| Westhill 2023-24 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 767 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Tue., 8/22 | V Boys Golf | Wilton | Away - Rolling Hills Country Club [Directions] | 3:30 p.m. | ||
| Wed., 8/23 | V Boys Golf | Fairfield Ludlowe | Home - EG Brennan Golf Course-E Gaynor Brennan Golf Course [Directions] | 3:15 p.m. | ||
| Mon., 8/28 | FR Football | Norwalk (Scrim.) | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:30 p.m. | ||
| Tue., 8/29 | V Boys Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | 3:30 p.m. | ||
| Wed., 8/30 | V Boys Soccer | Brien McMahon (Scrim.) | Home - Westhill HS-Front Turf [Directions] | 5:15 p.m. | ||
| Thu., 8/31 | V Football | Immaculate (Scrim.) | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:00 p.m. | ||
| Thu., 8/31 | V Boys Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Thu., 8/31 | V Girls Soccer | Jonathan Law (Scrim.) | Away - Jonathan Law HS-Lawmen Stadium [Directions] | 4:15 p.m. | ||
| Fri., 9/1 | V Boys Soccer | Brunswick School (Scrim.) | Home - Westhill HS-Westhill Front Turf Field [Directions] | 5:15 p.m. | ||
| Sat., 9/2 | V Girls Soccer | Hall (Scrim.) | Away - Conard HS-Jamboree Field [Directions] | 10:00 a.m. | ||
| Sat., 9/2 | V Girls Soccer | Tolland (Scrim.) | Away - Conard HS-South Field [Directions] | 11:30 a.m. | ||
| Sat., 9/2 | V Girls Soccer | Conard (Scrim.) | Away - Conard HS-McKee Stadium [Directions] | 12:15 p.m. | ||
| Tue., 9/5 | V Boys Golf | Ridgefield | Home - EG Brennan Golf Course-E Gaynor Brennan Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 9/5 | V Girls Volleyball | Stamford (Scrim.) | Away - Stamford HS-Kuczo Gymnasium [Directions] | 3:30 p.m. | W 0-0 | |
| Wed., 9/6 | V Boys Golf | Darien | Home - EG Brennan Golf Course-E Gaynor Brennan Golf Course [Directions] | Postponed | ||
| Thu., 9/7 | V Girls Soccer | Trumbull | Away - Trumbull HS-Cork Field [Directions] | 7:00 p.m. | L 0-8 | |
| Thu., 9/7 | V Girls Volleyball | Masuk | Home - Westhill HS-Main Gym [Directions] | 6:30 p.m. | L 3-2 [Detailed Results] | |
| Thu., 9/7 | JV Girls Volleyball | Masuk | Home - Westhill HS-Main Gym [Directions] | Postponed | ||
| Fri., 9/8 | V Girls Swimming and Diving | Fairfield Ludlowe | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Sat., 9/9 | V Football | Newington | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 12:00 p.m. | L 25-26 | |
| Sat., 9/9 | JV Football | Fairfield Ludlowe | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | ||
| Sat., 9/9 | V Boys Soccer | Southington | Home - Farmington Sports Arena-Field 1 [Directions] | 12:30 p.m. | W 3-1 | |
| Sat., 9/9 | JV Boys Soccer | Trumbull | Home - Westhill HS-Front Turf [Directions] | 10:30 a.m. | L 1-0 | |
| Sat., 9/9 | FR Boys Soccer | Trumbull | Away - Trumbull HS-JV Grass Field [Directions] | 11:00 a.m. | ||
| Sat., 9/9 | V Girls Soccer | Bethel | Away - Bethel HS-MS Turf Soccer Field [Directions] | 11:00 a.m. | L 0-4 | |
| Sat., 9/9 | JV Girls Soccer | Bethel | Away - Bethel HS-MS Turf Soccer Field [Directions] | 1:00 p.m. | ||
| Sat., 9/9 | V Girls Volleyball | Pomperaug | Away - Pomperaug HS-Main Gym [Directions] | 12:30 p.m. | W 3-2 [Detailed Results] | |
| Sat., 9/9 | JV Girls Volleyball | Pomperaug | Away - Pomperaug HS-Main Gym [Directions] | 11:00 a.m. | ||
| Mon., 9/11 | V Field Hockey | Wilton | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | L 5-1 | |
| Mon., 9/11 | JV Field Hockey | Wilton | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | ||
| Mon., 9/11 | FR Field Hockey | Wilton | Away - Wilton HS-Fuijitani Field -Turf [Directions] | 4:15 p.m. | ||
| Tue., 9/12 | V Boys Soccer | Darien | Away - Darien HS-DHS Center Oval - Turf [Directions] | 4:00 p.m. | T 2-2 | |
| Tue., 9/12 | JV Boys Soccer | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | W 3-1 | |
| Tue., 9/12 | FR Boys Soccer | Darien | Home - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | ||
| Tue., 9/12 | V Girls Volleyball | Southington | Home - Westhill HS-Main Gym [Directions] | 6:30 p.m. | L 3-0 [Detailed Results] | |
| Tue., 9/12 | JV Girls Volleyball | Southington | Home - Westhill HS-Main Gym [Directions] | 5:00 p.m. | ||
| Tue., 9/12 | FR Girls Volleyball | Southington | Home - Westhill HS-New Gym [Directions] | 5:00 p.m. | ||
| Wed., 9/13 | V Boys Cross Country | Fairfield Warde, Norwalk, Stamford | Home - Scofield Magnet MS-Cross Country Course [Directions] | 4:00 p.m. | ||
| Wed., 9/13 | FR Football | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 4:30 p.m. | ||
| Wed., 9/13 | V Girls Cross Country | Fairfield Warde, Norwalk, Stamford | Home - Scofield Magnet MS-Cross Country Course [Directions] | 4:00 p.m. | ||
| Wed., 9/13 | V Field Hockey | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 4:30 p.m. | L 10-0 | |
| Wed., 9/13 | JV Field Hockey | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 5:45 p.m. | ||
| Wed., 9/13 | FR Field Hockey | Staples | Home - Westhill HS-Front Turf [Directions] | 4:00 p.m. | ||
| Wed., 9/13 | V Girls Soccer | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 4:00 p.m. | L 0-6 | |
| Wed., 9/13 | JV Girls Soccer | Ridgefield | Away - Ridgefield HS-RHS Lower Grass Field [Directions] | 4:30 p.m. | ||
| Wed., 9/13 | V Girls Swimming and Diving | Trumbull | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Thu., 9/14 | V Boys Golf | Fairfield Warde | Away - Brooklawn Country Club [Directions] | 3:00 p.m. | ||
| Thu., 9/14 | JV Boys Golf | Fairfield Warde | Away - Brooklawn Country Club [Directions] | 3:00 p.m. | ||
| Thu., 9/14 | V Boys Soccer | Ridgefield | Home - Westhill HS-Westhill Front Turf Field [Directions] | 4:45 p.m. | W 1-0 | |
| Thu., 9/14 | FR Boys Soccer | Ridgefield | Away - Ridgefield HS-RHS Lower Grass Field [Directions] | 4:00 p.m. | ||
| Thu., 9/14 | V Girls Volleyball | Bassick | Home - Westhill HS-Main Gym [Directions] | 6:00 p.m. | W 3-0 [Detailed Results] | |
| Thu., 9/14 | JV Girls Volleyball | Bassick | Home - Westhill HS-Main Gym [Directions] | 4:30 p.m. | ||
| Fri., 9/15 | V Football | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 3:00 p.m. | L 0-49 | |
| Mon., 9/18 | JV Football | St. Joseph | Home - Rippowan MS-Rippowam Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 9/18 | V Field Hockey | Darien | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | L 0-11 | |
| Mon., 9/18 | JV Field Hockey | Darien | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | ||
| Mon., 9/18 | FR Field Hockey | Darien | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Mon., 9/18 | V Girls Soccer | Danbury | Home - Westhill HS-Westhill Front Turf Field [Directions] | 4:45 p.m. | L 1-3 | |
| Tue., 9/19 | V Boys Cross Country | Brien McMahon, Darien, Greenwich | Home - Scofield Magnet MS-Cross Country Course [Directions] | 4:00 p.m. | ||
| Tue., 9/19 | V Boys Golf | Staples | Away - Longshore Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 9/19 | V Boys Soccer | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 4:00 p.m. | L 3-0 | |
| Tue., 9/19 | JV Boys Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 4:00 p.m. | L 5-1 | |
| Tue., 9/19 | FR Boys Soccer | Danbury | Home - Rippowan MS-Rippowam Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 9/19 | V Girls Cross Country | Brien McMahon, Darien, Greenwich | Home - Scofield Magnet MS-Cross Country Course [Directions] | 4:00 p.m. | ||
| Wed., 9/20 | FR Football | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 5:30 p.m. | ||
| Wed., 9/20 | V Boys Golf | Danbury | Home - EG Brennan Golf Course-E Gaynor Brennan Golf Course [Directions] | 3:15 p.m. | ||
| Wed., 9/20 | V Field Hockey | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 4:00 p.m. | L 0-1 [Detailed Results] | |
| Wed., 9/20 | JV Field Hockey | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 5:30 p.m. | ||
| Wed., 9/20 | V Girls Soccer | Fairfield Ludlowe | Home - Westhill HS-Westhill Front Turf Field [Directions] | 4:45 p.m. | L 0-5 | |
| Wed., 9/20 | JV Girls Soccer | Fairfield Ludlowe | Home - Rippowan MS-Rippowam Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 9/20 | V Girls Swimming and Diving | Wilton | Away - Wilton YMCA [Directions] | 3:40 p.m. | ||
| Wed., 9/20 | V Girls Volleyball | Weston | Away - Weston HS-Gym (New) [Directions] | 5:30 p.m. | W 3-2 [Detailed Results] | |
| Wed., 9/20 | JV Girls Volleyball | Weston | Away - Weston HS-Gym (New) [Directions] | 4:00 p.m. | ||
| Wed., 9/20 | FR Girls Volleyball | Weston | Away - Weston HS-Gym (Old) [Directions] | 4:00 p.m. | ||
| Thu., 9/21 | V Boys Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 7:00 p.m. | L 1-0 | |
| Thu., 9/21 | JV Boys Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | 5:00 p.m. | L 2-0 | |
| Thu., 9/21 | FR Boys Soccer | Fairfield Ludlowe | Home - Rippowan MS-Rippowam Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 9/22 | V Field Hockey | Weston | Away - Weston HS-WHS Lower Turf Field [Directions] | 5:45 p.m. | L 0-2 | |
| Fri., 9/22 | JV Field Hockey | Weston | Away - Weston HS-WHS Lower Turf Field [Directions] | 4:15 p.m. | ||
| Fri., 9/22 | V Girls Soccer | Fairfield Warde | Home - Westhill HS-Westhill Front Turf Field [Directions] | 4:30 p.m. | L 0-2 | |
| Fri., 9/22 | V Girls Volleyball | Trumbull | Home - Westhill HS-Main Gym [Directions] | 6:00 p.m. | L 3-2 [Detailed Results] | |
| Fri., 9/22 | JV Girls Volleyball | Trumbull | Home - Westhill HS-Main Gym [Directions] | 4:30 p.m. | ||
| Sat., 9/23 | V Football | Enfield | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 1:00 p.m. | L 14-21 | |
| Sat., 9/23 | V Boys Soccer | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 12:00 p.m. | T 1-1 | |
| Sat., 9/23 | FR Boys Soccer | Fairfield Warde | Home - Westhill HS-Westhill Front Turf Field [Directions] | Postponed | ||
| Sat., 9/23 | FR Girls Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | Postponed | ||
| Tue., 9/26 | V Boys Soccer | Trumbull | Home - Westhill HS-Westhill Front Turf Field [Directions] | 4:00 p.m. | L 3-0 | |
| Tue., 9/26 | FR Girls Volleyball | Darien | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 9/27 | V Boys Cross Country | New Canaan, Staples, Trumbull | Away - Waveny Park [Directions] | 4:00 p.m. | ||
| Wed., 9/27 | V Boys Golf | Norwalk | Away - Oak Hills Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 9/27 | JV Boys Soccer | Brien McMahon | Home - Westhill HS-Front Turf [Directions] | 4:00 p.m. | L 4-2 | |
| Wed., 9/27 | V Girls Cross Country | New Canaan, Staples, Trumbull | Away - Waveny Park [Directions] | 4:00 p.m. | ||
