| Weston 2022-23 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 742 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Tue., 8/23 | V Boys Golf | Masuk | Home - Weston HS-Aspetuck Country Club [Directions] | 8:00 a.m. | Masuk 178 Weston 214 | |
| Wed., 8/24 | V Boys Golf | Pomperaug | Away - Pomperaug HS-Highfield Country Club [Directions] | 2:00 p.m. | Pomperaug 165 Weston 189 | |
| Sat., 8/27 | V Football | ATI, Bethel, New Fairfield, Seymour, Wolcott | Away - Immaculate HS-Mustang Valley | 9:30 a.m. | ||
| Sun., 8/28 | V Boys Soccer | Alumni Game | Home - Weston HS-WHS Stadium Field [Directions] | 6:00 p.m. | ||
| Mon., 8/29 | V Boys Golf | New Fairfield | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | Weston 199 New Fairfield 210 | |
| Tue., 8/30 | V Boys Golf | Bethel | Away - Bethel HS-Connecticut Country Club [Directions] | 3:00 p.m. | Bethel 174 Weston 208 | |
| Tue., 8/30 | V Boys Soccer | Norwalk (Scrim.) | Home - Weston HS-WHS Stadium Field [Directions] | 3:00 p.m. | ||
| Tue., 8/30 | JV Boys Soccer | Norwalk (Scrim.) | Home - Weston HS-WHS Stadium Field [Directions] | 4:30 p.m. | ||
| Wed., 8/31 | V Boys Golf | Masuk | Away - Whitney Farms Golf Course [Directions] | 3:00 p.m. | Masuk 163 Weston 192 | |
| Wed., 8/31 | V Girls Volleyball | Fairfield Ludlowe (Scrim.) | Home - Weston HS-Gym (New) [Directions] | 6:00 p.m. | ||
| Wed., 8/31 | JV Girls Volleyball | Fairfield Ludlowe (Scrim.) | Home - Weston HS-Gym (New) [Directions] | 4:30 p.m. | ||
| Wed., 8/31 | FR Girls Volleyball | Fairfield Ludlowe (Scrim.) | Home - Weston HS-Gym (Old) [Directions] | 4:30 p.m. | ||
| Thu., 9/1 | V Football | Seymour (Scrim.) | Away - Seymour HS-turf field [Directions] | 6:30 p.m. | ||
| Thu., 9/1 | V Field Hockey | Shepaug Valley (Scrim.) | Away - Shepaug Valley HS-Joan Gauthey Field [Directions] | 4:30 p.m. | ||
| Thu., 9/1 | V Girls Soccer | Fairfield Ludlowe (Scrim.) | Home - Weston HS-WHS Stadium Field [Directions] | 5:30 p.m. | ||
| Fri., 9/2 | JV Field Hockey | Rebel Rumble Field Hockey Jamboree | Away - New Fairfield HS-Marty Morgan Field | 4:00 p.m. | ||
| Sat., 9/3 | V Boys Soccer | Fairfield Warde (Scrim.) | Home - Weston HS-WHS Stadium Field [Directions] | 9:00 a.m. | ||
| Sat., 9/3 | JV Boys Soccer | Fairfield Warde (Scrim.) | Home - Weston HS-WHS Stadium Field [Directions] | 10:30 a.m. | ||
| Sat., 9/3 | V Field Hockey | New Fairfield, Amity, Bethel, Brookfield, Masuk, New Milford, Newtown, Ridgefield, Shepaug Valley | Away - New Fairfield HS-Marty Morgan Field | 9:00 a.m. | ||
| Sun., 9/4 | V Girls Soccer | Cheshire (Scrim.) | Away - Treadwell Park-Treadwell Town Park--Tilson Field [Directions] | 11:00 a.m. | ||
| Sun., 9/4 | V Girls Soccer | Newtown (Scrim.) | Away - Treadwell Park-Treadwell Town Park--Tilson Field [Directions] | 11:40 a.m. | ||
| Sun., 9/4 | V Girls Soccer | Pomperaug (Scrim.) | Away - Treadwell Park-Treadwell Town Park--Tilson Field [Directions] | 9:40 a.m. | ||
| Mon., 9/5 | V Girls Soccer | Darien (Scrim.) | Away - Darien HS-DHS Center Oval Turf Field [Directions] | 4:30 p.m. | ||
| Mon., 9/5 | JV Girls Soccer | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:30 p.m. | ||
| Wed., 9/7 | V Girls Soccer | Wilton (Scrim.) | Away - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | ||
| Wed., 9/7 | JV Girls Soccer | Wilton (Scrim.) | Away - Allen's Meadow-2A [Directions] | 4:00 p.m. | ||
| Thu., 9/8 | V Field Hockey | Brien McMahon | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:30 p.m. | W 3-0 | |
| Thu., 9/8 | JV Field Hockey | Brien McMahon | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 9/9 | V Football | Foran | Away - Foran HS -Foran High School - Turf Field [Directions] | 7:00 p.m. | L 41-43 | |
| Fri., 9/9 | V Girls Soccer | Stratford | Away - Penders Field-Penders Field - Stratford [Directions] | 6:00 p.m. | W 5-0 | |
| Fri., 9/9 | JV Girls Soccer | Stratford | Away - Penders Field-Penders Field - Stratford [Directions] | 4:00 p.m. | ||
| Fri., 9/9 | V Girls Swimming and Diving | New Milford | Away - Canterbury School-Higgins Aquatic Center [Directions] | 7:00 p.m. | Weston 96 New Milford 80 | |
| Fri., 9/9 | V Girls Volleyball | Staples | Home - Weston HS-Gym (New) [Directions] | 6:00 p.m. | L 0-3 | |
| Fri., 9/9 | JV Girls Volleyball | Staples | Home - Weston HS-Gym (New) [Directions] | 4:30 p.m. | ||
| Fri., 9/9 | FR Girls Volleyball | Staples | Home - Weston HS-Gym (Old) [Directions] | 4:30 p.m. | ||
| Sat., 9/10 | JV Football | Foran | Home - Weston HS-WHS Stadium Field [Directions] | 11:00 a.m. | ||
| Sat., 9/10 | V Boys Soccer | Suffield | Home - Weston HS-WHS Stadium Field [Directions] | 2:00 p.m. | W 1-0 | |
| Sat., 9/10 | JV Boys Soccer | Suffield | Home - Weston HS-WHS Lower Turf Field [Directions] | 2:00 p.m. | ||
| Sat., 9/10 | V Field Hockey | Fairfield Warde | Home - Weston HS-WHS Lower Turf Field [Directions] | 11:30 a.m. | W 1-0 | |
| Sat., 9/10 | JV Field Hockey | Fairfield Warde | Home - Weston HS-WHS Lower Turf Field [Directions] | 10:00 a.m. | ||
| Sat., 9/10 | V Girls Volleyball | CIAC Early Season Volleyball Tournament at the CT Sports Center in Woodbridge | Away - Not Listed | 8:00 a.m. | ||
| Mon., 9/12 | V Field Hockey | New Milford | Away - New Milford HS-Joe Wiser Stadium - NMHS [Directions] | 5:30 p.m. | L 1-2 | |
| Mon., 9/12 | JV Field Hockey | New Milford | Away - New Milford HS-Joe Wiser Stadium - NMHS [Directions] | 4:00 p.m. | ||
| Mon., 9/12 | V Girls Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:00 p.m. | L 1-3 | |
| Mon., 9/12 | JV Girls Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 9/13 | V Boys Golf | Brookfield | Away - Sunset Hill Golf Course [Directions] | 3:00 p.m. | Brookfield 155 Weston 193 | |
| Tue., 9/13 | V Boys Soccer | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 7:00 p.m. | W 2-0 | |
| Tue., 9/13 | V Girls Soccer | Masuk | Home - Weston HS-WHS Stadium Field [Directions] | 7:00 p.m. | L 1-2 | |
| Wed., 9/14 | V Boys Cross Country | Brookfield, Joel Barlow, Newtown | Away - Brookfield HS-BHS Track [Directions] | 5:00 p.m. | Weston 27 - Brookfield 30 Barlow 21 - Weston 35 Newtown 19 - Weston 44 | |
| Wed., 9/14 | V Boys Golf | Notre Dame-Fairfield | Away - Fairchild Wheeler Golf Course [Directions] | 3:00 p.m. | Weston 184 Notre Dame 213 | |
| Wed., 9/14 | V Girls Cross Country | Brookfield, Joel Barlow, Newtown | Away - Brookfield HS-BHS Track [Directions] | 4:30 p.m. | Brookfield 23 - Weston 34 Barlow 22 - Weston 36 Newtown 15- Weston 50 | |
| Wed., 9/14 | V Girls Volleyball | Wilton | Home - Weston HS-Gym (New) [Directions] | 6:00 p.m. | L 0-3 | |
| Wed., 9/14 | JV Girls Volleyball | Wilton | Home - Weston HS-Gym (New) [Directions] | 4:30 p.m. | ||
| Wed., 9/14 | FR Girls Volleyball | Wilton | Home - Weston HS-Gym (Old) [Directions] | 4:30 p.m. | ||
| Thu., 9/15 | V Boys Golf | New Milford | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | New Milford 177 Weston 195 | |
| Thu., 9/15 | V Boys Soccer | Immaculate | Home - Weston HS-WHS Stadium Field [Directions] | 6:00 p.m. | W 2-1 | |
| Thu., 9/15 | JV Boys Soccer | Immaculate | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 9/15 | V Girls Soccer | Immaculate | Away - Immaculate HS-Mustang Valley [Directions] | 4:00 p.m. | W 4-0 | |
| Fri., 9/16 | V Football | Bunnell | Home - Weston HS-WHS Stadium Field [Directions] | 7:00 p.m. | L 20-45 | |
| Fri., 9/16 | V Girls Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | L 0-3 | |
| Fri., 9/16 | JV Girls Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Sat., 9/17 | FR Football | Bunnell | Away - Bunnell HS-Mastroni Field [Directions] | 11:00 a.m. | ||
| Sat., 9/17 | JV Boys Soccer | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 1:15 p.m. | ||
| Sat., 9/17 | V Field Hockey | Lauralton Hall | Away - Lauralton Hall-Turf Field [Directions] | 10:30 a.m. | W 1-0 | |
| Sat., 9/17 | JV Field Hockey | Lauralton Hall | Away - Lauralton Hall-Turf Field [Directions] | 11:45 a.m. | ||
| Sat., 9/17 | V Girls Soccer | Watertown | Home - Weston HS-WHS Stadium Field [Directions] | 12:30 p.m. | W 1-0 | |
| Sat., 9/17 | JV Girls Soccer | Watertown | Home - Weston HS-WHS Stadium Field [Directions] | 10:30 a.m. | ||
| Mon., 9/19 | V Boys Golf | Pomperaug | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | Pomperaug 171 Weston 189 | |
| Mon., 9/19 | V Field Hockey | Immaculate | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | L 0-3 | |
| Mon., 9/19 | JV Field Hockey | Immaculate | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:30 p.m. | ||
| Mon., 9/19 | V Girls Volleyball | New Milford | Away - New Milford HS-Main Gym - NMHS [Directions] | 7:00 p.m. | L 1-3 | |
| Mon., 9/19 | JV Girls Volleyball | New Milford | Away - New Milford HS-Main Gym - NMHS [Directions] | 5:30 p.m. | ||
| Mon., 9/19 | FR Girls Volleyball | New Milford | Away - New Milford HS-Small Gym - NMHS [Directions] | 5:30 p.m. | ||
| Tue., 9/20 | V Boys Cross Country | New Milford, Notre Dame-Fairfield | Home - Weston HS-WHS Stadium Field [Directions] | 5:00 p.m. | New Milford 17 - Weston 46 Weston 17 - ND 50 | |
| Tue., 9/20 | V Boys Golf | Joel Barlow | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | Joel Barlow 180 Weston 203 | |
| Tue., 9/20 | V Boys Soccer | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 7:00 p.m. | L 2-3 | |
| Tue., 9/20 | JV Boys Soccer | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 5:00 p.m. | ||
| Tue., 9/20 | V Girls Cross Country | New Milford, Notre Dame-Fairfield | Home - Weston HS-WHS Stadium Field [Directions] | 4:30 p.m. | New Milford 16 - Weston 47 Weston 15 - ND 50 | |
| Tue., 9/20 | V Girls Soccer | Newtown | Home - Weston HS-WHS Stadium Field [Directions] | 6:00 p.m. | T 1-1 | |
| Tue., 9/20 | JV Girls Soccer | Newtown | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 9/20 | V Girls Swimming and Diving | New Fairfield | Home - Weston HS-Weston MS Pool [Directions] | 4:00 p.m. | Weston 98 New Fairfield 75 | |
| Wed., 9/21 | V Field Hockey | Joel Barlow | Away - Joel Barlow HS-Field I (Stadium) [Directions] | 6:45 p.m. | T 0-0 | |
| Wed., 9/21 | JV Field Hockey | Joel Barlow | Away - Joel Barlow HS-Field I (Stadium) [Directions] | 5:15 p.m. | ||
| Wed., 9/21 | V Girls Volleyball | Brookfield | Home - Weston HS-Gym (New) [Directions] | 6:00 p.m. | W 3-0 | |
| Wed., 9/21 | JV Girls Volleyball | Brookfield | Home - Weston HS-Gym (New) [Directions] | 4:30 p.m. | ||
| Wed., 9/21 | FR Girls Volleyball | Brookfield | Home - Weston HS-Gym (Old) [Directions] | 4:30 p.m. | ||
| Thu., 9/22 | V Boys Soccer | Stratford | Home - Weston HS-WHS Stadium Field [Directions] | 6:00 p.m. | W 3-0 | |
| Thu., 9/22 | JV Boys Soccer | Stratford | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 9/23 | JV Field Hockey | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | Postponed | ||
| Fri., 9/23 | V Girls Swimming and Diving | Stratford | Away - Flood MS-Flood MS Pool [Directions] | 4:15 p.m. | Weston 84 Stratford 76 | |
