| Wilton 2023-24 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 837 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Tue., 8/22 | V Boys Golf | Westhill | Home - Rolling Hills Country Club [Directions] | 3:30 p.m. | Wilton - 165 Westhill - 173 | |
| Wed., 8/23 | V Football | Fairfield Prep, TBA, Newtown, Staples (Scrim.) | Away - Fairfield University-Barlow Field [Directions] | 3:00 p.m. | ||
| Thu., 8/24 | FR Football | Staples (Scrim.) | Away - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Thu., 8/24 | V Boys Golf | Darien | Away - Woodway Country Club [Directions] | 3:15 p.m. | Wilton - 168 Darien - 168 | |
| Thu., 8/24 | JV Boys Golf | Darien | Away - Woodway Country Club [Directions] | 3:30 p.m. | ||
| Tue., 8/29 | V Boys Golf | Danbury | Away - Richter Park Golf Course [Directions] | 3:00 p.m. | Wilton - 157 Danbury - 179 | |
| Tue., 8/29 | JV Boys Golf | Danbury | Away - Richter Park Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 8/29 | V Field Hockey | Greenwich Academy (Scrim.) | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 6:15 p.m. | T 2-2 | |
| Tue., 8/29 | JV Field Hockey | Greenwich Academy (Scrim.) | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 5:30 p.m. | ||
| Thu., 8/31 | V Boys Soccer | Stamford (Scrim.) | Away - Stamford HS-SHS Upper Soccer Field [Directions] | 4:30 p.m. | ||
| Thu., 8/31 | V Girls Soccer | Brookfield, John Jay (NY) (Scrim.) | Home - Wilton HS-Lilly Field [Directions] | 4:30 p.m. | ||
| Thu., 8/31 | V Girls Soccer | John Jay (NY) (Scrim.) | Home - Wilton HS-Lilly Field [Directions] | 6:00 p.m. | ||
| Thu., 8/31 | JV Girls Soccer | Brookfield (Scrim.) | Home - Allen's Meadow-Field 2 [Directions] | 4:15 p.m. | ||
| Thu., 8/31 | JV Girls Soccer | John Jay (NY) (Scrim.) | Home - Allen's Meadow-Field 2 [Directions] | 5:45 p.m. | ||
| Fri., 9/1 | V Football | Danbury (Scrim.) | Home - Wilton HS-Fujitani Field - Turf [Directions] | 4:30 p.m. | ||
| Fri., 9/1 | V Boys Soccer | Foran Jamboree | Away - Foran HS -Kelley Martin Tighe Memorial Field | 4:00 p.m. | ||
| Sat., 9/2 | V Field Hockey | Sacred Heart of Greenwich (Scrim.) | Away - Sacred Heart of Greenwich | 9:00 a.m. | ||
| Sat., 9/2 | V Girls Volleyball | King and Low-Heywood Thomas, Naugatuck, Northwest Catholic, St. Joseph, Staples | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:00 a.m. | ||
| Tue., 9/5 | V Boys Soccer | Weston (Scrim.) | Home - Wilton HS-Lilly Field [Directions] | 6:00 p.m. | ||
| Tue., 9/5 | JV Boys Soccer | Weston (Scrim.) | Away - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | ||
| Tue., 9/5 | V Field Hockey | Sacred Heart of Greenwich (Scrim.) | Away - Sacred Heart of Greenwich | 4:30 p.m. | Cancelled | |
| Tue., 9/5 | JV Field Hockey | Sacred Heart of Greenwich (Scrim.) | Away - Sacred Heart of Greenwich | 4:30 p.m. | Cancelled | |
| Wed., 9/6 | V Boys Golf | Brien McMahon | Away - Oak Hills Golf Course [Directions] | 3:30 p.m. | Wilton - 143 McMahon - 153 | |
| Wed., 9/6 | JV Boys Golf | Brien McMahon | Away - Brien McMahon HS-Oak Hills Golf Course [Directions] | 3:30 p.m. | ||
| Wed., 9/6 | V Girls Volleyball | TBA | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:15 p.m. | ||
| Wed., 9/6 | JV Girls Volleyball | TBA | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:15 p.m. | ||
| Thu., 9/7 | V Field Hockey | Fairfield Warde | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 6:45 p.m. | W 7-0 | |
| Thu., 9/7 | JV Field Hockey | Fairfield Warde | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 5:30 p.m. | W 4-0 | |
| Thu., 9/7 | FR Field Hockey | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | Cancelled | |
| Thu., 9/7 | V Girls Soccer | Fairfield Warde | Home - Wilton HS-Lilly Field [Directions] | 6:30 p.m. | T 0-0 | |
| Fri., 9/8 | FR Boys Soccer | Fairfield Warde | Home - Allen's Meadow-Field 2 [Directions] | 4:30 p.m. | ||
| Fri., 9/8 | JV Girls Soccer | Fairfield Warde | Home - Allen's Meadow-Field #1 [Directions] | 4:15 p.m. | ||
| Fri., 9/8 | V Girls Swimming and Diving | New Canaan | Away - Waveny Park-Waveny Pool [Directions] | 3:30 p.m. | postponed | |
| Sat., 9/9 | V Boys Cross Country | Guilford | Home - Allen's Meadow-XC Course [Directions] | 9:00 a.m. | 15-50 | |
| Sat., 9/9 | V Boys Cross Country | Wilton Invitational | Home - Allen's Meadow-XC Course [Directions] | 9:00 a.m. | ||
| Sat., 9/9 | V Boys Cross Country | Woodland | Home - Allen's Meadow-XC Course [Directions] | 9:00 a.m. | ||
| Sat., 9/9 | V Boys Cross Country | Darien | Home - Allen's Meadow-XC Course [Directions] | 9:00 a.m. | ||
| Sat., 9/9 | V Boys Cross Country | New Canaan | Away - Waveny Park [Directions] | 9:30 a.m. | ||
| Sat., 9/9 | JV Football | Amistad | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 10:00 a.m. | ||
| Sat., 9/9 | FR Football | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 10:00 a.m. | W 16 to 6 | |
| Sat., 9/9 | V Girls Cross Country | Guilford | Home - Allen's Meadow-XC Course [Directions] | 9:00 a.m. | ||
| Sat., 9/9 | V Girls Cross Country | Woodland | Home - Allen's Meadow-XC Course [Directions] | 9:00 a.m. | ||
| Sat., 9/9 | V Girls Cross Country | New Canaan | Away - Waveny Park [Directions] | 9:30 a.m. | ||
| Sat., 9/9 | V Girls Soccer | Masuk | Home - Wilton HS-Lilly Field [Directions] | 11:00 a.m. | T 0-0 | |
| Sat., 9/9 | JV Girls Soccer | Masuk | Home - Wilton HS-Lilly Field [Directions] | 9:00 a.m. | W 2-1 | |
| Sat., 9/9 | V Girls Volleyball | Hamden | Away - Hamden HS-HHS Gym [Directions] | 5:15 p.m. | W 3-1 | |
| Sat., 9/9 | JV Girls Volleyball | Hamden | Away - Hamden HS-HHS Gym [Directions] | 4:00 p.m. | W 25-2121-16 | |
| Sun., 9/10 | V Football | Berlin | Away - Sage Park - Berlin-Scalise Field -Turf Field Sage Park Stadium [Directions] | 6:00 p.m. | W 34-0 | |
| Mon., 9/11 | V Field Hockey | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | W 1-5 | |
| Mon., 9/11 | JV Field Hockey | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | ||
| Mon., 9/11 | FR Field Hockey | Westhill | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 4:15 p.m. | ||
| Mon., 9/11 | JV Girls Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 5:00 p.m. | ||
| Mon., 9/11 | V Girls Volleyball | Weston | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:45 p.m. | W 3-1 | |
| Mon., 9/11 | JV Girls Volleyball | Weston | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | L 1-2 | |
| Tue., 9/12 | V Boys Cross Country | Trumbull, Darien, St. Joseph | Away - Trumbull HS-Cross Country Course [Directions] | 4:00 p.m. | ||
| Tue., 9/12 | V Boys Golf | Stamford | Home - Rolling Hills Country Club [Directions] | 3:30 p.m. | Wilton - 155 Stamford - 168 | |
| Tue., 9/12 | V Boys Soccer | Norwalk | Home - Wilton HS-Lilly Field [Directions] | 4:15 p.m. | L 0-1 | |
| Tue., 9/12 | JV Boys Soccer | Norwalk | Home - Allen's Meadow-Field 2 [Directions] | 4:15 p.m. | T 1-1 | |
| Tue., 9/12 | FR Boys Soccer | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 4:30 p.m. | L 1-0 | |
| Tue., 9/12 | V Girls Cross Country | Trumbull, Darien, St. Joseph | Away - Trumbull HS-Cross Country Course [Directions] | 4:15 p.m. | ||
| Wed., 9/13 | V Field Hockey | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 4:00 p.m. | W 1-8 | |
| Wed., 9/13 | JV Field Hockey | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 5:30 p.m. | W 6-0 | |
| Wed., 9/13 | V Girls Soccer | Darien | Away - Darien HS-[CIAC] Willow Brook Park [Directions] | 4:00 p.m. | T 2-2 | |
| Wed., 9/13 | JV Girls Soccer | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | T 1-1 | |
| Wed., 9/13 | V Girls Swimming and Diving | Fairfield Ludlowe | Home - Wilton YMCA [Directions] | 3:40 p.m. | Wilton - 95 Ludlowe - 75 | |
| Wed., 9/13 | V Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Wed., 9/13 | JV Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:30 p.m. | L 0-2 | |
| Thu., 9/14 | V Football | Norwalk | Home - Wilton HS-Fujitani Field - Turf [Directions] | 7:00 p.m. | W 48-0 | |
| Thu., 9/14 | FR Football | Darien | Away - Darien HS-DHS Stadium East [Directions] | 4:00 p.m. | W 14 to 0 | |
| Thu., 9/14 | V Boys Soccer | Darien | Home - Wilton HS-Lilly Field [Directions] | 5:15 p.m. | W 1-0 | |
| Thu., 9/14 | JV Boys Soccer | Darien | Home - Allen's Meadow-Field 2 [Directions] | 4:15 p.m. | W 5-1 | |
| Thu., 9/14 | FR Boys Soccer | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | W 2-1 | |
| Thu., 9/14 | FR Girls Soccer | Darien | Home - Allen's Meadow-Field #1 [Directions] | 4:15 p.m. | L 1-3 | |
| Mon., 9/18 | JV Football | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | 5:30 p.m. | ||
| Mon., 9/18 | V Boys Golf | New Canaan | Away - CCNC [Directions] | 3:30 p.m. | ||
| Mon., 9/18 | JV Boys Golf | New Canaan | Away - CCNC [Directions] | 3:30 p.m. | ||
| Mon., 9/18 | JV Girls Soccer | Greenwich | Home - Wilton HS-Lilly Field [Directions] | 4:15 p.m. | W 3-1 | |
| Mon., 9/18 | FR Girls Soccer | Greenwich | Away - Greenwich HS-Field 3 [Directions] | 4:45 p.m. | L 0-5 | |
| Tue., 9/19 | V Boys Cross Country | New Canaan, Fairfield Ludlowe, Norwalk | Away - Waveny Park [Directions] | 4:00 p.m. | ||
| Tue., 9/19 | V Boys Golf | Fairfield Warde | Home - Rolling Hills Country Club [Directions] | 3:30 p.m. | Wilton - 164 Warde - 167 | |
| Tue., 9/19 | JV Boys Golf | Fairfield Warde | Home - Rolling Hills Country Club [Directions] | 3:30 p.m. | ||
| Tue., 9/19 | V Boys Soccer | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:30 p.m. | L 0-3 | |
| Tue., 9/19 | JV Boys Soccer | Greenwich | Away - Greenwich HS-Field 3 [Directions] | 5:00 p.m. | L 0-7 | |
| Tue., 9/19 | FR Boys Soccer | Greenwich | Home - Allen's Meadow-Field 2 [Directions] | 4:30 p.m. | L 3-0 | |
| Tue., 9/19 | V Girls Cross Country | New Canaan, Fairfield Ludlowe, Norwalk | Away - Waveny Park [Directions] | 4:00 p.m. | ||
| Tue., 9/19 | FR Field Hockey | Greenwich | Away - Cos Cob Park, Benvenuto Field-Benvenuto Field [Directions] | 4:45 p.m. | W 5-3 | |
| Tue., 9/19 | V Girls Soccer | Greenwich | Home - Wilton HS-Lilly Field [Directions] | 6:00 p.m. | T 0-0 | |
| Wed., 9/20 | V Field Hockey | Greenwich | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 6:45 p.m. | L 1-4 | |
| Wed., 9/20 | JV Field Hockey | Greenwich | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 5:30 p.m. | T 1-1 | |
| Wed., 9/20 | V Girls Soccer | Trumbull | Home - Wilton HS-Lilly Field [Directions] | 6:30 p.m. | L 0-1 | |
| Wed., 9/20 | JV Girls Soccer | Trumbull | Home - Allen's Meadow-Field 2 [Directions] | 4:15 p.m. | L 1-4 | |
| Wed., 9/20 | FR Girls Soccer | Trumbull | Away - Trumbull HS-JV Grass Field [Directions] | 5:00 p.m. | L 2-3 | |
| Wed., 9/20 | V Girls Swimming and Diving | Westhill/Stamford | Home - Wilton YMCA [Directions] | 3:40 p.m. | Wilton 96 Westhill 66 | |
| Wed., 9/20 | V Girls Volleyball | Branford | Away - Branford HS-Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Wed., 9/20 | JV Girls Volleyball | Branford | Away - Branford HS-Gym [Directions] | 4:00 p.m. | W 2-0 | |
| Thu., 9/21 | FR Football | Joel Barlow | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 4:15 p.m. | W 25 to 6 | |
| Thu., 9/21 | V Boys Golf | Ridgefield, Greenwich | Away - Silver Spring Golf Course [Directions] | 3:00 p.m. | Wilton - 161 Ridgefield - 158 | |
| Thu., 9/21 | JV Boys Golf | Ridgefield | Away - Silver Spring Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 9/21 | V Boys Soccer | Trumbull | Away - Trumbull HS-Cork Field [Directions] | 4:00 p.m. | L 1-3 | |
| Thu., 9/21 | JV Boys Soccer | Trumbull | Away - Trumbull HS-The Pit [Directions] | 4:00 p.m. | L 2-3 | |
| Thu., 9/21 | FR Boys Soccer | Trumbull | Home - Allen's Meadow-Field 2 [Directions] | 4:30 p.m. | L 1-3 | |
| Fri., 9/22 | V Football | Platt | Home - Wilton HS-Fujitani Field - Turf [Directions] | 6:30 p.m. | W 32-14 | |
