| Weston 2018-19 Athletic Events Schedule | |||||||
|---|---|---|---|---|---|---|---|
| 879 Events Listed || Go Back || | |||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Bus Time | Note |
| TBA | JV Baseball | Joel Barlow | Home - Revson Field, Weston [Directions] | 4:00 p.m. | |||
| TBA | JV Baseball | Pomperaug | Away - PHS Baseball Field [Directions] | 4:30 p.m. | 8:15am | ||
| TBA | JV Baseball | Notre Dame-Fairfield | Away - Fabbri Field at Notre Dame [Directions] | TBA | 2:40pm | ||
| TBA | JV Baseball | Immaculate | Away - Immaculate [Directions] | TBA | 11:30am | ||
| TBA | JV Baseball | New Milford | Home - Revson Field, Weston [Directions] | TBA | |||
| TBA | JV Boys Ice Hockey | Newtown/New Fairfield | Home - Danbury Ice Arena [Directions] | TBA | |||
| TBA | JV Boys Soccer | Immaculate | Away - Immaculate HS [Directions] | TBA | 2:45pm | ||
| TBA | FR Girls Basketball | New Fairfield | Away - NFHS Gym [Directions] | 3:45 p.m. | 2:40pm | ||
| TBA | FR Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | TBA | 2:45pm | ||
| TBA | FR Girls Basketball | Joel Barlow | Away - JBHS Lower Gym [Directions] | TBA | 2:40pm | ||
| TBA | FR Girls Basketball | Notre Dame-Fairfield | Home - WHS Gymnasium [Directions] | TBA | |||
| TBA | JV Field Hockey | Bethel | Away - Hunt Field at Bethel HS [Directions] | TBA | 2:40pm | ||
| TBA | V Girls Soccer | Staples (Scrim.) | Away - Loeffler Field - Staples HS [Directions] | TBA | TBA | ||
| TBA | JV Girls Soccer | Pomperaug | Home - WHS Turf Field [Directions] | TBA | |||
| TBA | JV Girls Soccer | Staples (Scrim.) | Away - Wakeman Field E (grass) [Directions] | TBA | TBA | ||
| TBA | JV Softball | Bridgeport Central | Home - Weston MS [Directions] | 4:00 p.m. | |||
| TBA | JV Softball | Pomperaug | Away - PHS Softball Field [Directions] | 4:30 p.m. | 8:15am | ||
| TBA | JV Softball | Newtown | Home - Weston MS [Directions] | TBA | |||
| Wed., 8/29 | V Boys Soccer | Norwalk (Scrim.) | Home - WHS Turf Field [Directions] | 5:00 p.m. | |||
| Wed., 8/29 | JV Boys Soccer | Norwalk (Scrim.) | Home - WHS Turf Field [Directions] | 6:30 p.m. | |||
| Fri., 8/31 | V Football | St. Lukes (Scrim.) | Home - WHS Stadium Field [Directions] | 6:00 p.m. | |||
| Fri., 8/31 | JV Field Hockey | New Fairfield Jamboree | Away | 4:00 p.m. | 2:40pm | ||
| Fri., 8/31 | V Girls Soccer | Fairfield Ludlowe (Scrim.) | Home - WHS Turf Field [Directions] | 5:00 p.m. | |||
| Fri., 8/31 | V Girls Volleyball | Ridgefield (Scrim.) | Away - RHS Main Gym [Directions] | 3:30 p.m. | 2:40pm | ||
| Fri., 8/31 | JV Girls Volleyball | Ridgefield (Scrim.) | Away - RHS Main Gym [Directions] | 3:30 p.m. | 2:40pm | ||
| Fri., 8/31 | FR Girls Volleyball | Ridgefield (Scrim.) | Home - WHS Gymnasium [Directions] | 3:30 p.m. | |||
| Sat., 9/1 | V Boys Soccer | Fairfield Warde (Scrim.) | Home - WHS Turf Field [Directions] | 9:00 a.m. | |||
| Sat., 9/1 | JV Boys Soccer | Fairfield Warde (Scrim.) | Home - WHS Turf Field [Directions] | 10:30 a.m. | |||
| Sat., 9/1 | V Field Hockey | New Fairfield Jamboree | Away | 8:00 a.m. | 6:30am | ||
| Tue., 9/4 | V Girls Soccer | Fairfield Ludlowe (Scrim.) | Away - Sturges Park [Directions] | 3:30 p.m. | 2:40pm | ||
| Tue., 9/4 | JV Girls Soccer | Fairfield Ludlowe (Scrim.) | Away [Directions] | 3:30 p.m. | 2:40pm | ||
| Wed., 9/5 | V Girls Volleyball | Val Dickinson Jamboree | Away | TBA | TBA | ||
| Thu., 9/6 | V Boys Soccer | Pomperaug | Away - Sports Complex & Track [Directions] | 7:00 p.m. | W 8-0 | 3:15pm | |
| Thu., 9/6 | JV Boys Soccer | Pomperaug | Away - Sports Complex & Track [Directions] | 5:30 p.m. | 3:15pm | ||
| Thu., 9/6 | V Girls Soccer | Pomperaug | Home - WHS Turf Field [Directions] | 7:00 p.m. | T 0-0 | ||
| Fri., 9/7 | V Football | New Milford | Home - WHS Stadium Field [Directions] | 7:00 p.m. | W 35-0 | ||
| Fri., 9/7 | V Girls Swimming and Diving | Pomperaug | Home - Weston MS Pool [Directions] | 4:00 p.m. | Weston 97 Pomperaug 82 | ||
| Fri., 9/7 | V Girls Volleyball | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:30 p.m. | W 3-0 | 2:40pm | non league |
| Fri., 9/7 | JV Girls Volleyball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | 2:40pm | ||
| Fri., 9/7 | FR Girls Volleyball | Brookfield | Home - WHS Old Gymnasium [Directions] | 3:45 p.m. | |||
| Sat., 9/8 | JV Football | New Milford | Away - New Milford HS [Directions] | 11:00 a.m. | 8:30am | ||
| Sat., 9/8 | V Field Hockey | Fairfield Ludlowe | Away - Taft Field [Directions] | 2:00 p.m. | T 0-0 | 12:30pm | non league |
| Sat., 9/8 | JV Field Hockey | Fairfield Ludlowe | Away - Taft Field [Directions] | 3:30 p.m. | 12:30pm | ||
| Sat., 9/8 | V Girls Soccer | Haddam-Killingworth | Home - WHS Turf Field [Directions] | 6:00 p.m. | W 6-0 | nonleague | |
| Sat., 9/8 | JV Girls Soccer | Haddam-Killingworth | Home - WHS Turf Field [Directions] | 4:00 p.m. | |||
| Tue., 9/11 | V Boys Cross Country | New Milford, Kolbe Cathedral, Newtown | Home - WHS Stadium Field [Directions] | 5:00 p.m. | NM 15 - Weston 47 Newtown 16 - Weston 46 Weston 15 - Kolbe 50 | Yes | |
| Tue., 9/11 | V Boys Soccer | Kolbe Cathedral | Home - WHS Turf Field [Directions] | 5:30 p.m. | W 5-0 | ||
| Tue., 9/11 | V Girls Cross Country | New Milford, Kolbe Cathedral, Newtown | Home - WHS Stadium Field [Directions] | 4:30 p.m. | New Milford 23 Weston 32 Newtown 20 Weston 39 Weston 15 Kolbe 50 | ||
| Tue., 9/11 | V Girls Soccer | Kolbe Cathedral | Away - Veterans Park [Directions] | 4:00 p.m. | W 9-1 | 2:40pm | |
| Tue., 9/11 | V Girls Swimming and Diving | Immaculate | Home - Weston MS Pool [Directions] | 4:00 p.m. | Weston 96 Immaculate/Bethel 75 | ||
| Tue., 9/11 | V Girls Volleyball | Staples | Away - Staples H.S. Gym [Directions] | 4:00 p.m. | L 0-3 | 2:40pm | nonleague |
| Tue., 9/11 | JV Girls Volleyball | Staples | Away - Staples H.S. Gym [Directions] | 5:00 p.m. | 2:40pm | ||
| Tue., 9/11 | FR Girls Volleyball | Kennedy Catholic-Somers (NY) | Away | 4:00 p.m. | 2:40pm | ||
| Wed., 9/12 | V Field Hockey | Masuk | Home - WHS Turf Field [Directions] | 6:30 p.m. | T 1-1 | Non-League | |
| Wed., 9/12 | JV Field Hockey | Masuk | Home - WHS Turf Field [Directions] | 5:00 p.m. | |||
| Wed., 9/12 | V Girls Volleyball | Stamford | Home - WHS Gymnasium [Directions] | 5:30 p.m. | L 1-3 | nonleague | |
| Wed., 9/12 | JV Girls Volleyball | Stamford | Home - WHS Gymnasium [Directions] | 4:00 p.m. | |||
| Wed., 9/12 | FR Girls Volleyball | Pomperaug | Away [Directions] | 3:45 p.m. | 2:40pm | ||
| Thu., 9/13 | V Boys Soccer | Bethel | Home - WHS Turf Field [Directions] | 7:00 p.m. | W 4-1 | ||
| Thu., 9/13 | JV Boys Soccer | Bethel | Home - WHS Turf Field [Directions] | 5:00 p.m. | |||
| Thu., 9/13 | V Girls Soccer | Bethel | Away - Rourke Field [Directions] | 4:00 p.m. | W 7-0 | 2:40pm | |
| Thu., 9/13 | JV Girls Soccer | Bethel | Away - Bethel MS Field [Directions] | 4:00 p.m. | 2:40pm | ||
| Thu., 9/13 | FR Girls Soccer | Masuk | Home - WHS Stadium Field [Directions] | 5:30 p.m. | |||
| Fri., 9/14 | V Football | Jonathan Law | Home - WHS Stadium Field [Directions] | 7:00 p.m. | W 35-7 | Non-League | |
| Fri., 9/14 | V Girls Swimming and Diving | Brookfield | Away - The Y.M.C.A. [Directions] | 5:30 p.m. | Weston 96 Brookfield 85 | 4:00pm | |
| Fri., 9/14 | V Girls Volleyball | Joel Barlow | Away - JBHS Lower Gym [Directions] | 5:30 p.m. | L 0-3 | 2:40pm | Non-League |
| Fri., 9/14 | JV Girls Volleyball | Joel Barlow | Away - JBHS Lower Gym [Directions] | 4:00 p.m. | 2:40pm | ||
| Fri., 9/14 | FR Girls Volleyball | Kennedy Catholic-Somers (NY) | Home - WHS Gymnasium [Directions] | 4:30 p.m. | |||
| Sat., 9/15 | V Boys Cross Country | CT River Valley Invite | Away [Directions] | 9:30 a.m. | 6:30am | at Cromwell HS | |
| Sat., 9/15 | JV Football | Jonathan Law | Away - Lawmen Stadium [Directions] | 10:30 a.m. | 8:00am | ||
| Sat., 9/15 | V Girls Cross Country | Wilton | Away [Directions] | 9:30 a.m. | |||
| Sat., 9/15 | V Field Hockey | Bethel | Home - WHS Turf Field [Directions] | 11:30 a.m. | W 5-0 | Non-League | |
| Sat., 9/15 | JV Field Hockey | Bethel | Home - WHS Turf Field [Directions] | 10:00 a.m. | |||
| Sat., 9/15 | FR Girls Soccer | Pomperaug | Away [Directions] | 9:00 a.m. | 7:15am | ||
| Mon., 9/17 | V Boys Cross Country | Masuk, New Fairfield, Immaculate | Home [Directions] | 5:00 p.m. | NF 16 - Weston 43 Immaculate 15 - Weston 49 Weston 19 - Masuk 38 | ||
| Mon., 9/17 | V Boys Soccer | New Milford | Away - New Milford HS [Directions] | 4:15 p.m. | W 2-0 | 2:40pm | |
| Mon., 9/17 | JV Boys Soccer | New Milford | Away - New Milford HS [Directions] | 4:15 p.m. | 2:40pm | ||
| Mon., 9/17 | V Girls Cross Country | Masuk, New Fairfield, Immaculate | Home [Directions] | 4:30 p.m. | New Fairfield 20 Weston 41 Immaculate 20 Weston 42 Weston 15 Masuk 50 | ||
| Mon., 9/17 | V Field Hockey | Brookfield | Away - BHS Stadium Field [Directions] | 4:15 p.m. | W 1-0 | 2:40pm | |
| Mon., 9/17 | JV Field Hockey | Brookfield | Away - BHS Back Turf [Directions] | 6:00 p.m. | 2:40pm | ||
| Mon., 9/17 | V Girls Soccer | New Milford | Home - WHS Turf Field [Directions] | 7:00 p.m. | W 4-0 | ||
| Mon., 9/17 | JV Girls Soccer | New Milford | Home - WHS Turf Field [Directions] | 5:15 p.m. | |||
| Mon., 9/17 | FR Girls Soccer | Fairfield Warde | Home - WHS Turf Field [Directions] | 3:30 p.m. | |||
| Mon., 9/17 | V Girls Volleyball | Pomperaug | Away - PHS Main Gym [Directions] | 5:30 p.m. | W 3-1 | 2:40pm | Non-League |
| Mon., 9/17 | JV Girls Volleyball | Pomperaug | Away - PHS Main Gym [Directions] | 4:00 p.m. | 2:40pm | ||
| Mon., 9/17 | FR Girls Volleyball | New Milford | Home - WHS Gymnasium [Directions] | 3:45 p.m. | |||
| Tue., 9/18 | V Girls Volleyball | Ridgefield | Home - WHS Gymnasium [Directions] | 3:30 p.m. | W 3-2 | nonleague | |
| Tue., 9/18 | JV Girls Volleyball | Ridgefield | Home - WHS Old Gymnasium [Directions] | 3:30 p.m. | |||
| Thu., 9/20 | V Boys Soccer | Joel Barlow | Away - Field J (competition field) [Directions] | 4:00 p.m. | W 1-0 | 2:45pm | |
| Thu., 9/20 | JV Boys Soccer | Joel Barlow | Away - Field E (Softball) [Directions] | 4:00 p.m. | 2:45pm | ||
| Thu., 9/20 | V Girls Soccer | Joel Barlow | Home - WHS Turf Field [Directions] | 7:00 p.m. | W 2-1 | ||
| Thu., 9/20 | JV Girls Soccer | Joel Barlow | Home - WHS Turf Field [Directions] | 5:00 p.m. | |||
| Fri., 9/21 | V Football | Notre Dame-Fairfield | Home - WHS Stadium Field [Directions] | 7:00 p.m. | W 31-0 | ||
| Fri., 9/21 | V Field Hockey | Pomperaug | Away - Sports Complex & Track [Directions] | 7:30 p.m. | L 1-3 | 4:15pm | |
| Fri., 9/21 | JV Field Hockey | Pomperaug | Away - Sports Complex & Track [Directions] | 6:00 p.m. | 4:15pm | ||
| Fri., 9/21 | V Girls Swimming and Diving | Newtown | Away - Newtown HS Pool [Directions] | 4:00 p.m. | Weston 103 Newtown 81 | 2:40pm | |
| Fri., 9/21 | V Girls Volleyball | Notre Dame-Fairfield | Away - Sister Marion Rielly Auditorium at Notre Dame [Directions] | 5:30 p.m. | W 3-0 | 2:40pm | |
| Fri., 9/21 | JV Girls Volleyball | Notre Dame-Fairfield | Away - Sister Marion Rielly Auditorium at Notre Dame [Directions] | 4:00 p.m. | 2:40pm | ||
| Fri., 9/21 | FR Girls Volleyball | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | 3:45 p.m. | 2:40pm | ||
| Sat., 9/22 | JV Football | Brookfield | Away - BHS Back Turf [Directions] | Cancelled | Cancelled | 7:30am | |
| Sat., 9/22 | FR Girls Soccer | Staples | Away - Wakeman Field B (turf) [Directions] | 10:00 a.m. | 9:00am | ||
| Mon., 9/24 | FR Girls Soccer | Fairfield Ludlowe | Home - WHS Turf Field [Directions] | 5:15 p.m. | |||
| Mon., 9/24 | V Girls Volleyball | Immaculate | Home - WHS Gymnasium [Directions] | 5:30 p.m. | W 3-1 | ||
| Mon., 9/24 | JV Girls Volleyball | Immaculate | Home - WHS Gymnasium [Directions] | 4:00 p.m. | |||
| Tue., 9/25 | V Girls Swimming and Diving | New Fairfield | Away - New Fairfield HS [Directions] | 4:00 p.m. | Weston 96 New Fairfield 82 | 2:40pm | |
| Wed., 9/26 | JV Boys Soccer | Bunnell | Away - Bunnell Turf Field [Directions] | 5:00 p.m. | 3:15pm | ||
| Wed., 9/26 | V Girls Volleyball | New Milford | Away - New Milford HS [Directions] | 6:30 p.m. | L 0-3 | 3:30pm | |
| Wed., 9/26 | JV Girls Volleyball | New Milford | Away - New Milford HS [Directions] | 5:00 p.m. | 3:30pm | ||
| Wed., 9/26 | FR Girls Volleyball | Stratford | Away - Needham Memorial Gymnasium [Directions] | 3:45 p.m. | 2:40pm | ||
| Thu., 9/27 | V Boys Cross Country | Bethel, Notre Dame-Fairfield, Stratford | Away - Bethel HS [Directions] | 5:00 p.m. | Bethel 27 - Weston 28 Weston 15 - ND 50 Weston 15 - Stratford 50 | 3:00p,m | |
| Thu., 9/27 | V Boys Soccer | Bunnell | Away - Bunnell Turf Field [Directions] | 7:00 p.m. | W 5-0 | 5:15pm | |
