| Weston 2017-18 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 673 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| TBA | JV Baseball | New Milford | Away - New Milford HS [Directions] | 4:15 p.m. | 2:40pm | |
| TBA | JV Baseball | Fairfield Warde | Home - Revson Field, Weston [Directions] | TBA | ||
| TBA | JV Baseball | Joel Barlow | Home - Revson Field, Weston [Directions] | TBA | ||
| TBA | FR Baseball | Joel Barlow | Away - Field G (Baseball) [Directions] | 4:00 p.m. | 2:40pm | |
| TBA | FR Baseball | New Fairfield | Away - NFHS Baseball Field [Directions] | 4:15 p.m. | 2:40pm | |
| TBA | FR Baseball | New Milford | Away - New Milford HS [Directions] | 4:15 p.m. | 2:40pm | |
| TBA | FR Baseball | Stratford | Away - Penders Field [Directions] | TBA | 2:30pm | |
| TBA | FR Baseball | Ridgefield | Away - Governor's Park Field (aka Ciuccoli or Old HS) [Directions] | Cancelled | 2:40pm | |
| TBA | JV Boys Ice Hockey | Wooster | Home - Danbury Ice Arena [Directions] | TBA | ||
| TBA | JV Boys Lacrosse | Masuk | Home - WHS Turf Field [Directions] | TBA | ||
| TBA | V Boys Outdoor Track | Brookfield, Stratford, New Fairfield | Away - BHS Track [Directions] | 4:00 p.m. | 2:40pm | |
| TBA | JV Boys Soccer | Brookfield | Away - BHS Back Turf [Directions] | TBA | 2:40pm | |
| TBA | V Boys Tennis | Daniel Hand | Home - WHS Tennis Courts [Directions] | Cancelled | nonleague | |
| TBA | JV Boys Tennis | Fairfield Warde | Home - WHS Tennis Courts [Directions] | 10:00 a.m. | ||
| TBA | FR Girls Basketball | St. Joseph | Away - St. Joseph HS [Directions] | TBA | 2:40pm | |
| TBA | JV Field Hockey | Masuk | Away - Benedict Stadium Field @ Masuk HS [Directions] | 5:15 p.m. | 3:45p.m. | |
| TBA | JV Field Hockey | New Fairfield | Away - Rebel Turf [Directions] | TBA | 2:40pm | |
| TBA | JV Field Hockey | Old Saybrook | Home - WHS Turf Field [Directions] | TBA | ||
| TBA | JV Girls Soccer | Brookfield | Home - WHS Turf Field [Directions] | TBA | ||
| TBA | FR Girls Soccer | Pomperaug | Home - WHS Turf Field [Directions] | TBA | ||
| TBA | JV Softball | New Milford | Away - New Milford HS [Directions] | 4:15 p.m. | 2:40pm | |
| TBA | JV Softball | Stratford | Home - Weston MS [Directions] | 4:15 p.m. | ||
| TBA | JV Softball | New Fairfield | Away - NFHS [Directions] | 4:15 p.m. | 2:40pm | |
| TBA | JV Softball | New Fairfield | Home - Hurlbutt El. School, Weston [Directions] | TBA | ||
| TBA | JV Girls Tennis | Staples | Home - WHS Tennis Courts [Directions] | 3:00 p.m. | ||
| TBA | JV Girls Tennis | Fairfield Warde | Home - WHS Tennis Courts [Directions] | TBA | ||
| Fri., 9/8 | V Football | Bethel | Home - WHS Stadium Field [Directions] | W 33-17 | ||
| Fri., 9/8 | V Girls Soccer | New Fairfield | Away - Rebel Stadium [Directions] | W 4-0 | 2:40pm | |
| Fri., 9/8 | JV Girls Soccer | New Fairfield | Away - Rebel Stadium [Directions] | 4:00 p.m. | 2:40p.m. | |
| Fri., 9/8 | V Girls Swimming and Diving | Immaculate | Away - O'Neill Center, WCSU, Danbury [Directions] | Weston 102 Immaculate/Bethel 75 | 2:40pm | |
| Fri., 9/8 | V Girls Volleyball | Joel Barlow | Home - WHS Gymnasium [Directions] | L 0-3 | Non-League | |
| Fri., 9/8 | JV Girls Volleyball | Joel Barlow | Home - WHS Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 9/8 | FR Girls Volleyball | Pomperaug | Away - Auxiliary Gym [Directions] | 3:45 p.m. | 2:40pm | |
| Sat., 9/9 | JV Football | Bethel | Away - Bethel HS [Directions] | 11:00 a.m. | 9:30am | |
| Sat., 9/9 | V Boys Soccer | New Fairfield | Home - WHS Turf Field [Directions] | W 2-0 | ||
| Sat., 9/9 | JV Boys Soccer | New Fairfield | Home - WHS Stadium Field [Directions] | 3:30 p.m. | ||
| Sat., 9/9 | V Girls Soccer | Montville | Home - WHS Turf Field [Directions] | W 1-0 | Non-League | |
| Sat., 9/9 | JV Girls Soccer | Montville | Home - WHS Stadium Field [Directions] | 1:00 p.m. | ||
| Mon., 9/11 | FR Girls Soccer | Pomperaug | Home - WHS Turf Field [Directions] | 4:15 p.m. | ||
| Mon., 9/11 | V Girls Volleyball | Brookfield | Away - BHS Big Gym [Directions] | L 0-3 | 2:40pm | Non-League |
| Mon., 9/11 | JV Girls Volleyball | Brookfield | Away - BHS Big Gym [Directions] | 4:00 p.m. | 2:40pm | |
| Mon., 9/11 | FR Girls Volleyball | Immaculate | Away [Directions] | 3:45 p.m. | 2:40pm | |
| Tue., 9/12 | V Boys Cross Country | Pomperaug | Away - Sports Complex & Track [Directions] | Pomperaug - 21, Weston - 39 | 2:40pm | |
| Tue., 9/12 | V Boys Soccer | Bunnell | Home - WHS Turf Field [Directions] | W 3-1 | ||
| Tue., 9/12 | JV Boys Soccer | Bunnell | Home - WHS Stadium Field [Directions] | 5:15 p.m. | ||
| Tue., 9/12 | V Girls Cross Country | Pomperaug | Away - Sports Complex & Track [Directions] | Pomperaug 15 Weston 50 | 2:40p.m. | |
| Tue., 9/12 | V Field Hockey | Newtown | Home - WHS Turf Field [Directions] | L 1-3 | Non-League | |
| Tue., 9/12 | JV Field Hockey | Newtown | Home - WHS Turf Field [Directions] | 3:45 p.m. | ||
| Tue., 9/12 | V Girls Soccer | Bunnell | Away - Bunnell Turf Field [Directions] | W 4-2 | 3:30pm | |
| Tue., 9/12 | JV Girls Soccer | Bunnell | Away - Bunnell Turf Field [Directions] | 5:00 p.m. | 3:30p.m. | |
| Tue., 9/12 | V Girls Swimming and Diving | New Milford | Away - Canterbury School [Directions] | Weston 94 New Milford 82 | 5:30pm | |
| Wed., 9/13 | V Girls Volleyball | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | L 1-3 | 3:15pm | Non-League |
| Wed., 9/13 | JV Girls Volleyball | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | 4:45 p.m. | 3:15pm | |
| Wed., 9/13 | FR Girls Volleyball | New Milford | Home - WHS Old Gymnasium [Directions] | 3:45 p.m. | ||
| Thu., 9/14 | V Boys Soccer | New Milford | Home - WHS Turf Field [Directions] | T 2-2 | ||
| Thu., 9/14 | JV Boys Soccer | New Milford | Home - WHS Turf Field [Directions] | 5:00 p.m. | ||
| Thu., 9/14 | V Girls Soccer | New Milford | Away - New Milford HS [Directions] | L 2-3 | 2:40pm | |
| Thu., 9/14 | JV Girls Soccer | New Milford | Away - New Milford HS [Directions] | 4:15 p.m. | 2:40p.m. | |
| Fri., 9/15 | V Football | Sheehan | Away - Sheehan HS Riccitelli Field [Directions] | L 27-28 | 3:30pm | |
| Fri., 9/15 | V Girls Swimming and Diving | New Fairfield | Home - Weston MS Pool [Directions] | Weston 97 New Fairfield 82 | ||
| Fri., 9/15 | V Girls Volleyball | New Milford | Home - WHS Gymnasium [Directions] | W 3-0 | ||
| Fri., 9/15 | JV Girls Volleyball | New Milford | Home - WHS Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 9/15 | FR Girls Volleyball | SWC Freshman Jamboree | Away [Directions] | 3:30 p.m. | 2:40pm | at Masuk |
| Sat., 9/16 | V Boys Cross Country | River Valley Invitational | Away [Directions] | http://mysportsresults.com/Results/Results/7thCTRiverValleyInv-20170916.htm | 6:30am | at Cromwell High School |
| Sat., 9/16 | JV Football | Sheehan | Home - WHS Stadium Field [Directions] | 11:00 a.m. | ||
| Sat., 9/16 | V Girls Cross Country | River Valley Inviational | Away [Directions] | 8:30 a.m. | 6:30am | at Cromwell High School |
| Sat., 9/16 | V Field Hockey | Immaculate | Away - Mustang Valley [Directions] | L 0-6 | 8:30am | Non-League |
| Sat., 9/16 | JV Field Hockey | Immaculate | Away - Mustang Valley [Directions] | 11:45 a.m. | 8:30am | |
| Sat., 9/16 | V Girls Soccer | Lauralton Hall | Away - Lauralton Hall Field [Directions] | T 2-2 | 8:30am | |
| Sat., 9/16 | JV Girls Soccer | Lauralton Hall | Away - Lauralton Hall Field [Directions] | 10:00 a.m. | 8:30am | |
| Mon., 9/18 | FR Girls Soccer | Newtown | Away - Treadwell Town Park--Tilson Field [Directions] | 3:45 p.m. | 2:40p.m. | |
| Mon., 9/18 | V Girls Volleyball | Kolbe Cathedral | Away - Kolbe Cathedral Gym [Directions] | W 3-0 | 2:40pm | |
| Mon., 9/18 | JV Girls Volleyball | Kolbe Cathedral | Away - Kolbe Cathedral Gym [Directions] | 4:00 p.m. | 2:40pm | |
| Mon., 9/18 | FR Girls Volleyball | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | 3:45 p.m. | ||
| Tue., 9/19 | V Boys Cross Country | Immaculate, Masuk, Bethel | Home - WHS Stadium Field [Directions] | Weston 19 masuk 44 Weston 25 Bethel 30 Immaculate 20 Weston 39 | ||
| Tue., 9/19 | V Boys Soccer | Brookfield | Away - BHS Stadium Field [Directions] | W 3-2 | 2:40p.m. | |
| Tue., 9/19 | V Girls Cross Country | Immaculate, Masuk, Bethel | Home - WHS Stadium Field [Directions] | Weston 15 Masuk 48 Weston 20 Bethel 37 Immaculate 16 Weston 47 | ||
| Tue., 9/19 | V Field Hockey | New Fairfield | Away - Rebel Turf [Directions] | L 1-4 | 2:40pm | |
| Tue., 9/19 | V Girls Soccer | Brookfield | Home - WHS Turf Field [Directions] | L 0-1 | ||
| Tue., 9/19 | V Girls Volleyball | Brien McMahon | Home - WHS Gymnasium [Directions] | L 0-3 | ||
| Tue., 9/19 | JV Girls Volleyball | Brien McMahon | Home - WHS Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 9/22 | V Football | Stratford | Away - Penders Field [Directions] | L 16-21 | 4:00pm | |
| Fri., 9/22 | V Boys Soccer | Masuk | Away - Benedict Stadium Field @ Masuk HS [Directions] | L 1-4 | 2:40pm | |
| Fri., 9/22 | JV Boys Soccer | Masuk | Away - Masuk Middle Field [Directions] | 4:45 p.m. | 2:40pm | |
| Fri., 9/22 | V Field Hockey | Newtown | Away - Treadwell Town Park [Directions] | L 0-2 | 2:40pm | |
