [Detailed Results] | |
| Wed., 4/12 | V Boys Volleyball | Kolbe Cathedral | Away - Kolbe Cathedral HS-Gym [Directions] | 1:00 p.m. | W 3-0 | |
| Wed., 4/12 | JV Boys Volleyball | Kolbe Cathedral | Away - Kolbe Cathedral HS-Gym [Directions] | 11:30 a.m. | ||
| Wed., 4/12 | V Softball | Bethel | Away - Bethel HS-Kisling Field [Directions] | 4:00 p.m. | W 4-0 | |
| Wed., 4/12 | V Girls Tennis | Weston | Away - Weston HS-WHS Tennis Courts [Directions] | 10:00 a.m. | L 1-6 [Detailed Results] | |
| Thu., 4/13 | V Boys Lacrosse | Southington | Home - Pomperaug HS-Stadium [Directions] | 5:30 p.m. | L 18-11 | |
| Thu., 4/13 | JV Boys Lacrosse | Southington | Home - Pomperaug HS-Stadium [Directions] | Canceled | Cancelled | |
| Fri., 4/14 | V Baseball | Immaculate | Away - Immaculate HS-Baseball Diamond [Directions] | 4:00 p.m. | W 13-2 | |
| Fri., 4/14 | V Boys Volleyball | Newtown | Away - Newtown HS-Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 4/14 | JV Boys Volleyball | Newtown | Away - Newtown HS-Gym [Directions] | 5:30 p.m. | ||
| Fri., 4/14 | V Girls Outdoor Track | Pomperaug Distance Challenge | Home - Pomperaug HS-Stadium [Directions] | Canceled | Cancelled | |
| Fri., 4/14 | V Softball | Bristol Central | Home - Pomperaug HS-Softball Field [Directions] | 1:45 p.m. | L 0-8 | |
| Fri., 4/14 | JV Softball | Bethel | Home - Pomperaug HS-Softball Field [Directions] | 4:15 p.m. | ||
| Sat., 4/15 | FR Baseball | Nonnewaug | Home - Pomperaug HS-Baseball Field [Directions] | 11:00 a.m. | L 6-4 | |
| Sat., 4/15 | JV Boys Lacrosse | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | Postponed | ||
| Sat., 4/15 | V Girls Lacrosse | Watertown | Home - Pomperaug HS-Stadium [Directions] | 12:00 p.m. | W 18-4 | |
| Sat., 4/15 | JV Girls Lacrosse | Watertown | Home - Pomperaug HS-Stadium [Directions] | 10:00 a.m. | ||
| Sat., 4/15 | V Softball | Woodland | Away - Woodland HS-Softball Diamond [Directions] | 11:00 a.m. | L 0-7 | |
| Sat., 4/15 | JV Softball | Woodland | Away - Woodland HS-Softball Diamond [Directions] | 1:00 p.m. | ||
| Mon., 4/17 | V Baseball | Newtown | Away - Newtown HS-Nighthawk Ball Park [Directions] | 4:15 p.m. | L 5-4 | |
| Mon., 4/17 | FR Baseball | Masuk | Away - Wolfe Park-Baseball Field [Directions] | 4:15 p.m. | W 13-11 | |
| Mon., 4/17 | V Boys Outdoor Track | Newtown, Kolbe Cathedral, Stratford | Away - Newtown HS-Blue and Gold Stadium [Directions] | 4:00 p.m. | ||
| Mon., 4/17 | V Boys Volleyball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 5:30 p.m. | W 3-0 | |
| Mon., 4/17 | JV Boys Volleyball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 4/17 | V Girls Golf | Joel Barlow | Home - Pomperaug HS-Pomperaug Golf Course [Directions] | 3:00 p.m. | Pomperaug 226 - Joel Barelow 228 | |
| Mon., 4/17 | V Softball | Newtown | Away - Newtown HS-Lindell A. Hertberg Softball Field [Directions] | 4:15 p.m. | L 2-10 | |
| Tue., 4/18 | JV Baseball | Newtown | Home - Pomperaug HS-Baseball Field [Directions] | 4:15 p.m. | ||
| Tue., 4/18 | V Boys Lacrosse | Weston | Away - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | L 19-5 | |
| Tue., 4/18 | JV Boys Lacrosse | Weston | Away - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 4/18 | V Boys Tennis | Bethel | Away - Bethel HS-BHS Tennis Courts [Directions] | 3:45 p.m. | L 4-3 [Detailed Results] | |