| Thu., 9/27 | V Girls Cross Country | Bethel, Notre Dame-Fairfield, Stratford | Away - Bethel HS [Directions] | 4:30 p.m. | Weston 21 Bethel 38 Weston 15 Notre Dame 50 Weston 15 Stratford 50 | 2:40pm | |
| Thu., 9/27 | V Field Hockey | New Milford | Home - WHS Turf Field [Directions] | 5:30 p.m. | T 1-1 | ||
| Thu., 9/27 | JV Field Hockey | New Milford | Home - WHS Turf Field [Directions] | 4:00 p.m. | |||
| Thu., 9/27 | V Girls Soccer | Bunnell | Home - WHS Turf Field [Directions] | 7:15 p.m. | W 2-1 | ||
| Thu., 9/27 | JV Girls Soccer | Bunnell | Home - WHS Stadium Field [Directions] | 5:15 p.m. | |||
| Fri., 9/28 | V Boys Cross Country | Nonnewaug Invite | Away [Directions] | Cancelled | Cancelled | at Nonnewaug HS | |
| Fri., 9/28 | V Football | Pomperaug | Away - Sports Complex & Track [Directions] | 6:30 p.m. | L 22-24 | 3:45P | |
| Fri., 9/28 | V Boys Soccer | Notre Dame-Fairfield | Home - WHS Turf Field [Directions] | 4:30 p.m. | W 1-0 | ||
| Fri., 9/28 | V Girls Volleyball | Kolbe Cathedral | Home - WHS Gymnasium [Directions] | 5:30 p.m. | W 3-0 | ||
| Fri., 9/28 | JV Girls Volleyball | Kolbe Cathedral | Home - WHS Gymnasium [Directions] | 4:00 p.m. | |||
| Fri., 9/28 | FR Girls Volleyball | Newtown | Home - WHS Old Gymnasium [Directions] | 4:00 p.m. | |||
| Sat., 9/29 | JV Football | Pomperaug | Home - WHS Stadium Field [Directions] | Cancelled | Cancelled | ||
| Sat., 9/29 | V Field Hockey | Wilton | Home - WHS Turf Field [Directions] | 12:30 p.m. | L 0-4 | Non-League | |
| Sat., 9/29 | JV Field Hockey | Wilton | Home - WHS Turf Field [Directions] | 11:00 a.m. | |||
| Sat., 9/29 | V Girls Soccer | Montville | Away - Montville H.S. [Directions] | 4:00 p.m. | W 3-2 | 11:15am | |
| Sat., 9/29 | JV Girls Soccer | Montville | Away - Montville H.S. [Directions] | 2:00 p.m. | 11:15am | ||
| Sat., 9/29 | FR Girls Soccer | Newtown | Home - WHS Turf Field [Directions] | 9:00 a.m. | |||
| Mon., 10/1 | V Field Hockey | Watertown | Home - WHS Turf Field [Directions] | 5:30 p.m. | W 1-0 | ||
| Mon., 10/1 | JV Field Hockey | Watertown | Home - WHS Turf Field [Directions] | 4:00 p.m. | |||
| Mon., 10/1 | FR Girls Soccer | Pomperaug | Away [Directions] | 3:45 p.m. | 2:40pm | ||
| Tue., 10/2 | JV Boys Soccer | Brookfield | Home - WHS Turf Field [Directions] | 4:00 p.m. | |||
| Tue., 10/2 | V Girls Cross Country | Joel Barlow, Brookfield, Pomperaug | Away - JBHS Cross Country Loop [Directions] | 4:30 p.m. | 2:40pm | ||
| Tue., 10/2 | V Girls Soccer | Brookfield | Away - BHS Stadium Field [Directions] | 4:30 p.m. | W 2-1 | 2:40pm | |
| Tue., 10/2 | JV Girls Soccer | Brookfield | Away - BHS Stadium Field [Directions] | 6:00 p.m. | 2:40pm | ||
| Tue., 10/2 | V Girls Swimming and Diving | New Milford | Home - Weston MS Pool [Directions] | 4:00 p.m. | Weston 88 New Milford 58 | ||
| Tue., 10/2 | V Girls Volleyball | New Fairfield | Home - WHS Gymnasium [Directions] | 6:00 p.m. | W 3-0 | ||
| Tue., 10/2 | JV Girls Volleyball | New Fairfield | Home - WHS Gymnasium [Directions] | 4:30 p.m. | |||
| Tue., 10/2 | FR Girls Volleyball | New Fairfield | Home - WHS Old Gymnasium [Directions] | 4:30 p.m. | |||
| Wed., 10/3 | V Boys Cross Country | Joel Barlow, Brookfield, Pomperaug | Away - JBHS Cross Country Loop [Directions] | 4:30 p.m. | Weston 27 - JB 28 Brookfield 19 - Weston 36 Pomperaug 22 - Weston 37 | 2:40pm | |
| Wed., 10/3 | V Boys Soccer | Brookfield | Home - WHS Turf Field [Directions] | 7:30 p.m. | W 4-1 | ||
| Wed., 10/3 | V Girls Volleyball | Stratford | Home - WHS Gymnasium [Directions] | 6:00 p.m. | W 3-1 | ||
| Wed., 10/3 | JV Girls Volleyball | Stratford | Home - WHS Gymnasium [Directions] | 5:00 p.m. | |||
| Wed., 10/3 | FR Girls Volleyball | Immaculate | Home - WHS Old Gymnasium [Directions] | 5:15 p.m. | |||
| Fri., 10/5 | V Boys Soccer | Newtown | Home - WHS Turf Field [Directions] | 7:00 p.m. | L 0-1 | ||
| Fri., 10/5 | JV Boys Soccer | Newtown | Home - WHS Turf Field [Directions] | 5:00 p.m. | |||
| Fri., 10/5 | V Girls Soccer | Newtown | Away - Blue and Gold Stadium [Directions] | 4:30 p.m. | L 0-1 | 5:15pm | |
| Fri., 10/5 | JV Girls Soccer | Newtown | Away - Newtown HS Practice Field [Directions] | 4:30 p.m. | 2:40pm | ||
| Fri., 10/5 | V Girls Swimming and Diving | Bunnell | Away - Flood Pool [Directions] | 6:30 p.m. | Weston 87 Bunnell 77 | 5:00pm | |
| Fri., 10/5 | FR Girls Volleyball | Brookfield | Away - BHS Small Gym [Directions] | 4:00 p.m. | 2:40pm | ||
| Sat., 10/6 | V Girls Cross Country | Wickham Invitational | Away - Wickham Park | 9:00 a.m. | |||
| Sat., 10/6 | FR Girls Soccer | Pomperaug | Home - WHS Turf Field [Directions] | 9:00 a.m. | |||
| Mon., 10/8 | V Field Hockey | Immaculate | Away - Mustang Valley [Directions] | 11:30 p.m. | L 0-2 | 8:45am | |
| Mon., 10/8 | JV Field Hockey | Immaculate | Away - Mustang Valley [Directions] | 10:00 a.m. | 8:45am | ||
| Mon., 10/8 | V Girls Soccer | Notre Dame-Fairfield | Away - Park Avenue Field at Notre Dame [Directions] | 1:15 p.m. | T 3-3 | 11:45am | |
| Mon., 10/8 | FR Girls Soccer | Trumbull | Home - WHS Turf Field [Directions] | 4:00 p.m. | |||
| Tue., 10/9 | V Boys Cross Country | Bunnell | Home - WHS Stadium Field [Directions] | 5:00 p.m. | Weston 17 - Bunnell 43 | ||
| Tue., 10/9 | V Boys Soccer | Stratford | Away - Penders Field [Directions] | 7:00 p.m. | W 4-0 | 3:30pm | |
| Tue., 10/9 | JV Boys Soccer | Stratford | Away - Penders Field [Directions] | 5:00 p.m. | 3:30pm | ||
| Tue., 10/9 | V Girls Cross Country | Bunnell | Home - WHS Stadium Field [Directions] | 4:30 p.m. | Weston 15 Bunnell 50 | ||
| Tue., 10/9 | V Field Hockey | Masuk | Away - Benedict Stadium Field @ Masuk HS [Directions] | 7:00 p.m. | W 1-0 | 4:00pm | |
| Tue., 10/9 | JV Field Hockey | Masuk | Away - Benedict Stadium Field @ Masuk HS [Directions] | 5:45 p.m. | 4:00pm | ||
| Tue., 10/9 | V Girls Swimming and Diving | Stratford | Home - Weston MS Pool [Directions] | 5:00 p.m. | |||
| Tue., 10/9 | V Girls Volleyball | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | 5:30 p.m. | L 0-3 | 2:40pm | |
| Tue., 10/9 | JV Girls Volleyball | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | 4:00 p.m. | 2:40pm | ||
| Wed., 10/10 | V Field Hockey | Bethel | Away - Hunt Field at Bethel HS [Directions] | 6:00 p.m. | L 0-1 | 4:30pm | |
| Wed., 10/10 | V Girls Volleyball | Brookfield | Away - BHS Big Gym [Directions] | 5:30 p.m. | W 3-1 | 2:40pm | |
| Wed., 10/10 | JV Girls Volleyball | Brookfield | Away - BHS Big Gym [Directions] | 4:00 p.m. | 2:40pm | ||
| Fri., 10/12 | V Football | East Lyme | Away - ELHS Dick North Field [Directions] | 6:30 p.m. | W 34-11 | 2:15pm | Non-League |
| Fri., 10/12 | V Girls Soccer | Immaculate | Home - WHS Turf Field [Directions] | 7:00 p.m. | W 2-1 | ||
| Fri., 10/12 | JV Girls Soccer | Immaculate | Home - WHS Turf Field [Directions] | 5:00 p.m. | |||
| Fri., 10/12 | V Girls Swimming and Diving | Masuk | Away - Masuk Pool [Directions] | 4:00 p.m. | Weston 100 Masuk 88 | 2:40pm | |
| Fri., 10/12 | V Girls Volleyball | Pomperaug | Home - WHS Gymnasium [Directions] | 5:30 p.m. | W 3-2 | ||
| Fri., 10/12 | JV Girls Volleyball | Pomperaug | Home - WHS Gymnasium [Directions] | 4:00 p.m. | |||
| Fri., 10/12 | FR Girls Volleyball | Stratford | Home - WHS Old Gymnasium [Directions] | 3:45 p.m. | |||
| Sat., 10/13 | JV Football | East Lyme | Home - WHS Stadium Field [Directions] | 11:00 a.m. | |||
| Sat., 10/13 | V Boys Soccer | Immaculate | Away - Mustang Valley [Directions] | 3:30 p.m. | T 1-1 | 1:45pm | |
| Sat., 10/13 | V Field Hockey | Joel Barlow | Home - WHS Turf Field [Directions] | 10:00 a.m. | T 1-1 | ||
| Sat., 10/13 | JV Field Hockey | Joel Barlow | Home - WHS Turf Field [Directions] | 11:45 a.m. | |||
| Sat., 10/13 | V Girls Soccer | Stratford | Home - WHS Turf Field [Directions] | 3:30 p.m. | W 4-0 | ||
| Sat., 10/13 | JV Girls Soccer | Stratford | Home - WHS Turf Field [Directions] | 1:30 p.m. | |||
| Mon., 10/15 | FR Girls Soccer | Masuk | Home - WHS Turf Field [Directions] | 5:15 p.m. | |||
| Mon., 10/15 | V Girls Volleyball | Bethel | Away - Bethel HS [Directions] | 5:30 p.m. | W 3-0 | 2:40pm | |
| Mon., 10/15 | JV Girls Volleyball | Bethel | Away - Bethel HS [Directions] | 4:00 p.m. | 2:40pm | ||
| Mon., 10/15 | FR Girls Volleyball | Pomperaug | Home - WHS Gymnasium [Directions] | 3:45 p.m. | |||
| Tue., 10/16 | V Boys Soccer | Masuk | Home - WHS Turf Field [Directions] | 7:15 p.m. | W 2-1 | ||
| Tue., 10/16 | JV Boys Soccer | Masuk | Home - WHS Stadium Field [Directions] | 5:15 p.m. | |||
| Tue., 10/16 | V Field Hockey | New Fairfield | Home - WHS Turf Field [Directions] | 5:30 p.m. | L 0-1 | ||
| Tue., 10/16 | JV Field Hockey | New Fairfield | Home - WHS Turf Field [Directions] | 4:00 p.m. | |||
| Tue., 10/16 | V Girls Soccer | Masuk | Away - Benedict Stadium Field @ Masuk HS [Directions] | 7:00 p.m. | L 2-3 | 5:15pm | |
| Tue., 10/16 | JV Girls Soccer | Masuk | Away - Great Hollow Lake Fields at Wolfe Park [Directions] | 4:00 p.m. | 2:40pm | ||
| Tue., 10/16 | V Girls Swimming and Diving | Joel Barlow | Home - Weston MS Pool [Directions] | 4:00 p.m. | Weston 97 Joel Barlow 82 | ||
| Wed., 10/17 | V Boys Cross Country | SWC Championship Meet | Away [Directions] | 4:35 p.m. | 2:00pm | at Bethel | |
| Wed., 10/17 | V Girls Cross Country | SWC Championship Meet | Away [Directions] | 4:00 p.m. | 2:00pm | at Bethel | |
| Wed., 10/17 | V Girls Volleyball | Joel Barlow | Home - WHS Gymnasium [Directions] | 5:30 p.m. | L 0-3 | ||
| Wed., 10/17 | JV Girls Volleyball | Joel Barlow | Home - WHS Gymnasium [Directions] | 4:00 p.m. | |||
| Wed., 10/17 | FR Girls Volleyball | New Fairfield | Away - NFHS Gym [Directions] | 4:00 p.m. | 2:40pm | ||
| Thu., 10/18 | V Boys Soccer | New Fairfield | Away - Rebel Turf [Directions] | 6:00 p.m. | W 1-0 | 2:40pm | |
| Thu., 10/18 | JV Boys Soccer | New Fairfield | Away - Rebel Turf [Directions] | 4:00 p.m. | 2:45pm | ||
| Thu., 10/18 | V Field Hockey | Newtown | Home - WHS Turf Field [Directions] | 5:30 p.m. | L 1-2 | ||
| Thu., 10/18 | JV Field Hockey | Newtown | Home - WHS Turf Field [Directions] | 4:00 p.m. | |||
| Thu., 10/18 | V Girls Soccer | New Fairfield | Home - WHS Turf Field [Directions] | 7:15 p.m. | W 3-1 | ||
| Thu., 10/18 | JV Girls Soccer | New Fairfield | Home - WHS Stadium Field [Directions] | 5:15 p.m. | |||
| Fri., 10/19 | V Football | Bethel | Away - DeSantis Field at Bethel HS [Directions] | 7:00 p.m. | W 42-6 | 4:30pm | |
| Fri., 10/19 | V Girls Volleyball | Newtown | Away - Newtown HS Gymnasium [Directions] | 5:30 p.m. | L 1-3 | 2:40pm | |
| Fri., 10/19 | JV Girls Volleyball | Newtown | Away - Newtown HS Gymnasium [Directions] | 4:00 p.m. | 2:40pm | ||
| Sat., 10/20 | JV Football | Bethel | Home - WHS Stadium Field [Directions] | 11:00 a.m. | |||
| Sat., 10/20 | V Boys Soccer | New Milford | Home - WHS Turf Field [Directions] | 6:30 p.m. | W 1-0 | Non League | |
| Sat., 10/20 | JV Boys Soccer | New Milford | Home - WHS Turf Field [Directions] | 4:30 p.m. | |||
| Sat., 10/20 | V Field Hockey | Westhill | Away - J. Walter Kennedy Stadium [Directions] | 10:30 a.m. | W 2-1 | 7:45am | Non-League |
| Sat., 10/20 | JV Field Hockey | Westhill | Away - J. Walter Kennedy Stadium [Directions] | 9:00 a.m. | 7:45am | ||
| Sat., 10/20 | V Girls Soccer | Watertown | Away - John J. Mills Complex @ Watertown HS [Directions] | 4:00 p.m. | L 2-3 | 12:00pm | non league |
| Sat., 10/20 | JV Girls Soccer | Watertown | Away - John J. Mills Complex @ Watertown HS [Directions] | 2:00 p.m. | 12:00pm | ||
| Sat., 10/20 | FR Girls Volleyball | SWC Freshman Jamboree | Away [Directions] | 9:00 a.m. | 7:30am | at Pomperaug | |
| Mon., 10/22 | V Boys Soccer | Bethel | Away - DeSantis Field at Bethel HS [Directions] | 6:00 p.m. | W 2-1 | 2:40pm | Non-League |
| Mon., 10/22 | JV Boys Soccer | Bethel | Away - Bethel MS Field [Directions] | 4:00 p.m. | 2:45pm | ||
| Mon., 10/22 | FR Girls Soccer | Masuk | Away - Great Hollow Lake Fields at Wolfe Park [Directions] | 3:45 p.m. | 2:40pm | ||
| Mon., 10/22 | V Girls Volleyball | Bunnell | Home - WHS Gymnasium [Directions] | 5:30 p.m. | W 3-0 | ||
| Mon., 10/22 | JV Girls Volleyball | Bunnell | Home - WHS Gymnasium [Directions] | 4:00 p.m. | |||
| Mon., 10/22 | FR Girls Volleyball | Wright Tech | Home - WHS Old Gymnasium [Directions] | 4:00 p.m. | |||
| Tue., 10/23 | FR Girls Soccer | Newtown | Away - Treadwell Town Park--Tilson Field [Directions] | 3:45 p.m. | 2:40pm | ||
| Wed., 10/24 | V Boys Soccer | Abbott Tech | Home - WHS Turf Field [Directions] | 6:00 p.m. | W 8-0 | nonleague | |
| Wed., 10/24 | V Girls Swimming and Diving | SWC Championship Diving Meet | Home - Weston MS Pool [Directions] | 5:30 p.m. | warm-up 4:00pm | ||
| Wed., 10/24 | V Girls Volleyball | Stratford | Away - Needham Memorial Gymnasium [Directions] | 6:00 p.m. | L 0-3 | 3:30pm | Non-League |