| Fri., 9/22 | JV Field Hockey | Newtown | Away - Treadwell Town Park [Directions] | 5:30 p.m. | 2:40p.m. | |
| Fri., 9/22 | V Girls Soccer | Masuk | Home - WHS Turf Field [Directions] | W 4-2 | ||
| Fri., 9/22 | JV Girls Soccer | Masuk | Home - WHS Turf Field [Directions] | 5:00 p.m. | ||
| Fri., 9/22 | V Girls Swimming and Diving | Brookfield | Home - Weston MS Pool [Directions] | Weston 98 Brookfield 83 | ||
| Fri., 9/22 | V Girls Volleyball | New Fairfield | Away - NFHS Gym [Directions] | W 3-1 | 2:40pm | |
| Fri., 9/22 | JV Girls Volleyball | New Fairfield | Away - NFHS Gym [Directions] | 4:00 p.m. | 2:40pm | |
| Fri., 9/22 | FR Girls Volleyball | Masuk | Home - WHS Gymnasium [Directions] | 3:45 p.m. | 2:40pm | |
| Sat., 9/23 | V Boys Cross Country | Wickham Invite | Away - Wickham Park | Cancelled | 8:45AM | JV 1:10 Varsity 3PM |
| Sat., 9/23 | JV Football | Stratford | Home - Weston H.S. [Directions] | 11:00 a.m. | ||
| Sat., 9/23 | V Girls Cross Country | Ocean State Invite | Away - Warrick, RI. | 1:10 p.m. | 8:30AM | |
| Sat., 9/23 | FR Girls Soccer | Masuk | Away - Masuk Middle Field [Directions] | 9:00 a.m. | 7:45a.m. | |
| Mon., 9/25 | V Field Hockey | Brookfield | Home - WHS Turf Field [Directions] | T 1-1 | ||
| Mon., 9/25 | JV Field Hockey | Brookfield | Home - WHS Turf Field [Directions] | 5:00 p.m. | ||
| Mon., 9/25 | FR Girls Soccer | New Milford | Away - New Milford HS [Directions] | 3:45 p.m. | 2:40 pm | |
| Mon., 9/25 | V Girls Volleyball | Stratford | Away - Needham Memorial Gymnasium [Directions] | L 1-3 | 3:15pm | |
| Mon., 9/25 | JV Girls Volleyball | Stratford | Away - Needham Memorial Gymnasium [Directions] | 5:00 p.m. | 3:15pm | |
| Mon., 9/25 | FR Girls Volleyball | New Fairfield | Home - WHS Old Gymnasium [Directions] | 3:45 p.m. | ||
| Tue., 9/26 | V Boys Cross Country | Kolbe Cathedral, Stratford, New Fairfield | Home - WHS Stadium Field [Directions] | Weston 24 New Fairfield 35 Weston 15 Stratford 50 Weston 15 Kolbe 50 | ||
| Tue., 9/26 | V Boys Soccer | Immaculate | Home - WHS Turf Field [Directions] | L 1-2 | ||
| Tue., 9/26 | JV Boys Soccer | Immaculate | Home - WHS Turf Field [Directions] | 5:00 p.m. | ||
| Tue., 9/26 | V Girls Cross Country | Kolbe Cathedral, Stratford, New Fairfield | Home - WHS Stadium Field [Directions] | Weston 28 New Fairfield 35 Weston 15 Kolbe 50 Weston 15 Stratford 50 | ||
| Tue., 9/26 | V Girls Soccer | Immaculate | Away - Mustang Valley [Directions] | L 1-2 | 2:40pm | |
| Tue., 9/26 | JV Girls Soccer | Immaculate | Away - Immaculate HS [Directions] | 4:30 p.m. | 2:40p.m. | |
| Tue., 9/26 | V Girls Swimming and Diving | Newtown | Home - Weston MS Pool [Directions] | Weston 95 Newtown 86 | ||
| Wed., 9/27 | V Field Hockey | Pomperaug | Home - WHS Turf Field [Directions] | T 0-0 | ||
| Wed., 9/27 | JV Field Hockey | Pomperaug | Home - WHS Turf Field [Directions] | 5:00 p.m. | 4:15PM | |
| Wed., 9/27 | V Girls Volleyball | Masuk | Home - WHS Gymnasium [Directions] | W 3-1 | ||
| Wed., 9/27 | JV Girls Volleyball | Masuk | Home - WHS Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 9/27 | FR Girls Volleyball | Newtown | Away - Newtown HS Gymnasium [Directions] | 3:45 p.m. | 2:40pm | |
| Thu., 9/28 | V Boys Soccer | Newtown | Away - Blue and Gold Stadium [Directions] | L 0-2 | 3:15pm | |
| Thu., 9/28 | JV Boys Soccer | Newtown | Away - Blue and Gold Stadium [Directions] | 5:00 p.m. | 3:15pm | |
| Thu., 9/28 | V Girls Soccer | Newtown | Home - WHS Turf Field [Directions] | T 2-2 | ||
| Thu., 9/28 | JV Girls Soccer | Newtown | Home - WHS Turf Field [Directions] | 5:00 p.m. | ||
| Mon., 10/2 | FR Girls Soccer | Pomperaug | Away - PHS Soccer Field [Directions] | 4:00 p.m. | 2:40pm | |
| Mon., 10/2 | V Girls Volleyball | Brookfield | Home - WHS Gymnasium [Directions] | L 1-3 | ||
| Mon., 10/2 | JV Girls Volleyball | Brookfield | Home - WHS Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 10/2 | FR Girls Volleyball | Brookfield | Home - WHS Old Gymnasium [Directions] | 3:45 p.m. | ||
| Tue., 10/3 | V Boys Cross Country | Joel Barlow, Notre Dame-Fairfield, Brookfield | Away - JBHS Cross Country Loop [Directions] | Weston 25 - Barlow 30 Weston 15 - ND 50 Brookfield 26 - Weston 29 | 4:15PM | |
| Tue., 10/3 | V Boys Soccer | Pomperaug | Home - WHS Turf Field [Directions] | L 2-1 | ||
| Tue., 10/3 | JV Boys Soccer | Pomperaug | Home - WHS Turf Field [Directions] | 5:00 p.m. | ||
| Tue., 10/3 | V Girls Cross Country | Joel Barlow, Notre Dame-Fairfield, Brookfield | Away - JBHS Cross Country Loop [Directions] | Weston 15 Joel Barlow 46 Weston 23 Brookfield 32 Weston 15 Notre Dame 49 | 2:40pm | |
| Tue., 10/3 | V Field Hockey | Watertown | Away - John J. Mills Complex @ Watertown HS [Directions] | L 2-5 | 4:15 pm | |
| Tue., 10/3 | JV Field Hockey | Watertown | Away - John J. Mills Complex @ Watertown HS [Directions] | 5:30 p.m. | 3:45pm | |
| Tue., 10/3 | V Girls Soccer | Pomperaug | Away - Sports Complex & Track [Directions] | L 1-2 | 3:00pm | |
| Tue., 10/3 | JV Girls Soccer | Pomperaug | Away - PHS Soccer Field [Directions] | 4:30 p.m. | 3:00p.m. | |
| Tue., 10/3 | V Girls Swimming and Diving | Stratford | Away - Flood MS Pool [Directions] | Weston 95 Stratford 66 | 3:45pm | |
| Wed., 10/4 | V Girls Volleyball | Pomperaug | Away - PHS Main Gym [Directions] | L 1-3 | 2:40pm | |
| Wed., 10/4 | JV Girls Volleyball | Pomperaug | Away - PHS Main Gym [Directions] | 4:00 p.m. | 2:40pm | |
| Thu., 10/5 | V Boys Soccer | Kolbe Cathedral | Away - Veterans Park [Directions] | W 2-1 | 2:40pm | |
| Thu., 10/5 | V Field Hockey | New Milford | Away - New Milford HS [Directions] | L 0-6 | 2:40pm | |
| Thu., 10/5 | JV Field Hockey | New Milford | Away - New Milford HS [Directions] | 4:00 p.m. | 4:00p.m. | |
| Thu., 10/5 | V Girls Soccer | Kolbe Cathedral | Home - WHS Turf Field [Directions] | W 9-2 | ||
| Thu., 10/5 | V Girls Volleyball | Bethel | Home - WHS Gymnasium [Directions] | W 3-0 | ||
| Thu., 10/5 | JV Girls Volleyball | Bethel | Home - WHS Gymnasium [Directions] | 4:30 p.m. | ||
| Thu., 10/5 | FR Girls Volleyball | Immaculate | Home - WHS Old Gymnasium [Directions] | 3:45 p.m. | ||
| Fri., 10/6 | V Football | Pomperaug | Home - WHS Stadium Field [Directions] | W 29-3 | Homecoming | |
| Fri., 10/6 | V Girls Swimming and Diving | Bunnell | Home - Weston MS Pool [Directions] | Weston 96 Bunnell 72 | ||
| Fri., 10/6 | FR Girls Volleyball | New Milford | Away - New Milford HS [Directions] | 3:45 p.m. | 2:40pm | |
| Sat., 10/7 | V Boys Cross Country | Wickham Park Invitational | Away [Directions] | 1:00 p.m. | 10:00am | at Wickham Park, Manchester |
| Sat., 10/7 | JV Football | Pomperaug | Away - Sports Complex & Track [Directions] | 11:00 a.m. | 8:45am | |
| Sat., 10/7 | V Field Hockey | Brookfield | Away - BHS Stadium Field [Directions] | L 0-2 | 1:30pm | Non-League |
| Sat., 10/7 | JV Field Hockey | Brookfield | Away - BHS Stadium Field [Directions] | 3:00 p.m. | 1:30pm | |
| Sat., 10/7 | FR Girls Soccer | New Canaan | Home - WHS Turf Field [Directions] | 10:00 a.m. | ||
| Tue., 10/10 | V Boys Cross Country | Newtown, Bunnell, New Milford | Away - Newtown HS [Directions] | Weston 15-Bunnell 48 New Milford 22-Weston 34 Newtown 19-Weston 38 | 2:740PM | |
| Tue., 10/10 | V Boys Soccer | Joel Barlow | Home - WHS Turf Field [Directions] | L 0-2 | ||
| Tue., 10/10 | JV Boys Soccer | Joel Barlow | Home - WHS Stadium Field [Directions] | 5:15 p.m. | ||
| Tue., 10/10 | V Girls Cross Country | Newtown, Bunnell, New Milford | Away - Newtown HS [Directions] | Weston 15 Bunnell 50 Newtown 18 Weston 39 New Milford 26 Weston 29 | 2:40pm | |
| Tue., 10/10 | V Field Hockey | Immaculate | Home - WHS Turf Field [Directions] | W 2-1 | ||
| Tue., 10/10 | JV Field Hockey | Immaculate | Home - WHS Turf Field [Directions] | 3:45 p.m. | ||
| Tue., 10/10 | V Girls Soccer | Joel Barlow | Away - Field J (competition field) [Directions] | W 3-0 | 2:40pm | |
| Tue., 10/10 | JV Girls Soccer | Joel Barlow | Away - Field E (Softball) [Directions] | 4:00 p.m. | 2:40p.m. | |
| Tue., 10/10 | V Girls Swimming and Diving | Pomperaug | Away - PHS Pool [Directions] | Weston 101 Pomperaug 80 | 4:15pm | |
| Tue., 10/10 | V Girls Volleyball | Stamford | Away - Stamford HS [Directions] | L 0-3 | 2:40pm | non league |
| Tue., 10/10 | JV Girls Volleyball | Stamford | Away - Stamford HS [Directions] | 5:30 p.m. | 2:40 pm | |
| Wed., 10/11 | V Girls Volleyball | Joel Barlow | Away - JBHS Lower Gym [Directions] | L 0-3 | 2:40pm | |
| Wed., 10/11 | JV Girls Volleyball | Joel Barlow | Away - JBHS Lower Gym [Directions] | 4:00 p.m. | 2:40pm | |
| Wed., 10/11 | FR Girls Volleyball | New Fairfield | Away [Directions] | 3:45 p.m. | 2:40pm | |
| Thu., 10/12 | V Boys Soccer | Notre Dame-Fairfield | Away - Park Avenue Field at Notre Dame [Directions] | L 2-3 | 2:40 pm | |
| Thu., 10/12 | V Girls Soccer | Notre Dame-Fairfield | Home - WHS Turf Field [Directions] | L 1-2 | ||
| Fri., 10/13 | V Football | Creed | Home - WHS Stadium Field [Directions] | W 36-27 | ||
| Fri., 10/13 | V Girls Swimming and Diving | Masuk | Home - Weston MS Pool [Directions] | Weston 96 Masuk 82 | ||
| Fri., 10/13 | V Girls Volleyball | Newtown | Home - WHS Gymnasium [Directions] | L 1-3 | ||
