| Westhill 2022-23 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 776 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Sat., 8/27 | V Football | Stamford (Scrim.) | Away - Stamford HS-Boyle Stadium [Directions] | 10:00 a.m. | ||
| Sat., 8/27 | FR Football | Norwalk (Scrim.) | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | 10:00 a.m. | ||
| Tue., 8/30 | V Boys Golf | New Canaan | Away - CCNC [Directions] | 3:00 p.m. | Westhill HS: 167 NC: 162 | |
| Wed., 8/31 | V Boys Golf | Darien | Away - Woodway Country Club [Directions] | 3:15 p.m. | Darien: 178 Westhill: 180 | |
| Wed., 8/31 | V Boys Soccer | Brien McMahon (Scrim.) | Home - Westhill HS-Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Thu., 9/1 | V Boys Golf | Danbury | Away - Richter Park Golf Course [Directions] | 3:00 p.m. | Danbury: 180 Westhill: 173 | |
| Fri., 9/2 | V Football | Stratford (Scrim.) | Away - Penders Field-Penders Field - Stratford [Directions] | 6:00 p.m. | ||
| Fri., 9/2 | FR Football | Stratford (Scrim.) | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:00 p.m. | ||
| Tue., 9/6 | V Girls Soccer | Bethel (Scrim.) | Home - Westhill HS-Westhill Front Turf Field [Directions] | 5:00 p.m. | ||
| Wed., 9/7 | V Boys Golf | Greenwich | Home - EG Brennan Golf Course-E Gaynor Brennan Golf Course [Directions] | 3:15 p.m. | Greenwich: 160 Westhill: 170 | |
| Thu., 9/8 | V Boys Soccer | Trumbull | Away - Trumbull HS-Cork Field [Directions] | 5:30 p.m. | L 0-2 | |
| Thu., 9/8 | JV Boys Soccer | Trumbull | Away - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Thu., 9/8 | FR Boys Soccer | Trumbull | Home - Rippowan MS-Rippowam Turf Field [Directions] | 4:00 p.m. | L 0-1 | |
| Thu., 9/8 | V Field Hockey | Staples | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | L 0-10 | |
| Thu., 9/8 | JV Field Hockey | Staples | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | Postponed | ||
| Thu., 9/8 | V Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:30 p.m. | L 1-3 | |
| Thu., 9/8 | JV Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | Postponed | ||
| Fri., 9/9 | V Football | Bassick | Away - Kennedy Stadium (Bridgeport) [Directions] | 7:00 p.m. | W 41-6 | |
| Fri., 9/9 | V Girls Soccer | Trumbull | Home - Westhill HS-Westhill Front Turf Field [Directions] | 4:00 p.m. | L 4-0 | |
| Fri., 9/9 | JV Girls Soccer | Trumbull | Home - Rippowan MS-Rippowam Turf Field [Directions] | 4:00 p.m. | L 5-0 | |
| Fri., 9/9 | FR Girls Soccer | Trumbull | Away - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Fri., 9/9 | V Girls Swimming and Diving | Staples | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Sat., 9/10 | V Boys Soccer | Darien | Home - Westhill HS-Westhill Front Turf Field [Directions] | 12:00 p.m. | L 3-6 | |
| Sat., 9/10 | JV Boys Soccer | Darien | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 12:00 p.m. | ||
| Sat., 9/10 | FR Boys Soccer | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | W 4-5 | |
| Sat., 9/10 | V Girls Volleyball | Pomperaug | Home - Westhill HS-Main Gym [Directions] | 11:30 a.m. | W 3-0 | |
| Sat., 9/10 | JV Girls Volleyball | Pomperaug | Home - Westhill HS-Main Gym [Directions] | 10:00 a.m. | ||
| Mon., 9/12 | V Girls Soccer | Darien | Away - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | L 6-0 | |
| Mon., 9/12 | JV Girls Soccer | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 5:00 p.m. | L 3-0 | |
| Tue., 9/13 | V Boys Cross Country | Trumbull, Brien McMahon, Greenwich | Away - Trumbull HS-Cross Country Course [Directions] | 4:00 p.m. | ||
| Tue., 9/13 | V Boys Golf | Wilton | Home - EG Brennan Golf Course-E Gaynor Brennan Golf Course [Directions] | 3:15 p.m. | Wilton: 156 Westhill: 160 | |
| Tue., 9/13 | FR Boys Soccer | Brien McMahon | Home - Rippowan MS-Rippowam Turf Field [Directions] | 4:00 p.m. | L 1-4 | |
| Tue., 9/13 | V Girls Cross Country | Trumbull, Brien McMahon, Greenwich | Away - Trumbull HS-Cross Country Course [Directions] | 4:00 p.m. | ||
| Tue., 9/13 | V Field Hockey | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | L 0-10 | |
| Tue., 9/13 | JV Field Hockey | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Wed., 9/14 | V Boys Golf | Trumbull | Home - EG Brennan Golf Course-E Gaynor Brennan Golf Course [Directions] | 3:15 p.m. | Trumbull: 172 Westhill: 167 | |
| Wed., 9/14 | V Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 4:00 p.m. | T 1-1 | |
| Wed., 9/14 | JV Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 5:45 p.m. | ||
| Wed., 9/14 | V Girls Soccer | Brien McMahon | Home - Westhill HS-Westhill Front Turf Field [Directions] | 4:30 p.m. | L 8-0 | |
| Wed., 9/14 | JV Girls Soccer | Brien McMahon | Home - Rippowan MS-Rippowam Turf Field [Directions] | Postponed | [Detailed Results] | |
| Wed., 9/14 | V Girls Swimming and Diving | Danbury | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Wed., 9/14 | V Girls Volleyball | Bassick | Away - Bassick HS-Gym [Directions] | 5:00 p.m. | W 3-0 | |
| Wed., 9/14 | JV Girls Volleyball | Bassick | Away - Bassick HS-New gym [Directions] | 4:00 p.m. | ||
| Thu., 9/15 | FR Football | Fairfield Ludlowe | Home - Rippowan MS-Rippowam Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 9/15 | V Field Hockey | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 4:00 p.m. | L 2-1 | |
| Thu., 9/15 | JV Field Hockey | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 5:30 p.m. | ||
| Fri., 9/16 | V Boys Soccer | Bridgeport Central | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:45 p.m. | W 5-0 | |
| Fri., 9/16 | JV Boys Soccer | Bridgeport Central | Home - Rippowan MS-Rippowam Turf Field [Directions] | 4:30 p.m. | ||
| Fri., 9/16 | V Girls Swimming and Diving | New Canaan | Away - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Fri., 9/16 | V Girls Volleyball | Bunnell | Away - Bunnell HS-David Johnson Gymnasium [Directions] | 6:30 p.m. | W 3-0 | |
| Fri., 9/16 | JV Girls Volleyball | Bunnell | Away - Bunnell HS-David Johnson Gymnasium [Directions] | 5:00 p.m. | ||
| Sat., 9/17 | V Football | Trumbull | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 2:30 p.m. | L 7-49 | |
| Sat., 9/17 | V Field Hockey | Stamford | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 11:00 a.m. | L 0-4 | |
| Sat., 9/17 | JV Field Hockey | Stamford | Home - Westhill HS-Front Turf [Directions] | 12:30 p.m. | ||
| Mon., 9/19 | JV Football | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | ||
| Mon., 9/19 | V Boys Soccer | Staples | Away - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | L 4-3 | |
| Mon., 9/19 | JV Boys Soccer | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Mon., 9/19 | FR Boys Soccer | Staples | Home - Rippowan MS-Rippowam Turf Field [Directions] | 4:00 p.m. | W 1-0 | |
| Tue., 9/20 | V Boys Cross Country | Darien, Ridgefield, St. Joseph | Home - Scofield Magnet MS-Cross Country Course [Directions] | 4:00 p.m. | ||
| Tue., 9/20 | V Girls Cross Country | Darien, Ridgefield, St. Joseph | Home - Scofield Magnet MS-Cross Country Course [Directions] | 4:00 p.m. | ||
| Tue., 9/20 | V Field Hockey | Trumbull | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | L 0-2 | |
| Tue., 9/20 | JV Field Hockey | Trumbull | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | ||
| Tue., 9/20 | V Girls Soccer | Staples | Home - Westhill HS-Westhill Front Turf Field [Directions] | 4:30 p.m. | L 6-0 | |
| Tue., 9/20 | JV Girls Soccer | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | L 5-0 | |
| Wed., 9/21 | V Boys Golf | Brien McMahon | Away - Oak Hills Golf Course [Directions] | 3:15 p.m. | Westhill: 164 McMahon: 170 | |
| Thu., 9/22 | V Boys Golf | Staples | Home - EG Brennan Golf Course-E Gaynor Brennan Golf Course [Directions] | 3:15 p.m. | Staples: 156 Westhill: 172 | |
| Thu., 9/22 | V Boys Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 6:30 p.m. | L 3-0 | |
| Thu., 9/22 | JV Boys Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 4:15 p.m. | ||
| Thu., 9/22 | FR Boys Soccer | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 4:00 p.m. | L 4-3 | |
| Thu., 9/22 | V Girls Soccer | Norwalk | Home - Westhill HS-Westhill Front Turf Field [Directions] | 4:00 p.m. | L 1-0 | |
| Thu., 9/22 | JV Girls Soccer | Norwalk | Home - Rippowan MS-Rippowam Turf Field [Directions] | 4:00 p.m. | W 3-0 | |
| Thu., 9/22 | V Girls Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | L 3-1 | |
| Thu., 9/22 | JV Girls Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 4:30 p.m. | ||
| Thu., 9/22 | FR Girls Volleyball | Trumbull | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/24 | V Football | Wilbur Cross | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 1:00 p.m. | L 0-28 | |
| Sat., 9/24 | V Boys Soccer | East Hartford | Away - East Hartford HS-Farmington Sports Arena [Directions] | 12:30 p.m. | W 2-1 | |
| Sat., 9/24 | V Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 10:00 a.m. | L 1-8 | |
| Sat., 9/24 | JV Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 11:30 a.m. | ||
| Sat., 9/24 | V Girls Soccer | Joel Barlow | Away - Joel Barlow HS-Field I (Stadium) [Directions] | 12:30 p.m. | L 5-1 | |
| Sat., 9/24 | JV Girls Soccer | Joel Barlow | Away - Joel Barlow HS-Field E (Softball) [Directions] | 12:30 p.m. | L 5-0 | |
| Sat., 9/24 | V Girls Volleyball | Kolbe Cathedral | Home - Westhill HS-Main Gym [Directions] | 12:00 p.m. | W 3-0 | |
| Sat., 9/24 | JV Girls Volleyball | Kolbe Cathedral | Home - Westhill HS-Main Gym [Directions] | 10:30 a.m. | ||
| Tue., 9/27 | V Boys Golf | St. Joseph | Away - Tashua Knolls Golf Course [Directions] | 3:00 p.m. | St. Joseph: 162 Westhill: 169 | |
| Tue., 9/27 | JV Boys Golf | St. Joseph | Away - Tashua Knolls Golf Course-Tashua Glen [Directions] | 3:15 p.m. | ||
| Tue., 9/27 | V Girls Soccer | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 7:00 p.m. | L 4-0 | |
| Tue., 9/27 | JV Girls Soccer | Fairfield Warde | Away - Fairfield Warde HS-Fairfield Warde Grass Utility Field [Directions] | 4:00 p.m. | L 6-1 | |
| Tue., 9/27 | V Girls Volleyball | Darien | Home - Westhill HS-Main Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Tue., 9/27 | JV Girls Volleyball | Darien | Home - Westhill HS-Main Gym [Directions] | 4:30 p.m. | ||
| Tue., 9/27 | FR Girls Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 9/28 | V Boys Cross Country | New Canaan, Stamford, Wilton | Away - Waveny Park [Directions] | 4:30 p.m. | ||
| Wed., 9/28 | V Boys Golf | Fairfield Warde, Norwalk | Home - EG Brennan Golf Course-E Gaynor Brennan Golf Course [Directions] | 3:15 p.m. | Fairfield Warde: 156 Westhill: 160 Norwalk: 179 | |
| Wed., 9/28 | V Boys Soccer | Fairfield Warde | Home - Westhill HS-Westhill Front Turf Field [Directions] | 4:30 p.m. | T 1-1 | |
| Wed., 9/28 | JV Boys Soccer | Fairfield Warde | Away - Fairfield Warde HS-Fairfield Warde Grass Utility Field [Directions] | 4:00 p.m. | ||
