| Weston 2023-24 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 697 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Tue., 8/22 | V Boys Golf | Joel Barlow | Home - Weston HS-Aspetuck Country Club [Directions] | 10:00 a.m. | ||
| Thu., 8/24 | V Boys Golf | Newtown | Home - Weston HS-Aspetuck Country Club [Directions] | 9:30 a.m. | ||
| Sat., 8/26 | V Football | ATI, Bethel, Lewis Mills, Masuk, New Fairfield, Seymour, Harding | Away - Immaculate HS-Mustang Valley | 9:00 a.m. | ||
| Sat., 8/26 | Miscellaneous Events | SAT/ACT's | Home - TBA [Directions] | 8:00 a.m. | ||
| Sun., 8/27 | V Boys Soccer | Alumni Game | Home - Weston HS-WHS Stadium Field [Directions] | 6:00 p.m. | ||
| Tue., 8/29 | V Boys Soccer | Norwalk (Scrim.) | Home - Weston HS-WHS Stadium Field [Directions] | 5:00 p.m. | ||
| Tue., 8/29 | JV Boys Soccer | Norwalk (Scrim.) | Home - Weston HS-WHS Lower Turf Field [Directions] | 3:30 p.m. | ||
| Tue., 8/29 | V Girls Soccer | New Canaan (Scrim.) | Home - Weston HS-WHS Stadium Field [Directions] | 6:30 p.m. | ||
| Wed., 8/30 | V Boys Golf | Pomperaug | Away - Pomperaug HS-Highfield Country Club [Directions] | 3:00 p.m. | ||
| Thu., 8/31 | V Football | Seymour (Scrim.) | Home - Weston HS-WHS Stadium Field [Directions] | 6:00 p.m. | ||
| Thu., 8/31 | V Girls Soccer | Holy Cross (Scrim.) | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:30 p.m. | Cancelled | |
| Fri., 9/1 | V Field Hockey | New Fairfield, Bethel, Brookfield, New Milford, Newtown, Ridgefield, Shepaug Valley | Away - New Fairfield HS-Marty Morgan Field | 3:30 p.m. | ||
| Sat., 9/2 | V Boys Soccer | Trumbull (Scrim.) | Away - Trumbull HS-Cork Field [Directions] | 10:00 a.m. | ||
| Sat., 9/2 | JV Boys Soccer | Trumbull (Scrim.) | Away - Trumbull HS-JV Grass Field [Directions] | 10:00 a.m. | ||
| Sat., 9/2 | 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. | ||
| Sat., 9/2 | V Girls Soccer | Ridgefield (Scrim.) | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 10:00 a.m. | ||
| Tue., 9/5 | V Boys Golf | Immaculate | Away - Immaculate HS-Richter Park [Directions] | 3:00 p.m. | ||
| Tue., 9/5 | V Boys Soccer | Wilton (Scrim.) | Away - Wilton HS-Lilly Field [Directions] | 6:00 p.m. | ||
| Tue., 9/5 | JV Boys Soccer | Wilton (Scrim.) | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | ||
| Tue., 9/5 | V Girls Soccer | Fairfield Ludlowe (Scrim.) | Home - Weston HS-WHS Stadium Field [Directions] | 6:00 p.m. | ||
| Tue., 9/5 | JV Girls Soccer | Fairfield Ludlowe (Scrim.) | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:30 p.m. | ||
| Tue., 9/5 | V Girls Volleyball | New Canaan (Scrim.) | Away - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 9/6 | V Girls Volleyball | Fairfield Ludlowe (Scrim.) | Home - Weston HS-Gym (New) [Directions] | 5:30 p.m. | ||
| Wed., 9/6 | JV Girls Volleyball | Fairfield Ludlowe (Scrim.) | Home - Weston HS-Gym (New) [Directions] | 4:00 p.m. | ||
| Wed., 9/6 | FR Girls Volleyball | Fairfield Ludlowe (Scrim.) | Home - Weston HS-Gym (Old) [Directions] | 4:00 p.m. | ||
| Thu., 9/7 | V Girls Soccer | Greenwich Country Day (Scrim.) | Home - Weston HS-WHS Stadium Field [Directions] | 6:30 p.m. | ||
| Fri., 9/8 | V Football | Weaver | Home - Weston HS-WHS Stadium Field [Directions] | 7:00 p.m. | W 46-19 | |
| Fri., 9/8 | V Girls Volleyball | Brien McMahon | Away - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | L 0-3 | |
| Sat., 9/9 | V Boys Cross Country | Wilton Invitational | Away - Not Listed | 9:00 a.m. | ||
| Sat., 9/9 | JV Football | Pomperaug | Home - Weston HS-WHS Stadium Field [Directions] | 10:00 a.m. | ||
| Sat., 9/9 | V Girls Cross Country | Wilton Invitational | Away - Not Listed | 9:00 a.m. | ||
| Sat., 9/9 | V Field Hockey | Joel Barlow | Away - Joel Barlow HS-Field J (Competition Field) [Directions] | 1:30 p.m. | W 1-0 | |
| Sat., 9/9 | JV Field Hockey | Joel Barlow | Away - Joel Barlow HS-Field J (Competition Field) [Directions] | 12:00 p.m. | ||
| Sat., 9/9 | V Girls Volleyball | Norwalk | Away - Stamford HS-Kuczo Gymnasium [Directions] | 12:30 p.m. | W 3-1 | |
| Mon., 9/11 | V Field Hockey | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:15 p.m. | W 3-1 | |
| Mon., 9/11 | JV Field Hockey | Fairfield Warde | Away - Fairfield Warde HS-Fairfield Warde Grass Utility Field [Directions] | 5:30 p.m. | ||
| Mon., 9/11 | V Girls Volleyball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:45 p.m. | L 1-3 | |
| Mon., 9/11 | JV Girls Volleyball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Tue., 9/12 | V Boys Cross Country | Kolbe Cathedral, Bunnell, Stratford | Away - Seaside Park-Seaside Park [Directions] | 4:30 p.m. | Kolbe 23 Weston 34 Weston 22 Stratford 39 Weston 17 Bunnell 44 | |
| Tue., 9/12 | V Boys Soccer | Bethel | Home - Weston HS-WHS Stadium Field [Directions] | 6:00 p.m. | L 0-3 | |
| Tue., 9/12 | JV Boys Soccer | Bethel | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 9/12 | V Girls Cross Country | Kolbe Cathedral, Bunnell, Stratford | Away - Seaside Park-Seaside Park [Directions] | 5:00 p.m. | Weston 15 Kolbe 50 Weston 15 Stratford 50 Weston 16 Bunnell 47 | |
| Tue., 9/12 | V Girls Soccer | Bethel | Away - Bethel HS-MS Turf Soccer Field [Directions] | 6:30 p.m. | L 0-1 | |
| Tue., 9/12 | JV Girls Soccer | Bethel | Away - Bethel HS-Rockwell Field [Directions] | 4:15 p.m. | ||
| Tue., 9/12 | V Girls Swimming and Diving | New Fairfield | Away - New Fairfield HS-Pool [Directions] | 6:00 p.m. | Weston 99 New Fairfield 65 | |
| Wed., 9/13 | V Girls Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 5:30 p.m. | L 2-3 | |
| Wed., 9/13 | JV Girls Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Wed., 9/13 | FR Girls Volleyball | Staples | Away - Staples HS-Field House [Directions] | 4:00 p.m. | ||
| Thu., 9/14 | V Football | Notre Dame-Fairfield | Home - Weston HS-WHS Stadium Field [Directions] | 7:30 p.m. | L 0-35 | |
| Thu., 9/14 | V Boys Soccer | Pomperaug | Home - Weston HS-WHS Stadium Field [Directions] | 4:15 p.m. | L 0-1 | |
| Thu., 9/14 | JV Boys Soccer | Pomperaug | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:15 p.m. | ||
| Thu., 9/14 | V Girls Soccer | Pomperaug | Away - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | W 1-0 | |
| Thu., 9/14 | JV Girls Soccer | Pomperaug | Away - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Thu., 9/14 | V Girls Volleyball | Fairfield Warde | Home - Weston HS-Gym (New) [Directions] | 6:00 p.m. | L 0-3 | |
| Thu., 9/14 | JV Girls Volleyball | Fairfield Warde | Home - Weston HS-Gym (New) [Directions] | 4:30 p.m. | ||
| Thu., 9/14 | FR Girls Volleyball | Fairfield Warde | Home - Weston HS-Gym (Old) [Directions] | 4:30 p.m. | ||
| Sun., 9/17 | JV Football | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -McCarty Stadium [Directions] | 12:00 p.m. | ||
| Mon., 9/18 | V Field Hockey | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 7:00 p.m. | W 1-0 | |
| Mon., 9/18 | JV Field Hockey | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 5:30 p.m. | ||
| Mon., 9/18 | V Girls Volleyball | Bunnell | Home - Weston HS-Gym (New) [Directions] | 6:45 p.m. | W 3-0 | |
| Mon., 9/18 | JV Girls Volleyball | Bunnell | Home - Weston HS-Gym (New) [Directions] | 5:15 p.m. | ||
| Tue., 9/19 | V Boys Cross Country | Bethel, Immaculate | Home - Weston HS-WHS Stadium Field [Directions] | 4:30 p.m. | Weston 28 Immaculate 28 Bethel 24 Weston 31 | |
| Tue., 9/19 | V Boys Soccer | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 6:00 p.m. | L 2-7 | |
| Tue., 9/19 | JV Boys Soccer | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 4:00 p.m. | ||
| Tue., 9/19 | V Girls Cross Country | Bethel, Immaculate | Home - Weston HS-WHS Stadium Field [Directions] | 5:00 p.m. | Bethel 20 Weston 39 Weston 19 Immaculate 38 | |
| Tue., 9/19 | V Girls Soccer | Newtown | Home - Weston HS-WHS Stadium Field [Directions] | 6:00 p.m. | W 2-1 | |
| Tue., 9/19 | JV Girls Soccer | Newtown | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 9/20 | V Boys Golf | Bethel | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | ||
| Wed., 9/20 | V Field Hockey | Brookfield | Away - Brookfield HS-BHS Stadium Field [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 9/20 | JV Field Hockey | Brookfield | Away - Brookfield HS-BHS Stadium Field [Directions] | 4:00 p.m. | ||
| Wed., 9/20 | V Girls Volleyball | Westhill | Home - Weston HS-Gym (New) [Directions] | 5:30 p.m. | L 2-3 | |
| Wed., 9/20 | JV Girls Volleyball | Westhill | Home - Weston HS-Gym (New) [Directions] | 4:00 p.m. | ||
| Wed., 9/20 | FR Girls Volleyball | Westhill | Home - Weston HS-Gym (Old) [Directions] | 4:00 p.m. | ||
| Thu., 9/21 | V Boys Golf | Joel Barlow | Away - Redding Country Club [Directions] | 3:00 p.m. | ||
| Thu., 9/21 | V Boys Soccer | New Fairfield | Home - Weston HS-WHS Stadium Field [Directions] | 6:00 p.m. | L 1-3 | |
| Thu., 9/21 | JV Boys Soccer | New Fairfield | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 9/21 | V Girls Soccer | New Fairfield | Away - New Fairfield HS-Marty Morgan Field [Directions] | 6:00 p.m. | W 2-0 | |
| Thu., 9/21 | JV Girls Soccer | New Fairfield | Away - New Fairfield HS-Marty Morgan Field [Directions] | 4:00 p.m. | ||
| Fri., 9/22 | V Field Hockey | Westhill | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:45 p.m. | W 2-0 | |
| Fri., 9/22 | JV Field Hockey | Westhill | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:15 p.m. | ||
| Fri., 9/22 | V Girls Swimming and Diving | Brookfield | Away - Brookfield YMCA-Outside/Dome Pool [Directions] | 4:30 p.m. | Weston 100 Brookfield 84 | |
| Fri., 9/22 | V Girls Volleyball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 5:00 p.m. | W 3-1 | |
| Fri., 9/22 | JV Girls Volleyball | Brookfield | Away - Brookfield HS-BHS Small Gym [Directions] | 5:00 p.m. | ||
| Fri., 9/22 | FR Girls Volleyball | Brookfield | Away - Brookfield HS-BHS Small Gym [Directions] | 3:30 p.m. | ||
| Sat., 9/23 | V Football | Tolland | Away - Tolland HS-Stadium [Directions] | 1:00 p.m. | L 7-36 | |
| Sat., 9/23 | V Girls Soccer | Watertown | Away - Swift MS-Swift MS [Directions] | 12:00 p.m. | L 0-1 | |
| Sat., 9/23 | JV Girls Soccer | Watertown | Away - Swift MS-Soccer Field [Directions] | 2:00 p.m. | ||
| Tue., 9/26 | V Boys Cross Country | Brookfield, Masuk | Home - Weston HS-WHS Stadium Field [Directions] | 4:30 p.m. | Brookfield 18 Weston 28 Weston 23 Masuk 32 | |