| Tue., 4/18 | V Girls Golf | Weston | Home - Pomperaug HS-Pomperaug Golf Course [Directions] | 3:00 p.m. | Pomperaug 227 - Weston 230 | |
| Tue., 4/18 | V Girls Lacrosse | Weston | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | L 15-7 | |
| Tue., 4/18 | JV Girls Lacrosse | Weston | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Tue., 4/18 | V Girls Outdoor Track | Newtown, Kolbe Cathedral, Stratford | Away - Newtown HS-Blue and Gold Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/18 | JV Softball | Newtown | Home - Pomperaug HS-Softball Field [Directions] | 4:15 p.m. | ||
| Tue., 4/18 | V Girls Tennis | Bethel | Home - Edgewood Bath and Tennis Club [Directions] | 3:45 p.m. | L 1-6 [Detailed Results] | |
| Wed., 4/19 | V Baseball | New Fairfield | Home - Pomperaug HS-Baseball Field [Directions] | 4:15 p.m. | L 3-5 | |
| Wed., 4/19 | V Boys Tennis | Newtown | Away - Newtown HS-NHS Tennis Courts [Directions] | 3:45 p.m. | L 6-1 [Detailed Results] | |
| Wed., 4/19 | V Softball | New Fairfield | Home - Pomperaug HS-Softball Field [Directions] | 4:15 p.m. | W 16-6 | |
| Wed., 4/19 | V Girls Tennis | Newtown | Home - Edgewood Bath and Tennis Club [Directions] | 3:15 p.m. | L 0-7 [Detailed Results] | |
| Thu., 4/20 | JV Baseball | New Fairfield | Away - New Fairfield HS-Baseball Field [Directions] | 4:15 p.m. | ||
| Thu., 4/20 | V Boys Lacrosse | Brookfield | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | W 18-2 | |
| Thu., 4/20 | JV Boys Lacrosse | Brookfield | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Thu., 4/20 | V Boys Volleyball | Brookfield | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Thu., 4/20 | JV Boys Volleyball | Brookfield | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 4/20 | V Girls Lacrosse | Brookfield | Away - Brookfield HS-BHS Stadium Field [Directions] | 6:00 p.m. | W 10-6 | |
| Thu., 4/20 | JV Girls Lacrosse | Brookfield | Away - Brookfield HS-BHS Stadium Field [Directions] | 4:15 p.m. | ||
| Thu., 4/20 | JV Softball | New Fairfield | Away - New Fairfield HS-Softball Field [Directions] | Postponed | ||
| Fri., 4/21 | V Baseball | Bunnell | Away - Bunnell HS-Bunnell Baseball Field [Directions] | 4:15 p.m. | W 6-1 | |
| Fri., 4/21 | V Boys Volleyball | Oxford | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | W 3-1 | |
| Fri., 4/21 | V Softball | Bunnell | Away - Bunnell HS-Bunnell Softball FIeld [Directions] | 4:15 p.m. | W 18-1 | |
| Sat., 4/22 | V Baseball | New London | Away - Dodd Stadium-Baseball Stadium [Directions] | 12:00 p.m. | W 9-2 | |
| Sat., 4/22 | JV Baseball | Bunnell | Home - Pomperaug HS-Baseball Field [Directions] | 12:00 p.m. | ||
| Sat., 4/22 | V Girls Lacrosse | Stratford/Bunnell | Home - Pomperaug HS-Stadium [Directions] | 12:00 p.m. | W 18-2 | |
| Sat., 4/22 | JV Girls Lacrosse | Stratford/Bunnell | Home - Pomperaug HS-Stadium [Directions] | 10:15 a.m. | ||
| Sat., 4/22 | V Girls Outdoor Track | Bill Mongovan Memorial Meet at Bethel High School | Away - Not Listed | 9:00 a.m. | ||
| Sat., 4/22 | JV Softball | Bunnell | Home - Pomperaug HS-Softball Field [Directions] | 12:00 p.m. | ||
| Mon., 4/24 | V Baseball | Kolbe Cathedral | Away - Seaside Park-Field #10 [Directions] | 4:15 p.m. | L 0-3 | |
| Mon., 4/24 | FR Baseball | Newtown | Home - Pomperaug HS-Baseball Field [Directions] | 4:15 p.m. | L 2-1 | |
| Mon., 4/24 | V Boys Outdoor Track | Joel Barlow, Bunnell, New Fairfield | Away - Joel Barlow HS-Joel Barlow HS Stadium [Directions] | 4:00 p.m. | ||
