| Trumbull 2019-20 Athletic Events Schedule | |||||||
|---|---|---|---|---|---|---|---|
| 909 Events Listed || Go Back || | |||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Bus Time | Note |
| Sat., 8/31 | V Football | Bunnell | Home - Trumbull HS-McDougall Stadium [Directions] | 10:00 a.m. | |||
| Tue., 9/3 | V Boys Soccer | Amity (Scrim.) | Away - Amity Regional HS-Amity High School - Field # 3 [Directions] | 3:45 p.m. | 2:45 PM | ||
| Tue., 9/3 | V Girls Soccer | Joel Barlow (Scrim.) | Away - Joel Barlow HS-Field E [Directions] | 4:00 p.m. | 2:30 PM | ||
| Tue., 9/3 | JV Girls Soccer | Joel Barlow (Scrim.) | Away - Joel Barlow HS-Field A [Directions] | 4:00 p.m. | |||
| Thu., 9/5 | V Boys Soccer | Shelton (Scrim.) | Home - Trumbull HS-New Turf Field [Directions] | 6:30 p.m. | W 6-1 | ||
| Thu., 9/5 | JV Boys Soccer | Shelton (Scrim.) | Home - Trumbull HS-The Pit [Directions] | 4:30 p.m. | |||
| Thu., 9/5 | V Field Hockey | Weston (Scrim.) | Home - Trumbull HS-New Turf Field [Directions] | 4:00 p.m. | |||
| Fri., 9/6 | V Football | Masuk (Scrim.) | Home - Trumbull HS-McDougall Stadium [Directions] | 5:00 p.m. | |||
| Fri., 9/6 | FR Football | Staples (Scrim.) | Home - Trumbull HS-New Turf Field [Directions] | 6:00 p.m. | |||
| Fri., 9/6 | V Girls Cross Country | Darien (Scrim.) | Home - Trumbull HS-Cross Country Course [Directions] | 4:15 p.m. | |||
| Sat., 9/7 | V Boys Soccer | Amity, Bethel, Brookfield, Coginchaug, Seymour, Stamford, West Haven | Away - Amity Regional HS-Amity High School - Field # 3 | 9:00 a.m. | 7:45 AM | ||
| Sat., 9/7 | V Girls Soccer | Masuk (Scrim.) | Home - Trumbull HS-New Turf Field [Directions] | 4:00 p.m. | |||
| Sat., 9/7 | JV Girls Soccer | Masuk | Home - Trumbull HS-McDougall Stadium [Directions] | 4:00 p.m. | |||
| Sat., 9/7 | FR Girls Soccer | Masuk | Home - Trumbull HS-The Pit [Directions] | 4:00 p.m. | |||
| Sun., 9/8 | V Field Hockey | Hamden Field Hockey Playday | Away - Hamden HS-HHS Turf Field #1 | 12:00 p.m. | |||
| Tue., 9/10 | V Boys Cross Country | Brien McMahon, Darien, Trinity Catholic | Home - Trumbull HS-Cross Country Course [Directions] | 4:00 p.m. | |||
| Tue., 9/10 | V Boys Soccer | Weston (Scrim.) | Home - Trumbull HS-New Turf Field [Directions] | 6:00 p.m. | |||
| Tue., 9/10 | JV Boys Soccer | Weston (Scrim.) | Home - Trumbull HS-Indian Ledge Turf [Directions] | 6:00 p.m. | 5:00 PM; 1 Bus | ||
| Tue., 9/10 | V Girls Cross Country | Brien McMahon, Darien, Trinity Catholic | Home - Trumbull HS-Cross Country Course [Directions] | 4:00 p.m. | |||
| Tue., 9/10 | V Girls Soccer | Amity (Scrim.) | Home - Trumbull HS-New Turf Field [Directions] | 4:00 p.m. | |||
| Tue., 9/10 | JV Girls Soccer | Amity | Home - Trumbull HS-Indian Ledge Turf [Directions] | 4:00 p.m. | 3:00 PM, Return 5:45 PM; 1 Bus | ||
| Tue., 9/10 | V Girls Volleyball | Masuk (Scrim.) | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 5:30 p.m. | 2:45 PM | ||
| Tue., 9/10 | JV Girls Volleyball | Masuk (Scrim.) | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 4:00 p.m. | 2:45 PM | ||
| Wed., 9/11 | V Girls Volleyball | Seymour (Scrim.) | Home - Trumbull HS-THS Main Gym [Directions] | 3:15 p.m. | |||
| Thu., 9/12 | FR Football | Bridgeport Central | Away - Bridgeport Central HS-Kennedy Stadium [Directions] | 4:00 p.m. | 2:45 PM; 1 Bus | ||
| Thu., 9/12 | V Field Hockey | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | W 4-0 | 2:15 PM; 1 Bus | |
| Thu., 9/12 | JV Field Hockey | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | 2:15 PM; 1 Bus | ||
| Fri., 9/13 | V Football | Bridgeport Central | Home - Trumbull HS-McDougall Stadium [Directions] | 7:00 p.m. | W 42-6 | ||
| Fri., 9/13 | V Boys Soccer | Fairfield Ludlowe | Home - Trumbull HS-New Turf Field [Directions] | 4:00 p.m. | T 0-0 | ||
| Fri., 9/13 | JV Boys Soccer | Fairfield Ludlowe | Home - Trumbull HS-The Pit [Directions] | 4:00 p.m. | |||
| Fri., 9/13 | FR Boys Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | 4:00 p.m. | 2:45 PM; 1 Bus | ||
| Sat., 9/14 | V Boys Cross Country | Wilton | Away - Wilton HS-Allen Meadow [Directions] | 9:00 a.m. | 7:30 AM; 1 Bus | ||
| Sat., 9/14 | JV Football | Bridgeport Central | Away - Bridgeport Central HS-Kennedy Stadium [Directions] | 10:30 a.m. | 9:15 AM; 1 Bus | ||
| Sat., 9/14 | V Girls Cross Country | Wilton | Away - Wilton HS-Allen Meadow [Directions] | 9:00 a.m. | 7:30 AM; 1 Bus | ||
| Sat., 9/14 | V Girls Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 10:00 a.m. | W 1-0 | 8:45 AM; 1 Bus | |
| Sat., 9/14 | JV Girls Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 10:00 a.m. | 8:45 AM; 1 Bus | ||
| Sat., 9/14 | FR Girls Soccer | Fairfield Ludlowe | Home - Trumbull HS-New Turf Field [Directions] | 12:00 p.m. | |||
| Sat., 9/14 | V Girls Volleyball | Amity, Avon, Darien, East Haven, Fairfield Ludlowe, Glastonbury, Joel Barlow, New Britain, New Canaan, North Haven, Seymour, Simsbury, SMSA, St. Joseph, St. Paul Catholic, Suffield, Trinity Catholic, Woodland | Away - Connecticut Sports Center | 8:30 a.m. | 7:00 AM; 1 Bus | ||
| Mon., 9/16 | V Boys Soccer | Darien | Home - Trumbull HS-New Turf Field [Directions] | 5:30 p.m. | L 1-2 | ||
| Mon., 9/16 | JV Boys Soccer | Darien | Home - Trumbull HS-The Pit [Directions] | 4:00 p.m. | |||
| Mon., 9/16 | FR Boys Soccer | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | 2:45 PM; 1 Bus | ||
| Mon., 9/16 | V Field Hockey | New Canaan | Home - Trumbull HS-McDougall Stadium [Directions] | 7:00 p.m. | L 0-5 | ||
| Mon., 9/16 | JV Field Hockey | New Canaan | Home - Trumbull HS-McDougall Stadium [Directions] | 5:30 p.m. | |||
| Mon., 9/16 | V Girls Volleyball | Fairfield Ludlowe | Home - Trumbull HS-Gym [Directions] | 5:30 p.m. | L 2-3 | ||
| Mon., 9/16 | JV Girls Volleyball | Fairfield Ludlowe | Home - Trumbull HS-Gym [Directions] | 4:00 p.m. | |||
| Mon., 9/16 | FR Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:00 p.m. | 2:45 PM; 1 Bus | ||
| Tue., 9/17 | V Boys Cross Country | Fairfield Warde, Greenwich, St. Joseph | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | 2:45 PM; 1 Bus | ||
| Tue., 9/17 | V Girls Cross Country | Fairfield Warde, Greenwich, St. Joseph | Away - Fairfield Warde HS [Directions] | 4:00 p.m. | 2:45 PM; 2 Buses | ||
| Tue., 9/17 | V Girls Soccer | Darien | Away - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | L 2-1 | 2:15 PM, Dismiss 2:00 PM; 1 Bus | |
| Tue., 9/17 | JV Girls Soccer | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | 2:15 PM, Dismiss 2:00 PM; 1 Bus | ||
| Tue., 9/17 | FR Girls Soccer | Darien | Home - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | |||
| Wed., 9/18 | V Boys Soccer | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 7:00 p.m. | W 1-0 | 4:30 PM; 1 Bus | |
| Wed., 9/18 | JV Boys Soccer | Ridgefield | Away - Ridgefield HS-RHS Lower Grass Field [Directions] | 4:00 p.m. | 2:15 PM, Dismiss 2:00 PM; 1 Bus | ||
| Wed., 9/18 | FR Boys Soccer | Ridgefield | Home - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | |||
| Wed., 9/18 | V Girls Volleyball | Darien | Home - Trumbull HS-Gym [Directions] | 5:30 p.m. | W 3-2 | ||
| Wed., 9/18 | JV Girls Volleyball | Darien | Home - Trumbull HS-Gym [Directions] | 4:00 p.m. | |||
| Wed., 9/18 | FR Girls Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM; 1 Bus | ||
| Thu., 9/19 | V Girls Soccer | Ridgefield | Home - Trumbull HS-New Turf Field [Directions] | 4:00 p.m. | L 3-0 | ||
| Thu., 9/19 | JV Girls Soccer | Ridgefield | Home - Trumbull HS-The Pit [Directions] | Postponed | |||
| Fri., 9/20 | V Football | Greenwich | Home - Trumbull HS-McDougall Stadium [Directions] | 7:00 p.m. | L 7-42 | ||
| Fri., 9/20 | FR Football | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:30 p.m. | 2:45 PM; 1 Bus | ||
| Fri., 9/20 | V Girls Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:30 p.m. | W 3-0 | 2:15 PM, Dismiss 2:00 PM; 1 Bus | |
| Fri., 9/20 | JV Girls Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:00 p.m. | 2:15 PM, Dismiss 2:00 PM | ||
| Fri., 9/20 | FR Girls Volleyball | Ridgefield | Home - Trumbull HS-Gym [Directions] | 4:00 p.m. | |||
| Sat., 9/21 | JV Football | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 9:00 a.m. | 7:15 AM; 1 Bus | ||
| Sat., 9/21 | V Field Hockey | Wilton | Home - Trumbull HS-McDougall Stadium [Directions] | 10:00 a.m. | L 1-6 | ||
| Sat., 9/21 | JV Field Hockey | Wilton | Home - Trumbull HS-McDougall Stadium [Directions] | 11:30 a.m. | |||
| Sat., 9/21 | FR Girls Soccer | Ridgefield | Away - Ridgefield HS-RHS Lower Grass Field [Directions] | 5:00 p.m. | 3:15 PM, Dismiss 2:15 AM; 1 Bus | ||
| Mon., 9/23 | V Field Hockey | Fairfield Ludlowe | Home - Trumbull HS-McDougall Stadium [Directions] | 7:00 p.m. | L 1-2 | ||
| Mon., 9/23 | JV Field Hockey | Fairfield Ludlowe | Home - Trumbull HS-McDougall Stadium [Directions] | 5:30 p.m. | |||
| Mon., 9/23 | V Girls Soccer | Stamford | Away - Stamford HS-SHS Upper Soccer Field [Directions] | 4:00 p.m. | W 4-0 | 2:15 PM, Dismiss 2:00 PM; 1 Bus | |
| Mon., 9/23 | JV Girls Soccer | Stamford | Away - Rippowam MS-Upper Soccer/Footballl Field [Directions] | 4:00 p.m. | 2:15 PM, Dismiss 2:00 PM | ||
| Tue., 9/24 | V Boys Cross Country | New Canaan, Danbury, Wilton | Away - Waveny Park [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | ||
| Tue., 9/24 | V Boys Soccer | Staples | Home - Trumbull HS-New Turf Field [Directions] | 5:30 p.m. | T 2-2 | ||
| Tue., 9/24 | JV Boys Soccer | Staples | Home - Trumbull HS-The Pit [Directions] | 4:00 p.m. | |||
| Tue., 9/24 | FR Boys Soccer | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | 2:45 PM; 1 Bus | ||
| Tue., 9/24 | V Girls Cross Country | New Canaan, Danbury, Wilton | Away - Waveny Park [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM; 1 Bus | ||
| Wed., 9/25 | V Field Hockey | Norwalk | Home - Trumbull HS-McDougall Stadium [Directions] | 7:00 p.m. | L 1-4 | ||
| Wed., 9/25 | JV Field Hockey | Norwalk | Home - Trumbull HS-McDougall Stadium [Directions] | 5:30 p.m. | |||
| Wed., 9/25 | V Girls Soccer | Staples | Away - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | L 6-3 | 2:30 PM, Dismiss 2:15 PM; 1 Bus | |
| Wed., 9/25 | JV Girls Soccer | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM; 1 Bus | ||
| Wed., 9/25 | FR Girls Soccer | Staples | Home - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | |||
| Wed., 9/25 | V Girls Swimming and Diving | Greenwich | Away - Greenwich HS-Pool [Directions] | 4:30 p.m. | 2:45 PM; 1 Bus | ||
| Wed., 9/25 | V Girls Volleyball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 5:30 p.m. | W 3-2 | 2:15 PM; 1 Bus | |
| Wed., 9/25 | JV Girls Volleyball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 3:45 p.m. | 2:15 PM; 1 Bus | ||
| Thu., 9/26 | FR Football | Brookfield | Away - Brookfield HS-BHS Back Turf [Directions] | 7:00 p.m. | 2:15 PM, Dismiss 2:00 PM; 1 Bus | ||
| Thu., 9/26 | V Boys Soccer | Stamford | Home - Trumbull HS-New Turf Field [Directions] | 5:30 p.m. | W 4-0 | ||
| Thu., 9/26 | JV Boys Soccer | Stamford | Home - Trumbull HS-The Pit [Directions] | 4:00 p.m. | |||
