| Weston 2020-21 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 431 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Thu., 9/3 | Miscellaneous Events | Meet the Coaches Night | Home - Weston HS-Cafeteria [Directions] | 6:00 p.m. | Freshman and athletes new to WHS and their parent/guardian will meet in the Cafeteria starting at 6pm. All athletes and their parent/guardian will meet in individual team locations starting at 7:30. | |
| Thu., 10/1 | V Boys Soccer | Joel Barlow | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:15 p.m. | L 1-4 | |
| Thu., 10/1 | V Field Hockey | Joel Barlow | Away - Joel Barlow High-Stadium Field [Directions] | 6:45 p.m. | L 3-0 | |
| Thu., 10/1 | V Girls Soccer | Joel Barlow | Away - Joel Barlow HS-Field J (Competition Field) [Directions] | 4:15 p.m. | W 1-0 | |
| Thu., 10/1 | V Girls Volleyball | Joel Barlow | Home - Weston HS-Gym (New) [Directions] | 4:15 p.m. | L 0-3 | |
| Fri., 10/2 | V Football | Bethel | Away - Bethel HS-DeSantis Field at Bethel High [Directions] | 6:00 p.m. | W 33-14 | |
| Fri., 10/2 | V Girls Swimming and Diving | Joel Barlow | Home - Weston HS-Weston MS Pool [Directions] | 4:15 p.m. | Weston 96 Joel Barlow 76 | |
| Sat., 10/3 | V Boys Soccer | Kolbe Cathedral | Home - Weston HS-WHS Lower Turf Field [Directions] | 12:30 p.m. | W 8-0 | |
| Sat., 10/3 | V Field Hockey | Masuk | Home - Weston HS-WHS Lower Turf Field [Directions] | 3:30 p.m. | L 1-4 | |
| Sat., 10/3 | V Girls Soccer | Kolbe Cathedral | Away - Veterans Memorial Park CT [Directions] | 12:30 p.m. | W 6-0 | |
| Sat., 10/3 | V Girls Volleyball | Kolbe Cathedral | Home - Weston HS-Gym (New) [Directions] | 12:00 p.m. | W 3-0 | |
| Mon., 10/5 | V Girls Volleyball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 4:15 p.m. | L 1-3 | |
| Tue., 10/6 | V Boys Cross Country | Notre Dame-Fairfield | Home - Weston HS-WHS Stadium Field [Directions] | 5:00 p.m. | Weston 15 Notre Dame 50 | |
| Tue., 10/6 | V Boys Soccer | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 4:15 p.m. | W 1-0 | |
| Tue., 10/6 | V Girls Cross Country | Notre Dame-Fairfield | Home - Weston HS-WHS Stadium Field [Directions] | 4:30 p.m. | Weston 15 Notre Dame 50 | |
| Wed., 10/7 | V Girls Volleyball | Bullard Havens Tech | Home - Weston HS-Gym (New) [Directions] | 4:15 p.m. | W 3-0 | |
| Thu., 10/8 | V Boys Soccer | Bullard Havens Tech | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:15 p.m. | W 7-1 | |
| Thu., 10/8 | V Girls Soccer | Bullard Havens Tech | Away - Bullard Havens Tech-Soccer Field [Directions] | 4:15 p.m. | W 6-0 | |
| Fri., 10/9 | V Football | Stratford | Home - Weston HS-WHS Stadium Field [Directions] | 6:00 p.m. | W 34-13 | |
| Fri., 10/9 | V Field Hockey | Joel Barlow | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:15 p.m. | L 0-5 | |
| Fri., 10/9 | V Girls Swimming and Diving | Masuk | Away - Masuk HS-Pool [Directions] | 4:15 p.m. | Weston 101- Masuk 77 | |
| Sat., 10/10 | JV Boys Soccer | Stratford | Home - Weston HS-WHS Lower Turf Field [Directions] | 10:00 a.m. | ||
| Sat., 10/10 | JV Field Hockey | Immaculate | Away - Immaculate HS-Mustang Valley [Directions] | 10:00 a.m. | ||
| Sat., 10/10 | JV Field Hockey | Immaculate | Away - Immaculate HS-Mustang Valley [Directions] | Postponed | ||
| Sat., 10/10 | V Girls Soccer | Joel Barlow | Home - Weston HS-WHS Lower Turf Field [Directions] | 3:00 p.m. | W 4-1 | |
| Sat., 10/10 | JV Girls Soccer | Stratford | Away - Penders Field-Penders Field - Stratford [Directions] | 10:00 a.m. | ||
| Tue., 10/13 | V Boys Cross Country | Bunnell, Kolbe Cathedral | Away - Bunnell HS-Bunnell Track [Directions] | 5:00 p.m. | Weston 18 - Bunnell 45 Weston over Kolby no score | |
| Tue., 10/13 | V Boys Soccer | Notre Dame-Fairfield | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:15 p.m. | W 3-2 | |
| Tue., 10/13 | V Girls Cross Country | Bunnell, Kolbe Cathedral | Away - Bunnell HS-Bunnell Track [Directions] | 4:30 p.m. | Weston-42 Barlow-17 | |
| Tue., 10/13 | V Field Hockey | Bethel | Away - Bethel HS-Hunt Field at Bethel HS [Directions] | 4:15 p.m. | T 1-1 | |
| Tue., 10/13 | V Girls Soccer | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Park Ave Field [Directions] | 4:15 p.m. | L 1-4 | |
| Tue., 10/13 | V Girls Swimming and Diving | Stratford | Away - Flood MS-Flood MS Pool [Directions] | 4:15 p.m. | Weston 91 Stratford 71 | |
| Tue., 10/13 | V Girls Volleyball | Notre Dame-Fairfield | Home - Weston HS-Gym (New) [Directions] | 4:15 p.m. | W 3-1 | |
| Wed., 10/14 | V Field Hockey | Joel Barlow | Away - Joel Barlow High-Stadium Field [Directions] | 6:45 p.m. | L 0-5 | |
| Wed., 10/14 | V Girls Volleyball | Stratford | Away - Stratford HS-Gym [Directions] | 5:00 p.m. | L 1-3 | |
| Thu., 10/15 | V Football | Joel Barlow | Away - Joel Barlow HS-Field I (Stadium) [Directions] | 6:00 p.m. | W 35-21 | |
| Thu., 10/15 | V Boys Soccer | Stratford | Away - Penders Field-Penders Field - Stratford [Directions] | 5:00 p.m. | W 2-0 | |
| Thu., 10/15 | V Girls Soccer | Stratford | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:15 p.m. | W 5-1 | |
| Fri., 10/16 | V Girls Swimming and Diving | Masuk | Home - Weston HS-Weston MS Pool [Directions] | 4:15 p.m. | Weston 99 Masuk 76 | |
| Sat., 10/17 | JV Boys Soccer | Bethel | Away - Joel Barlow HS-Field J [Directions] | 11:30 a.m. | ||
| Sat., 10/17 | JV Boys Soccer | Joel Barlow | Away - Joel Barlow HS-Joel Barlow HS Stadium [Directions] | 1:00 p.m. | ||
| Sat., 10/17 | JV Field Hockey | Joel Barlow | Home - Weston HS-WHS Lower Turf Field [Directions] | 1:00 p.m. | ||
| Sat., 10/17 | JV Field Hockey | Masuk | Home - Weston HS-WHS Lower Turf Field [Directions] | 3:20 p.m. | ||
| Sat., 10/17 | JV Girls Soccer | Bunnell | Home - Weston HS-WHS Lower Turf Field [Directions] | 1:30 p.m. | ||
| Sat., 10/17 | JV Girls Soccer | Stratford | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:20 p.m. | ||
| Mon., 10/19 | V Field Hockey | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 4:15 p.m. | L 0-7 | |
| Mon., 10/19 | V Girls Volleyball | Bunnell | Home - Weston HS-Gym (New) [Directions] | 4:15 p.m. | W 3 -1 | |
| Tue., 10/20 | V Boys Cross Country | Bullard Havens Tech, Notre Dame-Fairfield | Home - Weston HS-WHS Stadium Field [Directions] | 5:00 p.m. | Weston 15 Notre Dame 49 Weston over Bullard Haven - No Score | |
| Tue., 10/20 | V Boys Soccer | Bunnell | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:15 p.m. | T 1-1 | |
| Tue., 10/20 | V Girls Cross Country | Bullard Havens Tech, Notre Dame-Fairfield | Home - Weston HS-WHS Stadium Field [Directions] | 4:30 p.m. | Weston 15 Bullard Haven 50 Weston 15 Notre Dame 50 | |
