| Trumbull 2020-21 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 538 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Thu., 10/1 | V Boys Cross Country | St. Joseph | Home - Trumbull HS-Cross Country Course [Directions] | 3:45 p.m. | ||
| Thu., 10/1 | JV Football | St. Joseph | Away - St. Joseph HS-Lower Grass Field [Directions] | 3:45 p.m. | ||
| Thu., 10/1 | FR Football | St. Joseph | Away - St. Joseph HS-Lower Grass Field [Directions] | 3:45 p.m. | ||
| Thu., 10/1 | V Girls Cross Country | St. Joseph | Home - Trumbull HS-Cross Country Course [Directions] | 3:45 p.m. | ||
| Thu., 10/1 | V Field Hockey | St. Joseph | Home - Trumbull HS-McDougall Stadium [Directions] | 3:45 p.m. | W 2-0 | |
| Thu., 10/1 | V Girls Soccer | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 3:45 p.m. | W 2-1 | |
| Thu., 10/1 | V Girls Swimming and Diving | Fairfield Warde | Home - Hillcrest MS-Pool [Directions] | 3:45 p.m. | ||
| Thu., 10/1 | V Girls Swimming and Diving | Fairfield Warde | Away - Westport YMCA [Directions] | TBA | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 8:30 p.m. | ||||||
| Thu., 10/1 | V Girls Volleyball | St. Joseph | Home - Trumbull HS-THS Main Gym [Directions] | 3:45 p.m. | W 3-0 | |
| Fri., 10/2 | V Football | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 3:45 p.m. | ||
| Fri., 10/2 | V Boys Soccer | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 3:45 p.m. | W 2-1 | |
| Sat., 10/3 | JV Boys Soccer | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 10:00 a.m. | ||
| Sat., 10/3 | FR Boys Soccer | Fairfield Prep | Away - Fairfield University-Rafferty Stadium [Directions] | 10:00 a.m. | ||
| Sat., 10/3 | JV Field Hockey | St. Joseph | Home - Trumbull HS-McDougall Stadium [Directions] | 1:00 p.m. | ||
| Sat., 10/3 | V Girls Soccer | Bridgeport Central | Away - Bridgeport Central HS-Kennedy Stadium Turf [Directions] | 9:00 a.m. | W 9-1 | |
| Sat., 10/3 | JV Girls Volleyball | St. Joseph | Home - Trumbull HS-THS Main Gym [Directions] | 1:00 p.m. | ||
| Sat., 10/3 | FR Girls Volleyball | St. Joseph | Home - Trumbull HS-Aux Gym [Directions] | 1:00 p.m. | ||
| Mon., 10/5 | V Boys Soccer | St. Joseph | Home - Trumbull HS-New Turf Field [Directions] | 3:45 p.m. | L 1-2 | |
| Mon., 10/5 | JV Girls Soccer | St. Joseph | Home - Trumbull HS-The Pit [Directions] | 3:45 p.m. | ||
| Tue., 10/6 | V Boys Cross Country | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | ||
| Tue., 10/6 | V Girls Cross Country | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | ||
| Wed., 10/7 | V Boys Soccer | Fairfield Prep | Home - Trumbull HS-Cork Field [Directions] | 3:45 p.m. | L 0-1 | |
| Wed., 10/7 | V Field Hockey | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 3:45 p.m. | ||
| Wed., 10/7 | V Girls Swimming and Diving | St. Joseph | Home - Hillcrest MS-Pool [Directions] | 3:45 p.m. | ||
| Wed., 10/7 | V Girls Swimming and Diving | St. Joseph | Away - Hillcrest MS-Pool [Directions] | 8:00 p.m. | ||
| Wed., 10/7 | V Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 3:45 p.m. | W 3-0 | |
| Thu., 10/8 | JV Football | Fairfield Ludlowe | Home - Trumbull HS-McDougall Stadium [Directions] | 3:45 p.m. | ||
| Thu., 10/8 | FR Football | Fairfield Ludlowe | Home - Trumbull HS-McDougall Stadium [Directions] | 3:45 p.m. | ||
| Thu., 10/8 | V Girls Soccer | Fairfield Warde | Home - Trumbull HS-New Turf Field [Directions] | 4:00 p.m. | T 2-2 | |
| Thu., 10/8 | V Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:30 p.m. | L 2-3 | |
| Fri., 10/9 | V Boys Cross Country | Fairfield Prep | Home - Trumbull HS-Cross Country Course [Directions] | 4:15 p.m. | ||
| Fri., 10/9 | V Football | Fairfield Ludlowe | Home - Trumbull HS-McDougall Stadium [Directions] | 3:45 p.m. | ||
| Fri., 10/9 | V Girls Cross Country | Fairfield Warde | Home - Trumbull HS-Cross Country Course [Directions] | 3:45 p.m. | ||
| Fri., 10/9 | V Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 5:30 p.m. | W 2-0 | |
| Sat., 10/10 | JV Boys Soccer | Fairfield Prep | Home - Trumbull HS-New Turf Field [Directions] | 10:00 a.m. | ||
| Sat., 10/10 | FR Boys Soccer | Fairfield Prep | Home - Trumbull HS-The Pit [Directions] | 10:00 a.m. | ||
| Sat., 10/10 | JV Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 9:00 a.m. | ||
| Sat., 10/10 | FR Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 10:30 a.m. | ||
| Sat., 10/10 | JV Girls Soccer | Fairfield Warde | Away - Fairfield Warde HS-Fairfield Warde Grass Utility Field [Directions] | 10:00 a.m. | ||
| Sat., 10/10 | FR Girls Soccer | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 10:00 a.m. | ||
| Sat., 10/10 | JV Girls Volleyball | Fairfield Ludlowe | Home - Trumbull HS-THS Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 10/10 | FR Girls Volleyball | Fairfield Ludlowe | Home - Trumbull HS-THS Main Gym [Directions] | 11:15 a.m. | ||
| Mon., 10/12 | V Boys Soccer | Fairfield Prep | Away - Fairfield University-Rafferty Stadium [Directions] | 5:30 p.m. | L 1-2 | |
| Tue., 10/13 | V Boys Cross Country | Fairfield Ludlowe | Home - Trumbull HS-Cross Country Course [Directions] | 3:45 p.m. | ||
| Tue., 10/13 | V Girls Cross Country | Fairfield Ludlowe | Home - Trumbull HS-Cross Country Course [Directions] | 3:45 p.m. | ||
| Tue., 10/13 | V Girls Soccer | Fairfield Ludlowe | Home - Trumbull HS-New Turf Field [Directions] | 3:45 p.m. | W 5-0 | |
| Tue., 10/13 | V Girls Swimming and Diving | Fairfield Warde | Home - New Canaan YMCA-Pool [Directions] | 4:15 p.m. | ||
| Tue., 10/13 | V Girls Volleyball | Fairfield Ludlowe | Home - Trumbull HS-THS Main Gym [Directions] | 3:45 p.m. | W 3-1 | |
| Wed., 10/14 | V Boys Soccer | Fairfield Warde | Away - Fairfield Warde HS-Varsity Grass Soccer Field [Directions] | 3:45 p.m. | L 0-2 | |
| Wed., 10/14 | V Field Hockey | Fairfield Ludlowe | Home - Trumbull HS-McDougall Stadium [Directions] | 3:45 p.m. | ||
| Thu., 10/15 | V Girls Soccer | St. Joseph | Home - Trumbull HS-New Turf Field [Directions] | 3:45 p.m. | L 1-2 | |
| Thu., 10/15 | V Girls Swimming and Diving | Fairfield Ludlowe | Home - Hillcrest MS-Pool [Directions] | 3:45 p.m. | ||
| Thu., 10/15 | V Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 10/16 | V Field Hockey | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 6:00 p.m. | ||
| Sat., 10/17 | JV Boys Soccer | Bridgeport Central | Away - Kennedy Stadium (Bridgeport) [Directions] | 9:00 a.m. | ||
| Sat., 10/17 | JV Field Hockey | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 12:00 p.m. | ||
| Sat., 10/17 | FR Field Hockey | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 1:30 p.m. | ||
| Sat., 10/17 | JV Girls Soccer | Fairfield Ludlowe | Home - Trumbull HS-New Turf Field [Directions] | 10:00 a.m. | ||
| Sat., 10/17 | FR Girls Soccer | Fairfield Ludlowe | Home - Trumbull HS-McDougall Stadium [Directions] | 10:00 a.m. | ||
| Sat., 10/17 | JV Girls Volleyball | Fairfield Warde | Home - Trumbull HS-THS Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 10/17 | FR Girls Volleyball | Fairfield Warde | Home - Trumbull HS-Aux Gym [Directions] | 11:15 a.m. | ||
| Mon., 10/19 | JV Football | Fairfield Prep | Home - Trumbull HS-McDougall Stadium [Directions] | 3:45 p.m. | ||
| Mon., 10/19 | FR Football | Fairfield Prep | Home - Trumbull HS-McDougall Stadium [Directions] | 3:45 p.m. | ||
| Mon., 10/19 | V Boys Soccer | Fairfield Warde | Home - Trumbull HS-New Turf Field [Directions] | 3:45 p.m. | W 2-1 | |
| Tue., 10/20 | V Football | Fairfield Prep | Home - Trumbull HS-McDougall Stadium [Directions] | 3:45 p.m. | ||
