| Weston 2021-22 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 772 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Sat., 8/28 | V Football | ATI, Amity, Bullard/Kolbe, Masuk, New Fairfield, Pomperaug | Away - Immaculate HS-Mustang Valley | 9:30 a.m. | ||
| Sun., 8/29 | V Boys Soccer | Alumni Game | Home - Weston HS-WHS Lower Turf Field [Directions] | 7:00 p.m. | ||
| Mon., 8/30 | V Boys Golf | Newtown | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | Newtown 178 Weston 193 | |
| Tue., 8/31 | V Boys Golf | Stratford | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | Weston 197 Stratford 264 | |
| Tue., 8/31 | V Boys Soccer | Norwalk (Scrim.) | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:30 p.m. | ||
| Tue., 8/31 | JV Boys Soccer | Norwalk (Scrim.) | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 9/1 | V Field Hockey | Mercy (Scrim.) | Home - Weston HS-WHS Lower Turf Field [Directions] | Canceled | Cancelled | Scrimmage |
| Thu., 9/2 | V Boys Soccer | Fairfield Ludlowe (Scrim.) | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | ||
| Thu., 9/2 | JV Boys Soccer | Fairfield Ludlowe (Scrim.) | Away - Tomlinson MS-Turf Field [Directions] | 3:30 p.m. | ||
| Thu., 9/2 | V Girls Soccer | Fairfield Ludlowe (Scrim.) | Home - Weston HS-WHS Lower Turf Field [Directions] | 7:00 p.m. | ||
| Thu., 9/2 | JV Girls Soccer | Fairfield Ludlowe (Scrim.) | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:30 p.m. | ||
| Thu., 9/2 | V Girls Volleyball | Fairfield Ludlowe (Scrim.) | Home - Weston HS-Gym (New) [Directions] | 4:00 p.m. | ||
| Thu., 9/2 | JV Girls Volleyball | Fairfield Ludlowe (Scrim.) | Home - Weston HS-Gym (Old) [Directions] | 4:00 p.m. | ||
| Fri., 9/3 | V Football | Seymour (Scrim.) | Home - Weston HS-WHS Stadium Field [Directions] | 6:00 p.m. | ||
| Fri., 9/3 | V Field Hockey | St. Joseph (Scrim.) | Home - Weston HS-WHS Lower Turf Field [Directions] | 3:00 p.m. | ||
| Fri., 9/3 | JV Field Hockey | St. Joseph (Scrim.) | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:30 p.m. | ||
| Sat., 9/4 | V Boys Soccer | Fairfield Warde (Scrim.) | Home - Weston HS-WHS Stadium Field [Directions] | 9:00 a.m. | ||
| Sat., 9/4 | JV Boys Soccer | Fairfield Warde (Scrim.) | Home - Weston HS-WHS Stadium Field [Directions] | 10:30 a.m. | ||
| Sun., 9/5 | V Girls Soccer | Newtown | Away - Treadwell Park-Treadwell Town Park--Tilson Field [Directions] | 10:20 a.m. | ||
| Sun., 9/5 | V Girls Soccer | Danbury | Away - Treadwell Park-Newtown Treadwell Park [Directions] | 9:00 a.m. | ||
| Sun., 9/5 | V Girls Soccer | Naugatuck | Home - Treadwell Park-Treadwell Town Park--Tilson Field [Directions] | 12:20 p.m. | ||
| Mon., 9/6 | V Field Hockey | Fairfield Warde (Scrim.) | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 12:30 p.m. | Scrximmage | |
| Mon., 9/6 | JV Field Hockey | Fairfield Warde (Scrim.) | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 2:00 p.m. | ||
| Mon., 9/6 | V Girls Soccer | Wilton (Scrim.) | Home - Weston HS-WHS Stadium Field [Directions] | 11:00 a.m. | ||
| Mon., 9/6 | JV Girls Soccer | Wilton (Scrim.) | Home - Weston HS-WHS Lower Turf Field [Directions] | 11:00 a.m. | ||
| Wed., 9/8 | V Boys Golf | Bethel | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | Bethel 178 Weston 178 | |
| Wed., 9/8 | V Boys Soccer | Darien (Scrim.) | Away - Darien HS-DHS Center Oval Turf Field [Directions] | 4:30 p.m. | ||
| Wed., 9/8 | JV Boys Soccer | Darien (Scrim.) | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:30 p.m. | ||
| Thu., 9/9 | V Boys Soccer | Fairfield Prep | Away - Fairfield University-Rafferty Stadium [Directions] | 4:00 p.m. | L 0-2 | |
| Thu., 9/9 | V Field Hockey | Masuk | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:30 p.m. | L 0-8 | |
| Thu., 9/9 | JV Field Hockey | Masuk | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:00 p.m. | ||
| Thu., 9/9 | V Girls Soccer | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 7:00 p.m. | W 3-1 | |
| Thu., 9/9 | V Girls Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 5:30 p.m. | W 3-2 | |
| Thu., 9/9 | JV Girls Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Thu., 9/9 | FR Girls Volleyball | Staples | Away - Staples HS-Field House [Directions] | 4:00 p.m. | ||
| Fri., 9/10 | V Football | New Fairfield | Home - Weston HS-WHS Stadium Field [Directions] | 7:00 p.m. | L 14-42 | |
| Fri., 9/10 | V Girls Swimming and Diving | New Milford | Home - Weston HS-Weston MS Pool [Directions] | 4:00 p.m. | Weston 101 New Milford 75 | |
| Sat., 9/11 | JV Football | New Fairfield | Away - New Fairfield HS-Stadium Field [Directions] | 11:00 a.m. | ||
| Sat., 9/11 | JV Boys Soccer | Fairfield Prep | Home - Weston HS-WHS Stadium Field [Directions] | 10:00 a.m. | ||
| Sat., 9/11 | V Field Hockey | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 11:30 a.m. | L 0-1 | |
| Sat., 9/11 | JV Field Hockey | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 1:30 p.m. | ||
| Sat., 9/11 | V Girls Soccer | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 10:00 a.m. | L 0-4 | |
| Sat., 9/11 | JV Girls Soccer | St. Joseph | Away - St. Joseph HS-Lower Grass Field [Directions] | Postponed | ||
| Sat., 9/11 | FR Girls Soccer | Westhill | Away - Westhill HS-Front Turf [Directions] | 10:30 a.m. | ||
| Sat., 9/11 | V Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 2:30 p.m. | W 3-2 | |
| Sat., 9/11 | JV Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 1:00 p.m. | ||
| Mon., 9/13 | V Field Hockey | Bethel | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:30 p.m. | L 2-1 | |
| Mon., 9/13 | JV Field Hockey | Bethel | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:00 p.m. | ||
| Mon., 9/13 | V Girls Volleyball | Brien McMahon | Home - Weston HS-Gym (New) [Directions] | 5:30 p.m. | W 3-0 | |
| Mon., 9/13 | JV Girls Volleyball | Brien McMahon | Home - Weston HS-Gym (New) [Directions] | 4:00 p.m. | ||
| Tue., 9/14 | V Boys Cross Country | Bunnell, Notre Dame-Fairfield, Stratford | Away - Bunnell HS-Bunnell XC Course [Directions] | 5:00 p.m. | W 15 - Bunnell 50 W 15 - ND 50 W 21 - Stratford 35 | |
| Tue., 9/14 | V Boys Golf | New Milford | Away - Candlewood Valley Country Club [Directions] | 3:00 p.m. | New Milford 173 Weston 189 | |
| Tue., 9/14 | V Boys Soccer | Masuk | Home - Weston HS-WHS Stadium Field [Directions] | 7:00 p.m. | T 2-2 | |
| Tue., 9/14 | JV Boys Soccer | Masuk | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:00 p.m. | ||
| Tue., 9/14 | V Girls Cross Country | Bunnell, Notre Dame-Fairfield, Stratford | Away - Bunnell HS-Bunnell XC Course [Directions] | 4:30 p.m. | Weston 27 Bunnell 28 Weston 15 Notre Dame 50 Weston 15 Stratford 50 | |
| Tue., 9/14 | V Girls Soccer | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 7:00 p.m. | T 0-0 | |
| Tue., 9/14 | JV Girls Soccer | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 5:00 p.m. | ||
| Tue., 9/14 | V Girls Swimming and Diving | St. Joseph | Home - Weston HS-Weston MS Pool [Directions] | 4:00 p.m. | Weston 93 St. Joes 80 | |
| Tue., 9/14 | V Girls Volleyball | Joel Barlow | Home - Weston HS-Gym (New) [Directions] | 5:30 p.m. | W 3-1 | |
| Tue., 9/14 | JV Girls Volleyball | Joel Barlow | Home - Weston HS-Gym (New) [Directions] | 4:00 p.m. | ||
| Wed., 9/15 | V Boys Golf | New Fairfield | Away - Club River Oaks [Directions] | 3:00 p.m. | Weston 176 New Fairfield 208 | |
| Wed., 9/15 | FR Girls Volleyball | Kennedy Catholic-Somers (NY) | Home - Weston HS-Gym (Old) [Directions] | 5:15 p.m. | ||
| Fri., 9/17 | V Football | Bethel | Away - Bethel HS-DeSantis Field at Bethel High [Directions] | 7:00 p.m. | W 38-7 | |
| Fri., 9/17 | V Boys Soccer | Immaculate | Away - Immaculate HS-Mustang Valley [Directions] | 4:00 p.m. | W 2-1 | |
| Fri., 9/17 | JV Boys Soccer | Immaculate | Away - Immaculate HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Fri., 9/17 | V Girls Soccer | Immaculate | Home - Weston HS-WHS Stadium Field [Directions] | 7:00 p.m. | W 3-0 | |
| Fri., 9/17 | V Girls Volleyball | Stamford | Home - Weston HS-Gym (New) [Directions] | 6:30 p.m. | W 3-0 | |
| Fri., 9/17 | JV Girls Volleyball | Stamford | Home - Weston HS-Gym (New) [Directions] | 5:00 p.m. | ||
| Fri., 9/17 | FR Girls Volleyball | Stamford | Home - Weston HS-Gym (Old) [Directions] | 5:00 p.m. | ||
| Sat., 9/18 | JV Football | Bethel | Home - Weston HS-WHS Stadium Field [Directions] | 11:00 a.m. | ||
| Sat., 9/18 | FR Girls Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 10:00 a.m. | ||
| Sat., 9/18 | FR Girls Volleyball | Bethel | Away - Bethel HS-BHS gym [Directions] | 10:00 a.m. | ||
| Mon., 9/20 | V Field Hockey | New Milford | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:30 p.m. | L 0-4 | |
| Mon., 9/20 | JV Field Hockey | New Milford | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:00 p.m. | ||
| Mon., 9/20 | FR Girls Soccer | Fairfield Warde | Away - Tunxis [Directions] | 4:00 p.m. | ||
| Mon., 9/20 | V Girls Volleyball | New Milford | Home - Weston HS-Gym (New) [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 9/20 | JV Girls Volleyball | New Milford | Home - Weston HS-Gym (New) [Directions] | 5:30 p.m. | ||
| Mon., 9/20 | FR Girls Volleyball | New Milford | Home - Weston HS-Gym (Old) [Directions] | 4:00 p.m. | ||
| Tue., 9/21 | V Boys Cross Country | Bethel, Newtown | Away - Bethel HS-BHS track [Directions] | 4:30 p.m. | Weston 21 Bethel 34 Weston 25 Newtown 31 | |
| Tue., 9/21 | V Boys Golf | Pomperaug | Away - Pomperaug HS-Highfield Country Club [Directions] | 3:00 p.m. | Pomperaug 160 Weston 193 | |
| Tue., 9/21 | V Boys Soccer | Newtown | Home - Weston HS-WHS Stadium Field [Directions] | 7:00 p.m. | W 1-0 | |
| Tue., 9/21 | JV Boys Soccer | Newtown | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:30 p.m. | ||
| Tue., 9/21 | V Girls Cross Country | Bethel, Newtown | Away - Bethel HS-BHS track [Directions] | 5:00 p.m. | Weston | |
| Tue., 9/21 | V Girls Soccer | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 7:00 p.m. | W 1-0 | |
| Tue., 9/21 | JV Girls Soccer | Newtown | Away - Newtown HS-NHS Practice Fields [Directions] | 4:00 p.m. | ||
| Tue., 9/21 | V Girls Swimming and Diving | New Fairfield | Away - New Fairfield HS-Pool [Directions] | 4:00 p.m. | Weston 103 New Fairfield 76 | |
| Tue., 9/21 | FR Girls Volleyball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 6:30 p.m. | ||
| Wed., 9/22 | V Field Hockey | Immaculate | Away - Immaculate HS-Mustang Valley [Directions] | 4:00 p.m. | L 1-3 | |
| Wed., 9/22 | JV Field Hockey | Immaculate | Away - Immaculate HS-Mustang Valley [Directions] | 5:30 p.m. | ||
| Wed., 9/22 | V Girls Volleyball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 5:30 p.m. | W 3-1 | |
| Wed., 9/22 | JV Girls Volleyball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 4:00 p.m. | ||
| Thu., 9/23 | V Boys Golf | Brookfield | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | Weston 188 Brookfield 194 | |
| Thu., 9/23 | V Boys Soccer | Stratford | Away - Penders Field-Penders Field - Stratford [Directions] | 5:30 p.m. | W 2-1 | |
| Thu., 9/23 | JV Boys Soccer | Stratford | Away - Penders Field-Penders Field - Stratford [Directions] | 7:00 p.m. | ||
| Thu., 9/23 | V Girls Soccer | Stratford | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:00 p.m. | W 2-0 | |
| Thu., 9/23 | JV Girls Soccer | Stratford | Home - Weston HS-WHS Stadium Field [Directions] | 7:00 p.m. | ||
| Fri., 9/24 | V Field Hockey | Joel Barlow | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:30 p.m. | L 0-3 | |
| Fri., 9/24 | JV Field Hockey | Joel Barlow | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:00 p.m. | ||