| Fri., 9/23 | V Girls Volleyball | Pomperaug | Away - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 9/23 | JV Girls Volleyball | Pomperaug | Away - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/23 | FR Girls Volleyball | Pomperaug | Away - Pomperaug HS-Auxiliary Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/24 | V Football | Lewis Mills | Away - Lewis Mills HS-Lewis Mills Track [Directions] | 12:00 p.m. | W 42-7 | |
| Sat., 9/24 | JV Football | Lewis Mills | Home - Weston HS-WHS Stadium Field [Directions] | Canceled | Cancelled | |
| Sat., 9/24 | V Field Hockey | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 10:00 a.m. | W 5-2 | |
| Sat., 9/24 | JV Girls Soccer | Masuk | Home - Weston HS-WHS Lower Turf Field [Directions] | 11:00 a.m. | ||
| Tue., 9/27 | V Boys Golf | Immaculate | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | Immaculate 173 Weston 190 | |
| Tue., 9/27 | V Boys Soccer | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Park Ave Field [Directions] | 4:00 p.m. | W 2-1 | |
| Tue., 9/27 | JV Boys Soccer | Fairfield Prep | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 9/27 | V Girls Soccer | Notre Dame-Fairfield | Home - Weston HS-WHS Stadium Field [Directions] | 6:00 p.m. | L 0-2 | |
| Tue., 9/27 | V Girls Swimming and Diving | Woodland | Away - Woodland HS-pool [Directions] | 4:30 p.m. | Weston 101.5 Woodland 78.5 | |
| Wed., 9/28 | V Boys Cross Country | Stratford, Bethel | Away - Wooster MS Field [Directions] | 5:00 p.m. | Weston 15 Stratford 50 Bethel 20 Weston 39 | |
| Wed., 9/28 | V Girls Cross Country | Stratford, Bethel | Away - Wooster MS Field [Directions] | 4:30 p.m. | Weston 15 Stratford 50 Bethel 20 Weston 38 | |
| Wed., 9/28 | V Field Hockey | Masuk | Home - Weston HS-WHS Lower Turf Field [Directions] | 7:00 p.m. | L 1-2 | |
| Wed., 9/28 | JV Field Hockey | Masuk | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:30 p.m. | ||
| Wed., 9/28 | V Girls Volleyball | Newtown | Home - Weston HS-Gym (New) [Directions] | 6:00 p.m. | L 1-3 | |
| Wed., 9/28 | JV Girls Volleyball | Newtown | Home - Weston HS-Gym (New) [Directions] | 4:30 p.m. | ||
| Wed., 9/28 | FR Girls Volleyball | Newtown | Home - Weston HS-Gym (Old) [Directions] | 4:30 p.m. | ||
| Thu., 9/29 | V Boys Golf | Stratford | Away - Mill River Country Club [Directions] | 3:00 p.m. | Weston 183 Stratford 228 | |
| Thu., 9/29 | V Boys Soccer | Pomperaug | Home - Weston HS-WHS Stadium Field [Directions] | 6:00 p.m. | W 1-0 | |
| Thu., 9/29 | JV Boys Soccer | Pomperaug | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 9/29 | V Girls Soccer | Pomperaug | Away - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | L 0-1 | |
| Thu., 9/29 | JV Girls Soccer | Pomperaug | Away - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Fri., 9/30 | V Football | Stratford | Away - Penders Field-Penders Field - Stratford [Directions] | 7:00 p.m. | L 24-26 | |
| Fri., 9/30 | V Field Hockey | New Fairfield | Away - New Fairfield HS-Marty Morgan Field [Directions] | 4:15 p.m. | T 2-2 | |
| Fri., 9/30 | JV Field Hockey | New Fairfield | Away - New Fairfield HS-Marty Morgan Field [Directions] | 5:30 p.m. | ||
| Fri., 9/30 | V Girls Volleyball | Bunnell | Away - Bunnell HS-David Johnson Gymnasium [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 9/30 | JV Girls Volleyball | Bunnell | Away - Bunnell HS-David Johnson Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 10/1 | JV Football | Stratford | Home - Weston HS-WHS Stadium Field [Directions] | 2:00 p.m. | ||
| Mon., 10/3 | V Boys Cross Country | Pomperaug, Bunnell, New Fairfield | Away - Pomperaug HS-Cross Country Course [Directions] | 5:00 p.m. | Pomperaug 20 Weston 43 Weston 27 Bunnell 28 New Fairfield 25 Weston 32 | |
| Mon., 10/3 | V Boys Soccer | Brookfield | Away - Brookfield HS-BHS Back Turf [Directions] | 6:00 p.m. | W 3-1 | |
| Mon., 10/3 | JV Boys Soccer | Brookfield | Away - Brookfield HS-BHS Back Turf [Directions] | 4:00 p.m. | ||
| Mon., 10/3 | V Girls Cross Country | Pomperaug, Bunnell, New Fairfield | Away - Pomperaug HS-Cross Country Course [Directions] | 4:30 p.m. | Pomperaug 15 Weston 48 Bunnell 22 Weston 33 New Fairfield 15 Weston 40 | |
| Mon., 10/3 | V Field Hockey | New Milford | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:30 p.m. | T 1-1 | |
| Mon., 10/3 | JV Field Hockey | New Milford | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 10/3 | V Girls Soccer | Brookfield | Home - Weston HS-WHS Stadium Field [Directions] | 6:00 p.m. | L 1-2 | |
| Mon., 10/3 | JV Girls Soccer | Brookfield | Home - Weston HS-WHS Stadium Field [Directions] | 4:00 p.m. | ||
| Mon., 10/3 | V Girls Swimming and Diving | Masuk | Home - Weston HS-Weston MS Pool [Directions] | 4:00 p.m. | Weston 98 Masuk 80 | |
| Mon., 10/3 | V Girls Volleyball | Notre Dame-Fairfield | Home - Weston HS-Gym (New) [Directions] | 6:00 p.m. | W 3-0 | |
| Mon., 10/3 | JV Girls Volleyball | Notre Dame-Fairfield | Home - Weston HS-Gym (New) [Directions] | 4:30 p.m. | ||
| Mon., 10/3 | FR Girls Volleyball | Pomperaug | Home - Weston HS-Gym (Old) [Directions] | 4:00 p.m. | ||
| Thu., 10/6 | V Boys Golf | CHAPPA Tournament | Away - Not Listed | 8:00 a.m. | ||
| Thu., 10/6 | V Boys Soccer | New Fairfield | Home - Weston HS-WHS Stadium Field [Directions] | 6:00 p.m. | W 2-1 | |
| Thu., 10/6 | JV Boys Soccer | New Fairfield | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 10/6 | V Girls Soccer | New Fairfield | Away - New Fairfield HS-Marty Morgan Field [Directions] | 6:00 p.m. | W 5-0 | |
| Thu., 10/6 | JV Girls Soccer | New Fairfield | Away - New Fairfield HS-Marty Morgan Field [Directions] | 4:00 p.m. | ||
| Thu., 10/6 | V Girls Swimming and Diving | Bunnell | Home - Weston HS-Weston MS Pool [Directions] | 7:00 p.m. | Weston 95 Bunnell 78 | |
| Fri., 10/7 | V Field Hockey | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 5:30 p.m. | L 2-0 | |
| Fri., 10/7 | JV Field Hockey | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 4:00 p.m. | ||
| Fri., 10/7 | V Girls Volleyball | Immaculate | Away - Immaculate HS [Directions] | 7:00 p.m. | W 3-0 | |
| Fri., 10/7 | JV Girls Volleyball | Immaculate | Away - Immaculate HS-Immaculate Gym [Directions] | 5:30 p.m. | ||
| Fri., 10/7 | FR Girls Volleyball | Immaculate | Away - Immaculate HS-Immaculate Gym [Directions] | 4:30 p.m. | ||
| Sat., 10/8 | V Girls Soccer | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 1:00 p.m. | L 0-3 | |
| Mon., 10/10 | V Boys Golf | Immaculate | Away - Immaculate HS-Richter Park [Directions] | 3:00 p.m. | Immaculate 164 Weston 183 | |
| Tue., 10/11 | V Boys Cross Country | Immaculate, Kolbe Cathedral, Masuk | Home - Weston HS-WHS Stadium Field [Directions] | 5:00 p.m. | Immaculate 20 Weston 43 Weston 28 Kolbe 29 Weston 25 Masuk 31 | |
| Tue., 10/11 | V Boys Soccer | Bethel | Away - Bethel HS-Rourke Field [Directions] | 4:00 p.m. | L 3-5 | |
| Tue., 10/11 | JV Boys Soccer | Bethel | Away - Bethel HS-Rockwell Field [Directions] | 4:00 p.m. | ||
| Tue., 10/11 | V Girls Cross Country | Immaculate, Kolbe Cathedral, Masuk | Home - Weston HS-WHS Stadium Field [Directions] | 4:30 p.m. | Immaculate 23 Weston 32 Weston 15 Kolbe 50 Masuk 21 Weston 36 | |
| Tue., 10/11 | V Girls Soccer | Bethel | Home - Weston HS-WHS Stadium Field [Directions] | 6:00 p.m. | T 1-1 | |
| Tue., 10/11 | JV Girls Soccer | Bethel | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 10/11 | V Girls Swimming and Diving | Bethel/Immaculate | Home - Weston HS-Weston MS Pool [Directions] | 4:00 p.m. | Weston 103 Bethel/Immaculate 75 | |
| Tue., 10/11 | V Girls Volleyball | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Tue., 10/11 | JV Girls Volleyball | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/11 | FR Girls Volleyball | New Fairfield | Away - New Fairfield HS-MS Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/12 | V Boys Golf | Newtown | Away - Rock Ridge Country Club [Directions] | 3:00 p.m. | Newtown 176 Weston 191 | |
| Wed., 10/12 | V Field Hockey | Pomperaug | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:30 p.m. | OT-L 0-1 | |
| Wed., 10/12 | JV Field Hockey | Pomperaug | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 10/13 | V Boys Golf | Bunnell | Home - Weston HS-Aspetuck Country Club [Directions] | Postponed | ||
| Thu., 10/13 | JV Girls Soccer | New Milford | Away - New Milford HS-Joe Wiser Stadium - NMHS [Directions] | Postponed | ||
| Thu., 10/13 | V Girls Volleyball | Stratford | Away - Stratford HS-Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Thu., 10/13 | JV Girls Volleyball | Stratford | Away - Stratford HS-Gym [Directions] | 5:00 p.m. | ||
| Thu., 10/13 | FR Girls Volleyball | Stratford | Away - Stratford HS-Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/14 | V Football | New Fairfield | Away - New Fairfield HS-Stadium Field [Directions] | 7:00 p.m. | L 20-26 | |
| Fri., 10/14 | V Boys Soccer | New Milford | Home - Weston HS-WHS Stadium Field [Directions] | 6:00 p.m. | W 3-1 | |
| Fri., 10/14 | JV Boys Soccer | New Milford | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | ||
| Fri., 10/14 | V Field Hockey | Bethel | Away - Bethel HS-MS Turf Soccer Field [Directions] | 4:00 p.m. | L 0-2 | |
| Fri., 10/14 | JV Field Hockey | Bethel | Away - Bethel HS-Hunt Field at Bethel HS [Directions] | 5:30 p.m. | ||
| Fri., 10/14 | V Girls Soccer | New Milford | Away - New Milford HS-Joe Wiser Stadium - NMHS [Directions] | 6:45 p.m. | W 4-0 | |
| Fri., 10/14 | V Girls Swimming and Diving | Pomperaug | Away - Pomperaug HS-PHS Pool [Directions] | 4:30 p.m. | Weston 96 - Pomperaug 88 | |
| Sat., 10/15 | JV Football | New Fairfield | Home - Weston HS-WHS Stadium Field [Directions] | 11:00 a.m. | ||
| Sat., 10/15 | V Field Hockey | Westhill | Home - Weston HS-WHS Lower Turf Field [Directions] | 11:30 a.m. | W 4-0 | |
| Sat., 10/15 | JV Field Hockey | Westhill | Home - Weston HS-WHS Lower Turf Field [Directions] | 10:00 a.m. | ||
| Sat., 10/15 | V Girls Volleyball | New Milford | Home - Weston HS-Gym (New) [Directions] | 1:30 p.m. | W 3-2 | |
| Sat., 10/15 | JV Girls Volleyball | New Milford | Home - Weston HS-Gym (New) [Directions] | 12:00 p.m. | ||
| Sat., 10/15 | FR Girls Volleyball | New Milford | Home - Weston HS-Gym (Old) [Directions] | 12:00 p.m. | ||
| Mon., 10/17 | V Boys Golf | SWC Championship at Fairchild Wheeler- Black | Away - Fairchild Wheeler Golf Course | 8:00 a.m. | ||
| Mon., 10/17 | V Field Hockey | Bethel | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:30 p.m. | W 1-0 | |
| Mon., 10/17 | JV Field Hockey | Bethel | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 10/17 | V Girls Volleyball | Kolbe Cathedral | Away - Kolbe Cathedral HS-Gym [Directions] | 5:45 p.m. | W 3-0 | |
| Mon., 10/17 | JV Girls Volleyball | Kolbe Cathedral | Away - Kolbe Cathedral HS-Gym [Directions] | 4:15 p.m. | ||
| Tue., 10/18 | V Boys Soccer | Joel Barlow | Home - Weston HS-WHS Stadium Field [Directions] | 6:00 p.m. | L 2-4 | |
