| Wilton 2021-22 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 892 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Wed., 8/25 | V Football | Fairfield Prep, Staples (Scrim.) | Away - Fairfield University-Rafferty Stadium [Directions] | 4:30 p.m. | ||
| Wed., 8/25 | FR Football | Fairfield Prep, Staples (Scrim.) | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 3:30 p.m. | ||
| Tue., 8/31 | V Boys Golf | Danbury | Away - Richter Park Golf Course [Directions] | 3:00 p.m. | Wilton - 160 Danbury - 194 | |
| Tue., 8/31 | JV Boys Golf | Danbury | Away - Richter Park Golf Course [Directions] | 3:20 p.m. | Incomplete teams | |
| Tue., 8/31 | V Field Hockey | Fairfield Ludlowe (Scrim.) | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 5:30 p.m. | ||
| Tue., 8/31 | JV Field Hockey | Fairfield Ludlowe (Scrim.) | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 7:00 p.m. | ||
| Wed., 9/1 | V Boys Golf | Staples | Home - Rolling Hills Country Club [Directions] | 3:15 p.m. | Wilton - 164 Staples - 166 | |
| Wed., 9/1 | JV Boys Golf | Staples | Home - Rolling Hills Country Club [Directions] | 3:15 p.m. | Wilton - 179 Loss | |
| Wed., 9/1 | V Girls Soccer | Holy Cross (Scrim.) | Home - Wilton HS-Lilly Field [Directions] | 5:00 p.m. | Cancelled | |
| Wed., 9/1 | JV Girls Soccer | Holy Cross (Scrim.) | Home - Allen's Meadow-2A [Directions] | 5:00 p.m. | Cancelled | |
| Thu., 9/2 | V Field Hockey | Sacred Heart of Greenwich (Scrim.) | Away - Sacred Heart of Greenwich | 5:00 p.m. | ||
| Thu., 9/2 | FR Field Hockey | Sacred Heart of Greenwich (Scrim.) | Away - Sacred Heart of Greenwich-Field # 2 | 5:00 p.m. | ||
| Thu., 9/2 | V Girls Volleyball | Jonathan Law (Scrim.) | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Thu., 9/2 | JV Girls Volleyball | Jonathan Law (Scrim.) | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Fri., 9/3 | V Boys Soccer | TBA, Jonathan Law, Litchfield, Masuk, Montville, Northwestern, Old Saybrook | Away - Not Listed-Kelley Martin Tighe Memorial Field | 4:00 p.m. | ||
| Sat., 9/4 | V Football | Danbury (Scrim.) | Away - John Perry Field, Rogers Park MS-John Perry Memorial Field, Rogers Park MS [Directions] | 9:00 a.m. | ||
| Sat., 9/4 | V Field Hockey | Sacred Heart of Greenwich (Scrim.) | Away - Sacred Heart of Greenwich | 9:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 9:30 a.m. | ||||||
| Sat., 9/4 | V Girls Soccer | Granby Memorial, Avon, Coventry, Enfield, Holy Cross, Notre Dame-Fairfield, Portland, Rocky Hill, Suffield | Away - Granby Memorial HS-Stadium Field | 8:00 a.m. | ||
| Sat., 9/4 | V Girls Volleyball | Fairfield Warde, King and Low-Heywood Thomas, Naugatuck, New Milford, St. Joseph | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:00 a.m. | ||
| Mon., 9/6 | V Girls Soccer | Weston (Scrim.) | Away - Weston HS-WHS Stadium Field [Directions] | 11:00 a.m. | ||
| Mon., 9/6 | JV Girls Soccer | Weston (Scrim.) | Away - Weston HS-WHS Lower Turf Field [Directions] | 11:00 a.m. | ||
| Wed., 9/8 | V Boys Golf | Darien | Away - Country Club of Darien [Directions] | 3:15 p.m. | Wilton - 165 Darien - 177 | |
| Wed., 9/8 | JV Boys Golf | Darien | Away - Country Club of Darien [Directions] | 3:15 p.m. | Wilton - 181 Win | |
| Thu., 9/9 | FR Football | Brien McMahon | Home - Wilton HS-Fuijitani Field -Turf [Directions] | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to 4:30 p.m. | ||||||
| Thu., 9/9 | JV Boys Golf | Ridgefield | Away - Ridgefield Golf Course [Directions] | 3:15 p.m. | Wilton - 186 Win | |
| Thu., 9/9 | V Girls Soccer | Fairfield Warde | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | T 0-0 | |
| Thu., 9/9 | JV Girls Soccer | Fairfield Warde | Home - Allen's Meadow-2A [Directions] | 4:15 p.m. | L 4-0 | |
| Thu., 9/9 | V Girls Volleyball | Wright Tech | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:45 p.m. | W 3-0 | |
| Thu., 9/9 | JV Girls Volleyball | Wright Tech | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | W 2-0 | |
| Fri., 9/10 | V Football | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 7:00 p.m. | W 28-0 | |
| Fri., 9/10 | V Field Hockey | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | L 0-5 | |
| Fri., 9/10 | JV Field Hockey | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | L 3-1 | |
| Sat., 9/11 | JV Football | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 9:00 a.m. | W 34-0 | |
| Sat., 9/11 | V Boys Soccer | Fairfield Warde | Away - Fairfield Warde HS-Varsity Grass Soccer Field [Directions] | 2:00 p.m. | L 1-3 | |
| Sat., 9/11 | JV Boys Soccer | Fairfield Warde | Away - Fairfield Warde HS-Varsity Grass Soccer Field [Directions] | 2:00 p.m. | L 7-1 | |
| Sat., 9/11 | FR Boys Soccer | Fairfield Warde | Away - Fairfield Warde HS-Fairfield Warde Grass Utility Field [Directions] | 10:00 a.m. | L 4-0 | |
| Sat., 9/11 | FR Field Hockey | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 10:00 a.m. | L 2-0 | |
| Sat., 9/11 | FR Girls Soccer | Fairfield Ludlowe | Home - Allen's Meadow-3A [Directions] | 10:00 a.m. | L 6-0 | |
| Sat., 9/11 | V Girls Volleyball | Immaculate | Away - Immaculate HS-Immaculate Gym [Directions] | 11:00 a.m. | W 3-0 | |
| Sat., 9/11 | JV Girls Volleyball | Immaculate | Away - Immaculate HS-Immaculate Gym [Directions] | 9:30 a.m. | W 2-0 | |
| Sat., 9/11 | FR Girls Volleyball | Danbury | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 10:00 a.m. | W 2-0 | |
| Mon., 9/13 | V Boys Golf | Fairfield Warde | Home - Rolling Hills Country Club [Directions] | 3:15 p.m. | Wilton - 157 Warde - 170 | |
| Mon., 9/13 | JV Boys Golf | Fairfield Warde | Home - Rolling Hills Country Club [Directions] | 3:15 p.m. | Wilton - 173 Win | |
| Mon., 9/13 | V Girls Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 7:15 p.m. | W 7-1 | |
| Mon., 9/13 | JV Girls Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 5:30 p.m. | W 6-0 | |
| Mon., 9/13 | V Girls Swimming and Diving | Fairfield Ludlowe | Away - Fairfield University-Pool [Directions] | 4:00 p.m. | Wilton 106 - Ludlowe 71 | |
| Mon., 9/13 | FR Girls Volleyball | Fairfield Warde | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | W 3-1 | |
| Tue., 9/14 | V Boys Cross Country | Trumbull, Brien McMahon, Fairfield Warde | Away - Trumbull HS-Cross Country Course [Directions] | 4:00 p.m. | Wilton - 32 Trumbull - 27 Wilton - 15 McMahon - 50 Wilton -29 Warde - 32 | |
| Tue., 9/14 | V Boys Golf | Westhill | Home - Rolling Hills Country Club [Directions] | 3:15 p.m. | Wilton - 169 Westhill - 184 | |
| Tue., 9/14 | JV Boys Golf | New Canaan | Home - Rolling Hills Country Club [Directions] | 3:15 p.m. | Wilton - 172 Win | |
| Tue., 9/14 | V Boys Soccer | Norwalk | Home - Wilton HS-Lilly Field [Directions] | 5:00 p.m. | L 1-3 | |
| Tue., 9/14 | JV Boys Soccer | Norwalk | Home - Allen's Meadow-2A [Directions] | 5:00 p.m. | L 2-0 | |
| Tue., 9/14 | V Girls Cross Country | Trumbull, Brien McMahon, Fairfield Warde | Away - Trumbull HS-Cross Country Course [Directions] | 4:00 p.m. | Wilton - 36 Trumbull - 19 Wilton - 19 McMahon - 44 Wilton - 24 Warde - 44 | |
| Tue., 9/14 | V Field Hockey | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | T 2-2 | |
| Tue., 9/14 | JV Field Hockey | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 5:15 p.m. | L 2-1 | |
| Tue., 9/14 | V Girls Volleyball | New Milford | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | W 3-2 | |
| Tue., 9/14 | JV Girls Volleyball | New Milford | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:00 p.m. | L 2-1 | |
| Fri., 9/17 | V Girls Soccer | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | T 0-0 | |
| Fri., 9/17 | JV Girls Soccer | New Canaan | Away - Conner Field, New Cannan [Directions] | 4:00 p.m. | L 2-1 | |
| Fri., 9/17 | V Girls Volleyball | Brookfield | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 9/17 | JV Girls Volleyball | Brookfield | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | W 2-1 | |
| Sat., 9/18 | V Boys Cross Country | Guilford | Home - Allen's Meadow-XC Course [Directions] | 9:00 a.m. | ||
| Sat., 9/18 | V Boys Cross Country | Norwalk | Home - Allen's Meadow-XC Course [Directions] | 9:00 a.m. | ||
| Sat., 9/18 | V Boys Cross Country | Staples | Home - Allen's Meadow-XC Course [Directions] | 9:00 a.m. | ||
| Sat., 9/18 | V Boys Cross Country | Cheshire | Home - Allen's Meadow-XC Course [Directions] | 9:00 a.m. | ||
| Sat., 9/18 | V Football | Fairfield Ludlowe | Home - Weston HS-WHS Stadium Field [Directions] | 7:00 p.m. | W 21-14 | |
| Sat., 9/18 | FR Football | Fairfield Ludlowe | Away - Fairfield University - Barlow Field-Barlow Field Fairfield University [Directions] | 9:00 a.m. | L 12-7 | |
| Sat., 9/18 | V Boys Soccer | New Canaan | Home - Wilton HS-Lilly Field [Directions] | 10:00 a.m. | W 2-1 | |
| Sat., 9/18 | JV Boys Soccer | New Canaan | Home - Wilton HS-Lilly Field [Directions] | 2:00 p.m. | W 1-0 | |
| Sat., 9/18 | FR Boys Soccer | Pomperaug | Home - Wilton HS-Lilly Field [Directions] | 12:00 p.m. | W 6-1 | |
| Sat., 9/18 | V Girls Cross Country | Norwalk | Home - Allen's Meadow-XC Course [Directions] | 9:00 a.m. | ||
| Sat., 9/18 | V Girls Cross Country | Cheshire | Home - Allen's Meadow-XC Course [Directions] | 9:00 a.m. | ||
| Sat., 9/18 | V Girls Cross Country | Guilford | Home - Allen's Meadow-XC Course [Directions] | 9:00 a.m. | ||
| Sat., 9/18 | V Girls Cross Country | Staples | Home - Staples HS-Staples Stadium [Directions] | 9:00 a.m. | ||
| Sat., 9/18 | V Girls Cross Country | Woodland | Home - Allen's Meadow-XC Course [Directions] | 9:30 a.m. | ||
| Sat., 9/18 | V Field Hockey | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 10:00 a.m. | W 5-1 | |
| Sat., 9/18 | JV Field Hockey | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 11:30 a.m. | W 10-0 | |
| Sat., 9/18 | FR Field Hockey | Darien | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 10:00 a.m. | L 5-0 | |
| Sat., 9/18 | FR Girls Soccer | Greenwich | Away - Greenwich HS-Field 7 [Directions] | 9:30 a.m. | L 4-0 | |
| Sat., 9/18 | FR Girls Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | Postponed | ||
| Mon., 9/20 | JV Football | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 7:00 p.m. | W 21-18 | |
| Mon., 9/20 | V Field Hockey | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 6:00 p.m. | W 6-1 | |
| Mon., 9/20 | JV Field Hockey | Danbury | Away - Danbury HS-Grass Field Hockey Field [Directions] | 4:30 p.m. | W 7-0 | |
| Mon., 9/20 | FR Girls Volleyball | Brookfield | Home - Wilton HS-Aux Gym [Directions] | 5:15 p.m. | W 2-1 | |
| Tue., 9/21 | V Boys Cross Country | New Canaan, Stamford, Staples | Home - Allen's Meadow-XC Course [Directions] | 4:00 p.m. | Wilton - 18 New Canaan - 30 Wilton - 15 Stamford - 48 Wilton - 40 Staples - 21 | |
| Tue., 9/21 | V Boys Golf | Stamford | Home - Rolling Hills Country Club [Directions] | 3:15 p.m. | Wilton - 163 Stamford - 198 | |
| Tue., 9/21 | JV Boys Golf | Darien | Home - Rolling Hills Country Club [Directions] | 3:15 p.m. | Wilton - 176 Lost | |
| Tue., 9/21 | V Girls Cross Country | New Canaan, Stamford, Staples | Home - Allen's Meadow-XC Course [Directions] | 4:00 p.m. | ||
| Tue., 9/21 | V Girls Diving | Westhill | Home - New Canaan YMCA-Pool [Directions] | 4:30 p.m. | ||
| Tue., 9/21 | FR Field Hockey | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 6:30 p.m. | W 3-1 | |
| Tue., 9/21 | V Girls Soccer | Brien McMahon | Home - Wilton HS-Lilly Field [Directions] | 4:30 p.m. | T 0-0 | |
| Tue., 9/21 | JV Girls Soccer | Brien McMahon | Home - Allen's Meadow-2A [Directions] | 4:30 p.m. | W 6-0 | |
| Wed., 9/22 | V Boys Golf | Greenwich | Home - Rolling Hills Country Club [Directions] | 3:15 p.m. | Wilton - 164 Greenwich - 162 | |
| Wed., 9/22 | JV Boys Golf | Greenwich | Home - Rolling Hills Country Club [Directions] | 3:15 p.m. | Wilton - 166 Won | |
| Wed., 9/22 | V Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 7:00 p.m. | T 1-1 | |
| Wed., 9/22 | JV Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 7:00 p.m. | L 3-0 | |
| Wed., 9/22 | FR Girls Soccer | Trumbull | Home - Allen's Meadow-3A [Directions] | 4:15 p.m. | L 1-0 | |
| Wed., 9/22 | V Girls Swimming and Diving | Westhill/Stamford | Home - Wilton YMCA [Directions] | 3:40 p.m. | Wilton 94 - Westhill/Stamford 91 | |
| Wed., 9/22 | V Girls Volleyball | Bridgeport Central | Away - Bridgeport Central HS-Barry McLeod Court [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 9/22 | JV Girls Volleyball | Bridgeport Central | Away - Bridgeport Central HS-Barry McLeod Court [Directions] | 4:00 p.m. | W 2-0 | |
| Wed., 9/22 | FR Girls Volleyball | Ridgefield | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | W 2-1 | |
| Thu., 9/23 | FR Football | North Haven | Away - North Haven MS-East Turf Field [Directions] | 6:00 p.m. | L 34-7 | |