| Wed., 10/24 | JV Girls Volleyball | Stratford | Away - Needham Memorial Gymnasium [Directions] | 5:00 p.m. | 3:30pm | ||
| Wed., 10/24 | FR Girls Volleyball | Wright Tech | Away - Wright Tech [Directions] | 4:00 p.m. | 2:40pm | ||
| Thu., 10/25 | V Boys Cross Country | Hatters Freshman Invite | Away [Directions] | 4:45 p.m. | 2:40pm | at Tarrywile Park | |
| Thu., 10/25 | V Field Hockey | Immaculate | Away - Mustang Valley [Directions] | 3:00 p.m. | L 0-4 | 1:15pm | SWC Quarterfinals |
| Thu., 10/25 | FR Girls Soccer | Staples | Home - WHS Turf Field [Directions] | 5:15 p.m. | |||
| Fri., 10/26 | V Boys Cross Country | CIAC Class MM Championship | Away - Wickham Park - East Hartford [Directions] | 3:10 p.m. | 11:00am | at Wickham Park - East Hartford | |
| Fri., 10/26 | V Football | New Fairfield | Home - WHS Stadium Field [Directions] | 7:00 p.m. | L 0-31 | Homecoming | |
| Fri., 10/26 | V Boys Soccer | Immaculate | Home - WHS Turf Field [Directions] | 3:30 p.m. | W 1-0 | SWC Quarter-finals | |
| Fri., 10/26 | V Girls Cross Country | CIAC Class M Championship | Away - Wickham Park - East Hartford [Directions] | 2:35 p.m. | 11:00am | at Wickham Park, East Hartford | |
| Fri., 10/26 | V Girls Soccer | Immaculate | Home - WHS Stadium Field [Directions] | 3:15 p.m. | L 1-2 | SWC Quarter-Finals | |
| Sat., 10/27 | JV Football | New Fairfield | Away - Rebel Stadium [Directions] | Cancelled | Cancelled | ||
| Sat., 10/27 | V Girls Swimming and Diving | SWC Championship Swim Meet | Away [Directions] | 3:00 p.m. | 12:15pm | at Masuk | |
| Sat., 10/27 | JV Girls Volleyball | Fairfield Warde JV Volleyball Invitationsl | Away [Directions] | 9:00 a.m. | 7:30am | at Fairfield Warde | |
| Mon., 10/29 | V Boys Soccer | Newtown | Home - WHS Turf Field [Directions] | 7:00 p.m. | W 2-0 | SWC Semifinals | |
| Mon., 10/29 | V Field Hockey | SWC Semifinals | Away | Cancelled | Cancelled | TBA | at home of higher seed |
| Mon., 10/29 | V Girls Volleyball | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | 6:00 p.m. | L 0-3 | 4:15pm | SWC Quarterfinals |
| Tue., 10/30 | V Girls Soccer | SWC Seminfinals | Away | Cancelled | Cancelled | TBA | at higher seed |
| Tue., 10/30 | Miscellaneous Events | Halloween Concert | Home - WHS Gymnasium [Directions] | 2:30-9:30 p.m. | |||
| Thu., 11/1 | V Boys Cross Country | CIAC Open Championship | Away - Wickham Park - East Hartford [Directions] | 2:00 p.m. | 10:30am | at Wickham Park - East Hartford | |
| Thu., 11/1 | V Boys Soccer | Joel Barlow | Away - Newtown HS [Directions] | 7:00 p.m. | W 1-0 | 5:00pm | at Newtown HS |
| Thu., 11/1 | V Girls Cross Country | CIAC Open Championship | Away - Wickham Park - East Hartford [Directions] | 2:45 p.m. | 10:30 | at Wickham Park, East Hartford | |
| Thu., 11/1 | V Field Hockey | SWC Championship | Away | Cancelled | Cancelled | at neutral site | |
| Thu., 11/1 | V Girls Soccer | Trumbull (Scrim.) | Away - New Turf Field [Directions] | 4:15 p.m. | 2:40pm | ||
| Thu., 11/1 | V Girls Soccer | Trumbull (Scrim.) | Away - New Turf Field [Directions] | 4:15 p.m. | 2:40pm | ||
| Thu., 11/1 | V Girls Volleyball | SWC Semifinals | Away | Cancelled | Cancelled | TBA | at home of higher seed |
| Fri., 11/2 | V Football | Stratford | Home - WHS Stadium Field [Directions] | 6:00 p.m. | W 41-0 | ||
| Fri., 11/2 | V Girls Soccer | SWC Championship | Away | Cancelled | Cancelled | TBA | at neutral site |
| Fri., 11/2 | V Girls Volleyball | Immaculate (Scrim.) | Home - WHS Gymnasium [Directions] | 3:45 p.m. | |||
| Sat., 11/3 | JV Football | Stratford | Away - Penders Field [Directions] | 2:30 p.m. | 12:30pm | ||
| Sat., 11/3 | V Boys Soccer | CIAC Tourney Qualifying Round | Home - WHS Turf Field [Directions] | Cancelled | Cancelled | ||
| Sat., 11/3 | V Girls Soccer | CIAC Tourney Qualifying Round | Home - WHS Turf Field [Directions] | Cancelled | Cancelled | ||
| Sat., 11/3 | V Girls Volleyball | SWC Championship | Away | Cancelled | Cancelled | TBA | at neutral site |
| Mon., 11/5 | V Field Hockey | CIAC Tourney Qualifying Round | Away - Site TBA | Cancelled | Cancelled | ||
| Mon., 11/5 | V Girls Soccer | Plainville | Home - WHS Stadium Field [Directions] | 6:00 p.m. | W 1-0 | ||
| Mon., 11/5 | V Girls Volleyball | Berlin | Away - BHS A-Gym [Directions] | 5:30 p.m. | W 3-1 | 2:40pm | |
| Tue., 11/6 | V Boys Soccer | CIAC Tourney 1st Round | Home - WHS Turf Field [Directions] | Cancelled | Cancelled | ||
| Tue., 11/6 | V Field Hockey | Immaculate | Away - Immaculate HS [Directions] | 5:30 p.m. | L 0-2 | 3:45pm | at WCSU |
| Wed., 11/7 | V Girls Soccer | Wolcott | Away - Wolcott HS, Monroe Field [Directions] | 5:00 p.m. | W 3-2 (9-8 in PKs) | 2:40pm | |
| Wed., 11/7 | V Girls Volleyball | Bullard Havens Tech | Away - BHT GYM [Directions] | 6:00 p.m. | W 3-0 | 4pm | |
| Thu., 11/8 | V Boys Soccer | Guilford | Home - WHS Turf Field [Directions] | 6:00 p.m. | W 1-0 (4-3 in PKs) | ||
| Thu., 11/8 | V Field Hockey | CIAC Tourney Quarterfinals | Away - Higher Seed | TBA | |||
| Thu., 11/8 | V Girls Swimming and Diving | CIAC Class S Diving Trials/Finals | Away - Bulkeley HS [Directions] | 5:30 p.m. | |||
| Fri., 11/9 | V Football | Brookfield | Away [Directions] | 5:00 p.m. | L 12-32 | 1:45pm | |
| Fri., 11/9 | V Girls Soccer | Granby Memorial | Away - Granby Memorial HS [Directions] | 2:00 p.m. | W 2-1 | 10:45am | |
| Fri., 11/9 | V Girls Volleyball | Granby Memorial | Away - Granby Memorial HS [Directions] | 5:00 p.m. | W 3-2 | 1:45pm | |
| Sat., 11/10 | V Boys Cross Country | New England Championship | Away - Derryfield Park (Manchester, NH) [Directions] | TBA | |||
| Sat., 11/10 | JV Football | Brookfield | Home - WHS Stadium Field [Directions] | Cancelled | Cancelled | ||
| Sat., 11/10 | V Boys Soccer | Wethersfield | Home - WHS Turf Field [Directions] | 6:00 p.m. | L 0-3 | CIAC Tourney Quarterfinals | |
| Sat., 11/10 | V Girls Cross Country | New England Championship | Away - Derryfield Park (Manchester, NH) [Directions] | TBA | |||
| Sat., 11/10 | V Girls Swimming and Diving | CIAC Class S Qualifying | Away - Cheshire Community Pool [Directions] | 10:00 a.m. | 6:45am | ||
| Mon., 11/12 | V Girls Soccer | Plainfield | Away [Directions] | 4:00 p.m. | L 1-2 (3-1 in PKs) | 1:00pm | CIAC Tourney Semifinals at Veterans Stadium, New Britain |
| Tue., 11/13 | V Boys Soccer | CIAC Tourney Semifinals (Possible Date) | Away - Site TBA | TBA | |||
| Tue., 11/13 | V Field Hockey | CIAC Tourney Semifinals (Possible Date) | Away - Site TBA | TBA | |||
| Tue., 11/13 | V Girls Soccer | CIAC Tourney Semifinals (Possible Date) | Away - Site TBA | Cancelled | Cancelled | ||
| Tue., 11/13 | V Girls Volleyball | Jonathan Law | Away [Directions] | 6:00 p.m. | W 3-1 | 4:00pm | CIAC Tourney Semifinals at Fairfield Ludlowe |
| Wed., 11/14 | V Boys Soccer | CIAC Tourney Semifinals (Possible Date) | Away - Site TBA | TBA | |||
| Wed., 11/14 | V Field Hockey | CIAC Tourney Semifinals (Possible Date) | Away - Site TBA | TBA | |||
| Wed., 11/14 | V Girls Swimming and Diving | CIAC Class S Finals | Away - Wesleyan [Directions] | 7:00 p.m. | 3:15PM | ||
| Thu., 11/15 | V Girls Swimming and Diving | CIAC Open Diving | Away - Middletown HS [Directions] | 5:30 p.m. | |||
| Fri., 11/16 | JV Football | Joel Barlow | Home - WHS Stadium Field [Directions] | Cancelled | Cancelled | ||
| Sat., 11/17 | V Boys Soccer | CIAC Tourney Final | Away - Site TBA | TBA | |||
| Sat., 11/17 | V Field Hockey | CIAC Tourney Final | Away - Wethersfield [Directions] | TBA | |||
| Sat., 11/17 | V Girls Soccer | CIAC Tourney Final | Away - Site TBA | TBA | |||
| Sat., 11/17 | V Girls Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 12:00 p.m. | TBA | ||
| Sat., 11/17 | V Girls Volleyball | Seymour | Away - East Haven [Directions] | 4:00 p.m. | 1:30pm | CIAC Tourney Final at East Haven | |
| Wed., 11/21 | V Football | Joel Barlow | Away - Field I (Stadium) [Directions] | 5:00 p.m. | W 48-17 | 2:30pm | |
| Tue., 11/27 | V Football | CIAC Tourney Quarterfinals | Away - Higher Seed | TBA | |||
| Fri., 11/30 | V Girls Basketball | Greenwich (Scrim.) | Away - GHS Gymnasium [Directions] | 4:00 p.m. | 2:40pm | ||
| Fri., 11/30 | JV Girls Basketball | Greenwich (Scrim.) | Away - GHS Gymnasium [Directions] | 4:00 p.m. | 2:40pm | ||
| Sat., 12/1 | V Wrestling | Norwalk (Scrim.) | Away [Directions] | 9:00 a.m. | 8:30am | ||
| Sun., 12/2 | V Football | CIAC Tourney Semifinals | Away - Higher Seed | TBA | |||
| Mon., 12/3 | V Girls Basketball | Darien (Scrim.) | Away - DHS Main Gym [Directions] | 4:00 p.m. | 3:00Ppm | ||
| Mon., 12/3 | JV Girls Basketball | Darien (Scrim.) | Away - DHS Main Gym [Directions] | 4:00 p.m. | 3:00pm | ||
| Wed., 12/5 | V Boys Basketball | Jonathan Law (Scrim.) | Away - Jonathan Law HS-Richetelli Gymnasium [Directions] | 6:00 p.m. | 4:30pm | ||
| Wed., 12/5 | V Girls Ice Hockey | Fairfield Ludlowe/Warde (Scrim.) | Away - Wonderland of Ice [Directions] | 3:15 p.m. | 2:15 pm | ||
| Thu., 12/6 | V Girls Basketball | Ridgefield (Scrim.) | Home - WHS Gymnasium [Directions] | 5:15 p.m. | |||
| Fri., 12/7 | V Boys Ice Hockey | Brien McMahon/Norwalk (Scrim.) | Home - Danbury Ice Arena [Directions] | 7:30 p.m. | W 3-2 | ||
| Fri., 12/7 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - The Rinks at Shelton [Directions] | 4:00 p.m. | L 8-2 | ||
| Sat., 12/8 | V Football | CIAC Tourney Final | Away - Site TBA | TBA | |||
| Sat., 12/8 | V Wrestling | Westhill (Scrim.) | Away [Directions] | 9:00 a.m. | 8:15am | ||
| Mon., 12/10 | V Boys Basketball | Wooster (Scrim.) | Home - WHS Old Gymnasium [Directions] | 5:30 p.m. | |||
| Mon., 12/10 | V Girls Basketball | New Milford | Home - WHS Gymnasium [Directions] | 6:00 p.m. | W 47-17 | nonleague | |
| Mon., 12/10 | JV Girls Basketball | New Milford | Home - WHS Gymnasium [Directions] | 4:15 p.m. | |||
| Wed., 12/12 | V Boys Ice Hockey | Wilton | Home - Danbury Ice Arena [Directions] | 7:40 p.m. | L 4-7 | ||
| Wed., 12/12 | V Wrestling | Pomperaug Coop | Home - WHS Gymnasium [Directions] | 6:00 p.m. | Pomperaug 48 weston 30 | Crossover Match | |
| Wed., 12/12 | V Girls Ice Hockey | Branford | Home - The Rinks at Shelton [Directions] | 4:00 p.m. | L 6-1 | ||
| Thu., 12/13 | V Boys Swimming and Diving | Newtown | Away [Directions] | 5:00 p.m. | Newtown 96 Weston 76 | 3:30pm | |
| Sat., 12/15 | V Boys Basketball | Staples | Home - WHS Gymnasium [Directions] | 6:00 p.m. | L 71-49 | Non-League | |
| Sat., 12/15 | JV Boys Basketball | Staples | Home - WHS Gymnasium [Directions] | 4:15 p.m. | |||
| Sat., 12/15 | FR Boys Basketball | Staples | Home - WHS Gymnasium [Directions] | 2:30 p.m. | |||
| Sat., 12/15 | V Boys Ice Hockey | Newington Coop | Home - Danbury Ice Arena [Directions] | 4:40 p.m. | L 10-11(OT) | ||
| Sat., 12/15 | V Boys Indoor Track | Hillhouse Varsity Invite | Away | 9:00 a.m. | 7:00am | ||
| Sat., 12/15 | V Boys Indoor Track | SCSU Rist Buster Relays | Away | 9:00 a.m. | 6:45am | at SCSU | |
| Sat., 12/15 | V Wrestling | Shelton Invitational | Away [Directions] | 9:30 a.m. | 7:30am | at Shelton HS | |
| Sat., 12/15 | V Girls Ice Hockey | West Haven/SHA | Away - Bennett Rink [Directions] | 1:00 p.m. | L 7-0 | 11:15 am | |
| Sat., 12/15 | V Girls Indoor Track | Hillhouse Varsity Invite | Away [Directions] | 9:00 a.m. | 7:00am | ||
| Sat., 12/15 | V Girls Indoor Track | Rist Buster Relays | Away | 9:00 a.m. | 6:45am | at SCSU | |
| Mon., 12/17 | V Girls Basketball | Brookfield | Home - WHS Gymnasium [Directions] | 7:00 p.m. | W 62-41 | Non-League | |
| Mon., 12/17 | JV Girls Basketball | Brookfield | Home - WHS Gymnasium [Directions] | 5:15 p.m. | |||
| Mon., 12/17 | FR Girls Basketball | Brookfield | Home - WHS Gymnasium [Directions] | 3:45 p.m. | |||
| Tue., 12/18 | V Boys Basketball | Westhill | Home - WHS Gymnasium [Directions] | 7:00 p.m. | L 64-47 | Non-League | |
| Tue., 12/18 | JV Boys Basketball | Westhill | Home - WHS Gymnasium [Directions] | 5:15 p.m. | |||
| Tue., 12/18 | FR Boys Basketball | Westhill | Home - WHS Gymnasium [Directions] | 3:30 p.m. | |||
| Wed., 12/19 | V Boys Ice Hockey | Shepaug Valley Ice Hockey | Away - Gunnery Rink [Directions] | 6:00 p.m. | W 10-3 | ||
| Wed., 12/19 | V Wrestling | New Fairfield | Away [Directions] | 6:00 p.m. | New Fairfield 55 Weston 45 | 4:00pm | |
| Wed., 12/19 | V Girls Ice Hockey | Hamden Coop | Home - The Rinks at Shelton [Directions] | 5:00 p.m. | L 8-0 | ||
| Thu., 12/20 | V Girls Basketball | Newtown | Home - WHS Gymnasium [Directions] | 7:00 p.m. | L 31-62 | ||
| Thu., 12/20 | JV Girls Basketball | Newtown | Home - WHS Gymnasium [Directions] | 5:15 p.m. | |||
| Thu., 12/20 | FR Girls Basketball | Newtown | Home - WHS Gymnasium [Directions] | 3:30 p.m. | |||
