| Wilton 2022-23 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 730 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Tue., 8/23 | V Boys Golf | New Canaan | Home - Rolling Hills Country Club [Directions] | 3:15 p.m. | Wilton - 161 New Canaan - 160 | |
| Wed., 8/24 | V Boys Golf | Brien McMahon | Home - Rolling Hills Country Club [Directions] | 3:15 p.m. | Wilton - 163 McMahon - 176 | |
| Mon., 8/29 | V Boys Golf | Danbury | Home - Rolling Hills Country Club [Directions] | 3:15 p.m. | Wilton - 167 Danbury - 177 | |
| Mon., 8/29 | JV Boys Golf | Danbury | Home - Rolling Hills Country Club [Directions] | 3:15 p.m. | ||
| Tue., 8/30 | JV Boys Golf | Darien | Home - Rolling Hills Country Club [Directions] | 3:30 p.m. | ||
| Wed., 8/31 | V Boys Golf | Staples | Away - Longshore Golf Course [Directions] | 3:00 p.m. | Wilton - 159 Staples - 156 | |
| Wed., 8/31 | JV Boys Golf | Staples | Away - Longshore Golf Course [Directions] | 3:00 p.m. | Wilton - 169 Staples - 174 | |
| Thu., 9/8 | FR Football | Norwich Free Academy | Away - Norwich Free Academy-Turf Field [Directions] | 6:30 p.m. | W 34-0 | |
| Thu., 9/8 | V Boys Soccer | Fairfield Warde | Home - Wilton HS-Lilly Field [Directions] | 5:30 p.m. | L 0-4 | |
| Thu., 9/8 | JV Boys Soccer | Fairfield Warde | Home - Allen's Meadow-2A [Directions] | 4:30 p.m. | W 1-0 | |
| Thu., 9/8 | FR Boys Soccer | Fairfield Warde | Away - Tunxis [Directions] | 4:30 p.m. | W 7-3 | |
| Thu., 9/8 | V Field Hockey | St. Joseph | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 6:30 p.m. | W 7-0 | |
| Thu., 9/8 | JV Field Hockey | St. Joseph | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 5:00 p.m. | W 6-0 | |
| Thu., 9/8 | V Girls Volleyball | Wright Tech | Away - J M Wright Tech School-Thomas R. Good Gymnasium [Directions] | 5:45 p.m. | W 3-0 | |
| Thu., 9/8 | JV Girls Volleyball | Wright Tech | Away - J M Wright Tech School-Thomas R. Good Gymnasium [Directions] | 4:30 p.m. | W 2-0 | |
| Fri., 9/9 | V Football | Norwich Free Academy | Away - Norwich Free Academy-Turf Field [Directions] | 7:00 p.m. | W 31-14 | |
| Fri., 9/9 | V Girls Soccer | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 6:00 p.m. | L 0-1 | |
| Fri., 9/9 | JV Girls Soccer | Fairfield Warde | Away - Fairfield Warde HS-Fairfield Warde Grass Utility Field [Directions] | 4:00 p.m. | L 1-2 | |
| Fri., 9/9 | FR Girls Soccer | Fairfield Warde | Home - Allen's Meadow-3A [Directions] | 4:00 p.m. | L 1-2 | |
| Sat., 9/10 | JV Football | Norwich Free Academy | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 12:00 p.m. | ||
| Sat., 9/10 | V Boys Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 7:00 p.m. | L 1-5 | |
| Sat., 9/10 | JV Boys Soccer | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | 5:00 p.m. | L 1-5 | |
| Sat., 9/10 | FR Boys Soccer | Norwalk | Home - Allen's Meadow-3A [Directions] | 4:30 p.m. | L 0-5 | |
| Mon., 9/12 | V Boys Golf | Fairfield Ludlowe | Home - Rolling Hills Country Club [Directions] | 3:15 p.m. | Wilton - 165 Ludlowe - 183 | |
| Mon., 9/12 | JV Boys Golf | Fairfield Ludlowe | Home - Rolling Hills Country Club [Directions] | 3:15 p.m. | Wilton-179 Ludlowe-189 | |
| Mon., 9/12 | V Field Hockey | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:30 p.m. | W 5-1 | |
| Mon., 9/12 | JV Field Hockey | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 5:30 p.m. | L 0-1 | |
| Mon., 9/12 | FR Field Hockey | Greenwich | Home - Wilton HS-Fujitani Field - Turf [Directions] | 6:30 p.m. | ||
| Mon., 9/12 | V Girls Soccer | Norwalk | Home - Wilton HS-Lilly Field [Directions] | 7:00 p.m. | W 7-1 | |
| Mon., 9/12 | JV Girls Soccer | Norwalk | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | W 7-0 | |
| Mon., 9/12 | V Girls Volleyball | New Milford | Away - New Milford HS-Main Gym - NMHS [Directions] | 7:00 p.m. | W 3-0 | |
| Mon., 9/12 | JV Girls Volleyball | New Milford | Away - New Milford HS-Main Gym - NMHS [Directions] | 5:30 p.m. | W 2-0 | |
| Mon., 9/12 | FR Girls Volleyball | New Milford | Away - New Milford HS-Small Gym - NMHS [Directions] | 5:30 p.m. | L 0-2 | |
| Tue., 9/13 | V Boys Golf | Westhill | Away - EG Brennan Golf Course-E Gaynor Brennan Golf Course [Directions] | 3:15 p.m. | Wilton - 156 Westhill - 160 | |
| Tue., 9/13 | V Boys Soccer | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 7:00 p.m. | L 1-3 | |
| Tue., 9/13 | JV Boys Soccer | New Canaan | Away - Saxe MS-Field 1 [Directions] | 4:30 p.m. | W 4-1 | |
| Tue., 9/13 | FR Boys Soccer | New Canaan | Home - Allen's Meadow-Field #1 [Directions] | 4:30 p.m. | ||
| Wed., 9/14 | V Boys Cross Country | Darien, Danbury, Norwalk | Away - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | Darien - 26 Wilton - 32 Danbury - 23 WIlton - 38 WIlton - 20 Norwalk - 39 | |
| Wed., 9/14 | V Boys Golf | Norwalk | Away - Oak Hills Golf Course [Directions] | 3:00 p.m. | Wilton - 160 Norwalk - 180 | |
| Wed., 9/14 | V Girls Cross Country | Darien, Danbury, Norwalk | Away - Darien HS-DHS Stadium Field [Directions] | 4:15 p.m. | Wilton - 17 Danbury - 42 Wilton - 15 Norwalk - 50 Wilton - 21 Darien - 38 | |
| Wed., 9/14 | V Girls Soccer | New Canaan | Home - Wilton HS-Lilly Field [Directions] | 7:00 p.m. | W 2-0 | |
| Wed., 9/14 | JV Girls Soccer | New Canaan | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | T 0-0 | |
| Wed., 9/14 | FR Girls Soccer | New Canaan | Away - Saxe MS-Field 1 [Directions] | 4:30 p.m. | L 0-3 | |
| Wed., 9/14 | V Girls Volleyball | Weston | Away - Weston HS-Gym (New) [Directions] | 6:00 p.m. | W 3-0 | |
| Wed., 9/14 | JV Girls Volleyball | Weston | Away - Weston HS-Gym (New) [Directions] | 4:30 p.m. | W 2-0 | |
| Wed., 9/14 | FR Girls Volleyball | Weston | Away - Weston HS-Gym (Old) [Directions] | 4:30 p.m. | L 0-3 | |
| Thu., 9/15 | FR Field Hockey | Darien | Home - Wilton HS-Fujitani Field - Turf [Directions] | 4:15 p.m. | L 1-3 | |
| Fri., 9/16 | V Football | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 7:00 p.m. | W 24-14 | |
| Fri., 9/16 | V Boys Soccer | Brien McMahon | Home - Wilton HS-Lilly Field [Directions] | 5:30 p.m. | L 0-5 | |
| Fri., 9/16 | JV Boys Soccer | Brien McMahon | Home - Allen's Meadow-Field #1 [Directions] | 4:30 p.m. | L 1-3 | |
| Sat., 9/17 | V Boys Cross Country | Wilton Invitational | Home - Allen's Meadow-XC Course [Directions] | 9:00 a.m. | ||
| Sat., 9/17 | V Boys Cross Country | Guilford | Home - Allen's Meadow-XC Course [Directions] | 9:00 a.m. | ||
| Sat., 9/17 | V Boys Cross Country | Cheshire | Home - Allen's Meadow-XC Course [Directions] | 9:00 a.m. | ||
| Sat., 9/17 | V Boys Cross Country | New Canaan | Home - Allen's Meadow-XC Course [Directions] | 9:00 a.m. | ||
| Sat., 9/17 | V Boys Cross Country | New Fairfield | Home - Allen's Meadow-XC Course [Directions] | 9:00 a.m. | ||
| Sat., 9/17 | V Boys Cross Country | Trumbull | Home - Allen's Meadow-XC Course [Directions] | 9:30 a.m. | ||
| Sat., 9/17 | V Boys Cross Country | Darien | Home - Allen's Meadow-XC Course [Directions] | 9:30 p.m. | ||
| Sat., 9/17 | V Boys Cross Country | Pomperaug | Home - Allen's Meadow-XC Course [Directions] | TBA | ||
| Sat., 9/17 | JV Football | Fairfield Ludlowe | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 10:00 a.m. | ||
| Sat., 9/17 | V Girls Cross Country | Trumbull | Home - Allen's Meadow-XC Course [Directions] | 9:00 a.m. | ||
| Sat., 9/17 | V Girls Cross Country | New Canaan | Home - Allen's Meadow-XC Course [Directions] | 9:00 a.m. | ||
| Sat., 9/17 | V Girls Cross Country | Cheshire | Home - Allen's Meadow-XC Course [Directions] | 9:00 a.m. | ||
| Sat., 9/17 | V Girls Cross Country | Guilford | Home - Allen's Meadow-XC Course [Directions] | 9:00 a.m. | ||
| Sat., 9/17 | V Girls Cross Country | New Fairfield | Home - Allen's Meadow-XC Course [Directions] | 9:00 a.m. | ||
| Sat., 9/17 | V Girls Cross Country | Bethel | Home - Allen's Meadow Field [Directions] | 9:00 a.m. | ||
| Sat., 9/17 | V Girls Cross Country | Darien | Home - Allen's Meadow-XC Course [Directions] | 9:30 a.m. | ||
| Sat., 9/17 | V Girls Cross Country | Daniel Hand | Home - Allen's Meadow-XC Course [Directions] | 9:30 a.m. | ||
| Sat., 9/17 | V Girls Cross Country | Pomperaug | Home - Allen's Meadow-XC Course [Directions] | TBA | ||
| Sat., 9/17 | V Field Hockey | Staples | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 3:30 p.m. | W 4-1 | |
| Sat., 9/17 | JV Field Hockey | Staples | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 2:00 p.m. | T 1-1 | |
| Sat., 9/17 | FR Field Hockey | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 10:00 a.m. | W 5-0 | |
| Sat., 9/17 | V Girls Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 10:00 a.m. | W 1-0 | |
| Sat., 9/17 | JV Girls Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | Postponed | ||
| Sat., 9/17 | V Girls Swimming and Diving | St. Joseph | Away - FLOOD MS [Directions] | 2:00 p.m. | Wilton - 97 St. Joseph - 64 | |
| Sat., 9/17 | V Girls Volleyball | Branford | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 12:00 p.m. | W 3-0 | |
| Sat., 9/17 | JV Girls Volleyball | Branford | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 10:00 a.m. | W 2-1 | |
| Mon., 9/19 | V Boys Soccer | Stamford | Away - Stamford HS-SHS Upper Soccer Field [Directions] | 4:30 p.m. | L 0-2 | |
| Mon., 9/19 | JV Boys Soccer | Stamford | Away - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | L 0-3 | |
| Mon., 9/19 | FR Boys Soccer | Stamford | Home - Allen's Meadow-3A [Directions] | 4:30 p.m. | L 3-4 | |
| Mon., 9/19 | V Girls Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Mon., 9/19 | JV Girls Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:30 p.m. | L 1-2 | |
| Tue., 9/20 | V Boys Cross Country | Brien McMahon, Fairfield Ludlowe, Staples | Home - Allen's Meadow-XC Course [Directions] | 4:00 p.m. | Wilton - 39 McMahon - 22 Wilton - 39 Ludlowe - 25 Wilton - 38 Staples - 23 | |
| Tue., 9/20 | V Boys Golf | Stamford | Away - Stamford High-Sterling Farms Golf Course [Directions] | 2:30 p.m. | Wilton 164 Stamford 184 | |
| Tue., 9/20 | JV Boys Golf | Ridgefield | Away - Ridgefield Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 9/20 | V Girls Cross Country | Brien McMahon, Fairfield Ludlowe, Staples | Home - Allen's Meadow-XC Course [Directions] | 4:00 p.m. | Wilton - 19 Staples - 42 Wilton - 20 Ludlowe - 39 Wilton - 16 McMahon - 47 | |
| Tue., 9/20 | V Girls Diving | New Canaan | Home - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Tue., 9/20 | V Field Hockey | Stamford | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 6:30 p.m. | W 7-0 | |