| Wed., 9/27 | V Field Hockey | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 6:15 p.m. | L 0-1 [Detailed Results] | |
| Wed., 9/27 | JV Field Hockey | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 5:00 p.m. | ||
| Wed., 9/27 | V Girls Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 7:00 p.m. | L 0-6 | |
| Wed., 9/27 | JV Girls Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 5:00 p.m. | ||
| Wed., 9/27 | V Girls Swimming and Diving | Norwalk/McMahon | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Wed., 9/27 | V Girls Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | L 3-0 [Detailed Results] | |
| Wed., 9/27 | JV Girls Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 9/28 | V Boys Golf | Stamford | Home - Woodway Country Club [Directions] | 1:00 p.m. | ||
| Thu., 9/28 | V Boys Soccer | Brien McMahon | Home - Westhill HS-Westhill Front Turf Field [Directions] | 4:00 p.m. | W 1-0 | |
| Thu., 9/28 | FR Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 5:30 p.m. | ||
| Fri., 9/29 | V Girls Swimming and Diving | Greenwich | Away - Greenwich HS-Pool [Directions] | 4:00 p.m. | ||
| Fri., 9/29 | FR Girls Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/30 | V Football | Staples | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 1:00 p.m. | L 0-49 | |
| Sat., 9/30 | V Boys Soccer | Norwalk | Home - Westhill HS-Westhill Front Turf Field [Directions] | 12:00 p.m. | W 1-0 | |
| Sat., 9/30 | JV Boys Soccer | Norwalk | Home - Westhill HS-Front Turf [Directions] | 10:00 a.m. | W 2-0 | |
| Sat., 9/30 | FR Boys Soccer | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 10:00 a.m. | ||
| Sat., 9/30 | V Girls Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 12:00 p.m. | T 0-0 | |
| Sat., 9/30 | JV Girls Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 10:00 a.m. | ||
| Mon., 10/2 | JV Football | Staples | Away - Staples HS-Staples Stadium [Directions] | 6:00 p.m. | ||
| Mon., 10/2 | JV Boys Soccer | Ridgefield | Home - Rippowan MS-Rippowam Turf Field [Directions] | 4:00 p.m. | L 4-0 | |
| Mon., 10/2 | V Field Hockey | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | L 0-4 | |
| Mon., 10/2 | JV Field Hockey | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 5:30 p.m. | ||
| Tue., 10/3 | V Boys Cross Country | Wilton, Danbury, Ridgefield | Away - Allen's Meadow-XC Course [Directions] | 4:00 p.m. | ||
| Tue., 10/3 | FR Boys Soccer | Stamford | Home - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | ||
| Tue., 10/3 | V Girls Cross Country | Wilton, Danbury, Ridgefield | Away - Allen's Meadow-XC Course [Directions] | 4:00 p.m. | ||
| Tue., 10/3 | V Girls Soccer | Stamford | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | L 1-3 | |
| Tue., 10/3 | JV Girls Soccer | Stamford | Home - Rippowan MS-Rippowam Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 10/3 | V Girls Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 4:30 p.m. | W 3-0 [Detailed Results] | |
| Tue., 10/3 | JV Girls Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 10/3 | FR Girls Volleyball | Danbury | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/4 | V Boys Golf | Brien McMahon | Home - EG Brennan Golf Course-E Gaynor Brennan Golf Course [Directions] | 3:15 p.m. | ||
| Wed., 10/4 | V Boys Soccer | Stamford | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | W 4-1 | |
| Wed., 10/4 | JV Boys Soccer | Stamford | Away - West Beach Field [Directions] | 4:00 p.m. | T 1-1 | |
| Wed., 10/4 | FR Field Hockey | Danbury | Away - Danbury HS-Grass Field Hockey Field [Directions] | 4:00 p.m. | ||
| Thu., 10/5 | V Field Hockey | Lauralton Hall | Away - Lauralton Hall-Turf Field [Directions] | 4:00 p.m. | L 0-5 | |
| Thu., 10/5 | JV Field Hockey | Lauralton Hall | Away - Lauralton Hall-Turf Field [Directions] | 5:30 p.m. | ||
| Thu., 10/5 | V Girls Soccer | St. Joseph | Home - Westhill HS-Westhill Front Turf Field [Directions] | 4:00 p.m. | L 0-10 | |
| Thu., 10/5 | JV Girls Soccer | St. Joseph | Home - Rippowan MS-Rippowam Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 10/5 | V Girls Swimming and Diving | Staples | Away - Staples HS-Staples High School Pool [Directions] | 4:30 p.m. | ||
| Thu., 10/5 | V Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:30 p.m. | W 3-0 [Detailed Results] | |
| Thu., 10/5 | JV Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 6:00 p.m. | ||
| Thu., 10/5 | FR Girls Volleyball | Fairfield Ludlowe | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/6 | V Boys Soccer | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 4:00 p.m. | T 2-2 | |
| Fri., 10/6 | V Field Hockey | Danbury | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | T 0-0 | |
| Fri., 10/6 | JV Field Hockey | Danbury | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | ||
| Fri., 10/6 | FR Girls Volleyball | Fairfield Warde | Home - Westhill HS-Freshman Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/7 | V Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 1:00 p.m. | L 3-0 [Detailed Results] | |
| Sat., 10/7 | JV Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 11:30 a.m. | ||
| Mon., 10/9 | V Girls Soccer | New Canaan | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | L 0-4 | |
| Mon., 10/9 | JV Girls Soccer | New Canaan | Home - Rippowan MS-Rippowam Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 10/9 | V Girls Volleyball | Brien McMahon | Home - Westhill HS-Main Gym [Directions] | 12:30 p.m. | W 3-0 [Detailed Results] | |
| Mon., 10/9 | JV Girls Volleyball | Brien McMahon | Home - Westhill HS-Main Gym [Directions] | 11:00 a.m. | ||
| Mon., 10/9 | FR Girls Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 10:00 a.m. | ||
| Tue., 10/10 | V Boys Cross Country | St. Joseph, Bridgeport Central, Fairfield Ludlowe | Away - St. Joseph HS-Trail [Directions] | 4:00 p.m. | ||
| Tue., 10/10 | V Boys Golf | New Canaan | Home - EG Brennan Golf Course-E Gaynor Brennan Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 10/10 | V Boys Soccer | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | L 2-1 | |
| Tue., 10/10 | JV Boys Soccer | New Canaan | Away - Saxe MS-Field 1 [Directions] | 4:00 p.m. | L 4-0 | |
| Tue., 10/10 | V Girls Cross Country | St. Joseph, Fairfield Ludlowe | Away - St. Joseph HS-Trail [Directions] | 4:00 p.m. | ||
| Tue., 10/10 | V Field Hockey | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 7:00 p.m. | L 1-3 | |
| Tue., 10/10 | JV Field Hockey | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 5:30 p.m. | ||
| Tue., 10/10 | FR Field Hockey | Trumbull | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | Canceled | Cancelled | |
| Wed., 10/11 | V Boys Golf | St. Joseph | Home - EG Brennan Golf Course-E Gaynor Brennan Golf Course [Directions] | 3:15 p.m. | ||
| Wed., 10/11 | FR Boys Soccer | New Canaan | Home - Rippowan MS-Rippowam Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 10/11 | V Girls Swimming and Diving | St. Joseph | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Wed., 10/11 | V Girls Volleyball | Norwalk | Home - Westhill HS-Main Gym [Directions] | 6:00 p.m. | W 3-0 [Detailed Results] | |
| Wed., 10/11 | JV Girls Volleyball | Norwalk | Home - Westhill HS-Main Gym [Directions] | 4:30 p.m. | ||
| Wed., 10/11 | FR Girls Volleyball | Norwalk | Home - Westhill HS-Freshman Gym [Directions] | 4:30 p.m. | ||
| Thu., 10/12 | FR Football | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 5:00 p.m. | ||
| Thu., 10/12 | JV Boys Soccer | Fairfield Warde | Away - Tunxis [Directions] | 4:00 p.m. | L 2-0 | |
| Thu., 10/12 | V Field Hockey | Brien McMahon | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | W 1-0 | |
| Thu., 10/12 | JV Field Hockey | Brien McMahon | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | ||
| Thu., 10/12 | V Girls Soccer | Wilton | Away - Wilton HS-Lilly Field [Directions] | 6:30 p.m. | L 0-3 | |
| Thu., 10/12 | JV Girls Soccer | Wilton | Away - Allen's Meadow-Field 2 [Directions] | 4:00 p.m. | ||
| Fri., 10/13 | V Football | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 7:00 p.m. | L 6-41 | |
| Fri., 10/13 | V Boys Soccer | Wilton | Home - Westhill HS-Westhill Front Turf Field [Directions] | 4:00 p.m. | W 4-2 | |
| Fri., 10/13 | FR Boys Soccer | Wilton | Away - Allen's Meadow-Field 2 [Directions] | 4:30 p.m. | ||
| Fri., 10/13 | V Girls Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | W 3-0 [Detailed Results] | |
| Fri., 10/13 | JV Girls Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 10/13 | FR Girls Volleyball | Stamford | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/14 | JV Boys Soccer | Wilton | Home - Westhill HS-Front Turf [Directions] | 10:30 a.m. | T 3-3 | |
| Sat., 10/14 | V Field Hockey | Norwalk | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 9:00 a.m. | L 0-6 | |
| Sat., 10/14 | JV Field Hockey | Norwalk | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 10:30 a.m. | ||
| Sat., 10/14 | FR Field Hockey | Norwalk | Away - Norwalk HS-Testa Field [Directions] | Canceled | Cancelled | |
| Sat., 10/14 | JV Girls Soccer | Danbury | Home - Westhill HS-Front Turf [Directions] | 12:30 p.m. | ||
| Mon., 10/16 | JV Football | Brien McMahon | Home - Rippowan MS-Rippowam Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 10/16 | V Field Hockey | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 6:30 p.m. | L 0-6 | |
| Mon., 10/16 | JV Field Hockey | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 4:00 p.m. | ||
| Mon., 10/16 | V Girls Soccer | Bridgeport Central | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | L 0-2 | |
| Mon., 10/16 | V Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:30 p.m. | W 3-2 [Detailed Results] | |
| Mon., 10/16 | JV Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 6:00 p.m. | ||
| Mon., 10/16 | FR Girls Volleyball | St. Joseph | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/17 | V Boys Soccer | Bridgeport Central | Away - Bridgeport Central-Kennedy Stadium Turf [Directions] | 6:15 p.m. | T 0-0 | |
| Tue., 10/17 | JV Boys Soccer | Bridgeport Central | Away - Kennedy Stadium (Bridgeport) [Directions] | 4:30 p.m. | W 5-3 | |
| Tue., 10/17 | V Girls Swimming and Diving | Fairfield Warde | Away - Fairfield University-Pool [Directions] | 4:00 p.m. | ||
| Tue., 10/17 | V Girls Volleyball | Ridgefield | Home - Westhill HS-Main Gym [Directions] | 6:00 p.m. | W 3-0 [Detailed Results] | |
| Tue., 10/17 | JV Girls Volleyball | Ridgefield | Home - Westhill HS-Main Gym [Directions] | 4:30 p.m. | ||
| Wed., 10/18 | V Boys Cross Country | FCIAC Championship | Away - Waveny Park | 2:15 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Not Listed-Waveny Park | ||||||