| Fri., 9/24 | FR Girls Soccer | Darien | Away - Darien HS-MMS (Middlesex) Lower Field at 30 Edgerton Street [Directions] | 4:00 p.m. | ||
| Fri., 9/24 | V Girls Swimming and Diving | Stratford | Home - Weston HS-Weston MS Pool [Directions] | 7:00 p.m. | Weston 96 Stratford 70 | |
| Fri., 9/24 | V Girls Volleyball | Pomperaug | Home - Weston HS-Gym (New) [Directions] | 5:30 p.m. | W 3-2 | |
| Fri., 9/24 | JV Girls Volleyball | Pomperaug | Home - Weston HS-Gym (New) [Directions] | 4:00 p.m. | ||
| Fri., 9/24 | FR Girls Volleyball | Pomperaug | Home - Weston HS-Gym (Old) [Directions] | 4:00 p.m. | ||
| Sat., 9/25 | V Girls Soccer | Fairfield Warde | Home - Weston HS-WHS Stadium Field [Directions] | 2:00 p.m. | W 1-0 | |
| Sat., 9/25 | JV Girls Soccer | Fairfield Warde | Home - Weston HS-WHS Stadium Field [Directions] | 12:00 p.m. | ||
| Mon., 9/27 | V Boys Golf | Notre Dame-Fairfield | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | Weston 187 Notre Dame 300 | |
| Mon., 9/27 | V Field Hockey | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 6:30 p.m. | L 0-3 | |
| Mon., 9/27 | JV Field Hockey | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 5:00 p.m. | ||
| Tue., 9/28 | V Boys Golf | Joel Barlow | Away - Redding Country Club [Directions] | 3:00 p.m. | Weston 178 Joel Barlow 192 | |
| Tue., 9/28 | V Boys Soccer | Notre Dame-Fairfield | Home - Weston HS-WHS Stadium Field [Directions] | 7:00 p.m. | W 6-0 | |
| Tue., 9/28 | V Girls Soccer | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Park Ave Field [Directions] | 4:00 p.m. | T 0-0 | |
| Tue., 9/28 | FR Girls Volleyball | Newtown | Away - Newtown HS-Gym [Directions] | 5:30 p.m. | ||
| Wed., 9/29 | V Boys Cross Country | Kolbe Cathedral, Masuk | Home - Weston HS-WHS Stadium Field [Directions] | 4:30 p.m. | Weston 15 Masuk 40 Weston 17 Kolbe 43 | |
| Wed., 9/29 | V Girls Cross Country | Kolbe Cathedral, Masuk | Home - Weston HS-WHS Stadium Field [Directions] | 5:00 p.m. | Weston 19 Masuk 36 Weston 15 Kolbe 50 | |
| Wed., 9/29 | V Field Hockey | New Fairfield | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:30 p.m. | OT-L 1-2 | |
| Wed., 9/29 | JV Field Hockey | New Fairfield | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:00 p.m. | ||
| Wed., 9/29 | FR Girls Soccer | Masuk | Away - Masuk HS-Masuk High School Middle Field [Directions] | 4:00 p.m. | ||
| Wed., 9/29 | V Girls Volleyball | Newtown | Away - Newtown HS-Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 9/29 | JV Girls Volleyball | Newtown | Away - Newtown HS-Gym [Directions] | 4:00 p.m. | ||
| Thu., 9/30 | V Boys Golf | Bunnell | Away - Bunnell HS-Oronoque C.C. [Directions] | 3:00 p.m. | Weston 180 Bunnell 237 | |
| Thu., 9/30 | V Boys Soccer | Pomperaug | Away - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | W 2-0 | |
| Thu., 9/30 | JV Boys Soccer | Pomperaug | Away - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Thu., 9/30 | V Girls Soccer | Pomperaug | Home - Weston HS-WHS Stadium Field [Directions] | 7:00 p.m. | T 0-0 | |
| Thu., 9/30 | JV Girls Soccer | Pomperaug | Home - Weston HS-WHS Lower Turf Field [Directions] | 7:00 p.m. | ||
| Fri., 10/1 | V Football | Sheehan | Away - Sheehan HS-Sheehan HS Riccitelli Field (Turf) [Directions] | 7:00 p.m. | L 14-32 | |
| Fri., 10/1 | V Girls Swimming and Diving | Masuk | Away - Masuk HS-Pool [Directions] | 4:00 p.m. | Weston 102 Masuk 75 | |
| Fri., 10/1 | V Girls Volleyball | Bunnell | Home - Weston HS-Gym (New) [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 10/1 | JV Girls Volleyball | Bunnell | Home - Weston HS-Gym (New) [Directions] | 4:00 p.m. | ||
| Sat., 10/2 | JV Football | Sheehan | Home - Weston HS-WHS Stadium Field [Directions] | 3:00 p.m. | ||
| Sat., 10/2 | FR Girls Soccer | Staples | Home - Weston HS-WHS Lower Turf Field [Directions] | 10:00 a.m. | ||
| Mon., 10/4 | V Boys Golf | Immaculate, Joel Barlow | Away - Immaculate HS-Ridgewood CC [Directions] | 3:00 p.m. | Weston 178 Immaculate 186 | |
| Mon., 10/4 | V Field Hockey | New Milford | Away - New Milford HS-Joe Wiser Stadium - NMHS [Directions] | 5:30 p.m. | W 2-0 | |
| Mon., 10/4 | JV Field Hockey | New Milford | Away - New Milford HS-Joe Wiser Stadium - NMHS [Directions] | 4:00 p.m. | ||
| Mon., 10/4 | FR Girls Soccer | Masuk | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | ||
| Mon., 10/4 | V Girls Volleyball | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Sister Marion Reilly Auditorium [Directions] | 6:15 p.m. | W 3-0 | |
| Mon., 10/4 | JV Girls Volleyball | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Sister Marion Reilly Auditorium [Directions] | 5:00 p.m. | ||
| Mon., 10/4 | FR Girls Volleyball | Fairfield Warde | Home - Weston HS-Gym (New) [Directions] | 4:00 p.m. | ||
| Tue., 10/5 | V Boys Cross Country | Brookfield, Joel Barlow, New Fairfield | Home - Weston HS-WHS Stadium Field [Directions] | 4:30 p.m. | Weston 25 Brookfield 32 Weston 21 New Fairfield 38 Joel Barlow 22 Weston 38 | |
| Tue., 10/5 | V Boys Golf | Masuk | Away - Whitney Farms Golf Course [Directions] | 3:00 p.m. | Weston 188 Masuk 198 | |
| Tue., 10/5 | V Boys Soccer | Brookfield | Home - Weston HS-WHS Stadium Field [Directions] | 7:00 p.m. | W 5-1 | |
| Tue., 10/5 | JV Boys Soccer | Brookfield | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:00 p.m. | ||
| Tue., 10/5 | V Girls Cross Country | Brookfield, Joel Barlow, New Fairfield | Home - Weston HS-WHS Stadium Field [Directions] | 5:00 p.m. | Weston 22 Barlow 35 Brookfield 24 Weston 31 New Fairfield 23 Weston 35 | |
| Tue., 10/5 | V Girls Soccer | Brookfield | Away - Brookfield HS-BHS Stadium Field [Directions] | 6:00 p.m. | T 0-0 | |
| Tue., 10/5 | JV Girls Soccer | Brookfield | Away - Brookfield HS-BHS Stadium Field [Directions] | 4:00 p.m. | ||
| Tue., 10/5 | V Girls Swimming and Diving | Bunnell | Away - Bunnell HS-Flood M.S. Pool [Directions] | 6:30 p.m. | Weston 95 Bunnell 67 | |
| Wed., 10/6 | V Boys Golf | Masuk | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | Masuk 163 Weston 188 | |
| Wed., 10/6 | V Field Hockey | Newtown | Home - Weston HS-WHS Lower Turf Field [Directions] | 7:00 p.m. | L 0-5 | |
| Wed., 10/6 | JV Field Hockey | Newtown | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:45 p.m. | ||
| Wed., 10/6 | FR Girls Soccer | Newtown | Away - Newtown HS-NHS Practice Fields [Directions] | Canceled | Cancelled | |
| Wed., 10/6 | V Girls Volleyball | Immaculate | Home - Weston HS-Gym (New) [Directions] | 7:00 p.m. | W 3-0 | |
| Wed., 10/6 | JV Girls Volleyball | Immaculate | Home - Weston HS-Gym (New) [Directions] | 5:30 p.m. | ||
| Wed., 10/6 | FR Girls Volleyball | Immaculate | Home - Weston HS-Gym (Old) [Directions] | 5:30 p.m. | ||
| Thu., 10/7 | JV Football | Bunnell | Away - Bunnell HS-Mastroni Field [Directions] | Canceled | Cancelled | |
| Thu., 10/7 | V Boys Golf | Immaculate | Away - Immaculate HS-Richter Park [Directions] | 3:00 p.m. | Immaculate 186 Weston 200 | |
| Thu., 10/7 | V Girls Soccer | New Fairfield | Home - Weston HS-WHS Stadium Field [Directions] | 7:00 p.m. | W 4-1 | |
| Thu., 10/7 | JV Girls Soccer | New Fairfield | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:00 p.m. | ||
| Thu., 10/7 | FR Girls Volleyball | Kennedy Catholic-Somers (NY) | Away - Kennedy Catholic HS | 4:30 p.m. | ||
| Fri., 10/8 | V Football | Bunnell | Home - Weston HS-WHS Stadium Field [Directions] | 7:00 p.m. | L 6-28 | |
| Fri., 10/8 | V Boys Soccer | New Fairfield | Away - New Fairfield HS-Marty Morgan Field [Directions] | 6:00 p.m. | W 5-1 | |
| Fri., 10/8 | JV Boys Soccer | New Fairfield | Away - New Fairfield HS-Marty Morgan Field [Directions] | 4:00 p.m. | ||
| Fri., 10/8 | V Girls Swimming and Diving | Bethel/Immaculate, Immaculate | Home - Weston HS-Weston MS Pool [Directions] | 7:00 p.m. | Weston 99 Bethel/Immaculate 76 | |
| Fri., 10/8 | V Girls Volleyball | New Fairfield | Home - Weston HS-Gym (New) [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 10/8 | JV Girls Volleyball | New Fairfield | Home - Weston HS-Gym (New) [Directions] | 4:00 p.m. | ||
| Fri., 10/8 | FR Girls Volleyball | New Fairfield | Home - Weston HS-Gym (Old) [Directions] | 4:00 p.m. | ||
| Sat., 10/9 | V Field Hockey | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 11:00 a.m. | OT-L 1-2 | |
| Sat., 10/9 | JV Field Hockey | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 12:30 p.m. | ||
| Sat., 10/9 | FR Girls Soccer | Greenwich | Home - Weston HS-WHS Lower Turf Field [Directions] | 10:00 a.m. | ||
| Mon., 10/11 | V Boys Golf | Pomperaug | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | Pomperaug 172 Weston 201 | |
| Tue., 10/12 | V Boys Cross Country | Immaculate, New Milford, Pomperaug | Away - Immaculate HS-Tarrywile [Directions] | 4:30 p.m. | New Milford 17 Weston 40 Pomperaug 20 Weston 39 Immaculate 25 Weston 33 | |
| Tue., 10/12 | V Boys Golf | SWC Championship at Fairchild Wheeler- Black | Away - Pomperaug HS-Fairchild Wheeler Golf Course | 8:30 a.m. | ||
| Tue., 10/12 | V Boys Soccer | Bethel | Home - Weston HS-WHS Stadium Field [Directions] | 7:00 p.m. | W 1-0 | |
| Tue., 10/12 | JV Boys Soccer | Bethel | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:00 p.m. | ||
| Tue., 10/12 | V Girls Cross Country | Immaculate, New Milford, Pomperaug | Away - Immaculate HS-Tarrywile [Directions] | 5:00 p.m. | ||
| Tue., 10/12 | V Girls Soccer | Bethel | Away - Bethel HS-DeSantis Field at Bethel High [Directions] | 6:00 p.m. | W 3-2 | |
| Tue., 10/12 | JV Girls Soccer | Bethel | Away - Bethel MS-Middle School soccer field [Directions] | 4:00 p.m. | ||
| Tue., 10/12 | V Girls Swimming and Diving | Pomperaug | Home - Weston HS-Weston MS Pool [Directions] | 4:00 p.m. | Weston 101 Pomperaug 74 | |
| Tue., 10/12 | V Girls Volleyball | Stratford | Home - Weston HS-Gym (New) [Directions] | 5:30 p.m. | W 3-1 | |
| Tue., 10/12 | JV Girls Volleyball | Stratford | Home - Weston HS-Gym (New) [Directions] | 4:00 p.m. | ||
| Tue., 10/12 | FR Girls Volleyball | Stratford | Home - Weston HS-Gym (Old) [Directions] | 4:00 p.m. | ||
| Wed., 10/13 | V Field Hockey | Pomperaug | Away - Pomperaug HS-Stadium [Directions] | 5:30 p.m. | L 0-1 | |
| Wed., 10/13 | JV Field Hockey | Pomperaug | Away - Pomperaug HS-Stadium [Directions] | 4:00 p.m. | ||
| Wed., 10/13 | FR Girls Soccer | Trumbull | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 10/14 | V Boys Soccer | New Milford | Away - New Milford HS-Joe Wiser Stadium - NMHS [Directions] | 6:00 p.m. | W 2-0 | |
| Thu., 10/14 | JV Boys Soccer | New Milford | Away - New Milford HS-Joe Wiser Stadium - NMHS [Directions] | 4:00 p.m. | ||
| Thu., 10/14 | V Girls Soccer | New Milford | Home - Weston HS-WHS Stadium Field [Directions] | 7:00 p.m. | W 6-0 | |
| Thu., 10/14 | JV Girls Soccer | New Milford | Home - Weston HS-WHS Lower Turf Field [Directions] | Postponed | ||
| Thu., 10/14 | V Girls Volleyball | New Milford | Away - New Milford HS-Main Gym - NMHS [Directions] | 5:30 p.m. | W 3-1 | |
| Thu., 10/14 | JV Girls Volleyball | New Milford | Away - New Milford HS-Main Gym - NMHS [Directions] | 6:45 p.m. | ||
| Thu., 10/14 | FR Girls Volleyball | New Milford | Away - New Milford HS-Small Gym - NMHS [Directions] | 5:30 p.m. | ||
| Fri., 10/15 | V Field Hockey | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 5:45 p.m. | L 0-2 | |
| Fri., 10/15 | JV Field Hockey | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 4:15 p.m. | ||
| Sat., 10/16 | V Football | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -McCarty Stadium [Directions] | 12:00 p.m. | L Weston | |
| Sat., 10/16 | FR Girls Soccer | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 9:00 a.m. | ||