| Fri., 9/22 | V Field Hockey | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 6:30 p.m. | L 2-1 | |
| Fri., 9/22 | JV Field Hockey | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 5:00 p.m. | W 5-0 | |
| Fri., 9/22 | FR Field Hockey | Norwalk | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 4:00 p.m. | W 7-2 | |
| Fri., 9/22 | V Girls Soccer | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 4:30 p.m. | W 4-0 | |
| Fri., 9/22 | JV Girls Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 4:30 p.m. | W 4-1 | |
| Fri., 9/22 | FR Girls Soccer | Danbury | Home - Allen's Meadow-Field #1 [Directions] | 4:15 p.m. | W 7-0 | |
| Fri., 9/22 | V Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Fri., 9/22 | JV Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:30 p.m. | L 1-2 | |
| Fri., 9/22 | FR Girls Volleyball | Fairfield Warde | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | L 0-3 | |
| Sat., 9/23 | JV Football | Brookfield | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 10:00 a.m. | ||
| Sat., 9/23 | V Boys Soccer | Danbury | Home - Wilton HS-Lilly Field [Directions] | 11:30 a.m. | T 0-0 | |
| Sat., 9/23 | JV Boys Soccer | Danbury | Home - Wilton HS-Lilly Field [Directions] | 9:00 a.m. | L 2-4 | |
| Sat., 9/23 | FR Boys Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 11:00 a.m. | L 9-0 | |
| Sat., 9/23 | V Girls Volleyball | Hamden | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 11:30 a.m. | W 3-1 | |
| Sat., 9/23 | JV Girls Volleyball | Hamden | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 10:00 a.m. | W 2-0 | |
| Tue., 9/26 | V Boys Cross Country | Greenwich, Bridgeport Central, Fairfield Warde | Away - Greenwich Point [Directions] | 4:00 p.m. | ||
| Tue., 9/26 | V Boys Golf | Norwalk | Home - Rolling Hills Country Club [Directions] | 3:30 p.m. | Wilton 152 Norwalk 168 | |
| Tue., 9/26 | V Boys Soccer | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 6:00 p.m. | L 1-2 | |
| Tue., 9/26 | FR Boys Soccer | Fairfield Warde | Away - Tunxis [Directions] | 4:15 p.m. | ||
| Tue., 9/26 | V Girls Cross Country | Greenwich, Fairfield Warde | Away - Greenwich Point [Directions] | 4:00 p.m. | ||
| Tue., 9/26 | JV Girls Soccer | Fairfield Warde | Home - Allen's Meadow-Field 2 [Directions] | 4:15 p.m. | W 6-1 | |
| Tue., 9/26 | FR Girls Soccer | Fairfield Warde | Home - Allen's Meadow-Field #1 [Directions] | 4:15 p.m. | W 3-0 | |
| Wed., 9/27 | V Boys Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 2:50 p.m. | Wilton - 159 Ludlowe - 156 | |
| Wed., 9/27 | JV Boys Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 2:50 p.m. | ||
| Wed., 9/27 | FR Field Hockey | Staples | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 4:00 p.m. | T 5-5 | |
| Wed., 9/27 | V Girls Soccer | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 6:30 p.m. | T 1-1 | |
| Wed., 9/27 | JV Girls Soccer | New Canaan | Away - Conner Field, New Cannan [Directions] | 4:00 p.m. | L 2-3 | |
| Wed., 9/27 | FR Girls Soccer | New Canaan | Home - Allen's Meadow-3A [Directions] | 4:30 p.m. | L 0-7 | |
| Wed., 9/27 | V Girls Volleyball | Norwalk | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:45 p.m. | W 3-0 | |
| Wed., 9/27 | JV Girls Volleyball | Norwalk | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | W 2-0 | |
| Wed., 9/27 | FR Girls Volleyball | Norwalk | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | W 2-0 | |
| Thu., 9/28 | FR Football | Greenwich | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 4:30 p.m. | W 19 to 0 | |
| Thu., 9/28 | V Boys Golf | Staples | Home - Rolling Hills Country Club [Directions] | 3:30 p.m. | Wilton - 164 Staples - 169 | |
| Thu., 9/28 | JV Boys Golf | Staples | Home - Rolling Hills Country Club [Directions] | 3:30 p.m. | ||
| Thu., 9/28 | V Boys Soccer | New Canaan | Home - Wilton HS-Lilly Field [Directions] | 4:30 p.m. | W 4-2 | |
| Thu., 9/28 | JV Boys Soccer | New Canaan | Home - Allen's Meadow-Field 2 [Directions] | 4:15 p.m. | W 3-2 | |
| Thu., 9/28 | FR Boys Soccer | New Canaan | Away - Conner Field, New Cannan [Directions] | 4:30 p.m. | W 1-2 | |
| Thu., 9/28 | V Field Hockey | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | L 7-0 | |
| Thu., 9/28 | JV Field Hockey | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 5:15 p.m. | T 2-2 | |
| Thu., 9/28 | V Girls Swimming and Diving | Darien | Home - New Canaan Y -Diving Only [Directions] | 2:00 p.m. | Wilton - 0 Darien 13 | |
| Thu., 9/28 | V Girls Swimming and Diving | Darien | Home - Wilton YMCA [Directions] | 3:40 p.m. | Wilton - 74 Darien - 98 | |
| Fri., 9/29 | V Football | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 5:00 p.m. | W 32-0 | |
| Fri., 9/29 | FR Girls Soccer | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | 4:30 p.m. | ||
| Fri., 9/29 | V Girls Volleyball | Darien | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:45 p.m. | L 0-3 | |
| Fri., 9/29 | JV Girls Volleyball | Darien | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | L 1-2 | |
| Sat., 9/30 | JV Football | Fairfield Warde | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 12:00 p.m. | ||
| Sat., 9/30 | V Boys Soccer | Staples | Away - Staples HS-Wakeman Field B (turf) [Directions] | 10:30 a.m. | L 0-4 | |
| Sat., 9/30 | JV Boys Soccer | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | 12:00 p.m. | ||
| Sat., 9/30 | FR Boys Soccer | Staples | Home - Allen's Meadow-Field 2 [Directions] | Postponed | ||
| Sat., 9/30 | V Field Hockey | Fairfield Ludlowe | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 9:00 a.m. | W 3-0 | |
| Sat., 9/30 | JV Field Hockey | Fairfield Ludlowe | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 10:30 a.m. | W 4-2 | |
| Sat., 9/30 | V Girls Soccer | Staples | Home - Wilton HS-Lilly Field [Directions] | 10:30 a.m. | W 1-0 | |
| Sat., 9/30 | JV Girls Soccer | Staples | Home - Wilton HS-Lilly Field [Directions] | 9:00 a.m. | W 3-2 | |
| Sat., 9/30 | FR Girls Soccer | Ridgefield | Away - Ridgefield HS-Tiger Hollow Turf Field II [Directions] | 12:00 p.m. | L 0-3 | |
| Mon., 10/2 | JV Boys Golf | Darien | Home - Rolling Hills Country Club [Directions] | 3:15 p.m. | ||
| Mon., 10/2 | V Field Hockey | Trumbull | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 6:30 p.m. | W 8-1 | |
| Mon., 10/2 | JV Field Hockey | Trumbull | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 5:00 p.m. | T 1-1 | |
| Mon., 10/2 | FR Girls Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Tue., 10/3 | V Boys Cross Country | Danbury, Ridgefield, Westhill | Home - Allen's Meadow-XC Course [Directions] | 4:00 p.m. | ||
| Tue., 10/3 | V Girls Cross Country | Danbury, Ridgefield, Westhill | Home - Allen's Meadow-XC Course [Directions] | 4:00 p.m. | ||
| Tue., 10/3 | V Girls Soccer | Ridgefield | Home - Wilton HS-Lilly Field [Directions] | 6:30 p.m. | L 0-1 | |
| Tue., 10/3 | JV Girls Soccer | Ridgefield | Home - Allen's Meadow-Field #1 [Directions] | 4:15 p.m. | L 1-2 | |
| Tue., 10/3 | V Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | L 0-3 | |
| Tue., 10/3 | JV Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | L 0-2 | |
| Tue., 10/3 | FR Girls Volleyball | Greenwich | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | L 0-3 | |
| Wed., 10/4 | V Boys Golf | Trumbull | Home - Rolling Hills Country Club [Directions] | 3:30 p.m. | Wilton - 153 Trumbull - 153 | |
| Wed., 10/4 | JV Boys Golf | Trumbull | Home - Rolling Hills Country Club [Directions] | 3:30 p.m. | ||
| Wed., 10/4 | V Boys Soccer | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 7:00 p.m. | W 4-1 | |
| Wed., 10/4 | JV Boys Soccer | Ridgefield | Away - Ridgefield HS-RHS Lower Grass Field [Directions] | 4:00 p.m. | L 0-4 | |
| Wed., 10/4 | FR Boys Soccer | Ridgefield | Home - Allen's Meadow-Field 2 [Directions] | 4:30 p.m. | L 2-3 | |
| Wed., 10/4 | V Field Hockey | Darien | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 7:00 p.m. | L 1-2 | |
| Wed., 10/4 | JV Field Hockey | Darien | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 5:30 p.m. | ||
| Wed., 10/4 | FR Field Hockey | Darien | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 10/4 | V Girls Swimming and Diving | Danbury | Home - Wilton YMCA [Directions] | 3:40 p.m. | Wilton 76 Danbury 54 | |
| Wed., 10/4 | FR Girls Volleyball | Trumbull | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | L 0-3 | |
| Thu., 10/5 | V Girls Soccer | Bridgeport Central | Away - Bridgeport Central-Kennedy Stadium Turf [Directions] | 4:00 p.m. | W 3-0 | |
| Thu., 10/5 | FR Girls Soccer | Shelton | Home - Allen's Meadow-Field 2 [Directions] | 4:15 p.m. | W 6-0 | |
| Thu., 10/5 | V Girls Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Thu., 10/5 | JV Girls Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 4:30 p.m. | L 0-2 | |
| Fri., 10/6 | V Boys Soccer | Bridgeport Central | Home - Wilton HS-Lilly Field [Directions] | 6:30 p.m. | L 1-2 | |
| Fri., 10/6 | JV Boys Soccer | Bridgeport Central | Home - Allen's Meadow-Field 2 [Directions] | 4:30 p.m. | W 3-0 | |
| Fri., 10/6 | FR Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Front Field [Directions] | 5:00 p.m. | ||
| Fri., 10/6 | V Girls Swimming and Diving | New Canaan | Home - Wilton YMCA [Directions] | 3:40 p.m. | Wilton 106 New Canaan 76 | |
| Fri., 10/6 | V Girls Volleyball | Danbury | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:45 p.m. | W 3-0 | |
| Fri., 10/6 | JV Girls Volleyball | Danbury | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | L 1-2 | |
| Sat., 10/7 | JV Football | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 10:00 a.m. | ||
| Sat., 10/7 | V Field Hockey | Glastonbury | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 2:00 p.m. | W 3-1 | |
| Sat., 10/7 | JV Field Hockey | Glastonbury | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 3:30 p.m. | W 5-0 | |
| Sat., 10/7 | V Girls Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 6:00 p.m. | W 2-0 | |
| Sat., 10/7 | JV Girls Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | Canceled | Cancelled | |
| Sat., 10/7 | FR Girls Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 10:00 a.m. | L 2-3 | |
| Mon., 10/9 | V Boys Golf | New Canaan | Home - Rolling Hills Country Club [Directions] | 3:15 p.m. | Wilton - 162 New Canaan - 168 | |
| Mon., 10/9 | JV Boys Golf | New Canaan | Home - Rolling Hills Country Club [Directions] | 3:15 p.m. | ||
| Mon., 10/9 | V Field Hockey | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | W 0-4 | |
| Mon., 10/9 | JV Field Hockey | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | W 6-0 | |
| Mon., 10/9 | V Girls Soccer | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 4:00 p.m. | L 0-4 | |
| Mon., 10/9 | JV Girls Soccer | St. Joseph | Away - St. Joseph HS-Lower Grass Field [Directions] | 4:00 p.m. | ||
| Pending changes awaiting acceptance by one or more parties involved: Date to 10/13, Facility to Allen's Meadow-Field 2 | ||||||
| Mon., 10/9 | V Girls Volleyball | New Canaan | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:45 p.m. | W 3-0 | |
| Mon., 10/9 | JV Girls Volleyball | New Canaan | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | L 1-2 | |
| Mon., 10/9 | FR Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | L 0-3 | |
| Tue., 10/10 | V Boys Golf | Greenwich | Home - Rolling Hills Country Club [Directions] | 3:30 p.m. | Wilton - 162 Greenwich - 150 | |
| Tue., 10/10 | JV Boys Golf | Greenwich | Home - Rolling Hills Country Club [Directions] | 3:30 p.m. | Wilton - 179 Greenwich - 180 | |
| Tue., 10/10 | V Boys Soccer | St. Joseph | Home - Wilton HS-Lilly Field [Directions] | 6:30 p.m. | W 3-2 | |
| Wed., 10/11 | V Boys Cross Country | Brien McMahon, Stamford, Staples | Home - Allen's Meadow-XC Course [Directions] | 4:00 p.m. | ||
| Wed., 10/11 | V Girls Cross Country | Brien McMahon, Stamford, Staples | Home - Allen's Meadow-XC Course [Directions] | 4:00 p.m. | ||