| Thu., 9/26 | FR Boys Soccer | Stamford | Away - Stamford HS-SHS Upper Soccer Field [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM; 1 Bus | ||
| Thu., 9/26 | V Girls Volleyball | Staples | Home - Trumbull HS-Gym [Directions] | 5:30 p.m. | W 3-0 | ||
| Thu., 9/26 | JV Girls Volleyball | Staples | Home - Trumbull HS-Gym [Directions] | 4:00 p.m. | |||
| Thu., 9/26 | FR Girls Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:00 p.m. | 2:45 PM; 1 Bus | ||
| Fri., 9/27 | V Football | Trinity Catholic | Home - Trumbull HS-McDougall Stadium [Directions] | 7:00 p.m. | W 21-20 | ||
| Fri., 9/27 | V Field Hockey | Greenwich | Away - Greenwich HS-Field 3 [Directions] | 4:30 p.m. | L 0-1 | 2:30 PM, Dismiss 2:15 PM; 1 Bus | |
| Fri., 9/27 | JV Field Hockey | Greenwich | Away - Greenwich HS-Field 3 [Directions] | 5:30 p.m. | 2:30 PM, Dismiss 2:15 PM | ||
| Fri., 9/27 | FR Girls Volleyball | Amity | Away - Amity Regional HS-Middle Practice Gym [Directions] | 3:45 p.m. | 2:30 PM, Dismiss 2:15 PM; 1 Bus | ||
| Sat., 9/28 | JV Football | Nonnewaug | Away - Nonnewaug HS-Turf Field [Directions] | 10:00 a.m. | 8:00 AM; 1 Bus | ||
| Sat., 9/28 | V Girls Cross Country | Ocean State Invitational | Away - Goddard Park | 8:45 a.m. | 5:00 AM; 1 Bus | ||
| Tue., 10/1 | V Boys Cross Country | Fairfield Ludlowe, Ridgefield, Staples | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | 2:45 PM; 1 Bus | ||
| Tue., 10/1 | V Boys Soccer | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 6:30 p.m. | W 6-0 | 4:15 PM; 1 Bus | |
| Tue., 10/1 | JV Boys Soccer | New Canaan | Away - Conner Field, New Cannan [Directions] | 4:00 p.m. | 2:45 PM; 1 Bus | ||
| Tue., 10/1 | FR Boys Soccer | New Canaan | Home - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | |||
| Tue., 10/1 | V Girls Cross Country | Fairfield Ludlowe, Ridgefield, Staples | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | 2:45 PM; 1 Bus | ||
| Tue., 10/1 | V Field Hockey | Danbury | Away - Danbury Sports Dome [Directions] | 4:00 p.m. | T 1-1 | 2:15 PM, Dismiss 2:00 PM; 1 Bus | |
| Tue., 10/1 | JV Field Hockey | Danbury | Away - Danbury Sports Dome [Directions] | 5:30 p.m. | 4:00 PM | ||
| Wed., 10/2 | V Girls Soccer | New Canaan | Home - Trumbull HS-New Turf Field [Directions] | 5:30 p.m. | L 0-2 | ||
| Wed., 10/2 | JV Girls Soccer | New Canaan | Home - Trumbull HS-The Pit [Directions] | 4:00 p.m. | |||
| Wed., 10/2 | FR Girls Soccer | New Canaan | Away - Saxe MS-Field 1 [Directions] | 4:00 p.m. | 2:45 PM; 1 Bus | ||
| Wed., 10/2 | V Girls Swimming and Diving | Norwalk/McMahon | Away - Norwalk HS-Pat Spinola Natatorium [Directions] | 3:30 p.m. | 2:00 PM, Dismiss 1:45 PM; 1 Bus | ||
| Thu., 10/3 | FR Football | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM; 1 Bus | ||
| Thu., 10/3 | V Boys Soccer | Westhill | Home - Trumbull HS-New Turf Field [Directions] | 6:00 p.m. | W 5-0 | ||
| Thu., 10/3 | JV Boys Soccer | Westhill | Home - Trumbull HS-New Turf Field [Directions] | 4:00 p.m. | |||
| Thu., 10/3 | FR Boys Soccer | Westhill | Away - Westhill HS-Front Turf [Directions] | 4:30 p.m. | 2:45 PM; 1 Bus | ||
| Thu., 10/3 | V Field Hockey | Darien | Home - Trumbull HS-McDougall Stadium [Directions] | 7:00 p.m. | L 0-3 | ||
| Thu., 10/3 | JV Field Hockey | Darien | Home - Trumbull HS-McDougall Stadium [Directions] | 5:30 p.m. | |||
| Thu., 10/3 | V Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | L 0-3 | 2:30 PM, Dismiss 2:15 PM; 1 Bus | |
| Thu., 10/3 | JV Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM | ||
| Thu., 10/3 | FR Girls Volleyball | New Canaan | Home - Trumbull HS-Gym [Directions] | 4:00 p.m. | |||
| Fri., 10/4 | V Football | Darien | Home - Trumbull HS-McDougall Stadium [Directions] | 7:00 p.m. | L 13-41 | ||
| Fri., 10/4 | V Girls Soccer | Westhill | Away - Westhill HS-Front Turf [Directions] | 4:00 p.m. | W 5-1 | 2:15 PM, Dismiss 2:00 PM; 1 Bus | |
| Fri., 10/4 | JV Girls Soccer | Westhill | Away - Rippowan MS-Rippowam Turf Field [Directions] | 4:00 p.m. | 2:15 PM, Dismiss 2:00 PM | ||
| Fri., 10/4 | FR Girls Soccer | Westhill | Home - Trumbull HS-JV Grass Field [Directions] | 4:30 p.m. | |||
| Fri., 10/4 | V Girls Swimming and Diving | Fairfield Ludlowe | Home - Hillcrest MS-Pool [Directions] | 4:00 p.m. | |||
| Fri., 10/4 | V Girls Volleyball | Westhill | Home - Trumbull HS-Gym [Directions] | 4:00 p.m. | W 3-1 | ||
| Fri., 10/4 | JV Girls Volleyball | Westhill | Home - Trumbull HS-Gym [Directions] | 5:30 p.m. | |||
| Sat., 10/5 | JV Football | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | 2:15 PM; 1 Bus | ||
| Sat., 10/5 | V Boys Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 7:00 p.m. | W 3-2 | 5:00 PM; 1 Bus | |
| Sat., 10/5 | JV Boys Soccer | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | 5:00 p.m. | 3:30 PM; 1 Bus | ||
| Sat., 10/5 | FR Boys Soccer | Norwalk | Home - Trumbull HS-JV Grass Field [Directions] | 12:00 p.m. | |||
| Sat., 10/5 | FR Field Hockey | Norwalk | Home - Trumbull HS-McDougall Stadium [Directions] | 12:00 p.m. | |||
| Sat., 10/5 | FR Girls Volleyball | Westhill | Away - Westhill HS-New Gym [Directions] | 11:00 a.m. | 9:30 AM; 1 Bus | ||
| Mon., 10/7 | V Boys Cross Country | Norwalk, Stamford, Westhill | Home - Trumbull HS-Cross Country Course [Directions] | 4:00 p.m. | |||
| Mon., 10/7 | V Girls Cross Country | Norwalk, Stamford, Westhill | Home - Trumbull HS-Cross Country Course [Directions] | 4:00 p.m. | |||
| Mon., 10/7 | V Girls Soccer | Norwalk | Home - Trumbull HS-New Turf Field [Directions] | 5:30 p.m. | W 6-0 | ||
| Mon., 10/7 | V Girls Swimming and Diving | Darien | Home - Hillcrest MS-Pool [Directions] | 4:00 p.m. | |||
| Mon., 10/7 | V Girls Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:00 p.m. | W 3-0 | 2:30 PM, Dismiss 2:15 PM; 1 Bus | |
| Mon., 10/7 | JV Girls Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 5:30 p.m. | 2:30 PM, Dismiss 2:15 PM | ||
| Mon., 10/7 | FR Girls Volleyball | Norwalk | Home - Trumbull HS-Gym [Directions] | 4:00 p.m. | |||
| Tue., 10/8 | V Field Hockey | St. Joseph | Home - Trumbull HS-McDougall Stadium [Directions] | 3:00 p.m. | W 6-0 | ||
| Tue., 10/8 | JV Field Hockey | St. Joseph | Home - Trumbull HS-McDougall Stadium [Directions] | 4:30 p.m. | |||
| Thu., 10/10 | V Boys Soccer | Trinity Catholic | Away - Trinity Catholic-Gaglio Field | 4:00 p.m. | W 8-0 | 2:15 PM, Dismiss 2:00 PM; 1 Bus | |
| Thu., 10/10 | V Field Hockey | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | L 0-5 | 2:30 PM, Dismiss 2:15 PM; 1 Bus | |
| Thu., 10/10 | JV Field Hockey | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 5:30 p.m. | 2:30 PM, Dismiss 2:15 PM | ||
| Fri., 10/11 | FR Field Hockey | Danbury | Home - Trumbull HS-New Turf Field [Directions] | 3:45 p.m. | |||
| Fri., 10/11 | V Girls Soccer | Trinity Catholic | Home - Trumbull HS-New Turf Field [Directions] | 5:30 p.m. | W 9-0 | ||
| Fri., 10/11 | V Girls Swimming and Diving | Ridgefield | Away - Barlow Mountain Pool [Directions] | 4:00 p.m. | 2:00 PM, Dismiss 1:45 PM; 1 Bus | ||
| Fri., 10/11 | V Girls Volleyball | Trinity Catholic | Away - Trinity Catholic-Gym | 4:00 p.m. | W 3-1 | 2:15 PM, Dismiss 2:00 PM; 1 Bus | |
| Fri., 10/11 | JV Girls Volleyball | Trinity Catholic | Away - Trinity Catholic-Gym | 5:30 p.m. | 2:00 PM, Dismiss 1:45 PM | ||
| Sat., 10/12 | V Boys Cross Country | Wickham Invitational | Away - Wickham Park | 10:00 a.m. | 7:30 AM; 1 Bus | ||
| Sat., 10/12 | V Boys Soccer | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 12:00 p.m. | T 0-0 | 11:00 AM | |
| Sat., 10/12 | JV Boys Soccer | St. Joseph | Away - St. Joseph HS-Lower Grass Field [Directions] | 12:00 p.m. | 11:00 AM | ||
| Sat., 10/12 | V Girls Cross Country | Invitational | Away - ESPN Wide World of Sports Complex | TBA | |||
| Sat., 10/12 | FR Field Hockey | Amity | Away - Amity Regional HS-Field Hockey Field [Directions] | 10:00 a.m. | 8:45 AM; 1 Bus | ||
| Sat., 10/12 | FR Girls Volleyball | Amity | Home - Trumbull HS-THS Main Gym [Directions] | 12:00 p.m. | |||
| Mon., 10/14 | JV Football | Danbury | Home - Trumbull HS-McDougall Stadium [Directions] | 5:00 p.m. | |||
| Mon., 10/14 | V Field Hockey | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 7:00 p.m. | W 2-0 | 3:30 PM; 1 Bus | |
| Mon., 10/14 | JV Field Hockey | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | 3:30 PM | ||
| Mon., 10/14 | V Girls Soccer | St. Joseph | Home - Trumbull HS-New Turf Field [Directions] | 5:30 p.m. | L 1-2 | ||
| Mon., 10/14 | JV Girls Soccer | St. Joseph | Home - Trumbull HS-New Turf Field [Directions] | 3:15 p.m. | |||
| Tue., 10/15 | V Boys Soccer | Fairfield Warde | Home - Trumbull HS-New Turf Field [Directions] | 5:30 p.m. | T 2-2 | ||
| Tue., 10/15 | JV Boys Soccer | Fairfield Warde | Home - Trumbull HS-The Pit [Directions] | 4:00 p.m. | |||
| Tue., 10/15 | FR Boys Soccer | Fairfield Warde | Away - Fairfield Warde HS-Fairfield Warde Grass Utility Field [Directions] | 4:00 p.m. | 2:45 PM | ||
| Tue., 10/15 | V Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 5:30 p.m. | W 3-0 | 3:00 PM; 1 Bus | |
| Tue., 10/15 | JV Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:00 p.m. | 3:00 PM | ||
| Tue., 10/15 | FR Girls Volleyball | St. Joseph | Home - Trumbull HS-Gym [Directions] | 4:00 p.m. | |||
| Thu., 10/17 | FR Football | Danbury | Home - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | |||
| Thu., 10/17 | V Boys Soccer | Wilton | Away - Wilton HS-Lilly Field [Directions] | 6:30 p.m. | L 0-2 | 4:30 PM | |
| Thu., 10/17 | JV Boys Soccer | Wilton | Away - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM; 1 Bus | ||
| Thu., 10/17 | FR Boys Soccer | Wilton | Home - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | |||
| Thu., 10/17 | FR Girls Soccer | Fairfield Warde | Home - Trumbull HS-New Turf Field [Directions] | 4:00 p.m. | |||
| Thu., 10/17 | V Girls Swimming and Diving | Fairfield Warde | Away - Fairfield University-Pool [Directions] | 4:00 p.m. | |||
| Thu., 10/17 | V Girls Volleyball | Fairfield Warde | Home - Trumbull HS-Gym [Directions] | 5:30 p.m. | W 3-2 | ||
| Thu., 10/17 | JV Girls Volleyball | Fairfield Warde | Home - Trumbull HS-Gym [Directions] | 4:00 p.m. | |||
| Thu., 10/17 | FR Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:00 p.m. | 2:45 PM; 1 Bus | ||
| Fri., 10/18 | V Field Hockey | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 4:00 p.m. | L 0-3 | 2:45 PM; 1 Bus | |
| Fri., 10/18 | JV Field Hockey | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 5:30 p.m. | 2:45 PM | ||
| Fri., 10/18 | V Girls Soccer | Wilton | Home - Trumbull HS-New Turf Field [Directions] | 3:30 p.m. | L 2-4 | ||
| Fri., 10/18 | JV Girls Soccer | Wilton | Home - Trumbull HS-The Pit [Directions] | 3:30 p.m. | |||
| Fri., 10/18 | FR Girls Soccer | Wilton | Away - Allen's Meadow-3B [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | ||
| Fri., 10/18 | V Girls Swimming and Diving | Danbury | Away - Western CT State Univ.-O'Neill Ctr, Blue-O'Neill Center [Directions] | 5:00 p.m. | 3:00 PM; 1 Bus | ||
