| Pomperaug 2023-24 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 799 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Mon., 8/21 | V Boys Golf | Multi-Team Scrimmage | Away - Rockledge Golf Club West Hartford | 3:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 8:30 a.m. | ||||||
| Tue., 8/22 | V Boys Golf | Bethel | Away - Bethel HS-Connecticut Country Club [Directions] | 2:00 p.m. | ||
| Wed., 8/23 | V Football | Wilby (Scrim.) | Home - Pomperaug HS-Stadium [Directions] | 4:00 p.m. | ||
| Wed., 8/23 | V Boys Golf | Brookfield | Away - Sunset Hill Golf Course [Directions] | 10:00 a.m. | ||
| Sat., 8/26 | V Football | Northwest United (Scrim.) | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Sun., 8/27 | V Boys Soccer | Alumni Game | Home - Pomperaug HS-Stadium [Directions] | 6:00 p.m. | ||
| Tue., 8/29 | V Boys Soccer | Nonnewaug (Scrim.) | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | ||
| Wed., 8/30 | V Boys Golf | Weston | Home - Pomperaug HS-Highfield Country Club [Directions] | 3:00 p.m. | ||
| Wed., 8/30 | V Field Hockey | Thomaston (Scrim.) | Home - Pomperaug HS-Stadium [Directions] | 3:30 p.m. | ||
| Wed., 8/30 | V Girls Soccer | Nonnewaug (Scrim.) | Home - Pomperaug HS-Stadium [Directions] | 5:30 p.m. | ||
| Thu., 8/31 | V Football | Woodland (Scrim.) | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | ||
| Thu., 8/31 | FR Football | Oxford (Scrim.) | Home - Pomperaug HS-Football Practice Field [Directions] | 5:30 p.m. | ||
| Thu., 8/31 | V Boys Soccer | Holy Cross (Scrim.) | Home - Pomperaug HS-Stadium [Directions] | 4:00 p.m. | ||
| Fri., 9/1 | V Boys Cross Country | Danbury (Scrim.) | Home - Pomperaug HS-Cross Country Course [Directions] | 4:30 p.m. | ||
| Fri., 9/1 | V Girls Cross Country | Danbury (Scrim.) | Home - Pomperaug HS-Cross Country Course [Directions] | 4:30 p.m. | ||
| Fri., 9/1 | V Girls Soccer | Cheshire (Scrim.) | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | ||
| Fri., 9/1 | JV Girls Soccer | Cheshire (Scrim.) | Home - Pomperaug HS-PHS Soccer Field [Directions] | 6:00 p.m. | ||
| Sat., 9/2 | V Boys Soccer | Cheshire (Scrim.) | Home - Pomperaug HS-Stadium [Directions] | 6:00 p.m. | ||
| Sat., 9/2 | JV Boys Soccer | Cheshire (Scrim.) | Home - Pomperaug HS-Stadium [Directions] | 4:00 p.m. | ||
| Sun., 9/3 | V Girls Soccer | Cheshire (Scrim.) | Away - Treadwell Park-Newtown Treadwell Park [Directions] | 10:20 a.m. | ||
| Sun., 9/3 | V Girls Soccer | Naugatuck (Scrim.) | Home - Treadwell Park-Newtown Treadwell Park [Directions] | 11:40 a.m. | ||
| Sun., 9/3 | V Girls Soccer | TBA | Home - Treadwell Park-Treadwell Town Park--Tilson Field [Directions] | 9:00 a.m. | ||
| Mon., 9/4 | V Boys Soccer | Scrimmage at Taft | Away - Not Listed | 9:30 a.m. | ||
| Mon., 9/4 | V Field Hockey | Amity, Danbury, TBA (Scrim.) | Home - Pomperaug HS-Stadium [Directions] | 9:00 a.m. | ||
| Tue., 9/5 | V Boys Golf | Joel Barlow | Away - Redding Country Club [Directions] | 3:00 p.m. | ||
| Tue., 9/5 | V Field Hockey | Cheshire (Scrim.) | Home - Pomperaug HS-Stadium [Directions] | 6:15 p.m. | ||
| Wed., 9/6 | FR Football | Sheehan (Scrim.) | Home - Pomperaug HS-Stadium [Directions] | Postponed | ||
| Thu., 9/7 | V Boys Soccer | Woodland | Home - Pomperaug HS-Stadium [Directions] | 6:00 p.m. | W 3-0 | |
| Thu., 9/7 | V Girls Soccer | Woodland | Home - Pomperaug HS-Stadium [Directions] | 8:00 p.m. | T 1-1 | |
| Fri., 9/8 | JV Boys Soccer | Woodland | Away - Pent Field - Beacon Falls Recreation Complex [Directions] | Postponed | ||
| Fri., 9/8 | V Girls Swimming and Diving | Stratford | Away - Flood MS-Flood MS Pool [Directions] | 4:30 p.m. | 84-70 Pomperaug | |
| Fri., 9/8 | V Girls Volleyball | Seymour | Away - Seymour HS-Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Fri., 9/8 | JV Girls Volleyball | Seymour | Away - Seymour HS-Gym [Directions] | 4:30 p.m. | ||
| Sat., 9/9 | V Football | Bullard/Kolbe | Away - John F Kennedy Stadium [Directions] | 3:30 p.m. | W 42-7 | |
| Sat., 9/9 | JV Football | Weston | Away - Weston HS-WHS Stadium Field [Directions] | 10:00 a.m. | ||
| Sat., 9/9 | V Girls Soccer | Mercy | Away - Xavier HS-Larry McHugh Field [Directions] | 2:00 p.m. | L 0-7 | |
| Sat., 9/9 | V Girls Volleyball | Westhill | Home - Pomperaug HS-Main Gym [Directions] | 12:30 p.m. | L 2-3 | |
| Sat., 9/9 | JV Girls Volleyball | Westhill | Home - Pomperaug HS-Main Gym [Directions] | 11:00 a.m. | ||
| Tue., 9/12 | V Boys Cross Country | Immaculate, Newtown | Home - Pomperaug HS-Cross Country Course [Directions] | 4:30 p.m. | Pomperaug 24 Immaculate 35 Pomperaug 22 Newtown 37 | |
| Tue., 9/12 | V Boys Soccer | Bunnell | Away - Bunnell HS-Mastroni Field [Directions] | 6:30 p.m. | L 1-0 | |
| Tue., 9/12 | JV Boys Soccer | Bunnell | Away - Bunnell HS-Mastroni Field [Directions] | 4:30 p.m. | ||
| Tue., 9/12 | V Girls Cross Country | Immaculate, Newtown | Home - Pomperaug HS-Cross Country Course [Directions] | 5:00 p.m. | Newtown 24 Pomperaug 33 Pomperaug 16 Immaculate 47 | |
| Tue., 9/12 | V Girls Soccer | Bunnell | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | W 6-0 | |
| Tue., 9/12 | JV Girls Soccer | Bunnell | Home - Pomperaug HS-Stadium [Directions] | 5:15 p.m. | ||
| Tue., 9/12 | V Girls Swimming and Diving | Newtown | Away - Newtown HS-pool [Directions] | 5:00 p.m. | 96/88 Pomperaug | |
| Wed., 9/13 | V Boys Golf | Masuk | Home - Pomperaug HS-Highfield Country Club [Directions] | Postponed | ||
| Wed., 9/13 | FR Boys Soccer | Bethel | Away - Bethel HS-Rockwell Field [Directions] | Postponed | ||
| Wed., 9/13 | V Field Hockey | Watertown | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | W 1-0 | |
| Wed., 9/13 | JV Field Hockey | Watertown | Home - Pomperaug HS-Stadium [Directions] | Canceled | Cancelled | |
| Thu., 9/14 | FR Football | Seymour | Away - Seymour HS-turf field [Directions] | 4:00 p.m. | ||
| Thu., 9/14 | V Boys Soccer | Weston | Away - Weston HS-WHS Stadium Field [Directions] | 4:15 p.m. | W 1-0 | |
| Thu., 9/14 | JV Boys Soccer | Weston | Away - Weston HS-WHS Lower Turf Field [Directions] | 4:15 p.m. | ||
| Thu., 9/14 | V Girls Soccer | Weston | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | L 0-1 | |
| Thu., 9/14 | JV Girls Soccer | Weston | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Fri., 9/15 | V Football | Brookfield | Home - Pomperaug HS-Stadium [Directions] | 4:30 p.m. | W 20-12 | |
| Fri., 9/15 | V Girls Volleyball | Amistad | Home - Pomperaug HS-Main Gym [Directions] | 4:30 p.m. | W 3-0 | |
| Fri., 9/15 | JV Girls Volleyball | Amistad | Home - Pomperaug HS-Main Gym [Directions] | 3:15 p.m. | ||
| Fri., 9/15 | FR Girls Volleyball | Bethel | Home - Pomperaug HS-Auxiliary Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/16 | JV Football | Brookfield | Away - Brookfield HS-BHS Back Turf [Directions] | 10:30 a.m. | ||
| Sat., 9/16 | FR Boys Soccer | Masuk | Away - Masuk HS-Masuk High School Middle Field [Directions] | 10:00 a.m. | ||
| Mon., 9/18 | V Field Hockey | New Fairfield | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | W 4-2 | |
| Mon., 9/18 | JV Field Hockey | New Fairfield | Home - Pomperaug HS-Stadium [Directions] | 5:15 p.m. | ||
| Mon., 9/18 | V Girls Volleyball | Joel Barlow | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Mon., 9/18 | JV Girls Volleyball | Joel Barlow | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 9/19 | V Boys Cross Country | Masuk, Notre Dame-Fairfield, Stratford | Away - Great Hollow Lake Field-Cross Country Trail [Directions] | 5:00 p.m. | PHS 15. Masuk 50 PHS 15 NDHS 48 PHS 15. Stratford 50 | |
| Tue., 9/19 | V Boys Golf | New Fairfield | Away - Club River Oaks [Directions] | 2:00 p.m. | ||
| Tue., 9/19 | V Boys Soccer | Bethel | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | T 1-1 | |
| Tue., 9/19 | JV Boys Soccer | Bethel | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Tue., 9/19 | V Girls Cross Country | Masuk, Notre Dame-Fairfield, Stratford | Away - Great Hollow Lake Field-Cross Country Trail [Directions] | 5:00 p.m. | PHS 18 Masuk 45 PHS 15 Stratford 50 PHS 15 NDHS 50 | |
| Tue., 9/19 | V Girls Soccer | Bethel | Away - Bethel HS-MS Turf Soccer Field [Directions] | 4:00 p.m. | L 0-2 | |
| Tue., 9/19 | JV Girls Soccer | Bethel | Away - Bethel HS-Rockwell Field [Directions] | 4:00 p.m. | ||
| Tue., 9/19 | V Girls Swimming and Diving | New Fairfield | Home - Pomperaug HS-PHS Pool [Directions] | 4:00 p.m. | 90/75 Pomperaug | |
| Wed., 9/20 | V Boys Golf | Stratford | Home - Pomperaug HS-Highfield Country Club [Directions] | 3:00 p.m. | ||
| Wed., 9/20 | V Field Hockey | Joel Barlow | Away - Joel Barlow HS-Field I (Stadium) [Directions] | 7:00 p.m. | W 3-1 | |
| Wed., 9/20 | JV Field Hockey | Joel Barlow | Away - Joel Barlow HS-Field I (Stadium) [Directions] | 5:30 p.m. | ||
| Wed., 9/20 | V Girls Volleyball | Bunnell | Away - Bunnell HS-David Johnson Gymnasium [Directions] | 6:00 p.m. | W 3-0 | |
| Wed., 9/20 | JV Girls Volleyball | Bunnell | Away - Bunnell HS-David Johnson Gymnasium [Directions] | 4:30 p.m. | ||
| Wed., 9/20 | FR Girls Volleyball | Nonnewaug (Scrim.) | Away - Nonnewaug HS-Gym [Directions] | 5:00 p.m. | ||
| Thu., 9/21 | FR Football | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 5:30 p.m. | ||
| Thu., 9/21 | V Boys Golf | Bunnell | Away - Bunnell HS-Blackhawk Country Club (Old OCC) [Directions] | 3:00 p.m. | ||
| Thu., 9/21 | V Boys Soccer | Newtown | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | T 2-2 | |
| Thu., 9/21 | JV Boys Soccer | Newtown | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Thu., 9/21 | FR Boys Soccer | New Milford | Home - Pomperaug HS-PHS Soccer Field [Directions] | 4:00 p.m. | ||
| Thu., 9/21 | V Girls Soccer | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 6:00 p.m. | L 0-2 | |
| Thu., 9/21 | JV Girls Soccer | Newtown | Away - Newtown HS-NHS Soccer Practice Fields [Directions] | 4:00 p.m. | ||
| Fri., 9/22 | V Football | Harding | Home - Pomperaug HS-Stadium [Directions] | 6:30 p.m. | W 41-8 | |
| Sat., 9/23 | JV Football | Harding | Away - Warren Harding HS-Lewis Field [Directions] | Canceled | Cancelled | |
| Sat., 9/23 | V Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 12:30 p.m. | L 3-5 | |
| Sat., 9/23 | JV Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | Canceled | Cancelled | |
| Tue., 9/26 | V Boys Cross Country | Bethel, Bunnell, New Milford | Home - Pomperaug HS-Cross Country Course [Directions] | 4:30 p.m. | NMHS 17 PHS 38 PHS 21 Bethel 38 PHS 16 Bunnell 47 | |
| Tue., 9/26 | V Boys Golf | Newtown | Home - Pomperaug HS-Highfield Country Club [Directions] | 3:00 p.m. | ||
| Tue., 9/26 | V Boys Soccer | New Fairfield | Away - New Fairfield HS-Marty Morgan Field [Directions] | 6:00 p.m. | W 2-0 | |
| Tue., 9/26 | JV Boys Soccer | New Fairfield | Away - New Fairfield HS-Marty Morgan Field [Directions] | 4:00 p.m. | ||
| Tue., 9/26 | V Girls Cross Country | Bethel, Bunnell, New Milford | Home - Pomperaug HS-Cross Country Course [Directions] | 5:00 p.m. | PHS 18 Bethel 41 PHS 15 Bunnell 50 NMHS 22 PHS 38 | |
| Tue., 9/26 | V Girls Soccer | New Fairfield | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | L 0-1 | |
| Tue., 9/26 | JV Girls Soccer | New Fairfield | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Tue., 9/26 | V Girls Swimming and Diving | Brookfield | Home - Pomperaug HS-PHS Pool [Directions] | 4:30 p.m. | 93/85 Pomp | |