| Tue., 9/26 | V Boys Soccer | Kolbe Cathedral | Away - Veterans Memorial Park CT [Directions] | 4:15 p.m. | W 5-0 | |
| Tue., 9/26 | V Girls Cross Country | Brookfield, Masuk | Home - Weston HS-WHS Stadium Field [Directions] | 5:00 p.m. | Weston 23 Masuk 32 Weston 28 Brookfield 31 | |
| Tue., 9/26 | V Girls Soccer | Kolbe Cathedral | Home - Weston HS-WHS Stadium Field [Directions] | 6:00 p.m. | W 7-0 | |
| Tue., 9/26 | V Girls Swimming and Diving | Newtown | Away - Newtown HS-pool [Directions] | 6:00 p.m. | Weston 101 Newtown 85 | |
| Tue., 9/26 | V Girls Volleyball | Pomperaug | Away - Pomperaug HS-Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Tue., 9/26 | JV Girls Volleyball | Pomperaug | Away - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 9/26 | FR Girls Volleyball | Pomperaug | Away - Pomperaug HS-Auxiliary Gym [Directions] | 4:00 p.m. | ||
| Wed., 9/27 | V Boys Golf | New Milford | Away - Candlewood Valley Country Club [Directions] | 3:00 p.m. | ||
| Wed., 9/27 | V Field Hockey | Immaculate | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:30 p.m. | L 0-1 | |
| Wed., 9/27 | JV Field Hockey | Immaculate | Home - Weston HS-WHS Lower Turf Field [Directions] | Postponed | ||
| Thu., 9/28 | V Boys Golf | CIAC Fall Golf Classic at Orange Hills GC | Away - Not Listed | 2:30 p.m. | ||
| Thu., 9/28 | V Boys Soccer | Immaculate | Home - Weston HS-WHS Stadium Field [Directions] | 6:00 p.m. | W 1-0 | |
| Thu., 9/28 | JV Boys Soccer | Immaculate | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 9/28 | V Girls Swimming and Diving | Joel Barlow | Home - Weston HS-Weston MS Pool [Directions] | 4:00 p.m. | Weston 92 Joel Barlow 50 | |
| Thu., 9/28 | V Girls Volleyball | Newtown | Home - Weston HS-Gym (New) [Directions] | 5:30 p.m. | L 1-3 | |
| Thu., 9/28 | JV Girls Volleyball | Newtown | Home - Weston HS-Gym (New) [Directions] | 4:00 p.m. | ||
| Thu., 9/28 | FR Girls Volleyball | Newtown | Home - Weston HS-Gym (Old) [Directions] | 4:00 p.m. | ||
| Fri., 9/29 | V Football | Bethel | Home - Weston HS-WHS Stadium Field [Directions] | 7:00 p.m. | W 21-7 | |
| Sat., 9/30 | V Field Hockey | St. Joseph | Home - Weston HS-WHS Lower Turf Field [Directions] | 11:30 a.m. | W 4-0 | |
| Sat., 9/30 | JV Field Hockey | St. Joseph | Home - Weston HS-WHS Lower Turf Field [Directions] | 10:00 a.m. | ||
| Sat., 9/30 | V Girls Soccer | Haddam-Killingworth | Home - Weston HS-WHS Stadium Field [Directions] | 10:00 a.m. | W 3-2 | |
| Sat., 9/30 | JV Girls Soccer | Haddam-Killingworth | Home - Weston HS-WHS Stadium Field [Directions] | 12:00 p.m. | ||
| Sat., 9/30 | V Girls Volleyball | Stamford | Home - Weston HS-Gym (New) [Directions] | 10:30 a.m. | L 1-3 | |
| Sat., 9/30 | JV Girls Volleyball | Stamford | Home - Weston HS-Gym (New) [Directions] | 12:00 p.m. | ||
| Sat., 9/30 | FR Girls Volleyball | Stamford | Home - Weston HS-Gym (Old) [Directions] | 10:30 a.m. | ||
| Mon., 10/2 | V Boys Golf | New Fairfield | Away - Quaker Hill CC [Directions] | 3:00 p.m. | ||
| Mon., 10/2 | V Field Hockey | Newtown | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:30 p.m. | W 2-0 | |
| Mon., 10/2 | JV Field Hockey | Newtown | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 10/2 | V Girls Volleyball | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Mon., 10/2 | JV Girls Volleyball | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | 4:30 p.m. | ||
| Mon., 10/2 | FR Girls Volleyball | New Fairfield | Away - New Fairfield HS-Old High School Gym [Directions] | 4:30 p.m. | ||
| Tue., 10/3 | V Boys Cross Country | Joel Barlow, New Fairfield, Pomperaug | Away - Joel Barlow HS-Cross Country Course [Directions] | 4:30 p.m. | Weston 25 Joel Barlow 36 Pomperaug 20 Weston 43 Weston 18 New Fairfield 45 | |
| Tue., 10/3 | V Boys Golf | Notre Dame-Fairfield | Away - Fairchild Wheeler Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 10/3 | V Boys Soccer | Brookfield | Away - Brookfield HS-BHS Back Turf [Directions] | 6:00 p.m. | T 3-3 | |
| Tue., 10/3 | JV Boys Soccer | Brookfield | Away - Brookfield HS-BHS Back Turf [Directions] | 4:00 p.m. | ||
| Tue., 10/3 | V Girls Cross Country | Joel Barlow, New Fairfield, Pomperaug | Away - Joel Barlow HS-Cross Country Course [Directions] | 5:00 p.m. | Joel Barlow 21 Weston 35 Pomperaug 17 Weston 46 New Fairfield 17 Weston 41 | |
| Tue., 10/3 | V Girls Soccer | Brookfield | Home - Weston HS-WHS Stadium Field [Directions] | 6:00 p.m. | W 2-1 | |
| Tue., 10/3 | JV Girls Soccer | Brookfield | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 10/3 | V Girls Swimming and Diving | Pomperaug | Home - Weston HS-Weston MS Pool [Directions] | 4:00 p.m. | Pomperaug 101 Weston 84 | |
| Wed., 10/4 | V Boys Golf | Masuk | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | ||
| Wed., 10/4 | V Boys Golf | Brookfield | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | ||
| Wed., 10/4 | V Field Hockey | New Fairfield | Away - New Fairfield HS-Marty Morgan Field [Directions] | 5:30 p.m. | L 0-1 | |
| Wed., 10/4 | JV Field Hockey | New Fairfield | Away - New Fairfield HS-Marty Morgan Field [Directions] | 4:00 p.m. | ||
| Wed., 10/4 | V Girls Volleyball | Kolbe Cathedral | Home - Weston HS-Gym (New) [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 10/4 | JV Girls Volleyball | Kolbe Cathedral | Home - Weston HS-Gym (New) [Directions] | 4:00 p.m. | ||
| Thu., 10/5 | V Boys Golf | CHAPPA Tournament at Longshore Golf Course, Westport | Away - Not Listed | 8:30 a.m. | ||
| Thu., 10/5 | V Boys Soccer | Stratford | Away - Penders Field-Penders Field - Stratford [Directions] | 7:00 p.m. | W 3-0 | |
| Thu., 10/5 | JV Boys Soccer | Stratford | Away - Penders Field-Penders Field - Stratford [Directions] | 5:00 p.m. | ||
| Thu., 10/5 | V Girls Soccer | Stratford | Home - Weston HS-WHS Stadium Field [Directions] | 7:00 p.m. | W 4-0 | |
| Thu., 10/5 | JV Girls Soccer | Stratford | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:15 p.m. | ||
| Fri., 10/6 | V Girls Swimming and Diving | New Milford | Away - O'Neill Arena - Canterbury Prep-Canterbury School Pool [Directions] | 7:00 p.m. | Weston 100 New Milford 77 | |
| Fri., 10/6 | V Girls Volleyball | Immaculate | Away - Immaculate HS [Directions] | 7:00 p.m. | L 2-3 | |
| Fri., 10/6 | JV Girls Volleyball | Immaculate | Away - Immaculate HS [Directions] | 5:30 p.m. | ||
| Fri., 10/6 | FR Girls Volleyball | Immaculate | Away - Immaculate HS [Directions] | 4:00 p.m. | ||
| Sat., 10/7 | V Boys Cross Country | Wickham Invitational | Away - Not Listed | 9:00 a.m. | ||
| Sat., 10/7 | V Girls Cross Country | Wickham Invitational | Away - Not Listed | 9:00 a.m. | ||
| Sat., 10/7 | V Field Hockey | Shepaug Valley | Home - Weston HS-WHS Lower Turf Field [Directions] | 11:30 a.m. | W 1-0 | |
| Sat., 10/7 | JV Field Hockey | Shepaug Valley | Home - Weston HS-WHS Lower Turf Field [Directions] | 10:00 a.m. | ||
| Sat., 10/7 | Miscellaneous Events | SAT's | Home - TBA [Directions] | 8:00 a.m. | ||
| Tue., 10/10 | V Boys Cross Country | New Milford, Newtown, Notre Dame-Fairfield | Away - New Milford HS-Joe Wiser Stadium - NMHS [Directions] | 4:30 p.m. | New Milford 20 Weston 35 Weston 27 Newtown 28 Weston 15 Notre Dame 49 | |
| Tue., 10/10 | V Boys Golf | Stratford | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | ||
| Tue., 10/10 | V Boys Golf | Bunnell | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | ||
| Tue., 10/10 | V Boys Soccer | Notre Dame-Fairfield | Home - Weston HS-WHS Stadium Field [Directions] | 6:00 p.m. | L 0-3 | |
| Tue., 10/10 | JV Boys Soccer | Cardinal Kung Academy | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 10/10 | V Girls Cross Country | New Milford, Newtown, Notre Dame-Fairfield | Away - New Milford HS-Joe Wiser Stadium - NMHS [Directions] | 5:00 p.m. | New Milford 15 Weston 50 Weston 15 Notre Dame 50 Newtown 17 Weston 42 | |
| Tue., 10/10 | V Girls Soccer | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Park Ave Field [Directions] | 7:00 p.m. | L 2-6 | |
| Tue., 10/10 | V Girls Swimming and Diving | Masuk | Home - Weston HS-Weston MS Pool [Directions] | 4:00 p.m. | Weston 100 Masuk 78 | |
| Tue., 10/10 | V Girls Volleyball | Bethel | Home - Weston HS-Gym (New) [Directions] | 5:30 p.m. | W 3-0 | |
| Tue., 10/10 | JV Girls Volleyball | Bethel | Home - Weston HS-Gym (New) [Directions] | 4:00 p.m. | ||
| Tue., 10/10 | FR Girls Volleyball | Bethel | Home - Weston HS-Gym (Old) [Directions] | 4:00 p.m. | ||
| Tue., 10/10 | Unified Sports Soccer | Bethel | Away - Bethel HS-DeSantis Field at Bethel High [Directions] | 3:00 p.m. | ||
| Wed., 10/11 | V Boys Golf | Newtown | Away - Rock Ridge Country Club [Directions] | 3:00 p.m. | ||
| Wed., 10/11 | V Field Hockey | Joel Barlow | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 10/11 | JV Field Hockey | Joel Barlow | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 10/12 | V Boys Soccer | New Milford | Away - New Milford HS-Joe Wiser Stadium - NMHS [Directions] | 6:00 p.m. | L 1-3 | |
| Thu., 10/12 | JV Boys Soccer | New Milford | Away - New Milford HS-Joe Wiser Stadium - NMHS [Directions] | 4:00 p.m. | ||
| Thu., 10/12 | V Girls Soccer | New Milford | Home - Weston HS-WHS Stadium Field [Directions] | 6:00 p.m. | W 3-0 | |
| Thu., 10/12 | JV Girls Soccer | New Milford | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 10/12 | V Girls Volleyball | Stratford | Home - Weston HS-Gym (New) [Directions] | 6:30 p.m. | W 3-1 | |
| Thu., 10/12 | JV Girls Volleyball | Stratford | Home - Weston HS-Gym (New) [Directions] | 5:00 p.m. | ||
| Thu., 10/12 | FR Girls Volleyball | Stratford | Home - Weston HS-Gym (Old) [Directions] | 5:00 p.m. | ||
| Fri., 10/13 | V Football | Pomperaug | Away - Pomperaug HS-Stadium [Directions] | 6:30 p.m. | L 7-38 | |
| Fri., 10/13 | V Girls Soccer | Shelton | Away - Shelton HS-Finn Stadium [Directions] | 6:00 p.m. | T 0-0 | |
| Fri., 10/13 | JV Girls Soccer | Shelton | Away - Shelton HS-Finn Stadium [Directions] | 4:30 p.m. | ||
| Fri., 10/13 | V Girls Swimming and Diving | Bunnell | Away - Bunnell HS-Flood M.S. Pool [Directions] | 6:00 p.m. | Weston 84 Bunnell 73 | |
| Sat., 10/14 | JV Football | Pomperaug | Home - Weston HS-WHS Stadium Field [Directions] | Canceled | Cancelled | |