| Tue., 10/18 | JV Boys Soccer | Joel Barlow | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 10/18 | V Girls Soccer | Joel Barlow | Away - Joel Barlow HS-Field J (Competition Field) [Directions] | 4:00 p.m. | L 4-5 | |
| Tue., 10/18 | JV Girls Soccer | Joel Barlow | Away - Joel Barlow HS-Field E (Softball) [Directions] | 4:00 p.m. | ||
| Tue., 10/18 | V Girls Swimming and Diving | Brookfield | Home - Weston HS-Weston MS Pool [Directions] | 4:00 p.m. | Weston 103 Brookfield 77 | |
| Wed., 10/19 | V Boys Cross Country | SWC cross country championships | Away - Bethel HS-BHS track | 4:00 p.m. | ||
| Wed., 10/19 | V Girls Cross Country | SWC cross country championships | Away - Bethel HS-BHS track | 3:30 p.m. | ||
| Wed., 10/19 | V Field Hockey | Brookfield | Away - Brookfield HS-BHS Stadium Field [Directions] | 5:30 p.m. | T 1-1 | |
| Wed., 10/19 | JV Field Hockey | Brookfield | Away - Brookfield HS-BHS Stadium Field [Directions] | 4:00 p.m. | ||
| Thu., 10/20 | V Boys Soccer | Bunnell | Home - Weston HS-WHS Stadium Field [Directions] | 7:00 p.m. | W 4-0 | |
| Thu., 10/20 | JV Boys Soccer | Bunnell | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:00 p.m. | ||
| Thu., 10/20 | V Girls Soccer | Bunnell | Away - Bunnell HS-Mastroni Field [Directions] | 5:00 p.m. | W 3-1 | |
| Thu., 10/20 | JV Girls Soccer | Bunnell | Away - Bunnell HS-Mastroni Field [Directions] | 7:00 p.m. | ||
| Thu., 10/20 | V Girls Volleyball | Masuk | Home - Weston HS-Gym (New) [Directions] | 7:00 p.m. | W 3-0 | |
| Thu., 10/20 | JV Girls Volleyball | Masuk | Home - Weston HS-Gym (New) [Directions] | 5:30 p.m. | ||
| Thu., 10/20 | FR Girls Volleyball | Masuk | Home - Weston HS-Gym (Old) [Directions] | 5:30 p.m. | ||
| Fri., 10/21 | V Football | Bethel | Home - Weston HS-WHS Stadium Field [Directions] | 7:00 p.m. | W 50-13 | |
| Fri., 10/21 | V Girls Swimming and Diving | Newtown | Home - Weston HS-Weston MS Pool [Directions] | 4:00 p.m. | Weston 96 Newtown 82 | |
| Sat., 10/22 | JV Football | New Milford | Home - Weston HS-WHS Stadium Field [Directions] | 2:00 p.m. | ||
| Sat., 10/22 | V Girls Volleyball | Bethel | Home - Weston HS-Gym (New) [Directions] | 3:00 p.m. | W 3-0 | |
| Sat., 10/22 | JV Girls Volleyball | East Haven, Lauralton Hall, Amity, Branford, Career Magnet, Coginchaug, Haddam-Killingworth, Foran, Lyman Hall, Manchester, Newtown, Rockville, South Windsor, Woodland | Away - East Haven HS-Gym | 8:00 a.m. | ||
| Sat., 10/22 | JV Girls Volleyball | Bethel | Home - Weston HS-Gym (New) [Directions] | 4:30 p.m. | ||
| Sat., 10/22 | FR Girls Volleyball | Bethel | Home - Weston HS-Gym (Old) [Directions] | 4:30 p.m. | ||
| Mon., 10/24 | V Boys Golf | CIAC Division II Championship | Away - Chippanee GC | 8:30 a.m. | ||
| Mon., 10/24 | V Boys Soccer | Kolbe Cathedral | Away - Veterans Memorial Park CT [Directions] | 4:15 p.m. | W 4-2 | |
| Mon., 10/24 | V Girls Soccer | Kolbe Cathedral | Home - Weston HS-WHS Stadium Field [Directions] | 6:00 p.m. | W 6-1 | |
| Mon., 10/24 | FR Girls Volleyball | Cardinal Kung Academy | Home - Weston HS-Gym (Old) [Directions] | 4:30 p.m. | ||
| Tue., 10/25 | V Girls Swimming and Diving | Joel Barlow | Home - Weston HS-Weston MS Pool [Directions] | 4:00 p.m. | Weston 94 Joel Barlow 74 | |
| Tue., 10/25 | V Girls Volleyball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Tue., 10/25 | JV Girls Volleyball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 4:30 p.m. | ||
| Wed., 10/26 | V Boys Soccer | Abbott Tech | Away - Broadview MS-Stephen A. Kaplanis Turf Field [Directions] | 3:30 p.m. | W 6-0 | |
| Wed., 10/26 | FR Girls Volleyball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 4:00 p.m. | ||
| Thu., 10/27 | V Field Hockey | New Milford | Away - New Milford HS-Joe Wiser Stadium - NMHS [Directions] | 6:00 p.m. | W 3-2 | |
| Thu., 10/27 | Unified Sports Soccer | Bethel | Away - Bethel HS-DeSantis Field at Bethel High [Directions] | 3:00 p.m. | ||
| Fri., 10/28 | V Football | Masuk | Home - Weston HS-WHS Stadium Field [Directions] | 7:00 p.m. | L 13-45 | |
| Fri., 10/28 | V Girls Soccer | Brookfield | Away - Brookfield HS-BHS Stadium Field [Directions] | 5:00 p.m. | L 1-3 | |
| Sat., 10/29 | V Boys Cross Country | CIAC Class M Championship | Away - Wickham Park | 2:40 p.m. | ||
| Sat., 10/29 | JV Football | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 10:00 a.m. | ||
| Sat., 10/29 | V Boys Soccer | Masuk | Home - Weston HS-WHS Stadium Field [Directions] | 5:00 p.m. | W 5-0 | |
| Sat., 10/29 | V Girls Cross Country | CIAC Class M Championship | Away - Wickham Park | 2:05 p.m. | ||
| Sat., 10/29 | V Girls Volleyball | Immaculate | Home - Weston HS-Gym (New) [Directions] | 4:30 p.m. | W 3-0 | |
| Tue., 11/1 | V Boys Soccer | Pomperaug | Home - Weston HS-WHS Stadium Field [Directions] | 6:00 p.m. | L 1-2 (PKs) | |
| Tue., 11/1 | V Field Hockey | Brookfield | Away - Brookfield HS-BHS Stadium Field [Directions] | 6:00 p.m. | L 1-2 | |
| Tue., 11/1 | V Girls Swimming and Diving | SWC Diving Championship | Away - New Fairfield HS-Pool | 5:30 p.m. | ||
| Wed., 11/2 | V Girls Volleyball | Newtown | Away - Newtown HS-Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Fri., 11/4 | V Boys Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Fri., 11/4 | V Football | Brookfield | Home - Weston HS-WHS Stadium Field [Directions] | 7:00 p.m. | W 34-14 | |
| Fri., 11/4 | V Girls Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Sat., 11/5 | JV Football | Brookfield | Away - Brookfield HS-BHS Stadium Field [Directions] | 10:00 a.m. | ||
| Mon., 11/7 | V Boys Soccer | WCA | Home - Weston HS-WHS Stadium Field [Directions] | 2:00 p.m. | W 6-1 | |
| Mon., 11/7 | V Field Hockey | Lewis Mills | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:00 p.m. | W 2-0 | |
| Mon., 11/7 | V Girls Volleyball | Valley Regional | Home - Weston HS-Gym (New) [Directions] | 6:00 p.m. | W 3-2 | |
| Tue., 11/8 | V Field Hockey | Stonington | Away - Stonington HS-Palmer Field (Turf Stadium) [Directions] | 5:00 p.m. | ||
| Tue., 11/8 | V Girls Soccer | Rocky Hill | Away - Rocky Hill HS-Stadium [Directions] | 6:00 p.m. | W 3-0 | |
| Wed., 11/9 | V Boys Soccer | Holy Cross | Home - Weston HS-WHS Stadium Field [Directions] | 5:00 p.m. | W 2-0 | |
| Wed., 11/9 | V Girls Swimming and Diving | CIAC Class S Diving Championships | Away - Sheehan | 5:30 p.m. | ||
| Wed., 11/9 | V Girls Volleyball | Seymour | Away - Seymour HS-Gym [Directions] | 6:00 p.m. | L 2-3 | |
| Wed., 11/9 | Unified Sports Soccer | Joel Barlow | Away - Joel Barlow HS-Field A [Directions] | 3:00 p.m. | ||
| Thu., 11/10 | V Girls Soccer | Tolland | Away - Tolland HS-Stadium [Directions] | 5:00 p.m. | W 3-2 | |
| Sat., 11/12 | JV Football | Jonathan Law | Away - Jonathan Law HS-Lawmen Stadium [Directions] | 2:00 p.m. | ||
| Sat., 11/12 | V Boys Soccer | Rocky Hill | Home - Weston HS-WHS Stadium Field [Directions] | 3:00 p.m. | W 3-2 | |
| Sat., 11/12 | V Girls Soccer | Mercy | Away - Xavier HS-Larry McHugh Field [Directions] | 5:30 p.m. | L 1-2 | |
| Sat., 11/12 | V Girls Swimming and Diving | CIAC Class S Trials | Away - Cheshire Community Pool | 6:00 p.m. | ||
| Mon., 11/14 | V Football | Notre Dame-Fairfield | Away - Sacred Heart University-Campus Field [Directions] | 6:30 p.m. | W 3-0 | |
| Tue., 11/15 | V Boys Soccer | Cromwell | Home - Pomperaug HS-Stadium [Directions] | 7:30 p.m. | W 6-3 | |
| Tue., 11/15 | V Girls Swimming and Diving | CIAC Class S Final | Away - SCSU | 6:00 p.m. | ||
| Wed., 11/16 | V | Unified Zumba | Home - Weston HS-Gym (New) [Directions] | 2:30 p.m. | ||
| Thu., 11/17 | JV Football | Joel Barlow | Away - Joel Barlow HS-Field I (Stadium) [Directions] | 5:30 p.m. | ||
| Thu., 11/17 | V Girls Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 11/19 | V Boys Soccer | Ellington | Away - Trinity Health Stadium-Dillon Stadium [Directions] | 1:30 p.m. | ||
| Sun., 11/20 | V Girls Swimming and Diving | CIAC State Open Swimming Championship | Away - Yale | 2:00 p.m. | ||
| Wed., 11/23 | V Football | Joel Barlow | Home - Weston HS-WHS Stadium Field [Directions] | 4:30 p.m. | L 20-56 | |
| Sat., 12/3 | V Boys Ice Hockey | Staples (Scrim.) | Home - Danbury Ice Arena-Patriot Rink [Directions] | 1:15 p.m. | ||
| Wed., 12/7 | V Boys Basketball | Oxford (Scrim.) | Away - Oxford HS-Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 12/7 | V Girls Basketball | Lauralton Hall (Scrim.) | Away - Lauralton Hall-Gym [Directions] | 4:30 p.m. | ||
| Fri., 12/9 | V Boys Basketball | Darien (Scrim.) | Away - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 12/9 | JV Boys Basketball | Darien (Scrim.) | Away - Darien HS-DHS Main Gym [Directions] | 7:00 p.m. | ||
| Fri., 12/9 | V Girls Basketball | Darien (Scrim.) | Home - Weston HS-Gym (New) [Directions] | 5:30 p.m. | ||
| Fri., 12/9 | JV Girls Basketball | Darien (Scrim.) | Home - Weston HS-Gym (New) [Directions] | 4:00 p.m. | ||
| Fri., 12/9 | V Girls Ice Hockey | Guilford Coop | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | L 5-7 | |
| Sat., 12/10 | V Boys Ice Hockey | Staples (Scrim.) | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 6:30 p.m. | ||
| Sat., 12/10 | V Boys Ice Hockey | Masuk (Scrim.) | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 8:15 p.m. | ||
| Mon., 12/12 | V Boys Ice Hockey | Housatonic Coop | Away - South Kent School-Ice Rink [Directions] | 3:45 p.m. | W 4-2 | |
| Mon., 12/12 | V Girls Basketball | Foran | Home - Weston HS-Gym (New) [Directions] | 7:00 p.m. | W 39-30 | |
| Mon., 12/12 | JV Girls Basketball | Foran | Home - Weston HS-Gym (New) [Directions] | 5:30 p.m. | ||
| Wed., 12/14 | V Wrestling | Pomperaug Coop | Home - Weston HS-Gym (New) [Directions] | 6:00 p.m. | 48 Weston 21 Pomperaug | |
| Wed., 12/14 | V Girls Basketball | Bunnell | Away - Bunnell HS-David Johnson Gymnasium [Directions] | 6:00 p.m. | W 45-20 | |
| Wed., 12/14 | JV Girls Basketball | Bunnell | Away - Bunnell HS-David Johnson Gymnasium [Directions] | 4:15 p.m. | ||
| Thu., 12/15 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice-New [Directions] | 4:40 p.m. | W 7-2 | |
| Fri., 12/16 | V Boys Indoor Track | At The Armory in NYC | Away - Weston HS | 4:00 p.m. | ||
| Fri., 12/16 | V Girls Indoor Track | At The Armory in NYC | Away - Weston HS-Gym (Old) | 4:00 p.m. | ||
| Sat., 12/17 | V Boys Basketball | Foran | Away - Foran HS -Edna L. Fraser Gymnasium [Directions] | 1:45 p.m. | W 49-38 | |
| Sat., 12/17 | JV Boys Basketball | Foran | Away - Foran HS -Edna L. Fraser Gymnasium [Directions] | 12:00 p.m. | ||
| Sat., 12/17 | FR Boys Basketball | Foran | Away - Foran HS -Edna L. Fraser Gymnasium [Directions] | 10:30 a.m. | ||
| Sat., 12/17 | V Boys Ice Hockey | Sheehan | Home - Danbury Ice Arena-Patriot Rink [Directions] | 3:30 p.m. | L 2-4 | |
| Sat., 12/17 | V Wrestling | Ludlowe Invitational | Away - Fairfield Ludlowe HS-Main Gym | 9:00 a.m. | ||
| Sat., 12/17 | V Girls Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 3:30 p.m. | L 29-38 | |