| Sat., 10/19 | V Football | Danbury | Away - Brookfield HS-BHS Stadium Field [Directions] | 6:00 p.m. | L 13-34 | 3:00 PM; 2 Buses | |
| Sat., 10/19 | V Boys Soccer | Danbury | Home - Trumbull HS-New Turf Field [Directions] | 6:00 p.m. | W 1-0 | ||
| Sat., 10/19 | JV Boys Soccer | Danbury | Home - Trumbull HS-New Turf Field [Directions] | 4:00 p.m. | |||
| Sat., 10/19 | FR Girls Soccer | Amity | Away - Amity Regional HS-Amity High School - Field # 3 [Directions] | 10:00 a.m. | 8:30 AM, Dismiss 7:00 AM; 1 Bus | ||
| Sat., 10/19 | V Girls Volleyball | Shelton | Away - Shelton HS-High School - Murray Gymnasium [Directions] | 11:30 a.m. | W 3-1 | 8:45 AM; 1 Bus | |
| Sat., 10/19 | JV Girls Volleyball | Shelton | Away - Shelton HS-High School - Murray Gymnasium [Directions] | 10:00 a.m. | 8:45 AM | ||
| Sat., 10/19 | Miscellaneous Events | Cheerleading vs. Danbury @ Brookfield | Home - TBA [Directions] | 6:00 p.m. | 4:30 PM; 2 Buses | ||
| Sun., 10/20 | FR Girls Soccer | Danbury | Home - Trumbull HS-McDougall Stadium [Directions] | 5:30 p.m. | |||
| Mon., 10/21 | V Field Hockey | Amity | Home - Trumbull HS-McDougall Stadium [Directions] | 7:00 p.m. | L 1-2 | ||
| Mon., 10/21 | JV Field Hockey | Amity | Home - Trumbull HS-McDougall Stadium [Directions] | 5:30 p.m. | |||
| Mon., 10/21 | V Girls Soccer | Danbury | Away - Mill Ridge Int. School-Turf Field [Directions] | 4:00 p.m. | W 1-0 | 2:15 PM, Dismiss 2:00 PM; 1 Bus | |
| Mon., 10/21 | JV Girls Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 3:45 p.m. | 2:15 PM, Dismiss 2:00 PM | ||
| Mon., 10/21 | FR Girls Soccer | Danbury | Home - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | |||
| Mon., 10/21 | V Girls Volleyball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:30 p.m. | W 3-0 | 2:15 PM, Dismiss 2:00 PM; 1 Bus | |
| Mon., 10/21 | JV Girls Volleyball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | 2:15 PM, Dismiss 2:00 PM | ||
| Mon., 10/21 | FR Girls Volleyball | Wilton | Home - Trumbull HS-Gym [Directions] | 4:00 p.m. | |||
| Tue., 10/22 | V Boys Soccer | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | W 4-1 | 2:45 PM; 1 Bus | |
| Tue., 10/22 | JV Boys Soccer | Greenwich | Away - Cos Cob Park-Benvenuto Field [Directions] | 4:30 p.m. | 2:45 PM | ||
| Tue., 10/22 | FR Boys Soccer | Greenwich | Home - Trumbull HS-JV Grass Field [Directions] | 4:30 p.m. | |||
| Wed., 10/23 | V Field Hockey | Ridgefield | Home - Trumbull HS-McDougall Stadium [Directions] | 7:00 p.m. | L 0-3 | ||
| Wed., 10/23 | JV Field Hockey | Ridgefield | Home - Trumbull HS-McDougall Stadium [Directions] | 5:30 p.m. | |||
| Wed., 10/23 | V Girls Soccer | Greenwich | Home - Trumbull HS-New Turf Field [Directions] | 6:00 p.m. | W 3-1 | ||
| Wed., 10/23 | JV Girls Soccer | Greenwich | Home - Trumbull HS-New Turf Field [Directions] | 4:00 p.m. | |||
| Wed., 10/23 | V Girls Swimming and Diving | Westhill/Stamford | Home - Hillcrest MS-Pool [Directions] | 4:00 p.m. | |||
| Wed., 10/23 | V Girls Volleyball | Danbury | Home - Trumbull HS-Gym [Directions] | 5:30 p.m. | W 3-0 | ||
| Wed., 10/23 | JV Girls Volleyball | Danbury | Home - Trumbull HS-Gym [Directions] | 4:00 p.m. | |||
| Wed., 10/23 | FR Girls Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 4:00 p.m. | 2:15 PM, Dismiss 2:00 PM; 1 Bus | ||
| Thu., 10/24 | FR Football | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | 4:00 p.m. | 2:45 PM; 1 Bus | ||
| Thu., 10/24 | V Boys Soccer | Bridgeport Central | Home - Trumbull HS-New Turf Field [Directions] | 6:00 p.m. | W 2-1 | ||
| Thu., 10/24 | JV Boys Soccer | Bridgeport Central | Home - Trumbull HS-The Pit [Directions] | 4:00 p.m. | |||
| Thu., 10/24 | FR Girls Soccer | Greenwich | Away - Cos Cob Park-Benvenuto Field [Directions] | 4:30 p.m. | 2:45 PM; 1 Bus | ||
| Fri., 10/25 | V Football | Norwalk | Home - Trumbull HS-McDougall Stadium [Directions] | 7:00 p.m. | L 14-42 | ||
| Fri., 10/25 | V Girls Soccer | Bridgeport Central | Away - Bridgeport Central HS-Kennedy Stadium [Directions] | 4:00 p.m. | W 8-0 | 2:45 PM; 1 Bus | |
| Fri., 10/25 | FR Girls Soccer | Amity | Home - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | |||
| Fri., 10/25 | V Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | L 2-3 | 2:15 PM, Dismiss 2:00 PM; 1 Bus | |
| Fri., 10/25 | JV Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | 2:15 PM, Dismiss 2:00 PM; 1 Bus | ||
| Fri., 10/25 | FR Girls Volleyball | Greenwich | Home - Trumbull HS-Gym [Directions] | 4:00 p.m. | |||
| Sat., 10/26 | V Boys Cross Country | CIAC Boys Class LL Divisional Championship | Away - Wickham Park | 3:45 p.m. | |||
| Sat., 10/26 | JV Football | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 2:00 p.m. | 12:30 PM; 1 Bus | ||
| Sat., 10/26 | V Girls Cross Country | CIAC Girls Class LL Divisional Championship | Away - Wickham Park | 3:10 p.m. | |||
| Sat., 10/26 | V Girls Soccer | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 1:00 p.m. | W 2-0 | 2:30 PM; 1 Bus | |
| Sat., 10/26 | JV Girls Soccer | Fairfield Warde | Away - Fairfield Warde HS-Varsity Grass Soccer Field [Directions] | 1:00 p.m. | 2:30 PM | ||
| Mon., 10/28 | V Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 6:30 p.m. | W 4-1 | 4:45 PM; 1 Bus | |
| Mon., 10/28 | JV Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 5:00 p.m. | 3:30 PM; 1 Bus | ||
| Mon., 10/28 | FR Boys Soccer | Brien McMahon | Home - Trumbull HS-Field 9 [Directions] | 4:00 p.m. | |||
| Mon., 10/28 | V Field Hockey | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | L 0-4 | 2:45 PM; 1 Bus | |
| Mon., 10/28 | JV Field Hockey | Fairfield Warde | Away - Fairfield Warde HS [Directions] | 5:30 p.m. | 2:45 PM; 1 Bus | ||
| Tue., 10/29 | V Field Hockey | Brien McMahon | Home - Trumbull HS-McDougall Stadium [Directions] | 7:00 p.m. | L 0-1 | ||
| Tue., 10/29 | JV Field Hockey | Brien McMahon | Home - Trumbull HS-McDougall Stadium [Directions] | 5:30 p.m. | |||
| Tue., 10/29 | V Girls Soccer | Brien McMahon | Home - Trumbull HS-New Turf Field [Directions] | 6:00 p.m. | L 3-0 | ||
| Tue., 10/29 | JV Girls Soccer | Brien McMahon | Home - Trumbull HS-New Turf Field [Directions] | 4:00 p.m. | |||
| Tue., 10/29 | V Girls Swimming and Diving | Westhill/Stamford | Home - Norwalk HS-Pat Spinola Natatorium [Directions] | 5:30 p.m. | |||
| Tue., 10/29 | V Girls Volleyball | Bridgeport Central | Home - Trumbull HS-Gym [Directions] | 5:30 p.m. | W 3-0 | ||
| Tue., 10/29 | JV Girls Volleyball | Bridgeport Central | Home - Trumbull HS-Gym [Directions] | 4:00 p.m. | |||
| Wed., 10/30 | FR Football | Fairfield Ludlowe | Home - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | |||
| Wed., 10/30 | V Girls Swimming and Diving | Staples | Home - Hillcrest MS-Pool [Directions] | 4:00 p.m. | |||
| Wed., 10/30 | V Girls Volleyball | Stamford | Home - Trumbull HS-Gym [Directions] | 5:30 p.m. | W 3-1 | ||
| Wed., 10/30 | JV Girls Volleyball | Stamford | Home - Trumbull HS-Gym [Directions] | 4:00 p.m. | |||
| Wed., 10/30 | FR Girls Volleyball | Stamford | Away - Stamford HS-Kuzco Gymnasium [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM; 1 Bus | ||
| Thu., 10/31 | V Boys Soccer | TBA | Home - Trumbull HS-New Turf Field [Directions] | Canceled | Cancelled | ||
| Thu., 10/31 | V Boys Soccer | Norwalk | Home - Trumbull HS-New Turf Field [Directions] | 3:30 p.m. | W 1-0 (4-2 PK) | ||
| Fri., 11/1 | V Boys Cross Country | CIAC Boys State Open Championship | Away - Wickham Park | 2:45 p.m. | |||
| Fri., 11/1 | V Football | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 6:00 p.m. | L 27-39 | 3:30 PM; 2 Buses | |
| Fri., 11/1 | FR Boys Soccer | Danbury | Home - Trumbull HS-McDougall Stadium [Directions] | 5:00 p.m. | 2:30 PM; 1 Bus | ||
| Fri., 11/1 | V Girls Cross Country | CIAC Girls State Open Championship | Away - Wickham Park | 2:00 p.m. | |||
| Fri., 11/1 | V Girls Soccer | Staples | Away - Staples HS-Wakeman Field B (turf) [Directions] | 3:00 p.m. | L 5-2 | ||
| Fri., 11/1 | FR Girls Soccer | Danbury | Home - Trumbull HS-New Turf Field [Directions] | 5:00 p.m. | 12:00 PM | ||
| Fri., 11/1 | FR Girls Soccer | Danbury | Home - Trumbull HS-McDougall Stadium [Directions] | 5:30 p.m. | |||
| Fri., 11/1 | JV Girls Swimming and Diving | Greenwich, Brien McMahon, Darien, Fairfield Ludlowe, New Canaan, Norwalk/McMahon, Ridgefield, Stamford, Staples, Westhill/Stamford, Wilton | Away - Greenwich HS-Pool | 6:00 p.m. | 3:30 PM | ||
| Fri., 11/1 | V Girls Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 5:30 p.m. | W 3-0 | 2:45 PM | |
| Fri., 11/1 | JV Girls Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:00 p.m. | 2:45 PM; 1 Bus | ||
| Fri., 11/1 | Miscellaneous Events | Cheerleading @ Ludlowe | Home - TBA [Directions] | 6:00 p.m. | 4:45 PM; 1 Bus | ||
| Sat., 11/2 | JV Football | Fairfield Ludlowe | Home - Trumbull HS-McDougall Stadium [Directions] | 10:30 a.m. | |||
| Sat., 11/2 | V Girls Swimming and Diving | FCIAC Girls Swimming Trials | Away - Greenwich HS-Pool | 4:30 p.m. | 1:30 PM; 1 Bus | ||
| Sat., 11/2 | JV Girls Volleyball | Fairfield Warde, Brookfield, Fairfield Ludlowe, Greenwich, Joel Barlow, Masuk, Newtown, Ridgefield, Stamford, Staples, Westhill | Away - Fairfield Warde HS-Large Gym | 9:00 a.m. | |||
| Tue., 11/5 | V Boys Soccer | Staples | Home - Fairfield Ludlowe HS-Taft Field [Directions] | 7:00 p.m. | W 4-1 | ||
| Tue., 11/5 | V Girls Swimming and Diving | FCIAC Girls Swimming Championships | Away - Greenwich HS-Pool | 6:30 p.m. | 3:30 PM; 1 Bus | ||
| Tue., 11/5 | V Girls Volleyball | New Canaan | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | |||
| Thu., 11/7 | V Boys Soccer | Fairfield Warde | Away - Norwalk HS-Testa Field [Directions] | 6:00 p.m. | W 1-0 | 12:00 PM | |
| Thu., 11/7 | V Girls Volleyball | Westhill | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:00 p.m. | |||
| Fri., 11/8 | V Football | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 7:00 p.m. | L 28-48 | 4:00 PM; 2 Buses | |
| Fri., 11/8 | FR Football | New Canaan | Home - Trumbull HS-McDougall Stadium [Directions] | 4:00 p.m. | |||
| Fri., 11/8 | Miscellaneous Events | Cheerleading @ New Canaan | Home - TBA [Directions] | 7:00 p.m. | 5:15 PM; 2 Buses | ||
| Mon., 11/11 | JV Football | New Canaan | Home - Trumbull HS-McDougall Stadium [Directions] | 4:00 p.m. | |||
| Mon., 11/11 | V Boys Soccer | Amity | Home - Trumbull HS-New Turf Field [Directions] | 3:00 p.m. | W 3-0 | ||
| Tue., 11/12 | V Girls Soccer | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 4:00 p.m. | 2:00 PM, Dismiss 1:45 AM; 1 Bus | ||
| Tue., 11/12 | V Girls Volleyball | Hamden | Home - Trumbull HS-THS Main Gym [Directions] | 5:00 p.m. | |||
| Wed., 11/13 | V Boys Soccer | Shelton | Home - Trumbull HS-New Turf Field [Directions] | 2:00 p.m. | |||
| Wed., 11/13 | V Girls Swimming and Diving | CIAC Girls Class LL Diving Championship | Away - Middletown HS-Pool | 5:30 p.m. | |||
| Thu., 11/14 | FR Football | Westhill | Home - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | |||
| Thu., 11/14 | V Girls Volleyball | Cheshire | Home - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | |||