| Wed., 9/28 | FR Boys Soccer | Fairfield Warde | Away - Tunxis [Directions] | 4:00 p.m. | W 3-6 | |
| Wed., 9/28 | V Girls Cross Country | New Canaan, Stamford, Wilton | Away - Waveny Park [Directions] | 4:30 p.m. | ||
| Wed., 9/28 | V Field Hockey | New Canaan | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | L 0-10 | |
| Wed., 9/28 | JV Field Hockey | New Canaan | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | ||
| Wed., 9/28 | V Girls Swimming and Diving | Wilton | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Thu., 9/29 | V Boys Golf | Stamford | Away - Stamford High-Sterling Farms Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 9/29 | V Girls Soccer | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 4:00 p.m. | L 7-0 | |
| Thu., 9/29 | JV Girls Soccer | St. Joseph | Away - St. Joseph HS-Lower Grass Field [Directions] | 4:00 p.m. | L 5-0 | |
| Thu., 9/29 | V Girls Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:30 p.m. | W 3-2 | |
| Thu., 9/29 | JV Girls Volleyball | Brien McMahon | Home - Westhill HS-New Gym [Directions] | 4:00 p.m. | ||
| Thu., 9/29 | FR Girls Volleyball | Brien McMahon | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/30 | V Boys Soccer | St. Joseph | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:30 p.m. | W 4-1 | |
| Fri., 9/30 | V Girls Swimming and Diving | Trumbull | Away - Bridgeport Univ Pool-Pool [Directions] | 4:00 p.m. | ||
| Sat., 10/1 | V Football | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 1:00 p.m. | L 14-62 | |
| Sat., 10/1 | V Field Hockey | St. Joseph | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 2:00 p.m. | L 0-1 | |
| Sat., 10/1 | JV Field Hockey | St. Joseph | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 3:45 p.m. | ||
| Sat., 10/1 | V Girls Volleyball | Bridgeport Central | Home - Westhill HS-Main Gym [Directions] | 12:00 p.m. | W 3-0 | |
| Sat., 10/1 | JV Girls Volleyball | Bridgeport Central | Home - Westhill HS-Main Gym [Directions] | 10:30 a.m. | ||
| Mon., 10/3 | V Boys Cross Country | Staples, Norwalk | Away - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Mon., 10/3 | JV Football | Greenwich | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | ||
| Mon., 10/3 | V Boys Golf | Ridgefield | Away - Ridgefield Golf Course [Directions] | 3:00 p.m. | Ridgefield: 161 Westhill: 173 | |
| Mon., 10/3 | V Girls Cross Country | Staples, Norwalk | Away - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Mon., 10/3 | V Field Hockey | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 7:00 p.m. | L 0-8 | |
| Mon., 10/3 | JV Field Hockey | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 5:00 p.m. | ||
| Mon., 10/3 | JV Girls Soccer | Wilton | Home - Rippowan MS-Rippowam Turf Field [Directions] | 4:00 p.m. | L 5-0 | |
| Mon., 10/3 | V Girls Swimming and Diving | Norwalk/McMahon | Away - Norwalk HS-Pat Spinola Natatorium [Directions] | 4:00 p.m. | ||
| Tue., 10/4 | V Girls Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:30 p.m. | W 3-0 | |
| Thu., 10/6 | V Boys Soccer | Wilton | Away - Wilton HS-Lilly Field [Directions] | 5:30 p.m. | W 4-1 | |
| Thu., 10/6 | JV Boys Soccer | Wilton | Away - Allen's Meadow-2A [Directions] | 4:30 p.m. | ||
| Thu., 10/6 | FR Boys Soccer | Wilton | Home - Rippowan MS-Rippowam Turf Field [Directions] | 4:30 p.m. | T 2-2 | |
| Thu., 10/6 | V Girls Swimming and Diving | Greenwich | Away - Greenwich HS-Pool [Directions] | 5:30 p.m. | ||
| Thu., 10/6 | V Girls Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 6:00 p.m. | W 3-2 | |
| Thu., 10/6 | JV Girls Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:30 p.m. | ||
| Thu., 10/6 | FR Girls Volleyball | Staples | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/7 | V Field Hockey | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 5:00 p.m. | L 1-2 | |
| Fri., 10/7 | JV Field Hockey | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 6:30 p.m. | ||
| Fri., 10/7 | V Girls Soccer | Wilton | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | T 0-0 | |
| Sat., 10/8 | FR Football | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 10:00 a.m. | ||
| Sat., 10/8 | FR Girls Volleyball | Norwalk | Home - Westhill HS-New Gym [Directions] | 10:30 a.m. | ||
| Mon., 10/10 | V Boys Soccer | Fairfield Ludlowe | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | T 1-1 | |
| Mon., 10/10 | JV Boys Soccer | Fairfield Ludlowe | Home - Westhill HS-Front Turf [Directions] | 4:00 p.m. | ||
| Mon., 10/10 | FR Boys Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | 4:00 p.m. | T 0-0 | |
| Mon., 10/10 | V Field Hockey | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 4:00 p.m. | L 0-10 | |
| Mon., 10/10 | JV Field Hockey | Norwalk | Away - Norwalk HS-Testa Field [Directions] | Postponed | ||
| Mon., 10/10 | V Girls Volleyball | Fairfield Warde | Home - Westhill HS-Main Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Mon., 10/10 | JV Girls Volleyball | Fairfield Warde | Home - Westhill HS-Main Gym [Directions] | 4:30 p.m. | ||
| Tue., 10/11 | V Boys Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 2:50 p.m. | Ludlowe: 158 Westhill: 175 | |
| Tue., 10/11 | V Girls Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 7:00 p.m. | L 7-0 | |
| Tue., 10/11 | JV Girls Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | 4:00 p.m. | L 5-0 | |
| Wed., 10/12 | V Boys Cross Country | Fairfield Ludlowe, Danbury, Fairfield Warde | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | ||
| Wed., 10/12 | V Boys Golf | Stamford | Home - EG Brennan Golf Course-E Gaynor Brennan Golf Course [Directions] | 3:15 p.m. | Stamford: 169 Westhill: 155 | |
| Wed., 10/12 | V Boys Soccer | Stamford | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | W 4-1 | |
| Wed., 10/12 | FR Boys Soccer | Stamford | Away - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | T 0-0 | |
| Wed., 10/12 | V Girls Cross Country | Fairfield Ludlowe, Danbury, Fairfield Warde | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | ||
| Wed., 10/12 | V Field Hockey | Ridgefield | Home - Westhill HS-Front Turf [Directions] | 4:00 p.m. | L 1-10 | |
| Wed., 10/12 | JV Field Hockey | Ridgefield | Home - Westhill HS-Front Turf [Directions] | Postponed | ||
| Wed., 10/12 | V Girls Volleyball | St. Joseph | Home - Westhill HS-Main Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Wed., 10/12 | JV Girls Volleyball | St. Joseph | Home - Westhill HS-Main Gym [Directions] | 4:30 p.m. | ||
| Wed., 10/12 | FR Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/13 | V Girls Soccer | Stamford | Away - Stamford HS-SHS Upper Soccer Field [Directions] | 4:00 p.m. | L 1-0 | |
| Thu., 10/13 | JV Girls Soccer | Stamford | Away - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | W 2-0 | |
| Fri., 10/14 | FR Football | Danbury | Home - Rippowan MS-Rippowam Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 10/14 | V Boys Soccer | Greenwich | Away - Greenwich HS-Field 7 [Directions] | 4:30 p.m. | W 1-0 | |
| Fri., 10/14 | JV Boys Soccer | Greenwich | Away - Cos Cob Park, Benvenuto Field-Benvenuto Field [Directions] | 4:45 p.m. | ||
| Fri., 10/14 | FR Boys Soccer | Greenwich | Home - Westhill HS-Front Turf [Directions] | 4:15 p.m. | L 0-1 | |
| Fri., 10/14 | V Girls Swimming and Diving | Ridgefield | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Fri., 10/14 | V Girls Volleyball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:30 p.m. | W 3-1 | |
| Fri., 10/14 | JV Girls Volleyball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:15 p.m. | ||
| Fri., 10/14 | FR Girls Volleyball | Wilton | Home - Westhill HS-Main Gym [Directions] | 4:30 p.m. | ||
| Sat., 10/15 | V Football | Ridgefield | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 1:00 p.m. | L 0-42 | |
| Sat., 10/15 | V Field Hockey | Weston | Away - Weston HS-WHS Lower Turf Field [Directions] | 11:30 a.m. | L 0-4 | |
| Sat., 10/15 | JV Field Hockey | Weston | Away - Weston HS-WHS Lower Turf Field [Directions] | 10:00 a.m. | ||
| Sat., 10/15 | V Girls Soccer | Greenwich | Home - Westhill HS-Westhill Front Turf Field [Directions] | 12:00 p.m. | L 3-1 | |
| Sat., 10/15 | JV Girls Soccer | Greenwich | Home - Westhill HS-Westhill Front Turf Field [Directions] | 10:00 a.m. | L 5-0 | |
| Sat., 10/15 | FR Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 10:00 a.m. | ||
| Mon., 10/17 | JV Football | Ridgefield | Away - Ridgefield HS-Tiger Hollow Turf Field II [Directions] | 4:00 p.m. | ||
| Mon., 10/17 | V Boys Soccer | Danbury | Home - Westhill HS-Westhill Front Turf Field [Directions] | 4:00 p.m. | W 1-0 | |
| Mon., 10/17 | FR Boys Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 4:00 p.m. | L 5-3 | |
| Mon., 10/17 | V Field Hockey | Fairfield Warde | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | L 0-1 | |
| Mon., 10/17 | JV Field Hockey | Fairfield Warde | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | ||
| Mon., 10/17 | V Girls Volleyball | Fairfield Ludlowe | Home - Westhill HS-Main Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Mon., 10/17 | JV Girls Volleyball | Fairfield Ludlowe | Home - Westhill HS-Main Gym [Directions] | 4:30 p.m. | ||
| Mon., 10/17 | FR Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:30 p.m. | ||
| Tue., 10/18 | V Girls Soccer | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 6:00 p.m. | L 6-0 | |
| Tue., 10/18 | JV Girls Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 4:00 p.m. | W 2-1 | |
| Wed., 10/19 | V Boys Cross Country | FCIAC Championship | Away - Waveny Park | 2:15 p.m. | ||
| Wed., 10/19 | V Girls Cross Country | FCIAC Championship | Away - Waveny Park | 2:15 p.m. | ||
| Wed., 10/19 | V Field Hockey | Wilton | Away - Wilton HS-Fuijitani Field -Turf [Directions] | 7:00 p.m. | L 0-9 | |
| Wed., 10/19 | JV Field Hockey | Wilton | Away - Wilton HS-Fuijitani Field -Turf [Directions] | 5:30 p.m. | ||
| Wed., 10/19 | V Girls Swimming and Diving | St. Joseph | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Wed., 10/19 | V Girls Volleyball | Stamford | Home - Westhill HS-Main Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Wed., 10/19 | JV Girls Volleyball | Stamford | Home - Westhill HS-Main Gym [Directions] | 4:30 p.m. | ||
| Thu., 10/20 | FR Football | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | 5:30 p.m. | ||
| Thu., 10/20 | V Boys Soccer | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 6:00 p.m. | T 2-2 | |
| Thu., 10/20 | JV Boys Soccer | Ridgefield | Away - Ridgefield HS-RHS Lower Grass Field [Directions] | 4:00 p.m. | ||
| Thu., 10/20 | FR Boys Soccer | Ridgefield | Home - Rippowan MS-Rippowam Turf Field [Directions] | 4:00 p.m. | L 0-2 | |
| Fri., 10/21 | V Football | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 7:00 p.m. | L 19-56 | |
| Fri., 10/21 | V Girls Soccer | Ridgefield | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | L 2-0 | |