| Wed., 10/11 | V Field Hockey | New Canaan | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 3:30 p.m. | W 4-3 | |
| Wed., 10/11 | JV Field Hockey | New Canaan | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 5:00 p.m. | W 5-3 | |
| Wed., 10/11 | FR Field Hockey | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | L 1-3 | |
| Wed., 10/11 | V Girls Swimming and Diving | Fairfield Warde | Home - Wilton YMCA [Directions] | 3:45 p.m. | Wilton 99 Warde 70 | |
| Wed., 10/11 | V Girls Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Wed., 10/11 | JV Girls Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:00 p.m. | L 0-2 | |
| Thu., 10/12 | FR Football | Staples | Away - Staples HS-Staples Stadium [Directions] | 6:00 p.m. | L 15 to 20 | |
| Thu., 10/12 | V Boys Golf | St. Joseph | Away - Tashua Knolls Golf Course [Directions] | 3:00 p.m. | Wilton - 160 St. Joseph - 145 | |
| Thu., 10/12 | JV Boys Golf | St. Joseph | Away - Tashua Knolls Golf Course-Tashua Glen [Directions] | 3:15 p.m. | ||
| Thu., 10/12 | V Girls Soccer | Westhill | Home - Wilton HS-Lilly Field [Directions] | 6:30 p.m. | W 3-0 | |
| Thu., 10/12 | JV Girls Soccer | Westhill | Home - Allen's Meadow-Field 2 [Directions] | 4:00 p.m. | W 6-1 | |
| Fri., 10/13 | V Boys Soccer | Westhill | Away - Westhill HS-Westhill Front Turf Field [Directions] | 4:00 p.m. | L 4-2 | |
| Fri., 10/13 | FR Boys Soccer | Westhill | Home - Allen's Meadow-Field 2 [Directions] | 4:30 p.m. | T 2-2 | |
| Fri., 10/13 | V Field Hockey | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 5:00 p.m. | W 2-3 | |
| Fri., 10/13 | JV Field Hockey | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 6:30 p.m. | W 4-1 | |
| Fri., 10/13 | FR Field Hockey | Ridgefield | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 4:00 p.m. | ||
| Fri., 10/13 | JV Girls Soccer | St. Joseph | Home - Allen's Meadow-Field #1 [Directions] | 4:00 p.m. | W 1-0 | |
| Fri., 10/13 | V Girls Swimming and Diving | Trumbull | Away - University of Bridgeport-Pool [Directions] | 4:00 p.m. | Wilton 80 Trumbull 90 | |
| Fri., 10/13 | V Girls Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:30 p.m. | L 2-3 | |
| Fri., 10/13 | JV Girls Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:00 p.m. | L 0-2 | |
| Fri., 10/13 | FR Girls Volleyball | Ridgefield | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | L 0-2 | |
| Sat., 10/14 | V Football | Staples | Home - Wilton HS-Fujitani Field - Turf [Directions] | 2:00 p.m. | L 22-29 | |
| Sat., 10/14 | JV Boys Soccer | Westhill | Away - Westhill HS-Front Turf [Directions] | 10:30 a.m. | T 3-3 | |
| Mon., 10/16 | JV Football | Staples | Away - Staples HS-Staples Stadium [Directions] | 6:00 p.m. | ||
| Mon., 10/16 | V Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 6:30 p.m. | L 4-0 | |
| Mon., 10/16 | JV Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 4:15 p.m. | L 1-0 | |
| Mon., 10/16 | V Field Hockey | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 5:00 p.m. | W 0-6 | |
| Mon., 10/16 | JV Field Hockey | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 6:30 p.m. | W 5-0 | |
| Mon., 10/16 | V Girls Soccer | Brien McMahon | Home - Wilton HS-Lilly Field [Directions] | 6:30 p.m. | L 0-1 | |
| Mon., 10/16 | JV Girls Soccer | Brien McMahon | Home - Allen's Meadow-Field 2 [Directions] | 4:15 p.m. | W 7-2 | |
| Mon., 10/16 | V Girls Volleyball | Bridgeport Central | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:45 p.m. | W 3-0 | |
| Mon., 10/16 | JV Girls Volleyball | Bridgeport Central | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | W 2-0 | |
| Tue., 10/17 | FR Boys Soccer | Brien McMahon | Home - Allen's Meadow-Field #1 [Directions] | 5:00 p.m. | ||
| Wed., 10/18 | V Boys Cross Country | FCIAC Championship | Away - Waveny Park | 2:15 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Not Listed-Waveny Park | ||||||
| Wed., 10/18 | V Girls Cross Country | FCIAC Championship | Away - Waveny Park | 2:15 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Not Listed-Waveny Park | ||||||
| Wed., 10/18 | V Field Hockey | Branford | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 6:30 p.m. | W 6-0 | |
| Wed., 10/18 | JV Field Hockey | Branford | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 5:00 p.m. | W 1-0 | |
| Wed., 10/18 | V Girls Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 7:00 p.m. | L 3-0 | |
| Wed., 10/18 | JV Girls Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | 4:30 p.m. | T 0-0 | |
| Wed., 10/18 | FR Girls Soccer | Fairfield Ludlowe | Home - Allen's Meadow-Field 2 [Directions] | 4:15 p.m. | L 3-9 | |
| Wed., 10/18 | V Girls Swimming and Diving | Ridgefield | Away - Barlow Mountain Pool [Directions] | 4:00 p.m. | Wilton 76 Ridgefield 94 | |
| Wed., 10/18 | V Girls Volleyball | St. Joseph | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:45 p.m. | L 1-3 | |
| Wed., 10/18 | JV Girls Volleyball | St. Joseph | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | L 0-2 | |
| Wed., 10/18 | FR Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:45 p.m. | L 0-3 | |
| Thu., 10/19 | FR Football | Fairfield Ludlowe | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 4:30 p.m. | L 15 to 22 | |
| Thu., 10/19 | V Boys Soccer | Fairfield Ludlowe | Home - Wilton HS-Lilly Field [Directions] | 6:30 p.m. | L 0-2 | |
| Thu., 10/19 | JV Boys Soccer | Fairfield Ludlowe | Home - Allen's Meadow-Field 2 [Directions] | 4:30 p.m. | ||
| Thu., 10/19 | FR Boys Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | 4:00 p.m. | ||
| Fri., 10/20 | V Girls Swimming and Diving | St. Joseph | Home - Wilton YMCA [Directions] | 3:40 p.m. | Wilton 91 St. Joseph 69 | |
| Fri., 10/20 | V Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Fri., 10/20 | JV Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:30 p.m. | L 1-2 | |
| Fri., 10/20 | FR Girls Volleyball | Westhill | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | L 0-3 | |
| Sat., 10/21 | V Football | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 2:00 p.m. | L 13-20 | |
| Mon., 10/23 | JV Football | New Canaan | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 4:15 p.m. | ||
| Mon., 10/23 | V Girls Soccer | Stamford | Away - West Beach Field [Directions] | 4:00 p.m. | L 2-1 | |
| Mon., 10/23 | JV Girls Soccer | Stamford | Away - Rippowam MS-Upper Soccer/Footballl Field [Directions] | 4:30 p.m. | W 5-1 | |
| Mon., 10/23 | V Girls Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 5:00 p.m. | L 0-3 | |
| Mon., 10/23 | JV Girls Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 6:00 p.m. | W 2-1 | |
| Mon., 10/23 | FR Girls Volleyball | Brien McMahon | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | L 0-3 | |
| Tue., 10/24 | V Boys Soccer | Stamford | Home - Wilton HS-Lilly Field [Directions] | 6:30 p.m. | L 0-5 | |
| Tue., 10/24 | JV Boys Soccer | Stamford | Home - Allen's Meadow-Field 2 [Directions] | 4:30 p.m. | ||
| Tue., 10/24 | FR Boys Soccer | Stamford | Away - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | ||
| Tue., 10/24 | JV Girls Soccer | John Jay (NY) | Home - Allen's Meadow-Field #1 [Directions] | 4:30 p.m. | W 2-1 | |
| Wed., 10/25 | V Field Hockey | Danbury | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 6:15 p.m. | W 6-0 | |
| Wed., 10/25 | JV Field Hockey | Danbury | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 5:00 p.m. | W 7-0 | |
| Wed., 10/25 | V Girls Volleyball | Fairfield Ludlowe | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:45 p.m. | L 2-3 | |
| Wed., 10/25 | JV Girls Volleyball | Fairfield Ludlowe | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | L 1-2 | |
| Wed., 10/25 | FR Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Aux Gym [Directions] | 4:00 p.m. | L 2-3 | |
| Thu., 10/26 | FR Football | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 5:00 p.m. | L 35 to 6 | |
| Fri., 10/27 | V Football | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 7:00 p.m. | W 24-10 | |
| Fri., 10/27 | V Field Hockey | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 2:00 p.m. | L 0-7 | |
| Fri., 10/27 | FR Field Hockey | Danbury | Away - Danbury HS-Grass Field Hockey Field [Directions] | 4:30 p.m. | ||
| Fri., 10/27 | V Girls Soccer | Fairfield Warde (Scrim.) | Home - Wilton HS-Lilly Field [Directions] | 4:30 p.m. | ||
| Fri., 10/27 | V Girls Volleyball | Stamford | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:45 p.m. | L 2-3 | |
| Fri., 10/27 | JV Girls Volleyball | Stamford | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | L 0-2 | |
| Fri., 10/27 | FR Girls Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | L 0-3 | |
| Sat., 10/28 | V Boys Cross Country | CIAC Class L Championship | Away - Wickham Park | 2:40 p.m. | ||
| Sat., 10/28 | JV Football | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Sat., 10/28 | V Girls Cross Country | CIAC Class L Championship | Away - Wickham Park | 2:05 p.m. | ||
| Sat., 10/28 | JV Girls Swimming and Diving | Greenwich, Danbury, Darien, Fairfield Ludlowe, New Canaan, Norwalk/McMahon, Ridgefield, St. Joseph, Staples, Trumbull, Westhill/Stamford | Away - Greenwich HS-Pool | 9:30 a.m. | ||
| Mon., 10/30 | FR Girls Volleyball | Staples | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Wed., 11/1 | V Girls Swimming and Diving | Greenwich, Danbury, Darien, Fairfield Ludlowe, Fairfield Warde, New Canaan, Norwalk/McMahon, Ridgefield, St. Joseph, Staples, Trumbull, Westhill/Stamford | Away - Greenwich HS-Pool | 5:30 p.m. | ||
| Thu., 11/2 | FR Football | St. Joseph | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 4:30 p.m. | W 19 to 15 | |
| Fri., 11/3 | V Football | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 7:00 p.m. | W 31-6 | |
| Sat., 11/4 | JV Football | Brien McMahon | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 10:00 a.m. | ||
| Sat., 11/4 | V Girls Swimming and Diving | Greenwich, Danbury, Darien, Fairfield Ludlowe, Fairfield Warde, New Canaan, Norwalk/McMahon, Ridgefield, St. Joseph, Staples, Trumbull, Westhill/Stamford | Away - Greenwich HS-Pool | 3:30 p.m. | ||
| Mon., 11/6 | V Boys Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Mon., 11/6 | V Girls Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Mon., 11/6 | V Girls Soccer | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 6:00 p.m. | ||
| Wed., 11/8 | V Field Hockey | Fairfield Ludlowe | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 5:00 p.m. | W 7-2 | |
| Wed., 11/8 | V Girls Swimming and Diving | CIAC Class L Diving Championship | Away - Middletown | 5:30 p.m. | ||
| Thu., 11/9 | FR Football | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 6:30 p.m. | W 20 to 6 | |
| Fri., 11/10 | V Football | Fairfield Ludlowe | Home - Wilton HS-Fujitani Field - Turf [Directions] | 7:00 p.m. | W 63-22 | |
| Fri., 11/10 | V Field Hockey | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 3:00 p.m. | W 0-1 | |
| Sat., 11/11 | JV Football | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 10:00 a.m. | ||
| Sat., 11/11 | V Girls Swimming and Diving | CIAC Class L Qualifying Meet | Away - Cornerstone Pool | 11:15 a.m. | ||
| Tue., 11/14 | V Field Hockey | Darien | Away - Norwalk HS-Testa Field [Directions] | 6:00 p.m. | OT-L 3-2 | |
| Tue., 11/14 | V Girls Swimming and Diving | CIAC Class L Finals | Away - Cornerstone Pool | 6:00 p.m. | ||
| Thu., 11/16 | FR Football | Shelton | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 4:30 p.m. | W 49 to 29 | |
| Thu., 11/16 | V Girls Swimming and Diving | CIAC State Open Diving | Away - Middletown | 5:30 p.m. | ||
| Fri., 11/17 | V Football | Shelton | Home - Wilton HS-Fujitani Field - Turf [Directions] | 7:00 p.m. | W 28-7 | |
| Sat., 11/18 | JV Football | Shelton | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 10:00 a.m. | ||