| Fri., 11/15 | V Boys Soccer | Staples | Home - Trumbull HS-New Turf Field [Directions] | 4:00 p.m. | W 2-1 (5-4 PK) | ||
| Sat., 11/16 | V Football | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 1:00 p.m. | W 35-0 | 10:00 AM; 2 Buses | |
| Sat., 11/16 | V Girls Swimming and Diving | CIAC Girls Class LL Trials | Away - East Hartford HS-Pool | 11:30 a.m. | |||
| Sat., 11/16 | V Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 2:00 p.m. | 11:30 AM; 1 Bus | ||
| Sat., 11/16 | Miscellaneous Events | Cheerleading @ Westhill | Home - TBA [Directions] | 1:00 p.m. | 11:15 AM; 2 Buses | ||
| Mon., 11/18 | JV Football | Westhill | Home - Trumbull HS-McDougall Stadium [Directions] | 4:00 p.m. | |||
| Mon., 11/18 | V Boys Soccer | Hall | Away - Xavier HS-Larry McHugh Field [Directions] | 6:30 p.m. | L 2-5 | ||
| Tue., 11/19 | V Girls Swimming and Diving | CIAC Girls Class LL Finals | Away - Bad-Site Wesleyan University-Freeman Athletic Center | 7:00 p.m. | |||
| Wed., 11/20 | V Girls Volleyball | Glastonbury | Home - Cheshire HS-Gym West [Directions] | 6:00 p.m. | |||
| Thu., 11/21 | FR Football | St. Joseph | Home - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | |||
| Thu., 11/21 | V Girls Swimming and Diving | CIAC Girls State Open Diving | Away - Middletown HS-Pool | 5:30 p.m. | |||
| Sat., 11/23 | JV Football | St. Joseph | Home - Trumbull HS-McDougall Stadium [Directions] | 10:30 a.m. | |||
| Sat., 11/23 | V Girls Volleyball | Westhill | Away - East Haven HS-Gym [Directions] | 7:00 p.m. | |||
| Sun., 11/24 | V Girls Swimming and Diving | CIAC Girls State Open Swimming | Away - Yale | 2:00 p.m. | |||
| Thu., 11/28 | V Football | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 10:30 a.m. | L 7-52 | 8:30 AM; 2 Buses | |
| Thu., 11/28 | Miscellaneous Events | Cheerleading @ Westhill | Home - TBA [Directions] | 10:30 a.m. | 9:45 AM; 2 Buses | ||
| Thu., 12/5 | V Boys Ice Hockey | Milford Coop (Scrim.) | Away - Milford Ice Pavillion-Ice Rink [Directions] | 3:50 p.m. | 2:45 PM; 1 Bus | ||
| Sat., 12/7 | V Girls Basketball | Daniel Hand (Scrim.) | Away - Daniel Hand HS-DHHS Gym [Directions] | 11:00 a.m. | 9:30 AM; 1 Bus | ||
| Sat., 12/7 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate (Scrim.) | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 5:15 p.m. | |||
| Wed., 12/11 | V Boys Basketball | Bunnell (Scrim.) | Away - Bunnell HS-Bunnell Main Gym [Directions] | 3:30 p.m. | 2:30 PM, Dismiss 2:15 PM; 1 Bus | ||
| Wed., 12/11 | V Boys Ice Hockey | Newington Coop (Scrim.) | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 6:30 p.m. | |||
| Wed., 12/11 | V Wrestling | Shared Practice | Home - Trumbull HS-Aux Gym [Directions] | 3:00 p.m. | |||
| Wed., 12/11 | V Girls Basketball | Newtown, Simsbury (Scrim.) | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | |||
| Wed., 12/11 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:30 p.m. | L 2-9 | ||
| Fri., 12/13 | V Boys Basketball | Shelton (Scrim.) | Away - Shelton HS-High School - Murray Gymnasium [Directions] | 3:45 p.m. | 3:00 PM; 1 Bus | ||
| Fri., 12/13 | V Girls Basketball | Farmington, Pomperaug (Scrim.) | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | |||
| Sat., 12/14 | V Boys Ice Hockey | Immaculate, Notre Dame-Fairfield, St. Joseph (Scrim.) | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 7:45 p.m. | |||
| Sat., 12/14 | V Wrestling | New Milford (Scrim.) | Away - New Milford HS-Small Gym - NMHS [Directions] | 9:00 a.m. | 7:30 AM; 1 Bus | ||
| Sat., 12/14 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:50 p.m. | L 1-10 | 7:00 PM; 1 Bus | |
| Sun., 12/15 | JV Girls Ice Hockey | New Canaan | Away - Stamford Twin Rinks-West [Directions] | 6:50 p.m. | 5:15 PM; 1 Bus | ||
| Wed., 12/18 | V Boys Ice Hockey | Watertown-Pomperaug | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 6:30 p.m. | W 7-2 | ||
| Wed., 12/18 | V Wrestling | Darien | Home - Trumbull HS-Aux Gym [Directions] | 4:00 p.m. | |||
| Wed., 12/18 | V Girls Basketball | Bridgeport Central | Away - Bridgeport Central HS-Barry McLeod Court [Directions] | 5:30 p.m. | W 66-10 | 3:00 PM | |
| Wed., 12/18 | JV Girls Basketball | Bridgeport Central | Away - Bridgeport Central HS-Barry McLeod Court [Directions] | 4:00 p.m. | 3:00 PM; 1 Bus | ||
| Wed., 12/18 | FR Girls Basketball | Danbury | Home - Trumbull HS-THS Main Gym [Directions] | 7:00 p.m. | |||
| Wed., 12/18 | V Girls Ice Hockey | New Canaan | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | L 1-8 | ||
| Thu., 12/19 | V Girls Basketball | Hamden | Home - Trumbull HS-THS Main Gym [Directions] | 7:15 p.m. | W 57-34 | ||
| Fri., 12/20 | V Boys Basketball | Waterford | Home - Trumbull HS-THS Main Gym [Directions] | 7:00 p.m. | W 67-57 | ||
| Fri., 12/20 | JV Boys Basketball | Waterford | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | |||
| Fri., 12/20 | FR Boys Basketball | Waterford | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | |||
| Fri., 12/20 | V Boys Indoor Track | Hillhouse Invitational | Away - Floyd Little Athletic Center | 4:00 p.m. | 2:15 PM, Dismiss 2:00 PM; 1 Bus | ||
| Fri., 12/20 | V Girls Indoor Track | Hillhouse Invitational | Away - Floyd Little Athletic Center | 4:00 p.m. | 2:15 PM, Dismiss 2:00 PM; 1 Bus | ||
| Sat., 12/21 | V Boys Basketball | Amity | Home - Trumbull HS-THS Main Gym [Directions] | 7:30 p.m. | W 46-36 | ||
| Sat., 12/21 | JV Boys Ice Hockey | Greenwich | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 4:30 p.m. | |||
| Sat., 12/21 | V Boys Indoor Track | Hillhouse Invitational | Away - Floyd Little Athletic Center | 10:00 a.m. | 8:15 AM; 1 Bus | ||
| Sat., 12/21 | V Wrestling | Manchester, Bristol Central, Glastonbury, Northwestern, South Windsor | Away - Manchester HS-Gym | 8:00 a.m. | 6:00 AM; 1 Bus | ||
| Sat., 12/21 | V Girls Basketball | Wilbur Cross | Home - Trumbull HS-THS Main Gym [Directions] | 5:45 p.m. | W 67-59 | ||
| Sat., 12/21 | V Girls Ice Hockey | Darien | Away - Darien Ice House-Ice Rink [Directions] | 4:00 p.m. | L 0-6 | 2:30 PM; 1 Bus | |
| Sat., 12/21 | V Girls Indoor Track | Hillhouse Invitational | Away - Floyd Little Athletic Center | 10:00 a.m. | 8:15 AM; 1 Bus | ||
| Sun., 12/22 | JV Girls Ice Hockey | Masuk Coop | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 5:30 p.m. | |||
| Mon., 12/23 | V Boys Ice Hockey | Branford | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 6:00 p.m. | L 0-3 | ||
| Mon., 12/23 | JV Wrestling | Trumbull JV Individual Tournament (4 mats) | Home - Trumbull HS-Aux Gym [Directions] | 8:00 a.m. | |||
| Mon., 12/23 | JV Wrestling | Xavier | Home - Trumbull HS-Aux Gym [Directions] | TBA | |||
| Mon., 12/23 | V Girls Basketball | Brien McMahon | Home - Trumbull HS-THS Main Gym [Directions] | 7:30 p.m. | W 66-18 | ||
| Mon., 12/23 | JV Girls Basketball | Brien McMahon | Home - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | |||
| Mon., 12/23 | FR Girls Basketball | Pomperaug | Away - Pomperaug HS-Main Gym [Directions] | 10:30 a.m. | 9:00 AM; 1 Bus | ||
| Mon., 12/23 | V Girls Ice Hockey | Branford | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 8:00 p.m. | L 2-6 | ||
| Thu., 12/26 | V Boys Indoor Track | North Shore Invitational | Away - Floyd Little Athletic Center | 9:00 a.m. | 6:30 AM; 1 Bus | ||
| Thu., 12/26 | V Girls Indoor Track | North Shore Invitational | Away - Armory Track (168th Street Armory, NYC) | 9:00 a.m. | 6:30 AM; 1 Bus | ||
| Fri., 12/27 | V Boys Basketball | Stratford | Away - Stratford HS-Gym [Directions] | 7:00 p.m. | L 63-64 | ||
| Fri., 12/27 | V Boys Ice Hockey | Portsmouth (NH) | Away - Whittemore Center Arena | 8:00 p.m. | W 4-2 | ||
| Fri., 12/27 | V Wrestling | Bristol Eastern | Away - Bristol Eastern HS-Gym [Directions] | 6:00 p.m. | 3:30 PM; 1 Bus | ||
| Fri., 12/27 | JV Girls Ice Hockey | TBA | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 5:15 p.m. | |||
| Sat., 12/28 | V Boys Basketball | Harding | Away - Stratford HS-Gym [Directions] | 3:00 p.m. | W 66-36 | ||
| Sat., 12/28 | V Boys Ice Hockey | Biddeford (ME) | Away - Whittemore Center Arena | 2:00 p.m. | W 3-0 | ||
| Sat., 12/28 | V Wrestling | Trumbull Duals (6 mats) | Home - Trumbull HS-Aux Gym [Directions] | 9:00 a.m. | |||
| Sat., 12/28 | V Girls Basketball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 6:00 p.m. | L 32-40 | ||
| Sat., 12/28 | V Girls Ice Hockey | Mercy/NW Catholic/East Hampton | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 6:00 p.m. | L 6-9 | ||
| Sun., 12/29 | V Boys Ice Hockey | Martha's Vineyard (MA) | Away - Martha's Vineyard Reg High | 1:00 p.m. | L 1-2 | TBA | |
| Mon., 12/30 | V Girls Basketball | Masuk | Home - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 4:00 p.m. | W 43-28 | ||
| Mon., 12/30 | V Girls Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | 2:10 p.m. | L 2-7 | 12:45 PM; 1 Bus | |
| Thu., 1/2 | V Boys Ice Hockey | St. Joseph | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 4:00 p.m. | W 6-3 | ||
| Fri., 1/3 | V Boys Basketball | Fairfield Ludlowe | Home - Trumbull HS-THS Main Gym [Directions] | 7:00 p.m. | W 72-58 | ||
| Fri., 1/3 | JV Boys Basketball | Fairfield Ludlowe | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | |||
| Fri., 1/3 | FR Boys Basketball | Fairfield Ludlowe | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | |||
| Fri., 1/3 | JV Boys Ice Hockey | Immaculate | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 4:00 p.m. | |||
| Fri., 1/3 | V Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 7:00 p.m. | W 46-44(OT) | 4:15 PM | |
| Fri., 1/3 | JV Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:30 p.m. | 4:15 PM; 1 Bus | ||
| Fri., 1/3 | FR Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:00 p.m. | 3:00 PM; 1 Bus | ||
| Fri., 1/3 | JV Girls Ice Hockey | Greenwich | Away - Greenwich - Dorothy Hamill-Rink [Directions] | 5:30 p.m. | 3:45 PM; 1 Bus | ||
| Fri., 1/3 | V Girls Indoor Track | Hispanic Games | Away - Armory Track (168th Street Armory, NYC) | 4:00 p.m. | 1:30 PM, Dismiss 1:15 PM; 1 Bus | ||
| Sat., 1/4 | V Boys Ice Hockey | Guilford | Away - East Haven HS-Veterans Rink [Directions] | 6:00 p.m. | W 8-3 | 4:00 PM; 1 Bus | |
| Sat., 1/4 | V Boys Indoor Track | FCIAC Qualifier #1 | Away - Staples HS-Field House | 10:00 a.m. | |||
| Sat., 1/4 | V Wrestling | Minnechaug (MA) | Away - Minnechaug Reg HS-Gym | 9:00 a.m. | 6:15 AM; 1 Bus | ||
| Sat., 1/4 | JV Wrestling | Bristol Eastern JV Meet | Away - TBA | 9:30 a.m. | 7:30 AM; 1 Bus | ||
| Sat., 1/4 | FR Girls Basketball | Pomperaug | Home - Trumbull HS-THS Main Gym [Directions] | 11:00 a.m. | |||
| Sat., 1/4 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 7:30 p.m. | L 6-12 | ||
| Sat., 1/4 | V Girls Indoor Track | FCIAC Qualifier #1 | Away - Staples HS-Field House | 10:00 a.m. | 8:30 AM; 1 Bus | ||
| Sat., 1/4 | V Girls Indoor Track | Hispanic Games | Away - Armory Track (168th Street Armory, NYC) | 9:00 a.m. | 6:30 AM; 1 Bus | ||
| Sun., 1/5 | V Girls Ice Hockey | Greenwich (Scrim.) | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 3:00 p.m. | |||