| Tue., 10/20 | V Girls Soccer | Bunnell | Away - Bunnell HS-Bunnell Turf Field [Directions] | 4:15 p.m. | W 8-1 | |
| Tue., 10/20 | V Girls Swimming and Diving | Bunnell | Home - Weston HS-Weston MS Pool [Directions] | 4:15 p.m. | Weston 94 Bunnell 79 | |
| Wed., 10/21 | V Girls Volleyball | Joel Barlow | Away - Joel Barlow High-Lower Gym [Directions] | 4:15 p.m. | L 0-3 | |
| Thu., 10/22 | V Boys Soccer | Joel Barlow | Away - Joel Barlow HS-Field J (Competition Field) [Directions] | 4:15 p.m. | W 3-0 | |
| Thu., 10/22 | V Girls Soccer | Joel Barlow | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:15 p.m. | W 3-1 | |
| Fri., 10/23 | V Boys Cross Country | Joel Barlow | Home - Weston HS-WHS Stadium Field [Directions] | 5:00 p.m. | Weston 24 Joel Barlow 32 | |
| Fri., 10/23 | V Girls Cross Country | Joel Barlow | Home - Weston HS-WHS Stadium Field [Directions] | 4:30 p.m. | Joel Barlow 16 Weston 44 | |
| Fri., 10/23 | V Field Hockey | Immaculate | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:15 p.m. | L 0-7 | |
| Fri., 10/23 | V Girls Swimming and Diving | Stratford | Home - Weston HS-Weston MS Pool [Directions] | 4:15 p.m. | Weston-99 Stratford-73 | |
| Sat., 10/24 | V Football | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -McCarty Stadium [Directions] | 2:00 p.m. | L 14-26 | |
| Sat., 10/24 | V Field Hockey | Immaculate | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | L 0-3 | |
| Sat., 10/24 | JV Field Hockey | Masuk | Away - Immaculate HS-Mustang Valley [Directions] | 10:00 a.m. | ||
| Sat., 10/24 | JV Field Hockey | Immaculate | Away - Immaculate HS-Mustang Valley [Directions] | 11:00 a.m. | ||
| Sat., 10/24 | JV Girls Soccer | Stratford | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 2:30 p.m. | ||
| Sat., 10/24 | JV Girls Soccer | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 4:00 p.m. | ||
| Mon., 10/26 | V Field Hockey | Immaculate | Away - Immaculate HS-Mustang Valley [Directions] | 4:15 p.m. | L 1-9 | |
| Mon., 10/26 | FR Girls Soccer | Masuk | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 10/26 | V Girls Volleyball | Kolbe Cathedral | Away - Kolbe Cathedral HS-Gym [Directions] | 4:15 p.m. | W 3-0 | |
| Tue., 10/27 | V Boys Cross Country | Joel Barlow | Away - Joel Barlow HS-Cross Country Course [Directions] | 5:00 p.m. | Joel Barlow 24 Weston 37 | |
| Tue., 10/27 | V Boys Soccer | Kolbe Cathedral | Away - Veterans Memorial Park CT [Directions] | 4:15 p.m. | W 7-0 | |
| Tue., 10/27 | V Girls Cross Country | Joel Barlow | Away - Joel Barlow HS-Cross Country Course [Directions] | 4:30 p.m. | ||
| Tue., 10/27 | V Girls Soccer | Kolbe Cathedral | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:15 p.m. | W 6-0 | |
| Tue., 10/27 | V Girls Swimming and Diving | Joel Barlow | Home - Weston HS-Weston MS Pool [Directions] | 4:15 p.m. | Weston 94 Barlow 75 | |
| Wed., 10/28 | V Field Hockey | Bethel | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:15 p.m. | T 0-0 | |
| Wed., 10/28 | V Girls Volleyball | Masuk | Home - Weston HS-Gym (New) [Directions] | 4:15 p.m. | W 3-0 | |
| Thu., 10/29 | V Boys Soccer | Masuk | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:15 p.m. | W 3-1 | |
| Fri., 10/30 | V Football | Bunnell | Home - Weston HS-WHS Stadium Field [Directions] | 6:00 p.m. | W 28-6 | |
| Fri., 10/30 | V Girls Cross Country | Masuk | Away - Great Hollow Lake Fields at Wolfe Park-Cross Country Trail [Directions] | 4:30 p.m. | Cancelled | |
| Fri., 10/30 | V Girls Cross Country | Masuk | Away - Great Hollow Lake Fields at Wolfe Park-Cross Country Trail [Directions] | 5:00 p.m. | Cancelled | |
| Sat., 10/31 | JV Field Hockey | Immaculate | Home - Weston HS-Stadium Field [Directions] | 10:00 a.m. | ||
| Sat., 10/31 | JV Field Hockey | Immaculate | Away - Weston HS-WHS Stadium Field [Directions] | 11:15 a.m. | ||
| Sat., 10/31 | JV Field Hockey | Bethel | Away - Weston HS-WHS Stadium Field [Directions] | 12:30 p.m. | ||
| Sat., 10/31 | JV Girls Soccer | Joel Barlow | Home - Weston HS-WHS Stadium Field [Directions] | 10:00 a.m. | ||
| Sat., 10/31 | JV Girls Soccer | Masuk | Home - Weston HS-WHS Stadium Field [Directions] | 12:50 p.m. | ||
| Mon., 11/2 | V Boys Cross Country | Masuk | Home - Weston HS-WHS Stadium Field [Directions] | 4:00 p.m. | Masuk 25 Weston 32 | |
| Mon., 11/2 | V Girls Cross Country | Masuk | Home - Weston HS-WHS Stadium Field [Directions] | 3:30 p.m. | Weston 33 Masuk 45 | |
| Mon., 11/2 | V Field Hockey | Bethel | Away - Bethel HS-Hunt Field at Bethel HS [Directions] | 4:15 p.m. | L 1-3 | |
| Mon., 11/2 | V Girls Volleyball | Bunnell | Home - Weston HS-Gym (New) [Directions] | 4:15 p.m. | W 3-0 | |
| Tue., 11/3 | V Boys Soccer | Bunnell | Away - Bunnell HS-Bunnell Turf Field [Directions] | 4:15 p.m. | W 2-1 | |
| Tue., 11/3 | V Girls Soccer | Bunnell | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:15 p.m. | W 6-0 | |
| Tue., 11/3 | V Girls Swimming and Diving | Bunnell | Away - Bunnell HS-Flood M.S. Pool [Directions] | 4:15 p.m. | Weston 86 Bunnel 76 | |
| Wed., 11/4 | V Field Hockey | Masuk | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:15 p.m. | ||
| Pending changes awaiting acceptance by one or more parties involved: Date to 11/7, Time to 12:00 p.m., Facility to Masuk HS-Benedict Stadium Field @ Masuk HS | ||||||
| Wed., 11/4 | V Girls Soccer | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Park Ave Field [Directions] | 2:00 p.m. | Cancelled | |
| Wed., 11/4 | V Girls Soccer | Notre Dame-Fairfield | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | ||
| Wed., 11/4 | V Girls Volleyball | Bullard Havens Tech | Away - Bullard Havens Tech-Gym [Directions] | Postponed | ||
| Thu., 11/5 | V Boys Soccer | Bullard Havens Tech | Away - Bullard Havens Tech-Soccer Field [Directions] | 4:15 p.m. | ||
| Thu., 11/5 | V Girls Soccer | Bullard Havens Tech | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:15 p.m. | ||
| Fri., 11/6 | V Boys Cross Country | SWC cross country championship qualifier | Away - TBA | TBA | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 1:00 p.m. | ||||||
| Fri., 11/6 | V Football | Pomperaug | Home - Weston HS-WHS Stadium Field [Directions] | 6:00 p.m. | ||
| Fri., 11/6 | V Girls Cross Country | SWC cross country championship qualifier | Away - TBA | 5:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 2:00 p.m. | ||||||
| Fri., 11/6 | V Girls Cross Country | Girls South Cross Country Championship Heat | Away - Bethel HS-DeSantis Field at Bethel High | 1:00 p.m. | ||