| Tue., 10/20 | V Girls Cross Country | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 3:30 p.m. | ||
| Tue., 10/20 | V Girls Volleyball | Fairfield Warde | Home - Trumbull HS-THS Main Gym [Directions] | 3:45 p.m. | W 3-0 | |
| Wed., 10/21 | V Boys Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 3:15 p.m. | L 1-3 | |
| Wed., 10/21 | V Field Hockey | Fairfield Warde | Home - Trumbull HS-McDougall Stadium [Directions] | 3:45 p.m. | W 1-0 | |
| Thu., 10/22 | V Girls Volleyball | St. Joseph | Home - Trumbull HS-THS Main Gym [Directions] | 3:45 p.m. | W 3-1 | |
| Fri., 10/23 | V Football | Bassick | Away - Kennedy Stadium (Bridgeport) [Directions] | 3:45 p.m. | ||
| Fri., 10/23 | V Field Hockey | St. Joseph | Home - Trumbull HS-McDougall Stadium [Directions] | 3:45 p.m. | ||
| Sat., 10/24 | V Boys Cross Country | Wilton | Away - Allen's Meadow-XC Course [Directions] | 11:00 a.m. | ||
| Sat., 10/24 | JV Boys Soccer | Fairfield Warde | Home - Trumbull HS-New Turf Field [Directions] | 10:00 a.m. | ||
| Sat., 10/24 | FR Boys Soccer | Fairfield Warde | Home - Trumbull HS-JV Grass Field [Directions] | 10:00 a.m. | ||
| Sat., 10/24 | V Girls Cross Country | Wilton | Away - Trumbull HS-Cross Country Course [Directions] | 10:45 a.m. | ||
| Sat., 10/24 | JV Field Hockey | Fairfield Ludlowe | Home - Trumbull HS-McDougall Stadium [Directions] | 10:00 a.m. | ||
| Sat., 10/24 | FR Field Hockey | Fairfield Ludlowe | Home - Trumbull HS-McDougall Stadium [Directions] | 11:15 a.m. | ||
| Sat., 10/24 | JV Girls Soccer | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 10:00 a.m. | ||
| Sat., 10/24 | V Girls Swimming and Diving | New Canaan | Home - Hillcrest MS-Pool [Directions] | 8:00 a.m. | ||
| Sat., 10/24 | JV Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 10:30 a.m. | ||
| Sat., 10/24 | FR Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 9:00 a.m. | ||
| Mon., 10/26 | V Boys Soccer | Bridgeport Central | Home - Trumbull HS-New Turf Field [Directions] | 3:45 p.m. | W 2-1 | |
| Tue., 10/27 | V Boys Cross Country | St. Joseph | Away - St. Joseph HS-Trail [Directions] | 4:30 p.m. | ||
| Tue., 10/27 | V Girls Cross Country | St. Joseph | Away - St. Joseph HS-Trail [Directions] | 3:45 p.m. | ||
| Tue., 10/27 | V Girls Soccer | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 6:00 p.m. | L 1-0 | |
| Tue., 10/27 | V Girls Swimming and Diving | Norwalk/McMahon | Away - Norwalk HS-Pat Spinola Natatorium [Directions] | 5:30 p.m. | ||
| Tue., 10/27 | V Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 3:45 p.m. | W 3-0 | |
| Wed., 10/28 | V Football | Harding | Home - Trumbull HS-McDougall Stadium [Directions] | 3:45 p.m. | ||
| Wed., 10/28 | V Boys Soccer | Harding | Away - Warren Harding HS-Lewis Field [Directions] | 3:30 p.m. | W 7-0 | |
| Wed., 10/28 | FR Boys Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 5:00 p.m. | ||
| Wed., 10/28 | V Field Hockey | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 3:45 p.m. | ||
| Wed., 10/28 | V Girls Soccer | Bridgeport Central | Home - Trumbull HS-New Turf Field [Directions] | 3:45 p.m. | W 8-0 | |
| Wed., 10/28 | V Girls Swimming and Diving | Darien | Away - Darien YMCA [Directions] | 3:00 p.m. | ||
| Pending changes awaiting acceptance by one or more parties involved: Date to 10/31, Time to 8:00 a.m. | ||||||
| Wed., 10/28 | V Girls Swimming and Diving | Darien | Home - Hillcrest MS-Pool [Directions] | 3:45 p.m. | ||
| Pending changes awaiting acceptance by one or more parties involved: Date to 10/31, Time to 8:00 a.m. | ||||||
| Thu., 10/29 | V Girls Diving | Diving vs. Ludlowe at the New Canaan YMCA | Home - TBA [Directions] | 8:20 p.m. | ||
| Thu., 10/29 | V Girls Swimming and Diving | Fairfield Ludlowe | Home - New Canaan YMCA-Pool [Directions] | 8:20 p.m. | ||
| Thu., 10/29 | V Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 10/30 | V Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 3:30 p.m. | ||
| Sat., 10/31 | JV Boys Soccer | Fairfield Ludlowe | Home - Trumbull HS-McDougall Stadium [Directions] | 10:00 a.m. | ||
| Sat., 10/31 | FR Boys Soccer | Fairfield Ludlowe | Home - Trumbull HS-JV Grass Field [Directions] | 12:00 p.m. | ||
| Sat., 10/31 | JV Field Hockey | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 10:00 a.m. | ||
| Sat., 10/31 | V Girls Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 12:00 p.m. | L 1-0 | |
| Sat., 10/31 | JV Girls Soccer | Fairfield Warde | Home - Trumbull HS-New Turf Field [Directions] | 10:00 a.m. | ||
| Sat., 10/31 | JV Girls Volleyball | Fairfield Ludlowe | Home - Trumbull HS-THS Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 10/31 | FR Girls Volleyball | Fairfield Ludlowe | Home - Trumbull HS-Aux Gym [Directions] | 11:15 a.m. | ||
| Mon., 11/2 | JV Football | Fairfield Warde | Home - Trumbull HS-McDougall Stadium [Directions] | 3:45 p.m. | ||
| Mon., 11/2 | FR Football | Fairfield Warde | Home - Trumbull HS-McDougall Stadium [Directions] | 3:45 p.m. | ||
| Mon., 11/2 | V Boys Soccer | Bassick | Home - Trumbull HS-New Turf Field [Directions] | 3:45 p.m. | W 1-0 | |
| Tue., 11/3 | V Field Hockey | Fairfield Ludlowe | Home - Trumbull HS-McDougall Stadium [Directions] | 3:45 p.m. | ||
| Tue., 11/3 | V Girls Soccer | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 3:00 p.m. | L 2-1 | |
| Tue., 11/3 | V Girls Volleyball | Fairfield Ludlowe | Home - Trumbull HS-THS Main Gym [Directions] | 3:45 p.m. | W 3-0 | |
| Wed., 11/4 | V Football | Fairfield Warde | Home - Trumbull HS-McDougall Stadium [Directions] | 3:45 p.m. | ||
| Wed., 11/4 | V Boys Soccer | St. Joseph | Home - Trumbull HS-New Turf Field [Directions] | 3:45 p.m. | L 0-1 | |
| Wed., 11/4 | V Girls Cross Country | FCIAC Regional Cross Country Championship | Away - Trumbull HS-Cross Country Course | 2:15 p.m. | ||
| Wed., 11/4 | V Girls Swimming and Diving | Norwalk/McMahon | Home - Hillcrest MS-Pool [Directions] | 3:45 p.m. | ||
| Thu., 11/5 | V Field Hockey | St. Joseph | Home - Trumbull HS-McDougall Stadium [Directions] | 3:45 p.m. | ||
| Thu., 11/5 | V Girls Soccer | Bridgeport Central | Away - Bridgeport Central HS-Kennedy Stadium Turf [Directions] | 3:30 p.m. | W 5-1 | |
| Thu., 11/5 | FR Girls Soccer | Fairfield Warde | Home - Trumbull HS-New Turf Field [Directions] | 3:45 p.m. | ||
| Thu., 11/5 | V Girls Volleyball | Fairfield Warde | Home - Trumbull HS-THS Main Gym [Directions] | 3:45 p.m. | W 3-0 | |
| Fri., 11/6 | V Boys Soccer | Bridgeport Central | Home - Trumbull HS-New Turf Field [Directions] | 3:45 p.m. | T 1-1 | |
| Sat., 11/7 | JV Boys Soccer | St. Joseph | Home - Trumbull HS-New Turf Field [Directions] | 10:00 a.m. | ||
| Sat., 11/7 | V Field Hockey | Fairfield Ludlowe | Home - Trumbull HS-McDougall Stadium [Directions] | 11:00 a.m. | ||
| Sat., 11/7 | JV Field Hockey | Fairfield Warde | Home - Trumbull HS-McDougall Stadium [Directions] | 1:00 p.m. | ||
| Sat., 11/7 | JV Girls Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 11:00 a.m. | ||
| Sat., 11/7 | FR Girls Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 9:00 a.m. | ||
| Sat., 11/7 | V Girls Volleyball | Fairfield Ludlowe | Home - Trumbull HS-THS Main Gym [Directions] | 2:00 p.m. | W 3-0 | |
| Sat., 11/7 | JV Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 10:30 a.m. | ||
| Sat., 11/7 | FR Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 9:00 a.m. | ||
| Wed., 2/10 | V Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:00 p.m. | L 82-83 | |