| Tue., 9/26 | V Girls Volleyball | Weston | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Tue., 9/26 | JV Girls Volleyball | Weston | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 9/26 | FR Girls Volleyball | Weston | Home - Pomperaug HS-Auxiliary Gym [Directions] | 4:00 p.m. | ||
| Wed., 9/27 | FR Football | New Milford | Home - Pomperaug HS-Stadium [Directions] | 3:45 p.m. | ||
| Wed., 9/27 | V Boys Golf | Immaculate | Home - Pomperaug HS-Highfield Country Club [Directions] | 3:00 p.m. | ||
| Wed., 9/27 | FR Boys Soccer | Newtown | Away - Newtown HS-NHS Soccer Practice Fields [Directions] | 3:30 p.m. | ||
| Wed., 9/27 | V Field Hockey | Bethel | Home - Pomperaug HS-Stadium [Directions] | 7:30 p.m. | W 8-0 | |
| Wed., 9/27 | JV Field Hockey | Bethel | Home - Pomperaug HS-Stadium [Directions] | 6:00 p.m. | ||
| Thu., 9/28 | V Boys Golf | 2023 CIAC Fall Golf Classic at Orange Hills Golf Course | Away - Pomperaug HS-Highfield Country Club | 2:30 p.m. | ||
| Thu., 9/28 | JV Boys Golf | Newtown | Away - Newtown Country Club [Directions] | 3:00 p.m. | ||
| Thu., 9/28 | V Boys Soccer | Kolbe Cathedral | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | W 2-0 | |
| Thu., 9/28 | V Girls Soccer | Kolbe Cathedral | Away - Veterans Memorial Park CT [Directions] | 4:15 p.m. | W 10-0 | |
| Fri., 9/29 | V Football | New Milford | Away - New Milford HS-Joe Wiser Stadium - NMHS [Directions] | 7:00 p.m. | L 6-20 | |
| Fri., 9/29 | V Girls Volleyball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 4:00 p.m. | W 3-2 | |
| Fri., 9/29 | JV Girls Volleyball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 5:30 p.m. | ||
| Fri., 9/29 | FR Girls Volleyball | Brookfield | Away - Brookfield HS-BHS Small Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/30 | V Boys Cross Country | Nonnewaug JV Invitational | Away - Not Listed | TBA | ||
| Sat., 9/30 | JV Football | New Milford | Home - Pomperaug HS-Stadium [Directions] | 10:30 a.m. | ||
| Sat., 9/30 | V Girls Cross Country | Nonnewaug JV Invitational | Away - Not Listed | TBA | ||
| Sat., 9/30 | V Field Hockey | New Milford | Home - Pomperaug HS-Stadium [Directions] | 3:30 p.m. | W 3-0 | |
| Sat., 9/30 | JV Field Hockey | New Milford | Home - Pomperaug HS-Stadium [Directions] | 2:00 p.m. | ||
| Sat., 9/30 | V Girls Volleyball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 11:15 p.m. | L 0-3 | |
| Sat., 9/30 | JV Girls Volleyball | Nonnewaug | Away - Nonnewaug HS-Gym [Directions] | 10:00 a.m. | ||
| Mon., 10/2 | V Boys Golf | Avon Invitational | Away - Hop Meadow Country Club | 11:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 11:00 a.m. | ||||||
| Mon., 10/2 | FR Boys Soccer | Masuk | Home - Pomperaug HS-PHS Soccer Field [Directions] | 3:45 p.m. | ||
| Mon., 10/2 | V Field Hockey | Immaculate | Away - Immaculate HS-Rogers Park, Danbury [Directions] | 4:00 p.m. | W 2-1 | |
| Mon., 10/2 | JV Field Hockey | Immaculate | Away - Immaculate HS-Rogers Park, Danbury [Directions] | 5:30 p.m. | ||
| Mon., 10/2 | V Girls Volleyball | Newtown | Away - Newtown HS-Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Mon., 10/2 | JV Girls Volleyball | Newtown | Away - Newtown HS-Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/3 | V Boys Cross Country | Joel Barlow, New Fairfield, Weston | Away - Joel Barlow HS-Cross Country Course [Directions] | 4:30 p.m. | PHS 25. JBHS 46 PHS 15 NFHS 50 PHS 20 Weston 43 | |
| Tue., 10/3 | V Boys Golf | Brookfield | Home - Pomperaug HS-Highfield Country Club [Directions] | 3:00 p.m. | ||
| Tue., 10/3 | V Boys Soccer | Immaculate | Away - MILL RIDGE PRIMARY SCHOOL-Field [Directions] | 3:15 p.m. | W 5-0 | |
| Tue., 10/3 | JV Boys Soccer | Immaculate | Away - Immaculate HS [Directions] | Postponed | ||
| Tue., 10/3 | V Girls Cross Country | Joel Barlow, New Fairfield, Weston | Away - Joel Barlow HS-Cross Country Course [Directions] | 5:00 p.m. | PHS 25 NFHS 34 PHS 22 JBHS 37 PHS 17 Weston 46 | |
| Tue., 10/3 | V Girls Swimming and Diving | Weston | Away - Weston HS-Weston MS Pool [Directions] | 4:00 p.m. | 101/84 Pomperaug | |
| Tue., 10/3 | FR Girls Volleyball | Newtown | Home - Pomperaug HS-Auxiliary Gym [Directions] | 5:15 p.m. | ||
| Wed., 10/4 | V Boys Golf | New Milford | Away - Candlewood Valley Country Club [Directions] | 3:00 p.m. | ||
| Wed., 10/4 | V Field Hockey | New Milford | Away - New Milford HS-Joe Wiser Stadium - NMHS [Directions] | 5:15 p.m. | OT-L 2-3 | |
| Wed., 10/4 | JV Field Hockey | New Milford | Away - New Milford HS-Joe Wiser Stadium - NMHS [Directions] | 3:45 p.m. | ||
| Wed., 10/4 | JV Girls Volleyball | New Fairfield | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/4 | FR Girls Volleyball | New Fairfield | Home - Pomperaug HS-Auxiliary Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/5 | V Boys Soccer | Brookfield | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | T 2-2 | |
| Thu., 10/5 | JV Boys Soccer | Brookfield | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Thu., 10/5 | FR Boys Soccer | Newtown | Home - Pomperaug HS-PHS Soccer Field [Directions] | 3:30 p.m. | ||
| Thu., 10/5 | V Girls Soccer | Brookfield | Away - Brookfield HS-BHS Back Turf [Directions] | 4:00 p.m. | L 1-5 | |
| Thu., 10/5 | JV Girls Soccer | Brookfield | Away - Cadigan Field-Cadigan - East [Directions] | 4:00 p.m. | ||
| Thu., 10/5 | V Girls Swimming and Diving | Joel Barlow | Home - Pomperaug HS-PHS Pool [Directions] | 4:00 p.m. | 92/61 Pomperaug | |
| Fri., 10/6 | V Field Hockey | New Fairfield | Away - New Fairfield HS-Marty Morgan Field [Directions] | 5:30 p.m. | W 4-3 | |
| Fri., 10/6 | JV Field Hockey | New Fairfield | Away - New Fairfield HS-Marty Morgan Field [Directions] | 4:00 p.m. | ||
| Fri., 10/6 | V Girls Volleyball | Kolbe Cathedral | Away - Kolbe Cathedral HS-Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 10/6 | JV Girls Volleyball | Kolbe Cathedral | Away - Kolbe Cathedral HS-Gym [Directions] | 4:15 p.m. | ||
| Sat., 10/7 | V Boys Cross Country | Brewster Invitational | Away - Not Listed | 4:30 p.m. | Cancelled | |
| Sat., 10/7 | V Boys Soccer | Watertown | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | W 2-0 | |
| Sat., 10/7 | FR Boys Soccer | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | Postponed | ||
| Sat., 10/7 | V Girls Cross Country | Brewster Invitational | Away - Not Listed | TBA | Cancelled | |
| Sat., 10/7 | V Girls Soccer | Watertown | Home - Pomperaug HS-Stadium [Directions] | 3:00 p.m. | T 1-1 | |
| Sat., 10/7 | V Girls Volleyball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 2:00 p.m. | L 2-3 | |
| Sat., 10/7 | JV Girls Volleyball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 12:30 p.m. | ||
| Sat., 10/7 | FR Girls Volleyball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 11:00 a.m. | ||
| Tue., 10/10 | V Boys Cross Country | Kolbe Cathedral, Brookfield | Away - Seaside Park-Seaside Park [Directions] | 4:30 p.m. | Brook 25. PHS 30 PHS 23 Kolbe 34 | |
| Tue., 10/10 | V Boys Golf | Notre Dame-Fairfield | Home - Pomperaug HS-Highfield Country Club [Directions] | 3:00 p.m. | ||
| Tue., 10/10 | V Boys Soccer | Stratford | Away - Penders Field-Penders Field - Stratford [Directions] | 7:00 p.m. | W 6-0 | |
| Tue., 10/10 | JV Boys Soccer | Stratford | Away - Penders Field-Penders Field - Stratford [Directions] | 5:00 p.m. | ||
| Tue., 10/10 | FR Boys Soccer | Shelton | Home - Pomperaug HS-PHS Soccer Field [Directions] | 3:30 p.m. | ||
| Tue., 10/10 | V Girls Cross Country | Kolbe Cathedral, Brookfield | Away - Seaside Park-Seaside Park [Directions] | 5:00 p.m. | PHS 15 Kolbe 50 PHS 24 Brookfield 35 | |
| Tue., 10/10 | JV Girls Soccer | Stratford | Home - Pomperaug HS-Stadium [Directions] | Postponed | ||
| Tue., 10/10 | V Girls Swimming and Diving | New Milford | Home - Pomperaug HS-PHS Pool [Directions] | 4:00 p.m. | 90/86 Pomperaug | |
| Tue., 10/10 | V Girls Volleyball | Immaculate | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | L 2-3 | |
| Tue., 10/10 | JV Girls Volleyball | Immaculate | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/10 | FR Girls Volleyball | Immaculate | Home - Pomperaug HS-Auxiliary Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/11 | V Boys Golf | Bethel, Masuk | Home - Pomperaug HS-Highfield Country Club [Directions] | 3:00 p.m. | ||
| Wed., 10/11 | V Field Hockey | Masuk | Home - Pomperaug HS-Stadium [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 10/11 | JV Field Hockey | Masuk | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | ||
| Wed., 10/11 | FR Girls Volleyball | Bethel | Away - Bethel HS-BHS gym [Directions] | Postponed | ||
| Thu., 10/12 | V Girls Soccer | Notre Dame-Fairfield | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | L 1-2 | |
| Thu., 10/12 | V Girls Volleyball | Bethel | Away - Bethel HS-Gym [Directions] | 5:30 p.m. | W 3-1 | |
| Thu., 10/12 | JV Girls Volleyball | Bethel | Away - Bethel HS-Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/13 | V Football | Weston | Home - Pomperaug HS-Stadium [Directions] | 6:30 p.m. | W 38-7 | |
| Fri., 10/13 | FR Boys Soccer | New Milford | Away - New Milford HS-Middle Soccer Field - NMHS [Directions] | 4:00 p.m. | ||
| Fri., 10/13 | V Field Hockey | Farmington | Away - Farmington HS-Turf Field [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 10/13 | JV Field Hockey | Farmington | Away - Farmington HS-Turf Field [Directions] | 4:15 p.m. | ||
| Fri., 10/13 | V Girls Soccer | Immaculate | Home - Pomperaug HS-Stadium [Directions] | 3:00 p.m. | W 3-0 | |
| Fri., 10/13 | V Girls Swimming and Diving | Masuk | Away - Masuk HS-Pool [Directions] | 4:00 p.m. | 90/85 Pomperaug | |
| Sat., 10/14 | JV Football | Weston | Away - Weston HS-WHS Stadium Field [Directions] | Canceled | Cancelled | |
| Sat., 10/14 | FR Football | ATI | Home - Pomperaug HS-Stadium [Directions] | 10:00 a.m. | ||
| Sat., 10/14 | V Boys Soccer | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Park Ave Field [Directions] | 12:00 p.m. | W 2-0 | |
| Mon., 10/16 | V Boys Soccer | Abbott Tech | Away - Broadview MS-Stephen A. Kaplanis Turf Field [Directions] | 3:30 p.m. | T 0-0 | |
| Mon., 10/16 | FR Boys Soccer | Bethel | Home - Pomperaug HS-PHS Soccer Field [Directions] | 3:45 p.m. | ||
| Mon., 10/16 | V Field Hockey | Brookfield | Away - Brookfield HS-BHS Back Turf [Directions] | 5:00 p.m. | W 6-0 | |
| Mon., 10/16 | JV Field Hockey | Brookfield | Away - Brookfield HS-BHS Back Turf [Directions] | 3:30 p.m. | ||
| Mon., 10/16 | V Girls Volleyball | Stratford | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | L 1-3 | |
| Mon., 10/16 | JV Girls Volleyball | Stratford | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 10/16 | FR Girls Volleyball | Stratford | Home - Pomperaug HS-Auxiliary Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/17 | V Boys Soccer | New Milford | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | L 2-0 | |
| Tue., 10/17 | JV Boys Soccer | New Milford | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Tue., 10/17 | V Girls Soccer | New Milford | Away - New Milford HS-Joe Wiser Stadium - NMHS [Directions] | 6:00 p.m. | W 3-1 | |
| Tue., 10/17 | JV Girls Soccer | New Milford | Away - New Milford HS-Joe Wiser Stadium - NMHS [Directions] | 4:00 p.m. | ||
| Tue., 10/17 | V Girls Swimming and Diving | Bunnell | Home - Pomperaug HS-PHS Pool [Directions] | 5:30 p.m. | 89/81 Pomperaug | |
| Tue., 10/17 | V Girls Volleyball | New Milford | Away - New Milford HS-Main Gym - NMHS [Directions] | 6:30 p.m. | L 2-3 | |
| Tue., 10/17 | JV Girls Volleyball | New Milford | Away - New Milford HS-Main Gym - NMHS [Directions] | 5:00 p.m. | ||