| Fri., 11/6 | V Girls Cross Country | Boys South Cross Country Championship Heat | Away - Bethel HS-DeSantis Field at Bethel High | 1:30 p.m. | ||
| Sat., 11/7 | V Field Hockey | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 12:00 p.m. | L 0-5 | |
| Sat., 11/7 | JV Field Hockey | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 1:30 p.m. | ||
| Wed., 12/9 | Miscellaneous Events | Meet the Coaches Night | Home - Weston HS-Cafeteria [Directions] | 6:00 p.m. | Freshman and athletes new to WHS and their parent/guardian will meet in the Cafeteria starting at 6pm. All athletes and their parent/guardian will meet in individual team locations starting at 7:30. | |
| Fri., 1/8 | V Boys Basketball | Fitch | Away - Fitch HS-Big Gym [Directions] | 3:00 p.m. | ||
| Fri., 1/8 | JV Boys Basketball | Fitch | Away - Fitch HS-Big Gym [Directions] | 1:30 p.m. | ||
| Fri., 1/8 | FR Boys Basketball | Fitch | Away - Fitch HS-Big Gym [Directions] | 11:45 a.m. | ||
| Wed., 2/10 | V Boys Swimming and Diving | Pomperaug | Away - Pomperaug HS-PHS Pool [Directions] | 5:00 p.m. | Pomperaug 96 Weston 73 | |
| Wed., 2/10 | V Girls Gymnastics | Norwalk, Staples | Home - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:30 p.m. | Ludlowe - 136.60 | Virtual Meet |
| Thu., 2/11 | V Boys Basketball | New Milford | Home - Weston HS-Gym (New) [Directions] | 7:15 p.m. | L 48-56 | |
| Thu., 2/11 | JV Boys Basketball | New Milford | Home - Weston HS-Gym (New) [Directions] | 5:45 p.m. | ||
| Thu., 2/11 | FR Boys Basketball | New Milford | Home - Weston HS-Gym (New) [Directions] | 3:45 p.m. | ||
| Thu., 2/11 | V Girls Basketball | New Milford | Away - New Milford HS-Main Gym - NMHS [Directions] | 6:00 p.m. | L 21-23 | |
| Thu., 2/11 | JV Girls Basketball | New Milford | Away - New Milford HS-Main Gym - NMHS [Directions] | 4:30 p.m. | ||
| Thu., 2/11 | V Girls Gymnastics | Staples, Fairfield Warde | Away - Westport YMCA [Directions] | 7:00 p.m. | ||
| Fri., 2/12 | V Girls Ice Hockey | Hamden Coop | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | W 4-3 | |
| Sat., 2/13 | V Boys Basketball | Newtown | Away - Newtown HS-Gym [Directions] | 1:45 p.m. | L 50-78 | |
| Sat., 2/13 | JV Boys Basketball | Newtown | Away - Newtown HS-Gym [Directions] | 12:00 p.m. | ||
| Sat., 2/13 | FR Boys Basketball | Newtown | Away - Newtown HS-Gym [Directions] | 10:00 a.m. | ||
| Sat., 2/13 | V Boys Ice Hockey | New Milford | Home - Danbury Ice Arena-Patriot Rink [Directions] | 6:15 p.m. | L 4-5(OT) | |
| Sat., 2/13 | V Girls Basketball | Newtown | Home - Weston HS-Gym (New) [Directions] | 1:45 p.m. | L 29-51 | |
| Sat., 2/13 | JV Girls Basketball | Newtown | Home - Weston HS-Gym (New) [Directions] | 12:00 p.m. | ||
| Sun., 2/14 | V Girls Gymnastics | Stamford | Home - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 4:00 p.m. | Ludlowe- 138.50 Stamford - 75.20 Westhill - 83.70 | In-Person |
| Sun., 2/14 | JV Girls Ice Hockey | West Haven/SHA | Away - West Haven HS-Bennett Rink [Directions] | 1:30 p.m. | ||
| Mon., 2/15 | V Boys Basketball | New Fairfield | Away - New Fairfield High-HS Gym [Directions] | 2:30 p.m. | L 35-58 | |
| Mon., 2/15 | JV Boys Basketball | New Fairfield | Away - New Fairfield High-HS Gym [Directions] | 1:00 p.m. | ||
| Mon., 2/15 | FR Boys Basketball | New Fairfield | Away - New Fairfield High-HS Gym [Directions] | 11:00 a.m. | ||
| Mon., 2/15 | V Girls Basketball | New Fairfield | Home - Weston HS-Gym (New) [Directions] | 2:30 p.m. | L 16-40 | |
| Mon., 2/15 | JV Girls Basketball | New Fairfield | Home - Weston HS-Gym (New) [Directions] | 1:00 p.m. | ||
| Mon., 2/15 | FR Girls Basketball | New Fairfield | Home - Weston HS-Gym (New) [Directions] | 11:00 a.m. | ||
| Tue., 2/16 | V Boys Swimming and Diving | New Fairfield | Home - Weston HS-Weston MS Pool [Directions] | 4:00 p.m. | Weston 96 New Fairfield 72 | |
| Wed., 2/17 | V Boys Basketball | Masuk | Home - Weston HS-Gym (New) [Directions] | 7:15 p.m. | L 56-66 | |
| Wed., 2/17 | JV Boys Basketball | Masuk | Home - Weston HS-Gym (New) [Directions] | 5:45 p.m. | ||
| Wed., 2/17 | FR Boys Basketball | Masuk | Home - Weston HS-Gym (New) [Directions] | 3:45 p.m. | ||
| Wed., 2/17 | V Boys Ice Hockey | Brookfield | Away - Danbury Ice Arena-Patriot Rink [Directions] | 7:45 p.m. | L 4-7 | |
| Wed., 2/17 | V Girls Basketball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 7:15 p.m. | W 38-29 | |
| Wed., 2/17 | JV Girls Basketball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 5:45 p.m. | ||
| Wed., 2/17 | FR Girls Basketball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 3:45 p.m. | ||
| Wed., 2/17 | V Girls Gymnastics | Darien | Home - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:30 p.m. | Ludlowe - 134.60 | Virtual Meet |
| Wed., 2/17 | V Girls Ice Hockey | Daniel Hand Coop | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | L 3-0 | |
| Fri., 2/19 | JV Girls Basketball | Notre Dame-Fairfield | Home - Weston HS-Gym (New) [Directions] | Canceled | Cancelled | |
| Sat., 2/20 | V Boys Basketball | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Sister Marion Reilly Auditorium [Directions] | 4:15 p.m. | Cancelled | |
| Sat., 2/20 | JV Boys Basketball | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Sister Marion Reilly Auditorium [Directions] | Canceled | Cancelled | |
| Sat., 2/20 | FR Boys Basketball | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Sister Marion Reilly Auditorium [Directions] | 12:30 p.m. | ||
| Sat., 2/20 | V Boys Ice Hockey | Newtown/New Fairfield | Home - Danbury Ice Arena-Patriot Rink [Directions] | 3:00 p.m. | L 1-2(OT) | |
| Sat., 2/20 | V Girls Basketball | Notre Dame-Fairfield | Home - Weston HS-Gym (New) [Directions] | 2:30 p.m. | L 26-74 | |
| Sat., 2/20 | FR Girls Basketball | Notre Dame-Fairfield | Home - Weston HS-Gym (New) [Directions] | 1:00 p.m. | ||
| Sun., 2/21 | V Girls Gymnastics | Greenwich | Home - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 1:00 p.m. | Ludlowe - 137.0 | Virtual Meet |
| Sun., 2/21 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 2:30 p.m. | L 4-1 | |
| Mon., 2/22 | JV Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to 4:00 p.m. | ||||||
| Tue., 2/23 | JV Boys Basketball | Joel Barlow | Home - Weston HS-Gym (New) [Directions] | 5:45 p.m. | ||
| Tue., 2/23 | FR Boys Basketball | Joel Barlow | Home - Weston HS-Gym (New) [Directions] | 3:45 p.m. | ||
| Tue., 2/23 | V Boys Ice Hockey | Brookfield | Home - Danbury Ice Arena-Patriot Rink [Directions] | 8:00 p.m. | L 2-9 | |