| Sat., 10/16 | V Girls Volleyball | Kolbe Cathedral | Home - Weston HS-Gym (New) [Directions] | 11:30 a.m. | W 3-0 | |
| Sat., 10/16 | JV Girls Volleyball | Kolbe Cathedral | Home - Weston HS-Gym (New) [Directions] | 10:00 a.m. | ||
| Sat., 10/16 | FR Girls Volleyball | Bethel | Home - Weston HS-Gym (Old) [Directions] | 10:00 a.m. | ||
| Mon., 10/18 | V Boys Golf | CIAC Fall Division II Boys Golf Championship | Away - Silo Point GC | 8:30 a.m. | ||
| Mon., 10/18 | V Field Hockey | Bethel | Away - Bethel HS-Hunt Field at Bethel HS [Directions] | 6:00 p.m. | L 1-3 | |
| Mon., 10/18 | JV Field Hockey | Bethel | Away - Bethel HS-Hunt Field at Bethel HS [Directions] | 4:15 p.m. | ||
| Mon., 10/18 | Unified Sports Soccer | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 3:00 p.m. | ||
| Tue., 10/19 | V Boys Soccer | Joel Barlow | Away - Joel Barlow HS-Field J (Competition Field) [Directions] | 4:00 p.m. | W 2-0 | |
| Tue., 10/19 | V Girls Soccer | Joel Barlow | Home - Weston HS-WHS Stadium Field [Directions] | 7:00 p.m. | W 2-1 | |
| Tue., 10/19 | JV Girls Soccer | Joel Barlow | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:00 p.m. | ||
| Tue., 10/19 | V Girls Swimming and Diving | Newtown | Away - Newtown HS-pool [Directions] | 6:00 p.m. | Weston 99 Newtown 79 | |
| Tue., 10/19 | V Girls Volleyball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 6:15 p.m. | W 3-0 | |
| Tue., 10/19 | JV Girls Volleyball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 5:00 p.m. | ||
| Tue., 10/19 | FR Girls Volleyball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 3:45 p.m. | ||
| Wed., 10/20 | V Boys Cross Country | SWC Championship | Away - Bethel HS-BHS track | 3:30 p.m. | ||
| Wed., 10/20 | V Girls Cross Country | SWC Championship | Away - Bethel HS-BHS track | 3:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 4:00 p.m. | ||||||
| Wed., 10/20 | V Field Hockey | Brookfield | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:30 p.m. | L 0-1 | |
| Wed., 10/20 | JV Field Hockey | Brookfield | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:00 p.m. | ||
| Wed., 10/20 | FR Girls Soccer | Ridgefield | Away - Ridgefield HS-RHS Lower Grass Field [Directions] | 4:30 p.m. | ||
| Thu., 10/21 | V Boys Soccer | Bunnell | Away - Bunnell HS-Mastroni Field [Directions] | 7:00 p.m. | T 2-2 | |
| Thu., 10/21 | JV Boys Soccer | Bunnell | Away - Bunnell HS-Mastroni Field [Directions] | 5:00 p.m. | ||
| Thu., 10/21 | V Girls Soccer | Bunnell | Home - Weston HS-WHS Stadium Field [Directions] | 6:00 p.m. | W 6-0 | |
| Thu., 10/21 | V Girls Volleyball | Bethel | Away - Bethel HS-BHS gym [Directions] | 5:30 p.m. | W 3-0 | |
| Thu., 10/21 | JV Girls Volleyball | Bethel | Away - Bethel HS-BHS gym [Directions] | 4:00 p.m. | ||
| Fri., 10/22 | V Football | Platt | Home - Weston HS-WHS Stadium Field [Directions] | 7:00 p.m. | L 21-22 | Homecoming |
| Fri., 10/22 | V Girls Swimming and Diving | Brookfield | Away - Brookfield YMCA-Outside/Dome Pool [Directions] | 5:45 p.m. | Weston 101 Brookfield 66 | |
| Sat., 10/23 | JV Football | Platt | Away - Platt HS-Platt Turf field [Directions] | 10:00 a.m. | ||
| Sat., 10/23 | V Boys Soccer | Seymour | Away - Seymour HS-Seymour High School Turf Field [Directions] | 1:30 p.m. | W 5-0 | |
| Sat., 10/23 | JV Boys Soccer | Joel Barlow | Away - Joel Barlow HS-Field E (Softball) [Directions] | 2:30 p.m. | ||
| Sat., 10/23 | JV Girls Soccer | Bunnell | Home - Weston HS-WHS Lower Turf Field [Directions] | 2:00 p.m. | ||
| Sat., 10/23 | FR Girls Soccer | Wilton | Away - Wilton HS-Lilly Field [Directions] | 10:00 a.m. | ||
| Mon., 10/25 | V Boys Soccer | Kolbe Cathedral | Home - Weston HS-WHS Stadium Field [Directions] | 7:00 p.m. | W 12-1 | |
| Mon., 10/25 | V Field Hockey | Fairfield Ludlowe | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:00 p.m. | L 0-1 | |
| Mon., 10/25 | JV Field Hockey | Fairfield Ludlowe | Home - Weston HS-WHS Lower Turf Field [Directions] | 3:30 p.m. | ||
| Mon., 10/25 | V Girls Soccer | Kolbe Cathedral | Away - Veterans Memorial Park CT [Directions] | 4:00 p.m. | W 6-0 | |
| Mon., 10/25 | V Girls Volleyball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Mon., 10/25 | JV Girls Volleyball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/26 | V Girls Swimming and Diving | Joel Barlow | Home - Weston HS-Weston MS Pool [Directions] | 4:00 p.m. | Weston 95 Joel Barlow 71 | |
| Wed., 10/27 | V Boys Soccer | Abbott Tech | Home - Weston HS-WHS Stadium Field [Directions] | 6:00 p.m. | W 4-0 | |
| Wed., 10/27 | V Girls Volleyball | Masuk | Home - Weston HS-Gym (New) [Directions] | 6:45 p.m. | W 3-0 | |
| Wed., 10/27 | JV Girls Volleyball | Masuk | Home - Weston HS-Gym (New) [Directions] | 5:15 p.m. | ||
| Wed., 10/27 | FR Girls Volleyball | Masuk | Home - Weston HS-Gym (Old) [Directions] | 5:15 p.m. | ||
| Fri., 10/29 | V Football | Foran | Home - Weston HS-WHS Stadium Field [Directions] | 7:00 p.m. | W 34-20 | |
| Sat., 10/30 | JV Football | Foran | Away - Foran HS -Foran High School - Turf Field [Directions] | 10:00 a.m. | ||
| Sat., 10/30 | V Boys Soccer | Bunnell | Home - Weston HS-WHS Stadium Field [Directions] | 4:00 p.m. | W 5-0 | |
| Sat., 10/30 | V Girls Soccer | Bethel | Home - Weston HS-WHS Stadium Field [Directions] | 1:30 p.m. | W 1-0 | |
| Mon., 11/1 | V Boys Cross Country | CIAC Boys Cross Country Class M Championship | Away - Wickham Park | 9:15 a.m. | ||
| Mon., 11/1 | V Boys Soccer | Bethel | Home - Weston HS-WHS Stadium Field [Directions] | 6:30 p.m. | W 2-1 | |
| Mon., 11/1 | V Girls Cross Country | CIAC Girls Cross Country Class M Championship | Away - Wickham Park | 9:45 a.m. | ||
| Mon., 11/1 | V Girls Volleyball | Stratford | Home - Weston HS-Gym (New) [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 11/2 | V Girls Soccer | Newtown | Home - Weston HS-WHS Stadium Field [Directions] | 6:30 p.m. | W 2-1 | |
| Wed., 11/3 | V Boys Soccer | Joel Barlow | Home - Newtown HS-Blue and Gold Stadium [Directions] | 7:00 p.m. | W 2-0 | |
| Wed., 11/3 | V Girls Swimming and Diving | SWC Diving Championship Meet | Home - Weston HS-Weston MS Pool [Directions] | 5:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 5:30 p.m. | ||||||
| Wed., 11/3 | V Girls Volleyball | Joel Barlow | Home - Weston HS-Gym (New) [Directions] | 6:00 p.m. | W 3-0 | |
| Thu., 11/4 | V Girls Soccer | Brookfield | Home - Newtown HS-Blue and Gold Stadium [Directions] | 7:00 p.m. | L 0-3 | |
| Fri., 11/5 | V Boys Cross Country | CIAC Boys Cross Country Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Fri., 11/5 | V Football | Newtown | Home - Weston HS-WHS Stadium Field [Directions] | 7:00 p.m. | L 28-35 | |
| Fri., 11/5 | V Girls Cross Country | CIAC Girls Cross Country Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Sat., 11/6 | JV Football | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 10:30 a.m. | ||
| Sat., 11/6 | V Girls Swimming and Diving | SWC Girls Swimming Championship Meet | Away - Masuk HS-Pool | 3:30 p.m. | ||
| Sat., 11/6 | V Girls Volleyball | Newtown | Home - Bethel HS-Gym [Directions] | 6:00 p.m. | W 3-2 | |
| Mon., 11/8 | V | Wilton | Home - Weston HS-WHS Lower Turf Field [Directions] | 2:45 p.m. | ||
| Mon., 11/8 | V Girls Soccer | Stonington | Home - Weston HS-WHS Stadium Field [Directions] | 6:00 p.m. | W 2-0 | |
| Tue., 11/9 | V Boys Soccer | Goodwin Tech | Home - Weston HS-WHS Stadium Field [Directions] | 2:00 p.m. | W 14-0 | |
| Wed., 11/10 | V Girls Soccer | Windham | Home - Weston HS-WHS Stadium Field [Directions] | 2:00 p.m. | W 4-0 | |
| Wed., 11/10 | V Girls Swimming and Diving | CIAC Class S Diving Championships | Away - Sheehan | 5:30 p.m. | ||
| Wed., 11/10 | V Girls Volleyball | Joel Barlow | Home - Weston HS-Gym (New) [Directions] | 6:00 p.m. | W 3-2 | |
| Thu., 11/11 | V Boys Soccer | Bacon Academy | Home - Weston HS-WHS Stadium Field [Directions] | 2:00 p.m. | L 1-2 (4-5 in PKs | |
| Fri., 11/12 | V Football | East Haven | Away - East Haven HS-EHHS Turf Field & Track [Directions] | 7:00 p.m. | W 54-0 | |
| Fri., 11/12 | V Girls Volleyball | Woodland | Home - Weston HS-Gym (New) [Directions] | 7:00 p.m. | W 3-1 | |
| Sat., 11/13 | JV Football | Jonathan Law | Home - Weston HS-WHS Stadium Field [Directions] | 11:00 a.m. | ||
| Sat., 11/13 | V Girls Soccer | Mercy | Away - Xavier HS-Larry McHugh Field [Directions] | 2:30 p.m. | ||
| Sat., 11/13 | V Girls Swimming and Diving | CIAC Class S Qualifying Meet | Away - Cheshire Community Pool | 6:00 p.m. | ||
| Tue., 11/16 | V Girls Volleyball | Ledyard | Home - Hillhouse HS-Gym [Directions] | 6:00 p.m. | ||
| Wed., 11/17 | V Girls Swimming and Diving | CIAC Class S Swimming Championships | Away - Cornerstone Pool | 6:00 p.m. | ||
| Thu., 11/18 | V Girls Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Fri., 11/19 | JV Football | Joel Barlow | Home - Weston HS-WHS Stadium Field [Directions] | 5:00 p.m. | ||
| Sat., 11/20 | V Girls Volleyball | Seymour | Home - East Haven HS-Gym [Directions] | 1:00 p.m. | ||
| Sun., 11/21 | V Girls Swimming and Diving | CIAC State Open Swimming Championships | Away - Cornerstone Pool | 2:00 p.m. | ||
| Thu., 11/25 | V Football | Joel Barlow | Away - Joel Barlow HS-Field I (Stadium) [Directions] | 10:00 a.m. | L 16-42 | |
| Sat., 12/4 | V Girls Ice Hockey | Hamden Coop (Scrim.) | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 5:30 p.m. | Scrimmage | |
| Tue., 12/7 | V Girls Basketball | Lauralton Hall (Scrim.) | Home - Weston HS-Gym (New) [Directions] | 6:30 p.m. | ||
| Wed., 12/8 | V Boys Basketball | New Canaan (Scrim.) | Away - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 12/8 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | L 4-3 OT | |
| Fri., 12/10 | V Girls Basketball | Darien (Scrim.) | Home - Weston HS-Gym (New) [Directions] | 6:30 p.m. | ||
| Fri., 12/10 | V Girls Ice Hockey | Hamden Coop | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | L 4-3 | |
| Mon., 12/13 | V Girls Basketball | Foran | Away - Foran HS -Edna L. Fraser Gymnasium [Directions] | 5:45 p.m. | L 20-43 | |
| Mon., 12/13 | JV Girls Basketball | Foran | Away - Foran HS -Edna L. Fraser Gymnasium [Directions] | 4:15 p.m. | ||
| Tue., 12/14 | V Boys Basketball | Oxford (Scrim.) | Away - Oxford HS-Main Gym [Directions] | Canceled | Cancelled | |
| Wed., 12/15 | V Wrestling | Pomperaug Coop | Away - Pomperaug HS-Auxiliary Gym [Directions] | 6:00 p.m. | Weston 39 Pomperaug 33 | |
| Wed., 12/15 | V Girls Basketball | Wilton | Home - Weston HS-Gym (New) [Directions] | 5:30 p.m. | L 28-42 | |
| Wed., 12/15 | JV Girls Basketball | Wilton | Home - Weston HS-Gym (New) [Directions] | 4:00 p.m. | ||
| Wed., 12/15 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Away - Hamden-Lou Astorino Ice Rink [Directions] | 3:45 p.m. | L 3-0 | |
| Thu., 12/16 | JV Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena-Patriot Rink [Directions] | 5:00 p.m. | ||
| Fri., 12/17 | V Boys Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 7:00 p.m. | L 21-42 | |
| Fri., 12/17 | JV Boys Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 12/17 | FR Boys Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 12/17 | V Boys Indoor Track | Coach Saint Invitational at NYC Armory | Away - Not Listed-NYC Armory | 5:00 p.m. | ||
| Fri., 12/17 | V Girls Indoor Track | Coach Saint Invitational at NYC Armory | Away - Not Listed-NYC Armory | 5:00 p.m. | ||
| Sat., 12/18 | V Boys Ice Hockey | Brien McMahon/Norwalk | Home - Danbury Ice Arena-Patriot Rink [Directions] | 11:00 a.m. | L 0-2 | |
| Sat., 12/18 | V Wrestling | Ludlowe Invitational | Away - Fairfield Ludlowe HS-Main Gym | 9:00 a.m. | ||
| Sat., 12/18 | FR Girls Basketball | Wilton | Home - Weston HS-Gym (New) [Directions] | 11:00 a.m. | ||
