| Weston 2013-14 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 760 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| TBA | JV Baseball | Immaculate | Home - Revson Field, Weston [Directions] | 4:00 p.m. | ||
| TBA | JV Baseball | Pomperaug | Away - Community Baseball Field [Directions] | 4:15 p.m. | 2:45pm | |
| TBA | JV Baseball | Newtown | Away - Newtown High School Baseball Field [Directions] | TBA | 2:45pm | |
| TBA | JV Baseball | Brookfield | Away - Huckleberry Hill Elementary School Baseball Field [Directions] | TBA | 2:45pm | |
| TBA | FR Baseball | Stratford | Away - Penders Field [Directions] | 4:15 p.m. | 2:45pm | |
| TBA | FR Baseball | Joel Barlow | Away - Redding Boys & Girls Club [Directions] | TBA | 2:40pm | |
| TBA | FR Baseball | Newtown | Away - Newtown High School Baseball Field [Directions] | TBA | 2:45pm | |
| TBA | JV Football | New Milford | Away - New Milford High School [Directions] | 4:00 p.m. | 2:45pm | Freshman/Sophomore game |
| TBA | V Boys Ice Hockey | Staples (Scrim.) | Home - Danbury Ice Arena [Directions] | TBA | ||
| TBA | JV Boys Ice Hockey | Wilton | Home - Wonderland of Ice - Bridgeport [Directions] | TBA | ||
| TBA | JV Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena [Directions] | TBA | ||
| TBA | JV Boys Lacrosse | Stratford | Away - Wooster Middle School Field [Directions] | TBA | 2:45pm | |
| TBA | JV Girls Basketball | Newtown | Away - Newtown High School Gymnasium [Directions] | TBA | 4:00pm | |
| TBA | JV Field Hockey | Immaculate | Home - WHS Turf Field [Directions] | 10:00 a.m. | ||
| TBA | FR Girls Lacrosse | Joel Barlow | Away - Joel Barlow High School [Directions] | TBA | 8:45am | |
| TBA | JV Softball | Immaculate | Away - Immaculate [Directions] | 10:00 a.m. | 8:15am | |
| TBA | JV Softball | Joel Barlow | Away - Field E (Softball) [Directions] | TBA | ||
| TBA | JV Softball | Pomperaug | Away - Community Softball Field [Directions] | TBA | ||
| TBA | JV Softball | Stratford | Home - Hurlbutt Elementary Field [Directions] | TBA | ||
| TBA | JV Softball | Newtown | Home - Hurlbutt El. School, Weston [Directions] | TBA | ||
| Wed., 8/28 | V Football | Wilton (Scrim.) | Away - Fujitani Field - Turf [Directions] | 4:00 p.m. | 2:45pm | |
| Wed., 8/28 | V Field Hockey | Ridgefield (Scrim.) | Home - WHS Turf Field [Directions] | 5:00 p.m. | ||
| Thu., 8/29 | V Boys Soccer | Norwalk (Scrim.) | Home - WHS Turf Field [Directions] | 4:45 p.m. | ||
| Thu., 8/29 | JV Boys Soccer | Norwalk (Scrim.) | Away - Nathan Hale Middle School [Directions] | 4:30 p.m. | 3:00pm | at Nathan Hale Middle School, Norwalk |
| Fri., 8/30 | V Girls Volleyball | Kennedy Catholic-Somers (NY) (Scrim.) | Home - WHS Gymnasium [Directions] | 3:15 p.m. | ||
| Fri., 8/30 | JV Girls Volleyball | Kennedy Catholic-Somers (NY) (Scrim.) | Home - WHS Old Gym [Directions] | 3:15 p.m. | ||
| Sat., 8/31 | V Boys Soccer | Fairfield Warde (Scrim.) | Home - WHS Turf Field [Directions] | 9:00 a.m. | JV scrimmage to follow | |
| Sat., 8/31 | V Girls Soccer | Bethel Jamboree | Away [Directions] | 10:00 a.m. | 8:30 am | |
| Tue., 9/3 | V Girls Volleyball | Ridgefield (Scrim.) | Away - RHS Main Gym [Directions] | 3:45 p.m. | 2:45pm | |
| Fri., 9/6 | JV Field Hockey | New Fairfield Play Day | Away | 4:00 p.m. | TBA | |
| Fri., 9/6 | V Girls Soccer | Brien McMahon (Scrim.) | Home - WHS Turf Field [Directions] | 5:00 p.m. | 2:45pm | |
| Sat., 9/7 | V Boys Soccer | Rye (NY) (Scrim.) | Home - WHS Turf Field [Directions] | 10:30 a.m. | ||
| Sat., 9/7 | V Field Hockey | New Fairfield Play Day | Away [Directions] | 08:00 a.m. | TBA | |
| Sat., 9/7 | V Girls Volleyball | Val Dickenson Memorial Jamboree | Away [Directions] | 9:00 a.m. | 8:00 am | |
| Mon., 9/9 | V Boys Soccer | Platt (Scrim.) | Home [Directions] | 4:30 p.m. | ||
| Tue., 9/10 | V Boys Cross Country | Oxford, Notre Dame-Fairfield, Stratford | Home - Weston High School [Directions] | Weston 16 Notre Dame 47 Weston 15 Oxford 50 Weston 18 Stratford 45 | ||
| Tue., 9/10 | V Girls Cross Country | Oxford, Notre Dame-Fairfield, Stratford | Home - Weston High School [Directions] | Notre Dame 25 Weston 30 Oxford 16 Weston 47 Stratford 25 Weston 30 | ||
| Tue., 9/10 | V Girls Volleyball | Stamford | Away - Stamford High School [Directions] | L 0-3 | 2:45pm | non-league |
| Tue., 9/10 | JV Girls Volleyball | Stamford | Away - Stamford High School [Directions] | 5:30 p.m. | 2:45pm | |
| Wed., 9/11 | V Boys Soccer | Pomperaug | Home - WHS Turf Field [Directions] | L 0-2 | ||
| Wed., 9/11 | JV Boys Soccer | Pomperaug | Away - Sports Complex & Track [Directions] | 6:30 p.m. | 3:00pm | |
| Wed., 9/11 | V Girls Soccer | Pomperaug | Home - WHS Turf Field [Directions] | L 0-4 | ||
| Wed., 9/11 | JV Girls Soccer | Pomperaug | Away - Sports Complex & Track [Directions] | 4:30 p.m. | 3:00pm | |
| Thu., 9/12 | V Football | Oxford | Home - WHS Stadium Field [Directions] | L 6-23 | ||
| Thu., 9/12 | V Field Hockey | Watertown | Home - WHS Turf Field [Directions] | W 1-0 | non-league game | |
| Thu., 9/12 | JV Field Hockey | Watertown | Home - WHS Turf Field [Directions] | 6:30 p.m. | ||
| Thu., 9/12 | V Girls Swimming and Diving | New Fairfield | Home - Weston Middle School Pool [Directions] | Weston 95 New Fairfield 83 | ||
| Thu., 9/12 | V Girls Volleyball | Bethel | Home - WHS Gymnasium [Directions] | W 3-2 | non-league | |
| Thu., 9/12 | JV Girls Volleyball | Bethel | Home - WHS Gymnasium [Directions] | 3:30 p.m. | ||
| Fri., 9/13 | V Boys Soccer | Kolbe Cathedral | Away - University of Bridgeport [Directions] | W 4-2 | 2:45pm | |
| Fri., 9/13 | V Girls Soccer | Kolbe Cathedral | Home - WHS Turf Field [Directions] | W 8-0 | ||
| Mon., 9/16 | V Boys Soccer | Bethel | Home - WHS Turf Field [Directions] | T 0-0 | ||
| Mon., 9/16 | JV Boys Soccer | Bethel | Home - WHS Turf Field [Directions] | 5:00 p.m. | ||
| Mon., 9/16 | V Girls Soccer | Bethel | Away - @ Bethel High School [Directions] | L 1-3 | 2:45 pm | |
| Mon., 9/16 | JV Girls Soccer | Bethel | Away - @ Bethel High School [Directions] | 4:15 p.m. | 2:45pm | |
| Mon., 9/16 | V Girls Volleyball | Pomperaug | Away - PHS Main Gym [Directions] | L 1-3 | 2:45pm | non-league |
| Mon., 9/16 | JV Girls Volleyball | Pomperaug | Away - PHS Main Gym [Directions] | 4:30 p.m. | 2:45pm | |
| Tue., 9/17 | V Boys Cross Country | New Milford, Brookfield, Immaculate | Away - New Milford High School [Directions] | Weston 15 Immaculate 47 Brookfield 20 Weston 39 New Milford 19 Weston 43 | 2:45pm | |
| Tue., 9/17 | V Girls Cross Country | New Milford, Brookfield, Immaculate | Away - New Milford High School [Directions] | Immaculate 15 Weston 50 New Milford 15 Weston 50 Brookfield 20 Weston 41 | ||
| Tue., 9/17 | V Field Hockey | Masuk | Away - Masuk Middle Field [Directions] | L 0-3 | 2:45pm | |
| Tue., 9/17 | JV Field Hockey | Masuk | Away - Masuk Middle Field [Directions] | 5:30 p.m. | 2:45 pm | |
| Tue., 9/17 | V Girls Swimming and Diving | New Milford | Away - Canterbury School [Directions] | Weston 93 New Milford 83 | 5:15pm | |
| Wed., 9/18 | V Girls Soccer | Stratford | Home - WHS Turf Field [Directions] | W 9-0 | ||
| Wed., 9/18 | JV Girls Soccer | Stratford | Home - WHS Turf Field [Directions] | 5:00 p.m. | ||
| Wed., 9/18 | V Girls Volleyball | New Milford | Away - New Milford High School [Directions] | W 3-1 | 2:45pm | |
| Wed., 9/18 | JV Girls Volleyball | New Milford | Away - New Milford High School [Directions] | 4:30 p.m. | 2:45pm | |
| Thu., 9/19 | V Boys Soccer | Stratford | Away - Penders Field [Directions] | T 2-2 | 5:15pm | |
| Thu., 9/19 | JV Boys Soccer | Stratford | Away - Wooster Middle School Field [Directions] | 4:15 p.m. | 2:45pm | |
| Thu., 9/19 | V Field Hockey | Bethel | Home - WHS Turf Field [Directions] | W 3-2 | ||
| Thu., 9/19 | JV Field Hockey | Bethel | Home - WHS Turf Field [Directions] | 5:00 p.m. | ||
| Fri., 9/20 | V Girls Swimming and Diving | Brookfield | Home - Weston Middle School Pool [Directions] | Weston 98 Brookfield 86 | ||
| Fri., 9/20 | V Girls Volleyball | Joel Barlow | Home - WHS Gymnasium [Directions] | L 0-3 | ||
| Fri., 9/20 | JV Girls Volleyball | Joel Barlow | Home - WHS Gymnasium [Directions] | 3:30 p.m. | ||
| Sat., 9/21 | V Boys Cross Country | CT River Valley Championships | Away [Directions] | EO Smith 50 Choate 65 Weston 95 Nonnewaug 102 Daniel Hand 115 5 0ther schools | 6:30am | at Cromwell High School |
| Sat., 9/21 | V Football | Stratford | Away - Penders Field [Directions] | W 20-14 | 10:30am | Cheer bus at 11:30am |
| Sat., 9/21 | V Girls Cross Country | CT River Valley Championship | Away [Directions] | Weston 221 8th place finish | 6:30am | at Cromwell High Scool |
| Sat., 9/21 | V Field Hockey | Joel Barlow | Away - Field I (Stadium) [Directions] | L 0-3 | 3:15pm | |
| Sat., 9/21 | JV Field Hockey | Joel Barlow | Away - Field I (Stadium) [Directions] | 4:30 p.m. | 3:15pm | |
| Mon., 9/23 | JV Football | Stratford | Home - WHS Stadium Field [Directions] | 4:00 p.m. | Freshman/Sophomore game | |
| Mon., 9/23 | V Girls Volleyball | Bethel | Away - @ Bethel High School [Directions] | L 1-3 | 2:45pm | |
| Mon., 9/23 | JV Girls Volleyball | Bethel | Away - @ Bethel High School [Directions] | 4:30 p.m. | 2:45pm | |
| Tue., 9/24 | V Boys Cross Country | Lauralton Hall, New Fairfield, Newtown | Away [Directions] | Newtown 27 Weston 30 New Fairfield 18 Weston 39 | 2:45pm | at Lauralton |
| Tue., 9/24 | V Boys Soccer | Newtown | Home - WHS Turf Field [Directions] | L 0-1 | ||
| Tue., 9/24 | JV Boys Soccer | Newtown | Home - WHS Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 9/24 | V Girls Cross Country | Lauralton Hall, New Fairfield, Newtown | Away [Directions] | Newtown 18 Weston 45 Lauralton 22 Weston 39 New Fairfield 15 Weston 48 | at Lauralton | |
| Tue., 9/24 | V Field Hockey | New Fairfield | Away - Rebel Turf [Directions] | L 0-9 | 2:45pm | |
| Tue., 9/24 | JV Field Hockey | New Fairfield | Away - Rebel Turf [Directions] | 6:00 p.m. | 2:45 pm | |
| Tue., 9/24 | V Girls Soccer | Newtown | Away - Blue and Gold Stadium [Directions] | L 0-3 | 3:15pm | |
| Tue., 9/24 | JV Girls Soccer | Newtown | Away - Blue and Gold Stadium [Directions] | 5:00 p.m. | 3:15pm | |
| Tue., 9/24 | V Girls Swimming and Diving | Newtown | Home - Weston Middle School Pool [Directions] | Weston 94 Newtown 90 | ||
| Wed., 9/25 | V Field Hockey | Fairfield Ludlowe | Away - Taft Field [Directions] | L 0-3 | 3:45pm | non-league game |
| Wed., 9/25 | V Girls Volleyball | Masuk | Home - WHS Gymnasium [Directions] | L 1-3 | ||
| Wed., 9/25 | JV Girls Volleyball | Masuk | Home - WHS Gymnasium [Directions] | 3:30 p.m. | ||
| Thu., 9/26 | V Boys Soccer | Masuk | Away - Masuk Stadium Field [Directions] | L 0-2 | 2:45pm | |