| Fri., 10/13 | JV Girls Volleyball | Newtown | Home - WHS Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 10/13 | FR Girls Volleyball | Brookfield | Away - BHS Small Gym [Directions] | 3:45 p.m. | 2:40pm | |
| Sat., 10/14 | JV Football | Creed | Away - Blake Field | 10:30 a.m. | 8:15am | |
| Sat., 10/14 | V Field Hockey | Masuk | Home - WHS Turf Field [Directions] | L 0-1 | ||
| Sat., 10/14 | JV Field Hockey | Masuk | Home - WHS Turf Field [Directions] | 3:00 p.m. | ||
| Sat., 10/14 | V Girls Soccer | Watertown | Home - WHS Turf Field [Directions] | L 0-2 | Non-League | |
| Sat., 10/14 | JV Girls Soccer | Watertown | Home - WHS Turf Field [Directions] | 11:00 a.m. | ||
| Sat., 10/14 | FR Girls Soccer | Masuk | Home - WHS Turf Field [Directions] | 9:00 a.m. | ||
| Mon., 10/16 | V Boys Soccer | Stratford | Home - WHS Turf Field [Directions] | W 7-0 | ||
| Mon., 10/16 | JV Boys Soccer | Stratford | Home - WHS Turf Field [Directions] | 5:00 p.m. | ||
| Mon., 10/16 | V Girls Soccer | Stratford | Away - Penders Field [Directions] | W 5-1 | 3:30pm | |
| Mon., 10/16 | JV Girls Soccer | Stratford | Away - Penders Field [Directions] | 5:00 p.m. | 3:30p.m. | |
| Mon., 10/16 | FR Girls Soccer | Masuk | Home - WHS Turf Field [Directions] | 3:45 p.m. | ||
| Mon., 10/16 | V Girls Volleyball | Bunnell | Away - Bunnell [Directions] | L 1-3 | 3:15pm | |
| Mon., 10/16 | JV Girls Volleyball | Bunnell | Away - Bunnell [Directions] | 5:00 p.m. | 3:15 | |
| Mon., 10/16 | FR Girls Volleyball | Newtown | Home - WHS Gymnasium [Directions] | 3:45 p.m. | ||
| Mon., 10/16 | Unified Sports Soccer | Brookfield | Home - WHS Old Gymnasium [Directions] | 2:30 p.m. | ||
| Tue., 10/17 | V Field Hockey | Bethel | Home - WHS Turf Field [Directions] | W 1-0 | ||
| Tue., 10/17 | JV Field Hockey | Bethel | Home - WHS Turf Field [Directions] | 5:00 p.m. | ||
| Tue., 10/17 | V Girls Swimming and Diving | Joel Barlow | Home - Weston MS Pool [Directions] | Weston 93 Joel Barlow 76 | ||
| Wed., 10/18 | V Girls Volleyball | Notre Dame-Fairfield | Home - WHS Gymnasium [Directions] | W 3-1 | ||
| Wed., 10/18 | JV Girls Volleyball | Notre Dame-Fairfield | Home - WHS Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 10/18 | FR Girls Volleyball | Pomperaug | Home - WHS Old Gymnasium [Directions] | 3:45 p.m. | ||
| Thu., 10/19 | V Field Hockey | Joel Barlow | Away - Field I (Stadium) [Directions] | L 0-2 | 4:00pm | |
| Thu., 10/19 | JV Field Hockey | Joel Barlow | Away - Field I (Stadium) [Directions] | 5:15 p.m. | 4:00pm | |
| Thu., 10/19 | V Girls Soccer | Bethel | Home - WHS Turf Field [Directions] | W 4-0 | ||
| Thu., 10/19 | JV Girls Soccer | Bethel | Home - WHS Turf Field [Directions] | 5:00 p.m. | ||
| Fri., 10/20 | V Football | New Milford | Away - New Milford HS [Directions] | L 14-15 | 4:00pm | |
| Fri., 10/20 | V Boys Soccer | Bethel | Away - DeSantis Field at Bethel HS [Directions] | L 0-2 | 4:45pm | |
| Fri., 10/20 | JV Boys Soccer | Bethel | Away - Bethel MS Field [Directions] | 4:00 p.m. | 2:40pm | |
| Fri., 10/20 | V Girls Volleyball | Immaculate | Away - Immaculate HS [Directions] | W 3-0 | 2:40pm | |
| Fri., 10/20 | JV Girls Volleyball | Immaculate | Away - Immaculate HS [Directions] | 4:00 p.m. | 2:40pm | |
| Fri., 10/20 | FR Girls Volleyball | SWC Freshman Jamboree | Away [Directions] | 3:30 p.m. | 2:40pm | at Pomperaug |
| Fri., 10/20 | FR Girls Volleyball | Jamboree @ Pomperaug | Away - Pomperaug H.S. | 4:00 p.m. | 2:40pm | |
| Sat., 10/21 | JV Football | New Milford | Home [Directions] | 11:00 a.m. | ||
| Sat., 10/21 | V Field Hockey | Trumbull | Home - WHS Turf Field [Directions] | L 0-1 | non-league | |
| Sat., 10/21 | JV Field Hockey | Trumbull | Home - WHS Turf Field [Directions] | 2:30 p.m. | ||
| Sat., 10/21 | FR Girls Soccer | New Milford | Home - WHS Turf Field [Directions] | Cancelled | ||
| Mon., 10/23 | V Boys Soccer | Abbott Tech | Home - Weston HS Soccer field [Directions] | W 6-0 | Non-League Game | |
| Mon., 10/23 | V Girls Volleyball | Staples | Home - WHS Gymnasium [Directions] | L 0-3 | nonleague match | |
| Mon., 10/23 | JV Girls Volleyball | Staples | Home - WHS Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 10/23 | FR Girls Volleyball | Staples | Home - WHS Old Gymnasium [Directions] | 3:30 p.m. | ||
| Wed., 10/25 | V Field Hockey | Old Saybrook | Home - WHS Turf Field [Directions] | W 2-0 | nonleague game | |
| Wed., 10/25 | JV Field Hockey | Old Saybrook | Home - WHS Turf Field [Directions] | 5:00 p.m. | ||
| Thu., 10/26 | V Boys Cross Country | Hatters Freshman Invitational | Away [Directions] | 4:45 p.m. | 2:45pm | at Danbury High School |
| Thu., 10/26 | V Field Hockey | Masuk | Away - Benedict Stadium Field @ Masuk HS [Directions] | W 1-0 | 2:40pm | Non-League |
| Sat., 10/28 | V Football | Notre Dame-Fairfield | Away - McCarty Stadium at Notre Dame [Directions] | W 35-19 | 10:30am | |
| Mon., 10/30 | JV Football | Notre Dame-Fairfield | Home - WHS Stadium Field [Directions] | Cancelled | ||
| Fri., 11/3 | V Football | Brookfield | Home - WHS Stadium Field [Directions] | W 14-13 | ||
| Sat., 11/4 | JV Football | Brookfield | Away - BHS Stadium Field [Directions] | 10:00 a.m. | 8:00am | |
| Fri., 11/10 | V Football | New Fairfield | Away [Directions] | W 27-0 | 4:00PM | |
| Sat., 11/11 | JV Football | New Fairfield | Home [Directions] | 11:00 a.m. | ||
| Fri., 11/17 | JV Football | Joel Barlow | Away [Directions] | 5:30 p.m. | 3:45pm | |
| Thu., 11/23 | V Football | Joel Barlow | Home - WHS Stadium Field [Directions] | L 14-50 | ||
| Fri., 12/8 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - The Rinks at Shelton [Directions] | L 6-1 | ||
| Mon., 12/11 | V Girls Basketball | Trinity Catholic | Home - WHS Gymnasium [Directions] | W 46-38 | non-league | |
| Mon., 12/11 | JV Girls Basketball | Trinity Catholic | Home - WHS Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 12/11 | Miscellaneous Events | Unified Bowling | Away - Nutmeg Bowl, Fairfield | 2:30 p.m. | 2:00pm | |
| Wed., 12/13 | V Wrestling | Newtown | Away - Newtown HS Gymnasium [Directions] | Newtown 54 Weston 24 | 5:00pm | Cross Over Match |
| Wed., 12/13 | V Girls Basketball | Harding | Home - WHS Gymnasium [Directions] | W 51-22 | Non-League | |
| Wed., 12/13 | JV Girls Basketball | Harding | Home - WHS Gymnasium [Directions] | 5:00 p.m. | ||
| Wed., 12/13 | V Girls Ice Hockey | Hamden Coop | Home - The Rinks at Shelton [Directions] | L 0-16 | ||
| Sat., 12/16 | V Boys Basketball | Jonathan Law | Home - WHS Gymnasium [Directions] | L 53-62 | non-league | |
| Sat., 12/16 | JV Boys Basketball | Jonathan Law | Home - WHS Gymnasium [Directions] | 4:15 p.m. | ||
| Sat., 12/16 | FR Boys Basketball | Jonathan Law | Home - WHS Gymnasium [Directions] | 2:30 p.m. | ||
| Sat., 12/16 | V Boys Ice Hockey | Daniel Hand | Home - Danbury Ice Arena [Directions] | L 5-6 | ||
| Sat., 12/16 | V Boys Indoor Track | Hillhouse Varsity Invite | Away [Directions] | 9:00 a.m. | 7:30am | |
| Sat., 12/16 | V Boys Indoor Track | Reindeer Relays | Away [Directions] | 9:30 a.m. | 7:30am | |
| Sat., 12/16 | V Wrestling | Shelton Invitational | Away [Directions] | 9:30 a.m. | 7:30am | at Shelton HS |
| Sat., 12/16 | V Girls Basketball | Weaver | Away - Classical Magnet [Directions] | W 60-51 | 2:15pm | Non-League |
| Sat., 12/16 | JV Girls Basketball | Weaver | Away - Classical Magnet [Directions] | 4:30 p.m. | 2:15pm | |
| Sat., 12/16 | V Girls Ice Hockey | Guilford Coop | Away - East Haven Ice Rink [Directions] | L 0-7 | 11:00 am | |
| Sat., 12/16 | V Girls Indoor Track | Hillhouse Varsity Invite | Away [Directions] | 9:00 a.m. | 7:00am | |
| Sat., 12/16 | V Girls Indoor Track | Reindeer Relays | Away [Directions] | 9:30 a.m. | 8:00am | |
| Sun., 12/17 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Home - The Rinks at Shelton [Directions] | L 0-8 | ||
| Mon., 12/18 | V Boys Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | L 55-57 | 4:00pm | Non League |
| Mon., 12/18 | JV Boys Basketball | Westhill | Away - Main Gymnasium [Directions] | 5:15 p.m. | 4:00pm | |
| Mon., 12/18 | FR Boys Basketball | Westhill | Away - Main Gymnasium [Directions] | 4:00 p.m. | 2:40pm | |
| Tue., 12/19 | V Boys Swimming and Diving | New Milford | Away - Canterbury School [Directions] | Weston 105 New Milford 72 | 5:15pm | |
| Wed., 12/20 | V Boys Basketball | New Milford | Home - WHS Gymnasium [Directions] | L 43-69 | Non-League | |
| Wed., 12/20 | JV Boys Basketball | New Milford | Home - WHS Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 12/20 | FR Boys Basketball | New Milford | Home - WHS Gymnasium [Directions] | 3:45 p.m. | ||
| Wed., 12/20 | V Boys Ice Hockey | Housatonic Coop | Away - Hotchkiss [Directions] | L 0-6 | ||
| Wed., 12/20 | V Wrestling | Stratford | Home - WHS Old Gymnasium [Directions] | Weston 66 Stratford 18 | ||
| Wed., 12/20 | V Wrestling | Stratford | Away [Directions] | Cancelled | 4:00pm | |
| Wed., 12/20 | V Girls Ice Hockey | Daniel Hand Coop | Away - Northford Ice Pavilion [Directions] | L 0-9 | 2:15 pm | |
| Thu., 12/21 | V Girls Basketball | SMSA | Home - WHS Gymnasium [Directions] | W 57-36 | non-league | |