| Fri., 12/21 | V Girls Ice Hockey | East Catholic Coop | Home - The Rinks at Shelton [Directions] | 4:00 p.m. | L 8-0 | ||
| Sat., 12/22 | V Boys Basketball | Achievement First | Home - WHS Gymnasium [Directions] | 2:30 p.m. | L 56-58 | Non-League | |
| Sat., 12/22 | JV Boys Basketball | Achievement First | Home - WHS Gymnasium [Directions] | 1:00 p.m. | |||
| Sat., 12/22 | V Girls Basketball | Weaver | Home - WHS Gymnasium [Directions] | 4:30 p.m. | L 41-54 | Non-League | |
| Sat., 12/22 | FR Girls Basketball | Masuk | Home - WHS Gymnasium [Directions] | 11:30 a.m. | |||
| Sun., 12/23 | V Boys Ice Hockey | Alumni Game | Home - Danbury Ice Arena [Directions] | 7:00 p.m. | |||
| Thu., 12/27 | V Boys Basketball | Bethel | Home - WHS Gymnasium [Directions] | 6:00 p.m. | W 63-61 | Non-League | |
| Thu., 12/27 | JV Boys Basketball | Bethel | Home - WHS Gymnasium [Directions] | 4:00 p.m. | |||
| Thu., 12/27 | V Boys Indoor Track | Jack Long Invite | Away [Directions] | 12:00 p.m. | 10:00am | at Hillhouse | |
| Thu., 12/27 | V Girls Indoor Track | Jack Long Invite | Away [Directions] | 12:00 p.m. | 10:00am | at Hillhouse | |
| Fri., 12/28 | V Wrestling | Harding/Bassick/Bridgeport Central | Away - Harding-Auxiliary Gym [Directions] | 1:00 p.m. | Weston 42 Harding 23 | 11:00am | Non-League |
| Sat., 12/29 | V Boys Basketball | Darien | Away - DHS Main Gym [Directions] | 5:00 p.m. | L 46-52 | 1:45pm | Non-League |
| Sat., 12/29 | JV Boys Basketball | Darien | Away - DHS Main Gym [Directions] | 3:00 p.m. | 1:45pm | ||
| Sat., 12/29 | V Boys Ice Hockey | Masuk | Away - The Rinks at Shelton [Directions] | 8:00 p.m. | W 8-0 | ||
| Wed., 1/2 | V Boys Ice Hockey | Byram Hills (NY) | Home - Danbury Ice Arena [Directions] | 7:40 p.m. | W 10-2 | ||
| Thu., 1/3 | JV Boys Ice Hockey | Immaculate | Home - Danbury Ice Arena [Directions] | 7:40 p.m. | |||
| Thu., 1/3 | V Boys Indoor Track | SWC JV Developmental Meet | Away | 3:00 p.m. | 2:40pm | at Danbury Sports Dome | |
| Thu., 1/3 | V Girls Gymnastics | Darien, Oxford | Home - GCA [Directions] | 6:30 p.m. | Ludlowe- 130.00 Oxford- 129.15 Warde- 126.40 Darien- 119.00 | ||
| Thu., 1/3 | V Girls Indoor Track | SWC JV Developmental Meet | Away | 3:00 p.m. | 2:40pm | at Danbury Sports Dome | |
| Fri., 1/4 | V Boys Basketball | Brookfield | Away - BHS Big Gym [Directions] | 7:00 p.m. | L 39-45 | 4:30pm | Non-League |
| Fri., 1/4 | JV Boys Basketball | Brookfield | Away - BHS Big Gym [Directions] | 5:15 p.m. | 2:40pm | ||
| Fri., 1/4 | FR Boys Basketball | Brookfield | Away - BHS Big Gym [Directions] | 3:30 p.m. | 2:40pm | ||
| Fri., 1/4 | V Wrestling | Stratford | Home - WHS Gymnasium [Directions] | 6:00 p.m. | Stratford 40 Weston 39 | ||
| Fri., 1/4 | V Girls Basketball | Immaculate | Away - Immaculate HS [Directions] | 7:00 p.m. | W 44-29 | 4:00pm | |
| Fri., 1/4 | JV Girls Basketball | Immaculate | Away - Immaculate HS [Directions] | 5:15 p.m. | 4:00pm | ||
| Fri., 1/4 | FR Girls Basketball | Immaculate | Away - Immaculate HS [Directions] | 3:30 p.m. | 2:40pm | ||
| Fri., 1/4 | V Girls Ice Hockey | Guilford Coop | Home - The Rinks at Shelton [Directions] | 4:00 p.m. | L 5-0 | ||
| Sat., 1/5 | V Boys Ice Hockey | Trinity Catholic | Away - Terry Conners Ice Rink | 2:20 p.m. | W 8-1 | ||
| Sat., 1/5 | V Boys Indoor Track | SWC Developmental Meet | Away | 8:00 a.m. | 5:30am | at Wesleyan | |
| Sat., 1/5 | V Girls Gymnastics | Pomperaug Invitational | Away - Pomperaug HS | 10:00 a.m. | 133.70 1st place | PU 8:15 at Ludlowe, 8:30 at Warde RE 1:00 | |
| Sat., 1/5 | V Girls Indoor Track | SWC Developmental Meet | Away | 8:00 a.m. | 5:30am | at Wesleyan | |
| Sun., 1/6 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Home - The Rinks at Shelton [Directions] | 4:30 p.m. | L 7-4 | ||
| Mon., 1/7 | FR Girls Basketball | Pomperaug | Away - PHS Main Gym [Directions] | 5:30 p.m. | 3:45pm | ||
| Tue., 1/8 | V Boys Swimming and Diving | Masuk | Away - Masuk Pool [Directions] | 4:00 p.m. | Masuk 95 Weston 82 | 2:40pm | |
| Tue., 1/8 | V Girls Basketball | Kolbe Cathedral | Home - WHS Gymnasium [Directions] | 7:00 p.m. | W 47-40 | ||
| Tue., 1/8 | JV Girls Basketball | Kolbe Cathedral | Home - WHS Gymnasium [Directions] | 5:15 p.m. | |||
| Tue., 1/8 | V Girls Gymnastics | Foran | Home - GCA in Fairfield [Directions] | 6:30 p.m. | 130.15 | PU 4:45 at Ludlowe RE 8:30 | |
| Wed., 1/9 | V Boys Basketball | Kolbe Cathedral | Away - Shehan Center [Directions] | 7:00 p.m. | L 30-51 | 3:45pm | |
| Wed., 1/9 | JV Boys Basketball | Kolbe Cathedral | Away - Shehan Center [Directions] | 5:15 p.m. | 3:45pm | ||
| Wed., 1/9 | V Boys Ice Hockey | Sheehan | Home - Danbury Ice Arena [Directions] | 8:40 p.m. | L 5-12 | ||
| Wed., 1/9 | V Boys Indoor Track | SWC JV Developmental Meet | Away | 3:00 p.m. | 2:40pm | at Danbury Sports Dome | |
| Wed., 1/9 | V Wrestling | Bunnell | Away - Bunnell [Directions] | 6:00 p.m. | Bunnell 39 Weston 37 | 4:15pm | Crossover Match |
| Wed., 1/9 | V Girls Indoor Track | SWC JV Developmental Meet | Away | 3:00 p.m. | 2:40pm | at Danbury Sports Dome | |
| Thu., 1/10 | JV Boys Ice Hockey | Newtown/New Fairfield | Home - Danbury Ice Arena [Directions] | 7:50 p.m. | |||
| Thu., 1/10 | V Girls Ice Hockey | Daniel Hand Coop | Away - Northford Ice Pavilion [Directions] | 4:00 p.m. | L 9-1 | 1:30 pm | |
| Fri., 1/11 | V Boys Basketball | Masuk | Home - WHS Gymnasium [Directions] | 7:00 p.m. | L 47-51 | ||
| Fri., 1/11 | JV Boys Basketball | Masuk | Home - WHS Gymnasium [Directions] | 5:15 p.m. | |||
| Fri., 1/11 | FR Boys Basketball | Masuk | Home - WHS Gymnasium [Directions] | 3:30 p.m. | |||
| Fri., 1/11 | V Boys Indoor Track | Yale Classic Invitational | Away | 1:00 p.m. | 10:30am | at Yale | |
| Fri., 1/11 | V Girls Basketball | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | 7:00 p.m. | L 41-51 | 4:45pm | |
| Fri., 1/11 | JV Girls Basketball | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | 5:15 p.m. | 2:40pm | ||
| Fri., 1/11 | FR Girls Basketball | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | 3:30 p.m. | 2:40pm | ||
| Fri., 1/11 | V Girls Gymnastics | Daniel Hand, Fairfield Warde | Home - GCA [Directions] | 6:30 p.m. | Ludlowe- 131.70 Warde- 125.30 Daniel Hand- 118.70 | ||
| Fri., 1/11 | V Girls Indoor Track | Yale Classic Invitational | Away | 1:00 p.m. | 10:30am | at Yale | |
| Sat., 1/12 | V Boys Indoor Track | Shoreline Invite | Away | 9:00 a.m. | 7:30am | at Hillhouse | |
| Sat., 1/12 | V Boys Indoor Track | Yale Classic Invitational | Away | TBA | at Yale | ||
| Sat., 1/12 | V Wrestling | Kearney Duals | Away [Directions] | 10:00 a.m. | Weston 56 Derby 18 Weston 78 Darien 6 Weston 43 Bunnell 33 | 8:45am | at Darien HS |
| Sat., 1/12 | V Girls Basketball | Wilton | Home - WHS Gymnasium [Directions] | 4:00 p.m. | W 54-46 | 4:15pm | Non-League |
| Sat., 1/12 | JV Girls Basketball | Wilton | Home - WHS Gymnasium [Directions] | 2:30 p.m. | 4:15pm | ||
| Sat., 1/12 | V Girls Ice Hockey | Notre Dame-Fairfield | Home - The Rinks at Shelton - Upper [Directions] | 8:50 p.m. | L 6-1 | ||
| Sat., 1/12 | V Girls Indoor Track | Shoreline Invite | Away [Directions] | 9:00 a.m. | 7:30am | at Hillhouse | |
| Sat., 1/12 | V Girls Indoor Track | Tale Classic Inviatational | Away | TBA | TBA | at Yale | |
| Mon., 1/14 | V Girls Gymnastics | Westhill, New Canaan | Home - GCA [Directions] | 6:30 p.m. | Ludlowe- 136.05 New Canaan- 118.50 Westhill- 112.00 | ||
| Tue., 1/15 | V Boys Basketball | Stratford | Home - WHS Gymnasium [Directions] | 7:00 p.m. | L 52-60 | ||
| Tue., 1/15 | JV Boys Basketball | Stratford | Home - WHS Gymnasium [Directions] | 5:15 p.m. | |||
| Tue., 1/15 | FR Boys Basketball | Stratford | Home - WHS Gymnasium [Directions] | 3:30 p.m. | |||
| Tue., 1/15 | V Boys Swimming and Diving | New Milford | Home - Weston MS Pool [Directions] | 4:00 p.m. | Weston 92 New Milford 88 | ||
| Tue., 1/15 | V Girls Basketball | Stratford | Away - Needham Memorial Gymnasium [Directions] | 7:00 p.m. | W 45-38 | 3:45pm | |
| Tue., 1/15 | JV Girls Basketball | Stratford | Away - Needham Memorial Gymnasium [Directions] | 5:15 p.m. | 3:45pm | ||
| Wed., 1/16 | V Boys Ice Hockey | Northeastern Shamrocks | Home - Danbury Ice Arena [Directions] | 4:10 p.m. | W 9-6 | ||
| Wed., 1/16 | V Boys Indoor Track | SWC JV Developmental Meet | Away | 3:00 p.m. | 2:40pm | at Danbury Sports Dome | |
| Wed., 1/16 | V Wrestling | Joel Barlow | Away - JBHS Upper Gym [Directions] | 6:00 p.m. | Joel Barlow 50 Weston 30 | 4:15pm | |
| Wed., 1/16 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - Winter Garden Rink-Ridgefield [Directions] | 8:30 p.m. | L 11-6 | 6:30 pm | |
| Wed., 1/16 | V Girls Indoor Track | SWC JV Developmental Meet | Away | 3:00 p.m. | 2:40pm | at Danbury Sports Dome | |
| Thu., 1/17 | JV Boys Ice Hockey | Newtown/New Fairfield | Home - Danbury Ice Arena [Directions] | 7:50 p.m. | |||
| Thu., 1/17 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Away - Hamden Ice Rink [Directions] | 4:30 p.m. | L 6-0 | 2:30 pm | Pick up @ Shelton |
| Fri., 1/18 | V Boys Basketball | Brookfield | Home - WHS Gymnasium [Directions] | 7:00 p.m. | L 29-59 | ||
| Fri., 1/18 | JV Boys Basketball | Brookfield | Home - WHS Gymnasium [Directions] | 5:15 p.m. | |||
| Fri., 1/18 | V Girls Basketball | Brookfield | Away - BHS Big Gym [Directions] | 7:00 p.m. | L 28-31 | 3:45pm | |
| Fri., 1/18 | JV Girls Basketball | Brookfield | Away - BHS Big Gym [Directions] | 5:15 p.m. | 3:45pm | ||
| Fri., 1/18 | FR Girls Basketball | Brookfield | Away - BHS Big Gym [Directions] | 3:45 p.m. | 2:40pm | ||
| Fri., 1/18 | V Girls Gymnastics | Greenwich | Away - Greenwich YWCA [Directions] | 6:00 p.m. | Ludlowe- 137.20 Greenwich- 135.00 | PU 4:00 at Warde, 4:15 at Ludlowe RE 8:00 | |
| Sat., 1/19 | V Boys Indoor Track | SCC Coaches Invite | Away [Directions] | 9:00 a.m. | 6:30am | at Floyd Little Athletic Center | |
| Sat., 1/19 | V Wrestling | New Milford Tournament | Away [Directions] | 9:30 a.m. | 7:15am | at New Milford HS | |
| Sat., 1/19 | V Girls Indoor Track | SCC Coaches Invite | Away [Directions] | 2:30 p.m. | 11:45am | at Floyd Little Athletic Center | |
| Tue., 1/22 | V Boys Basketball | New Fairfield | Away - NFHS Gym [Directions] | 7:00 p.m. | W 51-42 | 3:45pm | |
| Tue., 1/22 | JV Boys Basketball | New Fairfield | Away - NFHS Gym [Directions] | 5:15 p.m. | 3:45pm | ||
| Tue., 1/22 | FR Boys Basketball | New Fairfield | Away - NFHS Gym [Directions] | 3:30 p.m. | 2:40pm | ||
| Tue., 1/22 | V Boys Swimming and Diving | Joel Barlow-Bethel Swim | Home - Weston MS Pool [Directions] | 4:00 p.m. | Barlow/Bethel 105 Weston 81 | ||
| Tue., 1/22 | V Girls Basketball | New Fairfield | Home - WHS Gymnasium [Directions] | 7:00 p.m. | W 46-39 | ||
| Tue., 1/22 | JV Girls Basketball | New Fairfield | Home - WHS Gymnasium [Directions] | 5:15 p.m. | |||
| Tue., 1/22 | FR Girls Basketball | New Fairfield | Home - WHS Gymnasium [Directions] | 3:30 p.m. | |||
| Wed., 1/23 | V Boys Ice Hockey | New Milford | Home - Danbury Ice Arena [Directions] | 5:30 p.m. | W 6-2 | ||
| Wed., 1/23 | V Boys Indoor Track | SWC Developmental Meet | Away | 4:00 p.m. | 1:45pm | at Wesleyan | |
| Wed., 1/23 | V Wrestling | Brookfield/Shepaug | Home - WHS Gymnasium [Directions] | 6:00 p.m. | Brookfield 39 Weston 36 | ||
| Wed., 1/23 | V Girls Gymnastics | Trumbull, Fairfield Warde | Away - Gymnastics & Cheer Academy 85 Mill Plain Rd, Fairfield [Directions] | 6:30 p.m. | Ludlowe- 132.85 Trumbull- 128.65 | ||
| Wed., 1/23 | V Girls Indoor Track | SWC Developmental Meet | Away | 4:00 p.m. | 1:45pm | at Wesleyan | |
| Thu., 1/24 | V Boys Basketball | Bunnell | Away - Bunnell [Directions] | 7:00 p.m. | L 63-69 | 3:45pm | |
| Thu., 1/24 | JV Boys Basketball | Bunnell | Away - Bunnell [Directions] | 5:15 p.m. | 3:45pm | ||
| Thu., 1/24 | FR Boys Basketball | Bunnell | Away - Bunnell [Directions] | 3:30 p.m. | 2:40pm | ||
| Thu., 1/24 | V Girls Basketball | Bunnell | Home - WHS Gymnasium [Directions] | 7:00 p.m. | W 48-30 | ||
| Thu., 1/24 | JV Girls Basketball | Bunnell | Home - WHS Gymnasium [Directions] | 5:15 p.m. | |||
| Thu., 1/24 | V Girls Ice Hockey | Branford | Away - East Haven Ice Rink [Directions] | 8:00 p.m. | L 8-0 | 6:00 pm | Pick up @ Shelton |
| Fri., 1/25 | V Wrestling | Brien McMahon | Home - WHS Gymnasium [Directions] | 6:00 p.m. | Brien McMahon 47 Weston 27 | Non-League | |
| Fri., 1/25 | V Girls Basketball | SMSA | Away - SMSA [Directions] | 6:15 p.m. | W 51-48 | 2:40pm | Non-League |
| Fri., 1/25 | JV Girls Basketball | SMSA | Away - SMSA [Directions] | 4:45 p.m. | 2:40pm | ||
| Fri., 1/25 | V Girls Ice Hockey | West Haven/SHA | Home - The Rinks at Shelton [Directions] | 4:00 p.m. | L 6-1 | ||
| Sat., 1/26 | V Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena [Directions] | 6:40 p.m. | W 8-3 | ||