| Mon., 4/24 | V Boys Tennis | New Fairfield | Away - New Fairfield HS-Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Mon., 4/24 | V Girls Outdoor Track | Joel Barlow, Bunnell, New Fairfield | Away - Joel Barlow HS-Joel Barlow HS Stadium [Directions] | 4:00 p.m. | ||
| Mon., 4/24 | V Softball | Kolbe Cathedral | Away - Cal Ripken Field-Cal Ripken Field [Directions] | 4:15 p.m. | W 22-0 | |
| Mon., 4/24 | JV Softball | New Fairfield | Home - Pomperaug HS-Softball Field [Directions] | 4:30 p.m. | ||
| Mon., 4/24 | V Girls Tennis | New Fairfield | Home - Edgewood Bath and Tennis Club [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Tue., 4/25 | V Boys Lacrosse | New Fairfield | Away - New Fairfield HS-Marty Morgan Field [Directions] | 4:00 p.m. | L 17-6 | |
| Tue., 4/25 | JV Boys Lacrosse | New Fairfield | Away - New Fairfield HS-Marty Morgan Field [Directions] | 6:00 p.m. | ||
| Tue., 4/25 | V Boys Volleyball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 6:00 p.m. | L 2-3 | |
| Tue., 4/25 | JV Boys Volleyball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 4:30 p.m. | ||
| Tue., 4/25 | V Girls Golf | Bunnell | Home - Pomperaug HS-Pomperaug Golf Course [Directions] | 3:00 p.m. | Pomperaug 211 Bunnell 157 | |
| Tue., 4/25 | V Girls Lacrosse | New Fairfield | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | W 9-8 OT | |
| Tue., 4/25 | JV Girls Lacrosse | New Fairfield | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Wed., 4/26 | V Baseball | Immaculate | Home - Pomperaug HS-Baseball Field [Directions] | 4:15 p.m. | L 1-4 | |
| Wed., 4/26 | FR Baseball | New Fairfield | Away - New Fairfield HS-Baseball Field [Directions] | 4:15 p.m. | W 6-2 | |
| Wed., 4/26 | V Boys Tennis | Joel Barlow | Away - Joel Barlow HS-Tennis Courts [Directions] | 3:45 p.m. | L 5-2 [Detailed Results] | |
| Wed., 4/26 | V Boys Volleyball | Joel Barlow | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | L 1-3 | |
| Wed., 4/26 | JV Boys Volleyball | Joel Barlow | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 4/26 | V Girls Golf | Brookfield | Away - Sunset Hill Golf Course [Directions] | 3:00 p.m. | Pomperaug 225 Brookfield 231 | |
| Wed., 4/26 | V Softball | Immaculate | Home - Pomperaug HS-Softball Field [Directions] | 4:15 p.m. | W 11-6 | |
| Wed., 4/26 | V Girls Tennis | Joel Barlow | Home - Edgewood Bath and Tennis Club [Directions] | 4:00 p.m. | L 1-6 [Detailed Results] | |
| Thu., 4/27 | V Boys Lacrosse | Joel Barlow | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | L 13-11 | |
| Thu., 4/27 | JV Boys Lacrosse | Joel Barlow | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Thu., 4/27 | V Girls Golf | Immaculate | Away - Immaculate HS-Richter Park [Directions] | 3:00 p.m. | Pomperaug 241 Immaculate 204 | |
| Thu., 4/27 | V Girls Lacrosse | Joel Barlow | Away - Joel Barlow HS-Field J [Directions] | 4:00 p.m. | L 11-10 | |
| Thu., 4/27 | JV Girls Lacrosse | Joel Barlow | Away - Joel Barlow HS-Field J [Directions] | 5:30 p.m. | ||
| Fri., 4/28 | V Baseball | Brookfield | Away - Brookfield HS-Baseball Field [Directions] | 4:15 p.m. | L 1-7 | |
| Fri., 4/28 | FR Baseball | Joel Barlow | Home - Pomperaug HS-Baseball Field [Directions] | 4:15 p.m. | ||
| Fri., 4/28 | V Boys Outdoor Track | O;Grady Relays at Danbury High School | Away - Not Listed | Canceled | Cancelled | |