| Sat., 12/17 | JV Girls Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 1:00 p.m. | ||
| Sat., 12/17 | JV Girls Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 2:00 p.m. | ||
| Sat., 12/17 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Away - Hamden-Lou Astorino Ice Rink [Directions] | 6:30 p.m. | W 7-1 | |
| Mon., 12/19 | V Girls Basketball | Bridgeport Central | Away - Bridgeport Central HS-The Barry McLeod Court [Directions] | 5:30 p.m. | W 58-18 | |
| Mon., 12/19 | JV Girls Basketball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | 4:00 p.m. | ||
| Tue., 12/20 | JV Boys Ice Hockey | Bethel/Brookfield/Danbury/Immaculate | Home - Danbury Ice Arena-Patriot Rink [Directions] | 3:45 p.m. | ||
| Tue., 12/20 | V Wrestling | Brookfield/Shepaug | Away - Brookfield HS-BHS Small Gym [Directions] | 6:00 p.m. | Weston 72 Brookfield/Shepaug 12 | |
| Tue., 12/20 | V Girls Basketball | Notre Dame-Fairfield | Home - Weston HS-Gym (New) [Directions] | 7:00 p.m. | L 31-43 | |
| Tue., 12/20 | JV Girls Basketball | Notre Dame-Fairfield | Home - Weston HS-Gym (New) [Directions] | 5:30 p.m. | ||
| Wed., 12/21 | V Boys Basketball | Brien McMahon | Home - Weston HS-Gym (New) [Directions] | 7:00 p.m. | L 46-47 | |
| Wed., 12/21 | JV Boys Basketball | Brien McMahon | Home - Weston HS-Gym (New) [Directions] | 5:15 p.m. | ||
| Wed., 12/21 | FR Boys Basketball | Brien McMahon | Home - Weston HS-Gym (New) [Directions] | 4:00 p.m. | ||
| Wed., 12/21 | V Girls Ice Hockey | Daniel Hand Coop | Away - Northford-Red [Directions] | 4:00 p.m. | L 4-7 | |
| Thu., 12/22 | V Boys Swimming and Diving | Bunnell-Stratford | Away - Bunnell HS-Flood M.S. Pool [Directions] | 4:30 p.m. | Weston 91 Bunnell/Stratford 60 | |
| Thu., 12/22 | V Girls Basketball | New Milford | Home - Weston HS-Gym (New) [Directions] | 7:00 p.m. | L 40-51 | |
| Thu., 12/22 | JV Girls Basketball | New Milford | Home - Weston HS-Gym (New) [Directions] | 5:30 p.m. | ||
| Mon., 12/26 | V Boys Ice Hockey | Brien McMahon/Norwalk | Away - Sono Ice House-Main Rink [Directions] | 12:00 p.m. | L 2-5 | |
| Tue., 12/27 | V Boys Ice Hockey | Alumni Game | Home - Danbury Ice Arena-Patriot Rink [Directions] | 4:00 p.m. | ||
| Thu., 12/29 | V Boys Basketball | New Fairfield | Home - Weston HS-Gym (New) [Directions] | 1:00 p.m. | L 59-62 | |
| Thu., 12/29 | V Boys Ice Hockey | Westhill/Stamford | Home - Danbury Ice Arena-LIberty Rink [Directions] | 6:00 p.m. | L 2-7 | |
| Fri., 12/30 | V Boys Basketball | Woodlands (NY) | Away - Woodlands HS | 1:00 p.m. | W 62-60 | |
| Tue., 1/3 | V Boys Basketball | Harding | Home - Weston HS-Gym (New) [Directions] | 7:00 p.m. | W 62-40 | |
| Tue., 1/3 | JV Boys Basketball | Harding | Home - Weston HS-Gym (Old) [Directions] | 5:30 p.m. | ||
| Tue., 1/3 | V Girls Basketball | Bassick | Home - Weston HS-Gym (New) [Directions] | 5:00 p.m. | W 54-42 | |
| Tue., 1/3 | JV Girls Basketball | Bassick | Home - Weston HS-Gym (New) [Directions] | Postponed | ||
| Wed., 1/4 | FR Boys Basketball | Harding | Home - Weston HS-Gym (Old) [Directions] | 5:30 p.m. | ||
| Wed., 1/4 | V Boys Ice Hockey | Milford Coop | Away - Milford Ice Pavillion-Ice Rink [Directions] | 6:00 p.m. | W 3-0 | |
| Wed., 1/4 | V Wrestling | Bunnell | Away - Bunnell HS-David Johnson Gymnasium [Directions] | 6:00 p.m. | Weston 48 Bunnell 27 | |
| Wed., 1/4 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 5:45 p.m. | L 4-8 | |
| Thu., 1/5 | V Boys Basketball | Bethel | Away - Bethel HS-BHS gym [Directions] | 7:00 p.m. | W 54-31 | |
| Thu., 1/5 | JV Boys Basketball | Bethel | Away - Bethel HS-BHS gym [Directions] | 5:15 p.m. | ||
| Thu., 1/5 | FR Boys Basketball | Bethel | Away - Bethel HS-BHS gym [Directions] | 3:45 p.m. | ||
| Thu., 1/5 | V Boys Indoor Track | SWC Split Meet Developmental at Bethel | Away - Bethel HS-Bethel Track and Field Center | 4:00 p.m. | ||
| Thu., 1/5 | V Boys Swimming and Diving | Pomperaug | Home - Weston HS-Weston MS Pool [Directions] | 4:30 p.m. | Pomperaug 95 Weston 83 | |
| Thu., 1/5 | V | Bethel | Home - Weston HS-Gym (New) [Directions] | TBA | ||
| Thu., 1/5 | V Girls Basketball | Bethel | Home - Weston HS-Gym (New) [Directions] | 7:00 p.m. | W 48-40 | |
| Thu., 1/5 | JV Girls Basketball | Bethel | Home - Weston HS-Gym (New) [Directions] | 5:00 p.m. | ||
| Thu., 1/5 | V Girls Indoor Track | SWC Split Meet Developmental at Bethel | Away - Bethel HS-Bethel Track and Field Center | 4:00 p.m. | ||
| Fri., 1/6 | V Wrestling | Masuk | Home - Weston HS-Gym (New) [Directions] | 6:00 p.m. | Weston 54 Masuk 30 | |
| Fri., 1/6 | V Girls Ice Hockey | Mercy/NW Catholic/East Hampton | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | L 1-4 | |
| Sat., 1/7 | JV Boys Basketball | Cardinal Kung Academy | Home - Weston HS-Gym (New) [Directions] | 12:00 p.m. | ||
| Sat., 1/7 | FR Boys Basketball | Cardinal Kung Academy | Home - Weston HS-Gym (New) [Directions] | 10:30 a.m. | ||
| Sat., 1/7 | JV Boys Ice Hockey | Shepaug Valley Ice Hockey | Away - The Frederick Gunn School-Ice Rink [Directions] | 10:00 a.m. | ||
| Sat., 1/7 | FR Girls Basketball | Cardinal Kung Academy | Home - Weston HS-Gym (New) [Directions] | 9:00 a.m. | ||
| Sat., 1/7 | V Girls Gymnastics | Trumbull | Away - Next Dimension Gymnastics-Next Dimension [Directions] | 5:30 p.m. | Ludlowe - 131.65 Trumbull - 129.95 SJ - 125.05 | No Bus Needed |
| Sat., 1/7 | V Girls Gymnastics | St. Joseph, Fairfield Warde | Away - St. Joseph HS-Next Dimensions [Directions] | 5:30 p.m. | ||
| Sat., 1/7 | JV Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice-New [Directions] | 7:30 p.m. | ||
| Mon., 1/9 | V Boys Basketball | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | 7:00 p.m. | L 32-49 | |
| Mon., 1/9 | JV Boys Basketball | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | 5:30 p.m. | ||
| Mon., 1/9 | FR Boys Basketball | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | 4:00 p.m. | ||
| Mon., 1/9 | V Boys Ice Hockey | Housatonic Coop | Home - Danbury Ice Arena-Patriot Rink [Directions] | 8:00 p.m. | W 3-2 | |
| Mon., 1/9 | V Girls Basketball | New Fairfield | Home - Weston HS-Gym (New) [Directions] | 7:00 p.m. | L 25-34 | |
| Mon., 1/9 | JV Girls Basketball | New Fairfield | Home - Weston HS-Gym (New) [Directions] | 5:30 p.m. | ||
| Tue., 1/10 | V Boys Swimming and Diving | New Fairfield | Away - New Fairfield HS-Pool [Directions] | 4:00 p.m. | Weston 87 New Fairfield 52 | |
| Wed., 1/11 | V Boys Ice Hockey | New Milford | Home - Danbury Ice Arena-Patriot Rink [Directions] | 7:30 p.m. | L 2-6 | |
| Wed., 1/11 | V Boys Indoor Track | Developmental Meet | Away - Bethel HS-Track and Field Training Center | 4:00 p.m. | ||
| Wed., 1/11 | V Wrestling | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Sister Marion Reilly Auditorium [Directions] | 6:00 p.m. | Weston 75 Notre Dame 0 | |
| Wed., 1/11 | V Girls Gymnastics | New Canaan, Nonnewaug | Home - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:30 p.m. | Ludlowe - 130.80 Nonnewaug - 121.85 | |
| Wed., 1/11 | V Girls Ice Hockey | Hamden Coop | Away - Hamden-Lou Astorino Ice Rink [Directions] | 8:00 p.m. | L 3-9 | |
| Wed., 1/11 | V Girls Indoor Track | SWC Developmental | Away - Bethel HS-Track and Field Training Center | 4:00 p.m. | ||
| Thu., 1/12 | V Boys Basketball | Masuk | Home - Weston HS-Gym (New) [Directions] | 7:00 p.m. | W 58-49 | |
| Thu., 1/12 | JV Boys Basketball | Masuk | Home - Weston HS-Gym (New) [Directions] | 5:30 p.m. | ||
| Thu., 1/12 | FR Boys Basketball | Masuk | Home - Weston HS-Gym (New) [Directions] | 4:00 p.m. | ||
| Thu., 1/12 | V Wrestling | Wilton | Away - Wilton HS-Nicholas Zeoli Fieldhouse [Directions] | 6:00 p.m. | Weston 48 Wilton 33 | |
| Thu., 1/12 | V Girls Basketball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 7:00 p.m. | W 59-52 | |
| Thu., 1/12 | JV Girls Basketball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 5:15 p.m. | ||
| Fri., 1/13 | V Boys Indoor Track | At The Armory in NYC | Away - Not Listed | 4:00 p.m. | ||
| Fri., 1/13 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 4:00 p.m. | L 3-12 | |
| Fri., 1/13 | V Girls Indoor Track | At The Armory in NYC | Away - Not Listed | 4:00 p.m. | ||
| Sat., 1/14 | V Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena-Patriot Rink [Directions] | 12:00 p.m. | W 5-1 | |
| Sat., 1/14 | V Wrestling | Darien, Bunnell, Derby/Oxford/Holy Cross, New Fairfield | Away - Darien HS-DHS Main Gym [Directions] | 8:00 a.m. | ||
| Sat., 1/14 | V Girls Ice Hockey | Suffield Coop | Away - Enfield Twin Rinks-Rink 1 [Directions] | 6:20 p.m. | L 1-5 | |
| Mon., 1/16 | V Girls Gymnastics | Daniel Hand | Home - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 10:00 a.m. | Daniel Hand - 139.90 Ludlowe - 128.20 | |
| Tue., 1/17 | V Boys Basketball | New Milford | Home - Weston HS-Gym (New) [Directions] | 7:00 p.m. | W 64-60 | |
| Tue., 1/17 | JV Boys Basketball | New Milford | Home - Weston HS-Gym (New) [Directions] | 5:30 p.m. | ||
| Tue., 1/17 | FR Boys Basketball | New Milford | Home - Weston HS-Gym (New) [Directions] | 4:00 p.m. | ||
| Tue., 1/17 | V Boys Ice Hockey | John Jay (NY) | Home - Danbury Ice Arena-Patriot Rink [Directions] | 8:15 p.m. | L 2-4 | |
| Tue., 1/17 | V Boys Swimming and Diving | Newtown | Away - Newtown HS-pool [Directions] | 4:00 p.m. | Weston 91 Newtown 75 | |
| Tue., 1/17 | V Girls Basketball | New Milford | Away - New Milford HS-Main Gym - NMHS [Directions] | 6:00 p.m. | L 44-62 | |
| Tue., 1/17 | JV Girls Basketball | New Milford | Away - New Milford HS-Main Gym - NMHS [Directions] | 4:30 p.m. | ||
| Tue., 1/17 | V Girls Ice Hockey | West Haven/SHA | Away - West Haven HS-Bennett Rink [Directions] | 5:30 p.m. | L 1-5 | |
| Wed., 1/18 | V Boys Indoor Track | Developmental Meet | Away - Bethel HS-Track and Field Training Center | 4:00 p.m. | ||
| Wed., 1/18 | V Wrestling | New Fairfield | Home - Weston HS-Gym (New) [Directions] | 6:00 p.m. | New Fairfield 54 Weston 29 | |
| Wed., 1/18 | V Girls Gymnastics | Darien | Home - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:30 p.m. | Ludlowe - 138.15 Darien - 137.50 | |
| Wed., 1/18 | V Girls Indoor Track | Developmental Meet | Away - Bethel HS-Track and Field Training Center | 4:00 p.m. | ||
| Fri., 1/20 | V Boys Basketball | Newtown | Away - Newtown HS-Gym [Directions] | 7:00 p.m. | L 42-55 | |
| Fri., 1/20 | JV Boys Basketball | Newtown | Away - Newtown HS-Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/20 | FR Boys Basketball | Newtown | Away - Newtown HS-Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/20 | V Boys Ice Hockey | Shepaug Valley Ice Hockey | Away - The Frederick Gunn School-Ice Rink [Directions] | 8:30 p.m. | W 4-1 | |
| Fri., 1/20 | V Boys Indoor Track | At The Armory in NYC | Away - Weston HS-Gym (Old) | 4:00 p.m. | ||
| Fri., 1/20 | V Girls Basketball | Newtown | Home - Weston HS-Gym (New) [Directions] | 6:00 p.m. | L 22-42 | |