| Tue., 10/17 | FR Girls Volleyball | New Milford | Away - New Milford HS-Main Gym - NMHS [Directions] | 4:00 p.m. | ||
| Wed., 10/18 | V Boys Cross Country | SWC Champioship | Away - Bethel HS-BHS track | 3:00 p.m. | ||
| Wed., 10/18 | V Boys Golf | SWC Boys Golf Championship at Fairchild Wheeler-Black Course | Home - TBA [Directions] | 8:30 a.m. | ||
| Wed., 10/18 | JV Boys Soccer | Abbott Tech | Home - Pomperaug HS-PHS Soccer Field [Directions] | 3:45 p.m. | ||
| Wed., 10/18 | V Girls Cross Country | SWC Champioship | Away - Bethel HS-BHS track | 3:00 p.m. | ||
| Wed., 10/18 | V Field Hockey | Weston | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | T 0-0 | |
| Wed., 10/18 | JV Field Hockey | Weston | Home - Pomperaug HS-Stadium [Directions] | 5:30 p.m. | ||
| Wed., 10/18 | FR Girls Volleyball | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/19 | FR Football | Masuk | Home - Pomperaug HS-Stadium [Directions] | Postponed | ||
| Thu., 10/19 | V Boys Soccer | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 6:00 p.m. | T 0-0 | |
| Thu., 10/19 | JV Boys Soccer | Masuk | Away - Masuk HS-Masuk High School Middle Field [Directions] | 4:00 p.m. | ||
| Thu., 10/19 | V Girls Soccer | Masuk | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | W 2-1 | |
| Thu., 10/19 | JV Girls Soccer | Masuk | Home - Pomperaug HS-Stadium [Directions] | 5:15 p.m. | ||
| Thu., 10/19 | V Girls Volleyball | Notre Dame-Fairfield | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Thu., 10/19 | JV Girls Volleyball | Notre Dame-Fairfield | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/20 | V Football | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 7:00 p.m. | L 23-44 | |
| Fri., 10/20 | V Field Hockey | Granby Memorial | Home - Pomperaug HS-Stadium [Directions] | 5:30 p.m. | W 2-0 | |
| Fri., 10/20 | JV Field Hockey | Granby Memorial | Home - Pomperaug HS-Stadium [Directions] | Canceled | Cancelled | |
| Fri., 10/20 | V Girls Soccer | Stratford | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | W 4-0 | |
| Sat., 10/21 | JV Football | Masuk | Home - Pomperaug HS-Stadium [Directions] | 10:30 a.m. | ||
| Sat., 10/21 | JV Girls Soccer | Woodland | Home - Pomperaug HS-Stadium [Directions] | 1:30 p.m. | ||
| Sat., 10/21 | V Girls Volleyball | Oxford | Away - Oxford HS-Main Gym [Directions] | 11:00 a.m. | W 3-0 | |
| Sat., 10/21 | JV Girls Volleyball | Oxford | Away - Oxford HS-Gym 1 [Directions] | 10:00 a.m. | ||
| Mon., 10/23 | V Boys Golf | CIAC Division II Fall Championship | Away - Chippanee GC | 8:30 a.m. | ||
| Mon., 10/23 | V Boys Soccer | Joel Barlow | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | L 2-0 | |
| Mon., 10/23 | JV Boys Soccer | Joel Barlow | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Mon., 10/23 | FR Boys Soccer | Shelton | Away - Shelton HS-Lower Field [Directions] | 4:00 p.m. | ||
| Mon., 10/23 | V Girls Soccer | Joel Barlow | Away - Joel Barlow HS-Field J (Competition Field) [Directions] | 6:00 p.m. | L 0-1 | |
| Mon., 10/23 | JV Girls Soccer | Joel Barlow | Away - Joel Barlow HS-Field J (Competition Field) [Directions] | 4:00 p.m. | ||
| Mon., 10/23 | V Girls Volleyball | Masuk | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | L 2-3 | |
| Mon., 10/23 | JV Girls Volleyball | Masuk | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 10/23 | FR Girls Volleyball | Masuk | Home - Pomperaug HS-Auxiliary Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/24 | V Field Hockey | Newtown | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | L 0-3 | |
| Tue., 10/24 | JV Field Hockey | Newtown | Home - Pomperaug HS-Stadium [Directions] | 5:30 p.m. | ||
| Tue., 10/24 | V Girls Swimming and Diving | Bethel/Immaculate | Away - Bethel HS-WCSU- Oneil Center [Directions] | 3:45 p.m. | 85/60 | |
| Wed., 10/25 | FR Boys Soccer | Naugatuck | Home - Pomperaug HS-PHS Soccer Field [Directions] | 3:30 p.m. | ||
| Wed., 10/25 | V Girls Volleyball | Naugatuck | Home - Pomperaug HS-Main Gym [Directions] | 5:00 p.m. | L 1-3 | |
| Wed., 10/25 | JV Girls Volleyball | Naugatuck | Home - Pomperaug HS-Main Gym [Directions] | 3:30 p.m. | ||
| Wed., 10/25 | FR Girls Volleyball | Naugatuck | Home - Pomperaug HS-Auxiliary Gym [Directions] | 3:30 p.m. | ||
| Thu., 10/26 | FR Football | Stratford | Home - Pomperaug HS-Stadium [Directions] | 3:30 p.m. | ||
| Thu., 10/26 | V Field Hockey | Masuk | Home - Pomperaug HS-Stadium [Directions] | 6:15 p.m. | ||
| Thu., 10/26 | V Girls Volleyball | New Fairfield | Home - Pomperaug HS-Main Gym [Directions] | 3:45 p.m. | W 3-2 | |
| Thu., 10/26 | FR Girls Volleyball | Newtown | Away - Newtown HS-Gym [Directions] | 3:30 p.m. | ||
| Fri., 10/27 | V Football | Stratford | Away - Penders Field-Penders Field - Stratford [Directions] | 7:00 p.m. | W 34-6 | |
| Fri., 10/27 | FR Boys Soccer | Watertown | Home - Pomperaug HS-PHS Soccer Field [Directions] | 3:15 p.m. | ||
| Sat., 10/28 | V Boys Cross Country | CIAC Class MM Championship | Away - Wickham Park | 1:30 p.m. | ||
| Sat., 10/28 | JV Football | Stratford | Home - Pomperaug HS-Stadium [Directions] | Postponed | ||
| Sat., 10/28 | V Boys Soccer | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 3:00 p.m. | ||
| Sat., 10/28 | V Girls Cross Country | CIAC Class MM Championship | Away - Wickham Park | 12:55 p.m. | ||
| Sat., 10/28 | V Girls Volleyball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Mon., 10/30 | V Field Hockey | Immaculate | Home - Pomperaug HS-Stadium [Directions] | 6:30 p.m. | ||
| Mon., 10/30 | V Girls Swimming and Diving | Weston, Bethel/Immaculate, Brookfield, Immaculate, Joel Barlow, Masuk, New Fairfield, New Milford, Newtown | Away - Weston HS-Weston MS Pool | 5:30 p.m. | ||
| Mon., 10/30 | Unified Sports Soccer | Brookfield | Home - Pomperaug HS-Main Gym [Directions] | 3:00 p.m. | ||
| Tue., 10/31 | V Boys Soccer | Bethel | Away - Bethel HS-MS Turf Soccer Field [Directions] | 4:00 p.m. | ||
| Thu., 11/2 | FR Football | Newtown | Away - Newtown HS-NHS Back Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 11/2 | V Boys Swimming and Diving | TBA, Brookfield, Bunnell-Stratford, Immaculate, Joel Barlow-Bethel Swim, TBA, New Fairfield, Notre Dame-Fairfield, Stratford, Weston | Away - Masuk HS-Pool | 4:00 p.m. | ||
| Thu., 11/2 | V Field Hockey | New Milford | Home - Brookfield HS-BHS Stadium Field [Directions] | 7:00 p.m. | ||
| Thu., 11/2 | V Girls Swimming and Diving | SWC Swimming Championship | Away - Masuk HS-Pool | 5:00 p.m. | ||
| Fri., 11/3 | V Football | Newtown | Home - Pomperaug HS-Stadium [Directions] | 6:30 p.m. | L 10-25 | |
| Sat., 11/4 | JV Football | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 9:00 a.m. | ||
| Sat., 11/4 | V Boys Soccer | Holy Cross (Scrim.) | Home - Pomperaug HS-Stadium [Directions] | 12:00 p.m. | ||
| Mon., 11/6 | V Boys Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Mon., 11/6 | V Girls Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Mon., 11/6 | V Girls Soccer | Avon | Away - Avon HS-Turf Field [Directions] | 4:00 p.m. | L 1-6 | |
| Tue., 11/7 | V Boys Soccer | Wethersfield | Away - Wethersfield HS-Cottone Field [Directions] | 6:30 p.m. | ||
| Tue., 11/7 | V Field Hockey | Waterford | Home - Pomperaug HS-Stadium [Directions] | 6:00 p.m. | ||
| Tue., 11/7 | V Girls Volleyball | Rockville | Away - Rockville HS-Main gymnasium [Directions] | 6:00 p.m. | L 0-3 | |
| Thu., 11/9 | V Field Hockey | New Canaan | Home - Pomperaug HS-Stadium [Directions] | 4:00 p.m. | ||
| Thu., 11/9 | V Girls Swimming and Diving | CIAC Class M Diving Championship | Away - Middletown | 5:30 p.m. | ||
| Sat., 11/11 | V Football | Joel Barlow | Away - Joel Barlow HS-Field I (Stadium) [Directions] | 1:00 p.m. | L 7-28 | |
| Sat., 11/11 | V Girls Swimming and Diving | CIAC Class M Qualifying Meet | Away - East Lyme | 1:15 p.m. | ||
| Tue., 11/14 | FR Football | Joel Barlow | Home - Pomperaug HS-Stadium [Directions] | 4:00 p.m. | ||
| Tue., 11/14 | V Girls Swimming and Diving | CIAC Class M Finals | Away - SCSU | 6:00 p.m. | ||
| Thu., 11/16 | V Girls Swimming and Diving | CIAC State Open Diving | Away - Middletown | 5:30 p.m. | ||
| Sun., 11/19 | V Girls Swimming and Diving | CIAC State Open Swimming | Away - Yale | 1:00 p.m. | ||
| Mon., 11/20 | FR Football | New Milford | Home - Pomperaug HS-Stadium [Directions] | 5:30 p.m. | ||
| Tue., 11/21 | V Football | Notre Dame-Fairfield | Home - Pomperaug HS-Stadium [Directions] | 6:30 p.m. | W 23-13 | |
| Tue., 11/28 | V Football | CIAC Quarterfinals | Away - Higher Seed | 6:30 p.m. | ||
| Sat., 12/2 | V Boys Ice Hockey | New Milford (Scrim.) | Home - Taft School-Mays [Directions] | 7:30 p.m. | ||
| Sun., 12/3 | V Football | CIAC Semifinals | Away - Higher Seed | 12:30 p.m. | ||
| Mon., 12/4 | V Boys Basketball | Wilby (Scrim.) | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 12/4 | V Boys Ice Hockey | St. Joseph (Scrim.) | Away - Sports Center of Connecticut-Lower [Directions] | 2:30 p.m. | ||
| Wed., 12/6 | V Boys Basketball | Naugatuck (Scrim.) | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 5:00 p.m. | ||
| Wed., 12/6 | V Boys Ice Hockey | Suffield/Granby/Windsor Locks Wildcats (Scrim.) | Home - Taft School-Mays [Directions] | 7:45 p.m. | ||
| Wed., 12/6 | V Girls Basketball | Ridgefield (Scrim.) | Home - Pomperaug HS-Main Gym [Directions] | 5:00 p.m. | ||
| Fri., 12/8 | V Girls Basketball | Sacred Heart Academy (Scrim.) | Away - Sacred Heart Academy-Gym [Directions] | 4:45 p.m. | Cancelled | |
| Sat., 12/9 | V Football | CIAC Championship Games | Away - Site TBA | TBA | ||
| Sat., 12/9 | V Girls Basketball | Norwich Free Academy, E.O. Smith, East Hampton (Scrim.) | Away - Norwich Free Academy-Alumni Gym [Directions] | 3:00 p.m. | ||
| Mon., 12/11 | V Boys Basketball | Nonnewaug (Scrim.) | Away - Nonnewaug HS-Gym [Directions] | 5:00 p.m. | ||
| Mon., 12/11 | JV Boys Basketball | Nonnewaug (Scrim.) | Away - Nonnewaug HS-Gym [Directions] | 3:30 p.m. | ||
| Mon., 12/11 | V Girls Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 7:00 p.m. | W 51-49 | |
| Mon., 12/11 | JV Girls Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 12/11 | FR Girls Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 12/13 | V Boys Ice Hockey | Shepaug Valley Ice Hockey | Home - Taft School-Mays [Directions] | 7:45 p.m. | W 4-0 | |
| Wed., 12/13 | V Wrestling | New Milford | Away - New Milford HS-Small Gym - NMHS [Directions] | 6:00 p.m. | New Milford 72 Pomperaug Co-op 10 | |
| Fri., 12/15 | V Boys Indoor Track | Hillhouse Invitational at Floyd Little Athletic Center-New Haven | Away - Not Listed | 4:30 p.m. | ||
| Fri., 12/15 | V Girls Indoor Track | Hillhouse Invitational at Floyd Little Athletic Center-New Haven | Away - Pomperaug HS-Main Gym | 4:30 p.m. | ||
| Sat., 12/16 | V Boys Ice Hockey | Cheshire | Away - Hamden-Lou Astorino Ice Rink [Directions] | 8:15 p.m. | L 2-5 | |
| Sat., 12/16 | V Boys Indoor Track | Hillhouse Invitational at Floyd Little Athletic Center-New Haven | Away - Not Listed | 10:00 a.m. | ||
| Sat., 12/16 | V Wrestling | Ludlowe Invitational | Away - Fairfield Ludlowe HS-Main Gym | 9:00 a.m. | ||
| Sat., 12/16 | V Girls Basketball | East Lyme | Home - Pomperaug HS-Main Gym [Directions] | 11:30 a.m. | W 70-46 | |
| Sat., 12/16 | JV Girls Basketball | East Lyme | Home - Pomperaug HS-Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 12/16 | V Girls Indoor Track | Hillhouse Invitational at Floyd Little Athletic Center-New Haven | Away - Not Listed | 10:00 a.m. | ||