| Tue., 9/20 | JV Field Hockey | Stamford | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 5:00 p.m. | ||
| Tue., 9/20 | V Girls Soccer | Stamford | Home - Wilton HS-Lilly Field [Directions] | 5:30 p.m. | W 3-0 | |
| Tue., 9/20 | JV Girls Soccer | Stamford | Home - Wilton HS-Allen Meadow [Directions] | 4:00 p.m. | W 4-1 | |
| Tue., 9/20 | FR Girls Volleyball | Staples | Away - Staples HS-Field House [Directions] | 4:30 p.m. | L 0-3 | |
| Wed., 9/21 | V Boys Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | 3:30 p.m. | Wilton 162 Greenwich 151 | |
| Wed., 9/21 | FR Field Hockey | Darien | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:30 p.m. | L 1-3 | |
| Wed., 9/21 | V Girls Swimming and Diving | New Canaan | Home - Wilton YMCA [Directions] | 3:40 p.m. | WIlton 103 New Canaan - 83 | |
| Thu., 9/22 | FR Football | Bristol Central | Away - Bristol Central HS-BC Turf Field [Directions] | 4:30 p.m. | ||
| Thu., 9/22 | V Boys Soccer | Staples | Home - Wilton HS-Lilly Field [Directions] | 5:30 p.m. | W 2-1 | |
| Thu., 9/22 | JV Boys Soccer | Staples | Home - Allen's Meadow-2A [Directions] | Postponed | ||
| Thu., 9/22 | FR Boys Soccer | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | Postponed | ||
| Thu., 9/22 | V Girls Diving | Fairfield Ludlowe, Fairfield Warde | Home - New Canaan Y -Diving Only [Directions] | 3:30 p.m. | ||
| Thu., 9/22 | V Girls Volleyball | Fairfield Warde | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:30 p.m. | L 3-0 | |
| Thu., 9/22 | JV Girls Volleyball | Fairfield Warde | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:15 p.m. | W 2-1 | |
| Thu., 9/22 | FR Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:30 p.m. | L 0-3 | |
| Fri., 9/23 | V Football | Bristol Central | Home - Wilton HS-Fujitani Field - Turf [Directions] | 7:00 p.m. | W 14-6 | |
| Fri., 9/23 | V Field Hockey | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 4:30 p.m. | W 6-0 | |
| Fri., 9/23 | JV Field Hockey | Danbury | Away - Danbury HS-Grass Field Hockey Field [Directions] | 6:00 p.m. | W 8-0 | |
| Fri., 9/23 | FR Field Hockey | Danbury | Home - Wilton HS-Fuijitani Field -Turf [Directions] | Postponed | ||
| Fri., 9/23 | V Girls Soccer | Staples | Away - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | L 1-4 | |
| Fri., 9/23 | JV Girls Soccer | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | L 0-1 | |
| Fri., 9/23 | FR Girls Soccer | Staples | Home - Allen's Meadow-3A [Directions] | 4:00 p.m. | L 0-1 | |
| Fri., 9/23 | V Girls Swimming and Diving | Fairfield Ludlowe | Home - Wilton YMCA [Directions] | 3:40 p.m. | Wilton - 93 Ludlow - 69 | |
| Sat., 9/24 | JV Football | Bristol Central | Away - Bristol Central HS-BC Turf Field [Directions] | 10:30 a.m. | ||
| Sat., 9/24 | V Boys Soccer | Newington | Away - Farmington Soccer Academy [Directions] | 3:00 p.m. | L 0-2 | |
| Sat., 9/24 | FR Girls Volleyball | Kennedy Catholic-Somers (NY) | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 10:00 a.m. | L 0-3 | |
| Tue., 9/27 | JV Boys Golf | Greenwich | Home - Rolling Hills Country Club [Directions] | 3:15 p.m. | ||
| Tue., 9/27 | V Field Hockey | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 7:00 p.m. | W 4-1 | |
| Tue., 9/27 | JV Field Hockey | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 5:30 p.m. | L 0-2 | |
| Tue., 9/27 | FR Field Hockey | Trumbull | Home - Trumbull HS-McDougall Stadium [Directions] | Postponed | ||
| Tue., 9/27 | V Girls Soccer | Danbury | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | L 0-1 | |
| Tue., 9/27 | JV Girls Soccer | Danbury | Home - Allen's Meadow-2A [Directions] | 4:00 p.m. | L 0-1 | |
| Tue., 9/27 | FR Girls Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 4:30 p.m. | W 8-0 | |
| Tue., 9/27 | V Girls Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:30 p.m. | W 3-0 | |
| Tue., 9/27 | JV Girls Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 6:00 p.m. | W 2-0 | |
| Tue., 9/27 | FR Girls Volleyball | Norwalk | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Wed., 9/28 | V Boys Cross Country | New Canaan, Stamford, Westhill | Away - Waveny Park [Directions] | 4:30 p.m. | Wilton - 15 Westhill - 50 Wilton - 21 Stamford - 40 New Canaan - 21 Wilton - 36 | |
| Wed., 9/28 | V Boys Golf | St. Joseph | Home - Rolling Hills Country Club [Directions] | 3:15 p.m. | Wilton 169 St Joseph 162 | |
| Wed., 9/28 | JV Boys Golf | St. Joseph | Home - Rolling Hills Country Club [Directions] | 3:15 p.m. | Wilton-177 Sr. Joseph - 209 | |
| Wed., 9/28 | V Boys Soccer | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 6:00 p.m. | L 0-1 | |
| Wed., 9/28 | JV Boys Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 6:00 p.m. | L 2-5 | |
| Wed., 9/28 | FR Boys Soccer | Danbury | Home - Wilton HS-Lilly Field [Directions] | 4:30 p.m. | L 0-6 | |
| Wed., 9/28 | V Girls Cross Country | New Canaan, Stamford, Westhill | Away - Waveny Park [Directions] | 4:30 p.m. | Wilton - 26 Stamford - 31 New Canaan - 20 Wilton - 43 Westhill - 23 Wilton - 34 | |
| Wed., 9/28 | V Girls Swimming and Diving | Westhill/Stamford | Away - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Thu., 9/29 | FR Football | Greenwich | Away - Greenwich HS-Field 7 [Directions] | 4:30 p.m. | ||
| Thu., 9/29 | V Boys Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:00 p.m. | TRUMBULL 169 WILTON 166 | |
| Thu., 9/29 | JV Boys Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | Wilton - 156 Trumbull - 184 | |
| Thu., 9/29 | V Field Hockey | Norwalk | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 6:30 p.m. | W 6-0 | |
| Thu., 9/29 | JV Field Hockey | Norwalk | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 5:00 p.m. | ||
| Thu., 9/29 | FR Field Hockey | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | 5:30 p.m. | W 7-0 | |
| Thu., 9/29 | V Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 6:00 p.m. | L 2-3 | |
| Thu., 9/29 | JV Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:30 p.m. | L 1-2 | |
| Thu., 9/29 | FR Girls Volleyball | New Canaan | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:15 p.m. | L 0-3 | |
| Fri., 9/30 | V Boys Soccer | Bridgeport Central | Away - Bridgeport Central-Kennedy Stadium Turf [Directions] | 6:30 p.m. | W 3-0 | |
| Fri., 9/30 | JV Boys Soccer | Bridgeport Central | Away - Bridgeport Central HS-Kennedy Stadium [Directions] | 4:30 p.m. | W 2-1 | |
| Fri., 9/30 | V Girls Swimming and Diving | Fairfield Warde | Home - Wilton YMCA [Directions] | 3:40 p.m. | Wilton - 103 Warde - 76 | |
| Fri., 9/30 | FR Girls Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 10/1 | V Football | Brien McMahon | Home - Wilton HS-Fujitani Field - Turf [Directions] | 4:00 p.m. | W 28-11 | Homecoming |
| Sat., 10/1 | V Girls Soccer | Bridgeport Central | Home - Wilton HS-Lilly Field [Directions] | 1:30 p.m. | W 6-0 | |
| Sat., 10/1 | FR Girls Soccer | New Fairfield | Away - New Fairfield HS-Marty Morgan Field [Directions] | 10:00 a.m. | W 3-1 | |
| Sat., 10/1 | V Girls Volleyball | Brien McMahon | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 11:30 a.m. | W 3-0 | |
| Sat., 10/1 | JV Girls Volleyball | Brien McMahon | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 10:00 a.m. | L 1-2 | |
| Mon., 10/3 | V Boys Cross Country | Fairfield Warde, St. Joseph, Trumbull | Home - Allen's Meadow-XC Course [Directions] | 4:00 p.m. | Wilton 15 - Warde - 46 Wilton 15 - St. Joseph - 45 Wilton 23 - Trumbull - 33 | |
| Mon., 10/3 | JV Football | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 6:00 p.m. | ||
| Mon., 10/3 | V Boys Soccer | Ridgefield | Home - Wilton HS-Lilly Field [Directions] | 6:30 p.m. | L 2-3 | |
| Mon., 10/3 | V Girls Cross Country | Fairfield Warde, Guilford, St. Joseph, Trumbull | Home - Allen's Meadow-XC Course [Directions] | 4:00 p.m. | Wilton - 15 Warde - 46 Wilton - 15 St. Joseph - 45 Wilton - 23 Trumbull - 33 | |
| Mon., 10/3 | V Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 5:00 p.m. | W 3-1 | |
| Mon., 10/3 | JV Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 6:30 p.m. | ||
| Mon., 10/3 | FR Field Hockey | Fairfield Ludlowe | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 4:00 p.m. | W 5-0 | |
| Mon., 10/3 | JV Girls Soccer | Westhill | Away - Rippowan MS-Rippowam Turf Field [Directions] | 4:00 p.m. | W 5-0 | |
| Mon., 10/3 | V Girls Volleyball | Staples | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:45 p.m. | W 3-2 | |
| Mon., 10/3 | JV Girls Volleyball | Staples | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Mon., 10/3 | FR Girls Volleyball | Staples | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | L 0-3 | |
| Tue., 10/4 | V Girls Diving | Darien | Away - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Tue., 10/4 | V Field Hockey | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | L 1-4 | |
| Tue., 10/4 | JV Field Hockey | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Tue., 10/4 | FR Girls Volleyball | Stamford | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:15 p.m. | ||
| Thu., 10/6 | FM Football | Greenwich | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 4:30 p.m. | ||
| Thu., 10/6 | V Boys Soccer | Westhill | Home - Wilton HS-Lilly Field [Directions] | 5:30 p.m. | L 1-4 | |
| Thu., 10/6 | JV Boys Soccer | Westhill | Home - Allen's Meadow-2A [Directions] | 4:30 p.m. | ||
| Thu., 10/6 | FR Boys Soccer | Westhill | Away - Rippowan MS-Rippowam Turf Field [Directions] | 4:30 p.m. | T 2-2 | |
| Thu., 10/6 | V Field Hockey | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 4:30 p.m. | W 2-1 | |
| Thu., 10/6 | JV Field Hockey | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 6:00 p.m. | ||
| Thu., 10/6 | V Girls Swimming and Diving | Darien | Away - Darien YMCA [Directions] | 3:00 p.m. | Wilton - 74 Darfien - 106 | |
| Thu., 10/6 | V Girls Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | W 3-0 | |
| Thu., 10/6 | JV Girls Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | W 2-1 | |
| Fri., 10/7 | FR Football | Fairfield Warde | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 5:30 p.m. | ||
| Fri., 10/7 | FR Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 5:00 p.m. | L 2-6 | |
| Fri., 10/7 | V Girls Soccer | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | T 0-0 | |
| Sat., 10/8 | V Football | Tolland | Away - Tolland HS-Stadium [Directions] | 1:00 p.m. | W 49-7 | |
| Mon., 10/10 | V Boys Soccer | Trumbull | Home - Wilton HS-Lilly Field [Directions] | 5:30 p.m. | L 0-3 | |
| Mon., 10/10 | JV Boys Soccer | Trumbull | Home - Allen's Meadow-2A [Directions] | 4:30 p.m. | L 1-5 | |