| Thu., 9/23 | V Field Hockey | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 7:30 p.m. | T 0-0 | |
| Thu., 9/23 | JV Field Hockey | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | W 9-0 | |
| Thu., 9/23 | V Girls Soccer | Stamford | Away - Stamford HS-SHS Upper Soccer Field [Directions] | 4:30 p.m. | W 5-0 | |
| Thu., 9/23 | V Girls Swimming and Diving | Fairfield Warde | Away - Fairfield University-Pool [Directions] | 4:00 p.m. | Wilton - 95 FFLD Warde - 82 | |
| Fri., 9/24 | V Boys Soccer | Stamford | Home - Wilton HS-Lilly Field [Directions] | 5:00 p.m. | W 2-0 | |
| Fri., 9/24 | JV Boys Soccer | Stamford | Home - Allen's Meadow-2A [Directions] | 4:30 p.m. | W 2-1 | |
| Fri., 9/24 | FR Boys Soccer | Darien | Home - Allen's Meadow-3A [Directions] | 4:30 p.m. | W 3-0 | |
| Sat., 9/25 | V Football | North Haven | Home - Weston HS-WHS Stadium Field [Directions] | 6:00 p.m. | W 28-7 | |
| Sat., 9/25 | JV Football | North Haven | Away - North Haven MS-Vanacore Field [Directions] | 10:00 a.m. | Cancelled | |
| Sat., 9/25 | V Boys Soccer | New Milford | Away - New Milford HS-Joe Wiser Stadium - NMHS [Directions] | 10:00 a.m. | W 5-1 | |
| Sat., 9/25 | V Girls Diving | Darien | Home - New Canaan YMCA-Pool [Directions] | 9:00 a.m. | ||
| Sat., 9/25 | V Field Hockey | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 10:00 a.m. | W 4-0 | |
| Sat., 9/25 | JV Field Hockey | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 11:30 a.m. | W 8-0 | |
| Sat., 9/25 | JV Girls Soccer | Stamford | Away - Stamford HS-SHS Upper Soccer Field [Directions] | 10:00 a.m. | W 2-0 | |
| Sat., 9/25 | FR Girls Soccer | Westhill | Away - Westhill HS-Front Turf [Directions] | 10:00 a.m. | W 2-1 | |
| Sat., 9/25 | FR Girls Volleyball | Darien | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 10:00 a.m. | L 3-0 | |
| Mon., 9/27 | V Boys Golf | New Canaan | Away - CCNC [Directions] | 3:15 p.m. | Wilton - 158 New Canaan - 152 | |
| Mon., 9/27 | JV Boys Golf | New Canaan | Away - New Canaan HS-CCNC [Directions] | 3:15 p.m. | Wilton - 177 New Canaan - 169 Lost | |
| Mon., 9/27 | V Girls Soccer | Staples | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | T 0-0 | |
| Mon., 9/27 | V Girls Swimming and Diving | Darien | Home - Wilton YMCA [Directions] | 3:40 p.m. | Wilton - 77 Darien 100 | |
| Tue., 9/28 | V Boys Cross Country | Darien, Westhill | Away - Darien HS-DHS Stadium East [Directions] | 4:00 p.m. | WIlton - 19 Westhill - 46 Wilton - 30 Darien - 25 | |
| Tue., 9/28 | V Boys Golf | Trumbull | Home - Rolling Hills Country Club [Directions] | 3:15 p.m. | Wilton - 167 Trumbull - 183 | |
| Tue., 9/28 | JV Boys Golf | Trumbull | Home - Rolling Hills Country Club [Directions] | 3:15 p.m. | Wilton - 194 Trumbull - 195 Won | |
| Tue., 9/28 | V Boys Soccer | Staples | Away - Staples HS-Wakeman Field B (turf) [Directions] | 4:15 p.m. | T 0-0 | |
| Tue., 9/28 | JV Boys Soccer | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | 4:15 p.m. | L 5-0 | |
| Tue., 9/28 | V Girls Cross Country | Darien, Westhill | Away - Darien HS-DHS Stadium East [Directions] | 4:00 p.m. | Wilton - 19 Darien - 44 Wilton - 18 Westhill - 45 | |
| Tue., 9/28 | JV Girls Soccer | Staples | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | W 4-0 | |
| Tue., 9/28 | V Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 5:45 p.m. | W 3-2 | |
| Tue., 9/28 | JV Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:30 p.m. | L 2-1 | |
| Wed., 9/29 | V Boys Golf | Norwalk | Home - Rolling Hills Country Club [Directions] | 3:15 p.m. | Wilton - 163 Norwalk - 192 | |
| Wed., 9/29 | FR Boys Soccer | Fairfield Ludlowe | Home - Allen's Meadow-3A [Directions] | 4:15 p.m. | T 2-2 | |
| Wed., 9/29 | V Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 5:00 p.m. | W 5-1 | |
| Wed., 9/29 | JV Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 6:30 p.m. | W 3-0 | |
| Wed., 9/29 | FR Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Front Field [Directions] | 4:30 p.m. | W 1-0 | |
| Wed., 9/29 | FR Girls Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 4:30 p.m. | W 7-0 | |
| Wed., 9/29 | V Girls Swimming and Diving | New Canaan | Away - New Canaan YMCA-Pool [Directions] | 3:00 p.m. | Wilton - 81 New Canaan - 99 | |
| Wed., 9/29 | FR Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:30 p.m. | L 3-0 | |
| Thu., 9/30 | FR Football | Notre Dame-West Haven | Away - Veterans Field [Directions] | 4:00 p.m. | W 19-14 | |
| Thu., 9/30 | V Boys Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 2:50 p.m. | Wilton 160 Ludlowe 163 | |
| Thu., 9/30 | JV Boys Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 2:50 p.m. | Wilton - 176 Ludlow - 186 | |
| Thu., 9/30 | V Girls Soccer | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 5:00 p.m. | W 1-0 | |
| Thu., 9/30 | JV Girls Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 5:00 p.m. | W 2-0 | |
| Thu., 9/30 | V Girls Volleyball | Norwalk | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:30 p.m. | W 3-0 | |
| Thu., 9/30 | JV Girls Volleyball | Norwalk | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:15 p.m. | ||
| Fri., 10/1 | V Football | Notre Dame-West Haven | Away - Veterans Field [Directions] | 7:00 p.m. | L 35-36 (OT) | |
| Fri., 10/1 | V Boys Soccer | Danbury | Home - Wilton HS-Lilly Field [Directions] | 6:00 p.m. | W 1-0 | |
| Fri., 10/1 | JV Boys Soccer | Danbury | Home - Allen's Meadow-2A [Directions] | 4:30 p.m. | W 2-0 | |
| Fri., 10/1 | V Field Hockey | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 4:30 p.m. | L 0-6 | |
| Fri., 10/1 | JV Field Hockey | New Canaan | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 4:00 p.m. | ||
| Sat., 10/2 | JV Football | Notre Dame-West Haven | Away - Veterans Field [Directions] | 10:00 a.m. | W 22-6 | |
| Sat., 10/2 | FR Boys Soccer | Newtown | Home - Wilton HS-Lilly Field [Directions] | 10:00 a.m. | L 0-2 | |
| Sat., 10/2 | FR Field Hockey | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 10:30 a.m. | ||
| Sat., 10/2 | FR Girls Soccer | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 2:00 p.m. | ||
| Sat., 10/2 | V Girls Volleyball | New Canaan | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:30 p.m. | L 2-3 | |
| Sat., 10/2 | JV Girls Volleyball | New Canaan | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:15 p.m. | ||
| Sat., 10/2 | FR Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 10:00 a.m. | W 3-1 | |
| Mon., 10/4 | V Field Hockey | Ridgefield | Away - Ridgefield HS-Tiger Hollow Turf Field II [Directions] | 7:00 p.m. | T 2-2 | |
| Mon., 10/4 | JV Field Hockey | Ridgefield | Away - Ridgefield HS-Tiger Hollow Turf Field II [Directions] | Postponed | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 5:30 p.m. | ||||||
| Mon., 10/4 | V Girls Soccer | Bridgeport Central | Away - Bridgeport Central HS-Kennedy Stadium Turf [Directions] | 5:00 p.m. | W 6-0 | |
| Tue., 10/5 | V Boys Cross Country | Fairfield Ludlowe, Norwalk, Ridgefield | Home - Allen's Meadow-XC Course [Directions] | 4:00 p.m. | Wilton - 15 Norwalk - 46 WIlton - 17 Ridgefield - 41 Wilton - 28 Ludlowe - 28 Ludlow wins on 6th man tiebreaker | |
| Tue., 10/5 | V Boys Golf | Ridgefield | Away - Silver Spring Golf Course [Directions] | 3:15 p.m. | Wilton - 155 Ridgefield - 178 | |
| Tue., 10/5 | JV Boys Golf | Ridgefield | Away - Silver Spring Golf Course [Directions] | 3:15 p.m. | Wilton - 180 Ridgefield - 199 | |
| Tue., 10/5 | V Boys Soccer | Bridgeport Central | Home - Wilton HS-Lilly Field [Directions] | 6:00 p.m. | W 2-0 | Senior Night |
| Tue., 10/5 | JV Boys Soccer | Bridgeport Central | Home - Allen's Meadow-2A [Directions] | 4:30 p.m. | ||
| Tue., 10/5 | V Girls Cross Country | Fairfield Ludlowe, Norwalk, Ridgefield | Home - Allen's Meadow-XC Course [Directions] | 4:00 p.m. | Wilton - 36 Ludlowe-19 Wilton - 36 Ridgefield - 19 Wilton - 15 Norwalk - 50 | |
| Tue., 10/5 | V Girls Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 5:45 p.m. | L 1-3 | |
| Tue., 10/5 | JV Girls Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:30 p.m. | W 3-1 | |
| Wed., 10/6 | V Boys Golf | Brien McMahon | Away - Oak Hills Golf Course [Directions] | 3:30 p.m. | Wilton - 154 McMahon - 176 | |
| Wed., 10/6 | FR Boys Soccer | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 4:30 p.m. | W 8-0 | |
| Wed., 10/6 | V Field Hockey | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 6:00 p.m. | W 5-0 | |
| Wed., 10/6 | JV Field Hockey | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 7:15 p.m. | W 6-0 | |
| Wed., 10/6 | FR Field Hockey | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 5:15 p.m. | T 0-0 | |
| Wed., 10/6 | V Girls Soccer | Westhill | Home - Wilton HS-Lilly Field [Directions] | 6:00 p.m. | W 4-0 | Senior Night |
| Wed., 10/6 | FR Girls Soccer | Ridgefield | Home - Allen's Meadow-3A [Directions] | 4:15 p.m. | ||
| Wed., 10/6 | FR Girls Volleyball | Fairfield Ludlowe | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Thu., 10/7 | V Boys Golf | Chappa Tournament | Away - Not Listed-Longshore Golf Course | TBA | Wilton 65 | |
| Thu., 10/7 | V Boys Soccer | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | T 1-1 | |
| Thu., 10/7 | JV Boys Soccer | Westhill | Away - Rippowan MS-Rippowam Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 10/7 | V Girls Volleyball | Stamford | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:30 p.m. | W 3-0 | |
| Thu., 10/7 | JV Girls Volleyball | Stamford | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:15 p.m. | L 2-1 | |
| Fri., 10/8 | JV Boys Soccer | Trumbull | Away - Trumbull HS-The Pit [Directions] | 4:00 p.m. | L 0-3 | |
| Fri., 10/8 | V Girls Soccer | Trumbull | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | W 2-0 | |
| Fri., 10/8 | JV Girls Soccer | Trumbull | Home - Allen's Meadow-2A [Directions] | 4:00 p.m. | W 3-1 | |
| Sat., 10/9 | V Boys Soccer | Trumbull | Away - Trumbull HS-Cork Field [Directions] | 10:00 a.m. | T 2-2 | |
| Sat., 10/9 | FR Boys Soccer | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 11:30 a.m. | L 2-3 | |
| Sat., 10/9 | FR Field Hockey | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 9:00 a.m. | W 1-0 | |
| Sat., 10/9 | FR Girls Soccer | New Canaan | Away - Saxe MS-Field 1 [Directions] | 10:00 a.m. | ||
| Sat., 10/9 | V Girls Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 10:00 a.m. | W 3-0 | |
| Sat., 10/9 | JV Girls Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 11:30 a.m. | L 2-0 | |
| Sat., 10/9 | FR Girls Volleyball | Westhill | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 10:00 a.m. | W 3-0 | |
| Mon., 10/11 | V Girls Volleyball | Danbury | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:30 p.m. | W 3-0 | |
| Mon., 10/11 | JV Girls Volleyball | Danbury | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:15 p.m. | W 2-0 | |
| Tue., 10/12 | V Boys Golf | St. Joseph | Away - Tashua Knolls Golf Course [Directions] | 3:00 p.m. | Wilton 154 St Joseph 152 | |
| Tue., 10/12 | JV Boys Golf | St. Joseph | Away - Tashua Knolls Golf Course [Directions] | 3:00 p.m. | Wilton - 166 | |
| Tue., 10/12 | V Girls Cross Country | Greenwich, Danbury, St. Joseph | Away - Greenwich Point [Directions] | 4:00 p.m. | Wilton - 40 Greenwich - 20 Wilton - 20 Danbury - 41 Wilton - 15 St. Joseph - 50 | |
| Tue., 10/12 | V Girls Diving | St. Joseph, Trumbull | Home - New Canaan YMCA-Pool [Directions] | 4:00 p.m. | ||
| Tue., 10/12 | V Girls Soccer | Ridgefield | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | W 2-1 | |
| Tue., 10/12 | JV Girls Soccer | Ridgefield | Home - Allen's Meadow-2A [Directions] | 4:00 p.m. | W 3-1 | |
| Wed., 10/13 | V Boys Soccer | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 7:00 p.m. | L 0-4 | |
| Wed., 10/13 | JV Boys Soccer | Ridgefield | Away - Ridgefield HS-RHS Lower Grass Field [Directions] | 4:00 p.m. | T 0-0 | |
| Wed., 10/13 | FR Boys Soccer | New Canaan | Away - Saxe MS-Field 1 [Directions] | 4:00 p.m. | ||
| Wed., 10/13 | JV Field Hockey | Fairfield Warde | Home - Wilton HS-Fuijitani Field -Turf [Directions] | Postponed | ||
| Wed., 10/13 | FR Girls Soccer | Masuk | Home - Wilton HS-Lilly Field - Turf [Directions] | 6:00 p.m. | ||
| Wed., 10/13 | V Girls Swimming and Diving | Trumbull | Home - Wilton YMCA [Directions] | 4:00 p.m. | Wilton - 102 Trumbull - 75 | |
| Wed., 10/13 | V Girls Volleyball | Bridgeport Central | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:00 p.m. | W 3-0 | Senior Night |
| Wed., 10/13 | JV Girls Volleyball | Bridgeport Central | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Thu., 10/14 | FR Football | Darien | Away - Darien HS-DHS Stadium East [Directions] | 4:00 p.m. | ||
| Thu., 10/14 | V Boys Golf | FCIAC Championship | Away - Not Listed | TBA | ||