| Fri., 1/20 | JV Girls Basketball | Newtown | Home - Weston HS-Gym (New) [Directions] | 4:30 p.m. | ||
| Fri., 1/20 | V Girls Ice Hockey | Daniel Hand Coop | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | L 6-9 | |
| Fri., 1/20 | V Girls Indoor Track | At The Armory in NYC | Away - Weston HS-Gym (Old) | 4:00 p.m. | ||
| Sat., 1/21 | V Boys Indoor Track | At The Armory in NYC | Away - Not Listed | 12:00 p.m. | ||
| Sat., 1/21 | V Wrestling | New Milford Wrestling Tournament | Away - New Milford HS-Small Gym - NMHS | 8:00 a.m. | ||
| Sat., 1/21 | V Girls Indoor Track | At The Armory in NYC | Away - Not Listed | 12:00 p.m. | ||
| Mon., 1/23 | V Boys Basketball | Wright Tech | Away - J M Wright Tech School-Thomas R. Good Gymnasium [Directions] | 6:00 p.m. | W 57-32 | |
| Mon., 1/23 | JV Boys Basketball | Wright Tech | Away - J M Wright Tech School-Thomas R. Good Gymnasium [Directions] | 4:30 p.m. | ||
| Mon., 1/23 | V Girls Basketball | Wright Tech | Home - Weston HS-Gym (New) [Directions] | 5:30 p.m. | W 78-36 | |
| Tue., 1/24 | V Boys Indoor Track | Varsity Developmental Meet | Away - Southern Connecticut State University-indoor track | 4:00 p.m. | ||
| Tue., 1/24 | V Girls Indoor Track | Varsity Developmental Meet | Away - Southern Connecticut State University-indoor track | 4:00 p.m. | ||
| Wed., 1/25 | V Girls Gymnastics | Norwalk, Staples | Home - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:30 p.m. | Ludlowe - 133.05 Staples - 132.95 | |
| Thu., 1/26 | V Boys Ice Hockey | Trumbull | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | 5:00 p.m. | W 2-1 | |
| Thu., 1/26 | V Wrestling | Bethel | Home - Weston HS-Gym (Old) [Directions] | 6:00 p.m. | Weston 52 Bethel 30 | |
| Fri., 1/27 | V Boys Basketball | Bunnell | Away - Bunnell HS-David Johnson Gymnasium [Directions] | 7:00 p.m. | L 50-44 | |
| Fri., 1/27 | JV Boys Basketball | Bunnell | Away - Bunnell HS-David Johnson Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/27 | FR Boys Basketball | Bunnell | Away - Bunnell HS-David Johnson Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/27 | V Girls Basketball | Bunnell | Home - Weston HS-Gym (New) [Directions] | 7:00 p.m. | W 54-33 | |
| Fri., 1/27 | JV Girls Basketball | Bunnell | Home - Weston HS-Gym (New) [Directions] | 5:30 p.m. | ||
| Fri., 1/27 | V Girls Ice Hockey | Hall/Conard | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | L 2-5 | |
| Sat., 1/28 | V Boys Ice Hockey | Newtown/New Fairfield | Home - Danbury Ice Arena-Patriot Rink [Directions] | 12:00 p.m. | L 3-1 | |
| Sat., 1/28 | Miscellaneous Events | Counties Dance (juniors) | Home - TBA [Directions] | TBA | ||
| Sun., 1/29 | JV Girls Ice Hockey | West Haven/SHA | Away - West Haven HS-Bennett Rink [Directions] | 6:45 p.m. | ||
| Mon., 1/30 | V Boys Basketball | Brookfield | Home - Weston HS-Gym (New) [Directions] | 7:00 p.m. | L 64-69 | |
| Mon., 1/30 | JV Boys Basketball | Brookfield | Home - Weston HS-Gym (New) [Directions] | 5:30 p.m. | ||
| Mon., 1/30 | FR Boys Basketball | Brookfield | Home - Weston HS-Gym (New) [Directions] | 4:00 p.m. | ||
| Mon., 1/30 | V Girls Basketball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 7:00 p.m. | L 32-44 | |
| Mon., 1/30 | JV Girls Basketball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/31 | V Boys Basketball | Joel Barlow | Home - Weston HS-Gym (New) [Directions] | 7:00 p.m. | W 50-41 | |
| Tue., 1/31 | JV Boys Basketball | Joel Barlow | Home - Weston HS-Gym (New) [Directions] | 5:15 p.m. | ||
| Tue., 1/31 | FR Boys Basketball | Joel Barlow | Home - Weston HS-Gym (New) [Directions] | 3:45 p.m. | ||
| Tue., 1/31 | V Boys Swimming and Diving | Masuk | Away - Masuk HS-Pool [Directions] | 6:00 p.m. | Weston 97 Masuk 73 | |
| Tue., 1/31 | V Girls Basketball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 6:00 p.m. | W 52-36 | |
| Tue., 1/31 | JV Girls Basketball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 4:30 p.m. | ||
| Tue., 1/31 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 7:15 p.m. | L 1-2 | |
| Wed., 2/1 | V Boys Ice Hockey | Watertown-Pomperaug | Home - Danbury Ice Arena-Patriot Rink [Directions] | 5:30 p.m. | W 3-1 | |
| Wed., 2/1 | V Wrestling | Joel Barlow | Home - Weston HS-Gym (New) [Directions] | 6:00 p.m. | Weston 61 Barlow 18 | |
| Wed., 2/1 | V Girls Gymnastics | Stamford, Westhill | Home - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:30 p.m. | Ludlowe - 131.65 Stamford - 118.90 Westhill - 80.50 | |
| Wed., 2/1 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Conners - Stamford-Ice Rink [Directions] | 8:00 p.m. | L 0-3 | |
| Thu., 2/2 | V Boys Basketball | Kolbe Cathedral | Away - Cardinal Sheehan Center Bridgeport [Directions] | 7:00 p.m. | L 33-56 | |
| Thu., 2/2 | JV Boys Basketball | Kolbe Cathedral | Away - Cardinal Sheehan Center Bridgeport [Directions] | 5:15 p.m. | ||
| Thu., 2/2 | JV Boys Ice Hockey | Shepaug Valley Ice Hockey | Home - Danbury Ice Arena-Patriot Rink [Directions] | 8:15 p.m. | ||
| Thu., 2/2 | V Girls Basketball | Kolbe Cathedral | Home - Weston HS-Gym (New) [Directions] | 7:00 p.m. | L 40-43 | |
| Thu., 2/2 | JV Girls Basketball | Kolbe Cathedral | Home - Weston HS-Gym (New) [Directions] | 5:30 p.m. | ||
| Thu., 2/2 | V Girls Gymnastics | Greenwich, Fairfield Warde | Away - Greenwich YWCA [Directions] | 6:30 p.m. | Ludlowe - 129.80 | |
| Fri., 2/3 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | W 3-2 | |
| Fri., 2/3 | Miscellaneous Events | Red and Whites Dance (seniors) | Home - TBA [Directions] | TBA | ||
| Sat., 2/4 | V Boys Indoor Track | SWC Championship Meet | Away - Floyd Little Athletic Center-Field House | 5:00 p.m. | ||
| Sat., 2/4 | V Girls Ice Hockey | Guilford Coop | Away - East Haven HS-Veterans Rink [Directions] | 3:15 p.m. | L 2-3 | |
| Sat., 2/4 | V Girls Indoor Track | Bethel, Brookfield, Bunnell, Immaculate, Joel Barlow, Kolbe Cathedral, Masuk, New Fairfield, New Milford, Newtown, Notre Dame-Fairfield, Pomperaug, Stratford | Away - Floyd Little Athletic Center-Field House | 5:00 p.m. | ||
| Mon., 2/6 | V Boys Basketball | Stratford | Home - Weston HS-Gym (New) [Directions] | 7:00 p.m. | W 49-38 | |
| Mon., 2/6 | JV Boys Basketball | Stratford | Home - Weston HS-Gym (New) [Directions] | 5:30 p.m. | ||
| Mon., 2/6 | FR Boys Basketball | Stratford | Home - Weston HS-Gym (New) [Directions] | 4:00 p.m. | ||
| Mon., 2/6 | V Boys Ice Hockey | Masuk | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 8:00 p.m. | L 4-1 | |
| Mon., 2/6 | V Girls Basketball | Stratford | Away - Stratford HS-Gym [Directions] | 7:00 p.m. | L 38-52 | |
| Mon., 2/6 | JV Girls Basketball | Stratford | Away - Stratford HS-Gym [Directions] | 5:15 p.m. | ||
| Mon., 2/6 | V Girls Gymnastics | Foran, Wilton | Home - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:30 p.m. | Wilton- 132.25 Ludlowe - 131.45 Foran - 125.35 | |
| Mon., 2/6 | JV Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 4:00 p.m. | ||
| Tue., 2/7 | V Boys Swimming and Diving | New Milford | Home - Weston HS-Weston MS Pool [Directions] | 4:00 p.m. | Weston 97 New Milford 63 | |
| Tue., 2/7 | V Wrestling | Stratford | Away - Stratford HS-Gym [Directions] | 6:00 p.m. | Stratford 51 Weston 24 | |
| Wed., 2/8 | V Boys Ice Hockey | Bethel/Brookfield/Danbury/Immaculate | Home - Danbury Ice Arena-Patriot Rink [Directions] | 5:30 p.m. | W 4-2 | |
| Wed., 2/8 | V Girls Ice Hockey | West Haven/SHA | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | L 4-6 | |
| Thu., 2/9 | V Boys Basketball | Immaculate | Home - Weston HS-Gym (New) [Directions] | 7:00 p.m. | W 46-39 | |
| Thu., 2/9 | JV Boys Basketball | Immaculate | Home - Weston HS-Gym (New) [Directions] | 5:30 p.m. | ||
| Thu., 2/9 | FR Boys Basketball | Immaculate | Home - Weston HS-Gym (New) [Directions] | 4:00 p.m. | ||
| Thu., 2/9 | V Girls Basketball | Immaculate | Away - Immaculate HS-Immaculate Gym [Directions] | 7:00 p.m. | L 22-48 | |
| Thu., 2/9 | JV Girls Basketball | Immaculate | Away - Immaculate HS-Immaculate Gym [Directions] | 5:15 p.m. | ||
| Sat., 2/11 | V Boys Basketball | Fitch | Home - Weston HS-Gym (New) [Directions] | 3:00 p.m. | L 38-56 | |
| Sat., 2/11 | JV Boys Basketball | Fitch | Home - Weston HS-Gym (New) [Directions] | 1:15 p.m. | ||
| Sat., 2/11 | FR Boys Basketball | Fitch | Home - Weston HS-Gym (New) [Directions] | 11:30 a.m. | ||
| Sat., 2/11 | V Boys Ice Hockey | Northeastern Shamrocks | Away - Bolton Ice Palace-Ice Rink [Directions] | 7:00 p.m. | W 4-1 | |
| Sat., 2/11 | V Boys Indoor Track | CIAC Class M Championships | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Sat., 2/11 | V Wrestling | SWC Wrestling Championships | Away - Stratford HS-Gym | 8:30 a.m. | ||
| Sat., 2/11 | V Girls Gymnastics | FCIAC Meet | Home - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 9:30 a.m. | Ludlowe - 130.675 | |
| Sat., 2/11 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 8:00 p.m. | L 1-6 | |
| Sat., 2/11 | V Girls Indoor Track | CIAC Class M Championships | Away | 10:00 a.m. | ||
| Tue., 2/14 | V Boys Basketball | Pomperaug | Away - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | W 56-55 | |
| Tue., 2/14 | JV Boys Basketball | Pomperaug | Away - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/14 | FR Boys Basketball | Pomperaug | Away - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/14 | JV Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena-LIberty Rink [Directions] | 3:45 p.m. | ||
| Tue., 2/14 | V Boys Swimming and Diving | Joel Barlow-Bethel Swim | Home - Weston HS-Weston MS Pool [Directions] | 4:00 p.m. | Weston 89 JB/Bethel 68 | |
| Tue., 2/14 | V Girls Basketball | Pomperaug | Home - Weston HS-Gym (New) [Directions] | 7:00 p.m. | L 37-51 | |
| Tue., 2/14 | JV Girls Basketball | Pomperaug | Home - Weston HS-Gym (New) [Directions] | 5:30 p.m. | ||
| Tue., 2/14 | Unified Sports Basketball | Brookfield | Home - Weston HS-Gym (New) [Directions] | 4:00 p.m. | ||
| Wed., 2/15 | V Boys Ice Hockey | Masuk | Home - Danbury Ice Arena-Patriot Rink [Directions] | 5:30 p.m. | T 2-2(OT) | |
| Wed., 2/15 | V Girls Gymnastics | Fairfield Warde | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:30 p.m. | Warde- 138.75 Ludlowe- 132.40 | |
| Wed., 2/15 | V Girls Ice Hockey | Hamden Coop | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 5:00 p.m. | W 6-5 | |
| Fri., 2/17 | V Boys Basketball | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Sister Marion Reilly Auditorium [Directions] | 7:00 p.m. | L 33-64 | |
| Fri., 2/17 | JV Boys Basketball | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Sister Marion Reilly Auditorium [Directions] | 5:30 p.m. | ||
| Fri., 2/17 | FR Boys Basketball | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Sister Marion Reilly Auditorium [Directions] | 4:00 p.m. | ||
| Fri., 2/17 | V Wrestling | CIAC M Championship | Away - Jonathan Law | 4:00 p.m. | ||
| Fri., 2/17 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice-New [Directions] | 8:30 p.m. | W 4-3 | |