| Sat., 12/18 | V Girls Ice Hockey | West Haven/SHA | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 8:30 p.m. | L 4-1 | |
| Sun., 12/19 | JV Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 8:00 p.m. | ||
| Mon., 12/20 | V Boys Ice Hockey | Housatonic Coop | Away - South Kent School-Ice Rink [Directions] | 4:00 p.m. | W 5-1 | |
| Tue., 12/21 | V Boys Swimming and Diving | Bunnell-Stratford | Home - Weston HS-Weston MS Pool [Directions] | 4:00 p.m. | Weston 93 Bunnell/Stratford 61 | |
| Wed., 12/22 | V Boys Ice Hockey | Staples | Away - Milford Ice Pavillion-Ice Rink [Directions] | 5:25 p.m. | W 3-2 | |
| Wed., 12/22 | V Wrestling | Brookfield/Shepaug | Home - Weston HS-Gym (New) [Directions] | 6:00 p.m. | Weston 42 Brookfield 41 | |
| Thu., 12/23 | JV Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 5:00 p.m. | ||
| Tue., 12/28 | V Boys Basketball | Woodlands (NY) | Home - Weston HS-Gym (New) [Directions] | 2:00 p.m. | W 63-44 | |
| Tue., 12/28 | JV Girls Ice Hockey | Trumbull/St. Joseph | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 6:00 p.m. | ||
| Wed., 12/29 | V Boys Ice Hockey | Milford Coop | Home - Danbury Ice Arena-Patriot Rink [Directions] | 5:00 p.m. | W 7-1 | |
| Wed., 12/29 | V Wrestling | Harding/Bassick/Bridgeport Central | Away - Harding-Gym 1 [Directions] | Canceled | Cancelled | |
| Thu., 12/30 | V Boys Basketball | Blind Brook (NY) | Home - Weston HS-Gym (New) [Directions] | 2:00 p.m. | L 40-44 | |
| Mon., 1/3 | V Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 6:30 p.m. | L 46-61 | |
| Mon., 1/3 | JV Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 5:00 p.m. | ||
| Mon., 1/3 | V Boys Ice Hockey | Newtown/New Fairfield | Home - Danbury Ice Arena-Patriot Rink [Directions] | 8:00 p.m. | W 3-0 | |
| Wed., 1/5 | V Wrestling | Bunnell | Home - Weston HS-Gym (New) [Directions] | 6:00 p.m. | Weston 36 - Bunnell 42 | |
| Thu., 1/6 | V Girls Basketball | Pomperaug | Away - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | L 25-62 | |
| Thu., 1/6 | JV Girls Basketball | Pomperaug | Away - Pomperaug HS-Main Gym [Directions] | 5:45 p.m. | ||
| Thu., 1/6 | V Girls Indoor Track | SWC Varsity Indoor Meet | Away - Bethel HS | 4:00 p.m. | ||
| Thu., 1/6 | V Girls Indoor Track | SWC Indoor Track Meet | Away - Bethel HS-Track and Field Training Center | 4:00 p.m. | ||
| Fri., 1/7 | JV Girls Basketball | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Sister Marion Reilly Auditorium [Directions] | 5:15 p.m. | ||
| Sat., 1/8 | V Boys Basketball | Fitch | Away - Fitch HS-Big Gym [Directions] | 3:00 p.m. | L 44-70 | |
| Sat., 1/8 | JV Boys Basketball | Fitch | Away - Fitch HS-Big Gym [Directions] | 1:30 p.m. | ||
| Sat., 1/8 | FR Boys Basketball | Fitch | Away - Fitch HS-Big Gym [Directions] | 12:00 p.m. | ||
| Sat., 1/8 | V Boys Indoor Track | SWC JV Developmental | Away - Bethel HS-Track and Field Training Center | 3:00 p.m. | ||
| Pending changes awaiting acceptance by one or more parties involved: Date to 1/17, Time to 2:00 p.m. | ||||||
| Sat., 1/8 | V Girls Basketball | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Sister Marion Reilly Auditorium [Directions] | 10:00 a.m. | L Weston | |
| Sat., 1/8 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice-New [Directions] | 4:15 p.m. | W 4-3 | |
| Sat., 1/8 | V Girls Indoor Track | JV Developmental Meet | Away - Bethel HS-Track and Field Training Center | 3:00 p.m. | ||
| Pending changes awaiting acceptance by one or more parties involved: Date to 1/17, Time to 2:00 p.m. | ||||||
| Sun., 1/9 | V Girls Ice Hockey | East Catholic Coop | Away - Newington Ice Arena-Blue Rink [Directions] | 6:30 p.m. | L 5-1 | |
| Mon., 1/10 | V Boys Basketball | Bethel | Home - Weston HS-Gym (New) [Directions] | 7:00 p.m. | L 59-62 | |
| Mon., 1/10 | JV Boys Basketball | Bethel | Home - Weston HS-Gym (New) [Directions] | 5:15 p.m. | ||
| Mon., 1/10 | FR Boys Basketball | Bethel | Home - Weston HS-Gym (New) [Directions] | 3:45 p.m. | ||
| Mon., 1/10 | V Girls Basketball | Bethel | Away - Bethel HS-BHS gym [Directions] | 6:00 p.m. | L 25-43 | |
| Mon., 1/10 | JV Girls Basketball | Bethel | Away - Bethel HS-BHS gym [Directions] | 4:00 p.m. | ||
| Tue., 1/11 | V Boys Ice Hockey | Shepaug Valley Ice Hockey | Home - Danbury Ice Arena-Patriot Rink [Directions] | 8:30 p.m. | W 9-0 | |
| Tue., 1/11 | V Boys Swimming and Diving | New Fairfield | Home - Weston HS-Weston MS Pool [Directions] | 4:00 p.m. | Weston 93 New Fairfield 60 | |
| Tue., 1/11 | V Girls Basketball | New Milford | Away - New Milford HS-Main Gym - NMHS [Directions] | 5:30 p.m. | L Weston | |
| Tue., 1/11 | JV Girls Basketball | New Milford | Away - New Milford HS-Main Gym - NMHS [Directions] | 4:00 p.m. | ||
| Tue., 1/11 | V Girls Ice Hockey | West Haven/SHA | Away - West Haven HS-Bennett Rink [Directions] | 5:15 p.m. | L 2-1 | |
| Wed., 1/12 | V Boys Ice Hockey | Shepaug Valley Ice Hockey | Away - The Frederick Gunn School-Ice Rink [Directions] | 7:00 p.m. | W 7-2 | |
| Wed., 1/12 | V Boys Indoor Track | SWC JV Developmental | Away - Bethel HS-Track and Field Training Center | 4:00 p.m. | ||
| Wed., 1/12 | JV Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice-New [Directions] | 4:45 p.m. | ||
| Wed., 1/12 | V Girls Indoor Track | JV Developmental Meet | Away - Bethel HS-Track and Field Training Center | 4:00 p.m. | ||
| Thu., 1/13 | V Boys Basketball | New Fairfield | Home - Weston HS-Gym (New) [Directions] | 7:00 p.m. | W 74-46 | |
| Thu., 1/13 | JV Boys Basketball | New Fairfield | Home - Weston HS-Gym (New) [Directions] | 5:15 p.m. | ||
| Thu., 1/13 | FR Boys Basketball | New Fairfield | Home - Weston HS-Gym (New) [Directions] | 3:45 p.m. | ||
| Thu., 1/13 | JV Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena-Patriot Rink [Directions] | 4:45 p.m. | ||
| Thu., 1/13 | V Wrestling | Wilton | Home - Weston HS-Gym (New) [Directions] | 6:30 p.m. | Weston 53 Wilton 24 | |
| Thu., 1/13 | V Girls Basketball | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | 7:00 p.m. | L 21-36 | |
| Thu., 1/13 | JV Girls Basketball | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/14 | V Boys Swimming and Diving | Pomperaug | Away - Pomperaug HS-PHS Pool [Directions] | 5:00 p.m. | Pomperaug 94 Weston 59 | |
| Fri., 1/14 | V Girls Gymnastics | Norwalk, Staples | Home - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:00 p.m. | Staples - 131.60 Ludlowe - 130.55 | |
| Fri., 1/14 | V Girls Ice Hockey | Daniel Hand Coop | Away - Northford Ice Pavilion-Red [Directions] | 4:00 p.m. | W 5-1 | |
| Sat., 1/15 | V Boys Basketball | Foran | Home - Weston HS-Gym (New) [Directions] | 3:00 p.m. | L 56-63 | |
| Sat., 1/15 | JV Boys Basketball | Foran | Home - Weston HS-Gym (New) [Directions] | 1:30 p.m. | ||
| Sat., 1/15 | FR Boys Basketball | Foran | Home - Weston HS-Gym (New) [Directions] | 12:00 p.m. | ||
| Sat., 1/15 | V Wrestling | Darien, Bunnell, Derby/Oxford/Holy Cross | Away - Darien HS-DHS Main Gym [Directions] | 9:00 a.m. | Weston 60 vs Derby 18 Weston 36 vs. Darien 35 Weston 42 vs. Bunnell 36 | |
| Sat., 1/15 | V Girls Basketball | Harding | Home - Weston HS-Gym (New) [Directions] | 10:00 a.m. | W 41-24 | |
| Sat., 1/15 | JV Girls Basketball | Harding | Home - Weston HS-Gym (New) [Directions] | 8:30 a.m. | ||
| Sun., 1/16 | V Boys Ice Hockey | Sheehan | Away - Choate Rosemary Hall-Ice Rink [Directions] | 3:45 p.m. | L 3-4 | |
| Sun., 1/16 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 6:30 p.m. | W 5-1 | |
| Mon., 1/17 | V Boys Indoor Track | Varsity Developmental Race | Away - TBA | Postponed | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 9:00 a.m. | ||||||
| Mon., 1/17 | V Boys Indoor Track | Bethel, Brookfield, Bunnell, Immaculate, Joel Barlow, Kolbe Cathedral, Masuk, New Fairfield, New Milford, Newtown, Notre Dame-Fairfield, Pomperaug, Stratford | Away - Bethel HS-Track and Field Training Center | 2:00 p.m. | ||
| Mon., 1/17 | V Girls Gymnastics | Stamford, Westhill | Home - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 10:00 a.m. | Ludlowe - 130.50 | |
| Mon., 1/17 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Conners - Stamford-Ice Rink [Directions] | 1:00 p.m. | L 8-0 | |
| Mon., 1/17 | V Girls Indoor Track | Varsity Developmental Meet | Away - TBA-connell memorial rink | Postponed | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 9:00 a.m. | ||||||
| Mon., 1/17 | V Girls Indoor Track | Bethel, Brookfield, Bunnell, Immaculate, Joel Barlow, Kolbe Cathedral, Masuk, New Fairfield, New Milford, Newtown, Notre Dame-Fairfield, Pomperaug, Stratford | Away - Bethel HS-Track and Field Training Center | 2:00 p.m. | ||
| Tue., 1/18 | V Boys Basketball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 7:00 p.m. | L 54-65 | |
| Tue., 1/18 | JV Boys Basketball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 5:15 p.m. | ||
| Tue., 1/18 | FR Boys Basketball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 3:45 p.m. | ||
| Tue., 1/18 | V Boys Swimming and Diving | Newtown | Home - Weston HS-Weston MS Pool [Directions] | 7:00 p.m. | Newtown 90 Weston 78 | |
| Tue., 1/18 | V Girls Basketball | Masuk | Home - Weston HS-Gym (New) [Directions] | 7:00 p.m. | L 39-49 | |
| Tue., 1/18 | JV Girls Basketball | Masuk | Home - Weston HS-Gym (New) [Directions] | 5:15 p.m. | ||
| Wed., 1/19 | V Boys Ice Hockey | Brookfield | Home - Danbury Ice Arena-Patriot Rink [Directions] | 5:00 p.m. | W 5-0 | |
| Wed., 1/19 | V Boys Indoor Track | Brookfield, Bethel, Bunnell, Immaculate, Joel Barlow, Kolbe Cathedral, Masuk, New Fairfield, New Milford, Newtown, Notre Dame-Fairfield, Pomperaug, Stratford | Away - Floyd Little Athletic Center-Field House | 5:15 p.m. | ||
| Wed., 1/19 | V Wrestling | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | 6:00 p.m. | New Fairfield 52 Weston 30 | |
| Wed., 1/19 | V Girls Indoor Track | Brookfield, Bethel, Bunnell, Immaculate, Joel Barlow, Kolbe Cathedral, Masuk, New Fairfield, New Milford, Newtown, Notre Dame-Fairfield, Pomperaug, Stratford | Away - Floyd Little Athletic Center-Field House | 5:15 p.m. | ||
| Thu., 1/20 | JV Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena-Patriot Rink [Directions] | Postponed | ||
| Fri., 1/21 | V Boys Basketball | New Milford | Away - New Milford HS-Main Gym - NMHS [Directions] | 7:00 p.m. | W 59-47 | |
| Fri., 1/21 | JV Boys Basketball | New Milford | Away - New Milford HS-Main Gym - NMHS [Directions] | 5:15 p.m. | ||
| Fri., 1/21 | FR Boys Basketball | New Milford | Away - New Milford HS-Main Gym - NMHS [Directions] | 3:45 p.m. | ||
| Fri., 1/21 | V Girls Basketball | New Milford | Home - Weston HS-Gym (New) [Directions] | 7:00 p.m. | W 40-36 | |
| Fri., 1/21 | JV Girls Basketball | New Milford | Home - Weston HS-Gym (New) [Directions] | 5:15 p.m. | ||
| Fri., 1/21 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | L 2-0 | |
| Sat., 1/22 | V Boys Ice Hockey | Masuk | Home - Danbury Ice Arena-Patriot Rink [Directions] | 12:40 p.m. | W 3-2(OT) | |
| Sat., 1/22 | V Boys Indoor Track | New Balance Games at NYC Armory | Away - Not Listed | 1:00 p.m. | ||
| Sat., 1/22 | V Wrestling | The 35th Annual New Milford Wrestling Tournament | Away - New Milford HS-Main Gym - NMHS | 8:30 a.m. | ||
| Sat., 1/22 | V Girls Basketball | Bridgeport Central | Home - Weston HS-Gym (New) [Directions] | 4:00 p.m. | W 66-32 | |
| Sat., 1/22 | JV Girls Basketball | Bridgeport Central | Home - Weston HS-Gym (New) [Directions] | 2:15 p.m. | ||
| Sat., 1/22 | V Girls Gymnastics | Darien, Fairfield Warde | Away - Darien YMCA [Directions] | 2:30 p.m. | Ludlowe - 131.95 Darien - 128.30 | |