| Thu., 12/21 | JV Girls Basketball | SMSA | Home - WHS Gymnasium [Directions] | 4:30 p.m. | ||
| Fri., 12/22 | V Girls Basketball | Bunnell | Home - WHS Gymnasium [Directions] | W 51-35 | Non-League | |
| Fri., 12/22 | JV Girls Basketball | Bunnell | Home - WHS Gymnasium [Directions] | Cancelled | ||
| Fri., 12/22 | FR Girls Basketball | St. Joseph | Home - WHS Gymnasium [Directions] | 3:15 p.m. | ||
| Sat., 12/23 | V Boys Ice Hockey | Lyman Hall | Home - Danbury Ice Arena [Directions] | L 0-11 | ||
| Wed., 12/27 | V Boys Basketball | Haddam-Killingworth | Away [Directions] | W 65-31 | 10:00am | Plainville Holiday Tournament |
| Wed., 12/27 | JV Boys Basketball | Wright Tech | Away - Wright Tech [Directions] | 5:00 p.m. | 1:30pm | |
| Wed., 12/27 | FR Boys Basketball | Wright Tech | Away - Wright Tech [Directions] | 3:00 p.m. | 1:30pm | |
| Wed., 12/27 | V Boys Ice Hockey | Newtown/New Fairfield | Home - Danbury Ice Arena [Directions] | L 0-8 | ||
| Thu., 12/28 | V Boys Basketball | SMSA | Away [Directions] | W 60-49 | 4pm | Plainville Tournament Finals |
| Thu., 12/28 | V Boys Indoor Track | SCSU Invite | Away | 12:00 p.m. | 9:45am | at Southern CT State Univ. |
| Thu., 12/28 | V Wrestling | Harding/Bassick/Bridgeport Central | Away - Harding-Auxiliary Gym [Directions] | Weston 60 Harding 24 | 11:00am | nonleague |
| Thu., 12/28 | V Girls Indoor Track | SCSU Invite | Away | 12:00 p.m. | 9:45am | at Southern CT State Univ. |
| Sat., 12/30 | V Boys Ice Hockey | Newington Coop | Away - Newington Ice Arena - 300 Alumni Rd. in Newington [Directions] | L 0-11 | ||
| Tue., 1/2 | V Boys Swimming and Diving | Joel Barlow-Bethel Swim | Home - Weston MS Pool [Directions] | Weston 101 Joel Barlow 80 | ||
| Tue., 1/2 | V Girls Basketball | Masuk | Home - WHS Gymnasium [Directions] | W 53-37 | ||
| Tue., 1/2 | JV Girls Basketball | Masuk | Home - WHS Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/2 | FR Girls Basketball | Masuk | Home - WHS Gymnasium [Directions] | 3:30 p.m. | ||
| Wed., 1/3 | V Boys Ice Hockey | Masuk | Away - The Rinks at Shelton [Directions] | L 3-9 | ||
| Wed., 1/3 | V Boys Indoor Track | SWC JV Developmental | Away | 3:00 p.m. | 2:40pm | at Danbury Sports Dome |
| Wed., 1/3 | V Wrestling | Brookfield/Shepaug | Away - BHS Big Gym [Directions] | Weston 52 Brookfield 30 | 4:00pm | |
| Wed., 1/3 | V Girls Indoor Track | SWC JV Developmental | Away | 3:00 p.m. | 2:40pm | at Danbury Sports Dome |
| Sat., 1/6 | V Boys Basketball | Stafford | Away - Stafford HS [Directions] | W 57-28 | 2:30pm | nonleague |
| Sat., 1/6 | JV Boys Basketball | Stafford | Away [Directions] | 5:30 p.m. | 2:30pm | |
| Sat., 1/6 | V Boys Ice Hockey | Norwalk | Away - SoNo Ice House [Directions] | L 0-5 | ||
| Sat., 1/6 | V Boys Indoor Track | SWC Developmental | Away | 8:00 a.m. | 5:45am | at Wesleyan |
| Sat., 1/6 | V Girls Gymnastics | Pomperaug Invitational | Away - Pomperaug HS | 1st of 12 | PU:8:00 RE:1:30 | |
| Sat., 1/6 | V Girls Indoor Track | SWC Developmental | Away | 8:00 a.m. | 5:45am | at Wesleyan |
| Mon., 1/8 | V Wrestling | Bunnell | Home - WHS Gymnasium [Directions] | Weston 54 Bunnell 24 | ||
| Mon., 1/8 | V Girls Basketball | Bunnell | Away - Bunnell [Directions] | W 57-41 | 3:45pm | |
| Mon., 1/8 | JV Girls Basketball | Bunnell | Away - Bunnell [Directions] | 5:15 p.m. | 3:45pm | |
| Tue., 1/9 | V Boys Basketball | New Fairfield | Home - WHS Gymnasium [Directions] | W 41-38 | ||
| Tue., 1/9 | JV Boys Basketball | New Fairfield | Home - WHS Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/9 | FR Boys Basketball | New Fairfield | Home - WHS Gymnasium [Directions] | 3:30 p.m. | ||
| Tue., 1/9 | V Boys Swimming and Diving | Brookfield | Away - The Y.M.C.A. [Directions] | Weston 98 Brookfield 88 | 5:45pm | |
| Tue., 1/9 | V Girls Basketball | New Fairfield | Away - NFHS Gym [Directions] | W 49-33 | 3:45pm | |
| Tue., 1/9 | JV Girls Basketball | New Fairfield | Away - NFHS Gym [Directions] | 5:15 p.m. | 3:45pm | |
| Tue., 1/9 | FR Girls Basketball | New Fairfield | Away - NFHS Gym [Directions] | 3:30 p.m. | 2:40pm | |
| Wed., 1/10 | V Boys Ice Hockey | Sheehan | Away - Choate Rosemary Hall [Directions] | L 2-7 | ||
| Wed., 1/10 | V Boys Indoor Track | SWC JV Developmental | Away | 3:00 p.m. | 2:40pm | at Danbury Sports Dome |
| Wed., 1/10 | V Wrestling | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | Weston 54 Masuk 23 | 5:00pm | Cross Over Match |
| Wed., 1/10 | V Girls Indoor Track | SWC JV Developmental | Away | 3:00 p.m. | 2:40pm | at Danbury Sports Dome |
| Fri., 1/12 | V Boys Basketball | Notre Dame-Fairfield | Home - WHS Gymnasium [Directions] | L 85-52 | ||
| Fri., 1/12 | JV Boys Basketball | Notre Dame-Fairfield | Home - WHS Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/12 | FR Boys Basketball | Notre Dame-Fairfield | Home - WHS Gymnasium [Directions] | 3:30 p.m. | ||
| Fri., 1/12 | V Girls Basketball | Notre Dame-Fairfield | Away - Sister Marion Rielly Auditorium at Notre Dame [Directions] | L 44-45 | 3:45pm | |
| Fri., 1/12 | JV Girls Basketball | Notre Dame-Fairfield | Away - Sister Marion Rielly Auditorium at Notre Dame [Directions] | 5:15 p.m. | 3:45pm | |
| Fri., 1/12 | FR Girls Basketball | Notre Dame-Fairfield | Away - Sister Marion Rielly Auditorium at Notre Dame [Directions] | 3:30 p.m. | 2:40pm | |
| Fri., 1/12 | V Girls Gymnastics | Wilton | Home - Gymnastics & Cheer Academy [Directions] | Ludlowe - 133.40 Wilton- 127.65 | ||
| Sat., 1/13 | V Boys Ice Hockey | Shepaug Valley Ice Hockey | Home - Danbury Ice Arena [Directions] | W 6-3 | ||
| Sat., 1/13 | V Boys Indoor Track | SCC Coaches Invite | Away [Directions] | 2:30 p.m. | 12:00pm | |
| Sat., 1/13 | V Wrestling | Kearney Duals | Away [Directions] | Weston 54 Fairfield Prep 24 Weston 54 New Haven 30 Weston 43 Staples 42 | 8:45am | at Staples HS |
| Sat., 1/13 | V Girls Ice Hockey | Notre Dame-Fairfield | Away - Milford Ice Pavilion [Directions] | L 1-6 | 6:15 pm | |
| Sat., 1/13 | V Girls Indoor Track | SCC Coaches Invite | Away [Directions] | 9:00 a.m. | 6:45am | |
| Mon., 1/15 | V Boys Basketball | New Fairfield | Away - NFHS Gym [Directions] | W 43-39 | 10:30am | Non-League |
| Mon., 1/15 | JV Boys Basketball | New Fairfield | Away - NFHS MS Gym [Directions] | 12:00 p.m. | 10:30am | |
| Mon., 1/15 | V Boys Ice Hockey | Northeastern Shamrocks | Away - Bolton Ice Palace [Directions] | L 3-7 | ||
| Mon., 1/15 | V Boys Indoor Track | SWC Developmental | Away | 9:00 a.m. | 6:45am | at Wesleyan |
| Mon., 1/15 | V Girls Gymnastics | Fairfield Warde, Trumbull, Pomperaug, Nonnewaug | Home - Gymnastics & Cheer Academy [Directions] | Trumbull- 140.00 Ludlowe- 135.55 Pomperaug- 126.90 Warde- 122.80 Nonnewaug- 107.95 | ||
| Mon., 1/15 | V Girls Indoor Track | SWC Developmental | Away | 9:00 a.m. | 6:45am | at Wesleyan |
| Tue., 1/16 | V Boys Basketball | Stratford | Away - Needham Memorial Gymnasium [Directions] | L 48-67 | 3:45pm | |
| Tue., 1/16 | JV Boys Basketball | Stratford | Away - Needham Memorial Gymnasium [Directions] | 5:15 p.m. | 3:45pm | |
| Tue., 1/16 | FR Boys Basketball | Stratford | Away - Needham Memorial Gymnasium [Directions] | 3:30 p.m. | 2:40pm | |
| Tue., 1/16 | V Boys Swimming and Diving | Bunnell-Stratford | Home - Weston MS Pool [Directions] | Weston 92 Bunnell/Stratford 74 | ||
| Tue., 1/16 | V Girls Basketball | Stratford | Home - WHS Gymnasium [Directions] | W 66-39 | ||
| Tue., 1/16 | JV Girls Basketball | Stratford | Home - WHS Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/16 | V Girls Ice Hockey | Branford | Away - East Haven Ice Rink [Directions] | L 0-3 | 5:30 pm | |
| Thu., 1/18 | V Wrestling | Bethel | Home - WHS Gymnasium [Directions] | Bethel 51 Weston 18 | ||
| Fri., 1/19 | V Boys Basketball | New Milford | Away - New Milford HS [Directions] | L 54-68 | 3:45pm | |
| Fri., 1/19 | JV Boys Basketball | New Milford | Away - New Milford HS [Directions] | 5:15 p.m. | 3:45pm | |
| Fri., 1/19 | FR Boys Basketball | New Milford | Away - New Milford HS [Directions] | 3:30 p.m. | 2:40pm | |
| Fri., 1/19 | V Boys Indoor Track | Yale Classic Invitational | Away | 1:00 p.m. | 11:00am | |
| Fri., 1/19 | V Girls Basketball | New Milford | Home - WHS Gymnasium [Directions] | W 54-36 | ||
| Fri., 1/19 | JV Girls Basketball | New Milford | Home - WHS Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/19 | FR Girls Basketball | New Milford | Home - WHS Gymnasium [Directions] | Cancelled | ||
| Fri., 1/19 | FR Girls Basketball | Pomperaug | Home - WHS Gymnasium [Directions] | 3:30 p.m. | ||
| Fri., 1/19 | V Girls Ice Hockey | Guilford Coop | Home - The Rinks at Shelton [Directions] | L 0-3 | ||
| Fri., 1/19 | V Girls Indoor Track | Yale Classic Invitational | Away | 1:00 p.m. | 11:00am | |
| Sat., 1/20 | V Boys Indoor Track | Shoreline Invite | Away [Directions] | 11:00 a.m. | 8:00am | |
| Sat., 1/20 | V Boys Indoor Track | Yale Classic Invitational | Away | TBA | no bus | |
| Sat., 1/20 | V Wrestling | New Milford Tournament | Away [Directions] | 9:30 a.m. | 7:15am | at New Milford HS |
| Sat., 1/20 | V Girls Gymnastics | Foran | Home - Gymnastics & Cheer Academy [Directions] | Ludlowe- 135.60 Foran- 126.80 | ||
| Sat., 1/20 | V Girls Indoor Track | Shoreline Invite | Away [Directions] | 11:00 a.m. | 8:00am | |