| Sun., 11/19 | V Girls Swimming and Diving | CIAC State Open Swimming | Away - Yale | 1:00 p.m. | ||
| Tue., 11/28 | V Football | Platt | Home - Wilton HS-Fujitani Field - Turf [Directions] | 6:30 p.m. | W 35-14 | |
| Tue., 11/28 | V Football | CIAC Quarterfinals | Away - Higher Seed | 6:30 p.m. | ||
| Wed., 11/29 | V Girls Ice Hockey | Fairfield Ludlowe/Warde (Scrim.) | Away - Sacred Heart University-Martire Arena [Directions] | 5:15 p.m. | W 15-3 | |
| Thu., 11/30 | V | Weston | Home - Wilton HS [Directions] | 3:00 p.m. | ||
| Sun., 12/3 | V Football | CIAC Semifinals | Away - Higher Seed | 12:30 p.m. | ||
| Sun., 12/3 | V Football | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 12:30 p.m. | W 35-10 | |
| Wed., 12/6 | V Girls Ice Hockey | New Canaan | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:30 p.m. | L 8-2 | |
| Thu., 12/7 | V Girls Basketball | New Milford (Scrim.) | Away - New Milford HS-Main Gym - NMHS [Directions] | 4:30 p.m. | ||
| Sat., 12/9 | V Football | North Haven | Home - CCSU [Directions] | 10:30 a.m. | L 0-21 | |
| Sat., 12/9 | V Football | CIAC Championship Games | Away - Site TBA | TBA | ||
| Sat., 12/9 | V Girls Ice Hockey | Southington Coop | Away - Newington-Red Rink [Directions] | 7:00 p.m. | L 6-1 | |
| Mon., 12/11 | V Boys Basketball | New Fairfield (Scrim.) | Away - New Fairfield HS-High School Gym [Directions] | 5:00 p.m. | ||
| Mon., 12/11 | V Girls Basketball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 7:00 p.m. | L 43-52 | |
| Mon., 12/11 | JV Girls Basketball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 5:15 p.m. | ||
| Wed., 12/13 | V Boys Ice Hockey | Milford Coop | Away - Milford Ice Pavillion-Ice Rink [Directions] | 8:00 p.m. | W 7-1 | |
| Wed., 12/13 | V Girls Basketball | Bethel | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:00 p.m. | W 37-32 | |
| Wed., 12/13 | JV Girls Basketball | Bethel | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Wed., 12/13 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:30 p.m. | W 6-2 | |
| Thu., 12/14 | V Boys Diving | Darien, Greenwich | Away - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Thu., 12/14 | V Wrestling | Greenwich | Home - Wilton HS-Nicholas Zeoli Fieldhouse [Directions] | 6:00 p.m. | ||
| Fri., 12/15 | V Boys Ice Hockey | Bethel/Brookfield/Danbury/Immaculate | Away - Danbury Ice Arena-Patriot Rink [Directions] | 4:00 p.m. | L 8-1 | |
| Fri., 12/15 | V Girls Ice Hockey | Darien | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 4:00 p.m. | L 4-0 | |
| Sat., 12/16 | V Boys Basketball | Newtown | Away - Newtown HS-Gym [Directions] | 4:00 p.m. | W 75-61 | |
| Sat., 12/16 | JV Boys Basketball | Newtown | Away - Newtown HS-Gym [Directions] | 2:30 p.m. | ||
| Sat., 12/16 | V Boys Indoor Track | Danbury, New Canaan, Norwalk | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:30 a.m. | ||
| Sat., 12/16 | V Boys Indoor Track | Brien McMahon, Darien, Fairfield Warde, Ridgefield | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 12:30 p.m. | ||
| Sat., 12/16 | V Wrestling | Guilford Wrestling Invitational | Away - Guilford HS-Main gym at GHS | 9:00 a.m. | ||
| Sat., 12/16 | V Girls Indoor Track | Danbury, New Canaan, Norwalk | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:30 a.m. | ||
| Sat., 12/16 | V Girls Indoor Track | Brien McMahon, Darien, Fairfield Warde, Ridgefield | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 12:30 p.m. | ||
| Sun., 12/17 | JV Girls Ice Hockey | Trumbull/St. Joseph, Fairfield Ludlowe/Warde, Greenwich, Ridgefield/Danbury/Immaculate (Scrim.) | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 2:00 p.m. | ||
| Tue., 12/19 | V Boys Swimming and Diving | Danbury | Away - WCSU O'Neill Center Pool [Directions] | 5:00 p.m. | Wilton 85 Danbury 52 | |
| Wed., 12/20 | V Boys Basketball | Bassick | Away - Bassick HS-Gym [Directions] | 7:00 p.m. | W 91-57 | |
| Wed., 12/20 | JV Boys Basketball | Bassick | Away - Bassick HS-Gym [Directions] | 5:30 p.m. | ||
| Wed., 12/20 | FR Boys Basketball | Bassick | Away - Bassick HS-Gym [Directions] | 4:00 p.m. | ||
| Wed., 12/20 | V Boys Ice Hockey | Shepaug Valley Ice Hockey | Away - The Frederick Gunn School-Ice Rink [Directions] | 6:30 p.m. | L 6-2 | |
| Wed., 12/20 | V Wrestling | Trumbull | Home - Wilton HS-Nicholas Zeoli Fieldhouse [Directions] | 6:00 p.m. | ||
| Wed., 12/20 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:30 p.m. | L 6-2 | |
| Fri., 12/22 | V Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:30 p.m. | W 54-30 | |
| Fri., 12/22 | JV Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Aux Gym [Directions] | 4:00 p.m. | ||
| Fri., 12/22 | V Girls Ice Hockey | Greenwich | Away - Greenwich - Dorothy Hamill-Rink [Directions] | 5:15 p.m. | W 9-2 | |
| Sat., 12/23 | V Boys Basketball | Fitch | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:45 p.m. | W 70-61 | |
| Sat., 12/23 | JV Boys Basketball | Fitch | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 3:00 p.m. | ||
| Sat., 12/23 | V Boys Ice Hockey | Suffield/Granby/Windsor Locks Wildcats | Away - Simsbury - ISCC-Olympic [Directions] | 4:00 p.m. | L 2-1 | |
| Sat., 12/23 | V Wrestling | New Canaan, North Haven, Stamford | Home - Wilton HS-Nicholas Zeoli Fieldhouse [Directions] | 9:00 a.m. | ||
| Wed., 12/27 | V Boys Basketball | Platt | Home - Polson MS, Madison-Polson Big Gym/DHHS Campus [Directions] | 1:00 p.m. | W 71-44 | |
| Wed., 12/27 | V Girls Basketball | St. Paul Catholic | Away - Pomperaug HS-Main Gym [Directions] | 3:00 p.m. | L 50-40 | |
| Wed., 12/27 | V Girls Ice Hockey | Hamden Coop | Away - Hamden-Lou Astorino Ice Rink [Directions] | 12:00 p.m. | W 8-7 | |
| Thu., 12/28 | V Boys Basketball | Daniel Hand | Away - Polson MS, Madison-Polson Big Gym/DHHS Campus [Directions] | 1:00 p.m. | L 68-53 | |
| Fri., 12/29 | V Girls Basketball | Pomperaug | Away - Pomperaug HS-Main Gym [Directions] | 3:00 p.m. | L 48-43 | |
| Fri., 12/29 | V Girls Ice Hockey | Woodstock Academy Coop | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 3:30 p.m. | W 5-2 | |
| Wed., 1/3 | V Boys Ice Hockey | Staples | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:30 p.m. | W 6-3 | |
| Wed., 1/3 | V Boys Swimming and Diving | Staples | Home - Wilton YMCA [Directions] | 3:40 p.m. | Wilton 92 Staples 61 | |
| Wed., 1/3 | V Wrestling | Staples | Away - Staples HS-Field House [Directions] | 6:00 p.m. | ||
| Wed., 1/3 | V Girls Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | L 52-32 | |
| Wed., 1/3 | JV Girls Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to 4:00 p.m. | ||||||
| Wed., 1/3 | JV Girls Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 1/3 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Conners - Stamford-Ice Rink [Directions] | 5:30 p.m. | L 5-2 | |
| Fri., 1/5 | V Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 6:00 p.m. | L 68-53 | |
| Fri., 1/5 | JV Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/5 | FR Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Small Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/5 | V Girls Basketball | Fairfield Warde | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:00 p.m. | L 44-25 | |
| Fri., 1/5 | JV Girls Basketball | Fairfield Warde | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Sat., 1/6 | V Boys Ice Hockey | Trumbull | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | 3:00 p.m. | W 4-2 | |
| Sat., 1/6 | V Boys Indoor Track | Darien, New Canaan, Ridgefield | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:30 a.m. | ||
| Sat., 1/6 | V Boys Indoor Track | Danbury, Fairfield Ludlowe, Fairfield Warde, Norwalk | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 12:30 p.m. | ||
| Sat., 1/6 | V Wrestling | Warde Wrestling Invitational | Away - Fairfield Warde HS-Large Gym | TBA | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 9:00 a.m. | ||||||
| Sat., 1/6 | V Girls Indoor Track | Darien, New Canaan, Ridgefield | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:30 a.m. | ||
| Sat., 1/6 | V Girls Indoor Track | Danbury, Fairfield Ludlowe, Fairfield Warde, Norwalk | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 12:30 p.m. | ||
| Mon., 1/8 | V Boys Ice Hockey | Fox Lane (NY) | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 4:00 p.m. | W 7-3 | |
| Mon., 1/8 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Home - Wilton YMCA [Directions] | 3:40 p.m. | Wilton 102 Fairfield co-op 68 | |
| Tue., 1/9 | V Boys Basketball | Norwalk | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:00 p.m. | L 55-53 | |
| Tue., 1/9 | JV Boys Basketball | Norwalk | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:15 p.m. | ||
| Tue., 1/9 | FR Boys Basketball | Norwalk | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Tue., 1/9 | V Boys Diving | Fairfield Ludlowe | Home - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Tue., 1/9 | V Girls Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 6:15 p.m. | W 29-26 | |
| Tue., 1/9 | JV Girls Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:30 p.m. | ||
| Wed., 1/10 | V Boys Swimming and Diving | Ridgefield | Away - Barlow Mountain Pool [Directions] | 4:00 p.m. | Ridgefield 94 Wilton 91 | |
| Wed., 1/10 | V Wrestling | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/10 | V Girls Basketball | Kolbe Cathedral | Away - Cardinal Sheehan Center Bridgeport [Directions] | 7:00 p.m. | L 59-38 | |
| Wed., 1/10 | JV Girls Basketball | Kolbe Cathedral | Away - Cardinal Sheehan Center Bridgeport [Directions] | 5:15 p.m. | ||
| Wed., 1/10 | V Girls Gymnastics | Stamford, Westhill | Home - Wilton HS-Aux Gym [Directions] | 4:30 p.m. | Wilton - 136.15 Stamford - 113.85 Westhill - 95.6 | |
| Thu., 1/11 | JV Girls Ice Hockey | Greenwich Academy | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 4:00 p.m. | ||
| Fri., 1/12 | V Boys Basketball | Darien | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 7:00 p.m. | W 70-69 | |
| Fri., 1/12 | JV Boys Basketball | Darien | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:15 p.m. | ||
| Fri., 1/12 | FR Boys Basketball | Darien | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Fri., 1/12 | V Girls Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | W 51-38 | |
| Fri., 1/12 | JV Girls Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/12 | V Girls Gymnastics | Greenwich | Home - Wilton HS-Aux Gym [Directions] | 4:30 p.m. | 138.55 | |
| Sat., 1/13 | V Boys Ice Hockey | Westhill/Stamford | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:00 p.m. | L 2-1 | |
| Sat., 1/13 | V Boys Indoor Track | Brien McMahon, Fairfield Ludlowe, Fairfield Warde, New Canaan, Norwalk, Ridgefield, Trumbull | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:30 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 9:00 a.m. | ||||||
| Sat., 1/13 | V Wrestling | Bunnell, Amity, Canton, Notre Dame-Fairfield | Away - Bunnell HS-David Johnson Gymnasium [Directions] | 9:00 a.m. | ||
| Sat., 1/13 | V Girls Indoor Track | Brien McMahon, Fairfield Ludlowe, Fairfield Warde, New Canaan, Norwalk, Ridgefield | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:30 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 9:00 a.m. | ||||||
| Mon., 1/15 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 9:00 a.m. | W 4-3 | |
| Wed., 1/17 | V Boys Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 7:00 p.m. | W 59-47 | |
| Wed., 1/17 | JV Boys Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 1/17 | FR Boys Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 1/17 | V Boys Ice Hockey | Milford Coop | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:30 p.m. | L 2-0 | |
| Wed., 1/17 | V Boys Swimming and Diving | New Canaan | Away - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | Wilton - 82 New Canaan - 98 | |
| Wed., 1/17 | V Girls Basketball | Greenwich | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:15 p.m. | W 42-30 | |