| Sat., 10/14 | FR Boys Soccer | Newtown | Home - Weston HS-WHS Stadium Field [Directions] | 9:00 a.m. | ||
| Sat., 10/14 | V Field Hockey | Bethel | Home - Weston HS-WHS Lower Turf Field [Directions] | 10:00 a.m. | W 5-0 | |
| Sat., 10/14 | JV Field Hockey | Bethel | Home - Weston HS-WHS Lower Turf Field [Directions] | 11:30 a.m. | ||
| Mon., 10/16 | V Field Hockey | Bethel | Away - Bethel HS-MS Turf Soccer Field [Directions] | 6:30 p.m. | W 1-0 | |
| Mon., 10/16 | JV Field Hockey | Bethel | Away - Bethel HS-Hunt Field at Bethel HS [Directions] | 5:00 p.m. | ||
| Tue., 10/17 | V Boys Soccer | Masuk | Home - Weston HS-WHS Stadium Field [Directions] | 6:00 p.m. | L 2-4 | |
| Tue., 10/17 | JV Boys Soccer | Masuk | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 10/17 | V Girls Soccer | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 6:00 p.m. | L 1-3 | |
| Tue., 10/17 | JV Girls Soccer | Masuk | Away - Masuk HS-Masuk High School Middle Field [Directions] | 4:00 p.m. | ||
| Tue., 10/17 | V Girls Swimming and Diving | Bethel/Immaculate | Home - Weston HS-Weston MS Pool [Directions] | 7:00 p.m. | Weston 84 Bethel/Immaculate 66 | |
| Tue., 10/17 | V Girls Volleyball | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Sister Marion Reilly Auditorium [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 10/17 | JV Girls Volleyball | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Sister Marion Reilly Auditorium [Directions] | 4:30 p.m. | ||
| Wed., 10/18 | V Boys Cross Country | SWC Champioship | Away - Bethel HS-BHS track | 3:00 p.m. | ||
| Wed., 10/18 | V Boys Golf | SWC Boys Golf Championship at Fairchild Wheeler-Black Course | Away - TBA | 8:30 a.m. | ||
| Wed., 10/18 | V Girls Cross Country | SWC Champioship | Away - Bethel HS-BHS track | 3:00 p.m. | ||
| Wed., 10/18 | V Field Hockey | Pomperaug | Away - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | T 0-0 | |
| Wed., 10/18 | JV Field Hockey | Pomperaug | Away - Pomperaug HS-Stadium [Directions] | 5:30 p.m. | ||
| Thu., 10/19 | V Boys Soccer | Joel Barlow | Away - Joel Barlow HS-Field I (Stadium) [Directions] | 7:00 p.m. | L 0-2 | |
| Thu., 10/19 | JV Boys Soccer | Joel Barlow | Away - Joel Barlow HS-Field I (Stadium) [Directions] | 5:00 p.m. | ||
| Thu., 10/19 | V Girls Soccer | Joel Barlow | Home - Weston HS-WHS Stadium Field [Directions] | 6:00 p.m. | W 4-0 | |
| Thu., 10/19 | JV Girls Soccer | Joel Barlow | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 10/19 | V Girls Volleyball | New Milford | Home - Weston HS-Gym (New) [Directions] | 7:00 p.m. | W 3-0 | |
| Thu., 10/19 | JV Girls Volleyball | New Milford | Home - Weston HS-Gym (New) [Directions] | 5:30 p.m. | ||
| Thu., 10/19 | FR Girls Volleyball | New Milford | Home - Weston HS-Gym (Old) [Directions] | 5:30 p.m. | ||
| Fri., 10/20 | V Football | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 7:00 p.m. | L 7-42 | |
| Fri., 10/20 | V Girls Swimming and Diving | Woodland | Home - Weston HS-Weston MS Pool [Directions] | 4:00 p.m. | Weston | |
| Sat., 10/21 | V Field Hockey | Lauralton Hall | Home - Weston HS-WHS Lower Turf Field [Directions] | 3:30 p.m. | W 3-1 | |
| Sat., 10/21 | JV Field Hockey | Lauralton Hall | Home - Weston HS-WHS Lower Turf Field [Directions] | 2:00 p.m. | ||
| Sat., 10/21 | V Girls Soccer | Immaculate | Away - Immaculate HS-Mustang Valley [Directions] | 12:00 p.m. | W 6-1 | |
| Sat., 10/21 | V Girls Volleyball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 12:30 p.m. | W 3-1 | |
| Sat., 10/21 | JV Girls Volleyball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 11:30 a.m. | ||
| Sat., 10/21 | FR Girls Volleyball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 10:00 a.m. | ||
| Mon., 10/23 | V Boys Soccer | Bunnell | Home - Weston HS-WHS Stadium Field [Directions] | 7:00 p.m. | L 0-1 | |
| Mon., 10/23 | JV Boys Soccer | Bunnell | Home - Weston HS-WHS Stadium Field [Directions] | 5:15 p.m. | ||
| Mon., 10/23 | V Field Hockey | New Milford | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:30 p.m. | T 1-1 | |
| Mon., 10/23 | JV Field Hockey | New Milford | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 10/23 | V Girls Soccer | Bunnell | Away - Bunnell HS-Mastroni Field [Directions] | 6:00 p.m. | W 7-2 | |
| Mon., 10/23 | JV Girls Soccer | Bunnell | Away - Bunnell HS-Mastroni Field [Directions] | 4:00 p.m. | ||
| Mon., 10/23 | V Girls Volleyball | Joel Barlow | Home - Weston HS-Gym (New) [Directions] | 5:30 p.m. | L 0-3 | |
| Mon., 10/23 | JV Girls Volleyball | Joel Barlow | Home - Weston HS-Gym (New) [Directions] | 4:00 p.m. | ||
| Tue., 10/24 | V Girls Swimming and Diving | Stratford | Home - Weston HS-Weston MS Pool [Directions] | 4:00 p.m. | Weston 97 Stratford 71 | |
| Wed., 10/25 | V Boys Soccer | Abbott Tech | Home - Weston HS-WHS Stadium Field [Directions] | 6:00 p.m. | W 6-0 | |
| Wed., 10/25 | JV Girls Volleyball | Cardinal Kung Academy | Home - Weston HS-Gym (New) [Directions] | 4:00 p.m. | ||
| Thu., 10/26 | V Field Hockey | New Milford | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | L 0-2 | |
| Fri., 10/27 | V Football | New Fairfield | Home - Weston HS-WHS Stadium Field [Directions] | 7:00 p.m. | L 7-33 | |
| Sat., 10/28 | V Boys Cross Country | CIAC Class M Championship | Away - Wickham Park | 11:55 a.m. | ||
| Sat., 10/28 | JV Football | New Fairfield | Away - New Fairfield HS-Stadium Field [Directions] | Canceled | Cancelled | |
| Sat., 10/28 | V Girls Cross Country | CIAC Class SS Championship | Away - Wickham Park | 10:10 a.m. | ||
| Sat., 10/28 | V Girls Soccer | Newtown | Home - Weston HS-WHS Stadium Field [Directions] | 4:00 p.m. | L 0-2 | |
| Sat., 10/28 | V Girls Volleyball | Immaculate | Home - Weston HS-Gym (New) [Directions] | 6:00 p.m. | W 3-0 | |
| Sat., 10/28 | JV Girls Volleyball | Fairfield Warde, Brien McMahon, Darien, Fairfield Ludlowe, Greenwich Country Day, Greenwich, Shelton, Stamford, Trumbull | Away - Fairfield Warde HS-Large Gym | 9:00 a.m. | ||
| Sat., 10/28 | Miscellaneous Events | ACT's | Home - TBA [Directions] | 8:00 a.m. | ||
| Mon., 10/30 | V Girls Swimming and Diving | Bethel/Immaculate, Brookfield, Immaculate, Joel Barlow, Masuk, New Fairfield, New Milford, Newtown, Pomperaug | Home - Weston HS-Weston MS Pool [Directions] | 5:30 p.m. | Warm-ups start at 4pm. | |
| Wed., 11/1 | V Field Hockey | Joel Barlow (Scrim.) | Away - Joel Barlow HS-Field J [Directions] | 3:45 p.m. | ||
| Wed., 11/1 | V Girls Volleyball | Newtown | Away - Newtown HS-Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Thu., 11/2 | V Boys Swimming and Diving | TBA, Brookfield, Bunnell-Stratford, Immaculate, Joel Barlow-Bethel Swim, TBA, New Fairfield, Notre Dame-Fairfield, Pomperaug, Stratford | Away - Masuk HS-Pool | 4:00 p.m. | ||
| Thu., 11/2 | V Girls Swimming and Diving | SWC Swimming Championship | Away - Masuk HS-Pool | 5:00 p.m. | ||
| Fri., 11/3 | V Football | New Milford | Away - New Milford HS-Joe Wiser Stadium - NMHS [Directions] | 7:00 p.m. | L 26-46 | |
| Sat., 11/4 | JV Football | New Milford | Home - Weston HS-WHS Stadium Field [Directions] | Canceled | Cancelled | |
| Sat., 11/4 | V Girls Swimming and Diving | SWC Championship Swim Meet at Masuk | Away - Not Listed | 3:30 p.m. | ||
| Sat., 11/4 | V Girls Volleyball | SWC Championships at a neutral site | Away - Not Listed | 6:00 p.m. | ||
| Mon., 11/6 | V Boys Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Mon., 11/6 | V Girls Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Mon., 11/6 | V Girls Soccer | Tolland | Home - Weston HS-WHS Stadium Field [Directions] | 5:30 p.m. | W 1-0 | |
| Mon., 11/6 | V Girls Volleyball | Kaynor Tech | Away - Kaynor Technical School-Kaynor Gymnasium [Directions] | 4:00 p.m. | W 3-0 | |
| Tue., 11/7 | V Field Hockey | Watertown | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:30 p.m. | W 2-0 | |
| Wed., 11/8 | V Girls Soccer | Lewis Mills | Away - Nassahegan Recreation Complex-Nassahegan Field [Directions] | 4:00 p.m. | L 1-2 | |
| Wed., 11/8 | V Girls Swimming and Diving | CIAC Class S Diving Championship | Away - Sheehan | 5:30 p.m. | ||
| Wed., 11/8 | V Girls Volleyball | Suffield | Away - Suffield HS [Directions] | 5:00 p.m. | L 1-3 | |
| Wed., 11/8 | Unified Sports Soccer | Bethel | Home - Weston HS-Gym (New) [Directions] | 3:00 p.m. | ||
| Thu., 11/9 | V Field Hockey | Canton | Away - Canton HS-Canton H.S. Turf [Directions] | 5:00 p.m. | L 0-3 | |
| Fri., 11/10 | V Football | Brookfield | Home - Weston HS-WHS Stadium Field [Directions] | 7:00 p.m. | L 50-28 | |
| Sat., 11/11 | JV Football | Brookfield | Away - Brookfield HS-BHS Back Turf [Directions] | Canceled | Cancelled | |
| Sat., 11/11 | V Girls Swimming and Diving | CIAC Class S Qualifying Meet | Away - Cheshire Community Pool | 6:15 p.m. | ||
| Wed., 11/15 | V Girls Swimming and Diving | CIAC Class S Finals | Away - SCSU | 6:00 p.m. | ||
| Thu., 11/16 | V Girls Swimming and Diving | CIAC State Open Diving | Away - Middletown | 5:30 p.m. | ||
| Fri., 11/17 | JV Football | Joel Barlow | Home - Weston HS-WHS Stadium Field [Directions] | Canceled | Cancelled | |
| Sun., 11/19 | V Girls Swimming and Diving | CIAC State Open Swimming | Away - Yale | 1:00 p.m. | ||
| Mon., 11/20 | JV Football | Bethel | Away - Bethel HS-DeSantis Field at Bethel High [Directions] | Canceled | Cancelled | |
| Thu., 11/23 | V Football | Joel Barlow | Away - Joel Barlow HS-Field I (Stadium) [Directions] | 10:00 a.m. | L 6-30 | |
| Thu., 11/30 | V | Wilton | Away - Wilton HS [Directions] | 3:00 p.m. | ||
| Tue., 12/5 | V Girls Basketball | Staples (Scrim.) | Home - Weston HS-Gym (New) [Directions] | 5:15 p.m. | ||
| Wed., 12/6 | V Girls Ice Hockey | Guilford Coop | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | W 3-2 | |
| Wed., 12/6 | Miscellaneous Events | Winter Freshman/New Athlete and Parent Orientation | Home - Weston HS-Cafeteria [Directions] | 6:00 p.m. | All freshmen athletes and any athlete new to our school along with a parent/guardian who did not attend this meeting in the fall must be in attendance in order to participate this winter. | |
| Thu., 12/7 | V Boys Basketball | Oxford (Scrim.) | Home - Weston HS-Gym (New) [Directions] | 5:30 p.m. | 4 Varsity quarters and 2 JV quarters | |
| Mon., 12/11 | V Boys Basketball | Wooster (Scrim.) | Home - Weston HS-Gym (New) [Directions] | 5:30 p.m. | ||