| Thu., 9/26 | JV Boys Soccer | Masuk | Away - Great Hollow Lake Fields at Wolfe Park [Directions] | 4:15 p.m. | 2:45pm | |
| Thu., 9/26 | V Girls Soccer | Masuk | Home - WHS Turf Field [Directions] | T 1-1 | ||
| Thu., 9/26 | JV Girls Soccer | Masuk | Home - WHS Turf Field [Directions] | 5:00 p.m. | ||
| Fri., 9/27 | V Field Hockey | Newtown | Away - Blue and Gold Stadium [Directions] | L 0-2 | 2:45pm | |
| Fri., 9/27 | JV Field Hockey | Newtown | Away - Blue and Gold Stadium [Directions] | 6:00 p.m. | 2:45 pm | |
| Fri., 9/27 | V Girls Swimming and Diving | Stratford | Away - Flood Middle School Pool [Directions] | Weston 90 Stratford 63 | 4:00pm | |
| Fri., 9/27 | V Girls Volleyball | Brookfield | Home - WHS Gymnasium [Directions] | L 2-3 | ||
| Fri., 9/27 | JV Girls Volleyball | Brookfield | Home - WHS Gymnasium [Directions] | 3:30 p.m. | ||
| Sat., 9/28 | V Boys Cross Country | Ocean State Invitational | Away | 11:00 a.m. | 8:30 am | |
| Sat., 9/28 | V Football | Immaculate | Away - Mustang Valley [Directions] | W 42-20 | 10:45am | Cheer bus at 11:45pm |
| Sat., 9/28 | V Boys Soccer | Notre Dame-Fairfield | Home - WHS Turf Field [Directions] | W 5-1 | ||
| Sat., 9/28 | V Girls Cross Country | Ocean State Invitational | Away | 11:00 a.m. | 8:30 am | |
| Sat., 9/28 | V Girls Soccer | Notre Dame-Fairfield | Away - Park Avenue Field at Notre Dame [Directions] | W 1-0 | 2:15 pm | |
| Mon., 9/30 | JV Football | Immaculate | Home - WHS Stadium Field [Directions] | 4:00 p.m. | Freshman/Sophomore game | |
| Mon., 9/30 | V Boys Soccer | Joel Barlow | Away - Field J [Directions] | L 0-5 | 2:45pm | |
| Mon., 9/30 | JV Boys Soccer | Joel Barlow | Away - Field E (Softball) [Directions] | 4:15 p.m. | 2:45pm | |
| Mon., 9/30 | V Girls Soccer | Joel Barlow | Home - WHS Turf Field [Directions] | L 1-3 | ||
| Mon., 9/30 | JV Girls Soccer | Joel Barlow | Home - WHS Turf Field [Directions] | 5:00 p.m. | ||
| Mon., 9/30 | V Girls Volleyball | New Fairfield | Home - WHS Gymnasium [Directions] | W 3-1 | ||
| Mon., 9/30 | JV Girls Volleyball | New Fairfield | Home - WHS Gymnasium [Directions] | 3:30 p.m. | ||
| Tue., 10/1 | V Boys Cross Country | Masuk, Pomperaug, Kolbe Cathedral | Away [Directions] | Weston 21 Masuk 40 Weston 15 Kolbe 50 Pomperaug 21 Weston 36 | 2:45pm | |
| Tue., 10/1 | V Girls Cross Country | Masuk, Pomperaug, Kolbe Cathedral | Away [Directions] | Weston 15 Kolbe 50 Weston 27 Masuk 28 Pomperaug 15 Weston 48 | ||
| Tue., 10/1 | V Field Hockey | Brookfield | Home - WHS Turf Field [Directions] | L 0-2 | ||
| Tue., 10/1 | JV Field Hockey | Brookfield | Home - WHS Turf Field [Directions] | 5:00 p.m. | ||
| Tue., 10/1 | V Girls Swimming and Diving | Bunnell | Home - Weston Middle School Pool [Directions] | Weston 95 Bunnell 68 | ||
| Wed., 10/2 | V Field Hockey | Watertown | Away - John J. Mills Complex @ Watertown High School [Directions] | W 5-1 | 2:45pm | |
| Wed., 10/2 | JV Field Hockey | Watertown | Away - John J. Mills Complex @ Watertown High School [Directions] | 4:45 p.m. | 2:45 pm | |
| Wed., 10/2 | V Girls Volleyball | Stratford | Away - SHS Needham Gymnasium [Directions] | L 2-3 | 2:45pm | |
| Wed., 10/2 | JV Girls Volleyball | Stratford | Away - SHS Needham Gymnasium [Directions] | 5:00 p.m. | 2:45pm | |
| Thu., 10/3 | V Boys Soccer | Bunnell | Home - WHS Turf Field [Directions] | W 1-0 | ||
| Thu., 10/3 | JV Boys Soccer | Bunnell | Home - WHS Turf Field [Directions] | 5:00 p.m. | ||
| Thu., 10/3 | V Girls Soccer | Bunnell | Away - Bunnell Turf Field [Directions] | W 2-1 | 5:00pm | |
| Thu., 10/3 | V Girls Volleyball | Lauralton Hall | Away - Lauralton Hall Gymnasium [Directions] | W 3-1 | 2:45pm | |
| Thu., 10/3 | JV Girls Volleyball | Lauralton Hall | Away - Lauralton Hall Gymnasium [Directions] | 4:30 p.m. | 2:45pm | |
| Fri., 10/4 | V Girls Swimming and Diving | Pomperaug | Away - PHS Pool [Directions] | Weston 98 Pomperaug 88 | 4:15pm | |
| Sat., 10/5 | V Football | New Milford | Home - WHS Stadium Field [Directions] | L 20-35 | ||
| Sat., 10/5 | V Boys Soccer | Seymour | Away - Seymour High Main Field [Directions] | W 1-0 | 2:30pm | |
| Sat., 10/5 | JV Boys Soccer | Seymour | Away - Seymour High Main Field [Directions] | 4:00 p.m. | 2:30pm | |
| Sat., 10/5 | JV Girls Soccer | Bunnell | Away - Bunnell Turf Field [Directions] | 3:30 p.m. | 2:00pm | |
| Mon., 10/7 | V Girls Volleyball | Pomperaug | Home - WHS Gymnasium [Directions] | W 3-0 | ||
| Mon., 10/7 | JV Girls Volleyball | Pomperaug | Home - WHS Gymnasium [Directions] | 3:30 p.m. | ||
| Tue., 10/8 | V Boys Cross Country | Bethel, Bunnell, Joel Barlow | Home [Directions] | Weston 20 Bunnell 35 Weston 18 Bethel 43 Weston 22 Joel Barlow 33 | 2:45pm | |
| Tue., 10/8 | V Boys Soccer | New Milford | Home - WHS Turf Field [Directions] | T 1-1 | ||
| Tue., 10/8 | V Girls Cross Country | Bethel, Bunnell, Joel Barlow | Home [Directions] | Bunnell 19 Weston 40 Bethel 17 Weston 46 Joel Barlow 15 Weston 50 | ||
| Tue., 10/8 | V Field Hockey | Pomperaug | Home - WHS Turf Field [Directions] | L 1-5 | ||
| Tue., 10/8 | JV Field Hockey | Pomperaug | Home - WHS Turf Field [Directions] | 5:30 p.m. | ||
| Tue., 10/8 | V Girls Soccer | New Milford | Away - New Milford High School [Directions] | W 1-0 | 2:45 pm | |
| Tue., 10/8 | JV Girls Soccer | New Milford | Away - New Milford High School [Directions] | 4:15 p.m. | 2:45pm | |
| Tue., 10/8 | V Girls Swimming and Diving | Masuk | Home - Weston Middle School Pool [Directions] | Weston 93 Masuk 85 | ||
| Wed., 10/9 | JV Boys Soccer | New Milford | Home - WHS Turf Field [Directions] | 7:00 p.m. | ||
| Wed., 10/9 | V Girls Volleyball | Notre Dame-Fairfield | Away - Sister Marion Rielly Auditorium at Notre Dame [Directions] | W 3-1 | 3:15pm | |
| Wed., 10/9 | JV Girls Volleyball | Notre Dame-Fairfield | Away - Sister Marion Rielly Auditorium at Notre Dame [Directions] | 4:30 p.m. | 3:15pm | |
| Thu., 10/10 | V Boys Soccer | New Fairfield | Away - Rebel Turf [Directions] | T 3-3 | 2:45pm | |
| Thu., 10/10 | JV Boys Soccer | New Fairfield | Away - Rebel Turf [Directions] | 4:15 p.m. | 2:45pm | |
| Thu., 10/10 | V Field Hockey | New Milford | Away - New Milford High School [Directions] | L 0-3 | 2:45pm | |
| Thu., 10/10 | JV Field Hockey | New Milford | Away - New Milford High School [Directions] | 5:30 p.m. | 2:45 pm | |
| Thu., 10/10 | V Girls Soccer | New Fairfield | Home - WHS Turf Field [Directions] | W 5-0 | ||
| Thu., 10/10 | JV Girls Soccer | New Fairfield | Home - WHS Turf Field [Directions] | 5:00 p.m. | ||
| Thu., 10/10 | V Girls Volleyball | Nonnewaug | Away - Nonnewaug High School Gym [Directions] | W 3-0 | 2:45pm | |
| Fri., 10/11 | V Girls Swimming and Diving | Lauralton Hall | Away - Foran High School Pool [Directions] | Weston 99 Laurelton Hall 82 | 5:00pm | |
| Fri., 10/11 | JV Girls Volleyball | Immaculate | Away - Immaculate High School [Directions] | 4:00 p.m. | 2:45pm | |
| Sat., 10/12 | V Football | Notre Dame-Fairfield | Away - McCarty Stadium at Notre Dame [Directions] | W 62-32 | 10:45am | Cheer bus at 11:45am |
| Sat., 10/12 | V Boys Soccer | Brookfield | Home - WHS Turf Field [Directions] | T 0-0 | ||
| Sat., 10/12 | JV Boys Soccer | Brookfield | Home - WHS Turf Field [Directions] | 2:00 p.m. | ||
| Sat., 10/12 | V Field Hockey | Immaculate | Home - WHS Turf Field [Directions] | L 2-4 | ||
| Sat., 10/12 | V Girls Soccer | Brookfield | Away - BHS Stadium Field [Directions] | T 2-2 | 2:15pm | |
| Sat., 10/12 | JV Girls Soccer | Brookfield | Away - BHS Stadium Field [Directions] | 4:00 p.m. | 2:15pm | |
| Mon., 10/14 | JV Football | Notre Dame-Fairfield | Home - WHS Stadium Field [Directions] | 4:00 p.m. | Freshman/Sophomore game | |
| Mon., 10/14 | V Girls Soccer | Lauralton Hall | Home - WHS Turf Field [Directions] | T 0-0 | ||
| Mon., 10/14 | JV Girls Soccer | Lauralton Hall | Home - WHS Turf Field [Directions] | 5:00 p.m. | ||
| Tue., 10/15 | V Girls Volleyball | Brien McMahon | Home [Directions] | L 1-3 | ||
| Tue., 10/15 | JV Girls Volleyball | Brien McMahon | Home - WHS Gymnasium [Directions] | 3:45 p.m. | ||
| Wed., 10/16 | V Field Hockey | Lauralton Hall | Away - Lauralton Hall Field [Directions] | L 0-6 | 2:45pm | |
| Wed., 10/16 | JV Field Hockey | Lauralton Hall | Away - Lauralton Hall Field [Directions] | 6:00 p.m. | 2:45 pm | |
| Wed., 10/16 | V Girls Soccer | Naugatuck | Home - WHS Turf Field [Directions] | W 2-1 | ||
| Wed., 10/16 | JV Girls Soccer | Naugatuck | Home - WHS Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 10/16 | V Girls Volleyball | Oxford | Away - OHS-Main Gym [Directions] | W 3-0 | 2:45pm | |
| Wed., 10/16 | JV Girls Volleyball | Oxford | Away - OHS-Main Gym [Directions] | 4:30 p.m. | 2:45pm | |
| Thu., 10/17 | V Boys Cross Country | SWC Championship Meet | Away [Directions] | 3:30 p.m. | 2:15pm | at Bethel |
| Thu., 10/17 | V Boys Soccer | Oxford | Home - WHS Turf Field [Directions] | W 7-1 | ||
| Thu., 10/17 | JV Boys Soccer | Oxford | Home - WHS Turf Field [Directions] | 5:00 p.m. | ||
| Thu., 10/17 | V Girls Cross Country | SWC Championship Meet | Away [Directions] | 4:00 p.m. | 2:15pm | at Bethel |
| Thu., 10/17 | V Girls Soccer | Oxford | Away - OHS Wolverine Field [Directions] | W 5-1 | 4:00pm | |
| Thu., 10/17 | JV Girls Soccer | Oxford | Away - OHS Soccer Field-West [Directions] | Cancelled | 4:00pm | |
| Thu., 10/17 | V Girls Swimming and Diving | Oxford | Away - OHS Pool [Directions] | Weston 95 Oxford 73 | 2:45pm | |
| Fri., 10/18 | V Field Hockey | Masuk | Home - WHS Turf Field [Directions] | L 0-1 | ||
| Fri., 10/18 | JV Field Hockey | Masuk | Home - WHS Turf Field [Directions] | 5:00 p.m. | ||
| Fri., 10/18 | V Girls Volleyball | Kolbe Cathedral | Home - WHS Gymnasium [Directions] | W 3-1 | ||
| Fri., 10/18 | JV Girls Volleyball | Kolbe Cathedral | Home - WHS Gymnasium [Directions] | 3:30 p.m. | ||
| Sat., 10/19 | V Football | Holy Cross | Home - WHS Stadium Field [Directions] | L 7-37 | Non-League, HOMECOMING | |
| Mon., 10/21 | JV Football | Holy Cross | Away - Holy Cross HS [Directions] | 4:15 p.m. | 2:45pm | Freshman/Sophomore game |
| Mon., 10/21 | V Boys Soccer | Immaculate | Away - Mustang Valley [Directions] | T 1-1 | 2:45pm | |
| Mon., 10/21 | JV Boys Soccer | Immaculate | Away - Immaculate High School [Directions] | 4:15 p.m. | 2:45pm | |
| Mon., 10/21 | V Girls Soccer | Immaculate | Home - WHS Turf Field [Directions] | L 2-3 | ||
| Mon., 10/21 | JV Girls Soccer | Immaculate | Home - WHS Turf Field [Directions] | 5:00 p.m. | ||
| Mon., 10/21 | V Girls Volleyball | Bunnell | Away - Bunnell [Directions] | L 0-3 | 4:00pm | |
| Mon., 10/21 | JV Girls Volleyball | Bunnell | Away - Bunnell [Directions] | 5:15 p.m. | 4:00pm | |