| Wed., 10/18 | V Girls Cross Country | FCIAC Championship | Away - Waveny Park | 2:15 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Not Listed-Waveny Park | ||||||
| Wed., 10/18 | FR Field Hockey | Ridgefield | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:30 p.m. | ||
| Wed., 10/18 | V Girls Soccer | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:30 p.m. | L 1-3 | |
| Wed., 10/18 | JV Girls Soccer | Greenwich | Away - Greenwich HS-Field 3 [Directions] | 4:45 p.m. | ||
| Wed., 10/18 | V Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | W 3-0 [Detailed Results] | |
| Wed., 10/18 | JV Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/18 | FR Girls Volleyball | New Canaan | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/19 | FR Football | Darien | Home - Rippowan MS-Rippowam Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 10/19 | V Boys Soccer | Greenwich | Home - Westhill HS-Front Turf [Directions] | 4:00 p.m. | L 2-1 | |
| Thu., 10/19 | JV Boys Soccer | Greenwich | Away - Greenwich HS-Field 3 [Directions] | 4:45 p.m. | L 6-0 | |
| Thu., 10/19 | FR Boys Soccer | Greenwich | Away - Greenwich HS-Cos Cob Park, Benvenuto Field [Directions] | 4:45 p.m. | ||
| Fri., 10/20 | V Field Hockey | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 5:15 p.m. | T 2-2 | |
| Fri., 10/20 | JV Field Hockey | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | ||
| Fri., 10/20 | FR Field Hockey | Fairfield Warde | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | Canceled | Cancelled | |
| Fri., 10/20 | V Girls Soccer | Darien | Home - Westhill HS-Westhill Front Turf Field [Directions] | 4:00 p.m. | L 0-4 | |
| Fri., 10/20 | JV Girls Soccer | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 10/20 | JV Girls Soccer | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 10/20 | V Girls Volleyball | Wilton | Home - Westhill HS-Main Gym [Directions] | 6:00 p.m. | W 3-0 [Detailed Results] | |
| Fri., 10/20 | JV Girls Volleyball | Wilton | Home - Westhill HS-Main Gym [Directions] | 4:30 p.m. | ||
| Fri., 10/20 | FR Girls Volleyball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Sat., 10/21 | V Football | Danbury | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 1:00 p.m. | L 20-38 | |
| Sat., 10/21 | JV Girls Soccer | Trumbull | Away - Trumbull HS-Cork Field [Directions] | 11:00 a.m. | ||
| Mon., 10/23 | JV Football | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 10/23 | V Field Hockey | Greenwich | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | L 0-4 | |
| Mon., 10/23 | JV Field Hockey | Greenwich | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | ||
| Mon., 10/23 | FR Field Hockey | Greenwich | Away - Greenwich HS-Field 4 [Directions] | 4:00 p.m. | ||
| Mon., 10/23 | V Girls Soccer | Staples | Away - Staples HS-Wakeman Field B (turf) [Directions] | 4:30 p.m. | L 0-7 | |
| Mon., 10/23 | JV Girls Soccer | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | 4:30 p.m. | ||
| Mon., 10/23 | V Girls Swimming and Diving | Danbury | Away - WCSU O'Neill Center Pool [Directions] | 3:45 p.m. | ||
| Mon., 10/23 | V Girls Volleyball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | 5:30 p.m. | W 3-0 [Detailed Results] | |
| Mon., 10/23 | JV Girls Volleyball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | 4:00 p.m. | ||
| Tue., 10/24 | V Boys Golf | CIAC Division I Fall Championship | Away - Stanley GC | 8:30 a.m. | ||
| Tue., 10/24 | V Boys Soccer | Staples | Home - Westhill HS-Westhill Front Turf Field [Directions] | 4:00 p.m. | L 4-3 | |
| Tue., 10/24 | JV Boys Soccer | Staples | Home - Rippowan MS-Rippowam Turf Field [Directions] | 4:00 p.m. | T 1-1 | |
| Tue., 10/24 | FR Boys Soccer | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | 4:30 p.m. | ||
| Tue., 10/24 | JV Girls Soccer | Fairfield Warde | Away - Tunxis [Directions] | 4:30 p.m. | ||
| Wed., 10/25 | V Field Hockey | Fairfield Ludlowe | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | L 0-3 | |
| Wed., 10/25 | JV Field Hockey | Fairfield Ludlowe | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | ||
| Wed., 10/25 | FR Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Front Field [Directions] | 4:00 p.m. | ||
| Wed., 10/25 | V Girls Volleyball | Greenwich | Home - Westhill HS-Main Gym [Directions] | 4:30 p.m. | W 3-0 [Detailed Results] | |
| Wed., 10/25 | JV Girls Volleyball | Greenwich | Home - Westhill HS-Main Gym [Directions] | 3:00 p.m. | ||
| Wed., 10/25 | FR Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 10/26 | FR Football | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:30 p.m. | ||
| Fri., 10/27 | V Football | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 7:00 p.m. | L 6-21 | |
| Fri., 10/27 | V Girls Volleyball | Staples | Home - Westhill HS-Main Gym [Directions] | 6:00 p.m. | W 3-2 [Detailed Results] | |
| Fri., 10/27 | JV Girls Volleyball | Staples | Home - Westhill HS-Main Gym [Directions] | 4:30 p.m. | ||
| Fri., 10/27 | FR Girls Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:30 p.m. | ||
| Sat., 10/28 | JV Girls Swimming and Diving | Greenwich, Danbury, Darien, Fairfield Ludlowe, New Canaan, Norwalk/McMahon, Ridgefield, St. Joseph, Staples, Trumbull, Wilton | Away - Greenwich HS-Pool | 9:30 a.m. | ||
| Mon., 10/30 | JV Football | Ridgefield | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | Postponed | ||
| Mon., 10/30 | V Girls Volleyball | St. Joseph | Home - Westhill HS-Main Gym [Directions] | 6:00 p.m. | W 3-1 [Detailed Results] | |
| Tue., 10/31 | V Boys Cross Country | CIAC Class LL Championship | Away - Wickham Park | 3:15 p.m. | ||
| Tue., 10/31 | V Girls Cross Country | CIAC Class LL Championship | Away - Wickham Park | 2:30 p.m. | ||
| Wed., 11/1 | V Girls Swimming and Diving | Greenwich, Danbury, Darien, Fairfield Ludlowe, Fairfield Warde, New Canaan, Norwalk/McMahon, Ridgefield, St. Joseph, Staples, Trumbull, Wilton | Away - Greenwich HS-Pool | 5:30 p.m. | ||
| Thu., 11/2 | FR Football | Brien McMahon | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | Canceled | Cancelled | |
| Thu., 11/2 | V Boys Soccer | Brien McMahon (Scrim.) | Away - Brien McMahon HS-Casagrande Field [Directions] | Canceled | Cancelled | |
| Thu., 11/2 | V Girls Volleyball | Darien | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:00 p.m. | L 3-0 [Detailed Results] | |
| Sat., 11/4 | V Football | Greenwich | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 1:00 p.m. | L 8-43 | |
| Sat., 11/4 | V Girls Swimming and Diving | Greenwich, Danbury, Darien, Fairfield Ludlowe, Fairfield Warde, New Canaan, Norwalk/McMahon, Ridgefield, St. Joseph, Staples, Trumbull, Wilton | Away - Greenwich HS-Pool | 3:30 p.m. | ||
| Mon., 11/6 | V Boys Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Mon., 11/6 | JV Football | Greenwich | Away - Greenwich HS-Field 7 [Directions] | 3:30 p.m. | ||
| Mon., 11/6 | V Girls Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Tue., 11/7 | V Boys Soccer | East Hartford | Away - East Hartford HS-Soccer Field [Directions] | 2:00 p.m. | W 2-1 | |
| Tue., 11/7 | V Girls Volleyball | West Haven | Home - Westhill HS-Main Gym [Directions] | 6:00 p.m. | W 3-0 [Detailed Results] | |
| Thu., 11/9 | FR Football | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 5:00 p.m. | ||
| Thu., 11/9 | V Boys Soccer | Wilbur Cross | Away - Wilbur Cross HS-Wilbur Cross Athletic Complex [Directions] | 6:00 p.m. | ||
| Thu., 11/9 | V Girls Swimming and Diving | CIAC Class LL Diving Championship | Away - Sheehan | 5:30 p.m. | ||
| Thu., 11/9 | V Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 5:00 p.m. | ||
| Fri., 11/10 | V Football | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 7:00 p.m. | L 14-49 | |
| Sat., 11/11 | JV Football | Trumbull | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | Canceled | Cancelled | |
| Sat., 11/11 | V Boys Soccer | Stamford | Away - On The Road-Darien HS Stadium [Directions] | 10:00 a.m. | ||
| Sat., 11/11 | V Girls Swimming and Diving | CIAC Class LL Qualifying Meet | Away - Cornerstone Pool | 4:30 p.m. | ||
| Tue., 11/14 | V Girls Swimming and Diving | CIAC Class LL Finals | Away - Wesleyan | 6:00 p.m. | ||
| Thu., 11/16 | V Girls Swimming and Diving | CIAC State Open Diving | Away - Middletown | 5:30 p.m. | ||
| Sat., 11/18 | JV Football | Stamford | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 11:00 a.m. | ||
| Sun., 11/19 | V Girls Swimming and Diving | CIAC State Open Swimming | Away - Yale | 1:00 p.m. | ||
| Thu., 11/23 | V Football | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 10:00 a.m. | ||
| Tue., 11/28 | V Football | CIAC Quarterfinals | Away - Higher Seed | 6:30 p.m. | ||
| Tue., 11/28 | V Girls Ice Hockey | Greenwich (Scrim.) | Away - Greenwich - Dorothy Hamill-Rink [Directions] | 5:15 p.m. | ||
| Sat., 12/2 | V Girls Ice Hockey | Rinks of Shelton Jambo | Away - Not Listed-Rinks At Shelton | 4:30 p.m. | ||
| Sun., 12/3 | V Football | CIAC Semifinals | Away - Higher Seed | 12:30 p.m. | ||
| Wed., 12/6 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Terry Conners - Stamford-Ice Rink [Directions] | 7:45 p.m. | W 7-0 | 7:50 Start |
| Thu., 12/7 | V Boys Ice Hockey | Masuk (Scrim.) | Home - Terry Conners - Stamford-Ice Rink [Directions] | 7:20 p.m. | ||
| Fri., 12/8 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 3:30 p.m. | W 3-0 | |
| Sat., 12/9 | V Football | CIAC Championship Games | Away - Site TBA | TBA | ||
| Mon., 12/11 | V Girls Ice Hockey | Simsbury | Away - Simsbury Farms Ice Rink-Ice Rink [Directions] | 4:00 p.m. | W 5-0 | |
| Tue., 12/12 | V Boys Basketball | Hamden (Scrim.) | Away - Hamden HS-HHS Gym [Directions] | 3:15 p.m. | ||
| Tue., 12/12 | V Girls Basketball | Shelton | Home - Westhill HS-Main Gym [Directions] | 6:00 p.m. | L 34-33 | |
| Tue., 12/12 | JV Girls Basketball | Shelton | Home - Westhill HS-Main Gym [Directions] | 4:30 p.m. | ||
| Wed., 12/13 | V Wrestling | Fairfield Warde | Home - Westhill HS-New Gym [Directions] | 6:00 p.m. | ||
| Wed., 12/13 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Home - Terry Conners - Stamford-Ice Rink [Directions] | 5:30 p.m. | W 3-0 | |
| Thu., 12/14 | V Boys Basketball | Joel Barlow | Home - Westhill HS-Main Gym [Directions] | 7:00 p.m. | W 55-50 | |
| Thu., 12/14 | JV Boys Basketball | Joel Barlow | Home - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 12/14 | FR Boys Basketball | Joel Barlow | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 12/16 | V Boys Basketball | Wright Tech | Home - Westhill HS-Main Gym [Directions] | 2:00 p.m. | W 76-16 | |