| Mon., 12/11 | JV Boys Ice Hockey | Bethel/Brookfield/Danbury/Immaculate | Home - Danbury Ice Arena-Patriot Rink [Directions] | 4:00 p.m. | ||
| Mon., 12/11 | V Girls Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 6:15 p.m. | L 30-56 | |
| Mon., 12/11 | JV Girls Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:30 p.m. | ||
| Wed., 12/13 | V Boys Ice Hockey | Housatonic Coop | Away - South Kent School-Ice Rink [Directions] | 8:40 p.m. | W 5-1 | |
| Wed., 12/13 | V Wrestling | Masuk | Home - Weston HS-Gym (New) [Directions] | 6:00 p.m. | Weston 64 - Masuk 18 | |
| Wed., 12/13 | V Girls Ice Hockey | Hamden Coop | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:30 p.m. | L 6-0 | |
| Thu., 12/14 | V Girls Basketball | Darien | Home - Weston HS-Gym (New) [Directions] | 6:00 p.m. | L 31-41 | |
| Thu., 12/14 | JV Girls Basketball | Darien | Home - Weston HS-Gym (New) [Directions] | 4:15 p.m. | ||
| Fri., 12/15 | V Boys Indoor Track | Coach St. Classic at the Armory in NYC | Away - Not Listed | 5:00 p.m. | ||
| Fri., 12/15 | V Girls Indoor Track | Coach St. Classic at the Armory in NYC | Away - Not Listed | 5:00 p.m. | ||
| Sat., 12/16 | V Boys Ice Hockey | Newington Coop | Home - Danbury Ice Arena-Patriot Rink [Directions] | 1:30 p.m. | L 3-2 | |
| Sat., 12/16 | V Wrestling | Darien Invitational | Away - Darien HS-DHS Main Gym | 9:00 a.m. | ||
| Sat., 12/16 | V Girls Basketball | New Canaan | Home - Weston HS-Gym (New) [Directions] | 12:15 p.m. | L 32-42 | |
| Sat., 12/16 | JV Girls Basketball | New Canaan | Home - Weston HS-Gym (New) [Directions] | 10:30 a.m. | ||
| Sun., 12/17 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Away - Hamden-Lou Astorino Ice Rink [Directions] | 3:00 p.m. | L 3-2 | |
| Tue., 12/19 | V Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 7:00 p.m. | W 71-51 | |
| Tue., 12/19 | JV Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 12/19 | FR Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 12/20 | V Boys Ice Hockey | Staples | Home - Danbury Ice Arena-Patriot Rink [Directions] | 8:00 p.m. | L 3-1 | |
| Wed., 12/20 | V Wrestling | Brookfield/Shepaug | Home - Weston HS-Gym (New) [Directions] | 6:00 p.m. | Weston 48 Brookfield 36 | |
| Wed., 12/20 | V | Unified Bowling at Nutmeg Bowling Alley | Home - Weston HS-Gym (Old) [Directions] | 3:30 p.m. | ||
| Wed., 12/20 | V Girls Basketball | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | 7:00 p.m. | L 18-48 | |
| Wed., 12/20 | JV Girls Basketball | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | 5:30 p.m. | ||
| Wed., 12/20 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | T 2-2 | |
| Thu., 12/21 | V Boys Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 7:00 p.m. | L 44-51 | |
| Thu., 12/21 | JV Boys Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 12/21 | FR Boys Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 12/21 | V Boys Swimming and Diving | New Fairfield | Home - Weston HS-Weston MS Pool [Directions] | 4:00 p.m. | Weston 81 New Fairfield 70 | |
| Sat., 12/23 | V Girls Ice Hockey | West Haven/SHA | Away - West Haven HS-Bennett Rink [Directions] | 1:00 p.m. | L 3-1 | |
| Tue., 12/26 | V Boys Ice Hockey | TBA | Home - Danbury Ice Arena-Patriot Rink [Directions] | 5:30 p.m. | ||
| Wed., 12/27 | V Boys Basketball | Stamford | Home - New Fairfield HS-High School Gym [Directions] | 6:00 p.m. | L 53-74 | |
| Wed., 12/27 | JV Boys Basketball | Stamford | Home - New Fairfield HS-High School Gym [Directions] | 3:00 p.m. | ||
| Wed., 12/27 | V Boys Ice Hockey | Milford Coop | Home - Danbury Ice Arena-Patriot Rink [Directions] | 5:30 p.m. | W 6-0 | |
| Fri., 12/29 | V Boys Basketball | Bridgeport Central | Away - New Fairfield HS-High School Gym [Directions] | 5:00 p.m. | W 67-57 | |
| Tue., 1/2 | V Girls Basketball | Bassick | Away - Bassick HS-Gym [Directions] | 5:30 p.m. | W 63-45 | |
| Tue., 1/2 | JV Girls Basketball | Bassick | Away - Bassick HS-Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/3 | V Boys Ice Hockey | Newtown/New Fairfield | Home - Danbury Ice Arena-Patriot Rink [Directions] | 5:30 p.m. | L 3-0 | |
| Wed., 1/3 | V Wrestling | Newtown | Away - Newtown HS-Gym [Directions] | 7:00 p.m. | Newtown 66 Weston 15 | |
| Thu., 1/4 | V Boys Basketball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 7:00 p.m. | L 55-57 | |
| Thu., 1/4 | JV Boys Basketball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 5:30 p.m. | ||
| Thu., 1/4 | FR Boys Basketball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 4:00 p.m. | ||
| Thu., 1/4 | JV Boys Ice Hockey | Newtown/New Fairfield | Home - Danbury Ice Arena-Patriot Rink [Directions] | 8:15 p.m. | ||
| Thu., 1/4 | V Boys Swimming and Diving | Newtown | Home - Weston HS-Weston MS Pool [Directions] | 4:00 p.m. | Weston 97 Newtown 77 | |
| Thu., 1/4 | V Girls Basketball | Masuk | Home - Weston HS-Gym (New) [Directions] | 6:00 p.m. | L 32-51 | |
| Thu., 1/4 | JV Girls Basketball | Masuk | Home - Weston HS-Gym (New) [Directions] | 4:15 p.m. | ||
| Fri., 1/5 | V Boys Ice Hockey | Westhill/Stamford | Away - Terry Conners - Stamford-Ice Rink [Directions] | 3:30 p.m. | L 2-1 | |
| Sat., 1/6 | V Boys Basketball | Harding | Away - Warren Harding HS-Gym [Directions] | 2:00 p.m. | W 54-53 | |
| Sat., 1/6 | JV Boys Basketball | Harding | Away - Warren Harding HS-Gym [Directions] | 12:30 p.m. | ||
| Sat., 1/6 | FR Boys Basketball | Harding | Away - Warren Harding HS-Gym [Directions] | 11:00 a.m. | ||
| Sat., 1/6 | V Boys Indoor Track | SWC Developmental at Bethel | Away - Bethel HS-Bethel Track and Field Center | 2:00 p.m. | ||
| Sat., 1/6 | V Girls Gymnastics | Daniel Hand, Fairfield Warde, TBA | Away - Polson MS, Small Gym-Polson Middle School/DHHS Campus [Directions] | 10:00 a.m. | Ludlowe 127.90 | |
| Sat., 1/6 | V Girls Ice Hockey | Suffield Coop | Away - Enfield Twin Rinks-Rink 1 [Directions] | 4:10 p.m. | L 2-0 | |
| Sat., 1/6 | V Girls Indoor Track | Bethel | Home - Bethel HS-Track and Field Training Center [Directions] | 2:00 p.m. | ||
| Mon., 1/8 | V Boys Basketball | New Milford | Away - New Milford HS-Main Gym - NMHS [Directions] | 7:00 p.m. | W 58-30 | |
| Mon., 1/8 | JV Boys Basketball | New Milford | Away - New Milford HS-Main Gym - NMHS [Directions] | 5:30 p.m. | ||
| Mon., 1/8 | FR Boys Basketball | New Milford | Away - New Milford HS-Main Gym - NMHS [Directions] | 4:00 p.m. | ||
| Mon., 1/8 | V Girls Basketball | New Milford | Home - Weston HS-Gym (New) [Directions] | 6:00 p.m. | L 33-57 | |
| Mon., 1/8 | JV Girls Basketball | New Milford | Home - Weston HS-Gym (New) [Directions] | 4:15 p.m. | ||
| Wed., 1/10 | V Wrestling | Notre Dame-Fairfield | Home - Weston HS-Gym (New) [Directions] | 6:00 p.m. | Weston 60 Notre Dame 6 | |
| Wed., 1/10 | V Girls Ice Hockey | West Haven/SHA | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:45 p.m. | W 3-1 | |
| Thu., 1/11 | V Boys Basketball | Newtown | Home - Weston HS-Gym (New) [Directions] | 7:00 p.m. | W 60-50 | |
| Thu., 1/11 | JV Boys Basketball | Newtown | Home - Weston HS-Gym (New) [Directions] | 5:15 p.m. | ||
| Thu., 1/11 | FR Boys Basketball | Newtown | Home - Weston HS-Gym (New) [Directions] | 3:45 p.m. | ||
| Thu., 1/11 | V Boys Ice Hockey | John Jay (NY) | Home - Danbury Ice Arena-Patriot Rink [Directions] | 8:15 p.m. | W 6-1 | |
| Thu., 1/11 | V Girls Basketball | Newtown | Away - Newtown HS-Gym [Directions] | 7:00 p.m. | L 34-62 | |
| Thu., 1/11 | JV Girls Basketball | Newtown | Away - Newtown HS-Gym [Directions] | 5:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 5:15 p.m. | ||||||
| Fri., 1/12 | V Boys Indoor Track | The Yale High School Classic at Coxe Cage, Yale | Away - Not Listed | 1:00 p.m. | ||
| Fri., 1/12 | V Wrestling | Darien | Home - Weston HS-Gym (New) [Directions] | 6:00 p.m. | Weston 54 Darien 21 | |
| Fri., 1/12 | V Girls Indoor Track | The Yale High School Classic at Coxe Cage, Yale | Away - Not Listed | 1:00 p.m. | ||
| Sat., 1/13 | V Boys Indoor Track | The Yale High School Classic at Coxe Cage, Yale | Away - Not Listed | 8:00 a.m. | ||
| Sat., 1/13 | V Boys Indoor Track | Bethel, Bunnell, Kolbe Cathedral, Masuk, New Fairfield, Pomperaug | Away - Bethel HS-Track and Field Training Center | 9:00 a.m. | ||
| Sat., 1/13 | V Boys Swimming and Diving | Fairfield Prep | Away - Fairfield University-RecPlex Pool [Directions] | 2:00 p.m. | Fairfield Prep 102 Weston 70 | |
| Sat., 1/13 | V Girls Ice Hockey | Mercy/NW Catholic/East Hampton | Away - Cromwell-Upper Rink [Directions] | 7:00 p.m. | L 2-0 | |
| Sat., 1/13 | V Girls Indoor Track | The Yale High School Classic at Coxe Cage, Yale | Away - Not Listed | 8:00 a.m. | ||
| Sat., 1/13 | V Girls Indoor Track | Bethel, Bunnell, Kolbe Cathedral, Masuk, New Fairfield, Pomperaug, Stratford | Away - Bethel HS-Track and Field Training Center | 9:00 a.m. | ||
| Mon., 1/15 | V Boys Ice Hockey | Cheshire | Home - Danbury Ice Arena-Patriot Rink [Directions] | 3:00 p.m. | L 6-3 | |
| Wed., 1/17 | V Boys Basketball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 7:00 p.m. | W 47-37 | |
| Wed., 1/17 | JV Boys Basketball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 5:15 p.m. | ||
| Wed., 1/17 | FR Boys Basketball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 3:30 p.m. | ||
| Wed., 1/17 | V Boys Ice Hockey | Masuk | Home - Danbury Ice Arena-Patriot Rink [Directions] | 5:30 p.m. | L 3-1 | |
| Wed., 1/17 | V Wrestling | New Fairfield | Away - New Fairfield HS-Old High School Gym [Directions] | 6:00 p.m. | Weston 48 New Fairfield 36 | |
| Wed., 1/17 | V Girls Basketball | Brookfield | Home - Weston HS-Gym (New) [Directions] | 6:00 p.m. | L 45-62 | |
| Wed., 1/17 | JV Girls Basketball | Brookfield | Home - Weston HS-Gym (New) [Directions] | 4:15 p.m. | ||
| Wed., 1/17 | V Girls Gymnastics | Fairfield Warde, Jonathan Law, St. Joseph, Trumbull | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:00 p.m. | Trumbull - 143.55 Ludlowe - 134.80 Law - 132.30 Warde- 104.70 SJ - 73.15 | |
| Wed., 1/17 | V Girls Ice Hockey | Hamden Coop | Away - Hamden-Lou Astorino Ice Rink [Directions] | 5:00 p.m. | L 6-1 | |
| Thu., 1/18 | JV Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena-Patriot Rink [Directions] | 3:45 p.m. | ||
| Thu., 1/18 | V Boys Swimming and Diving | Masuk | Home - Weston HS-Weston MS Pool [Directions] | 4:00 p.m. | Weston 98 Masuk 78 | |