| Tue., 2/23 | V Boys Swimming and Diving | Newtown | Away - Newtown HS-pool [Directions] | 6:00 p.m. | Newtown 95 Weston 76 | |
| Tue., 2/23 | V Girls Basketball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 6:00 p.m. | L 42-50 | |
| Tue., 2/23 | JV Girls Basketball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | Canceled | Cancelled | |
| Tue., 2/23 | FR Girls Basketball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/24 | V Girls Gymnastics | Wilton | Home - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:30 p.m. | Ludlowe - 138.35 | Virtual Meet |
| Wed., 2/24 | V Girls Ice Hockey | Hamden Coop | Away - Hamden-Lou Astorino Ice Rink [Directions] | 3:45 p.m. | W 5-1 | |
| Thu., 2/25 | V Boys Swimming and Diving | Bunnell-Stratford | Home - Weston HS-Weston MS Pool [Directions] | 3:30 p.m. | Weston 117 | |
| Thu., 2/25 | V Girls Gymnastics | Wilton | Away - Wilton HS-Aux Gym [Directions] | 3:45 p.m. | ||
| Fri., 2/26 | JV Boys Basketball | Bunnell | Away - Bunnell HS-Bunnell Main Gym [Directions] | 5:45 p.m. | ||
| Fri., 2/26 | FR Boys Basketball | Bunnell | Away - Bunnell HS-Bunnell Main Gym [Directions] | 3:45 p.m. | ||
| Fri., 2/26 | V Boys Swimming and Diving | Bunnell-Stratford | Away - Bunnell HS-Flood M.S. Pool [Directions] | 6:00 p.m. | Bunnell 54 | |
| Fri., 2/26 | V Girls Basketball | Bunnell | Home - Weston HS-Gym (New) [Directions] | 6:00 p.m. | W 42-32 | |
| Fri., 2/26 | JV Girls Basketball | Bunnell | Home - Weston HS-Gym (New) [Directions] | 4:30 p.m. | ||
| Fri., 2/26 | V Girls Ice Hockey | West Haven/SHA | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | L 5-2 | |
| Sat., 2/27 | V Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena-Colonial Rink [Directions] | 11:30 a.m. | ||
| Mon., 3/1 | V Boys Basketball | Brookfield | Home - Weston HS-Gym (New) [Directions] | 7:15 p.m. | Cancelled | |
| Mon., 3/1 | JV Boys Basketball | Brookfield | Home - Weston HS-Gym (New) [Directions] | 5:45 p.m. | ||
| Mon., 3/1 | FR Boys Basketball | Brookfield | Home - Weston HS-Gym (Old) [Directions] | 5:45 p.m. | ||
| Mon., 3/1 | V Boys Ice Hockey | Brien McMahon/Norwalk | Away - Sono Ice House-Main Rink [Directions] | 8:30 p.m. | L 2-4 | |
| Mon., 3/1 | V Girls Basketball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 6:00 p.m. | L 25-37 | |
| Mon., 3/1 | JV Girls Basketball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 4:00 p.m. | ||
| Mon., 3/1 | V Girls Ice Hockey | Jonathan Law | Away - Milford Ice Pavillion-Ice Rink [Directions] | 4:40 p.m. | L 3-0 | |
| Tue., 3/2 | JV Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena-Patriot Rink [Directions] | 5:20 p.m. | ||
| Tue., 3/2 | V Boys Swimming and Diving | Masuk | Home - Weston HS-Weston MS Pool [Directions] | 4:00 p.m. | Masuk 91 Weston 68 | |
| Tue., 3/2 | FR Girls Basketball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 4:00 p.m. | ||
| Wed., 3/3 | V Boys Ice Hockey | Wilton | Home - Danbury Ice Arena-Patriot Rink [Directions] | 5:00 p.m. | Cancelled | |
| Wed., 3/3 | V Boys Indoor Track | Pomperaug | Home - TBA [Directions] | 4:00 p.m. | ||
| Wed., 3/3 | V Girls Gymnastics | Fairfield Warde | Home - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:30 p.m. | Ludlowe - 141.50 | |
| Wed., 3/3 | V Girls Indoor Track | Pomperaug | Home - TBA [Directions] | 4:00 p.m. | ||
| Thu., 3/4 | V Boys Basketball | Kolbe Cathedral | Away - Kolbe Cathedral HS-Cardinal Shehan Center [Directions] | 7:00 p.m. | L 21-52 | |
| Thu., 3/4 | JV Boys Basketball | Kolbe Cathedral | Away - Kolbe Cathedral HS-Cardinal Shehan Center [Directions] | 5:15 p.m. | ||
| Thu., 3/4 | V Girls Basketball | Kolbe Cathedral | Home - Weston HS-Gym (New) [Directions] | 6:00 p.m. | L 22-47 | |
| Thu., 3/4 | JV Girls Basketball | Kolbe Cathedral | Home - Weston HS-Gym (New) [Directions] | 4:30 p.m. | ||
| Fri., 3/5 | V Boys Swimming and Diving | New Milford | Home - Weston HS-Weston MS Pool [Directions] | 7:00 p.m. | New Milford 85 Weston 83 | |
| Fri., 3/5 | V Girls Ice Hockey | Guilford Coop | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | L 8-0 | |
| Fri., 3/5 | JV Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice-New [Directions] | 8:15 p.m. | ||
| Sat., 3/6 | V Boys Basketball | Stratford | Home - Weston HS-Gym (New) [Directions] | 2:45 p.m. | L 37-43 | |
| Sat., 3/6 | JV Boys Basketball | Stratford | Home - Weston HS-Gym (New) [Directions] | 1:00 p.m. | ||
| Sat., 3/6 | FR Boys Basketball | Stratford | Home - Weston HS-Gym (New) [Directions] | 11:00 a.m. | ||
| Sat., 3/6 | JV Girls Basketball | Stratford | Away - Stratford HS-Gym [Directions] | Canceled | Cancelled | |
| Sun., 3/7 | V Girls Gymnastics | St. Joseph, Trumbull | Home - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 1:00 p.m. | Ludlowe - 141.10 | In-person/Hub Meet |
| Mon., 3/8 | V Boys Ice Hockey | Masuk | Home - Danbury Ice Arena-Patriot Rink [Directions] | 4:45 p.m. | ||
| Tue., 3/9 | V Boys Basketball | Pomperaug | Away - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | W 66-56 | |
| Tue., 3/9 | JV Boys Basketball | Pomperaug | Away - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 3/9 | FR Boys Basketball | Pomperaug | Away - Pomperaug HS-Main Gym [Directions] | 3:45 p.m. | ||
| Tue., 3/9 | V Girls Basketball | Pomperaug | Home - Weston HS-Gym (New) [Directions] | 7:15 p.m. | L 39-62 | |
| Tue., 3/9 | JV Girls Basketball | Pomperaug | Home - Weston HS-Gym (New) [Directions] | 5:45 p.m. | ||
| Tue., 3/9 | FR Girls Basketball | Pomperaug | Home - Weston HS-Gym (New) [Directions] | 3:45 p.m. | ||
| Wed., 3/10 | V Boys Basketball | Bunnell | Away - Bunnell HS-Bunnell Main Gym [Directions] | 5:00 p.m. | L 35-57 | |
| Thu., 3/11 | V Girls Gymnastics | Greenwich | Away - Greenwich YWCA [Directions] | 6:00 p.m. | ||
| Thu., 3/11 | JV Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 5:00 p.m. | ||
| Fri., 3/12 | V Boys Basketball | Immaculate | Home - Weston HS-Gym (New) [Directions] | 7:15 p.m. | L 38-63 | |
| Fri., 3/12 | JV Boys Basketball | Immaculate | Home - Weston HS-Gym (New) [Directions] | 5:45 p.m. | ||
| Fri., 3/12 | FR Boys Basketball | Immaculate | Home - Weston HS-Gym (New) [Directions] | 3:45 p.m. | ||
| Fri., 3/12 | V Boys Indoor Track | New Milford | Home - TBA [Directions] | 6:30 p.m. | ||
| Fri., 3/12 | V Girls Basketball | Immaculate | Away - Immaculate HS-Immaculate Gym [Directions] | 7:15 p.m. | L 35-37 | |
| Fri., 3/12 | JV Girls Basketball | Immaculate | Away - Immaculate HS-Immaculate Gym [Directions] | 5:45 p.m. | ||