| Mon., 12/18 | V Girls Basketball | Bunnell | Away - Bunnell HS-David Johnson Gymnasium [Directions] | 6:00 p.m. | W 65-25 | |
| Mon., 12/18 | JV Girls Basketball | Bunnell | Away - Bunnell HS-David Johnson Gymnasium [Directions] | 4:15 p.m. | ||
| Tue., 12/19 | V Boys Basketball | Foran | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | W 71-49 | |
| Tue., 12/19 | JV Boys Basketball | Foran | Home - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 12/19 | FR Boys Basketball | Foran | Home - Pomperaug HS-Main Gym [Directions] | 3:30 p.m. | ||
| Tue., 12/19 | FR Girls Basketball | Naugatuck | Away - Naugatuck HS-Edward Mariano Gymnasium [Directions] | 3:15 p.m. | ||
| Tue., 12/19 | V Girls Gymnastics | Jonathan Law, Oxford | Away - Jonathan Law HS-Old Gym [Directions] | 6:00 p.m. | 123.2 | |
| Wed., 12/20 | V Boys Ice Hockey | South Windsor | Home - Taft School-Mays [Directions] | 7:45 p.m. | L 2-3 | |
| Wed., 12/20 | V Wrestling | New Fairfield | Home - Pomperaug HS-Auxiliary Gym [Directions] | 6:00 p.m. | Pomperaug 21 New Fairfield 55 | |
| Thu., 12/21 | V Boys Swimming and Diving | Newtown | Home - Pomperaug HS-PHS Pool [Directions] | 4:30 p.m. | Pomperaug 94 Newtown 79 | |
| Fri., 12/22 | V Boys Basketball | Stamford | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | L 48-39 | |
| Fri., 12/22 | JV Boys Basketball | Stamford | Home - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 12/22 | FR Boys Basketball | Stamford | Home - Pomperaug HS-Main Gym [Directions] | Canceled | Cancelled | |
| Fri., 12/22 | V Boys Swimming and Diving | PHS Alumni Meet | Home - Pomperaug HS-PHS Pool [Directions] | 7:00 p.m. | ||
| Fri., 12/22 | V Girls Basketball | Simsbury | Away - Simsbury HS-Simsbury / Main Gym [Directions] | 5:15 p.m. | L 49-35 | |
| Fri., 12/22 | JV Girls Basketball | Simsbury | Away - Simsbury HS-Simsbury / Main Gym [Directions] | 3:45 p.m. | ||
| Sat., 12/23 | V Boys Ice Hockey | North Branford | Home - Taft School-Mays [Directions] | 7:30 p.m. | W 4-2 | |
| Sat., 12/23 | V Wrestling | Nonnewaug, St. Paul Catholic, Terryville-Thomaston (2 mats) | Home - Pomperaug HS-Main Gym [Directions] | 10:00 a.m. | Pomperaug 31 Nonnewaug 47 Pomperaug 55 St. Paul 12 Pomperaug 48 Terryville-Thomaston 30 | |
| Wed., 12/27 | V Boys Basketball | Immaculate | Away - Immaculate HS-Immaculate Gym [Directions] | 5:00 p.m. | L 46-47 | |
| Wed., 12/27 | V Boys Ice Hockey | North Haven | Home - Taft School-Mays [Directions] | 7:45 p.m. | L 3-4 OT | |
| Wed., 12/27 | V Girls Basketball | Glastonbury | Home - Pomperaug HS-Main Gym [Directions] | 5:00 p.m. | L 51-41 | |
| Fri., 12/29 | V Boys Basketball | West Haven | Home - Immaculate HS-Immaculate Gym [Directions] | 3:00 p.m. | L 73-89 | |
| Fri., 12/29 | V Girls Basketball | Wilton | Home - Pomperaug HS-Main Gym [Directions] | 3:00 p.m. | W 48-43 | |
| Sat., 12/30 | V Boys Ice Hockey | Daniel Hand | Home - Taft School-Mays [Directions] | 7:30 p.m. | W 3-2 | |
| Sat., 12/30 | V Wrestling | Trumbull Duals (6 mats) | Away - Trumbull HS-McDougall Stadium | 9:00 a.m. | Pomperaug 15 Trumbull 66 Pomperaug 6 NFA 75 Pomperaug 18 Manchester 66 Pomperaug 36 Masuk 33 Pomperaug 42 JV All-Stars 39 | |
| Tue., 1/2 | V Boys Indoor Track | Wilton Wright Invitational at SCSU- New Haven | Away - Not Listed | 4:00 p.m. | ||
| Tue., 1/2 | V Girls Indoor Track | Wilton Wright Invitational at SCSU- New Haven | Away - Not Listed | 4:00 p.m. | ||
| Wed., 1/3 | V Boys Ice Hockey | Farmington Valley Generals | Away - Avon Old Farms-Jennings Rink [Directions] | 7:30 p.m. | W 4-1 | |
| Wed., 1/3 | V Boys Swimming and Diving | New Fairfield | Away - New Fairfield HS-Pool [Directions] | 4:00 p.m. | Pomperaug 100 New Fairfield 57 | |
| Wed., 1/3 | V Wrestling | Bethel | Away - Bethel HS-BHS gym [Directions] | 6:00 p.m. | Pomperaug 48 Bethel 27 | |
| Thu., 1/4 | V Boys Basketball | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Sister Marion Reilly Auditorium [Directions] | 7:00 p.m. | L 65-53 | |
| Thu., 1/4 | JV Boys Basketball | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Sister Marion Reilly Auditorium [Directions] | 5:30 p.m. | ||
| Thu., 1/4 | FR Boys Basketball | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Sister Marion Reilly Auditorium [Directions] | 4:00 p.m. | ||
| Thu., 1/4 | V Girls Basketball | Notre Dame-Fairfield | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | W 55-49 | |
| Thu., 1/4 | JV Girls Basketball | Notre Dame-Fairfield | Home - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | ||
| Thu., 1/4 | FR Girls Basketball | New Fairfield | Home - Pomperaug HS-Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 1/5 | V Boys Ice Hockey | Tri-Town | Away - Enfield Twin Rinks-Rink 2 [Directions] | 7:50 p.m. | W 4-1 | |
| Sat., 1/6 | V Boys Basketball | Jonathan Law | Home - Pomperaug HS-Main Gym [Directions] | 1:00 p.m. | W 65-46 | |
| Sat., 1/6 | JV Boys Basketball | Jonathan Law | Home - Pomperaug HS-Main Gym [Directions] | 11:30 a.m. | ||
| Sat., 1/6 | FR Boys Basketball | Jonathan Law | Home - Pomperaug HS-Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 1/6 | V Boys Ice Hockey | Hamden | Away - Hamden-Lou Astorino Ice Rink [Directions] | 4:15 p.m. | W 4-1 | |
| Sat., 1/6 | V Boys Indoor Track | Bethel, Brookfield, Immaculate, Kolbe Cathedral, Notre Dame-Fairfield, Stratford | Away - Bethel HS-Track and Field Training Center | 9:00 a.m. | ||
| Sat., 1/6 | V Wrestling | Bristol Central Invitational | Away - Bristol Central HS-Charles C. Marsh Gymnasium | 9:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 8:00 a.m. | ||||||
| Sat., 1/6 | JV Wrestling | Bristol Eastern, Avon, Berlin, Branford, Bristol Central, East Hartford, Enfield, Farmington, Guilford, Ledyard, Middletown, New Fairfield, New Milford, Plainville, Ridgefield, Staples, Terryville-Thomaston, Wethersfield, Hall | Away - Bristol Eastern HS-Gym | 9:00 a.m. | ||
| Sat., 1/6 | V Girls Indoor Track | Bethel, Brookfield, Bunnell, Immaculate, Kolbe Cathedral, Notre Dame-Fairfield, Stratford | Away - Bethel HS-Track and Field Training Center | 9:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 2:00 p.m. | ||||||
| Mon., 1/8 | V Boys Basketball | Stratford | Away - Stratford HS-Gym [Directions] | 7:00 p.m. | W 53-59 | |
| Mon., 1/8 | JV Boys Basketball | Stratford | Away - Stratford HS-Gym [Directions] | 5:15 p.m. | ||
| Mon., 1/8 | FR Boys Basketball | Stratford | Away - Stratford HS-Gym [Directions] | 3:30 p.m. | ||
| Mon., 1/8 | V Girls Basketball | Stratford | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | W 68-29 | |
| Mon., 1/8 | JV Girls Basketball | Stratford | Home - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 1/8 | FR Girls Basketball | Naugatuck | Home - Pomperaug HS-Main Gym [Directions] | 3:30 p.m. | ||
| Tue., 1/9 | V Boys Swimming and Diving | New Milford | Home - Pomperaug HS-PHS Pool [Directions] | 4:00 p.m. | Pomperaug 86 New Milford 62 | |
| Wed., 1/10 | V Boys Ice Hockey | Eastern CT Eagles | Home - Taft School-Mays [Directions] | 7:45 p.m. | W 5-2 | |
| Wed., 1/10 | V Boys Indoor Track | James Barber Invitational at SCSU- New Haven | Away - Not Listed | 4:00 p.m. | ||
| Wed., 1/10 | V Girls Indoor Track | James Barber Invitational at SCSU- New Haven | Away - Not Listed | 4:00 p.m. | ||
| Thu., 1/11 | V Boys Basketball | Masuk | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | L 54-56 | |
| Thu., 1/11 | JV Boys Basketball | Masuk | Home - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | ||
| Thu., 1/11 | FR Boys Basketball | Masuk | Home - Pomperaug HS-Main Gym [Directions] | 3:30 p.m. | ||
| Thu., 1/11 | V Wrestling | Joel Barlow | Home - Pomperaug HS-Auxiliary Gym [Directions] | 6:00 p.m. | Pomperaug 42 Joel Barlow 27 | |
| Thu., 1/11 | V Girls Basketball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 7:00 p.m. | L 62-50 | |
| Thu., 1/11 | JV Girls Basketball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 5:15 p.m. | ||
| Sat., 1/13 | V Boys Ice Hockey | Branford | Away - Northford-Red [Directions] | 2:30 p.m. | W 3-2 OT | |
| Sat., 1/13 | V Boys Indoor Track | Bethel, Bunnell, Kolbe Cathedral, Masuk, New Fairfield, Weston | Away - Bethel HS-Track and Field Training Center | 9:00 a.m. | ||
| Sat., 1/13 | V Wrestling | Art Powers Dual (4 mats) | Away - Berlin HS-Jim Day Gymnasium | 9:30 a.m. | Pomperaug 16 RHAM 63 Pomperaug 24 Bristol Central 54 Pomperaug Bradford 51 Pomperaug 19 Pomperaug 33 Montville 42 | |
| Sat., 1/13 | V Girls Basketball | Thomaston | Home - Pomperaug HS-Main Gym [Directions] | 1:30 p.m. | W 50-33 | |
| Sat., 1/13 | JV Girls Basketball | Thomaston | Home - Pomperaug HS-Main Gym [Directions] | 12:00 p.m. | ||
| Sat., 1/13 | V Girls Gymnastics | Brookfield, Danbury, Joel Barlow, New Milford, Oxford | Away - Gymnastics Revolution | 2:00 p.m. | 124.3 | |
| Sat., 1/13 | V Girls Indoor Track | Bethel, Bunnell, Kolbe Cathedral, Masuk, New Fairfield, Stratford, Weston | Away - Bethel HS-Track and Field Training Center | 9:00 a.m. | ||
| Mon., 1/15 | V Girls Gymnastics | Joel Barlow, Oxford | Home - Kinetic Kids [Directions] | 10:00 a.m. | 119.1 | |
| Wed., 1/17 | V Wrestling | Notre Dame-Fairfield | Home - Pomperaug HS-Auxiliary Gym [Directions] | 6:00 p.m. | Pomperaug 72 Notre-Dame Fairfield 12 | |
| Wed., 1/17 | V Girls Basketball | New Milford | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | W 60-49 | |
| Wed., 1/17 | JV Girls Basketball | New Milford | Home - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | ||
| Thu., 1/18 | V Boys Basketball | New Milford | Away - New Milford HS-Main Gym - NMHS [Directions] | 7:00 p.m. | W 59-48 | |
| Thu., 1/18 | JV Boys Basketball | New Milford | Away - New Milford HS-Main Gym - NMHS [Directions] | 5:30 p.m. | ||
| Thu., 1/18 | FR Boys Basketball | New Milford | Away - New Milford HS-Main Gym - NMHS [Directions] | 4:00 p.m. | ||
| Thu., 1/18 | V Boys Swimming and Diving | Brookfield | Home - Pomperaug HS-PHS Pool [Directions] | 4:00 p.m. | Pomperaug 97 Brookfield 81 | |
| Fri., 1/19 | V Boys Basketball | Joel Barlow | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | W 68-43 | |
| Fri., 1/19 | JV Boys Basketball | Joel Barlow | Home - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/19 | FR Boys Basketball | Joel Barlow | Home - Pomperaug HS-Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 1/19 | V Girls Basketball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 7:00 p.m. | W 55-54 | |
| Fri., 1/19 | JV Girls Basketball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/19 | FR Girls Basketball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 4:00 p.m. | ||
| Sat., 1/20 | V Boys Ice Hockey | Lyman Hall | Home - Taft School-Mays [Directions] | 7:30 p.m. | W 5-1 | |
| Sat., 1/20 | V Wrestling | New Milford, Amity, Bethel, Bunnell, Enfield, Joel Barlow, Maloney, Masuk, Norwalk, RHAM, Stratford, Terryville-Thomaston, Harding/Bassick/Bridgeport Central, Weston | Away - New Milford HS-Main Gym - NMHS | 9:00 a.m. | ||
| Sat., 1/20 | V Competitive Cheerleading | Cheer Competition-Seymour Middle School | Away - Not Listed | 11:00 a.m. | ||
| Sat., 1/20 | V Girls Gymnastics | Newtown, Nonnewaug, Oxford | Away - Newtown Gymnastics [Directions] | 4:00 p.m. | 92.00 | |
| Mon., 1/22 | V Boys Basketball | Weston | Away - Weston HS-Gym (New) [Directions] | 7:00 p.m. | W 47-42 | |
| Mon., 1/22 | JV Boys Basketball | Weston | Away - Weston HS-Gym (New) [Directions] | 5:15 p.m. | ||
| Mon., 1/22 | FR Boys Basketball | Weston | Away - Weston HS-Gym (New) [Directions] | 3:45 p.m. | ||