| Fri., 10/21 | JV Girls Soccer | Ridgefield | Home - Rippowan MS-Rippowam Turf Field [Directions] | 4:00 p.m. | L 5-0 | |
| Fri., 10/21 | V Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | L 1-3 | |
| Fri., 10/21 | JV Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Sat., 10/22 | JV Football | Danbury | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 10:00 a.m. | ||
| Sat., 10/22 | JV Boys Soccer | Stamford | Home - Westhill HS-Front Turf [Directions] | 12:00 p.m. | ||
| Sat., 10/22 | V Field Hockey | Lauralton Hall | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 1:00 p.m. | L 1-2 | |
| Sat., 10/22 | JV Field Hockey | Lauralton Hall | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 2:45 p.m. | ||
| Sat., 10/22 | FR Girls Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 10:00 a.m. | ||
| Mon., 10/24 | V Boys Soccer | New Canaan | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | L 1-2 | |
| Mon., 10/24 | JV Boys Soccer | New Canaan | Home - Rippowan MS-Rippowam Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 10/24 | FR Boys Soccer | New Canaan | Away - Saxe MS-Field 1 [Directions] | 4:30 p.m. | ||
| Mon., 10/24 | V Girls Volleyball | Danbury | Home - Westhill HS-Main Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Mon., 10/24 | JV Girls Volleyball | Danbury | Home - Westhill HS-Main Gym [Directions] | 4:30 p.m. | ||
| Mon., 10/24 | FR Girls Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 4:30 p.m. | ||
| Tue., 10/25 | V Girls Soccer | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 7:00 p.m. | L 4-1 | |
| Tue., 10/25 | JV Girls Soccer | New Canaan | Away - Saxe MS-Field 1 [Directions] | 4:30 p.m. | ||
| Wed., 10/26 | JV Boys Soccer | Danbury | Home - Rippowan MS-Rippowam Turf Field [Directions] | 3:15 p.m. | ||
| Wed., 10/26 | V Girls Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:45 p.m. | W 3-1 | |
| Wed., 10/26 | JV Girls Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:30 p.m. | ||
| Wed., 10/26 | FR Girls Volleyball | Ridgefield | Home - Westhill HS-Main Gym [Directions] | 5:00 p.m. | ||
| Thu., 10/27 | FR Football | Fairfield Warde | Home - Rippowan MS-Rippowam Turf Field [Directions] | 3:45 p.m. | ||
| Thu., 10/27 | V Girls Soccer | Bridgeport Central | Away - Kennedy Stadium (Bridgeport) [Directions] | 4:00 p.m. | W 3-1 | |
| Thu., 10/27 | V Girls Volleyball | New Canaan | Home - Westhill HS-Main Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Thu., 10/27 | JV Girls Volleyball | New Canaan | Home - Westhill HS-Main Gym [Directions] | 4:30 p.m. | ||
| Fri., 10/28 | V Football | Bridgeport Central | Away - Bridgeport Central-Kennedy Stadium Turf [Directions] | 6:00 p.m. | W 46-32 | |
| Fri., 10/28 | FR Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:30 p.m. | ||
| Sat., 10/29 | V Boys Cross Country | CIAC Class LL Championship | Away - Wickham Park | 10:45 a.m. | ||
| Sat., 10/29 | JV Girls Swimming and Diving | Greenwich, Brien McMahon, Danbury, Darien, Fairfield Ludlowe, Fairfield Warde, New Canaan, Norwalk/McMahon, Ridgefield, St. Joseph, Stamford, Staples, Trumbull, Wilton | Away - Greenwich HS-Pool | 10:15 a.m. | ||
| Sat., 10/29 | JV Girls Volleyball | Fairfield Warde, Fairfield Ludlowe, Greenwich, TBA, Newtown, Stamford, Trumbull | Away - Fairfield Warde HS-Large Gym | 9:00 a.m. | ||
| Sat., 10/29 | FR Girls Volleyball | Greenwich | Home - Westhill HS-New Gym [Directions] | 10:30 a.m. | ||
| Mon., 10/31 | V Girls Volleyball | King and Low-Heywood Thomas (Scrim.) | Home - King School-Upper School Gym [Directions] | 4:00 p.m. | ||
| Tue., 11/1 | V Boys Golf | CIAC Division I Championship | Away - Stanley GC | 9:00 a.m. | ||
| Tue., 11/1 | V Girls Swimming and Diving | TBA, Brien McMahon, Danbury, Fairfield Ludlowe, Fairfield Warde, TBA, New Canaan, Norwalk/McMahon, Ridgefield, St. Joseph, Stamford, Staples, Trumbull, Wilton | Away - Greenwich HS-Pool | 5:15 p.m. | ||
| Tue., 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 | 5:15 p.m. | ||
| Tue., 11/1 | V Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:30 p.m. | ||
| Tue., 11/1 | JV Girls Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 11/2 | V Girls Swimming and Diving | FCIAC Diving Championship | Home - Westhill HS-Westhill Pool [Directions] | 5:00 p.m. | ||
| Thu., 11/3 | V Boys Soccer | Brien McMahon (Scrim.) | Home - Westhill HS-Front Turf [Directions] | 4:00 p.m. | ||
| Fri., 11/4 | V Boys Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Fri., 11/4 | V Football | Staples | Away - Staples HS-Staples Stadium [Directions] | 7:00 p.m. | L 0-49 | |
| Fri., 11/4 | FR Football | Brien McMahon | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 3:15 p.m. | ||
| Fri., 11/4 | V Girls Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Fri., 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 | 6:30 p.m. | ||
| Fri., 11/4 | V Girls Swimming and Diving | TBA, Brien McMahon, Danbury, Fairfield Ludlowe, Fairfield Warde, TBA, New Canaan, Norwalk/McMahon, Ridgefield, St. Joseph, Stamford, Staples, Trumbull, Wilton | Away - Greenwich HS-Pool | 6:30 p.m. | ||
| Sat., 11/5 | JV Football | Staples | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 11:30 a.m. | ||
| Mon., 11/7 | V Boys Soccer | Fairfield Prep | Away - Fairfield University-Rafferty Stadium [Directions] | 5:00 p.m. | ||
| Tue., 11/8 | V Girls Volleyball | Manchester | Home - Westhill HS-Main Gym [Directions] | 5:00 p.m. | W 3-0 | |
| Thu., 11/10 | FR Football | Stamford | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 2:30 p.m. | ||
| Thu., 11/10 | V Girls Swimming and Diving | CIAC Class LL Diving Championships | Away - Sheehan | 5:30 p.m. | ||
| Thu., 11/10 | V Girls Volleyball | Cheshire | Away - Cheshire HS-Gym West [Directions] | 6:00 p.m. | ||
| Sat., 11/12 | V Football | St. Joseph | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 12:00 p.m. | L 7-63 | |
| Sat., 11/12 | V Girls Swimming and Diving | CIAC Class LL Trials | Away - Cornerstone Pool | 11:15 a.m. | ||
| Mon., 11/14 | JV Football | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | Canceled | Cancelled | |
| Wed., 11/16 | V Girls Swimming and Diving | CIAC Class LL Final | Away - Cornerstone Pool | 6:00 p.m. | ||
| Thu., 11/17 | V Girls Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 11/19 | JV Football | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 1:00 p.m. | ||
| Sun., 11/20 | V Girls Swimming and Diving | CIAC State Open Swimming Championship | Away - Yale | 2:00 p.m. | ||
| Thu., 11/24 | V Football | Stamford | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 10:00 a.m. | L 6-33 | |
| Wed., 11/30 | V Girls Ice Hockey | Greenwich (Scrim.) | Away - Greenwich - Dorothy Hamill-Rink [Directions] | 5:15 p.m. | ||
| Tue., 12/6 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Terry Conners - Stamford-Ice Rink [Directions] | 7:30 p.m. | W 2-1 (OT) | |
| Thu., 12/8 | V Boys Basketball | Immaculate (Scrim.) | Home - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Sat., 12/10 | V Boys Basketball | Hamden (Scrim.) | Home - Westhill HS-Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 12/10 | V Girls Ice Hockey | Mercy/NW Catholic/East Hampton | Away - Cromwell-Upper Rink [Directions] | 5:20 p.m. | L 3-0 | |
| Mon., 12/12 | V Girls Basketball | King and Low-Heywood Thomas | Home - Westhill HS-Main Gym [Directions] | 3:15 p.m. | ||
| Wed., 12/14 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland of Ice-Stadium [Directions] | 8:00 p.m. | L 2-5 | |
| Wed., 12/14 | V Wrestling | St. Joseph | Home - Westhill HS-Main Gym [Directions] | 6:00 p.m. | ||
| Wed., 12/14 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Terry Conners - Stamford-Ice Rink [Directions] | 8:00 p.m. | W 9-0 | |
| Fri., 12/16 | V Boys Basketball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 7:00 p.m. | L 35-45 | |
| Fri., 12/16 | JV Boys Basketball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 5:15 p.m. | ||
| Fri., 12/16 | V Boys Swimming and Diving | Greenwich | Away - Greenwich HS-Pool [Directions] | 4:15 p.m. | ||
| Sat., 12/17 | V Boys Ice Hockey | Amity | Away - West Haven HS-Bennett Rink [Directions] | 8:00 p.m. | W 5-4 | |
| Sat., 12/17 | V Boys Indoor Track | Staples, Greenwich, Stamford, Trumbull | Away - Staples HS-Field House [Directions] | 1:30 p.m. | ||
| Sat., 12/17 | V Wrestling | Ludlowe Invitational | Away - Fairfield Ludlowe HS-Main Gym | 9:00 a.m. | ||
| Sat., 12/17 | V Girls Ice Hockey | Avon | Away - Newington-Blue Rink [Directions] | 4:35 p.m. | L 5-0 | |
| Sat., 12/17 | V Girls Indoor Track | Staples, Greenwich, Stamford, Trumbull | Away - Staples HS-Field House [Directions] | 1:30 p.m. | ||
| Mon., 12/19 | V Girls Basketball | Harding | Away - Warren Harding HS-Gym [Directions] | 6:00 p.m. | W 47-16 | |
| Mon., 12/19 | JV Girls Basketball | Harding | Away - Warren Harding HS-Gym [Directions] | 4:30 p.m. | ||
| Tue., 12/20 | V Boys Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 7:00 p.m. | L 35-77 | |
| Tue., 12/20 | JV Boys Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 12/20 | FR Boys Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 12/21 | V Wrestling | Staples | Away - Staples HS-Staples Gym [Directions] | 7:00 p.m. | ||
| Wed., 12/21 | V Girls Basketball | Immaculate | Away - Immaculate HS-Immaculate Gym [Directions] | 7:00 p.m. | L 28-66 | |
| Wed., 12/21 | JV Girls Basketball | Immaculate | Away - Immaculate HS-Immaculate Gym [Directions] | 5:15 p.m. | ||
| Thu., 12/22 | JV Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice-Stadium [Directions] | 3:30 p.m. | ||
| Sat., 12/24 | V Wrestling | Norwalk, Fairfield Ludlowe, New Canaan | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 9:00 a.m. | ||
| Tue., 12/27 | V Boys Basketball | Bethel | Home - Westhill HS-Main Gym [Directions] | 6:00 p.m. | L 43-47 | |
| Wed., 12/28 | V Boys Ice Hockey | Shepaug Valley Ice Hockey | Home - Terry Conners - Stamford-Ice Rink [Directions] | 4:10 p.m. | W 9-3 | |
| Wed., 12/28 | V Girls Basketball | Brookfield | Home - Westhill HS-Main Gym [Directions] | 6:00 p.m. | L 28-66 | |
| Wed., 12/28 | JV Girls Basketball | Brookfield | Home - Westhill HS-Main Gym [Directions] | 4:15 p.m. | ||
| Wed., 12/28 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Terry Conners - Stamford-Ice Rink [Directions] | 2:15 p.m. | W 4-3 | |
| Thu., 12/29 | V Boys Basketball | Bridgeport Central | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | L 38-65 | |
| Thu., 12/29 | V Boys Ice Hockey | JBWA | Away - Danbury Ice Arena-LIberty Rink [Directions] | 6:00 p.m. | W 7-2 | |
| Thu., 12/29 | V Girls Ice Hockey | Hamden Coop | Away - Hamden-Lou Astorino Ice Rink [Directions] | 12:00 p.m. | W 3-1 | |
| Fri., 12/30 | V Wrestling | Nighthawk Invitational Duals: Branford, Joel Barlow, Norwalk, East Haven, Fairfield Prep, Notre Dame & Westhill | Away - Newtown HS-Gym | 10:00 a.m. | ||