| Mon., 10/10 | FR Boys Soccer | Trumbull | Away - Trumbull HS-The Pit [Directions] | 4:00 p.m. | L 1-2 | |
| Mon., 10/10 | V Field Hockey | Ridgefield | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 6:30 p.m. | T 0-0 | |
| Mon., 10/10 | JV Field Hockey | Ridgefield | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 5:00 p.m. | ||
| Mon., 10/10 | FR Field Hockey | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 5:00 p.m. | ||
| Pending changes awaiting acceptance by one or more parties involved: Date to 10/13, Time to 6:30 p.m. | ||||||
| Mon., 10/10 | V Girls Volleyball | Danbury | Away - Danbury HS-New Gym [Directions] | 4:30 p.m. | W 3-0 | |
| Mon., 10/10 | JV Girls Volleyball | Danbury | Away - Danbury HS-New Gym [Directions] | 6:00 p.m. | W 2-0 | |
| Mon., 10/10 | FR Girls Volleyball | Danbury | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:15 p.m. | L 1-3 | |
| Tue., 10/11 | V Boys Cross Country | Greenwich, Ridgefield | Away - Greenwich Point [Directions] | 4:00 p.m. | ||
| Tue., 10/11 | JV Football | Greenwich | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 4:00 p.m. | ||
| Tue., 10/11 | V Girls Cross Country | Greenwich, Ridgefield | Away - Greenwich Point [Directions] | 4:00 p.m. | ||
| Tue., 10/11 | FR Field Hockey | Danbury | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 6:15 p.m. | W 8-0 | |
| Tue., 10/11 | V Girls Soccer | Trumbull | Away - Trumbull HS-Cork Field [Directions] | 5:30 p.m. | T 1-1 | |
| Tue., 10/11 | JV Girls Soccer | Trumbull | Away - Trumbull HS-The Pit [Directions] | 4:00 p.m. | L 0-1 | |
| Tue., 10/11 | FR Girls Soccer | Trumbull | Home - Allen's Meadow-Field #1 [Directions] | 4:00 p.m. | L 1-2 | |
| Tue., 10/11 | V Girls Swimming and Diving | Ridgefield | Home - New Canaan Y -Diving Only [Directions] | 3:30 p.m. | ||
| Wed., 10/12 | V Boys Golf | Darien | Home - Rolling Hills Country Club [Directions] | 3:15 p.m. | Darien 178 Wilton 174 | |
| Wed., 10/12 | JV Boys Golf | Darien | Home - Rolling Hills Country Club [Directions] | 3:15 p.m. | ||
| Wed., 10/12 | JV Boys Soccer | Ridgefield | Home - Allen's Meadow-2A [Directions] | 4:30 p.m. | ||
| Wed., 10/12 | FR Boys Soccer | Ridgefield | Away - Ridgefield HS-RHS Lower Grass Field [Directions] | 4:30 p.m. | L 2-9 | |
| Wed., 10/12 | V Field Hockey | Brien McMahon | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 5:45 p.m. | W 8-1 | |
| Wed., 10/12 | JV Field Hockey | Brien McMahon | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 4:15 p.m. | ||
| Wed., 10/12 | V Girls Swimming and Diving | Ridgefield | Home - Wilton YMCA [Directions] | 3:40 p.m. | Wilton - 77 Ridgefield - 103 | |
| Wed., 10/12 | V Girls Volleyball | Bridgeport Central | Away - Bridgeport Central HS-The Barry McLeod Court [Directions] | 5:45 p.m. | W 3-0 | |
| Wed., 10/12 | JV Girls Volleyball | Bridgeport Central | Away - Bridgeport Central HS-The Barry McLeod Court [Directions] | 4:30 p.m. | W 2-0 | |
| Thu., 10/13 | FR Football | Staples | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 6:00 p.m. | ||
| Thu., 10/13 | V Boys Golf | Fairfield Warde | Away - Smith Richardson Golf Course [Directions] | 3:30 p.m. | Wilton 157 Warde 151 | |
| Thu., 10/13 | JV Boys Golf | Fairfield Warde | Away - Smith Richardson Golf Course [Directions] | 3:00 p.m. | Wilton - 160 Warde - 176 | |
| Thu., 10/13 | V Girls Soccer | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 4:00 p.m. | L 0-3 | |
| Thu., 10/13 | JV Girls Soccer | Ridgefield | Away - Ridgefield HS-RHS Lower Grass Field [Directions] | 4:00 p.m. | L 0-1 | |
| Thu., 10/13 | FR Girls Soccer | Ridgefield | Home - Allen's Meadow-3A [Directions] | 5:00 p.m. | T 0-0 | |
| Fri., 10/14 | V Football | Darien | Home - Wilton HS-Fujitani Field - Turf [Directions] | 7:00 p.m. | L 15-18 | |
| Fri., 10/14 | FR Boys Soccer | Fairfield Ludlowe | Home - Allen's Meadow-3A [Directions] | 4:30 p.m. | L 1-3 | |
| Fri., 10/14 | V Girls Volleyball | Westhill | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:30 p.m. | L 1-3 | |
| Fri., 10/14 | JV Girls Volleyball | Westhill | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:15 p.m. | W 2-0 | |
| Fri., 10/14 | FR Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:30 p.m. | L 0-3 | |
| Sat., 10/15 | JV Football | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 10:00 a.m. | ||
| Sat., 10/15 | V Boys Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 10:00 a.m. | L 1-3 | |
| Sat., 10/15 | JV Boys Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 10:00 a.m. | L 1-6 | |
| Sat., 10/15 | V Girls Soccer | Fairfield Ludlowe | Home - Wilton HS-Lilly Field [Directions] | 12:00 p.m. | L 0-2 | |
| Sat., 10/15 | JV Girls Soccer | Fairfield Ludlowe | Home - Wilton HS-Lilly Field [Directions] | 9:00 a.m. | L 0-1 | |
| Sat., 10/15 | FR Girls Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 12:00 p.m. | L 1-5 | |
| Mon., 10/17 | V Boys Soccer | Greenwich | Home - Wilton HS-Lilly Field [Directions] | 5:30 p.m. | L 2-3 | |
| Mon., 10/17 | JV Boys Soccer | Greenwich | Home - Allen's Meadow-2A [Directions] | 4:30 p.m. | ||
| Mon., 10/17 | FR Boys Soccer | Greenwich | Away - Greenwich HS-Cos Cob Park, Benvenuto Field [Directions] | 4:45 p.m. | L 2-4 | |
| Mon., 10/17 | V Girls Volleyball | Trumbull | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:45 p.m. | W 3-1 | |
| Mon., 10/17 | JV Girls Volleyball | Trumbull | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | L 0-2 | |
| Mon., 10/17 | FR Girls Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 5:00 p.m. | L 0-3 | |
| Tue., 10/18 | V Boys Golf | Ridgefield | Home - Rolling Hills Country Club [Directions] | 3:15 p.m. | Wilton 165 Ridgefield 173 | |
| Tue., 10/18 | JV Boys Golf | Ridgefield | Home - Rolling Hills Country Club [Directions] | 3:15 p.m. | ||
| Tue., 10/18 | FR Field Hockey | New Canaan | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 5:30 p.m. | W 3-2 | |
| Tue., 10/18 | V Girls Soccer | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | T 0-0 | |
| Tue., 10/18 | JV Girls Soccer | Greenwich | Away - Cos Cob Park, Benvenuto Field-Benvenuto Field [Directions] | 4:30 p.m. | ||
| Tue., 10/18 | FR Girls Soccer | Greenwich | Home - Allen's Meadow-3A [Directions] | 4:00 p.m. | L 3-7 | |
| Wed., 10/19 | FR Football | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | ||
| Wed., 10/19 | V Field Hockey | Westhill | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 7:00 p.m. | W 9-0 | |
| Wed., 10/19 | JV Field Hockey | Westhill | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 5:30 p.m. | ||
| Wed., 10/19 | V Girls Volleyball | Ridgefield | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:00 p.m. | W 3-0 | |
| Wed., 10/19 | JV Girls Volleyball | Ridgefield | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | W 2-1 | |
| Wed., 10/19 | FR Girls Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:30 p.m. | ||
| Thu., 10/20 | FR Boys Soccer | Darien | Home - Allen's Meadow-Field #1 [Directions] | 4:30 p.m. | ||
| Thu., 10/20 | V Field Hockey | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 5:30 p.m. | W 8-0 | |
| Thu., 10/20 | JV Field Hockey | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:30 p.m. | ||
| Thu., 10/20 | FR Field Hockey | Trumbull | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 6:00 p.m. | W 7-3 | |
| Thu., 10/20 | V Girls Soccer | Darien | Home - Wilton HS-Lilly Field [Directions] | 7:00 p.m. | L 0-2 | |
| Thu., 10/20 | JV Girls Soccer | Darien | Home - Allen's Meadow-2A [Directions] | 4:30 p.m. | L 0-1 | |
| Fri., 10/21 | V Football | New Canaan | Home - Wilton HS-Fujitani Field - Turf [Directions] | 7:00 p.m. | L 0-45 | |
| Fri., 10/21 | V Boys Soccer | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 7:00 p.m. | L 3-6 | |
| Fri., 10/21 | JV Boys Soccer | Darien | Away - Darien HS-DHS Center Oval - Turf [Directions] | 4:00 p.m. | ||
| Fri., 10/21 | FR Girls Soccer | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | L 0-2 | |
| Fri., 10/21 | V Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:30 p.m. | W 3-1 | |
| Fri., 10/21 | JV Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 6:00 p.m. | W 2-0 | |
| Fri., 10/21 | FR Girls Volleyball | Fairfield Ludlowe | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:15 p.m. | L 0-3 | |
| Sat., 10/22 | JV Football | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 10:00 a.m. | ||
| Sat., 10/22 | V Field Hockey | Glastonbury | Away - Glastonbury HS-Turf Field [Directions] | 3:30 p.m. | W 2-0 | |
| Sat., 10/22 | JV Field Hockey | Glastonbury | Away - Glastonbury HS-Turf Field [Directions] | 2:00 p.m. | ||
| Mon., 10/24 | V Boys Soccer | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 4:30 p.m. | L 2-3 | |
| Mon., 10/24 | JV Boys Soccer | St. Joseph | Away - St. Joseph HS-Lower Grass Field [Directions] | 4:30 p.m. | ||
| Mon., 10/24 | V Girls Swimming and Diving | Trumbull | Home - Wilton YMCA [Directions] | 3:40 p.m. | Wilton - 104 Trumbull - 79 | |
| Mon., 10/24 | V Girls Volleyball | Greenwich | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:45 p.m. | W 3-2 | |
| Mon., 10/24 | JV Girls Volleyball | Greenwich | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | L 1-2 | |
| Mon., 10/24 | FR Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | L 0-3 | |
| Tue., 10/25 | V Field Hockey | Branford | Away - Branford HS-Athletic Turf Field [Directions] | 7:00 p.m. | W 3-0 | |
| Tue., 10/25 | JV Field Hockey | Branford | Away - Branford HS-Athletic Turf Field [Directions] | 5:15 p.m. | ||
| Tue., 10/25 | V Girls Soccer | St. Joseph | Home - Wilton HS-Lilly Field [Directions] | 7:00 p.m. | L 0-4 | |
| Tue., 10/25 | JV Girls Soccer | St. Joseph | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | T 0-0 | |
| Tue., 10/25 | FR Girls Volleyball | Darien | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Wed., 10/26 | V Girls Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Wed., 10/26 | JV Girls Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:30 p.m. | ||
| Thu., 10/27 | FR Football | New Canaan | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 6:00 p.m. | ||
| Thu., 10/27 | JV Girls Soccer | Brien McMahon | Home - Allen's Meadow-2A [Directions] | 4:00 p.m. | ||
| Fri., 10/28 | V Football | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 7:00 p.m. | L 7-31 | |
| Fri., 10/28 | V Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 5:45 p.m. | L 1-3 | |
| Fri., 10/28 | JV Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:30 p.m. | ||
| Fri., 10/28 | FR Girls Volleyball | St. Joseph | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Sat., 10/29 | JV Football | Ridgefield | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 10:00 a.m. | ||