| Thu., 10/14 | V Field Hockey | Fairfield Warde | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 5:30 p.m. | W 6-0 | |
| Thu., 10/14 | JV Field Hockey | Fairfield Warde | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 7:00 p.m. | W 9-0 | |
| Thu., 10/14 | JV Girls Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 4:30 p.m. | T 1-1 | |
| Fri., 10/15 | V Boys Soccer | Fairfield Ludlowe | Home - Wilton HS-Lilly Field [Directions] | 7:00 p.m. | L 1-2 | |
| Fri., 10/15 | JV Boys Soccer | Fairfield Ludlowe | Home - Allen's Meadow-2A [Directions] | 4:30 p.m. | L 1-0 | |
| Fri., 10/15 | V Girls Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 5:15 p.m. | T 1-1 | |
| Fri., 10/15 | V Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 5:45 p.m. | W 3-0 | |
| Fri., 10/15 | JV Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:30 p.m. | ||
| Sat., 10/16 | V Football | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 1:30 p.m. | L 36-56 | |
| Sat., 10/16 | FR Boys Soccer | Staples | Home - Allen's Meadow-3A [Directions] | 10:00 a.m. | ||
| Sat., 10/16 | V Field Hockey | Glastonbury | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 3:30 p.m. | T 2-2 | |
| Sat., 10/16 | JV Field Hockey | Glastonbury | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 5:00 p.m. | W 5-0 | |
| Sat., 10/16 | FR Field Hockey | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 11:00 a.m. | ||
| Sat., 10/16 | FR Girls Soccer | Fairfield Warde | Away - Fairfield Warde HS-Varsity Grass Soccer Field [Directions] | 10:00 a.m. | ||
| Sat., 10/16 | FR Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 10:00 a.m. | L 3-2 | |
| Mon., 10/18 | JV Football | Darien | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 4:00 p.m. | ||
| Mon., 10/18 | V Boys Golf | CIAC Fall Division I Boys Golf Championship | Away - Chippanee GC | 8:30 a.m. | ||
| Mon., 10/18 | V Boys Golf | CIAC Tournament | Away - Not Listed | 3:15 p.m. | ||
| Mon., 10/18 | V Field Hockey | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | W 6-0 | |
| Mon., 10/18 | JV Field Hockey | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | Cancelled | |
| Mon., 10/18 | FR Field Hockey | Fairfield Warde | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 6:30 p.m. | ||
| Mon., 10/18 | V Girls Soccer | Greenwich | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | T 0-0 | |
| Mon., 10/18 | JV Girls Soccer | Greenwich | Home - Allen's Meadow-2A [Directions] | 4:00 p.m. | T 0-0 | |
| Mon., 10/18 | V Girls Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 6:30 p.m. | L 1-3 | |
| Mon., 10/18 | JV Girls Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 5:00 p.m. | ||
| Tue., 10/19 | V Boys Soccer | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:15 p.m. | L 0-7 | |
| Tue., 10/19 | JV Boys Soccer | Greenwich | Away - Cos Cob Park-Binney Park [Directions] | 4:30 p.m. | T 1-1 | |
| Wed., 10/20 | V Boys Cross Country | FCIAC Championships | Away - Not Listed-Waveny Park | 4:00 p.m. | Wilton - 159 | |
| Wed., 10/20 | FR Boys Soccer | Fairfield Ludlowe | Home - Allen's Meadow-3A [Directions] | 4:00 p.m. | ||
| Wed., 10/20 | V Girls Cross Country | FCIAC Championships | Away - Not Listed-Waveny Park | 4:00 p.m. | Wilton - 158 | |
| Wed., 10/20 | V Field Hockey | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 4:00 p.m. | W 7-1 | |
| Wed., 10/20 | JV Field Hockey | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 5:30 p.m. | W 4-0 | |
| Wed., 10/20 | FR Field Hockey | Ridgefield | Away - Scotts Ridge MS-SRMS Turf [Directions] | 5:00 p.m. | T 1-1 | |
| Wed., 10/20 | FR Girls Soccer | Staples | Home - Allen's Meadow-3A [Directions] | 4:15 p.m. | ||
| Wed., 10/20 | V Girls Swimming and Diving | Ridgefield | Away - Barlow Mountain Pool [Directions] | 4:00 p.m. | Wilton 78 Ridgefield 102 | |
| Wed., 10/20 | V Girls Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 7:00 p.m. | L 2-3 | |
| Wed., 10/20 | JV Girls Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:30 p.m. | W 2-0 | |
| Thu., 10/21 | FR Football | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 4:30 p.m. | ||
| Thu., 10/21 | FR Field Hockey | Norwalk | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 6:30 p.m. | W 4-0 | |
| Thu., 10/21 | V Girls Soccer | Darien | Away - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | W 1-0 | |
| Thu., 10/21 | JV Girls Soccer | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | L 2-0 | |
| Thu., 10/21 | V Girls Swimming and Diving | St. Joseph | Home - Wilton YMCA [Directions] | 3:40 p.m. | Wilton 98 St. Joseph 77 | |
| Fri., 10/22 | V Boys Soccer | Darien | Home - Wilton HS-Lilly Field [Directions] | 5:00 p.m. | L 2-4 | |
| Fri., 10/22 | JV Boys Soccer | Darien | Home - Allen's Meadow-2A [Directions] | 4:00 p.m. | ||
| Fri., 10/22 | V Girls Volleyball | Fairfield Ludlowe | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 10/22 | JV Girls Volleyball | Fairfield Ludlowe | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:15 p.m. | ||
| Sat., 10/23 | V Football | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 2:00 p.m. | W 20-17 | |
| Sat., 10/23 | FR Boys Soccer | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 11:00 a.m. | ||
| Sat., 10/23 | FR Field Hockey | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 10:00 a.m. | ||
| Sat., 10/23 | FR Girls Soccer | Weston | Home - Wilton HS-Lilly Field [Directions] | 10:00 a.m. | ||
| Sat., 10/23 | FR Girls Volleyball | Stamford | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 10:00 a.m. | W 3-0 | |
| Mon., 10/25 | JV Football | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 5:00 p.m. | L 33-0 | |
| Mon., 10/25 | V Field Hockey | Branford | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 7:00 p.m. | W 2-0 | |
| Mon., 10/25 | JV Field Hockey | Branford | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 5:00 p.m. | W 5-0 | |
| Mon., 10/25 | V Girls Soccer | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 4:00 p.m. | L 0-1 | |
| Mon., 10/25 | JV Girls Soccer | St. Joseph | Away - St. Joseph HS-Lower Grass Field [Directions] | 4:00 p.m. | W 2-0 | |
| Tue., 10/26 | FR Girls Volleyball | Staples | Away - Staples HS-Field House [Directions] | Postponed | W 3-2 | |
| Wed., 10/27 | V Boys Soccer | St. Joseph | Home - Wilton HS-Lilly Field [Directions] | 7:00 p.m. | W 2-1 | |
| Wed., 10/27 | FR Boys Soccer | Ridgefield | Home - Allen's Meadow-3A [Directions] | 4:15 p.m. | ||
| Wed., 10/27 | V Field Hockey | Greenwich | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 5:30 p.m. | L 0-2 | |
| Wed., 10/27 | JV Field Hockey | Greenwich | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 4:00 p.m. | W 3-1 | |
| Wed., 10/27 | V Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 10/27 | JV Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 10/27 | FR Girls Volleyball | Trumbull | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Thu., 10/28 | FR Football | Ridgefield | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 6:00 p.m. | ||
| Thu., 10/28 | V Girls Soccer | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 6:00 p.m. | W 1-0 | |
| Thu., 10/28 | FR Girls Soccer | Ridgefield | Away - Ridgefield HS-Upper Grass Field [Directions] | 4:30 p.m. | ||
| Thu., 10/28 | V Girls Volleyball | Darien | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:30 p.m. | L 1-3 | |
| Thu., 10/28 | JV Girls Volleyball | Darien | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:15 p.m. | ||
| Fri., 10/29 | V Girls Volleyball | St. Joseph | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 10/29 | JV Girls Volleyball | St. Joseph | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:15 p.m. | ||
| Sat., 10/30 | V Boys Cross Country | CIAC Class Meets | Away - Not Listed-Wickham Park | 4:00 p.m. | ||
| Sat., 10/30 | V Boys Cross Country | CIAC Open Championship | Away - Not Listed-Wickham Park | TBA | ||
| Sat., 10/30 | V Football | Ridgefield | Home - Wilton HS-Fujitani Field - Turf [Directions] | 2:00 p.m. | W 14-7 | Homecoming |
| Sat., 10/30 | V Girls Cross Country | CIAC Class Meets | Away - Not Listed-Wickham Park | 4:00 p.m. | ||
| Sat., 10/30 | V Girls Cross Country | CIAC Open Championship | Away - Not Listed-Wickham Park | TBA | ||
| Sat., 10/30 | V Field Hockey | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 10:00 a.m. | L 4-5 | |
| Sat., 10/30 | FR Girls Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 9:00 a.m. | ||
| Mon., 11/1 | V Boys Cross Country | CIAC Boys Cross Country Class L Championship | Away - Wickham Park | 11:25 a.m. | ||
| Mon., 11/1 | JV Football | Ridgefield | Away - Ridgefield HS-Tiger Hollow Turf Field II [Directions] | 5:30 p.m. | ||
| Mon., 11/1 | V Girls Cross Country | CIAC Girls Cross Country Class L Championship | Away - Wickham Park | 11:55 a.m. | ||
| Mon., 11/1 | V Girls Soccer | Fairfield Ludlowe | Away - Wilton HS-Lilly Field - Turf [Directions] | 7:00 p.m. | W 1-0 | |
| Tue., 11/2 | V Girls Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Wed., 11/3 | FR Football | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 5:00 p.m. | ||
| Wed., 11/3 | V Girls Swimming and Diving | FCIAC Girls Swim Trials | Away - Greenwich HS | 5:00 p.m. | ||
| Thu., 11/4 | V Girls Soccer | Staples | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 7:00 p.m. | L 0-1 | |
| Thu., 11/4 | V Girls Swimming and Diving | FCIAC Girls Diving Finals | Away - Fairfield County Interscholastic Athletic Conferen-Westhill HS | 5:00 p.m. | ||
| Fri., 11/5 | V Boys Cross Country | CIAC Boys Cross Country Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Fri., 11/5 | V Football | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 6:30 p.m. | W 37-21 | |
| Fri., 11/5 | V Boys Soccer | Brien McMahon (Scrim.) | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | ||
| Fri., 11/5 | V Girls Cross Country | CIAC Girls Cross Country Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Sat., 11/6 | JV Football | Fairfield Warde | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 10:30 a.m. | ||
| Sat., 11/6 | V Girls Swimming and Diving | FCIAC Girls Swim Finals | Away - Fairfield County Interscholastic Athletic Conferen-Greenwich HS | 4:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Greenwich HS | ||||||
| Mon., 11/8 | V | Weston | Away - Weston HS-WHS Lower Turf Field [Directions] | 2:45 p.m. | ||
| Mon., 11/8 | V Girls Soccer | Enfield | Home - Wilton HS-Lilly Field [Directions] | 5:00 p.m. | W 2-0 | |
| Mon., 11/8 | V Girls Volleyball | Hamden | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 11/9 | V Boys Soccer | Bristol Central | Away - Bristol Central HS-BC Turf Field [Directions] | 3:30 p.m. | L 1-3 | |
| Wed., 11/10 | V Field Hockey | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 2:00 p.m. | W 1-0 | |
| Wed., 11/10 | V Girls Soccer | Manchester | Away - Memorial Field @ MHS [Directions] | 3:45 p.m. | W 3-1 | |
| Wed., 11/10 | V Girls Swimming and Diving | CIAC Class L Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Thu., 11/11 | FR Football | Norwalk | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 6:00 p.m. | ||
| Thu., 11/11 | V Girls Volleyball | Maloney | Away - Maloney HS-Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 11/12 | V Football | Norwalk | Home - Wilton HS-Fujitani Field - Turf [Directions] | 7:00 p.m. | L 21-41 | Youth Night |
| Fri., 11/12 | V Field Hockey | Hall | Away - Hall HS-Stadium (Turf Field) [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 11/12 | V Girls Soccer | Danbury | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | W 2-1 | |
| Sat., 11/13 | V Boys Cross Country | New England Championships | Away - Not Listed | TBA | ||
| Sat., 11/13 | JV Football | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 10:00 a.m. | ||
| Sat., 11/13 | V Girls Cross Country | New England Championships | Away - Allen's Meadow-XC Course | 4:00 p.m. | ||
| Sat., 11/13 | V Girls Swimming and Diving | CIAC Class L Qualifying Meet | Away - Cornerstone Pool | 3:15 p.m. | ||
| Sat., 11/13 | V Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 11:00 a.m. | L 0-3 | |
| Tue., 11/16 | V Field Hockey | Darien | Away - Norwalk HS-Testa Field [Directions] | 6:00 p.m. | W 1-0 | |
| Tue., 11/16 | V Girls Soccer | Fairfield Ludlowe | Away - Bunnell HS-Multi-Sport Turf Field [Directions] | 6:00 p.m. | W 2-1 | |
| Tue., 11/16 | V Girls Swimming and Diving | CIAC Class L Swimming Championships | Away - SCSU | 6:00 p.m. | ||
| Thu., 11/18 | FR Football | Pomperaug | Away - Pomperaug HS-Stadium [Directions] | 5:00 p.m. | ||
| Thu., 11/18 | V Girls Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Fri., 11/19 | V Football | Pomperaug | Home - Wilton HS-Fujitani Field - Turf [Directions] | 7:00 p.m. | W 43-0 | Senior Night |