| Sat., 12/16 | V Boys Ice Hockey | Amity | Home - Terry Conners - Stamford-Ice Rink [Directions] | 8:00 p.m. | W 2-1 | |
| Sat., 12/16 | V Boys Indoor Track | Staples, Greenwich, Stamford, Trumbull | Away - Staples HS-Field House [Directions] | 1:00 p.m. | ||
| Sat., 12/16 | V Wrestling | Ludlowe Invitational | Away - Fairfield Ludlowe HS-Main Gym | 9:00 a.m. | ||
| Sat., 12/16 | V Girls Basketball | Wright Tech | Home - Westhill HS-Main Gym [Directions] | 12:00 p.m. | W 55-34 | |
| Sat., 12/16 | V Girls Indoor Track | Staples, Greenwich, Stamford, Trumbull | Away - Staples HS-Field House [Directions] | 1:00 p.m. | ||
| Mon., 12/18 | V Boys Diving | Darien | Away - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Mon., 12/18 | V Girls Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | 7:00 p.m. | L 3-0 | |
| Tue., 12/19 | V Boys Swimming and Diving | Darien | Away - Darien YMCA [Directions] | 3:00 p.m. | ||
| Wed., 12/20 | V Boys Ice Hockey | Daniel Hand | Home - Terry Conners - Stamford-Ice Rink [Directions] | 5:30 p.m. | W 4-1 | |
| Wed., 12/20 | V Wrestling | Darien | Away - Darien HS-DHS South Gym [Directions] | 5:00 p.m. | ||
| Wed., 12/20 | V Girls Ice Hockey | Greenwich | Home - Terry Conners - Stamford-Ice Rink [Directions] | 7:30 p.m. | W 4-1 | |
| Fri., 12/22 | V Boys Basketball | Ridgefield | Home - Westhill HS-Main Gym [Directions] | 6:00 p.m. | L 71-44 | |
| Fri., 12/22 | JV Boys Basketball | Ridgefield | Home - Westhill HS-Main Gym [Directions] | 4:30 p.m. | ||
| Fri., 12/22 | FR Boys Basketball | Ridgefield | Home - Westhill HS-Main Gym [Directions] | 3:00 p.m. | ||
| Fri., 12/22 | V Girls Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 7:00 p.m. | L 53-17 | |
| Fri., 12/22 | JV Girls Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 12/22 | FR Girls Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 12/23 | V Boys Ice Hockey | Hamden | Home - Terry Conners - Stamford-Ice Rink [Directions] | 4:30 p.m. | W 7-2 | |
| Sat., 12/23 | V Wrestling | Trumbull, Brookfield/Shepaug, Conard, Ridgefield, Staples | Away - Trumbull HS-THS Main Gym | 9:00 a.m. | ||
| Sat., 12/23 | V Girls Ice Hockey | East Catholic Coop | Home - Terry Conners - Stamford-Ice Rink [Directions] | 2:30 p.m. | W 3-1 | |
| Wed., 12/27 | V Girls Basketball | Lauralton Hall | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | L 42-16 | |
| Wed., 12/27 | JV Girls Basketball | Lauralton Hall | Home - Westhill HS-Main Gym [Directions] | 2:30 p.m. | ||
| Thu., 12/28 | V Boys Ice Hockey | John Bapst (ME) | Home - East Haven HS-Patsy DiLungo Rink [Directions] | 2:00 p.m. | W 7-1 | |
| Fri., 12/29 | FR Boys Basketball | Harding | Away - Warren Harding HS-Gym [Directions] | 12:00 p.m. | ||
| Fri., 12/29 | V Wrestling | Glastonbury, Daniel Hand, Lyman Memorial/Windham Tech, New Britain, Newington, Hall | Away - Glastonbury HS-Gym | 9:00 a.m. | ||
| Fri., 12/29 | V Girls Basketball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 5:00 p.m. | L 57-26 | |
| Fri., 12/29 | JV Girls Basketball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 3:30 p.m. | ||
| Sat., 12/30 | V Boys Ice Hockey | Staples | Home - Terry Conners - Stamford-Ice Rink [Directions] | 2:15 p.m. | W 3-0 | |
| Wed., 1/3 | V Boys Swimming and Diving | Trumbull | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Wed., 1/3 | V Wrestling | Brien McMahon | Home - Westhill HS-New Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/3 | V Girls Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 7:00 p.m. | L 63-20 | |
| Wed., 1/3 | JV Girls Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/3 | FR Girls Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/3 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Terry Conners - Stamford-Ice Rink [Directions] | 5:30 p.m. | W 5-2 | |
| Fri., 1/5 | V Boys Basketball | Trumbull | Home - Westhill HS-Main Gym [Directions] | 7:00 p.m. | L 69-50 | |
| Fri., 1/5 | JV Boys Basketball | Trumbull | Home - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/5 | FR Boys Basketball | Trumbull | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/5 | V Boys Ice Hockey | JBWA | Home - Terry Conners - Stamford-Ice Rink [Directions] | 3:30 p.m. | W 2-1 | |
| Fri., 1/5 | V Girls Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 6:30 p.m. | L 44-16 | |
| Fri., 1/5 | JV Girls Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 5:00 p.m. | ||
| Sat., 1/6 | V Boys Basketball | Bethel | Away - Bethel HS-BHS gym [Directions] | 3:00 p.m. | L 57-47 | |
| Sat., 1/6 | JV Boys Basketball | Bethel | Away - Bethel HS-BHS gym [Directions] | 1:30 p.m. | ||
| Sat., 1/6 | FR Boys Basketball | Bethel | Away - Bethel HS-BHS gym [Directions] | 12:00 p.m. | ||
| Sat., 1/6 | V Boys Ice Hockey | Brien McMahon/Norwalk | Home - Terry Conners - Stamford-Ice Rink [Directions] | 12:30 p.m. | W 7-3 | |
| Sat., 1/6 | V Boys Indoor Track | Staples, Brien McMahon, Greenwich, Stamford | Away - Staples HS-Field House [Directions] | 1:00 p.m. | ||
| Sat., 1/6 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Away - Fairfield University-Pool [Directions] | 2:00 p.m. | ||
| Sat., 1/6 | V Wrestling | Warde Wrestling Invitational | Away - Fairfield Warde HS-Large Gym | TBA | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 9:00 a.m. | ||||||
| Sat., 1/6 | V Girls Indoor Track | Staples, Brien McMahon, Greenwich, Stamford | Away - Staples HS-Field House [Directions] | 1:00 p.m. | ||
| Tue., 1/9 | V Boys Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 5:15 p.m. | L 59-51 | |
| Tue., 1/9 | JV Boys Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/9 | V Girls Basketball | Darien | Home - Westhill HS-Main Gym [Directions] | 5:30 p.m. | L 42-23 | |
| Tue., 1/9 | JV Girls Basketball | Darien | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/10 | V Wrestling | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 6:00 p.m. | ||
| Wed., 1/10 | V Girls Gymnastics | Wilton, Stamford | Away - Wilton HS-Aux Gym [Directions] | 4:30 p.m. | 95.60 | |
| Wed., 1/10 | V Girls Ice Hockey | Hamden Coop | Home - Terry Conners - Stamford-Ice Rink [Directions] | 5:30 p.m. | L 2-1 | |
| Thu., 1/11 | V Boys Basketball | Bassick | Home - Westhill HS-Main Gym [Directions] | 7:00 p.m. | L 60-59 | |
| Thu., 1/11 | JV Boys Basketball | Bassick | Home - Westhill HS-Main Gym [Directions] | 5:15 p.m. | ||
| Thu., 1/11 | FR Boys Basketball | Bassick | Home - Westhill HS-Main Gym [Directions] | 3:45 p.m. | ||
| Thu., 1/11 | V Girls Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 7:00 p.m. | L 72-9 | |
| Thu., 1/11 | JV Girls Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 1/11 | FR Girls Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 1/11 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 8:00 p.m. | W 3-1 | |
| Sat., 1/13 | V Boys Ice Hockey | Wilton | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:00 p.m. | W 2-1 | |
| Sat., 1/13 | V Boys Indoor Track | Staples, Bridgeport Central, Danbury, Darien, Greenwich, St. Joseph, Stamford | Away - Staples HS-Field House | 10:00 a.m. | ||
| Sat., 1/13 | V Wrestling | Staples, Fairfield Prep, Guilford, Foran, Maloney, Northwestern, Simsbury, Stratford | Away - Staples HS-Staples Gym | 8:45 a.m. | ||
| Sat., 1/13 | V Girls Indoor Track | Staples, Bridgeport Central, Danbury, Darien, Greenwich, St. Joseph, Stamford | Away - Staples HS-Field House | 10:00 a.m. | ||
| Mon., 1/15 | V Boys Ice Hockey | East Haven Coop | Away - East Haven HS-Patsy DiLungo Rink [Directions] | 1:00 p.m. | W Forfeit | |
| Wed., 1/17 | V Boys Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 7:00 p.m. | L 64-36 | |
| Wed., 1/17 | JV Boys Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/17 | FR Boys Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/17 | V Boys Ice Hockey | Darien | Home - Terry Conners - Stamford-Ice Rink [Directions] | 7:30 p.m. | L 4-2 | |
| Wed., 1/17 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Away - Norwalk HS-Pat Spinola Natatorium [Directions] | 4:00 p.m. | ||
| Wed., 1/17 | V Girls Basketball | Danbury | Home - Westhill HS-Main Gym [Directions] | 7:00 p.m. | L 59-21 | |
| Wed., 1/17 | JV Girls Basketball | Danbury | Home - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/17 | FR Girls Basketball | Danbury | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/17 | V Girls Gymnastics | New Canaan, Stamford | Home - Westhill HS-New Gym [Directions] | 6:00 p.m. | 75.80 | |
| Wed., 1/17 | V Girls Ice Hockey | Darien | Home - Terry Conners - Stamford-Ice Rink [Directions] | 5:30 p.m. | W 2-1 | |
| Fri., 1/19 | V Boys Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 7:00 p.m. | L 49-29 | |
| Fri., 1/19 | JV Boys Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/19 | FR Boys Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/19 | V Girls Basketball | Fairfield Ludlowe | Home - Westhill HS-Main Gym [Directions] | 7:00 p.m. | L 54-11 | |
| Fri., 1/19 | JV Girls Basketball | Fairfield Ludlowe | Home - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/19 | FR Girls Basketball | Fairfield Ludlowe | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 1/20 | V Boys Indoor Track | Staples, Darien, Fairfield Ludlowe, Fairfield Warde, Norwalk, Ridgefield, Trumbull | Away - Staples HS-Field House | 10:00 a.m. | ||
| Sat., 1/20 | V Wrestling | Conard, Brien McMahon, Fairfield Ludlowe, New Fairfield, South Windsor | Away - Conard HS-Main Gym | 9:00 a.m. | ||
| Sat., 1/20 | V Girls Gymnastics | Darien, New Canaan, Stamford | Away - Darien YMCA [Directions] | 2:30 p.m. | 55.00 | |
| Sat., 1/20 | V Girls Ice Hockey | Mercy/NW Catholic/East Hampton | Home - Terry Conners - Stamford-Ice Rink [Directions] | 7:45 p.m. | W 3-1 | 7:50 Start time |
| Sat., 1/20 | V Girls Indoor Track | Staples, Darien, Fairfield Ludlowe, Fairfield Warde, Norwalk, Ridgefield, Trumbull | Away - Staples HS-Field House | 10:00 a.m. | ||
| Mon., 1/22 | V Boys Swimming and Diving | Wilton | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Tue., 1/23 | V Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 7:00 p.m. | L 68-56 | |
| Tue., 1/23 | JV Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/23 | FR Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/23 | V Girls Basketball | Fairfield Warde | Home - Westhill HS-Main Gym [Directions] | 7:00 p.m. | L 42-15 | |
| Tue., 1/23 | JV Girls Basketball | Fairfield Warde | Home - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/23 | FR Girls Basketball | Fairfield Warde | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/24 | V Boys Ice Hockey | St. Joseph | Home - Terry Conners - Stamford-Ice Rink [Directions] | 5:30 p.m. | W 4-2 | |