| Thu., 11/3 | FR Football | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 4:00 p.m. | ||
| Fri., 11/4 | V Football | Fairfield Warde | Home - Wilton HS-Fujitani Field - Turf [Directions] | 7:00 p.m. | W 28-14 | |
| Sat., 11/5 | JV Football | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 10:30 a.m. | ||
| Tue., 11/8 | V Girls Volleyball | Staples | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:00 p.m. | ||
| Thu., 11/10 | V Football | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 6:30 p.m. | W 28-0 | |
| Thu., 11/10 | FR Football | Ridgefield | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 4:00 p.m. | ||
| Fri., 11/11 | V Field Hockey | Ridgefield | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 4:00 p.m. | ||
| Sat., 11/12 | JV Football | Norwalk | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 10:00 a.m. | ||
| Sat., 11/12 | V Girls Soccer | Staples | Away - Staples HS-Wakeman Field B (turf) [Directions] | 2:00 p.m. | ||
| Thu., 11/17 | FR Football | Brien McMahon | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 4:30 p.m. | ||
| Sat., 11/19 | JV Football | Southington | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 10:30 a.m. | ||
| Tue., 11/29 | V Football | SMSA Coop | Away - Weaver HS-Turf Field [Directions] | 6:30 p.m. | ||
| Sun., 12/4 | V Football | North Haven | Away - North Haven MS-East Turf Field [Directions] | 12:30 p.m. | ||
| Tue., 12/6 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Conners - Stamford-Ice Rink [Directions] | 7:30 p.m. | L 1-2 | |
| Thu., 12/8 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice-New [Directions] | 4:40 p.m. | W 6-1 | |
| Tue., 12/13 | V Wrestling | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 6:30 p.m. | ||
| Wed., 12/14 | V Boys Ice Hockey | Staples | Away - Milford Ice Pavillion-Ice Rink [Directions] | 6:00 p.m. | L 3-4(OT) | |
| Wed., 12/14 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 6:15 p.m. | W 4-1 | |
| Thu., 12/15 | V Boys Swimming and Diving | Darien | Away - Darien YMCA [Directions] | 3:00 p.m. | Wilton 101 Darien 69 | |
| Thu., 12/15 | V Girls Basketball | Immaculate | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 7:00 p.m. | L 44-51 | |
| Thu., 12/15 | JV Girls Basketball | Immaculate | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:15 p.m. | W 56-28 | |
| Fri., 12/16 | V Boys Basketball | Newtown | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 7:00 p.m. | W 82-60 | |
| Fri., 12/16 | JV Boys Basketball | Newtown | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:15 p.m. | W 56-48 | |
| Fri., 12/16 | FR Boys Basketball | Newtown | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | W 71-64 | |
| Fri., 12/16 | V Boys Diving | Darien | Away - New Canaan Y -Diving Only [Directions] | 3:30 p.m. | ||
| Fri., 12/16 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 4:00 p.m. | L 1-2 | |
| Sat., 12/17 | V Boys Basketball | Hamden | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 7:00 p.m. | W 62-52 | |
| Sat., 12/17 | JV Boys Basketball | Hamden | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:30 p.m. | L 56-60 | |
| Sat., 12/17 | FR Boys Basketball | Hamden | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:15 p.m. | L 60-43 | |
| Sat., 12/17 | V Boys Indoor Track | Danbury, New Canaan, Norwalk | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:00 a.m. | ||
| Sat., 12/17 | V Boys Indoor Track | Brien McMahon, Darien, Fairfield Warde, Ridgefield | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 12:00 p.m. | ||
| Sat., 12/17 | V Girls Indoor Track | Danbury, New Canaan, Norwalk | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:00 a.m. | ||
| Sat., 12/17 | V Girls Indoor Track | Brien McMahon, Darien, Fairfield Warde, Ridgefield | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 12:00 p.m. | ||
| Mon., 12/19 | V Girls Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | 8:20 p.m. | L 3-10 | |
| Tue., 12/20 | V Boys Basketball | Bassick | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 7:15 p.m. | W 72-54 | |
| Tue., 12/20 | JV Boys Basketball | Bassick | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:45 p.m. | W 63-61 | |
| Tue., 12/20 | FR Boys Basketball | Bassick | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | W 74-24 | |
| Wed., 12/21 | V Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena-Patriot Rink [Directions] | 7:30 p.m. | L 2-5 | |
| Wed., 12/21 | V Wrestling | Fairfield Warde | Away - Fairfield Warde HS-Small Gym [Directions] | 6:30 p.m. | ||
| Tue., 12/27 | V Wrestling | Trumbull, Brien McMahon, St. Joseph | Away - Trumbull HS-THS Main Gym [Directions] | 9:00 a.m. | ||
| Tue., 12/27 | V Girls Basketball | Wethersfield | Away - Pomperaug HS-Main Gym [Directions] | 3:00 p.m. | L 22-50 | |
| Tue., 12/27 | JV Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | 6:00 p.m. | ||
| Tue., 12/27 | JV Girls Ice Hockey | West Haven/SHA | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | Canceled | Cancelled | |
| Wed., 12/28 | V Boys Basketball | Amity | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 3:00 p.m. | W 60-49 | |
| Wed., 12/28 | V Girls Ice Hockey | Hall/Conard | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 3:30 p.m. | W 5-4(OT) | |
| Thu., 12/29 | V Girls Basketball | Naugatuck | Home - Pomperaug HS-Main Gym [Directions] | 3:00 p.m. | W 39-32 | |
| Fri., 12/30 | V Boys Basketball | Daniel Hand | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 3:00 p.m. | W 58-45 | |
| Fri., 12/30 | V Boys Ice Hockey | Newtown/New Fairfield | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 6:00 p.m. | L 4-5 | |
| Fri., 12/30 | V Girls Basketball | Fairfield Ludlowe | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 10:00 a.m. | L 21-59 | |
| Fri., 12/30 | V Girls Ice Hockey | Woodstock Academy Coop | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 4:00 p.m. | L 4-5 | |
| Tue., 1/3 | V Girls Basketball | Danbury | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:00 p.m. | L 31-57 | |
| Tue., 1/3 | JV Girls Basketball | Danbury | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | W 34-26 | |
| Wed., 1/4 | V Boys Ice Hockey | Trumbull | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | 8:00 p.m. | L 1-6 | |
| Wed., 1/4 | V Wrestling | Stamford | Home - Wilton HS-Nicholas Zeoli Fieldhouse [Directions] | 6:00 p.m. | ||
| Wed., 1/4 | V Girls Ice Hockey | Masuk Coop | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 5:45 p.m. | W 8-4 | |
| Fri., 1/6 | V Boys Basketball | Fairfield Warde | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 7:00 p.m. | L 65-73 | |
| Fri., 1/6 | JV Boys Basketball | Fairfield Warde | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:30 p.m. | L 57-67 | |
| Fri., 1/6 | FR Boys Basketball | Fairfield Warde | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | L 41-60 | |
| Fri., 1/6 | V Boys Swimming and Diving | Trumbull | Away - Univ of Bridgeport Pool [Directions] | 4:00 p.m. | Wilton 116 Trumbull 52 | |
| Fri., 1/6 | V Girls Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 6:00 p.m. | L 29-48 | |
| Fri., 1/6 | JV Girls Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:30 p.m. | L 37-39 | |
| Sat., 1/7 | V Boys Ice Hockey | Bethel/Brookfield/Danbury/Immaculate | Away - Danbury Ice Arena-Patriot Rink [Directions] | 1:30 p.m. | L 3-6 | |
| Sat., 1/7 | V Boys Indoor Track | Darien, New Canaan, Ridgefield | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:00 a.m. | ||
| Sat., 1/7 | V Boys Indoor Track | Danbury, Fairfield Ludlowe, Fairfield Warde, Norwalk | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 12:00 p.m. | ||
| Sat., 1/7 | V Wrestling | Warde Invitational | Away - Fairfield Warde HS-Large Gym | 9:00 a.m. | ||
| Sat., 1/7 | V Girls Indoor Track | Darien, New Canaan, Ridgefield | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:00 a.m. | ||
| Sat., 1/7 | V Girls Indoor Track | Danbury, Fairfield Ludlowe, Fairfield Warde, Norwalk | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 12:00 p.m. | ||
| Mon., 1/9 | V Boys Ice Hockey | Milford Coop | Away - Milford Ice Pavillion-Ice Rink [Directions] | 4:00 p.m. | L 0-4 | |
| Mon., 1/9 | JV Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 4:30 p.m. | ||
| Tue., 1/10 | V Boys Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 7:00 p.m. | W 70-58 | |
| Tue., 1/10 | JV Boys Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 5:30 p.m. | W 63-51 | |
| Tue., 1/10 | FR Boys Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:00 p.m. | W 38-25 | |
| Tue., 1/10 | V Girls Basketball | Norwalk | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:00 p.m. | L 22-40 | |
| Tue., 1/10 | JV Girls Basketball | Norwalk | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | W 25-22 | |
| Tue., 1/10 | V Girls Gymnastics | Darien, New Canaan | Home - Wilton HS-Aux Gym [Directions] | 4:30 p.m. | 136.95-Wilton 132.85 - Darien 97.25 - New Canaan | |
| Wed., 1/11 | V Boys Ice Hockey | Westhill/Stamford | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:30 p.m. | L 1-7 | |
| Wed., 1/11 | V Wrestling | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 7:00 p.m. | ||
| Wed., 1/11 | JV Girls Basketball | Fairfield Ludlowe | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:15 p.m. | W 32-29 | |
| Wed., 1/11 | V Girls Ice Hockey | Darien | Away - Darien Ice House-Ice Rink [Directions] | 8:50 p.m. | L 3-6 | |
| Thu., 1/12 | V Boys Swimming and Diving | Danbury | Home - Wilton YMCA [Directions] | 3:40 p.m. | Wilton - 67 Danbury 0 40 | |
| Thu., 1/12 | V Wrestling | Weston | Home - Wilton HS-Nicholas Zeoli Fieldhouse [Directions] | 6:00 p.m. | ||
| Thu., 1/12 | V Girls Gymnastics | Greenwich | Away - Greenwich YWCA [Directions] | 6:30 p.m. | 139.7-Wilton 128.85 - Greenwich | |
| Fri., 1/13 | V Boys Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 7:00 p.m. | L 56-59(2OT) | |
| Fri., 1/13 | JV Boys Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | W 68-39 | |
| Fri., 1/13 | FR Boys Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | W 44-43 | |
| Fri., 1/13 | V Girls Basketball | New Canaan | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:00 p.m. | W 41-39(OT) | |
| Fri., 1/13 | JV Girls Basketball | New Canaan | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | W 30-12 | |
| Fri., 1/13 | V Girls Ice Hockey | Masuk Coop | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 4:00 p.m. | W 12-3 | |