| Sat., 1/26 | V Wrestling | Norwalk JV Tournament | Away [Directions] | 9:00 a.m. | 8:00am | at Norwalk HS | |
| Mon., 1/28 | V Boys Basketball | New Milford | Home - WHS Gymnasium [Directions] | 7:00 p.m. | W 70-51 | ||
| Mon., 1/28 | JV Boys Basketball | New Milford | Home - WHS Gymnasium [Directions] | 5:15 p.m. | |||
| Mon., 1/28 | FR Boys Basketball | New Milford | Home - WHS Gymnasium [Directions] | 3:45 p.m. | |||
| Mon., 1/28 | V Girls Basketball | New Milford | Away - New Milford HS [Directions] | 6:00 p.m. | W 50-34 | 2:45pm | |
| Mon., 1/28 | JV Girls Basketball | New Milford | Away - New Milford HS [Directions] | 4:30 p.m. | 2:45pm | ||
| Mon., 1/28 | Miscellaneous Events | Unified Basketball | Home - WHS Gymnasium [Directions] | 2:30 p.m. | vs. IPPI | ||
| Thu., 1/31 | JV Boys Ice Hockey | Lyman Hall | Home - Danbury Ice Arena [Directions] | 7:50 p.m. | |||
| Thu., 1/31 | V Boys Swimming and Diving | Brookfield | Home - Weston MS Pool [Directions] | 4:00 p.m. | Brookfield 94 Weston 87 | ||
| Thu., 1/31 | V Girls Basketball | Pomperaug | Home - WHS Gymnasium [Directions] | 7:00 p.m. | L 33-46 | ||
| Thu., 1/31 | JV Girls Basketball | Pomperaug | Home - WHS Gymnasium [Directions] | 5:15 p.m. | |||
| Thu., 1/31 | FR Girls Basketball | Pomperaug | Home - WHS Gymnasium [Directions] | 3:30 p.m. | |||
| Thu., 1/31 | V Girls Gymnastics | Staples | Home - GCA [Directions] | 6:30 p.m. | Ludlowe- 136.20 Staples- 124.05 | ||
| Fri., 2/1 | V Boys Basketball | Pomperaug | Away - PHS Main Gym [Directions] | 7:00 p.m. | L 58-61 | 3:45pm | |
| Fri., 2/1 | JV Boys Basketball | Pomperaug | Away - PHS Main Gym [Directions] | 5:15 p.m. | 3:45pm | ||
| Fri., 2/1 | FR Boys Basketball | Pomperaug | Away - PHS Main Gym [Directions] | 3:30 p.m. | 2:40pm | ||
| Fri., 2/1 | V Wrestling | Notre Dame-Fairfield | Home - WHS Gymnasium [Directions] | 6:00 p.m. | Weston 66 ND Ffld 15 | ||
| Fri., 2/1 | V Competitive Cheerleading | SWC Competition | Away [Directions] | 7:00 p.m. | 4:45pm | at Newtown | |
| Fri., 2/1 | V Girls Ice Hockey | Daniel Hand Coop | Home - The Rinks at Shelton [Directions] | 5:00 p.m. | L 8-0 | ||
| Sat., 2/2 | V Boys Ice Hockey | Shepaug Valley Ice Hockey | Home - Danbury Ice Arena [Directions] | 4:50 p.m. | L 4-6 | ||
| Sat., 2/2 | V Boys Indoor Track | SWC Championship Meet | Away | 5:00 p.m. | 2:40pm | at Floyd Little Athletic Center | |
| Sat., 2/2 | V Wrestling | Luldowe JV Tournament | Away [Directions] | 9:30 a.m. | 7:45am | at Fairfield Ludlowe HS | |
| Sat., 2/2 | V Girls Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | L 27-34 | 2:15pm | Non-League |
| Sat., 2/2 | V Girls Ice Hockey | Avon | Away - Newington Ice Arena [Directions] | 8:50 p.m. | L 6-1 | 6:50 pm | Pick up @ Masuk |
| Sat., 2/2 | V Girls Indoor Track | SWC Championship Meet | Away | 5:00 p.m. | 2:40pm | at Floyd Little Athletic Center | |
| Mon., 2/4 | V Boys Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 7:00 p.m. | L 58-68 | 3:45pm | Non-League |
| Mon., 2/4 | JV Boys Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 5:30 p.m. | 3:45pm | ||
| Mon., 2/4 | FR Boys Basketball | Greenwich | Home - WHS Gymnasium [Directions] | 5:30 p.m. | |||
| Mon., 2/4 | V Boys Ice Hockey | Norwich Free Academy | Home - Danbury Ice Arena [Directions] | 7:10 p.m. | L 2-3 | ||
| Mon., 2/4 | V Wrestling | Bethel | Away [Directions] | 6:00 p.m. | Weston 48 Bethel 30 | 4:00pm | Crossover Match |
| Mon., 2/4 | V Girls Basketball | Harding | Away - Harding-Miska Gymnasium [Directions] | 5:30 p.m. | W 56-43 | 2:40pm | Non-League |
| Mon., 2/4 | JV Girls Basketball | Harding | Away - Harding-Miska Gymnasium [Directions] | 4:00 p.m. | 2:40pm | ||
| Mon., 2/4 | Miscellaneous Events | Unified Basketball | Home - WHS Gymnasium [Directions] | 3:00 p.m. | vs. Bethel and Joel Barlow | ||
| Tue., 2/5 | V Boys Swimming and Diving | Bunnell-Stratford | Away - Flood M.S. [Directions] | 6:00 p.m. | Weston 78 Bunnell/Stratford 58 | 4:30pm | |
| Tue., 2/5 | V Girls Gymnastics | Wilton, Fairfield Warde | Away [Directions] | 4:30 p.m. | Wilton- 139.50 Ludlowe- 138.35 | PU 3:00 Warde, 3:15 Ludlowe RE 7:00 | |
| Tue., 2/5 | V Girls Ice Hockey | Guilford Coop | Away - East Haven Ice Rink [Directions] | 7:30 p.m. | L 6-3 | 5:00 pm | Pick up @ Shelton |
| Wed., 2/6 | V Boys Basketball | Joel Barlow | Home - WHS Gymnasium [Directions] | 7:15 p.m. | L 42-51 | ||
| Wed., 2/6 | JV Boys Basketball | Joel Barlow | Away - Lower Gym [Directions] | 5:00 p.m. | 2:40pm | ||
| Wed., 2/6 | FR Boys Basketball | Joel Barlow | Home - WHS Gymnasium [Directions] | 3:30 p.m. | |||
| Wed., 2/6 | V Boys Ice Hockey | Housatonic Coop | Home - Danbury Ice Arena [Directions] | 5:30 p.m. | L 4-6 | ||
| Wed., 2/6 | V Girls Basketball | Joel Barlow | Home - WHS Gymnasium [Directions] | 5:30 p.m. | W 43-20 | 4:00pm | |
| Wed., 2/6 | JV Girls Basketball | Joel Barlow | Away - JBHS Lower Gym [Directions] | 3:30 p.m. | 2:40pm | ||
| Fri., 2/8 | V Girls Ice Hockey | Notre Dame-Fairfield | Away - The Rinks at Shelton [Directions] | 5:00 p.m. | L 0-6 | ||
| Sat., 2/9 | JV Boys Ice Hockey | Brookfield | Home [Directions] | 7:40 p.m. | |||
| Sat., 2/9 | V Boys Indoor Track | CIAC Class M Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 10:00 a.m. | 7:45am | ||
| Sat., 2/9 | V Wrestling | SWC Championship Tournament | Away [Directions] | 9:30 a.m. | 7:00am | at New Milford HS | |
| Sat., 2/9 | V Girls Basketball | Notre Dame-Fairfield | Home - WHS Gymnasium [Directions] | 4:45 p.m. | L 25-51 | ||
| Sat., 2/9 | JV Girls Basketball | Notre Dame-Fairfield | Home - WHS Gymnasium [Directions] | 3:00 p.m. | |||
| Sat., 2/9 | V Girls Gymnastics | FCIAC Championships | Away - Westhill HS | 10:00 a.m. | Ludlowe- 133.90 2nd | PU at Ludlowe 8:30 RE 1:30 | |
| Sat., 2/9 | V Girls Indoor Track | CIAC Class M Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 10:00 a.m. | 7:45am | ||
| Sun., 2/10 | V Boys Basketball | Notre Dame-Fairfield | Away - Sister Marion Rielly Auditorium at Notre Dame [Directions] | 4:00 p.m. | L 52-64 | 2:00pm | |
| Sun., 2/10 | JV Boys Basketball | Notre Dame-Fairfield | Away - Sister Marion Rielly Auditorium at Notre Dame [Directions] | 2:15 p.m. | 11:15am | ||
| Sun., 2/10 | FR Boys Basketball | Notre Dame-Fairfield | Away - Sister Marion Rielly Auditorium at Notre Dame [Directions] | 12:30 p.m. | 11:15am | ||
| Mon., 2/11 | V Boys Ice Hockey | Brookfield | Home - Danbury Ice Arena [Directions] | 7:50 p.m. | W 11-2 | ||
| Wed., 2/13 | V Boys Ice Hockey | Daniel Hand | Away - Northford Ice Pavilion [Directions] | 4:30 p.m. | L 4-8 | ||
| Wed., 2/13 | V Girls Basketball | Bethel | Home - WHS Gymnasium [Directions] | 7:00 p.m. | L 19-42 | ||
| Wed., 2/13 | JV Girls Basketball | Bethel | Home - WHS Gymnasium [Directions] | 5:15 p.m. | |||
| Wed., 2/13 | FR Girls Basketball | Ridgefield | Home - WHS Gymnasium [Directions] | 3:45 p.m. | |||
| Wed., 2/13 | V Girls Gymnastics | Fairfield Warde | Home - GCA [Directions] | 6:30 p.m. | Ludlowe- 136.45 Warde- 124.70 | ||
| Thu., 2/14 | V Boys Basketball | Newtown | Away - Newtown HS Gymnasium [Directions] | 7:00 p.m. | L 48-74 | 3:45pm | |
| Thu., 2/14 | JV Boys Basketball | Newtown | Away - Newtown HS Gymnasium [Directions] | 5:30 p.m. | 3:45pm | ||
| Thu., 2/14 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton Rinks [Directions] | 5:30 p.m. | L 1-7 | ||
| Fri., 2/15 | V Boys Ice Hockey | Housatonic Coop | Away - Hotchkiss [Directions] | 8:15 p.m. | W 6-2 | ||
| Fri., 2/15 | V Wrestling | CIAC Class M Championships | Away - Guilford [Directions] | 4:45 p.m. | 1:30pm | ||
| Fri., 2/15 | V Girls Basketball | Kolbe Cathedral | Away [Directions] | 7:00 p.m. | L 27-53 | 5:00pm | SWC Quarterfinals |
| Fri., 2/15 | V Girls Ice Hockey | Simsbury | Home - The Rinks at Shelton [Directions] | 5:30 p.m. | L 0-4 | ||
| Sat., 2/16 | V Boys Basketball | Bethel | Away - Bethel HS [Directions] | 3:15 p.m. | L 42-49 | 12:15pm | |
| Sat., 2/16 | JV Boys Basketball | Bethel | Away - Bethel HS [Directions] | 1:30 p.m. | 12:15pm | ||
| Sat., 2/16 | FR Boys Basketball | Bethel | Away [Directions] | 12:00 p.m. | 10:45am | ||
| Sat., 2/16 | V Boys Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | 9:45am | ||
| Sat., 2/16 | V Wrestling | CIAC Class M Championships | Away - Guilford HS [Directions] | 9:00 a.m. | |||
| Sat., 2/16 | V Girls Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | 9:45am | ||
| Sun., 2/17 | V Boys Ice Hockey | Lyman Hall | Away - Northford Ice Pavilion [Directions] | 8:10 p.m. | L 5-7 | ||
| Sun., 2/17 | V Girls Ice Hockey | Hamden Coop | Away - Lou Astorino Ice Rink [Directions] | 1:15 p.m. | L 0-8 | 11:30 am | Pick up @ Shelton |
| Mon., 2/18 | V Boys Ice Hockey | Brien McMahon/Norwalk | Away - SoNo Ice House [Directions] | 8:40 p.m. | W 8-1 | ||
| Mon., 2/18 | V Girls Basketball | SWC Semifinals | Away | Cancelled | Cancelled | Home of higher seed | |
| Tue., 2/19 | V Boys Basketball | Immaculate | Home - WHS Gymnasium [Directions] | 7:00 p.m. | L 42-85 | ||
| Tue., 2/19 | JV Boys Basketball | Immaculate | Home - WHS Gymnasium [Directions] | 5:15 p.m. | |||
| Tue., 2/19 | FR Boys Basketball | Immaculate | Home - WHS Gymnasium [Directions] | 3:30 p.m. | |||
| Tue., 2/19 | V Boys Swimming and Diving | New Fairfield | Away - New Fairfield HS [Directions] | 4:00 p.m. | 2:40pm | ||
| Wed., 2/20 | V Girls Basketball | SWC Championship Game | Away | Cancelled | Cancelled | ||
| Thu., 2/21 | FR Boys Basketball | Brookfield | Home - WHS Gymnasium [Directions] | Cancelled | Cancelled | ||
| Fri., 2/22 | V Boys Basketball | SWC Quarterfinals | Away | Cancelled | Cancelled | at home of higher seed | |
| Fri., 2/22 | V Wrestling | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 3:00 p.m. | |||
| Fri., 2/22 | V Girls Basketball | Greenwich (Scrim.) | Home - WHS Gymnasium [Directions] | 4:30 p.m. | |||
| Sat., 2/23 | V Boys Ice Hockey | Milford Coop | Home - Danbury Ice Arena [Directions] | 8:10 p.m. | W 6-3 | ||
| Sat., 2/23 | V Wrestling | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 9:00 a.m. | |||
| Sat., 2/23 | V Girls Gymnastics | CIAC Divisional Championships | Away - Jonathan Law HS [Directions] | TBA | |||
| Mon., 2/25 | V Boys Basketball | SWC Semifinals | Away | Cancelled | Cancelled | at home of higher seed | |
| Mon., 2/25 | V Boys Ice Hockey | New Milford | Away - Canterbury School [Directions] | 7:00 p.m. | W 6-3 | ||
| Mon., 2/25 | V Boys Swimming and Diving | Pomperaug | Home - Weston MS Pool [Directions] | 6:00 p.m. | |||
| Tue., 2/26 | V Girls Basketball | Plainfield | Away - Higher Seed [Directions] | 6:00 p.m. | W 36-35 | 2:40pm | |
| Wed., 2/27 | V Boys Swimming and Diving | SWC Dive Championships | Away [Directions] | 3:30 p.m. | warm-up at 2:30pm | ||
| Thu., 2/28 | V Boys Basketball | SWC Championship Game | Away | Cancelled | Cancelled | ||
| Fri., 3/1 | V Boys Swimming and Diving | SWC Championship Meet | Away [Directions] | 5:00 p.m. | 2:40pm | warm-up at 3:30pm | |
| Fri., 3/1 | V Girls Basketball | Kolbe Cathedral | Away - Sheehan Center [Directions] | 5:00 p.m. | L 24-57 | 3:00pm | |
| Sat., 3/2 | V Boys Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | TBA | |||
| Sat., 3/2 | V Girls Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | TBA | |||
| Mon., 3/4 | V Boys Basketball | CIAC Tourney 1st Round | Away - Higher Seed | Cancelled | Cancelled | ||
| Wed., 3/6 | V Boys Basketball | CIAC Tourney 2nd Round | Away - Higher Seed | Cancelled | Cancelled | ||
| Wed., 3/6 | V Boys Swimming and Diving | CIAC Class M Diving Trials/Finals | Away - Bulkeley HS [Directions] | 5:30 p.m. | |||
| Wed., 3/6 | V Girls Gymnastics | CIAC Open Championship | Away - New Milford HS [Directions] | 4:00 p.m. | PU 1:30 at Ludlowe, 1:45 at Warde RE 7:00 | ||
| Thu., 3/7 | V Girls Basketball | CIAC Tourney Quarterfinals | Away - Higher Seed | Cancelled | Cancelled | ||
| Fri., 3/8 | V Boys Basketball | CIAC Tourney Quarterfinals | Away - Higher Seed | Cancelled | Cancelled | ||
| Sat., 3/9 | V Boys Swimming and Diving | CIAC Class M Qualifying | Away - Cornerstone Pool [Directions] | 4:00 p.m. | |||
| Mon., 3/11 | V Boys Swimming and Diving | CIAC Class M Finals | Away - Wesleyan Univ. [Directions] | 1:30 p.m. | |||
| Mon., 3/11 | V Girls Basketball | CIAC Tourney Semifinals | Away - Site TBA | Cancelled | Cancelled | ||
| Tue., 3/12 | V Boys Basketball | CIAC Tourney Semifinals | Away - Site TBA | Cancelled | Cancelled | ||
| Tue., 3/12 | V Boys Swimming and Diving | CIAC Open Diving | Away - Bulkeley [Directions] | 5:30 p.m. | |||
| Wed., 3/13 | Miscellaneous Events | Spectrum | Home - WHS Gymnasium [Directions] | 7:00 p.m. | |||
| Thu., 3/14 | V Boys Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 7:00 p.m. | |||