| Tue., 1/3 | V Girls Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 5:30 p.m. | L 43-62 | |
| Tue., 1/3 | JV Girls Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/4 | V Boys Ice Hockey | Brien McMahon/Norwalk | Home - Terry Conners - Stamford-Ice Rink [Directions] | 5:40 p.m. | W 9-2 | |
| Wed., 1/4 | V Boys Swimming and Diving | Staples | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Wed., 1/4 | V Wrestling | Greenwich | Home - Westhill HS-Main Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/4 | V Girls Ice Hockey | New Canaan | Home - Terry Conners - Stamford-Ice Rink [Directions] | 7:30 p.m. | W 3-2 | |
| Thu., 1/5 | V Boys Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 7:00 p.m. | L 41-64 | |
| Thu., 1/5 | JV Boys Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 1/5 | FR Boys Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 1/5 | V Girls Basketball | Trumbull | Home - Westhill HS-Main Gym [Directions] | 6:00 p.m. | L 18-48 | |
| Thu., 1/5 | JV Girls Basketball | Trumbull | Home - Westhill HS-Main Gym [Directions] | 4:30 p.m. | ||
| Thu., 1/5 | V Girls Gymnastics | Darien, New Canaan, Stamford | Home - Westhill HS-New Gym [Directions] | 6:00 p.m. | 52.7 | |
| Fri., 1/6 | V Boys Swimming and Diving | Ridgefield | Away - Barlow Mountain Pool [Directions] | 4:00 p.m. | ||
| Sat., 1/7 | V Boys Ice Hockey | Watertown-Pomperaug | Home - Terry Conners - Stamford-Ice Rink [Directions] | 8:10 p.m. | W 4-3 | |
| Sat., 1/7 | V Wrestling | Warde Invitational | Away - Fairfield Warde HS-Large Gym | 9:00 a.m. | ||
| Mon., 1/9 | V Girls Gymnastics | Greenwich, Stamford | Home - Westhill HS-New Gym [Directions] | 6:00 p.m. | 58.6 | |
| Tue., 1/10 | V Boys Basketball | Darien | Home - Westhill HS-Main Gym [Directions] | 7:00 p.m. | L 48-62 | |
| Tue., 1/10 | JV Boys Basketball | Darien | Home - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/10 | FR Boys Basketball | Darien | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/10 | V Girls Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 6:00 p.m. | L 24-28 | |
| Tue., 1/10 | JV Girls Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:30 p.m. | ||
| Wed., 1/11 | V Boys Ice Hockey | Wilton | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:30 p.m. | W 7-1 | |
| Wed., 1/11 | V Wrestling | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 7:00 p.m. | ||
| Wed., 1/11 | V Girls Basketball | Bassick | Away - Bassick HS-Gym [Directions] | 6:00 p.m. | L 36-51 | |
| Wed., 1/11 | JV Girls Basketball | Bassick | Away - Bassick HS-Gym [Directions] | 4:30 p.m. | ||
| Wed., 1/11 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Terry Conners - Stamford-Ice Rink [Directions] | 8:00 p.m. | W 3-1 | |
| Thu., 1/12 | V Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 7:00 p.m. | L 46-72 | |
| Thu., 1/12 | JV Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 1/12 | FR Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 1/12 | V Girls Basketball | Brien McMahon | Home - Westhill HS-Main Gym [Directions] | 6:00 p.m. | L 26-57 | |
| Thu., 1/12 | JV Girls Basketball | Brien McMahon | Home - Westhill HS-Main Gym [Directions] | 4:30 p.m. | ||
| Fri., 1/13 | V Boys Swimming and Diving | Darien | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Fri., 1/13 | V Wrestling | Shelton, Masuk | Away - Shelton HS-Auxillary Gym [Directions] | 4:30 p.m. | ||
| Fri., 1/13 | V Girls Ice Hockey | Greenwich | Away - Greenwich - Dorothy Hamill-Rink [Directions] | 5:15 p.m. | L 3-1 | |
| Sat., 1/14 | V Boys Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 3:00 p.m. | L 38-70 | |
| Sat., 1/14 | V Boys Ice Hockey | Darien | Away - Darien Ice House-Ice Rink [Directions] | 7:10 p.m. | L 1-6 | |
| Sat., 1/14 | V Boys Indoor Track | Wilton, Fairfield Warde, Norwalk, Trumbull | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 12:00 p.m. | ||
| Sat., 1/14 | V Girls Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 12:00 p.m. | L 36-51 | |
| Sat., 1/14 | V Girls Indoor Track | Wilton, Fairfield Warde, Norwalk, Trumbull | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 12:00 p.m. | ||
| Sat., 1/14 | Unified Sports Basketball | Stamford | Away - Stamford HS-SHS Aux Gym [Directions] | 1:45 p.m. | ||
| Mon., 1/16 | V Boys Basketball | Bridgeport Central | Home - Westhill HS-Main Gym [Directions] | 1:30 p.m. | L 50-63 | |
| Mon., 1/16 | JV Boys Basketball | Bridgeport Central | Home - Westhill HS-Main Gym [Directions] | 12:00 p.m. | ||
| Mon., 1/16 | FR Boys Basketball | Bridgeport Central | Home - Westhill HS-Main Gym [Directions] | 10:30 a.m. | ||
| Mon., 1/16 | V Boys Ice Hockey | East Haven Coop | Home - Terry Conners - Stamford-Ice Rink [Directions] | 1:45 p.m. | W 4-2 | |
| Tue., 1/17 | V Wrestling | Wilton | Home - Westhill HS-New Gym [Directions] | 6:00 p.m. | ||
| Tue., 1/17 | V Girls Basketball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | 6:00 p.m. | W 47-33 | |
| Tue., 1/17 | JV Girls Basketball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | 4:30 p.m. | ||
| Wed., 1/18 | V Boys Basketball | East Lyme | Home - Westhill HS-Main Gym [Directions] | 7:00 p.m. | L 49-77 | |
| Wed., 1/18 | JV Boys Basketball | East Lyme | Home - Westhill HS-Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 1/18 | V Boys Swimming and Diving | Trumbull | Away - Univ of Bridgeport Pool [Directions] | 4:00 p.m. | ||
| Wed., 1/18 | V Girls Ice Hockey | Darien | Away - Darien Ice House-Ice Rink [Directions] | 4:00 p.m. | L 3-2 | |
| Thu., 1/19 | V Boys Ice Hockey | St. Joseph | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | 7:30 p.m. | W 5-2 | |
| Thu., 1/19 | V Girls Gymnastics | Staples, Norwalk, Stamford | Away - Staples HS-Westport YMCA [Directions] | 7:00 p.m. | 70.25 | |
| Fri., 1/20 | V Boys Basketball | Fairfield Ludlowe | Home - Westhill HS-Main Gym [Directions] | 7:00 p.m. | L 41-47 | |
| Fri., 1/20 | JV Boys Basketball | Fairfield Ludlowe | Home - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/20 | FR Boys Basketball | Fairfield Ludlowe | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/20 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Fri., 1/20 | V Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:30 p.m. | L 24-62 | |
| Fri., 1/20 | JV Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/20 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 4:00 p.m. | T 2-2 | |
| Sat., 1/21 | V Boys Indoor Track | Staples, Fairfield Warde, Ridgefield, Trumbull | Away - Staples HS-Field House [Directions] | 1:30 p.m. | ||
| Sat., 1/21 | V Wrestling | Conard, Fairfield Ludlowe, New Fairfield, Plainville | Away - Conard HS-Main Gym [Directions] | 9:00 a.m. | ||
| Sat., 1/21 | V Girls Gymnastics | Trumbull, Stamford | Away - Next Dimension Gymnastics-Next Dimension [Directions] | 5:30 p.m. | 30.2 | |
| Sat., 1/21 | V Girls Gymnastics | St. Joseph, Stamford | Away - St. Joseph HS-Next Dimensions [Directions] | 5:30 p.m. | 30.2 | |
| Sat., 1/21 | V Girls Indoor Track | Staples, Fairfield Warde, Ridgefield, Trumbull | Away - Staples HS-Field House [Directions] | 1:30 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 1:30 p.m. | ||||||
| Mon., 1/23 | V Girls Gymnastics | Stamford, Wilton | Home - Westhill HS-New Gym [Directions] | 6:00 p.m. | 68.65 | |
| Mon., 1/23 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Home - Terry Conners - Stamford-Ice Rink [Directions] | 5:10 p.m. | W 3-2 | |
| Tue., 1/24 | V Boys Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 7:00 p.m. | L 60-41 | |
| Tue., 1/24 | JV Boys Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/24 | FR Boys Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/24 | V Girls Basketball | Staples | Home - Westhill HS-Main Gym [Directions] | 6:00 p.m. | L 32-56 | |
| Tue., 1/24 | JV Girls Basketball | Staples | Home - Westhill HS-Main Gym [Directions] | 4:30 p.m. | ||
| Wed., 1/25 | V Boys Ice Hockey | New Canaan | Home - Terry Conners - Stamford-Ice Rink [Directions] | 7:30 p.m. | L 6-3 | |
| Wed., 1/25 | V Boys Swimming and Diving | New Canaan | Away - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Wed., 1/25 | V Girls Ice Hockey | Greenwich | Home - Terry Conners - Stamford-Ice Rink [Directions] | 5:30 p.m. | W 2-1 | |
| Thu., 1/26 | V Wrestling | Danbury | Away - Danbury HS-New gym [Directions] | Postponed | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 6:00 p.m. | ||||||
| Fri., 1/27 | V Boys Basketball | New Canaan | Home - Westhill HS-Main Gym [Directions] | 7:00 p.m. | L 72-26 | |
| Fri., 1/27 | JV Boys Basketball | New Canaan | Home - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/27 | FR Boys Basketball | New Canaan | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/27 | V Girls Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 6:00 p.m. | L 19-45 | |
| Fri., 1/27 | JV Girls Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:30 p.m. | ||
| Sat., 1/28 | V Boys Ice Hockey | Trumbull | Home - Terry Conners - Stamford-Ice Rink [Directions] | 7:50 p.m. | W 4-0 | |
| Sat., 1/28 | V Wrestling | Brookfield Wrestling Tournament | Away - Brookfield HS-BHS Small Gym | 9:30 a.m. | ||
| Sat., 1/28 | V Girls Basketball | Greenwich | Home - Westhill HS-Main Gym [Directions] | 12:30 p.m. | L 30-60 | |
| Sat., 1/28 | JV Girls Basketball | Greenwich | Home - Westhill HS-Main Gym [Directions] | 11:00 a.m. | ||
| Sat., 1/28 | V Girls Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | 8:40 p.m. | L 6-0 | |
| Mon., 1/30 | V Boys Swimming and Diving | Wilton | Away - Wilton YMCA [Directions] | 3:40 p.m. | ||
| Tue., 1/31 | V Boys Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 7:00 p.m. | L 67-45 | |
| Tue., 1/31 | JV Boys Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/31 | FR Boys Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/31 | V Girls Basketball | Norwalk | Home - Westhill HS-Main Gym [Directions] | 6:00 p.m. | L 28-60 | |
| Tue., 1/31 | JV Girls Basketball | Norwalk | Home - Westhill HS-Main Gym [Directions] | 4:30 p.m. | ||
| Wed., 2/1 | V Boys Ice Hockey | Brien McMahon/Norwalk | Away - Sono Ice House-Main Rink [Directions] | 8:50 p.m. | W 4-2 | |
| Wed., 2/1 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Wed., 2/1 | V Wrestling | Trumbull | Home - Westhill HS-Main Gym [Directions] | 6:00 p.m. | ||
| Wed., 2/1 | V Girls Gymnastics | Fairfield Ludlowe, Stamford | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:30 p.m. | 80.5 | |
| Wed., 2/1 | V Girls Gymnastics | Fairfield Warde | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:30 p.m. | 80.5 | |
| Wed., 2/1 | V Girls Ice Hockey | Masuk Coop | Home - Terry Conners - Stamford-Ice Rink [Directions] | 8:00 p.m. | W 3-0 | |
| Thu., 2/2 | V Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 7:00 p.m. | L 88-29 | |