| Sat., 1/20 | V Girls Indoor Track | Yale Classic Invitational | Away | TBA | no bus | |
| Mon., 1/22 | V Boys Ice Hockey | New Milford | Away - Canterbury School [Directions] | L 0-14 | ||
| Mon., 1/22 | V Girls Gymnastics | Greenwich, Fairfield Warde | Home - Gymnastics & Cheer Academy [Directions] | Greenwich- 141.90 Ludlowe- 132.90 | ||
| Mon., 1/22 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton Rinks [Directions] | W 5-1 | ||
| Tue., 1/23 | V Girls Basketball | Immaculate | Home - WHS Gymnasium [Directions] | W 49-33 | ||
| Tue., 1/23 | JV Girls Basketball | Immaculate | Home - WHS Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/23 | FR Girls Basketball | Immaculate | Home - WHS Gymnasium [Directions] | 3:30 p.m. | ||
| Wed., 1/24 | V Boys Basketball | Immaculate | Away - Immaculate HS [Directions] | L 33-57 | 3:45pm | |
| Wed., 1/24 | JV Boys Basketball | Immaculate | Away - Immaculate HS [Directions] | 5:15 p.m. | 3:45pm | |
| Wed., 1/24 | FR Boys Basketball | Immaculate | Away - Immaculate HS [Directions] | 3:30 p.m. | 2:40pm | |
| Wed., 1/24 | V Boys Indoor Track | SWC JV Developmental | Away | 3:00 p.m. | 2:40pm | at Danbury Sports Dome |
| Wed., 1/24 | V Boys Swimming and Diving | Pomperaug | Away - PHS Pool [Directions] | Pomperaug 99 Weston 87 | 4:15pm | |
| Wed., 1/24 | V Wrestling | Notre Dame-Fairfield | Away - Sister Marion Rielly Auditorium at Notre Dame [Directions] | Weston 51 Notre Dame 37 | 5:00pm | |
| Wed., 1/24 | V Girls Indoor Track | SWC JV Developmental | Away | 3:00 p.m. | 2:40pm | at Danbury Sports Dome |
| Thu., 1/25 | JV Boys Ice Hockey | Newtown/New Fairfield | Home - Danbury Ice Arena [Directions] | 7:50 p.m. | ||
| Fri., 1/26 | V Boys Basketball | Newtown | Home - WHS Gymnasium [Directions] | W 64-57 | ||
| Fri., 1/26 | JV Boys Basketball | Newtown | Home - WHS Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/26 | FR Boys Basketball | Newtown | Home - WHS Gymnasium [Directions] | 3:30 p.m. | ||
| Fri., 1/26 | V Wrestling | Brien McMahon | Home - WHS Old Gymnasium [Directions] | Brien McMahon 48 Weston 30 | nonleague | |
| Fri., 1/26 | V Girls Basketball | Newtown | Away - Newtown HS Gymnasium [Directions] | L 40-31 | 3:45pm | |
| Fri., 1/26 | JV Girls Basketball | Newtown | Away - Newtown HS Gymnasium [Directions] | 5:15 p.m. | 3:45pm | |
| Fri., 1/26 | FR Girls Basketball | Newtown | Away - Newtown HS Gymnasium [Directions] | 3:30 p.m. | 2:40pm | |
| Fri., 1/26 | V Girls Ice Hockey | Daniel Hand Coop | Home - The Rinks at Shelton [Directions] | L 1-6 | ||
| Sat., 1/27 | V Boys Ice Hockey | Wethersfield | Home - Danbury Ice Arena [Directions] | L 1-5 | ||
| Sat., 1/27 | V Girls Basketball | New Milford | Away - New Milford HS [Directions] | W 36-21 | 2:00pm | nonleague |
| Sat., 1/27 | JV Girls Basketball | New Milford | Away - New Milford HS [Directions] | 3:30 p.m. | 2:00pm | |
| Sat., 1/27 | FR Girls Basketball | New Milford | Away - New Milford HS [Directions] | Cancelled | ||
| Sun., 1/28 | V Girls Gymnastics | Darien, Fairfield Warde | Away - Gymnastics & Cheer Academy, Fairfield [Directions] | Ludlowe- 133.00 Darien- 126.90 | ||
| Sun., 1/28 | V Girls Ice Hockey | Notre Dame-Fairfield | Home - The Rinks at Shelton [Directions] | L 1-5 | ||
| Mon., 1/29 | Unified Sports Basketball | The Institute of Professional Practice | Home - WHS Gymnasium [Directions] | 2:30 p.m. | ||
| Tue., 1/30 | V Boys Basketball | Bethel | Home - WHS Gymnasium [Directions] | W 59-52 | ||
| Tue., 1/30 | JV Boys Basketball | Bethel | Home - WHS Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/30 | FR Boys Basketball | Bethel | Home - WHS Gymnasium [Directions] | 3:30 p.m. | ||
| Tue., 1/30 | V Boys Swimming and Diving | Newtown | Home - Weston MS Pool [Directions] | Weston 96 Newtown 88 | ||
| Tue., 1/30 | V Girls Basketball | Bethel | Away - Bethel HS [Directions] | L 32-42 | 3:45pm | |
| Tue., 1/30 | JV Girls Basketball | Bethel | Away - Bethel HS [Directions] | 5:15 p.m. | 3:45pm | |
| Tue., 1/30 | V Girls Gymnastics | Daniel Hand | Away - Polson Gymnastics Gym/DHHS Campus [Directions] | Hand- 133.50 Ludlowe- 131.50 | PU:2:30 RE:6:30 | |
| Wed., 1/31 | FR Boys Basketball | New Fairfield | Away - NFHS MS Gym [Directions] | 6:00 p.m. | 4:30pm | travel with Wreslting |
| Wed., 1/31 | V Boys Ice Hockey | Brookfield | Away - Danbury Ice Arena [Directions] | L 3-5 | ||
| Wed., 1/31 | V Wrestling | New Fairfield | Home - WHS Gymnasium [Directions] | Weston 42 New Fairfield 37 | 4:00pm | travel with Frosh Boys Bball |
| Wed., 1/31 | V Girls Basketball | Bassick | Away - Bassick Gymnasium [Directions] | W 52-45 | 2:40pm | non-league |
| Wed., 1/31 | JV Girls Basketball | Bassick | Away - Bassick Gymnasium [Directions] | 4:00 p.m. | 2:40pm | |
| Wed., 1/31 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Conners Ice Rink [Directions] | L 0-2 | 5:00 pm | |
| Thu., 2/1 | V Girls Ice Hockey | Lauralton Hall | Away - Wonderland of Ice [Directions] | W 1-0 (Forfeit( | 1:45 pm | |
| Fri., 2/2 | JV Boys Basketball | Joel Barlow | Away - JBHS Lower Gym [Directions] | 5:00 p.m. | 2:40pm | |
| Fri., 2/2 | FR Boys Basketball | Joel Barlow | Away - JBHS Lower Gym [Directions] | 3:30 p.m. | 2:40pm | |
| Fri., 2/2 | JV Boys Ice Hockey | Brookfield | Home - Danbury Ice Arena [Directions] | 4:30 p.m. | ||
| Fri., 2/2 | JV Girls Basketball | Joel Barlow | Home - WHS Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 2/2 | FR Girls Basketball | Joel Barlow | Home - WHS Gymnasium [Directions] | 3:30 p.m. | ||
| Fri., 2/2 | V Girls Gymnastics | Westhill, New Canaan | Home - Gymnastics & Cheer Academy [Directions] | Ludlowe- 134.95 Westhill- 110.40 New Canaan- 108.8 | ||
| Fri., 2/2 | V Girls Ice Hockey | West Haven/SHA | Home - The Rinks at Shelton [Directions] | L 0-6 | ||
| Sat., 2/3 | V Boys Basketball | Joel Barlow | Away - JBHS Lower Gym [Directions] | L 46-48 | 11:30am | |
| Sat., 2/3 | V Girls Basketball | Joel Barlow | Home - WHS Gymnasium [Directions] | W 37-28 | ||
| Mon., 2/5 | Miscellaneous Events | Unified Bowling | Away - Nutmeg Bowl, Fairfield | 2:30 p.m. | 2:00pm | |
| Tue., 2/6 | V Boys Basketball | Pomperaug | Home - WHS Gymnasium [Directions] | L 52-60 | ||
| Tue., 2/6 | JV Boys Basketball | Pomperaug | Home - WHS Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 2/6 | FR Boys Basketball | Pomperaug | Home - WHS Gymnasium [Directions] | 3:30 p.m. | ||
| Tue., 2/6 | V Boys Swimming and Diving | Bethel | Away - WCSU Pool [Directions] | Weston 89 Bethel 75 | 2:40pm | |
| Tue., 2/6 | V Wrestling | New Milford | Away - New Milford HS [Directions] | Weston 6 New Milford 68 | 4:15pm | Cross Over Match |
| Tue., 2/6 | V Girls Basketball | Pomperaug | Away - PHS Main Gym [Directions] | L 50-60 | 3:45pm | |
| Tue., 2/6 | JV Girls Basketball | Pomperaug | Away - PHS Main Gym [Directions] | 5:15 p.m. | 3:45pm | |
| Tue., 2/6 | FR Girls Basketball | Pomperaug | Away - PHS Main Gym [Directions] | 3:30 p.m. | 2:40pm | |
| Tue., 2/6 | V Girls Gymnastics | Staples | Home - Gymnastics & Cheer Academy [Directions] | Ludlowe-131.65 Staples-121.35 | ||
| Thu., 2/8 | V Boys Basketball | Kolbe Cathedral | Home - WHS Gymnasium [Directions] | L 73-47 | ||
| Thu., 2/8 | JV Boys Basketball | Kolbe Cathedral | Home - WHS Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 2/9 | FR Boys Basketball | Wright Tech | Home - WHS Gymnasium [Directions] | 3:30 p.m. | ||
| Fri., 2/9 | V Girls Basketball | Kolbe Cathedral | Away - Shehan Center [Directions] | L 30-33 | 3:45pm | |
| Fri., 2/9 | JV Girls Basketball | Kolbe Cathedral | Away - Shehan Center [Directions] | 5:15 p.m. | 3:45pm | |
| Fri., 2/9 | V Girls Ice Hockey | Branford | Home - The Rinks at Shelton [Directions] | L 0-4 | ||
| Sat., 2/10 | V Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena [Directions] | L 3-6 | ||
| Sun., 2/11 | V Boys Ice Hockey | Eastern CT Eagles | Away - Connecticut College [Directions] | L 3-8 | ||
| Sun., 2/11 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Away - The Rinks at Shelton [Directions] | L 0-8 | ||
| Tue., 2/13 | V Boys Basketball | Brookfield | Away - BHS Big Gym [Directions] | L 56-70 | 3:45pm | |
| Tue., 2/13 | JV Boys Basketball | Brookfield | Away - BHS Big Gym [Directions] | 5:15 p.m. | 3:45pm | |
| Tue., 2/13 | FR Boys Basketball | Brookfield | Away - BHS Big Gym [Directions] | 3:30 p.m. | 2:40pm | |
| Tue., 2/13 | V Boys Swimming and Diving | New Fairfield | Home - Weston MS Pool [Directions] | Weston 102 New Fairfield 82 | ||
| Tue., 2/13 | V Girls Basketball | Brookfield | Home - WHS Gymnasium [Directions] | W 50-24 | ||
| Tue., 2/13 | JV Girls Basketball | Brookfield | Home - WHS Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 2/13 | FR Girls Basketball | Immaculate | Home - WHS Gymnasium [Directions] | 3:45 p.m. | ||
| Tue., 2/13 | V Girls Ice Hockey | West Haven/SHA | Away - Bennett Rink [Directions] | L 0-5 | 4:45 pm | |
| Wed., 2/14 | V Girls Ice Hockey | Hamden Coop | Away - Lou Astorino Ice Rink [Directions] | L 0-6 | 5:00 pm | |
| Thu., 2/15 | V Boys Basketball | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | L 40-47 | 3:45pm | |