| Sat., 1/22 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 6:30 p.m. | L 3-1 | |
| Sat., 1/22 | V Girls Indoor Track | New Balance Games at NYC Armory | Away - Not Listed | 1:00 p.m. | ||
| Sun., 1/23 | JV Girls Ice Hockey | West Haven/SHA | Away - West Haven HS-Bennett Rink [Directions] | 6:25 p.m. | ||
| Mon., 1/24 | V Girls Gymnastics | Greenwich | Home - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:30 p.m. | Ludlowe - 128.8 | |
| Tue., 1/25 | V Boys Basketball | Newtown | Home - Weston HS-Gym (New) [Directions] | 7:00 p.m. | L 45-77 | |
| Tue., 1/25 | JV Boys Basketball | Newtown | Home - Weston HS-Gym (New) [Directions] | 5:15 p.m. | ||
| Tue., 1/25 | FR Boys Basketball | Newtown | Home - Weston HS-Gym (New) [Directions] | 3:45 p.m. | ||
| Tue., 1/25 | V Boys Ice Hockey | Fox Lane (NY) | Home - Danbury Ice Arena-Patriot Rink [Directions] | 8:30 p.m. | W 9-2 | |
| Tue., 1/25 | V Girls Basketball | Newtown | Away - Newtown HS-Gym [Directions] | 7:00 p.m. | L 20-24 | |
| Tue., 1/25 | JV Girls Basketball | Newtown | Away - Newtown HS-Gym [Directions] | 5:15 p.m. | ||
| Wed., 1/26 | V Boys Indoor Track | SWC JV Developmental | Away - Bethel HS-Track and Field Training Center | 4:00 p.m. | ||
| Wed., 1/26 | V Wrestling | Bethel | Away - Bethel HS-BHS gym [Directions] | 6:00 p.m. | Weston 42 Bethel 39 | |
| Wed., 1/26 | V Girls Gymnastics | St. Joseph, Trumbull | Home - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:30 p.m. | Ludlowe - 137.30 Trumbull - 136.40 St. Joseph - 135.85 | |
| Wed., 1/26 | V Girls Ice Hockey | Hamden Coop | Away - Hamden-Lou Astorino Ice Rink [Directions] | 3:30 p.m. | L 3-1 | |
| Wed., 1/26 | V Girls Indoor Track | JV Developmental Meet | Away - Bethel HS-Track and Field Training Center | 4:00 p.m. | ||
| Fri., 1/28 | V Boys Basketball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 5:15 p.m. | L 38-58 | |
| Fri., 1/28 | JV Boys Basketball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 3:30 p.m. | ||
| Fri., 1/28 | FR Boys Basketball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 2:00 p.m. | ||
| Fri., 1/28 | V Girls Basketball | Joel Barlow | Home - Weston HS-Gym (New) [Directions] | 5:15 p.m. | W 40-26 | |
| Fri., 1/28 | JV Girls Basketball | Joel Barlow | Home - Weston HS-Gym (New) [Directions] | 3:30 p.m. | ||
| Fri., 1/28 | V Girls Ice Hockey | Guilford Coop | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | L 6-1 | |
| Sat., 1/29 | V Wrestling | Norwalk, Brien McMahon, Darien, Fairfield Ludlowe, Fairfield Warde, Greens Farms Academy, Greenwich, TBA, TBA, TBA, Notre Dame-Fairfield, Ridgefield, St. Joseph, Staples, Trumbull | Away - Norwalk HS-Tom Scarso Gymnasium | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to 9:00 a.m. | ||||||
| Sun., 1/30 | JV Girls Ice Hockey | West Haven/SHA | Away - West Haven HS-Bennett Rink [Directions] | 6:15 p.m. | No Bus | |
| Mon., 1/31 | V Boys Basketball | Bunnell | Home - Weston HS-Gym (New) [Directions] | 7:00 p.m. | L 52-53 | |
| Mon., 1/31 | JV Boys Basketball | Bunnell | Home - Weston HS-Gym (New) [Directions] | 5:15 p.m. | ||
| Mon., 1/31 | FR Boys Basketball | Bunnell | Home - Weston HS-Gym (New) [Directions] | 3:45 p.m. | ||
| Mon., 1/31 | V Girls Basketball | Bunnell | Away - Bunnell HS-David Johnson Gymnasium [Directions] | 6:00 p.m. | W 54-40 | |
| Mon., 1/31 | JV Girls Basketball | Bunnell | Away - Bunnell HS-David Johnson Gymnasium [Directions] | 4:15 p.m. | ||
| Mon., 1/31 | V Girls Gymnastics | Foran | Home - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:00 p.m. | Ludlowe - 132.30 Foran - 112.25 | |
| Tue., 2/1 | V Boys Ice Hockey | John Jay (NY) | Away - John Jay HS (Crossriver) | 6:00 p.m. | L 3-8 | |
| Tue., 2/1 | V Boys Indoor Track | Last Chance Meet | Away - Bethel HS-BHS gym | 4:00 p.m. | ||
| Tue., 2/1 | V Boys Swimming and Diving | Masuk | Home - Weston HS-Weston MS Pool [Directions] | 4:00 p.m. | Weston | |
| Tue., 2/1 | V Girls Indoor Track | Last Chance Meet | Away - Bethel HS-Track and Field Training Center | 4:00 p.m. | ||
| Wed., 2/2 | V Wrestling | Joel Barlow | Away - Joel Barlow High-Upper Gym [Directions] | 6:00 p.m. | Weston 59 Joel Barlow 22 | |
| Wed., 2/2 | V Girls Gymnastics | Wilton, Fairfield Warde | Away - Wilton HS-Aux Gym [Directions] | 5:30 p.m. | Ludlowe - 134.60 Wilton - 133.45 | |
| Wed., 2/2 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 3:30 p.m. | W 3-2 | No Bus |
| Thu., 2/3 | V Boys Basketball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 7:00 p.m. | L 40-51 | |
| Thu., 2/3 | JV Boys Basketball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 5:15 p.m. | ||
| Thu., 2/3 | FR Boys Basketball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 3:30 p.m. | ||
| Thu., 2/3 | V Boys Ice Hockey | New Milford | Away - Canterbury School-O'Neill Arena [Directions] | 7:00 p.m. | L 1-5 | |
| Thu., 2/3 | V Girls Basketball | Brookfield | Home - Weston HS-Gym (New) [Directions] | 7:00 p.m. | W 45-24 | |
| Thu., 2/3 | JV Girls Basketball | Brookfield | Home - Weston HS-Gym (New) [Directions] | 5:15 p.m. | ||
| Sat., 2/5 | V Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena-Patriot Rink [Directions] | 5:45 p.m. | W 6-0 | |
| Sat., 2/5 | V Boys Indoor Track | SWC Indoor Track Championships | Away - Floyd Little Athletic Center-Field House | 5:00 p.m. | ||
| Sat., 2/5 | V Girls Basketball | New Canaan | Home - Weston HS-Gym (New) [Directions] | 4:00 p.m. | L 28-32 | |
| Sat., 2/5 | JV Girls Basketball | New Canaan | Home - Weston HS-Gym (New) [Directions] | 2:30 p.m. | ||
| Sat., 2/5 | V Girls Indoor Track | SWC Indoor Track Championship | Away - Floyd Little Athletic Center-Field House | 5:00 p.m. | ||
| Sun., 2/6 | JV Girls Ice Hockey | Trumbull/St. Joseph | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:45 p.m. | ||
| Mon., 2/7 | V Boys Basketball | Kolbe Cathedral | Home - Weston HS-Gym (New) [Directions] | 6:00 p.m. | L 59-44 | |
| Mon., 2/7 | JV Boys Basketball | Kolbe Cathedral | Home - Weston HS-Gym (New) [Directions] | 4:15 p.m. | ||
| Mon., 2/7 | V Wrestling | Stratford | Home - Weston HS-Gym (Old) [Directions] | 6:00 p.m. | Weston 18 Stratford 58 | |
| Mon., 2/7 | V | Brookfield | Home - Weston HS-Gym (New) [Directions] | 2:45 p.m. | ||
| Mon., 2/7 | V Girls Basketball | Kolbe Cathedral | Away - Cardinal Sheehan Center Bridgeport [Directions] | 7:00 p.m. | L 34-50 | |
| Mon., 2/7 | JV Girls Basketball | Kolbe Cathedral | Away - Cardinal Sheehan Center Bridgeport [Directions] | 5:15 p.m. | ||
| Tue., 2/8 | V Boys Ice Hockey | SCW Knights | Home - Danbury Ice Arena-Patriot Rink [Directions] | 8:30 p.m. | W 6-3 | |
| Tue., 2/8 | V Boys Swimming and Diving | New Milford | Away - Canterbury School-Higgins Aquatic Center [Directions] | 7:00 p.m. | New Milford 90 Weston 80 | |
| Wed., 2/9 | V Boys Basketball | Jonathan Law | Away - Jonathan Law HS-James L. Richetelli Memorial Gymnasium [Directions] | 7:00 p.m. | L 31-39 | |
| Wed., 2/9 | JV Boys Basketball | Jonathan Law | Away - Jonathan Law HS-James L. Richetelli Memorial Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 2/9 | FR Boys Basketball | Jonathan Law | Away - Jonathan Law HS-James L. Richetelli Memorial Gymnasium [Directions] | 3:45 p.m. | ||
| Thu., 2/10 | V Boys Indoor Track | Class M Championship | Away - Floyd Little Athletic Center | 4:00 p.m. | ||
| Thu., 2/10 | V Girls Basketball | Stratford | Home - Weston HS-Gym (New) [Directions] | 7:00 p.m. | W 41-30 | |
| Thu., 2/10 | JV Girls Basketball | Stratford | Home - Weston HS-Gym (New) [Directions] | 5:15 p.m. | ||
| Thu., 2/10 | V Girls Ice Hockey | Guilford Coop | Away - Milford Ice Pavillion-Ice Rink [Directions] | 6:10 p.m. | L 9-2 | |
| Thu., 2/10 | V Girls Indoor Track | Class M Championship | Away - Floyd Little Athletic Center | 4:00 p.m. | ||
| Fri., 2/11 | V Boys Basketball | Stratford | Away - Stratford HS-Gym [Directions] | 7:00 p.m. | L 30-69 | |
| Fri., 2/11 | JV Boys Basketball | Stratford | Away - Stratford HS-Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/11 | FR Boys Basketball | Stratford | Away - Stratford HS-Gym [Directions] | 3:30 p.m. | ||
| Fri., 2/11 | V Girls Ice Hockey | Conard | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | L 3-1 | |
| Sat., 2/12 | V Boys Ice Hockey | Northeastern Shamrocks | Home - Danbury Ice Arena-Patriot Rink [Directions] | 3:50 p.m. | W 6-2 | |
| Sat., 2/12 | V Wrestling | New Milford, Brookfield, Bunnell, Joel Barlow, Masuk, SWC Tournament, New Fairfield, Newtown, Pomperaug, Stratford | Away - New Milford HS-Main Gym - NMHS | 8:30 a.m. | ||
| Sat., 2/12 | V Girls Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 12:00 p.m. | W 56-34 | |
| Sat., 2/12 | JV Girls Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 10:30 a.m. | ||
| Sat., 2/12 | V Girls Gymnastics | FCIAC Gymnastics Championships | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 | 11:00 a.m. | ||
| Sat., 2/12 | V Girls Gymnastics | FCIAC Gymnastics Meet | Home - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | TBA | Ludlowe - 137.10 | |
| Sun., 2/13 | JV Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | ||
| Tue., 2/15 | V Boys Basketball | Immaculate | Away - Immaculate HS-Immaculate Gym [Directions] | 7:00 p.m. | L 21-49 | |
| Tue., 2/15 | JV Boys Basketball | Immaculate | Away - Immaculate HS-Immaculate Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/15 | FR Boys Basketball | Immaculate | Away - Immaculate HS-Immaculate Gym [Directions] | 3:45 p.m. | ||
| Tue., 2/15 | V Boys Swimming and Diving | Joel Barlow-Bethel Swim | Home - Weston HS-Weston MS Pool [Directions] | 4:00 p.m. | Weston 97 Barlow/Bethel 72 | |
| Tue., 2/15 | V Girls Basketball | Immaculate | Home - Weston HS-Gym (New) [Directions] | 7:00 p.m. | W 45-39 | |
| Tue., 2/15 | JV Girls Basketball | Immaculate | Home - Weston HS-Gym (New) [Directions] | 5:15 p.m. | ||
| Wed., 2/16 | V Boys Ice Hockey | SCW Knights | Away - Champions Skating Rink - Cromwell-Upper Rink [Directions] | 3:10 p.m. | W 6-0 | |
| Wed., 2/16 | V Girls Gymnastics | Fairfield Warde | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:00 p.m. | Ludlowe - 137.10 | |
| Thu., 2/17 | V Girls Ice Hockey | Daniel Hand Coop | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | L 3-2(OT) | |
| Fri., 2/18 | V Boys Basketball | Pomperaug | Home - Weston HS-Gym (New) [Directions] | 7:00 p.m. | L 60-63 | |
| Fri., 2/18 | JV Boys Basketball | Pomperaug | Home - Weston HS-Gym (New) [Directions] | 5:15 p.m. | ||
| Fri., 2/18 | FR Boys Basketball | Pomperaug | Home - Weston HS-Gym (New) [Directions] | 3:45 p.m. | ||
| Fri., 2/18 | V Wrestling | Class M Championship - Day 1 | Away - East Haven | 3:00 p.m. | ||
| Fri., 2/18 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | W 3-1 | |
| Sat., 2/19 | V Boys Ice Hockey | Masuk | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 7:15 p.m. | W 4-0 | |
| Sat., 2/19 | V Boys Indoor Track | State Open | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/19 | V Girls Basketball | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Sister Marion Reilly Auditorium [Directions] | 2:00 p.m. | ||
| Sat., 2/19 | V Girls Basketball | SWC Quarterfinals at Home of Higher Seed | Away - Not Listed | 7:00 p.m. | ||
| Sat., 2/19 | V Girls Indoor Track | State Open | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Mon., 2/21 | V Girls Ice Hockey | Hamden Coop | Away - Hamden-Lou Astorino Ice Rink [Directions] | 2:00 p.m. | ||
| Tue., 2/22 | V Boys Basketball | Notre Dame-Fairfield | Home - Weston HS-Gym (New) [Directions] | 7:00 p.m. | L 42-73 | |
| Tue., 2/22 | JV Boys Basketball | Notre Dame-Fairfield | Home - Weston HS-Gym (New) [Directions] | 5:15 p.m. | ||