| Thu., 2/2 | JV Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 2/2 | FR Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 2/2 | V Boys Indoor Track | FCIAC Championships | Away - Floyd Little Athletic Center-Field House | 5:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Not Listed-Floyd Little Athletic Center | ||||||
| Thu., 2/2 | V Girls Basketball | Ridgefield | Home - Westhill HS-Main Gym [Directions] | 6:00 p.m. | L 18-62 | |
| Thu., 2/2 | JV Girls Basketball | Ridgefield | Home - Westhill HS-Main Gym [Directions] | 4:30 p.m. | ||
| Thu., 2/2 | JV Girls Ice Hockey | Greenwich (Scrim.) | Away - Greenwich - Dorothy Hamill-Rink [Directions] | 8:00 p.m. | ||
| Thu., 2/2 | V Girls Indoor Track | FCIAC, Bridgeport Central, Brien McMahon, Danbury, Darien, Fairfield Ludlowe, Fairfield Warde, Greenwich, New Canaan, Norwalk, Ridgefield, St. Joseph, Stamford, Staples, Trumbull, Wilton | Away - Floyd Little Athletic Center-Field House | 5:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Not Listed-Floyd Little Athletic Center | ||||||
| Sat., 2/4 | V Boys Ice Hockey | Staples | Away - Milford Ice Pavillion-Ice Rink [Directions] | 8:00 p.m. | W 7-0 | |
| Sat., 2/4 | V Wrestling | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 12:00 p.m. | ||
| Sat., 2/4 | V Girls Ice Hockey | Daniel Hand Coop | Home - Terry Conners - Stamford-Ice Rink [Directions] | 8:00 p.m. | L 4-3 | |
| Mon., 2/6 | V Boys Ice Hockey | Bethel/Brookfield/Danbury/Immaculate | Away - Danbury Ice Arena-Patriot Rink [Directions] | 8:00 p.m. | W 8-1 | |
| Tue., 2/7 | V Boys Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 7:00 p.m. | L 76-51 | |
| Tue., 2/7 | JV Boys Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:15 p.m. | ||
| Tue., 2/7 | FR Boys Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Tue., 2/7 | V Girls Basketball | Wilton | Home - Westhill HS-Main Gym [Directions] | 6:00 p.m. | L 21-45 | |
| Tue., 2/7 | JV Girls Basketball | Wilton | Home - Westhill HS-Main Gym [Directions] | 4:30 p.m. | ||
| Wed., 2/8 | V Boys Ice Hockey | Staples | Home - Terry Conners - Stamford-Ice Rink [Directions] | 7:30 p.m. | W 5-2 | |
| Wed., 2/8 | V Girls Ice Hockey | Darien | Home - Terry Conners - Stamford-Ice Rink [Directions] | 5:30 p.m. | L 1-0 | |
| Thu., 2/9 | Unified Sports Basketball | Stamford | Home - Westhill HS-New Gym [Directions] | 3:00 p.m. | ||
| Fri., 2/10 | JV Boys Basketball | Stamford | Home - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/10 | FR Boys Basketball | Stamford | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 2/10 | V Boys Swimming and Diving | Danbury | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| 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, Wilton | Away - New Canaan HS-Main Gym | 4:00 p.m. | ||
| Fri., 2/10 | JV Girls Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Sat., 2/11 | V Boys Ice Hockey | Wilton | Home - Terry Conners - Stamford-Ice Rink [Directions] | 7:00 p.m. | W 7-0 | |
| Sat., 2/11 | V Boys Indoor Track | CIAC Class LL Championships | Away - Floyd Little Athletic Center | 4:00 p.m. | ||
| Sat., 2/11 | V Girls Ice Hockey | Simsbury | Home - Terry Conners - Stamford-Ice Rink [Directions] | 5:00 p.m. | L 2-1 | |
| Sat., 2/11 | V Girls Indoor Track | CIAC Class LL Championships | Away - Floyd Little Athletic Center | 4:00 p.m. | ||
| Mon., 2/13 | V Boys Basketball | St. Joseph | Home - Westhill HS-Main Gym [Directions] | 7:00 p.m. | L 66-80 | |
| Mon., 2/13 | JV Boys Basketball | St. Joseph | Home - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/13 | FR Boys Basketball | St. Joseph | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 2/13 | V Girls Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 7:00 p.m. | L 22-63 | |
| Mon., 2/13 | JV Girls Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/15 | V Boys Basketball | Danbury | Home - Westhill HS-Main Gym [Directions] | 7:00 p.m. | L 41-84 | |
| Wed., 2/15 | JV Boys Basketball | Danbury | Home - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/15 | FR Boys Basketball | Danbury | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/15 | V Boys Ice Hockey | Trumbull | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | 8:00 p.m. | W 5-4 | |
| Wed., 2/15 | V Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 7:00 p.m. | L 19-55 | |
| Wed., 2/15 | JV Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/17 | V Wrestling | CIAC LL Championship | Away - Trumbull | 4:00 p.m. | ||
| Fri., 2/17 | V Girls Ice Hockey | East Catholic Coop | Away - Newington-Blue Rink [Directions] | 8:30 p.m. | L 3-0 | |
| Sat., 2/18 | V Boys Ice Hockey | Hall | Home - Terry Conners - Stamford-Ice Rink [Directions] | 6:20 p.m. | W 4-1 | |
| Sat., 2/18 | V Boys Indoor Track | CIAC State Open Championships | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/18 | V Wrestling | CIAC LL Championship | Away - Trumbull | 10:30 a.m. | ||
| Sat., 2/18 | V Girls Ice Hockey | Mercy/NW Catholic/East Hampton | Home - Terry Conners - Stamford-Ice Rink [Directions] | 8:00 p.m. | L 1-0 | |
| Sat., 2/18 | V Girls Indoor Track | CIAC State Open Championships | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Mon., 2/20 | V Boys Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 7:00 p.m. | L 34-61 | |
| Mon., 2/20 | JV Boys Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 2/20 | FR Boys Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 2/20 | V Boys Ice Hockey | North Haven | Away - Northford-Red [Directions] | 1:00 p.m. | L 2-1 | |
| Wed., 2/22 | V Boys Basketball | Fairfield Warde | Home - Westhill HS-Main Gym [Directions] | 7:00 p.m. | L 55-68 | |
| Wed., 2/22 | JV Boys Basketball | Fairfield Warde | Home - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/22 | FR Boys Basketball | Fairfield Warde | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/22 | V Girls Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | 7:40 p.m. | ||
| Thu., 2/23 | V Boys Basketball | Wright Tech (Scrim.) | Away - J M Wright Tech School-Thomas R. Good Gymnasium [Directions] | 5:00 p.m. | ||
| Thu., 2/23 | JV Boys Basketball | Wright Tech (Scrim.) | Away - J M Wright Tech School-Thomas R. Good Gymnasium [Directions] | 3:30 p.m. | ||
| Fri., 2/24 | V Wrestling | CIAC State Open | Away - Floyd Little Athletic Center | 12:45 p.m. | ||
| Sat., 2/25 | V Wrestling | CIAC State Open | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Sat., 2/25 | V Girls Gymnastics | CIAC Divisional Championships | Away - Jonathan Law | TBA | ||
| 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 Ice Hockey | Simsbury | Away - Simsbury - ISCC-NHL [Directions] | 5:00 p.m. | ||
| Thu., 3/2 | V Boys Ice Hockey | Wilton | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 6:30 p.m. | ||
| Thu., 3/2 | V Girls Ice Hockey | East Catholic Coop | Away - Newington-Blue Rink [Directions] | 4:00 p.m. | ||
| Fri., 3/3 | V Boys Basketball | Brien McMahon (Scrim.) | Home - Westhill HS-Main Gym [Directions] | 3:30 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, Wilton | 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., 3/4 | V Boys Ice Hockey | Trumbull | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 8:30 p.m. | ||
| Sat., 3/4 | V Girls Gymnastics | CIAC State Open | Away - New Milford | 4:00 p.m. | ||
| Tue., 3/7 | V Boys Ice Hockey | Watertown-Pomperaug | Home - Terry Conners - Stamford-Ice Rink [Directions] | 7:30 p.m. | ||
| Wed., 3/8 | V Boys Basketball | East Catholic | Away - East Catholic HS-Gym [Directions] | 6:30 p.m. | ||
| Thu., 3/9 | V Boys Swimming and Diving | CIAC Class LL Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Fri., 3/10 | V Boys Ice Hockey | Woodstock Academy | Away - Koeppel Community Sports Center - Trinity College-Albert Creighton Williams '64 Rink [Directions] | 6:00 p.m. | ||
| Sat., 3/11 | V Boys Swimming and Diving | CIAC Class LL Trials | Away - Cornerstone Pool | 4:30 p.m. | ||
| Thu., 3/16 | V Boys Swimming and Diving | CIAC Class LL Finals | Away - Cornerstone Pool | 1:30 p.m. | ||
| Fri., 3/17 | V Boys Swimming and Diving | CIAC Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/18 | V Boys Swimming and Diving | CIAC State Open Championship | Away - Yale | 1:00 p.m. | ||
| Thu., 3/23 | V Boys Volleyball | Joel Barlow (Scrim.) | Home - Westhill HS-Main Gym [Directions] | 4:30 p.m. | ||
| Fri., 3/24 | V Softball | Darien (Scrim.) | Away - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | ||
| Sat., 3/25 | V Boys Lacrosse | Amity (Scrim.) | Home - Hamden HS-HHS Turf #1 [Directions] | 11:00 a.m. | ||
| Sat., 3/25 | V Boys Lacrosse | Montville (Scrim.) | Home - Hamden HS-HHS Turf #1 [Directions] | 9:00 a.m. | ||
| Sat., 3/25 | V Boys Lacrosse | Hamden (Scrim.) | Home - Hamden HS-HHS Turf #1 [Directions] | 12:00 p.m. | ||
| Sat., 3/25 | V Softball | TBA | Away - TBA | 10:00 a.m. | Cancelled | |
| Sat., 3/25 | V Softball | TBA | Away - TBA | 11:45 a.m. | Cancelled | |
| Sat., 3/25 | V Softball | Stamford (Scrim.) | Away - Darien HS-DHS - Softball - JV Field [Directions] | 1:30 p.m. | Cancelled | |
| Sun., 3/26 | V Girls Lacrosse | New Milford/Danbury Girls Lacrosse Preseason Play Day (first game at 9:30) | Away - New Milford HS-Joe Wiser Stadium - NMHS | 9:00 a.m. | ||
| Mon., 3/27 | V Boys Volleyball | Greenwich (Scrim.) | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 3/28 | V Baseball | Brien McMahon (Scrim.) | Away - Brien McMahon HS-Pride Field [Directions] | 4:00 p.m. | ||
| Tue., 3/28 | FR Baseball | Darien (Scrim.) | Away - Darien HS-DHS Baseball - JV Field [Directions] | 3:30 p.m. | L 5-9 | |
| Wed., 3/29 | V Baseball | Iona Prep (NY) (Scrim.) | Away - IONA PREP-Baseball Field | 4:30 p.m. | ||
| Wed., 3/29 | JV Baseball | Iona Prep (NY) (Scrim.) | Home - Westhill HS-Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 3/29 | V Boys Lacrosse | Bethel (Scrim.) | Away - Bethel HS-MS turf lacrosse field [Directions] | 4:15 p.m. | ||
| Wed., 3/29 | V Softball | New Canaan (Scrim.) | Away - Waveny Park-Orchard Field [Directions] | 4:00 p.m. | ||
| Thu., 3/30 | FR Baseball | Staples (Scrim.) | Home - Rippowan MS-Rippowam Baseball Field [Directions] | 4:00 p.m. | L 20-5 | |
| Sat., 4/1 | JV Baseball | Glastonbury | Home - Rippowan MS-Rippowam Baseball Field [Directions] | 2:00 p.m. | ||
| Sat., 4/1 | V Boys Volleyball | Brookfield | Home - Westhill HS-Main Gym [Directions] | 11:00 a.m. | W 3-0 | |
| Sat., 4/1 | JV Boys Volleyball | Brookfield | Home - Westhill HS-Main Gym [Directions] | 12:30 p.m. | ||
| Sat., 4/1 | V Girls Lacrosse | Lauralton Hall | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 11:00 a.m. | L 8-18 | |
| Sat., 4/1 | JV Girls Lacrosse | Lauralton Hall | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | Canceled | Cancelled | |
| Sat., 4/1 | JV Softball | Sheehan | Away - Sheehan HS-Sheehan HS Softball Field [Directions] | Canceled | Cancelled | |