| Sat., 11/20 | JV Football | Ridgefield | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 10:30 a.m. | ||
| Sat., 11/20 | JV Football | Pomperaug | Away - Pomperaug HS-Stadium [Directions] | Canceled | Cancelled | |
| Sat., 11/20 | V Field Hockey | New Canaan | Away - Wethersfield HS-Cottone Field [Directions] | 12:00 p.m. | L 1-3 | |
| Sat., 11/20 | V Girls Soccer | Staples | Away - Dillon Stadium [Directions] | 4:00 p.m. | T 0-0 | |
| Sun., 11/21 | V Girls Swimming and Diving | CIAC State Open Swimming Championships | Away - Cornerstone Pool | 2:00 p.m. | ||
| Wed., 12/8 | V Boys Basketball | Bullard Havens Tech (Scrim.) | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:00 p.m. | ||
| Wed., 12/8 | V Girls Basketball | Westhill (Scrim.) | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Wed., 12/8 | V Girls Ice Hockey | Darien | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:30 p.m. | L 2-6 | |
| Thu., 12/9 | V Girls Basketball | Lauralton Hall (Scrim.) | Away - Lauralton Hall-Gym [Directions] | 5:00 p.m. | ||
| Thu., 12/9 | JV Girls Basketball | TBA | Away - TBA | 4:30 p.m. | ||
| Mon., 12/13 | V Boys Basketball | Derby (Scrim.) | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:00 p.m. | ||
| Tue., 12/14 | V Girls Basketball | Immaculate | Away - Immaculate HS-Immaculate Gym [Directions] | 7:15 p.m. | W 47-38 | |
| Tue., 12/14 | JV Girls Basketball | Immaculate | Away - Immaculate HS-Immaculate Gym [Directions] | 5:30 p.m. | W 37-33 | |
| Tue., 12/14 | FR Girls Basketball | Immaculate | Away - Immaculate HS-Immaculate Gym [Directions] | 4:00 p.m. | W 48-16 | |
| Wed., 12/15 | V Wrestling | Staples | Home - Wilton HS-Nicholas Zeoli Fieldhouse [Directions] | 7:00 p.m. | Staples-63 Wilton-18 | |
| Wed., 12/15 | V Girls Basketball | Weston | Away - Weston HS-Gym (New) [Directions] | 5:30 p.m. | W 42-28 | |
| Wed., 12/15 | JV Girls Basketball | Weston | Away - Weston HS-Gym (New) [Directions] | 4:00 p.m. | W 39-23 | |
| Wed., 12/15 | V Girls Ice Hockey | New Canaan | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:30 p.m. | L 1-10 | |
| Fri., 12/17 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 3:50 p.m. | W 7-4 | |
| Sat., 12/18 | V Boys Basketball | Newtown | Away - Newtown HS-Gym [Directions] | 3:00 p.m. | W 55-52 | |
| Sat., 12/18 | JV Boys Basketball | Newtown | Away - Newtown HS-Gym [Directions] | 11:30 a.m. | ||
| Sat., 12/18 | V Boys Indoor Track | Danbury, New Canaan, Norwalk | Home - Wilton HS [Directions] | 8:30 a.m. | ||
| Sat., 12/18 | FR Girls Basketball | Weston | Away - Weston HS-Gym (New) [Directions] | 11:00 a.m. | ||
| Sat., 12/18 | V Girls Indoor Track | New Canaan, Danbury, Norwalk | Away - Wilton HS-Wilton Field House [Directions] | 8:30 a.m. | ||
| Sun., 12/19 | JV Girls Ice Hockey | Masuk Coop | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 8:00 p.m. | W 6-3 | |
| Mon., 12/20 | V Girls Basketball | Kolbe Cathedral | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 7:00 p.m. | W 46-42 | |
| Mon., 12/20 | JV Girls Basketball | Kolbe Cathedral | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:15 p.m. | ||
| Wed., 12/22 | V Wrestling | Danbury, Fairfield Ludlowe | Away - Danbury HS-New gym [Directions] | 5:00 p.m. | ||
| Wed., 12/22 | FR Girls Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 12/22 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Conners - Stamford-Ice Rink [Directions] | 7:50 p.m. | L 1-8 | |
| Tue., 12/28 | FR Boys Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | Canceled | Cancelled | |
| Tue., 12/28 | JV Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | 7:45 p.m. | ||
| Wed., 12/29 | V Wrestling | Danbury, Bristol Eastern, Brookfield, Coventry (RI), Enfield, Abbott Tech, TBA, TBA, TBA, TBA, New Canaan, New Fairfield, New Milford, Norwalk, Staples | Away - Danbury HS-Main Gym | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to 9:15 a.m. | ||||||
| Thu., 12/30 | V Boys Basketball | East Lyme | Away - Platt HS-Gym [Directions] | 1:00 p.m. | W 64-45 | |
| Mon., 1/3 | V Boys Basketball | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | 7:00 p.m. | W 75-36 | |
| Mon., 1/3 | JV Boys Basketball | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | 5:30 p.m. | ||
| Mon., 1/3 | FR Boys Basketball | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | 4:15 p.m. | ||
| Mon., 1/3 | JV Girls Ice Hockey | West Haven/SHA | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | Postponed | ||
| Tue., 1/4 | V Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 6:00 p.m. | L 34-50 | |
| Tue., 1/4 | JV Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 4:30 p.m. | ||
| Wed., 1/5 | V Wrestling | Greenwich | Home - Wilton HS-Nicholas Zeoli Fieldhouse [Directions] | 6:00 p.m. | Greenwich 66 Wilton 12 | |
| Thu., 1/6 | FR Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:45 p.m. | ||
| Thu., 1/6 | FR Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 5:00 p.m. | ||
| Fri., 1/7 | JV Girls Basketball | Fairfield Warde | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | Postponed | ||
| Sat., 1/8 | V Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:00 p.m. | W 50-44 | |
| Sat., 1/8 | JV Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 2:15 p.m. | ||
| Sat., 1/8 | V Boys Indoor Track | Qualifying Meet #2A | Away - Wilton HS-Wilton Field House | 8:30 a.m. | ||
| Sat., 1/8 | V Wrestling | Shelton, Brookfield/Shepaug | Away - Shelton HS-Auxillary Gym [Directions] | 10:00 a.m. | ||
| Sat., 1/8 | V Wrestling | Warde Invitational | Away - Fairfield Warde HS-Large Gym | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to 9:00 a.m. | ||||||
| Sat., 1/8 | V Wrestling | Warde Invitational | Away - Fairfield Warde HS-Small Gym | TBA | ||
| Sat., 1/8 | V Girls Basketball | Fairfield Warde | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | L 29-40 | |
| Sat., 1/8 | FR Girls Basketball | Fairfield Warde | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | Postponed | ||
| Sat., 1/8 | V Girls Gymnastics | Darien, New Canaan | Away - Darien YMCA [Directions] | 2:30 p.m. | Wilton 118.45 | |
| Sat., 1/8 | V Girls Indoor Track | Qualifying Meet #2A | Away - Wilton HS-Wilton Field House | 8:30 a.m. | ||
| Sun., 1/9 | JV Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice-Stadium [Directions] | 5:00 p.m. | ||
| Tue., 1/11 | V Boys Basketball | Norwalk | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:15 p.m. | W 74-50 | |
| Tue., 1/11 | JV Boys Basketball | Norwalk | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | Postponed | ||
| Tue., 1/11 | V Girls Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 6:15 p.m. | L 38-51 | |
| Tue., 1/11 | JV Girls Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | Postponed | ||
| Tue., 1/11 | V Girls Ice Hockey | Darien | Away - Darien Ice House-Ice Rink [Directions] | 7:50 p.m. | L 0-7 | |
| Wed., 1/12 | FR Boys Basketball | Norwalk | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | Postponed | ||
| Wed., 1/12 | V Boys Swimming and Diving | Ridgefield | Away - Barlow Mountain Pool [Directions] | 4:00 p.m. | Ridgefield 105 Wilton 66 | |
| Wed., 1/12 | V Wrestling | Darien | Away - Darien HS-DHS South Gym [Directions] | 4:30 p.m. | ||
| Thu., 1/13 | V Wrestling | Weston | Away - Weston HS-Gym (New) [Directions] | 6:30 p.m. | ||
| Fri., 1/14 | V Boys Basketball | New Canaan | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:15 p.m. | W 63-40 | |
| Fri., 1/14 | JV Boys Basketball | New Canaan | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Fri., 1/14 | V Girls Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 6:15 p.m. | W 34-31 | |
| Fri., 1/14 | JV Girls Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:30 p.m. | ||
| Sat., 1/15 | V Boys Basketball | Daniel Hand | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:00 p.m. | L 66-69 | |
| Sat., 1/15 | FR Boys Basketball | New Canaan | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Sat., 1/15 | V Boys Indoor Track | FCIAC, New Canaan, Norwalk, Ridgefield | Away - Wilton HS-Wilton Field House | 8:30 a.m. | ||
| Sat., 1/15 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Away - Fairfield University-Pool [Directions] | 11:30 a.m. | Wilton 78 Fairfield Coop 100 | |
| Sat., 1/15 | V Girls Basketball | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | 1:15 p.m. | W 44-37 | |
| Sat., 1/15 | JV Girls Basketball | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | 11:30 a.m. | ||
| Sat., 1/15 | FR Girls Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 1/15 | V Girls Indoor Track | FCIAC, New Canaan, Norwalk, Ridgefield | Away - Wilton HS-Wilton Field House | 8:30 a.m. | ||
| Mon., 1/17 | V Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 6:15 p.m. | W 59-52 | |
| Mon., 1/17 | JV Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:30 p.m. | ||
| Mon., 1/17 | FR Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 3:00 p.m. | ||
| Mon., 1/17 | V Girls Basketball | Brien McMahon | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:15 p.m. | W 66-24 | |
| Mon., 1/17 | JV Girls Basketball | Brien McMahon | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Mon., 1/17 | FR Girls Basketball | New Fairfield | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 3:00 p.m. | ||
| Mon., 1/17 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 3:30 p.m. | L 2-6 | |
| Mon., 1/17 | JV Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice-New [Directions] | 3:30 p.m. | ||
| Wed., 1/19 | V Boys Swimming and Diving | New Canaan | Away - New Canaan YMCA-Pool [Directions] | 3:00 p.m. | Wilton 77 New Canaan 100 | |
| Wed., 1/19 | V Wrestling | Fairfield Warde | Away - Fairfield Warde HS-Small Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/19 | V Girls Ice Hockey | Greenwich | Away - Greenwich - Dorothy Hamill-Rink [Directions] | 7:15 p.m. | L 5-9 | |
| Fri., 1/21 | V Boys Basketball | Stamford | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 7:00 p.m. | W 64-47 | |
| Fri., 1/21 | JV Boys Basketball | Stamford | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:30 p.m. | ||
| Sat., 1/22 | FR Boys Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 11:30 a.m. | ||
| Sat., 1/22 | V Boys Indoor Track | FCIAC, Brien McMahon, Danbury, Darien | Away - Wilton HS-Wilton Field House | 8:30 a.m. | ||
| Sat., 1/22 | V Wrestling | The 35th Annual New Milford Wrestling Tournament | Away - New Milford HS-Main Gym - NMHS | 8:30 a.m. | ||
| Sat., 1/22 | V Girls Basketball | Southington | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:00 p.m. | L 27-39 | |
| Sat., 1/22 | JV Girls Basketball | Southington | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:15 p.m. | ||
| Sat., 1/22 | FR Girls Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 10:00 a.m. | ||
| Sat., 1/22 | V Girls Gymnastics | Trumbull, Foran, St. Joseph | Away - Next Dimension Gymnastics-Next Dimension [Directions] | 6:00 p.m. | 123.55 | |
| Sat., 1/22 | V Girls Ice Hockey | Masuk Coop | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 6:30 p.m. | W 3-1 | |
| Sat., 1/22 | V Girls Indoor Track | Qualifying Meet #4A | Away - Wilton HS-Wilton Field House | 8:30 a.m. | ||
| Mon., 1/24 | V Boys Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 7:00 p.m. | W 50-47 | |
| Mon., 1/24 | JV Boys Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 5:15 p.m. | ||
| Mon., 1/24 | FR Boys Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Mon., 1/24 | V Boys Swimming and Diving | Westhill/Stamford | Away - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | Wilton 77 Westhill 97 | |
| Mon., 1/24 | V Girls Basketball | Staples | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 7:00 p.m. | L 29-41 | |
| Mon., 1/24 | JV Girls Basketball | Staples | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:30 p.m. | ||
| Mon., 1/24 | FR Girls Basketball | Staples | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Tue., 1/25 | V Girls Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 6:00 p.m. | W 57-45 | |
| Tue., 1/25 | JV Girls Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | ||
| Tue., 1/25 | V Girls Gymnastics | Stamford, Westhill | Home - Wilton HS-Aux Gym [Directions] | 5:00 p.m. | 127.4 | |
| Wed., 1/26 | V Wrestling | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 7:00 p.m. | ||
| Wed., 1/26 | V Girls Ice Hockey | Northwest Catholic | Away - Champions Skating Rink - Cromwell-Upper Rink [Directions] | Canceled | Cancelled | |
| Wed., 1/26 | V Girls Ice Hockey | Mercy/NW Catholic/East Hampton | Away - Simsbury - ISCC-NHL [Directions] | 7:50 p.m. | L 5-6 | |
| Thu., 1/27 | V Boys Basketball | St. Joseph | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 7:00 p.m. | W 62-47 | |