| Thu., 2/15 | JV Boys Basketball | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | 5:15 p.m. | 3:45pm | |
| Thu., 2/15 | FR Boys Basketball | Masuk | Away - David Strong Gymnasium @ Masuk HS [Directions] | 3:30 p.m. | 2:40pm | |
| Thu., 2/15 | V Boys Swimming and Diving | Holy Cross | Home - Weston MS Pool [Directions] | Holy Cross 95 Weston 91 | Non-League | |
| Thu., 2/15 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - So No Icehouse - Norwalk [Directions] | L 2-7 | 4:30 pm | |
| Fri., 2/16 | V Boys Ice Hockey | Wilton | Away - Winter Garden Rink-Ridgefield [Directions] | W 5-4(OT) | ||
| Fri., 2/16 | V Girls Gymnastics | Oxford, Newtown, Pomperaug, Nonnewaug | Away - Auxiliary Gym [Directions] | Ludlowe-135.45 Newtown- 130.80 Oxford- 130.45 | PU:4:15 RE:7:30 | |
| Fri., 2/16 | V Girls Ice Hockey | Lauralton Hall | Home - The Rinks at Shelton [Directions] | W Forfeit | ||
| Tue., 2/20 | V Boys Basketball | Bunnell | Home - WHS Gymnasium [Directions] | L 68-74 | ||
| Tue., 2/20 | JV Boys Basketball | Bunnell | Home - WHS Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 2/20 | FR Boys Basketball | Bunnell | Home - WHS Gymnasium [Directions] | 3:30 p.m. | ||
| Tue., 2/20 | V Boys Swimming and Diving | Masuk | Home - Weston MS Pool [Directions] | 4:00 p.m. | ||
| Wed., 2/21 | V Boys Ice Hockey | Masuk | Home - Danbury Ice Arena [Directions] | L 1-6 | ||
| Thu., 2/22 | JV Girls Basketball | Wright Tech | Away - Wright Tech HS [Directions] | 3:45 p.m. | 2:45pm | |
| Sat., 2/24 | V Boys Ice Hockey | Milford Coop | Away - Milford Ice Pavilion [Directions] | W 7-4 | ||
| Mon., 2/26 | Unified Sports Basketball | The Institute of Professional Practice | Home - WHS Gymnasium [Directions] | 2:30 p.m. | ||
| Tue., 2/27 | V Boys Ice Hockey | Housatonic Coop | Home - Danbury Ice Arena [Directions] | L 3-6 | ||
| Wed., 2/28 | V Boys Ice Hockey | Shepaug Valley Ice Hockey | Away - Gunnery Rink [Directions] | L 3-4(OT) | ||
| Mon., 3/12 | Miscellaneous Events | Unified Bowling | Away - Nutmeg Bowl, Fairfield | 2:30 p.m. | 2:00pm | |
| Sat., 3/31 | V Baseball | Westhill | Away - Westhill Baseball Field [Directions] | L 0-11 | 8:45am | nonleague |
| Sat., 3/31 | JV Baseball | Westhill | Away - Rippowam MS [Directions] | 10:30 a.m. | 8:45am | |
| Sat., 3/31 | FR Baseball | Westhill | Home - Revson Field, Weston [Directions] | 10:30 a.m. | ||
| Sat., 3/31 | V Boys Tennis | Wilton | Home - WHS Tennis Courts [Directions] | W 4-3 | non-league | |
| Sat., 3/31 | V Softball | Abbott Tech | Away - Hatters Park [Directions] | L 12-24 | 10:15am | nonleague |
| Sat., 3/31 | V Girls Tennis | Wilton | Away - Wilton Tennis Courts [Directions] | L 2-5 | 10:00am | non-league |
| Wed., 4/4 | V Boys Golf | New Milford | Home - Aspetuck Valley Country Club [Directions] | Weston 185 New Milford 234 | Non-League | |
| Wed., 4/4 | V Boys Lacrosse | Bethel | Home - WHS Turf Field [Directions] | W 17-4 | 3:00pm | |
| Wed., 4/4 | JV Boys Lacrosse | Bethel | Home - WHS Stadium Field [Directions] | 5:15 p.m. | 3:00pm | |
| Wed., 4/4 | V Girls Lacrosse | Bethel | Home - WHS Turf Field [Directions] | W 17-7 | ||
| Wed., 4/4 | JV Girls Lacrosse | Bethel | Home - WHS Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 4/5 | V Baseball | Wilton | Away - WHS Varsity Baseball Field [Directions] | L 0-3 | 2:45pm | nonleague |
| Thu., 4/5 | JV Baseball | Wilton | Away - JV Baseball Field [Directions] | 4:00 p.m. | 2:45pm | |
| Thu., 4/5 | V Boys Lacrosse | Masuk | Home - WHS Turf Field [Directions] | W 13-2 | ||
| Thu., 4/5 | V Girls Golf | Stratford | Away - Mill River C.C. [Directions] | Weston 231 Stratford 332 | ||
| Thu., 4/5 | V Girls Lacrosse | Masuk | Away - Benedict Stadium Field @ Masuk HS [Directions] | L 3-10 | 3:30pm | |
| Thu., 4/5 | JV Girls Lacrosse | Masuk | Away - Benedict Stadium Field @ Masuk HS [Directions] | 5:00 p.m. | 3:30pm | |
| Thu., 4/5 | V Girls Tennis | Newtown | Home - WHS Tennis Courts [Directions] | W 7-0 | Non-League | |
| Fri., 4/6 | V Boys Outdoor Track | Fairfield Ludlowe, Bridgeport Central | Away - Taft Field [Directions] | Cancelled | nonleague | |
| Sat., 4/7 | V Baseball | Joel Barlow | Home - Revson Field, Weston [Directions] | W 7-6 | nonleague | |
| Sat., 4/7 | V Boys Lacrosse | William Floyd (NY) | Away | W 8-5 | TBA | nonleague at Bayport Blue Point HS |
| Sat., 4/7 | V Girls Lacrosse | Daniel Hand | Home - WHS Turf Field [Directions] | L 7-20 | nonleague | |
| Sat., 4/7 | JV Girls Lacrosse | Daniel Hand | Home - WHS Turf Field [Directions] | 10:00 a.m. | ||
| Mon., 4/9 | V Baseball | Brien McMahon | Away - Pride Field BMHS [Directions] | W 9-7 | 10:15am | nonleague |
| Mon., 4/9 | JV Baseball | Brien McMahon | Away - Roton Field [Directions] | 12:00 p.m. | 10:15am | |
| Mon., 4/9 | V Boys Golf | Brookfield | Home - Aspetuck Valley Country Club [Directions] | Weston 179 Brookfield 222 | ||
| Mon., 4/9 | V Boys Tennis | Brookfield | Away - BHS Tennis Courts [Directions] | W 7-0 | 2:40pm | |
| Mon., 4/9 | V Girls Golf | Notre Dame-Fairfield | Home - Aspetuck Valley Country Club [Directions] | Weston 277 Notre Dame-Fairfield 282 | ||
| Mon., 4/9 | JV Softball | Wright Tech | Home - Hurlbutt El. School, Weston [Directions] | 4:00 p.m. | ||
| Mon., 4/9 | V Girls Tennis | Brookfield | Home - WHS Tennis Courts [Directions] | W 7-0 | ||
| Tue., 4/10 | V Boys Golf | New Milford | Away - Candlewood Valley [Directions] | Weston 174 New Milford 208 | ||
| Tue., 4/10 | V Boys Lacrosse | Joel Barlow | Home - WHS Turf Field [Directions] | W 6-5 | ||
| Tue., 4/10 | JV Boys Lacrosse | Joel Barlow | Home - WHS Turf Field [Directions] | 6:00 p.m. | ||
| Tue., 4/10 | V Girls Golf | Brookfield | Home - Aspetuck Valley Country Club [Directions] | Brookfield 243 Weston 264 | ||
| Tue., 4/10 | V Girls Lacrosse | Joel Barlow | Away - Field I (Stadium) [Directions] | L 2-12 | 2:40pm | |
| Tue., 4/10 | JV Girls Lacrosse | Joel Barlow | Away - Field I (Stadium) [Directions] | 4:00 p.m. | 2:40pm | |
| Tue., 4/10 | V Softball | Bridgeport Central | Home - Hurlbutt El. School, Weston [Directions] | L 13-21 | nonleague | |
| Tue., 4/10 | JV Softball | Bridgeport Central | Home - Hurlbutt El. School, Weston [Directions] | 1:00 p.m. | ||
| Tue., 4/10 | V Girls Tennis | Bunnell | Away - Bunnell Tennis Courts [Directions] | W 5-2 | 10:00am | |
| Wed., 4/11 | V Baseball | Immaculate | Away - Immaculate [Directions] | L 2-4 | 2:30pm | Non-League |
| Wed., 4/11 | FR Baseball | Bethel | Home - Revson Field, Weston [Directions] | 4:15 p.m. | ||
| Wed., 4/11 | V Boys Tennis | Immaculate | Away - Rogers Park [Directions] | W 7-0 | 2:30pm | |
| Wed., 4/11 | V Softball | Bunnell | Home - Hurlbutt El. School, Weston [Directions] | W 15-9 | Non-League | |
| Wed., 4/11 | V Girls Tennis | Immaculate | Home - WHS Tennis Courts [Directions] | W 5-2 | ||
| Thu., 4/12 | JV Baseball | Immaculate | Home - Revson Field, Weston [Directions] | 4:15 p.m. | ||
| Thu., 4/12 | V Boys Lacrosse | Pomperaug | Home - WHS Turf Field [Directions] | W 7-3 | ||
| Thu., 4/12 | JV Boys Lacrosse | Pomperaug | Home - WHS Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 4/12 | V Girls Lacrosse | Pomperaug | Away - Sports Complex & Track [Directions] | L 6-17 | 3:15pm | |
| Thu., 4/12 | JV Girls Lacrosse | Pomperaug | Away - Sports Complex & Track [Directions] | 5:15 p.m. | 3:15pm | |
| Thu., 4/12 | V Softball | Wilton | Home - Hurlbutt El. School, Weston [Directions] | L 2-14 | nonleague | |
| Thu., 4/12 | JV Softball | Bunnell | Away - Bunnell Softball Field [Directions] | 4:15 p.m. | 2:40pm | |
| Fri., 4/13 | V Baseball | Brookfield | Away - BHS Baseball Field [Directions] | W 6-4 | 2:40pm | Non-League |
| Fri., 4/13 | FR Baseball | Brookfield | Home - Revson Field, Weston [Directions] | 4:15 p.m. | ||
| Fri., 4/13 | V Softball | New Fairfield | Home - Hurlbutt El. School, Weston [Directions] | L 3-8 | Non-League | |
| Sat., 4/14 | JV Baseball | Brookfield | Home - Revson Field, Weston [Directions] | 10:00 a.m. | ||
| Sat., 4/14 | JV Boys Lacrosse | Fordham Prep (NY) | Home - WHS Turf Field [Directions] | 3:00 p.m. | ||
| Tue., 4/17 | V Boys Lacrosse | Immaculate | Away - Mustang Valley [Directions] | W 17-3 | 2:40pm | |
| Tue., 4/17 | V Boys Outdoor Track | Bunnell, Kolbe Cathedral | Home - WHS Track [Directions] | Weston 95 Bunnell 55 Weston 148 Kolbe 2 Bunnell 133 Kolbe 2 | ||
| Tue., 4/17 | V Girls Golf | Joel Barlow | Home - Aspetuck Valley Country Club [Directions] | Joel Barlow 246 Weston 226 | ||
| Tue., 4/17 | V Softball | Stratford | Away - Birdseye Field [Directions] | L 5-17 | 2:40pm | Non-League |
| Wed., 4/18 | V Baseball | Joel Barlow | Away - Field G (Baseball) [Directions] | W 11-0 | 2:40pm | |
| Wed., 4/18 | FR Baseball | Joel Barlow | Home - Revson Field, Weston [Directions] | 4:15 p.m. | ||
| Wed., 4/18 | V Boys Tennis | Bethel | Away - Bethel HS [Directions] | W 7-0 | 2:40pm | |
| Wed., 4/18 | V Girls Golf | Joel Barlow | Away - Redding Country Club [Directions] | Joel Barlow 228 Weston 242 | ||
| Wed., 4/18 | V Girls Outdoor Track | Bunnell, Kolbe Cathedral | Away - Bunnell Track [Directions] | Weston 113 Bunnell 37 Weston 130 Kolbe 20 | 2:40pm | |