| Mon., 4/3 | V Baseball | Hall | Away - Hall HS-Varsity Baseball Diamond [Directions] | 3:45 p.m. | W 5-4 | |
| Mon., 4/3 | JV Baseball | Hall | Away - Hall HS-JV Baseball Diamond [Directions] | 3:45 p.m. | W 9-4 | |
| Mon., 4/3 | FR Baseball | Darien | Away - Darien HS-Town Hall Baseball Field [Directions] | 4:00 p.m. | L 10-11 | |
| Mon., 4/3 | FR Boys Lacrosse | Trumbull | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 4:30 p.m. | ||||||
| Tue., 4/4 | V Baseball | Glastonbury | Home - Westhill HS-Varsity Baseball Field [Directions] | 4:15 p.m. | L 2-9 | |
| Tue., 4/4 | V Boys Volleyball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 5:30 p.m. | L 2-3 | |
| Tue., 4/4 | JV Boys Volleyball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 4/4 | V Girls Lacrosse | Notre Dame-Fairfield | Away - Notre Dame - Fairfield -Park Ave Field [Directions] | 4:00 p.m. | W 18-5 | |
| Tue., 4/4 | FR Girls Lacrosse | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | Canceled | Cancelled | |
| Tue., 4/4 | V Softball | Greenwich | Away - Greenwich HS-Softball Field [Directions] | 4:30 p.m. | W 7-2 | |
| Wed., 4/5 | FR Baseball | Hamden | Home - Rippowan MS-Rippowam Baseball Field [Directions] | 4:30 p.m. | L 13-0 | |
| Wed., 4/5 | V Boys Lacrosse | Notre Dame-Fairfield | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | W 17-5 | |
| Wed., 4/5 | FR Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Fairfield Warde Grass Utility Field [Directions] | 4:30 p.m. | ||
| Thu., 4/6 | V Boys Lacrosse | Fairfield Warde | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | L 11-15 | |
| Thu., 4/6 | JV Boys Lacrosse | Fairfield Warde | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | ||
| Thu., 4/6 | V Boys Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:30 p.m. | W 3-1 | |
| Thu., 4/6 | JV Boys Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 6:00 p.m. | ||
| Thu., 4/6 | V Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:30 p.m. | L 9-12 | |
| Thu., 4/6 | JV Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | Postponed | ||
| Thu., 4/6 | FR Girls Lacrosse | Staples | Home - Westhill HS-Westhill Front Turf Field [Directions] | Canceled | Cancelled | |
| Sat., 4/8 | V Baseball | Ridgefield | Away - Governor Field [Directions] | 11:00 a.m. | L 4-5 | |
| Sat., 4/8 | JV Baseball | Ridgefield | Away - East Ridge MS-Baseball Field [Directions] | 11:00 a.m. | W 11-0 | |
| Sat., 4/8 | FR Baseball | Ridgefield | Home - Rippowan MS-Rippowam Baseball Field [Directions] | 12:00 p.m. | L 12-8 | |
| Sat., 4/8 | V Boys Lacrosse | Brien McMahon | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 12:00 p.m. | W 12-11 | |
| Sat., 4/8 | JV Boys Lacrosse | Brien McMahon | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 10:00 a.m. | ||
| Sat., 4/8 | V Boys Volleyball | Kolbe Cathedral | Home - Westhill HS-Main Gym [Directions] | 11:00 a.m. | W 3-0 | |
| Sat., 4/8 | JV Boys Volleyball | Kolbe Cathedral | Home - Westhill HS-Main Gym [Directions] | 12:30 p.m. | ||
| Sat., 4/8 | V Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 11:00 a.m. | L 8-16 | |
| Sat., 4/8 | JV Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 12:30 p.m. | ||
| Sat., 4/8 | V Softball | Branford | Home - Westhill HS-Varsity Softball Field [Directions] | 12:00 p.m. | W 7-2 | |
| Mon., 4/10 | FR Boys Lacrosse | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Mon., 4/10 | V Boys Tennis | Trumbull | Away - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | W 4-2 [Detailed Results] | |
| Mon., 4/10 | V Softball | Brien McMahon | Home - Westhill HS-Varsity Softball Field [Directions] | 4:00 p.m. | W 3-2 | |
| Mon., 4/10 | V Girls Tennis | Trumbull | Home - Westhill HS-Westhill Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Tue., 4/11 | V Baseball | Joel Barlow | Home - Cubeta Stadium [Directions] | 7:00 p.m. | L 1-8 | |
| Tue., 4/11 | FR Baseball | Joel Barlow | Home - Westhill HS-Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Tue., 4/11 | V Boys Lacrosse | Bunnell-Stratford | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | W 13-11 | |
| Tue., 4/11 | JV Boys Lacrosse | Bunnell-Stratford | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/11 | V Boys Outdoor Track | Stamford | Home - Westhill HS-Upper Grass Field [Directions] | 3:00 p.m. | ||
| Tue., 4/11 | V Boys Tennis | Darien | Home - Westhill HS-Westhill Tennis Courts [Directions] | 4:30 p.m. | L 6-1 [Detailed Results] | |
| Tue., 4/11 | V Girls Outdoor Track | Stamford | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 3:00 p.m. | ||
| Tue., 4/11 | V Softball | Sheehan | Away - Sheehan HS-Sheehan HS Softball Field [Directions] | 4:30 p.m. | L 5-6 | |
| Tue., 4/11 | V Girls Tennis | Darien | Away - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Wed., 4/12 | FR Baseball | Darien | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | L 4-5 | |
| Wed., 4/12 | FR Boys Lacrosse | Stamford | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:00 p.m. | ||
| Wed., 4/12 | V Boys Outdoor Track | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 3:30 p.m. | ||
| Wed., 4/12 | V Boys Volleyball | East Hartford | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 4/12 | JV Boys Volleyball | East Hartford | Home - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 4/12 | V Girls Outdoor Track | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 3:30 p.m. | ||
| Wed., 4/12 | V Softball | Greenwich | Home - Westhill HS-Varsity Softball Field [Directions] | 4:00 p.m. | W 8-1 | |
| Thu., 4/13 | V Boys Lacrosse | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | W 12-7 | |
| Thu., 4/13 | JV Boys Lacrosse | Trumbull | Away - Trumbull HS-Cork Field [Directions] | 4:15 p.m. | ||
| Thu., 4/13 | V Boys Tennis | Brien McMahon | Away - Brien McMahon HS-Tennis Courts [Directions] | 4:15 p.m. | W 7-0 [Detailed Results] | |
| Thu., 4/13 | V Girls Lacrosse | Trumbull | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | W OT 10-9 | |
| Thu., 4/13 | JV Girls Lacrosse | Trumbull | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | ||
| Thu., 4/13 | V Girls Tennis | Brien McMahon | Home - Westhill HS-Westhill Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Fri., 4/14 | V Baseball | Trumbull | Home - Westhill HS-Varsity Baseball Field [Directions] | 4:00 p.m. | L 1-3 | |
| Fri., 4/14 | JV Baseball | Trumbull | Home - Rippowan MS-Rippowam Baseball Field [Directions] | 4:00 p.m. | L 7-3 | |
| Fri., 4/14 | FR Baseball | Trumbull | Away - Trumbull HS-Varsity Baseball Field [Directions] | 4:00 p.m. | L 2-6 | |
| Fri., 4/14 | FR Boys Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | 4:00 p.m. | ||
| Fri., 4/14 | V Boys Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:00 p.m. | W 3-1 | |
| Fri., 4/14 | JV Boys Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 4/14 | FR Girls Lacrosse | Fairfield Warde | Home - Westhill HS-Westhill Front Turf Field [Directions] | Canceled | Cancelled | |
| Fri., 4/14 | V Softball | Trumbull | Away - Trumbull HS-Varsity Softball Diamond [Directions] | 3:30 p.m. | L 14-2 | |
| Fri., 4/14 | JV Softball | Trumbull | Away - Trumbull HS-JV Softball Diamond [Directions] | 5:30 p.m. | ||
| Sat., 4/15 | V Boys Lacrosse | West Haven | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 1:00 p.m. | W 15-1 | |
| Sat., 4/15 | JV Boys Lacrosse | West Haven | Home - Westhill HS-Westhill Front Turf Field [Directions] | 11:00 a.m. | ||
| Sat., 4/15 | V Girls Lacrosse | New Milford | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 11:00 a.m. | W 14-5 | |
| Sat., 4/15 | JV Girls Lacrosse | New Milford | Home - Westhill HS-Westhill Front Turf Field [Directions] | 1:00 p.m. | ||
| Mon., 4/17 | V Baseball | Darien | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | W 11-8 | |
| Mon., 4/17 | JV Baseball | Darien | Away - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | L 4-2 | |
| Mon., 4/17 | FR Baseball | Darien | Home - Rippowan MS-Rippowam Baseball Field [Directions] | 4:00 p.m. | L 6-2 | |
| Mon., 4/17 | FR Boys Lacrosse | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 4/17 | V Boys Outdoor Track | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Mon., 4/17 | V Boys Volleyball | Danbury | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 4/17 | JV Boys Volleyball | Danbury | Home - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 4/17 | FR Girls Lacrosse | Darien | Home - Westhill HS-Westhill Front Turf Field [Directions] | Canceled | Cancelled | |
| Mon., 4/17 | V Girls Outdoor Track | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Mon., 4/17 | V Softball | Darien | Home - Westhill HS-Varsity Softball Field [Directions] | 4:00 p.m. | L 6-10 | |
| Tue., 4/18 | V Boys Tennis | Staples | Away - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | W 4-3 [Detailed Results] | |
| Tue., 4/18 | V Girls Tennis | Staples | Home - Westhill HS-Westhill Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Wed., 4/19 | V Baseball | Brien McMahon | Home - Cubeta Stadium [Directions] | 7:00 p.m. | W 6-5 | |
| Wed., 4/19 | JV Baseball | Brien McMahon | Home - Westhill HS-Varsity Baseball Field [Directions] | 4:00 p.m. | W 4-1 | |
| Wed., 4/19 | V Boys Volleyball | Norwalk | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | W 3-1 | |
| Wed., 4/19 | JV Boys Volleyball | Norwalk | Home - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 4/19 | FR Girls Lacrosse | Trumbull | Away - Trumbull HS-JV Grass Field [Directions] | Canceled | Cancelled | |
| Wed., 4/19 | V Softball | Brien McMahon | Away - Brien McMahon HS-Softball Diamond [Directions] | 4:15 p.m. | L 4-5 | |
| Wed., 4/19 | JV Softball | Brien McMahon | Away - Brien McMahon HS-Softball Diamond [Directions] | 6:00 p.m. | ||
| Thu., 4/20 | V Boys Tennis | Norwalk | Away - Norwalk HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Thu., 4/20 | V Girls Tennis | Norwalk | Home - Westhill HS-Westhill Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Fri., 4/21 | V Baseball | Bridgeport Central | Away - Bridgeport Central HS-Baseball Diamond [Directions] | 4:30 p.m. | W 10-0 | |
| Fri., 4/21 | FR Boys Lacrosse | Trumbull | Away - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | ||
| Fri., 4/21 | V Boys Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:15 p.m. | W 3-0 | |
| Fri., 4/21 | JV Boys Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Fri., 4/21 | V Softball | Bridgeport Central | Home - Westhill HS-Varsity Softball Field [Directions] | 4:00 p.m. | W 12-0 | |
| Fri., 4/21 | JV Softball | Bridgeport Central | Home - Westhill HS-Varsity Softball Field [Directions] | 6:00 p.m. | ||
| Fri., 4/21 | V Girls Tennis | Bridgeport Central | Away - Bridgeport Central HS-Central High School Tennis Courts [Directions] | 4:30 p.m. | W 7-0 | |
| Sat., 4/22 | V Baseball | Hamden | Home - Westhill HS-Varsity Baseball Field [Directions] | 11:00 a.m. | W 8-7 | |