| Thu., 1/27 | JV Boys Basketball | St. Joseph | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:30 p.m. | ||
| Thu., 1/27 | FR Boys Basketball | St. Joseph | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Thu., 1/27 | V Girls Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 7:15 p.m. | L 40-50 | |
| Thu., 1/27 | JV Girls Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 5:45 p.m. | ||
| Thu., 1/27 | FR Girls Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:30 p.m. | ||
| Fri., 1/28 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Home - Wilton YMCA [Directions] | 3:40 p.m. | Wilton 71 Norwalk. BM 106 | |
| Fri., 1/28 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 4:00 p.m. | W 10-2 | |
| Sat., 1/29 | V Wrestling | Brookfield, Bethel, Canton, Danbury, Darien, Joel Barlow, Montville, New Canaan, Newtown, Pomperaug, Stratford, Harding | Away - Brookfield HS-BHS Small & Big Gym | Canceled | Cancelled | |
| Pending changes awaiting acceptance by one or more parties involved: Date to 1/30, Time to 11:00 a.m. | ||||||
| Mon., 1/31 | V Boys Swimming and Diving | Greenwich | Home - Wilton YMCA [Directions] | 3:40 p.m. | ||
| Mon., 1/31 | V Wrestling | Stamford | Home - Wilton HS-Nicholas Zeoli Fieldhouse [Directions] | 7:00 p.m. | ||
| Tue., 2/1 | V Boys Basketball | Bridgeport Central | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:15 p.m. | W 80-43 | |
| Tue., 2/1 | JV Boys Basketball | Bridgeport Central | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Tue., 2/1 | V Girls Basketball | Bridgeport Central | Away - Bridgeport Central HS-Barry McLeod Court [Directions] | 6:00 p.m. | W 76-29 | |
| Tue., 2/1 | JV Girls Basketball | Bridgeport Central | Away - Bridgeport Central HS-Barry McLeod Court [Directions] | 4:30 p.m. | ||
| Tue., 2/1 | V Girls Gymnastics | Staples, Norwalk | Away - Westport YMCA [Directions] | 6:30 p.m. | 129.85 | |
| Wed., 2/2 | FR Girls Basketball | Danbury | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:00 p.m. | ||
| Wed., 2/2 | V Girls Gymnastics | Fairfield Ludlowe, Fairfield Warde | Home - Wilton HS-Aux Gym [Directions] | 5:30 p.m. | 133.45 | |
| Wed., 2/2 | V Girls Ice Hockey | Mercy/NW Catholic/East Hampton | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:30 p.m. | L 5-8 | |
| Thu., 2/3 | V Boys Diving | Darien | Home - New Canaan YMCA-Pool [Directions] | 3:00 p.m. | ||
| Thu., 2/3 | V Boys Indoor Track | FCIAC Indoor Track Championships | Away - Floyd Little Athletic Center-Field House | 4:30 p.m. | ||
| Thu., 2/3 | JV Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 8:00 p.m. | ||
| Thu., 2/3 | V Girls Indoor Track | FCIAC Indoor Track Championships | Away - Floyd Little Athletic Center-Field House | 4:30 p.m. | ||
| Fri., 2/4 | V Wrestling | Ridgefield | Away - Ridgefield HS-Aux Gym [Directions] | Canceled | Cancelled | |
| Sat., 2/5 | V Boys Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 2:00 p.m. | L 55-68 | |
| Sat., 2/5 | JV Boys Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 12:30 p.m. | ||
| Sat., 2/5 | FR Boys Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 11:00 a.m. | ||
| Sat., 2/5 | V Wrestling | Ridgefield, Trumbull, Westhill | Away - Ridgefield HS-Aux Gym [Directions] | 11:00 a.m. | ||
| Sat., 2/5 | V Girls Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 1:00 p.m. | W 42-25 | |
| Sat., 2/5 | JV Girls Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 11:30 a.m. | ||
| Sat., 2/5 | V Girls Ice Hockey | Stamford/Westhill/Staples | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:30 p.m. | L 1-10 | Senior Night |
| Mon., 2/7 | V Girls Basketball | Westhill | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:15 p.m. | W 45-27 | |
| Mon., 2/7 | JV Girls Basketball | Westhill | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Tue., 2/8 | V Boys Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | W 69-52 | |
| Tue., 2/8 | JV Boys Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 4:30 p.m. | ||
| Tue., 2/8 | V Wrestling | Newtown, Joel Barlow, St. Joseph | Away - Newtown HS-Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/8 | V Girls Basketball | Trumbull | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:15 p.m. | W 61-24 | |
| Tue., 2/8 | JV Girls Basketball | Trumbull | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Tue., 2/8 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 3:30 p.m. | W 5-3 | |
| Wed., 2/9 | FR Boys Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | ||
| Wed., 2/9 | V Boys Swimming and Diving | St. Joseph, Trumbull | Home - Wilton YMCA [Directions] | 3:40 p.m. | ||
| Wed., 2/9 | V Girls Ice Hockey | Greenwich | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 4:00 p.m. | L 5-7 | |
| Thu., 2/10 | V Boys Diving | Greenwich | Home - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Thu., 2/10 | V Girls Gymnastics | Greenwich | Home - Wilton HS-Aux Gym [Directions] | 5:00 p.m. | 132.0 | |
| Fri., 2/11 | V Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 7:00 p.m. | L 47-74 | |
| Fri., 2/11 | JV Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/11 | V Boys Swimming and Diving | Darien | Home - Wilton YMCA [Directions] | 3:30 p.m. | ||
| Fri., 2/11 | V Wrestling | FCIAC, Danbury, Darien, Fairfield Ludlowe, Fairfield Warde, Greenwich, TBA, New Canaan, Norwalk, Ridgefield, St. Joseph, Stamford, Staples, Trumbull, Westhill | Away - New Canaan HS-Main Gym | 4:30 p.m. | ||
| Fri., 2/11 | V Girls Basketball | Ridgefield | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:15 p.m. | W 41-23 | |
| Fri., 2/11 | JV Girls Basketball | Ridgefield | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Fri., 2/11 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 5:30 p.m. | L 2-3 | |
| Sat., 2/12 | FR Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 9:30 a.m. | ||
| Sat., 2/12 | V Boys Indoor Track | Class L Championship | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Sat., 2/12 | V Wrestling | FCIAC Wrestling Championships Wrestlebacks | Away - New Canaan HS-Main Gym | 10:00 a.m. | ||
| Sat., 2/12 | FR Girls Basketball | Ridgefield | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 10:30 a.m. | ||
| Sat., 2/12 | V Girls Gymnastics | FCIAC Gymnastics Championships | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 | 11:00 a.m. | 133.15 | |
| Sat., 2/12 | V Girls Indoor Track | Class L Championship | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Mon., 2/14 | V Boys Basketball | Fairfield Ludlowe | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:15 p.m. | W 68-47 | |
| Mon., 2/14 | JV Boys Basketball | Fairfield Ludlowe | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Mon., 2/14 | V Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 6:30 p.m. | L 36-52 | |
| Mon., 2/14 | JV Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:00 p.m. | ||
| Mon., 2/14 | V Girls Ice Hockey | Conard | Away - Veterans Memorial Ice Rink - West Hartford-Ice Rink [Directions] | 7:20 p.m. | L 0-5 | |
| Tue., 2/15 | FR Boys Basketball | Fairfield Ludlowe | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Tue., 2/15 | V Boys Swimming and Diving | Danbury | Away - WCSU O'Neill Center - Blue Gym-O'Neill Center [Directions] | 5:30 p.m. | ||
| Tue., 2/15 | FR Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Aux Gym [Directions] | 4:30 p.m. | ||
| Tue., 2/15 | V Girls Gymnastics | Norwalk, Staples | Home - Wilton HS-Aux Gym [Directions] | 4:30 p.m. | 128.75 | Senior Night |
| Wed., 2/16 | V Boys Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 7:00 p.m. | W 45-37 | |
| Wed., 2/16 | JV Boys Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 2/16 | FR Boys Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 2/16 | V Boys Swimming and Diving | Staples | Home - Wilton YMCA [Directions] | 3:40 p.m. | ||
| Wed., 2/16 | V Girls Basketball | Greenwich | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 7:00 p.m. | W 42-38 | |
| Wed., 2/16 | JV Girls Basketball | Greenwich | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:30 p.m. | ||
| Wed., 2/16 | FR Girls Basketball | Greenwich | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Fri., 2/18 | V Boys Basketball | Fitch | Away - Fitch HS-Big Gym [Directions] | 6:30 p.m. | W 63-61 | |
| Fri., 2/18 | JV Boys Basketball | Fitch | Away - Fitch HS-Big Gym [Directions] | 5:00 p.m. | ||
| Fri., 2/18 | FR Boys Basketball | Fitch | Away - Fitch HS-Big Gym [Directions] | 3:15 p.m. | ||
| Fri., 2/18 | V Wrestling | Class L Championship - Day 1 | Away - Wilton | 3:00 p.m. | ||
| Fri., 2/18 | V Girls Gymnastics | New Milford | Away - New Milford HS-Small Gym - NMHS [Directions] | 5:00 p.m. | 127.9 | |
| Fri., 2/18 | V Girls Ice Hockey | Masuk Coop | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | L 1-3 | |
| Sat., 2/19 | V Boys Indoor Track | State Open | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/19 | V Wrestling | Class L Championship - Day 2 | Away - Wilton | 9:00 a.m. | ||
| Sat., 2/19 | V Girls Basketball | Ridgefield | Away - Staples HS-Staples Gym [Directions] | 5:00 p.m. | L 44-42 | |
| Sat., 2/19 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:30 p.m. | W 8-2 | |
| Sat., 2/19 | V Girls Indoor Track | State Open | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Mon., 2/21 | V Boys Basketball | Darien | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 7:00 p.m. | W 62-56 | |
| Mon., 2/21 | JV Boys Basketball | Darien | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:15 p.m. | ||
| Mon., 2/21 | FR Boys Basketball | Darien | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Mon., 2/21 | V Girls Ice Hockey | Guilford Coop | Away - Northford Ice Pavilion-Red [Directions] | 12:00 p.m. | L 4-8 | |
| Wed., 2/23 | V Boys Basketball | Danbury | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 7:00 p.m. | W 65-47 | |
| Wed., 2/23 | JV Boys Basketball | Danbury | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:15 p.m. | ||
| Wed., 2/23 | FR Boys Basketball | Danbury | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Sat., 2/26 | V Boys Basketball | Danbury | Home - Fairfield Warde HS-Gym [Directions] | 2:00 p.m. | W 68-40 | |
| Sat., 2/26 | V Girls Gymnastics | CIAC Class M Divisional Championship | Away - Richetelli Gymnasium @Jonathan Law | 10:00 a.m. | ||
| Mon., 2/28 | V Girls Basketball | Trumbull | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:30 p.m. | W 48-30 | |
| Tue., 3/1 | V Boys Basketball | Westhill | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:30 p.m. | W 67-43 | |
| Tue., 3/1 | V Boys Swimming and Diving | FCIAC Boys' Swim Trials | Away - Greenwich HS | 5:30 p.m. | ||
| Wed., 3/2 | V Boys Swimming and Diving | FCIAC Diving Finals | Away - Westhill High-Westhill HS | 5:00 p.m. | ||
| Thu., 3/3 | V Boys Basketball | Ridgefield | Away - Wilton HS [Directions] | 7:00 p.m. | L 40-46 | |
| Thu., 3/3 | V Boys Swimming and Diving | FCIAC Boys' Swim Finals | Away - Greenwich HS | 6:30 p.m. | ||
| Thu., 3/3 | V Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 6:00 p.m. | W 41-37 | |
| Sat., 3/5 | V Girls Gymnastics | State Open | Away - New Milford | 10:00 a.m. | ||
| Mon., 3/7 | V Girls Basketball | Hillhouse | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 7:00 p.m. | W 44-34 | |
| Thu., 3/10 | V Boys Basketball | Newtown | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:30 p.m. | W 57-49 | |
| Thu., 3/10 | V Boys Swimming and Diving | CIAC Class M Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Fri., 3/11 | V Boys Basketball | Holy Cross | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:30 p.m. | W 63-62 | |
| Fri., 3/11 | V Girls Basketball | Enfield | Away - New Britain HS-Gym [Directions] | 7:45 p.m. | W 48-37 | |
| Sun., 3/13 | V Boys Swimming and Diving | CIAC Class M Qualifying Meet | Away - Cornerstone Pool | 1:00 p.m. | ||
| Tue., 3/15 | V Boys Basketball | Bristol Central | Away - Floyd Little Athletic Center-FieldHouse [Directions] | 7:00 p.m. | L 54-52 | |
| Wed., 3/16 | V Boys Swimming and Diving | CIAC Class M Swimming Championships | Away - Cornerstone Pool | 6:00 p.m. | ||
| Thu., 3/17 | V Boys Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/19 | V Boys Swimming and Diving | CIAC State Open Swimming Championships | Away - Cornerstone Pool | 3:15 p.m. | ||
| Sun., 3/20 | V Girls Basketball | East Hartford | Away - Mohegan Sun Arena-Arena [Directions] | 6:15 p.m. | L 33-54 | |
| Sat., 3/26 | V Boys Lacrosse | New Fairfield (Scrim.) | Away - New Fairfield HS-Marty Morgan Field [Directions] | 9:00 a.m. | ||
| Sat., 3/26 | V Softball | Brookfield (Scrim.) | Home - Wilton HS-Varsity Softball Field [Directions] | 11:00 a.m. | ||
| Mon., 3/28 | V Baseball | Brien McMahon (Scrim.) | Away - Brien McMahon HS-Pride Field [Directions] | 4:15 p.m. | Cancelled | |