| Mon., 1/22 | V Girls Basketball | Weston | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | W 52-15 | |
| Mon., 1/22 | JV Girls Basketball | Weston | Home - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 1/22 | FR Girls Basketball | Naugatuck | Home - Pomperaug HS-Main Gym [Directions] | 3:30 p.m. | ||
| Tue., 1/23 | V Boys Swimming and Diving | Joel Barlow-Bethel Swim | Home - Pomperaug HS-PHS Pool [Directions] | 4:30 p.m. | Pomperaug 93 Joel Barlow/Bethel 63 | |
| Wed., 1/24 | V Wrestling | Weston | Away - Weston HS-Gym (Old) [Directions] | 6:00 p.m. | Pomperaug 24 Weston 54 | |
| Wed., 1/24 | V Girls Basketball | Woodland | Away - Woodland HS-Gym [Directions] | 6:00 p.m. | W 56-45 | |
| Wed., 1/24 | JV Girls Basketball | Woodland | Away - Woodland HS-Gym [Directions] | 4:30 p.m. | ||
| Fri., 1/26 | V Boys Basketball | Bethel | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | W 65-45 | |
| Fri., 1/26 | JV Boys Basketball | Bethel | Home - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/26 | FR Boys Basketball | Bethel | Home - Pomperaug HS-Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 1/26 | V Girls Basketball | Bethel | Away - Bethel HS-BHS gym [Directions] | 6:00 p.m. | W 52-42 | |
| Fri., 1/26 | JV Girls Basketball | Bethel | Away - Bethel HS-BHS gym [Directions] | 4:15 p.m. | ||
| Sat., 1/27 | V Boys Ice Hockey | Conard | Home - Taft School-Mays [Directions] | 7:30 p.m. | T 1-1 | |
| Sat., 1/27 | V Boys Indoor Track | Brookfield, Bunnell, Immaculate, New Fairfield, Notre Dame-Fairfield, Stratford | Away - Brookfield HS-Bethel Indoor Track | 2:00 p.m. | ||
| Sat., 1/27 | V Boys Swimming and Diving | Inter squad meet | Home - Pomperaug HS-PHS Pool [Directions] | 5:00 p.m. | ||
| Sat., 1/27 | V Wrestling | Brookfield Invitational | Away - Brookfield HS-BHS Small & Big Gym | 9:30 a.m. | ||
| Sat., 1/27 | FR Girls Basketball | Woodland | Away - Woodland HS-Gym [Directions] | 11:45 a.m. | ||
| Sat., 1/27 | V Girls Indoor Track | Brookfield, Bunnell, Immaculate, New Fairfield, Notre Dame-Fairfield, Stratford | Away - Brookfield HS-Bethel Indoor Track | 2:00 p.m. | ||
| Mon., 1/29 | V Boys Basketball | New Fairfield | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | W 63-51 | |
| Mon., 1/29 | JV Boys Basketball | New Fairfield | Home - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 1/29 | FR Boys Basketball | New Fairfield | Home - Pomperaug HS-Main Gym [Directions] | 3:30 p.m. | ||
| Mon., 1/29 | V Girls Basketball | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | 7:00 p.m. | W 50-38 | |
| Mon., 1/29 | JV Girls Basketball | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | 5:15 p.m. | ||
| Mon., 1/29 | FR Girls Basketball | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | 3:45 p.m. | ||
| Wed., 1/31 | V Boys Swimming and Diving | Naugatuck | Away - Naugatuck HS-Alex Gimbo Sullivan Pool [Directions] | 4:00 p.m. | ||
| Wed., 1/31 | V Wrestling | Brookfield/Shepaug | Away - Brookfield HS-BHS Big Gym [Directions] | 6:00 p.m. | Pomperaug 18 Brookfield 54 | |
| Wed., 1/31 | Unified Sports Basketball | Oxford | Home - Pomperaug HS-Auxiliary Gym [Directions] | 2:30 p.m. | ||
| Thu., 2/1 | V Boys Basketball | Immaculate | Away - Immaculate HS-Immaculate Gym [Directions] | 7:00 p.m. | L 61-54 | |
| Thu., 2/1 | JV Boys Basketball | Immaculate | Away - Immaculate HS [Directions] | 5:15 p.m. | ||
| Thu., 2/1 | FR Boys Basketball | Immaculate | Away - Immaculate HS-Immaculate Gym [Directions] | 3:30 p.m. | ||
| Thu., 2/1 | V Girls Basketball | Immaculate | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | W 46-38 | |
| Thu., 2/1 | JV Girls Basketball | Immaculate | Home - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/2 | V Competitive Cheerleading | SWC Championships at Newtown High School | Away - Not Listed | 6:00 p.m. | ||
| Sat., 2/3 | V Boys Ice Hockey | JBWA | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 8:30 p.m. | W 4-2 | |
| Sat., 2/3 | V Boys Indoor Track | SWC Championship | Away - Floyd Little Athletic Center-Field House | 5:00 p.m. | ||
| Sat., 2/3 | V Boys Swimming and Diving | Hall, Amity, Conard, East Lyme NFA, Glastonbury, Oxford, Southington, Woodland, Xavier | Away - Cornerstone Aquatics Center-Pool | 3:00 p.m. | ||
| Sat., 2/3 | V Girls Gymnastics | Joel Barlow, Oxford | Away - Kinetic Kids [Directions] | 5:00 p.m. | 97.7 | |
| Sat., 2/3 | V Girls Indoor Track | SWC Championship | Away - Floyd Little Athletic Center-Field House | 5:00 p.m. | ||
| Mon., 2/5 | V Boys Basketball | Kolbe Cathedral | Away - Cardinal Sheehan Center Bridgeport [Directions] | 7:00 p.m. | L 37-64 | |
| Mon., 2/5 | JV Boys Basketball | Kolbe Cathedral | Away - Cardinal Sheehan Center Bridgeport [Directions] | 5:15 p.m. | ||
| Mon., 2/5 | V Boys Indoor Track | Last Chance Qualifier at Floyd Little Training Center-New Haven | Away - Not Listed | 4:30 p.m. | ||
| Mon., 2/5 | V Wrestling | Stratford | Home - Pomperaug HS-Auxiliary Gym [Directions] | 6:00 p.m. | Pomperaug 18 Stratford 47 | |
| Mon., 2/5 | V Girls Basketball | Kolbe Cathedral | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | L 65-60 | |
| Mon., 2/5 | JV Girls Basketball | Kolbe Cathedral | Home - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 2/5 | V Girls Gymnastics | Jonathan Law, Oxford | Away - Jonathan Law HS-Old Gym [Directions] | 6:00 p.m. | 94.45 | |
| Mon., 2/5 | V Girls Indoor Track | Last Chance Qualifier at Floyd Little Training Center-New Haven | Away - Not Listed | 4:30 p.m. | ||
| Tue., 2/6 | V Boys Swimming and Diving | Bunnell-Stratford | Home - Pomperaug HS-PHS Pool [Directions] | 5:30 p.m. | ||
| Wed., 2/7 | V Boys Ice Hockey | Masuk | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 8:00 p.m. | L 2-4 | |
| Thu., 2/8 | V Boys Basketball | Brookfield | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | W 62-56 | |
| Thu., 2/8 | JV Boys Basketball | Brookfield | Home - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | ||
| Thu., 2/8 | FR Boys Basketball | Brookfield | Home - Pomperaug HS-Main Gym [Directions] | 3:30 p.m. | ||
| Thu., 2/8 | V Boys Swimming and Diving | Weston | Home - Pomperaug HS-PHS Pool [Directions] | 4:00 p.m. | ||
| Thu., 2/8 | V Girls Basketball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 7:00 p.m. | W 57-51 | |
| Thu., 2/8 | JV Girls Basketball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/9 | V Boys Ice Hockey | Guilford | Home - Taft School-Mays [Directions] | 7:30 p.m. | W 4-2 | |
| Fri., 2/9 | V Girls Gymnastics | SWC Gymnastics Championships | Away - New Milford HS-Main Gym - NMHS | 5:00 p.m. | 103.35 | |
| Sat., 2/10 | V Boys Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 2:30 p.m. | W 50-52 | |
| Sat., 2/10 | JV Boys Basketball | Northwestern | Away - Northwestern Regional H.S.-Main Gym [Directions] | 1:00 p.m. | ||
| Sat., 2/10 | V Boys Indoor Track | CIAC L Divisional Championship | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Sat., 2/10 | V Wrestling | SWC Wrestling Championships at Newtown High School | Away - Newtown HS-Gym | 9:00 a.m. | ||
| Sat., 2/10 | V Competitive Cheerleading | Hatter Fest-Danbury High School | Away - Not Listed | 1:00 p.m. | ||
| Sat., 2/10 | V Girls Indoor Track | CIAC L Divisional Championship | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Mon., 2/12 | V Boys Swimming and Diving | Masuk | Away - Masuk HS-Pool [Directions] | 4:00 p.m. | ||
| Mon., 2/12 | V Girls Basketball | Newtown | Home - Pomperaug HS-Main Gym [Directions] | 6:30 p.m. | W 55-54 | |
| Mon., 2/12 | JV Girls Basketball | Newtown | Home - Pomperaug HS-Main Gym [Directions] | 5:00 p.m. | ||
| Tue., 2/13 | FR Girls Basketball | Newtown | Home - Pomperaug HS-Main Gym [Directions] | Canceled | Cancelled | |
| Wed., 2/14 | V Boys Basketball | Newtown | Away - Newtown HS-Gym [Directions] | 7:00 p.m. | L 65-55 | |
| Wed., 2/14 | JV Boys Basketball | Newtown | Away - Newtown HS-Gym [Directions] | Postponed | ||
| Wed., 2/14 | FR Boys Basketball | Newtown | Away - Newtown HS-Gym [Directions] | Postponed | ||
| Wed., 2/14 | V Boys Ice Hockey | East Haven Coop | Home - Taft School-Mays [Directions] | 7:45 p.m. | L 0-3 | |
| Thu., 2/15 | FR Boys Basketball | Wolcott | Away - Wolcott HS-Main Gym [Directions] | 4:15 p.m. | ||
| Thu., 2/15 | V Girls Gymnastics | New Milford, Brookfield, Danbury, Oxford, Wilton | Away - New Milford HS-Small Gym - NMHS | 5:30 p.m. | 99.4 | |
| Fri., 2/16 | V Boys Basketball | Bunnell | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | L 73-66 | |
| Fri., 2/16 | JV Boys Basketball | Bunnell | Home - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/16 | FR Boys Basketball | Bunnell | Home - Pomperaug HS-Auxiliary Gym [Directions] | 5:00 p.m. | ||
| Fri., 2/16 | V Wrestling | CIAC LL Divisional Championship | Away - Trumbull | TBA | ||
| Sat., 2/17 | V Boys Ice Hockey | Amity | Away - West Haven HS-Bennett Rink [Directions] | 3:00 p.m. | ||
| Sat., 2/17 | V Boys Indoor Track | CIAC State Open Divisional Championship | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/17 | V Girls Basketball | Bethel | Home - Pomperaug HS-Main Gym [Directions] | 1:00 p.m. | ||
| Sat., 2/17 | V Girls Gymnastics | Hamden, Newtown, Nonnewaug, Oxford | Home - Kinetic Kids [Directions] | 5:00 p.m. | 113.45 | |
| Sat., 2/17 | V Girls Indoor Track | CIAC State Open Championship | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Mon., 2/19 | V Boys Basketball | Amity | Home - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | L 52-49 | |
| Mon., 2/19 | JV Boys Basketball | Amity | Home - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 2/19 | FR Boys Basketball | Amity | Home - Pomperaug HS-Main Gym [Directions] | 3:30 p.m. | ||
| Tue., 2/20 | V Girls Basketball | New Fairfield | Home - Pomperaug HS-Main Gym [Directions] | 6:00 p.m. | ||
| Wed., 2/21 | V Boys Ice Hockey | West Haven Coop | Away - West Haven HS-Bennett Rink [Directions] | 6:00 p.m. | ||
| Wed., 2/21 | Unified Sports Basketball | Newtown Unified Basketball Tournament at Newtown Youth Academy | Away - Newtown Youth Academy (NYA)-Court | 3:00 p.m. | ||
| Fri., 2/23 | V Boys Basketball | Kolbe Cathedral | Away - Cardinal Sheehan Center Bridgeport [Directions] | 6:30 p.m. | ||
| Fri., 2/23 | V Boys Ice Hockey | Westhill/Stamford | Home - Taft School-Mays [Directions] | 6:30 p.m. | ||
| Fri., 2/23 | V Wrestling | CIAC State Open & Girls Championship | Away - Floyd Little Athletic Center | TBA | ||
| Sat., 2/24 | V Competitive Cheerleading | Oxford High School Cheer Competition | Away - Not Listed | 1:00 p.m. | ||
| Wed., 2/28 | V Boys Ice Hockey | Amity | Away - West Haven HS-Bennett Rink [Directions] | 8:00 p.m. | ||
| Wed., 2/28 | V Boys Swimming and Diving | Brookfield, Masuk, Weston | Home - Pomperaug HS-PHS Pool [Directions] | 6:00 p.m. | ||
| Wed., 2/28 | Unified Sports Basketball | Bethel | Home - Pomperaug HS-Auxiliary Gym [Directions] | 3:00 p.m. | ||
| Fri., 3/1 | V Boys Swimming and Diving | Masuk, Bethel, Brookfield, Bunnell-Stratford, Immaculate, Joel Barlow-Bethel Swim, New Fairfield, New Milford, Newtown, Stratford, Weston | Away - Masuk HS-Pool | 5:00 p.m. | ||
| Fri., 3/1 | V Girls Basketball | Bethel | Home - Pomperaug HS-Main Gym [Directions] | 6:00 p.m. | L 49-53 | |
| Sat., 3/2 | V Boys Swimming and Diving | TBA, Naugatuck | Home - Pomperaug HS-PHS Pool [Directions] | 5:00 p.m. | ||
| Sat., 3/2 | V Competitive Cheerleading | Cheerleading State Championships at Trumbull High School | Away - Not Listed | 5:00 p.m. | ||