| Sat., 1/14 | V Boys Ice Hockey | Masuk | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 8:45 p.m. | L 1-6 | |
| Sat., 1/14 | V Boys Indoor Track | Brien McMahon, New Canaan, Ridgefield | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:00 a.m. | ||
| Sat., 1/14 | V Boys Indoor Track | Fairfield Warde, Norwalk, Trumbull, Westhill | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 12:00 p.m. | ||
| Sat., 1/14 | V Girls Basketball | Southington | Away - Southington HS-Gym West [Directions] | 1:30 p.m. | L 23-53 | |
| Sat., 1/14 | JV Girls Basketball | Southington | Away - Southington HS-Gym West [Directions] | 12:00 p.m. | W 34-20 | |
| Sat., 1/14 | V Girls Indoor Track | Brien McMahon, New Canaan, Ridgefield | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:00 a.m. | ||
| Sat., 1/14 | V Girls Indoor Track | Fairfield Warde, Norwalk, Trumbull, Westhill | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 12:00 p.m. | ||
| Mon., 1/16 | V Girls Ice Hockey | Greenwich | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 3:00 p.m. | W 5-2 | |
| Tue., 1/17 | V Boys Basketball | Brien McMahon | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 7:00 p.m. | W 70-59 | |
| Tue., 1/17 | JV Boys Basketball | Brien McMahon | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:15 p.m. | W 75-46 | |
| Tue., 1/17 | FR Boys Basketball | Brien McMahon | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | W 62-47 | |
| Tue., 1/17 | V Wrestling | Westhill | Away - Westhill HS-New Gym [Directions] | 6:00 p.m. | ||
| Tue., 1/17 | V Girls Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 5:45 p.m. | W 45-31 | |
| Tue., 1/17 | JV Girls Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:15 p.m. | W 24-19 | |
| Wed., 1/18 | V Boys Ice Hockey | Fox Lane (NY) | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:30 p.m. | W 7-3 | |
| Fri., 1/20 | V Boys Basketball | Trumbull | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 7:00 p.m. | W 70-67 | |
| Fri., 1/20 | JV Boys Basketball | Trumbull | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:30 p.m. | ||
| Fri., 1/20 | FR Boys Basketball | Trumbull | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | W 54-38 | |
| Fri., 1/20 | V Boys Ice Hockey | Brien McMahon/Norwalk | Away - Sono Ice House-Main Rink [Directions] | 7:10 p.m. | W 4-3 | |
| Fri., 1/20 | V Girls Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 7:00 p.m. | L 27-32 | |
| Fri., 1/20 | JV Girls Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | L 23-31 | |
| Fri., 1/20 | V Girls Ice Hockey | Stamford/Westhill/Staples | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 4:00 p.m. | T 2-2 | |
| Sat., 1/21 | V Boys Indoor Track | Brien McMahon, New Canaan, St. Joseph | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:00 a.m. | ||
| Sat., 1/21 | V Boys Indoor Track | Bridgeport Central, Danbury, Fairfield Ludlowe, Greenwich | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 12:00 p.m. | ||
| Sat., 1/21 | V Wrestling | New Milford Wrestling Tournament | Away - New Milford HS-Small Gym - NMHS | 8:00 a.m. | ||
| Sat., 1/21 | V Girls Indoor Track | Brien McMahon, New Canaan, St. Joseph | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:00 a.m. | ||
| Sat., 1/21 | V Girls Indoor Track | Bridgeport Central, Danbury, Fairfield Ludlowe, Greenwich | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 12:00 p.m. | ||
| Mon., 1/23 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Home - Wilton YMCA [Directions] | 3:40 p.m. | Wilton - 90 FFLD - 80 | |
| Mon., 1/23 | V Girls Basketball | Harding | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:00 p.m. | W 56-21 | |
| Mon., 1/23 | JV Girls Basketball | Harding | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | W 44-5 | |
| Mon., 1/23 | V Girls Gymnastics | Westhill, Stamford | Away - Westhill HS-New Gym [Directions] | 6:00 p.m. | 127.55 - Wilton 113.05 Stamford 68.65 - Westhill | |
| Tue., 1/24 | V Boys Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 7:00 p.m. | W 51-48 | |
| Tue., 1/24 | JV Boys Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/24 | FR Boys Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | W 59-46 | |
| Tue., 1/24 | V Girls Basketball | Stamford | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:00 p.m. | L 39-50 | |
| Tue., 1/24 | JV Girls Basketball | Stamford | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | W 33-26 | |
| Wed., 1/25 | V Boys Ice Hockey | Staples | Away - Milford Ice Pavillion-Ice Rink [Directions] | 6:00 p.m. | W 3-2 | |
| Thu., 1/26 | V Boys Diving | Fairfield Ludlowe, TBA | Home - New Canaan Y -Diving Only [Directions] | 3:30 p.m. | ||
| Thu., 1/26 | V Wrestling | Ridgefield | Home - Wilton HS-Nicholas Zeoli Fieldhouse [Directions] | 6:00 p.m. | ||
| Fri., 1/27 | V Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 7:00 p.m. | W 70-61 | |
| Fri., 1/27 | JV Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/27 | FR Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:00 p.m. | W 47-42 | |
| Fri., 1/27 | V Girls Basketball | St. Joseph | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:00 p.m. | L 39-47 | |
| Fri., 1/27 | JV Girls Basketball | St. Joseph | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | L 40-50 | |
| Sat., 1/28 | V Boys Ice Hockey | Fox Lane (NY) | Away - Fox Lane HS-Brewster Ice Arena | 8:30 p.m. | W 7-4 | |
| Sat., 1/28 | V Boys Indoor Track | Brien McMahon, New Canaan, St. Joseph | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:00 a.m. | ||
| Sat., 1/28 | V Wrestling | Brookfield Wrestling Tournament | Away - Brookfield HS-BHS Small Gym | 9:30 a.m. | ||
| Sat., 1/28 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:00 p.m. | W 6-4 | |
| Sat., 1/28 | V Girls Indoor Track | Brien McMahon, New Canaan, St. Joseph | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:00 a.m. | ||
| Mon., 1/30 | V Boys Swimming and Diving | Westhill/Stamford | Home - Wilton YMCA [Directions] | 3:40 p.m. | Wilton -92 Westhill - 84 | |
| Tue., 1/31 | V Boys Basketball | Staples | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 7:00 p.m. | W 69-68 OT | |
| Tue., 1/31 | JV Boys Basketball | Staples | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:15 p.m. | ||
| Tue., 1/31 | FR Boys Basketball | Staples | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | L 49-60 | |
| Tue., 1/31 | V Girls Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 6:00 p.m. | L 20-56 | |
| Tue., 1/31 | JV Girls Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:30 p.m. | L 29-35 | |
| Tue., 1/31 | V Girls Ice Hockey | Darien | Away - Darien Ice House-Ice Rink [Directions] | 8:20 p.m. | L 0-9 | |
| Wed., 2/1 | V Boys Ice Hockey | Trumbull | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:30 p.m. | L 3-6 | |
| Wed., 2/1 | V Boys Swimming and Diving | New Canaan | Home - Wilton YMCA [Directions] | 3:40 p.m. | Wilton - 80 New Canaan - 100 | |
| Wed., 2/1 | V Wrestling | New Canaan | Home - Wilton HS-Nicholas Zeoli Fieldhouse [Directions] | 6:00 p.m. | ||
| Wed., 2/1 | V Girls Ice Hockey | Daniel Hand Coop | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 6:30 p.m. | W 6-0 | |
| Thu., 2/2 | JV Boys Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 2/2 | FR Boys Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | W 49-44 | |
| Thu., 2/2 | V Boys Swimming and Diving | Ridgefield | Home - Wilton YMCA [Directions] | 3:40 p.m. | Wilton - 80 Ridgefield - 103 | |
| Thu., 2/2 | V Girls Basketball | Darien | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:00 p.m. | W 35-29 | |
| Thu., 2/2 | JV Girls Basketball | Darien | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | W 30-23 | |
| Thu., 2/2 | V Girls Gymnastics | Staples, Norwalk | Away - Staples HS-Westport YMCA [Directions] | 7:00 p.m. | 136.55 - Wilton 138.35 - Staples | |
| Sat., 2/4 | V Boys Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 3:00 p.m. | L 39-70 | |
| Sat., 2/4 | V Boys Ice Hockey | SCW Knights | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 6:15 p.m. | L 3-8 | |
| Sat., 2/4 | V Wrestling | Canton, Granby Memorial, Griswold/Wheeler, Morgan | Away - Canton HS-Gym [Directions] | 10:00 a.m. | ||
| Sat., 2/4 | V Girls Gymnastics | St. Joseph, Trumbull | Home - Wilton HS-Aux Gym [Directions] | 4:30 p.m. | 135.05 - Wilton 128.65 - Trumbull 124.6 - St. Joe's | |
| Sat., 2/4 | V Girls Ice Hockey | Hall/Conard | Away - Veterans Memorial Ice Rink - West Hartford-Ice Rink [Directions] | 1:30 p.m. | L 6-7 OT | |
| Mon., 2/6 | V Wrestling | Darien | Home - Wilton HS-Nicholas Zeoli Fieldhouse [Directions] | 6:00 p.m. | ||
| Mon., 2/6 | V Girls Gymnastics | Fairfield Ludlowe, Foran | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:30 p.m. | 133.15-Wilton 141.00 - Warde 125.35 - Foran 131.45 - Ludlowe | |
| Mon., 2/6 | V Girls Gymnastics | Fairfield Warde | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:30 p.m. | 134.25 | |
| Mon., 2/6 | JV Girls Ice Hockey | Masuk Coop | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 4:00 p.m. | ||
| Tue., 2/7 | V Boys Basketball | Westhill | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 7:00 p.m. | W 76-51 | |
| Tue., 2/7 | JV Boys Basketball | Westhill | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:15 p.m. | ||
| Tue., 2/7 | FR Boys Basketball | Westhill | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | W 50-30 | |
| Tue., 2/7 | V Girls Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 6:00 p.m. | W 45-21 | |
| Tue., 2/7 | JV Girls Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:30 p.m. | W 45-14 | |
| Wed., 2/8 | V Boys Ice Hockey | Milford Coop | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:30 p.m. | T 3-3 | |
| Wed., 2/8 | V Boys Swimming and Diving | Greenwich | Away - Greenwich HS-Pool [Directions] | 4:15 p.m. | Wilton - 43 Greenwich - 143 | |
| Wed., 2/8 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 4:30 p.m. | W 9-2 | |
| Thu., 2/9 | JV Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice-Stadium [Directions] | 3:30 p.m. | ||
| Fri., 2/10 | V Boys Basketball | Ridgefield | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:30 p.m. | L 55-69 | |
| Fri., 2/10 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Away - Norwalk HS-Pat Spinola Natatorium [Directions] | 6:00 p.m. | Wilton - 85 Norwalk - 98 | |
| Fri., 2/10 | V Wrestling | New Canaan, Bridgeport Central, Brien McMahon, Danbury, Darien, FCIAC, Fairfield Ludlowe, Fairfield Warde, Greenwich, Norwalk, Ridgefield, St. Joseph, Stamford, Staples, Trumbull, Westhill | Away - New Canaan HS-Main Gym | 4:00 p.m. | ||