| Fri., 3/12 | FR Girls Basketball | Immaculate | Away - Immaculate HS-Immaculate Gym [Directions] | 3:45 p.m. | ||
| Fri., 3/12 | V Girls Ice Hockey | Jonathan Law | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | Cancelled | |
| Fri., 3/12 | V Girls Ice Hockey | Hamden Coop | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | Cancelled | |
| Fri., 3/12 | V Girls Indoor Track | New Milford | Home - TBA [Directions] | 6:30 p.m. | ||
| Sat., 3/13 | V Boys Basketball | Joel Barlow | Home - Weston HS-Gym (New) [Directions] | 12:00 p.m. | L 46-64 | |
| Sat., 3/13 | V Boys Ice Hockey | Masuk | Home - Danbury Ice Arena-Patriot Rink [Directions] | 7:45 p.m. | L 5-6 | |
| Sun., 3/14 | V Girls Basketball | Stratford | Away - Stratford HS-Gym [Directions] | 1:00 p.m. | W 38-26 | |
| Sun., 3/14 | V Girls Gymnastics | New Canaan | Home - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 1:00 p.m. | Ludlowe - 140.00 | Virtual Meet |
| Sun., 3/14 | JV Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 7:00 p.m. | ||
| Mon., 3/15 | V Boys Basketball | Immaculate | Away - Immaculate HS-Immaculate Gym [Directions] | 6:00 p.m. | L 34-71 | |
| Mon., 3/15 | V Boys Ice Hockey | Wilton | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 3:15 p.m. | ||
| Mon., 3/15 | V Girls Ice Hockey | West Haven/SHA | Away - West Haven HS-Bennett Rink [Directions] | 3:45 p.m. | Cancelled | |
| Tue., 3/16 | V Boys Swimming and Diving | Brookfield | Home - Weston HS-Weston MS Pool [Directions] | 4:00 p.m. | ||
| Tue., 3/16 | V Girls Basketball | Newtown | Away - Newtown HS [Directions] | 6:00 p.m. | L 26-38 | |
| Tue., 3/16 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Away - Hamden-Lou Astorino Ice Rink [Directions] | 4:30 p.m. | Cancelled | |
| Wed., 3/17 | V Boys Ice Hockey | Housatonic Coop | Home - Danbury Ice Arena-Patriot Rink [Directions] | 6:45 p.m. | ||
| Wed., 3/17 | V Girls Ice Hockey | Guilford Coop | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 8:00 p.m. | L 2-8 | |
| Thu., 3/18 | V Boys Ice Hockey | Masuk | Home - Danbury Ice Arena-Patriot Rink [Directions] | 8:00 p.m. | L 1-6 | |
| Thu., 3/18 | V Boys Swimming and Diving | Joel Barlow-Bethel Swim | Home - Weston HS-Weston MS Pool [Directions] | 3:45 p.m. | Weston 86 Barlow/Bethel 77 | |
| Fri., 3/19 | JV Girls Ice Hockey | West Haven/SHA | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | Canceled | Cancelled | |
| Sat., 3/20 | V Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena-Patriot Rink [Directions] | 3:10 p.m. | ||
| Tue., 3/23 | V Girls Gymnastics | New Canaan | Away - Chelsea Piers - -Gym [Directions] | 7:30 p.m. | ||
| Mon., 3/29 | Miscellaneous Events | Meet the Coaches Night | Home - Weston HS-Cafeteria [Directions] | 6:00 p.m. | Freshman and athletes new to WHS and their parent/guardian will meet in the Cafeteria starting at 6pm. All athletes and their parent/guardian will meet in individual team locations starting at 7:30. | |
| Sat., 4/10 | JV Baseball | Stratford | Home - Weston HS-Revson #2 (JV) [Directions] | Postponed | ||
| Sat., 4/10 | V Boys Lacrosse | Masuk | Home - Weston HS-WHS Lower Turf Field [Directions] | 2:00 p.m. | W 8-6 | |
| Sat., 4/10 | JV Boys Lacrosse | New Fairfield | Home - Weston HS-WHS Lower Turf Field [Directions] | Postponed | ||
| Sat., 4/10 | JV Boys Lacrosse | Masuk | Home - Weston HS-WHS Lower Turf Field [Directions] | Canceled | Cancelled | |
| Sat., 4/10 | V Boys Tennis | Brookfield | Home - Weston HS-WHS Tennis Courts [Directions] | 12:00 p.m. | W 7-0 [Detailed Results] | |
| Sat., 4/10 | V Girls Lacrosse | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 12:00 p.m. | L 8-11 | |
| Sat., 4/10 | V Softball | Stratford | Away - DeLuca Field-Deluca Field [Directions] | 3:00 p.m. | W 19-5 | |
| Sat., 4/10 | V Girls Tennis | Brookfield | Away - Brookfield HS-BHS Tennis Courts [Directions] | 12:00 p.m. | W 5-2 | |
| Mon., 4/12 | V Baseball | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Fabbri Field [Directions] | 2:00 p.m. | W 10-0 | |
| Mon., 4/12 | V Boys Golf | Pomperaug | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | Pomperaug 179 Weston 205 | |
| Mon., 4/12 | V Girls Golf | Masuk | Home - Weston HS-Aspetuck Country Club [Directions] | 1:00 p.m. | Masuk 237 Weston 298 | |
| Mon., 4/12 | V Softball | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Park Ave Field [Directions] | 4:15 p.m. | L 0-22 | |
| Tue., 4/13 | JV Baseball | Notre Dame-Fairfield | Home - Weston HS-Revson #2 (JV) [Directions] | 2:00 p.m. | ||
| Tue., 4/13 | V Boys Lacrosse | Stratford | Away - Penders Field-Penders Field - Stratford [Directions] | 5:00 p.m. | W 18-0 | |
| Tue., 4/13 | V Boys Tennis | Joel Barlow | Away - Joel Barlow HS-Tennis Courts [Directions] | 12:00 p.m. | W 5-2 [Detailed Results] | |
| Tue., 4/13 | V Girls Lacrosse | Stratford/Bunnell | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | W 16-2 | |
| Tue., 4/13 | V Girls Tennis | Joel Barlow | Home - Weston HS-WHS Tennis Courts [Directions] | 12:00 p.m. | L 3-4 | |
| Wed., 4/14 | V Baseball | New Fairfield | Home - Weston HS-Revson #1 (Varsity) [Directions] | 4:00 p.m. | L 3-11 | |
| Wed., 4/14 | V Boys Tennis | Newtown | Home - Weston HS-WHS Tennis Courts [Directions] | 1:00 p.m. | W 7-0 [Detailed Results] | |
| Wed., 4/14 | V Girls Tennis | Newtown | Away - Newtown HS-NHS Tennis Courts [Directions] | 11:00 a.m. | W 6-1 | |
| Thu., 4/15 | JV Baseball | New Fairfield | Away - New Fairfield HS-Baseball Field [Directions] | Postponed | ||
| Thu., 4/15 | JV Softball | New Fairfield | Away - New Fairfield HS-Softball Field [Directions] | Postponed | ||
| Sat., 4/17 | JV Baseball | Brookfield | Home - Weston HS-Revson #2 (JV) [Directions] | 2:00 p.m. | ||
| Sat., 4/17 | V Girls Lacrosse | Joel Barlow | Away - Joel Barlow HS-Joel Barlow HS Stadium [Directions] | 10:00 a.m. | L 5-9 | |
| Sat., 4/17 | V Softball | Brookfield | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 12:30 p.m. | L 7-19 | |
| Sat., 4/17 | JV Softball | Brookfield | Home - Weston HS-Softball - MS Field (JV) [Directions] | 10:00 a.m. | ||
| Mon., 4/19 | V Baseball | New Fairfield | Away - New Fairfield High-Baseball Field [Directions] | 4:15 p.m. | L 0-10 | |
| Mon., 4/19 | V Boys Outdoor Track | Stratford | Home - Weston HS-WHS Track [Directions] | 4:00 p.m. | Weston 105 Stratford 26 | |
| Mon., 4/19 | V Boys Tennis | Newtown | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Mon., 4/19 | V Girls Outdoor Track | Stratford | Home - Weston HS-WHS Track [Directions] | 4:00 p.m. | Weston 107 Stratford 38 | |