| Fri., 4/28 | V Boys Tennis | Wilcox Tech | Home - Edgewood Bath and Tennis Club [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Fri., 4/28 | V Girls Outdoor Track | O;Grady Relays at Danbury High School | Away - Not Listed | Canceled | Cancelled | |
| Fri., 4/28 | V Softball | Brookfield | Away - Brookfield HS-BHS Softball Field [Directions] | 4:15 p.m. | W 10-7 | |
| Sat., 4/29 | V Boys Lacrosse | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 9:00 a.m. | W 11-8 | |
| Sat., 4/29 | V Boys Outdoor Track | O;Grady Relays at Danbury High School | Away - Not Listed | Canceled | Cancelled | |
| Sat., 4/29 | V Girls Lacrosse | Lauralton Hall | Home - Pomperaug HS-Stadium [Directions] | 3:00 p.m. | W 16-10 | |
| Sat., 4/29 | JV Girls Lacrosse | Lauralton Hall | Home - Pomperaug HS-Stadium [Directions] | 1:00 p.m. | ||
| Sat., 4/29 | V Girls Outdoor Track | O;Grady Relays at Danbury High School | Away - Pomperaug HS-Stadium | Canceled | Cancelled | |
| Mon., 5/1 | V Boys Outdoor Track | Bethel, Masuk | Home - Pomperaug HS-Stadium [Directions] | 4:00 p.m. | ||
| Mon., 5/1 | V Boys Tennis | Bunnell | Home - Edgewood Bath and Tennis Club [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Mon., 5/1 | V Girls Tennis | Bunnell | Away - Bunnell HS-Bunnell Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Tue., 5/2 | JV Baseball | Stratford | Away - Wooster MS Field [Directions] | Postponed | ||
| Tue., 5/2 | FR Baseball | Bethel | Away - Bethel HS-MS Turf baseball field [Directions] | 4:30 p.m. | W 8-7 | |
| Tue., 5/2 | V Boys Lacrosse | Bunnell-Stratford | Away - Bunnell HS-Penders Field (Longbrook Park) [Directions] | 6:30 p.m. | W 20-5 | |
| Tue., 5/2 | JV Boys Lacrosse | Bunnell-Stratford | Away - Bunnell HS-Penders Field (Longbrook Park) [Directions] | 5:00 p.m. | ||
| Tue., 5/2 | V Girls Golf | Newtown, Immaculate | Away - Newtown Country Club [Directions] | 3:00 p.m. | Pomperaug 246, Newtown 198, Immaculate 204 | |
| Tue., 5/2 | V Girls Outdoor Track | Bethel, Masuk | Home - Pomperaug HS-Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/2 | JV Softball | Stratford | Away - DeLuca Field-Deluca Field [Directions] | Postponed | ||
| Wed., 5/3 | FR Baseball | New Milford | Away - New Milford HS-Baseball Sub Varsity Field - NMHS [Directions] | 4:15 p.m. | L 2-0 | |
| Wed., 5/3 | V Boys Volleyball | Daniel Hand | Home - Pomperaug HS-Main Gym [Directions] | 5:45 p.m. | W 3-0 | |
| Wed., 5/3 | JV Boys Volleyball | Daniel Hand | Home - Pomperaug HS-Main Gym [Directions] | 4:45 p.m. | ||
| Wed., 5/3 | V Girls Lacrosse | Branford | Home - Pomperaug HS-Stadium [Directions] | 6:00 p.m. | W 12-7 | |
| Thu., 5/4 | JV Baseball | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Fabbri Field [Directions] | Canceled | Cancelled | |
| Thu., 5/4 | V Boys Tennis | Nonnewaug | Away - Nonnewaug HS-Tennis Courts [Directions] | 3:00 p.m. | L 3-4 [Detailed Results] | |
| Thu., 5/4 | V Girls Golf | Stratford | Home - Pomperaug HS-Pomperaug Golf Course [Directions] | 3:00 p.m. | Pomperaug 231,Stratford 266 | |
| Thu., 5/4 | JV Softball | Naugatuck | Home - Pomperaug HS-Softball Field [Directions] | 4:00 p.m. | ||
| Thu., 5/4 | V Girls Tennis | Stratford | Away - Flood MS-Flood MS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Fri., 5/5 | V Baseball | Stratford | Home - Pomperaug HS-Baseball Field [Directions] | 4:15 p.m. | W 8-2 | |