| Fri., 2/10 | V Girls Basketball | Ridgefield | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | L 36-44 | |
| Fri., 2/10 | V Girls Ice Hockey | Mercy/NW Catholic/East Hampton | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 4:00 p.m. | L 1-5 | |
| Sat., 2/11 | JV Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 1:00 p.m. | ||
| Sat., 2/11 | FR Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 11:30 a.m. | W 45-43 | |
| Sat., 2/11 | V Boys Ice Hockey | Westhill/Stamford | Away - Terry Conners - Stamford-Ice Rink [Directions] | 7:00 p.m. | L 0-7 | |
| Sat., 2/11 | JV Girls Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 10:00 a.m. | L 25-28 | |
| Mon., 2/13 | V Boys Basketball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | 7:00 p.m. | L 54-59 | |
| Mon., 2/13 | JV Boys Basketball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | 5:15 p.m. | ||
| Mon., 2/13 | FR Boys Basketball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | 4:00 p.m. | W 55-45 | |
| Mon., 2/13 | V Boys Swimming and Diving | Staples | Away - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | Wilton - 80 Staples - 100 | |
| Mon., 2/13 | V Girls Basketball | Bridgeport Central | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:00 p.m. | W 49-17 | |
| Mon., 2/13 | JV Girls Basketball | Bridgeport Central | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | W 44-28 | |
| Wed., 2/15 | V Boys Basketball | Greenwich | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 7:00 p.m. | W 62-52 | |
| Wed., 2/15 | JV Boys Basketball | Greenwich | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:15 p.m. | ||
| Wed., 2/15 | FR Boys Basketball | Greenwich | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | W 56-32 | |
| Wed., 2/15 | V Boys Ice Hockey | Brien McMahon/Norwalk | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:30 p.m. | L 4-6 | |
| Wed., 2/15 | V Girls Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 7:00 p.m. | W 52-49 | |
| Wed., 2/15 | JV Girls Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | L 26-28 | |
| Wed., 2/15 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 4:00 p.m. | W 3-0 | |
| Thu., 2/16 | V Girls Gymnastics | New Milford, Brookfield | Away - New Milford HS-Small Gym - NMHS [Directions] | 5:00 p.m. | Wilton - 138.7 New Milford - 135.95 Brookfield - 122.45 | |
| Fri., 2/17 | V Boys Ice Hockey | Staples | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 4:00 p.m. | L 0-5 | |
| Sat., 2/18 | V Girls Ice Hockey | Daniel Hand Coop | Away - Northford-Red [Directions] | 2:30 p.m. | W 7-4 | |
| Mon., 2/20 | V Boys Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 7:00 p.m. | W 67-46 | |
| Mon., 2/20 | JV Boys Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/20 | FR Boys Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:00 p.m. | W 62-57 | |
| Wed., 2/22 | V Boys Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 7:00 p.m. | L 51-71 | |
| Wed., 2/22 | JV Boys Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/22 | FR Boys Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 4:00 p.m. | W 5146 | |
| Wed., 2/22 | V Boys Ice Hockey | Bethel/Brookfield/Danbury/Immaculate | Away - Danbury Ice Arena-Patriot Rink [Directions] | 5:30 p.m. | L 4-7 | |
| Sat., 2/25 | V Boys Ice Hockey | Shepaug Valley Ice Hockey | Home - Ridgefield - Winter Garden-Ice Rink [Directions] | 6:20 p.m. | L 2-4 | |
| Mon., 2/27 | V Girls Ice Hockey | West Haven/SHA | Away - West Haven HS-Bennett Rink [Directions] | 4:00 p.m. | L 3-5 | |
| Tue., 2/28 | V Boys Swimming and Diving | FCIAC Swim Trial Boys | Away - Greenwich HS-Pool | 5:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 3/1 | ||||||
| Wed., 3/1 | V Girls Basketball | New Britain | Away - New Britain HS-Gym [Directions] | 6:30 p.m. | ||
| Fri., 3/3 | V Boys Swimming and Diving | Greenwich, Danbury, Darien, Farfield Ludlowe/Warde, Fairfield Warde, TBA, New Canaan, Norwalk/Brien McMahon, Ridgefield, St. Joseph, Staples, Trumbull, Westhill/Stamford | Away - Greenwich HS-Pool | 6:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 5:30 p.m. | ||||||
| Sat., 4/1 | V Boys Lacrosse | Somers (NY) | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 6:00 p.m. | W 17-5 | |
| Sat., 4/1 | JV Boys Lacrosse | Somers (NY) | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 4:00 p.m. | L 8-10 | |
| Sat., 4/1 | V Girls Lacrosse | Shenendehowa (NY) | Away - Shenendehowa HS-Shen East Turf Stadium | 3:00 p.m. | W 17-2 | |
| Mon., 4/3 | V Baseball | O'Brien Tech | Away - Emmett O' Brien Reg Voc Tech School-O'Brien Tech Athletic Complex [Directions] | 4:30 p.m. | L 3-4 | |
| Mon., 4/3 | V Softball | Foran | Away - Foran HS -Danielle Kemp Memorial Field [Directions] | 4:30 p.m. | L 3-5 | |
| Tue., 4/4 | V Boys Lacrosse | John Jay (NY) | Away - John Jay HS (Crossriver) | 6:00 p.m. | W 11-6 | |
| Tue., 4/4 | FR Boys Lacrosse | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | 4:30 p.m. | ||
| Tue., 4/4 | V Boys Outdoor Track | Fairfield Warde | Home - Wilton HS-Track [Directions] | 4:00 p.m. | ||
| Tue., 4/4 | V Girls Golf | Darien | Home - Silvermine Golf Club [Directions] | 3:15 p.m. | ||
| Tue., 4/4 | V Girls Lacrosse | Canandaigua Academy (NY) | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | W 13-6 | |
| Tue., 4/4 | FR Girls Lacrosse | Ridgefield | Away - Scotts Ridge MS-SRMS Turf [Directions] | 4:30 p.m. | ||
| Tue., 4/4 | V Girls Outdoor Track | Fairfield Warde | Home - Wilton HS-Track [Directions] | 4:00 p.m. | ||
| Tue., 4/4 | V Softball | New Milford | Home - Wilton HS-Varsity Softball Field [Directions] | 4:15 p.m. | L 3-6 | |
| Wed., 4/5 | JV Girls Lacrosse | New Canaan | Home - Wilton HS-Lilly Field [Directions] | 4:30 p.m. | T 10-10 | |
| Wed., 4/5 | FR Girls Lacrosse | Staples | Home - Allen's Meadow-Lacrosse Field #5 [Directions] | 4:00 p.m. | W 16-2 | |
| Thu., 4/6 | JV Boys Lacrosse | St. Anthonys (NY) | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 4:30 p.m. | ||
| Thu., 4/6 | V Girls Golf | Fairfield Ludlowe | Home - Silvermine Golf Club [Directions] | 3:30 p.m. | ||
| Thu., 4/6 | V Softball | New Fairfield | Away - New Fairfield HS-Softball Field [Directions] | 4:30 p.m. | L 9-11 | |
| Sat., 4/8 | V Boys Lacrosse | Fairfield Prep | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 7:00 p.m. | L 5-14 | |
| Sat., 4/8 | JV Boys Lacrosse | Fairfield Prep | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 4:30 p.m. | ||
| Sat., 4/8 | FR Boys Lacrosse | Fairfield Prep | Away - Fairfield University - Barlow Field-Barlow Field Fairfield University [Directions] | 9:30 a.m. | ||
| Sat., 4/8 | V Girls Lacrosse | Bronxville (NY) | Home - Wilton HS-Lilly Field [Directions] | 10:00 a.m. | W 14-6 | |
| Mon., 4/10 | V Baseball | Wilbur Cross | Home - Wilton HS-Varsity Baseball Field [Directions] | 6:00 p.m. | W 11-1 | |
| Mon., 4/10 | JV Baseball | Wilbur Cross | Home - Wilton HS-JV Baseball Field [Directions] | 3:45 p.m. | ||
| Mon., 4/10 | FR Boys Lacrosse | Greenwich | Away - Greenwich HS-Field 7 [Directions] | 11:00 a.m. | ||
| Mon., 4/10 | V Boys Tennis | Fairfield Warde | Home - Wilton HS-Tennis Courts [Directions] | 1:00 p.m. | W 5-2 [Detailed Results] | |
| Mon., 4/10 | V Softball | Darien | Home - Wilton HS-Varsity Softball Field [Directions] | 4:00 p.m. | W 3-2 (9) | |
| Mon., 4/10 | V Girls Tennis | Fairfield Warde | Away - Fairfield Warde HS-Blake Courts [Directions] | 12:00 p.m. | W 5-2 [Detailed Results] | |
| Mon., 4/10 | JV Girls Tennis | Fairfield Warde | Away - Fairfield Warde HS-Knapps Courts [Directions] | 12:00 p.m. | ||
| Tue., 4/11 | V Baseball | Guilford | Home - Wilton HS-Varsity Baseball Field [Directions] | 2:00 p.m. | L 4-1 | |
| Tue., 4/11 | V Boys Lacrosse | Brien McMahon | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 7:00 p.m. | W 16-2 | |
| Tue., 4/11 | JV Boys Lacrosse | Brien McMahon | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 4:30 p.m. | ||
| Tue., 4/11 | V Boys Tennis | Norwalk | Away - Norwalk HS-Tennis Courts [Directions] | 1:00 p.m. | W 7-0 [Detailed Results] | |
| Tue., 4/11 | V Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 5:00 p.m. | W 20-2 | |
| Tue., 4/11 | JV Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 6:30 p.m. | W 16-1 | |
| Tue., 4/11 | FR Girls Lacrosse | Fairfield Ludlowe | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | W 6-4 | |
| Tue., 4/11 | V Girls Tennis | Norwalk | Home - Wilton HS-Tennis Courts [Directions] | 10:30 a.m. | W 6-1 [Detailed Results] | |
| Tue., 4/11 | JV Girls Tennis | Ridgefield | Away - Ridgefield HS-RHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/12 | FR Boys Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | ||
| Wed., 4/12 | V Softball | New Canaan | Home - Wilton HS-Varsity Softball Field [Directions] | 4:30 p.m. | W 1-0 | |
| Thu., 4/13 | V Boys Lacrosse | Stepinac (NY) | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 7:00 p.m. | L 7-12 | |
| Thu., 4/13 | JV Boys Lacrosse | Stepinac (NY) | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 4:30 p.m. | ||
| Thu., 4/13 | V Boys Tennis | New Canaan | Away - New Canaan HS-NCHS Tennis Courts [Directions] | 1:30 p.m. | W 6-1 [Detailed Results] | |
| Thu., 4/13 | V Girls Lacrosse | Guilford | Away - Guilford HS-Kavanaugh Turf Field and Track [Directions] | 12:00 p.m. | W 18-3 | |
| Thu., 4/13 | JV Girls Lacrosse | Guilford | Away - Guilford HS-Kavanaugh Turf Field and Track [Directions] | 1:30 p.m. | W 16-1 | |
| Thu., 4/13 | JV Softball | New Canaan | Home - Wilton HS-JV Softball Field [Directions] | 4:00 p.m. | ||
| Thu., 4/13 | V Girls Tennis | New Canaan | Home - Wilton HS-Tennis Courts [Directions] | 12:00 p.m. | L 0-7 [Detailed Results] | |
| Fri., 4/14 | V Baseball | Fairfield Warde | Away - Fairfield Warde HS-Baseball Diamond [Directions] | 4:00 p.m. | L 6-0 | |
| Fri., 4/14 | JV Baseball | Fairfield Warde | Away - Tunxis [Directions] | 4:00 p.m. | ||
| Fri., 4/14 | FR Baseball | Fairfield Warde | Home - Allen's Meadow-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Fri., 4/14 | FR Boys Lacrosse | Stamford | Home - Allen's Meadow-Lacrosse Field #1 [Directions] | 4:30 p.m. | ||
| Fri., 4/14 | FR Girls Lacrosse | Trumbull | Away - Trumbull HS-JV Grass Field [Directions] | 4:30 p.m. | W 12-3 | |
| Fri., 4/14 | V Softball | Fairfield Warde | Home - Wilton HS-Varsity Softball Field [Directions] | 4:00 p.m. | W 12-5 | |
| Fri., 4/14 | JV Softball | Fairfield Warde | Home - Wilton HS-JV Softball Field [Directions] | Postponed | ||
| Sat., 4/15 | JV Baseball | Weston | Away - Weston HS-Revson #2 (JV) [Directions] | Suspended | ||