| Mon., 1/6 | JV Boys Ice Hockey | Darien | Away - Stamford Twin Rinks-West [Directions] | 8:40 p.m. | 6:45 PM; 1 Bus | ||
| Mon., 1/6 | V Girls Ice Hockey | Greenwich | Away - Greenwich - Dorothy Hamill-Rink [Directions] | 5:15 p.m. | L 0-6 | 3:30 PM; 1 Bus | |
| Tue., 1/7 | V Boys Basketball | Darien | Home - Trumbull HS-THS Main Gym [Directions] | 7:00 p.m. | W 69-56 | ||
| Tue., 1/7 | JV Boys Basketball | Darien | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | |||
| Tue., 1/7 | FR Boys Basketball | Darien | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | |||
| Tue., 1/7 | V Girls Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 7:00 p.m. | L 18-33 | 3:45 PM | |
| Tue., 1/7 | JV Girls Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | 3:45 PM; 1 Bus | ||
| Tue., 1/7 | FR Girls Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | 2:45 PM; 1 Bus | ||
| Wed., 1/8 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Away - Norwalk HS-Pat Spinola Natatorium [Directions] | 3:30 p.m. | 2:00 PM, Dismiss 1:45 PM; 1 Bus | ||
| Wed., 1/8 | V Wrestling | Staples | Home - Trumbull HS-Aux Gym [Directions] | 6:00 p.m. | |||
| Wed., 1/8 | V Girls Ice Hockey | Masuk Coop | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | 4:00 p.m. | W 6-5 | ||
| Fri., 1/10 | V Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 7:00 p.m. | L 70-73 | 3:45 PM | |
| Fri., 1/10 | JV Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:30 p.m. | 3:45 PM; 1 Bus | ||
| Fri., 1/10 | FR Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:00 p.m. | 2:15 PM, Dismiss 2:00 PM; 1 Bus | ||
| Fri., 1/10 | V Boys Indoor Track | Yale Invitational | Away - Yale University | 4:00 p.m. | 2:15 PM, Dismiss 2:00 PM; 1 Bus | ||
| Fri., 1/10 | V Wrestling | Guilford, Ledyard, Middletown | Away - Guilford HS-Main gym at GHS [Directions] | 4:30 p.m. | 2:30 PM, Dismiss 2:15 PM; 1 Bus | ||
| Fri., 1/10 | V Girls Basketball | Ridgefield | Home - Trumbull HS-THS Main Gym [Directions] | 7:00 p.m. | W 42-34 | ||
| Fri., 1/10 | JV Girls Basketball | Ridgefield | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | |||
| Fri., 1/10 | FR Girls Basketball | Ridgefield | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | |||
| Fri., 1/10 | V Girls Indoor Track | Yale Invitational | Away - Yale University | 4:00 p.m. | 2:15 PM, Dismiss 2:00 PM; 1 Bus | ||
| Sat., 1/11 | V Boys Ice Hockey | North Haven | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 8:30 p.m. | L 1-2(OT) | ||
| Sat., 1/11 | V Boys Indoor Track | FCIAC Qualifier #2 | Away - Staples HS-Field House | 10:00 a.m. | 8:30 AM; 2 Buses | ||
| Sat., 1/11 | V Boys Indoor Track | Yale Invitational | Away - Yale University | 9:30 a.m. | 8:00 AM; 1 Bus | ||
| Sat., 1/11 | JV Wrestling | Trumbull JV Duals (4 mats) | Home - Trumbull HS-Aux Gym [Directions] | 9:00 a.m. | |||
| Sat., 1/11 | V Girls Gymnastics | New Canaan, St. Joseph, Wilton | Home - Next Dimension [Directions] | 6:30 p.m. | Trumbull 128.9, Wilton 128.8, New Canaan 93.45 | ||
| Sat., 1/11 | V Girls Ice Hockey | Stamford/Westhill/Staples | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 6:30 p.m. | L 5-9 | ||
| Sat., 1/11 | V Girls Indoor Track | FCIAC Qualifier #2 | Away - Staples HS-Field House | 10:00 a.m. | 8:30 AM; 2 Buses | ||
| Sat., 1/11 | V Girls Indoor Track | Yale Invitational | Away - Yale University | 9:00 a.m. | 8:00 AM; 1 Bus | ||
| Mon., 1/13 | V Boys Ice Hockey | St. Joseph | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | 7:00 p.m. | W 8-1 | ||
| Mon., 1/13 | V Boys Swimming and Diving | Danbury | Home - Hillcrest MS-Pool [Directions] | 5:00 p.m. | |||
| Mon., 1/13 | V Girls Gymnastics | Westhill, St. Joseph, Stamford | Away - Westhill HS-New Gym [Directions] | 6:00 p.m. | Trumbull 126.3, Westhill 115.6, Stamford 70.7 | 4:00 PM; 1 Bus | |
| Tue., 1/14 | JV Boys Ice Hockey | Ridgefield | Away - Danbury Ice Arena-Colonial Rink [Directions] | 9:20 p.m. | 7:00 PM; 1 Bus | ||
| Wed., 1/15 | V Wrestling | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 6:00 p.m. | 4:15 PM; 1 Bus | ||
| Wed., 1/15 | FR Girls Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:00 p.m. | 2:15 PM, Dismiss 2:00 PM; 1 Bus | ||
| Fri., 1/17 | V Boys Basketball | Staples | Home - Trumbull HS-THS Main Gym [Directions] | 7:00 p.m. | W 71-59 | ||
| Fri., 1/17 | JV Boys Basketball | Staples | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | |||
| Fri., 1/17 | FR Boys Basketball | Staples | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | |||
| Fri., 1/17 | JV Boys Ice Hockey | St. Joseph | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 9:00 p.m. | |||
| Fri., 1/17 | V Boys Indoor Track | SCC Invitational | Away - Floyd Little Athletic Center | 4:00 p.m. | 2:15 PM, Dismiss 2:00 PM; 1 Bus | ||
| Fri., 1/17 | V Boys Swimming and Diving | New Canaan | Away - New Canaan YMCA-Pool [Directions] | 3:00 p.m. | 1:45 PM, Dismiss 1:30 AM; 1 Bus | ||
| Fri., 1/17 | V Girls Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 7:00 p.m. | W 44-40 | 4:00 PM | |
| Fri., 1/17 | JV Girls Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 5:30 p.m. | 4:00 PM; 1 Bus | ||
| Fri., 1/17 | FR Girls Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:00 p.m. | 2:45 PM; 1 Bus | ||
| Fri., 1/17 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 5:30 p.m. | L 0-8 | TBA | |
| Fri., 1/17 | V Girls Indoor Track | SCC Invitational | Away - Floyd Little Athletic Center | 4:00 p.m. | 2:15 PM, Dismiss 2:00 PM; 1 Bus | ||
| Sat., 1/18 | V Boys Indoor Track | FCIAC Qualifier #3 | Away - Staples HS-Field House | 10:00 a.m. | |||
| Sat., 1/18 | V Boys Indoor Track | New Balance Games | Away - Armory Track (168th Street Armory, NYC) | 8:00 a.m. | 7:15 AM; 1 Bus | ||
| Sat., 1/18 | V Wrestling | The Colter Abely Mid-Season Classic | Away - Mercy HS-Gym 1 | 9:00 a.m. | 6:45 AM; 1 Bus | ||
| Sat., 1/18 | V Girls Indoor Track | FCIAC Qualifier #3 | Away - Staples HS-Field House | 10:00 a.m. | 8:30 AM; 2 Buses | ||
| Sat., 1/18 | V Girls Indoor Track | New Balance Games | Away - Armory Track (168th Street Armory, NYC) | 9:00 a.m. | 7:15 AM; 1 Bus | ||
| Mon., 1/20 | JV Boys Ice Hockey | Staples | Away - Milford Ice Pavillion-Ice Rink [Directions] | 3:00 p.m. | 1:30 PM; 1 Bus | ||
| Mon., 1/20 | JV Wrestling | Bristol Eastern, Bristol Central, Daniel Hand, TBA, New Milford | Away - Bristol Eastern HS | 9:00 a.m. | 6:45 AM; 1 Bus | ||
| Mon., 1/20 | V Girls Gymnastics | Darien, St. Joseph | Home - Next Dimension [Directions] | 10:00 a.m. | Trumbull 133.6, Darien 130.9 | ||
| Mon., 1/20 | V Girls Ice Hockey | Notre Dame-Fairfield | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 2:30 p.m. | L 1-4 | ||
| Tue., 1/21 | V Boys Basketball | Stamford | Home - Trumbull HS-THS Main Gym [Directions] | 7:00 p.m. | L 82-86 | ||
| Tue., 1/21 | JV Boys Basketball | Stamford | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | |||
| Tue., 1/21 | FR Boys Basketball | Stamford | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | |||
| Tue., 1/21 | V Girls Basketball | Stamford | Away - Stamford HS-Kuzco Gymnasium [Directions] | 7:00 p.m. | W 46-41 | 3:45 PM | |
| Tue., 1/21 | JV Girls Basketball | Stamford | Away - Stamford HS-Kuzco Gymnasium [Directions] | 5:15 p.m. | 3:45 PM; 1 Bus | ||
| Tue., 1/21 | FR Girls Basketball | Stamford | Away - Stamford HS-Kuzco Gymnasium [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM; 1 Bus | ||
| Wed., 1/22 | V Boys Ice Hockey | Greenwich | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 8:30 p.m. | L 1-4 | ||
| Thu., 1/23 | V Girls Gymnastics | Greenwich | Away - Greenwich YWCA [Directions] | 6:00 p.m. | Trumbull 129.35, Greenwich 124.35 | ||
| Thu., 1/23 | V Girls Gymnastics | TBA, Staples | Away - TBA | 6:00 p.m. | |||
| Fri., 1/24 | V Boys Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 7:00 p.m. | L 48-50 | 3:45 PM | |
| Fri., 1/24 | JV Boys Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 5:15 p.m. | 3:45 PM; 1 Bus | ||
| Fri., 1/24 | FR Boys Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | 2:45 PM; 1 Bus | ||
| Fri., 1/24 | V Girls Basketball | New Canaan | Home - Trumbull HS-THS Main Gym [Directions] | 7:00 p.m. | L 29-33 | ||
| Fri., 1/24 | JV Girls Basketball | New Canaan | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | |||
| Fri., 1/24 | FR Girls Basketball | New Canaan | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | |||
| Sat., 1/25 | V Boys Ice Hockey | North Branford | Away - Northford Ice Pavilion-Red [Directions] | 3:30 p.m. | W 4-3 | 1:30 PM; 1 Bus | |
| Sat., 1/25 | V Boys Indoor Track | Wilton, Danbury, Fairfield Ludlowe, New Canaan, Norwalk, St. Joseph, Westhill | Away - Wilton HS-Nicholas Zeoli Field House | 9:30 a.m. | 8:00 AM; 2 Buses | ||
| Sat., 1/25 | V Wrestling | CONNECTICUT CHALLENGE | Away - Southington HS-Gym West | 6:00 a.m. | 6:45 AM; 1 Bus | ||
| Sat., 1/25 | JV Wrestling | Godleski Invitational JV Tournament | Away - Norwalk HS-Tom Scarso Gymnasium | 9:00 a.m. | 7:15 AM; 1 Bus | ||
| Sat., 1/25 | V Girls Ice Hockey | Guilford Coop | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 7:15 p.m. | L 1-11 | ||
| Sat., 1/25 | V Girls Indoor Track | Wilton, Danbury, Fairfield Ludlowe, New Canaan, Norwalk, St. Joseph, Westhill | Away - Wilton HS-Nicholas Zeoli Field House | 9:30 a.m. | 8:00 AM; 2 Buses | ||
| Mon., 1/27 | V Boys Basketball | Westhill | Home - Trumbull HS-THS Main Gym [Directions] | 7:00 p.m. | W 65-58 | ||
| Mon., 1/27 | JV Boys Basketball | Westhill | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | |||
| Mon., 1/27 | FR Boys Basketball | Westhill | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | |||
| Mon., 1/27 | JV Boys Ice Hockey | Fairfield Warde/Ludlowe | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 4:00 p.m. | |||
| Mon., 1/27 | V Boys Swimming and Diving | Greenwich | Away - Greenwich HS-Pool [Directions] | 4:00 p.m. | 2:15 PM, Dismiss 2:00 PM; 1 Bus | ||
| Mon., 1/27 | V Girls Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 5:30 p.m. | W 67-51 | 2:30 PM, Dismiss 2:15 PM | |
| Mon., 1/27 | JV Girls Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM; 1 Bus | ||
| Mon., 1/27 | V Girls Ice Hockey | Daniel Hand Coop | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 8:30 p.m. | W 6-5 OT | ||
| Tue., 1/28 | V Wrestling | Danbury | Away - Danbury HS-New Gym [Directions] | 5:00 p.m. | 3:00 PM; 1 Bus | ||
| Wed., 1/29 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 6:30 p.m. | L 1-2 | ||
| Wed., 1/29 | V Boys Swimming and Diving | Wilton | Home - Hillcrest MS-Pool [Directions] | 4:00 p.m. | |||
| Wed., 1/29 | JV Wrestling | Fairfield Warde | Home - Trumbull HS-Aux Gym [Directions] | 4:00 p.m. | |||
| Thu., 1/30 | V Boys Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 7:00 p.m. | W 58-55 | 4:00 PM | |
| Thu., 1/30 | JV Boys Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 5:30 p.m. | 4:00 PM; 1 Bus | ||
| Thu., 1/30 | FR Boys Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:00 p.m. | 2:45 PM; 1 Bus | ||