| Thu., 3/14 | Miscellaneous Events | Spectrum Weather Date | Home [Directions] | 7:00 p.m. | |||
| Sat., 3/16 | V Boys Basketball | CIAC Tourney Final (Possible Date) | Away - Mohegan Sun Arena [Directions] | Cancelled | Cancelled | ||
| Sat., 3/16 | V Girls Basketball | CIAC Tourney Final (Possible Date) | Away - Mohegan Sun Arena [Directions] | Cancelled | Cancelled | ||
| Sun., 3/17 | V Boys Basketball | CIAC Tourney Final (Possible Date) | Away - Mohegan Sun Arena [Directions] | Cancelled | Cancelled | ||
| Sun., 3/17 | V Girls Basketball | CIAC Tourney Final (Possible Date) | Away - Mohegan Sun Arena [Directions] | Cancelled | Cancelled | ||
| Thu., 3/21 | V Baseball | Jonathan Law (Scrim.) | Away - Jonathan Law HS Baseball Field [Directions] | 4:00 p.m. | 2:40pm | ||
| Sat., 3/23 | V Baseball | Fitch (Scrim.) | Away - Fitch HS-Baseball Field [Directions] | 12:00 p.m. | 9:30am | ||
| Sat., 3/23 | V Boys Lacrosse | Weston Jamboree | Home - WHS Turf Field [Directions] | 10:00 a.m. | 4 teams on two fields | ||
| Sat., 3/23 | V Boys Lacrosse | Weston Jamboree | Home - WHS Stadium Field [Directions] | 12:00 p.m. | 4 teams on two fields | ||
| Mon., 3/25 | V Baseball | Norwalk (Scrim.) | Away - Callahan Complex at Nathan Hale Upper [Directions] | 4:00 p.m. | 2:40pm | ||
| Mon., 3/25 | JV Baseball | Norwalk (Scrim.) | Away - City Hall Field [Directions] | 4:00 p.m. | 2:40 | ||
| Tue., 3/26 | V Boys Tennis | Choate Rosemary Hall (Scrim.) | Away - Choate Tennis Courts | 4:00 p.m. | 2:45P | ||
| Tue., 3/26 | V Girls Lacrosse | Trumbull (Scrim.) | Home - WHS Turf Field [Directions] | 5:30 p.m. | |||
| Tue., 3/26 | JV Girls Lacrosse | Trumbull (Scrim.) | Home - WHS Turf Field [Directions] | 4:00 p.m. | |||
| Tue., 3/26 | V Softball | Wilton (Scrim.) | Away - WHS Varsity Softball Field [Directions] | 3:45 p.m. | 2:40pm | ||
| Wed., 3/27 | V Boys Lacrosse | Somers (NY) (Scrim.) | Home - WHS Turf Field [Directions] | 5:00 p.m. | |||
| Wed., 3/27 | V Boys Tennis | Westhill (Scrim.) | Away - Westhill Tennis Courts [Directions] | 4:00 p.m. | 2:45pm | ||
| Thu., 3/28 | JV Boys Lacrosse | Wilton (Scrim.) | Away - Allen's Field [Directions] | 4:00 p.m. | 2:45pm | ||
| Thu., 3/28 | V Boys Tennis | Greens Farms Academy (Scrim.) | Away | 3:30 p.m. | 2:40p.m. | ||
| Thu., 3/28 | V Girls Lacrosse | Staples (Scrim.) | Away - Ginny Parker Field - Staples [Directions] | 5:00 p.m. | 2:40pm | ||
| Thu., 3/28 | JV Girls Lacrosse | Staples (Scrim.) | Away - Ginny Parker Field - Staples [Directions] | 3:45 p.m. | 2:40pm | ||
| Thu., 3/28 | V Softball | Norwalk (Scrim.) | Home - Hurlbutt El. School, Weston [Directions] | 4:00 p.m. | |||
| Thu., 3/28 | V Girls Tennis | Hopkins School (Scrim.) | Home - WHS Tennis Courts [Directions] | 4:30 p.m. | |||
| Fri., 3/29 | JV Softball | Norwalk (Scrim.) | Away - Naramake School [Directions] | 4:00 p.m. | 2:40pm | ||
| Sat., 3/30 | V Baseball | Westhill | Home - Wilton HS Varsity Field [Directions] | 12:00 p.m. | L 0-12 | 10:00am | non league |
| Sat., 3/30 | JV Baseball | Westhill | Home - Wilton HS JV Field [Directions] | 9:30 a.m. | 8:15am | ||
| Sat., 3/30 | V Boys Tennis | Wilton | Away - Wilton Tennis Courts [Directions] | 12:00 p.m. | L 1-6 | 11:00am | non league |
| Sat., 3/30 | JV Boys Tennis | Wilton | Away - Middlebrook School [Directions] | 12:00 p.m. | 11:00am | ||
| Sat., 3/30 | V Softball | Abbott Tech | Home - Hurlbutt El. School, Weston [Directions] | 12:00 p.m. | W 7-2 | non league | |
| Sat., 3/30 | JV Softball | Brookfield | Away - BHS Softball Field [Directions] | 1:00 p.m. | 11:30am | ||
| Sat., 3/30 | V Girls Tennis | Wilton | Home - WHS Tennis Courts [Directions] | 12:00 p.m. | L 2-5 | non league | |
| Sat., 3/30 | JV Girls Tennis | Wilton | Home - WHS Tennis Courts [Directions] | 1:30 p.m. | |||
| Mon., 4/1 | V Boys Golf | Newtown | Home - Aspetuck Valley Country Club [Directions] | 3:00 p.m. | Weston 184 Newtown 208 | Non-League | |
| Mon., 4/1 | V Girls Golf | Brookfield | Home - Aspetuck Valley Country Club [Directions] | 3:00 p.m. | Weston 275 Brookfield 303 | ||
| Mon., 4/1 | V Girls Lacrosse | Stamford | Away - Boyle Stadium, SHS [Directions] | 4:15 p.m. | W 15-5 | 2:40pm | non league |
| Mon., 4/1 | JV Girls Lacrosse | Stamford | Away - Boyle Stadium, SHS [Directions] | 5:30 p.m. | 2:40pm | ||
| Mon., 4/1 | V Softball | Bridgeport Central | Home - Hurlbutt El. School, Weston [Directions] | 4:15 p.m. | W 6-3 | non league | |
| Tue., 4/2 | V Baseball | Ridgefield | Away - Governor's Park Field (aka Ciuccoli or Old HS) [Directions] | 4:15 p.m. | L 1-5 | 2:40pm | non league |
| Tue., 4/2 | JV Baseball | Ridgefield | Away - East Ridge MS [Directions] | 4:15 p.m. | 2:40pm | ||
| Tue., 4/2 | V Boys Lacrosse | Notre Dame-West Haven | Away - Veteran's Stadium [Directions] | 6:00 p.m. | W 9-6 | 2:40pm | non league |
| Tue., 4/2 | JV Boys Lacrosse | Notre Dame-West Haven | Away - Veteran's Stadium [Directions] | 4:00 p.m. | 2:40pm | ||
| Tue., 4/2 | JV Boys Tennis | Fairfield Ludlowe | Away - Tomlinson MS Tennis Courts [Directions] | 4:00 p.m. | 2:45pm | ||
| Tue., 4/2 | JV Girls Tennis | Fairfield Ludlowe | Away - Dwight Elementary School Courts [Directions] | 4:00 p.m. | 2:45pm | ||
| Wed., 4/3 | V Boys Golf | Stratford | Away - Mill River C.C. [Directions] | 3:00 p.m. | Weston 181 Stratford 265 | ||
| Wed., 4/3 | V Softball | Trinity Catholic | Away - Trinity Catholic's Smith Field | 4:15 p.m. | L 8-9 | 2:40pm | non league |
| Thu., 4/4 | V Baseball | Wilton | Away - WHS Varsity Baseball Field [Directions] | 4:15 p.m. | L 4-5 | non league | |
| Thu., 4/4 | V Boys Lacrosse | Immaculate | Home - WHS Turf Field [Directions] | 6:00 p.m. | W 21-1 | ||
| Thu., 4/4 | JV Boys Lacrosse | Immaculate | Home - WHS Turf Field [Directions] | 4:00 p.m. | |||
| Thu., 4/4 | V Girls Golf | Stratford | Away - Mill River C.C. [Directions] | 3:00 p.m. | Weston 262 Stratford 318 | ||
| Thu., 4/4 | V Girls Lacrosse | Immaculate | Away - Mustang Valley [Directions] | 4:00 p.m. | W 15-8 | 2:40pm | |
| Thu., 4/4 | JV Girls Lacrosse | Immaculate | Away - Mustang Valley [Directions] | 5:30 p.m. | 2:40pm | ||
| Thu., 4/4 | JV Softball | Masuk | Away - Wolfe Park Softball Field - # 4 [Directions] | 4:00 p.m. | 2:40pm | ||
| Fri., 4/5 | V Girls Lacrosse | Fairfield Warde | Home - WHS Turf Field [Directions] | 4:00 p.m. | L 7-8 | non league | |
| Sat., 4/6 | V Boys Lacrosse | Fordham Prep (NY) | Home - WHS Turf Field [Directions] | 1:00 p.m. | W 10-2 | non league | |
| Sat., 4/6 | JV Boys Lacrosse | Fordham Prep (NY) | Home - WHS Turf Field [Directions] | 11:00 a.m. | |||
| Sat., 4/6 | V Boys Tennis | Glastonbury | Home - WHS Tennis Courts [Directions] | 1:00 p.m. | W Weston | non league | |
| Sat., 4/6 | JV Boys Tennis | Glastonbury | Home - WHS Tennis Courts [Directions] | 2:30 p.m. | |||
| Sat., 4/6 | JV Softball | Danbury | Away [Directions] | 12:00 p.m. | 10:30am | ||
| Sat., 4/6 | V Girls Tennis | Glastonbury | Away - Glastonbury HS [Directions] | 1:00 p.m. | W Weston | 9:00am | non league |
| Sat., 4/6 | JV Girls Tennis | Glastonbury | Away [Directions] | 2:30 p.m. | 9:00am | ||
| Mon., 4/8 | V Baseball | Stratford | Away - Penders Field [Directions] | 4:15 p.m. | W 12-7 | ||
| Mon., 4/8 | V Boys Golf | New Milford | Home - Aspetuck Valley Country Club [Directions] | 3:00 p.m. | Weston 165 New Milford 196 | ||
| Mon., 4/8 | V Boys Outdoor Track | Joel Barlow, Notre Dame-Fairfield, Newtown | Away - Field I (Stadium) [Directions] | 4:00 p.m. | Weston 118 Joel Barlow 32 Weston 107 Newtown 43 Weston 137 Notre Dame 8 | 2:40pm | |
| Mon., 4/8 | V Boys Tennis | Newtown | Away [Directions] | 3:45 p.m. | W 7-0 | 2:40pm | |
| Mon., 4/8 | V Girls Golf | Notre Dame-Fairfield | Home - Aspetuck Valley Country Club [Directions] | 3:00 p.m. | Notre Dame Fairfield 267 Weston 274 | ||
| Mon., 4/8 | V Softball | Bunnell | Away - Bunnell Softball Field [Directions] | 4:15 p.m. | W 16-4 | 2:40pm | Non-League |
| Mon., 4/8 | V Girls Tennis | Newtown | Home - WHS Tennis Courts [Directions] | 3:45 p.m. | W 6-1 | ||
| Tue., 4/9 | V Boys Golf | Brookfield | Away - Sunset Hill Golf Course [Directions] | 3:00 p.m. | Weston 163 Brookfield 180 | ||
| Tue., 4/9 | V Boys Lacrosse | New Milford | Home - WHS Turf Field [Directions] | 6:00 p.m. | W 21-1 | ||
| Tue., 4/9 | JV Boys Lacrosse | New Milford | Home - WHS Turf Field [Directions] | 4:00 p.m. | |||
| Tue., 4/9 | V Girls Lacrosse | New Milford | Away - New Milford HS [Directions] | 6:00 p.m. | W 12-8 | 2:40pm | |
| Tue., 4/9 | JV Girls Lacrosse | New Milford | Away - New Milford HS [Directions] | 4:00 p.m. | 2:40pm | ||
| Tue., 4/9 | V Girls Outdoor Track | Newtown, Notre Dame-Fairfield, Joel Barlow | Away [Directions] | 4:00 p.m. | Newtown 91 Weston 59 Weston 76.5 JB 54.5 Weston over ND | 2:40pm | |
| Tue., 4/9 | V Girls Tennis | Notre Dame-Fairfield | Away - Veteran's Park - Bridgeport [Directions] | 3:45 p.m. | W 7-0 | 2:40pm | |
| Wed., 4/10 | V Baseball | Notre Dame-Fairfield | Home - Revson Field, Weston [Directions] | 4:15 p.m. | W 7-0 | Non-League | |
| Wed., 4/10 | V Boys Tennis | New Fairfield | Home [Directions] | 3:45 p.m. | W 7-0 | ||
| Wed., 4/10 | V Girls Golf | Newtown | Away - Newtown Country Club [Directions] | 3:00 p.m. | Newtown 251 Weston 254 | ||
| Wed., 4/10 | V Softball | Bethel | Home - Hurlbutt El. School, Weston [Directions] | 4:15 p.m. | L 8-10 | Non-League | |
| Thu., 4/11 | JV Baseball | Pomperaug | Home - Revson Field, Weston [Directions] | 4:15 p.m. | |||
| Thu., 4/11 | V Girls Lacrosse | Bunnell | Away - Bunnell Turf Field [Directions] | 7:00 p.m. | W 15-5 | 3:40pm | |
| Thu., 4/11 | JV Girls Lacrosse | Bunnell | Away - Bunnell Turf Field [Directions] | 5:15 p.m. | 3:40pm | ||
| Thu., 4/11 | JV Softball | Pomperaug | Home - Weston MS [Directions] | 4:15 p.m. | |||
| Thu., 4/11 | V Girls Tennis | New Fairfield | Home - WHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | ||
| Fri., 4/12 | V Baseball | New Fairfield | Away - NFHS Baseball Field [Directions] | 4:15 p.m. | L 7-8 | 2:40pm | Non-League |
| Fri., 4/12 | V Boys Tennis | New Canaan | Away - NCHS Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | 2:40pm | non league |
| Fri., 4/12 | V Girls Tennis | Joel Barlow | Home - WHS Tennis Courts [Directions] | 3:45 p.m. | W 6-1 | ||
| Sat., 4/13 | V Boys Lacrosse | Connetquot (NY) | Away [Directions] | 2:00 p.m. | W 12-8 | 12:00pm | non league at New Fairfield |
| Sat., 4/13 | V Boys Tennis | New Milford | Home - WHS Tennis Courts [Directions] | 3:00 p.m. | W 7-0 | ||
| Sat., 4/13 | V Girls Lacrosse | Fairfield Ludlowe | Home - WHS Turf Field [Directions] | 2:30 p.m. | L 7-11 | non league | |
| Sat., 4/13 | JV Girls Lacrosse | Fairfield Ludlowe | Home - WHS Turf Field [Directions] | 1:00 p.m. | |||
| Sat., 4/13 | V Girls Tennis | New Milford | Away - New Milford HS [Directions] | 3:00 p.m. | W 7-0 | 1:30pm | |
| Mon., 4/15 | V Boys Golf | Notre Dame-Fairfield | Home - Aspetuck Valley Country Club [Directions] | 3:00 p.m. | Weston 189 Notre Dame of Fairfield 239 | ||
| Tue., 4/16 | JV Baseball | New Fairfield | Away - NFHS Baseball Field [Directions] | 4:15 p.m. | [Detailed Results] | 2:40pm | |
| Tue., 4/16 | V Boys Lacrosse | Newtown | Away - Blue and Gold Stadium [Directions] | 7:00 p.m. | L 5-9 | 5:00pm | |
| Tue., 4/16 | JV Boys Lacrosse | Newtown | Away - Blue and Gold Stadium [Directions] | 5:15 p.m. | 3:15pm | ||
| Tue., 4/16 | V Boys Tennis | Brookfield | Home - WHS Tennis Courts [Directions] | 10:00 a.m. | W 6-1 | ||
| Tue., 4/16 | V Girls Lacrosse | Newtown | Home - WHS Turf Field [Directions] | 5:30 p.m. | L 8-9 | ||
| Tue., 4/16 | JV Girls Lacrosse | Newtown | Home - WHS Turf Field [Directions] | 4:00 p.m. | |||
| Tue., 4/16 | V Softball | Immaculate | Home - Hurlbutt El. School, Weston [Directions] | 4:15 p.m. | L 10-11 | Non-League | |
| Tue., 4/16 | JV Softball | New Fairfield | Away - NFHS Softball Field [Directions] | 4:15 p.m. | 2:40pm | ||
| Tue., 4/16 | V Girls Tennis | Brookfield | Away - BHS Tennis Courts [Directions] | 10:00 a.m. | W 7-0 | 8:30am | |
| Wed., 4/17 | V Baseball | New Fairfield | Home - Revson Field, Weston [Directions] | 3:30 p.m. | W 11-8 | ||
| Wed., 4/17 | V Softball | New Fairfield | Home - Hurlbutt El. School, Weston [Directions] | 4:15 p.m. | L 0-4 | ||
| Thu., 4/18 | V Baseball | Notre Dame-Fairfield | Away - Fabbri Field at Notre Dame [Directions] | 3:30 p.m. | W 8-5 [Detailed Results] | 2:40pm | |
| Thu., 4/18 | JV Baseball | Notre Dame-Fairfield | Home - Revson Field, Weston [Directions] | 10:00 a.m. | [Detailed Results] | ||
| Thu., 4/18 | V Boys Golf | Joel Barlow | Away - Redding Country Club [Directions] | 10:00 a.m. | Joel Barlow 173 Wedton 178 | ||