| Tue., 3/29 | V Baseball | Norwalk (Scrim.) | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 4:00 p.m. | ||
| Tue., 3/29 | V Boys Lacrosse | Stepinac (NY) (Scrim.) | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 5:00 p.m. | ||
| Tue., 3/29 | V Softball | Immaculate (Scrim.) | Home - Wilton HS-Varsity Softball Field [Directions] | 4:15 p.m. | Cancelled | |
| Wed., 3/30 | V Baseball | Darien (Scrim.) | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 3/30 | JV Baseball | Darien (Scrim.) | Away - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | ||
| Wed., 3/30 | V Softball | Bethel (Scrim.) | Home - Wilton HS-Varsity Softball Field [Directions] | 4:00 p.m. | ||
| Thu., 3/31 | V Girls Lacrosse | Newtown (Scrim.) | Away - Newtown HS-Blue and Gold Stadium [Directions] | 6:00 p.m. | ||
| Thu., 3/31 | V Softball | Norwalk (Scrim.) | Home - Wilton HS-Varsity Softball Field [Directions] | 4:00 p.m. | ||
| Sat., 4/2 | V Baseball | Weston | Home - Wilton HS-Varsity Baseball Field [Directions] | 4:00 p.m. | W 11-1 | |
| Sat., 4/2 | JV Baseball | Weston | Home - Wilton HS-JV Baseball Field [Directions] | 2:00 p.m. | ||
| Sat., 4/2 | V Boys Lacrosse | Newtown (Scrim.) | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 2:00 p.m. | ||
| Sat., 4/2 | V Girls Lacrosse | Greenwich Academy (Scrim.) | Away - Greenwich Academy-Turf field | 4:30 p.m. | ||
| Sat., 4/2 | JV Girls Lacrosse | Greenwich Academy (Scrim.) | Away - Greenwich Academy-2nd Field | 4:30 p.m. | ||
| Sat., 4/2 | V Softball | Weston | Home - Wilton HS-Varsity Softball Field [Directions] | 2:00 p.m. | W 8-5 | |
| Sat., 4/2 | JV Girls Tennis | Weston | Away - Weston HS-WHS Tennis Courts [Directions] | Postponed | ||
| Mon., 4/4 | V Boys Outdoor Track | New Canaan | Away - New Canaan HS-NCHS Track [Directions] | 4:00 p.m. | Wilton 84 New Canaan 66 | |
| Mon., 4/4 | V Boys Tennis | Weston | Home - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | W 6-1 [Detailed Results] | |
| Mon., 4/4 | JV Boys Tennis | Weston | Home - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 4/4 | V Girls Outdoor Track | New Canaan | Away - New Canaan HS-NCHS Track [Directions] | 4:00 p.m. | Wilton 73 New Canaan 72 | |
| Mon., 4/4 | V Softball | Greenwich | Home - Wilton HS-Varsity Softball Field [Directions] | 4:00 p.m. | W 12-0 | |
| Mon., 4/4 | JV Softball | Greenwich | Home - Wilton HS-JV Softball Field [Directions] | Postponed | ||
| Mon., 4/4 | V Girls Tennis | St. Lukes (Scrim.) | Away - St Lukes School | 4:00 p.m. | ||
| Tue., 4/5 | V Girls Golf | Darien | Home - Silvermine Golf Club [Directions] | 3:30 p.m. | Wilton - 192 Darien - 209 | |
| Tue., 4/5 | V Girls Lacrosse | Guilford | Home - Wilton HS-Lilly Field [Directions] | 6:00 p.m. | W 20-11 | |
| Tue., 4/5 | V Softball | New Milford | Away - New Milford HS-Softball Varsity Field - NMHS [Directions] | 4:15 p.m. | W 3-1 | |
| Wed., 4/6 | FR Boys Lacrosse | Trumbull | Home - Wilton HS-Veterans Memorial Stadium [Directions] | Canceled | Cancelled | |
| Wed., 4/6 | V Girls Golf | Ridgefield | Home - Silvermine Golf Club [Directions] | 3:30 p.m. | Wilton - 203 Ridgefield - 216 | |
| Wed., 4/6 | JV Girls Golf | Ridgefield | Home - Silvermine Golf Club [Directions] | 3:30 p.m. | ||
| Wed., 4/6 | FR Girls Lacrosse | Trumbull | Away - Trumbull HS-The Pit [Directions] | 4:30 p.m. | ||
| Thu., 4/7 | V Boys Lacrosse | Fordham Prep (NY) | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 6:30 p.m. | W 16-3 | |
| Thu., 4/7 | JV Boys Lacrosse | Fordham Prep (NY) | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 4:30 p.m. | ||
| Thu., 4/7 | JV Boys Tennis | New Canaan | Home - Wilton Middlebrook School-JV Tennis Courts [Directions] | Rainout | ||
| Fri., 4/8 | V Baseball | Wright Tech | Home - Wilton HS-Varsity Baseball Field [Directions] | 4:15 p.m. | W 11-0 | |
| Fri., 4/8 | FR Boys Lacrosse | Darien | Home - Wilton HS-Whitten Field [Directions] | 4:00 p.m. | ||
| Fri., 4/8 | V Boys Tennis | St. Lukes | Home - Wilton HS-Tennis Courts [Directions] | 3:30 p.m. | ||
| Fri., 4/8 | FR Girls Lacrosse | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Sat., 4/9 | V Baseball | Pomperaug | Away - Community House Park-Baseball Field [Directions] | 11:00 a.m. | W 13-2 | |
| Sat., 4/9 | FR Baseball | Pomperaug | Away - Community House Park-Baseball Field [Directions] | Canceled | Cancelled | |
| Sat., 4/9 | V Boys Lacrosse | Fairfield Prep | Away - Fairfield University-Rafferty Stadium [Directions] | 6:00 p.m. | W 11-7 | |
| Sat., 4/9 | JV Boys Lacrosse | Fairfield Prep | Away - Fairfield University-Rafferty Stadium [Directions] | 4:00 p.m. | ||
| Sat., 4/9 | V Girls Lacrosse | Rye (NY) | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | W 14-1 | |
| Mon., 4/11 | V Baseball | Branford | Away - Branford HS-Baseball Diamond [Directions] | 4:30 p.m. | W 8-3 | |
| Mon., 4/11 | FR Boys Lacrosse | Staples | Away - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Mon., 4/11 | V Boys Outdoor Track | Stamford | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 4:00 p.m. | Wilton - 114 Stamford - 23 | |
| Mon., 4/11 | V Boys Tennis | Fairfield Warde | Away - Fairfield Warde HS-Blake Courts [Directions] | 4:30 p.m. | W 6-1 [Detailed Results] | |
| Mon., 4/11 | JV Boys Tennis | Fairfield Warde | Away - Fairfield Warde HS-Knapps Courts [Directions] | 4:30 p.m. | ||
| Mon., 4/11 | FR Girls Lacrosse | Staples | Home - Wilton HS-Allen Meadow [Directions] | 4:00 p.m. | ||
| Mon., 4/11 | V Girls Outdoor Track | Stamford | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 4:00 p.m. | Wilton - 109 Stamford - 22 | |
| Mon., 4/11 | V Girls Tennis | Fairfield Warde | Home - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Mon., 4/11 | JV Girls Tennis | Trumbull | Home - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/12 | V Boys Lacrosse | Stamford | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 6:30 p.m. | W 15-0 | |
| Tue., 4/12 | JV Boys Lacrosse | Stamford | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 4:30 p.m. | ||
| Tue., 4/12 | V Boys Tennis | Norwalk | Home - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Tue., 4/12 | JV Boys Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/12 | V Softball | New Fairfield | Home - Wilton HS-Varsity Softball Field [Directions] | 4:00 p.m. | W 6-3 | |
| Tue., 4/12 | V Girls Tennis | Norwalk | Away - Norwalk HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 4/12 | JV Girls Tennis | Ridgefield | Home - Wilton Middlebrook School-JV Tennis Courts [Directions] | Postponed | ||
| Wed., 4/13 | FR Boys Lacrosse | Greenwich | Home - Allen's Meadow-Lacrosse Field #1 [Directions] | 4:30 p.m. | ||
| Wed., 4/13 | V Girls Golf | Fairfield Ludlowe | Home - Silvermine Golf Club [Directions] | 3:30 p.m. | Wilton - 197 Ludlowe - 201 | |
| Wed., 4/13 | JV Girls Golf | Fairfield Ludlowe | Home - Silvermine Golf Club [Directions] | 3:30 p.m. | ||
| Wed., 4/13 | V Girls Lacrosse | New Canaan | Home - Wilton HS-Lilly Field [Directions] | 6:00 p.m. | L 14-6 | |
| Wed., 4/13 | JV Girls Lacrosse | New Canaan | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | ||
| Wed., 4/13 | JV Girls Tennis | Staples | Home - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 4/14 | JV Baseball | Fairfield Warde | Home - Wilton HS-JV Baseball Field [Directions] | 4:00 p.m. | ||
| Thu., 4/14 | FR Baseball | Fairfield Warde | Away - Fairfield Warde HS-Baseball Diamond [Directions] | Postponed | ||
| Thu., 4/14 | FR Boys Lacrosse | Ridgefield | Home - Allen's Meadow-Lacrosse Field #1 [Directions] | Postponed | ||
| Thu., 4/14 | V Boys Tennis | New Canaan | Home - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Thu., 4/14 | V Girls Golf | Trumbull | Home - Silvermine Golf Club [Directions] | 3:30 p.m. | Wilton - 195 Trumbull - 171 | |
| Thu., 4/14 | FR Girls Lacrosse | Ridgefield | Away - Scotts Ridge MS-SRMS Turf [Directions] | Postponed | ||
| Thu., 4/14 | V Softball | Fairfield Warde | Away - Fairfield Warde HS-Softball Diamond [Directions] | 4:00 p.m. | L 0-3 | |
| Thu., 4/14 | JV Softball | Fairfield Warde | Away - Fairfield Warde HS-Softball Diamond [Directions] | Postponed | ||
| Sat., 4/16 | V Boys Lacrosse | Ridgefield | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 7:00 p.m. | W 15-12 | |
| Sat., 4/16 | JV Boys Lacrosse | Ridgefield | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 4:30 p.m. | ||
| Sat., 4/16 | V Girls Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 11:00 a.m. | W 18-9 | |
| Sat., 4/16 | JV Girls Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 12:30 p.m. | ||
| Sat., 4/16 | V Softball | Stratford | Away - DeLuca Field-Deluca Field [Directions] | 11:00 a.m. | W 16-1 | |
| Mon., 4/18 | V Baseball | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 4:00 p.m. | L 10-3 | |
| Mon., 4/18 | JV Baseball | Norwalk | Away - City Hall Field [Directions] | 4:00 p.m. | ||
| Mon., 4/18 | FR Baseball | Norwalk | Home - Allen's Meadow-Baseball Diamond [Directions] | Postponed | ||
| Mon., 4/18 | FR Boys Lacrosse | Westhill | Home - Allen's Meadow-Lacrosse Field #1 [Directions] | 4:30 p.m. | ||
| Mon., 4/18 | V Boys Tennis | Brien McMahon | Away - Brien McMahon HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Mon., 4/18 | FR Girls Lacrosse | Ridgefield | Home - Wilton HS-Allen Meadow [Directions] | Canceled | Cancelled | |
| Mon., 4/18 | V Softball | Norwalk | Home - Wilton HS-Varsity Softball Field [Directions] | 4:00 p.m. | L 1-5 | |
| Mon., 4/18 | JV Softball | Norwalk | Home - Wilton HS-JV Softball Field [Directions] | Postponed | ||
| Mon., 4/18 | V Girls Tennis | Brien McMahon | Home - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 4/19 | V Boys Lacrosse | Chaminade (NY) | Away - Chaminade-OTT FIELD | 5:00 p.m. | L 5-17 | |
| Tue., 4/19 | JV Boys Lacrosse | Chaminade (NY) | Away - Chaminade HS | 2:30 p.m. | ||
| Tue., 4/19 | V Boys Tennis | Stamford | Home - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Tue., 4/19 | JV Boys Tennis | Darien | Home - Wilton Middlebrook School-JV Tennis Courts [Directions] | Postponed | ||
| Tue., 4/19 | V Girls Lacrosse | Sacred Heart-Hempstead (NY) | Home - Wilton HS-Lilly Field [Directions] | 11:00 a.m. | W 16-4 | |
| Tue., 4/19 | V Girls Tennis | Stamford | Away - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Wed., 4/20 | V Baseball | New Canaan | Away - Mead Park-Baseball Field [Directions] | 4:00 p.m. | L 11-1 | |
| Wed., 4/20 | JV Baseball | New Canaan | Away - Waveny Park-Coppo Field [Directions] | 4:00 p.m. | ||
| Wed., 4/20 | FR Baseball | New Canaan | Home - Allen's Meadow-Baseball Diamond [Directions] | Postponed | ||
| Wed., 4/20 | V Softball | New Canaan | Home - Wilton HS-Varsity Softball Field [Directions] | 4:00 p.m. | L 0-3 | |
| Wed., 4/20 | JV Softball | New Canaan | Home - Wilton HS-JV Softball Field [Directions] | Canceled | Cancelled | |
| Thu., 4/21 | V Baseball | Fairfield Warde | Home - Wilton HS-Varsity Baseball Field [Directions] | 12:00 p.m. | L 2-1 | |
| Thu., 4/21 | V Boys Lacrosse | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 7:00 p.m. | W 15-2 | |
| Thu., 4/21 | JV Boys Lacrosse | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 5:00 p.m. | ||
| Thu., 4/21 | V Boys Tennis | Staples | Away - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | L 1-6 [Detailed Results] | |
| Thu., 4/21 | JV Boys Tennis | Staples | Away - Staples HS-Town Farms Tennis Courts [Directions] | Postponed | ||
| Thu., 4/21 | V Girls Lacrosse | Norwalk | Home - Wilton HS-Lilly Field [Directions] | 6:00 p.m. | W 19-0 | |
| Thu., 4/21 | JV Girls Lacrosse | Norwalk | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | ||
| Thu., 4/21 | V Girls Tennis | Staples | Home - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | L 3-4 | |
| Fri., 4/22 | V Baseball | Brien McMahon | Home - Wilton HS-Varsity Baseball Field [Directions] | 4:00 p.m. | W 9-8 | |
| Fri., 4/22 | JV Baseball | Brien McMahon | Home - Wilton HS-JV Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 4/22 | FR Boys Lacrosse | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 4/22 | FR Girls Lacrosse | Darien | Home - Wilton HS-Allen Meadow [Directions] | 4:00 p.m. | ||
| Fri., 4/22 | V Softball | Brien McMahon | Away - Norwalk HS - Ray Barry Field-Softball Field [Directions] | 4:00 p.m. | L 4-7 | |
| Fri., 4/22 | JV Softball | Brien McMahon | Away - Norwalk HS - Ray Barry Field-Softball Field [Directions] | Canceled | Cancelled | |
| Sat., 4/23 | V Boys Lacrosse | Staples | Away - Staples HS-Staples Stadium [Directions] | 3:00 p.m. | L 6-8 | |
| Sat., 4/23 | JV Boys Lacrosse | Staples | Away - Staples HS-Wakeman Field B (turf) [Directions] | 12:30 p.m. | ||
| Sat., 4/23 | V Girls Lacrosse | Staples | Home - Wilton HS-Lilly Field [Directions] | 6:00 p.m. | W 17-8 | |