| Tue., 4/20 | V Baseball | Notre Dame-Fairfield | Home - Weston HS-Revson #1 (Varsity) [Directions] | 4:15 p.m. | W 21-7 | |
| Tue., 4/20 | JV Baseball | New Fairfield | Home - Weston HS-Revson #2 (JV) [Directions] | 4:15 p.m. | ||
| Tue., 4/20 | V Boys Golf | New Milford | Away - Candlewood Valley Country Club [Directions] | 3:00 p.m. | Weston 194 New Milford 197 | |
| Tue., 4/20 | V Boys Lacrosse | Immaculate | Away - Immaculate HS-Mustang Valley [Directions] | 4:00 p.m. | W 18-1 | |
| Tue., 4/20 | V Girls Lacrosse | Immaculate | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:30 p.m. | W 14-3 | |
| Tue., 4/20 | V Softball | Notre Dame-Fairfield | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 4:15 p.m. | L 0-9 | |
| Tue., 4/20 | JV Softball | New Fairfield | Home - Weston HS-Softball - MS Field (JV) [Directions] | Postponed | ||
| Tue., 4/20 | V Girls Tennis | Notre Dame-Fairfield | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | W 6-1 | |
| Thu., 4/22 | JV Baseball | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Fabbri Field [Directions] | Postponed | ||
| Thu., 4/22 | V Boys Lacrosse | Newtown | Home - Weston HS-WHS Lower Turf Field [Directions] | 7:15 p.m. | W 7-6 | |
| Thu., 4/22 | JV Boys Lacrosse | Newtown | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:30 p.m. | ||
| Thu., 4/22 | V Boys Outdoor Track | New Milford | Home - Weston HS-WHS Track [Directions] | 4:00 p.m. | Weston 89 New Milford 59 | |
| Thu., 4/22 | JV Boys Tennis | Wilton | Home - Weston HS-WHS Tennis Courts [Directions] | 5:00 p.m. | ||
| Thu., 4/22 | V Girls Lacrosse | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 6:00 p.m. | L 5-14 | |
| Thu., 4/22 | V Girls Outdoor Track | New Milford | Home - Weston HS-WHS Track [Directions] | 4:00 p.m. | Weston 112 New Milford 28 | |
| Thu., 4/22 | V Girls Tennis | Newtown | Away - Newtown HS-NHS Tennis Courts [Directions] | 3:45 p.m. | W 6-1 | |
| Thu., 4/22 | JV Girls Tennis | Wilton | Away - Wilton Middlebrook School-JV Tennis Courts [Directions] | 5:00 p.m. | ||
| Fri., 4/23 | V Baseball | Bethel | Home - Weston HS-Revson #1 (Varsity) [Directions] | 4:15 p.m. | L 1-2 | |
| Fri., 4/23 | V Boys Tennis | New Fairfield | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Fri., 4/23 | V Softball | Bethel | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 4:15 p.m. | L 4-13 | |
| Fri., 4/23 | V Girls Tennis | New Fairfield | Away - New Fairfield High-Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Sat., 4/24 | V Baseball | Stratford | Away - Penders Field-Penders Field - Stratford [Directions] | 1:30 p.m. | W 3-1 | |
| Sat., 4/24 | JV Baseball | Bethel | Away - Bethel HS-Hunt Field at Bethel HS [Directions] | 10:00 a.m. | ||
| Sat., 4/24 | V Boys Lacrosse | Bunnell-Stratford | Away - Bunnell HS-Bunnell Turf Field [Directions] | 12:00 p.m. | W 12-1 | |
| Sat., 4/24 | JV Boys Lacrosse | Bunnell-Stratford | Away - Bunnell HS-Bunnell Turf Field [Directions] | Canceled | Cancelled | |
| Sat., 4/24 | V Softball | New Fairfield | Away - New Fairfield HS-Softball Field [Directions] | 1:00 p.m. | W 14-2 | |
| Sat., 4/24 | V Softball | New Fairfield | Away - New Fairfield HS-Softball Field [Directions] | 3:30 p.m. | W 13-5 | |
| Mon., 4/26 | V Baseball | Kolbe Cathedral | Away - Kolbe Cathedral HS-Seaside Park [Directions] | 4:15 p.m. | W 13-2 | |
| Mon., 4/26 | V Boys Golf | Newtown | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | Weston 179 Newtown 208 | |
| Mon., 4/26 | V Boys Outdoor Track | Brookfield | Home - Weston HS-WHS Track [Directions] | 4:00 p.m. | Weston 102 Brookfield 42 | |
| Mon., 4/26 | V Boys Tennis | New Milford | Away - New Milford HS-Tennis Courts - NMHS [Directions] | 3:45 p.m. | W 6-1 [Detailed Results] | |
| Mon., 4/26 | V Girls Golf | Bunnell | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | Weston 256 | |
| Mon., 4/26 | V Girls Outdoor Track | Brookfield | Home - Weston HS-WHS Track [Directions] | 4:00 p.m. | Weston 97 Brookfield 37 | |
| Mon., 4/26 | V Softball | Kolbe Cathedral | Away - Kolbe Cathedral HS-Seaside Park [Directions] | 4:15 p.m. | W 22-12 | |
| Mon., 4/26 | V Girls Tennis | New Milford | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Tue., 4/27 | V Boys Golf | Masuk | Away - Whitney Farms Golf Course [Directions] | 3:00 p.m. | Masuk 169 Weston 185 | |
| Tue., 4/27 | V Boys Lacrosse | Notre Dame-Fairfield | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:00 p.m. | W 16-0 | |
| Tue., 4/27 | V Girls Golf | Pomperaug | Away - Pomperaug HS-Pomperaug Golf Course [Directions] | 3:00 p.m. | Weston 237 Pomperaug 252 | |
| Tue., 4/27 | V Girls Lacrosse | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Park Ave Field [Directions] | 4:00 p.m. | W 13-0 | |
| Tue., 4/27 | JV Softball | Stratford | Home - Weston HS-Softball - MS Field (JV) [Directions] | 4:15 p.m. | ||
| Tue., 4/27 | JV Girls Tennis | Darien | Away - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/28 | V Baseball | Pomperaug | Away - Pomperaug HS-Baseball Field [Directions] | 4:15 p.m. | W 8-4 | |
| Wed., 4/28 | V Boys Golf | New Fairfield | Away - Club River Oaks [Directions] | 3:00 p.m. | Weston 169 New Fairfield 212 | |
| Wed., 4/28 | V Boys Tennis | Joel Barlow | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | W 5-2 [Detailed Results] | |
| Wed., 4/28 | JV Boys Tennis | Darien | Away - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/28 | V Girls Golf | Brookfield | Away - Sunset Hill Golf Course [Directions] | 3:00 p.m. | Weston 218 Brookfield 259 | |
| Wed., 4/28 | V Softball | Pomperaug | Away - Pomperaug HS-Softball Field [Directions] | 4:15 p.m. | L 1-6 | |
| Wed., 4/28 | V Girls Tennis | Joel Barlow | Away - Joel Barlow HS-Tennis Courts [Directions] | 3:45 p.m. | W 5-2 | |
| Thu., 4/29 | V | Pomperaug | Away - Pomperaug HS-Stadium [Directions] | 5:30 p.m. | W 17-3 | |
| Thu., 4/29 | JV | Pomperaug | Away - Pomperaug HS-Stadium [Directions] | 7:15 p.m. | ||
| Thu., 4/29 | JV Baseball | Pomperaug | Home - Weston HS-Revson #2 (JV) [Directions] | Postponed | ||
| Thu., 4/29 | V Boys Outdoor Track | Bethel | Away - Bethel HS-BHS track [Directions] | 4:00 p.m. | Cancelled | |
| Thu., 4/29 | V Girls Lacrosse | Pomperaug | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:30 p.m. | W 13-9 | |
| Thu., 4/29 | V Girls Outdoor Track | Bethel | Away - Bethel HS-BHS track [Directions] | 4:00 p.m. | Cancelled | |
| Thu., 4/29 | JV Softball | Pomperaug | Home - Weston HS-Softball - MS Field (JV) [Directions] | Postponed | ||
| Fri., 4/30 | V Baseball | Masuk | Home - Weston HS-Revson #1 (Varsity) [Directions] | 4:15 p.m. | L 6-18 | |