| Sat., 3/2 | V Girls Gymnastics | CIAC State Open | Away - New Milford | 12:00 p.m. | ||
| Mon., 3/4 | V Boys Basketball | Platt Tech | Away - Platt Tech.-Gym [Directions] | 6:30 p.m. | W 60-49 | |
| Tue., 3/5 | V Boys Ice Hockey | Hamden | Away - Hamden-Lou Astorino Ice Rink [Directions] | 7:30 p.m. | W 4-0 | |
| Tue., 3/5 | V Boys Ice Hockey | CIAC Div II First Round | Away - Higher Seed | TBA | ||
| Wed., 3/6 | V Boys Basketball | Bristol Eastern | Away - Bristol Eastern HS-Gym [Directions] | 6:30 p.m. | L 49-66 | |
| Thu., 3/7 | V Boys Swimming and Diving | CIAC Class M Diving Championship | Away - Middletown | 5:30 p.m. | ||
| Fri., 3/8 | V Boys Ice Hockey | Cheshire | Away - West Haven HS-Bennett Rink [Directions] | 6:00 p.m. | L 1-2 | |
| Fri., 3/8 | V Boys Ice Hockey | CIAC Div II Quarterfinal | Away - Site TBA | TBA | ||
| Sat., 3/9 | V Boys Swimming and Diving | CIAC Class M Qualifying Meet | Away - Cheshire Community Pool | 6:45 p.m. | ||
| Mon., 3/11 | V Boys Swimming and Diving | CIAC Class M Finals | Away - Wesleyan | 6:00 p.m. | ||
| Tue., 3/12 | V Boys Ice Hockey | CIAC Div II Semifinal | Away - Site TBA | TBA | ||
| Thu., 3/14 | V Boys Swimming and Diving | CIAC State Open Diving | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/16 | V Boys Swimming and Diving | CIAC State Open Swimming | Away - Yale | 1:00 p.m. | ||
| Mon., 3/18 | V Boys Ice Hockey | CIAC Div II Final | Away - Site TBA | TBA | ||
| Fri., 3/22 | V Baseball | Shepaug Valley (Scrim.) | Away - Washington Primary School-Ted Alex Field [Directions] | 3:45 p.m. | ||
| Fri., 3/22 | V Boys Tennis | Nonnewaug (Scrim.) | Away - Nonnewaug HS-Tennis Courts [Directions] | 3:45 p.m. | ||
| Fri., 3/22 | V Girls Lacrosse | Norwalk (Scrim.) | Home - Pomperaug HS-Stadium [Directions] | 6:00 p.m. | ||
| Fri., 3/22 | V Softball | Seymour (Scrim.) | Home - Pomperaug HS-Softball Field [Directions] | 3:45 p.m. | ||
| Sat., 3/23 | V Boys Lacrosse | Greens Farms Academy (Scrim.) | Away - Shelton HS-Lower Field | Canceled | Cancelled | |
| Sat., 3/23 | V Boys Lacrosse | Wooster (Scrim.) | Away - Shelton HS-Finn Stadium | Canceled | Cancelled | |
| Sat., 3/23 | V Boys Lacrosse | Stamford (Scrim.) | Home - Shelton HS-Finn Stadium [Directions] | Canceled | Cancelled | |
| Sat., 3/23 | V Boys Lacrosse | Amity (Scrim.) | Home - Shelton HS-Lower Field [Directions] | Canceled | Cancelled | |
| Sat., 3/23 | V Boys Volleyball | Joel Barlow, Farmington, Glastonbury, Iona Prep (NY), New Canaan, Simsbury, Trumbull | Away - Joel Barlow HS-Lower Gym | 8:30 a.m. | ||
| Sat., 3/23 | V Softball | Trumbull (Scrim.) | Away - Trumbull HS-Varsity Softball Diamond [Directions] | 11:00 a.m. | Cancelled | |
| Sat., 3/23 | V Softball | Trumbull (Scrim.) | Away - Trumbull HS-Varsity Softball Diamond [Directions] | 1:00 p.m. | Cancelled | |
| Mon., 3/25 | V Girls Tennis | Joel Barlow (Scrim.) | Away - Joel Barlow HS-Tennis Courts [Directions] | 3:45 p.m. | ||
| Tue., 3/26 | V Baseball | Nonnewaug (Scrim.) | Away - Nonnewaug HS-Baseball Diamond [Directions] | 3:30 p.m. | ||
| Tue., 3/26 | JV Baseball | Nonnewaug (Scrim.) | Home - Pomperaug HS-Baseball Field [Directions] | 3:45 p.m. | ||
| Tue., 3/26 | V Boys Lacrosse | Shelton (Scrim.) | Away - Shelton HS-Finn Stadium [Directions] | 7:00 p.m. | ||
| Tue., 3/26 | V Boys Volleyball | Southington (Scrim.) | Away - Southington HS-Gym West [Directions] | 4:00 p.m. | ||
| Tue., 3/26 | V Girls Lacrosse | Cheshire (Scrim.) | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | ||
| Tue., 3/26 | JV Girls Lacrosse | Cheshire (Scrim.) | Home - Pomperaug HS-Stadium [Directions] | 5:30 p.m. | ||
| Tue., 3/26 | V Softball | Holy Cross (Scrim.) | Away - Municipal Stadium Complex (Waterbury, CT)-Joan Joyce Diamond [Directions] | 4:00 p.m. | ||
| Wed., 3/27 | V Softball | Holy Cross (Scrim.) | Home - Pomperaug HS-Softball Field [Directions] | 3:45 p.m. | ||
| Thu., 3/28 | V Boys Tennis | Cheshire (Scrim.) | Away - Cheshire HS-Tennis Courts [Directions] | Canceled | Cancelled | |
| Thu., 3/28 | V Girls Lacrosse | Daniel Hand (Scrim.) | Away - Madison Surf Club-Strong Field [Directions] | 4:00 p.m. | ||
| Fri., 3/29 | V Girls Tennis | Naugatuck (Scrim.) | Home - Edgewood Bath and Tennis Club [Directions] | 10:00 a.m. | ||
| Sat., 3/30 | V Boys Volleyball | Wolcott Tech | Away - Oliver Wolcott Technical HS-Wolcott Tech Gym [Directions] | 11:00 a.m. | W 3-0 | |
| Sat., 3/30 | JV Boys Volleyball | Wolcott Tech | Away - Oliver Wolcott Technical HS-Wolcott Tech Gym [Directions] | 9:30 a.m. | ||
| Sat., 3/30 | V Softball | Amity | Away - Amity Regional HS-Amity HS - Softball Field [Directions] | 11:00 a.m. | L 0-1 | |
| Mon., 4/1 | V Baseball | Abbott Tech | Home - Pomperaug HS-Baseball Field [Directions] | 4:15 p.m. | W 1-0 | |
| Mon., 4/1 | V Boys Lacrosse | Holy Cross | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | W 20-5 | |
| Mon., 4/1 | JV Boys Lacrosse | Holy Cross | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Mon., 4/1 | V Boys Volleyball | St. Joseph | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Mon., 4/1 | JV Boys Volleyball | St. Joseph | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 4/1 | V Softball | Danbury | Home - Pomperaug HS-Softball Field [Directions] | 4:00 p.m. | W 1-0 | |
| Wed., 4/3 | V Boys Volleyball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 4/3 | JV Boys Volleyball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 4:15 p.m. | ||
| Thu., 4/4 | V Boys Lacrosse | Weston | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | L 5-11 | |
| Thu., 4/4 | JV Boys Lacrosse | Weston | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Thu., 4/4 | V Girls Golf | Notre Dame-Fairfield | Home - Pomperaug HS-Pomperaug Golf Course [Directions] | Postponed | ||
| Thu., 4/4 | V Girls Lacrosse | Weston | Away - Weston HS-WHS Lower Turf Field [Directions] | 5:30 p.m. | ||
| Thu., 4/4 | JV Girls Lacrosse | Weston | Away - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 4/5 | V Baseball | Oxford | Away - Oxford HS-Baseball Field [Directions] | Rainout | ||
| Fri., 4/5 | JV Baseball | Bunnell | Away - Bunnell HS-Bunnell Baseball Field [Directions] | 4:15 p.m. | ||
| Fri., 4/5 | V Boys Volleyball | Daniel Hand | Away - Daniel Hand HS-DHHS Gym [Directions] | 4:15 p.m. | W 3-0 | |
| Fri., 4/5 | V Softball | Oxford | Home - Pomperaug HS-Softball Field [Directions] | 4:00 p.m. | L 11-15 | |
| Sat., 4/6 | V Baseball | New London | Home - Pomperaug HS-Baseball Field [Directions] | 12:00 p.m. | ||
| Sat., 4/6 | JV Girls Lacrosse | New Fairfield | Home - Pomperaug HS-Stadium [Directions] | Canceled | Cancelled | |
| Sat., 4/6 | JV Softball | Oxford | Home - Pomperaug HS-Softball Field [Directions] | Postponed | ||
| Mon., 4/8 | V Baseball | Joel Barlow | Away - Joel Barlow HS-Baseball Field [Directions] | 4:15 p.m. | ||
| Mon., 4/8 | V Boys Tennis | Newtown | Home - Edgewood Bath and Tennis Club [Directions] | 4:00 p.m. | ||
| Mon., 4/8 | V Boys Volleyball | Joel Barlow | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Mon., 4/8 | JV Boys Volleyball | Joel Barlow | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 4/8 | V Girls Golf | Weston | Away - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | ||
| Mon., 4/8 | V Girls Outdoor Track | New Fairfield, Brookfield, Stratford | Away - New Fairfield HS-Stadium Field [Directions] | 4:00 p.m. | ||
| Mon., 4/8 | V Softball | Brookfield | Away - Brookfield HS-BHS Softball Field [Directions] | 4:30 p.m. | ||
| Mon., 4/8 | JV Softball | Bethel | Away - Bethel HS-Turf Softball Field [Directions] | 6:00 p.m. | ||
| Mon., 4/8 | V Girls Tennis | Newtown | Away - Newtown HS-NHS Tennis Courts [Directions] | 4:30 p.m. | W 6-1 | |
| Tue., 4/9 | V Baseball | Oxford | Away - Oxford HS-Baseball Field [Directions] | 3:45 p.m. | ||
| Tue., 4/9 | JV Baseball | Newtown | Away - Fairfield Hills-Baseball Field [Directions] | Postponed | ||
| Tue., 4/9 | FR Baseball | Wolcott | Home - Pomperaug HS-Baseball Field [Directions] | 3:45 p.m. | ||
| Tue., 4/9 | V Boys Lacrosse | Brookfield | Away - Brookfield HS-BHS Back Turf [Directions] | 7:00 p.m. | L 7-8 | |
| Tue., 4/9 | JV Boys Lacrosse | Brookfield | Away - Brookfield HS-BHS Back Turf [Directions] | 5:00 p.m. | ||
| Tue., 4/9 | V Boys Outdoor Track | Brookfield, New Fairfield, Stratford | Away - Brookfield HS-BHS Track [Directions] | 4:00 p.m. | ||
| Tue., 4/9 | V Boys Tennis | Bethel | Home - Edgewood Bath and Tennis Club [Directions] | 6:00 p.m. | ||
| Tue., 4/9 | V Girls Lacrosse | Brookfield | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | ||
| Tue., 4/9 | JV Girls Lacrosse | Brookfield | Home - Pomperaug HS-Stadium [Directions] | 5:15 p.m. | ||
| Tue., 4/9 | JV Softball | Wolcott | Home - Pomperaug HS-Softball Field [Directions] | 3:45 p.m. | ||
| Tue., 4/9 | V Girls Tennis | Bethel | Away - Bethel HS-BHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Wed., 4/10 | FR Baseball | Masuk | Home - Pomperaug HS-Baseball Field [Directions] | 4:15 p.m. | ||
| Wed., 4/10 | V Boys Tennis | New Fairfield | Home - Edgewood Bath and Tennis Club [Directions] | 3:45 p.m. | ||
| Wed., 4/10 | V Boys Volleyball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 5:30 p.m. | W 3-2 | |
| Wed., 4/10 | JV Boys Volleyball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 4/10 | V Girls Golf | Brookfield | Away - Sunset Hill Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 4/10 | V Girls Tennis | New Fairfield | Away - New Fairfield HS-Tennis Courts [Directions] | 4:15 p.m. | W 7-0 | |
| Thu., 4/11 | JV Baseball | Joel Barlow | Home - Pomperaug HS-Baseball Field [Directions] | Canceled | Cancelled | |
| Thu., 4/11 | V Girls Golf | Joel Barlow | Away - Redding Country Club [Directions] | 3:00 p.m. | ||
| Thu., 4/11 | V Girls Lacrosse | Stratford/Bunnell | Away - Penders Field-Penders Field - Stratford [Directions] | 5:00 p.m. | ||
| Thu., 4/11 | JV Girls Lacrosse | Stratford/Bunnell | Away - Penders Field-Penders Field - Stratford [Directions] | Canceled | Cancelled | |
| Sat., 4/13 | FR Baseball | Joel Barlow | Home - Pomperaug HS-Baseball Field [Directions] | Canceled | Cancelled | |
| Sat., 4/13 | V Boys Lacrosse | Amity | Home - Pomperaug HS-Stadium [Directions] | 12:00 p.m. | W 13-5 | |
| Sat., 4/13 | JV Boys Lacrosse | Amity | Home - Pomperaug HS-Stadium [Directions] | 10:00 a.m. | ||
| Sat., 4/13 | V Boys Tennis | Wilcox Tech | Home - Edgewood Bath and Tennis Club [Directions] | 10:00 a.m. | ||
| Sat., 4/13 | V Girls Lacrosse | Branford | Away - Branford HS-Athletic Turf Field [Directions] | 11:00 a.m. | ||
| Sat., 4/13 | JV Girls Lacrosse | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 10:00 a.m. | ||
| Mon., 4/15 | V Baseball | Naugatuck | Away - Naugatuck HS-Raymond Legenza Field [Directions] | 3:45 p.m. | ||
| Mon., 4/15 | FR Baseball | Naugatuck | Away - Naugatuck HS-Raymond Legenza Field [Directions] | 11:00 a.m. | ||
| Mon., 4/15 | V Boys Tennis | Naugatuck | Home - Edgewood Bath and Tennis Club [Directions] | 11:00 a.m. | ||
| Mon., 4/15 | V Softball | Newtown | Home - Pomperaug HS-Softball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/15 | V Girls Tennis | Joel Barlow | Away - Joel Barlow HS-Tennis Courts [Directions] | 10:00 a.m. | W 4-3 | |
| Tue., 4/16 | JV Baseball | Notre Dame-Fairfield | Home - Pomperaug HS-Baseball Field [Directions] | 4:15 p.m. | ||
| Tue., 4/16 | V Boys Lacrosse | New Fairfield | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | L 4-10 | |