| Tue., 2/22 | FR Boys Basketball | Notre Dame-Fairfield | Home - Weston HS-Gym (New) [Directions] | 3:45 p.m. | ||
| Tue., 2/22 | V Boys Swimming and Diving | Brookfield | Away - Brookfield YMCA-Outside/Dome Pool [Directions] | 6:10 p.m. | Brookfield 87 Weston 83 | |
| Wed., 2/23 | V Boys Ice Hockey | Staples | Home - Danbury Ice Arena-Patriot Rink [Directions] | 5:00 p.m. | W 5-3 | |
| Sat., 2/26 | V Wrestling | State Open - Day 1 | Away - Floyd Little Athletic Center | 12:45 p.m. | ||
| Sat., 2/26 | V Girls Gymnastics | CIAC Class L Divisional Championship | Away - Richetelli Gymnasium @Jonathan Law | 2:00 p.m. | ||
| Mon., 2/28 | FR Boys Basketball | Staples | Home - Weston HS-Gym (New) [Directions] | 5:30 p.m. | ||
| Mon., 2/28 | V Boys Ice Hockey | Housatonic Coop | Home - Danbury Ice Arena-Patriot Rink [Directions] | 8:00 p.m. | W 6-4 | |
| Mon., 2/28 | V Girls Basketball | Berlin | Away - Berlin HS-Gibney Gymnasium [Directions] | 6:30 p.m. | ||
| Wed., 3/2 | V Boys Ice Hockey | Masuk | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 7:30 p.m. | ||
| Fri., 3/4 | V Boys Ice Hockey | Brookfield | Home - West Haven HS-Bennett Rink [Directions] | 8:00 p.m. | ||
| Fri., 3/4 | V Boys Swimming and Diving | SWC Boys Swimming Championship | Away - Masuk HS-Pool | 5:00 p.m. | ||
| Mon., 3/7 | V Boys Ice Hockey | Shepaug Valley Ice Hockey | Home - Danbury Ice Arena-Patriot Rink [Directions] | 8:00 p.m. | ||
| Thu., 3/10 | V Boys Ice Hockey | Enfield/East Granby/Stafford | Home - Newington Ice Arena-Blue Rink [Directions] | 6:00 p.m. | ||
| Thu., 3/10 | V Boys Swimming and Diving | CIAC Class M Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sun., 3/13 | V Boys Swimming and Diving | CIAC Class M Qualifying Meet | Away - Cornerstone Pool | 1:00 p.m. | ||
| Mon., 3/14 | V Boys Ice Hockey | Newington Coop | Away - Northford Ice Pavilion-Red [Directions] | 5:00 p.m. | ||
| Wed., 3/16 | V Boys Swimming and Diving | CIAC Class M Swimming Championships | Away - Cornerstone Pool | 6:00 p.m. | ||
| Thu., 3/17 | V Boys Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/19 | V Boys Swimming and Diving | CIAC State Open Swimming Championships | Away - Cornerstone Pool | 3:15 p.m. | ||
| Sat., 3/26 | V Baseball | Fairfield Ludlowe (Scrim.) | Home - Weston HS-Revson #1 (Varsity) [Directions] | 11:00 a.m. | ||
| Sat., 3/26 | JV Baseball | Fairfield Ludlowe (Scrim.) | Home - Weston HS-Revson #2 (JV) [Directions] | 11:00 a.m. | ||
| Sat., 3/26 | V Boys Lacrosse | John Jay (NY) (Scrim.) | Away - John Jay Senior HS | 11:00 a.m. | ||
| Sat., 3/26 | V Girls Lacrosse | Staples, Bishop Guertin (NH), Fairfield Ludlowe, Greenwich Academy, Greenwich, Guilford, TBA, New Canaan, Sacred Heart of Greenwich, St. Joseph | Away - Staples HS-Staples Stadium | 9:00 a.m. | ||
| Sat., 3/26 | JV Girls Lacrosse | Joel Barlow (Scrim.) | Away - Joel Barlow HS-Joel Barlow HS Stadium [Directions] | 1:00 p.m. | ||
| Sat., 3/26 | V Softball | Mercy (Scrim.) | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 11:30 a.m. | ||
| Tue., 3/29 | V Baseball | Staples (Scrim.) | Home - Weston HS-Revson #1 (Varsity) [Directions] | 4:00 p.m. | Cancelled | |
| Tue., 3/29 | V Softball | Greens Farms Academy (Scrim.) | Away - Greens Farms Academy-Softball Diamond | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to 3:45 p.m. | ||||||
| Wed., 3/30 | V Softball | Danbury (Scrim.) | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 4:00 p.m. | ||
| Thu., 3/31 | V Baseball | Norwalk (Scrim.) | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 4:00 p.m. | ||
| Thu., 3/31 | V Girls Lacrosse | Brien McMahon (Scrim.) | Home - Weston HS-WHS Lower Turf Field [Directions] | 3:30 p.m. | ||
| Thu., 3/31 | JV Girls Lacrosse | Brien McMahon (Scrim.) | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:00 p.m. | ||
| Fri., 4/1 | V Boys Tennis | Ridgefield (Scrim.) | Home - Weston HS-WHS Tennis Courts [Directions] | 3:30 p.m. | ||
| Pending changes awaiting acceptance by one or more parties involved: Date to 4/5, Time to 4:15 p.m. | ||||||
| Sat., 4/2 | V Baseball | Wilton | Away - Wilton HS-Varsity Baseball Field [Directions] | 4:00 p.m. | L 1-11 | |
| Sat., 4/2 | JV Baseball | Wilton | Away - Wilton HS-JV Baseball Field [Directions] | 2:00 p.m. | ||
| Sat., 4/2 | V Boys Lacrosse | Long Island Lutheran (NY) (Scrim.) | Home - Weston HS-WHS Lower Turf Field [Directions] | 1:00 p.m. | ||
| Sat., 4/2 | V Boys Tennis | New Canaan (Scrim.) | Away - New Canaan HS-NCHS Tennis Courts [Directions] | 1:00 p.m. | ||
| Sat., 4/2 | V Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 2:00 p.m. | W Weston | |
| Sat., 4/2 | JV Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 12:15 p.m. | ||
| Sat., 4/2 | V Softball | Wilton | Away - Wilton HS-Varsity Softball Field [Directions] | 2:00 p.m. | L 5-8 | |
| Sat., 4/2 | JV Girls Tennis | Wilton | Home - Weston HS-WHS Tennis Courts [Directions] | Postponed | ||
| Mon., 4/4 | V Baseball | New Canaan | Away - Mead Park-Baseball Field [Directions] | 4:00 p.m. | L 5-14 | |
| Mon., 4/4 | V Boys Tennis | Wilton | Away - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | L 1-6 [Detailed Results] | |
| Mon., 4/4 | JV Boys Tennis | Wilton | Away - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 4/4 | V Girls Lacrosse | Daniel Hand | Away - Madison Surf Club-Strong Field [Directions] | 5:30 p.m. | W 11-9 | |
| Mon., 4/4 | JV Girls Lacrosse | Daniel Hand | Away - Madison Surf Club-Strong Field [Directions] | 4:00 p.m. | ||
| Mon., 4/4 | V Softball | Brien McMahon | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 4:00 p.m. | W 5-4 | |
| Mon., 4/4 | JV Softball | Brien McMahon | Home - Weston HS-Softball - MS Field (JV) [Directions] | Canceled | Cancelled | |
| Mon., 4/4 | V Girls Tennis | Ridgefield (Scrim.) | Away - Ridgefield HS-RHS Tennis Courts [Directions] | 4:30 p.m. | ||
| Tue., 4/5 | V Baseball | Bethel | Home - Weston HS-Revson #1 (Varsity) [Directions] | 4:15 p.m. | L 2-4 | |
| Tue., 4/5 | JV Boys Lacrosse | Trumbull | Away - Trumbull HS-Cork Field [Directions] | 4:00 p.m. | ||
| Tue., 4/5 | V Boys Tennis | Brookfield | Away - Brookfield HS-BHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Tue., 4/5 | V Girls Golf | Bunnell, Pomperaug | Away - Bunnell HS-Oronoque C.C. [Directions] | 3:00 p.m. | Weston 285 Bunnell 321 Pomperaug 249 Weston 285 | |
| Tue., 4/5 | V Girls Golf | Pomperaug | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | ||
| Tue., 4/5 | V Softball | Bethel | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 4:15 p.m. | L 0-5 | |
| Tue., 4/5 | V Girls Tennis | Brookfield | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Thu., 4/7 | JV Softball | Bethel | Away - Bethel HS-Kisling Field [Directions] | Canceled | Cancelled | |
| Fri., 4/8 | V Baseball | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 4:00 p.m. | L 8-5 | |
| Fri., 4/8 | V Boys Tennis | Fairfield Ludlowe | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | L 3-4 [Detailed Results] | |
| Sat., 4/9 | JV Baseball | Bethel | Away - Bethel HS-Hunt Field at Bethel HS [Directions] | Postponed | ||
| Sat., 4/9 | V Boys Lacrosse | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 12:00 p.m. | W 17-9 | |
| Sat., 4/9 | JV Boys Lacrosse | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 1:30 p.m. | ||
| Sat., 4/9 | V Girls Lacrosse | Stamford | Home - Weston HS-WHS Lower Turf Field [Directions] | 12:00 p.m. | W 13-6 | |
| Sat., 4/9 | JV Girls Lacrosse | Stamford | Home - Weston HS-WHS Lower Turf Field [Directions] | 10:15 a.m. | ||
| Sat., 4/9 | JV Girls Tennis | Fairfield Ludlowe | Away - Dwight Elementary School-Tennis Courts [Directions] | Postponed | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 10:30 a.m. | ||||||
| Mon., 4/11 | V Baseball | Pomperaug | Away - Community House Park-Baseball Field [Directions] | 4:15 p.m. | L 1-2 | |
| Mon., 4/11 | JV Boys Tennis | Hall | Away - Hall HS-Tennis Courts [Directions] | Canceled | Cancelled | |
| Mon., 4/11 | V Softball | Pomperaug | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 4:15 p.m. | L 3-6 | |
| Mon., 4/11 | V Girls Tennis | Bethel | Away - Bethel HS-BHS Tennis Courts [Directions] | 3:45 p.m. | W 6-1 | |
| Tue., 4/12 | JV Baseball | Pomperaug | Home - Weston HS-Revson #2 (JV) [Directions] | 4:15 p.m. | ||
| Tue., 4/12 | V Boys Lacrosse | Greenwich | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | L 14-5 | |
| Tue., 4/12 | JV Boys Lacrosse | Greenwich | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 4/12 | V Girls Lacrosse | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | W 21-9 | |
| Tue., 4/12 | JV Girls Lacrosse | Trumbull | Away - Trumbull HS-Cork Field [Directions] | 4:00 p.m. | ||
| Wed., 4/13 | V Baseball | Newtown | Away - Newtown HS-Baseball Field [Directions] | 4:30 p.m. | W 14-10 | |
| Wed., 4/13 | V Boys Tennis | Pomperaug | Home - Weston HS-WHS Tennis Courts [Directions] | 11:00 a.m. | W 7-0 [Detailed Results] | |
| Wed., 4/13 | V Softball | Newtown | Away - Newtown HS-NHS Softball Field [Directions] | 4:00 p.m. | L 2-12 | |
| Thu., 4/14 | JV Baseball | Newtown | Home - Weston HS-Revson #2 (JV) [Directions] | 4:15 p.m. | ||
| Thu., 4/14 | V Boys Lacrosse | Brookfield | Away - Brookfield HS-BHS Stadium Field [Directions] | 4:00 p.m. | W 17-7 | |
| Thu., 4/14 | V Girls Lacrosse | Brookfield | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | W 15-9 | |
| Thu., 4/14 | JV Girls Lacrosse | Brookfield | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:15 p.m. | ||
| Sat., 4/16 | V Baseball | Stamford | Home - Weston HS-Revson #1 (Varsity) [Directions] | 12:00 p.m. | W 8-7 | |
| Sat., 4/16 | V Softball | Bunnell | Away - Bunnell HS-Bunnell Softball FIeld [Directions] | 11:00 a.m. | L 3-4 | |
| Mon., 4/18 | V Boys Lacrosse | Immaculate | Away - Immaculate HS-Mustang Valley [Directions] | 4:00 p.m. | W 18-0 | |
| Mon., 4/18 | V Boys Tennis | Newtown | Away - Newtown HS-NHS Tennis Courts [Directions] | 3:30 p.m. | W 7-0 [Detailed Results] | |
| Mon., 4/18 | V Girls Lacrosse | Immaculate | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | W 19-3 | |
| Mon., 4/18 | V Girls Outdoor Track | Masuk, New Fairfield, Stratford | Home - Weston HS-WHS Track [Directions] | 4:00 p.m. | Weston 110 New Fairfield 35 Weston 115 Masuk 30 Weston 109 Stratford 35 | |
| Mon., 4/18 | V Softball | New Fairfield | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 4:15 p.m. | L 11-13 | |
| Mon., 4/18 | V Girls Tennis | Newtown | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | W 6-1 | |
| Tue., 4/19 | V Boys Lacrosse | Pomperaug | Away - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | W 20-6 | |
| Tue., 4/19 | JV Boys Lacrosse | Pomperaug | Away - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Tue., 4/19 | V Boys Outdoor Track | Masuk, New Fairfield, Stratford | Away - Masuk HS-Edmund Butler Track @ Masuk HS [Directions] | 4:00 p.m. | Weston 103 Masuk 47 Weston 111 Stratford 39 Weston 111 New Fairfield 39 | |
| Tue., 4/19 | V Girls Golf | Pomperaug | Away - Pomperaug HS-Pomperaug Golf Course [Directions] | 3:00 p.m. | Pomperaug 231 Weston 241 | |
| Tue., 4/19 | V Girls Lacrosse | Pomperaug | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | W 12-6 | |
| Tue., 4/19 | JV Girls Lacrosse | Pomperaug | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:15 p.m. | ||
| Tue., 4/19 | JV Softball | New Fairfield | Away - New Fairfield HS-Softball Field [Directions] | Canceled | Cancelled | |
| Tue., 4/19 | V Girls Tennis | Glastonbury | Home - Weston HS-WHS Tennis Courts [Directions] | 4:30 p.m. | L 2-5 | |
| Wed., 4/20 | V Baseball | Kolbe Cathedral | Away - Seaside Park-Field #1 (UB Field) [Directions] | 4:15 p.m. | W 15-3 | |