| Wed., 2/10 | V Boys Ice Hockey | Staples | Away - Milford Ice Pavillion-Ice Rink [Directions] | 6:30 p.m. | W 8-3 | |
| Wed., 2/10 | V Boys Swimming and Diving | Staples | Away - Staples HS-Staples High School Pool [Directions] | 4:30 p.m. | ||
| Wed., 2/10 | V Girls Basketball | Ridgefield | Home - Trumbull HS-THS Main Gym [Directions] | 5:00 p.m. | L 40-47 | |
| Wed., 2/10 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:45 p.m. | L 3-5 | |
| Fri., 2/12 | V Boys Basketball | Fairfield Ludlowe | Home - Trumbull HS-THS Main Gym [Directions] | 5:00 p.m. | L 45-51 | |
| Fri., 2/12 | V Boys Swimming and Diving | Staples | Home - Hillcrest MS-Pool [Directions] | 3:30 p.m. | ||
| Fri., 2/12 | V Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:00 p.m. | W 55-52 | |
| Sat., 2/13 | JV Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 11:30 a.m. | ||
| Sat., 2/13 | FR Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 2/13 | V Boys Ice Hockey | Watertown-Pomperaug | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 8:30 p.m. | W 4-2 | |
| Sat., 2/13 | JV Girls Basketball | Ridgefield | Home - Trumbull HS-THS Main Gym [Directions] | 11:30 a.m. | ||
| Sat., 2/13 | FR Girls Basketball | Ridgefield | Home - Trumbull HS-THS Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 2/13 | V Girls Gymnastics | Staples | Home - Next Dimension Gymnastics-Next Dimension [Directions] | 2:00 p.m. | TRUMBULL-137.4; Staples-127.75 | |
| Sat., 2/13 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Conners - Stamford-Ice Rink [Directions] | 6:00 p.m. | W 7-1 | |
| Sun., 2/14 | JV Girls Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | 12:30 p.m. | ||
| Mon., 2/15 | V Boys Ice Hockey | Wilton | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 2:15 p.m. | ||
| Mon., 2/15 | V Girls Ice Hockey | Greenwich | Away - Greenwich - Dorothy Hamill-Rink [Directions] | 3:00 p.m. | W 2-1 | |
| Tue., 2/16 | V Boys Basketball | New Canaan | Home - Trumbull HS-THS Main Gym [Directions] | 5:00 p.m. | L 36-55 | |
| Tue., 2/16 | V Girls Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 5:00 p.m. | W 46-24 | |
| Wed., 2/17 | JV Boys Basketball | Westhill | Home - Trumbull HS-THS Main Gym [Directions] | 3:30 p.m. | ||
| Wed., 2/17 | FR Boys Basketball | Westhill | Home - Trumbull HS-THS Main Gym [Directions] | 5:00 p.m. | ||
| Wed., 2/17 | V Boys Ice Hockey | Westhill/Stamford | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 6:30 p.m. | W 8-1 | |
| Wed., 2/17 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Home - Hillcrest MS-Pool [Directions] | 3:30 p.m. | ||
| Wed., 2/17 | FR Girls Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 3:30 p.m. | ||
| Wed., 2/17 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 5:30 p.m. | W 9-1 | |
| Wed., 2/17 | JV Girls Ice Hockey | West Haven/SHA | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 5:30 p.m. | ||
| Fri., 2/19 | V Boys Swimming and Diving | Danbury, St. Joseph | Home - Hillcrest MS-Pool [Directions] | Postponed | ||
| Pending changes awaiting acceptance by one or more parties involved: Date to 2/26, Time to 4:30 p.m. | ||||||
| Fri., 2/19 | JV Girls Ice Hockey | New Canaan | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | Postponed | ||
| Sat., 2/20 | V Boys Basketball | St. Joseph | Home - Trumbull HS-THS Main Gym [Directions] | 12:30 p.m. | L 61-72 | |
| Sat., 2/20 | JV Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 10:30 a.m. | ||
| Sat., 2/20 | FR Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 9:00 a.m. | ||
| Sat., 2/20 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 6:30 p.m. | L 1-5 | |
| Sat., 2/20 | V Girls Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 2:00 p.m. | W 49-39 | |
| Sat., 2/20 | JV Girls Basketball | St. Joseph | Home - Trumbull HS-THS Main Gym [Directions] | 10:30 a.m. | ||
| Sat., 2/20 | FR Girls Basketball | St. Joseph | Home - Trumbull HS-THS Main Gym [Directions] | 9:00 a.m. | ||
| Sat., 2/20 | V Girls Gymnastics | Wilton | Home - Next Dimension Gymnastics-Next Dimension [Directions] | 9:30 a.m. | TRUMBULL-143.7 | |
| Sat., 2/20 | V Girls Gymnastics | Hub Meet | Away - TBA | 9:45 a.m. | ||
| Sat., 2/20 | V Girls Ice Hockey | New Canaan | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | L 9-0 | |
| Sun., 2/21 | JV Boys Ice Hockey | Ridgefield | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:10 p.m. | ||
| Sun., 2/21 | V Girls Gymnastics | Greenwich | Home - Next Dimension Gymnastics-Next Dimension [Directions] | 1:00 p.m. | TRUMBULL-138.4 | |
| Sun., 2/21 | JV Girls Ice Hockey | West Haven/SHA | Away - West Haven HS-Bennett Rink [Directions] | 1:30 p.m. | ||
| Mon., 2/22 | V Boys Diving | Fairfield Ludlowe | Home - Hillcrest MS-Pool [Directions] | 7:40 p.m. | ||
| Mon., 2/22 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 4:40 p.m. | ||
| Mon., 2/22 | JV Girls Ice Hockey | Masuk Coop | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to 4:00 p.m. | ||||||
| Wed., 2/24 | JV Boys Basketball | Fairfield Warde | Home - Trumbull HS-THS Main Gym [Directions] | 5:00 p.m. | ||
| Wed., 2/24 | FR Boys Basketball | Fairfield Warde | Home - Trumbull HS-THS Main Gym [Directions] | 3:30 p.m. | ||
| Wed., 2/24 | JV Boys Ice Hockey | Staples | Away - Milford Ice Pavillion-Ice Rink [Directions] | Canceled | Cancelled | |
| Wed., 2/24 | JV Girls Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | Canceled | Cancelled | |
| Wed., 2/24 | FR Girls Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:30 p.m. | ||
| Wed., 2/24 | V Girls Ice Hockey | Stamford/Westhill/Staples | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | W 11-5 | |
| Thu., 2/25 | V Boys Basketball | Staples | Home - Trumbull HS-THS Main Gym [Directions] | 5:00 p.m. | L 56-63 | |
| Thu., 2/25 | V Boys Ice Hockey | St. Joseph | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | 3:15 p.m. | W 3-1 | |
| Thu., 2/25 | V Girls Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 5:00 p.m. | L 38-44 | |
| Fri., 2/26 | JV Boys Ice Hockey | Fairfield Warde/Ludlowe | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 5:00 p.m. | ||
| Sat., 2/27 | V Boys Basketball | Westhill | Home - Trumbull HS-THS Main Gym [Directions] | 12:30 p.m. | W 65-58 | |
| Sat., 2/27 | JV Boys Basketball | Westhill | Home - Trumbull HS-THS Main Gym [Directions] | 10:30 a.m. | ||
| Sat., 2/27 | FR Boys Basketball | Westhill | Home - Trumbull HS-THS Main Gym [Directions] | 9:00 a.m. | ||
| Sat., 2/27 | V Boys Ice Hockey | Westhill/Stamford | Away - Terry Conners - Stamford-Ice Rink [Directions] | 6:50 p.m. | ||
| Sat., 2/27 | V Girls Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 2:15 p.m. | W 59-37 | |
| Sat., 2/27 | JV Girls Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | Canceled | Cancelled | |
| Sat., 2/27 | FR Girls Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | Canceled | Cancelled | |
| Sat., 2/27 | V Girls Ice Hockey | Darien | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 8:30 p.m. | L 1-9 | |
| Sun., 2/28 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 2:30 p.m. | W 9-1 | |
| Tue., 3/2 | V Boys Basketball | Bridgeport Central | Home - Trumbull HS-THS Main Gym [Directions] | 5:15 p.m. | W 61-42 | |
| Tue., 3/2 | V Girls Basketball | Bridgeport Central | Home - Trumbull HS-THS Main Gym [Directions] | 3:30 p.m. | W 50-13 | |
| Wed., 3/3 | V Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 5:00 p.m. | W 64-40 | |
| Wed., 3/3 | JV Boys Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Wed., 3/3 | V Boys Swimming and Diving | Westhill/Stamford | Home - Hillcrest MS-Pool [Directions] | 3:30 p.m. | ||