| Thu., 4/18 | V Boys Lacrosse | New Fairfield | Home - WHS Turf Field [Directions] | 6:00 p.m. | L 4-17 | ||
| Thu., 4/18 | JV Boys Lacrosse | New Fairfield | Home - WHS Turf Field [Directions] | 4:00 p.m. | |||
| Thu., 4/18 | V Girls Lacrosse | New Fairfield | Away - Rebel Turf [Directions] | 6:00 p.m. | L 4-14 | 2:40pm | |
| Thu., 4/18 | JV Girls Lacrosse | New Fairfield | Away - Rebel Turf [Directions] | 4:00 p.m. | 2:40pm | ||
| Thu., 4/18 | V Softball | Notre Dame-Fairfield | Away - Park Avenue Field at Notre Dame [Directions] | 3:30 p.m. | L 1-16 | 2:40pm | |
| Tue., 4/23 | V Baseball | Bethel | Away - Hunt Field at Bethel HS [Directions] | 4:00 p.m. | L 9-13 | 2:40pm | |
| Tue., 4/23 | V Boys Lacrosse | Brookfield | Away - BHS Stadium Field [Directions] | 6:00 p.m. | W 14-1 | 4:00pm | |
| Tue., 4/23 | JV Boys Lacrosse | Brookfield | Away - BHS Back Turf [Directions] | 4:00 p.m. | 2:40pm | ||
| Tue., 4/23 | V Boys Tennis | Bunnell | Away [Directions] | 5:00 p.m. | W 7-0 | 4:15pm | |
| Tue., 4/23 | V Girls Golf | Newtown | Home - Aspetuck Valley Country Club [Directions] | 3:00 p.m. | Newtown 242 Weston 259 | ||
| Tue., 4/23 | V Girls Lacrosse | Brookfield | Home - WHS Turf Field [Directions] | 5:30 p.m. | L 9-12 | ||
| Tue., 4/23 | JV Girls Lacrosse | Brookfield | Home - WHS Turf Field [Directions] | 4:00 p.m. | |||
| Tue., 4/23 | V Girls Outdoor Track | Brookfield, Bunnell, New Fairfield | Home - WHS Track [Directions] | 4:00 p.m. | Weston 109 New Fairfield 41 Weston 96 Bookfield 44 Weston 101 Bnnell 49 | ||
| Tue., 4/23 | V Softball | Bethel | Away - Kisling Field [Directions] | 4:15 p.m. | W 4-3 | 2:40pm | |
| Tue., 4/23 | JV Softball | Bethel | Home - Hurlbutt El. School, Weston [Directions] | 4:15 p.m. | |||
| Wed., 4/24 | V Baseball | Kolbe Cathedral | Home - Joel Barlow HS [Directions] | 4:30 p.m. | W 9-6 | ||
| Wed., 4/24 | V Boys Golf | Newtown | Away [Directions] | 3:00 p.m. | Newtown 175 Weston 183 | ||
| Wed., 4/24 | V Boys Outdoor Track | Brookfield, Bunnell, New Fairfield | Away - BHS Track [Directions] | 4:00 p.m. | Weston 105.5 Brookfield 44.5 Weston 108 Bunnell. 42 Weston 110 New Fairfield 40 | 2:40pm | |
| Wed., 4/24 | V Boys Tennis | Immaculate | Home - WHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | ||
| Wed., 4/24 | V Softball | Kolbe Cathedral | Home - Hurlbutt El. School, Weston [Directions] | 4:15 p.m. | W 19-11 | ||
| Wed., 4/24 | V Girls Tennis | Immaculate | Away - O'Neill Center, WCSU, Danbury [Directions] | 3:45 p.m. | W 7-0 | 2:40pm | |
| Thu., 4/25 | V Baseball | Masuk | Home - Revson Field, Weston [Directions] | 4:00 p.m. | L 4-5 | Non-League | |
| Thu., 4/25 | V Boys Lacrosse | Bethel | Home - WHS Turf Field [Directions] | 6:00 p.m. | W 18-6 | ||
| Thu., 4/25 | JV Boys Lacrosse | Bethel | Home - WHS Turf Field [Directions] | 4:00 p.m. | |||
| Thu., 4/25 | V Boys Tennis | Masuk | Home - WHS Tennis Courts [Directions] | 3:45 p.m. | W 6-1 | ||
| Thu., 4/25 | V Girls Golf | Joel Barlow | Away - Redding Country Club [Directions] | 2:00 p.m. | Joel Barlow 262 Weston 298 | ||
| Thu., 4/25 | V Girls Lacrosse | Bethel | Away - Rockwell Field [Directions] | 4:00 p.m. | W 16-8 | 2:40pm | |
| Thu., 4/25 | JV Girls Lacrosse | Bethel | Away - Rockwell Field [Directions] | 5:30 p.m. | 2:40pm | ||
| Thu., 4/25 | JV Softball | Wright Tech | Home - Weston MS [Directions] | 3:45 p.m. | |||
| Thu., 4/25 | V Girls Tennis | Masuk | Away - Wolfe Park Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | 2:40pm | |
| Fri., 4/26 | V Boys Outdoor Track | O'Grady Relays | Away [Directions] | 4:00 p.m. | 2:40pm | at Bethel HS | |
| Fri., 4/26 | V Girls Outdoor Track | O'Grady Relays | Away [Directions] | 4:00 p.m. | 2:40pm | at Bethel HS | |
| Sat., 4/27 | V Boys Outdoor Track | O'Grady Relays | Away [Directions] | 9:00 a.m. | 7:30am | at Bethel HS | |
| Sat., 4/27 | V Girls Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 6:15 p.m. | L 8-9 | 3:15pm | non league |
| Sat., 4/27 | JV Girls Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 4:30 p.m. | 3:15pm | ||
| Sat., 4/27 | V Girls Outdoor Track | O'Grady Relays | Away [Directions] | 9:00 a.m. | 7:30am | at Bethel HS | |
| Mon., 4/29 | V Baseball | Masuk | Away - John Giampaolo Baseball Field @ Masuk HS [Directions] | 4:00 p.m. | L 2-7 | 2:40pm | |
| Mon., 4/29 | JV Baseball | Bethel | Away - Parloa Field [Directions] | 4:15 p.m. | |||
| Mon., 4/29 | V Boys Golf | Pomperaug | Home - Aspetuck Valley Country Club [Directions] | 3:00 p.m. | Weston 174 Pomperaug 174 (Weston wins on tiebreak) | ||
| Mon., 4/29 | V Boys Outdoor Track | Masuk, Immaculate, Bethel | Away - Masuk HS Track [Directions] | 4:00 p.m. | Weston | 2:40pm | |
| Mon., 4/29 | V Boys Tennis | Bethel | Home - WHS Tennis Courts [Directions] | 5:00 p.m. | W 6-1 | ||
| Mon., 4/29 | V Girls Golf | Masuk | Home - Aspetuck Valley Country Club [Directions] | 3:45 p.m. | Masuk 201 Weston 274 | ||
| Mon., 4/29 | V Girls Golf | Joel Barlow | Home - Aspetuck Valley Country Club [Directions] | 3:45 p.m. | Weston 274 Joel Barlow 288 | ||
| Mon., 4/29 | V Softball | Masuk | Away - Masuk HS Softball Field [Directions] | 4:15 p.m. | L 0-19 | 2:40pm | |
| Mon., 4/29 | V Girls Tennis | Bethel | Away - Bethel HS [Directions] | 3:45 p.m. | W 7-0 | 2:40pm | |
| Tue., 4/30 | JV Baseball | Masuk | Away - Masuk HS [Directions] | 4:15 p.m. | |||
| Tue., 4/30 | V Boys Lacrosse | Notre Dame-Fairfield | Away - Park Avenue Field at Notre Dame [Directions] | 4:00 p.m. | W 19-0 | 2:40pm | |
| Tue., 4/30 | V Boys Tennis | Joel Barlow | Away - Tennis Courts [Directions] | 4:45 p.m. | L 3-4 | 4:00pm | |
| Tue., 4/30 | V Girls Golf | Bunnell | Away - Oronoque Country Club [Directions] | 3:00 p.m. | Weston 267 Bunnell 306 | ||
| Tue., 4/30 | V Girls Lacrosse | Notre Dame-Fairfield | Home - WHS Turf Field [Directions] | 5:30 p.m. | W 17-1 | ||
| Tue., 4/30 | JV Girls Lacrosse | Notre Dame-Fairfield | Home - WHS Turf Field [Directions] | 4:00 p.m. | |||
| Tue., 4/30 | V Girls Outdoor Track | Masuk, Immaculate, Bethel | Home - WHS Track [Directions] | 4:00 p.m. | Weston 106 Bethel 44 Weston 114 Immaculate 31 Weston 98 Masuk 51 | ||
| Tue., 4/30 | JV Softball | Masuk | Home - Hurlbutt El. School, Weston [Directions] | 4:15 p.m. | |||
| Wed., 5/1 | V Baseball | Bunnell | Home - Revson Field, Weston [Directions] | 4:15 p.m. | L 2-6 | ||
| Wed., 5/1 | JV Baseball | Bunnell | Away - Bunnell Baseball Field [Directions] | 4:15 p.m. | 2:40pm | ||
| Wed., 5/1 | V Boys Golf | Masuk | Away - Whitney Farms Golf Course [Directions] | 3:00 p.m. | Weston 181 Masuk 191 | Non-League | |
| Wed., 5/1 | JV Boys Tennis | Ridgefield | Home - WHS Tennis Courts [Directions] | 5:00 p.m. | |||
| Wed., 5/1 | V Girls Golf | Immaculate | Home - Aspetuck Valley Country Club [Directions] | 3:45 p.m. | Immaculate 221 Weston 259 | ||
| Wed., 5/1 | V Softball | Bunnell | Home - Hurlbutt El. School, Weston [Directions] | 4:00 p.m. | W 13-1 | ||
| Wed., 5/1 | JV Girls Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | 2:40pm | ||
| Thu., 5/2 | V Boys Golf | Woodland Hawk Invitational | Away | 8:00 a.m. | non league at Oxford Greens | ||
| Thu., 5/2 | V Boys Lacrosse | Brien McMahon | Home - WHS Turf Field [Directions] | 7:00 p.m. | W 17-11 | non league | |
| Thu., 5/2 | JV Boys Lacrosse | Brien McMahon | Home - WHS Turf Field [Directions] | 5:00 p.m. | |||
| Thu., 5/2 | V Boys Tennis | Pomperaug | Away - Edgewood Bath and Tennis Club [Directions] | 3:45 p.m. | W 7-0 | 2:40pm | |
| Thu., 5/2 | V Girls Lacrosse | Stratford/Bunnell | Away - Penders Field [Directions] | 4:15 p.m. | W 11-8 | 2:40pm | |
| Thu., 5/2 | JV Girls Lacrosse | Stratford/Bunnell | Away - Penders Field [Directions] | 5:45 p.m. | 2:40pm | ||
| Thu., 5/2 | JV Softball | Bunnell | Away - Wigwam Lane Field [Directions] | 4:15 p.m. | 2:40pm | ||
| Thu., 5/2 | V Girls Tennis | Pomperaug | Home - WHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | ||
| Sat., 5/4 | V Baseball | New Milford | Away - New Milford HS [Directions] | 3:00 p.m. | L 1-5 | 2:40pm | |
| Sat., 5/4 | V Boys Lacrosse | Guilford | Away - Kavanaugh Turf Field at GHS [Directions] | 1:00 p.m. | W 9-6 | 10:30am | non league |
| Sat., 5/4 | JV Boys Lacrosse | Guilford | Away - Kavanaugh Turf Field at GHS [Directions] | 11:00 a.m. | 9:00am | ||
| Sat., 5/4 | V Softball | Pomperaug | Home - Hurlbutt El. School, Weston [Directions] | 1:00 p.m. | L 2-8 | ||
| Sat., 5/4 | JV Softball | New Milford | Home - Hurlbutt El. School, Weston [Directions] | 3:00 p.m. | |||
| Mon., 5/6 | V Baseball | Newtown | Home - Newtown HS Baseball Field [Directions] | 4:15 p.m. | L 4-10 | ||
| Mon., 5/6 | V Boys Lacrosse | Masuk | Away - Benedict Stadium Field @ Masuk HS [Directions] | 6:45 p.m. | W 9-3 | 5:00pm | |
| Mon., 5/6 | JV Boys Lacrosse | Masuk | Away - Benedict Stadium Field @ Masuk HS [Directions] | 5:00 p.m. | 3:15pm | ||
| Mon., 5/6 | V Boys Outdoor Track | Kolbe Cathedral, Stratford, New Milford | Home - WHS Track [Directions] | 4:00 p.m. | Weston 93 New Milford 57 Weston 117 Stratford 28 Weston 127 Kolbe 17 | ||
| Mon., 5/6 | V Boys Tennis | Stratford | Home - WHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | ||
| Mon., 5/6 | JV Boys Tennis | Trumbull | Home [Directions] | 4:45 p.m. | |||
| Mon., 5/6 | V Girls Golf | Stratford | Home - Aspetuck Valley Country Club [Directions] | 3:45 p.m. | Stratford 266 Weston 280 | ||
| Mon., 5/6 | V Softball | Newtown | Home - Hurlbutt El. School, Weston [Directions] | 4:15 p.m. | L 1-15 | ||
| Mon., 5/6 | V Girls Tennis | Stratford | Away - Flood M.S. Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | 2:40pm | |
| Mon., 5/6 | JV Girls Tennis | Trumbull | Away - Unity Park [Directions] | 4:00 p.m. | 2:45pm | ||
| Tue., 5/7 | V Baseball | Pomperaug | Home - Revson Field, Weston [Directions] | 4:15 p.m. | W 10-0 | ||
| Tue., 5/7 | JV Baseball | Newtown | Away - Baseball Field at Fairfield Hills Complex [Directions] | 4:00 p.m. | 2:40pm | ||
| Tue., 5/7 | V Boys Golf | New Fairfield | Away - River Oaks [Directions] | 3:00 p.m. | Weston 178 New Fairfield 198 | ||
| Tue., 5/7 | V Girls Golf | Notre Dame-Fairfield | Away - Fairchild Wheeler Golf Course [Directions] | 3:00 p.m. | Weston 241 Notre Dame 244 | ||
| Tue., 5/7 | V Girls Lacrosse | Masuk | Home - WHS Turf Field [Directions] | 4:00 p.m. | L 6-7 | ||
| Tue., 5/7 | JV Girls Lacrosse | Masuk | Home - WHS Turf Field [Directions] | 5:30 p.m. | |||
| Tue., 5/7 | V Softball | Stratford | Away - DeLuca Field [Directions] | 4:15 p.m. | L 8-9 | 4:15pm | |
| Tue., 5/7 | JV Softball | Newtown | Away - Newtown HS Softball Field [Directions] | 4:15 p.m. | 2:40pm | ||
| Wed., 5/8 | V Baseball | Stratford | Home - Revson Field, Weston [Directions] | 4:00 p.m. | L 4-7 | Non-League | |
| Wed., 5/8 | V Boys Golf | Pomperaug | Away - Heritage Village C.C. [Directions] | 3:00 p.m. | Pomperaug 166 Weston 175 | Non-League | |
| Wed., 5/8 | V Boys Tennis | Staples | Home - WHS Tennis Courts [Directions] | 3:45 p.m. | L 0-7 | non league | |
| Wed., 5/8 | JV Boys Tennis | Staples | Home - WHS Tennis Courts [Directions] | 5:00 p.m. | |||
| Wed., 5/8 | V Girls Outdoor Track | New Milford, Stratford, Kolbe Cathedral | Away - New Milford HS [Directions] | 4:00 p.m. | Weston 111 New Milford 37 Weston 120 Kolbe 21 Weston 133 Stratford 12 | 2:40pm | |
| Wed., 5/8 | V Softball | Stratford | Home - Hurlbutt El. School, Weston [Directions] | 4:15 p.m. | L 1-8 | Non-League | |
| Wed., 5/8 | JV Softball | Brookfield | Home - Weston MS [Directions] | 4:00 p.m. | |||
| Wed., 5/8 | V Girls Tennis | Staples | Away - Staples HS-Tennis Courts [Directions] | 3:45 p.m. | L 1-6 | 2:40pm | non league |
| Wed., 5/8 | JV Girls Tennis | Staples | Away - Town Farms Tennis Courts [Directions] | 4:00 p.m. | 2:40pm | ||
| Thu., 5/9 | V Baseball | Brookfield | Away - BHS Baseball Field [Directions] | 4:15 p.m. | W 15-1 | 2:40pm | |
| Thu., 5/9 | JV Baseball | Stratford | Home - Revson Field, Weston [Directions] | 4:15 p.m. | |||
| Thu., 5/9 | V Boys Lacrosse | Joel Barlow | Away - Field I (Stadium) [Directions] | 6:00 p.m. | W 15-8 | 4:30pm | |
| Thu., 5/9 | JV Boys Lacrosse | Joel Barlow | Away - Field J (competition field) [Directions] | 4:00 p.m. | 2:40pm | ||
| Thu., 5/9 | V Girls Lacrosse | Joel Barlow | Home - WHS Turf Field [Directions] | 5:30 p.m. | L 8-13 | ||
| Thu., 5/9 | JV Girls Lacrosse | Joel Barlow | Home - WHS Turf Field [Directions] | 4:00 p.m. | |||
| Thu., 5/9 | V Softball | New Milford | Away - New Milford HS [Directions] | 4:15 p.m. | L 8-9 | 2:40pm | |
| Thu., 5/9 | V Softball | Brookfield | Away - Cadigan Field [Directions] | 7:00 p.m. | L 2-7 | 2:40pm | |
| Thu., 5/9 | V Girls Tennis | Bunnell | Home - WHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | ||