| Tue., 10/22 | V Boys Cross Country | Bethel | Away [Directions] | 4:30 p.m. | 2:45 pm | |
| Tue., 10/22 | V Girls Cross Country | Bethel | Away [Directions] | 4:30 p.m. | 2:45 pm | |
| Tue., 10/22 | V Field Hockey | Brookfield | Away - BHS Stadium Field [Directions] | L 0-1 | 3:45pm | non-league game |
| Tue., 10/22 | JV Field Hockey | Brookfield | Away - BHS Stadium Field [Directions] | 5:30 p.m. | 3:45 pm | |
| Tue., 10/22 | V Girls Swimming and Diving | Joel Barlow | Away - Western CT State University - O'Neill Center [Directions] | 7:00 p.m. | 5:45pm | |
| Wed., 10/23 | V Girls Volleyball | Newtown | Home - WHS Gymnasium [Directions] | L 0-3 | ||
| Wed., 10/23 | JV Girls Volleyball | Newtown | Home - WHS Gymnasium [Directions] | 3:30 p.m. | ||
| Fri., 10/25 | V Football | Newtown | Away - Blue and Gold Stadium [Directions] | L 13-47 | 4:30pm | Cheer bus at 5:30pm |
| Fri., 10/25 | V Boys Soccer | SWC Quarterfinals | Away | Cancelled | TBA | at home of higher seed |
| Fri., 10/25 | V Field Hockey | SWC Quarterfinals | Away | Cancelled | TBA | at home of higher seed |
| Fri., 10/25 | V Girls Soccer | Immaculate | Away - Mustang Valley [Directions] | L 0-1 | 1:30pm | SWC Quarterfinals |
| Sat., 10/26 | V Boys Cross Country | CIAC Class M Championship | Away - Wickham Park - East Hartford [Directions] | finished 6th with a score of 178 | ||
| Sat., 10/26 | JV Football | Newtown | Home - WHS Stadium Field [Directions] | 10:00 a.m. | Freshman/Sophomore game | |
| Sat., 10/26 | V Girls Cross Country | CIAC Class M Championship | Away - Wickham Park - East Hartford [Directions] | 11:55 a.m. | ||
| Mon., 10/28 | V Boys Soccer | SWC Semifinals | Away [Directions] | Cancelled | TBA | at Pomperaug |
| Mon., 10/28 | V Girls Volleyball | SWC Quarterfinals | Away | TBA | TBA | at home of higher seed |
| Tue., 10/29 | V Field Hockey | SWC Semifinals | Home - WHS Turf Field [Directions] | Cancelled | Hosting games at 5:30 and 7:30pm | |
| Tue., 10/29 | V Girls Soccer | SWC Semifinals | Away [Directions] | Cancelled | TBA | at Brookfield |
| Wed., 10/30 | V Boys Soccer | SWC Championship Game | Away [Directions] | Cancelled | TBA | at Bunnell |
| Wed., 10/30 | V Girls Swimming and Diving | SWC Diving Championships | Away | 6:00 p.m. | at Masuk, warmups at 4:30pm | |
| Wed., 10/30 | V Girls Volleyball | SWC Semifinals | Away | TBA | TBA | |
| Fri., 11/1 | V Boys Cross Country | CIAC Open Championship | Away - Wickham Park - East Hartford [Directions] | 2:00 p.m. | ||
| Fri., 11/1 | V Girls Cross Country | CIAC Open Championship | Away - Wickham Park - East Hartford [Directions] | 2:45 p.m. | ||
| Fri., 11/1 | V Field Hockey | SWC Championship | Away | Cancelled | at Brookfield | |
| Fri., 11/1 | V Girls Soccer | SWC Championship Game | Away [Directions] | Cancelled | TBA | at Newtown |
| Sat., 11/2 | V Football | Brookfield | Home - WHS Stadium Field [Directions] | L 20-49 | ||
| Sat., 11/2 | V Girls Swimming and Diving | SWC Championship Meet | Away [Directions] | 4:00 p.m. | 12:00pm | At Masuk, warm-ups at 2pm |
| Sat., 11/2 | V Girls Volleyball | SWC Championship Game | Home - WHS Gymnasium [Directions] | 7:00 p.m. | ||
| Mon., 11/4 | JV Football | Brookfield | Away - BHS Back Turf [Directions] | 4:00 p.m. | 2;45pm | Freshman/Sophomore game |
| Mon., 11/4 | V Girls Soccer | Montville | Home - WHS Turf Field [Directions] | W 5-1 | ADMISSION - $8 for Adults, $5 for Students/Senior Citizens | |
| Mon., 11/4 | V Girls Volleyball | East Catholic | Away [Directions] | L 2-3 | 3:15pm | |
| Tue., 11/5 | V Boys Soccer | Stonington | Away - Palmer Field (Turf) [Directions] | W 1-0 | 1:00pm | |
| Wed., 11/6 | V Girls Soccer | Lewis Mills | Away - Nassahegan Field - Burlington [Directions] | W 3-1 | 1:00pm | |
| Wed., 11/6 | V Girls Swimming and Diving | CIAC Class S Diving Trials/Finals | Away - Middletown HS [Directions] | 5:30 p.m. | ||
| Thu., 11/7 | V Boys Soccer | Granby Memorial | Home [Directions] | W 2-1 | ||
| Fri., 11/8 | V Girls Soccer | Woodland | Away [Directions] | W 2-1 | 11:30am | CIAC State Quarterfinals |
| Sat., 11/9 | V Boys Cross Country | New England Championship | Away - Derryfield Park-Manchester, NH [Directions] | TBA | ||
| Sat., 11/9 | V Football | Pomperaug | Home - WHS Stadium Field [Directions] | L 0-21 | ||
| Sat., 11/9 | V Boys Soccer | Lyman Hall | Away - Lyman Hall Fitzgerald Field [Directions] | L 0-2 | 1:30 pm | State Quarterfinals |
| Sat., 11/9 | V Girls Cross Country | New England Championship | Away - Derryfield Park-Manchester, NH [Directions] | TBA | ||
| Sat., 11/9 | V Girls Swimming and Diving | CIAC Class S Qualifying | Away - Plainville HS [Directions] | 2:00 p.m. | 11:30 am | |
| Mon., 11/11 | JV Football | Pomperaug | Away - Sports Complex & Track [Directions] | 4:00 p.m. | 2:45pm | Freshman/Sophomore game |
| Tue., 11/12 | V Girls Soccer | Haddam-Killingworth | Away [Directions] | L 0-1 | 4:00pm | State Semifinals at West Haven HS |
| Wed., 11/13 | V Girls Swimming and Diving | CIAC Class S Finals | Away - Wesleyan Univ. [Directions] | 7:00 p.m. | ||
| Fri., 11/15 | V Football | Masuk | Away - Masuk Stadium Field [Directions] | L 14-39 | 4:30pm | Cheer bus at 5:30pm |
| Fri., 11/15 | V Girls Swimming and Diving | CIAC Open Diving | Away - Plainville HS [Directions] | 5:30 p.m. | ||
| Sat., 11/16 | JV Football | Masuk | Home - WHS Stadium Field [Directions] | 10:00 a.m. | Freshman/Sophomore game | |
| Sat., 11/16 | V Girls Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 12:00 p.m. | ||
| Sat., 11/23 | JV Football | Joel Barlow | Home - WHS Stadium Field [Directions] | 11:00 a.m. | 2:45pm | Freshman/Sophomore game |
| Thu., 11/28 | V Football | Joel Barlow | Home - WHS Stadium Field [Directions] | L 14-46 | ||
| Wed., 12/4 | V Girls Basketball | Darien (Scrim.) | Home - WHS Gymnasium [Directions] | 3:45 p.m. | ||
| Fri., 12/6 | V Boys Ice Hockey | Staples (Scrim.) | Away - Milford Ice Pavilion [Directions] | 8:00 p.m. | ||
| Sat., 12/7 | V Boys Basketball | Wilton (Scrim.) | Home - WHS Gymnasium [Directions] | 2:00 p.m. | JV and Varsity in one gym | |
| Sat., 12/7 | V Wrestling | Norwalk (Scrim.) | Away - Norwalk High Gym [Directions] | 9:00 a.m. | 8:30am | |
| Sat., 12/7 | V Girls Basketball | New Canaan (Scrim.) | Home - WHS Gymnasium [Directions] | 11:00 a.m. | ||
| Mon., 12/9 | V Girls Basketball | Trinity Catholic (Scrim.) | Home - WHS Gymnasium [Directions] | 3:15 p.m. | ||
| Wed., 12/11 | V Boys Basketball | Norwalk (Scrim.) | Away - Norwalk High Gym [Directions] | 4:00 p.m. | 4:00pm | |
| Wed., 12/11 | V Wrestling | Staples (Scrim.) | Away [Directions] | 3:00 p.m. | 2:45pm | |
| Thu., 12/12 | V Boys Ice Hockey | Ossining/Sleepy Hollow/Irvington (NY) (Scrim.) | Home - Danbury Ice Arena [Directions] | 7:50 p.m. | ||
| Sat., 12/14 | V Boys Basketball | Fairfield Ludlowe (Scrim.) | Away [Directions] | 10:00 a.m. | 8:45am | |
| Sat., 12/14 | V Wrestling | Westhill, Masuk, Greenwich, Harding/Bassick/Bridgeport Central (Scrim.) | Away - Wrestling Room [Directions] | Cancelled | 8:15am | |
| Mon., 12/16 | V Boys Basketball | Cheshire (Scrim.) | Away - Cheshire Academy [Directions] | 05:00 p.m. | 4:20pm | |
| Wed., 12/18 | V Boys Ice Hockey | Housatonic Coop | Home - Danbury Ice Arena [Directions] | L 1-4 | ||
| Wed., 12/18 | V Wrestling | New Fairfield | Away - NFHS Gym [Directions] | New Fairfield 46 Weston 18 | 4:00pm | |
| Wed., 12/18 | V Girls Basketball | New Fairfield | Away - NFHS Gym [Directions] | L 24-53 | 3:45pm | |
| Wed., 12/18 | JV Girls Basketball | New Fairfield | Away - WHS Gymnasium [Directions] | 5:15 p.m. | 3:45pm | |
| Thu., 12/19 | V Girls Basketball | Bethel | Home - WHS Gymnasium [Directions] | L 31-60 | ||
| Thu., 12/19 | JV Girls Basketball | Bethel | Home - WHS Gymnasium [Directions] | 5:15 p.m. | ||
| Thu., 12/19 | V Girls Gymnastics | Staples, Greenwich, Joel Barlow | Away [Directions] | Staples 125.65 Greenwich 120.65 Joel Barlow 101.8 Weston 89.35 | 4:30pm | |
| Fri., 12/20 | V Boys Indoor Track | New Haven Varsity Invite | Away | 4:00 p.m. | 2:00 pm | 1 bus |
| Fri., 12/20 | V Girls Indoor Track | New Haven Varsity Invite | Away | 4:00 p.m. | 2:00 pm | 1 bus |
| Sat., 12/21 | V Boys Basketball | Bristol Central | Home - WHS Gymnasium [Directions] | L 55-58 | Non League | |
| Sat., 12/21 | JV Boys Basketball | Bristol Central | Home - WHS Gymnasium [Directions] | 3:45 p.m. | ||
| Sat., 12/21 | FR Boys Basketball | Bristol Central | Home - WHS Gymnasium [Directions] | 2:00 p.m. | ||
| Sat., 12/21 | V Boys Ice Hockey | Masuk | Away - The Rinks at Shelton [Directions] | L 0-8 | ||
| Sat., 12/21 | V Boys Indoor Track | Reindeer Relays | Away [Directions] | 9:30 a.m. | 7:45 am | at Wilton-2 buses |
| Sat., 12/21 | V Wrestling | Shelton Invitational | Away [Directions] | 9:00 a.m. | 7:30am | |
| Sat., 12/21 | V Girls Basketball | Windsor | Home - WHS Gymnasium [Directions] | L 31-53 | Non League | |
| Sat., 12/21 | JV Girls Basketball | Windsor | Home - WHS Old Gym [Directions] | 5:30 p.m. | ||
| Sat., 12/21 | V Girls Indoor Track | Reindeer Relays | Away [Directions] | 9:30 a.m. | 7:45 am | at Wilton-2 buses |
| Mon., 12/23 | V Boys Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | L 36-67 | 2:45pm | Non League |
| Mon., 12/23 | JV Boys Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 4:15 p.m. | 2:45pm | |
| Mon., 12/23 | FR Boys Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 2:30 p.m. | 1:00pm | |
| Mon., 12/23 | V Boys Ice Hockey | Eastern CT Eagles | Away - Connecticut College [Directions] | W 4-1 | ||
| Mon., 12/23 | V Girls Basketball | Branford | Away - James L MacVeigh Alumni Athletic Complex - Gym [Directions] | L 24-47 | 2:45pm | Non League |
| Mon., 12/23 | JV Girls Basketball | Branford | Away - James L MacVeigh Alumni Athletic Complex - Gym [Directions] | 5:15 p.m. | 2:45pm | |
| Fri., 12/27 | V Boys Basketball | Brien McMahon | Home - WHS Gymnasium [Directions] | W 54-52 | Holiday Tournament | |
| Fri., 12/27 | V Boys Ice Hockey | Lyman Hall | Away - Northford Ice Pavillion [Directions] | L 0-4 | ||
| Fri., 12/27 | V Girls Basketball | Northwestern | Home - WHS Gymnasium [Directions] | L 22-40 | Non League | |
| Fri., 12/27 | JV Girls Basketball | Northwestern | Home - WHS Gymnasium [Directions] | 2:15 p.m. | ||
| Sat., 12/28 | V Boys Basketball | Stamford | Home - WHS Gymnasium [Directions] | W 44-36 | Consolation game at 6pm, Championships at 8pm | |
| Sat., 12/28 | V Boys Ice Hockey | Alumni Game | Home - Danbury Ice Arena [Directions] | 7:50 p.m. | ||
| Sat., 12/28 | V Boys Indoor Track | JV/V Developmental Meet | Away - Danbury Sports Dome | 09:00 a.m. | 7:45 am | |