| Sat., 2/18 | V Boys Ice Hockey | Bethel/Brookfield/Danbury/Immaculate | Away - Danbury Ice Arena-Patriot Rink [Directions] | 11:30 a.m. | W 5-2 | |
| Sat., 2/18 | V Boys Indoor Track | CIAC State Open Championships | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/18 | V Wrestling | CIAC M Championship | Away - Jonathan Law | 10:30 a.m. | ||
| Sat., 2/18 | V Girls Indoor Track | CIAC State Open Championships | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Mon., 2/20 | V Girls Ice Hockey | Guilford Coop | Away - East Haven HS-Veterans Rink [Directions] | 8:00 p.m. | ||
| Wed., 2/22 | V Boys Ice Hockey | Staples | Away - Milford Ice Pavillion-Ice Rink [Directions] | 6:00 p.m. | W 4-3 | |
| Thu., 2/23 | V Boys Swimming and Diving | Brookfield | Home - Weston HS-Weston MS Pool [Directions] | 4:00 p.m. | Weston 101 Brookfield 69 | |
| Fri., 2/24 | V Boys Basketball | Kolbe Cathedral | Away - Cardinal Sheehan Center Bridgeport [Directions] | 6:00 p.m. | L 30-55 | |
| Fri., 2/24 | V Wrestling | CIAC State Open | Away - Floyd Little Athletic Center | 12:45 p.m. | ||
| Sat., 2/25 | V Boys Ice Hockey | Cheshire | Away - Hamden-Lou Astorino Ice Rink [Directions] | 7:00 p.m. | L 2-4 | |
| Sat., 2/25 | V Wrestling | CIAC State Open | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Sat., 2/25 | V Girls Gymnastics | CIAC Divisional Championships | Away - Jonathan Law | TBA | ||
| Mon., 2/27 | V Girls Basketball | RHAM | Away - RHAM HS-Gym [Directions] | 5:00 p.m. | ||
| Tue., 2/28 | JV Boys Ice Hockey | Shepaug Valley Ice Hockey | Away - The Frederick Gunn School-Ice Rink [Directions] | Canceled | Cancelled | |
| Wed., 3/1 | V Boys Ice Hockey | New Milford | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | 6:30 p.m. | ||
| Thu., 3/2 | V Girls Basketball | New London | Away - New London HS-Conway Gym [Directions] | 6:30 p.m. | ||
| Fri., 3/3 | V Boys Ice Hockey | Masuk | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | 4:45 p.m. | ||
| Sat., 3/4 | V Girls Gymnastics | CIAC State Open | Away - New Milford | 4:00 p.m. | ||
| Mon., 3/6 | V Boys Ice Hockey | Wilton | Home - Danbury Ice Arena-Patriot Rink [Directions] | 8:00 p.m. | ||
| Tue., 3/7 | V Boys Basketball | North Haven | Home - Weston HS-Gym (New) [Directions] | 6:30 p.m. | W 61-56 | |
| Wed., 3/8 | V Boys Swimming and Diving | CIAC Class S Diving Championships | Away - Sheehan | 5:30 p.m. | ||
| Thu., 3/9 | V Boys Basketball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 6:30 p.m. | ||
| Thu., 3/9 | V Boys Ice Hockey | Conard | Away - West Haven HS-Bennett Rink [Directions] | 6:00 p.m. | ||
| Sat., 3/11 | V Boys Swimming and Diving | CIAC Class S Trials | Away - East Hartford | 4:30 p.m. | ||
| Thu., 3/16 | V Boys Swimming and Diving | CIAC Class S Finals | Away - SCSU | 1:00 p.m. | ||
| Fri., 3/17 | V Boys Swimming and Diving | CIAC Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/18 | V Boys Swimming and Diving | CIAC State Open Championship | Away - Yale | 1:00 p.m. | ||
| Thu., 3/23 | V Boys Lacrosse | John Jay (NY) (Scrim.) | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | ||
| Thu., 3/23 | JV Boys Lacrosse | John Jay (NY) (Scrim.) | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:30 p.m. | ||
| Thu., 3/23 | V Softball | Stamford (Scrim.) | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 4:00 p.m. | ||
| Fri., 3/24 | V Baseball | Staples (Scrim.) | Away - Staples HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Sat., 3/25 | V Girls Lacrosse | Play Day - Girls Lax | Away - Staples HS-Ginny Parker Field | 9:00 a.m. | ||
| Mon., 3/27 | V Baseball | Norwalk (Scrim.) | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 4:00 p.m. | ||
| Mon., 3/27 | JV Baseball | Norwalk (Scrim.) | Away - City Hall Field [Directions] | 4:00 p.m. | ||
| Mon., 3/27 | V Girls Lacrosse | Fairfield Ludlowe (Scrim.) | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:00 p.m. | ||
| Mon., 3/27 | JV Girls Lacrosse | Fairfield Ludlowe (Scrim.) | Home - Weston HS-WHS Lower Turf Field [Directions] | 3:30 p.m. | ||
| Tue., 3/28 | V Boys Tennis | Fairfield Warde (Scrim.) | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | ||
| Tue., 3/28 | V Softball | Greens Farms Academy (Scrim.) | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 4:00 p.m. | ||
| Tue., 3/28 | V Girls Tennis | Fairfield Warde (Scrim.) | Away - Fairfield Warde HS-Blake Courts [Directions] | 4:00 p.m. | ||
| Tue., 3/28 | JV Girls Tennis | Fairfield Warde (Scrim.) | Away - Fairfield Warde HS-Blake Courts [Directions] | 4:00 p.m. | ||
| Wed., 3/29 | V Baseball | Fairfield Ludlowe (Scrim.) | Away - Kiwanis Field-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 3/29 | JV Baseball | Fairfield Ludlowe (Scrim.) | Away - Owen Fish Park-Owen Fish [Directions] | 4:00 p.m. | ||
| Wed., 3/29 | V Boys Lacrosse | Notre Dame-West Haven (Scrim.) | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | ||
| Wed., 3/29 | JV Boys Lacrosse | Notre Dame-West Haven (Scrim.) | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 3/30 | V Boys Lacrosse | Wilton (Scrim.) | Away - Wilton HS-Veterans Memorial Stadium [Directions] | 6:00 p.m. | ||
| Thu., 3/30 | JV Boys Lacrosse | Wilton (Scrim.) | Away - Wilton HS-Veterans Memorial Stadium [Directions] | 4:00 p.m. | ||
| Thu., 3/30 | V Softball | Brien McMahon (Scrim.) | Away - Brien McMahon HS-Softball Diamond [Directions] | 4:00 p.m. | ||
| Thu., 3/30 | V Girls Tennis | Ridgefield (Scrim.) | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | ||
| Sat., 4/1 | V Girls Lacrosse | Fairfield Warde | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | W 18-7 | |
| Mon., 4/3 | V Baseball | New Canaan | Home - Weston HS-Revson #1 (Varsity) [Directions] | 4:30 p.m. | L 2-13 | |
| Mon., 4/3 | JV Baseball | New Canaan | Home - Weston HS-Revson #2 (JV) [Directions] | 4:30 p.m. | ||
| Mon., 4/3 | V Boys Tennis | Fairfield Ludlowe | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | L 1-6 [Detailed Results] | |
| Mon., 4/3 | V Girls Lacrosse | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | W 17-5 | |
| Mon., 4/3 | JV Girls Lacrosse | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Mon., 4/3 | V Softball | Joel Barlow | Away - Joel Barlow High-Field E (Softball) [Directions] | 4:15 p.m. | W 10-8 | |
| Mon., 4/3 | V Girls Tennis | St. Joseph | Away - St. Joseph HS-Tennis Courts [Directions] | 4:00 p.m. | W 5-2 [Detailed Results] | |
| Tue., 4/4 | V Boys Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 7:00 p.m. | W 9-6 | |
| Tue., 4/4 | JV Boys Lacrosse | Fairfield Ludlowe | Away - Tomlinson MS-Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 4/5 | V Baseball | Stamford | Away - Stamford HS-SHS Baseball Diamond [Directions] | 4:00 p.m. | W 13-11 | |
| Wed., 4/5 | JV Baseball | Stamford | Away - Belltown Park-Barrett Field, Belltown Park [Directions] | 4:00 p.m. | ||
| Wed., 4/5 | V Boys Lacrosse | Immaculate | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | W 18-0 | |
| Wed., 4/5 | V Boys Tennis | Brookfield | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Wed., 4/5 | V Girls Tennis | Brookfield | Away - Brookfield HS-BHS Tennis Courts [Directions] | 3:45 p.m. | W 6-1 [Detailed Results] | |
| Thu., 4/6 | V Baseball | Wright Tech | Home - Weston HS-Revson #1 (Varsity) [Directions] | 4:00 p.m. | W 15-5 | |
| Thu., 4/6 | V Boys Tennis | Trumbull | Away - Trumbull HS-Tennis Courts [Directions] | 3:45 p.m. | L 3-4 [Detailed Results] | |
| Thu., 4/6 | V Girls Golf | Masuk | Away - Whitney Farms Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 4/6 | V Softball | Wright Tech | Away - Scalzi Park-Scalzi #3 [Directions] | 3:45 p.m. | W 22-2 | |
| Thu., 4/6 | V Girls Tennis | Trumbull | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | W 6-1 [Detailed Results] | |
| Sat., 4/8 | JV Baseball | Newtown | Home - Weston HS-Revson #2 (JV) [Directions] | 11:00 a.m. | ||
| Sat., 4/8 | V Boys Lacrosse | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 12:00 p.m. | L 8-12 | |
| Sat., 4/8 | JV Boys Lacrosse | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 10:00 a.m. | ||
| Sat., 4/8 | V Boys Tennis | St. Joseph | Home - Weston HS-WHS Tennis Courts [Directions] | 11:00 a.m. | W 7-0 [Detailed Results] | |
| Sat., 4/8 | V Girls Lacrosse | Daniel Hand | Home - Weston HS-WHS Lower Turf Field [Directions] | 11:30 a.m. | W 9-3 | |
| Sat., 4/8 | JV Girls Lacrosse | Daniel Hand | Home - Weston HS-WHS Lower Turf Field [Directions] | 10:00 a.m. | ||
| Sat., 4/8 | V Softball | Lyman Hall | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 11:00 a.m. | L 4-14 | |
| Sat., 4/8 | V Girls Tennis | Greenwich | Away - Greenwich HS-Tennis Courts [Directions] | 12:00 p.m. | L 0-7 [Detailed Results] | |
| Mon., 4/10 | V Baseball | Pomperaug | Away - Pomperaug HS-Baseball Field [Directions] | 4:15 p.m. | W 4-2 | |
| Mon., 4/10 | V Boys Tennis | Bethel | Away - Bethel HS-BHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Mon., 4/10 | V Softball | Pomperaug | Away - Pomperaug HS-Softball Field [Directions] | 4:15 p.m. | L 2-21 | |
| Mon., 4/10 | V Girls Tennis | Bethel | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Tue., 4/11 | JV Baseball | Pomperaug | Home - Weston HS-Revson #2 (JV) [Directions] | 4:15 p.m. | ||
| Tue., 4/11 | V Boys Tennis | Hall | Away - University of St. Joseph [Directions] | 11:00 a.m. | L 2-5 [Detailed Results] | |
| Wed., 4/12 | V Baseball | Newtown | Home - Weston HS-Revson #1 (Varsity) [Directions] | 4:15 p.m. | W 2-1 (10) | |
| Wed., 4/12 | V Boys Tennis | Pomperaug | Away - Edgewood Bath and Tennis Club [Directions] | 10:00 a.m. | W 6-1 [Detailed Results] | |
| Wed., 4/12 | V Softball | Newtown | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 4:15 p.m. | L 0-24 | |
| Wed., 4/12 | V Girls Tennis | Pomperaug | Home - Weston HS-WHS Tennis Courts [Directions] | 10:00 a.m. | W 6-1 [Detailed Results] | |
| Thu., 4/13 | JV Baseball | Newtown | Away - Newtown HS-Nighthawk Ball Park [Directions] | 4:15 p.m. | ||
| Thu., 4/13 | V Boys Lacrosse | Brookfield | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | W 20-3 | |
| Thu., 4/13 | JV Boys Lacrosse | Brookfield | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 4/13 | V Girls Lacrosse | Brookfield | Away - Brookfield HS-BHS Stadium Field [Directions] | 6:00 p.m. | W 12-7 | |
| Thu., 4/13 | JV Girls Lacrosse | Brookfield | Away - Brookfield HS-BHS Stadium Field [Directions] | 4:15 p.m. | ||
| Sat., 4/15 | JV Baseball | Wilton | Home - Weston HS-Revson #2 (JV) [Directions] | Suspended | ||
| Sat., 4/15 | V Boys Lacrosse | Iona Prep (NY) | Away - IONA PREP-Lacrosse Field | 3:00 p.m. | L 7-15 | |
| Sat., 4/15 | JV Boys Lacrosse | Iona Prep (NY) | Away - Iona Preparatory School-Stadium | 1:00 p.m. | ||
| Sat., 4/15 | JV Girls Lacrosse | Fairfield Warde | Home - Weston HS-WHS Lower Turf Field [Directions] | Canceled | Cancelled | |
| Sat., 4/15 | V Softball | Bunnell | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 11:00 a.m. | W 8-7 | |