| Fri., 1/19 | V Boys Basketball | Immaculate | Away - Immaculate HS-Immaculate Gym [Directions] | 7:00 p.m. | W 55-54 | |
| Fri., 1/19 | JV Boys Basketball | Immaculate | Away - Immaculate HS [Directions] | 5:15 p.m. | ||
| Fri., 1/19 | FR Boys Basketball | Immaculate | Away - Immaculate HS-Immaculate Gym [Directions] | 3:30 p.m. | ||
| Fri., 1/19 | V Girls Basketball | Immaculate | Home - Weston HS-Gym (New) [Directions] | 6:00 p.m. | L 39-56 | |
| Fri., 1/19 | JV Girls Basketball | Immaculate | Home - Weston HS-Gym (New) [Directions] | 4:15 p.m. | ||
| Fri., 1/19 | V Girls Gymnastics | Fairfield Warde, Foran | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:00 p.m. | Ludlowe - 136.15 Warde - 130.90 Foran - 123.80 | |
| Fri., 1/19 | V Girls Ice Hockey | Daniel Hand Coop | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 5:30 p.m. | W 4-1 | |
| Sat., 1/20 | V Boys Indoor Track | Hall of Fame Classic at the Armory in NYC | Away - Not Listed | 1:00 p.m. | ||
| Sat., 1/20 | V Wrestling | New Milford, Amity, Bethel, Bunnell, Enfield, Joel Barlow, Maloney, Masuk, Norwalk, Pomperaug Coop, RHAM, Stratford, Terryville-Thomaston, Harding/Bassick/Bridgeport Central | Away - New Milford HS-Main Gym - NMHS | 9:00 a.m. | ||
| Sat., 1/20 | JV Wrestling | Danbury, Enfield, Fairfield Ludlowe, Fairfield Warde, New Canaan, New Fairfield, Newtown, Norwalk, Ridgefield, Simsbury, Southington, Stamford, Trumbull | Away - Danbury HS-Main Gym | 9:30 a.m. | ||
| Sat., 1/20 | V Girls Indoor Track | Hall of Fame Classic at the Armory at NYC | Away - Not Listed | 1:00 p.m. | ||
| Mon., 1/22 | V Boys Basketball | Pomperaug | Home - Weston HS-Gym (New) [Directions] | 7:00 p.m. | L 42-47 | |
| Mon., 1/22 | JV Boys Basketball | Pomperaug | Home - Weston HS-Gym (New) [Directions] | 5:15 p.m. | ||
| Mon., 1/22 | FR Boys Basketball | Pomperaug | Home - Weston HS-Gym (New) [Directions] | 3:45 p.m. | ||
| Mon., 1/22 | V Girls Basketball | Pomperaug | Away - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | L 15-52 | |
| Mon., 1/22 | JV Girls Basketball | Pomperaug | Away - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 1/22 | V Girls Gymnastics | Fairfield Warde, Greenwich, New Canaan | Home - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:30 p.m. | Ludlowe - 133.55 Greenwich - 120.95 Warde - 119.70 New Canaan - 57.35 | |
| Mon., 1/22 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 3:30 p.m. | L 5-1 | |
| Wed., 1/24 | V Boys Basketball | Wright Tech | Home - Weston HS-Gym (New) [Directions] | 7:00 p.m. | W 103-26 | |
| Wed., 1/24 | JV Boys Basketball | Wright Tech | Home - Weston HS-Gym (New) [Directions] | 5:15 p.m. | W 103-26 | |
| Wed., 1/24 | FR Boys Basketball | Wright Tech | Home - Weston HS-Gym (New) [Directions] | 3:45 p.m. | ||
| Wed., 1/24 | V Boys Ice Hockey | Housatonic Coop | Home - Danbury Ice Arena-Patriot Rink [Directions] | 8:00 p.m. | W 5-1 | |
| Wed., 1/24 | V Wrestling | Pomperaug Coop | Home - Weston HS-Gym (Old) [Directions] | 6:00 p.m. | Weston 54 Pomperaug 24 | |
| Wed., 1/24 | V Girls Basketball | Wright Tech | Away - J M Wright Tech School-Thomas R. Good Gymnasium [Directions] | 4:30 p.m. | W 68-47 | |
| Wed., 1/24 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | L 4-3 | |
| Thu., 1/25 | JV Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena-Patriot Rink [Directions] | Canceled | Cancelled | |
| Thu., 1/25 | V Boys Swimming and Diving | New Milford | Away - O'Neill Arena - Canterbury Prep-Canterbury School Pool [Directions] | 7:00 p.m. | Weston 96 New Milford 61 | |
| Fri., 1/26 | V Boys Basketball | Bunnell | Home - Weston HS-Gym (New) [Directions] | 7:00 p.m. | L 64-70 | |
| Fri., 1/26 | JV Boys Basketball | Bunnell | Home - Weston HS-Gym (New) [Directions] | 5:15 p.m. | ||
| Fri., 1/26 | FR Boys Basketball | Bunnell | Home - Weston HS-Gym (Old) [Directions] | 5:30 p.m. | ||
| Fri., 1/26 | V Girls Basketball | Bunnell | Away - Bunnell HS-David Johnson Gymnasium [Directions] | 6:00 p.m. | W 41-25 | |
| Fri., 1/26 | JV Girls Basketball | Bunnell | Away - Bunnell HS-David Johnson Gymnasium [Directions] | 4:15 p.m. | ||
| Fri., 1/26 | V Girls Gymnastics | Stamford, Westhill | Home - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:00 p.m. | Ludlowe - 123.35 Warde- 106.95 Stamford - 66.80 Westhill - 46.05 | |
| Sat., 1/27 | V Boys Ice Hockey | Masuk | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:45 p.m. | W 2-1 | |
| Sat., 1/27 | V Boys Indoor Track | Bethel, Joel Barlow, Kolbe Cathedral, Masuk, New Milford, Newtown | Away - Bethel HS-Track and Field Training Center | 9:00 a.m. | ||
| Sat., 1/27 | JV Wrestling | Norwalk, Brien McMahon, Darien, Fairfield Prep, Fairfield Ludlowe, Fairfield Warde, Greenwich, New Canaan, New Milford, St. Joseph, Stamford, Staples, Trumbull, Westhill, Wilton | Away - Norwalk HS-Tom Scarso Gymnasium | 8:00 a.m. | ||
| Sat., 1/27 | V Girls Ice Hockey | Hall/Conard | Away - Veterans Memorial Ice Rink - West Hartford-Ice Rink [Directions] | 1:30 p.m. | L 5-0 | |
| Sat., 1/27 | V Girls Indoor Track | Bethel, Joel Barlow, Kolbe Cathedral, Masuk, New Milford, Newtown | Away - Bethel HS-Track and Field Training Center | 9:00 a.m. | ||
| Sat., 1/27 | Miscellaneous Events | Counties Ball | Home - TBA [Directions] | TBA | ||
| Mon., 1/29 | V Boys Basketball | Stratford | Away - Stratford HS-Gym [Directions] | 7:00 p.m. | W 70-59 | |
| Mon., 1/29 | JV Boys Basketball | Stratford | Away - Stratford HS-Gym [Directions] | 5:15 p.m. | ||
| Mon., 1/29 | FR Boys Basketball | Stratford | Away - Stratford HS-Gym [Directions] | 3:30 p.m. | ||
| Mon., 1/29 | V Girls Basketball | Stratford | Home - Weston HS-Gym (New) [Directions] | 6:00 p.m. | W 58-55 | |
| Mon., 1/29 | JV Girls Basketball | Stratford | Home - Weston HS-Gym (New) [Directions] | 4:15 p.m. | ||
| Tue., 1/30 | V Boys Ice Hockey | Northeastern Shamrocks | Home - Danbury Ice Arena-Patriot Rink [Directions] | 8:15 p.m. | L 3-2 | |
| Tue., 1/30 | V Boys Swimming and Diving | Joel Barlow-Bethel Swim | Home - Weston HS-Weston MS Pool [Directions] | 4:00 p.m. | Weston 86 Barlow Bethel 67 | |
| Tue., 1/30 | V Girls Gymnastics | Wilton, Fairfield Warde | Away - Wilton HS-Aux Gym [Directions] | 4:30 p.m. | Cancelled | |
| Wed., 1/31 | V Boys Ice Hockey | Brien McMahon/Norwalk | Home - Danbury Ice Arena-Patriot Rink [Directions] | 8:00 p.m. | W 3-2 | |
| Wed., 1/31 | V Wrestling | Joel Barlow | Away - Joel Barlow High-Upper Gym [Directions] | 6:00 p.m. | Weston 48 Joel Barlow 30 | |
| Thu., 2/1 | V Boys Basketball | Notre Dame-Fairfield | Home - Weston HS-Gym (New) [Directions] | 7:00 p.m. | L 50-59 | |
| Thu., 2/1 | JV Boys Basketball | Notre Dame-Fairfield | Home - Weston HS-Gym (New) [Directions] | 5:15 p.m. | ||
| Thu., 2/1 | FR Boys Basketball | Notre Dame-Fairfield | Home - Weston HS-Gym (New) [Directions] | 3:45 p.m. | L 50-59 | |
| Thu., 2/1 | JV Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena-Patriot Rink [Directions] | 3:45 p.m. | ||
| Thu., 2/1 | V Girls Basketball | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Sister Marion Reilly Auditorium [Directions] | 6:00 p.m. | L 38-50 | |
| Thu., 2/1 | JV Girls Basketball | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Sister Marion Reilly Auditorium [Directions] | 4:30 p.m. | W 45-30 | |
| Thu., 2/1 | V Girls Gymnastics | TBA, Wilton | Away - TBA | 7:00 p.m. | ||
| Pending changes awaiting acceptance by one or more parties involved: Time to 6:00 p.m., Facility to Gymnastics and Cheerleading Academy at Connecticut-Gym 1 | ||||||
| Fri., 2/2 | V Girls Ice Hockey | Daniel Hand Coop | Away - Northford-Red [Directions] | 4:20 p.m. | W 2-1 | |
| Fri., 2/2 | Miscellaneous Events | Red and White Ball | Home - TBA [Directions] | TBA | ||
| Sat., 2/3 | V Boys Ice Hockey | Watertown-Pomperaug | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | 8:30 p.m. | L 4-2 | |
| Sat., 2/3 | V Boys Indoor Track | SWC Championship | Away - Floyd Little Athletic Center-Field House | 5:00 p.m. | ||
| Sat., 2/3 | JV Wrestling | Ludlowe JV Tournament | Away - Fairfield Ludlowe HS-Main Gym | TBA | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 9:30 a.m. | ||||||
| Sat., 2/3 | V Girls Basketball | Lauralton Hall | Home - Weston HS-Gym (New) [Directions] | 12:00 p.m. | W 59-45 | |
| Sat., 2/3 | JV Girls Basketball | Lauralton Hall | Home - Weston HS-Gym (New) [Directions] | 10:30 a.m. | ||
| Sat., 2/3 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Conners - Stamford-Ice Rink [Directions] | 6:30 p.m. | L 2-0 | |
| Sat., 2/3 | V Girls Indoor Track | SWC Championship | Away - Floyd Little Athletic Center-Field House | 5:00 p.m. | ||
| Mon., 2/5 | V Boys Basketball | Bethel | Home - Weston HS-Gym (New) [Directions] | 7:00 p.m. | W 71-28 | |
| Mon., 2/5 | JV Boys Basketball | Bethel | Home - Weston HS-Gym (New) [Directions] | 4:45 p.m. | ||
| Mon., 2/5 | FR Boys Basketball | Bethel | Home - Weston HS-Gym (New) [Directions] | 3:30 p.m. | ||
| Mon., 2/5 | JV Boys Ice Hockey | Newtown/New Fairfield | Home - Danbury Ice Arena-Patriot Rink [Directions] | 4:00 p.m. | ||
| Mon., 2/5 | V Wrestling | New Milford | Away - New Milford HS-Small Gym - NMHS [Directions] | 6:00 p.m. | New Milford 72 Weston 12 | |
| Mon., 2/5 | V Girls Basketball | Bethel | Away - Bethel HS-BHS gym [Directions] | 6:00 p.m. | L 28-46 | |
| Mon., 2/5 | JV Girls Basketball | Bethel | Away - Bethel HS-BHS gym [Directions] | 4:15 p.m. | ||
| Mon., 2/5 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 8:30 p.m. | W 6-0 | |
| Mon., 2/5 | Unified Sports Basketball | Bethel | Home - Weston HS-Gym (New) [Directions] | 6:00 p.m. | ||
| Tue., 2/6 | V Boys Swimming and Diving | Brookfield | Away - Brookfield YMCA-Outside/Dome Pool [Directions] | 4:30 p.m. | Weston 100 Brookfield 81 | |
| Tue., 2/6 | V Boys Swimming and Diving | Brookfield | Away - Brookfield YMCA-Outside/Dome Pool [Directions] | 7:00 p.m. | ||
| Wed., 2/7 | V Boys Ice Hockey | Shepaug Valley Ice Hockey | Home - Danbury Ice Arena-Patriot Rink [Directions] | 5:30 p.m. | L 2-1 | |
| Wed., 2/7 | V Girls Gymnastics | Darien, Fairfield Warde | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:00 p.m. | Darien - 135.80 Ludlowe - 132.75 | |
| Thu., 2/8 | V Boys Basketball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 7:00 p.m. | W 70-56 | |