| Wed., 4/20 | JV Baseball | New Fairfield | Home - Weston HS-Revson #2 (JV) [Directions] | 3:45 p.m. | ||
| Wed., 4/20 | V Boys Tennis | New Fairfield | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Wed., 4/20 | V Softball | Kolbe Cathedral | Away - Cal Ripken Field-Cal Ripken Field [Directions] | 4:15 p.m. | W 7-3 | |
| Wed., 4/20 | V Girls Tennis | New Fairfield | Away - New Fairfield HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Thu., 4/21 | V Boys Lacrosse | Newtown | Home - Weston HS-WHS Lower Turf Field [Directions] | 7:30 p.m. | W 8-4 | |
| Thu., 4/21 | JV Boys Lacrosse | Newtown | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:30 p.m. | ||
| Thu., 4/21 | V Boys Tennis | Fairfield Prep | Home - Weston HS-WHS Tennis Courts [Directions] | 3:30 p.m. | L 3-4 [Detailed Results] | |
| Thu., 4/21 | V Girls Lacrosse | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 5:30 p.m. | L 9-10 | |
| Thu., 4/21 | JV Girls Lacrosse | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 7:00 p.m. | ||
| Thu., 4/21 | V Softball | Bethel | Away - Bethel HS-Kisling Field [Directions] | 4:15 p.m. | L 6-7 | |
| Fri., 4/22 | V Baseball | Joel Barlow | Home - Weston HS-Revson #1 (Varsity) [Directions] | 4:00 p.m. | L 2-13 | |
| Fri., 4/22 | JV Baseball | Joel Barlow | Home - Weston HS-Revson #2 (JV) [Directions] | 4:00 p.m. | ||
| Fri., 4/22 | JV Girls Tennis | Fairfield Ludlowe | Home - Weston HS-WHS Tennis Courts [Directions] | 3:00 p.m. | ||
| Sat., 4/23 | V Girls Lacrosse | Notre Dame-Fairfield | Home - Weston HS-WHS Lower Turf Field [Directions] | 1:30 p.m. | W 19-6 | |
| Sat., 4/23 | JV Girls Lacrosse | Notre Dame-Fairfield | Home - Weston HS-WHS Lower Turf Field [Directions] | 12:00 p.m. | ||
| Sat., 4/23 | V Softball | Greenwich | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 12:00 p.m. | L 5-8 | |
| Mon., 4/25 | V Baseball | Immaculate | Home - Weston HS-Revson #1 (Varsity) [Directions] | 4:15 p.m. | W 11-0 | |
| Mon., 4/25 | V Boys Tennis | Joel Barlow | Away - Joel Barlow HS-Tennis Courts [Directions] | 3:45 p.m. | W 4-3 [Detailed Results] | |
| Mon., 4/25 | V Girls Golf | Immaculate | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | Immaculate 213 Weston 268 | |
| Mon., 4/25 | V Girls Outdoor Track | Joel Barlow, Pomperaug | Away - Joel Barlow HS-Joel Barlow HS Stadium [Directions] | 4:00 p.m. | Weston 91 Joel Barlow 56 Weston 100 Pomperaug 50 | |
| Mon., 4/25 | V Softball | Immaculate | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 4:15 p.m. | L 7-16 | |
| Tue., 4/26 | V Boys Lacrosse | Joel Barlow | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | W 12-7 | |
| Tue., 4/26 | JV Boys Lacrosse | Joel Barlow | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 4/26 | V Boys Outdoor Track | Pomperaug, Joel Barlow | Away - Pomperaug HS-Stadium [Directions] | 4:00 p.m. | Weston 98 Barlow 51 Weston 87 Pomperaug 63 | |
| Tue., 4/26 | V Girls Lacrosse | Joel Barlow | Away - Joel Barlow HS-Joel Barlow HS Stadium [Directions] | 4:00 p.m. | W 5-4 | |
| Tue., 4/26 | JV Girls Lacrosse | Joel Barlow | Away - Joel Barlow HS-Joel Barlow HS Stadium [Directions] | 5:30 p.m. | ||
| Wed., 4/27 | V Baseball | Brookfield | Away - Brookfield HS-Baseball Field [Directions] | 4:15 p.m. | L 1-5 | |
| Wed., 4/27 | V Boys Tennis | Bunnell | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Wed., 4/27 | V Girls Golf | Masuk | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | Masuk 204 Weston 273 | |
| Wed., 4/27 | V Softball | Brookfield | Away - Cadigan Field-Field #1 [Directions] | 6:00 p.m. | L 5-13 | |
| Wed., 4/27 | V Girls Tennis | Bunnell | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Thu., 4/28 | V Baseball | New Fairfield | Home - Weston HS-Revson #1 (Varsity) [Directions] | 5:30 p.m. | W 10-9 | |
| Thu., 4/28 | JV Baseball | Brookfield | Away - Brookfield HS-Baseball Field [Directions] | 5:00 p.m. | ||
| Thu., 4/28 | V Boys Lacrosse | Bunnell-Stratford | Away - Stratford HS @ Longbrook Park-Penders Field (Longbrook Park) [Directions] | 6:30 p.m. | W 19-7 | |
| Thu., 4/28 | JV Boys Lacrosse | Bunnell-Stratford | Away - Stratford HS @ Longbrook Park-Penders Field (Longbrook Park) [Directions] | 5:00 p.m. | ||
| Thu., 4/28 | V Girls Golf | Brookfield | Away - Sunset Hill Golf Course [Directions] | 3:00 p.m. | Brookfield 234 Weston 237 | |
| Thu., 4/28 | JV Softball | Brookfield | Home - Weston HS-Softball - MS Field (JV) [Directions] | Canceled | Cancelled | |
| Thu., 4/28 | V Girls Tennis | Pomperaug | Away - Edgewood Bath and Tennis Club [Directions] | 3:45 p.m. | W 7-0 | |
| Fri., 4/29 | V Baseball | Stratford | Away - Penders Field-Penders Field - Stratford [Directions] | 4:15 p.m. | L 4-5 | |
| Fri., 4/29 | V Boys Outdoor Track | O'Grady Relays at Danbury High School | Away - Not Listed | 5:00 p.m. | ||
| Fri., 4/29 | V Boys Tennis | Joel Barlow | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | W 6-1 [Detailed Results] | |
| Fri., 4/29 | V Girls Outdoor Track | O'Grady Relays at Danbury High School | Away - Not Listed | 5:00 p.m. | ||
| Fri., 4/29 | V Softball | Stratford | Away - DeLuca Field-Deluca Field [Directions] | 4:15 p.m. | W 18-1 | |
| Sat., 4/30 | JV Baseball | Stratford | Home - Weston HS-Revson #1 (Varsity) [Directions] | 12:00 p.m. | ||
| Sat., 4/30 | V Boys Lacrosse | Iona Prep (NY) | Home - Weston HS-WHS Lower Turf Field [Directions] | 12:00 p.m. | L 13-5 | |
| Sat., 4/30 | JV Boys Lacrosse | Iona Prep (NY) | Home - Weston HS-WHS Lower Turf Field [Directions] | 10:00 a.m. | ||
| Sat., 4/30 | V Boys Outdoor Track | O'Grady Relays at Danbury High School | Away - Not Listed | 10:00 a.m. | ||
| Sat., 4/30 | JV Boys Tennis | Fairfield Ludlowe | Away - Tomlinson MS-Tennis Courts [Directions] | 10:00 a.m. | ||
| Sat., 4/30 | V Girls Outdoor Track | O'Grady Relays at Danbury High School | Away - Not Listed | 10:00 a.m. | ||
| Sat., 4/30 | JV Softball | Stratford | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | Canceled | Cancelled | |
| Sat., 4/30 | V Girls Tennis | Fairfield Ludlowe | Home - Weston HS-WHS Tennis Courts [Directions] | 9:00 a.m. | L 6-1 | |
| Mon., 5/2 | V Boys Lacrosse | Bethel | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | W 21-6 | |
| Mon., 5/2 | JV Boys Lacrosse | Staples | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 5/2 | JV Boys Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | Postponed | ||
| Mon., 5/2 | V Girls Golf | Newtown | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | Newtown 218 Weston 251 | |
| Mon., 5/2 | V Girls Outdoor Track | Bethel, Brookfield, Bunnell | Away - Bethel HS-BHS track [Directions] | 4:00 p.m. | Weston 68 Brookfield 53 Weston 77 Bunnell 62 Bethel 77 Weston 56 | |
| Mon., 5/2 | JV Girls Tennis | Ridgefield | Home - Weston HS-WHS Tennis Courts [Directions] | Postponed | ||
| Tue., 5/3 | V Baseball | New Milford | Away - New Milford HS-Baseball Varsity Field - NMHS [Directions] | 4:15 p.m. | L 0-2 | |
| Tue., 5/3 | JV Baseball | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Fabbri Field [Directions] | 4:00 p.m. | ||
| Tue., 5/3 | V Boys Lacrosse | Fairfield Ludlowe | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | L 3-9 | |
| Tue., 5/3 | JV Boys Lacrosse | Fairfield Ludlowe | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 5/3 | V Boys Outdoor Track | Bethel, Brookfield, Bunnell | Home - Weston HS-WHS Track [Directions] | 4:00 p.m. | Weston 75 Bethel 75 Weston 109 Bunnell 41 Weston 112 Brookfield 33 | |
| Tue., 5/3 | V Girls Golf | Joel Barlow | Away - Redding Country Club [Directions] | 3:30 p.m. | Joel Barlow 238 Weston 264 | |
| Tue., 5/3 | V Girls Lacrosse | Bethel | Away - Bethel HS-DeSantis Field at Bethel High [Directions] | 4:30 p.m. | W 18-11 | |
| Tue., 5/3 | JV Girls Lacrosse | Bethel | Away - Bethel HS-DeSantis Field @ Bethel High School [Directions] | 6:00 p.m. | ||
| Tue., 5/3 | V Softball | New Milford | Away - New Milford HS-Softball Varsity Field - NMHS [Directions] | 4:15 p.m. | L 7-19 | |
| Tue., 5/3 | V Girls Tennis | Joel Barlow | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | W 4-3 | |
| Wed., 5/4 | V Girls Lacrosse | Stratford/Bunnell | Away - Penders Field-Penders Field - Stratford [Directions] | 6:30 p.m. | W 20-8 | |
| Wed., 5/4 | JV Girls Lacrosse | Stratford/Bunnell | Away - Penders Field-Penders Field - Stratford [Directions] | 5:00 p.m. | ||
| Thu., 5/5 | V Baseball | Notre Dame-Fairfield | Home - Weston HS-Revson #1 (Varsity) [Directions] | 4:15 p.m. | W 3-1 | |
| Thu., 5/5 | JV Baseball | New Milford | Home - Weston HS-Revson #2 (JV) [Directions] | 4:15 p.m. | ||
| Thu., 5/5 | JV Boys Lacrosse | Brookfield | Away - Brookfield HS-BHS Stadium Field [Directions] | 6:00 p.m. | ||
| Thu., 5/5 | V Girls Tennis | Notre Dame-Fairfield | Away - Veteran's Park - Bridgeport-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Fri., 5/6 | V Boys Tennis | Staples | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | Cancelled | |
| Sat., 5/7 | V Baseball | Brookfield | Home - Weston HS-Revson #1 (Varsity) [Directions] | 12:00 p.m. | Cancelled | |
| Sat., 5/7 | JV Baseball | Immaculate | Away - Immaculate HS-Baseball Diamond [Directions] | Postponed | ||
| Sat., 5/7 | V Boys Lacrosse | Daniel Hand | Away - Madison Surf Club-Strong Field [Directions] | 7:00 p.m. | L 5-7 | |
| Sat., 5/7 | JV Boys Lacrosse | Daniel Hand | Away - Madison Surf Club-Strong Field [Directions] | 5:00 p.m. | ||
| Sat., 5/7 | JV Boys Tennis | Fairfield Ludlowe | Home - Weston HS-WHS Tennis Courts [Directions] | Postponed | ||
| Sat., 5/7 | V Girls Lacrosse | Fitch | Home - Weston HS-WHS Lower Turf Field [Directions] | 1:00 p.m. | W 18-7 | |
| Sat., 5/7 | JV Girls Lacrosse | Fitch | Home - Weston HS-WHS Lower Turf Field [Directions] | 11:30 a.m. | ||
| Mon., 5/9 | V Baseball | Masuk | Away - Masuk HS-John Giampaolo Baseball Field @ Masuk HS [Directions] | 4:15 p.m. | L 2-15 | |
| Mon., 5/9 | V Boys Lacrosse | Notre Dame-Fairfield | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:30 p.m. | W 21-1 | |
| Mon., 5/9 | V Boys Tennis | New Milford | Away - New Milford HS-Tennis Courts - NMHS [Directions] | 3:45 p.m. | W 7-0 | |
| Mon., 5/9 | V | Unified Track and Field | Home - Weston HS-WHS Stadium Field [Directions] | 3:00 p.m. | ||
| Mon., 5/9 | V Girls Golf | Brookfield, Stratford | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | Weston 260 Stratford 277 Brookfield 258 Weston 260 | |
| Mon., 5/9 | V Girls Outdoor Track | Newtown, New Milford | Away - Newtown HS-Blue and Gold Stadium [Directions] | 4:00 p.m. | weston 113 NM 37 newtown 83.5 weston 66.5 | |
| Mon., 5/9 | V Softball | Masuk | Away - Masuk HS-Masuk High School Softball Field [Directions] | 4:15 p.m. | L 1-17 | |
| Mon., 5/9 | V Girls Tennis | New Milford | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Tue., 5/10 | JV Baseball | Masuk | Home - Weston HS-Revson #2 (JV) [Directions] | 4:00 p.m. | ||
| Tue., 5/10 | V Boys Lacrosse | New Fairfield | Away - New Fairfield HS-Marty Morgan Field [Directions] | 4:45 p.m. | W 9-0 | |
| Tue., 5/10 | JV Boys Lacrosse | New Fairfield | Away - New Fairfield HS-Marty Morgan Field [Directions] | 6:30 p.m. | ||
| Tue., 5/10 | V Boys Outdoor Track | New Milford, Newtown | Away - New Milford HS-Joe Wiser Stadium - NMHS [Directions] | 4:00 p.m. | Weston 87 Newtown 63 Weston 90 New Milford 59 | |
| Tue., 5/10 | V Girls Lacrosse | New Fairfield | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | W 11-9 | |
| Tue., 5/10 | JV Girls Lacrosse | New Fairfield | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:15 p.m. | ||