| Wed., 4/18 | V Softball | Joel Barlow | Away - Field E (Softball) [Directions] | L 1-20 | ||
| Wed., 4/18 | JV Softball | Danbury | Away [Directions] | 4:00 p.m. | 2:40pm | |
| Thu., 4/19 | V Boys Golf | Stratford | Home - Aspetuck Valley Country Club [Directions] | Weston 182 Stratford 288 | ||
| Thu., 4/19 | V Boys Lacrosse | New Fairfield | Away - Rebel Turf [Directions] | L 3-9 | 2:40pm | |
| Thu., 4/19 | JV Boys Lacrosse | New Fairfield | Away - Rebel Turf [Directions] | 6:00 p.m. | 2:40pm | |
| Thu., 4/19 | V Girls Lacrosse | New Fairfield | Home - WHS Turf Field [Directions] | L 6-16 | ||
| Thu., 4/19 | JV Girls Lacrosse | New Fairfield | Home - WHS Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 4/20 | FR Baseball | Joel Barlow | Home - Revson Field, Weston [Directions] | 4:00 p.m. | ||
| Fri., 4/20 | V Boys Tennis | Masuk | Away - Wolfe Park Tennis Courts [Directions] | W 7-0 | 2:40pm | |
| Fri., 4/20 | V Softball | Bunnell | Away - Bunnell Softball Field [Directions] | W 13-5 | ||
| Fri., 4/20 | V Girls Tennis | Masuk | Home - WHS Tennis Courts [Directions] | W 7-0 | ||
| Sat., 4/21 | V Baseball | Bunnell | Away - Bunnell Baseball Field [Directions] | W 2-1 | 11:15am | |
| Sat., 4/21 | JV Baseball | Bunnell | Home - Revson Field, Weston [Directions] | 10:00 a.m. | ||
| Sat., 4/21 | V Boys Lacrosse | Notre Dame-West Haven | Home - WHS Turf Field [Directions] | W 13-10 | nonleague | |
| Sat., 4/21 | JV Boys Lacrosse | Notre Dame-West Haven | Home - WHS Turf Field [Directions] | 12:30 p.m. | ||
| Sat., 4/21 | V Boys Outdoor Track | Tournament Game - Opponent Not Known | Away - Plainfield HS | 9:30 a.m. | 6:30am | |
| Sat., 4/21 | JV Boys Tennis | Wilton | Home - WHS Tennis Courts [Directions] | 12:00 p.m. | ||
| Sat., 4/21 | V Girls Lacrosse | Stamford | Home - WHS Turf Field [Directions] | W 15-5 | nonleague | |
| Sat., 4/21 | JV Girls Lacrosse | Stamford | Home - WHS Turf Field [Directions] | 9:00 a.m. | ||
| Sat., 4/21 | JV Softball | Bunnell | Home - Hurlbutt El. School, Weston [Directions] | 10:00 a.m. | ||
| Sat., 4/21 | V Girls Tennis | Bethel | Home - WHS Tennis Courts [Directions] | W 7-0 | ||
| Sat., 4/21 | JV Girls Tennis | Wilton | Away - Wilton Tennis Courts [Directions] | 10:00 a.m. | 9:15am | |
| Mon., 4/23 | V Baseball | Masuk | Home - Revson Field, Weston [Directions] | L 3-6 | ||
| Mon., 4/23 | FR Baseball | Masuk | Home - Revson Field, Weston [Directions] | 4:15 p.m. | ||
| Mon., 4/23 | V Boys Golf | Newtown | Home - Aspetuck Valley Country Club [Directions] | Weston 182 Newtown 190 | ||
| Mon., 4/23 | V Boys Tennis | Pomperaug | Home - WHS Tennis Courts [Directions] | W 7-0 | ||
| Mon., 4/23 | V Girls Golf | Immaculate | Home - Aspetuck Valley Country Club [Directions] | Weston 234 Immaculate 264 | ||
| Mon., 4/23 | V Girls Outdoor Track | Pomperaug, Joel Barlow, New Milford | Home - WHS Track [Directions] | Weston 80 Pomperaug 70 Weston 91 New Milford 62 Weston 88 Joel Barlow 52 | ||
| Mon., 4/23 | V Softball | Masuk | Home - Hurlbutt El. School, Weston [Directions] | L 0-12 | ||
| Mon., 4/23 | V Girls Tennis | Pomperaug | Away - PHS Tennis Courts [Directions] | W 6-1 | 2:40pm | |
| Tue., 4/24 | V Baseball | Immaculate | Home - Revson Field, Weston [Directions] | L 1-2 | ||
| Tue., 4/24 | JV Baseball | Masuk | Away - John Giampaolo Baseball Field @ Masuk HS [Directions] | 4:15 p.m. | 2:40pm | |
| Tue., 4/24 | V Boys Golf | Masuk | Away - Whitney Farms Golf Course [Directions] | Masuk 172 Weston 188 | ||
| Tue., 4/24 | V Boys Lacrosse | Notre Dame-Fairfield | Home - WHS Turf Field [Directions] | W 17-1 | ||
| Tue., 4/24 | JV Boys Lacrosse | Notre Dame-Fairfield | Home - WHS Turf Field [Directions] | Cancelled | ||
| Tue., 4/24 | V Boys Outdoor Track | Pomperaug, Joel Barlow, New Milford | Away - Sports Complex & Track [Directions] | Weston 81 Pomperaug 69 Weston 112.5 Barlow. 37.5 New Milford 84 Weston 66 | 2:40pm | |
| Tue., 4/24 | V Boys Tennis | Newtown | Home - WHS Tennis Courts [Directions] | W 7-0 | ||
| Tue., 4/24 | V Girls Golf | Brookfield | Away - Sunset Hill Golf Course [Directions] | Weston 204 Brookfield 220 | ||
| Tue., 4/24 | V Girls Lacrosse | Notre Dame-Fairfield | Away - Park Avenue Field at Notre Dame [Directions] | W 16-5 | 2:40pm | |
| Tue., 4/24 | JV Girls Lacrosse | Notre Dame-Fairfield | Away - Park Avenue Field at Notre Dame [Directions] | 5:30 p.m. | 2:40pm | |
| Tue., 4/24 | V Softball | Immaculate | Home - Hurlbutt El. School, Weston [Directions] | L 13-15 | ||
| Tue., 4/24 | JV Softball | Masuk | Away - Wolfe Park Softball Field - # 4 [Directions] | 4:15 p.m. | 2:40pm | |
| Tue., 4/24 | V Girls Tennis | Stratford | Home - WHS Tennis Courts [Directions] | W 7-0 | ||
| Wed., 4/25 | JV Softball | Danbury | Home - Weston MS [Directions] | Cancelled | ||
| Thu., 4/26 | V Baseball | Fairfield Warde | Home - Revson Field, Weston [Directions] | L 6-11 | nonleague | |
| Thu., 4/26 | JV Baseball | Immaculate | Away - Immaculate [Directions] | 4:15 p.m. | 2:40pm | |
| Thu., 4/26 | V Boys Lacrosse | Daniel Hand | Home - WHS Turf Field [Directions] | W 6-5 | nonleague | |
| Thu., 4/26 | JV Boys Lacrosse | Daniel Hand | Home - WHS Stadium Field [Directions] | 5:30 p.m. | ||
| Thu., 4/26 | V Boys Tennis | Glastonbury | Away - Glastonbury HS [Directions] | W 6-1 | nonleague | |
| Thu., 4/26 | V Girls Lacrosse | Stratford/Bunnell | Home - WHS Turf Field [Directions] | W 16-10 | ||
| Thu., 4/26 | JV Girls Lacrosse | Stratford/Bunnell | Home - WHS Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 4/26 | V Softball | Brien McMahon | Home - Weston [Directions] | W 12-6 | 2:40pm | nonleague |
| Thu., 4/26 | V Girls Tennis | Newtown | Away - Newtown HS [Directions] | W 6-1 | 2:40pm | |
| Thu., 4/26 | JV Girls Tennis | Fairfield Ludlowe | Home - WHS Tennis Courts [Directions] | 5:00 p.m. | ||
| Fri., 4/27 | JV Baseball | Bethel | Away - Parloa Park [Directions] | 4:00 p.m. | 2:40pm | |
| Fri., 4/27 | JV Softball | Bethel | Away - Kisling field [Directions] | 4:00 p.m. | 2:40pm | |
| Sat., 4/28 | FR Baseball | Bethel | Away - Hunt Field at Bethel HS [Directions] | 1:00 p.m. | 11:30am | |
| Sat., 4/28 | V Boys Lacrosse | North Rockland (NY) | Home - WHS Turf Field [Directions] | W 15-7 | nonleague | |
| Sat., 4/28 | V Boys Outdoor Track | O'Grady Relays | Away [Directions] | 9:00 a.m. | 7:20am | at Danbury HS |
| Sat., 4/28 | V Boys Tennis | Bunnell | Home - WHS Tennis Courts [Directions] | W 7-0 | ||
| Sat., 4/28 | JV Boys Tennis | Staples | Home - WHS Tennis Courts [Directions] | 10:00 a.m. | ||
| Sat., 4/28 | V Girls Lacrosse | North Rockland (NY) | Home - WHS Turf Field [Directions] | L 8-17 | nonleague | |
| Sat., 4/28 | V Girls Outdoor Track | O'Grady Relays | Away [Directions] | 9:00 a.m. | 7:20am | at Danbury HS |
| Sat., 4/28 | V Softball | Bethel | Home - Hurlbutt El. School, Weston [Directions] | L 4-9 | ||
| Sat., 4/28 | V Girls Tennis | Glastonbury | Home - WHS Tennis Courts [Directions] | L 1-6 | nonleague | |
| Sat., 4/28 | JV Girls Tennis | Staples | Away - Staples HS-Tennis Courts [Directions] | 12:30 p.m. | 11:45am | |
| Mon., 4/30 | V Baseball | Kolbe Cathedral | Away - Veterans Park [Directions] | L 2-5 | 2:40pm | |
| Mon., 4/30 | JV Baseball | Joel Barlow | Home - Revson Field, Weston [Directions] | 4:00 p.m. | ||
| Mon., 4/30 | V Boys Golf | Pomperaug | Home - Aspetuck Valley Country Club [Directions] | Weston 183 Pomperaug 185 | Non-League | |
| Mon., 4/30 | V Girls Golf | Masuk | Home - Aspetuck Valley Country Club [Directions] | Masuk 217 Weston 223 | ||
| Mon., 4/30 | V Girls Outdoor Track | Newtown, Immaculate | Home - WHS Track [Directions] | Weston 97 Immaculate 53 Newtown 105 Weston 45 | 2:40pm | |
| Mon., 4/30 | V Softball | Kolbe Cathedral | Away - Cal Ripken Field at Longfellow Park [Directions] | W 15-1 | ||
| Mon., 4/30 | V Girls Tennis | Notre Dame-Fairfield | Home - WHS Tennis Courts [Directions] | W 7-0 | ||
| Tue., 5/1 | V Baseball | Bethel | Home - Revson Field, Weston [Directions] | W 4-0 | ||
| Tue., 5/1 | V Boys Golf | Pomperaug | Away [Directions] | Weston 178 Pomperaug 184 | 1:45pm | |
| Tue., 5/1 | V Boys Lacrosse | Newtown | Home - WHS Turf Field [Directions] | L 4-10 | ||
| Tue., 5/1 | JV Boys Lacrosse | Newtown | Home - WHS Turf Field [Directions] | 5:00 p.m. | ||
| Tue., 5/1 | V Boys Outdoor Track | Newtown, Immaculate | Home - Weston HS [Directions] | Newtown 103 Weston 47 Weston 114 Immaculate 31 | ||
| Tue., 5/1 | V Boys Tennis | New Canaan | Home - WHS Tennis Courts [Directions] | L 3-4 | nonleague | |
| Tue., 5/1 | JV Boys Tennis | New Canaan | Home - WHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/1 | V Girls Golf | Bunnell | Away - Oronoque Country Club [Directions] | Weston 218 Bunnell 276 | ||
| Tue., 5/1 | V Girls Lacrosse | Newtown | Away - Blue and Gold Stadium [Directions] | L 5-12 | 3:30pm | |
| Tue., 5/1 | JV Girls Lacrosse | Newtown | Away - Blue and Gold Stadium [Directions] | 5:15 p.m. | 3:30pm | |
| Tue., 5/1 | JV Softball | Wright Tech | Home - Weston MS [Directions] | 4:00 p.m. | ||
| Wed., 5/2 | V Baseball | Pomperaug | Away - PHS Baseball Field [Directions] | L 2-9 | 2:40pm | |
| Wed., 5/2 | FR Baseball | Pomperaug | Home - Revson Field, Weston [Directions] | 4:15 p.m. | ||