| Fri., 5/5 | V Boys Lacrosse | Bethel | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | W 13-7 | |
| Fri., 5/5 | JV Boys Lacrosse | Bethel | Home - Pomperaug HS-Stadium [Directions] | 5:15 p.m. | ||
| Fri., 5/5 | V Boys Outdoor Track | Freshman/Soph Meet at Middletown High School | Away - Not Listed | TBA | ||
| Fri., 5/5 | V Boys Tennis | Stratford | Home - Edgewood Bath and Tennis Club [Directions] | 4:00 p.m. | W 6-1 [Detailed Results] | |
| Fri., 5/5 | V Boys Volleyball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 5/5 | JV Boys Volleyball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 4:30 p.m. | ||
| Fri., 5/5 | V Girls Lacrosse | Bethel | Away - Bethel HS-MS turf lacrosse field [Directions] | 5:45 p.m. | W 15-4 | |
| Fri., 5/5 | JV Girls Lacrosse | Bethel | Away - Bethel HS-MS turf lacrosse field [Directions] | 4:00 p.m. | ||
| Fri., 5/5 | V Girls Outdoor Track | Freshman/Soph Meet at Middletown High School | Away - TBA | TBA | ||
| Sat., 5/6 | V Baseball | Naugatuck | Home - Pomperaug HS-Baseball Field [Directions] | 10:00 a.m. | W 3-2 | |
| Sat., 5/6 | JV Baseball | Abbott Tech | Away - Abbott V-T School-Abbott Tech Baseball Field, School Campus [Directions] | 11:00 a.m. | ||
| Sat., 5/6 | V Boys Outdoor Track | Freshman/Soph Meet at Middletown High School | Away - Not Listed | TBA | ||
| Sat., 5/6 | V Boys Volleyball | Wolcott Tech | Home - Pomperaug HS-Main Gym [Directions] | 10:30 a.m. | W 3-0 | |
| Sat., 5/6 | JV Boys Volleyball | Wolcott Tech | Home - Pomperaug HS-Main Gym [Directions] | 12:00 p.m. | ||
| Sat., 5/6 | V Girls Outdoor Track | Freshman/Soph Meet at Middletown High School | Away - Not Listed | TBA | ||
| Sat., 5/6 | V Softball | Nonnewaug | Home - Pomperaug HS-Softball Field [Directions] | 11:00 a.m. | W 11-5 | |
| Mon., 5/8 | V Baseball | New Milford | Away - New Milford HS-Baseball Varsity Field - NMHS [Directions] | 4:15 p.m. | W 5-3 | |
| Mon., 5/8 | FR Baseball | Masuk | Home - Pomperaug HS-Baseball Field [Directions] | 4:15 p.m. | L 9-4 | |
| Mon., 5/8 | V Boys Outdoor Track | Brookfield, Immaculate, Notre Dame-Fairfield | Home - Pomperaug HS-Stadium [Directions] | 4:00 p.m. | ||
| Mon., 5/8 | V Boys Tennis | Naugatuck | Away - Naugatuck HS-Tennis Courts [Directions] | 3:30 p.m. | W 6-1 [Detailed Results] | |
| Mon., 5/8 | V Boys Volleyball | Oxford | Away - Oxford HS-Main Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Mon., 5/8 | V Girls Golf | Masuk, Newtown | Home - Pomperaug HS-Pomperaug Golf Course [Directions] | 3:00 p.m. | Pomperaug 227, Newtown 201, Masuk 198 | |
| Mon., 5/8 | V Girls Lacrosse | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 7:00 p.m. | L 10-8 | |
| Mon., 5/8 | JV Girls Lacrosse | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 5:00 p.m. | ||
| Mon., 5/8 | V Softball | New Milford | Away - New Milford HS-Softball Varsity Field - NMHS [Directions] | 4:15 p.m. | L 9-3 | |
| Mon., 5/8 | JV Softball | Newtown | Home - Pomperaug HS-Softball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/8 | V Girls Tennis | Notre Dame-Fairfield | Away - Veteran's Park - Bridgeport-Tennis Courts [Directions] | 3:45 p.m. | W 6-1 [Detailed Results] | |
| Tue., 5/9 | JV Baseball | New Milford | Home - Pomperaug HS-Baseball Field [Directions] | 4:15 p.m. | ||
| Tue., 5/9 | V Boys Lacrosse | Newtown | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | L 5-4 | |