| Sat., 4/23 | JV Girls Lacrosse | Staples | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | ||
| Sat., 4/23 | JV Girls Tennis | Darien | Away - Darien HS-DHS Tennis Courts [Directions] | 10:00 a.m. | ||
| Mon., 4/25 | V Baseball | Stamford | Away - Cubeta Stadium [Directions] | 7:00 p.m. | W 8-5 | |
| Mon., 4/25 | JV Baseball | Stamford | Away - Stamford HS-SHS Baseball Diamond [Directions] | 4:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 4:30 p.m. | ||||||
| Mon., 4/25 | FR Baseball | Stamford | Home - Allen's Meadow-Baseball Diamond [Directions] | Canceled | Cancelled | |
| Mon., 4/25 | FR Boys Lacrosse | Trumbull | Away - Trumbull HS-The Pit [Directions] | Postponed | ||
| Mon., 4/25 | V Boys Tennis | Danbury | Home - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | Senior Day |
| Mon., 4/25 | V Girls Golf | Darien | Away - Wee Burn CC [Directions] | 3:00 p.m. | Wilton - 204 Darien - 233 | |
| Mon., 4/25 | FR Girls Lacrosse | Trumbull | Home - Wilton HS-Allen Meadow [Directions] | 4:00 p.m. | ||
| Mon., 4/25 | V Softball | Stamford | Home - Wilton HS-Varsity Softball Field [Directions] | 4:30 p.m. | L 2-7 | |
| Mon., 4/25 | JV Softball | Stamford | Home - Wilton HS-JV Softball Field [Directions] | Postponed | ||
| Mon., 4/25 | V Girls Tennis | Danbury | Away - Danbury HS-DHS Tennis Courts [Directions] | 5:30 p.m. | W 7-0 | |
| Tue., 4/26 | V Boys Lacrosse | Fairfield Ludlowe | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 7:00 p.m. | W 11-4 | |
| Tue., 4/26 | JV Boys Lacrosse | Fairfield Ludlowe | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 4:30 p.m. | ||
| Tue., 4/26 | V Girls Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | 3:30 p.m. | Wilton - 212 Greenwich - 184 | |
| Tue., 4/26 | V Girls Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:30 p.m. | W 18-5 | |
| Tue., 4/26 | JV Girls Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 6:00 p.m. | ||
| Tue., 4/26 | JV Girls Tennis | St. Joseph | Home - Wilton Middlebrook School-JV Tennis Courts [Directions] | Postponed | ||
| Wed., 4/27 | V Baseball | Staples | Home - Wilton HS-Varsity Baseball Field [Directions] | 4:30 p.m. | L 12-2 | |
| Wed., 4/27 | JV Baseball | Staples | Home - Wilton HS-JV Baseball Field [Directions] | 4:30 p.m. | ||
| Wed., 4/27 | FR Baseball | Staples | Away - Staples HS-Baseball Diamond [Directions] | Postponed | ||
| Wed., 4/27 | FR Boys Lacrosse | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Wed., 4/27 | V Boys Tennis | Bridgeport Central | Home - Wilton HS-Tennis Courts [Directions] | 4:30 p.m. | W 7-0 [Detailed Results] | |
| Wed., 4/27 | FR Girls Lacrosse | New Canaan | Home - Wilton HS-Allen Meadow [Directions] | 4:00 p.m. | ||
| Wed., 4/27 | V Softball | Staples | Away - Staples HS-Wakeman Field [Directions] | 4:30 p.m. | L 8-12 | |
| Wed., 4/27 | JV Softball | Staples | Away - Staples HS-Staples Softball Field [Directions] | 5:30 p.m. | ||
| Wed., 4/27 | V Girls Tennis | New Canaan | Home - Wilton HS-Tennis Courts [Directions] | 5:30 p.m. | L 3-4 | |
| Thu., 4/28 | V Boys Tennis | Westhill | Away - Westhill HS-Westhill Tennis Courts [Directions] | 4:00 p.m. | L 3-4 [Detailed Results] | |
| Thu., 4/28 | JV Boys Tennis | New Canaan | Home - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 4/28 | JV Girls Golf | Darien | Home - Silvermine Golf Club [Directions] | 3:00 p.m. | ||
| Thu., 4/28 | V Girls Lacrosse | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:30 p.m. | W 16-2 | |
| Thu., 4/28 | JV Girls Lacrosse | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Thu., 4/28 | V Girls Tennis | Westhill | Home - Wilton HS-Tennis Courts [Directions] | 4:30 p.m. | L 3-4 | |
| Fri., 4/29 | V Baseball | Danbury | Away - Danbury HS-V Baseball Field [Directions] | 4:30 p.m. | L 5-7 | |
| Fri., 4/29 | JV Baseball | Danbury | Away - Danbury HS-JV Baseball Field [Directions] | 4:30 p.m. | ||
| Fri., 4/29 | FR Boys Lacrosse | Stamford | Away - Stamford HS-Upper Lacrosse Field [Directions] | 5:00 p.m. | ||
| Fri., 4/29 | V Boys Outdoor Track | Fairfield Ludlowe | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 4:00 p.m. | ||
| Fri., 4/29 | V Girls Outdoor Track | Fairfield Ludlowe | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 4:00 p.m. | ||
| Fri., 4/29 | V Softball | Danbury | Home - Wilton HS-Varsity Softball Field [Directions] | 4:00 p.m. | L 0-4 | |
| Sat., 4/30 | FR Baseball | Danbury | Home - Allen's Meadow-Baseball Diamond [Directions] | 10:00 a.m. | ||
| Sat., 4/30 | V Boys Lacrosse | Darien | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 7:00 p.m. | L 7-9 | |
| Sat., 4/30 | JV Boys Lacrosse | Darien | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 4:30 p.m. | ||
| Sat., 4/30 | V Boys Tennis | Joel Barlow | Home - Wilton HS-Tennis Courts [Directions] | 3:00 p.m. | W 5-2 [Detailed Results] | |
| Sat., 4/30 | V Girls Lacrosse | Northport (NY) | Away - Northport HS-Baseball Diamond | 2:30 p.m. | L 7-8 | |
| Sat., 4/30 | JV Softball | Danbury | Home - Wilton HS-JV Softball Field [Directions] | Postponed | ||
| Mon., 5/2 | JV Baseball | Bassick | Away - Seaside Park (U. of Bridgeport)-Baseball Diamond [Directions] | Postponed | ||
| Mon., 5/2 | FR Boys Lacrosse | Staples | Home - Allen's Meadow-Lacrosse Field #1 [Directions] | 4:30 p.m. | ||
| Mon., 5/2 | V Girls Golf | Danbury | Home - Silvermine Golf Club [Directions] | 3:30 p.m. | Wilton - 178 Danbury - 227 | |
| Mon., 5/2 | V Girls Lacrosse | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 4:15 p.m. | L 8-12 | |
| Mon., 5/2 | JV Girls Lacrosse | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Mon., 5/2 | FR Girls Lacrosse | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 4:30 p.m. | ||
| Mon., 5/2 | V Girls Outdoor Track | Westhill | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 4:30 p.m. | Wilton - 92 Fairfield Warde - 53 | |
| Mon., 5/2 | JV Softball | Bridgeport Central | Home - Wilton HS-JV Softball Field [Directions] | Canceled | Cancelled | |
| Tue., 5/3 | V Boys Lacrosse | Yorktown (NY) | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 7:00 p.m. | W 12-7 | |
| Tue., 5/3 | JV Boys Lacrosse | Yorktown (NY) | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 4:30 p.m. | ||
| Tue., 5/3 | V Boys Tennis | Ridgefield | Away - Ridgefield HS-RHS Tennis Courts [Directions] | 4:00 p.m. | W 6-1 [Detailed Results] | |
| Tue., 5/3 | JV Boys Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/3 | V Girls Golf | New Canaan | Away - CCNC [Directions] | 3:30 p.m. | Wilton-188 New Canaan - 160 | |
| Tue., 5/3 | V Softball | Bridgeport Central | Home - Wilton HS-Varsity Softball Field [Directions] | 4:00 p.m. | W 15-0 | |
| Tue., 5/3 | V Girls Tennis | Ridgefield | Home - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Tue., 5/3 | JV Girls Tennis | Ridgefield | Home - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/4 | V Girls Golf | Ridgefield | Away - Ridgefield Golf Course [Directions] | 2:30 p.m. | Wilton - 203 Ridgefield - 210 | |
| Wed., 5/4 | V Girls Lacrosse | Sacred Heart of Greenwich (Scrim.) | Home - Wilton HS-Lilly Field [Directions] | 5:00 p.m. | ||
| Wed., 5/4 | JV Softball | Westhill | Away - Westhill HS-Varsity Softball Field [Directions] | Postponed | ||
| Thu., 5/5 | V Baseball | Bridgeport Central | Away - Bridgeport Central HS-Baseball Diamond [Directions] | 4:30 p.m. | W 17-1 | |
| Thu., 5/5 | FR Baseball | Westhill | Home - Wilton HS-Varsity Baseball Field [Directions] | 4:30 p.m. | ||
| Thu., 5/5 | V Boys Lacrosse | Brien McMahon | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 7:00 p.m. | W 18-7 | Senior Night |
| Thu., 5/5 | JV Boys Lacrosse | Brien McMahon | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 4:30 p.m. | ||
| Thu., 5/5 | JV Boys Tennis | Fairfield Ludlowe | Home - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/5 | V Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 5:00 p.m. | W 19-1 | |
| Thu., 5/5 | JV Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | Canceled | Cancelled | |
| Thu., 5/5 | V Softball | Trumbull | Away - Trumbull HS-Varsity Softball Diamond [Directions] | 4:30 p.m. | L 4-5 | |
| Thu., 5/5 | JV Softball | Trumbull | Away - Trumbull HS-JV Softball Diamond [Directions] | Postponed | ||
| Thu., 5/5 | V Girls Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Tennis Courts [Directions] | 4:00 p.m. | L 3-4 | |
| Thu., 5/5 | JV Girls Tennis | Fairfield Ludlowe | Away - Tomlinson MS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 5/6 | FR Boys Lacrosse | Fairfield Ludlowe | Home - Allen's Meadow-Lacrosse Field #1 [Directions] | 4:30 p.m. | ||
| Fri., 5/6 | JV Boys Tennis | Greenwich | Away - Central MS [Directions] | Postponed | ||
| Fri., 5/6 | FR Girls Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | Postponed | ||
| Fri., 5/6 | JV Girls Tennis | Greenwich | Home - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | ||
| Sat., 5/7 | V Boys Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 6:30 p.m. | W 6-4 | |
| Sat., 5/7 | JV Boys Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 3:30 p.m. | ||
| Sat., 5/7 | V Girls Lacrosse | Cheshire | Away - Cheshire HS-Cheshire High School Main Game field [Directions] | 6:00 p.m. | W 15-7 | |
| Sat., 5/7 | JV Girls Lacrosse | Cheshire | Away - Cheshire HS-Cheshire High School Main Game field [Directions] | 4:30 p.m. | ||
| Mon., 5/9 | V Baseball | Ridgefield | Home - Wilton HS-Varsity Baseball Field [Directions] | 4:30 p.m. | L 14-7 | |
| Mon., 5/9 | JV Baseball | Ridgefield | Home - Wilton HS-JV Baseball Field [Directions] | 4:30 p.m. | ||
| Mon., 5/9 | FR Baseball | Ridgefield | Away - Governor Field [Directions] | Canceled | Cancelled | |
| Mon., 5/9 | FR Boys Lacrosse | Greenwich | Away - Greenwich HS-Field 4 [Directions] | 4:30 p.m. | ||
| Mon., 5/9 | V Boys Outdoor Track | Fairfield Warde | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 4:00 p.m. | Wilton - 72 Fairfield Warde - 73 | |
| Mon., 5/9 | V Boys Tennis | Greenwich | Away - Greenwich HS-Tennis Courts [Directions] | 4:00 p.m. | L 3-4 [Detailed Results] | |
| Mon., 5/9 | JV Boys Tennis | Greenwich | Away - Central MS [Directions] | Canceled | Cancelled | |
| Mon., 5/9 | V | Weston, TBA | Away - Weston HS-WHS Stadium Field [Directions] | 3:00 p.m. | ||
| Mon., 5/9 | V Girls Golf | St. Joseph | Home - Silvermine Golf Club [Directions] | 3:30 p.m. | Wilton - 187 St. Joseph - 211 | |
| Mon., 5/9 | V Girls Outdoor Track | Fairfield Warde | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 4:00 p.m. | ||
| Mon., 5/9 | V Softball | Ridgefield | Away - Ridgefield HS-Varsity Field [Directions] | 4:30 p.m. | W 5-3 | |
| Mon., 5/9 | JV Softball | Ridgefield | Away - Ridgefield HS-JV Field [Directions] | Canceled | Cancelled | |
| Mon., 5/9 | V Girls Tennis | Greenwich | Home - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Mon., 5/9 | JV Girls Tennis | Greenwich | Home - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/10 | V Baseball | Harding | Away - Warren Harding HS-Baseball Field [Directions] | 4:00 p.m. | W 15-2 | |
| Tue., 5/10 | V Boys Lacrosse | John Jay (NY) | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 4:30 p.m. | W 13-6 | |
| Tue., 5/10 | JV Boys Lacrosse | John Jay (NY) | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 6:30 p.m. | ||
| Tue., 5/10 | V Boys Tennis | Darien | Home - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | L 3-4 [Detailed Results] | |
| Tue., 5/10 | JV Boys Tennis | Darien | Home - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/10 | V Girls Golf | Fairfield Warde | Home - Silvermine Golf Club [Directions] | 3:30 p.m. | Wilton - 172 Warde - 207 | |
| Tue., 5/10 | JV Girls Golf | Fairfield Warde | Away - Carl Dickman Par 3 [Directions] | 3:15 p.m. | ||
| Tue., 5/10 | JV Girls Golf | Fairfield Ludlowe | Away - Carl Dickman Par 3 [Directions] | 3:15 p.m. | ||
| Tue., 5/10 | V Girls Lacrosse | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | W 17-1 | |
| Tue., 5/10 | JV Girls Lacrosse | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Tue., 5/10 | V Softball | Westhill | Away - Westhill HS-Varsity Softball Field [Directions] | 4:30 p.m. | W 12-1 | |
| Tue., 5/10 | V Girls Tennis | Darien | Away - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | L 1-6 | |
| Tue., 5/10 | JV Girls Tennis | Darien | Away - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/11 | V Baseball | Fairfield Ludlowe | Away - Kiwanis Field-Baseball Diamond [Directions] | 4:30 p.m. | W 10-6 | |
| Wed., 5/11 | JV Baseball | Fairfield Ludlowe | Away - Owen Fish Park-Owen Fish [Directions] | 4:30 p.m. | ||
| Wed., 5/11 | V Girls Lacrosse | Greenwich Academy (Scrim.) | Home - Wilton HS-Lilly Field [Directions] | 6:00 p.m. | ||