| Sat., 12/28 | V Wrestling | Fairfield Prep | Home [Directions] | Weston 14; Fairfield Prep 66 | ||
| Sat., 12/28 | V Girls Indoor Track | JV/V Developmental Meet | Away - Danbury Sports Dome | 9:00 a.m. | 7:45 am | |
| Sat., 1/4 | V Boys Ice Hockey | Eastern CT Eagles | Home - Wonderland of Ice - Bridgeport [Directions] | W 6-5 (OT) | ||
| Sat., 1/4 | V Boys Indoor Track | SWC League Meet | Away | 9:00 a.m. | 7:00am | at Wesleyan-2 buses |
| Sat., 1/4 | V Wrestling | Norwalk JV Tournament | Away | 9:00 a.m. | 8:30am | |
| Sat., 1/4 | V Girls Gymnastics | Pompersug Invite | Away | 131.55 2nd/13 teams | TBA | |
| Sat., 1/4 | V Girls Indoor Track | SWC League Meet | Away | 9:00 a.m. | 7:o00 am | at Wesleyan-2 buses |
| Mon., 1/6 | V Girls Gymnastics | Staples | Away [Directions] | Ludlowe- 130.55 Staples- 124.55 | @ Gymnastics and Cheer Academy | |
| Tue., 1/7 | V Boys Basketball | Old Lyme | Away - Old Lyme High School [Directions] | W 54-39 | 3:15pm | Non League |
| Tue., 1/7 | JV Boys Basketball | Old Lyme | Away - Old Lyme High School [Directions] | 5:30 p.m. | 3:15pm | |
| Tue., 1/7 | V Girls Basketball | Lauralton Hall | Home - WHS Gymnasium [Directions] | L 10-77 | ||
| Tue., 1/7 | JV Girls Basketball | Lauralton Hall | Home - WHS Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 1/8 | V Boys Ice Hockey | Lyman Hall | Home - Wonderland of Ice - Bridgeport [Directions] | L 3-5 | ||
| Wed., 1/8 | V Boys Indoor Track | JV Developmental Meet | Away - Danbury Sports Dome | 03:00 p.m. | 2:45 pm | |
| Wed., 1/8 | V Wrestling | Bethel | Home - WHS Gymnasium [Directions] | Bethel 51 Weston 24 | ||
| Wed., 1/8 | V Girls Basketball | Notre Dame-Fairfield | Away - Sister Marion Rielly Auditorium at Notre Dame [Directions] | L 21-44 | 4:00pm | |
| Wed., 1/8 | JV Girls Basketball | Notre Dame-Fairfield | Away - Sister Marion Rielly Auditorium at Notre Dame [Directions] | 5:15 p.m. | 4:00pm | |
| Wed., 1/8 | V Girls Gymnastics | Trumbull | Home - Gymnastics & Cheer Academy 85 Mill Plain Rd, Fairfield [Directions] | Ludlowe- 131.85 Trumbull- 131.95 | @ Gymnastics and Cheer Academy | |
| Wed., 1/8 | V Girls Indoor Track | JV Developmental Meet | Away - Danbury Sports Dome | 3:00 p.m. | 2:40 pm | |
| Thu., 1/9 | FR Boys Basketball | Newtown | Home - WHS Gymnasium [Directions] | 3:30 p.m. | ||
| Thu., 1/9 | V Boys Swimming and Diving | Joel Barlow-Bethel Swim | Away - Western CT State University - O'Neill Center [Directions] | Weston 91 Joel Barlow 85 | 5:15pm | |
| Thu., 1/9 | V Girls Basketball | New Fairfield | Home - WHS Gymnasium [Directions] | L 31-55 | Non League | |
| Thu., 1/9 | JV Girls Basketball | New Fairfield | Home - WHS Gymnasium [Directions] | 5:15 p.m. | Non League | |
| Thu., 1/9 | V Girls Gymnastics | Foran, Joel Barlow | Away [Directions] | Foran 112.25 Weston 110.85 | 4:30pm | |
| Fri., 1/10 | V Boys Basketball | Notre Dame-Fairfield | Home - WHS Gymnasium [Directions] | L 61-62 | ||
| Fri., 1/10 | JV Boys Basketball | Notre Dame-Fairfield | Home - WHS Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/10 | V Boys Ice Hockey | Housatonic Coop | Away - Hotchkiss [Directions] | L 1-2 | ||
| Sat., 1/11 | JV Boys Ice Hockey | Newtown/New Fairfield | Home - Danbury Ice Arena [Directions] | 8:10 p.m. | ||
| Sat., 1/11 | V Boys Indoor Track | SCC Invite | Away [Directions] | 2:30 p.m. | 12:45pm | at Hillhouse |
| Sat., 1/11 | V Wrestling | Canton Duals | Away [Directions] | Weston 48 Gilbert 30 Canton 49 Weston 28 | 7:00am | |
| Sat., 1/11 | V Girls Gymnastics | Darien, Joel Barlow, Trumbull | Away - DARIEN YMCA [Directions] | Trumbull 133.45 Darien 124.85 Joel Barlow 114.75 Weston 98.4 | 12:45pm | at Darien YMCA |
| Sat., 1/11 | V Girls Indoor Track | SCC Invite | Away [Directions] | 9:00 a.m. | 6:45 am | at Hillhouse- 1 bus |
| Mon., 1/13 | V Wrestling | Brookfield/Shepaug | Away - BHS Small Gym [Directions] | Weston 66 Brookfield 6 | 3:00pm | |
| Tue., 1/14 | V Boys Basketball | New Milford | Home - WHS Gymnasium [Directions] | W 69-39 | ||
| Tue., 1/14 | JV Boys Basketball | New Milford | Home - WHS Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/14 | FR Boys Basketball | New Milford | Home - WHS Gymnasium [Directions] | 3:30 p.m. | ||
| Tue., 1/14 | V Boys Swimming and Diving | Brookfield | Home - Weston Middle School Pool [Directions] | Brookfield 99 Weston 85 | ||
| Tue., 1/14 | V Girls Basketball | New Milford | Away - New Milford High School [Directions] | L 14-47 | 3:45pm | |
| Tue., 1/14 | JV Girls Basketball | New Milford | Away - New Milford High School [Directions] | 5:15 p.m. | 3:45pm | |
| Tue., 1/14 | V Girls Gymnastics | Pomperaug, Nonnewaug, Joel Barlow | Away - Auxiliary Gym [Directions] | Pomperaug 127.2 Nonnewaug 126.16 Joel Barlow 105.59 Weston 83.45 | 4:00pm | |
| Wed., 1/15 | V Boys Indoor Track | JV Developmental Meet | Away - Danbury Sports Dome | 3:00 p.m. | 2:40 pm | |
| Wed., 1/15 | V Wrestling | Oxford | Away - OHS-Main Gym [Directions] | Oxford 66 Weston 12 | 4:00pm | |
| Wed., 1/15 | V Girls Basketball | Branford | Home - WHS Gymnasium [Directions] | L 21-43 | Non League | |
| Wed., 1/15 | JV Girls Basketball | Branford | Home - WHS Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 1/15 | V Girls Indoor Track | JV Developmental Meet | Away - Danbury Sports Dome | 3:00 p.m. | 2:40 pm | |
| Fri., 1/17 | V Boys Basketball | Brookfield | Away - BHS Big Gym [Directions] | W 56-44 | 3:45pm | |
| Fri., 1/17 | JV Boys Basketball | Brookfield | Away - BHS Big Gym [Directions] | 5:15 p.m. | 3:45pm | |
| Fri., 1/17 | FR Boys Basketball | Brookfield | Away - BHS Big Gym [Directions] | 3:45 p.m. | 2:40pm | |
| Fri., 1/17 | V Boys Indoor Track | Yale Classic | Away | 1:00 p.m. | 11:15am | at Yale, varsity only |
| Fri., 1/17 | V Boys Swimming and Diving | New Fairfield | Away - New Fairfield HS [Directions] | New Fairfield 94 Weston 91 | 2:45pm | |
| Fri., 1/17 | V Girls Basketball | Brookfield | Home - WHS Gymnasium [Directions] | L 27-45 | ||
| Fri., 1/17 | JV Girls Basketball | Brookfield | Home - WHS Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/17 | V Girls Indoor Track | Yale Classic | Away | 1:00 p.m. | 11:15am | at Yale, varsity only |
| Sat., 1/18 | V Boys Ice Hockey | Shepaug Valley Ice Hockey | Home - Danbury Ice Arena [Directions] | L 3-4 | ||
| Sat., 1/18 | V Boys Indoor Track | Yale Classic | Away | TBA | at Yale, varsity only | |
| Sat., 1/18 | V Wrestling | New Milford Tournament | Away [Directions] | 9:30 a.m. | 7:15am | |
| Sat., 1/18 | V Girls Gymnastics | Darien, Fairfield Warde | Away - DARIEN YMCA [Directions] | Cancelled | PUFL:12:30 RE:3:30 | |
| Sat., 1/18 | V Girls Indoor Track | Yale Classic | Away | TBA | at Yale, varsity only-no bus | |
| Mon., 1/20 | V Boys Indoor Track | SWC League Meet | Away | 9:00 a.m. | 7:00am | at Wesleyan-2 buses |
| Mon., 1/20 | V Girls Gymnastics | Fairfield Warde | Away - Gymnastics & Cheer Academy 85 Mill Plain Rd, Fairfield [Directions] | Ludlowe- 134.85 Warde- 130.75 | ||
| Mon., 1/20 | V Girls Indoor Track | SWC League Meet | Away | 9:00 a.m. | 7:00 am | at Wesleyan-2 buses |
| Wed., 1/22 | V Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena [Directions] | L 2-3 | ||
| Wed., 1/22 | V Boys Indoor Track | JV Developmental Meet | Away - Danbury Sports Dome | 3:00 p.m. | 2:40 pm | |
| Wed., 1/22 | V Girls Indoor Track | JV Developmental Meet | Away - Danbury Sports Dome | 3:00 a.m. | 2:40 pm | |
| Thu., 1/23 | V Boys Basketball | Pomperaug | Away - PHS Main Gym [Directions] | W 68-65 | 3:45pm | |
| Thu., 1/23 | JV Boys Basketball | Pomperaug | Away - PHS Main Gym [Directions] | 5:15 p.m. | 3:45pm | |
| Thu., 1/23 | FR Boys Basketball | Pomperaug | Away - PHS Main Gym [Directions] | 3:30 p.m. | 2:40pm | |
| Thu., 1/23 | V Wrestling | Joel Barlow | Home - WHS Gymnasium [Directions] | Weston 15 Immaculate/Joel Barlow 57 | ||
| Thu., 1/23 | V Girls Gymnastics | Wilton | Away - Wilton High School Aux. Gym [Directions] | Ludlowe- 139.00 Wilton- 139.40 | PUFW:2:20 PUFL:2:35 RE:5:30 | |
| Fri., 1/24 | V Boys Swimming and Diving | Watertown | Away - Frank M. Reinhold Pool @ Watertown High School [Directions] | Weston 94 Watertown 90 | 2:45pm | |
| Fri., 1/24 | V Girls Basketball | Pomperaug | Home - WHS Gymnasium [Directions] | L 27-70 | ||
| Fri., 1/24 | JV Girls Basketball | Pomperaug | Home - WHS Gymnasium [Directions] | 5:15 p.m. | ||
| Sat., 1/25 | V Boys Indoor Track | SWC Last Chance Invite | Away [Directions] | 6:00 p.m. | 5:00pm | at Wilton |
| Sat., 1/25 | V Wrestling | Staples Duals | Away [Directions] | 10:00 a.m. | 8:45am | |
| Sat., 1/25 | V Girls Indoor Track | SWC Last Chance Invite | Away [Directions] | 6:00 p.m. | 5:00pm | at Wilton |
| Mon., 1/27 | V Boys Basketball | Kolbe Cathedral | Home - WHS Gymnasium [Directions] | W 60-55 | ||
| Mon., 1/27 | JV Boys Basketball | Kolbe Cathedral | Home - WHS Gymnasium [Directions] | 5:15 p.m. | ||
| Mon., 1/27 | V Boys Ice Hockey | Shepaug Valley Ice Hockey | Away - Gunnery Rink [Directions] | W 3-2 | ||
| Mon., 1/27 | V Boys Indoor Track | JV Developmental Meet | Away - Danbury Sports Dome | Cancelled | 2:40 pm | |
| Mon., 1/27 | V Girls Gymnastics | New Canaan, Westhill | Home - Gymnastics Cheer Academy [Directions] | Ludlowe- 128.10, Westhill- 98.7, New Canaan- 96.3 | ||
| Mon., 1/27 | V Girls Indoor Track | JV Developmental Meet | Away - Danbury Sports Dome | Cancelled | 2:40 pm | |
| Tue., 1/28 | V Boys Basketball | Stratford | Away - Needham Memorial Gymnasium [Directions] | W 62-53 | 3:45pm | |
| Tue., 1/28 | JV Boys Basketball | Stratford | Away - Needham Memorial Gymnasium [Directions] | 5:15 p.m. | 3:45pm | |
| Tue., 1/28 | FR Boys Basketball | Stratford | Away [Directions] | 3:30 p.m. | 2:40pm | |
| Tue., 1/28 | V Boys Swimming and Diving | Newtown | Home - Weston Middle School Pool [Directions] | Weston 94 Newtown 91 | ||
| Tue., 1/28 | V Girls Basketball | Stratford | Home - WHS Gymnasium [Directions] | L 40-49 | ||
| Tue., 1/28 | JV Girls Basketball | Stratford | Home - WHS Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 1/29 | V Boys Ice Hockey | New Fairfield | Home - Danbury Ice Arena [Directions] | L 0-5 | ||
| Wed., 1/29 | V Wrestling | Stratford | Home - WHS Gymnasium [Directions] | Stratford 53 Weston 30 | ||
| Thu., 1/30 | V Boys Swimming and Diving | New Milford | Home - Weston Middle School Pool [Directions] | 4:00 p.m. | ||
| Fri., 1/31 | V Boys Basketball | Immaculate | Home - WHS Gymnasium [Directions] | W 59-50 | ||
| Fri., 1/31 | JV Boys Basketball | Immaculate | Home - WHS Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/31 | FR Boys Basketball | Immaculate | Home - WHS Gymnasium [Directions] | 3:30 p.m. | ||