| Fri., 4/30 | JV Baseball | Masuk | Away - Masuk HS-John Giampaolo Baseball Field @ Masuk HS [Directions] | 4:15 p.m. | ||
| Fri., 4/30 | V Boys Tennis | Brookfield | Away - Brookfield HS-BHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Fri., 4/30 | JV Boys Tennis | Staples | Away - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 4/30 | V Softball | Masuk | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 4:15 p.m. | L 0-29 | |
| Fri., 4/30 | V Girls Tennis | Brookfield | Home - Weston HS-WHS Tennis Courts [Directions] | 4:45 p.m. | W 6-1 | |
| Sat., 5/1 | V Baseball | Brookfield | Away - Dunkin' Donuts Park (Hartford, CT)-Yard Goats [Directions] | 1:00 p.m. | W 9-2 | |
| Sat., 5/1 | V Boys Lacrosse | Joel Barlow | Away - Joel Barlow HS-Joel Barlow HS Stadium [Directions] | 12:00 p.m. | W 8-3 | |
| Sat., 5/1 | JV Boys Lacrosse | Joel Barlow | Away - Joel Barlow HS-Joel Barlow HS Stadium [Directions] | 2:00 p.m. | ||
| Sat., 5/1 | JV Boys Tennis | Darien | Home - Weston HS-WHS Tennis Courts [Directions] | 10:00 a.m. | ||
| Sat., 5/1 | V Girls Lacrosse | Joel Barlow | Home - Weston HS-WHS Lower Turf Field [Directions] | 2:30 p.m. | L 7-13 | |
| Sat., 5/1 | JV Softball | Masuk | Away - Masuk HS-Masuk High School Softball Field [Directions] | Canceled | Cancelled | |
| Mon., 5/3 | V Baseball | Bunnell | Away - Bunnell HS-Bunnell Baseball Field [Directions] | 4:00 p.m. | W 8-4 | |
| Mon., 5/3 | V Boys Golf | New Fairfield | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | Weston 196 New Fairfield 217 | |
| Mon., 5/3 | V Boys Lacrosse | Brookfield | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | W 17-0 | |
| Mon., 5/3 | JV Boys Lacrosse | Brookfield | Home - Weston HS-WHS Lower Turf Field [Directions] | Postponed | ||
| Mon., 5/3 | V Boys Tennis | Bunnell | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Mon., 5/3 | V Girls Golf | Notre Dame-Fairfield | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | Weston 235 Notre Dame of Fairfield 236 | |
| Mon., 5/3 | V Girls Lacrosse | Brookfield | Away - Brookfield HS-BHS Stadium Field [Directions] | 6:00 p.m. | W 15-7 | |
| Mon., 5/3 | V Softball | Bunnell | Away - Bunnell HS-Bunnell Softball FIeld [Directions] | 4:15 p.m. | W 14-10 | |
| Mon., 5/3 | V Girls Tennis | Bunnell | Away - Bunnell HS-Bunnell Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Tue., 5/4 | JV Baseball | Bunnell | Home - Weston HS-Revson #2 (JV) [Directions] | Postponed | ||
| Tue., 5/4 | V Boys Golf | Joel Barlow | Away - Redding Country Club [Directions] | 3:00 p.m. | Joel Barlow 184 Weston 186 | |
| Tue., 5/4 | JV Softball | Bunnell | Home - Weston HS-Softball - MS Field (JV) [Directions] | 4:15 p.m. | ||
| Pending changes awaiting acceptance by one or more parties involved: Date to 5/20, Time to 5:00 p.m. | ||||||
| Wed., 5/5 | V Boys Lacrosse | New Fairfield | Away - New Fairfield HS-Marty Morgan Field [Directions] | 4:30 p.m. | L 4-9 | |
| Wed., 5/5 | JV Boys Lacrosse | New Fairfield | Away - New Fairfield HS-Rebel Turf [Directions] | 6:15 p.m. | ||
| Wed., 5/5 | V Girls Golf | Immaculate | Away - Immaculate HS-Richter Park [Directions] | 3:00 p.m. | Immaculate 200 Weston 265 | |
| Wed., 5/5 | V Girls Lacrosse | New Fairfield | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | L 11-16 | |
| Thu., 5/6 | V Baseball | New Milford | Home - Weston HS-Revson #1 (Varsity) [Directions] | 4:15 p.m. | W 2-0 | |
| Thu., 5/6 | JV Baseball | New Milford | Away - New Milford HS-Baseball Varsity Field - NMHS [Directions] | 4:15 p.m. | ||
| Thu., 5/6 | V Boys Golf | Pomperaug | Away - Pomperaug HS-Silo Point Country Club [Directions] | 3:00 p.m. | Pomperaug 164 Weston 183 | |
| Thu., 5/6 | V Boys Outdoor Track | Pomperaug | Away - Pomperaug HS-Stadium [Directions] | 4:30 p.m. | Weston 118 Pomperaug 32 | |
| Thu., 5/6 | V Girls Golf | Masuk | Away - Whitney Farms Golf Course [Directions] | 3:00 p.m. | Masuk 209 Weston 270 | |
| Thu., 5/6 | V Girls Outdoor Track | Pomperaug | Away - Pomperaug HS-Stadium [Directions] | 4:30 p.m. | Weston 85 Pomperaug 60 | |
| Thu., 5/6 | V Softball | New Milford | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 4:15 p.m. | L 0-8 | |
| Thu., 5/6 | JV Softball | New Milford | Away - New Milford HS-Softball JV Field - NMHS [Directions] | Postponed | ||
| Thu., 5/6 | Miscellaneous Events | SWC Leadership Dinner | Home - TBA [Directions] | 4:00 p.m. | ||
| Fri., 5/7 | V Baseball | Newtown | Away - Newtown HS-Nighthawk Ball Park [Directions] | 4:15 p.m. | W 4-3 | |
| Fri., 5/7 | V Boys Tennis | Masuk | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Fri., 5/7 | V Softball | Newtown | Away - Newtown HS-NHS Softball Field [Directions] | 4:15 p.m. | L 0-11 | |
| Fri., 5/7 | V Girls Tennis | Masuk | Away - Wolfe Park-Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Sat., 5/8 | JV Baseball | Newtown | Home - Weston HS-Revson #2 (JV) [Directions] | 10:00 a.m. | ||
| Sat., 5/8 | JV Boys Tennis | Wilton | Away - Wilton Middlebrook School-JV Tennis Courts [Directions] | 2:00 p.m. | ||
| Sat., 5/8 | JV Softball | Newtown | Home - Weston HS-Softball - MS Field (JV) [Directions] | 10:00 a.m. | ||
| Sat., 5/8 | JV Softball | Bethel | Away - Bethel HS-Kisling Field [Directions] | 2:00 p.m. | ||
| Sat., 5/8 | JV Girls Tennis | Wilton | Home - Weston HS-WHS Tennis Courts [Directions] | 2:00 p.m. | ||
| Mon., 5/10 | V Baseball | Stratford | Away - Penders Field-Penders Field - Stratford [Directions] | 4:15 p.m. | W 16-6 | |
| Mon., 5/10 | V Boys Golf | Stratford | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | Weston 195 Stratford 257 | |
| Mon., 5/10 | V Boys Outdoor Track | Bunnell, Kolbe Cathedral | Home - Weston HS-WHS Track [Directions] | 4:00 p.m. | Weston 109 Bunnell 40 Weston 115 Kolbe 14 | |
| Mon., 5/10 | V Boys Tennis | Bethel | Away - Bethel HS-BHS Tennis Courts [Directions] | 3:45 p.m. | W 6-1 [Detailed Results] | |
| Mon., 5/10 | V Girls Golf | Pomperaug | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | Weston 271 Pomperaug 304 | |
| Mon., 5/10 | V Girls Lacrosse | Bethel | Away - Bethel HS-DeSantis Field at Bethel High [Directions] | 6:45 p.m. | W 19-11 | |
| Mon., 5/10 | V Girls Outdoor Track | Bunnell, Kolbe Cathedral | Home - Weston HS-WHS Track [Directions] | 4:00 p.m. | Weston 121 Kolbe 20 Weston 122 Bunnell 24 | |
| Mon., 5/10 | V Girls Tennis | Bethel | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Tue., 5/11 | JV Baseball | Stratford | Home - Weston HS-Revson #2 (JV) [Directions] | 4:15 p.m. | ||