| Wed., 1/24 | V Wrestling | Danbury | Home - Westhill HS-New Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/24 | V Girls Ice Hockey | New Canaan | Home - Terry Conners - Stamford-Ice Rink [Directions] | 7:30 p.m. | L 2-0 | |
| Thu., 1/25 | V Girls Gymnastics | Staples, Stamford | Away - Staples HS-Westport YMCA [Directions] | 7:00 p.m. | ||
| Fri., 1/26 | V Boys Basketball | Brien McMahon | Home - Westhill HS-Main Gym [Directions] | 7:00 p.m. | L 43-32 | |
| Fri., 1/26 | JV Boys Basketball | Brien McMahon | Home - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/26 | FR Boys Basketball | Brien McMahon | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/26 | V Boys Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | 8:15 p.m. | L 1-7 | |
| Fri., 1/26 | V Boys Swimming and Diving | Danbury | Away - WCSU O'Neill Center Pool [Directions] | 5:30 p.m. | ||
| Fri., 1/26 | V Girls Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 5:30 p.m. | L 67-17 | |
| Fri., 1/26 | JV Girls Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/26 | V Girls Gymnastics | Fairfield Ludlowe, Stamford | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:00 p.m. | 46.05 | |
| Sat., 1/27 | FR Boys Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 10:30 a.m. | ||
| Sat., 1/27 | V Boys Indoor Track | FCIAC West Divisionals | Away - Staples HS-Field House | 10:00 a.m. | ||
| Sat., 1/27 | V Wrestling | Brookfield Invitational | Away - Brookfield HS-BHS Small & Big Gym | 9:30 a.m. | ||
| Sat., 1/27 | JV Wrestling | Norwalk, Brien McMahon, Darien, Fairfield Prep, Fairfield Ludlowe, Fairfield Warde, Greenwich, New Canaan, New Milford, St. Joseph, Stamford, Staples, Trumbull, Weston, Wilton | Away - Norwalk HS-Tom Scarso Gymnasium | 8:00 a.m. | ||
| Sat., 1/27 | FR Girls Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 9:00 a.m. | ||
| Sat., 1/27 | V Girls Ice Hockey | Greenwich | Away - Greenwich - Dorothy Hamill-Rink [Directions] | 5:30 p.m. | W 7-2 | |
| Sat., 1/27 | V Girls Indoor Track | FCIAC West Divisionals | Away - Staples HS-Field House | 10:00 a.m. | ||
| Mon., 1/29 | V Girls Gymnastics | St. Joseph, Stamford, Trumbull | Home - Westhill HS-New Gym [Directions] | 6:00 p.m. | 94.85 | |
| Tue., 1/30 | V Boys Basketball | Norwalk | Home - Westhill HS-Main Gym [Directions] | 7:00 p.m. | L 86-49 | |
| Tue., 1/30 | JV Boys Basketball | Norwalk | Home - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/30 | FR Boys Basketball | Norwalk | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/30 | V Girls Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 6:15 p.m. | L 61-17 | |
| Tue., 1/30 | JV Girls Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:30 p.m. | ||
| Tue., 1/30 | V Girls Ice Hockey | West Haven/SHA | Away - West Haven HS-Bennett Rink [Directions] | 5:30 p.m. | W 3-1 | |
| Wed., 1/31 | V Boys Ice Hockey | Trumbull | Home - Terry Conners - Stamford-Ice Rink [Directions] | 7:50 p.m. | W 7-0 | |
| Wed., 1/31 | V Boys Swimming and Diving | New Canaan | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Wed., 1/31 | V Wrestling | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 6:00 p.m. | ||
| Wed., 1/31 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 4:00 p.m. | W 7-3 | |
| Thu., 2/1 | V Girls Gymnastics | Greenwich, Stamford | Away - Greenwich YWCA [Directions] | 6:30 p.m. | 88.55 | |
| Fri., 2/2 | JV Boys Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 7:00 p.m. | ||
| Fri., 2/2 | FR Boys Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 2/2 | V Boys Swimming and Diving | Greenwich | Away - Greenwich HS-Pool [Directions] | 4:15 p.m. | ||
| Fri., 2/2 | JV Girls Basketball | Stamford | Home - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/2 | FR Girls Basketball | Stamford | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 2/3 | V Boys Basketball | Stamford | Home - Westhill HS-Main Gym [Directions] | 2:00 p.m. | L 56-44 | |
| Sat., 2/3 | V Boys Ice Hockey | Brien McMahon/Norwalk | Away - Sono Ice House-Main Rink [Directions] | 8:50 p.m. | W 12-4 | |
| Sat., 2/3 | V Wrestling | Lancer Duals | Away - Waterford HS-Francis X. Sweeney Field House | 10:00 a.m. | ||
| Sat., 2/3 | V Girls Basketball | Stamford | Home - Westhill HS-Main Gym [Directions] | 12:00 p.m. | L 44-10 | |
| Sat., 2/3 | V Competitive Cheerleading | FCIAC Cheer Championship | Away - Trumbull HS-THS Main Gym | 10:00 a.m. | ||
| Sat., 2/3 | V Girls Ice Hockey | Masuk Coop | Home - Terry Conners - Stamford-Ice Rink [Directions] | 6:30 p.m. | W 2-0 | |
| Sat., 2/3 | Unified Sports Basketball | Stamford | Home - Westhill HS-New Gym [Directions] | Canceled | Cancelled | |
| Mon., 2/5 | V Girls Basketball | St. Joseph | Home - Westhill HS-Main Gym [Directions] | 7:00 p.m. | L 56-16 | |
| Mon., 2/5 | JV Girls Basketball | St. Joseph | Home - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/5 | FR Girls Basketball | St. Joseph | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/6 | V Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 7:00 p.m. | L 67-55 | |
| Tue., 2/6 | JV Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/6 | FR Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/6 | V Boys Ice Hockey | West Haven Coop | Away - West Haven HS-Bennett Rink [Directions] | 7:30 p.m. | W 2-1 | |
| Tue., 2/6 | V Wrestling | Norwalk | Home - Westhill HS-New Gym [Directions] | 6:00 p.m. | ||
| Wed., 2/7 | V Boys Swimming and Diving | Staples | Away - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Wed., 2/7 | V Girls Ice Hockey | Darien | Away - Darien Ice House-Ice Rink [Directions] | 6:20 p.m. | L 3-1 | |
| Thu., 2/8 | V Boys Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 7:00 p.m. | L 56-53 | |
| Thu., 2/8 | JV Boys Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 2/8 | FR Boys Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 2/8 | V Boys Indoor Track | CIAC LL Divisional Championship | Away - Floyd Little Athletic Center | 4:30 p.m. | ||
| Thu., 2/8 | V Girls Basketball | New Canaan | Home - Westhill HS-Main Gym [Directions] | 7:00 p.m. | L 57-12 | |
| Thu., 2/8 | JV Girls Basketball | New Canaan | Home - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 2/8 | FR Girls Basketball | New Canaan | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 2/8 | V Girls Indoor Track | CIAC LL Divisional Championship | Away - Floyd Little Athletic Center | 4:30 p.m. | ||
| Fri., 2/9 | V Boys Swimming and Diving | Ridgefield | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Fri., 2/9 | V Wrestling | New Canaan, Bridgeport Central, Brien McMahon, Danbury, Darien, FCIAC, Fairfield Ludlowe, Fairfield Warde, Greenwich, Norwalk, Ridgefield, St. Joseph, Stamford, Staples, Trumbull, Wilton | Away - New Canaan HS-Main Gym | 4:30 p.m. | ||
| Sat., 2/10 | V Boys Basketball | Weston | Away - Weston HS-Gym (New) [Directions] | 1:00 p.m. | L 45-60 | |
| Sat., 2/10 | JV Boys Basketball | Weston | Away - Weston HS-Gym (New) [Directions] | 11:30 a.m. | ||
| Sat., 2/10 | FR Boys Basketball | Weston | Away - Weston HS-Gym (New) [Directions] | 10:00 a.m. | ||
| Sat., 2/10 | V Boys Ice Hockey | South Windsor | Away - South Windsor Arena-Ice Rink [Directions] | 8:20 p.m. | T 2-2 | |
| Sat., 2/10 | V Girls Basketball | Weston | Home - Westhill HS-Main Gym [Directions] | 12:00 p.m. | L 51-21 | |
| Sat., 2/10 | JV Girls Basketball | Weston | Home - Westhill HS-Main Gym [Directions] | 10:15 a.m. | ||
| Sat., 2/10 | V Girls Ice Hockey | Southington Coop | Home - Terry Conners - Stamford-Ice Rink [Directions] | 6:00 p.m. | L 6-2 | 6:10 start Vs. Avon |
| Mon., 2/12 | V Boys Basketball | Wilton | Home - Westhill HS-Main Gym [Directions] | 7:00 p.m. | L 70-50 | |
| Mon., 2/12 | JV Boys Basketball | Wilton | Home - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/12 | FR Boys Basketball | Wilton | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 2/12 | V Girls Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:00 p.m. | L 78-21 | |
| Mon., 2/12 | JV Girls Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Wed., 2/14 | V Boys Basketball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | 7:00 p.m. | W 55-44 | |
| Wed., 2/14 | JV Boys Basketball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | 5:30 p.m. | ||
| Wed., 2/14 | FR Boys Basketball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | 4:00 p.m. | ||
| Wed., 2/14 | V Boys Ice Hockey | Wilton | Home - Terry Conners - Stamford-Ice Rink [Directions] | 7:00 p.m. | W 4-1 | |
| Wed., 2/14 | V Girls Basketball | Bridgeport Central | Home - Westhill HS-Main Gym [Directions] | 7:00 p.m. | ||
| Wed., 2/14 | JV Girls Basketball | Bridgeport Central | Home - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/14 | FR Girls Basketball | Bridgeport Central | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 2/16 | V Wrestling | CIAC LL Divisional Championship | Away - Trumbull | TBA | ||
| Sat., 2/17 | V Boys Ice Hockey | Trumbull | Away - Total Mortgage Arena - Harbor Yard-Ice Rink [Directions] | 12:30 p.m. | W 3-1 | |
| Sat., 2/17 | V Boys Indoor Track | CIAC State Open Divisional Championship | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/17 | V Girls Indoor Track | CIAC State Open Championship | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Mon., 2/19 | V Boys Basketball | Greenwich | Home - Westhill HS-Main Gym [Directions] | 5:30 p.m. | L 57-46 | |
| Mon., 2/19 | JV Boys Basketball | Greenwich | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 2/19 | FR Boys Basketball | Greenwich | Home - Westhill HS-Main Gym [Directions] | 2:30 p.m. | ||
| Mon., 2/19 | V Boys Ice Hockey | Staples | Away - Milford Ice Pavillion-Ice Rink [Directions] | 4:00 p.m. | W 4-0 | |
| Wed., 2/21 | V Boys Basketball | Staples | Home - Westhill HS-Main Gym [Directions] | 7:00 p.m. | L 65-41 | |
| Wed., 2/21 | JV Boys Basketball | Staples | Home - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/21 | FR Boys Basketball | Staples | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/21 | V Girls Ice Hockey | Darien | Away - Darien Ice House-Ice Rink [Directions] | 7:40 p.m. | L 2-1 | |
| Thu., 2/22 | Unified Sports Basketball | Stamford | Away - Stamford HS-SHS Aux Gym [Directions] | 3:00 p.m. | ||
| Fri., 2/23 | V Boys Ice Hockey | Watertown-Pomperaug | Away - Taft School-Mays [Directions] | 6:30 p.m. | W 4-1 | |
| Fri., 2/23 | V Wrestling | CIAC State Open & Girls Championship | Away - Floyd Little Athletic Center | TBA | ||