| Wed., 3/3 | V Girls Basketball | Brien McMahon | Home - Trumbull HS-THS Main Gym [Directions] | 5:15 p.m. | W 59-10 | |
| Wed., 3/3 | JV Girls Basketball | Staples | Home - Trumbull HS-THS Main Gym [Directions] | 3:30 p.m. | ||
| Wed., 3/3 | FR Girls Basketball | Staples | Home - Trumbull HS-THS Main Gym [Directions] | Canceled | Cancelled | |
| Wed., 3/3 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | W 10-2 | |
| Thu., 3/4 | JV Boys Ice Hockey | Ridgefield | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 4:00 p.m. | ||
| Thu., 3/4 | V Boys Swimming and Diving | St. Joseph | Home - Hillcrest MS-Pool [Directions] | 3:30 p.m. | ||
| Fri., 3/5 | V Boys Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:00 p.m. | L 49-54 | |
| Fri., 3/5 | V Girls Basketball | Greenwich | Home - Trumbull HS-THS Main Gym [Directions] | 5:00 p.m. | W 62-34 | |
| Sat., 3/6 | JV Boys Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 11:00 a.m. | ||
| Sat., 3/6 | FR Boys Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 9:30 a.m. | ||
| Sat., 3/6 | V Boys Ice Hockey | Staples | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 8:30 p.m. | W 6-1 | |
| Sat., 3/6 | JV Girls Basketball | Danbury | Home - Trumbull HS-THS Main Gym [Directions] | Canceled | Cancelled | |
| Sat., 3/6 | FR Girls Basketball | Danbury | Home - Trumbull HS-THS Main Gym [Directions] | Canceled | Cancelled | |
| Sat., 3/6 | V Girls Ice Hockey | Greenwich | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 8:30 p.m. | T 2-2(OT) | |
| Sun., 3/7 | V Girls Gymnastics | Fairfield Ludlowe, St. Joseph | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 1:00 p.m. | TRUMBULL-138.0; Ludlowe-141.1 | |
| Sun., 3/7 | V Girls Gymnastics | Fairfield Warde | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 3:00 p.m. | Warde-137.6 | |
| Mon., 3/8 | V Boys Basketball | Wilton | Home - Trumbull HS-THS Main Gym [Directions] | 6:30 p.m. | L 47-54 | |
| Mon., 3/8 | JV Boys Ice Hockey | St. Joseph | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 4:00 p.m. | ||
| Mon., 3/8 | V Girls Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:00 p.m. | W 54-32 | |
| Wed., 3/10 | JV Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | Canceled | Cancelled | |
| Wed., 3/10 | V Boys Diving | Westhill | Away - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Wed., 3/10 | V Boys Ice Hockey | Brien McMahon/Norwalk | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 8:00 p.m. | W 4-2 | |
| Wed., 3/10 | V Boys Indoor Track | Brien McMahon | Home - Trumbull HS-McDougall Stadium [Directions] | 3:30 p.m. | ||
| Wed., 3/10 | V Boys Swimming and Diving | New Canaan | Home - Hillcrest MS-Pool [Directions] | 3:30 p.m. | ||
| Wed., 3/10 | JV Girls Basketball | Fairfield Ludlowe | Home - Trumbull HS-THS Main Gym [Directions] | 5:00 p.m. | ||
| Wed., 3/10 | FR Girls Basketball | Fairfield Ludlowe | Home - Trumbull HS-THS Main Gym [Directions] | 3:30 p.m. | ||
| Wed., 3/10 | V Girls Gymnastics | New Canaan | Away - Chelsea Piers - -Gym [Directions] | 7:30 p.m. | New Canaan-86.65 | |
| Wed., 3/10 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 5:30 p.m. | W 5-0 | |
| Wed., 3/10 | V Girls Indoor Track | Brien McMahon | Home - Trumbull HS-McDougall Stadium [Directions] | 3:30 p.m. | ||
| Thu., 3/11 | V Boys Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 4:30 p.m. | L 59-70 | |
| Thu., 3/11 | FR Boys Basketball | St. Joseph | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 3/11 | JV Girls Ice Hockey | Masuk Coop | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 5:00 p.m. | ||
| Fri., 3/12 | V Boys Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:30 p.m. | W 43-41 | |
| Fri., 3/12 | V Boys Ice Hockey | Immaculate | Away - Danbury Ice Arena-Patriot Rink [Directions] | 7:45 p.m. | W 4-3 | |
| Fri., 3/12 | V Girls Basketball | Darien | Home - Trumbull HS-THS Main Gym [Directions] | 5:00 p.m. | W 54-19 | |
| Sat., 3/13 | JV Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 9:00 a.m. | ||
| Sat., 3/13 | V Boys Ice Hockey | Immaculate | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 8:30 p.m. | W 5-4 | |
| Sat., 3/13 | JV Girls Basketball | New Canaan | Home - Trumbull HS-THS Main Gym [Directions] | 11:30 a.m. | ||
| Sat., 3/13 | FR Girls Basketball | New Canaan | Home - Trumbull HS-THS Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 3/13 | V Girls Gymnastics | Westhill | Home - Next Dimension Gymnastics-Next Dimension [Directions] | 2:00 p.m. | TRUMBULL 139.85 Westhill 101.95 | |
| Sat., 3/13 | V Girls Gymnastics | Darien | Away - Darien YMCA [Directions] | 2:30 p.m. | Darien-125.85 | |
| Sun., 3/14 | V Girls Gymnastics | Darien | Home - Next Dimension Gymnastics-Next Dimension [Directions] | 1:00 p.m. | TRUMBULL-137.65 | |
| Sun., 3/14 | JV Girls Ice Hockey | West Haven/SHA | Away - West Haven HS-Bennett Rink [Directions] | Canceled | Cancelled | |
| Mon., 3/15 | JV Boys Ice Hockey | St. Joseph | Away - Sports Center of Connecticut-Lower [Directions] | 3:00 p.m. | ||
| Mon., 3/15 | V Girls Basketball | Danbury | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | W 62-43 | |
| Mon., 3/15 | V Girls Ice Hockey | Stamford/Westhill/Staples | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 3:15 p.m. | W 6-2 | |
| Tue., 3/16 | V Boys Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 6:00 p.m. | L 37-57 | |
| Wed., 3/17 | V Boys Ice Hockey | Wilton | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:30 p.m. | ||
| Wed., 3/17 | V Girls Basketball | Westhill | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | W 50-33 | |
| Thu., 3/18 | JV Boys Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 3/18 | FR Boys Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 3/18 | JV Boys Ice Hockey | Staples | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 4:00 p.m. | ||
| Thu., 3/18 | JV Girls Basketball | Fairfield Ludlowe | Home - Trumbull HS-THS Main Gym [Directions] | 5:00 p.m. | ||
| Thu., 3/18 | FR Girls Basketball | Fairfield Ludlowe | Home - Trumbull HS-THS Main Gym [Directions] | 3:30 p.m. | ||
| Thu., 3/18 | V Girls Gymnastics | Greenwich, St. Joseph | Away - Greenwich YWCA [Directions] | 6:00 p.m. | Greenwich-131.3 | |
| Thu., 3/18 | V Girls Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | 7:15 p.m. | ||
| Fri., 3/19 | V Boys Swimming and Diving | St. Joseph, Staples | Home - Hillcrest MS-Pool [Directions] | 3:30 p.m. | ||
| Sat., 3/20 | JV Boys Basketball | Greenwich | Home - Trumbull HS-THS Main Gym [Directions] | 11:00 a.m. | ||
| Sat., 3/20 | FR Boys Basketball | Greenwich | Home - Trumbull HS-THS Main Gym [Directions] | 9:30 a.m. | ||
| Sat., 3/20 | V Boys Ice Hockey | Brien McMahon/Norwalk | Away - Sono Ice House-Main Rink [Directions] | Canceled | Cancelled | |
| Sat., 3/20 | V Girls Basketball | Stamford | Home - Trumbull HS-THS Main Gym [Directions] | 1:00 p.m. | W 55-27 | |
| Sat., 3/20 | JV Girls Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 10:30 a.m. | ||
| Sat., 3/20 | FR Girls Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 9:00 a.m. | ||
| Mon., 3/22 | JV Girls Basketball | Danbury | Home - Trumbull HS-THS Main Gym [Directions] | 7:00 p.m. | ||
| Mon., 3/22 | FR Girls Basketball | Danbury | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 3/24 | V Girls Basketball | Danbury | Home - Trumbull HS-THS Main Gym [Directions] | 5:00 p.m. | ||