| Wed., 1/17 | JV Girls Basketball | Greenwich | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:45 p.m. | ||
| Thu., 1/18 | V Wrestling | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 6:30 p.m. | ||
| Fri., 1/19 | V Boys Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 7:00 p.m. | L 76-51 | |
| Fri., 1/19 | JV Boys Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/19 | FR Boys Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/19 | V Girls Basketball | Trumbull | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:00 p.m. | L 35-40 | |
| Fri., 1/19 | JV Girls Basketball | Trumbull | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Fri., 1/19 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 4:00 p.m. | W 6-3 | |
| Sat., 1/20 | V Boys Ice Hockey | Shepaug Valley Ice Hockey | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:00 p.m. | W 2-1 | |
| Sat., 1/20 | V Boys Indoor Track | Bridgeport Central, Brien McMahon, Danbury, Greenwich, New Canaan, St. Joseph, Stamford | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:30 a.m. | ||
| Sat., 1/20 | V Girls Indoor Track | Hillhouse Invitational | Away - . | 9:00 a.m. | ||
| Sat., 1/20 | V Girls Indoor Track | Bridgeport Central, Brien McMahon, Danbury, Greenwich, New Canaan, St. Joseph, Stamford | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:30 a.m. | ||
| Mon., 1/22 | V Boys Swimming and Diving | Westhill/Stamford | Away - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | Wilton 88 Westhill 72 | |
| Wed., 1/24 | V Boys Basketball | Danbury | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 7:00 p.m. | W 61-53 | |
| Wed., 1/24 | JV Boys Basketball | Danbury | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:15 p.m. | ||
| Wed., 1/24 | FR Boys Basketball | Danbury | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Wed., 1/24 | V Boys Ice Hockey | Brien McMahon/Norwalk | Away - Sono Ice House-Main Rink [Directions] | 8:50 p.m. | L 6-5 | |
| Wed., 1/24 | V Boys Swimming and Diving | Greenwich | Home - Wilton YMCA [Directions] | 3:30 p.m. | Greenwich 110 Wilton 76 | |
| Wed., 1/24 | V Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 7:00 p.m. | W 47-43 | |
| Wed., 1/24 | JV Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 1/25 | V Boys Diving | Norwalk | Home - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Thu., 1/25 | V Wrestling | Fairfield Ludlowe | Home - Wilton HS-Nicholas Zeoli Fieldhouse [Directions] | 6:00 p.m. | ||
| Fri., 1/26 | V Boys Basketball | New Canaan | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 7:00 p.m. | W 46-38 | |
| Fri., 1/26 | JV Boys Basketball | New Canaan | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:15 p.m. | ||
| Fri., 1/26 | FR Boys Basketball | New Canaan | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Fri., 1/26 | V Boys Ice Hockey | Fox Lane (NY) | Away - Fox Lane HS | 4:15 p.m. | L 4-2 | |
| Fri., 1/26 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Home - Wilton YMCA [Directions] | 3:30 p.m. | Norwalk 96 Wilton 88 | |
| Fri., 1/26 | V Girls Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 6:00 p.m. | L 36-29 | |
| Fri., 1/26 | JV Girls Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:30 p.m. | ||
| Fri., 1/26 | V Girls Ice Hockey | Daniel Hand Coop | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 4:00 p.m. | W 5-3 | |
| Sat., 1/27 | V Boys Indoor Track | Divisional Championship | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:30 a.m. | ||
| Sat., 1/27 | V Wrestling | Brookfield Invitational | Away - Brookfield HS-BHS Small & Big Gym | 9:30 a.m. | ||
| Sat., 1/27 | JV Wrestling | Norwalk, Brien McMahon, Darien, Fairfield Prep, Fairfield Ludlowe, Fairfield Warde, Greenwich, New Canaan, New Milford, St. Joseph, Stamford, Staples, Trumbull, Westhill, Weston | Away - Norwalk HS-Tom Scarso Gymnasium | 8:00 a.m. | ||
| Sat., 1/27 | V Girls Gymnastics | Trumbull | Away - Next Dimension Gymnastics-Next Dimension [Directions] | 4:30 p.m. | 121.6 | |
| Sat., 1/27 | V Girls Gymnastics | St. Joseph | Away - Next Dimension Gymnastics-Next Dimension [Directions] | 4:30 p.m. | ||
| Sat., 1/27 | JV Girls Ice Hockey | Choate Rosemary Hall | Away - Choate Rosemary Hall-Ice Rink | 2:30 p.m. | ||
| Sat., 1/27 | V Girls Indoor Track | Divisional Championships | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:30 a.m. | ||
| Tue., 1/30 | V Boys Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 7:00 p.m. | L 68-76 | |
| Tue., 1/30 | JV Boys Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/30 | FR Boys Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/30 | V Girls Basketball | Staples | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:00 p.m. | W 40-31 | |
| Tue., 1/30 | JV Girls Basketball | Staples | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Tue., 1/30 | V Girls Gymnastics | Fairfield Ludlowe, Fairfield Warde | Home - Wilton HS-Aux Gym [Directions] | 4:30 p.m. | Cancelled | |
| Wed., 1/31 | V Boys Ice Hockey | Housatonic Coop | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:30 p.m. | W 5-3 | |
| Wed., 1/31 | V Boys Swimming and Diving | Darien | Home - Wilton YMCA [Directions] | 3:30 p.m. | Wilton 101 Darien 80 | |
| Wed., 1/31 | V Wrestling | Fairfield Warde | Home - Wilton HS-Nicholas Zeoli Fieldhouse [Directions] | 6:00 p.m. | ||
| Wed., 1/31 | V Girls Ice Hockey | Stamford/Westhill/Staples | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 4:00 p.m. | L 7-3 | |
| Thu., 2/1 | FR Boys Basketball | Ridgefield | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Thu., 2/1 | V Boys Indoor Track | FCIAC Championship Floyd Little Athletic Center | Away - Not Listed | TBA | ||
| Thu., 2/1 | JV Girls Basketball | Ridgefield | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:00 p.m. | ||
| Thu., 2/1 | V Girls Gymnastics | Fairfield Warde, Norwalk, Staples | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:00 p.m. | ||
| Thu., 2/1 | V Girls Gymnastics | TBA, Fairfield Ludlowe | Away - TBA | 7:00 p.m. | ||
| Pending changes awaiting acceptance by one or more parties involved: Time to 6:00 p.m., Facility to Gymnastics and Cheerleading Academy at Connecticut-Gym 1 | ||||||
| Fri., 2/2 | V Boys Ice Hockey | SCW Knights | Away - Cromwell-Lower Rink [Directions] | 4:30 p.m. | W 3-1 | |
| Sat., 2/3 | V Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 7:00 p.m. | L 52-46 | |
| Sat., 2/3 | JV Boys Basketball | Ridgefield | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 12:00 p.m. | ||
| Sat., 2/3 | V Boys Ice Hockey | Trumbull | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:00 p.m. | W 3-1 | |
| Sat., 2/3 | V Wrestling | Morgan, Canton, Granby Memorial, Griswold/Wheeler | Away - Morgan School-Gym [Directions] | 9:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 10:00 a.m. | ||||||
| Sat., 2/3 | V Girls Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:00 p.m. | L 52-44 | |
| Sat., 2/3 | V Competitive Cheerleading | FCIAC Cheer Championship | Away - Trumbull HS-THS Main Gym | 10:00 a.m. | ||
| Sat., 2/3 | V Girls Gymnastics | Darien | Away - Darien YMCA [Directions] | 2:30 p.m. | 130.0 | |
| Mon., 2/5 | V Boys Swimming and Diving | Trumbull | Home - Wilton YMCA [Directions] | 3:40 p.m. | Wilton 96 Trumbull 62 | |
| Mon., 2/5 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Sacred Heart University-Martire Arena [Directions] | 5:15 p.m. | W 9-7 | |
| Tue., 2/6 | V Boys Basketball | Bridgeport Central | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 7:00 p.m. | W 63-32 | |
| Tue., 2/6 | JV Boys Basketball | Bridgeport Central | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:30 p.m. | ||
| Tue., 2/6 | FR Boys Basketball | Bridgeport Central | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Tue., 2/6 | V Wrestling | Darien | Away - Darien HS-DHS South Gym [Directions] | 6:00 p.m. | ||
| Tue., 2/6 | V Girls Basketball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | 6:00 p.m. | W 59-33 | |
| Tue., 2/6 | JV Girls Basketball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | 4:30 p.m. | ||
| Tue., 2/6 | V Girls Gymnastics | Norwalk, Staples | Home - Wilton HS-Aux Gym [Directions] | 4:30 p.m. | 135.6 | |
| Wed., 2/7 | V Boys Ice Hockey | Bethel/Brookfield/Danbury/Immaculate | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:30 p.m. | L 3-1 | |
| Wed., 2/7 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 3:45 p.m. | L 3-1 | |
| Fri., 2/9 | V Boys Basketball | St. Joseph | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 7:00 p.m. | W 70-51 | |
| Fri., 2/9 | JV Boys Basketball | St. Joseph | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:15 p.m. | ||
| Fri., 2/9 | FR Boys Basketball | St. Joseph | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Fri., 2/9 | V Wrestling | New Canaan, Bridgeport Central, Brien McMahon, Danbury, Darien, FCIAC, Fairfield Ludlowe, Fairfield Warde, Greenwich, Norwalk, Ridgefield, St. Joseph, Stamford, Staples, Trumbull, Westhill | Away - New Canaan HS-Main Gym | 4:30 p.m. | ||
| Fri., 2/9 | V Girls Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 6:00 p.m. | L 42-40 | |
| Fri., 2/9 | JV Girls Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:30 p.m. | ||
| Fri., 2/9 | V Girls Ice Hockey | Southington Coop | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 4:00 p.m. | L 6-4 | |
| Sat., 2/10 | V Boys Ice Hockey | Staples | Away - Milford Ice Pavillion-Ice Rink [Directions] | 8:00 p.m. | W 4-0 | |
| Sat., 2/10 | V Boys Indoor Track | CIAC L Divisional Championship | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Sat., 2/10 | V Girls Gymnastics | FCIAC's at GCA | Away - . | 4:30 p.m. | 127.95 | |
| Sat., 2/10 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Away - Hamden-Lou Astorino Ice Rink [Directions] | 8:15 p.m. | L 4-2 | |
| Mon., 2/12 | V Boys Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 7:00 p.m. | W 70-50 | |
| Mon., 2/12 | JV Boys Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/12 | FR Boys Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 2/12 | V Boys Ice Hockey | Brien McMahon/Norwalk | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 3:00 p.m. | W 4-3 | |
| Mon., 2/12 | V Girls Basketball | Westhill | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:00 p.m. | W 78-24 | |
| Mon., 2/12 | JV Girls Basketball | Westhill | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Wed., 2/14 | V Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 7:00 p.m. | W 64-61 | |
| Wed., 2/14 | JV Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 2/14 | FR Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 2/14 | V Boys Ice Hockey | Westhill/Stamford | Away - Terry Conners - Stamford-Ice Rink [Directions] | 7:00 p.m. | L 4-1 | |
| Wed., 2/14 | V Girls Basketball | Brien McMahon | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:00 p.m. | W 48-28 | |
| Wed., 2/14 | JV Girls Basketball | Brien McMahon | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Thu., 2/15 | V Girls Gymnastics | New Milford, Brookfield, Danbury, Oxford, Pomperaug | Away - New Milford HS-Small Gym - NMHS | 5:30 p.m. | 130.3 | |
| Thu., 2/15 | V Girls Ice Hockey | Mercy/NW Catholic/East Hampton | Away - Cromwell-Lower Rink [Directions] | 4:30 p.m. | L 9-3 | |
| Fri., 2/16 | V Wrestling | CIAC L Divisional Championship | Away - Wilton | TBA | ||
| Fri., 2/16 | V Girls Ice Hockey | Masuk Coop | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 4:00 p.m. | W 5-2 | |
| Sat., 2/17 | V Boys Indoor Track | CIAC State Open Divisional Championship | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/17 | V Girls Basketball | St. Joseph | Away - Staples HS-Staples Gym [Directions] | 4:15 p.m. | ||
| Sat., 2/17 | JV Girls Ice Hockey | Suffield Coop | Away - Enfield Twin Rinks-Rink 1 [Directions] | 6:20 p.m. | ||