| Sat., 2/24 | V Boys Ice Hockey | Darien | Away - Darien Ice House-Ice Rink [Directions] | 5:00 p.m. | ||
| Thu., 2/29 | V Girls Ice Hockey | Mercy/NW Catholic/East Hampton | Home - Terry Conners - Stamford-Ice Rink [Directions] | 7:20 p.m. | W 2-1 | |
| Thu., 2/29 | Unified Sports Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 3:00 p.m. | ||
| Sat., 3/2 | V Girls Ice Hockey | Darien | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | 5:30 p.m. | W 2-1 | |
| Tue., 3/5 | V Boys Ice Hockey | Lyman Hall | Home - Terry Conners - Stamford-Ice Rink [Directions] | 7:40 p.m. | W 5-3 | |
| Tue., 3/5 | V Boys Ice Hockey | CIAC Div II First Round | Away - Higher Seed | TBA | ||
| Wed., 3/6 | V Girls Ice Hockey | New Canaan | Away - Quinnipiac University-TD Bank Sports Center [Directions] | 7:00 p.m. | ||
| Thu., 3/7 | V Boys Swimming and Diving | CIAC Class LL Diving Championship | Away - Sheehan | 5:30 p.m. | ||
| Fri., 3/8 | V Boys Ice Hockey | Amity | Home - Wonderland of Ice-Stadium [Directions] | 8:15 p.m. | L 2-3 | |
| Fri., 3/8 | V Boys Ice Hockey | CIAC Div II Quarterfinal | Away - Site TBA | TBA | ||
| Sat., 3/9 | V Boys Swimming and Diving | CIAC Class LL Qualifying Meet | Away - Cornerstone Pool | 4:30 p.m. | ||
| Tue., 3/12 | V Boys Ice Hockey | CIAC Div II Semifinal | Away - Site TBA | TBA | ||
| Tue., 3/12 | V Boys Swimming and Diving | CIAC Class LL Finals | Away - Wesleyan | 6:00 p.m. | ||
| Thu., 3/14 | V Boys Swimming and Diving | CIAC State Open Diving | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/16 | V Boys Swimming and Diving | CIAC State Open Swimming | Away - Yale | 1:00 p.m. | ||
| Mon., 3/18 | V Boys Ice Hockey | CIAC Div II Final | Away - Site TBA | TBA | ||
| Thu., 3/21 | V Baseball | Darien (Scrim.) | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 3:45 p.m. | ||
| Thu., 3/21 | JV Baseball | Darien (Scrim.) | Away - Darien HS-DHS Baseball - JV Field [Directions] | 3:45 p.m. | ||
| Fri., 3/22 | V Softball | Darien (Scrim.) | Away - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | ||
| Sat., 3/23 | V Baseball | Fairfield Ludlowe (Scrim.) | Away - Brien McMahon HS-Pride Field [Directions] | Canceled | Cancelled | |
| Sat., 3/23 | V Baseball | Brien McMahon (Scrim.) | Home - Brien McMahon HS-Pride Field [Directions] | 2:00 p.m. | Cancelled | |
| Sat., 3/23 | V Boys Lacrosse | Jonathan Law (Scrim.) | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 10:00 a.m. | ||
| Sat., 3/23 | V Boys Volleyball | Stamford (Scrim.) | Home - Westhill HS-Main Gym [Directions] | 10:00 a.m. | ||
| Sun., 3/24 | V Girls Lacrosse | New Milford Jamboree | Away - New Milford HS-Joe Wiser Stadium - NMHS | 8:00 a.m. | ||
| Mon., 3/25 | V Baseball | Brien McMahon (Scrim.) | Away - Brien McMahon HS-Pride Field [Directions] | 4:00 p.m. | ||
| Mon., 3/25 | FR Baseball | Darien (Scrim.) | Away - Darien HS-DHS Baseball - JV Field [Directions] | 3:45 p.m. | L 4-15 | |
| Tue., 3/26 | FR Baseball | Fairfield Ludlowe (Scrim.) | Away - Owen Fish Park-Owen Fish [Directions] | 4:00 p.m. | L 6-7 | |
| Tue., 3/26 | V Boys Lacrosse | Bethel (Scrim.) | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | ||
| Tue., 3/26 | V Boys Volleyball | New Canaan (Scrim.) | Away - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 3/27 | V Baseball | TBA | Home - Westhill HS-Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 3/27 | V Girls Lacrosse | Lyman Hall (Scrim.) | Home - Westhill HS-Westhill Front Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 3/27 | V Softball | Lauralton Hall (Scrim.) | Home - Westhill HS-Varsity Softball Field [Directions] | 4:15 p.m. | ||
| Sat., 3/30 | V Baseball | Daniel Hand | Away - Daniel Hand HS-Polson Baseball Field /DHHS Campus [Directions] | 1:00 p.m. | L 7-2 | |
| Sat., 3/30 | JV Baseball | Daniel Hand | Away - Town Campus - Madison-Baseball Field [Directions] | 11:00 a.m. | W 8-2 | |
| Sat., 3/30 | V Boys Volleyball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 12:00 p.m. | W 3-0 | |
| Sat., 3/30 | V Girls Lacrosse | Stratford/Bunnell | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 12:00 p.m. | ||
| Sat., 3/30 | JV Girls Lacrosse | Stratford/Bunnell | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 1:30 p.m. | ||
| Sat., 3/30 | V Softball | Lyman Hall | Away - Lyman Hall HS-Varsity Softball Field [Directions] | 11:00 a.m. | ||
| Mon., 4/1 | V Boys Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | W 3-0 | |
| Mon., 4/1 | JV Boys Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 4/2 | FR Boys Lacrosse | Trumbull | Away - Trumbull HS-Cork Field [Directions] | 4:00 p.m. | ||
| Tue., 4/2 | V Girls Lacrosse | Notre Dame-Fairfield | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:30 p.m. | ||
| Wed., 4/3 | JV Baseball | Joel Barlow | Away - Joel Barlow HS-Boys & Girls Club of Easton/Redding [Directions] | 4:00 p.m. | ||
| Wed., 4/3 | V Boys Volleyball | Kolbe Cathedral | Away - Kolbe Cathedral HS-Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Wed., 4/3 | JV Boys Volleyball | Kolbe Cathedral | Away - Kolbe Cathedral HS-Gym [Directions] | 4:30 p.m. | ||
| Wed., 4/3 | JV Softball | King and Low-Heywood Thomas (Scrim.) | Away - King and Low-Heywood Thomas-Softball Diamond | 4:45 p.m. | ||
| Thu., 4/4 | V Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | L 5-15 | |
| Thu., 4/4 | JV Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 5:30 p.m. | ||
| Thu., 4/4 | V Boys Outdoor Track | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Thu., 4/4 | V Girls Lacrosse | Fairfield Warde | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | ||
| Thu., 4/4 | JV Girls Lacrosse | Fairfield Warde | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | ||
| Thu., 4/4 | V Girls Outdoor Track | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Fri., 4/5 | JV Baseball | Immaculate | Away - Immaculate HS-Baseball Diamond [Directions] | Postponed | ||
| Fri., 4/5 | V Boys Volleyball | Amity | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 4/5 | JV Boys Volleyball | Amity | Home - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 4/5 | V Softball | Immaculate | Home - Westhill HS-Varsity Softball Field [Directions] | 4:00 p.m. | ||
| Sat., 4/6 | V Baseball | Immaculate | Away - Rogers Park (Danbury, CT)-Rogers Park [Directions] | 6:00 p.m. | W 6-3 | |
| Sat., 4/6 | FR Baseball | Trumbull | Home - Westhill HS-Varsity Baseball Field [Directions] | 11:00 a.m. | L 10-0 | |
| Sat., 4/6 | V Boys Lacrosse | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 10:30 a.m. | W 8-7 | |
| Sat., 4/6 | JV Boys Lacrosse | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 12:00 p.m. | ||
| Sat., 4/6 | V Girls Lacrosse | Brien McMahon | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 12:00 p.m. | ||
| Sat., 4/6 | JV Girls Lacrosse | Brien McMahon | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 1:30 p.m. | ||
| Mon., 4/8 | V Baseball | Ridgefield | Home - Cubeta Stadium [Directions] | 7:00 p.m. | W 14-8 | |
| Mon., 4/8 | FR Boys Lacrosse | St. Joseph | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:00 p.m. | ||
| Mon., 4/8 | V Boys Tennis | Trumbull | Home - Westhill HS-Westhill Tennis Courts [Directions] | 5:00 p.m. | W 6-1 | |
| Mon., 4/8 | V Softball | Brien McMahon | Away - Brien McMahon HS-Softball Diamond [Directions] | 5:00 p.m. | ||
| Mon., 4/8 | V Girls Tennis | Trumbull | Away - Trumbull HS-Tennis Courts [Directions] | 5:00 p.m. | W 7-0 | |
| Tue., 4/9 | V Baseball | New Canaan | Away - Mead Park-Baseball Field [Directions] | 4:00 p.m. | L 8-4 | |
| Tue., 4/9 | JV Baseball | Ridgefield | Home - Rippowan MS-Rippowam Baseball Field [Directions] | 4:00 p.m. | L 1-3 | |
| Tue., 4/9 | FR Baseball | Ridgefield | Away - East Ridge MS-Baseball Field [Directions] | 4:00 p.m. | L 8-9 | |
| Tue., 4/9 | V Boys Outdoor Track | Danbury | Away - Danbury HS-Stadium Track [Directions] | 4:30 p.m. | ||
| Tue., 4/9 | V Boys Tennis | Darien | Away - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 4-3 [Detailed Results] | |
| Tue., 4/9 | V Boys Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Tue., 4/9 | JV Boys Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 4/9 | V Girls Outdoor Track | Danbury | Away - Danbury HS-Stadium Track [Directions] | 4:30 p.m. | ||
| Tue., 4/9 | V Softball | Joel Barlow | Home - Westhill HS-Varsity Softball Field [Directions] | 4:00 p.m. | ||
| Tue., 4/9 | V Girls Tennis | Darien | Home - Westhill HS-Westhill Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Wed., 4/10 | JV Baseball | New Canaan | Away - Waveny Park-Coppo Field [Directions] | 4:00 p.m. | L 6-9 | |
| Wed., 4/10 | FR Baseball | New Canaan | Away - New Canaan HS-Connor Field [Directions] | 4:00 p.m. | L 2-10 | |
| Wed., 4/10 | FR Boys Lacrosse | Darien | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:00 p.m. | ||
| Wed., 4/10 | V Softball | Greenwich | Away - Greenwich HS-Softball Field [Directions] | 4:30 p.m. | ||
| Thu., 4/11 | V Boys Lacrosse | Trumbull | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | L 7-9 | |
| Thu., 4/11 | JV Boys Lacrosse | Trumbull | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:45 p.m. | ||
| Thu., 4/11 | V Girls Lacrosse | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | ||
| Thu., 4/11 | JV Girls Lacrosse | Trumbull | Away - Trumbull HS-Cork Field [Directions] | 4:15 p.m. | ||
| Fri., 4/12 | FR Boys Lacrosse | Wilton | Away - Wilton HS-Fujitani Field - Turf [Directions] | 4:15 p.m. | ||
| Fri., 4/12 | V Boys Volleyball | Trumbull | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | W 3-1 | |
| Fri., 4/12 | JV Boys Volleyball | Trumbull | Home - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 4/12 | JV Softball | Trumbull | Home - TBA [Directions] | TBA | ||
| Sat., 4/13 | V Boys Lacrosse | Bunnell-Stratford | Away - Bunnell HS-Mastroni Field [Directions] | 12:00 p.m. | W 14-0 | |
| Sat., 4/13 | V Girls Lacrosse | New Milford | Away - New Milford HS-Joe Wiser Stadium - NMHS [Directions] | 3:00 p.m. | ||
| Mon., 4/15 | V Baseball | Darien | Home - Westhill HS-Varsity Baseball Field [Directions] | 12:00 p.m. | L 0-10 | |
| Mon., 4/15 | JV Baseball | Darien | Home - Rippowan MS-Rippowam Baseball Field [Directions] | 12:00 p.m. | L 0-12 | |
| Mon., 4/15 | FR Baseball | Darien | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 11:00 a.m. | L 1-11 | |
| Mon., 4/15 | FR Boys Lacrosse | Stamford | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 12:00 p.m. | ||
| Mon., 4/15 | V Boys Tennis | Danbury | Away - Danbury HS-DHS Tennis Courts [Directions] | 2:00 p.m. | W 7-0 [Detailed Results] | |