| Thu., 2/8 | JV Boys Basketball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 5:30 p.m. | ||
| Thu., 2/8 | FR Boys Basketball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 4:00 p.m. | ||
| Thu., 2/8 | V Boys Swimming and Diving | Pomperaug | Away - Pomperaug HS-PHS Pool [Directions] | 4:00 p.m. | Pomperaug 96 Weston 79 | |
| Thu., 2/8 | V Girls Basketball | Joel Barlow | Home - Weston HS-Gym (New) [Directions] | 6:00 p.m. | L 34-48 | |
| Thu., 2/8 | JV Girls Basketball | Joel Barlow | Home - Weston HS-Gym (New) [Directions] | 4:15 p.m. | ||
| Fri., 2/9 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | L 3-0 | |
| Fri., 2/9 | Unified Sports Basketball | Brookfield | Home - Weston HS-Gym (New) [Directions] | 2:45 p.m. | ||
| Sat., 2/10 | V Boys Basketball | Westhill | Home - Weston HS-Gym (New) [Directions] | 1:00 p.m. | W 60-45 | |
| Sat., 2/10 | JV Boys Basketball | Westhill | Home - Weston HS-Gym (New) [Directions] | 11:30 a.m. | ||
| Sat., 2/10 | FR Boys Basketball | Westhill | Home - Weston HS-Gym (New) [Directions] | 10:00 a.m. | ||
| Sat., 2/10 | V Boys Ice Hockey | Bethel/Brookfield/Danbury/Immaculate | Away - Danbury Ice Arena-Patriot Rink [Directions] | 3:30 p.m. | W 4-1 | |
| Sat., 2/10 | V Boys Indoor Track | Class M State Championship Meet at Floyd Little Athletic Center | Away - Not Listed | 4:00 p.m. | ||
| Sat., 2/10 | V Boys Indoor Track | CIAC M Divisional Championship | Away - Floyd Little Athletic Center | 4:00 p.m. | ||
| Sat., 2/10 | V Wrestling | SWC Wrestling Championships at Newtown High School | Away - Newtown HS-Gym | 9:00 a.m. | ||
| Sat., 2/10 | V Girls Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 12:00 p.m. | W 51-21 | |
| Sat., 2/10 | JV Girls Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 10:15 a.m. | ||
| Sat., 2/10 | V Girls Gymnastics | St. Joseph | Home - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 12:00 p.m. | ||
| Sat., 2/10 | V Girls Gymnastics | FCIAC Championships | Home - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 2:00 p.m. | 136.25 - 2nd | |
| Sat., 2/10 | V Girls Indoor Track | CIAC M Divisional Championship | Away - Floyd Little Athletic Center | 4:00 p.m. | ||
| Sat., 2/10 | V Girls Indoor Track | Class M State Championship Meet at Floyd Little Athletic Center | Away - Not Listed | 4:00 p.m. | ||
| Mon., 2/12 | V Boys Ice Hockey | Guilford | Away - East Haven HS-Patsy DiLungo Rink [Directions] | 8:00 p.m. | L 5-1 | |
| Wed., 2/14 | V Boys Basketball | Kolbe Cathedral | Home - Weston HS-Gym (New) [Directions] | 7:00 p.m. | L 43-67 | |
| Wed., 2/14 | JV Boys Basketball | Kolbe Cathedral | Home - Weston HS-Gym (New) [Directions] | 5:15 p.m. | ||
| Wed., 2/14 | FR Boys Basketball | Kolbe Cathedral | Home - Weston HS-Gym (New) [Directions] | 3:45 p.m. | ||
| Wed., 2/14 | V Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena-Patriot Rink [Directions] | 5:30 p.m. | W 5-2 | |
| Wed., 2/14 | V Boys Swimming and Diving | Bunnell-Stratford | Home - Weston HS-Weston MS Pool [Directions] | 4:00 p.m. | Weston 93 Bunnell-Stratford 68 | |
| Wed., 2/14 | V Girls Basketball | Kolbe Cathedral | Away - Cardinal Sheehan Center Bridgeport [Directions] | 7:00 p.m. | L 27-63 | |
| Wed., 2/14 | JV Girls Basketball | Kolbe Cathedral | Away - Cardinal Sheehan Center Bridgeport [Directions] | 5:15 p.m. | ||
| Wed., 2/14 | V Girls Gymnastics | Fairfield Warde | Home - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 5:45 p.m. | Ludlowe - 135.50 Warde - 125.15 | |
| Wed., 2/14 | V Girls Ice Hockey | Guilford Coop | Away - East Haven HS-Patsy DiLungo Rink [Directions] | 3:30 p.m. | L 1-0 | |
| Wed., 2/14 | V Girls Ice Hockey | Guilford Coop | Away - East Haven HS-Patsy DiLungo Rink [Directions] | 3:30 p.m. | ||
| Thu., 2/15 | JV Girls Basketball | Cardinal Kung Academy | Home - Weston HS-Gym (New) [Directions] | 4:00 p.m. | ||
| Thu., 2/15 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Sacred Heart University-Martire Arena [Directions] | 4:00 p.m. | W 3-1 | |
| Fri., 2/16 | V Boys Basketball | New Fairfield | Home - Weston HS-Gym (New) [Directions] | 7:00 p.m. | W 60-45 | |
| Fri., 2/16 | JV Boys Basketball | New Fairfield | Home - Weston HS-Gym (New) [Directions] | 5:15 p.m. | ||
| Fri., 2/16 | FR Boys Basketball | New Fairfield | Home - Weston HS-Gym (New) [Directions] | 3:45 p.m. | ||
| Fri., 2/16 | V Wrestling | CIAC CLASS S Tournament at Killingly | Away - Not Listed | 4:00 p.m. | ||
| Fri., 2/16 | V Wrestling | CIAC S Divisional Championship | Away - Killingly | TBA | ||
| Fri., 2/16 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 4:00 p.m. | L 5-2 | |
| Sat., 2/17 | V Boys Indoor Track | CIAC State Open Divisional Championship | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/17 | V Girls Indoor Track | CIAC State Open Championship | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Mon., 2/19 | V Girls Ice Hockey | West Haven/SHA | Away - West Haven HS-Bennett Rink [Directions] | 12:00 p.m. | ||
| Wed., 2/21 | V Boys Ice Hockey | New Milford | Away - Canterbury School-O'Neill Arena [Directions] | 7:15 p.m. | L 3-2 | |
| Fri., 2/23 | V Boys Basketball | Newtown | Away - Newtown HS-Gym [Directions] | 7:00 p.m. | W 63-59 | |
| Fri., 2/23 | V Wrestling | CIAC State Open & Girls Championship | Away - Floyd Little Athletic Center | TBA | ||
| Sat., 2/24 | V Boys Ice Hockey | Daniel Hand | Away - Northford-Red [Directions] | 5:00 p.m. | L 0-2 | |
| Sat., 2/24 | V Girls Gymnastics | CIAC Class L Divisional Championship | Away - Jonathan Law | 1:00 p.m. | ||
| Mon., 2/26 | V Boys Basketball | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Sister Marion Reilly Auditorium [Directions] | 6:30 p.m. | ||
| Tue., 2/27 | V Girls Basketball | Northwest Catholic | Away - Northwest Catholic HS (Primary)-Johnson Gym [Directions] | 6:30 p.m. | L 34-66 | |
| Wed., 2/28 | V Boys Swimming and Diving | Pomperaug, Brookfield, Masuk | Away - Pomperaug HS-PHS Pool [Directions] | 6:00 p.m. | ||
| Fri., 3/1 | V Boys Swimming and Diving | Masuk, Bethel, Brookfield, Bunnell-Stratford, Immaculate, Joel Barlow-Bethel Swim, New Fairfield, New Milford, Newtown, Pomperaug, Stratford | Away - Masuk HS-Pool | 5:00 p.m. | ||
| Sat., 3/2 | V Girls Gymnastics | CIAC State Open | Away - New Milford | 12:00 p.m. | ||
| Mon., 3/4 | V Boys Basketball | New Fairfield | Home - Weston HS-Gym (New) [Directions] | 6:30 p.m. | W 49-41 | |
| Mon., 3/4 | V Boys Ice Hockey | Masuk | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 5:00 p.m. | L 0-7 | |
| Mon., 3/4 | V Boys Ice Hockey | CIAC Div III First Round | Away - Higher Seed | TBA | ||
| Wed., 3/6 | V Boys Basketball | Cromwell | Away - Cromwell HS-Jake Salafia Gymnasium [Directions] | 6:30 p.m. | W 51-45 | |
| Wed., 3/6 | V Boys Swimming and Diving | CIAC Class S Diving Championship | Away - Sheehan | 5:30 p.m. | ||
| Wed., 3/6 | V | Unified Zumba | Home - Weston HS-Gym (New) [Directions] | 2:30 p.m. | ||
| Thu., 3/7 | V Boys Ice Hockey | CIAC Div III Quarterfinal | Away - Site TBA | TBA | ||
| Fri., 3/8 | V Boys Basketball | Weaver | Away - Weaver HS-Doc Hurley Fieldhouse [Directions] | 6:00 p.m. | L 68-69 | |
| Fri., 3/8 | V Boys Swimming and Diving | CIAC Class S Qualifying Meet | Away - Cornerstone Pool | 5:15 p.m. | ||
| Mon., 3/11 | V Boys Ice Hockey | CIAC Div III Semifinal | Away - Site TBA | TBA | ||
| Mon., 3/11 | V Boys Swimming and Diving | CIAC Class S Finals | Away - Cornerstone Pool | 6:00 p.m. | ||
| Thu., 3/14 | V Boys Ice Hockey | CIAC Div III Final | Away - Site TBA | TBA | ||
| Thu., 3/14 | V Boys Swimming and Diving | CIAC State Open Diving | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/16 | V Boys Swimming and Diving | CIAC State Open Swimming | Away - Yale | 1:00 p.m. | ||
| Wed., 3/20 | Miscellaneous Events | Spring Freshman/New Athlete and Parent Orientation | Home - Weston HS-Cafeteria [Directions] | 6:00 p.m. | All freshmen athletes and any athlete new to our school along with a parent/guardian who did not attend this meeting in the fall or winter must be in attendance in order to participate this spring. | |
| Thu., 3/21 | V Baseball | Fairfield Ludlowe (Scrim.) | Home - Weston HS-Revson #1 (Varsity) [Directions] | 3:45 p.m. | ||
| Thu., 3/21 | JV Baseball | Fairfield Ludlowe (Scrim.) | Home - Weston HS-Revson #2 (JV) [Directions] | 3:45 p.m. | ||
| Fri., 3/22 | V Boys Tennis | Trumbull (Scrim.) | Away - Trumbull HS-Tennis Courts [Directions] | 4:30 p.m. | ||
| Fri., 3/22 | V Girls Lacrosse | Brien McMahon (Scrim.) | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:30 p.m. | ||
| Fri., 3/22 | V Girls Tennis | Staples (Scrim.) | Home - Weston HS-WHS Tennis Courts [Directions] | 3:30 p.m. | ||
| Sat., 3/23 | V Boys Lacrosse | Notre Dame-West Haven (Scrim.) | Away - Notre Dame HS-Veteran's Stadium [Directions] | 11:00 a.m. | ||
| Pending changes awaiting acceptance by one or more parties involved: Date to 3/22, Time to 6:00 p.m. | ||||||
| Sat., 3/23 | JV Girls Lacrosse | Brien McMahon (Scrim.) | Home - Weston HS-WHS Lower Turf Field [Directions] | Postponed | ||
| Mon., 3/25 | V Baseball | Norwalk (Scrim.) | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 4:00 p.m. | ||
| Mon., 3/25 | JV Baseball | Norwalk (Scrim.) | Away - City Hall Field [Directions] | 4:00 p.m. | ||
| Mon., 3/25 | V Boys Tennis | Ridgefield (Scrim.) | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | ||
| Mon., 3/25 | V Softball | Greens Farms Academy (Scrim.) | Away - Greens Farms Academy-Softball Diamond | 4:00 p.m. | ||
| Mon., 3/25 | V Girls Tennis | Ridgefield (Scrim.) | Away - Ridgefield HS-RHS Tennis Courts [Directions] | 3:45 p.m. | ||
| Tue., 3/26 | V Baseball | Staples (Scrim.) | Home - Weston HS-Revson #1 (Varsity) [Directions] | 3:45 p.m. | ||
| Wed., 3/27 | V Boys Lacrosse | Greenwich Country Day (Scrim.) | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 3/27 | V Girls Lacrosse | Norwalk (Scrim.) | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | 4:30 p.m. | ||
| Wed., 3/27 | JV Girls Lacrosse | Norwalk (Scrim.) | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | 5:45 p.m. | ||
| Wed., 3/27 | V Girls Tennis | Wilton (Scrim.) | Away - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 3/27 | JV Girls Tennis | Wilton (Scrim.) | Away - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 3/28 | V Softball | Wilton (Scrim.) | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | Canceled | Cancelled | |