| Sat., 4/15 | V Boys Lacrosse | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 3:00 p.m. | W 9-3 | |
| Sat., 4/15 | JV Boys Lacrosse | Greenwich | Away - Greenwich HS-Field 4 [Directions] | 2:00 p.m. | ||
| Sat., 4/15 | V Girls Lacrosse | North Shore (NY) | Away - North Shore HS | 3:00 p.m. | W 10-9 | |
| Mon., 4/17 | V Baseball | Norwalk | Home - Wilton HS-Varsity Baseball Field [Directions] | 4:15 p.m. | L 0-1 | |
| Mon., 4/17 | JV Baseball | Norwalk | Home - Wilton HS-JV Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/17 | FR Baseball | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 4:30 p.m. | ||
| Mon., 4/17 | FR Boys Lacrosse | New Canaan | Home - Allen's Meadow-Lacrosse Field #1 [Directions] | 4:30 p.m. | ||
| Mon., 4/17 | JV Boys Tennis | Fairfield Warde | Away - Fairfield Warde HS-Knapps Courts [Directions] | 4:00 p.m. | ||
| Mon., 4/17 | FR Girls Lacrosse | New Canaan | Home - Wilton HS-Allen Meadow [Directions] | 4:45 p.m. | W 14-5 | |
| Mon., 4/17 | V Softball | Norwalk | Away - Norwalk HS-Ray Barry Field [Directions] | 4:30 p.m. | W 10-5 | |
| Tue., 4/18 | FR Boys Lacrosse | Darien | Home - Allen's Meadow-Lacrosse Field #1 [Directions] | 4:30 p.m. | ||
| Tue., 4/18 | V Boys Outdoor Track | Harding, Bassick, Bridgeport Central | Away - Warren Harding HS-Lewis Field [Directions] | 4:00 p.m. | ||
| Tue., 4/18 | V Girls Lacrosse | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:30 p.m. | W 13-3 | |
| Tue., 4/18 | JV Girls Lacrosse | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 6:00 p.m. | W 14-2 | |
| Tue., 4/18 | FR Girls Lacrosse | Staples | Away - Staples HS-Ginny Parker Field [Directions] | Postponed | ||
| Tue., 4/18 | V Girls Outdoor Track | Harding, Bassick, Bridgeport Central | Away - Warren Harding HS-Lewis Field [Directions] | 4:00 p.m. | ||
| Tue., 4/18 | JV Softball | Norwalk | Away - Naramake School Field [Directions] | 4:00 p.m. | ||
| Tue., 4/18 | V Girls Tennis | Stamford | Home - Wilton HS-Tennis Courts [Directions] | 4:30 p.m. | W 6-1 [Detailed Results] | |
| Wed., 4/19 | V Baseball | New Canaan | Home - Wilton HS-Varsity Baseball Field [Directions] | 4:15 p.m. | W 3-2 | |
| Wed., 4/19 | JV Baseball | New Canaan | Home - Wilton HS-JV Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 4/19 | FR Baseball | New Canaan | Away - New Canaan HS-Coppo Field [Directions] | 4:00 p.m. | ||
| Wed., 4/19 | FR Boys Lacrosse | Trumbull | Home - Allen's Meadow-Lacrosse Field #1 [Directions] | 4:30 p.m. | ||
| Wed., 4/19 | V Boys Tennis | Brien McMahon | Home - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Wed., 4/19 | V Girls Golf | Fairfield Warde | Away - Smith Richardson Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 4/19 | V Softball | New Canaan | Away - Waveny Park-Orchard Field [Directions] | 6:30 p.m. | W 11-5 | |
| Wed., 4/19 | V Girls Tennis | Brien McMahon | Away - Brien McMahon HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Thu., 4/20 | JV Baseball | Weston | Away - Weston HS-Revson #2 (JV) [Directions] | 4:30 p.m. | ||
| Thu., 4/20 | V Boys Lacrosse | Staples | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 7:00 p.m. | W 6-4 | |
| Thu., 4/20 | JV Boys Lacrosse | Staples | Home - Wilton HS-Fuijitani Field -Turf [Directions] | 4:30 p.m. | ||
| Thu., 4/20 | V Boys Tennis | Staples | Home - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | W 5-2 [Detailed Results] | |
| Thu., 4/20 | JV Boys Tennis | Staples | Home - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 4/20 | V Girls Golf | Greenwich | Home - Silvermine Golf Club [Directions] | 3:30 p.m. | ||
| Thu., 4/20 | V Girls Lacrosse | Staples | Home - Wilton HS-Lilly Field [Directions] | 6:00 p.m. | W 18-1 | |
| Thu., 4/20 | JV Girls Lacrosse | Staples | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | ||
| Thu., 4/20 | FR Girls Lacrosse | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | 5:00 p.m. | ||
| Thu., 4/20 | V Girls Tennis | Staples | Away - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | L 2-5 [Detailed Results] | |
| Thu., 4/20 | JV Girls Tennis | Staples | Away - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 4/21 | V Baseball | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 4:00 p.m. | W 7-1 | |
| Fri., 4/21 | JV Baseball | Brien McMahon | Away - City Hall Field [Directions] | 4:00 p.m. | ||
| Fri., 4/21 | FR Boys Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Turf Field II [Directions] | 4:30 p.m. | ||
| Fri., 4/21 | V Boys Tennis | Stamford | Away - Stamford HS-SHS Tennis Courts [Directions] | 4:30 p.m. | W 6-1 [Detailed Results] | |
| Fri., 4/21 | V Softball | Brien McMahon | Home - Wilton HS-Varsity Softball Field [Directions] | 4:00 p.m. | L 2-3 | |
| Sat., 4/22 | V Baseball | Weston | Away - Weston HS-Revson #1 (Varsity) [Directions] | 11:00 a.m. | W 20-4 | |
| Sat., 4/22 | V Boys Lacrosse | Yorktown (NY) | Away - Yorktown Heights HS-Lacrosse Field | 6:30 p.m. | W 10-9 | |
| Sat., 4/22 | JV Boys Lacrosse | Yorktown (NY) | Away - Yorktown Heights HS-Lacrosse Field | 4:30 p.m. | ||
| Sat., 4/22 | V Girls Outdoor Track | Bethel | Away - Bethel Berry School- Kisling Field [Directions] | 8:30 a.m. | ||
| Sat., 4/22 | JV Softball | Brien McMahon | Home - Wilton HS-JV Softball Field [Directions] | 10:00 a.m. | ||
| Mon., 4/24 | V Baseball | Stamford | Home - Wilton HS-Varsity Baseball Field [Directions] | 4:30 p.m. | L 1-0 | |
| Mon., 4/24 | JV Baseball | Stamford | Home - Wilton HS-JV Baseball Field [Directions] | 4:30 p.m. | ||
| Mon., 4/24 | FR Baseball | Stamford | Away - Stamford HS-SHS Baseball Diamond [Directions] | 4:30 p.m. | ||
| Mon., 4/24 | FR Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Fairfield Warde Grass Utility Field [Directions] | 4:30 p.m. | ||
| Mon., 4/24 | V Boys Tennis | Danbury | Away - Danbury HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Mon., 4/24 | V Girls Golf | Darien | Away - Wee Burn CC [Directions] | 3:00 p.m. | ||
| Mon., 4/24 | JV Girls Golf | Darien | Away - Wee Burn CC [Directions] | 3:00 p.m. | ||
| Mon., 4/24 | V Softball | Stamford | Away - Troy Complex-Diamond 1 [Directions] | 7:00 p.m. | W 5-4 | |
| Mon., 4/24 | V Girls Tennis | Danbury | Home - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Mon., 4/24 | JV Girls Tennis | Fairfield Warde | Home - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/25 | V Boys Lacrosse | St. Joseph | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 7:00 p.m. | W 16-7 | |
| Tue., 4/25 | JV Boys Lacrosse | St. Joseph | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 5:00 p.m. | ||
| Tue., 4/25 | V Boys Outdoor Track | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Tue., 4/25 | V Boys Tennis | Bridgeport Central | Home - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Tue., 4/25 | V Girls Lacrosse | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 4:00 p.m. | W 17-0 | |
| Tue., 4/25 | JV Girls Lacrosse | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 5:30 p.m. | ||
| Tue., 4/25 | V Girls Outdoor Track | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Tue., 4/25 | JV Softball | Staples | Home - Wilton HS-JV Softball Field [Directions] | 4:00 p.m. | ||
| Tue., 4/25 | V Girls Tennis | Bridgeport Central | Home - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Tue., 4/25 | JV Girls Tennis | Trumbull | Away - Tashua Knolls Golf Course-Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/26 | V Baseball | Staples | Away - Staples HS-Baseball Diamond [Directions] | 4:30 p.m. | L 2-0 | |
| Wed., 4/26 | JV Baseball | Staples | Away - Staples HS-Wakeman Field [Directions] | 4:30 p.m. | ||
| Wed., 4/26 | FR Baseball | Staples | Home - Allen's Meadow-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 4/26 | FR Boys Lacrosse | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:30 p.m. | ||
| Wed., 4/26 | FR Girls Lacrosse | Darien | Home - Wilton HS-Allen Meadow [Directions] | 4:00 p.m. | ||
| Wed., 4/26 | V Softball | Staples | Home - Wilton HS-Varsity Softball Field [Directions] | 4:00 p.m. | L 2-3 | |
| Thu., 4/27 | V Girls Golf | New Canaan | Home - Silvermine Golf Club [Directions] | 3:30 p.m. | ||
| Thu., 4/27 | V Girls Lacrosse | Ridgefield | Home - Wilton HS-Lilly Field [Directions] | 6:00 p.m. | W 21-6 | |
| Thu., 4/27 | JV Girls Lacrosse | Ridgefield | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | ||
| Fri., 4/28 | V Baseball | Danbury | Home - Wilton HS-Varsity Baseball Field [Directions] | 4:15 p.m. | W 1-0 | |
| Fri., 4/28 | JV Baseball | Danbury | Home - Wilton HS-JV Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 4/28 | FR Boys Lacrosse | Fairfield Ludlowe | Home - Allen's Meadow-Lacrosse Field #1 [Directions] | 4:30 p.m. | ||
| Fri., 4/28 | V Boys Tennis | Westhill | Home - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | W 5-2 [Detailed Results] | |
| Fri., 4/28 | FR Girls Lacrosse | Westhill | Away - Westhill HS-Westhill Front Turf Field [Directions] | Canceled | Cancelled | |
| Sat., 4/29 | V Boys Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 4:30 p.m. | W 11-6 | |
| Sat., 4/29 | JV Boys Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Turf Field II [Directions] | 2:00 p.m. | ||
| Sat., 4/29 | JV Softball | Stamford | Away - Stamford HS-SHS Softball Diamond [Directions] | Postponed | ||
| Sat., 4/29 | JV Softball | Danbury | Home - Wilton HS-JV Softball Field [Directions] | Postponed | ||
| Mon., 5/1 | V Baseball | Bridgeport Central | Home - Wilton HS-Varsity Baseball Field [Directions] | 6:00 p.m. | W 10-1 | |
| Mon., 5/1 | JV Baseball | Bridgeport Central | Home - Wilton HS-JV Baseball Field [Directions] | Canceled | Cancelled | |
| Mon., 5/1 | FR Boys Lacrosse | Greenwich | Home - Allen's Meadow-Lacrosse Field #1 [Directions] | 4:30 p.m. | ||
| Mon., 5/1 | V Boys Tennis | Trumbull | Home - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | W 6-1 [Detailed Results] | |
| Mon., 5/1 | V Girls Tennis | Trumbull | Away - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Mon., 5/1 | JV Girls Tennis | Trumbull | Home - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/2 | V Boys Outdoor Track | New Canaan | Away - New Canaan HS-NCHS Track [Directions] | 4:00 p.m. | ||
| Tue., 5/2 | V Girls Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 5/2 | V Girls Outdoor Track | New Canaan | Away - New Canaan HS-NCHS Track [Directions] | 4:00 p.m. | ||
| Wed., 5/3 | V Baseball | Westhill | Away - Westhill HS-Varsity Baseball Field [Directions] | 4:00 p.m. | L 12-3 | |