| Fri., 1/31 | V Girls Basketball | Immaculate | Away - Immaculate High School [Directions] | L 20-44 | 3:45pm | |
| Fri., 1/31 | JV Girls Basketball | Immaculate | Away - Immaculate High School [Directions] | 5:15 p.m. | 3:45pm | |
| Fri., 1/31 | V Girls Gymnastics | Joel Barlow | Home - Wilton YMCA [Directions] | Weston 109.9 Joel Barlow 58.5 | ||
| Sat., 2/1 | V Boys Ice Hockey | Masuk | Home - Danbury Ice Arena [Directions] | L 0-7 | ||
| Sat., 2/1 | V Boys Indoor Track | SWC Championship Meet | Away [Directions] | 5:00 p.m. | 3:00pm | at Hillhouse-2 buses |
| Sat., 2/1 | V Wrestling | Bunnell | Home - WHS Gymnasium [Directions] | Weston 33 Bunnell 29 | ||
| Sat., 2/1 | V Girls Basketball | Kolbe Cathedral | Away - Shehan Center [Directions] | L 18-57 | 1:45pm | |
| Sat., 2/1 | JV Girls Basketball | Kolbe Cathedral | Away - Shehan Center [Directions] | 3:00 p.m. | 1:45pm | |
| Sat., 2/1 | V Girls Indoor Track | SWC Championship Meet | Away [Directions] | 5:00 p.m. | 3:00 pm | at Hillhouse-2 buses |
| Tue., 2/4 | V Boys Basketball | Joel Barlow | Away - Lower Gym [Directions] | W 73-67 | 4:00pm | |
| Tue., 2/4 | JV Boys Basketball | Joel Barlow | Away - Lower Gym [Directions] | 5:15 p.m. | 4:00pm | |
| Tue., 2/4 | FR Boys Basketball | Joel Barlow | Away - Lower Gym [Directions] | 3:30 p.m. | 2:45pm | |
| Tue., 2/4 | V Boys Swimming and Diving | Oxford | Away - OHS Pool [Directions] | 4:30 p.m. | 2:45pm | |
| Tue., 2/4 | V Girls Basketball | Joel Barlow | Home - WHS Gymnasium [Directions] | L 18-42 | ||
| Tue., 2/4 | JV Girls Basketball | Joel Barlow | Home - WHS Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 2/4 | V Girls Gymnastics | New Milford, Oxford, Newtown, Joel Barlow | Away - New Milford High School [Directions] | New Milford 127.6 Newtown 127.6 Weston 113.4 Joel Barlow 81.4 Oxford 74.95 | 4:00pm | |
| Thu., 2/6 | V Wrestling | Pomperaug Coop | Away - Auxiliary Gym [Directions] | Pomperaug 45 Weston 27 | 4:00pm | |
| Thu., 2/6 | V Girls Basketball | Newtown | Away - Newtown High School Gymnasium [Directions] | L 20-41 | 4:00pm | |
| Thu., 2/6 | V Girls Gymnastics | Wilton, Joel Barlow | Away - Wilton High School Aux. Gym [Directions] | Wilton 134.80 Weston 115.05 Joel Barlow 82.1 | 4:30pm | |
| Fri., 2/7 | V Boys Basketball | Newtown | Home - WHS Gymnasium [Directions] | W 52-50 | ||
| Fri., 2/7 | JV Boys Basketball | Newtown | Home - WHS Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 2/7 | FR Boys Basketball | Newtown | Home - WHS Gymnasium [Directions] | 3:30 p.m. | ||
| Fri., 2/7 | V Boys Indoor Track | Class M Championships | Away [Directions] | 4:00 p.m. | 1:30 pm | 1 bus |
| Fri., 2/7 | V Girls Indoor Track | Class M Championships | Away [Directions] | 4:00 p.m. | 1:30 pm | at Hillhouse-1 bus |
| Sat., 2/8 | V Boys Ice Hockey | New Milford | Home - Danbury Ice Arena [Directions] | L 1-10 | ||
| Sat., 2/8 | V Wrestling | Ludlowe JV Tournament | Away [Directions] | 9:00 a.m. | 7:45am | |
| Mon., 2/10 | V Boys Basketball | Bunnell | Away - Bunnell [Directions] | L 49-79 | 3:45pm | |
| Mon., 2/10 | JV Boys Basketball | Bunnell | Away - Bunnell [Directions] | 5:15 p.m. | 3:45pm | |
| Mon., 2/10 | FR Boys Basketball | Bunnell | Away - Bunnell [Directions] | 3:45 p.m. | 2:40pm | |
| Mon., 2/10 | V Boys Ice Hockey | Byram Hills (NY) | Home - Danbury Ice Arena [Directions] | W 4-3 | ||
| Mon., 2/10 | V Girls Basketball | Bunnell | Home - WHS Gymnasium [Directions] | L 25-63 | ||
| Mon., 2/10 | JV Girls Basketball | Bunnell | Home - WHS Gymnasium [Directions] | 5:15 p.m. | ||
| Mon., 2/10 | V Girls Gymnastics | Foran | Away - Foran High School [Directions] | Ludlowe- 123.60 Foran- 105.10 | PUFW:4:15 PUFL:4:30 RE:8:00 | |
| Tue., 2/11 | V Boys Swimming and Diving | Bethel | Home - Weston Middle School Pool [Directions] | weston 98 Bethel 82 | ||
| Tue., 2/11 | V Wrestling | Newtown | Home - WHS Gymnasium [Directions] | Newtown 72 Weston 3 | ||
| Tue., 2/11 | V Girls Gymnastics | New Milford, Lauralton Hall, Joel Barlow | Away - New Milford High School [Directions] | New Milford 135.5 Weston 125 Joel Barlow 62.4 | 4:00pm | |
| Tue., 2/11 | V Girls Gymnastics | Greenwich | Home - Gymnastics Cheer Academy [Directions] | Ludlowe- 125.85 Greenwich- 124.80 | ||
| Wed., 2/12 | V Boys Ice Hockey | Sheehan | Home - Danbury Ice Arena [Directions] | L 4-7 | ||
| Wed., 2/12 | V Boys Swimming and Diving | Bunnell-Stratford | Away - Flood Middle School [Directions] | Weston 85 Bunnell/Stratford 76 | 3:15pm | |
| Sat., 2/15 | V Girls Gymnastics | FCIAC Championship @ Westhill | Away | 2nd- 132.05 | PUFL:9:00 REPU:1:00 | @ Westhill HS |
| Sun., 2/16 | V Wrestling | SWC Tournament | Away [Directions] | 12:30 p.m. | 9:15am | at Pomperaug, 10:30 weigh in |
| Mon., 2/17 | JV Boys Ice Hockey | Wilton | Away - Winter Garden Rink-Ridgefield [Directions] | 4:00 p.m. | ||
| Mon., 2/17 | V Boys Indoor Track | State Open | Away [Directions] | 3:00 p.m. | 12:45pm | 1 bus |
| Mon., 2/17 | V Girls Indoor Track | State Open | Away [Directions] | 3:00 p.m. | 12:45pm | at Hillhouse-1 bus |
| Wed., 2/19 | V Boys Ice Hockey | Norwalk | Away - SoNo Ice House [Directions] | L 2-3 | ||
| Wed., 2/19 | V Boys Swimming and Diving | Masuk | Home - Weston Middle School Pool [Directions] | 4:00 p.m. | ||
| Wed., 2/19 | V Girls Basketball | Masuk | Home - WHS Gymnasium [Directions] | L 31-46 | ||
| Wed., 2/19 | JV Girls Basketball | Masuk | Home - WHS Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 2/19 | V Girls Gymnastics | SWC Championship Meet | Away [Directions] | 120.1 | 3:30pm | at New Milford |
| Thu., 2/20 | V Boys Basketball | Ridgefield | Away - RHS Main Gym [Directions] | L 50-65 | 3:45pm | Non league |
| Thu., 2/20 | JV Boys Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 5:15 p.m. | 3:45pm | |
| Thu., 2/20 | FR Boys Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | 2:45pm | |
| Thu., 2/20 | V Girls Gymnastics | New Milford, Wilton | Away - New Milford High School [Directions] | Ludlowe- 128.8 New Milford- 122.55 | PU:2:45 RE:6:30 | |
| Fri., 2/21 | V Boys Basketball | Bethel | Away - Bethel High School [Directions] | W 81-71 | 3:45pm | |
| Fri., 2/21 | JV Boys Basketball | Bethel | Away [Directions] | 5:15 p.m. | 3:45pm | |
| Fri., 2/21 | FR Boys Basketball | Bethel | Away - Bethel High School [Directions] | 3:45 p.m. | 2:40pm | |
| Fri., 2/21 | V Wrestling | Class S State Tournament | Away [Directions] | 4:30 p.m. | 1:15pm (drop off only) | at Windham |
| Fri., 2/21 | V Girls Basketball | Oxford | Away - OHS-Main Gym [Directions] | L 21-46 | 11:30am | |
| Fri., 2/21 | JV Girls Basketball | Oxford | Away - OHS-Main Gym [Directions] | 5:15 p.m. | 3:45pm | |
| Fri., 2/21 | V Girls Gymnastics | Daniel Hand | Away - Polson Gymnastics Gym/DHHS Campus [Directions] | Ludlowe- 132.05 Hand- 136.0 | PU:3:15 RE:7:30 | |
| Sat., 2/22 | V Boys Basketball | Masuk | Away - David Strong Gymnasium @ Masuk High School [Directions] | L 66-82 | 2:45pm | |
| Sat., 2/22 | JV Boys Basketball | Masuk | Away - David Strong Gymnasium @ Masuk High School [Directions] | 4:15 p.m. | 2:45pm | |
| Sat., 2/22 | FR Boys Basketball | Masuk | Away - David Strong Gymnasium @ Masuk High School [Directions] | 2:30 p.m. | 1:15pm | |
| Sat., 2/22 | V Boys Ice Hockey | Woodstock Academy | Away - Jahn Hockey Rink - Pomfret School [Directions] | L 5-6 (OT) | ||
| Sat., 2/22 | V Wrestling | Class S State Tournament | Away [Directions] | 9:15 a.m. | 12:00pm (pick up at Windham) | at Windham |
| Sat., 2/22 | V Girls Basketball | SWC Quarterfinals | Away | TBA | TBA | |
| Mon., 2/24 | V Boys Basketball | Oxford | Home - WHS Gymnasium [Directions] | W 86-33 | ||
| Mon., 2/24 | JV Boys Basketball | Oxford | Home - WHS Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 2/25 | V Boys Basketball | New Fairfield | Home - WHS Gymnasium [Directions] | L 45-60 | ||
| Tue., 2/25 | JV Boys Basketball | New Fairfield | Home - WHS Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 2/25 | FR Boys Basketball | New Fairfield | Home - WHS Gymnasium [Directions] | 3:30 p.m. | ||
| Tue., 2/25 | V Boys Swimming and Diving | Pomperaug | Home - Weston Middle School Pool [Directions] | Pomperaug 97 Weston 78 | ||
| Tue., 2/25 | V Girls Basketball | SWC Semifinals | Away | TBA | TBA | |
| Thu., 2/27 | V Girls Basketball | SWC Championship Game | Away | TBA | ||
| Fri., 2/28 | V Boys Ice Hockey | Newtown/New Fairfield | Home - Danbury Ice Arena [Directions] | L 3-5 | ||
| Fri., 2/28 | V Wrestling | CIAC State Open Tournament | Away [Directions] | 4:30 p.m. | at New Haven Athletic Center | |
| Sat., 3/1 | V Boys Basketball | Pomperaug | Away [Directions] | W 61-57 | 10:15am | SWC Quarterfinals at Bunnell |
| Sat., 3/1 | V Boys Ice Hockey | Sheehan | Away - Choate Rosemary Hall [Directions] | L 3-9 | ||
| Sat., 3/1 | V Boys Indoor Track | NE Championships | Away | TBA | Reggie Lewis Center, Boston | |
| Sat., 3/1 | V Wrestling | CIAC State Open Tournament | Away [Directions] | 9:15 a.m. | at New Haven Athletic Center | |
| Tue., 3/4 | V Boys Basketball | Bunnell | Away [Directions] | L 45-46 | 4:00pm | SWC Semifinals at Newtown |
| Tue., 3/4 | V Boys Ice Hockey | Norwalk | Away - SoNo Ice House [Directions] | L 2-6 | ||
| Wed., 3/5 | V Boys Swimming and Diving | SWC Dive Championships | Away [Directions] | 6:00 p.m. | at New Fairfield warm ups at 4:30pm | |
| Thu., 3/6 | V Boys Basketball | SWC Championship Game | Away [Directions] | Cancelled | ||
| Fri., 3/7 | V Boys Swimming and Diving | SWC Swim Championships | Away [Directions] | 6:00 p.m. | 3:00pm | at Masuk warm up at 4:00pm |
| Fri., 3/7 | V Wrestling | New England Championships | Away | 4:30 p.m. | at Providence RI | |
| Sat., 3/8 | V Wrestling | New England Championships | Away | 9:15 a.m. | at Providence RI | |
| Tue., 3/11 | V Boys Basketball | Joel Barlow | Home - WHS Gymnasium [Directions] | L 46-49 | ||
| Wed., 3/12 | V Boys Swimming and Diving | CIAC Class S Diving Trials/Finals | Away - Plainville HS [Directions] | 5:30 p.m. | ||
| Sat., 3/15 | V Boys Swimming and Diving | CIAC Class S Qualifying | Away - Plainville HS [Directions] | 3:30 p.m. | 11:30 AM | |
| Tue., 3/18 | V Boys Swimming and Diving | CIAC Class S Finals | Away - Wesleyan Univ. [Directions] | 7:15 p.m. | 3:15 PM | at Wesleyan |
| Thu., 3/20 | V Boys Swimming and Diving | CIAC Open Diving | Away - Middletown [Directions] | 5:30 p.m. | ||
| Sat., 3/22 | V Boys Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 2:30 p.m. | ||
| Thu., 3/27 | V Girls Lacrosse | Staples (Scrim.) | Home - WHS Turf Field [Directions] | 3:30 p.m. | ||
| Sat., 3/29 | V Boys Lacrosse | Preseason Play Day | Home - WHS Turf Field [Directions] | 9:00 a.m. | 6 teams using both turf fields from 9 - 1 pm | |