| Sat., 3/27 | V Girls Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 7:00 p.m. | L 43-46 | |
| Sat., 3/27 | V Girls Gymnastics | FCIAC Championship | Home - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 8:30 a.m. | 137.5 | |
| Sat., 4/10 | V Baseball | St. Joseph | Away - St. Joseph HS-Baseball Diamond [Directions] | 11:00 a.m. | W 5-1 | |
| Sat., 4/10 | JV Baseball | St. Joseph | Home - Trumbull HS-Varsity Baseball Field [Directions] | 11:00 a.m. | W 5-0 | |
| Sat., 4/10 | FR Baseball | Ridgefield | Away - Governor Field [Directions] | 10:00 a.m. | W 13-3 | |
| Sat., 4/10 | FR Baseball | Ridgefield | Away - Governor Field [Directions] | 12:00 p.m. | W 11-10 | |
| Sat., 4/10 | V Boys Lacrosse | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 12:00 p.m. | W 19-5 | |
| Sat., 4/10 | JV Boys Lacrosse | Norwalk | Away - Norwalk HS-Testa Field [Directions] | Postponed | ||
| Sat., 4/10 | V Boys Tennis | Westhill | Home - Trumbull HS-Tennis Courts [Directions] | 11:00 a.m. | L 1-6 | |
| Sat., 4/10 | V Boys Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 12:00 p.m. | W 3-0 | |
| Sat., 4/10 | JV Boys Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 4/10 | V Softball | St. Joseph | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 11:00 a.m. | L 0-12 | |
| Sat., 4/10 | V Girls Tennis | Westhill | Away - Westhill HS-Westhill Tennis Courts [Directions] | 10:00 a.m. | L 0-7 | |
| Mon., 4/12 | V Boys Volleyball | Ridgefield | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | W 3-1 | |
| Mon., 4/12 | JV Boys Volleyball | Ridgefield | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 4/13 | V Boys Tennis | Darien | Home - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Tue., 4/13 | JV Boys Tennis | Darien | Home - Unity Park [Directions] | 4:00 p.m. | ||
| Tue., 4/13 | V Girls Tennis | Darien | Away - Darien HS-DHS Tennis Courts [Directions] | 10:00 a.m. | L 0-7 | |
| Tue., 4/13 | JV Girls Tennis | Darien | Away - Weed Beach Tennis Courts [Directions] | 10:00 a.m. | ||
| Wed., 4/14 | V Boys Tennis | Danbury | Away - Danbury HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Wed., 4/14 | V Boys Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 4/14 | JV Boys Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 4/14 | V Girls Tennis | Danbury | Home - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Thu., 4/15 | V Girls Lacrosse | Guilford | Away - Guilford HS-New Turf field at GHS [Directions] | 3:45 p.m. | L 5-17 | |
| Fri., 4/16 | V Baseball | New Canaan | Away - Mead Park-Baseball Field [Directions] | 4:00 p.m. | L 3-0 | |
| Fri., 4/16 | FR Boys Lacrosse | Stamford | Away - Stamford HS-Upper Lacrosse Field [Directions] | 5:00 p.m. | ||
| Sat., 4/17 | FR Baseball | New Canaan | Home - Trumbull HS-Varsity Baseball Field [Directions] | 10:00 a.m. | W 10-0 | |
| Sat., 4/17 | FR Baseball | New Canaan | Home - Trumbull HS-Varsity Baseball Field [Directions] | 12:00 p.m. | W 15-1 | |
| Sat., 4/17 | V Boys Volleyball | Greenwich | Home - Trumbull HS-THS Main Gym [Directions] | 11:30 a.m. | W 3-0 | |
| Sat., 4/17 | JV Boys Volleyball | Greenwich | Home - Trumbull HS-THS Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 4/17 | V Girls Lacrosse | St. Joseph | Home - Trumbull HS-McDougall Stadium [Directions] | 12:00 p.m. | L 10-11 | |
| Sat., 4/17 | JV Softball | New Canaan | Away - Waveny Park-Orchard Field [Directions] | 11:00 a.m. | ||
| Mon., 4/19 | V Baseball | Fairfield Warde | Away - Fairfield Warde HS-Baseball Diamond [Directions] | 4:00 p.m. | W 1-0 | |
| Mon., 4/19 | JV Baseball | Fairfield Warde | Home - Trumbull HS-Varsity Baseball Field [Directions] | 4:00 p.m. | W 5-1 | |
| Mon., 4/19 | V Boys Golf | Wilton | Away - Rolling Hills Country Club [Directions] | 3:15 p.m. | THS 212 WHS 176 | |
| Mon., 4/19 | JV Boys Golf | Wilton | Away - Rolling Hills Country Club [Directions] | 3:15 p.m. | ||
| Mon., 4/19 | V Boys Lacrosse | Notre Dame-West Haven | Home - Trumbull HS-McDougall Stadium [Directions] | 5:30 p.m. | W 10-9 | |
| Mon., 4/19 | JV Boys Lacrosse | Notre Dame-West Haven | Home - Trumbull HS-Cork Field [Directions] | 4:00 p.m. | ||
| Mon., 4/19 | FR Boys Lacrosse | Danbury | Home - Trumbull HS-The Pit [Directions] | Canceled | Cancelled | |
| Mon., 4/19 | V Boys Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Tennis Courts [Directions] | 4:00 p.m. | L 3-4 | |
| Mon., 4/19 | JV Boys Tennis | Fairfield Ludlowe | Away - Dwight Elementary School-Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 4/19 | V Boys Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 4/19 | V Softball | Fairfield Warde | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 4:15 p.m. | W 3-1 | |
| Mon., 4/19 | V Girls Tennis | Fairfield Ludlowe | Home - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Mon., 4/19 | JV Girls Tennis | Fairfield Ludlowe | Home - Unity Park [Directions] | 4:00 p.m. | ||
| Tue., 4/20 | JV Baseball | New Canaan | Home - Trumbull HS-Varsity Baseball Field [Directions] | 4:00 p.m. | W 5-2 | |
| Tue., 4/20 | V Boys Golf | New Canaan | Away - CCNC [Directions] | 3:15 p.m. | THS 189 NCHS 156 | |
| Tue., 4/20 | V Boys Outdoor Track | Westhill | Home - Trumbull HS-McDougall Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/20 | V Boys Tennis | Greenwich | Home - Trumbull HS-Tennis Courts [Directions] | 4:30 p.m. | L 0-7 | |
| Tue., 4/20 | V Girls Golf | Wilton | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | THS-197 WHS-XXX | |
| Tue., 4/20 | V Girls Outdoor Track | Westhill | Home - Trumbull HS-McDougall Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/20 | V Softball | New Canaan | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 4:15 p.m. | W 13-1 | |
| Tue., 4/20 | JV Softball | Fairfield Warde | Away - Melville Park [Directions] | Canceled | Cancelled | |
| Tue., 4/20 | V Girls Tennis | Greenwich | Away - Greenwich HS-Tennis Courts [Directions] | 4:30 p.m. | L 0-7 | |
| Tue., 4/20 | JV Girls Tennis | Greenwich | Away - Binney Park [Directions] | 4:30 p.m. | ||
| Wed., 4/21 | V Boys Volleyball | Fairfield Warde | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 4/21 | JV Boys Volleyball | Fairfield Warde | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 4/22 | V Baseball | Harding | Away - Warren Harding HS-Baseball Field [Directions] | 4:00 p.m. | W 10-0 | |
| Thu., 4/22 | V Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 6:00 p.m. | L 3-16 | |
| Thu., 4/22 | JV Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | ||
| Thu., 4/22 | FR Boys Lacrosse | Westhill | Home - Trumbull HS-The Pit [Directions] | 4:30 p.m. | ||
| Thu., 4/22 | V Boys Tennis | Bridgeport Central | Away - Bridgeport Central HS-Central High School Tennis Courts [Directions] | 3:30 p.m. | W 7-0 | |
| Thu., 4/22 | V Girls Lacrosse | Fairfield Warde | Home - Trumbull HS-McDougall Stadium [Directions] | 5:30 p.m. | W 12-5 | |
| Thu., 4/22 | JV Girls Lacrosse | Fairfield Warde | Home - Trumbull HS-Cork Field [Directions] | 4:00 p.m. | L 10-2 | |
| Thu., 4/22 | V Softball | Fairfield Ludlowe | Away - Sturges Park (Ludlowe HS)-Softball Diamond [Directions] | 4:00 p.m. | L 15-5 | |
| Thu., 4/22 | JV Softball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 6:00 p.m. | ||
| Thu., 4/22 | V Girls Tennis | Bridgeport Central | Home - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Fri., 4/23 | FR Boys Lacrosse | Fairfield Ludlowe | Home - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Fri., 4/23 | V Softball | Harding | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 4:15 p.m. | W 12-0 | |