| Sat., 3/30 | V Baseball | Stamford | Away - Stamford HS-Cubeta Stadium [Directions] | 12:00 p.m. | ||
| Sat., 3/30 | V Girls Tennis | St. Joseph | Home - Weston HS-WHS Tennis Courts [Directions] | 10:00 a.m. | ||
| Mon., 4/1 | V Boys Tennis | Wilton | Away - Wilton HS-Tennis Courts [Directions] | 3:30 p.m. | ||
| Mon., 4/1 | V Softball | Shelton | Away - Shelton HS-Softball Diamond [Directions] | 4:15 p.m. | ||
| Mon., 4/1 | V Girls Tennis | Fairfield Warde | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | ||
| Tue., 4/2 | V Boys Lacrosse | Wilton | Away - Wilton HS-Veterans Memorial Stadium [Directions] | 6:30 p.m. | ||
| Tue., 4/2 | JV Boys Lacrosse | Wilton | Away - Wilton HS-Veterans Memorial Stadium [Directions] | 4:00 p.m. | ||
| Wed., 4/3 | V | Unified Zumba | Home - Weston HS-Gym (New) [Directions] | 2:30 p.m. | ||
| Thu., 4/4 | V Boys Lacrosse | Pomperaug | Away - Pomperaug HS-Stadium [Directions] | 7:00 p.m. | ||
| Thu., 4/4 | JV Boys Lacrosse | Pomperaug | Away - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Thu., 4/4 | V Girls Lacrosse | Pomperaug | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:30 p.m. | ||
| Thu., 4/4 | JV Girls Lacrosse | Pomperaug | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 4/5 | V Baseball | Bethel | Away - Bethel HS-MS Turf baseball field [Directions] | 4:00 p.m. | ||
| Fri., 4/5 | V Boys Tennis | Staples | Home - Weston HS-WHS Tennis Courts [Directions] | 3:30 p.m. | ||
| Fri., 4/5 | V Softball | Greenwich | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 4:15 p.m. | ||
| Fri., 4/5 | V Girls Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Sat., 4/6 | V Baseball | Wilton | Away - Wilton HS-Varsity Baseball Field [Directions] | 11:00 a.m. | ||
| Sat., 4/6 | V Boys Lacrosse | Iona Prep (NY) | Home - Weston HS-WHS Lower Turf Field [Directions] | 12:00 p.m. | ||
| Sat., 4/6 | JV Boys Lacrosse | Iona Prep (NY) | Home - Weston HS-WHS Lower Turf Field [Directions] | 10:00 a.m. | ||
| Sat., 4/6 | V Girls Lacrosse | Amity | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Sat., 4/6 | JV Girls Lacrosse | Amity | Home - Weston HS-WHS Lower Turf Field [Directions] | 2:30 p.m. | ||
| Mon., 4/8 | V Boys Tennis | New Fairfield | Home - Weston HS-WHS Tennis Courts [Directions] | 4:45 p.m. | ||
| Mon., 4/8 | V Girls Golf | Pomperaug | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | ||
| Mon., 4/8 | V Softball | Notre Dame-Fairfield | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 4:15 p.m. | ||
| Mon., 4/8 | V Girls Tennis | New Fairfield | Away - New Fairfield HS-Tennis Courts [Directions] | 4:45 p.m. | ||
| Tue., 4/9 | JV Baseball | Wilton | Away - Wilton HS-JV Baseball Field [Directions] | 4:15 p.m. | ||
| Tue., 4/9 | V Boys Lacrosse | Newtown | Home - Weston HS-WHS Lower Turf Field [Directions] | 7:00 p.m. | ||
| Tue., 4/9 | JV Boys Lacrosse | Newtown | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:00 p.m. | ||
| Tue., 4/9 | V Boys Outdoor Track | Bunnell, Immaculate, Notre Dame-Fairfield | Home - Weston HS-WHS Track [Directions] | 4:00 p.m. | ||
| Tue., 4/9 | V Girls Golf | Notre Dame-Fairfield | Away - Fairchild Wheeler Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 4/9 | V Girls Lacrosse | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 6:30 p.m. | ||
| Tue., 4/9 | JV Girls Lacrosse | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 5:00 p.m. | ||
| Tue., 4/9 | V Girls Outdoor Track | Bunnell, Immaculate, Notre Dame-Fairfield | Home - Weston HS-WHS Track [Directions] | 4:00 p.m. | ||
| Wed., 4/10 | V Boys Tennis | Joel Barlow | Away - Joel Barlow HS-Tennis Courts [Directions] | 3:45 p.m. | ||
| Wed., 4/10 | V | Unified Wiffleball (outside?) | Home - Weston HS-Gym (New) [Directions] | 2:30 p.m. | ||
| Wed., 4/10 | V Girls Golf | Masuk | Away - Fairchild Wheeler Golf Course-Aspetuck Country Club [Directions] | 3:15 p.m. | ||
| Wed., 4/10 | V Softball | Bunnell | Away - Bunnell HS-Bunnell Softball FIeld [Directions] | 4:15 p.m. | ||
| Wed., 4/10 | V Girls Tennis | Joel Barlow | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | ||
| Thu., 4/11 | V Boys Lacrosse | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Park Ave Field [Directions] | 4:00 p.m. | ||
| Thu., 4/11 | V Girls Golf | Brookfield | Away - Sunset Hill Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 4/11 | V Girls Lacrosse | Notre Dame-Fairfield | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:30 p.m. | ||
| Thu., 4/11 | JV Girls Lacrosse | Notre Dame-Fairfield | Home - Weston HS-WHS Lower Turf Field [Directions] | Canceled | Cancelled | |
| Fri., 4/12 | V Girls Lacrosse | Greenwich | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | ||
| Fri., 4/12 | JV Girls Lacrosse | Greenwich | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:30 p.m. | ||
| Mon., 4/15 | V Baseball | New Fairfield | Home - Weston HS-Revson #1 (Varsity) [Directions] | 4:15 p.m. | L 2-14 | |
| Mon., 4/15 | JV Baseball | Brookfield | Home - Weston HS-Revson #2 (JV) [Directions] | 3:00 p.m. | ||
| Mon., 4/15 | V Boys Tennis | Bunnell | Home - Weston HS-WHS Tennis Courts [Directions] | 10:00 a.m. | ||
| Mon., 4/15 | V Softball | New Fairfield | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 4:15 p.m. | ||
| Mon., 4/15 | V Girls Tennis | Bunnell | Away - Bunnell HS-Bunnell Tennis Courts [Directions] | 10:00 a.m. | ||
| Tue., 4/16 | JV Baseball | New Fairfield | Away - New Fairfield HS-Baseball Field [Directions] | 4:15 p.m. | ||
| Tue., 4/16 | V Boys Lacrosse | Joel Barlow | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | ||
| Tue., 4/16 | JV Boys Lacrosse | Joel Barlow | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 4/16 | V Boys Tennis | Guilford | Away - Guilford HS-GHS Tennis Courts [Directions] | 3:45 p.m. | ||
| Tue., 4/16 | V Girls Golf | Pomperaug | Away - Pomperaug HS-Pomperaug Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 4/16 | V Girls Lacrosse | Joel Barlow | Away - Joel Barlow HS-Field J [Directions] | 5:30 p.m. | ||
| Tue., 4/16 | JV Girls Lacrosse | Joel Barlow | Away - Joel Barlow HS-Field J [Directions] | 4:00 p.m. | ||
| Wed., 4/17 | V Baseball | Kolbe Cathedral | Away - Seaside Park #10 [Directions] | 1:00 p.m. | ||
| Wed., 4/17 | V Softball | Kolbe Cathedral | Away - Cal Ripken Field-Cal Ripken Field [Directions] | 4:15 p.m. | ||
| Thu., 4/18 | V Boys Lacrosse | Bunnell-Stratford | Away - Bunnell HS-Mastroni Field [Directions] | 6:00 p.m. | ||
| Fri., 4/19 | V Baseball | Bethel | Away - Bethel HS-Hunt Field at Bethel HS [Directions] | 3:15 p.m. | ||
| Fri., 4/19 | V Softball | Bethel | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 3:30 p.m. | ||
| Sat., 4/20 | JV Baseball | Bethel | Away - Bethel HS-MS Turf baseball field [Directions] | 11:00 a.m. | ||
| Sat., 4/20 | V Boys Lacrosse | Brookfield | Away - Brookfield HS-BHS Stadium Field [Directions] | 12:00 p.m. | ||
| Sat., 4/20 | JV Boys Lacrosse | Brookfield | Away - Brookfield HS-BHS Stadium Field [Directions] | 10:00 a.m. | ||
| Sat., 4/20 | V Girls Lacrosse | Brookfield | Home - Weston HS-WHS Lower Turf Field [Directions] | 11:30 a.m. | ||
| Sat., 4/20 | JV Girls Lacrosse | Brookfield | Home - Weston HS-WHS Lower Turf Field [Directions] | 10:00 a.m. | ||
| Mon., 4/22 | V Girls Golf | Immaculate | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | ||
| Tue., 4/23 | V Baseball | Immaculate | Home - Weston HS-Revson #1 (Varsity) [Directions] | 4:15 p.m. | ||
| Tue., 4/23 | JV Baseball | Immaculate | Away - Immaculate HS-Baseball Diamond [Directions] | Postponed | ||
| Tue., 4/23 | V Boys Lacrosse | Bethel | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | ||
| Tue., 4/23 | JV Boys Lacrosse | Bethel | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | V Boys Outdoor Track | Pomperaug, Joel Barlow | Away - Pomperaug HS-Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | V Boys Tennis | Stratford | Away - Flood MS-Flood MS Tennis Courts [Directions] | 3:45 p.m. | ||
| Tue., 4/23 | V Girls Golf | Joel Barlow | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | ||
| Tue., 4/23 | V Girls Lacrosse | Bethel | Away - Bethel HS-MS turf lacrosse field [Directions] | 6:00 p.m. | ||
| Tue., 4/23 | JV Girls Lacrosse | Bethel | Away - Bethel HS-MS turf lacrosse field [Directions] | 4:15 p.m. | ||
| Tue., 4/23 | V Girls Outdoor Track | Joel Barlow, Pomperaug | Home - Weston HS-WHS Track [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | V Softball | Immaculate | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 4:15 p.m. | ||
| Tue., 4/23 | V Girls Tennis | Stratford | Home - Weston HS-WHS Tennis Courts [Directions] | 4:45 p.m. | ||
| Wed., 4/24 | V Baseball | Brookfield | Away - Brookfield HS-BHS Baseball Field [Directions] | 4:15 p.m. | ||
| Wed., 4/24 | V Boys Tennis | Pomperaug | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | ||
| Wed., 4/24 | V Softball | Brookfield | Away - Brookfield HS-BHS Softball Field [Directions] | 4:15 p.m. | ||
| Wed., 4/24 | V Girls Tennis | Pomperaug | Away - Edgewood Bath and Tennis Club [Directions] | 3:45 p.m. | ||
| Thu., 4/25 | JV Baseball | Brookfield | Home - Weston HS-Revson #2 (JV) [Directions] | 4:15 p.m. | ||
| Thu., 4/25 | V Boys Lacrosse | Greenwich | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | ||
| Thu., 4/25 | JV Boys Lacrosse | Greenwich | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 4/25 | V Girls Golf | Stratford | Away - Mill River Country Club [Directions] | 3:00 p.m. | ||
| Thu., 4/25 | V Girls Lacrosse | Stratford/Bunnell | Away - Penders Field-Penders Field - Stratford [Directions] | 6:30 p.m. | ||
| Thu., 4/25 | JV Girls Lacrosse | Stratford/Bunnell | Away - Penders Field-Penders Field - Stratford [Directions] | 5:00 p.m. | ||
| Fri., 4/26 | V Baseball | Stratford | Away - Penders Field-Penders Field - Stratford [Directions] | 4:15 p.m. | ||
| Fri., 4/26 | V Boys Tennis | Newtown | Away - Newtown HS-NHS Tennis Courts [Directions] | 3:30 p.m. | ||
| Fri., 4/26 | V Softball | Stratford | Away - DeLuca Field-Deluca Field [Directions] | 4:15 p.m. | ||
| Fri., 4/26 | V Girls Tennis | Newtown | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | ||