| Sat., 4/22 | V Boys Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 12:00 p.m. | L 6-11 | |
| Sat., 4/22 | JV Boys Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 10:00 a.m. | ||
| Sat., 4/22 | V Girls Lacrosse | Fairfield Ludlowe | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 11:00 a.m. | L 4-15 | |
| Sat., 4/22 | JV Girls Lacrosse | Fairfield Ludlowe | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 12:30 p.m. | ||
| Mon., 4/24 | V Baseball | Staples | Home - Westhill HS-Varsity Baseball Field [Directions] | 4:00 p.m. | W 5-4 | |
| Mon., 4/24 | JV Baseball | Staples | Home - Rippowan MS-Rippowam Baseball Field [Directions] | 4:00 p.m. | L 7-1 | |
| Mon., 4/24 | FR Baseball | Staples | Away - Staples HS-Baseball Diamond [Directions] | 4:30 p.m. | L 6-16 | |
| Mon., 4/24 | FR Boys Lacrosse | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | 4:15 p.m. | ||
| Mon., 4/24 | V Boys Tennis | Fairfield Warde | Home - Westhill HS-Westhill Tennis Courts [Directions] | 4:00 p.m. | L 4-3 [Detailed Results] | |
| Mon., 4/24 | V Boys Volleyball | New Canaan | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | L 0-3 | |
| Mon., 4/24 | JV Boys Volleyball | New Canaan | Home - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 4/24 | V Girls Lacrosse | New Canaan | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | L 2-17 | |
| Mon., 4/24 | JV Girls Lacrosse | New Canaan | Home - Westhill HS-Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Mon., 4/24 | V Softball | Staples | Away - Staples HS-Wakeman Field [Directions] | 4:15 p.m. | L 6-7 | |
| Mon., 4/24 | JV Softball | Staples | Away - Staples HS-Staples Softball Field [Directions] | Canceled | Cancelled | |
| Mon., 4/24 | V Girls Tennis | Fairfield Warde | Away - Fairfield Warde HS-Blake Courts [Directions] | 4:30 p.m. | L 2-5 | |
| Tue., 4/25 | V Boys Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 4:30 p.m. | L 3-17 | |
| Tue., 4/25 | JV Boys Lacrosse | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | Postponed | ||
| Tue., 4/25 | V Boys Outdoor Track | Staples | Away - Staples HS-Staples Stadium [Directions] | 4:15 p.m. | ||
| Tue., 4/25 | V Boys Tennis | St. Joseph | Home - Westhill HS-Westhill Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Tue., 4/25 | V Girls Outdoor Track | Staples | Away - Staples HS-Staples Stadium [Directions] | 4:15 p.m. | ||
| Tue., 4/25 | V Girls Tennis | St. Joseph | Away - St. Joseph HS-Tennis Courts [Directions] | 4:00 p.m. | W 4-3 | |
| Wed., 4/26 | V Baseball | Norwalk | Home - Westhill HS-Varsity Baseball Field [Directions] | 4:00 p.m. | L 4-6 | |
| Wed., 4/26 | FR Baseball | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 4:00 p.m. | W 21-7 | |
| Wed., 4/26 | FR Boys Lacrosse | Fairfield Warde | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | ||
| Wed., 4/26 | V Boys Volleyball | Darien | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | L 0-3 | |
| Wed., 4/26 | JV Boys Volleyball | Darien | Home - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 4/26 | FR Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Fairfield Warde Grass Utility Field [Directions] | Canceled | Cancelled | |
| Thu., 4/27 | V Boys Lacrosse | Danbury | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | W 16-2 | |
| Thu., 4/27 | JV Boys Lacrosse | Danbury | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | ||
| Thu., 4/27 | V Girls Lacrosse | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 4:30 p.m. | L 6-9 | |
| Thu., 4/27 | JV Girls Lacrosse | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 6:00 p.m. | ||
| Thu., 4/27 | V Softball | Norwalk | Away - Norwalk HS-Brien McMahon Softball Field [Directions] | 6:15 p.m. | L 2-14 | |
| Thu., 4/27 | JV Softball | Norwalk | Away - Naramake School Field [Directions] | Postponed | ||
| Fri., 4/28 | JV Baseball | Fairfield Warde | Away - Tunxis [Directions] | 4:30 p.m. | L 2-1 | |
| Fri., 4/28 | FR Baseball | Fairfield Warde | Home - Rippowan MS-Rippowam Baseball Field [Directions] | 4:00 p.m. | L 10-0 | |
| Fri., 4/28 | FR Boys Lacrosse | Stamford | Away - Stamford HS-Upper Lacrosse Field [Directions] | 5:00 p.m. | ||
| Fri., 4/28 | V Boys Tennis | Wilton | Away - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | L 5-2 [Detailed Results] | |
| Fri., 4/28 | V Boys Volleyball | Stamford | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 4/28 | JV Boys Volleyball | Stamford | Home - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 4/28 | FR Girls Lacrosse | Wilton | Home - Westhill HS-Westhill Front Turf Field [Directions] | Canceled | Cancelled | |
| Fri., 4/28 | V Softball | Fairfield Warde | Home - Westhill HS-Varsity Softball Field [Directions] | 4:00 p.m. | L 4-15 | |
| Fri., 4/28 | JV Softball | Fairfield Warde | Home - Westhill HS-Varsity Softball Field [Directions] | Postponed | ||
| Sat., 4/29 | V Boys Lacrosse | Shelton | Away - Shelton HS-Finn Stadium [Directions] | 11:00 a.m. | L 5-6 | |
| Sat., 4/29 | JV Boys Lacrosse | Shelton | Away - Shelton HS-Finn Stadium [Directions] | 12:45 p.m. | ||
| Sat., 4/29 | V Girls Lacrosse | Shelton | Away - Shelton HS-Finn Stadium [Directions] | 2:30 p.m. | L 11-12(OT) | |
| Sat., 4/29 | JV Girls Lacrosse | Shelton | Away - Shelton HS-Finn Stadium [Directions] | 4:15 p.m. | ||
| Mon., 5/1 | V Baseball | St. Joseph | Away - St. Joseph HS-Baseball Diamond [Directions] | 4:00 p.m. | L 2-3 | |
| Mon., 5/1 | JV Baseball | St. Joseph | Away - Unity Park-Field 1 [Directions] | 4:00 p.m. | W 6-1 | |
| Mon., 5/1 | V Boys Lacrosse | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 6:30 p.m. | W 16-7 | |
| Mon., 5/1 | JV Boys Lacrosse | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 4:30 p.m. | ||
| Mon., 5/1 | FR Boys Lacrosse | New Canaan | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | ||
| Mon., 5/1 | V Boys Tennis | Fairfield Ludlowe | Home - Westhill HS-Westhill Tennis Courts [Directions] | 4:30 p.m. | W 6-1 | |
| Mon., 5/1 | V Boys Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | W 3-1 | |
| Mon., 5/1 | JV Boys Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 6:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 5:15 p.m. | ||||||
| Mon., 5/1 | V Softball | St. Joseph | Home - Westhill HS-Varsity Softball Field [Directions] | 4:00 p.m. | L 4-7 | |
| Tue., 5/2 | V Boys Outdoor Track | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/2 | V Girls Lacrosse | Stamford | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | L 7-18 | |
| Tue., 5/2 | JV Girls Lacrosse | Stamford | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | ||
| Tue., 5/2 | V Girls Outdoor Track | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 4:00 p.m. | ||
| Wed., 5/3 | V Baseball | Wilton | Home - Westhill HS-Varsity Baseball Field [Directions] | 4:00 p.m. | W 12-3 | |
| Wed., 5/3 | JV Baseball | Wilton | Home - Rippowan MS-Rippowam Baseball Field [Directions] | 4:00 p.m. | W 3-2 | |
| Wed., 5/3 | FR Baseball | Wilton | Away - Allen's Meadow-Baseball Diamond [Directions] | 4:00 p.m. | L 2-12 | |
| Wed., 5/3 | FR Boys Lacrosse | Fairfield Ludlowe | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | ||
| Wed., 5/3 | V Boys Tennis | Stamford | Home - Westhill HS-Westhill Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Wed., 5/3 | V Boys Volleyball | Fairfield Ludlowe | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 5/3 | JV Boys Volleyball | Fairfield Ludlowe | Home - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 5/3 | FR Girls Lacrosse | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | Postponed | ||
| Wed., 5/3 | V Softball | Wilton | Away - Wilton HS-Varsity Softball Field [Directions] | 6:00 p.m. | W 8-2 | |
| Wed., 5/3 | JV Softball | Wilton | Away - Wilton HS-JV Softball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/3 | V Girls Tennis | Stamford | Away - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | W 4-3 | |
| Thu., 5/4 | V Boys Tennis | Greenwich | Away - Greenwich HS-Tennis Courts [Directions] | 4:30 p.m. | L 0-7 | |
| Thu., 5/4 | V Girls Tennis | Greenwich | Home - Westhill HS-Westhill Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Fri., 5/5 | V Baseball | Fairfield Ludlowe | Away - Kiwanis Field-Baseball Diamond [Directions] | 4:00 p.m. | W 5-4 | |
| Fri., 5/5 | JV Baseball | Fairfield Ludlowe | Away - Owen Fish Park-Owen Fish [Directions] | 4:00 p.m. | W 6-2 | |
| Fri., 5/5 | FR Baseball | Fairfield Ludlowe | Home - Rippowan MS-Rippowam Baseball Field [Directions] | 4:00 p.m. | W 4-1 | |
| Fri., 5/5 | FR Boys Lacrosse | Greenwich | Away - Cos Cob Park, Benvenuto Field-Benvenuto Field [Directions] | 4:30 p.m. | ||
| Fri., 5/5 | V Boys Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 5/5 | JV Boys Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 5:30 p.m. | ||
| Fri., 5/5 | V Softball | Fairfield Ludlowe | Home - Westhill HS-Varsity Softball Field [Directions] | 4:00 p.m. | L 2-8 | |
| Fri., 5/5 | JV Softball | Fairfield Ludlowe | Home - Westhill HS-Varsity Softball Field [Directions] | 6:00 p.m. | ||
| Fri., 5/5 | V Girls Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Tennis Courts [Directions] | 4:00 p.m. | L 1-6 | |
| Sat., 5/6 | V Baseball | Fairfield Warde | Away - Fairfield Warde HS-Baseball Diamond [Directions] | 3:00 p.m. | L 4-11 | |
| Sat., 5/6 | FR Baseball | St. Joseph | Home - Westhill HS-Varsity Baseball Field [Directions] | 11:00 a.m. | W 8-6 | |
| Sat., 5/6 | V Boys Lacrosse | Immaculate | Away - Immaculate HS [Directions] | 2:00 p.m. | W 10-4 | |
| Sat., 5/6 | V Boys Outdoor Track | ORG-JAKE INVITATIONAL | Away - Amity Regional HS-Amity HS Track | 9:00 a.m. | ||
| Sat., 5/6 | V Girls Lacrosse | Immaculate | Away - Immaculate HS-Mustang Valley [Directions] | 4:00 p.m. | W 16-5 | |
| Sat., 5/6 | JV Softball | Stamford | Home - Westhill HS-Varsity Softball Field [Directions] | Canceled | Cancelled | |
| Sat., 5/6 | V Girls Tennis | Wilton | Home - Westhill HS-Westhill Tennis Courts [Directions] | 3:00 p.m. | L 3-4 | |
| Sun., 5/7 | V Softball | Stamford | Home - Westhill HS-Varsity Softball Field [Directions] | 1:00 p.m. | W 6-1 | |
| Mon., 5/8 | V Baseball | Stamford | Away - Cubeta Stadium [Directions] | 7:00 p.m. | W 7-4 | |
| Mon., 5/8 | JV Baseball | Stamford | Away - Cubeta Stadium [Directions] | 3:30 p.m. | W 7-3 | |
| Mon., 5/8 | FR Baseball | Stamford | Home - Westhill HS-Varsity Baseball Field [Directions] | 4:00 p.m. | L 16-13 | |
| Mon., 5/8 | V Boys Tennis | Danbury | Home - Westhill HS-Westhill Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Mon., 5/8 | V Boys Volleyball | Fairfield Warde | Home - Westhill HS-Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Mon., 5/8 | JV Boys Volleyball | Brien McMahon | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 5/8 | V Girls Tennis | Danbury | Away - Danbury HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Tue., 5/9 | V Boys Lacrosse | Staples | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | L 1-23 | |