| Sat., 2/17 | V Girls Indoor Track | CIAC State Open Championship | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Mon., 2/19 | V Boys Basketball | Fairfield Ludlowe | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 7:00 p.m. | W 61-35 | |
| Mon., 2/19 | JV Boys Basketball | Fairfield Ludlowe | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:15 p.m. | ||
| Mon., 2/19 | FR Boys Basketball | Fairfield Ludlowe | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Tue., 2/20 | V Girls Ice Hockey | East Catholic Coop | Away - Newington-Red Rink [Directions] | 4:30 p.m. | L 7-0 | |
| Wed., 2/21 | V Boys Basketball | Stamford | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 7:00 p.m. | ||
| Wed., 2/21 | JV Boys Basketball | Stamford | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:15 p.m. | ||
| Wed., 2/21 | FR Boys Basketball | Stamford | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Wed., 2/21 | V Girls Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | 6:00 p.m. | ||
| Fri., 2/23 | V Wrestling | CIAC State Open & Girls Championship | Away - Floyd Little Athletic Center | TBA | ||
| Sat., 2/24 | V Boys Basketball | Staples | Away - Fairfield Warde HS-Gym [Directions] | 4:00 p.m. | ||
| Sat., 2/24 | V Boys Ice Hockey | Housatonic Coop | Away - South Kent School-Ice Rink [Directions] | 7:00 p.m. | W 7-4 | |
| Sat., 2/24 | V Girls Gymnastics | CIAC Class M Divisional Championship | Away - Jonathan Law | 9:00 a.m. | ||
| Tue., 2/27 | V Girls Basketball | Lyman Hall | Away - Lyman Hall HS-Gymnasium [Directions] | 6:30 p.m. | W 50-46 | |
| Fri., 3/1 | V Girls Basketball | Holy Cross | Away - Holy Cross-gym [Directions] | 6:30 p.m. | L 46-59 | |
| Sat., 3/2 | V Girls Gymnastics | CIAC State Open | Away - New Milford | 12:00 p.m. | ||
| Mon., 3/4 | V Boys Basketball | Middletown | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:00 p.m. | W 70-69 | |
| Mon., 3/4 | V Boys Ice Hockey | Rocky Hill Coop | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 3:00 p.m. | L 1-4 | |
| Mon., 3/4 | V Boys Ice Hockey | CIAC Div III First Round | Away - Higher Seed | TBA | ||
| Wed., 3/6 | V Boys Basketball | Bloomfield | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:30 p.m. | L 74-88 | |
| Thu., 3/7 | V Boys Ice Hockey | CIAC Div III Quarterfinal | Away - Site TBA | TBA | ||
| Thu., 3/7 | V Boys Swimming and Diving | CIAC Class M Diving Championship | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/9 | V Boys Swimming and Diving | CIAC Class M Qualifying Meet | Away - Cheshire Community Pool | 6:45 p.m. | ||
| Mon., 3/11 | V Boys Ice Hockey | CIAC Div III Semifinal | Away - Site TBA | TBA | ||
| Mon., 3/11 | V Boys Swimming and Diving | CIAC Class M Finals | Away - Wesleyan | 6:00 p.m. | ||
| Thu., 3/14 | V Boys Ice Hockey | CIAC Div III Final | Away - Site TBA | TBA | ||
| Thu., 3/14 | V Boys Swimming and Diving | CIAC State Open Diving | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/16 | V Boys Swimming and Diving | CIAC State Open Swimming | Away - Yale | 1:00 p.m. | ||
| Wed., 3/20 | V Baseball | New Canaan (Scrim.) | Home - Wilton HS-Varsity Baseball Field [Directions] | 4:15 p.m. | ||
| Thu., 3/21 | V Softball | Greenwich (Scrim.) | Home - Wilton HS-Varsity Softball Field [Directions] | 4:15 p.m. | ||
| Thu., 3/21 | JV Softball | Greenwich (Scrim.) | Home - Wilton HS-JV Softball Field [Directions] | 4:15 p.m. | ||
| Fri., 3/22 | V Softball | Brookfield (Scrim.) | Away - Brookfield HS-BHS Softball Field [Directions] | 4:30 p.m. | ||
| Fri., 3/22 | JV Softball | Brookfield (Scrim.) | Away - Cadigan Field-Field #1 [Directions] | 4:30 p.m. | ||
| Sat., 3/23 | V Girls Lacrosse | New Canaan (Scrim.) | Home - Wilton HS-Lilly Field [Directions] | Canceled | Cancelled | |
| Sat., 3/23 | JV Girls Lacrosse | New Canaan (Scrim.) | Home - Wilton HS-Lilly Field [Directions] | Canceled | Cancelled | |
| Mon., 3/25 | V Boys Lacrosse | Iona Prep (NY) (Scrim.) | Home - Greenwich HS-Field 3 [Directions] | 4:45 p.m. | ||
| Mon., 3/25 | V Boys Lacrosse | Greenwich (Scrim.) | Away - Greenwich HS-Field 3 [Directions] | 5:45 p.m. | ||
| Mon., 3/25 | V Boys Tennis | Joel Barlow (Scrim.) | Home - Wilton HS-Tennis Courts [Directions] | 3:30 p.m. | ||
| Tue., 3/26 | V Baseball | Darien (Scrim.) | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:15 p.m. | ||
| Tue., 3/26 | JV Baseball | Darien (Scrim.) | Away - Darien HS-DHS Baseball - JV Field [Directions] | 4:15 p.m. | ||
| Tue., 3/26 | V Boys Lacrosse | Notre Dame-West Haven (Scrim.) | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 4:30 p.m. | ||
| Tue., 3/26 | V Girls Lacrosse | Amity (Scrim.) | Home - Wilton HS-Lilly Field [Directions] | 4:30 p.m. | ||
| Wed., 3/27 | V Baseball | Norwalk (Scrim.) | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 4:00 p.m. | ||
| Wed., 3/27 | JV Baseball | Norwalk (Scrim.) | Away - City Hall Field [Directions] | 4:00 p.m. | ||
| Wed., 3/27 | V Softball | New Milford (Scrim.) | Home - Wilton HS-Varsity Softball Field [Directions] | 4:00 p.m. | ||
| Wed., 3/27 | JV Softball | New Milford (Scrim.) | Home - Wilton HS-JV Softball Field [Directions] | 4:00 p.m. | ||
| Wed., 3/27 | V Girls Tennis | Weston (Scrim.) | Home - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 3/27 | JV Girls Tennis | Weston (Scrim.) | Home - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 3/28 | V Girls Lacrosse | Newtown (Scrim.) | Away - Newtown HS-Blue and Gold Stadium [Directions] | 4:15 p.m. | ||
| Thu., 3/28 | V Softball | Weston (Scrim.) | Away - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 4:00 p.m. | Cancelled | |
| Thu., 3/28 | V Girls Tennis | vs GFA | Home - Wilton HS-Tennis Courts [Directions] | 3:45 p.m. | ||
| Sat., 3/30 | V Baseball | Branford | Home - Wilton HS-Varsity Baseball Field [Directions] | 11:00 a.m. | ||
| Sat., 3/30 | JV Baseball | Branford | Home - Wilton HS-JV Baseball Field [Directions] | 11:00 a.m. | ||
| Sat., 3/30 | V Boys Lacrosse | Somers (NY) | Away - Somers HS | 12:00 p.m. | ||
| Sat., 3/30 | JV Boys Lacrosse | Somers (NY) | Away - Somers HS | 10:00 a.m. | ||
| Mon., 4/1 | V Boys Tennis | Weston | Home - Wilton HS-Tennis Courts [Directions] | 3:30 p.m. | W 7-0 [Detailed Results] | |
| Mon., 4/1 | V Softball | New Fairfield | Home - Wilton HS-Varsity Softball Field [Directions] | 4:15 p.m. | L 3-8 | |
| Mon., 4/1 | JV Softball | New Fairfield | Home - Wilton HS-JV Softball Field [Directions] | 4:15 p.m. | ||
| Mon., 4/1 | V Girls Tennis | St. Lukes | Home - Wilton Middlebrook School-JV Tennis Courts [Directions] | 3:30 p.m. | ||
| Tue., 4/2 | V Boys Lacrosse | Weston | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 6:30 p.m. | ||
| Tue., 4/2 | JV Boys Lacrosse | Weston | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/2 | FR Boys Lacrosse | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 4/2 | V Girls Lacrosse | Brien McMahon | Home - Wilton HS-Lilly Field [Directions] | 6:00 p.m. | ||
| Tue., 4/2 | JV Girls Lacrosse | Brien McMahon | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | ||
| Tue., 4/2 | FR Girls Lacrosse | Darien | Home - Wilton HS-Allen Meadow [Directions] | Postponed | ||
| Thu., 4/4 | FR Boys Lacrosse | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | Postponed | ||
| Thu., 4/4 | V Boys Tennis | St. Lukes | Home - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 4/4 | V Girls Golf | Darien | Home - Silvermine Golf Club [Directions] | Postponed | ||
| Thu., 4/4 | V Girls Lacrosse | North Shore (NY) | Home - Wilton HS-Lilly Field [Directions] | 5:00 p.m. | ||
| Thu., 4/4 | FR Girls Lacrosse | New Canaan | Home - Wilton HS-Allen Meadow [Directions] | 3:30 p.m. | ||
| Fri., 4/5 | V Girls Lacrosse | Cheshire | Away - Cheshire HS-Main Game Field [Directions] | 6:00 p.m. | ||
| Fri., 4/5 | JV Girls Lacrosse | Cheshire | Away - Cheshire HS-Main Game Field [Directions] | Postponed | ||
| Fri., 4/5 | V Softball | Sheehan | Home - Wilton HS-Varsity Softball Field [Directions] | 4:15 p.m. | L 0-9 | |
| Sat., 4/6 | V Baseball | Weston | Home - Wilton HS-Varsity Baseball Field [Directions] | 11:00 a.m. | ||
| Sat., 4/6 | V Boys Lacrosse | Stepinac (NY) | Home - Wilton HS-Veterans Memorial Stadium [Directions] | Canceled | Cancelled | |
| Sat., 4/6 | V Boys Lacrosse | Stepinac (NY) | Away - IONA PREP-Lacrosse Field | 3:00 p.m. | ||
| Sat., 4/6 | JV Boys Lacrosse | Stepinac (NY) | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 12:30 p.m. | ||
| Sat., 4/6 | JV Boys Lacrosse | Stepinac (NY) | Away - Stepinac HS-Field | Canceled | Cancelled | |
| Mon., 4/8 | V Baseball | Stamford | Home - Wilton HS-Varsity Baseball Field [Directions] | 5:30 p.m. | ||
| Mon., 4/8 | FR Boys Lacrosse | Staples | Home - Allen's Meadow-Lacrosse Field #1 [Directions] | 5:00 p.m. | ||
| Mon., 4/8 | V Boys Tennis | Fairfield Warde | Away - Fairfield Warde HS-Blake Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Mon., 4/8 | JV Boys Tennis | Fairfield Warde | Away - Fairfield Warde HS-Knapps Courts [Directions] | 4:00 p.m. | ||
| Mon., 4/8 | JV Boys Volleyball | Brien McMahon | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:15 p.m. | ||
| Mon., 4/8 | V Girls Lacrosse | Bronxville (NY) | Away - Bronxville HS | Canceled | Cancelled | |
| Mon., 4/8 | FR Girls Lacrosse | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 5:00 p.m. | ||
| Mon., 4/8 | V Softball | Darien | Away - Darien HS-DHS Softball - Varsity Field [Directions] | 4:30 p.m. | L 3-6 | |
| Mon., 4/8 | V Girls Tennis | Fairfield Warde | Home - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | W 5-2 [Detailed Results] | |
| Mon., 4/8 | JV Girls Tennis | Fairfield Warde | Home - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/9 | V Baseball | O'Brien Tech | Home - Wilton HS-Varsity Baseball Field [Directions] | 3:30 p.m. | ||
| Tue., 4/9 | V Baseball | O'Brien Tech | Home - Wilton HS-Varsity Baseball Field [Directions] | 6:30 p.m. | ||
| Tue., 4/9 | JV Baseball | Weston | Home - Wilton HS-JV Baseball Field [Directions] | 4:15 p.m. | ||
| Tue., 4/9 | V Boys Lacrosse | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 4:00 p.m. | ||
| Tue., 4/9 | JV Boys Lacrosse | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 5:30 p.m. | ||
| Tue., 4/9 | V Boys Outdoor Track | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Tue., 4/9 | V Boys Tennis | Norwalk | Home - Wilton HS-Allen Meadow [Directions] | 4:00 p.m. | W 6-1 [Detailed Results] | |
| Tue., 4/9 | V Girls Golf | Darien | Away - Woodway Country Club [Directions] | 3:00 p.m. | ||
| Tue., 4/9 | V Girls Outdoor Track | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Tue., 4/9 | V Girls Tennis | Norwalk | Away - Grassroots Tennis and Education-Grassroots Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Wed., 4/10 | FR Boys Lacrosse | Trumbull | Away - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Wed., 4/10 | V Boys Outdoor Track | New Canaan | Home - Wilton HS-Track [Directions] | 4:00 p.m. | ||
| Wed., 4/10 | JV Boys Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 5:45 p.m. | ||
| Wed., 4/10 | V Girls Golf | Ridgefield | Home - Silvermine Golf Club [Directions] | 3:30 p.m. | ||
| Wed., 4/10 | V Girls Outdoor Track | New Canaan | Home - Wilton HS-Track [Directions] | 4:00 p.m. | ||
| Wed., 4/10 | V Softball | New Canaan | Away - New Canaan HS-Orchard Field [Directions] | 6:45 p.m. | L 1-3 | |
| Wed., 4/10 | JV Girls Tennis | Greenwich Academy | Away - Greenwich Academy - Everett Field | 4:15 p.m. | ||
| Thu., 4/11 | V Boys Lacrosse | Glastonbury | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 7:00 p.m. | ||
| Thu., 4/11 | JV Boys Lacrosse | Glastonbury | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 4:30 p.m. | ||
| Thu., 4/11 | V Girls Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 3:30 p.m. | ||