| Tue., 4/16 | JV Boys Lacrosse | New Fairfield | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Tue., 4/16 | V Boys Volleyball | Xavier | Home - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | L 0-3 | |
| Tue., 4/16 | JV Boys Volleyball | Xavier | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 4/16 | V Girls Golf | Weston | Home - Pomperaug HS-Pomperaug Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 4/16 | V Girls Lacrosse | New Fairfield | Away - New Fairfield HS-Marty Morgan Field [Directions] | 5:30 p.m. | ||
| Tue., 4/16 | JV Girls Lacrosse | New Fairfield | Away - New Fairfield HS-Marty Morgan Field [Directions] | 4:00 p.m. | ||
| Tue., 4/16 | JV Softball | Newtown | Away - Newtown HS-Lindell A. Hertberg Softball Field [Directions] | 12:00 p.m. | ||
| Wed., 4/17 | V Baseball | New Fairfield | Away - New Fairfield HS-Baseball Field [Directions] | 4:15 p.m. | ||
| Wed., 4/17 | FR Baseball | Newtown | Away - Fairfield Hills-Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 4/17 | V Boys Tennis | Bunnell | Away - Bunnell HS-Bunnell Tennis Courts [Directions] | 10:00 a.m. | ||
| Wed., 4/17 | V Softball | New Fairfield | Away - New Fairfield HS-Softball Field [Directions] | 4:15 p.m. | ||
| Wed., 4/17 | V Girls Tennis | Bunnell | Home - Edgewood Bath and Tennis Club [Directions] | 10:00 a.m. | W 7-0 | |
| Thu., 4/18 | JV Baseball | New Fairfield | Home - Pomperaug HS-Baseball Field [Directions] | Rainout | ||
| Thu., 4/18 | V Boys Lacrosse | Joel Barlow | Away - Joel Barlow HS-Field J [Directions] | 6:00 p.m. | ||
| Thu., 4/18 | JV Boys Lacrosse | Joel Barlow | Away - Joel Barlow HS-Field J [Directions] | 4:00 p.m. | ||
| Thu., 4/18 | V Boys Volleyball | New Milford | Away - New Milford HS-Main Gym - NMHS [Directions] | 6:00 p.m. | W 3-0 | |
| Thu., 4/18 | JV Boys Volleyball | New Milford | Away - New Milford HS-Main Gym - NMHS [Directions] | 4:30 p.m. | ||
| Thu., 4/18 | V Girls Lacrosse | Joel Barlow | Home - Pomperaug HS-Stadium [Directions] | 4:30 p.m. | ||
| Thu., 4/18 | JV Girls Lacrosse | Joel Barlow | Home - Pomperaug HS-Stadium [Directions] | 3:00 p.m. | ||
| Thu., 4/18 | JV Softball | New Fairfield | Home - Pomperaug HS-Softball Field [Directions] | Rainout | ||
| Fri., 4/19 | V Baseball | Bunnell | Home - Pomperaug HS-Baseball Field [Directions] | 4:15 p.m. | ||
| Fri., 4/19 | V Softball | Bunnell | Home - Pomperaug HS-Softball Field [Directions] | 4:15 p.m. | ||
| Sat., 4/20 | V Boys Lacrosse | Watertown | Home - Pomperaug HS-Stadium [Directions] | 3:30 p.m. | ||
| Sat., 4/20 | JV Boys Lacrosse | Watertown | Home - Pomperaug HS-Stadium [Directions] | Canceled | Cancelled | |
| Sat., 4/20 | JV Boys Volleyball | Shelton, Newtown, South Windsor | Away - Shelton HS-Murray Gymnasium [Directions] | Canceled | Cancelled | |
| Sat., 4/20 | V Girls Outdoor Track | Mongovan Invitational at Bethel High School | Away - Not Listed | 9:00 a.m. | ||
| Sat., 4/20 | JV Softball | Bunnell | Away - Bunnell HS-Bunnell Softball FIeld [Directions] | Postponed | ||
| Mon., 4/22 | V Baseball | Kolbe Cathedral | Home - Pomperaug HS-Baseball Field [Directions] | 4:15 p.m. | ||
| Mon., 4/22 | FR Baseball | New Fairfield | Away - New Fairfield HS-Baseball Field [Directions] | 4:15 p.m. | ||
| Mon., 4/22 | V Boys Lacrosse | Bunnell-Stratford | Home - Pomperaug HS-Stadium [Directions] | 6:00 p.m. | ||
| Mon., 4/22 | V Boys Volleyball | Cheshire | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Mon., 4/22 | JV Boys Volleyball | Cheshire | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 4/22 | V Softball | Kolbe Cathedral | Home - Pomperaug HS-Softball Field [Directions] | 4:15 p.m. | ||
| Tue., 4/23 | V Boys Outdoor Track | Joel Barlow, Weston | Home - Pomperaug HS-Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | V Girls Golf | Bunnell | Home - Pomperaug HS-Pomperaug Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 4/23 | V Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | JV Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 5:30 p.m. | ||
| Tue., 4/23 | V Girls Outdoor Track | Weston, Joel Barlow | Away - Weston HS-WHS Track [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | V Softball | Naugatuck | Home - Pomperaug HS-Softball Field [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | V Baseball | Immaculate | Away - Immaculate HS-Baseball Diamond [Directions] | 4:15 p.m. | ||
| Wed., 4/24 | V Girls Golf | Brookfield | Home - Pomperaug HS-Pomperaug Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 4/24 | V Softball | Immaculate | Away - Immaculate HS-Softball Diamond [Directions] | 4:15 p.m. | ||
| Wed., 4/24 | V Girls Tennis | Weston | Home - Edgewood Bath and Tennis Club [Directions] | 3:45 p.m. | ||
| Thu., 4/25 | JV Baseball | Immaculate | Home - Pomperaug HS-Baseball Field [Directions] | 4:15 p.m. | ||
| Thu., 4/25 | V Boys Lacrosse | Bethel | Away - Bethel HS-MS turf lacrosse field [Directions] | 4:00 p.m. | ||
| Thu., 4/25 | JV Boys Lacrosse | Bethel | Away - Bethel HS-MS turf lacrosse field [Directions] | 5:45 p.m. | ||
| Thu., 4/25 | V Boys Tennis | Weston | Away - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | ||
| Thu., 4/25 | V Girls Golf | Immaculate | Away - Richter Park Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 4/25 | V Girls Lacrosse | Bethel | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Thu., 4/25 | JV Girls Lacrosse | Bethel | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | ||
| Thu., 4/25 | JV Softball | Danbury | Away - Danbury HS-JV Softball Field [Directions] | 6:00 p.m. | ||
| Fri., 4/26 | V Baseball | Brookfield | Home - Pomperaug HS-Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 4/26 | V Boys Outdoor Track | O'Grady Relays at Danbury High School | Away - Not Listed | TBA | ||
| Fri., 4/26 | V Boys Volleyball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | 6:00 p.m. | ||
| Fri., 4/26 | JV Boys Volleyball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | 4:30 p.m. | ||
| Fri., 4/26 | V Girls Outdoor Track | O'Grady Relays at Danbury High School | Away - Pomperaug HS-Stadium | TBA | ||
| Fri., 4/26 | V Softball | Brookfield | Home - Pomperaug HS-Softball Field [Directions] | 4:15 p.m. | ||
| Sat., 4/27 | JV Baseball | Brookfield | Away - Brookfield HS-BHS Baseball Field [Directions] | 10:00 a.m. | ||
| Sat., 4/27 | FR Baseball | Bethel | Home - Pomperaug HS-Baseball Field [Directions] | 11:00 a.m. | ||
| Sat., 4/27 | V Boys Outdoor Track | O'Grady Relays | Away - Danbury HS-Danbury HS Stadium | 9:00 a.m. | ||
| Sat., 4/27 | V Boys Outdoor Track | O'Grady Relays at Danbury High School | Away - Pomperaug HS-Stadium | TBA | ||
| Sat., 4/27 | V Boys Tennis | Joel Barlow | Home - Edgewood Bath and Tennis Club [Directions] | 9:30 a.m. | ||
| Sat., 4/27 | V Girls Lacrosse | North Branford | Away - North Branford HS-NBHS Front Field [Directions] | 9:30 a.m. | ||
| Sat., 4/27 | JV Girls Lacrosse | North Branford | Away - North Branford HS-NBHS Front Field [Directions] | 11:00 a.m. | ||
| Sat., 4/27 | V Girls Outdoor Track | O'Grady Relays at Danbury High School | Away - Pomperaug HS-Stadium | TBA | ||
| Sat., 4/27 | JV Softball | Brookfield | Away - Brookfield HS-BHS Softball Field [Directions] | 10:00 a.m. | ||
| Mon., 4/29 | V Baseball | Stratford | Away - Penders Field-Penders Field - Stratford [Directions] | 4:15 p.m. | ||
| Mon., 4/29 | FR Baseball | New Milford | Home - Pomperaug HS-Baseball Field [Directions] | 4:15 p.m. | ||
| Mon., 4/29 | V Boys Tennis | Stratford | Away - Flood MS-Flood MS Tennis Courts [Directions] | 3:45 p.m. | ||
| Mon., 4/29 | V Boys Volleyball | Bunnell | Home - Pomperaug HS-Main Gym [Directions] | 6:15 p.m. | ||
| Mon., 4/29 | JV Boys Volleyball | Bunnell | Home - Pomperaug HS-Main Gym [Directions] | 5:00 p.m. | ||
| Mon., 4/29 | V Girls Outdoor Track | Bethel, Immaculate, Masuk | Home - Pomperaug HS-Stadium [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | V Softball | Stratford | Away - DeLuca Field-Deluca Field [Directions] | 4:15 p.m. | ||
| Mon., 4/29 | V Girls Tennis | Stratford | Home - Edgewood Bath and Tennis Club [Directions] | 4:45 p.m. | ||
| Tue., 4/30 | JV Baseball | Stratford | Home - Pomperaug HS-Baseball Field [Directions] | 4:45 p.m. | ||
| Tue., 4/30 | V Boys Outdoor Track | Masuk, Bethel, Immaculate | Away - Masuk HS-Edmund Butler Track @ Masuk HS [Directions] | 4:00 p.m. | ||
| Tue., 4/30 | V Girls Golf | Newtown, Immaculate | Away - Newtown Country Club [Directions] | 3:00 p.m. | ||
| Tue., 4/30 | V Girls Lacrosse | Newtown | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | ||
| Tue., 4/30 | JV Girls Lacrosse | Newtown | Home - Pomperaug HS-Stadium [Directions] | 5:15 p.m. | ||
| Tue., 4/30 | JV Softball | Stratford | Home - Pomperaug HS-Softball Field [Directions] | Postponed | ||
| Wed., 5/1 | V Baseball | Masuk | Away - Masuk HS-John Giampaolo Baseball Field @ Masuk HS [Directions] | 4:15 p.m. | ||
| Wed., 5/1 | FR Baseball | Masuk | Away - Wolfe Park-Baseball Field [Directions] | 4:15 p.m. | ||
| Wed., 5/1 | V Boys Tennis | Wilcox Tech | Away - Wilcox Tech-Tennis Courts [Directions] | 3:45 p.m. | ||
| Wed., 5/1 | V Softball | Masuk | Away - Masuk HS-Masuk High School Softball Field [Directions] | 4:15 p.m. | ||
| Wed., 5/1 | V Girls Tennis | Notre Dame-Fairfield | Home - Edgewood Bath and Tennis Club [Directions] | 3:45 p.m. | ||
| Thu., 5/2 | JV Baseball | Stratford | Home - Pomperaug HS-Baseball Field [Directions] | Canceled | Cancelled | |
| Thu., 5/2 | V Boys Lacrosse | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 7:30 p.m. | ||
| Thu., 5/2 | JV Boys Lacrosse | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 5:00 p.m. | ||
| Thu., 5/2 | V Boys Tennis | Nonnewaug | Away - Nonnewaug HS-Tennis Courts [Directions] | 3:45 p.m. | ||
| Thu., 5/2 | V Girls Golf | Lauralton Hall, Notre Dame-Fairfield | Home - Pomperaug HS-Pomperaug Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 5/2 | V Girls Lacrosse | Amity | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | ||
| Thu., 5/2 | JV Girls Lacrosse | Amity | Home - Pomperaug HS-Stadium [Directions] | 5:15 p.m. | ||
| Thu., 5/2 | JV Softball | Masuk | Home - Pomperaug HS-Softball Field [Directions] | 4:15 p.m. | ||
| Fri., 5/3 | V Baseball | Joel Barlow | Home - Pomperaug HS-Baseball Field [Directions] | 4:15 p.m. | ||
| Fri., 5/3 | V Boys Lacrosse | Notre Dame-Fairfield | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | ||
| Fri., 5/3 | V Boys Outdoor Track | Middletown Freshman/Sophomore Meet | Away - Not Listed | TBA | ||
| Fri., 5/3 | V Boys Tennis | New Milford | Home - Edgewood Bath and Tennis Club [Directions] | 3:45 p.m. | [Detailed Results] | |
| Fri., 5/3 | V Boys Volleyball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 6:30 p.m. | ||
| Fri., 5/3 | JV Boys Volleyball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 5:00 p.m. | ||
| Fri., 5/3 | V Girls Lacrosse | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Park Ave Field [Directions] | 6:30 p.m. | ||
| Fri., 5/3 | V Girls Outdoor Track | Middletown Freshman/Sophomore Meet | Away - Not Listed | TBA | ||
| Fri., 5/3 | V Softball | Joel Barlow | Home - Pomperaug HS-Softball Field [Directions] | 4:15 p.m. | ||
| Fri., 5/3 | V Girls Tennis | New Milford | Away - New Milford HS-Tennis Courts - NMHS [Directions] | 3:45 p.m. | ||
| Sat., 5/4 | JV Baseball | Joel Barlow | Away - Joel Barlow HS-Baseball Field [Directions] | 4:15 p.m. | ||
| Sat., 5/4 | V Boys Outdoor Track | Middletown Varsity Meet | Away - Not Listed | TBA | ||