| Thu., 1/30 | V Boys Diving | Wilton | Away - New Canaan YMCA-Pool [Directions] | 5:30 p.m. | |||
| Thu., 1/30 | V Girls Basketball | Norwalk | Home - Trumbull HS-THS Main Gym [Directions] | 7:00 p.m. | W 70-37 | ||
| Thu., 1/30 | JV Girls Basketball | Norwalk | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | |||
| Thu., 1/30 | FR Girls Basketball | St. Joseph | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | |||
| Thu., 1/30 | V Girls Gymnastics | New Milford, St. Joseph | Away - New Milford HS-Small Gym - NMHS [Directions] | 5:00 p.m. | Trumbull 126.2, New Milford 131.85 | 3:00 PM; 1 Bus | |
| Thu., 1/30 | V Girls Ice Hockey | Mercy/NW Catholic/East Hampton | Away - Champions - Cromwell-Lower Rink [Directions] | 5:30 p.m. | L 2-6 | 3:30 PM; 1 Bus | |
| Fri., 1/31 | V Boys Swimming and Diving | Westhill/Stamford | Away - Westhill HS-Westhill Pool [Directions] | 4:00 p.m. | 1:45 PM; 1 Bus | ||
| Fri., 1/31 | V Wrestling | Fairfield Warde, John Jay (NY), New Canaan | Away - Fairfield Warde HS-Small Gym [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | ||
| Sat., 2/1 | V Boys Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | 5:20 p.m. | L 2-3 | 3:45 PM; 1 Bus | |
| Sat., 2/1 | V Boys Indoor Track | Western Division Championship | Away - Staples HS-Field House | 10:00 a.m. | 8:30 AM; 2 Buses | ||
| Sat., 2/1 | V Girls Gymnastics | Foran, Norwalk, St. Joseph, Staples | Home - Next Dimension [Directions] | 6:30 p.m. | Trumbull 131.3, Staples 126.5, Norwalk 114.3 | ||
| Sat., 2/1 | V Girls Indoor Track | Western Division Championship | Away - Staples HS-Field House | 10:00 a.m. | 8:30 AM; 2 Buses | ||
| Mon., 2/3 | V Boys Basketball | Trinity Catholic | Away - Trinity Catholic-Gym | 7:00 p.m. | L 51-71 | 3:45 PM | |
| Mon., 2/3 | JV Boys Basketball | Trinity Catholic | Away - Trinity Catholic-Gym | 5:30 p.m. | 3:45 PM; 1 Bus | ||
| Mon., 2/3 | FR Boys Basketball | Trinity Catholic | Away - Trinity Catholic-Gym | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM; 1 Bus | ||
| Mon., 2/3 | V Boys Ice Hockey | Brien McMahon/Norwalk | Away - Sono Ice House-Main Rink [Directions] | 8:40 p.m. | W 3-1 | 6:30 PM; 1 Bus | |
| Mon., 2/3 | V Girls Basketball | Trinity Catholic | Home - Trumbull HS-THS Main Gym [Directions] | 5:45 p.m. | W 58-32 | ||
| Mon., 2/3 | FR Girls Basketball | Stamford | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | |||
| Mon., 2/3 | V Girls Ice Hockey | Masuk Coop | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 8:30 p.m. | W 5-4 | ||
| Wed., 2/5 | V Wrestling | Fairfield Ludlowe | Home - Trumbull HS-Aux Gym [Directions] | 6:00 p.m. | |||
| Wed., 2/5 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:30 p.m. | L 3-9 | 6:45 PM; 1 Bus | |
| Thu., 2/6 | V Boys Indoor Track | FCIAC Championships | Away - Norwalk HS-Testa Field | 4:30 p.m. | 12:00 PM | ||
| Thu., 2/6 | V Girls Gymnastics | Fairfield Ludlowe, Fairfield Warde | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:30 p.m. | Trumbull 128.7, Warde 133.7, Ludlowe 135.2 | 5:00 PM; 1 Bus | |
| Thu., 2/6 | V Girls Indoor Track | FCIAC Championships | Away - Floyd Little Athletic Center-Field House | 4:30 p.m. | |||
| Fri., 2/7 | V Boys Basketball | St. Joseph | Away - Fairfield University-Gym [Directions] | 7:45 p.m. | W 85-81 | 6:00 PM; 1 Bus | |
| Fri., 2/7 | JV Boys Ice Hockey | Brien McMahon/Norwalk | Away - Sono Ice House-Main Rink [Directions] | 6:30 p.m. | 5:00 PM; 1 Bus | ||
| Fri., 2/7 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Home - Hillcrest MS-Pool [Directions] | 4:00 p.m. | |||
| Fri., 2/7 | V Wrestling | Norwalk, St. Joseph, Wilton (2 mats) | Home - Trumbull HS-Aux Gym [Directions] | 4:00 p.m. | |||
| Fri., 2/7 | V Girls Basketball | St. Joseph | Home - Trumbull HS-Fairfield University [Directions] | 6:00 p.m. | W 61-36 | ||
| Sat., 2/8 | JV Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 11:30 a.m. | 9:00 AM | ||
| Sat., 2/8 | FR Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 10:00 a.m. | 9:00 AM; 1 Bus | ||
| Sat., 2/8 | V Boys Ice Hockey | Ridgefield | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:50 p.m. | L 3-5 | 7:00 PM; 1 Bus | |
| Sat., 2/8 | JV Wrestling | Fairfield Ludlowe, Brien McMahon, Bristol Central, Fairfield Warde, Greenwich, Maloney, TBA, Stamford, Staples, Weston | Away - Fairfield Ludlowe HS-Main Gym | 9:30 a.m. | 8:00 AM; 1 Bus | ||
| Sat., 2/8 | JV Girls Basketball | St. Joseph | Home - Trumbull HS-THS Main Gym [Directions] | 11:30 a.m. | |||
| Sat., 2/8 | FR Girls Basketball | St. Joseph | Home - Trumbull HS-THS Main Gym [Directions] | 10:00 a.m. | |||
| Sat., 2/8 | V Girls Gymnastics | St. Joseph | Home - Next Dimension [Directions] | 6:30 p.m. | Trumbull 130.15, St. Joseph 138.55 | ||
| Sat., 2/8 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Conners - Stamford-Ice Rink [Directions] | 4:00 p.m. | L 5-10 | 2:30 PM; 1 Bus | |
| Sun., 2/9 | V Girls Ice Hockey | Daniel Hand Coop | Away - Northford Ice Pavilion-Red [Directions] | 3:40 p.m. | W 6-3 | 2:00 PM | |
| Mon., 2/10 | V Boys Basketball | Fairfield Warde | Home - Trumbull HS-THS Main Gym [Directions] | 7:00 p.m. | L 48-60 | ||
| Mon., 2/10 | JV Boys Basketball | Fairfield Warde | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | |||
| Mon., 2/10 | FR Boys Basketball | Fairfield Warde | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | |||
| Mon., 2/10 | JV Boys Ice Hockey | New Canaan | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 4:00 p.m. | |||
| Mon., 2/10 | V Boys Swimming and Diving | Darien | Home - Hillcrest MS-Pool [Directions] | 4:00 p.m. | |||
| Mon., 2/10 | V Girls Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 7:00 p.m. | W 53-40 | 4:00 PM | |
| Mon., 2/10 | JV Girls Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 5:15 p.m. | 4:00 PM; 1 Bus | ||
| Mon., 2/10 | FR Girls Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:00 p.m. | 2:45 PM; 1 Bus | ||
| Tue., 2/11 | V Wrestling | Westhill | Away - Westhill HS-New Gym [Directions] | 6:00 p.m. | 3:45 PM; 1 Bus | ||
| Wed., 2/12 | V Boys Ice Hockey | Staples | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 6:30 p.m. | T 1-1 | ||
| Wed., 2/12 | V Boys Swimming and Diving | Staples | Away - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | 2:45 PM; 1 Bus | ||
| Wed., 2/12 | JV Girls Ice Hockey | West Haven/SHA | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 5:15 p.m. | |||
| Thu., 2/13 | V Boys Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 7:00 p.m. | L 69-73 | 3:45 PM | |
| Thu., 2/13 | JV Boys Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:15 p.m. | 3:45 PM; 1 Bus | ||
| Thu., 2/13 | FR Boys Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM; 1 Bus | ||
| Thu., 2/13 | V Boys Indoor Track | CIAC Boys Class LL Divisional Championship | Away - Floyd Little Athletic Center-Field House | 4:00 p.m. | |||
| Thu., 2/13 | V Girls Basketball | Wilton | Home - Trumbull HS-THS Main Gym [Directions] | 7:00 p.m. | W 58-36 | ||
| Thu., 2/13 | JV Girls Basketball | Wilton | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | |||
| Thu., 2/13 | FR Girls Basketball | New Canaan | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | |||
| Thu., 2/13 | V Girls Indoor Track | CIAC Girls Class LL Divisional Championship | Away - Floyd Little Athletic Center-FieldHouse | 4:00 p.m. | |||
| Fri., 2/14 | V Wrestling | FCIAC's | Away - New Canaan HS-Main Gym | 4:30 p.m. | 1:45 PM, Dismiss 1:30 PM; 1 Bus | ||
| Sat., 2/15 | V Boys Ice Hockey | Wilton | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 1:30 p.m. | W 4-2 | ||
| Sat., 2/15 | V Wrestling | FCIAC Wrestling Championship | Away - New Canaan HS-Main Gym | 10:00 a.m. | 8:00 AM; 1 Bus | ||
| Sat., 2/15 | V Girls Gymnastics | FCIAC Gymnastics Championship | Away - Westhill HS-New Gym | 11:00 a.m. | 128.75 | 9:00 AM; 1 Bus | |
| Mon., 2/17 | V Boys Basketball | Danbury | Home - Trumbull HS-THS Main Gym [Directions] | 7:00 p.m. | L 47-51 | ||
| Mon., 2/17 | JV Boys Basketball | Danbury | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | |||
| Mon., 2/17 | FR Boys Basketball | Danbury | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | |||
| Mon., 2/17 | JV Boys Ice Hockey | Fairfield Prep | Away - Wonderland of Ice-Stadium [Directions] | 10:30 a.m. | 9:00 AM; 1 Bus | ||
| Mon., 2/17 | JV Wrestling | Simsbury, East Haven, Rocky Hill | Away - Simsbury HS [Directions] | 9:00 a.m. | |||
| Mon., 2/17 | V Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 7:00 p.m. | L 43-48 | 3:45 PM | |
| Mon., 2/17 | JV Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 5:30 p.m. | 3:45 PM; 1 Bus | ||
| Mon., 2/17 | FR Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | ||
| Wed., 2/19 | V Boys Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 7:00 p.m. | W 48-45 | 3:45 PM | |
| Wed., 2/19 | JV Boys Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:15 p.m. | 3:45 PM; 1 Bus | ||
| Wed., 2/19 | FR Boys Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM; 1 Bus | ||
| Wed., 2/19 | V Boys Ice Hockey | Westhill/Stamford | Away - Terry Conners - Stamford-Ice Rink [Directions] | 7:50 p.m. | L 3-4 | 6:15 PM; 1 Bus | |
| Wed., 2/19 | V Girls Basketball | Greenwich | Home - Trumbull HS-THS Main Gym [Directions] | 7:00 p.m. | W 56-50 | ||
| Wed., 2/19 | JV Girls Basketball | Greenwich | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | |||
| Wed., 2/19 | FR Girls Basketball | Greenwich | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | |||
| Thu., 2/20 | JV Boys Ice Hockey | Notre Dame-West Haven | Away - West Haven HS-Bennett Rink [Directions] | 4:00 p.m. | 3:00 PM; 1 Bus | ||
| Fri., 2/21 | V Wrestling | CIAC Class LL Divisional Championship | Away - Trumbull HS-Gym | 3:00 p.m. | |||
| Sat., 2/22 | V Boys Ice Hockey | Trinity Catholic | Away - Terry Conners - Stamford-Ice Rink | 2:20 p.m. | W 6-1 | 12:45 PM; 1 Bus | |
| Sat., 2/22 | V Boys Indoor Track | CIAC Boys State Open Championship | Away - Floyd Little Athletic Center-Field House | 12:00 p.m. | |||
| Sat., 2/22 | V Wrestling | CIAC Class LL Divisional Championship | Away - Trumbull HS-Gym | 9:00 a.m. | |||
| Sat., 2/22 | V Girls Basketball | Stamford | Home - Staples HS-Staples Gym [Directions] | 12:00 p.m. | |||
| Sat., 2/22 | V Girls Indoor Track | CIAC Girls State Open Championship | Away - Floyd Little Athletic Center-FieldHouse | 12:00 p.m. | |||
| Mon., 2/24 | V Boys Basketball | Bridgeport Central | Home - Trumbull HS-THS Main Gym [Directions] | 7:00 p.m. | W 77-56 | ||
| Mon., 2/24 | JV Boys Basketball | Bridgeport Central | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | |||
| Mon., 2/24 | FR Boys Basketball | Bridgeport Central | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | |||
| Tue., 2/25 | V Girls Basketball | Ridgefield | Home - Trumbull HS-THS Main Gym [Directions] | 7:45 p.m. | |||
| Tue., 2/25 | Miscellaneous Events | FCIAC G. Basketball Semi-Finals | Home - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | |||
| Wed., 2/26 | V Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 7:00 p.m. | W 88-81 | 4:00 PM | |