| Thu., 4/11 | V Softball | Immaculate | Away - Immaculate HS-Softball Diamond [Directions] | 4:30 p.m. | W 15-9 | |
| Fri., 4/12 | FR Boys Lacrosse | Westhill | Home - Wilton HS-Fujitani Field - Turf [Directions] | 4:15 p.m. | ||
| Fri., 4/12 | V Girls Lacrosse | Shenendehowa (NY) | Home - Wilton HS-Lilly Field [Directions] | 6:00 p.m. | ||
| Fri., 4/12 | FR Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Fairfield Warde Grass Utility Field [Directions] | 6:30 p.m. | ||
| Fri., 4/12 | JV Softball | Fairfield Warde | Away - Melville Park [Directions] | Postponed | ||
| Sat., 4/13 | V Baseball | Fairfield Warde | Home - Wilton HS-Varsity Baseball Field [Directions] | 1:00 p.m. | ||
| Sat., 4/13 | JV Baseball | Fairfield Warde | Home - Wilton HS-JV Baseball Field [Directions] | 1:00 p.m. | ||
| Sat., 4/13 | FR Baseball | Fairfield Warde | Away - Fairfield Warde HS-Baseball Diamond [Directions] | 2:00 p.m. | ||
| Sat., 4/13 | V Boys Lacrosse | Greenwich | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 3:30 p.m. | ||
| Sat., 4/13 | JV Boys Lacrosse | Greenwich | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 12:00 p.m. | ||
| Sat., 4/13 | V Girls Lacrosse | Greenwich | Home - Wilton HS-Lilly Field [Directions] | 2:00 p.m. | ||
| Sat., 4/13 | JV Girls Lacrosse | Greenwich | Home - Wilton HS-Lilly Field [Directions] | 12:00 p.m. | ||
| Sat., 4/13 | V Softball | Fairfield Warde | Away - Fairfield Warde HS-Softball Diamond [Directions] | 2:00 p.m. | ||
| Mon., 4/15 | V Baseball | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 4:00 p.m. | ||
| Mon., 4/15 | JV Baseball | Norwalk | Away - City Hall Field [Directions] | 4:00 p.m. | ||
| Mon., 4/15 | FR Baseball | Norwalk | Home - Allen's Meadow-Baseball Diamond [Directions] | 4:15 p.m. | ||
| Mon., 4/15 | FR Boys Lacrosse | New Canaan | Home - Wilton HS-Fujitani Field - Turf [Directions] | 4:15 p.m. | ||
| Mon., 4/15 | V Boys Tennis | Greenwich | Away - Greenwich HS-Tennis Courts [Directions] | 4:15 p.m. | L 5-2 [Detailed Results] | |
| Mon., 4/15 | V Softball | Norwalk | Home - Wilton HS-Varsity Softball Field [Directions] | 6:00 p.m. | ||
| Mon., 4/15 | JV Softball | Norwalk | Home - Wilton HS-JV Softball Field [Directions] | Postponed | ||
| Mon., 4/15 | V Girls Tennis | Greenwich | Home - Wilton HS-Tennis Courts [Directions] | 11:00 a.m. | L 1-6 [Detailed Results] | |
| Tue., 4/16 | FR Boys Lacrosse | Ridgefield | Home - Allen's Meadow-Lacrosse Field #1 [Directions] | 1:00 p.m. | ||
| Tue., 4/16 | V Boys Tennis | Trumbull | Away - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | L 5-2 [Detailed Results] | |
| Tue., 4/16 | JV Boys Tennis | Trumbull | Away - Tashua Knolls Golf Course-Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/16 | V Girls Lacrosse | Rye (NY) | Away - Rye HS-Field | 5:00 p.m. | ||
| Tue., 4/16 | JV Girls Lacrosse | Rye (NY) | Away - Rye HS | 6:30 p.m. | ||
| Tue., 4/16 | V Girls Tennis | Trumbull | Home - Wilton HS-Allen Meadow [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Tue., 4/16 | JV Girls Tennis | Trumbull | Home - Wilton Middlebrook School-JV Tennis Courts [Directions] | Postponed | ||
| Wed., 4/17 | V Baseball | Darien | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 4/17 | JV Baseball | Darien | Away - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | ||
| Wed., 4/17 | FR Baseball | Darien | Home - Wilton HS-JV Baseball Field [Directions] | 4:15 p.m. | ||
| Wed., 4/17 | V Boys Tennis | Darien | Home - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | L 4-0 [Detailed Results] | |
| Wed., 4/17 | V Softball | Darien | Home - Wilton HS-Varsity Softball Field [Directions] | 5:00 p.m. | ||
| Thu., 4/18 | V Boys Lacrosse | Staples | Away - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Thu., 4/18 | JV Boys Lacrosse | Staples | Away - Staples HS-Staples Stadium [Directions] | 3:00 p.m. | ||
| Thu., 4/18 | V Girls Lacrosse | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Thu., 4/18 | JV Girls Lacrosse | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 5:30 p.m. | ||
| Fri., 4/19 | V Baseball | Greenwich | Home - Wilton HS-Varsity Baseball Field [Directions] | 4:15 p.m. | ||
| Fri., 4/19 | JV Baseball | Greenwich | Home - Wilton HS-JV Baseball Field [Directions] | 4:15 p.m. | ||
| Fri., 4/19 | FR Baseball | Greenwich | Away - Havemeyer Field-Havermeyer Field [Directions] | 4:30 p.m. | ||
| Fri., 4/19 | FR Boys Lacrosse | Fairfield Prep | Home - Allen's Meadow-Lacrosse Field #1 [Directions] | 4:15 p.m. | ||
| Fri., 4/19 | V Boys Tennis | Danbury | Home - Wilton HS-Tennis Courts [Directions] | 2:30 p.m. | W 7-0 [Detailed Results] | |
| Fri., 4/19 | V Softball | Greenwich | Away - Greenwich HS-Softball Field [Directions] | 4:00 p.m. | ||
| Fri., 4/19 | JV Softball | Greenwich | Away - Julian Curtiss School [Directions] | Postponed | ||
| Fri., 4/19 | V Girls Tennis | Danbury | Away - Danbury HS-DHS Tennis Courts [Directions] | 12:00 p.m. | W 6-1 [Detailed Results] | |
| Sat., 4/20 | V Boys Lacrosse | Yorktown (NY) | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 7:00 p.m. | ||
| Sat., 4/20 | JV Boys Lacrosse | Yorktown (NY) | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 4:30 p.m. | ||
| Sat., 4/20 | V Girls Lacrosse | Yorktown (NY) | Home - Wilton HS-Lilly Field [Directions] | 5:00 p.m. | ||
| Sat., 4/20 | JV Girls Lacrosse | Yorktown (NY) | Home - Wilton HS-Lilly Field [Directions] | 3:00 p.m. | ||
| Mon., 4/22 | V Baseball | Trumbull | Home - Wilton HS-Varsity Baseball Field [Directions] | 4:15 p.m. | ||
| Mon., 4/22 | JV Baseball | Trumbull | Home - Wilton HS-JV Baseball Field [Directions] | 4:15 p.m. | ||
| Mon., 4/22 | FR Baseball | Trumbull | Away - Trumbull HS-Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/22 | FR Boys Lacrosse | Ridgefield | Home - Allen's Meadow-Lacrosse Field #1 [Directions] | Canceled | Cancelled | |
| Mon., 4/22 | V Boys Tennis | New Canaan | Home - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | L 6-1 [Detailed Results] | |
| Mon., 4/22 | JV Boys Tennis | New Canaan | Home - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 4/22 | V Girls Golf | New Canaan | Home - Silvermine Golf Club [Directions] | 3:30 p.m. | ||
| Mon., 4/22 | FR Girls Lacrosse | Ridgefield | Away - Scotts Ridge MS-SRMS Turf [Directions] | 4:00 p.m. | ||
| Mon., 4/22 | V Softball | Trumbull | Away - Trumbull HS-Varsity Softball Diamond [Directions] | 4:15 p.m. | ||
| Mon., 4/22 | JV Softball | Trumbull | Away - Trumbull HS-JV Softball Diamond [Directions] | 4:15 p.m. | ||
| Mon., 4/22 | V Girls Tennis | New Canaan | Away - New Canaan HS-NCHS Tennis Courts [Directions] | 4:00 p.m. | L 1-6 [Detailed Results] | |
| Mon., 4/22 | JV Girls Tennis | New Canaan | Home - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | V Boys Lacrosse | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 4:30 p.m. | ||
| Tue., 4/23 | JV Boys Lacrosse | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | Postponed | ||
| Tue., 4/23 | V Boys Outdoor Track | Fairfield Warde | Home - Wilton HS-Track [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | V Boys Tennis | Staples | Away - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | L 6-1 [Detailed Results] | |
| Tue., 4/23 | JV Boys Tennis | Staples | Away - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | JV Boys Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 4/23 | V Girls Golf | Darien | Away - Wee Burn CC [Directions] | 3:15 p.m. | ||
| Tue., 4/23 | JV Girls Golf | Darien | Home - Silvermine Golf Club [Directions] | 3:00 p.m. | ||
| Tue., 4/23 | V Girls Lacrosse | St. Joseph | Home - Wilton HS-Lilly Field [Directions] | 6:00 p.m. | ||
| Tue., 4/23 | JV Girls Lacrosse | St. Joseph | Home - Wilton HS-Lilly Field [Directions] | Postponed | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 4:00 p.m. | ||||||
| Tue., 4/23 | V Girls Outdoor Track | Fairfield Warde | Home - Wilton HS-Track [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | V Girls Tennis | Staples | Home - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | W 6-1 [Detailed Results] | |
| Tue., 4/23 | JV Girls Tennis | Staples | Home - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | V Baseball | Danbury | Away - Danbury HS-V Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | JV Baseball | Danbury | Away - Danbury HS-JV Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | FR Baseball | Danbury | Home - Allen's Meadow-Baseball Diamond [Directions] | 4:15 p.m. | ||
| Wed., 4/24 | FR Boys Lacrosse | Greenwich | Away - Greenwich HS-Field 4 [Directions] | 5:00 p.m. | ||
| Wed., 4/24 | JV Boys Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:45 p.m. | ||
| Wed., 4/24 | V Softball | Danbury | Home - Wilton HS-Varsity Softball Field [Directions] | 6:00 p.m. | ||
| Wed., 4/24 | JV Softball | Danbury | Home - Wilton HS-JV Softball Field [Directions] | 4:15 p.m. | ||
| Wed., 4/24 | V Girls Tennis | Darien | Away - Darien HS-DHS Tennis Courts [Directions] | 5:00 p.m. | L 2-4 | |
| Thu., 4/25 | V Boys Lacrosse | Ridgefield | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 7:00 p.m. | ||
| Thu., 4/25 | JV Boys Lacrosse | Ridgefield | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 4:30 p.m. | ||
| Thu., 4/25 | V Boys Tennis | Ridgefield | Away - Ridgefield HS-RHS Tennis Courts [Directions] | 4:00 p.m. | W 4-3 [Detailed Results] | |
| Thu., 4/25 | JV Boys Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 4/25 | V Girls Golf | Greenwich | Away - Fairview Country Club [Directions] | 3:30 p.m. | ||
| Thu., 4/25 | V Girls Tennis | Ridgefield | Home - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Thu., 4/25 | JV Girls Tennis | Ridgefield | Home - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 4/26 | V Baseball | New Canaan | Away - Mead Park-Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 4/26 | JV Baseball | New Canaan | Away - Waveny Park-Coppo Field [Directions] | 4:00 p.m. | ||
| Fri., 4/26 | FR Baseball | New Canaan | Home - Allen's Meadow-Baseball Diamond [Directions] | 4:15 p.m. | ||
| Fri., 4/26 | FR Boys Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | 4:00 p.m. | ||
| Fri., 4/26 | JV Boys Tennis | Darien | Home - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 4/26 | FR Girls Lacrosse | Fairfield Ludlowe | Home - Wilton HS-Allen Meadow [Directions] | 4:00 p.m. | ||
| Fri., 4/26 | V Softball | New Canaan | Home - Wilton HS-Varsity Softball Field [Directions] | 6:00 p.m. | ||
| Fri., 4/26 | JV Softball | New Canaan | Home - Wilton HS-JV Softball Field [Directions] | 4:15 p.m. | ||
| Fri., 4/26 | JV Girls Tennis | Darien | Away - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Sat., 4/27 | V Boys Lacrosse | Chaminade (NY) | Away - CHAMINADE-OTT FIELD | 1:00 p.m. | ||
| Sat., 4/27 | JV Boys Lacrosse | Chaminade (NY) | Away - CHAMINADE-OTT FIELD | 10:00 a.m. | ||
| Sat., 4/27 | V Boys Outdoor Track | O'Grady Relays | Away - Danbury HS-Danbury HS Stadium | 9:00 a.m. | ||
| Sat., 4/27 | V Girls Lacrosse | West Islip (NY) | Away - West Islip HS | 11:00 a.m. | ||
| Sat., 4/27 | JV Softball | Fairfield Warde | Home - Wilton HS-Varsity Softball Field [Directions] | 11:00 a.m. | ||
| Sat., 4/27 | JV Softball | Brien McMahon | Home - Wilton HS-Varsity Softball Field [Directions] | 9:00 a.m. | ||
| Mon., 4/29 | V Baseball | Staples | Home - Wilton HS-Varsity Baseball Field [Directions] | 4:15 p.m. | ||
| Mon., 4/29 | JV Baseball | Staples | Home - Wilton HS-JV Baseball Field [Directions] | 4:15 p.m. | ||
| Mon., 4/29 | FR Baseball | Staples | Away - Staples HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | FR Boys Lacrosse | Darien | Home - Allen's Meadow-Lacrosse Field #1 [Directions] | 4:15 p.m. | ||
| Mon., 4/29 | V Girls Golf | Fairfield Ludlowe, Fairfield Warde | Home - Silvermine Golf Club [Directions] | 3:30 p.m. | ||