| Mon., 4/15 | V Boys Volleyball | New Canaan | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 4/15 | JV Boys Volleyball | New Canaan | Home - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 4/15 | V Softball | Darien | Away - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | ||
| Mon., 4/15 | V Girls Tennis | Danbury | Home - Westhill HS-Westhill Tennis Courts [Directions] | 11:00 a.m. | W 5-2 | |
| Tue., 4/16 | V Baseball | Trumbull | Away - Trumbull HS-Varsity Baseball Field [Directions] | 4:00 p.m. | L 0-2 | |
| Tue., 4/16 | JV Baseball | Trumbull | Away - Trumbull HS-JV Baseball Field [Directions] | 4:00 p.m. | W 9-5 | |
| Tue., 4/16 | V Boys Lacrosse | Masuk | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | L 8-18 | |
| Tue., 4/16 | V Boys Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Tennis Courts [Directions] | 2:00 p.m. | W 1-6 [Detailed Results] | |
| Tue., 4/16 | V Softball | Trumbull | Home - Westhill HS-Varsity Softball Field [Directions] | 4:30 p.m. | ||
| Tue., 4/16 | V Girls Tennis | Fairfield Ludlowe | Home - Westhill HS-Westhill Tennis Courts [Directions] | 11:00 a.m. | L 1-6 | |
| Wed., 4/17 | V Baseball | Ridgefield | Away - Governor Field [Directions] | 2:00 p.m. | L 0-7 | |
| Wed., 4/17 | JV Baseball | Ridgefield | Away - East Ridge MS-Baseball Field [Directions] | 2:00 p.m. | W 9-8 | |
| Wed., 4/17 | FR Baseball | Ridgefield | Home - Rippowan MS-Rippowam Baseball Field [Directions] | 12:00 p.m. | L 2-15 | |
| Wed., 4/17 | V Boys Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:30 p.m. | W 3-0 | |
| Wed., 4/17 | JV Boys Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 5:45 p.m. | ||
| Wed., 4/17 | V Softball | Ridgefield | Home - Westhill HS-Varsity Softball Field [Directions] | 12:00 p.m. | ||
| Thu., 4/18 | V Girls Lacrosse | West Haven | Away - West Haven HS-Ken Strong Stadium [Directions] | 11:00 a.m. | ||
| Fri., 4/19 | V Baseball | Danbury | Home - Westhill HS-Varsity Baseball Field [Directions] | 2:00 p.m. | W 9-0 | |
| Fri., 4/19 | JV Baseball | Danbury | Home - Rippowan MS-Rippowam Baseball Field [Directions] | 2:00 p.m. | W 7-6 | |
| Fri., 4/19 | FR Baseball | Danbury | Away - Danbury HS-V Baseball Field [Directions] | 12:00 p.m. | ||
| Fri., 4/19 | V Boys Tennis | Fairfield Warde | Away - Fairfield Warde HS-Blake Courts [Directions] | 2:30 p.m. | W 7-0 [Detailed Results] | |
| Fri., 4/19 | V Boys Volleyball | Staples | Home - Westhill HS-Main Gym [Directions] | 12:30 p.m. | ||
| Fri., 4/19 | JV Boys Volleyball | Staples | Home - Westhill HS-Main Gym [Directions] | 11:00 a.m. | ||
| Fri., 4/19 | V Softball | Danbury | Away - Danbury HS-V Softball field [Directions] | 12:00 p.m. | ||
| Fri., 4/19 | JV Softball | Danbury | Away - Danbury HS-JV Softball Field [Directions] | Postponed | ||
| Sat., 4/20 | V Boys Lacrosse | Fairfield Ludlowe | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 12:00 p.m. | ||
| Sat., 4/20 | JV Boys Lacrosse | Fairfield Ludlowe | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 10:30 a.m. | ||
| Sat., 4/20 | V Girls Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 10:00 a.m. | ||
| Sat., 4/20 | JV Girls Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 11:30 a.m. | ||
| Mon., 4/22 | V Baseball | Fairfield Ludlowe | Home - Westhill HS-Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/22 | JV Baseball | Fairfield Ludlowe | Home - Rippowan MS-Rippowam Baseball Field [Directions] | 4:00 p.m. | L 2-8 | |
| Mon., 4/22 | FR Baseball | Fairfield Ludlowe | Away - Kiwanis Field-Baseball Diamond [Directions] | 4:00 p.m. | W 9-7 | |
| Mon., 4/22 | FR Boys Lacrosse | Fairfield Ludlowe | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | ||
| Mon., 4/22 | V Boys Tennis | Brien McMahon | Home - Westhill HS-Westhill Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Mon., 4/22 | V Softball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 4:15 p.m. | ||
| Mon., 4/22 | JV Softball | Fairfield Ludlowe | Away - Tom Hayden Field [Directions] | Postponed | ||
| Mon., 4/22 | V Girls Tennis | Brien McMahon | Away - Brien McMahon HS-Tennis Courts [Directions] | 4:00 p.m. | W 4-3 | |
| Tue., 4/23 | V Baseball | Fairfield Warde | Home - Westhill HS-Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | JV Baseball | Fairfield Warde | Home - Rippowan MS-Rippowam Baseball Field [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | FR Baseball | Fairfield Warde | Away - Fairfield Warde HS-Baseball Diamond [Directions] | 4:00 p.m. | L 0-10 | |
| Tue., 4/23 | V Boys Lacrosse | New Canaan | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | JV Boys Lacrosse | New Canaan | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | ||
| Tue., 4/23 | V Boys Outdoor Track | Staples | Away - Staples HS-Staples Stadium [Directions] | 4:30 p.m. | ||
| Tue., 4/23 | V Boys Tennis | Norwalk | Home - Westhill HS-Westhill Tennis Courts [Directions] | 4:30 p.m. | W 7-0 [Detailed Results] | |
| Tue., 4/23 | V Boys Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | JV Boys Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 6:00 p.m. | ||
| Tue., 4/23 | V Girls Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 6:00 p.m. | ||
| Tue., 4/23 | JV Girls Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 4:30 p.m. | ||
| Tue., 4/23 | V Girls Outdoor Track | Staples | Away - Staples HS-Staples Stadium [Directions] | 4:30 p.m. | ||
| Tue., 4/23 | V Softball | Fairfield Warde | Away - Fairfield Warde HS-Softball Diamond [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | JV Softball | Fairfield Warde | Away - Fairfield Warde HS-Softball Diamond [Directions] | 5:30 p.m. | ||
| Tue., 4/23 | V Girls Tennis | Norwalk | Away - Grassroots Tennis and Education-Grassroots Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | FR Boys Lacrosse | Stamford | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | ||
| Thu., 4/25 | V Baseball | Joel Barlow | Away - Joel Barlow HS-Baseball Field [Directions] | 4:00 p.m. | ||
| Thu., 4/25 | V Boys Lacrosse | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 4:30 p.m. | ||
| Thu., 4/25 | JV Boys Lacrosse | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 6:00 p.m. | ||
| Thu., 4/25 | V Boys Tennis | Stamford | Away - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Thu., 4/25 | V Boys Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 4/25 | JV Boys Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 4/25 | V Girls Lacrosse | Danbury | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | ||
| Thu., 4/25 | JV Girls Lacrosse | Danbury | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | ||
| Thu., 4/25 | V Girls Tennis | Stamford | Home - Westhill HS-Westhill Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 4/26 | V Baseball | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 5:00 p.m. | ||
| Fri., 4/26 | JV Baseball | Brien McMahon | Away - Roton MS [Directions] | 4:00 p.m. | W 7-5 | |
| Fri., 4/26 | FR Boys Lacrosse | Staples | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | ||
| Fri., 4/26 | V Softball | Brien McMahon | Home - Westhill HS-Varsity Softball Field [Directions] | 4:00 p.m. | ||
| Fri., 4/26 | JV Softball | Brien McMahon | Home - TBA [Directions] | Postponed | ||
| Fri., 4/26 | V Girls Tennis | Fairfield Warde | Home - Westhill HS-Westhill Tennis Courts [Directions] | 3:30 p.m. | ||
| Sat., 4/27 | FR Baseball | Danbury | Home - Westhill HS-Varsity Baseball Field [Directions] | 11:00 a.m. | L 5-0 | |
| Sat., 4/27 | V Boys Lacrosse | Shelton | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 1:00 p.m. | ||
| Sat., 4/27 | JV Boys Lacrosse | Shelton | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 11:00 a.m. | ||
| Sat., 4/27 | V Boys Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 11:00 a.m. | ||
| Sat., 4/27 | JV Boys Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 12:30 p.m. | ||
| Sat., 4/27 | JV Softball | New Canaan | Away - Wilton HS-JV Softball Field [Directions] | 11:00 a.m. | ||
| Mon., 4/29 | V Baseball | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | JV Baseball | Norwalk | Away - City Hall Field [Directions] | 4:00 p.m. | L 0-8 | |
| Mon., 4/29 | FR Baseball | Norwalk | Home - Westhill HS-Varsity Baseball Field [Directions] | 4:00 p.m. | W 5-15 | |
| Mon., 4/29 | V Boys Tennis | St. Joseph | Away - St. Joseph HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Mon., 4/29 | V Softball | Norwalk | Home - Westhill HS-Varsity Softball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | JV Softball | Norwalk | Home - Westhill HS-Varsity Softball Field [Directions] | 6:00 p.m. | ||
| Tue., 4/30 | V Boys Lacrosse | Amity | Away - Amity Regional HS-AHS Grass Field # 3 [Directions] | 4:00 p.m. | ||
| Tue., 4/30 | JV Boys Lacrosse | Amity | Away - Amity Regional HS-AHS Grass Field # 3 [Directions] | 5:45 p.m. | ||
| Tue., 4/30 | V Boys Outdoor Track | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 4:30 p.m. | ||
| Tue., 4/30 | V Boys Tennis | New Canaan | Away - New Canaan HS-NCHS Tennis Courts [Directions] | 4:00 p.m. | L 2-5 | |
| Tue., 4/30 | V Boys Volleyball | Greenwich | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 4/30 | JV Boys Volleyball | Greenwich | Home - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 4/30 | V Girls Outdoor Track | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 4:30 p.m. | ||
| Tue., 4/30 | V Girls Tennis | New Canaan | Home - Westhill HS-Westhill Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | V Baseball | Stamford | Home - Cubeta Stadium [Directions] | 7:00 p.m. | ||
| Wed., 5/1 | JV Baseball | Stamford | Home - Westhill HS-Varsity Baseball Field [Directions] | 4:00 p.m. | L 4-5 | |
| Wed., 5/1 | FR Baseball | Stamford | Away - Belltown Park-Barrett Field, Belltown Park [Directions] | 4:00 p.m. | W 5-3 | |
| Wed., 5/1 | FR Boys Lacrosse | Greenwich | Away - Greenwich HS-Field 4 [Directions] | Canceled | Cancelled | |
| Wed., 5/1 | V Boys Tennis | Ridgefield | Home - Westhill HS-Westhill Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Wed., 5/1 | JV Softball | Stamford | Away - Troy Complex-Diamond 1 [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | V Girls Tennis | Ridgefield | Away - Ridgefield HS-RHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/2 | V Boys Tennis | Wilton | Home - Westhill HS-Westhill Tennis Courts [Directions] | 4:00 p.m. | W 4-3 | |
| Thu., 5/2 | V Boys Volleyball | Fairfield Ludlowe | Home - Westhill HS-Main Gym [Directions] | 4:30 p.m. | ||
| Thu., 5/2 | JV Boys Volleyball | Fairfield Ludlowe | Home - Westhill HS-Main Gym [Directions] | 6:00 p.m. | ||