| Wed., 5/11 | JV Girls Lacrosse | Greenwich Academy (Scrim.) | Home - Wilton HS-Lilly Field [Directions] | 4:30 p.m. | ||
| Wed., 5/11 | FR Girls Lacrosse | Trumbull | Home - Wilton HS-Lilly Field [Directions] | 7:30 p.m. | ||
| Wed., 5/11 | V Softball | Fairfield Ludlowe | Home - Wilton HS-Varsity Softball Field [Directions] | 5:00 p.m. | L 0-14 | |
| Wed., 5/11 | JV Softball | Fairfield Ludlowe | Home - Wilton HS-JV Softball Field [Directions] | Canceled | Cancelled | |
| Wed., 5/11 | V Girls Tennis | Bridgeport Central | Away - Bridgeport Central HS-Central High School Tennis Courts [Directions] | 4:30 p.m. | W 7-0 | |
| Thu., 5/12 | V Baseball | Greenwich | Home - Wilton HS-Varsity Baseball Field [Directions] | 6:00 p.m. | W 4-3 | |
| Thu., 5/12 | FR Baseball | Fairfield Ludlowe | Home - Allen's Meadow-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Thu., 5/12 | V Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 6:30 p.m. | W 15-1 | |
| Thu., 5/12 | JV Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:30 p.m. | ||
| Thu., 5/12 | V Boys Outdoor Track | Darien | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 4:00 p.m. | ||
| Thu., 5/12 | V Boys Tennis | St. Joseph | Home - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Thu., 5/12 | V Girls Lacrosse | Fairfield Warde | Home - Wilton HS-Lilly Field [Directions] | 7:00 p.m. | W 18-6 | Senior Night |
| Thu., 5/12 | JV Girls Lacrosse | Fairfield Warde | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | ||
| Thu., 5/12 | V Girls Outdoor Track | Darien | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 4:00 p.m. | ||
| Thu., 5/12 | V Girls Tennis | St. Joseph | Away - St. Joseph HS-Tennis Courts [Directions] | 4:30 p.m. | W 4-3 | |
| Thu., 5/12 | JV Girls Tennis | St. Joseph | Home - Wilton Middlebrook School-JV Tennis Courts [Directions] | Canceled | Cancelled | |
| Fri., 5/13 | JV Baseball | Greenwich | Home - Wilton HS-JV Baseball Field [Directions] | 4:30 p.m. | ||
| Fri., 5/13 | FR Boys Lacrosse | New Canaan | Home - Allen's Meadow-Lacrosse Field #1 [Directions] | 4:30 p.m. | ||
| Fri., 5/13 | V Boys Tennis | Fairfield Ludlowe | Home - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Fri., 5/13 | FR Girls Lacrosse | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Fri., 5/13 | V Softball | Greenwich | Away - Greenwich HS-Softball Field [Directions] | 4:30 p.m. | W 10-2 | |
| Fri., 5/13 | JV Softball | Greenwich | Away - Julian Curtiss School [Directions] | Canceled | Cancelled | |
| Fri., 5/13 | V Girls Tennis | Trumbull | Home - Wilton HS-Tennis Courts [Directions] | 4:30 p.m. | W 7-0 | |
| Fri., 5/13 | JV Girls Tennis | Trumbull | Home - Wilton HS-Tennis Courts [Directions] | 4:30 p.m. | ||
| Sat., 5/14 | V Baseball | Westhill | Home - Wilton HS-Varsity Baseball Field [Directions] | 2:00 p.m. | L 0-5 | |
| Sat., 5/14 | FR Baseball | Greenwich | Away - Greenwich HS-Baseball Field [Directions] | 10:00 a.m. | ||
| Sat., 5/14 | V Boys Lacrosse | Greenwich | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 7:00 p.m. | W 9-3 | |
| Sat., 5/14 | JV Boys Lacrosse | Greenwich | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 4:30 p.m. | ||
| Sat., 5/14 | V Boys Tennis | Trumbull | Away - Trumbull HS-Tennis Courts [Directions] | 11:00 a.m. | W 7-0 [Detailed Results] | |
| Sat., 5/14 | JV Boys Tennis | Trumbull | Away - Trumbull HS-Tennis Courts [Directions] | 12:30 p.m. | ||
| Sun., 5/15 | V Girls Tennis | Weston | Home - Wilton HS-Tennis Courts [Directions] | 11:00 a.m. | W 6-1 | |
| Mon., 5/16 | V Girls Golf | New Canaan | Home - Silvermine Golf Club [Directions] | 3:30 p.m. | Wilton - 173 New Canaan - 156 | |
| Tue., 5/17 | V Baseball | Trumbull | Home - Wilton HS-Varsity Baseball Field [Directions] | 4:30 p.m. | L 0-7 | |
| Tue., 5/17 | JV Baseball | Trumbull | Home - Wilton HS-JV Baseball Field [Directions] | 4:30 p.m. | ||
| Tue., 5/17 | V Boys Lacrosse | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 4:30 p.m. | W 13-11 | |
| Tue., 5/17 | V Boys Outdoor Track | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/17 | V Girls Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 3:30 p.m. | Wilton - 202 Ludlowe - 233 | |
| Tue., 5/17 | JV Girls Golf | Darien, New Canaan | Away - Wee Burn CC [Directions] | 3:00 p.m. | ||
| Tue., 5/17 | V Girls Lacrosse | St. Joseph | Home - Wilton HS-Lilly Field [Directions] | 6:00 p.m. | W 19-8 | |
| Tue., 5/17 | JV Girls Lacrosse | St. Joseph | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | ||
| Tue., 5/17 | V Girls Outdoor Track | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/17 | V Softball | Darien | Home - Wilton HS-Varsity Softball Field [Directions] | 7:00 p.m. | L 1-16 | |
| Tue., 5/17 | V Girls Tennis | Westhill | Away - Westhill HS-Westhill Tennis Courts [Directions] | 4:00 p.m. | L 3-4 | |
| Wed., 5/18 | JV Boys Lacrosse | St. Joseph | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 4:00 p.m. | ||
| Wed., 5/18 | V Boys Tennis | Westhill | Away - Westhill HS-Westhill Tennis Courts [Directions] | 4:00 p.m. | L 3-4 | |
| Wed., 5/18 | JV Girls Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 4:30 p.m. | ||
| Wed., 5/18 | V Softball | St. Joseph | Home - Wilton HS-Varsity Softball Field [Directions] | 4:00 p.m. | L 0-6 | |
| Wed., 5/18 | JV Softball | St. Joseph | Home - Wilton HS-JV Softball Field [Directions] | Canceled | Cancelled | |
| Thu., 5/19 | V Baseball | Darien | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | W 2-1 | |
| Thu., 5/19 | JV Baseball | Darien | Away - Darien HS-DHS Baseball - JV Field [Directions] | Canceled | Cancelled | |
| Thu., 5/19 | JV Baseball | St. Joseph | Away - Unity Park-Field 1 [Directions] | Canceled | Cancelled | |
| Thu., 5/19 | FR Baseball | St. Joseph | Home - Allen's Meadow-Baseball Diamond [Directions] | Postponed | ||
| Thu., 5/19 | FR Boys Lacrosse | Fairfield Prep | Home - Allen's Meadow-Lacrosse Field #1 [Directions] | Postponed | ||
| Thu., 5/19 | V Girls Golf | Staples | Home - Silvermine Golf Club [Directions] | 3:30 p.m. | Wilton - 170 Staples - 157 | |
| Thu., 5/19 | V Girls Lacrosse | Fairfield Ludlowe | Home - Wilton HS-Lilly Field [Directions] | 7:00 p.m. | W 15-0 | |
| Thu., 5/19 | FR Girls Lacrosse | Ridgefield | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | ||
| Thu., 5/19 | V | Unified Track Meet | Away - Not Listed | 3:30 a.m. | ||
| Fri., 5/20 | V Baseball | St. Joseph | Away - St. Joseph HS-Baseball Diamond [Directions] | 1:00 p.m. | L 7-1 | |
| Fri., 5/20 | FR Baseball | Darien | Home - Allen's Meadow-Baseball Diamond [Directions] | 4:15 p.m. | ||
| Fri., 5/20 | FR Boys Lacrosse | Ridgefield | Away - Scotts Ridge MS-SRMS Turf [Directions] | 4:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Ridgefield HS-Tiger Hollow Stadium | ||||||
| Fri., 5/20 | Miscellaneous Events | Jr. Prom | Home - Wilton HS [Directions] | TBA | ||
| Sat., 5/21 | V Boys Lacrosse | New Canaan | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 7:00 p.m. | W 9-5 | |
| Mon., 5/23 | V Girls Lacrosse | New Canaan | Home - Norwalk HS-Testa Field [Directions] | 5:00 p.m. | L 6-15 | |
| Mon., 5/23 | V Girls Outdoor Track | FCIAC Championships | Away - Wilton HS-Fujitani Field - Turf | 3:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Danbury HS-Wilton HS-Fujitani Field - Turf | ||||||
| Tue., 5/24 | FR Baseball | Trumbull | Away - Trumbull HS-JV Baseball Field [Directions] | 6:00 p.m. | ||
| Tue., 5/24 | V Boys Lacrosse | Staples | Away - Brien McMahon HS-Casagrande Field [Directions] | 5:00 p.m. | W 7-6 | |
| Tue., 5/24 | V Boys Outdoor Track | FCIAC Championships | Away - Danbury HS-Stadium Track | 3:30 p.m. | ||
| Wed., 5/25 | FR Boys Lacrosse | Fairfield Prep | Home - Allen's Meadow-Lacrosse Field #1 [Directions] | 4:30 p.m. | ||
| Wed., 5/25 | V Softball | New Canaan (Scrim.) | Away - Waveny Park-Orchard Field [Directions] | 5:30 p.m. | ||
| Thu., 5/26 | V Baseball | New Canaan (Scrim.) | Home - Wilton HS-Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Thu., 5/26 | JV Boys Tennis | Weston | Home - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/26 | V Girls Golf | Danbury | Home - Silvermine Golf Club [Directions] | 3:30 p.m. | Wilton - 180 Danbury - 214 | |
| Fri., 5/27 | V Girls Tennis | Ridgefield | Home - Wilton HS-Tennis Courts [Directions] | 3:30 p.m. | W 6-1 | |
| Sat., 5/28 | V Boys Lacrosse | Darien | Home - Brien McMahon HS-Casagrande Field [Directions] | 11:00 a.m. | L 6-12 | |
| Tue., 5/31 | V Baseball | Notre Dame-West Haven | Away - Quigley Stadium [Directions] | 3:30 p.m. | L 1-10 | |
| Tue., 5/31 | V Boys Tennis | New Milford | Home - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 5/31 | V Girls Lacrosse | Southington | Home - Wilton HS-Lilly Field [Directions] | 5:00 p.m. | W 17-1 | |
| Tue., 5/31 | V Softball | Bristol Central | Away - Bristol Central HS-Softball Field [Directions] | 4:00 p.m. | ||
| Tue., 5/31 | V Girls Tennis | Farmington | Away - Farmington HS [Directions] | 1:00 p.m. | W 5-2 | |
| Wed., 6/1 | V Boys Lacrosse | Pomperaug | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 4:30 p.m. | W 17-2 | |
| Wed., 6/1 | V Boys Outdoor Track | CIAC Class L Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Wed., 6/1 | V Boys Tennis | Darien | Away - Darien HS-DHS Tennis Courts [Directions] | 3:00 p.m. | L 1-4 | |
| Wed., 6/1 | V Girls Outdoor Track | CIAC Class L Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Wed., 6/1 | V Girls Tennis | Glastonbury | Away - Glastonbury HS-Tennis Courts [Directions] | 1:00 p.m. | W 6-1 | |
| Fri., 6/3 | V Girls Lacrosse | Cheshire | Home - Wilton HS-Lilly Field [Directions] | 5:00 p.m. | W 17-6 | |
| Fri., 6/3 | V Girls Tennis | Amity | Away - Amity Regional HS-Tennis Courts [Directions] | 3:00 p.m. | L 3-4 | |
| Sat., 6/4 | V Boys Lacrosse | Daniel Hand | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 1:30 p.m. | W 10-9 | |
| Sat., 6/4 | Miscellaneous Events | Sr. Prom | Home - Wilton HS [Directions] | TBA | ||
| Mon., 6/6 | V Boys Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/6 | V Boys Tennis | CIAC Individual Invitational - Opening Round, Singles and Doubles | Away - Wesleyan | 10:00 a.m. | ||
| Mon., 6/6 | V | Weston | Home - Wilton HS-Track [Directions] | 3:00 p.m. | ||
| Mon., 6/6 | V Girls Golf | CIAC Division I Championship | Away - Tashua Knolls GC | 8:30 a.m. | ||
| Mon., 6/6 | V Girls Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/6 | V Girls Tennis | CIAC Individual Invitational - Opening Round, Singles and Doubles | Away - Wesleyan | 10:00 a.m. | ||
| Tue., 6/7 | V Boys Tennis | CIAC Individual Invitational - Round of 16 | Away - Wesleyan | 9:00 a.m. | ||
| Tue., 6/7 | V Girls Lacrosse | Darien | Away - Greenwich HS-Cardinal Stadium [Directions] | 7:00 p.m. | ||
| Tue., 6/7 | V Girls Tennis | CIAC Individual Invitational - Round of 16 | Away - Wesleyan | 9:00 a.m. | ||
| Wed., 6/8 | V Boys Lacrosse | Cheshire | Away - Jonathan Law HS-Lawmen Stadium [Directions] | 7:30 p.m. | ||
| Wed., 6/8 | V Boys Tennis | CIAC Individual Invitational - Quarterfinals | Away - Wesleyan | 3:00 p.m. | ||
| Wed., 6/8 | V Girls Tennis | CIAC Individual Invitational - Quarterfinals | Away - Wesleyan | 3:00 p.m. | ||
| Thu., 6/9 | V Boys Tennis | CIAC Individual Invitational - Semifinals | Away - Wesleyan | 3:00 p.m. | ||
| Thu., 6/9 | V Girls Tennis | CIAC Individual Invitational - Semifinals | Away - Wesleyan | 3:00 p.m. | ||
| Fri., 6/10 | V Boys Tennis | CIAC Individual Invitational - Finals | Away - Wesleyan | 3:00 p.m. | ||
| Fri., 6/10 | V Girls Tennis | CIAC Individual Invitational - Finals | Away - Wesleyan | 3:00 p.m. | ||
| Sat., 6/11 | V Girls Golf | CIAC Girls State Open | Away - Black Hall Club | 1:00 p.m. | ||
| Sun., 6/12 | V Boys Lacrosse | Notre Dame-West Haven | Home - Sacred Heart University [Directions] | 12:30 p.m. | ||
| Mon., 6/13 | V Boys Outdoor Track | CIAC Boys Hammer Throw Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Mon., 6/13 | V Girls Outdoor Track | CIAC Girls Hammer Throw Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Tue., 6/14 | V Boys Outdoor Track | CIAC Decathlon Championship Day 1 | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 6/14 | V Girls Outdoor Track | CIAC Heptathlon Championship Day 1 | Away - Willow Brook Park | 10:30 a.m. | ||
| Tue., 6/14 | V Girls Outdoor Track | CIAC Girls Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/15 | V Boys Outdoor Track | CIAC Decathlon Championship Day 2 | Away - Willow Brook Park | 10:00 a.m. | ||
| Wed., 6/15 | V Boys Outdoor Track | CIAC Boys Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/15 | V Girls Outdoor Track | CIAC Heptathlon Championship Day 2 | Away - Willow Brook Park | 10:00 a.m. | ||