| Wed., 5/3 | JV Baseball | Westhill | Away - Rippowan MS-Rippowam Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/3 | FR Baseball | Westhill | Home - Allen's Meadow-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 5/3 | FR Boys Lacrosse | Stamford | Away - Stamford HS-Upper Lacrosse Field [Directions] | 5:00 p.m. | ||
| Wed., 5/3 | V Boys Tennis | Ridgefield | Home - Wilton HS-Tennis Courts [Directions] | 4:45 p.m. | W 5-2 [Detailed Results] | |
| Wed., 5/3 | JV Boys Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 5:00 p.m. | ||
| Wed., 5/3 | FR Girls Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | 4:00 p.m. | ||
| Wed., 5/3 | V Softball | Westhill | Home - Wilton HS-Varsity Softball Field [Directions] | 6:00 p.m. | L 2-8 | |
| Wed., 5/3 | JV Softball | Westhill | Home - Wilton HS-JV Softball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/3 | V Girls Tennis | Ridgefield | Away - Ridgefield HS-RHS Tennis Courts [Directions] | 5:00 p.m. | W 5-2 [Detailed Results] | |
| Wed., 5/3 | JV Girls Tennis | Ridgefield | Home - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:45 p.m. | ||
| Thu., 5/4 | V Boys Lacrosse | Darien | Away - Darien HS-DHS Center Oval Turf Field [Directions] | 4:30 p.m. | L 8-9 | |
| Thu., 5/4 | JV Boys Lacrosse | Darien | Away - Darien HS-DHS Center Oval - Turf [Directions] | 6:00 p.m. | ||
| Thu., 5/4 | V Boys Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Thu., 5/4 | JV Boys Tennis | Fairfield Ludlowe | Away - Tomlinson MS-Tennis Courts [Directions] | 4:30 p.m. | ||
| Thu., 5/4 | V Girls Lacrosse | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 6:30 p.m. | L 7-17 | |
| Thu., 5/4 | JV Girls Lacrosse | Darien | Away - Darien HS-DHS Stadium East [Directions] | 5:00 p.m. | ||
| Thu., 5/4 | V Softball | Bridgeport Central | Away - Bridgeport Central-Varsity Softball Field [Directions] | 4:30 p.m. | W 16-0 (5) | |
| Thu., 5/4 | V Girls Tennis | Fairfield Ludlowe | Home - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | L 1-6 [Detailed Results] | |
| Fri., 5/5 | V Baseball | Trumbull | Away - Trumbull HS-Varsity Baseball Field [Directions] | 4:30 p.m. | W 10-9 | |
| Fri., 5/5 | JV Baseball | Trumbull | Away - Trumbull HS-JV Baseball Field [Directions] | 4:30 p.m. | ||
| Fri., 5/5 | FR Baseball | Trumbull | Home - Allen's Meadow-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Fri., 5/5 | V Boys Tennis | Weston | Home - Wilton HS-Tennis Courts [Directions] | 4:15 p.m. | W 6-1 [Detailed Results] | |
| Fri., 5/5 | JV Boys Tennis | Weston | Home - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 5/5 | FR Girls Lacrosse | Greenwich | Home - Wilton HS-Allen Meadow [Directions] | 4:30 p.m. | ||
| Fri., 5/5 | V Softball | Trumbull | Home - Wilton HS-Varsity Softball Field [Directions] | 4:30 p.m. | W 1-0 | |
| Fri., 5/5 | JV Softball | Trumbull | Home - Wilton HS-JV Softball Field [Directions] | 4:30 p.m. | ||
| Sat., 5/6 | V Boys Lacrosse | Chaminade (NY) | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 5:00 p.m. | W 11-10 | |
| Sat., 5/6 | JV Boys Lacrosse | Chaminade (NY) | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 2:30 p.m. | ||
| Sat., 5/6 | V Girls Lacrosse | Cheshire | Home - Wilton HS-Lilly Field [Directions] | 6:00 p.m. | W 18-4 | |
| Sat., 5/6 | JV Girls Lacrosse | Cheshire | Home - Wilton HS-Lilly Field [Directions] | 4:30 p.m. | ||
| Sat., 5/6 | V Girls Tennis | Westhill | Away - Westhill HS-Westhill Tennis Courts [Directions] | 3:00 p.m. | W 4-3 | |
| Mon., 5/8 | V Baseball | Ridgefield | Away - Governor Field [Directions] | 4:00 p.m. | L 2-0 | |
| Mon., 5/8 | JV Baseball | Ridgefield | Away - East Ridge MS-Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/8 | FR Baseball | Ridgefield | Home - Allen's Meadow-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Mon., 5/8 | V Boys Tennis | Greenwich | Home - Wilton HS-Tennis Courts [Directions] | 4:30 p.m. | L 6-1 [Detailed Results] | |
| Mon., 5/8 | V Girls Golf | Danbury | Home - Silvermine Golf Club [Directions] | 3:30 p.m. | ||
| Mon., 5/8 | V Softball | Ridgefield | Home - Wilton HS-Varsity Softball Field [Directions] | 4:15 p.m. | L 0-1 | |
| Mon., 5/8 | V Girls Tennis | Greenwich | Away - Greenwich HS-Tennis Courts [Directions] | 4:30 p.m. | L 1-6 [Detailed Results] | |
| Mon., 5/8 | JV Girls Tennis | Greenwich | Away - Binney Park [Directions] | 4:30 p.m. | ||
| Tue., 5/9 | FR Baseball | Danbury | Away - Danbury HS-V Baseball Field [Directions] | 4:00 p.m. | ||
| Tue., 5/9 | V Boys Lacrosse | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 4:30 p.m. | W 14-1 | |
| Tue., 5/9 | JV Boys Lacrosse | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 6:00 p.m. | ||
| Tue., 5/9 | V Boys Outdoor Track | Ridgefield | Home - Wilton HS-Track [Directions] | 4:00 p.m. | ||
| Tue., 5/9 | V Boys Tennis | Darien | Away - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | L 4-3 [Detailed Results] | |
| Tue., 5/9 | JV Boys Tennis | Darien | Away - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/9 | V Girls Golf | Staples | Away - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 5/9 | V Girls Lacrosse | Danbury | Home - Wilton HS-Lilly Field [Directions] | 6:00 p.m. | W 19-1 | |
| Tue., 5/9 | JV Girls Lacrosse | Danbury | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | ||
| Tue., 5/9 | V Girls Outdoor Track | Ridgefield | Home - Wilton HS-Track [Directions] | 4:00 p.m. | ||
| Tue., 5/9 | V Softball | Danbury | Away - Danbury HS-V Softball field [Directions] | 4:30 p.m. | W 8-2 | |
| Tue., 5/9 | V Girls Tennis | Darien | Home - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | L 1-6 [Detailed Results] | |
| Wed., 5/10 | V Baseball | Fairfield Ludlowe | Home - Wilton HS-Varsity Baseball Field [Directions] | 4:15 p.m. | L 7-0 | |
| Wed., 5/10 | JV Baseball | Fairfield Ludlowe | Home - Wilton HS-JV Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/10 | FR Baseball | Fairfield Ludlowe | Away - Kiwanis Field-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 5/10 | FR Boys Lacrosse | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 4:30 p.m. | ||
| Wed., 5/10 | FR Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Fairfield Warde Grass Utility Field [Directions] | 4:30 p.m. | ||
| Wed., 5/10 | V Softball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 4:30 p.m. | L 0-8 | |
| Wed., 5/10 | JV Softball | Fairfield Ludlowe | Away - Tom Hayden Field [Directions] | Postponed | ||
| Thu., 5/11 | V Boys Lacrosse | New Canaan | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 7:00 p.m. | L 6-8 | |
| Thu., 5/11 | JV Boys Lacrosse | New Canaan | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 4:30 p.m. | ||
| Thu., 5/11 | V Boys Tennis | St. Joseph | Away - St. Joseph HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Thu., 5/11 | JV Boys Tennis | Greenwich | Away - Central MS [Directions] | 4:30 p.m. | ||
| Thu., 5/11 | V Girls Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 4:30 p.m. | L 6-13 | |
| Thu., 5/11 | JV Girls Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 6:00 p.m. | ||
| Thu., 5/11 | FR Girls Lacrosse | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:30 p.m. | ||
| Thu., 5/11 | JV Softball | Greenwich | Home - Wilton HS-JV Softball Field [Directions] | 4:00 p.m. | ||
| Thu., 5/11 | V Girls Tennis | St. Joseph | Home - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | W 5-2 [Detailed Results] | |
| Fri., 5/12 | JV Boys Tennis | Trumbull | Away - Tashua Knolls Golf Course-Tennis Courts [Directions] | 4:30 p.m. | ||
| Fri., 5/12 | V Softball | Greenwich | Home - Wilton HS-Varsity Softball Field [Directions] | 7:00 p.m. | W 9-2 | |
| Sat., 5/13 | V Baseball | Greenwich | Away - Greenwich HS-Baseball Field [Directions] | 10:30 a.m. | L 6-5 | |
| Sat., 5/13 | JV Baseball | Greenwich | Away - Julian Curtiss School [Directions] | 10:30 a.m. | ||
| Sat., 5/13 | FR Baseball | Greenwich | Home - Allen's Meadow-Baseball Diamond [Directions] | 2:30 p.m. | ||
| Sat., 5/13 | V Boys Lacrosse | Fordham Prep (NY) | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 6:00 p.m. | W 14-8 | |
| Sat., 5/13 | JV Boys Lacrosse | Fordham Prep (NY) | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 3:30 p.m. | ||
| Sat., 5/13 | JV Softball | New Canaan | Away - Waveny Park-Orchard Field [Directions] | 2:30 p.m. | ||
| Mon., 5/15 | V Baseball | Darien | Home - Wilton HS-Varsity Baseball Field [Directions] | 4:15 p.m. | L 4-2 | |
| Mon., 5/15 | JV Baseball | Darien | Home - Wilton HS-JV Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/15 | FR Baseball | Darien | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Mon., 5/15 | V Girls Golf | Ridgefield | Home - Silvermine Golf Club [Directions] | 3:30 p.m. | ||
| Mon., 5/15 | V Softball | Darien | Away - Darien HS-DHS Softball - Varsity Field [Directions] | 4:30 p.m. | W 8-2 | |
| Tue., 5/16 | FR Boys Lacrosse | Trumbull | Away - Trumbull HS-JV Grass Field [Directions] | 4:30 p.m. | ||
| Tue., 5/16 | V Girls Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 3:30 p.m. | ||
| Tue., 5/16 | FR Girls Lacrosse | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 4:30 p.m. | ||
| Tue., 5/16 | JV Softball | Ridgefield | Home - Wilton HS-JV Softball Field [Directions] | 4:45 p.m. | ||
| Wed., 5/17 | V Baseball | St. Joseph | Home - Wilton HS-Varsity Baseball Field [Directions] | 4:15 p.m. | L 9-5 | |
| Wed., 5/17 | JV Baseball | St. Joseph | Home - Wilton HS-Freshman Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/17 | FR Baseball | St. Joseph | Away - St. Joseph HS-Baseball Diamond [Directions] | 4:30 p.m. | ||
| Wed., 5/17 | V Boys Lacrosse | Glastonbury | Away - Glastonbury HS-Field 1 [Directions] | 6:00 p.m. | W 6-4 | |
| Wed., 5/17 | JV Boys Lacrosse | Glastonbury | Away - Glastonbury HS-Field 11 [Directions] | 4:30 p.m. | ||
| Wed., 5/17 | V Boys Outdoor Track | St. Joseph | Home - Wilton HS-Track [Directions] | 4:00 p.m. | ||
| Wed., 5/17 | V Girls Outdoor Track | St. Joseph | Home - Wilton HS-Track [Directions] | 4:00 p.m. | ||
| Wed., 5/17 | V Softball | St. Joseph | Away - St. Joseph HS-Softball Diamond [Directions] | 4:30 p.m. | L 14-5 | |
| Wed., 5/17 | JV Softball | St. Joseph | Away - Long Hill Administration Bldg-Softball Field [Directions] | Postponed | ||
| Thu., 5/18 | FR Boys Lacrosse | Staples | Home - Allen's Meadow-Lacrosse Field #1 [Directions] | 4:30 p.m. | ||
| Thu., 5/18 | V Girls Golf | St. Joseph | Away - Tashua Knolls Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 5/18 | JV Softball | Danbury | Home - Wilton HS-JV Softball Field [Directions] | 4:15 p.m. | ||
| Tue., 5/23 | V Girls Golf | New Canaan | Away - CCNC [Directions] | 3:30 p.m. | ||