| Tue., 4/1 | V Baseball | Brien McMahon (Scrim.) | Home - Revson Field, Weston [Directions] | 3:30 p.m. | ||
| Tue., 4/1 | V Boys Lacrosse | Fairfield Warde (Scrim.) | Away - Tetreau/Davis Field [Directions] | 4:00 p.m. | 2:45pm | |
| Tue., 4/1 | JV Boys Lacrosse | Fairfield Warde (Scrim.) | Away - Tetreau/Davis Field [Directions] | 5:30 p.m. | 2:45pm | |
| Wed., 4/2 | V Baseball | Fairfield Ludlowe (Scrim.) | Away - Kiwanis Field [Directions] | 3:45 p.m. | 2:45pm | |
| Wed., 4/2 | V Softball | Norwalk (Scrim.) | Away - Ray Barry Field, NHS [Directions] | 3:45 p.m. | 2:40pm | |
| Thu., 4/3 | V Boys Lacrosse | Wilton (Scrim.) | Home - WHS Turf Field [Directions] | 4:45 p.m. | varsity and JV | |
| Thu., 4/3 | V Softball | Trinity Catholic (Scrim.) | Home - Hurlbutt El. School, Weston [Directions] | 4:15 p.m. | ||
| Fri., 4/4 | V Boys Tennis | Ridgefield (Scrim.) | Away - RHS Tennis Courts [Directions] | 3:45 p.m. | 2:40pm | |
| Fri., 4/4 | V Girls Tennis | Ridgefield (Scrim.) | Home - WHS Tennis Courts [Directions] | 3:45 p.m. | ||
| Sat., 4/5 | V Boys Lacrosse | Glastonbury (Scrim.) | Away [Directions] | 9:00 a.m. | 7:15am | |
| Sat., 4/5 | V Girls Lacrosse | Stamford (Scrim.) | Home - WHS Turf Field [Directions] | 1:00 p.m. | varsity and JV alternating periods | |
| Sat., 4/5 | JV Girls Lacrosse | Stamford (Scrim.) | Home - WHS Turf Field [Directions] | Cancelled | ||
| Sat., 4/5 | V Softball | Shepaug Valley (Scrim.) | Away - Dick Ayer Field [Directions] | 12:00 p.m. | ||
| Mon., 4/7 | V Boys Lacrosse | Norwalk (Scrim.) | Home - WHS Turf Field [Directions] | 04:45 p.m. | ||
| Mon., 4/7 | JV Boys Lacrosse | Norwalk (Scrim.) | Home - WHS Stadium Field [Directions] | 4:45 p.m. | ||
| Mon., 4/7 | V Softball | Trumbull (Scrim.) | Home - Hurlbutt El. School, Weston [Directions] | 4:00 p.m. | ||
| Wed., 4/9 | V Baseball | Wilton | Home - Revson Field, Weston [Directions] | W 7-4 | non league | |
| Wed., 4/9 | JV Baseball | Wilton | Home - Revson Field, Weston [Directions] | 4:00 p.m. | ||
| Wed., 4/9 | FR Baseball | New Fairfield | Away - NFHS Baseball Field [Directions] | 4:15 p.m. | 2:45pm | |
| Wed., 4/9 | JV Boys Golf | Pomperaug | Home - Aspetuck Valley Country Club [Directions] | 3:00 p.m. | ||
| Wed., 4/9 | V Boys Lacrosse | Staples | Home - WHS Turf Field [Directions] | L 4-12 | non league | |
| Wed., 4/9 | JV Boys Lacrosse | Staples | Home - WHS Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 4/9 | V Girls Golf | Joel Barlow | Away - Redding Country Club [Directions] | Weston 250 Joel Barlow 254 | ||
| Wed., 4/9 | V Girls Lacrosse | Lauralton Hall | Away - Lauralton Hall Field [Directions] | W 16-7 | 2:45pm | non league |
| Wed., 4/9 | JV Girls Lacrosse | Lauralton Hall | Away - Lauralton Hall Field [Directions] | 5:30 p.m. | 2:45pm | |
| Wed., 4/9 | V Girls Outdoor Track | Darien, Wilton | Home - WHS Track [Directions] | 4:00 p.m. | ||
| Wed., 4/9 | V Softball | Abbott Tech | Away - Hatters Park [Directions] | W 24-12 | 2:40pm | non league |
| Wed., 4/9 | V Girls Tennis | Newtown | Home - WHS Tennis Courts [Directions] | W 5-2 | non league | |
| Thu., 4/10 | V Boys Outdoor Track | Wilton, Darien | Away [Directions] | 4:00 p.m. | 2:45 pm | |
| Thu., 4/10 | V Boys Tennis | Amity | Home - WHS Tennis Courts [Directions] | L 0-7 | ||
| Thu., 4/10 | V Girls Golf | Masuk | Away - Whitney Farms Golf Course [Directions] | Weston 230 Masuk 261 | ||
| Thu., 4/10 | V Softball | Stratford | Home - Hurlbutt El. School, Weston [Directions] | W 11-7 | non league | |
| Fri., 4/11 | V Baseball | Platt Tech | Away - Platt Tech baseball field [Directions] | W 11-0 | 2:45pm | non league |
| Fri., 4/11 | FR Baseball | Stratford | Home - Revson Field, Weston [Directions] | 4:15 p.m. | ||
| Fri., 4/11 | V Boys Lacrosse | Bethel | Away - DeSantis Field at Bethel High School [Directions] | W 12-5 | 2:45pm | |
| Fri., 4/11 | JV Boys Lacrosse | Bethel | Away - DeSantis Field at Bethel High School [Directions] | 6:00 p.m. | 4:30pm | |
| Fri., 4/11 | V Girls Lacrosse | Pomperaug | Home - WHS Turf Field [Directions] | W 18-8 | ||
| Fri., 4/11 | JV Girls Lacrosse | Pomperaug | Home - WHS Turf Field [Directions] | 4:30 p.m. | ||
| Fri., 4/11 | V Softball | Kolbe Cathedral | Home - Hurlbutt El. School, Weston [Directions] | L 1-9 | non league | |
| Fri., 4/11 | V Girls Tennis | New Milford | Home - WHS Tennis Courts [Directions] | W 7-0 | ||
| Sat., 4/12 | V Baseball | Westhill | Away - Westhill Baseball Field [Directions] | W 4-3 | 8:00am | non league |
| Sat., 4/12 | V Girls Tennis | Staples | Home - WHS Tennis Courts [Directions] | L 2-5 | ||
| Mon., 4/14 | V Baseball | Newtown | Home - Revson Field, Weston [Directions] | W 9-5 | non league | |
| Mon., 4/14 | V Boys Golf | Immaculate | Home - Aspetuck Valley Country Club [Directions] | Weston 173 Immaculate 222 | ||
| Mon., 4/14 | V Boys Tennis | Immaculate | Home - WHS Tennis Courts [Directions] | W 7-0 | ||
| Mon., 4/14 | V Softball | Joel Barlow | Away - Field E (Softball) [Directions] | L 2-15 | 12:30pm | non league |
| Mon., 4/14 | V Girls Tennis | Immaculate | Away [Directions] | W 6-1 | 9:00am | |
| Wed., 4/16 | V Boys Tennis | Wilton | Away - WHS Tennis Courts [Directions] | L 1-6 | 12:00pm | |
| Wed., 4/16 | V Girls Tennis | Bethel | Home - WHS Tennis Courts [Directions] | W 4-3 | ||
| Thu., 4/17 | V Baseball | Newtown | Away - Newtown High School Baseball Field [Directions] | W 9-4 | 12:15pm | |
| Thu., 4/17 | JV Baseball | Bunnell | Home - Revson Field, Weston [Directions] | 3:00 p.m. | ||
| Thu., 4/17 | FR Baseball | Joel Barlow | Home - Revson Field, Weston [Directions] | 12:00 p.m. | ||
| Thu., 4/17 | V Boys Golf | New Milford | Home - Aspetuck Valley Country Club [Directions] | New Milford 182 Weston 187 | non league | |
| Thu., 4/17 | V Boys Lacrosse | Newtown | Home - WHS Turf Field [Directions] | L 2-10 | ||
| Thu., 4/17 | JV Boys Lacrosse | Newtown | Home - WHS Turf Field [Directions] | 5:45 p.m. | ||
| Thu., 4/17 | V Boys Tennis | Bethel | Away - TBA [Directions] | W 7-0 | 8:30am | |
| Thu., 4/17 | V Girls Lacrosse | Newtown | Away - Blue and Gold Stadium [Directions] | L 9-15 | 10:30am | |
| Thu., 4/17 | JV Girls Lacrosse | Newtown | Away - Blue and Gold Stadium [Directions] | 12:00 p.m. | 10:30pm | |
| Thu., 4/17 | V Softball | Newtown | Away - Newtown High School Softball Field [Directions] | L 1-14 | 12:15pm | |
| Sat., 4/19 | V Baseball | Bunnell | Home - Revson Field, Weston [Directions] | L 1-6 | Non Leage | |
| Sat., 4/19 | JV Baseball | Newtown | Home - Revson Field, Weston [Directions] | 10:00 a.m. | ||
| Sat., 4/19 | V Boys Lacrosse | North Kingstown (RI) | Home - WHS Turf Field [Directions] | W 10-6 | non league | |
| Sat., 4/19 | V Girls Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | W 21-6 | 8:45am | non league |
| Sat., 4/19 | JV Girls Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 10:00 a.m. | 8:45am | |
| Mon., 4/21 | V Baseball | Masuk | Home - Revson Field, Weston [Directions] | L 3-8 | ||
| Mon., 4/21 | FR Baseball | Bunnell | Home - Revson Field, Weston [Directions] | 4:15 p.m. | ||
| Mon., 4/21 | V Boys Golf | Notre Dame-Fairfield | Home - Aspetuck Valley Country Club [Directions] | Weston 181 Notre Dame 211 | ||
| Mon., 4/21 | V Boys Lacrosse | New Fairfield | Home - WHS Turf Field [Directions] | W 7-6 | ||
| Mon., 4/21 | JV Boys Lacrosse | New Fairfield | Home - WHS Turf Field [Directions] | 5:00 p.m. | ||
| Mon., 4/21 | V Boys Tennis | Brookfield | Home - WHS Tennis Courts [Directions] | W 7-0 | ||
| Mon., 4/21 | V Girls Golf | Bunnell | Home - Aspetuck Valley Country Club [Directions] | Weston 232 Bunnell 281 | ||
| Mon., 4/21 | V Girls Outdoor Track | Bethel, Kolbe Cathedral, Lauralton Hall | Home - WHS Track [Directions] | Weston 92 Bethel 57 Weston 122.5 LH 23.5 Weston 129 Kolbe 6 | ||
| Mon., 4/21 | V Softball | Masuk | Home - Hurlbutt El. School, Weston [Directions] | L 0-14 | ||
| Mon., 4/21 | V Girls Tennis | Brookfield | Away - BHS Tennis Courts [Directions] | W 6-1 | 2:45pm | |
| Tue., 4/22 | JV Baseball | Masuk | Away - John Giampaolo Field @ Masuk [Directions] | 4:15 p.m. | 2:45pm | |
| Tue., 4/22 | V Boys Lacrosse | Stratford | Away - Penders Field [Directions] | W 14-7 | 5:15pm | non league |
| Tue., 4/22 | V Boys Outdoor Track | Bethel, Kolbe Cathedral | Away - DeSantis Field at Bethel High School [Directions] | Weston 76 Bethel 74 Weston 146 Kolbe 3 | 2:45pm | |
| Tue., 4/22 | V Girls Golf | Lauralton Hall | Away - Racebrook Country Club [Directions] | Weston- 217 Lauralton Hall- 250 | ||
| Tue., 4/22 | V Girls Lacrosse | Notre Dame-Fairfield | Home - WHS Turf Field [Directions] | W 19-3 | non league | |
| Tue., 4/22 | FR Girls Lacrosse | Wilton | Home - WHS Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 4/22 | V Softball | Notre Dame-Fairfield | Away - Park Avenue Field at Notre Dame [Directions] | L 5-15 | 2:45pm | non league |
| Wed., 4/23 | V Baseball | Stratford | Away - Penders Field [Directions] | W 12-1 | 5:00pm | |
| Wed., 4/23 | FR Baseball | Pomperaug | Away - Community Baseball Field [Directions] | 4:15 p.m. | 2:45pm | |
| Wed., 4/23 | V Boys Golf | New Fairfield | Away - River Oaks [Directions] | Weston 184 New Fairfield 204 | 1:15pm | |
| Wed., 4/23 | V Boys Tennis | New Milford | Away - New Milford High School [Directions] | W 6-1 | 2:45pm | |
| Wed., 4/23 | V Softball | Stratford | Away - DeLuca Field [Directions] | W 13-12 | 5:00pm | |
| Wed., 4/23 | V Girls Tennis | Lauralton Hall | Home - WHS Tennis Courts [Directions] | W 5-2 | ||
| Thu., 4/24 | JV Baseball | Stratford | Home - Revson Field, Weston [Directions] | 4:15 p.m. | ||
| Thu., 4/24 | FR Baseball | Bethel | Home - Revson Field, Weston [Directions] | 4:15 p.m. | ||
| Thu., 4/24 | V Boys Golf | New Milford | Away - Candlewood Valley [Directions] | New Milford 169 Weston 177 | ||
| Thu., 4/24 | V Boys Lacrosse | Brookfield | Away - BHS Stadium Field [Directions] | W 10-9 | 5:00pm | |
| Thu., 4/24 | JV Boys Lacrosse | Brookfield | Away - BHS Stadium Field [Directions] | 5:15 p.m. | 3:45pm | |
| Thu., 4/24 | V Boys Tennis | Joel Barlow | Home - WHS Tennis Courts [Directions] | W 5-2 | ||
| Thu., 4/24 | V Girls Lacrosse | Brookfield | Home - WHS Turf Field [Directions] | T 11-11 | ||
| Thu., 4/24 | JV Girls Lacrosse | Brookfield | Home - WHS Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 4/24 | JV Softball | Stratford | Home - Hurlbutt El. School, Weston [Directions] | 4:15 p.m. | ||
| Thu., 4/24 | V Girls Tennis | Joel Barlow | Away - Tennis Courts [Directions] | W 4-3 | 2:45pm | |
| Fri., 4/25 | V Baseball | New Milford | Home - Revson Field, Weston [Directions] | W 6-5 | ||
| Fri., 4/25 | FR Baseball | Newtown | Home - Revson Field, Weston [Directions] | 4:15 p.m. | ||