| Wed., 5/2 | V Boys Golf | Joel Barlow | Home - Aspetuck Valley Country Club [Directions] | Weston 182 Joel Barlow 183 | ||
| Wed., 5/2 | V Boys Tennis | New Fairfield | Home - WHS Tennis Courts [Directions] | W 7-0 | ||
| Wed., 5/2 | V Softball | Pomperaug | Away - PHS Softball Field [Directions] | L 0-14 | ||
| Wed., 5/2 | V Girls Tennis | New Fairfield | Away [Directions] | W 5-2 | 2:40pm | |
| Thu., 5/3 | JV Baseball | Pomperaug | Home - Revson Field, Weston [Directions] | 4:15 p.m. | ||
| Thu., 5/3 | V Boys Golf | Woodland Invitational | Away | 8:00 a.m. | at Oxford Greens (4 players) | |
| Thu., 5/3 | V Boys Tennis | New Milford | Away - New Milford HS [Directions] | W 7-0 | 2:40pm | |
| Thu., 5/3 | JV Softball | Pomperaug | Home - Weston MS [Directions] | 4:15 p.m. | ||
| Thu., 5/3 | V Girls Tennis | New Milford | Home - WHS Tennis Courts [Directions] | W 7-0 | ||
| Fri., 5/4 | V Baseball | Stratford | Home - Penders Field [Directions] | L 1-7 | ||
| Fri., 5/4 | FR Baseball | Pomperaug | Away - PHS Baseball Field [Directions] | 4:15 p.m. | 2:40pm | |
| Fri., 5/4 | V Boys Lacrosse | Brookfield | Home - WHS Turf Field [Directions] | W 18-5 | ||
| Fri., 5/4 | JV Boys Lacrosse | Brookfield | Home - WHS Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 5/4 | V Boys Tennis | Stratford | Away - Stratford [Directions] | W 7-0 | 2:40pm | |
| Fri., 5/4 | V Girls Lacrosse | Brookfield | Away - BHS Stadium Field [Directions] | W 9-8 | 2:40pm | |
| Fri., 5/4 | JV Girls Lacrosse | Brookfield | Away - BHS Back Turf [Directions] | 4:15 p.m. | 2:40pm | |
| Fri., 5/4 | V Softball | Stratford | Home - Hurlbutt El. School, Weston [Directions] | W 11-8 | ||
| Fri., 5/4 | JV Softball | Danbury | Home - Weston MS [Directions] | 4:00 p.m. | ||
| Fri., 5/4 | V Girls Tennis | Joel Barlow | Home - WHS Tennis Courts [Directions] | W 4-3 | Non-League | |
| Sat., 5/5 | JV Baseball | Stratford | Away - Penders Field [Directions] | 6:30 p.m. | 4:30pm | |
| Sat., 5/5 | V Boys Tennis | Guilford | Away - Tennis Courts at GHS [Directions] | L 3-4 | 9:30am | nonleague |
| Sat., 5/5 | JV Softball | Stratford | Away - Birdseye Rec Complex [Directions] | 3:00 p.m. | 1:30pm | |
| Sat., 5/5 | JV Girls Tennis | Wilton | Home - WHS Tennis Courts [Directions] | 2:00 p.m. | ||
| Mon., 5/7 | V Baseball | Newtown | Away - Baseball Field at Fairfield Hills Complex [Directions] | L 5-10 | 4:15pm | |
| Mon., 5/7 | FR Baseball | Masuk | Away - Wolfe Park [Directions] | 4:15 p.m. | 2:45pm | |
| Mon., 5/7 | V Boys Golf | New Fairfield | Home - Aspetuck Valley Country Club [Directions] | Weston 182 New Fairfield 222 | ||
| Mon., 5/7 | V Boys Tennis | Joel Barlow | Home - WHS Tennis Courts [Directions] | W 6-1 | ||
| Mon., 5/7 | V Girls Golf | Stratford | Home - Aspetuck Valley Country Club [Directions] | Weston 243 Stratford 316 | ||
| Mon., 5/7 | V Girls Lacrosse | Norwalk | Home - WHS Turf Field [Directions] | W 9-7 | nonleague | |
| Mon., 5/7 | JV Girls Lacrosse | Norwalk | Home - WHS Turf Field [Directions] | 5:00 p.m. | ||
| Mon., 5/7 | V Girls Outdoor Track | Masuk, Notre Dame-Fairfield, Bethel | Home - WHS Track [Directions] | Weston 109 Masuk 45 Weston 141 Notre Dame 6 Weston 119 Bethel 31 | ||
| Mon., 5/7 | V Softball | Newtown | Away - Treadwell Town Park [Directions] | L 0-12 | 4:15pm | |
| Mon., 5/7 | V Girls Tennis | Joel Barlow | Away - Tennis Courts [Directions] | W 6-1 | 2:40pm | |
| Tue., 5/8 | JV Baseball | Newtown | Home - Revson Field, Weston [Directions] | 4:15 p.m. | ||
| Tue., 5/8 | V Boys Golf | Bunnell | Away - Oronoque Country Club [Directions] | Weston 182 Bunnell 212 | ||
| Tue., 5/8 | V Boys Lacrosse | Brien McMahon | Away - Brien McMahon HS [Directions] | W 14-2 | 5:45pm | nonleague |
| Tue., 5/8 | V Boys Outdoor Track | Masuk, Notre Dame-Fairfield, Bethel | Away - Edmund Butler Track @ Masuk HS [Directions] | Masuk 81 Weston 69 Weston 94 Bethel 56 Weston 135 Notre Dame 6 | 2:40pm | |
| Tue., 5/8 | V Boys Tennis | Staples | Away - Staples HS-Tennis Courts [Directions] | L 3-4 | 2:45pm | nonleague |
| Tue., 5/8 | V Girls Golf | Notre Dame-Fairfield | Away - Fairchild Wheeler Golf Course [Directions] | Weston 225 Notre Dame 232 | ||
| Tue., 5/8 | JV Softball | Newtown | Home - Weston MS [Directions] | 4:15 p.m. | ||
| Tue., 5/8 | V Girls Tennis | Staples | Home - WHS Tennis Courts [Directions] | L 2-5 | nonleague | |
| Wed., 5/9 | V Baseball | Notre Dame-Fairfield | Home - Revson Field, Weston [Directions] | L 5-7 | ||
| Wed., 5/9 | FR Baseball | Newtown | Away - Newtown HS Baseball Field [Directions] | 4:15 p.m. | 2:40pm | |
| Wed., 5/9 | JV Boys Tennis | Wilton | Away - Middlebrook School [Directions] | 4:00 p.m. | 3:15pm | |
| Wed., 5/9 | V Girls Lacrosse | Immaculate | Home - WHS Turf Field [Directions] | W 12-7 | ||
| Wed., 5/9 | JV Girls Lacrosse | Immaculate | Home - WHS Turf Field [Directions] | 6:30 p.m. | ||
| Wed., 5/9 | V Softball | Notre Dame-Fairfield | Home - Hurlbutt El. School, Weston [Directions] | L 0-12 | ||
| Wed., 5/9 | JV Girls Tennis | Fairfield Ludlowe | Away - Dwight Elementary School Courts [Directions] | 4:00 p.m. | 2:45pm | |
| Thu., 5/10 | V Baseball | New Fairfield | Away - NFHS Baseball Field [Directions] | W 8-6 | 2:40pm | |
| Thu., 5/10 | JV Baseball | Notre Dame-Fairfield | Away - Fabbri Field at Notre Dame [Directions] | 4:15 p.m. | 2:40pm | |
| Thu., 5/10 | V Boys Golf | Notre Dame-Fairfield | Away - Fairchild Wheeler Golf Course [Directions] | Weston 163 Notre Dame 195 | ||
| Thu., 5/10 | V Boys Tennis | Fairfield Prep | Away - Walsh Athletic Center Courts, Fairfield University [Directions] | W 5-2 | 2:40pm | nonleague |
| Thu., 5/10 | JV Boys Tennis | Fairfield Warde | Away - FWHS Knapps Courts [Directions] | Cancelled | 2:40pm | |
| Thu., 5/10 | V Softball | New Fairfield | Away - NFHS Softball Field [Directions] | L 0-13 | ||
| Thu., 5/10 | V Girls Tennis | Daniel Hand | Home - WHS Tennis Courts [Directions] | L 1-6 | nonleague | |
| Thu., 5/10 | JV Girls Tennis | Fairfield Warde | Away - Fairfield Woods MS Courts [Directions] | Cancelled | 2:40pm | |
| Fri., 5/11 | V Boys Lacrosse | New Milford | Away - New Milford HS [Directions] | W 13-6 | 2:40pm | |
| Fri., 5/11 | JV Boys Lacrosse | New Milford | Away - New Milford HS [Directions] | 4:00 p.m. | 2:40pm | |
| Fri., 5/11 | V Girls Lacrosse | New Milford | Home - WHS Turf Field [Directions] | W 15-6 | ||
| Fri., 5/11 | JV Girls Lacrosse | New Milford | Home - WHS Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 5/14 | V Baseball | New Milford | Home - Revson Field, Weston [Directions] | L 2-5 | ||
| Mon., 5/14 | JV Baseball | New Fairfield | Away - NFHS [Directions] | 4:15 p.m. | 2:40pm | |
| Mon., 5/14 | V Boys Golf | Immaculate | Home - Aspetuck Valley Country Club [Directions] | Weston 171 Immaculate 173 | ||
| Mon., 5/14 | V Boys Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | L 11-12 | 3:30pm | nonleague game |
| Mon., 5/14 | JV Boys Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | 5:00 p.m. | 3:30pm | |
| Mon., 5/14 | V Girls Golf | Newtown | Home - Aspetuck Valley Country Club [Directions] | Newtown 198 Weston 219 | ||
| Mon., 5/14 | V Girls Lacrosse | Bunnell | Home - WHS Turf Field [Directions] | W 14-7 | ||
| Mon., 5/14 | JV Girls Lacrosse | Bunnell | Home - WHS Turf Field [Directions] | 5:00 p.m. | ||
| Mon., 5/14 | V Girls Outdoor Track | New Fairfield, Stratford, Brookfield | Away [Directions] | 4:00 p.m. | ||
| Mon., 5/14 | V Softball | New Milford | Home - Hurlbutt El. School, Weston [Directions] | L 7-13 | ||
| Thu., 5/17 | V Boys Outdoor Track | Stratford | Home - WHS Track [Directions] | Weston 109 Stratford 41 | ||
| Thu., 5/17 | V Boys Outdoor Track | Bethel | Away - Bethel HS [Directions] | Cancelled | 2:40P | |
| Thu., 5/17 | V Girls Outdoor Track | Bethel | Away - Bethel HS [Directions] | Cancelled | 2:40P | |
| Fri., 5/18 | JV Boys Tennis | Staples | Away - Town Farms Tennis Courts [Directions] | 3:30 p.m. | 2:40pm | |
| Sun., 5/20 | V Softball | Brookfield | Home - Hurlbutt El. School, Weston [Directions] | L 0-12 | ||
| Mon., 5/21 | V Girls Golf | Masuk | Away - Whitney Farms Golf Course [Directions] | Masuk 206 Weston 229 | ||
| Tue., 5/22 | V Girls Golf | Bunnell | Home - Aspetuck Valley Country Club [Directions] | Weston 225 Bunnell 302 | ||
| Wed., 5/23 | V Baseball | Brookfield | Home - BHS Baseball Field [Directions] | W 3-0 | ||
| Wed., 5/23 | FR Baseball | Wilton | Away - Wilton JV Field [Directions] | 4:00 p.m. | ||
| Wed., 5/23 | V Boys Golf | Bethel, Brookfield | Away - Redding Country Club [Directions] | Weston 184 Bethel 302 Weston 184 Brookfield 201 | ||
| Wed., 5/23 | V Girls Golf | Newtown, Stratford | Away - Heritage Golf Course [Directions] | Newtown 215 Weston 228 | ||
| Thu., 5/24 | JV Baseball | Brookfield | Home - Revson Field, Weston [Directions] | 4:00 p.m. | 2:40pm | |
| Thu., 5/24 | FR Baseball | Brookfield | Home - Revson Field, Weston [Directions] | 4:00 p.m. | 2:40pm | |
| Thu., 5/24 | V Girls Golf | Immaculate | Away - Richter Park [Directions] | Weston 205 Immaculate 254 | ||
| Thu., 5/24 | Miscellaneous Events | Middle School Track Meet | Away - WHS Track | 4:00 p.m. | ||