| Tue., 5/9 | JV Boys Lacrosse | Newtown | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Tue., 5/9 | V Girls Outdoor Track | Brookfield, Immaculate, Notre Dame-Fairfield | Away - Brookfield HS-BHS Track [Directions] | 4:00 p.m. | ||
| Tue., 5/9 | V Softball | Stratford | Home - Pomperaug HS-Softball Field [Directions] | 4:15 p.m. | W 13-3 | |
| Wed., 5/10 | V Baseball | Masuk | Home - Pomperaug HS-Baseball Field [Directions] | 4:15 p.m. | L 2-8 | |
| Wed., 5/10 | V Boys Tennis | New Milford | Away - New Milford HS-Tennis Courts - NMHS [Directions] | 3:45 p.m. | L 5-2 [Detailed Results] | |
| Wed., 5/10 | V Boys Volleyball | Masuk | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | L 2-3 | |
| Wed., 5/10 | JV Boys Volleyball | Masuk | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 5/10 | V Softball | Masuk | Home - Pomperaug HS-Softball Field [Directions] | 4:15 p.m. | L 5-8 | |
| Wed., 5/10 | V Girls Tennis | New Milford | Home - Edgewood Bath and Tennis Club [Directions] | 4:00 p.m. | W 6-1 [Detailed Results] | |
| Thu., 5/11 | JV Baseball | Masuk | Away - Masuk HS-John Giampaolo Baseball Field @ Masuk HS [Directions] | 4:15 p.m. | ||
| Thu., 5/11 | V Boys Lacrosse | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Park Ave Field [Directions] | 4:00 p.m. | W 16-2 | |
| Thu., 5/11 | JV Boys Volleyball | New Milford | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 5/11 | V Girls Golf | Stratford, Immaculate | Away - Mill River Country Club [Directions] | 3:00 p.m. | Pomperaug 240, Stratford 260, Immaculate 224 | |
| Thu., 5/11 | V Girls Lacrosse | Notre Dame-Fairfield | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | W 19-1 | |
| Thu., 5/11 | JV Girls Lacrosse | Notre Dame-Fairfield | Home - Pomperaug HS-Stadium [Directions] | Canceled | Cancelled | |
| Thu., 5/11 | JV Softball | Trumbull | Home - Pomperaug HS-Softball Field [Directions] | 4:00 p.m. | ||
| Fri., 5/12 | V Baseball | Seymour | Home - Pomperaug HS-Baseball Field [Directions] | 3:30 p.m. | W 5-4 | |
| Fri., 5/12 | FR Baseball | Newtown | Away - Newtown HS-Nighthawk Ball Park [Directions] | 4:15 p.m. | L 11-1 | |
| Fri., 5/12 | V Boys Volleyball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Fri., 5/12 | JV Boys Volleyball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 4:15 p.m. | ||
| Fri., 5/12 | V Softball | Naugatuck | Home - Pomperaug HS-Softball Field [Directions] | 4:00 p.m. | L 0-4 | |
| Sat., 5/13 | V Baseball | Notre Dame-Fairfield | Home - Pomperaug HS-Baseball Field [Directions] | 11:00 a.m. | W 6-4 | |
| Sat., 5/13 | V Boys Outdoor Track | Freshmen SWC track meet | Away - Bethel HS-BHS track | 4:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 5/18 | ||||||
| Sat., 5/13 | V Girls Outdoor Track | Freshmen SWC track meet | Away - Bethel HS-BHS track | 4:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 5/18 | ||||||
| Sat., 5/13 | V Softball | Notre Dame-Fairfield | Home - Pomperaug HS-Softball Field [Directions] | 11:00 a.m. | L 9-5 | |
| Sat., 5/13 | JV Softball | Danbury | Home - Community House Park-Softball Field [Directions] | 11:30 a.m. | ||
| Sat., 5/13 | JV Softball | Danbury | Home - Community House Park-Softball Field [Directions] | 9:30 a.m. | ||
| Mon., 5/15 | V Baseball | Joel Barlow | Away - Joel Barlow HS-Baseball Field [Directions] | 4:15 p.m. | L 6-5 | |