| Mon., 4/17 | V Boys Outdoor Track | Bunnell, Masuk, Notre Dame-Fairfield | Away - Bunnell HS-Bunnell Track [Directions] | 4:00 p.m. | Weston - 81 Bunnell - 67 Weston - 100 Masuk - 39 Weston - 97 Notre Dame - 42 | |
| Mon., 4/17 | V Girls Golf | Bunnell | Away - Bunnell HS-Oronoque C.C. [Directions] | 3:00 p.m. | ||
| Tue., 4/18 | V Baseball | New Fairfield | Away - New Fairfield HS-Baseball Field [Directions] | 4:15 p.m. | L 1-2 (8) | |
| Tue., 4/18 | JV Baseball | New Fairfield | Home - Weston HS-Revson #2 (JV) [Directions] | 4:15 p.m. | ||
| Tue., 4/18 | V Boys Lacrosse | Pomperaug | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | W 19-5 | |
| Tue., 4/18 | JV Boys Lacrosse | Pomperaug | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 4/18 | V Boys Tennis | Newtown | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Tue., 4/18 | V Girls Golf | Pomperaug | Away - Pomperaug HS-Pomperaug Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 4/18 | V Girls Lacrosse | Pomperaug | Away - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | W 15-7 | |
| Tue., 4/18 | JV Girls Lacrosse | Pomperaug | Away - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Tue., 4/18 | V Girls Outdoor Track | Masuk, Bunnell, Notre Dame-Fairfield | Away - Masuk HS-Edmund Butler Track @ Masuk HS [Directions] | 4:00 p.m. | Weston 99 bunnel 51 Weston 98 masuk 50 Weston 97 ND 47 | |
| Tue., 4/18 | V Softball | New Fairfield | Away - New Fairfield HS-Softball Field [Directions] | 4:15 p.m. | L 6-10 | |
| Tue., 4/18 | V Girls Tennis | Newtown | Away - Newtown HS-NHS Tennis Courts [Directions] | 3:45 p.m. | W 4-3 [Detailed Results] | |
| Wed., 4/19 | V Baseball | Kolbe Cathedral | Home - Weston HS-Revson #1 (Varsity) [Directions] | 4:15 p.m. | W 4-3 | |
| Wed., 4/19 | V Boys Tennis | New Fairfield | Away - New Fairfield HS-Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Wed., 4/19 | V Girls Golf | Immaculate | Away - Richter Park Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 4/19 | V Softball | Kolbe Cathedral | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 4:15 p.m. | W 9-6 | |
| Wed., 4/19 | V Girls Tennis | New Fairfield | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Thu., 4/20 | V Baseball | Bethel | Away - Bethel HS-Hunt Field at Bethel HS [Directions] | 6:00 p.m. | L 5-6 (8) | |
| Thu., 4/20 | JV Baseball | Wilton | Home - Weston HS-Revson #2 (JV) [Directions] | 4:30 p.m. | ||
| Thu., 4/20 | V Boys Lacrosse | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 7:00 p.m. | W 19-5 | |
| Thu., 4/20 | JV Boys Lacrosse | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 5:00 p.m. | ||
| Thu., 4/20 | V Boys Tennis | Daniel Hand | Away - Polson MS, Madison-Polson Tennis Courts/DHHS Campus [Directions] | 3:45 p.m. | L 3-4 [Detailed Results] | |
| Thu., 4/20 | V Girls Golf | Brookfield | Away - Sunset Hill Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 4/20 | V Girls Lacrosse | Newtown | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:30 p.m. | L 8-18 | |
| Thu., 4/20 | JV Girls Lacrosse | Newtown | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 4/20 | V Softball | Bethel | Away - Bethel HS-Kisling Field [Directions] | 6:00 p.m. | L 3-13 | |
| Sat., 4/22 | V Baseball | Wilton | Home - Weston HS-Revson #1 (Varsity) [Directions] | 11:00 a.m. | L 4-20 | |
| Sat., 4/22 | JV Baseball | Bethel | Home - Weston HS-Revson #2 (JV) [Directions] | 1:00 p.m. | ||
| Sat., 4/22 | V Boys Lacrosse | Notre Dame-Fairfield | Home - Weston HS-WHS Lower Turf Field [Directions] | 11:00 a.m. | W 20-0 | |
| Sat., 4/22 | V Girls Lacrosse | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Park Ave Field [Directions] | 10:30 a.m. | W 16-4 | |
| Sat., 4/22 | JV Girls Lacrosse | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Park Ave Field [Directions] | Canceled | Cancelled | |
| Sat., 4/22 | V Softball | Greenwich | Away - Greenwich HS-Softball Field [Directions] | 11:00 a.m. | L 2-5 | |
| Sat., 4/22 | V Girls Tennis | Glastonbury | Away - Glastonbury HS-Tennis Courts [Directions] | 11:00 a.m. | L 2-5 [Detailed Results] | |
| Mon., 4/24 | V Boys Outdoor Track | Immaculate, Newtown | Home - Weston HS-WHS Track [Directions] | 4:00 p.m. | Weston - 106 Immaculate - 42 Newtown - 96.5 Weston - 53.5 | |
| Mon., 4/24 | V Boys Tennis | Joel Barlow | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | W 5-2 [Detailed Results] | |
| Mon., 4/24 | V Girls Golf | Immaculate | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | ||
| Mon., 4/24 | V Girls Outdoor Track | Immaculate, Newtown | Home - Weston HS-WHS Track [Directions] | 4:00 p.m. | Weston 131 Immaculate 13 Weston 87 Newtown 63 | |
| Mon., 4/24 | V Softball | Immaculate | Away - Immaculate HS-Softball Diamond [Directions] | 4:15 p.m. | L 8-15 | |
| Mon., 4/24 | V Girls Tennis | Joel Barlow | Away - Joel Barlow HS-Tennis Courts [Directions] | 3:45 p.m. | W 4-3 [Detailed Results] | |
| Tue., 4/25 | V Baseball | Immaculate | Away - Immaculate HS-Baseball Diamond [Directions] | 4:15 p.m. | L 0-9 | |
| Tue., 4/25 | V Boys Lacrosse | Joel Barlow | Away - Joel Barlow HS-Joel Barlow HS Stadium [Directions] | 7:00 p.m. | W 14-6 | |
| Tue., 4/25 | JV Boys Lacrosse | Joel Barlow | Away - Joel Barlow HS-Joel Barlow HS Stadium [Directions] | 5:30 p.m. | ||
| Tue., 4/25 | V Girls Lacrosse | Joel Barlow | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:30 p.m. | W 11-8 | |
| Tue., 4/25 | JV Girls Lacrosse | Joel Barlow | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 4/26 | V Baseball | Brookfield | Home - Weston HS-Revson #1 (Varsity) [Directions] | 4:15 p.m. | L 5-9 | |
| Wed., 4/26 | V Boys Tennis | Bunnell | Away - Bunnell HS-Bunnell Tennis Courts [Directions] | 3:45 p.m. | W 6-1 [Detailed Results] | |
| Wed., 4/26 | V Softball | Brookfield | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 4:15 p.m. | L 0-19 | |
| Wed., 4/26 | V Girls Tennis | Bunnell | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Thu., 4/27 | V Boys Lacrosse | Bunnell-Stratford | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | W 20-3 | |
| Thu., 4/27 | JV Boys Lacrosse | Bunnell-Stratford | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 4/28 | V Baseball | Stratford | Home - Weston HS-Revson #1 (Varsity) [Directions] | 4:15 p.m. | W 5-2 | |
| Fri., 4/28 | JV Baseball | Brookfield | Home - Weston HS-Revson #2 (JV) [Directions] | 4:00 p.m. | ||
| Fri., 4/28 | V Boys Outdoor Track | O'Grady Relays @ Danbury High School | Home - Weston HS-WHS Track [Directions] | 4:00 p.m. | ||
| Fri., 4/28 | V Softball | Stratford | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 4:15 p.m. | L 5-10 | |
| Sat., 4/29 | JV Baseball | Stratford | Away - Penders Field-Penders Field - Stratford [Directions] | Postponed | ||
| Sat., 4/29 | V Boys Lacrosse | St. Joseph | Home - Weston HS-WHS Lower Turf Field [Directions] | 12:00 p.m. | L 5-6 | |
| Sat., 4/29 | JV Boys Lacrosse | St. Joseph | Home - Weston HS-WHS Lower Turf Field [Directions] | 10:00 a.m. | ||
| Sat., 4/29 | V Boys Outdoor Track | O'Grady Relays @ Danbury High School | Away - Not Listed | 9:00 a.m. | ||
| Sat., 4/29 | V Girls Lacrosse | Amity | Away - Amity Regional HS-William Johnson Stadium Field [Directions] | 11:00 a.m. | W 13-9 | |
| Sat., 4/29 | JV Girls Lacrosse | Amity | Away - Amity Regional HS-William Johnson Stadium Field [Directions] | 12:45 p.m. | ||
| Sat., 4/29 | V Girls Outdoor Track | O'Grady Relays at Danbury High School | Away - Not Listed | 9:00 a.m. | ||
| Mon., 5/1 | V Boys Outdoor Track | Brookfield, Joel Barlow, Kolbe Cathedral | Away - Brookfield HS-BHS Track [Directions] | 4:00 p.m. | Weston-88 Brookfield - 60 Weston - 111.5Barlow - 38.5 Weston - 107 Kolbe - 38 | |
| Mon., 5/1 | V Girls Golf | Newtown | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | ||
| Mon., 5/1 | V Softball | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Park Ave Field [Directions] | 4:15 p.m. | L 0-12 | |
| Tue., 5/2 | V Boys Lacrosse | Bethel | Away - Bethel HS-MS turf lacrosse field [Directions] | 4:15 p.m. | W 20-2 | |
| Tue., 5/2 | JV Boys Lacrosse | Bethel | Away - Bethel HS-MS turf lacrosse field [Directions] | 6:15 p.m. | ||
| Tue., 5/2 | V Girls Golf | Masuk | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | ||
| Tue., 5/2 | V Girls Lacrosse | Bethel | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:30 p.m. | W 17-4 | |
| Tue., 5/2 | JV Girls Lacrosse | Bethel | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 5/2 | V Girls Outdoor Track | Brookfield, Joel Barlow, Kolbe Cathedral | Home - Weston HS-WHS Track [Directions] | 4:00 p.m. | weston 104 kolbe 36 weston 104 brookfield 44 weston 82 joel barlow 62 | |
| Wed., 5/3 | V Boys Tennis | Stratford | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Wed., 5/3 | V Girls Golf | Bunnell | Away - Bunnell HS-Oronoque C.C. [Directions] | 3:00 p.m. | ||
| Wed., 5/3 | V Softball | New Milford | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 4:15 p.m. | L 2-15 | |
| Wed., 5/3 | V Girls Tennis | Stratford | Away - Flood MS-Flood MS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Thu., 5/4 | V Baseball | Notre Dame-Fairfield | Away - Bunnell HS [Directions] | 5:30 p.m. | W 6-4 | |
| Thu., 5/4 | JV Baseball | New Milford | Away - New Milford HS-Baseball Sub Varsity Field - NMHS [Directions] | 4:15 p.m. | ||
| Thu., 5/4 | V Girls Lacrosse | Stratford/Bunnell | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:30 p.m. | W 16-2 | |
| Thu., 5/4 | JV Girls Lacrosse | Stratford/Bunnell | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 5/5 | V Boys Tennis | Wilton | Away - Wilton HS-Tennis Courts [Directions] | 4:15 p.m. | L Weston [Detailed Results] | |
| Fri., 5/5 | JV Boys Tennis | Wilton | Away - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | ||
| Sat., 5/6 | V Baseball | Jonathan Law | Away - Jonathan Law HS-Baseball Field [Directions] | 3:00 p.m. | L 6-8 | |
| Sat., 5/6 | JV Baseball | Masuk | Home - Weston HS-Revson #1 (Varsity) [Directions] | 10:00 a.m. | ||
| Sat., 5/6 | V Girls Lacrosse | Canton | Away - Canton HS-Canton H.S. Turf [Directions] | 1:45 p.m. | W 16-5 | |
| Sat., 5/6 | JV Girls Lacrosse | Canton | Away - Canton HS-Canton H.S. Turf [Directions] | 12:30 p.m. | ||
| Sat., 5/6 | JV Girls Tennis | Cardinal Kung Academy | Home - Weston HS-WHS Tennis Courts [Directions] | 10:00 a.m. | ||
| Mon., 5/8 | V Baseball | Masuk | Home - Weston HS-Revson #1 (Varsity) [Directions] | 4:15 p.m. | W 5-4 | |
| Mon., 5/8 | V Boys Outdoor Track | Bethel, New Fairfield, Stratford | Away - Bethel HS-BHS track [Directions] | 4:00 p.m. | Weston 91 Stratford 54 Weston 81 New Fairfield 69 Bethel 105 Weston 45 | |
| Mon., 5/8 | V Boys Tennis | New Milford | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Mon., 5/8 | V Girls Golf | Brookfield, Stratford | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | ||