| Fri., 5/10 | V Boys Outdoor Track | Loucks Games | Away | TBA | |||
| Fri., 5/10 | V Girls Outdoor Track | Loucks Games | Away | TBA | |||
| Sat., 5/11 | V Boys Lacrosse | Daniel Hand | Away - DHHS Turf Field [Directions] | 12:00 p.m. | W 6-5 | 9:45am | non league |
| Sat., 5/11 | JV Boys Lacrosse | Daniel Hand | Away - DHHS Turf Field [Directions] | 10:00 a.m. | 8:00am | ||
| Sat., 5/11 | V Boys Outdoor Track | Loucks Games | Away | TBA | |||
| Sat., 5/11 | V Girls Outdoor Track | Loucks Games | Away | TBA | |||
| Mon., 5/13 | V Boys Lacrosse | Pomperaug | Away - Sports Complex & Track [Directions] | 7:00 p.m. | W 18-1 | 5:00pm | |
| Mon., 5/13 | JV Boys Lacrosse | Pomperaug | Away - Sports Complex & Track [Directions] | 5:00 p.m. | 3:15pm | ||
| Mon., 5/13 | V Girls Lacrosse | Pomperaug | Home - WHS Turf Field [Directions] | 6:00 p.m. | W 11-10 | ||
| Mon., 5/13 | JV Girls Lacrosse | Pomperaug | Home - WHS Turf Field [Directions] | 4:15 p.m. | |||
| Tue., 5/14 | JV Baseball | Wilton | Away - JV Baseball Field [Directions] | 4:00 p.m. | 2:40pm | ||
| Tue., 5/14 | V Boys Golf | Immaculate | Home [Directions] | 3:00 p.m. | Immaculate 177 Weston 186 | non league | |
| Tue., 5/14 | V Boys Tennis | Fairfield Prep | Home - WHS Tennis Courts [Directions] | 3:45 p.m. | L 0-5 | non league | |
| Tue., 5/14 | JV Boys Tennis | Fairfield Prep | Home - WHS Tennis Courts [Directions] | 5:00 p.m. | |||
| Tue., 5/14 | V Girls Golf | Brookfield | Away - Sunset Hill Golf Course [Directions] | 4:00 p.m. | Weston 234 Brookfield 243 | ||
| Tue., 5/14 | V Softball | Immaculate | Home - Hurlbutt El. School, Weston [Directions] | 3:30 p.m. | L 12-13 | 2:40pm | |
| Wed., 5/15 | V Baseball | Immaculate | Away - Bethel HS [Directions] | 7:00 p.m. | L 6-5 | 5:00pm | |
| Wed., 5/15 | JV Baseball | Joel Barlow | Away - Field G (Baseball) [Directions] | 4:15 p.m. | 2:40pm | ||
| Wed., 5/15 | V Boys Outdoor Track | Pomperaug | Home - WHS Track [Directions] | 4:00 p.m. | Weston 85 Pomperaug 65 | ||
| Wed., 5/15 | JV Boys Tennis | Fairfield Warde | Away [Directions] | 3:45 p.m. | 2:40pm | ||
| Wed., 5/15 | V Girls Golf | Masuk | Away - Whitney Farms Golf Course [Directions] | 3:00 p.m. | Masuk 214 Weston 273 | ||
| Wed., 5/15 | V Girls Outdoor Track | Pomperaug | Home - Sports Complex & Track [Directions] | 4:00 p.m. | Weston 97 Pomperaug 53 | 2:40pm | |
| Wed., 5/15 | V Softball | Joel Barlow | Home - Hurlbutt El. School, Weston [Directions] | 4:15 p.m. | L 5-13 | ||
| Wed., 5/15 | JV Softball | Wright Tech | Away - Scalzi Park Softball Field #3 [Directions] | 3:45 p.m. | 2:40pm | ||
| Wed., 5/15 | V Girls Tennis | Fairfield Warde | Home - WHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | non league | |
| Wed., 5/15 | JV Girls Tennis | Fairfield Warde | Home - WHS Tennis Courts [Directions] | 5:00 p.m. | |||
| Thu., 5/16 | V Boys Golf | Immaculate | Away [Directions] | 3:00 p.m. | Immaculate 172 Weston 197 | ||
| Thu., 5/16 | V Boys Lacrosse | Pomperaug | Home [Directions] | 6:00 p.m. | W 14-5 | SWC Quarter-Finals | |
| Thu., 5/16 | V Boys Tennis | SWC Tournament | Away [Directions] | 12:00 p.m. | 10:45am | at Wolfe Park | |
| Thu., 5/16 | V Girls Lacrosse | Newtown | Away - Blue and Gold Stadium [Directions] | 5:00 p.m. | L 4-12 | 3:00pm | SWC Quarter-finals |
| Thu., 5/16 | V Girls Tennis | SWC Tournament | Away [Directions] | 12:00 p.m. | 11:00am | at Joel Barlow | |
| Fri., 5/17 | JV Baseball | Immaculate | Home - Revson Field, Weston [Directions] | 4:15 p.m. | |||
| Sat., 5/18 | V Baseball | Joel Barlow | Home - Revson Field, Weston [Directions] | 3:00 p.m. | W 11-10 | ||
| Sat., 5/18 | V Softball | SWC Quarterfinals | Away | Cancelled | Cancelled | Home of higher seed | |
| Mon., 5/20 | V Boys Tennis | SWC Tournament | Away [Directions] | 3:00 p.m. | 1:45pm | at Wolfe Park | |
| Mon., 5/20 | V Girls Lacrosse | SWC Semifinals | Away | Cancelled | Cancelled | at home of higher seed | |
| Mon., 5/20 | V Girls Tennis | SWC Tournament | Away [Directions] | 3:00 p.m. | 2:00pm | at Joel Barlow | |
| Tue., 5/21 | V Baseball | New Milford | Away - New Milford HS [Directions] | 3:00 p.m. | W 7-6 | 1:00pm | SWC Quarterfinals |
| Tue., 5/21 | JV Baseball | Brookfield | Home - Revson Field, Weston [Directions] | Cancelled | Cancelled | ||
| Tue., 5/21 | V Boys Golf | Masuk | Home - Aspetuck Valley Country Club [Directions] | 3:00 p.m. | Weston 178 Masuk 197 | ||
| Tue., 5/21 | V Boys Lacrosse | Newtown | Away [Directions] | 7:00 p.m. | W 13-4 | 5:00pm | SWC Semifinals |
| Tue., 5/21 | V Girls Golf | Bunnell | Home - Aspetuck Valley Country Club [Directions] | 3:45 p.m. | Weston 268 Bunnell 311 | ||
| Tue., 5/21 | V Softball | SWC Semifinals | Away | Cancelled | Cancelled | at DeLuca Field | |
| Wed., 5/22 | V Baseball | Masuk | Away [Directions] | 4:00 p.m. | W 3-1 | 1:45pm | SWC Semifinals at Bethel |
| Wed., 5/22 | V Boys Golf | Bethel | Home - Aspetuck Valley Country Club [Directions] | 3:00 p.m. | Weston 171 Bethel 209 | ||
| Wed., 5/22 | V Boys Outdoor Track | SWC Championship Meet | Home - WHS Track [Directions] | 3:00 p.m. | |||
| Wed., 5/22 | V Girls Lacrosse | SWC Championship Game | Away | Cancelled | Cancelled | at neutral site | |
| Wed., 5/22 | V Girls Outdoor Track | SWC Championship Meet | Home - WHS Track [Directions] | 3:00 p.m. | |||
| Wed., 5/22 | V Softball | SWC Championship Game | Away | Cancelled | Cancelled | at DeLuca Field | |
| Wed., 5/22 | JV Softball | Stratford | Home - Hurlbutt El. School, Weston [Directions] | 4:00 p.m. | |||
| Thu., 5/23 | V Boys Golf | CHAPPA Tournament | Away | TBA | 2 man tournament | ||
| Thu., 5/23 | V Boys Lacrosse | New Fairfield | Away [Directions] | 5:00 p.m. | 3:00pm | SWC Championship Game at Brookfield | |
| Thu., 5/23 | V Girls Golf | Immaculate | Away - Richter Park [Directions] | 3:00 p.m. | Immaculate 232 Weston 251 | ||
| Fri., 5/24 | V Baseball | Bethel | Away [Directions] | 7:00 p.m. | L 1-5 | SWC Championship Game at Penders Field | |
| Fri., 5/24 | V Boys Tennis | CIAC Tourney Through Rnd. of 16 | Away - Bristol Eastern HS and Page Park | 8:30 a.m. | 6:15am | ||
| Fri., 5/24 | V Girls Lacrosse | Wolcott | Home - WHS Turf Field [Directions] | 5:00 p.m. | W 13-1 | CIAC Tourney Qualifying Round | |
| Fri., 5/24 | V Girls Tennis | North Branford | Home - WHS Tennis Courts [Directions] | 2:00 p.m. | W 7-0 | CIAC Tourney 1st Rounds | |
| Fri., 5/24 | V Girls Tennis | CIAC Tourney Qualifying Round | Away - Highest Seed | Cancelled | Cancelled | ||
| Sat., 5/25 | V Baseball | Torrington | Home - Revson Field, Weston [Directions] | 2:00 p.m. | W 9-5 | CIAC Tourney Qualifying Round | |
| Sat., 5/25 | V Boys Lacrosse | CIAC Tourney Qualifying Round | Away - Higher Seed | TBA | |||
| Sat., 5/25 | V Boys Tennis | CIAC Tourney Through Quarterfinals | Away - Bristol Eastern HS | TBA | |||
| Sat., 5/25 | V Softball | CIAC Tourney Qualifying Round | Away - Higher Seed | Cancelled | Cancelled | ||
| Tue., 5/28 | V Boys Golf | SWC Championship Match | Away | 8:30 a.m. | at Ridgewood CC | ||
| Tue., 5/28 | V Girls Golf | SWC Tournament | Away | 8:00 a.m. | |||
| Tue., 5/28 | V Softball | CIAC Tourney 1st Round | Away - Higher Seed | Cancelled | Cancelled | ||
| Wed., 5/29 | V Baseball | Berlin | Away - Sage Park - Zipadelli Field [Directions] | 3:00 p.m. | L 6-8 | 12:00pm | CIAC Tourney 1st Round |
| Wed., 5/29 | V Boys Lacrosse | RHAM | Home - Higher Seed [Directions] | 4:00 p.m. | W 14-5 | CIAC Tourney 1st Round | |
| Wed., 5/29 | V Boys Outdoor Track | CIAC Class MM Championship | Away - Middletown HS [Directions] | 3:00 p.m. | |||
| Wed., 5/29 | V Boys Tennis | CIAC Tourney Quarterfinals | Away - Wesleyan University [Directions] | 2:45 p.m. | |||
| Wed., 5/29 | V Girls Lacrosse | St. Paul Catholic | Away - St. Paul Catholic H.S. [Directions] | 2:00 p.m. | W 19-9 | 11:45am | CIAC Tourney 1st Round |
| Wed., 5/29 | V Girls Outdoor Track | CIAC Class M Championship | Away - Willow Brook Park [Directions] | 10:00 a.m. | 7:00am | ||
| Wed., 5/29 | V Softball | CIAC Tourney 2nd Round | Away - Higher Seed | Cancelled | Cancelled | ||
| Wed., 5/29 | V Girls Tennis | Stonington | Away - SHS Tennis Courts [Directions] | 2:00 p.m. | W 7-0 | CIAC Tourney Quarterfinals | |
| Thu., 5/30 | V Baseball | CIAC Tourney 2nd Round | Away - Higher Seed | Cancelled | Cancelled | ||
| Thu., 5/30 | V Boys Tennis | CIAC Tourney Semifinals | Away - Wesleyan University [Directions] | 4:00 p.m. | |||
| Thu., 5/30 | V Girls Lacrosse | Old Lyme | Away - Old Lyme HS [Directions] | 4:00 p.m. | W 16-10 | 1:15pm | CIAC Tourney Quarterfinals |
| Thu., 5/30 | V Girls Tennis | Old Lyme | Away - Old Lyme HS [Directions] | 2:15 p.m. | W 7-0 | CIAC Tourney Semifinals | |
| Fri., 5/31 | V Boys Tennis | CIAC Tourney Finals | Away - Wesleyan University [Directions] | 4:00 p.m. | |||
| Fri., 5/31 | V Softball | CIAC Tourney Quarterfinals | Away - Higher Seed | Cancelled | Cancelled | ||
| Fri., 5/31 | V Girls Tennis | Valley Regional | Away - Conard HS [Directions] | 3:00 p.m. | W 7-0 | 12:15pm | CIAC Tourney Final |
| Sat., 6/1 | V Baseball | CIAC Tourney Quarterfinals | Away - Higher Seed | Cancelled | Cancelled | ||
| Sat., 6/1 | V Boys Lacrosse | Farmington | Home - WHS Turf Field [Directions] | 3:00 p.m. | W 14-0 | CIAC Tourney Quarterfinals | |
| Sat., 6/1 | V Boys Tennis | State Open Singles Rd. of 16/Doubles Quarterfinals | Away - Wesleyan [Directions] | 10:00 a.m. | |||
| Sat., 6/1 | V Girls Tennis | State Open Qualifying, 1st and 2nd Rounds | Away - Singles @ Conard/Doubles @ Hall | 1:00 p.m. | |||
| Mon., 6/3 | V Boys Golf | CIAC Div. II Championship | Away - Stanley GC - New Britain [Directions] | 8:00 a.m. | |||
| Mon., 6/3 | V Boys Outdoor Track | CIAC Open Championship | Away - Willow Brook Park [Directions] | 2:00 p.m. | |||
| Mon., 6/3 | V Boys Tennis | State Open Singles Quarterfinals/Doubles Semifinals | Away - Wesleyan University [Directions] | 4:00 p.m. | |||
| Mon., 6/3 | V Girls Lacrosse | New Fairfield | Away - Bunnell HS [Directions] | 5:00 p.m. | 3:00pm | CIAC Tourney Semifinals | |
| Mon., 6/3 | V Girls Outdoor Track | CIAC Open Championship | Away - Willow Brook Park [Directions] | 2:00 p.m. | |||
| Mon., 6/3 | V Girls Tennis | State Open Round of 16/Quarterfinals | Away - Yale University [Directions] | 12:00 p.m. | |||
| Tue., 6/4 | V Baseball | CIAC Tourney Semifinals | Away - Site TBA | Cancelled | Cancelled | ||
| Tue., 6/4 | V Boys Tennis | State Open Singles Semifinals | Away - Wesleyan University [Directions] | 4:00 p.m. | |||
| Tue., 6/4 | V Girls Golf | CIAC Girls Golf Championship | Away - Tashua Knolls CC [Directions] | 8:30 a.m. | |||
| Tue., 6/4 | V Softball | CIAC Tourney Semifinals | Away - Site TBA | Cancelled | Cancelled | ||
| Tue., 6/4 | V Girls Tennis | State Open Semifinals | Away - Yale University [Directions] | 3:00 p.m. | |||
| Wed., 6/5 | V Boys Lacrosse | Notre Dame-West Haven | Away - Brien McMahon HS [Directions] | 5:00 p.m. | W 10-8 | 3:00pm | CIAC Tourney Semifinals |
| Wed., 6/5 | V Boys Tennis | State Open Finals | Away - Connecticut Tennis Center [Directions] | TBA | |||
| Wed., 6/5 | V Girls Tennis | State Open Finals | Away - Connecticut Tennis Center [Directions] | TBA | |||
| Sat., 6/8 | V Baseball | CIAC Tourney Final | Away - Palmer Field, Middletown [Directions] | Cancelled | Cancelled | ||
| Sat., 6/8 | V Boys Golf | CIAC Open Championship | Away - Black Hall GC | 1:00 p.m. | |||
| Sat., 6/8 | V Boys Lacrosse | New Fairfield | Away - Brien McMahon HS [Directions] | 1:00 p.m. | 11am | CIAC Tourney Final | |
| Sat., 6/8 | V Boys Outdoor Track | New England Championship | Away - Thornton Academy, Saco, ME [Directions] | TBA | |||
| Sat., 6/8 | V Girls Golf | CIAC Open Championship | Away - Black Hall GC | 1:00 p.m. | |||
| Sat., 6/8 | V Girls Lacrosse | CIAC Tourney Final | Away - Site TBA | TBA | |||
| Sat., 6/8 | V Girls Outdoor Track | New England Championship | Away - Thornton Academy, Saco, ME [Directions] | TBA | |||
| Sat., 6/8 | V Softball | CIAC Tourney Final | Away - Site TBA | Cancelled | Cancelled | ||
| Tue., 6/11 | V Boys Outdoor Track | CIAC Decathlon Champ. | Away - Manchester [Directions] | 11:00 a.m. | |||
| Tue., 6/11 | V Girls Outdoor Track | CIAC Heptathlon/Hammer/Steeplechase Champ. | Away - Manchester [Directions] | 11:30 a.m. | |||
| Wed., 6/12 | V Boys Outdoor Track | CIAC Decathlon/Hammer/Steeplechase Champ. | Away - Manchester [Directions] | 11:00 a.m. | |||
| Wed., 6/12 | V Girls Outdoor Track | CIAC Heptathlon Champ. | Away - Manchester [Directions] | 11:00 a.m. | |||
| Wed., 6/19 | V Boys Golf | New England Championships | Away - Bretwood GC - Keene, NH | 8:00 a.m. | |||
| Wed., 6/19 | V Girls Golf | New England Championships | Away - Bretwood GC - Keene, NH | 8:00 a.m. | |||