| Fri., 4/25 | V Boys Outdoor Track | O'Grady Relays | Away - Danbury High School | TBA | TBA | no bus needed |
| Fri., 4/25 | V Boys Tennis | Staples | Away - Staples HS-Tennis Courts [Directions] | L 0-7 | 2:45pm | non league |
| Fri., 4/25 | FR Girls Lacrosse | Ridgefield | Home - WHS Turf Field [Directions] | 4:45 p.m. | ||
| Fri., 4/25 | V Girls Outdoor Track | O'Grady Relays | Away | TBA | no bus needed | |
| Fri., 4/25 | V Softball | New Milford | Home - Hurlbutt El. School, Weston [Directions] | L 3-11 | ||
| Sat., 4/26 | V Boys Outdoor Track | O'Grady Relays | Away - Danbury high School [Directions] | TBA | 7:30 am | 2 buses |
| Sat., 4/26 | V Girls Lacrosse | North Branford | Away - Albertus Magnus [Directions] | W 18-2 | 12:00pm | non league at Albertus Magnus |
| Sat., 4/26 | JV Girls Lacrosse | North Branford | Away - Albertus Magnus [Directions] | 4:30 p.m. | 12:00pm | at Albertus Magnus |
| Sat., 4/26 | V Girls Outdoor Track | O'Grady Relays | Away [Directions] | TBA | 7:30 am | 2 buses |
| Mon., 4/28 | V Baseball | Bethel | Away - Hunt Field at Bethel High School [Directions] | W 12-3 | 2:45pm | |
| Mon., 4/28 | FR Baseball | Masuk | Away - Wolfe Park [Directions] | 4:15 p.m. | 2:45pm | |
| Mon., 4/28 | V Boys Golf | Bethel | Home - Aspetuck Valley Country Club [Directions] | Weston 187 Bethel 196 | ||
| Mon., 4/28 | V Boys Lacrosse | New Milford | Away - New Milford High School [Directions] | L 6-11 | 4:00pm | |
| Mon., 4/28 | JV Boys Lacrosse | New Milford | Away - New Milford High School [Directions] | 4:00 p.m. | 2:45pm | |
| Mon., 4/28 | V Boys Tennis | Newtown | Home - WHS Tennis Courts [Directions] | W 5-2 | ||
| Mon., 4/28 | V Girls Golf | Brookfield | Home - Aspetuck Valley Country Club [Directions] | Weston 233 Brookfield 277 | ||
| Mon., 4/28 | V Girls Lacrosse | New Milford | Home - WHS Turf Field [Directions] | W 13-9 | ||
| Mon., 4/28 | JV Girls Lacrosse | New Milford | Home - WHS Turf Field [Directions] | 5:00 p.m. | ||
| Mon., 4/28 | V Girls Outdoor Track | Masuk, Notre Dame-Fairfield, Oxford | Home - WHS Track [Directions] | Weston 76 Oxford 74 Weston 104.33 Masuk 45.33 Weston 125.33 ND 20.33 | ||
| Mon., 4/28 | V Softball | Bethel | Away - Kasack Field at Johnson School [Directions] | L 4-16 | 2:45pm | |
| Mon., 4/28 | V Girls Tennis | Newtown | Away - Newtown High School [Directions] | W 4-3 | 2:45pm | |
| Tue., 4/29 | V Baseball | Brookfield | Home - Revson Field, Weston [Directions] | W 9-5 | ||
| Tue., 4/29 | JV Baseball | Bethel | Home - Revson Field, Weston [Directions] | 4:15 p.m. | ||
| Tue., 4/29 | FR Baseball | New Milford | Away - New Milford High School [Directions] | 4:15 p.m. | 2:45pm | |
| Tue., 4/29 | V Boys Outdoor Track | Masuk, Notre Dame-Fairfield, Oxford | Away - Masuk HS Track [Directions] | Weston 79 Masuk 71 Weston 112 Oxford 38 Weston 130 Notre Dame 19 | 2:45pm | |
| Tue., 4/29 | V Boys Tennis | Masuk | Away - Wolfe Park Tennis Courts [Directions] | W 4-0 | 2:45pm | |
| Tue., 4/29 | V Girls Golf | Lauralton Hall | Home - Aspetuck Valley Country Club [Directions] | Weston- 216 Lauralton Hall- 270 | ||
| Tue., 4/29 | V Softball | Brookfield | Home - Hurlbutt El. School, Weston [Directions] | L 3-23 | ||
| Tue., 4/29 | V Girls Tennis | Masuk | Home - WHS Tennis Courts [Directions] | W 6-0 | ||
| Thu., 5/1 | V Boys Golf | Woodland Hawk Invitational | Away | Cancelled | at Oxford Greens | |
| Thu., 5/1 | V Boys Lacrosse | Brien McMahon | Home - WHS Turf Field [Directions] | L 6-12 | non league | |
| Thu., 5/1 | V Boys Tennis | Pomperaug | Away - PHS Tennis Courts [Directions] | W 5-2 | 2:45pm | |
| Thu., 5/1 | V Girls Lacrosse | Ridgefield | Home - WHS Turf Field [Directions] | W 13-6 | non league | |
| Thu., 5/1 | JV Girls Lacrosse | Ridgefield | Home - WHS Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 5/1 | V Girls Tennis | Pomperaug | Home - WHS Tennis Courts [Directions] | W 6-1 | ||
| Fri., 5/2 | V Baseball | Notre Dame-Fairfield | Home - Revson Field, Weston [Directions] | L 4-5 | ||
| Fri., 5/2 | FR Baseball | New Fairfield | Home - Revson Field, Weston [Directions] | 4:15 p.m. | ||
| Fri., 5/2 | V Softball | Notre Dame-Fairfield | Home - Hurlbutt El. School, Weston [Directions] | L 4-8 | ||
| Sat., 5/3 | JV Baseball | Notre Dame-Fairfield | Away - Fabbri Field at Notre Dame [Directions] | 10:00 a.m. | 8:45am | |
| Sat., 5/3 | V Boys Lacrosse | Pelham Memorial (NY) | Away | L 7-9 | TBA | |
| Sat., 5/3 | FR Girls Lacrosse | Ridgefield | Away - Tiger Hollow Turf Field II [Directions] | 11:00 a.m. | 10:15am | |
| Mon., 5/5 | V Baseball | Kolbe Cathedral | Away - Veterans Park [Directions] | W 12-2 | 2:45pm | |
| Mon., 5/5 | V Boys Golf | Masuk | Home - Aspetuck Valley Country Club [Directions] | Masuk 172 Weston 176 | ||
| Mon., 5/5 | JV Boys Golf | Masuk | Home - Aspetuck Valley Country Club [Directions] | 3:00 p.m. | ||
| Mon., 5/5 | V Girls Golf | Masuk | Home - Aspetuck Valley Country Club [Directions] | Weston 210 Masuk 211 | ||
| Mon., 5/5 | V Girls Lacrosse | Joel Barlow | Away - Joel Barlow High School [Directions] | L 9-11 | 4:00pm | |
| Mon., 5/5 | JV Girls Lacrosse | Joel Barlow | Away - Joel Barlow High School [Directions] | 4:00 p.m. | 2:45pm | |
| Mon., 5/5 | FR Girls Lacrosse | Joel Barlow | Away - Field D [Directions] | 5:30 p.m. | 2:45pm | |
| Mon., 5/5 | V Girls Outdoor Track | Pomperaug, New Milford, Joel Barlow | Away - Sports Complex & Track [Directions] | Weston 81 Joel Barlow 69 Weston 93 Pomperaug 57 New Milford 75 Weston 71 | 2:45pm | |
| Mon., 5/5 | V Softball | Kolbe Cathedral | Away - Seaside Park [Directions] | L 4-6 | 2:45pm | |
| Mon., 5/5 | V Girls Tennis | Stratford | Home - WHS Tennis Courts [Directions] | W 7-0 | ||
| Tue., 5/6 | V Baseball | Oxford | Away - OHS Baseball Field [Directions] | W 6-2 | 2:45pm | non league |
| Tue., 5/6 | V Boys Outdoor Track | Joel Barlow, New Milford, Pomperaug | Home - WHS Track [Directions] | Weston 116.5 Barlow 33.5 Weston 83 New Milford 67 Weston 83 Pomperaug 67 | ||
| Tue., 5/6 | V Girls Lacrosse | New Fairfield | Away - Rebel Turf [Directions] | L 18-19 | 2:45pm | |
| Tue., 5/6 | JV Girls Lacrosse | New Fairfield | Away - Rebel Turf [Directions] | 4:00 p.m. | 2:45pm | |
| Wed., 5/7 | JV Baseball | Oxford | Home - Revson Field, Weston [Directions] | 4:15 p.m. | ||
| Wed., 5/7 | FR Baseball | Brookfield | Away - Huckleberry Hill Elementary School Baseball Field [Directions] | 4:00 p.m. | 2:45pm | |
| Wed., 5/7 | V Boys Golf | Newtown | Away - Rock Ridge Country Club [Directions] | Newtown 157 Weston 175 | 1:30pm | |
| Wed., 5/7 | JV Boys Golf | Newtown | Away [Directions] | 3:00 p.m. | 1:30pm | |
| Wed., 5/7 | V Softball | Lauralton Hall | Home - Hurlbutt El. School, Weston [Directions] | L 1-14 | ||
| Wed., 5/7 | V Girls Tennis | Notre Dame-Fairfield | Away - Sacred Heart University [Directions] | W 7-0 | 2:45pm | |
| Thu., 5/8 | V Baseball | Immaculate | Away - Immaculate High School [Directions] | W 5-1 | 2:45pm | |
| Thu., 5/8 | V Boys Golf | Pomperaug | Away - Heritage Village C.C. [Directions] | Pomperaug 154 Weston 172 | 1:30pm | |
| Thu., 5/8 | JV Boys Golf | Pomperaug | Away [Directions] | 3:00 p.m. | 1:30pm | |
| Thu., 5/8 | V Boys Lacrosse | Pomperaug | Away - Sports Complex & Track [Directions] | W 19-8 | 5:00pm | non league |
| Thu., 5/8 | JV Boys Lacrosse | Pomperaug | Away - Sports Complex & Track [Directions] | 5:00 p.m. | 3:15pm | |
| Thu., 5/8 | V Girls Golf | Bunnell | Away - Oronoque Country Club [Directions] | Weston 220 Bunnell 265 | ||
| Thu., 5/8 | V Girls Lacrosse | Bethel | Home - WHS Turf Field [Directions] | W 16-10 | non league | |
| Thu., 5/8 | JV Girls Lacrosse | Bethel | Home - WHS Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 5/8 | V Softball | Immaculate | Away - Immaculate High School [Directions] | L 2-4 | 2:45pm | |
| Sat., 5/10 | V Boys Lacrosse | North Rockland (NY) | Home - Wilton HS Stadium Field [Directions] | L 4-7 | 8:30am | at Wilton High School |
| Sat., 5/10 | FR Girls Lacrosse | Wilton | Away - Lilly Field - Turf [Directions] | 10:00 a.m. | 8:45am | |
| Mon., 5/12 | V Baseball | Joel Barlow | Home - Revson Field, Weston [Directions] | W 9-1 | ||
| Mon., 5/12 | JV Baseball | New Milford | Away - New Milford High School [Directions] | 4:15 p.m. | 8:30am | |
| Mon., 5/12 | V Boys Golf | Brookfield | Home - Aspetuck Valley Country Club [Directions] | Weston 168 Brookfield 184 | ||
| Mon., 5/12 | V Boys Tennis | Bunnell | Home - WHS Tennis Courts [Directions] | W 6-1 | ||
| Mon., 5/12 | V Girls Golf | Joel Barlow | Home - Aspetuck Valley Country Club [Directions] | Joel Barlow 215 Weston 226 | ||
| Mon., 5/12 | V Girls Outdoor Track | Brookfield, New Fairfield, Newtown | Away - BHS Stadium Field [Directions] | Newtown 83 Weston 67 Weston 95 New Fairfield 55 Weston 94 Brookfield 56 | 2:45pm | |
| Mon., 5/12 | V Softball | Joel Barlow | Home - Hurlbutt El. School, Weston [Directions] | L 4-7 | ||
| Mon., 5/12 | V Girls Tennis | Bunnell | Away - Bunnell Tennis Courts [Directions] | W 6-1 | 2:45pm | |
| Tue., 5/13 | JV Baseball | Oxford | Away - OHS Baseball Field [Directions] | 4:15 p.m. | 2:45pm | |
| Tue., 5/13 | V Boys Lacrosse | Notre Dame-Fairfield | Home - WHS Turf Field [Directions] | W 16-3 | non league | |
| Tue., 5/13 | JV Boys Lacrosse | Notre Dame-Fairfield | Home - WHS Turf Field [Directions] | 5:00 p.m. | ||
| Tue., 5/13 | V Boys Outdoor Track | Newtown, New Fairfield, Brookfield | Away - Blue and Gold Stadium [Directions] | Weston 84 Brookfield 66 New Fairfield 89 Weston 61 Newtown 79.5 Weston 70.5 | 2:45pm | |
| Tue., 5/13 | V Boys Tennis | Darien | Away - DHS Tennis Courts [Directions] | W 6-1 | 2:45pm | |
| Tue., 5/13 | V Girls Lacrosse | Immaculate | Away - Mustang Valley [Directions] | W 19-10 | 2:45pm | non league |
| Tue., 5/13 | JV Girls Lacrosse | Immaculate | Away - Mustang Valley [Directions] | 5:30 p.m. | 2:45pm | |
| Tue., 5/13 | V Girls Tennis | Wilton | Home - WHS Tennis Courts [Directions] | L 3-4 | ||
| Wed., 5/14 | V Baseball | New Fairfield | Away - NFHS Baseball Field [Directions] | W 7-2 | 2:45pm | |
| Wed., 5/14 | FR Baseball | Bunnell | Away - Flood Middle School [Directions] | 4:15 p.m. | 2:45pm | |
| Wed., 5/14 | V Boys Golf | Bunnell | Away - Oronoque Country Club [Directions] | Bunnell 172 Weston 174 | ||
| Wed., 5/14 | V Boys Tennis | New Fairfield | Away - New Fairfield HS [Directions] | W 6-1 | 2:45pm | |
| Wed., 5/14 | V Girls Golf | Brookfield | Away - Sunset Hill Golf Course [Directions] | Weston 207 Brookfield 252 | ||
| Wed., 5/14 | V Girls Lacrosse | Immaculate | Home - WHS Turf Field [Directions] | W 12-7 | non league | |