| Mon., 4/29 | JV Girls Lacrosse | Darien | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | FR Girls Lacrosse | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | V Softball | Staples | Away - Staples HS-Wakeman Field [Directions] | 4:30 p.m. | ||
| Mon., 4/29 | JV Softball | Staples | Away - Staples HS-Staples Softball Field [Directions] | Postponed | ||
| Mon., 4/29 | V Girls Tennis | Bridgeport Central | Away - Bridgeport Central HS-Central High School Tennis Courts [Directions] | 4:30 p.m. | W 7-0 [Detailed Results] | |
| Mon., 4/29 | JV Girls Tennis | New Canaan | Home - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/30 | V Boys Outdoor Track | St. Joseph | Away - St. Joseph HS-Track [Directions] | 4:00 p.m. | ||
| Tue., 4/30 | V Boys Tennis | St. Joseph | Home - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Tue., 4/30 | JV Boys Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 6:00 p.m. | ||
| Tue., 4/30 | V Girls Golf | Trumbull | Home - Silvermine Golf Club [Directions] | 3:30 p.m. | ||
| Tue., 4/30 | V Girls Outdoor Track | St. Joseph | Away - St. Joseph HS-Track [Directions] | 4:00 p.m. | ||
| Tue., 4/30 | JV Girls Tennis | Greenwich | Home - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | V Baseball | Ridgefield | Home - Wilton HS-Varsity Baseball Field [Directions] | 4:15 p.m. | ||
| Wed., 5/1 | JV Baseball | Ridgefield | Home - Wilton HS-JV Baseball Field [Directions] | 4:15 p.m. | ||
| Wed., 5/1 | FR Baseball | Ridgefield | Away - Governor Field [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | FR Boys Lacrosse | Stamford | Home - Allen's Meadow-Lacrosse Field #1 [Directions] | 4:15 p.m. | ||
| Wed., 5/1 | V Boys Tennis | Bridgeport Central | Home - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Wed., 5/1 | FR Girls Lacrosse | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | Canceled | Cancelled | |
| Wed., 5/1 | V Softball | Ridgefield | Away - Ridgefield HS-Varsity Softball Field [Directions] | 4:30 p.m. | ||
| Wed., 5/1 | V Girls Tennis | St. Joseph | Away - St. Joseph HS-Tennis Courts [Directions] | 4:00 p.m. | W 6-1 [Detailed Results] | |
| Thu., 5/2 | V Boys Lacrosse | Darien | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 7:00 p.m. | ||
| Thu., 5/2 | JV Boys Lacrosse | Darien | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 4:30 p.m. | ||
| Thu., 5/2 | V Boys Tennis | Westhill | Away - Westhill HS-Westhill Tennis Courts [Directions] | 4:00 p.m. | L 4-3 [Detailed Results] | |
| Thu., 5/2 | V Girls Lacrosse | Darien | Home - Wilton HS-Lilly Field [Directions] | 4:30 p.m. | ||
| Thu., 5/2 | V Girls Tennis | Westhill | Home - Wilton HS-Allen Meadow [Directions] | 4:00 p.m. | W 5-2 | |
| Fri., 5/3 | V Baseball | Bridgeport Central | Away - Bridgeport Central HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Fri., 5/3 | JV Baseball | Bridgeport Central | Away - Seaside Park #10 [Directions] | Canceled | Cancelled | |
| Fri., 5/3 | FR Baseball | Bridgeport Central | Home - Allen's Meadow-Baseball Diamond [Directions] | Canceled | Cancelled | |
| Fri., 5/3 | JV Boys Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | Canceled | Cancelled | |
| Fri., 5/3 | FR Girls Lacrosse | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Fri., 5/3 | V Softball | Bridgeport Central | Home - Wilton HS-Varsity Softball Field [Directions] | 6:00 p.m. | ||
| Fri., 5/3 | JV Softball | Bridgeport Central | Home - Wilton HS-JV Softball Field [Directions] | 4:15 p.m. | ||
| Sat., 5/4 | V Girls Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 3:00 p.m. | ||
| Sat., 5/4 | JV Girls Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 1:00 p.m. | ||
| Mon., 5/6 | V Baseball | St. Joseph | Away - St. Joseph HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | JV Baseball | St. Joseph | Away - Unity Park-Field 1 [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | FR Baseball | St. Joseph | Home - Allen's Meadow-Baseball Diamond [Directions] | 4:15 p.m. | ||
| Mon., 5/6 | V Boys Lacrosse | Danbury | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 6:30 p.m. | ||
| Mon., 5/6 | JV Boys Lacrosse | Danbury | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | FR Boys Lacrosse | Staples | Away - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Mon., 5/6 | V Boys Tennis | Brien McMahon | Away - Brien McMahon HS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | JV Boys Tennis | Fairfield Warde | Home - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | JV Boys Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:15 p.m. | ||
| Mon., 5/6 | V Girls Golf | Danbury | Home - Silvermine Golf Club [Directions] | 3:30 p.m. | ||
| Mon., 5/6 | FR Girls Lacrosse | Staples | Home - Wilton HS-Allen Meadow [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | V Softball | St. Joseph | Home - Wilton HS-Varsity Softball Field [Directions] | 6:00 p.m. | ||
| Mon., 5/6 | JV Softball | St. Joseph | Home - Wilton HS-JV Softball Field [Directions] | 4:15 p.m. | ||
| Mon., 5/6 | V Girls Tennis | Brien McMahon | Home - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | JV Girls Tennis | Fairfield Warde | Home - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | V Boys Outdoor Track | Stamford | Home - Wilton HS-Track [Directions] | 4:30 p.m. | ||
| Tue., 5/7 | V Boys Tennis | Fairfield Ludlowe | Home - Wilton HS-Allen Meadow [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | JV Boys Tennis | Fairfield Ludlowe | Home - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | V Girls Lacrosse | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 6:00 p.m. | ||
| Tue., 5/7 | JV Girls Lacrosse | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 4:30 p.m. | ||
| Tue., 5/7 | V Girls Outdoor Track | Stamford | Home - Wilton HS-Track [Directions] | 4:30 p.m. | ||
| Tue., 5/7 | V Girls Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | JV Girls Tennis | Fairfield Ludlowe | Away - Dwight Elementary School-Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | V Baseball | Westhill | Home - Wilton HS-Varsity Baseball Field [Directions] | 6:30 p.m. | ||
| Wed., 5/8 | JV Baseball | Westhill | Home - Wilton HS-JV Baseball Field [Directions] | 4:15 p.m. | ||
| Wed., 5/8 | FR Baseball | Westhill | Away - Rippowan MS-Rippowam Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | V Softball | Westhill | Away - Westhill HS-Varsity Softball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | JV Softball | Westhill | Away - TBA [Directions] | TBA | ||
| Wed., 5/8 | JV Girls Tennis | St. Joseph | Home - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/9 | V Boys Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 6:30 p.m. | ||
| Thu., 5/9 | JV Boys Lacrosse | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Thu., 5/9 | V Boys Tennis | Stamford | Home - Wilton HS-Tennis Courts [Directions] | 4:30 p.m. | ||
| Thu., 5/9 | JV Boys Tennis | Staples | Away - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/9 | V Girls Golf | Ridgefield | Away - Ridgefield Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 5/9 | V Girls Lacrosse | New Canaan | Home - Wilton HS-Lilly Field [Directions] | 6:00 p.m. | ||
| Thu., 5/9 | JV Girls Lacrosse | New Canaan | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | ||
| Thu., 5/9 | V Softball | Brien McMahon | Away - Brien McMahon HS-Softball Diamond [Directions] | 6:00 p.m. | ||
| Thu., 5/9 | JV Softball | Brien McMahon | Away - Brookside Elementary School [Directions] | 4:30 p.m. | ||
| Thu., 5/9 | V Girls Tennis | Stamford | Away - Stamford HS-SHS Tennis Courts [Directions] | 4:30 p.m. | ||
| Thu., 5/9 | JV Girls Tennis | Staples | Away - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 5/10 | JV Baseball | Brien McMahon | Home - Wilton HS-JV Baseball Field [Directions] | 5:30 p.m. | ||
| Fri., 5/10 | JV Boys Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 4:30 p.m. | ||
| Fri., 5/10 | FR Girls Lacrosse | Ridgefield | Home - Wilton HS-Allen Meadow [Directions] | 4:00 p.m. | ||
| Sat., 5/11 | V Baseball | Brien McMahon | Home - Wilton HS-Varsity Baseball Field [Directions] | 12:00 p.m. | ||
| Sat., 5/11 | V Boys Lacrosse | Fordham Prep (NY) | Away - Manhattan College | 1:00 p.m. | ||
| Sat., 5/11 | JV Boys Lacrosse | Fordham Prep (NY) | Away - Manhattan College | 10:00 a.m. | ||
| Sat., 5/11 | JV Boys Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 1:30 p.m. | ||
| Pending changes awaiting acceptance by one or more parties involved: Date to 5/9, Time to 5:30 p.m. | ||||||
| Sat., 5/11 | V Girls Lacrosse | Guilford | Home - Wilton HS-Lilly Field [Directions] | 10:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 12:00 p.m. | ||||||
| Sat., 5/11 | JV Girls Lacrosse | Guilford | Home - Wilton HS-Lilly Field [Directions] | 11:30 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 9:30 a.m. | ||||||
| Mon., 5/13 | V Baseball | Fairfield Ludlowe | Away - Kiwanis Field-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | JV Baseball | Fairfield Ludlowe | Away - Owen Fish Park-Owen Fish [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | FR Baseball | Fairfield Ludlowe | Home - Allen's Meadow-Baseball Diamond [Directions] | 4:15 p.m. | ||
| Mon., 5/13 | FR Boys Lacrosse | Fairfield Prep | Away - Fairfield University - Barlow Field-Barlow Field Fairfield University [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | JV Boys Tennis | Greenwich | Away - Central MS [Directions] | 4:30 p.m. | ||
| Mon., 5/13 | JV Boys Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:30 p.m. | ||
| Mon., 5/13 | V Girls Golf | Staples | Home - Silvermine Golf Club [Directions] | 3:30 p.m. | ||
| Mon., 5/13 | V Softball | Fairfield Ludlowe | Home - Wilton HS-Varsity Softball Field [Directions] | 6:00 p.m. | ||
| Mon., 5/13 | JV Softball | Fairfield Ludlowe | Home - Wilton HS-JV Softball Field [Directions] | 4:15 p.m. | ||
| Mon., 5/13 | JV Girls Tennis | Greenwich | Home - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:15 p.m. | ||
| Tue., 5/14 | V Girls Golf | Danbury | Home - Silvermine Golf Club [Directions] | 3:30 p.m. | ||
| Wed., 5/15 | V Baseball | Stamford | Away - Stamford HS-SHS Baseball Diamond [Directions] | 4:30 p.m. | ||
| Wed., 5/15 | JV Baseball | Stamford | Away - Belltown Park-Barrett Field, Belltown Park [Directions] | 4:30 p.m. | ||
| Wed., 5/15 | FR Baseball | Stamford | Home - Allen's Meadow-Baseball Diamond [Directions] | 4:15 p.m. | ||
| Wed., 5/15 | V Boys Lacrosse | Fairfield Prep | Away - Fairfield University-Rafferty Stadium [Directions] | 5:00 p.m. | ||
| Wed., 5/15 | JV Boys Lacrosse | Fairfield Prep | Away - Fairfield University-Barlow Field [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | FR Boys Lacrosse | Greenwich | Home - Allen's Meadow-Lacrosse Field #1 [Directions] | 4:15 p.m. | ||
| Wed., 5/15 | V Boys Outdoor Track | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | JV Boys Volleyball | Brien McMahon | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:15 p.m. | ||
| Wed., 5/15 | FR Girls Lacrosse | Ridgefield | Away - Scotts Ridge MS-SRMS Turf [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | V Girls Outdoor Track | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | V Softball | Stamford | Home - Wilton HS-Varsity Softball Field [Directions] | 7:00 p.m. | ||
| Wed., 5/15 | JV Softball | Stamford | Home - Wilton HS-JV Softball Field [Directions] | 4:30 p.m. | ||
| Thu., 5/16 | V Girls Golf | St. Joseph | Home - Silvermine Golf Club [Directions] | 3:30 p.m. | ||
| Thu., 5/16 | JV Girls Tennis | Greenwich | Home - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 5/17 | FR Girls Lacrosse | Trumbull | Home - Wilton HS-Allen Meadow [Directions] | 4:00 p.m. | ||
| Tue., 5/21 | V Girls Golf | New Canaan | Away - CCNC [Directions] | 3:30 p.m. | ||