| Fri., 4/26 | JV Girls Tennis | Cardinal Kung Academy | Home - Weston HS-WHS Tennis Courts [Directions] | 5:00 p.m. | ||
| Sat., 4/27 | V Baseball | Foran | Home - Weston HS-Revson #1 (Varsity) [Directions] | 11:00 a.m. | ||
| Sat., 4/27 | JV Baseball | Stratford | Home - Weston HS-Revson #2 (JV) [Directions] | 2:00 p.m. | ||
| Sat., 4/27 | V Boys Lacrosse | Daniel Hand | Away - Madison Surf Club-Strong Field [Directions] | 1:00 p.m. | ||
| Sat., 4/27 | JV Boys Lacrosse | Daniel Hand | Away - Daniel Hand HS-Janssen Field #2/DHHS Campus [Directions] | 11:00 a.m. | ||
| Sat., 4/27 | V Boys Outdoor Track | O'Grady Relays at Danbury HS | Away - Not Listed | 9:00 a.m. | ||
| Sat., 4/27 | V Boys Tennis | Hall, Southington (Scrim.) | Away - Hall HS-Tennis Courts [Directions] | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to 9:30 a.m. | ||||||
| Sat., 4/27 | V Girls Lacrosse | Daniel Hand | Away - Madison Surf Club-Strong Field [Directions] | 11:00 a.m. | ||
| Sat., 4/27 | JV Girls Lacrosse | J.V Girls Lacrosse Tournament | Away - Newtown HS-Blue and Gold Stadium | 9:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 12:00 p.m. | ||||||
| Sat., 4/27 | V Girls Outdoor Track | O'Grady Relays at Danbury High School | Away - Not Listed | 9:00 a.m. | ||
| Mon., 4/29 | V Baseball | Notre Dame-Fairfield | Home - Weston HS-Revson #1 (Varsity) [Directions] | 4:15 p.m. | ||
| Mon., 4/29 | V Boys Tennis | Daniel Hand | Home - Weston HS-WHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | V Girls Golf | Newtown | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | ||
| Mon., 4/29 | V Girls Outdoor Track | Newtown, New Fairfield, New Milford | Away - Newtown HS-Blue and Gold Stadium [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | V Girls Tennis | Notre Dame-Fairfield | Away - Veteran's Park - Bridgeport-Tennis Courts [Directions] | 3:45 p.m. | ||
| Tue., 4/30 | JV Baseball | Bethel | Away - Bethel HS-MS Turf baseball field [Directions] | 4:15 p.m. | ||
| Tue., 4/30 | V Boys Lacrosse | New Fairfield | Away - New Fairfield HS-Marty Morgan Field [Directions] | 4:30 p.m. | ||
| Tue., 4/30 | JV Boys Lacrosse | New Fairfield | Away - New Fairfield HS-Marty Morgan Field [Directions] | 6:15 p.m. | ||
| Tue., 4/30 | V Girls Golf | Bunnell | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | ||
| Tue., 4/30 | V Girls Lacrosse | New Fairfield | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:30 p.m. | ||
| Tue., 4/30 | JV Girls Lacrosse | New Fairfield | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 4/30 | V Softball | Joel Barlow | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | V Baseball | Joel Barlow | Away - Joel Barlow HS-Baseball Field [Directions] | 4:15 p.m. | ||
| Wed., 5/1 | V Boys Outdoor Track | Newtown, New Fairfield, New Milford | Away - Newtown HS-Blue and Gold Stadium [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | V Boys Tennis | New Milford | Away - New Milford HS-Tennis Courts - NMHS [Directions] | 3:45 p.m. | ||
| Wed., 5/1 | V Girls Golf | Bunnell | Away - Bunnell HS-Blackhawk Country Club (Old OCC) [Directions] | 3:00 p.m. | ||
| Wed., 5/1 | V Softball | Joel Barlow | Away - Joel Barlow High-Field E (Softball) [Directions] | 4:15 p.m. | ||
| Wed., 5/1 | V Girls Tennis | New Milford | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | ||
| Thu., 5/2 | V Baseball | Bunnell | Home - Weston HS-Revson #1 (Varsity) [Directions] | 4:15 p.m. | ||
| Thu., 5/2 | JV Baseball | Joel Barlow | Home - Weston HS-Revson #2 (JV) [Directions] | 4:00 p.m. | ||
| Thu., 5/2 | V Softball | Bunnell | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 4:15 p.m. | ||
| Fri., 5/3 | V Boys Lacrosse | New Milford | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | ||
| Fri., 5/3 | JV Boys Lacrosse | New Milford | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 5/3 | V Boys Tennis | Masuk | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | ||
| Fri., 5/3 | V Girls Lacrosse | New Milford | Away - New Milford HS-Joe Wiser Stadium - NMHS [Directions] | 5:30 p.m. | ||
| Fri., 5/3 | JV Girls Lacrosse | New Milford | Away - New Milford HS-North Turf Field - NMHS [Directions] | 4:00 p.m. | ||
| Fri., 5/3 | V Girls Tennis | Masuk | Away - Wolfe Park-Tennis Courts [Directions] | 3:45 p.m. | ||
| Sat., 5/4 | V Baseball | Brookfield | Home - Weston HS-Revson #1 (Varsity) [Directions] | 3:00 p.m. | ||
| Sat., 5/4 | JV Baseball | Kolbe Cathedral | Away - Seaside Park #10 [Directions] | 10:00 a.m. | ||
| Mon., 5/6 | V Baseball | Masuk | Away - Masuk HS-John Giampaolo Baseball Field @ Masuk HS [Directions] | 4:15 p.m. | ||
| Mon., 5/6 | V Boys Tennis | Immaculate | Away - Rogers Park (Danbury, CT)-Tennis Courts [Directions] | 3:45 p.m. | ||
| Mon., 5/6 | V Girls Golf | Brookfield | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | ||
| Mon., 5/6 | V Girls Outdoor Track | Bethel, Stratford | Away - Bethel HS-BHS track [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | V Softball | Masuk | Away - Masuk HS-Masuk High School Softball Field [Directions] | 4:15 p.m. | ||
| Mon., 5/6 | V Girls Tennis | Immaculate | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | ||
| Tue., 5/7 | JV Baseball | Masuk | Home - Weston HS-Revson #2 (JV) [Directions] | 4:15 p.m. | ||
| Tue., 5/7 | V Boys Lacrosse | Masuk | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | ||
| Tue., 5/7 | V Boys Outdoor Track | Bethel, Stratford | Home - Weston HS-WHS Track [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | V Girls Lacrosse | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 6:30 p.m. | ||
| Tue., 5/7 | JV Girls Lacrosse | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 5:00 p.m. | ||
| Wed., 5/8 | V Baseball | New Milford | Away - New Milford HS-Baseball Varsity Field - NMHS [Directions] | 4:15 p.m. | ||
| Wed., 5/8 | V Boys Tennis | Brookfield | Away - Brookfield HS-BHS Tennis Courts [Directions] | 3:45 p.m. | ||
| Wed., 5/8 | V Girls Golf | Joel Barlow, Immaculate | Away - Redding Country Club [Directions] | 3:00 p.m. | ||
| Wed., 5/8 | V Softball | New Milford | Away - New Milford HS-Softball Varsity Field - NMHS [Directions] | 4:15 p.m. | ||
| Wed., 5/8 | V Girls Tennis | Brookfield | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | ||
| Thu., 5/9 | JV Baseball | New Milford | Home - Weston HS-Revson #2 (JV) [Directions] | 4:15 p.m. | ||
| Thu., 5/9 | V Boys Lacrosse | Immaculate | Away - Immaculate HS-Mustang Valley [Directions] | 4:00 p.m. | ||
| Thu., 5/9 | V Girls Golf | Newtown | Away - Newtown Country Club [Directions] | 3:00 p.m. | ||
| Thu., 5/9 | V Girls Lacrosse | Immaculate | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:30 p.m. | ||
| Fri., 5/10 | V Baseball | Pomperaug | Home - Weston HS-Revson #1 (Varsity) [Directions] | 4:15 p.m. | ||
| Fri., 5/10 | V Boys Tennis | Bethel | Home - Weston HS-WHS Tennis Courts [Directions] | 3:45 p.m. | ||
| Fri., 5/10 | V Softball | Pomperaug | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 4:15 p.m. | ||
| Fri., 5/10 | V Girls Tennis | Bethel | Away - Bethel HS-BHS Tennis Courts [Directions] | 3:45 p.m. | ||
| Sat., 5/11 | JV Baseball | Pomperaug | Away - Community House Park-Baseball Field [Directions] | 11:00 a.m. | ||
| Sat., 5/11 | V Girls Lacrosse | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 12:00 p.m. | ||
| Sat., 5/11 | JV Girls Lacrosse | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 1:30 p.m. | ||
| Sat., 5/11 | V Softball | Lyman Hall | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 12:00 p.m. | ||
| Mon., 5/13 | V Baseball | Newtown | Away - Newtown HS-Nighthawk Ball Park [Directions] | 4:15 p.m. | ||
| Mon., 5/13 | V Boys Lacrosse | Fairfield Ludlowe | Home - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | ||
| Mon., 5/13 | JV Boys Lacrosse | Fairfield Ludlowe | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | V Girls Golf | Notre Dame-Fairfield | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | ||
| Mon., 5/13 | V Girls Golf | Stratford | Home - Weston HS-Aspetuck Country Club [Directions] | 3:00 p.m. | ||
| Mon., 5/13 | V Girls Outdoor Track | Masuk, Brookfield, Kolbe Cathedral | Away - Masuk HS-Edmund Butler Track @ Masuk HS [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | V Softball | Newtown | Away - Treadwell Park-Newtown Treadwell Park [Directions] | 7:00 p.m. | ||
| Tue., 5/14 | JV Baseball | Newtown | Home - Weston HS-Revson #2 (JV) [Directions] | 4:15 p.m. | ||
| Tue., 5/14 | V Boys Outdoor Track | Masuk, Brookfield, Kolbe Cathedral | Away - Masuk HS-Edmund Butler Track @ Masuk HS [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | V Boys Tennis | Amity | Away - Amity Regional HS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | V Girls Lacrosse | Staples | Home - Weston HS-WHS Lower Turf Field [Directions] | 5:30 p.m. | ||
| Tue., 5/14 | JV Girls Lacrosse | Staples | Home - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | V Baseball | Abbott Tech | Away - Abbott V-T School-Abbott Tech Baseball Field, School Campus [Directions] | 3:45 p.m. | ||
| Wed., 5/15 | V Softball | Abbott Tech | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 4:00 p.m. | ||
| Thu., 5/16 | JV Baseball | Bethel | Home - Weston HS-Revson #2 (JV) [Directions] | 4:00 p.m. | ||
| Thu., 5/16 | V Boys Outdoor Track | SWC Freshmen Meet | Away - Bethel HS-BHS track | 4:00 p.m. | ||
| Thu., 5/16 | V Girls Golf | Masuk | Away - Whitney Farms Golf Course [Directions] | 3:00 p.m. | ||
| Sat., 5/18 | JV Baseball | Bunnell | Away - Bunnell HS-Bunnell Baseball Field [Directions] | 12:00 p.m. | ||
| Mon., 5/20 | V Baseball | Wright Tech | Home - Weston HS-Revson #1 (Varsity) [Directions] | 4:00 p.m. | ||
| Mon., 5/20 | V Boys Outdoor Track | SWC Outdoor Track Championship | Away - Bethel HS-BHS track | 3:00 p.m. | ||
| Mon., 5/20 | V Girls Outdoor Track | SWC Outdoor Track Championship | Away - Bethel HS-BHS track | 3:00 p.m. | ||
| Mon., 5/20 | V Softball | Wright Tech | Home - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 4:00 p.m. | ||
| Fri., 6/7 | Miscellaneous Events | Unified Trip | Home - TBA [Directions] | 7:30 a.m. | Unified Field Trip | |
| Sat., 6/8 | Miscellaneous Events | SAT's | Home - TBA [Directions] | 8:00 a.m. | ||
| Sat., 6/15 | V Field Hockey | Alumni Game | Home - Weston HS-WHS Lower Turf Field [Directions] | 12:00 p.m. | ||