| Wed., 2/26 | JV Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 5:15 p.m. | 4:00 PM; 1 Bus | ||
| Wed., 2/26 | FR Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:00 p.m. | 2:45 PM; 1 Bus | ||
| Wed., 2/26 | V Boys Ice Hockey | Darien | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 8:30 p.m. | L 0-8 | ||
| Wed., 2/26 | V Boys Swimming and Diving | Ridgefield | Home - Hillcrest MS-Pool [Directions] | 3:30 p.m. | |||
| Thu., 2/27 | Miscellaneous Events | FCIAC G. Basketball Finals | Home - Trumbull HS-Gym [Directions] | 7:00 p.m. | |||
| Fri., 2/28 | V Wrestling | CIAC State Open Championship | Away - Floyd Little Athletic Center-Field House | 3:00 p.m. | |||
| Sat., 2/29 | V Wrestling | CIAC State Open Championship | Away - Floyd Little Athletic Center-Field House | 9:00 a.m. | |||
| Sat., 2/29 | V Girls Gymnastics | CIAC Class L Divisional Championship | Away - Jonathan Law HS-James L. Richetelli Memorial Gymnasium | 9:00 a.m. | |||
| Mon., 3/2 | V Girls Basketball | West Haven | Home - Trumbull HS-THS Main Gym [Directions] | 6:30 p.m. | |||
| Tue., 3/3 | V Boys Basketball | Stratford (Scrim.) | Home - Trumbull HS-THS Main Gym [Directions] | 4:30 p.m. | |||
| Tue., 3/3 | JV Boys Ice Hockey | Immaculate | Home - Danbury Ice Arena-LIberty Rink [Directions] | 5:00 p.m. | |||
| Tue., 3/3 | V Boys Swimming and Diving | FCIAC Swimming Trials | Away - Greenwich HS-Pool | 5:30 p.m. | |||
| Wed., 3/4 | V Boys Swimming and Diving | FCIAC Diving Championship | Away - Westhill HS-Westhill Pool | 4:30 p.m. | |||
| Thu., 3/5 | V Boys Swimming and Diving | FCIAC Boys Swim Finals | Away - Greenwich HS-Pool | 6:30 p.m. | |||
| Thu., 3/5 | V Girls Basketball | Conard | Home - Trumbull HS-THS Main Gym [Directions] | 6:30 p.m. | |||
| Fri., 3/6 | V Boys Basketball | Masuk (Scrim.) | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 3:30 p.m. | |||
| Sat., 3/7 | V Girls Gymnastics | CIAC State Open Championship | Away - New Milford HS-Main Gym - NMHS | Postponed | |||
| Mon., 3/9 | V Boys Basketball | Fairfield Prep | Home - Trumbull HS-THS Main Gym [Directions] | 5:15 p.m. | |||
| Mon., 3/9 | V Boys Ice Hockey | North Haven | Away - Northford Ice Pavilion-Red [Directions] | 8:15 p.m. | |||
| Mon., 3/9 | V Girls Basketball | Greenwich | Home - Trumbull HS-THS Main Gym [Directions] | 7:00 p.m. | |||
| Wed., 3/11 | V Boys Swimming and Diving | CIAC Boys Class LL Diving Championship | Away - Middletown HS-MHS Pool | Canceled | Cancelled | ||
| Fri., 3/13 | Miscellaneous Events | CIAC G. Basketball Semi-Finals | Home - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | |||
| Sat., 3/14 | V Boys Swimming and Diving | CIAC Boys Class LL Trials | Away - East Hartford HS-Pool | Canceled | Cancelled | ||
| Mon., 3/16 | Miscellaneous Events | CIAC G. Basketball Semi-Finals | Home - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | |||
| Tue., 3/17 | V Boys Swimming and Diving | CIAC Boys Class LL Finals | Away - Wesleyan University-Pool | Canceled | Cancelled | ||
| Thu., 3/19 | V Boys Swimming and Diving | CIAC Boys State Open Diving | Away - Bulkeley HS-Pool | Canceled | Cancelled | ||
| Thu., 3/19 | Miscellaneous Events | B. Volleyball | Home - Trumbull HS-THS Main Gym [Directions] | 3:00 p.m. | |||
| Sat., 3/21 | V Boys Swimming and Diving | CIAC Boys State Open Swimming | Away - Yale | Canceled | Cancelled | ||
| Thu., 3/26 | V Softball | Woodland (Scrim.) | Home - Trumbull HS-Varsity Softball Diamond [Directions] | Cancelled | Cancelled | ||
| Sat., 3/28 | V Baseball | Bunnell (Scrim.) | Home - Trumbull HS-Baseball Diamond [Directions] | Cancelled | |||
| Sat., 3/28 | V Softball | Maloney, TBA (Scrim.) | Home - Trumbull HS-Varsity Softball Diamond [Directions] | Cancelled | |||
| Sat., 3/28 | V Softball | Maloney | Home - Trumbull HS-Varsity Softball Diamond [Directions] | Cancelled | |||
| Sat., 3/28 | V Girls Volleyball | Glastonbury | Away - Glastonbury HS-Gym [Directions] | Postponed | 3:30 PM; 1 Bus | ||
| Mon., 3/30 | V Baseball | Staples (Scrim.) | Away - Staples HS-Baseball Diamond [Directions] | Cancelled | 2:45 PM; 1 Bus | ||
| Mon., 3/30 | V Softball | Shelton (Scrim.) | Home - Trumbull HS-Varsity Softball Diamond [Directions] | Cancelled | Cancelled | ||
| Mon., 3/30 | JV Softball | Shelton (Scrim.) | Home - Trumbull HS-JV Softball Diamond [Directions] | Cancelled | Cancelled | ||
| Tue., 3/31 | V Softball | Lauralton Hall (Scrim.) | Away - Lauralton Hall-Softball Varsity Diamond [Directions] | Cancelled | 3:00 PM; 1 Bus | ||
| Wed., 4/1 | V Baseball | Notre Dame-Fairfield (Scrim.) | Away - Notre Dame - Fairfield -Fabbri Field [Directions] | Cancelled | 2:45 PM; 1 Bus | ||
| Wed., 4/1 | V Baseball | Seymour (Scrim.) | Home - Trumbull HS-Varsity Baseball Field [Directions] | Cancelled | Cancelled | ||
| Wed., 4/1 | JV Baseball | Seymour (Scrim.) | Home - Trumbull HS-JV Baseball Field [Directions] | Cancelled | Cancelled | ||
| Wed., 4/1 | V Boys Lacrosse | Weston (Scrim.) | Home - Trumbull HS-McDougall Stadium [Directions] | Cancelled | |||
| Wed., 4/1 | JV Boys Lacrosse | Weston (Scrim.) | Home - Trumbull HS-New Turf Field [Directions] | Cancelled | |||
| Thu., 4/2 | V Baseball | Newtown (Scrim.) | Home - Trumbull HS-Varsity Baseball Field [Directions] | Cancelled | |||
| Thu., 4/2 | JV Baseball | Newtown (Scrim.) | Home - Trumbull HS-JV Baseball Field [Directions] | Cancelled | |||
| Thu., 4/2 | V Girls Lacrosse | Stratford/Bunnell (Scrim.) | Away - Penders Field-Penders Field - Stratford [Directions] | Cancelled | Cancelled | 3:45 PM; 1 Bus | |
| Thu., 4/2 | V Softball | Oxford (Scrim.) | Home - Trumbull HS-Varsity Softball Diamond [Directions] | Cancelled | |||
| Thu., 4/2 | JV Softball | Oxford (Scrim.) | Home - Trumbull HS-JV Softball Diamond [Directions] | Cancelled | |||
| Sat., 4/4 | V Baseball | Masuk | Home - Trumbull HS-Varsity Baseball Field [Directions] | Cancelled | |||
| Sat., 4/4 | JV Baseball | Masuk | Away - Masuk HS-John Giampaolo Baseball Field @ Masuk HS [Directions] | Cancelled | |||
| Sat., 4/4 | FR Baseball | Masuk | Home - Trumbull HS-JV Baseball Field [Directions] | Cancelled | |||
| Sat., 4/4 | V Boys Lacrosse | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | Cancelled | 12:00 PM | ||
| Sat., 4/4 | JV Boys Lacrosse | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | Cancelled | 12:00 PM | ||
| Sat., 4/4 | V Boys Volleyball | Masuk | Home - Trumbull HS-THS Main Gym [Directions] | Cancelled | |||
| Sat., 4/4 | JV Boys Volleyball | Masuk | Home - Trumbull HS-THS Main Gym [Directions] | Cancelled | |||
| Sat., 4/4 | V Girls Lacrosse | Lauralton Hall | Home - Trumbull HS-McDougall Stadium [Directions] | Cancelled | |||
| Sat., 4/4 | JV Girls Lacrosse | Lauralton Hall | Home - Trumbull HS-McDougall Stadium [Directions] | Cancelled | |||
| Sat., 4/4 | V Softball | Seymour (Scrim.) | Home - Trumbull HS-Varsity Softball Diamond [Directions] | Cancelled | Cancelled | ||
| Sat., 4/4 | JV Softball | Seymour (Scrim.) | Home - Trumbull HS-JV Softball Diamond [Directions] | Cancelled | Cancelled | ||
| Mon., 4/6 | V Baseball | Amity | Away - Amity Regional HS-John Janenda Field [Directions] | Cancelled | 12:00 PM | ||
| Mon., 4/6 | JV Baseball | Amity | Home - Trumbull HS-Varsity Baseball Field [Directions] | Cancelled | |||
| Mon., 4/6 | V Boys Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | Cancelled | 12:00 PM | ||
| Mon., 4/6 | JV Boys Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | Cancelled | 12:00 PM | ||
| Mon., 4/6 | V Softball | Bristol Eastern | Home - Trumbull HS-Varsity Softball Diamond [Directions] | Cancelled | |||
| Mon., 4/6 | JV Softball | Bristol Eastern | Home - Trumbull HS-JV Softball Diamond [Directions] | Cancelled | |||
| Tue., 4/7 | FR Baseball | Amity | Away - Amity Regional HS-John Janenda Field [Directions] | Cancelled | 12:00 PM | ||
| Tue., 4/7 | V Boys Lacrosse | East Catholic | Home - Trumbull HS-McDougall Stadium [Directions] | Cancelled | |||
| Tue., 4/7 | JV Boys Lacrosse | East Catholic | Home - Trumbull HS-The Pit [Directions] | Cancelled | |||
| Tue., 4/7 | V Boys Tennis | Fairfield Ludlowe | Home - Trumbull HS-Tennis Courts [Directions] | Cancelled | |||
| Tue., 4/7 | V Boys Volleyball | Joel Barlow | Home - Trumbull HS-THS Main Gym [Directions] | Cancelled | |||
| Tue., 4/7 | JV Boys Volleyball | Joel Barlow | Home - Trumbull HS-THS Main Gym [Directions] | Cancelled | |||
| Tue., 4/7 | V Girls Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | Cancelled | 12:00 PM | ||
| Tue., 4/7 | V Girls Lacrosse | Stamford | Home - Trumbull HS-New Turf Field [Directions] | Cancelled | |||
| Tue., 4/7 | JV Girls Lacrosse | Stamford | Home - Trumbull HS-New Turf Field [Directions] | Cancelled | |||
| Tue., 4/7 | V Girls Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Tennis Courts [Directions] | Cancelled | 12:00 PM | ||
| Wed., 4/8 | FR Boys Lacrosse | Staples | Away - Staples HS-Wakeman Field B (turf) [Directions] | Cancelled | |||
| Wed., 4/8 | V Boys Tennis | Darien | Home - Trumbull HS-Tennis Courts [Directions] | Cancelled | |||
| Wed., 4/8 | V Girls Golf | Danbury | Away - Richter Park Golf Course [Directions] | Cancelled | 12:00 PM | ||
| Wed., 4/8 | V Girls Tennis | Darien | Away - Darien HS-DHS Tennis Courts [Directions] | Cancelled | 12:00 PM | ||
| Thu., 4/9 | V Baseball | Fairfield Prep | Away - Fairfield University-Alumni Diamond [Directions] | Cancelled | 12:00 PM | ||
| Thu., 4/9 | V Boys Outdoor Track | Stamford | Home - Trumbull HS-McDougall Stadium [Directions] | Cancelled | |||
| Thu., 4/9 | V Boys Volleyball | Shelton | Away - Shelton HS-High School - Murray Gymnasium [Directions] | Cancelled | |||
| Thu., 4/9 | JV Boys Volleyball | Shelton | Away - Shelton HS-High School - Murray Gymnasium [Directions] | Cancelled | |||
| Thu., 4/9 | V Girls Outdoor Track | Stamford | Home - Trumbull HS-McDougall Stadium [Directions] | Cancelled | |||
| Thu., 4/9 | V Softball | Staples | Home - Trumbull HS-Varsity Softball Diamond [Directions] | Cancelled | |||
| Thu., 4/9 | JV Softball | Staples | Home - Trumbull HS-JV Softball Diamond [Directions] | Cancelled | |||
| Sat., 4/11 | V Boys Lacrosse | North Haven | Away - North Haven MS-East Turf Field [Directions] | Cancelled | |||
| Sat., 4/11 | JV Boys Lacrosse | North Haven | Away - North Haven MS-East Turf Field [Directions] | Cancelled | |||
| Sat., 4/11 | V Girls Lacrosse | Masuk | Home - Trumbull HS-McDougall Stadium [Directions] | Cancelled | |||
| Sat., 4/11 | JV Girls Lacrosse | Masuk | Home - Trumbull HS-McDougall Stadium [Directions] | Cancelled | |||
| Mon., 4/13 | V Baseball | Fairfield Ludlowe | Home - Trumbull HS-Varsity Baseball Field [Directions] | Cancelled | |||
| Mon., 4/13 | JV Baseball | Fairfield Ludlowe | Home - Trumbull HS-JV Baseball Field [Directions] | Cancelled | |||
| Mon., 4/13 | FR Baseball | Fairfield Ludlowe | Away - Kiwanis Field-Baseball Diamond [Directions] | Cancelled | 12:00 PM | ||
| Mon., 4/13 | FR Boys Lacrosse | Amity | Away - Amity Regional HS-Amity High School - Field # 2 [Directions] | Cancelled | 12:00 PM | ||