| Sat., 4/24 | V Baseball | Fairfield Ludlowe | Home - Trumbull HS-Varsity Baseball Field [Directions] | 11:00 a.m. | W 4-0 | |
| Sat., 4/24 | JV Baseball | Fairfield Ludlowe | Home - Trumbull HS-JV Baseball Field [Directions] | 11:00 a.m. | W 6-5 | |
| Sat., 4/24 | FR Baseball | St. Joseph | Away - St. Joseph HS-Baseball Diamond [Directions] | 10:30 a.m. | W 8-4 | |
| Sat., 4/24 | FR Baseball | St. Joseph | Away - St. Joseph HS-Baseball Diamond [Directions] | 12:30 p.m. | W 12-2 | |
| Sat., 4/24 | V Boys Volleyball | Danbury | Home - Trumbull HS-THS Main Gym [Directions] | 11:30 a.m. | W 3-0 | |
| Sat., 4/24 | JV Boys Volleyball | Danbury | Home - Trumbull HS-THS Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 4/24 | V Girls Lacrosse | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 11:00 a.m. | W 17-5 | |
| Sat., 4/24 | JV Girls Lacrosse | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 12:15 p.m. | W 7-4 | |
| Sat., 4/24 | JV Softball | Harding | Away - Warren Harding HS-Beardsley Park #3 [Directions] | Canceled | Cancelled | |
| Sat., 4/24 | JV Softball | Fairfield Warde | Away - Fairfield Warde HS-Softball Diamond [Directions] | 1:00 p.m. | ||
| Mon., 4/26 | V Baseball | Westhill | Home - Trumbull HS-Varsity Baseball Field [Directions] | 4:00 p.m. | W 6-3 | |
| Mon., 4/26 | JV Baseball | Westhill | Away - Westhill HS-Varsity Baseball Field [Directions] | 4:00 p.m. | W 16-1 | |
| Mon., 4/26 | V Boys Golf | Staples | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | THS 199 Staples 169 | |
| Mon., 4/26 | FR Boys Lacrosse | Greenwich | Home - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Mon., 4/26 | V Boys Tennis | Stamford | Away - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Mon., 4/26 | V Boys Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 4/26 | JV Boys Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 4/26 | V Girls Golf | Darien | Home - Tashua Knolls Golf Course [Directions] | 3:30 p.m. | THS-205 DHS-227 | |
| Mon., 4/26 | JV Girls Golf | Darien | Home - Tashua Knolls Golf Course [Directions] | 3:30 p.m. | THS-229 DHS-220 | |
| Mon., 4/26 | V Girls Lacrosse | Cheshire | Away - Cheshire HS-Cheshire High School Main Game field [Directions] | 6:00 p.m. | L 4-20 | |
| Mon., 4/26 | JV Girls Lacrosse | Cheshire | Away - Cheshire HS-Bartlem Park [Directions] | 4:30 p.m. | L 14-0 | |
| Mon., 4/26 | V Softball | Westhill | Away - Westhill HS-Varsity Softball Field [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 4/26 | JV Softball | Westhill | Away - Westhill HS-Varsity Softball Field [Directions] | 6:00 p.m. | ||
| Mon., 4/26 | V Girls Tennis | Stamford | Home - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Tue., 4/27 | V Boys Golf | Fairfield Ludlowe | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | THS 201 Ludlowe 168 | |
| Tue., 4/27 | V Boys Lacrosse | Brien McMahon | Home - Trumbull HS-McDougall Stadium [Directions] | 5:30 p.m. | W 12-9 | |
| Tue., 4/27 | JV Boys Lacrosse | Brien McMahon | Home - Trumbull HS-Cork Field [Directions] | 4:30 p.m. | ||
| Tue., 4/27 | V Boys Outdoor Track | Staples | Away - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/27 | V Boys Tennis | Staples | Home - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Tue., 4/27 | V Girls Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 3:00 p.m. | THS-197 FLHS-189 | |
| Tue., 4/27 | V Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 6:00 p.m. | W 15-9 | |
| Tue., 4/27 | JV Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 7:15 p.m. | L 10-1 | |
| Tue., 4/27 | V Girls Outdoor Track | Staples | Away - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/27 | V Girls Tennis | Staples | Away - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Tue., 4/27 | JV Girls Tennis | Staples | Away - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/28 | V Baseball | Darien | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | W 10-6 | |
| Wed., 4/28 | V Boys Golf | Westhill | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | THS 188 Westhill 195 | |
| Wed., 4/28 | FR Boys Lacrosse | Staples | Home - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Wed., 4/28 | V Boys Tennis | Ridgefield | Home - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | L 1-6 | |
| Wed., 4/28 | JV Boys Tennis | Ridgefield | Home - Unity Park [Directions] | 4:00 p.m. | ||
| Wed., 4/28 | V Boys Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 4/28 | V Girls Golf | St. Joseph | Away - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | THS-191 SJHS-193 | |
| Wed., 4/28 | JV Girls Golf | St. Joseph | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Wed., 4/28 | JV Softball | Darien | Away - Darien HS-DHS - Softball - JV Field [Directions] | Canceled | Cancelled | |
| Wed., 4/28 | V Girls Tennis | Ridgefield | Away - Ridgefield HS-RHS Tennis Courts [Directions] | 4:00 p.m. | L 1-6 | |
| Wed., 4/28 | JV Girls Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 4/29 | V Boys Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Turf [Directions] | 3:45 p.m. | L 13-7 | |
| Thu., 4/29 | JV Boys Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 5:45 p.m. | ||
| Thu., 4/29 | V Girls Lacrosse | Fairfield Ludlowe | Home - Trumbull HS-McDougall Stadium [Directions] | 5:30 p.m. | L 5-17 | |
| Fri., 4/30 | V Baseball | Staples | Home - Trumbull HS-Varsity Baseball Field [Directions] | 4:00 p.m. | L 15-5 | |
| Fri., 4/30 | JV Baseball | Staples | Away - Staples HS-Baseball Diamond [Directions] | 4:00 p.m. | L 9-8 | |
| Fri., 4/30 | FR Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Fairfield Warde Grass Utility Field [Directions] | 4:15 p.m. | ||
| Fri., 4/30 | V Boys Outdoor Track | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium Track [Directions] | 4:00 p.m. | ||
| Fri., 4/30 | V Boys Tennis | Wilton | Away - Wilton HS-Wilton Varsity Tennis Courts [Directions] | 4:30 p.m. | L 0-7 | |
| Fri., 4/30 | JV Boys Tennis | Wilton | Away - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 4/30 | V Boys Volleyball | New Canaan | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | L 2-3 | |
| Fri., 4/30 | JV Boys Volleyball | New Canaan | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 4/30 | V Girls Outdoor Track | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 4:00 p.m. | ||
| Fri., 4/30 | V Softball | Staples | Away - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | L 2-3 | |
| Sat., 5/1 | JV Baseball | Darien | Home - Trumbull HS-JV Baseball Field [Directions] | 10:00 a.m. | W 10-0 | |
| Sat., 5/1 | FR Baseball | Danbury | Home - Trumbull HS-Varsity Baseball Field [Directions] | 10:00 a.m. | W 14-4 | |
| Sat., 5/1 | FR Baseball | Danbury | Home - Trumbull HS-Varsity Baseball Field [Directions] | 12:00 p.m. | W 12-4 | |
| Sat., 5/1 | V Boys Lacrosse | St. Joseph | Home - Trumbull HS-McDougall Stadium [Directions] | 12:00 p.m. | W 11-10 | |
| Sat., 5/1 | JV Boys Lacrosse | St. Joseph | Home - Trumbull HS-McDougall Stadium [Directions] | 10:00 a.m. | ||
| Sat., 5/1 | V Girls Lacrosse | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 12:00 p.m. | L 9-12 | |
| Mon., 5/3 | V Baseball | Brien McMahon | Home - Trumbull HS-Varsity Baseball Field [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 5/3 | V Boys Golf | Darien | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | THS 177 DHS 169 | |
| Mon., 5/3 | JV Boys Golf | Darien | Home - Tashua Knolls Golf Course-Tashua Glen [Directions] | 3:15 p.m. | ||