| Tue., 5/10 | V Softball | Notre Dame-Fairfield | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 4:15 p.m. | W 5-4 | |
| Tue., 5/10 | JV Softball | Masuk | Home - Weston HS-Softball - MS Field (JV) [Directions] | Canceled | Cancelled | |
| Wed., 5/11 | V Baseball | Joel Barlow | Away - Joel Barlow HS-Baseball Field [Directions] | 4:15 p.m. | L 1-11 | |
| Wed., 5/11 | V Girls Golf | Masuk | Away - Whitney Farms Golf Course [Directions] | 2:45 p.m. | Masuk 223 Weston 247 | |
| Wed., 5/11 | V Softball | Joel Barlow | Away - Joel Barlow High-Field E (Softball) [Directions] | 4:15 p.m. | W 6-5 | |
| Wed., 5/11 | V Girls Tennis | Masuk | Away - Wolfe Park-Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Thu., 5/12 | V Baseball | Pomperaug | Home - Weston HS-Revson #1 (Varsity) [Directions] | 4:15 p.m. | W 11-1 | |
| Thu., 5/12 | V Boys Lacrosse | New Milford | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | W 11-2 | |
| Thu., 5/12 | JV Boys Lacrosse | New Milford | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 5/12 | V Boys Tennis | Bethel | Home - Weston HS-WHS Tennis Courts [Directions] | 5:15 p.m. | W 7-0 [Detailed Results] | |
| Thu., 5/12 | V Girls Golf | Newtown | Away - Newtown Country Club [Directions] | 2:30 p.m. | Newtown 186 Weston 267 | |
| Thu., 5/12 | V Girls Lacrosse | New Milford | Away - New Milford HS-Joe Wiser Stadium - NMHS [Directions] | 6:00 p.m. | W 15-2 | |
| Thu., 5/12 | JV Girls Lacrosse | New Milford | Away - New Milford HS-North Turf Field - NMHS [Directions] | 4:15 p.m. | ||
| Thu., 5/12 | JV Softball | Joel Barlow | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 4:00 p.m. | ||
| Thu., 5/12 | V Girls Tennis | Stratford | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Fri., 5/13 | Miscellaneous Events | WHS PROM | Home - Weston HS-Admin field [Directions] | 6:00 p.m. | ||
| Sat., 5/14 | V Boys Tennis | Stratford | Away - Flood MS-Flood MS Tennis Courts [Directions] | 11:00 a.m. | W 7-0 [Detailed Results] | |
| Sat., 5/14 | JV Softball | Joel Barlow | Away - Joel Barlow HS-Field E [Directions] | 2:00 p.m. | ||
| Sun., 5/15 | V Girls Tennis | Wilton | Away - Wilton HS-Tennis Courts [Directions] | 11:00 a.m. | L 1-6 | |
| Mon., 5/16 | JV Boys Lacrosse | Masuk | Home - Weston HS-WHS Lower Turf Field [Directions] | Canceled | Cancelled | |
| Mon., 5/16 | V Girls Golf | Joel Barlow | Home - Weston HS-Aspetuck Country Club [Directions] | 2:00 p.m. | Joel Barlow 238 Weston 244 | |
| Tue., 5/17 | V Baseball | Brookfield | Home - Weston HS-Revson #1 (Varsity) [Directions] | 4:15 p.m. | L 16-0 | |
| Tue., 5/17 | JV Baseball | Bunnell | Away - Bunnell HS-Bunnell Baseball Field [Directions] | 4:00 p.m. | ||
| Tue., 5/17 | V Boys Lacrosse | Masuk | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | W 10-5 | |
| Tue., 5/17 | JV Boys Lacrosse | Stamford | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 5/17 | V Boys Outdoor Track | Immaculate, Kolbe Cathedral, Notre Dame-Fairfield | Home - Weston HS-WHS Track [Directions] | 4:00 p.m. | Weston 113 Immaculate 27 Weston 128 Kolbe 18 Weston 132 Notre Dame 2 | |
| Tue., 5/17 | V Boys Tennis | Immaculate | Away - Immaculate HS-Rogers Park, Danbury [Directions] | 2:30 p.m. | W 7-0 | |
| Tue., 5/17 | V Boys Tennis | Masuk | Away - Wolfe Park-Tennis Courts [Directions] | 5:00 p.m. | W 7-0 | |
| Tue., 5/17 | V Girls Golf | Notre Dame-Fairfield | Away - Fairchild Wheeler Golf Course [Directions] | 3:00 p.m. | Cancelled | |
| Tue., 5/17 | V Girls Lacrosse | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 6:30 p.m. | W 13-11 | |
| Tue., 5/17 | JV Girls Lacrosse | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 5:00 p.m. | ||
| Tue., 5/17 | V Girls Outdoor Track | Immaculate, Kolbe Cathedral, Notre Dame-Fairfield | Home - Weston HS-WHS Track [Directions] | 4:00 p.m. | weston 121 kolbe 11 weston 121 ND 21 weston 110.5 Imm 22.5 | |
| Tue., 5/17 | V Softball | Bunnell | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 4:15 p.m. | L 7-13 | |
| Wed., 5/18 | V Baseball | Bunnell | Home - Weston HS-Revson #1 (Varsity) [Directions] | 4:15 p.m. | W 9-1 | |
| Wed., 5/18 | JV Baseball | Pomperaug | Away - Community House Park-Baseball Field [Directions] | 4:15 p.m. | ||
| Wed., 5/18 | V Softball | Abbott Tech | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 3:45 p.m. | W 21-9 | |
| Wed., 5/18 | V Girls Tennis | Immaculate | Away - Immaculate HS-Rogers Park, Danbury [Directions] | 3:45 p.m. | W 7-0 | |
| Thu., 5/19 | V Boys Lacrosse | Bethel | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | W 10-2 | |
| Thu., 5/19 | V Boys Tennis | SWC Boys Tennis Championships | Away - Rogers Park (Danbury, CT)-Tennis Courts | 12:00 p.m. | ||
| Thu., 5/19 | V Girls Golf | Bunnell | Away - Bunnell HS-Mill River CC [Directions] | 3:00 p.m. | Weston 240 Bunnell 322 | |
| Thu., 5/19 | V Girls Golf | Stratford | Away - Mill River Country Club [Directions] | 3:00 p.m. | Weston 240 Stratford 258 | |
| Thu., 5/19 | V Girls Lacrosse | Brookfield | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:30 p.m. | W 10-8 | |
| Thu., 5/19 | JV Softball | New Milford | Home - Weston HS-Softball - MS Field (JV) [Directions] | Postponed | ||
| Thu., 5/19 | V Girls Tennis | SWC Girls Tennis Championships | Away - Joel Barlow HS-Tennis Courts | 2:00 p.m. | ||
| Fri., 5/20 | V Boys Outdoor Track | SWC Freshmen Invite | Away - Bethel HS-BHS track | 4:00 p.m. | ||
| Fri., 5/20 | V Softball | New Fairfield | Away - New Fairfield HS-Softball Field [Directions] | 4:15 p.m. | W 8-2 | |
| Sat., 5/21 | V Baseball | Joel Barlow | Away - Joel Barlow HS-Baseball Field [Directions] | 3:00 p.m. | L 4-5 | |
| Sat., 5/21 | V Boys Tennis | Hall | Away - Hall HS-Tennis Courts [Directions] | 10:00 a.m. | W 4-3 [Detailed Results] | |
| Mon., 5/23 | V Baseball | SWC Semifinals at Home of Higher Seed | Away - Not Listed | TBA | ||
| Mon., 5/23 | JV Baseball | Joel Barlow | Home - Weston HS-Revson #2 (JV) [Directions] | 4:00 p.m. | ||
| Mon., 5/23 | V Boys Tennis | SWC Boys Tennis Championships | Away - Rogers Park (Danbury, CT)-Rogers Park | 11:30 a.m. | [Detailed Results] | |
| Mon., 5/23 | V Girls Lacrosse | Masuk | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | W 7-5 | |
| Mon., 5/23 | V Girls Tennis | SWC Championship Tournament | Away - Joel Barlow HS-Tennis Courts | 2:00 p.m. | ||
| Tue., 5/24 | V Boys Lacrosse | New Fairfield | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | W 16-3 | |
| Tue., 5/24 | V Boys Outdoor Track | Bunnell, Bethel, Brookfield, Immaculate, Joel Barlow, Kolbe Cathedral, Masuk, New Fairfield, New Milford, Newtown, Notre Dame-Fairfield, Pomperaug, Stratford | Away - New Milford HS-Track | 3:00 p.m. | ||
| Tue., 5/24 | V Girls Golf | Immaculate, Stratford | Away - Immaculate HS-Richter Park [Directions] | 3:00 p.m. | Immaculate 196 Weston 240 | |
| Tue., 5/24 | V Girls Outdoor Track | Bunnell, Bethel, Brookfield, Immaculate, Joel Barlow, Kolbe Cathedral, Masuk, New Fairfield, New Milford, Newtown, Notre Dame-Fairfield, Pomperaug, Stratford | Away - New Milford HS-Track | 3:00 p.m. | ||
| Wed., 5/25 | V Boys Tennis | Daniel Hand | Home - Weston HS-WHS Tennis Courts [Directions] | 4:00 p.m. | L 2-5 | |
| Wed., 5/25 | V Girls Lacrosse | New Fairfield | Home - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | L 6-9 | |
| Thu., 5/26 | V Boys Lacrosse | New Milford | Home - Newtown HS-Blue and Gold Stadium [Directions] | 7:00 p.m. | W 11-2 | |
| Thu., 5/26 | JV Boys Tennis | Wilton | Away - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | ||
| Sat., 5/28 | V Baseball | Cromwell | Away - Cromwell HS-Fran Monnes Baseball Field [Directions] | 1:00 p.m. | W 2-1 | |
| Tue., 5/31 | V Baseball | Nonnewaug | Away - Nonnewaug HS-Baseball Diamond [Directions] | 3:30 p.m. | W 7-4 | |
| Tue., 5/31 | V Boys Tennis | Torrington | Home - Weston HS-WHS Tennis Courts [Directions] | 1:00 p.m. | W 7-0 | |
| Tue., 5/31 | V Girls Golf | SWC Girls Golf Championship Tournament @ Fairchild Wheeler Golf Course | Away - Fairchild Wheeler Golf Course | 8:00 a.m. | ||
| Tue., 5/31 | V Girls Lacrosse | East Catholic | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | W 14-7 | |
| Tue., 5/31 | V Girls Tennis | Sacred Heart Academy | Home - Weston HS-WHS Tennis Courts [Directions] | 3:00 p.m. | W 7-0 | |
| Wed., 6/1 | V Baseball | Sheehan | Away - Sheehan HS-Neubauer Baseball Field @ Sheehan HS [Directions] | 4:00 p.m. | ||
| Wed., 6/1 | V Boys Lacrosse | Granby Memorial | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | W 20-1 | |
| Wed., 6/1 | V Boys Tennis | Notre Dame-West Haven | Away - U New Haven-UNH Tennis Courts [Directions] | 3:00 p.m. | W 4-2 | |
| Wed., 6/1 | V Girls Tennis | Waterford | Home - Weston HS-WHS Tennis Courts [Directions] | 3:00 p.m. | W 5-2 | |
| Thu., 6/2 | V Baseball | Sheehan | Away - Sheehan HS-Neubauer Baseball Field @ Sheehan HS [Directions] | 1:00 p.m. | ||
| Thu., 6/2 | V Boys Outdoor Track | CIAC Class M Championship | Away - Willow Brook Park | 3:00 p.m. | ||
| Thu., 6/2 | V Girls Outdoor Track | CIAC Class M Championship | Away - Willow Brook Park | 3:00 p.m. | ||
| Fri., 6/3 | V Boys Tennis | Avon | Away - Newington Tennis Center [Directions] | 1:30 p.m. | L 1-6 | |
| Fri., 6/3 | V Girls Lacrosse | Canton | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:00 p.m. | W 12-11 | |
| Fri., 6/3 | V Girls Tennis | Stonington | Away - Stonington HS-SHS Tennis Courts [Directions] | 1:30 p.m. | L 2-5 | |
| Sat., 6/4 | V Boys Lacrosse | Sheehan | Away - Sheehan HS-Sheehan HS Riccitelli Field (Turf) [Directions] | 2:30 p.m. | W 10-9 | |
| Mon., 6/6 | V Boys Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/6 | V Boys Tennis | CIAC Individual Invitational - Opening Round, Singles and Doubles | Away - Wesleyan | 10:00 a.m. | ||
| Mon., 6/6 | V | Wilton | Away - Wilton HS-Track [Directions] | 3:00 p.m. | ||
| Mon., 6/6 | V Girls Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/6 | V Girls Tennis | CIAC Individual Invitational - Opening Round, Singles and Doubles | Away - Wesleyan | 10:00 a.m. | ||
| Tue., 6/7 | V Boys Tennis | CIAC Individual Invitational - Round of 16 | Away - Wesleyan | 9:00 a.m. | ||
| Tue., 6/7 | V Girls Lacrosse | New Fairfield | Home - Jonathan Law HS-Lacrosse Field [Directions] | 7:00 p.m. | ||
| Tue., 6/7 | V Girls Tennis | CIAC Individual Invitational - Round of 16 | Away - Wesleyan | 9:00 a.m. | ||
| Wed., 6/8 | V Boys Lacrosse | Haddam-Killingworth | Home - Fairfield Warde-Gym 1 [Directions] | 4:00 p.m. | W 16-4 | |
| Wed., 6/8 | V Boys Tennis | CIAC Individual Invitational - Quarterfinals | Away - Wesleyan | 3:00 p.m. | ||
| Wed., 6/8 | V Girls Golf | CIAC Division II Championship | Away - Timberlin GC | 8:30 a.m. | ||
| Wed., 6/8 | V Girls Tennis | CIAC Individual Invitational - Quarterfinals | Away - Wesleyan | 3:00 p.m. | ||
| Thu., 6/9 | V Boys Tennis | CIAC Individual Invitational - Semifinals | Away - Wesleyan | 3:00 p.m. | ||
| Thu., 6/9 | V Girls Tennis | CIAC Individual Invitational - Semifinals | Away - Wesleyan | 3:00 p.m. | ||
| Fri., 6/10 | V Boys Tennis | CIAC Individual Invitational - Finals | Away - Wesleyan | 3:00 p.m. | ||
| Fri., 6/10 | V Girls Tennis | CIAC Individual Invitational - Finals | Away - Wesleyan | 3:00 p.m. | ||
| Sat., 6/11 | V Girls Golf | CIAC Girls State Open | Away - Black Hall Club | 1:00 p.m. | ||
| Sun., 6/12 | V Boys Lacrosse | Northwest Catholic | Home - Sacred Heart University [Directions] | 10:00 a.m. | ||
| Wed., 6/15 | V Boys Outdoor Track | CIAC Decathlon Championship Day 2 | Away - Willow Brook Park | 10:00 a.m. | ||
| Wed., 6/15 | V Boys Outdoor Track | CIAC Boys Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||