| Tue., 5/9 | JV Boys Lacrosse | Staples | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/9 | V Boys Outdoor Track | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 4:00 p.m. | ||
| Tue., 5/9 | V Boys Tennis | Ridgefield | Away - Ridgefield HS-RHS Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Tue., 5/9 | V Girls Outdoor Track | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 4:00 p.m. | ||
| Tue., 5/9 | V Girls Tennis | Ridgefield | Home - Westhill HS-Westhill Tennis Courts [Directions] | 5:00 p.m. | W 7-0 | |
| Wed., 5/10 | V Baseball | Greenwich | Home - Cubeta Stadium [Directions] | 7:00 p.m. | W 16-6 | |
| Wed., 5/10 | JV Baseball | Greenwich | Home - Westhill HS-Varsity Baseball Field [Directions] | 4:00 p.m. | W 5-0 | |
| Wed., 5/10 | FR Baseball | Greenwich | Away - Greenwich HS-Baseball Field [Directions] | 4:30 p.m. | L 3-13 | |
| Wed., 5/10 | FR Boys Lacrosse | Darien | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | ||
| Wed., 5/10 | V Boys Tennis | Bridgeport Central | Home - Westhill HS-Westhill Tennis Courts [Directions] | 4:30 p.m. | W 7-0 | |
| Wed., 5/10 | V Boys Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 5/10 | JV Boys Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 5/10 | V Girls Lacrosse | Staples | Away - Staples HS-Staples Stadium [Directions] | 6:00 p.m. | L 8-21 | |
| Wed., 5/10 | JV Girls Lacrosse | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 4:15 p.m. | ||
| Wed., 5/10 | FR Girls Lacrosse | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | Canceled | Cancelled | |
| Thu., 5/11 | V Boys Tennis | New Canaan | Home - Westhill HS-Westhill Tennis Courts [Directions] | 4:30 p.m. | L 4-3 | |
| Thu., 5/11 | V Girls Lacrosse | Norwalk | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | L 9-16 | |
| Thu., 5/11 | JV Girls Lacrosse | Norwalk | Home - Westhill HS-Westhill Front Turf Field [Directions] | 5:30 p.m. | ||
| Thu., 5/11 | V Softball | Danbury | Home - Westhill HS-Varsity Softball Field [Directions] | 3:30 p.m. | L 1-6 | |
| Thu., 5/11 | JV Softball | Danbury | Home - Westhill HS-Varsity Softball Field [Directions] | 5:30 p.m. | ||
| Thu., 5/11 | V Girls Tennis | New Canaan | Away - New Canaan HS-NCHS Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Fri., 5/12 | FR Baseball | Danbury | Home - Rippowan MS-Rippowam Baseball Field [Directions] | 4:00 p.m. | W 6-1 | |
| Fri., 5/12 | V Boys Volleyball | Trumbull | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | L 1-3 | |
| Fri., 5/12 | JV Boys Volleyball | Trumbull | Home - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Sat., 5/13 | V Baseball | Danbury | Away - Danbury HS-V Baseball Field [Directions] | 11:00 a.m. | L 2-4 | |
| Sat., 5/13 | JV Baseball | Danbury | Away - Danbury HS-JV Baseball Field [Directions] | 11:00 a.m. | W 10-1 | |
| Sat., 5/13 | V Boys Lacrosse | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 6:00 p.m. | W 8-4 | |
| Sat., 5/13 | JV Boys Lacrosse | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 3:30 p.m. | ||
| Mon., 5/15 | V Baseball | Ridgefield | Home - Westhill HS-Varsity Baseball Field [Directions] | 4:00 p.m. | L 2-5 | |
| Mon., 5/15 | JV Baseball | Ridgefield | Home - Rippowan MS-Rippowam Baseball Field [Directions] | 4:00 p.m. | W 7-0 | |
| Mon., 5/15 | FR Baseball | Ridgefield | Away - Governor Field [Directions] | 4:30 p.m. | L 6-9 | |
| Mon., 5/15 | V Boys Lacrosse | St. Joseph | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | L 4-18 | |
| Mon., 5/15 | JV Boys Lacrosse | St. Joseph | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 3:30 p.m. | ||
| Mon., 5/15 | V Boys Volleyball | Bridgeport Central | Away - Bridgeport Central HS-The Barry McLeod Court [Directions] | 6:00 p.m. | W 3-0 | |
| Mon., 5/15 | JV Boys Volleyball | Bridgeport Central | Away - Bridgeport Central HS-The Barry McLeod Court [Directions] | 4:30 p.m. | ||
| Mon., 5/15 | V Softball | Ridgefield | Away - Ridgefield HS-Varsity Softball Field [Directions] | 4:00 p.m. | L 0-13 | |
| Tue., 5/16 | V Girls Lacrosse | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 4:00 p.m. | L 9-17 | |
| Tue., 5/16 | JV Girls Lacrosse | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 5:30 p.m. | ||
| Tue., 5/16 | FR Girls Lacrosse | Trumbull | Home - Westhill HS-Westhill Front Turf Field [Directions] | Canceled | Cancelled | |
| Tue., 5/16 | V Girls Tennis | Greenwich | Away - Greenwich HS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/17 | V Baseball | New Canaan | Away - Mead Park-Baseball Field [Directions] | 4:00 p.m. | L 2-12 | |
| Wed., 5/17 | JV Baseball | New Canaan | Away - Waveny Park-Coppo Field [Directions] | 4:00 p.m. | W 14-0 | |
| Wed., 5/17 | FR Baseball | New Canaan | Home - Rippowan MS-Rippowam Baseball Field [Directions] | 4:00 p.m. | L 7-19 | |
| Wed., 5/17 | V Boys Outdoor Track | Danbury | Away - Danbury HS-Stadium Track [Directions] | 4:00 p.m. | ||
| Wed., 5/17 | V Boys Volleyball | Ridgefield | Home - Westhill HS-Main Gym [Directions] | 5:30 p.m. | W 3-1 | |
| Wed., 5/17 | JV Boys Volleyball | Ridgefield | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 5/17 | V Girls Outdoor Track | Danbury | Away - Danbury HS-Stadium Track [Directions] | 4:00 p.m. | ||
| Wed., 5/17 | V Softball | New Canaan | Home - Westhill HS-Varsity Softball Field [Directions] | 4:30 p.m. | L 2-9 | |
| Thu., 5/18 | FR Boys Lacrosse | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 5:00 p.m. | ||
| Thu., 5/18 | FR Girls Lacrosse | Norwalk | Home - Westhill HS-Westhill Front Turf Field [Directions] | Canceled | Cancelled | |
| Fri., 5/19 | V Baseball | St. Joseph | Away - St. Joseph HS-Baseball Diamond [Directions] | 12:30 p.m. | W 3-2 | |
| Fri., 5/19 | JV Baseball | Norwalk | Home - Westhill HS-Varsity Baseball Field [Directions] | 4:00 p.m. | W 11-1 | |
| Sat., 5/20 | V Boys Lacrosse | Jonathan Law | Away - Jonathan Law HS-Lawmen Stadium [Directions] | 2:00 p.m. | W 14-6 | |
| Sat., 5/20 | JV Boys Lacrosse | Jonathan Law | Away - Jonathan Law HS-Lawmen Stadium [Directions] | 3:30 p.m. | ||
| Sat., 5/20 | V Boys Volleyball | Fairfield Ludlowe | Home - Westhill HS-Main Gym [Directions] | 2:00 p.m. | ||
| Sat., 5/20 | JV Girls Lacrosse | West Haven | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | Canceled | Cancelled | |
| Mon., 5/22 | V Baseball | Trumbull | Away - Cubeta Stadium [Directions] | 7:00 p.m. | W 4-2 | |
| Mon., 5/22 | V Softball | Kolbe Cathedral | Away - Seaside Park-Field #2 (UB Field) [Directions] | 4:15 p.m. | W 14-2 | |
| Tue., 5/23 | V Boys Outdoor Track | FCIAC Track Championship | Away - Danbury HS-Danbury HS Stadium | 2:30 p.m. | ||
| Tue., 5/23 | V Girls Outdoor Track | FCIAC Track Championship | Away - Danbury HS-DHS Stadium | 2:30 p.m. | ||
| Tue., 5/23 | V Softball | Darien (Scrim.) | Away - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 5/24 | V Boys Volleyball | Darien | Away - Fairfield Warde HS-Gym [Directions] | 5:00 p.m. | ||
| Wed., 5/24 | V Girls Lacrosse | West Haven | Home - Westhill HS-Westhill Front Turf Field [Directions] | 5:00 p.m. | W 17-5 | |
| Thu., 5/25 | V Baseball | Fairfield Warde | Away - Cubeta Stadium [Directions] | 7:00 p.m. | L 1-6 | |
| Fri., 5/26 | V Boys Lacrosse | Hall | Away - Hall HS-Stadium (Turf Field) [Directions] | 4:00 p.m. | L 10-12 | |
| Fri., 5/26 | V Boys Tennis | Conard | Away - Wolcott Park-Tennis Courts [Directions] | 11:00 a.m. | ||
| Fri., 5/26 | V Softball | Staples (Scrim.) | Away - Staples HS-Wakeman Field [Directions] | 4:30 p.m. | ||
| Fri., 5/26 | V Girls Tennis | Maloney | Away - Maloney HS-Tennis Courts [Directions] | 3:45 p.m. | ||
| Tue., 5/30 | V Baseball | Manchester | Away - Mt. Nebo Park-Baseball Diamond [Directions] | 3:30 p.m. | W 2-0 | |
| Tue., 5/30 | V Boys Tennis | Greenwich | Away - Greenwich HS-Tennis Courts [Directions] | 2:15 p.m. | ||
| Tue., 5/30 | V Softball | Cheshire | Away - Cheshire HS-Softball Diamond [Directions] | 4:15 p.m. | ||
| Wed., 5/31 | V Baseball | Darien | Home - Cubeta Stadium [Directions] | 3:30 p.m. | W 4-0 | |
| Wed., 5/31 | V Boys Outdoor Track | CIAC Class LL Championships | Away - Willow Brook Park | 10:00 a.m. | ||
| Wed., 5/31 | V Boys Volleyball | Fairfield Ludlowe | Home - Westhill HS-Main Gym [Directions] | 5:00 p.m. | ||
| Wed., 5/31 | V Girls Outdoor Track | CIAC Class LL Championships | Away - Willow Brook Park | 10:00 a.m. | ||
| Sat., 6/3 | V Baseball | West Haven | Home - Cubeta Stadium [Directions] | 3:00 p.m. | ||
| Sat., 6/3 | V Boys Volleyball | Conard | Away - Conard HS-Main Gym [Directions] | 3:30 p.m. | ||
| Mon., 6/5 | V Boys Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/5 | V Boys Tennis | CIAC Individual Invitational Opening Rounds | Away - Wesleyan | 10:00 a.m. | ||
| Mon., 6/5 | V Girls Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/5 | V Girls Tennis | CIAC Individual Invitational Opening Rounds | Away - Wesleyan | 10:00 a.m. | ||
| Tue., 6/6 | V Baseball | Staples | Away - Municipal Stadium Complex (Waterbury, CT)-Municipal Stadium [Directions] | 3:30 p.m. | ||
| Tue., 6/6 | V Boys Tennis | CIAC Individual Invitational Round of 16 | Away - Wesleyan | 12:00 p.m. | ||
| Tue., 6/6 | V Boys Tennis | CIAC Individual Invitational Quarterfinals | Away - Wesleyan | 3:30 p.m. | ||
| Tue., 6/6 | V Girls Tennis | CIAC Individual Invitational Round of 16 | Away - Wesleyan | 12:00 p.m. | ||
| Tue., 6/6 | V Girls Tennis | CIAC Individual Invitational Quarterfinals | Away - Wesleyan | 3:30 p.m. | ||
| Wed., 6/7 | V Boys Tennis | CIAC Individual Invitational Semifinals | Away - Wesleyan | 3:30 p.m. | ||
| Wed., 6/7 | V Girls Tennis | CIAC Individual Invitational Semifinals | Away - Wesleyan | 3:30 p.m. | ||
| Thu., 6/8 | V Boys Tennis | CIAC Individual Invitational Finals | Away - Wesleyan | 3:30 p.m. | ||
| Thu., 6/8 | V Girls Tennis | CIAC Individual Invitational Finals | Away - Wesleyan | 3:30 p.m. | ||
| Mon., 6/12 | V Boys Outdoor Track | CIAC Hammer Throw Championship | Away - Willow Brook Park | 2:00 p.m. | ||
| Mon., 6/12 | V Girls Outdoor Track | CIAC Hammer Throw Championship | Away - Willow Brook Park | 4:00 p.m. | ||
| Tue., 6/13 | V Boys Outdoor Track | CIAC Decathlon Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 6/13 | V Girls Outdoor Track | CIAC Heptathlon Championship | Away - Willow Brook Park | 10:30 a.m. | ||
| Tue., 6/13 | V Girls Outdoor Track | CIAC Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/14 | V Boys Outdoor Track | CIAC Decathlon Championship | Away - Willow Brook Park | 8:30 a.m. | ||
| Wed., 6/14 | V Boys Outdoor Track | CIAC Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/14 | V Girls Outdoor Track | CIAC Heptathlon Championship | Away - Willow Brook Park | 8:30 a.m. | ||