| Mon., 5/3 | FR Boys Lacrosse | Wilton | Home - Trumbull HS-The Pit [Directions] | Postponed | ||
| Mon., 5/3 | V Boys Tennis | St. Joseph | Away - St. Joseph HS-Tennis Courts [Directions] | 3:30 p.m. | W 6-1 | |
| Mon., 5/3 | V Girls Golf | Ridgefield | Away - Ridgefield Golf Course [Directions] | 2:30 p.m. | THS-203 RHS-204 | |
| Mon., 5/3 | JV Girls Golf | Ridgefield | Away - Ridgefield Golf Course [Directions] | 2:30 p.m. | ||
| Mon., 5/3 | V Softball | Brien McMahon | Away - Brien McMahon HS-Softball Diamond [Directions] | 4:00 p.m. | W 16-2 | |
| Mon., 5/3 | V Girls Tennis | St. Joseph | Home - Trumbull HS-Tennis Courts [Directions] | 3:30 p.m. | L 0-7 | |
| Mon., 5/3 | JV Girls Tennis | St. Joseph | Home - Unity Park [Directions] | 3:30 p.m. | ||
| Tue., 5/4 | V Baseball | Bridgeport Central | Home - Trumbull HS-Varsity Baseball Field [Directions] | 4:00 p.m. | W 24-0 | |
| Tue., 5/4 | V Boys Lacrosse | Shelton | Away - Shelton HS-Finn Stadium [Directions] | 5:30 p.m. | W 11-5 | |
| Tue., 5/4 | V Boys Outdoor Track | Stamford | Home - Trumbull HS-McDougall Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/4 | V Boys Tennis | New Canaan | Away - New Canaan HS-NCHS Tennis Courts [Directions] | 4:30 p.m. | L 0-7 | |
| Tue., 5/4 | V Boys Volleyball | Staples | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Tue., 5/4 | JV Boys Volleyball | Staples | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 5/4 | V Girls Golf | Wilton | Away - Silvermine Golf Club [Directions] | 3:30 p.m. | THS-178 WHS-227 | |
| Tue., 5/4 | V Girls Outdoor Track | Stamford | Home - Trumbull HS-McDougall Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/4 | JV Softball | Brien McMahon | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 4:00 p.m. | ||
| Tue., 5/4 | V Girls Tennis | New Canaan | Home - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Tue., 5/4 | JV Girls Tennis | New Canaan | Home - Unity Park [Directions] | 4:00 p.m. | ||
| Wed., 5/5 | JV Baseball | Stamford | Away - Stamford HS-SHS Baseball Diamond [Directions] | 4:00 p.m. | W 10-0 | |
| Wed., 5/5 | V Boys Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | 3:30 p.m. | THS 186 GHS 157 | |
| Wed., 5/5 | FR Boys Lacrosse | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | Canceled | Cancelled | |
| Thu., 5/6 | V Baseball | Stamford | Home - Trumbull HS-Varsity Baseball Field [Directions] | 5:30 p.m. | W 9-2 | |
| Thu., 5/6 | V Boys Golf | Fairfield Warde | Away - Smith Richardson Golf Course [Directions] | 3:00 p.m. | THS 186 Warde 178 | |
| Thu., 5/6 | V Boys Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 6:00 p.m. | L 17-8 | |
| Thu., 5/6 | JV Boys Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | Canceled | Cancelled | |
| Thu., 5/6 | V Boys Tennis | Brien McMahon | Home - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Thu., 5/6 | V Boys Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | L 0-3 | |
| Thu., 5/6 | JV Boys Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 5/6 | V Girls Golf | Ridgefield | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | THS-195 RHS-217 | |
| Thu., 5/6 | JV Girls Golf | Ridgefield | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Thu., 5/6 | V Girls Lacrosse | Ridgefield | Home - Trumbull HS-McDougall Stadium [Directions] | 5:30 p.m. | L 2-13 | |
| Thu., 5/6 | V Softball | Stamford | Away - Stamford HS-SHS Softball Diamond [Directions] | 4:30 p.m. | W 7-5 | |
| Thu., 5/6 | JV Softball | Stamford | Home - Trumbull HS-Varsity Softball Diamond [Directions] | Canceled | Cancelled | |
| Thu., 5/6 | V Girls Tennis | Brien McMahon | Away - Brien McMahon HS-Tennis Courts [Directions] | 4:00 p.m. | L 2-5 | |
| Fri., 5/7 | V Baseball | Ridgefield | Away - Governor Field [Directions] | 4:00 p.m. | W 8-2 | |
| Fri., 5/7 | JV Baseball | Ridgefield | Home - Trumbull HS-Varsity Baseball Field [Directions] | 4:00 p.m. | L 4-0 | |
| Fri., 5/7 | FR Boys Lacrosse | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 4:30 p.m. | ||
| Fri., 5/7 | V Boys Outdoor Track | Twilight 5 K | Home - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | ||
| Fri., 5/7 | V Girls Outdoor Track | Twilight 5 K | Home - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | ||
| Fri., 5/7 | V Softball | Ridgefield | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 4:30 p.m. | W 17-5 | |
| Fri., 5/7 | V Girls Tennis | Wilton | Home - Trumbull HS-Tennis Courts [Directions] | 5:00 p.m. | L 1-6 | |
| Fri., 5/7 | JV Girls Tennis | Wilton | Home - Unity Park [Directions] | 5:00 p.m. | ||
| Sat., 5/8 | JV Baseball | Brien McMahon | Home - Trumbull HS-Varsity Baseball Field [Directions] | 9:30 a.m. | W 5-4 | |
| Sat., 5/8 | FR Baseball | Wilton | Away - Wilton HS-JV Baseball Field [Directions] | 12:15 p.m. | W 5-2 | |
| Sat., 5/8 | FR Baseball | Wilton | Away - Wilton HS-JV Baseball Field [Directions] | 2:15 p.m. | W 7-3 | |
| Sat., 5/8 | V Boys Lacrosse | Staples | Away - Staples HS-Staples Stadium [Directions] | 3:00 p.m. | L 19-8 | |
| Sat., 5/8 | JV Boys Lacrosse | Staples | Away - Staples HS-Staples Stadium [Directions] | 12:30 p.m. | ||
| Sat., 5/8 | V Softball | Darien | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 3:00 p.m. | W 3-1 | |
| Sat., 5/8 | JV Softball | Ridgefield | Away - Ridgefield HS-JV Field [Directions] | 10:00 a.m. | ||
| Mon., 5/10 | JV Baseball | Greenwich | Home - Trumbull HS-Varsity Baseball Field [Directions] | 4:00 p.m. | W 6-1 | |
| Mon., 5/10 | FR Boys Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 4:00 p.m. | ||
| Mon., 5/10 | V Boys Outdoor Track | Greenwich, St. Joseph | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Mon., 5/10 | V Boys Tennis | Fairfield Warde | Home - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | L 07 | |
| Mon., 5/10 | JV Boys Tennis | Fairfield Warde | Home - Unity Park [Directions] | 4:00 p.m. | ||
| Mon., 5/10 | V Girls Golf | New Canaan | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | THS-196 NCHS-175 | |
| Mon., 5/10 | JV Girls Golf | New Canaan | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Mon., 5/10 | V Girls Outdoor Track | Greenwich, St. Joseph | Home - Trumbull HS-McDougall Stadium [Directions] | 4:00 p.m. | ||
| Mon., 5/10 | V Softball | Greenwich | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 4:15 p.m. | W 10-0 | |
| Mon., 5/10 | V Girls Tennis | Fairfield Warde | Away - Fairfield Warde HS-Blake Courts [Directions] | 4:00 p.m. | W 4-3 | |
| Mon., 5/10 | JV Girls Tennis | Fairfield Warde | Away - Fairfield Woods-Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/11 | V Baseball | Greenwich | Away - Greenwich HS-Baseball Field [Directions] | 4:30 p.m. | W 2-0 (10) | |
| Tue., 5/11 | V Boys Lacrosse | Greenwich | Home - Trumbull HS-McDougall Stadium [Directions] | 5:30 p.m. | L 16-8 | |
| Tue., 5/11 | JV Boys Lacrosse | Greenwich | Home - Trumbull HS-Cork Field [Directions] | 4:30 p.m. | ||
| Tue., 5/11 | V Boys Tennis | Norwalk | Away - Norwalk HS-Tennis Courts [Directions] | 4:30 p.m. | W 5-2 | |
| Tue., 5/11 | JV Boys Tennis | Staples | Home - Unity Park [Directions] | Postponed | ||
| Tue., 5/11 | V Boys Volleyball | St. Joseph | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Tue., 5/11 | V Girls Lacrosse | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:30 p.m. | L 5-15 | |
| Tue., 5/11 | JV Softball | Greenwich | Away - Greenwich HS-Softball Field [Directions] | 4:30 p.m. | ||