| Mon., 5/15 | JV Baseball | Abbott Tech | Home - Pomperaug HS-Baseball Field [Directions] | 4:15 p.m. | ||
| Mon., 5/15 | V Boys Lacrosse | New Milford | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | L 15-9 | |
| Mon., 5/15 | JV Boys Lacrosse | New Milford | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Mon., 5/15 | V Boys Outdoor Track | Weston, New Milford | Away - Weston HS-WHS Track [Directions] | 4:00 p.m. | ||
| Mon., 5/15 | V Boys Tennis | Masuk | Home - Edgewood Bath and Tennis Club [Directions] | 4:00 p.m. | L 4-3 [Detailed Results] | |
| Mon., 5/15 | V Boys Volleyball | Cheshire | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | L 2-3 | |
| Mon., 5/15 | JV Boys Volleyball | Cheshire | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 5/15 | V Girls Golf | Brookfield | Home - Pomperaug HS-Pomperaug Golf Course [Directions] | 3:00 p.m. | Pomperaug 230, Brookfield 248 | |
| Mon., 5/15 | V Girls Lacrosse | New Milford | Away - New Milford HS-Joe Wiser Stadium - NMHS [Directions] | 5:45 p.m. | W 16-5 | |
| Mon., 5/15 | JV Girls Lacrosse | New Milford | Away - New Milford HS-North Turf Field - NMHS [Directions] | 4:00 p.m. | ||
| Mon., 5/15 | V Softball | Joel Barlow | Away - Joel Barlow High-Field E (Softball) [Directions] | 4:15 p.m. | W 13-0 | |
| Mon., 5/15 | V Girls Tennis | Masuk | Away - Wolfe Park-Tennis Courts [Directions] | 3:45 p.m. | L 3-4 [Detailed Results] | |
| Tue., 5/16 | JV Baseball | Joel Barlow | Home - Pomperaug HS-Baseball Field [Directions] | 4:15 p.m. | ||
| Tue., 5/16 | V Girls Golf | Weston | Away - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | Pomperaug 250, Weston 212 | |
| Tue., 5/16 | V Girls Outdoor Track | New Milford, Weston | Home - Pomperaug HS-Stadium [Directions] | 4:00 p.m. | ||
| Wed., 5/17 | JV Baseball | Brookfield | Home - Pomperaug HS-Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/17 | FR Baseball | New Fairfield | Home - Community House Park-Baseball Field [Directions] | 4:15 p.m. | W 7-6 | |
| Wed., 5/17 | V Girls Golf | Bunnell, Stratford | Away - Bunnell HS-Blackhawk Country Club (Old OCC) [Directions] | 3:00 p.m. | Pomperaug 250, Bunnell 309, Stratford 254 | |
| Wed., 5/17 | JV Softball | Brookfield | Home - Pomperaug HS-Softball Field [Directions] | 4:00 p.m. | ||
| Thu., 5/18 | V Boys Volleyball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | 6:00 p.m. | W 3-2 | |
| Thu., 5/18 | JV Boys Volleyball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | 4:30 p.m. | ||
| Sat., 5/20 | V Boys Volleyball | Newtown | Home - Pomperaug HS-Main Gym [Directions] | 11:30 a.m. | W 3-0 | |
| Sat., 5/20 | JV Boys Volleyball | Newtown | Home - Pomperaug HS-Main Gym [Directions] | 10:00 a.m. | ||
| Mon., 5/22 | V Boys Outdoor Track | SWC Outdoor Track Championship | Away - Bunnell HS-Bunnell Track | 3:00 p.m. | ||
| Mon., 5/22 | V Girls Outdoor Track | SWC Outdoor Track Championship | Away - Bunnell HS-Track | 3:00 p.m. | ||
| Tue., 5/23 | JV Baseball | Stratford | Away - Penders Field-Penders Field - Stratford [Directions] | 4:15 p.m. | ||
| Tue., 5/23 | V Boys Tennis | Wilcox Tech | Away - Wilcox Tech-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Tue., 5/23 | V Girls Golf | Masuk | Away - Whitney Farms Golf Course [Directions] | 2:15 p.m. | ||
| Tue., 5/23 | V Girls Tennis | Litchfield | Home - Edgewood Bath and Tennis Club [Directions] | 3:45 p.m. | L 2-5 [Detailed Results] | |