| Sat., 5/4 | V Girls Outdoor Track | Fast Times at Ridgefield High School Meet | Away - Not Listed | 4:00 p.m. | ||
| Sat., 5/4 | V Girls Outdoor Track | Middletown Varsity Meet | Away - Not Listed | TBA | ||
| Sat., 5/4 | V Softball | Naugatuck | Away - Naugatuck HS-Softball Diamond [Directions] | 12:00 p.m. | ||
| Sat., 5/4 | JV Softball | Naugatuck | Away - Naugatuck HS-Softball Diamond [Directions] | 10:00 a.m. | ||
| Mon., 5/6 | V Boys Lacrosse | Canton | Away - Canton HS-Canton H.S. Turf [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | JV Boys Lacrosse | Canton | Away - Canton HS-Canton H.S. Turf [Directions] | 5:30 p.m. | ||
| Mon., 5/6 | V Boys Tennis | Masuk | Away - Wolfe Park-Tennis Courts [Directions] | 3:45 p.m. | ||
| Mon., 5/6 | V Boys Volleyball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 6:00 p.m. | ||
| Mon., 5/6 | JV Boys Volleyball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 4:30 p.m. | ||
| Mon., 5/6 | JV Girls Lacrosse | Newtown | Away - Newtown HS-Back Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | V Girls Outdoor Track | Kolbe Cathedral, New Milford, Notre Dame-Fairfield | Home - Pomperaug HS-Stadium [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | V Softball | New Milford | Home - Pomperaug HS-Softball Field [Directions] | 4:15 p.m. | ||
| Mon., 5/6 | JV Softball | Brookfield | Away - PTAK Fields-Brookfield PTAK Softball Field [Directions] | Canceled | Cancelled | |
| Mon., 5/6 | V Girls Tennis | Masuk | Home - Edgewood Bath and Tennis Club [Directions] | 3:45 p.m. | ||
| Tue., 5/7 | V Baseball | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Fabbri Field [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | JV Baseball | New Milford | Away - New Milford HS-Baseball Sub Varsity Field - NMHS [Directions] | 4:15 p.m. | ||
| Tue., 5/7 | FR Baseball | Newtown | Home - Pomperaug HS-Baseball Field [Directions] | 4:15 p.m. | ||
| Tue., 5/7 | V Boys Lacrosse | New Milford | Away - New Milford HS-North Turf Field - NMHS [Directions] | 7:00 p.m. | ||
| Tue., 5/7 | JV Boys Lacrosse | New Milford | Away - New Milford HS-North Turf Field - NMHS [Directions] | 5:00 p.m. | ||
| Tue., 5/7 | V Boys Outdoor Track | New Milford, Kolbe Cathedral, Notre Dame-Fairfield | Away - New Milford HS-Joe Wiser Stadium - NMHS [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | V Girls Golf | Masuk, Newtown | Home - Pomperaug HS-Pomperaug Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 5/7 | V Girls Lacrosse | New Milford | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | ||
| Tue., 5/7 | JV Girls Lacrosse | New Milford | Home - Pomperaug HS-Stadium [Directions] | 5:15 p.m. | ||
| Tue., 5/7 | JV Softball | New Milford | Away - New Milford HS-Softball JV Field - NMHS [Directions] | Postponed | ||
| Wed., 5/8 | FR Baseball | New Fairfield | Home - Pomperaug HS-Baseball Field [Directions] | Postponed | ||
| Wed., 5/8 | V Boys Tennis | Immaculate | Away - Rogers Park (Danbury, CT)-Tennis Courts [Directions] | 3:45 p.m. | ||
| Wed., 5/8 | V Softball | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Park Ave Field [Directions] | 5:30 p.m. | ||
| Wed., 5/8 | V Girls Tennis | Immaculate | Home - Edgewood Bath and Tennis Club [Directions] | 3:45 p.m. | ||
| Thu., 5/9 | V Boys Lacrosse | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 6:00 p.m. | ||
| Thu., 5/9 | V Girls Golf | Notre Dame-Fairfield, Stratford | Away - Fairchild Wheeler Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 5/9 | V Girls Lacrosse | Masuk | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | ||
| Thu., 5/9 | JV Girls Lacrosse | Masuk | Home - Pomperaug HS-Stadium [Directions] | 5:15 p.m. | ||
| Fri., 5/10 | V Boys Volleyball | Brookfield | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 5/10 | JV Boys Volleyball | Brookfield | Home - Pomperaug HS-Main Gym [Directions] | Canceled | Cancelled | |
| Sat., 5/11 | V Baseball | Newtown | Home - Pomperaug HS-Baseball Field [Directions] | 12:00 p.m. | ||
| Sat., 5/11 | JV Baseball | Weston | Home - Pomperaug HS-Baseball Field [Directions] | Postponed | ||
| Sat., 5/11 | FR Baseball | Nonnewaug | Away - Nonnewaug HS-Baseball Diamond [Directions] | 10:00 a.m. | ||
| Sat., 5/11 | V Boys Lacrosse | Wolcott | Home - Pomperaug HS-Stadium [Directions] | 12:00 p.m. | ||
| Sat., 5/11 | JV Boys Lacrosse | Wolcott | Home - Pomperaug HS-Stadium [Directions] | Canceled | Cancelled | |
| Sat., 5/11 | V Girls Lacrosse | Lauralton Hall | Away - Lauralton Hall-Turf Field [Directions] | 3:45 p.m. | ||
| Sat., 5/11 | JV Girls Lacrosse | Lauralton Hall | Away - Lauralton Hall-Turf Field [Directions] | 5:15 p.m. | ||
| Sat., 5/11 | JV Softball | New Fairfield | Home - Pomperaug HS-Softball Field [Directions] | 10:30 a.m. | ||
| Mon., 5/13 | V Baseball | Bethel | Home - Pomperaug HS-Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | FR Baseball | Bethel | Away - Bethel HS-MS Turf baseball field [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | V Boys Lacrosse | Immaculate | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | ||
| Mon., 5/13 | V Boys Tennis | Brookfield | Home - Edgewood Bath and Tennis Club [Directions] | 3:45 p.m. | ||
| Mon., 5/13 | V Boys Volleyball | Rockville | Away - Rockville HS-Main gymnasium [Directions] | 5:00 p.m. | ||
| Mon., 5/13 | JV Boys Volleyball | Rockville | Away - Rockville HS-Main gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | V Girls Golf | Joel Barlow | Home - Pomperaug HS-Pomperaug Golf Course [Directions] | 3:00 p.m. | ||
| Mon., 5/13 | V Girls Lacrosse | Immaculate | Away - Immaculate HS-Mustang Valley [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | V Girls Outdoor Track | Newtown, Bunnell | Away - Newtown HS-Blue and Gold Stadium [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | V Softball | Bethel | Home - Pomperaug HS-Softball Field [Directions] | 4:15 p.m. | ||
| Mon., 5/13 | JV Softball | Brookfield | Away - Brookfield HS-BHS Softball Field [Directions] | Canceled | Cancelled | |
| Mon., 5/13 | V Girls Tennis | Brookfield | Away - Brookfield HS-BHS Tennis Courts [Directions] | 3:45 p.m. | ||
| Tue., 5/14 | V Baseball | New Milford | Home - Pomperaug HS-Baseball Field [Directions] | 4:15 p.m. | ||
| Tue., 5/14 | JV Baseball | Bethel | Away - Bethel HS-Hunt Field at Bethel HS [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | V Boys Outdoor Track | Bunnell, Newtown | Home - Pomperaug HS-Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | V Boys Volleyball | Wolcott Tech | Home - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 5/14 | JV Boys Volleyball | Wolcott Tech | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | V Girls Golf | Bunnell | Away - Bunnell HS-Blackhawk Country Club (Old OCC) [Directions] | 3:00 p.m. | ||
| Tue., 5/14 | V Softball | Weston | Away - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 4:15 p.m. | ||
| Wed., 5/15 | FR Baseball | New Milford | Away - New Milford HS-Baseball Sub Varsity Field - NMHS [Directions] | Canceled | Cancelled | |
| Wed., 5/15 | V Boys Volleyball | Newtown | Home - Pomperaug HS-Main Gym [Directions] | 4:45 p.m. | ||
| Wed., 5/15 | JV Boys Volleyball | Newtown | Home - Pomperaug HS-Main Gym [Directions] | 3:30 p.m. | ||
| Thu., 5/16 | V Baseball | Weston | Away - Penders Field-Penders Field - Stratford [Directions] | 4:00 p.m. | ||
| Thu., 5/16 | V Boys Outdoor Track | SWC Freshmen Meet | Away - Bethel HS-BHS track | 4:00 p.m. | ||
| Thu., 5/16 | V Girls Lacrosse | New Fairfield | Away - New Fairfield HS-Marty Morgan Field [Directions] | 5:30 p.m. | ||
| Thu., 5/16 | V Girls Outdoor Track | SWC Freshmen Meet | Away - Bethel HS-BHS gym | 4:00 p.m. | ||
| Thu., 5/16 | JV Softball | Woodland | Away - Woodland HS-Softball Diamond [Directions] | Canceled | Cancelled | |
| Fri., 5/17 | V Boys Volleyball | Kolbe Cathedral | Away - Kolbe Cathedral HS-Gym [Directions] | 6:00 p.m. | ||
| Fri., 5/17 | JV Boys Volleyball | Kolbe Cathedral | Away - Kolbe Cathedral HS-Gym [Directions] | 4:30 p.m. | ||
| Fri., 5/17 | V Softball | Woodland | Home - Pomperaug HS-Softball Field [Directions] | 4:00 p.m. | ||
| Sat., 5/18 | V Softball | Notre Dame-Fairfield | Home - Pomperaug HS-Softball Field [Directions] | 12:00 p.m. | ||
| Mon., 5/20 | V Boys Outdoor Track | SWC Outdoor Track Championship | Away - Bethel HS-BHS track | 3:00 p.m. | ||
| Mon., 5/20 | V Boys Volleyball | Masuk | Home - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 5/20 | JV Boys Volleyball | Masuk | Home - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 5/20 | V Girls Outdoor Track | SWC Outdoor Track Championship | Away - Bethel HS-BHS track | 3:00 p.m. | ||
| Mon., 5/20 | V Softball | Masuk | Away - DeLuca Field-Deluca Field [Directions] | 7:00 p.m. | ||
| Mon., 5/20 | V Softball | Masuk | Home - DeLuca Field-Deluca Field [Directions] | 7:00 p.m. | ||
| Tue., 5/21 | V Baseball | Plainville | Home - Pomperaug HS-Dunkin Park- Hartford [Directions] | 6:30 p.m. | ||
| Tue., 5/21 | FR Baseball | New Fairfield | Home - Pomperaug HS-Baseball Field [Directions] | 4:00 p.m. | ||
| Tue., 5/21 | V Girls Golf | Masuk, Stratford | Away - Whitney Farms Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 5/21 | V Girls Tennis | Litchfield | Home - Edgewood Bath and Tennis Club [Directions] | 3:30 p.m. | ||
| Wed., 5/22 | V Baseball | Seymour | Away - French Park [Directions] | 3:45 p.m. | ||
| Wed., 5/22 | V Boys Lacrosse | Hall (Scrim.) | Home - Pomperaug HS-Stadium [Directions] | 4:30 p.m. | ||
| Wed., 5/22 | V Boys Volleyball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 5:00 p.m. | ||
| Wed., 5/22 | V Girls Lacrosse | Norwalk (Scrim.) | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | 4:15 p.m. | ||
| Fri., 5/24 | V Boys Tennis | New Milford | Home - Edgewood Bath and Tennis Club [Directions] | 1:00 p.m. | ||
| Fri., 5/24 | V Softball | Immaculate (Scrim.) | Home - Pomperaug HS-Softball Field [Directions] | 4:15 p.m. | ||
| Fri., 5/24 | V Girls Tennis | Bethel | Home - Edgewood Bath and Tennis Club [Directions] | 4:00 p.m. | ||
| Tue., 5/28 | V Baseball | Wilcox Tech | Away - Wilcox Tech-Baseball Diamond [Directions] | 3:30 p.m. | ||
| Tue., 5/28 | V Boys Tennis | Cheshire | Away - Cheshire HS-Tennis Courts [Directions] | 3:45 p.m. | ||
| Tue., 5/28 | V Girls Golf | SWC Girls Golf Championship | Away - Brownson Country Club | 8:00 a.m. | ||
| Tue., 5/28 | V Girls Lacrosse | Hall | Home - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Tue., 5/28 | V Softball | Killingly | Home - Pomperaug HS-Softball Field [Directions] | 4:00 p.m. | ||
| Tue., 5/28 | V Girls Tennis | Guilford | Away - Guilford HS-GHS Tennis Courts [Directions] | 3:45 p.m. | ||
| Wed., 5/29 | V Baseball | East Lyme | Away - East Lyme HS-ELHS Baseball Diamond [Directions] | 3:30 p.m. | ||
| Wed., 5/29 | V Boys Lacrosse | St. Paul Catholic | Home - Pomperaug HS-Stadium [Directions] | 6:30 p.m. | ||
| Wed., 5/29 | V Boys Volleyball | Putnam | Home - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 5/29 | V Softball | St. Joseph | Away - St. Joseph HS-Softball Diamond [Directions] | 4:00 p.m. | ||
| Thu., 5/30 | V Girls Lacrosse | Simsbury | Away - Holden Field-Turf [Directions] | 6:00 p.m. | ||
| Fri., 5/31 | V Boys Volleyball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 5:00 p.m. | ||
| Sat., 6/1 | V Boys Lacrosse | East Lyme | Away - East Lyme HS-Dick North Turf Field [Directions] | 3:00 p.m. | ||
| Fri., 6/7 | V Football | TBA | Home - Pomperaug HS-Stadium [Directions] | 6:30 p.m. | ||