| Thu., 5/2 | V Softball | Stamford | Away - Troy Complex-Diamond 1 [Directions] | 6:30 p.m. | ||
| Thu., 5/2 | V Girls Tennis | Wilton | Away - Wilton HS-Allen Meadow [Directions] | 4:00 p.m. | ||
| Fri., 5/3 | V Baseball | St. Joseph | Home - Westhill HS-Varsity Baseball Field [Directions] | 4:30 p.m. | ||
| Fri., 5/3 | JV Baseball | St. Joseph | Home - Rippowan MS-Rippowam Baseball Field [Directions] | 4:00 p.m. | W 12-3 | |
| Fri., 5/3 | FR Baseball | St. Joseph | Away - St. Joseph HS-Baseball Diamond [Directions] | 4:00 p.m. | L 2-5 | |
| Fri., 5/3 | FR Boys Lacrosse | Trumbull | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | ||
| Fri., 5/3 | V Softball | St. Joseph | Away - St. Joseph HS-Softball Diamond [Directions] | 4:00 p.m. | ||
| Sat., 5/4 | V Boys Lacrosse | Immaculate | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 2:00 p.m. | ||
| Sat., 5/4 | V Boys Volleyball | St. Joseph | Home - Westhill HS-Main Gym [Directions] | 2:30 p.m. | ||
| Sat., 5/4 | JV Boys Volleyball | St. Joseph | Home - Westhill HS-Main Gym [Directions] | Postponed | ||
| Sat., 5/4 | V Girls Lacrosse | Immaculate | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 12:00 p.m. | ||
| Mon., 5/6 | V Baseball | New Canaan | Home - Cubeta Stadium [Directions] | 7:00 p.m. | ||
| Mon., 5/6 | V Boys Tennis | Bridgeport Central | Away - Bridgeport Central HS-Central High School Tennis Courts [Directions] | 5:00 p.m. | W 7-0 | |
| Mon., 5/6 | V Boys Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | JV Boys Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 5:30 p.m. | ||
| Mon., 5/6 | V Softball | New Canaan | Away - Waveny Park-Orchard Field [Directions] | 6:00 p.m. | ||
| Mon., 5/6 | JV Softball | New Canaan | Away - Waveny Park-Orchard Field [Directions] | Canceled | Cancelled | |
| Mon., 5/6 | V Girls Tennis | Bridgeport Central | Home - Westhill HS-Westhill Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | JV Baseball | New Canaan | Home - Rippowan MS-Rippowam Baseball Field [Directions] | 4:00 p.m. | L 4-13 | |
| Tue., 5/7 | FR Baseball | New Canaan | Away - New Canaan HS-Coppo Field [Directions] | 4:00 p.m. | W 5-4 | |
| Tue., 5/7 | V Boys Lacrosse | Staples | Away - Staples HS-Staples Stadium [Directions] | 7:00 p.m. | ||
| Tue., 5/7 | JV Boys Lacrosse | Staples | Away - Staples HS-Wakeman Field B (turf) [Directions] | 4:30 p.m. | ||
| Tue., 5/7 | V Boys Outdoor Track | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | V Boys Tennis | Greenwich | Home - Westhill HS-Westhill Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Tue., 5/7 | V Girls Lacrosse | Staples | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | ||
| Tue., 5/7 | JV Girls Lacrosse | Staples | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | V Girls Outdoor Track | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | V Girls Tennis | Greenwich | Away - Greenwich HS-Tennis Courts [Directions] | 4:15 p.m. | ||
| Wed., 5/8 | V Baseball | Wilton | Away - Wilton HS-Varsity Baseball Field [Directions] | 6:30 p.m. | ||
| Wed., 5/8 | JV Baseball | Wilton | Away - Wilton HS-JV Baseball Field [Directions] | 4:15 p.m. | L 6-3 | |
| Wed., 5/8 | FR Baseball | Wilton | Home - Rippowan MS-Rippowam Baseball Field [Directions] | Postponed | ||
| Wed., 5/8 | V Boys Volleyball | Danbury | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | JV Boys Volleyball | Danbury | Home - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 5/8 | V Softball | Wilton | Home - Westhill HS-Varsity Softball Field [Directions] | 4:30 p.m. | ||
| Wed., 5/8 | JV Softball | Wilton | Home - Roxbury Elementary School-Softball Field [Directions] | 4:45 p.m. | ||
| Wed., 5/8 | JV Softball | Wilton | Home - TBA [Directions] | TBA | ||
| Wed., 5/8 | V Girls Tennis | St. Joseph | Home - Westhill HS-Westhill Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/9 | V Boys Lacrosse | Norwalk | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | ||
| Thu., 5/9 | JV Boys Lacrosse | Norwalk | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | ||
| Thu., 5/9 | V Boys Tennis | Staples | Home - Westhill HS-Westhill Tennis Courts [Directions] | 4:00 p.m. | L 3-4 | |
| Thu., 5/9 | V Girls Lacrosse | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | 5:30 p.m. | ||
| Thu., 5/9 | JV Girls Lacrosse | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | 3:45 p.m. | ||
| Thu., 5/9 | V Girls Tennis | Staples | Away - Staples HS-Staples Tennis Courts [Directions] | 4:30 p.m. | ||
| Fri., 5/10 | V Boys Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | ||
| Sat., 5/11 | V Boys Lacrosse | Stamford | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:15 p.m. | ||
| Sat., 5/11 | JV Boys Lacrosse | Stamford | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 3:00 p.m. | ||
| Sat., 5/11 | V Girls Lacrosse | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 12:00 p.m. | ||
| Sat., 5/11 | JV Girls Lacrosse | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 10:30 a.m. | ||
| Mon., 5/13 | V Baseball | Greenwich | Away - Havemeyer Field-Havermeyer Field [Directions] | 4:30 p.m. | ||
| Mon., 5/13 | JV Baseball | Greenwich | Away - Julian Curtiss School [Directions] | 4:30 p.m. | L 3-9 | |
| Mon., 5/13 | FR Baseball | Greenwich | Home - Westhill HS-Varsity Baseball Field [Directions] | 4:00 p.m. | W 4-13 | |
| Mon., 5/13 | FR Boys Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | Postponed | ||
| Mon., 5/13 | V Boys Volleyball | Bridgeport Central | Home - Westhill HS-Main Gym [Directions] | 6:00 p.m. | ||
| Mon., 5/13 | JV Boys Volleyball | Wilton | Home - Westhill HS-Main Gym [Directions] | 4:30 p.m. | ||
| Mon., 5/13 | V Softball | Greenwich | Home - Westhill HS-Varsity Softball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | JV Softball | Greenwich | Home - Westhill HS-Varsity Softball Field [Directions] | 6:00 p.m. | ||
| Mon., 5/13 | V Girls Tennis | Greenwich | Away - Greenwich HS-Tennis Courts [Directions] | 4:30 p.m. | ||
| Tue., 5/14 | V Baseball | Bridgeport Central | Home - Westhill HS-Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | V Boys Lacrosse | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 4:30 p.m. | ||
| Tue., 5/14 | JV Boys Lacrosse | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 6:00 p.m. | ||
| Tue., 5/14 | V Boys Outdoor Track | Stamford | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 2:30 p.m. | ||
| Tue., 5/14 | V Boys Tennis | Darien | Home - Westhill HS-Westhill Tennis Courts [Directions] | 4:00 p.m. | L 3-4 | |
| Tue., 5/14 | V Girls Lacrosse | St. Joseph | Home - Westhill HS-Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Tue., 5/14 | JV Girls Lacrosse | St. Joseph | Home - Westhill HS-Westhill Front Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | V Girls Outdoor Track | Stamford | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 2:30 p.m. | ||
| Tue., 5/14 | V Softball | Staples | Home - Westhill HS-Varsity Softball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | FR Boys Lacrosse | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 5:00 p.m. | ||
| Wed., 5/15 | V Boys Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:45 p.m. | ||
| Wed., 5/15 | JV Boys Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:30 p.m. | ||
| Thu., 5/16 | V Baseball | Staples | Home - Allen's Meadow [Directions] | 5:00 p.m. | ||
| Thu., 5/16 | V Boys Outdoor Track | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 3:00 p.m. | ||
| Thu., 5/16 | V Girls Lacrosse | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 6:00 p.m. | ||
| Thu., 5/16 | JV Girls Lacrosse | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 4:30 p.m. | ||
| Thu., 5/16 | V Girls Outdoor Track | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 3:00 p.m. | ||
| Thu., 5/16 | JV Softball | Bridgeport Central | Away - Bridgeport Central HS-Softball Diamond 2 [Directions] | Canceled | Cancelled | |
| Thu., 5/16 | JV Softball | New Canaan | Home - Westhill HS-Varsity Softball Field [Directions] | Postponed | ||
| Fri., 5/17 | FR Baseball | Darien | Home - Westhill HS-Varsity Baseball Field [Directions] | 4:00 p.m. | L 20-1 | |
| Sat., 5/18 | V Boys Volleyball | Trumbull | Home - Westhill HS-Main Gym [Directions] | 2:00 p.m. | ||
| Sat., 5/18 | V Softball | Bridgeport Central | Away - Bridgeport Central-Varsity Softball Field [Directions] | 10:00 a.m. | ||
| Mon., 5/20 | V Boys Volleyball | Darien | Away - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | ||
| Tue., 5/21 | JV Baseball | Staples | Away - Staples HS-Wakeman Field [Directions] | 4:30 p.m. | ||
| Tue., 5/21 | FR Baseball | Staples | Away - Staples HS-Baseball Diamond [Directions] | 4:30 p.m. | W 10-8 | |
| Tue., 5/21 | V Boys Outdoor Track | FCIAC Championship | Away - Danbury HS-Danbury HS Stadium | 4:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 2:30 p.m. | ||||||
| Tue., 5/21 | V Girls Outdoor Track | FCIAC Championship | Away - Danbury HS-Danbury HS Stadium | 2:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 2:30 p.m. | ||||||
| Tue., 5/21 | V Softball | Darien (Scrim.) | Away - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 5/22 | V Softball | Staples (Scrim.) | Away - Staples HS-Wakeman Softball Field [Directions] | 4:30 p.m. | ||
| Thu., 5/23 | V Baseball | Darien (Scrim.) | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 3:45 p.m. | ||
| Fri., 5/24 | V Boys Tennis | Southington | Home - Westhill HS-Westhill Tennis Courts [Directions] | 3:30 p.m. | ||
| Fri., 5/24 | V Softball | New Canaan (Scrim.) | Away - Waveny Park-Orchard Field [Directions] | 4:00 p.m. | ||
| Fri., 5/24 | V Girls Tennis | Shelton | Away - Shelton HS-Tennis Courts [Directions] | 3:45 p.m. | ||
| Sat., 5/25 | V Girls Tennis | Greenwich | Away - Greenwich HS-Tennis Courts [Directions] | 10:00 a.m. | ||
| Tue., 5/28 | V Baseball | Southington | Away - Southington HS-4 Baseball Varsity Field [Directions] | 3:30 p.m. | ||
| Tue., 5/28 | V Boys Tennis | Greenwich | Away - Greenwich HS-Tennis Courts [Directions] | 4:30 p.m. | ||
| Tue., 5/28 | V Softball | Naugatuck | Away - Naugatuck HS-Softball Diamond [Directions] | 4:30 p.m. | ||
| Wed., 5/29 | V Boys Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 4:30 p.m. | ||
| Wed., 5/29 | V Boys Volleyball | Southington | Home - Westhill HS-Main Gym [Directions] | 6:00 p.m. | ||
| Wed., 5/29 | V Softball | Middletown | Away - Pat Kidney Sports Complex-Lucille Lu Gecewicz Softball Field [Directions] | 4:00 p.m. | ||
| Sat., 6/1 | V Boys Volleyball | East Hartford | Home - Westhill HS-Main Gym [Directions] | 12:00 p.m. | ||