| Tue., 5/11 | V Girls Tennis | Norwalk | Home - Trumbull HS-Tennis Courts [Directions] | 5:15 p.m. | W 7-0 | |
| Wed., 5/12 | V Baseball | St. Joseph | Home - Trumbull HS-Varsity Baseball Field [Directions] | 4:00 p.m. | L 4-2 | |
| Wed., 5/12 | JV Baseball | St. Joseph | Away - St. Joseph HS-Baseball Diamond [Directions] | 4:00 p.m. | W 7-4 | |
| Wed., 5/12 | V Boys Golf | Stamford | Away - Stamford High-Sterling Farms Golf Course [Directions] | 3:15 p.m. | THS 182 Stamford 233 | |
| Wed., 5/12 | FR Boys Lacrosse | Ridgefield | Home - Trumbull HS-The Pit [Directions] | Canceled | Cancelled | |
| Wed., 5/12 | JV Boys Tennis | Weston | Away - Weston HS-WHS Tennis Courts [Directions] | 5:30 p.m. | ||
| Wed., 5/12 | V Girls Golf | Greenwich | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | THS-194 GHS-198 | |
| Wed., 5/12 | V Girls Lacrosse | Staples | Home - Trumbull HS-McDougall Stadium [Directions] | 5:30 p.m. | L 7-15 | |
| Wed., 5/12 | V Softball | St. Joseph | Away - St. Joseph HS-Softball Diamond [Directions] | 4:30 p.m. | L 3-4 | |
| Wed., 5/12 | JV Girls Tennis | Weston | Home - Unity Park [Directions] | 4:00 p.m. | ||
| Thu., 5/13 | V Boys Golf | Ridgefield | Away - Silver Spring Golf Course [Directions] | 3:15 p.m. | THS 189 RHS 166 | |
| Thu., 5/13 | V Boys Lacrosse | Amity | Away - Amity Regional HS-Amity High School - Field # 3 [Directions] | 4:00 p.m. | L 10-9 | |
| Thu., 5/13 | JV Boys Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/13 | V Boys Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:30 p.m. | L 2-3 | |
| Thu., 5/13 | JV Boys Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 5/13 | V Girls Golf | Danbury | Away - Richter Park Golf Course [Directions] | 3:15 p.m. | THS-186 DHS-225 | |
| Thu., 5/13 | JV Softball | St. Joseph | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 4:00 p.m. | ||
| Fri., 5/14 | V Baseball | Danbury | Home - Trumbull HS-Varsity Baseball Field [Directions] | 4:00 p.m. | L 4-0 | |
| Fri., 5/14 | JV Baseball | Danbury | Away - Danbury HS-V Baseball Field [Directions] | 4:00 p.m. | W 7-4 | |
| Fri., 5/14 | FR Boys Lacrosse | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:30 p.m. | ||
| Fri., 5/14 | V Boys Outdoor Track | Danbury | Away - Danbury HS-DHS Stadium [Directions] | 4:00 p.m. | ||
| Fri., 5/14 | V Boys Volleyball | Westhill | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 5/14 | JV Boys Volleyball | Westhill | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 5/14 | V Girls Outdoor Track | Danbury | Away - Danbury HS-DHS Stadium [Directions] | 4:00 p.m. | ||
| Fri., 5/14 | V Softball | Danbury | Away - Danbury HS-V Softball field [Directions] | 4:15 p.m. | L 2-3 | |
| Sat., 5/15 | FR Baseball | Darien | Home - Trumbull HS-JV Baseball Field [Directions] | Canceled | Cancelled | |
| Sat., 5/15 | V Boys Lacrosse | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 1:00 p.m. | W 18-1 | |
| Sat., 5/15 | JV Boys Lacrosse | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 11:00 a.m. | ||
| Sat., 5/15 | V Girls Lacrosse | Westhill | Home - Trumbull HS-McDougall Stadium [Directions] | 3:00 p.m. | W 12-9 | |
| Sat., 5/15 | JV Softball | Danbury | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 3:00 p.m. | ||
| Mon., 5/17 | V Baseball | Wilton | Away - Wilton HS-Varsity Baseball Field [Directions] | 4:00 p.m. | W 5-2 | |
| Mon., 5/17 | JV Baseball | Wilton | Home - Trumbull HS-Varsity Baseball Field [Directions] | 4:00 p.m. | W 13-3 | |
| Mon., 5/17 | V Boys Golf | Norwalk | Away - Oak Hills Golf Course [Directions] | 3:15 p.m. | ||
| Mon., 5/17 | V Boys Lacrosse | Danbury | Home - Trumbull HS-McDougall Stadium [Directions] | 7:00 p.m. | W 18-9 | |
| Mon., 5/17 | JV Boys Lacrosse | Danbury | Home - Trumbull HS-McDougall Stadium [Directions] | 5:15 p.m. | ||
| Mon., 5/17 | FR Boys Lacrosse | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | 4:15 p.m. | ||
| Mon., 5/17 | JV Boys Tennis | Weston | Home - Unity Park [Directions] | 4:30 p.m. | ||
| Mon., 5/17 | V Boys Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Gym [Directions] | 4:30 p.m. | W 3-0 | |
| Mon., 5/17 | JV Boys Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Gym [Directions] | 6:00 p.m. | ||
| Mon., 5/17 | V Girls Lacrosse | Norwalk | Home - Trumbull HS-New Turf Field [Directions] | 6:00 p.m. | W 18-4 | |
| Mon., 5/17 | V Softball | Wilton | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 4:15 p.m. | W 12-2 | |
| Tue., 5/18 | FR Baseball | Darien | Home - Trumbull HS-JV Baseball Field [Directions] | 4:00 p.m. | ||
| Tue., 5/18 | V Boys Golf | Danbury | Away - Richter Park Golf Course [Directions] | 3:30 p.m. | THS 185 DHS 174 | |
| Tue., 5/18 | V Girls Golf | Staples | Away - Longshore Golf Course [Directions] | 3:30 p.m. | THS-196 SHS-187 | |
| Tue., 5/18 | V Girls Lacrosse | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | W 12-9 | |
| Tue., 5/18 | JV Softball | Wilton | Away - Wilton HS-JV Softball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/19 | V Baseball | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 6:00 p.m. | W 13-0 (5) | |
| Wed., 5/19 | JV Baseball | Norwalk | Home - Trumbull HS-Varsity Baseball Field [Directions] | 4:00 p.m. | W 4-2 | |
| Wed., 5/19 | V Boys Lacrosse | Haddam-Killingworth | Away - Haddam Killingworth HS (HK)-HKHS Press Box Field [Directions] | 4:00 p.m. | W 18-8 | |
| Wed., 5/19 | FR Boys Lacrosse | Stamford | Home - Trumbull HS-New Turf Field [Directions] | 4:30 p.m. | ||
| Wed., 5/19 | V Boys Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 5/19 | JV Boys Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 5/19 | V Girls Golf | Fairfield Warde | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | THS-191 FWHS-189 | |
| Wed., 5/19 | V Softball | Norwalk | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 4:15 p.m. | W 5-1 | |
| Wed., 5/19 | JV Girls Tennis | Weston | Away - Weston HS-WHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/20 | V Boys Golf | Brien McMahon | Away - Oak Hills Golf Course [Directions] | 3:15 p.m. | THS 183 BMH 193 | |
| Thu., 5/20 | V Boys Lacrosse | Stamford | Home - Trumbull HS-McDougall Stadium [Directions] | 5:30 p.m. | W 18-6 | |
| Thu., 5/20 | JV Boys Lacrosse | Stamford | Home - Trumbull HS-Cork Field [Directions] | 4:30 p.m. | ||
| Thu., 5/20 | V Girls Lacrosse | Lauralton Hall | Away - Lauralton Hall-Turf Field [Directions] | 4:30 p.m. | L 8-12 | |
| Thu., 5/20 | JV Softball | Norwalk | Away - Naramake School Field [Directions] | 4:15 p.m. | ||
| Fri., 5/21 | FR Boys Lacrosse | Greenwich | Away - Greenwich HS-Cos Cob Park, Benvenuto Field [Directions] | 4:45 p.m. | ||
| Sat., 5/22 | JV Softball | St. Joseph | Away - St. Joseph HS-Softball Diamond [Directions] | 10:00 a.m. | ||
| Mon., 5/24 | V Boys Golf | Shelton | Away - Brownson Country Club [Directions] | 3:00 p.m. | ||
| Tue., 5/25 | V Boys Golf | St. Joseph | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | THS 179 St. Joe's 167 | |
| Tue., 5/25 | V Girls Golf | New Canaan | Away - New Canaan HS-CCNC [Directions] | 3:30 p.m. | THS-207 NCHS-175 | |
| Tue., 5/25 | JV Softball | St. Joseph | Home - Trumbull HS-JV Softball Diamond [Directions] | Canceled | Cancelled | |
| Tue., 5/25 | JV Softball | Staples | Home - Trumbull HS-Varsity Softball Diamond [Directions] | Canceled | Cancelled | |
| Wed., 5/26 | V Girls Golf | Danbury | Home - Tashua Knolls Golf Course [Directions] | 3:00 p.m. | THS-170 DHS-208 | |
| Wed., 6/2 | V Boys Golf | St. Joseph | Away - Tashua Knolls Golf Course [Directions] | 3:00 p.m. | ||