| Mon., 5/8 | V Softball | Masuk | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 4:15 p.m. | L 0-19 | |
| Mon., 5/8 | V Girls Tennis | New Milford | Away - New Milford HS-Tennis Courts - NMHS [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Tue., 5/9 | JV Baseball | Masuk | Away - Masuk HS-John Giampaolo Baseball Field @ Masuk HS [Directions] | 4:15 p.m. | ||
| Tue., 5/9 | V Boys Lacrosse | New Fairfield | Home - Weston HS-WHS Lower Turf Field [Directions] | 7:00 p.m. | W 11-7 | |
| Tue., 5/9 | JV Boys Lacrosse | New Fairfield | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:15 p.m. | ||
| Tue., 5/9 | V Girls Lacrosse | New Fairfield | Away - New Fairfield HS-Marty Morgan Field [Directions] | 4:15 p.m. | W 10-8 | |
| Tue., 5/9 | JV Girls Lacrosse | New Fairfield | Away - New Fairfield HS-Marty Morgan Field [Directions] | 6:00 p.m. | ||
| Tue., 5/9 | V Girls Outdoor Track | New Fairfield, Bethel, Stratford | Away - New Fairfield HS-Stadium Field [Directions] | 4:00 p.m. | weston 76 bethel 72 weston 93 NF 54 weston 103 stratford 31 | |
| Wed., 5/10 | V Baseball | Joel Barlow | Home - Weston HS-Revson #1 (Varsity) [Directions] | 4:15 p.m. | L 0-14 | |
| Wed., 5/10 | V Boys Tennis | Masuk | Away - Wolfe Park-Tennis Courts [Directions] | 3:45 p.m. | W 5-2 [Detailed Results] | |
| Wed., 5/10 | V Girls Golf | Joel Barlow | Away - Redding Country Club [Directions] | 3:00 p.m. | ||
| Wed., 5/10 | V Softball | Joel Barlow | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 4:30 p.m. | W 14-2 | |
| Wed., 5/10 | V Girls Tennis | Masuk | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Thu., 5/11 | V Baseball | New Milford | Home - Weston HS-Revson #1 (Varsity) [Directions] | 4:15 p.m. | L 1-4 | |
| Thu., 5/11 | JV Baseball | Joel Barlow | Away - Joel Barlow HS-Baseball Field [Directions] | 4:15 p.m. | ||
| Thu., 5/11 | V Boys Lacrosse | New Milford | Away - New Milford HS-Joe Wiser Stadium - NMHS [Directions] | 7:00 p.m. | W 12-5 | |
| Thu., 5/11 | JV Boys Lacrosse | New Milford | Away - New Milford HS-North Turf Field - NMHS [Directions] | 5:00 p.m. | ||
| Thu., 5/11 | V Girls Golf | Newtown | Away - Newtown Country Club [Directions] | 3:00 p.m. | ||
| Thu., 5/11 | V Girls Lacrosse | New Milford | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:30 p.m. | W 14-2 | |
| Thu., 5/11 | JV Girls Lacrosse | New Milford | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 5/11 | V Girls Tennis | Notre Dame-Fairfield | Home - Weston HS-WHS Tennis Courts [Directions] | 4:15 p.m. | W 7-0 [Detailed Results] | |
| Fri., 5/12 | V Girls Outdoor Track | Loucks Games, White Plains, NY | Away - Not Listed | 9:00 a.m. | ||
| Fri., 5/12 | V Softball | New Fairfield | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 4:00 p.m. | L 4-12 | |
| Sat., 5/13 | V Baseball | ValleyReg/Westbrook | Away - Valley Regional HS-Baseball Diamond [Directions] | 12:00 p.m. | W 2-0 | |
| Sat., 5/13 | V Boys Lacrosse | Daniel Hand | Home - Weston HS-WHS Lower Turf Field [Directions] | 12:00 p.m. | W 11-9 | |
| Sat., 5/13 | JV Boys Lacrosse | Daniel Hand | Home - Weston HS-WHS Lower Turf Field [Directions] | 10:00 a.m. | ||
| Sat., 5/13 | V Boys Outdoor Track | Loucks Games, White Plains, NY | Away - . | 9:00 a.m. | ||
| Sat., 5/13 | V Boys Outdoor Track | Freshmen SWC track meet | Away - Bethel HS-BHS track | 4:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 5/18 | ||||||
| Sat., 5/13 | V Girls Lacrosse | Immaculate | Away - Immaculate HS-Mustang Valley [Directions] | 12:00 p.m. | W 16-2 | |
| Sat., 5/13 | V Girls Outdoor Track | Loucks Games, White Plains, NY | Away - Not Listed | 9:00 a.m. | ||
| Mon., 5/15 | V Baseball | Bunnell | Away - Bunnell HS-Bunnell Baseball Field [Directions] | 6:00 p.m. | W 4-2 | |
| Mon., 5/15 | V Boys Lacrosse | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 6:00 p.m. | W 16-4 | |
| Mon., 5/15 | V Boys Outdoor Track | New Milford, Pomperaug | Home - Weston HS-WHS Track [Directions] | 4:00 p.m. | Weston 81 New Milford 69 Weston 84.5 Pomperaug 65.5 | |
| Mon., 5/15 | V Boys Tennis | Immaculate | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 [Detailed Results] | |
| Mon., 5/15 | V Girls Golf | Joel Barlow | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | ||
| Mon., 5/15 | V Girls Lacrosse | Masuk | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | W 16-9 | |
| Mon., 5/15 | JV Girls Lacrosse | Masuk | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:30 p.m. | ||
| Mon., 5/15 | V Softball | Bunnell | Away - Bunnell HS-Bunnell Softball FIeld [Directions] | 4:15 p.m. | W 6-4 | |
| Mon., 5/15 | V Girls Tennis | Immaculate | Away - Rogers Park (Danbury, CT)-Tennis Courts [Directions] | 3:45 p.m. | W 6-1 [Detailed Results] | |
| Tue., 5/16 | V Baseball | Brookfield | Away - Brookfield HS-Baseball Field [Directions] | 4:15 p.m. | L 5-15 | |
| Tue., 5/16 | JV Baseball | Bunnell | Home - Weston HS-Revson #2 (JV) [Directions] | 4:15 p.m. | ||
| Tue., 5/16 | V Girls Golf | Pomperaug | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | ||
| Tue., 5/16 | V Girls Outdoor Track | Pomperaug, New Milford | Away - Pomperaug HS-Stadium [Directions] | 4:00 p.m. | Weston 86 New Milford 63 Weston 85 Pomperaug 65 | |
| Tue., 5/16 | V Softball | Abbott Tech | Away - Hatters Park-Hatters #1 [Directions] | 3:45 p.m. | W 23-1 | |
| Thu., 5/18 | V Boys Lacrosse | Masuk | Home - Weston HS-WHS Lower Turf Field [Directions] | 7:00 p.m. | W 16-4 | |
| Thu., 5/18 | V Girls Golf | Stratford | Away - Mill River Country Club [Directions] | 3:00 p.m. | ||
| Thu., 5/18 | V Girls Lacrosse | Brookfield | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:00 p.m. | W 17-7 | |
| Sun., 5/21 | V Baseball | Brookfield | Away - Brookfield HS-Baseball Field [Directions] | 2:00 p.m. | L 1-8 | |
| Mon., 5/22 | V Boys Outdoor Track | SWC Outdoor Track Championship | Away - Bunnell HS-Bunnell Track | 3:00 p.m. | ||
| Mon., 5/22 | V Girls Lacrosse | New Fairfield | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | L 7-8 | |
| Mon., 5/22 | V Girls Outdoor Track | SWC Outdoor Track Championship | Away - Bunnell HS-Track | 3:00 p.m. | ||
| Tue., 5/23 | V Boys Lacrosse | Newtown | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | W 9-3 | |
| Thu., 5/25 | V Boys Lacrosse | New Milford | Home - Newtown HS-Blue and Gold Stadium [Directions] | 6:30 p.m. | W 12-6 | |
| Sat., 5/27 | V Boys Tennis | Branford | Home - Weston HS-WHS Tennis Courts [Directions] | 1:00 p.m. | W 7-0 [Detailed Results] | |
| Sat., 5/27 | V Girls Lacrosse | Ridgefield (Scrim.) | Home - Weston HS-WHS Lower Turf Field [Directions] | 9:00 a.m. | ||
| Sun., 5/28 | V Girls Tennis | Sacred Heart Academy | Home - Weston HS-WHS Tennis Courts [Directions] | 1:00 p.m. | W 5-2 | |
| Tue., 5/30 | V Baseball | Bullard Havens Tech | Away - Beardsley Park [Directions] | 3:30 p.m. | W 7-2 | |
| Tue., 5/30 | V Boys Outdoor Track | CIAC Class M Championships | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 5/30 | V Boys Tennis | Ledyard | Home - Weston HS-WHS Tennis Courts [Directions] | 3:00 p.m. | W 7-0 [Detailed Results] | |
| Tue., 5/30 | V Girls Golf | SWC Girls Golf Championship | Away - Fairchild Wheeler Golf Course | 8:00 a.m. | ||
| Tue., 5/30 | V Girls Lacrosse | Lewis Mills | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | W 16-2 | |
| Tue., 5/30 | V Girls Outdoor Track | CIAC Class M Championships | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 5/30 | V Girls Outdoor Track | CIAC Class M Championship Meet at Willowbrook Park, New Britain | Away - Not Listed | 10:00 a.m. | ||
| Tue., 5/30 | V Girls Tennis | Woodland | Home - Weston HS-WHS Tennis Courts [Directions] | 1:00 p.m. | W 7-0 | |
| Wed., 5/31 | V Baseball | Joel Barlow | Away - Joel Barlow HS-Baseball Field [Directions] | 3:30 p.m. | L 3-10 | |
| Wed., 5/31 | V Boys Lacrosse | Waterford | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:30 p.m. | W 15-2 | |
| Wed., 5/31 | V Boys Tennis | Ellington | Away - Ellington HS-Tennis Courts [Directions] | 3:00 p.m. | W 6-1 [Detailed Results] | |
| Wed., 5/31 | V Girls Tennis | Stonington | Away - Stonington HS-SHS Tennis Courts [Directions] | 5:00 p.m. | L 2-5 | |
| Thu., 6/1 | Unified Sports Basketball | Bethel | Away - Bethel HS-Kisling Field [Directions] | 4:00 p.m. | ||
| Fri., 6/2 | V Girls Lacrosse | Somers | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:00 p.m. | W 18-9 | |
| Sat., 6/3 | V Boys Lacrosse | Stonington | Home - Weston HS-WHS Lower Turf Field [Directions] | 3:00 p.m. | W 20-5 | |
| Mon., 6/5 | V Boys Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/5 | V Boys Tennis | CIAC Individual Invitational Opening Rounds | Away - Wesleyan | 10:00 a.m. | ||
| Mon., 6/5 | V Girls Golf | CIAC Division II Championship | Away - Tashua Knolls GC | 8:30 a.m. | ||
| Mon., 6/5 | V Girls Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/5 | V Girls Tennis | CIAC Individual Invitational Opening Rounds | Away - Wesleyan | 10:00 a.m. | ||
| Tue., 6/6 | V Boys Tennis | CIAC Individual Invitational Round of 16 | Away - Wesleyan | 12:00 p.m. | ||
| Tue., 6/6 | V Boys Tennis | CIAC Individual Invitational Quarterfinals | Away - Wesleyan | 3:30 p.m. | ||
| Tue., 6/6 | V Girls Tennis | CIAC Individual Invitational Round of 16 | Away - Wesleyan | 12:00 p.m. | ||
| Tue., 6/6 | V Girls Tennis | CIAC Individual Invitational Quarterfinals | Away - Wesleyan | 3:30 p.m. | ||
| Wed., 6/7 | V Boys Tennis | CIAC Individual Invitational Semifinals | Away - Wesleyan | 3:30 p.m. | ||
| Wed., 6/7 | V Girls Tennis | CIAC Individual Invitational Semifinals | Away - Wesleyan | 3:30 p.m. | ||
| Thu., 6/8 | V Boys Tennis | CIAC Individual Invitational Finals | Away - Wesleyan | 3:30 p.m. | ||
| Thu., 6/8 | V Girls Tennis | CIAC Individual Invitational Finals | Away - Wesleyan | 3:30 p.m. | ||
| Fri., 6/9 | V Boys Lacrosse | New Fairfield | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:30 p.m. | W 14-5 | |
| Sat., 6/10 | V Girls Golf | CIAC State Open Championship | Away - Black Hall Club | 1:00 p.m. | ||
| Sat., 6/10 | V Girls Lacrosse | Canton | Home - Weston HS-WHS Lower Turf Field [Directions] | 1:30 p.m. | W 15-8 | |
| Sun., 6/11 | V Boys Lacrosse | St. Joseph | Away - Sacred Heart University [Directions] | 10:00 a.m. | ||
| Tue., 6/13 | V Boys Outdoor Track | CIAC Decathlon Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 6/13 | V Girls Lacrosse | New Fairfield | Home - Sacred Heart University-Campus Field [Directions] | 8:00 p.m. | ||
| Tue., 6/13 | V Girls Outdoor Track | CIAC Heptathlon Championship | Away - Willow Brook Park | 10:30 a.m. | ||
| Tue., 6/13 | V Girls Outdoor Track | CIAC Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/14 | V Boys Outdoor Track | CIAC Decathlon Championship | Away - Willow Brook Park | 8:30 a.m. | ||
| Wed., 6/14 | V Boys Outdoor Track | CIAC Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/14 | V Girls Outdoor Track | CIAC Heptathlon Championship | Away - Willow Brook Park | 8:30 a.m. | ||