| Tue., 5/11 | V Boys Golf | Notre Dame-Fairfield | Away - Fairchild Wheeler Golf Course [Directions] | 3:00 p.m. | Weston 179 Notre Dame-Fairfield 275 | |
| Tue., 5/11 | V Boys Lacrosse | Bethel | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | W 19-2 | |
| Tue., 5/11 | JV Boys Lacrosse | Bethel | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 5/11 | V Boys Tennis | Immaculate | Away - Immaculate HS-Rogers Park [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Tue., 5/11 | V Girls Golf | Newtown | Away - Newtown Country Club [Directions] | 3:00 p.m. | Newtown 192 Weston 244 | |
| Tue., 5/11 | V Softball | Joel Barlow | Away - Joel Barlow High-Field E (Softball) [Directions] | 4:00 p.m. | W 13-10 | |
| Tue., 5/11 | JV Softball | Stratford | Away - Birdseye Rec Complex-Birdseye 2 [Directions] | 4:15 p.m. | ||
| Tue., 5/11 | V Girls Tennis | Immaculate | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Wed., 5/12 | V Baseball | Brookfield | Home - Weston HS-Revson #1 (Varsity) [Directions] | 4:15 p.m. | W 6-1 | |
| Wed., 5/12 | JV Boys Tennis | Trumbull | Home - Weston HS-WHS Tennis Courts [Directions] | 5:30 p.m. | ||
| Wed., 5/12 | V Softball | Brookfield | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 4:15 p.m. | L 5-13 | |
| Wed., 5/12 | V Girls Tennis | Stratford | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Wed., 5/12 | JV Girls Tennis | Trumbull | Away - Unity Park [Directions] | 4:00 p.m. | ||
| Thu., 5/13 | V Baseball | Joel Barlow | Away - Joel Barlow HS-Baseball Field [Directions] | 4:15 p.m. | W 9-2 | |
| Thu., 5/13 | V Boys Lacrosse | New Milford | Away - New Milford HS-Joe Wiser Stadium - NMHS [Directions] | 7:15 p.m. | W 14-4 | |
| Thu., 5/13 | JV Boys Lacrosse | New Milford | Away - New Milford HS-North Turf Field - NMHS [Directions] | 5:45 p.m. | ||
| Thu., 5/13 | V Boys Outdoor Track | Immaculate | Home - Weston HS-WHS Track [Directions] | 4:00 p.m. | Cancelled | |
| Thu., 5/13 | V Boys Tennis | Pomperaug | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Thu., 5/13 | V Girls Golf | Immaculate | Away - Immaculate HS-Richter Park [Directions] | 3:00 p.m. | Immaculate 210 Weston 271 | |
| Thu., 5/13 | V Girls Lacrosse | New Milford | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | W 15-3 | |
| Thu., 5/13 | V Girls Outdoor Track | Immaculate | Home - Weston HS-WHS Track [Directions] | 4:00 p.m. | Cancelled | |
| Thu., 5/13 | V Softball | Stratford | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 4:15 p.m. | W 10-3 | |
| Thu., 5/13 | V Girls Tennis | Pomperaug | Away - Edgewood Bath and Tennis Club [Directions] | 3:45 p.m. | W 5-2 | |
| Fri., 5/14 | JV Boys Tennis | Fairfield Warde | Home - Weston HS-WHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 5/14 | Miscellaneous Events | WHS PROM | Home - TBA [Directions] | 6:00 p.m. | ||
| Sat., 5/15 | JV Baseball | Joel Barlow | Home - Weston HS-Revson #2 (JV) [Directions] | 10:00 a.m. | ||
| Sat., 5/15 | V Boys Lacrosse | Newtown | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | L 5-9 | |
| Sat., 5/15 | JV Boys Lacrosse | Newtown | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Sat., 5/15 | V Girls Lacrosse | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 12:30 p.m. | L 9-15 | |
| Sat., 5/15 | JV Girls Tennis | Darien | Home - Weston HS-WHS Tennis Courts [Directions] | 2:00 p.m. | ||
| Mon., 5/17 | V Baseball | Immaculate | Home - Weston HS-Revson #1 (Varsity) [Directions] | 4:15 p.m. | W 4-1 | |
| Mon., 5/17 | V Boys Golf | Joel Barlow | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | Weston 189 Joel Barlow 214 | |
| Mon., 5/17 | JV Boys Tennis | Trumbull | Away - Unity Park [Directions] | 4:30 p.m. | ||
| Mon., 5/17 | V Girls Golf | Bunnell | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | Weston 258 Bunnell 318 | |
| Mon., 5/17 | V Girls Lacrosse | Bunnell | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:00 p.m. | W 15-4 | |
| Mon., 5/17 | V Softball | Immaculate | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 4:15 p.m. | L 0-4 | |
| Tue., 5/18 | JV Baseball | Immaculate | Away - Immaculate HS-Baseball Diamond [Directions] | 4:15 p.m. | ||
| Tue., 5/18 | V Boys Golf | Masuk | Away - Whitney Farms Golf Course [Directions] | 3:00 p.m. | Masuk 159 Weston 185 | |
| Tue., 5/18 | V Boys Lacrosse | Joel Barlow | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | L 5-7 | |
| Tue., 5/18 | JV Boys Lacrosse | Joel Barlow | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 5/18 | V Boys Outdoor Track | Newtown, Kolbe Cathedral | Away - Newtown HS-Blue and Gold Stadium [Directions] | 5:15 p.m. | Weston 98 1/2 Newtown 50 1/2 | |
| Tue., 5/18 | V Boys Tennis | Stratford | Away - Flood MS-Flood MS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Tue., 5/18 | JV Softball | New Fairfield | Away - New Fairfield HS-Softball Field [Directions] | 4:15 p.m. | ||
| Wed., 5/19 | JV Baseball | Brookfield | Away - Brookfield HS-Baseball Field [Directions] | Canceled | Cancelled | |
| Wed., 5/19 | V Boys Golf | Bunnell | Away - Bunnell HS-Oronoque C.C. [Directions] | 3:00 p.m. | Weston 190 Bunnell 315 | |
| Wed., 5/19 | V Girls Golf | Brookfield | Away - Sunset Hill Golf Course [Directions] | 3:00 p.m. | Brookfield 236 Weston 240 | |
| Wed., 5/19 | JV Softball | Brookfield | Away - Brookfield HS-BHS Softball Field [Directions] | 4:15 p.m. | ||
| Wed., 5/19 | JV Girls Tennis | Trumbull | Home - Weston HS-WHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/20 | JV Softball | Bunnell | Home - Weston HS-Softball - MS Field (JV) [Directions] | 5:00 p.m. | ||
| Thu., 5/20 | JV Girls Tennis | Fairfield Warde | Away - Fairfield Woods-Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 5/21 | Miscellaneous Events | College Athlete Signing Ceremony | Home - Weston HS-Gym (New) [Directions] | 2:30 p.m. | ||
| Mon., 5/24 | V Boys Golf | Brookfield | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | Weston 194 Brookfield 199 | |
| Mon., 5/24 | V Boys Golf | Immaculate | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | Immaculate 170 Weston 194 | |
| Mon., 5/24 | V Girls Golf | Stratford | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | Weston 244 Stratford 284 | |
| Tue., 5/25 | V Boys Golf | Bethel | Away - Bethel HS-Connecticut Country Club [Directions] | 3:00 p.m. | Weston 181 Bethel 202 | |
| Tue., 5/25 | V Boys Outdoor Track | SWC Boys Championship Track Meet | Away - Bethel HS-BHS track | 3:00 p.m. | ||
| Tue., 5/25 | V Girls Golf | Joel Barlow | Away - Redding Country Club [Directions] | 3:00 p.m. | Joel Barlow 238 Weston 275 | |