| Wed., 5/14 | JV Girls Lacrosse | Immaculate | Home - WHS Turf Field [Directions] | 3:30 p.m. | ||
| Wed., 5/14 | V Softball | New Fairfield | Away - NFHS Softball Field [Directions] | W 8-6 | 2:45pm | |
| Wed., 5/14 | V Girls Tennis | Lauralton Hall | Away - Eisenhower Park [Directions] | L 2-5 | 2:45pm | non league |
| Thu., 5/15 | V Baseball | Oxford | Home - Revson Field, Weston [Directions] | W 7-4 | ||
| Thu., 5/15 | JV Baseball | New Fairfield | Home - Revson Field, Weston [Directions] | 4:15 p.m. | ||
| Thu., 5/15 | V Boys Golf | Joel Barlow | Away - Redding Country Club [Directions] | Joel Barlow 176 Weston 183 | ||
| Thu., 5/15 | V Boys Lacrosse | Westhill | Home - WHS Turf Field [Directions] | W 11-4 | non league | |
| Thu., 5/15 | JV Boys Lacrosse | Westhill | Home - WHS Stadium Field [Directions] | 5:30 p.m. | ||
| Thu., 5/15 | V Boys Tennis | Glastonbury | Home - WHS Tennis Courts [Directions] | W 4-3 | ||
| Thu., 5/15 | V Girls Golf | Staples | Away [Directions] | Staples 168 Weston 218 | non league | |
| Thu., 5/15 | V Girls Lacrosse | Masuk | Home - WHS Turf Field [Directions] | W 17-3 | non league | |
| Thu., 5/15 | JV Girls Lacrosse | Masuk | Home - WHS Turf Field [Directions] | 5:30 p.m. | ||
| Thu., 5/15 | V Softball | Oxford | Home - Hurlbutt El. School, Weston [Directions] | L 0-9 | ||
| Thu., 5/15 | JV Softball | New Fairfield | Home - Weston Middle School [Directions] | 4:00 p.m. | ||
| Thu., 5/15 | V Girls Tennis | New Fairfield | Home - WHS Tennis Courts [Directions] | W 6-1 | ||
| Sat., 5/17 | JV Baseball | Joel Barlow | Away - Veteran's Field - Easton [Directions] | 11:00 a.m. | 8:45am | |
| Sat., 5/17 | V Boys Lacrosse | Masuk | Away - Masuk Stadium Field [Directions] | W 16-2 | 2:15pm | non league |
| Sat., 5/17 | JV Boys Lacrosse | Masuk | Away - Masuk Stadium Field [Directions] | 2:30 p.m. | 1:00pm | |
| Mon., 5/19 | V Baseball | Bunnell | Away - Bunnell Baseball Field [Directions] | L 1-2 | 2:45pm | |
| Mon., 5/19 | FR Baseball | Masuk | Home - Revson Field, Weston [Directions] | 4:15 p.m. | ||
| Mon., 5/19 | V Boys Golf | Joel Barlow | Home - Aspetuck Valley Country Club [Directions] | Weston 177 Joel Barlow 184 | non league | |
| Mon., 5/19 | V Boys Golf | Stratford | Home - Aspetuck Valley Country Club [Directions] | Weston 177 Stratford 206 | ||
| Mon., 5/19 | V Boys Lacrosse | Joel Barlow | Home - WHS Turf Field [Directions] | L 5-6 | ||
| Mon., 5/19 | JV Boys Lacrosse | Joel Barlow | Home - WHS Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 5/19 | V Boys Tennis | Joel Barlow | Home - WHS Tennis Courts [Directions] | W 6-1 | SWC Semifinals | |
| Mon., 5/19 | V Girls Golf | Immaculate | Home - Aspetuck Valley Country Club [Directions] | Weston 225 Immaculate 225 | ||
| Mon., 5/19 | V Softball | Bunnell | Away - Bunnell Softball Field [Directions] | L 2-7 | 2:45pm | |
| Mon., 5/19 | V Girls Tennis | Bunnell | Home - WHS Tennis Courts [Directions] | W 6-1 | SWC Team Semifinals | |
| Tue., 5/20 | V Baseball | Pomperaug | Home - Revson Field, Weston [Directions] | W 5-3 | ||
| Tue., 5/20 | JV Baseball | Bunnell | Away - Bunnell Baseball Field [Directions] | 4:15 p.m. | 2:45pm | |
| Tue., 5/20 | V Boys Golf | Newtown | Home - Aspetuck Valley Country Club [Directions] | Newtown 163 Weston 169 | ||
| Tue., 5/20 | V Boys Outdoor Track | Bunnell, Immaculate, Stratford | Away - Bunnell Track [Directions] | Weston 124 Immaculate 25 Weston 121 Stratford 29 Bunnell 91.5 Weston 58.5 | 2:45pm | |
| Tue., 5/20 | V Boys Tennis | Newtown | Home - WHS Tennis Courts [Directions] | W 6-1 | at home of higher seed | |
| Tue., 5/20 | V Girls Golf | Greenwich | Home - Fairchild Wheeler [Directions] | Greenwich 174 Weston 212 | non league | |
| Tue., 5/20 | V Girls Lacrosse | Stratford/Bunnell | Home - WHS Turf Field [Directions] | W 16-5 | non league | |
| Tue., 5/20 | JV Girls Lacrosse | Stratford/Bunnell | Home - WHS Turf Field [Directions] | 3:30 p.m. | ||
| Tue., 5/20 | V Girls Outdoor Track | Bunnell, Immaculate, Stratford | Away - Bunnell Track [Directions] | Weston 109 Stratford 37 Weston 103 Immaculate 47 Weston 87 Bunnell 62 | 2:45pm | |
| Tue., 5/20 | V Softball | Pomperaug | Home - Hurlbutt El. School, Weston [Directions] | L 2-10 | ||
| Tue., 5/20 | V Girls Tennis | Joel Barlow | Home - WHS Tennis Courts [Directions] | L 3-4 | SWC Championship | |
| Wed., 5/21 | FR Baseball | New Milford | Home - Revson Field, Weston [Directions] | 4:15 p.m. | ||
| Wed., 5/21 | V Boys Tennis | Stratford | Away - Short Beach Tennis Courts [Directions] | W 7-0 | 9:00 am | |
| Wed., 5/21 | FR Girls Lacrosse | New Milford | Home - WHS Turf Field [Directions] | 4:15 p.m. | ||
| Wed., 5/21 | JV Softball | New Milford | Away - New Milford High School [Directions] | 4:15 p.m. | ||
| Thu., 5/22 | V Boys Golf | CHAPPA Tournament | Away | TBA | Long Shore CC | |
| Thu., 5/22 | V Boys Lacrosse | Brookfield | Home - WHS Turf Field [Directions] | L 4-9 | SWC Quarterfinals | |
| Thu., 5/22 | V Boys Tennis | Fairfield Prep | Away - Walsh Athletic Center Courts, Fairfield University [Directions] | Cancelled | 2:40pm | |
| Thu., 5/22 | V Girls Golf | Woodstock Academy | Away - Quinnatisset Country Club [Directions] | Weston 212 Woodstock Academy 212 | ||
| Sat., 5/24 | V Baseball | New Milford | Home - Revson Field, Weston [Directions] | W 3-2 | SWC Quarterfinals | |
| Sat., 5/24 | V Girls Lacrosse | Joel Barlow | Away [Directions] | L 8-9 | 2:30pm | SWC Quarterfinals |
| Tue., 5/27 | V Boys Golf | Coaches Cup | Away | TBA | Rock Ridge CC | |
| Tue., 5/27 | V Boys Lacrosse | SWC Semifinals | Away [Directions] | Cancelled | at New Fairfield at 5pm or 7pm | |
| Tue., 5/27 | V Girls Golf | Immaculate | Away [Directions] | Weston 218 Immaculate 234 | ||
| Tue., 5/27 | V Girls Lacrosse | SWC Semifinals | Away [Directions] | Cancelled | TBA | SWC Semifinals at Newtown |
| Tue., 5/27 | JV Softball | New Fairfield | Home - Hurlbutt El. School, Weston [Directions] | Cancelled | ||
| Wed., 5/28 | V Girls Golf | Cheshire | Away - Country Club- Southington [Directions] | Cheshire 213 Weston 215 | non league | |
| Wed., 5/28 | JV Softball | Brookfield | Away - BHS Softball Field [Directions] | Cancelled | ||
| Wed., 5/28 | V Girls Tennis | SWC Individual Tournament | Away [Directions] | 3:30 p.m. | TBA | at Joel Barlow |
| Thu., 5/29 | V Baseball | Pomperaug | Away [Directions] | L 0-3 | 5:15pm | SWC Semifinals at Bethel |
| Thu., 5/29 | V Baseball | SWC Championship Game | Away [Directions] | Cancelled | at Bethel | |
| Thu., 5/29 | V Boys Lacrosse | SWC Championship Game | Away [Directions] | Cancelled | at Pomperaug | |
| Thu., 5/29 | V Boys Outdoor Track | SWC Championship Meet | Away [Directions] | 3:00 p.m. | 1:30pm | at Bunnell |
| Thu., 5/29 | V Boys Tennis | SWC Individual Tournament | Away [Directions] | 12:00 p.m. | 11am | at Rogers Park |
| Thu., 5/29 | V Boys Tennis | SWC Individual Tournament | Away [Directions] | 3:30 p.m. | TBA | at Rogers Park |
| Thu., 5/29 | V Girls Lacrosse | SWC Championship Game | Away [Directions] | Cancelled | TBA | at Pomperaug |
| Thu., 5/29 | V Girls Outdoor Track | SWC Championship Meet | Away [Directions] | 3:00 p.m. | 1:30pm | at Bunnell |
| Thu., 5/29 | V Girls Tennis | SWC Individual Tournament | Away [Directions] | 12:00 p.m. | 11:15am | at Joel Barlow |
| Fri., 5/30 | V Boys Golf | SWC Championships | Away | 7:30 a.m. | at Ridgewood CC | |
| Fri., 5/30 | JV Softball | New Fairfield | Home - Hurlbutt El. School, Weston [Directions] | 4:00 p.m. | ||
| Sat., 5/31 | V Girls Tennis | Wethersfield | Home - WHS Tennis Courts [Directions] | W 7-0 | CIAC State Tournament | |
| Mon., 6/2 | V Baseball | Bullard Havens Tech | Home - Revson Field, Weston [Directions] | W 3-0 | CIAC First Round Game | |
| Mon., 6/2 | V Boys Golf | Pomperaug | Home - Aspetuck Valley Country Club [Directions] | Pomperaug 165 Weston 171 | non league | |
| Mon., 6/2 | V Boys Outdoor Track | CIAC Class M Championship | Away - Sheehan HS [Directions] | 2:30 p.m. | ||
| Mon., 6/2 | V Girls Outdoor Track | CIAC Class M Championship | Away - Sheehan HS [Directions] | 2:30 p.m. | ||
| Mon., 6/2 | V Girls Tennis | East Lyme | Home - WHS Tennis Courts [Directions] | W 7-0 | CIAC State Tournament 2nd round | |
| Tue., 6/3 | V Baseball | Haddam-Killingworth | Home - Revson Field, Weston [Directions] | L 6-9 | CIAC State Tournament 2nd Round | |
| Tue., 6/3 | V Girls Golf | SWC Championships | Away | 9:00 a.m. | at Orange Hills CC | |
| Tue., 6/3 | V Girls Lacrosse | Lauralton Hall | Home - WHS Turf Field [Directions] | W 19-11 | CIAC State Tournament | |
| Tue., 6/3 | V Girls Tennis | Farmington | Home - WHS Tennis Courts [Directions] | W 7-0 | CIAC Quarterfinal | |
| Wed., 6/4 | V Boys Lacrosse | Granby Memorial | Away - Granby Memorial High School [Directions] | W 9-7 | 2:45pm | CIAC State Tournament |
| Wed., 6/4 | V Girls Tennis | Sheehan | Home - WHS Tennis Courts [Directions] | W 7-0 | CIAC State Semifinals | |
| Fri., 6/6 | V Girls Lacrosse | Old Lyme | Away - Old Lyme High School [Directions] | L 13-14 | 12:45pm | CIAC State Quarterfinal |
| Fri., 6/6 | V Girls Tennis | Wilton | Away [Directions] | L 2-5 | CIAC State Championship Match at Joel Barlow | |
| Sat., 6/7 | V Boys Lacrosse | Northwest Catholic | Away - St. Thomas Seminary, Bloomfield [Directions] | L 10-11 | 12:00pm | CIAC State Quarterfinal |
| Mon., 6/9 | V Boys Golf | CIAC Div. III Championship | Away - Tallwood CC - Hebron [Directions] | 7:00 a.m. | ||
| Mon., 6/9 | V Boys Outdoor Track | CIAC Open Championship | Away - Middletown [Directions] | 1:30 p.m. | ||
| Mon., 6/9 | V Girls Outdoor Track | CIAC Open Championship | Away - Middletown [Directions] | 1:30 p.m. | ||
| Tue., 6/10 | V Girls Golf | CIAC Girls Golf Championship | Away - Orange Hill CC - Orange [Directions] | 7:00 a.m. | ||
| Sat., 6/14 | V Boys Outdoor Track | New England Championship | Away - Norwell (MA) HS | TBA | ||
| Sat., 6/14 | V Girls Outdoor Track | New England Championship | Away - Norwell (MA) HS | TBA | ||
| Mon., 6/16 | V Boys Golf | New England Championships | Away - Bretwood GC - Keene, NH | TBA | ||
| Mon., 6/16 | V Girls Golf | New England Championships | Away - Bretwood GC - Keene, NH | TBA | ||
| Tue., 6/17 | V Boys Outdoor Track | CIAC Decathlon Champ. | Away - USCG Academy [Directions] | 11:00 a.m. | ||
| Tue., 6/17 | V Girls Outdoor Track | CIAC Heptathlon/Hammer/Steeplechase Champ. | Away - USCG Academy | 11:30 a.m. | ||
| Wed., 6/18 | V Boys Outdoor Track | CIAC Decathlon/Hammer/Steeplechase Champ. | Away - Willowbrook Park - New Britain [Directions] | 11:00 a.m. | ||
| Wed., 6/18 | V Girls Outdoor Track | CIAC Heptathlon Champ. | Away - USCG Academy [Directions] | 11:00 a.m. | ||