| Mon., 4/13 | V Boys Tennis | Ridgefield | Away - Ridgefield HS-RHS Tennis Courts [Directions] | Cancelled | |||
| Mon., 4/13 | V Softball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | Cancelled | 12:00 PM | ||
| Mon., 4/13 | JV Softball | Fairfield Ludlowe | Away - Haydon Field-Softball Diamond [Directions] | Cancelled | 12:00 PM | ||
| Mon., 4/13 | V Girls Tennis | Ridgefield | Home - Trumbull HS-Tennis Courts [Directions] | Cancelled | |||
| Tue., 4/14 | V Boys Lacrosse | Masuk | Home - Trumbull HS-McDougall Stadium [Directions] | Cancelled | |||
| Tue., 4/14 | JV Boys Lacrosse | Masuk | Home - Trumbull HS-New Turf Field [Directions] | Cancelled | |||
| Tue., 4/14 | V Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | Cancelled | |||
| Tue., 4/14 | JV Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | Cancelled | |||
| Tue., 4/14 | FR Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Fairfield Warde Grass Utility Field [Directions] | Cancelled | 12:00 PM | ||
| Wed., 4/15 | V Baseball | Darien | Home - Trumbull HS-Varsity Baseball Field [Directions] | Cancelled | |||
| Wed., 4/15 | JV Baseball | Darien | Home - Trumbull HS-JV Baseball Field [Directions] | Cancelled | |||
| Wed., 4/15 | FR Baseball | Darien | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | Cancelled | |||
| Wed., 4/15 | FR Boys Lacrosse | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | Cancelled | 12:00 PM | ||
| Wed., 4/15 | V Boys Tennis | Staples | Home - Trumbull HS-Tennis Courts [Directions] | Cancelled | |||
| Wed., 4/15 | V Softball | Darien | Away - Darien HS-DHS Softball - Varsity Field [Directions] | Cancelled | |||
| Wed., 4/15 | V Girls Tennis | Staples | Away - Staples HS-Staples Tennis Courts [Directions] | Cancelled | |||
| Thu., 4/16 | V Boys Lacrosse | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | Cancelled | 12:00 PM | ||
| Thu., 4/16 | JV Boys Lacrosse | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | Cancelled | 12:00 PM | ||
| Thu., 4/16 | FR Boys Lacrosse | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | Cancelled | |||
| Thu., 4/16 | V Girls Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | Cancelled | 12:00 PM | ||
| Thu., 4/16 | JV Girls Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | Cancelled | 12:00 PM | ||
| Thu., 4/16 | FR Girls Lacrosse | Norwalk | Home - Trumbull HS-The Pit [Directions] | Cancelled | |||
| Thu., 4/16 | V Softball | Ridgefield | Home - Trumbull HS-Varsity Softball Diamond [Directions] | Cancelled | |||
| Thu., 4/16 | JV Softball | Ridgefield | Home - Trumbull HS-JV Softball Diamond [Directions] | Cancelled | |||
| Fri., 4/17 | V Baseball | Ridgefield | Away - Governor Field [Directions] | Cancelled | |||
| Fri., 4/17 | JV Baseball | Ridgefield | Away - East Ridge MS-Baseball Field [Directions] | Cancelled | |||
| Fri., 4/17 | FR Baseball | Ridgefield | Home - Trumbull HS-Varsity Baseball Field [Directions] | Cancelled | |||
| Fri., 4/17 | FR Boys Lacrosse | Ridgefield | Away - Ridgefield HS-RHS Lower Grass Field [Directions] | Cancelled | |||
| Fri., 4/17 | V Boys Volleyball | Staples | Home - Trumbull HS-THS Main Gym [Directions] | Cancelled | |||
| Fri., 4/17 | JV Boys Volleyball | Staples | Home - Trumbull HS-THS Main Gym [Directions] | Cancelled | |||
| Fri., 4/17 | FR Girls Lacrosse | Ridgefield | Home - Trumbull HS-The Pit [Directions] | Cancelled | |||
| Sat., 4/18 | V Boys Lacrosse | Danbury | Home - Trumbull HS-McDougall Stadium [Directions] | Cancelled | |||
| Sat., 4/18 | JV Boys Lacrosse | Danbury | Home - Trumbull HS-McDougall Stadium [Directions] | Cancelled | |||
| Sat., 4/18 | V Boys Volleyball | Newtown | Home - Trumbull HS-THS Main Gym [Directions] | Cancelled | |||
| Sat., 4/18 | JV Boys Volleyball | Newtown | Home - Trumbull HS-THS Main Gym [Directions] | Cancelled | |||
| Sat., 4/18 | V Girls Lacrosse | West Haven | Home - Trumbull HS-New Turf Field [Directions] | Cancelled | |||
| Sat., 4/18 | JV Girls Lacrosse | West Haven | Home - Trumbull HS-New Turf Field [Directions] | Cancelled | |||
| Mon., 4/20 | V Baseball | Waterford | Home - Trumbull HS-Varsity Baseball Field [Directions] | Cancelled | |||
| Mon., 4/20 | JV Baseball | Waterford | Home - Trumbull HS-JV Baseball Field [Directions] | Cancelled | |||
| Mon., 4/20 | FR Boys Lacrosse | Westhill | Home - Trumbull HS-The Pit [Directions] | Cancelled | |||
| Mon., 4/20 | V Boys Tennis | Stamford | Home - Trumbull HS-Tennis Courts [Directions] | Cancelled | |||
| Mon., 4/20 | JV Boys Tennis | Ridgefield | Home - Unity Park [Directions] | Cancelled | |||
| Mon., 4/20 | V Boys Volleyball | Westhill | Home - Trumbull HS-THS Main Gym [Directions] | Cancelled | |||
| Mon., 4/20 | JV Boys Volleyball | Westhill | Home - Trumbull HS-THS Main Gym [Directions] | Cancelled | |||
| Mon., 4/20 | FR Girls Lacrosse | Westhill | Away - Westhill HS-Westhill Front Turf Field [Directions] | Cancelled | |||
| Mon., 4/20 | V Softball | Bassick | Away - Ripken Field-Softball [Directions] | Cancelled | |||
| Mon., 4/20 | V Softball | Bassick | Away - Ripken Field-Softball [Directions] | Cancelled | |||
| Mon., 4/20 | V Girls Tennis | Stamford | Away - Stamford HS-SHS Tennis Courts [Directions] | Cancelled | |||
| Mon., 4/20 | JV Girls Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | Cancelled | |||
| Tue., 4/21 | V Boys Golf | Fairfield Ludlowe | Home - Tashua Knolls Golf Course [Directions] | Cancelled | |||
| Tue., 4/21 | JV Boys Golf | Fairfield Ludlowe | Home - Tashua Knolls Golf Course [Directions] | Cancelled | |||
| Tue., 4/21 | V Boys Lacrosse | Stamford | Home - Trumbull HS-McDougall Stadium [Directions] | Cancelled | |||
| Tue., 4/21 | JV Boys Lacrosse | Stamford | Home - Trumbull HS-New Turf Field [Directions] | Cancelled | |||
| Tue., 4/21 | V Boys Tennis | New Canaan | Away - New Canaan HS-NCHS Tennis Courts [Directions] | Cancelled | |||
| Tue., 4/21 | V Girls Golf | Wilton | Home - Tashua Knolls Golf Course [Directions] | Cancelled | |||
| Tue., 4/21 | V Girls Tennis | New Canaan | Home - Trumbull HS-Tennis Courts [Directions] | Cancelled | |||
| Wed., 4/22 | V Baseball | Staples | Home - Trumbull HS-Varsity Baseball Field [Directions] | Cancelled | |||
| Wed., 4/22 | JV Baseball | Staples | Home - Trumbull HS-JV Baseball Field [Directions] | Cancelled | |||
| Wed., 4/22 | FR Baseball | Staples | Away - Staples HS-Baseball Diamond [Directions] | Cancelled | |||
| Wed., 4/22 | V Boys Golf | Trinity Catholic | Away - Sterling Farms Golf Course | Cancelled | |||
| Wed., 4/22 | FR Boys Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | Cancelled | |||
| Wed., 4/22 | V Boys Outdoor Track | Westhill | Home - Trumbull HS-McDougall Stadium [Directions] | Cancelled | |||
| Wed., 4/22 | V Boys Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | Cancelled | |||
| Wed., 4/22 | JV Boys Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | Cancelled | |||
| Wed., 4/22 | V Girls Golf | Darien | Home - Tashua Knolls Golf Course [Directions] | Cancelled | |||
| Wed., 4/22 | JV Girls Golf | Darien | Home - Tashua Knolls Golf Course [Directions] | Cancelled | |||
| Wed., 4/22 | FR Girls Lacrosse | Fairfield Ludlowe | Home - Trumbull HS-The Pit [Directions] | Cancelled | |||
| Wed., 4/22 | V Girls Outdoor Track | Westhill | Home - Trumbull HS-McDougall Stadium [Directions] | Cancelled | |||
| Wed., 4/22 | V Softball | Staples | Away - Staples HS-Wakeman Field [Directions] | Cancelled | |||
| Wed., 4/22 | JV Softball | Staples | Away - Staples HS-Staples Softball Field [Directions] | Cancelled | |||
| Thu., 4/23 | V Boys Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | Cancelled | |||
| Thu., 4/23 | JV Boys Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | Cancelled | |||
| Thu., 4/23 | V Boys Tennis | Westhill | Home - Trumbull HS-Tennis Courts [Directions] | Cancelled | |||
| Thu., 4/23 | V Girls Lacrosse | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | Cancelled | |||
| Thu., 4/23 | JV Girls Lacrosse | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | Cancelled | |||
| Thu., 4/23 | V Girls Tennis | Westhill | Away - Westhill HS-Westhill Tennis Courts [Directions] | Cancelled | |||
| Fri., 4/24 | V Baseball | Stamford | Home - Trumbull HS-Varsity Baseball Field [Directions] | Cancelled | |||
| Fri., 4/24 | JV Baseball | Stamford | Home - Trumbull HS-JV Baseball Field [Directions] | Cancelled | |||
| Fri., 4/24 | FR Baseball | Stamford | Away - Stamford HS-SHS Baseball Diamond [Directions] | Cancelled | |||
| Fri., 4/24 | V Boys Volleyball | Stamford | Away - Stamford HS-Kuzco Gymnasium [Directions] | Cancelled | |||
| Fri., 4/24 | JV Boys Volleyball | Stamford | Away - Stamford HS-Kuzco Gymnasium [Directions] | Cancelled | |||
| Fri., 4/24 | V Softball | Stamford | Away - Stamford HS-SHS Softball Diamond [Directions] | Cancelled | |||
| Fri., 4/24 | JV Softball | Stamford | Away - Cummings Park Field #4-Stamford JV Softball at Cummings Park [Directions] | Cancelled | |||
| Sat., 4/25 | V Boys Lacrosse | Norwalk | Home - Trumbull HS-New Turf Field [Directions] | Cancelled | |||
| Sat., 4/25 | JV Boys Lacrosse | Norwalk | Home - Trumbull HS-New Turf Field [Directions] | Cancelled | |||
| Sat., 4/25 | V Girls Lacrosse | Danbury | Home - Trumbull HS-McDougall Stadium [Directions] | Cancelled | Cancelled | ||
| Sat., 4/25 | JV Girls Lacrosse | Danbury | Home - Trumbull HS-McDougall Stadium [Directions] | Cancelled | |||
| Sat., 4/25 | FR Girls Lacrosse | Danbury | Home - Trumbull HS-The Pit [Directions] | Cancelled | |||
| Sat., 4/25 | Miscellaneous Events | Booth Hill Fathers | Home - Trumbull HS-Gym [Directions] | 5:00 p.m. | |||
| Sun., 4/26 | Miscellaneous Events | Lax Fund Raiser | Home - Trumbull HS-McDougall Stadium [Directions] | 11:00 a.m. | |||
| Mon., 4/27 | V Baseball | New Canaan | Away - Mead Park-Baseball Field [Directions] | Cancelled | |||
| Mon., 4/27 | JV Baseball | New Canaan | Away - New Canaan HS-Coppo Field [Directions] | Cancelled | |||
| Mon., 4/27 | FR Baseball | New Canaan | Home - Trumbull HS-Varsity Baseball Field [Directions] | Cancelled | |||
| Mon., 4/27 | FR Boys Lacrosse | Darien | Home - Trumbull HS-The Pit [Directions] | Cancelled | |||
| Mon., 4/27 | V Boys Outdoor Track | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | Cancelled | |||
| Mon., 4/27 | V Boys Tennis | Norwalk | Away - Norwalk HS-Tennis Courts [Directions] | Cancelled | |||
| Mon., 4/27 | V Boys Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | Cancelled | |||
| Mon., 4/27 | JV Boys Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | Cancelled | |||
| Mon., 4/27 | FR Girls Lacrosse | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | Cancelled | |||
| Mon., 4/27 | V Girls Outdoor Track | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | Cancelled | |||
| Mon., 4/27 | V Softball | New Canaan | Home - Trumbull HS-Varsity Softball Diamond [Directions] | Cancelled | |||
| Mon., 4/27 | JV Softball | New Canaan | Home - Trumbull HS-JV Softball Diamond [Directions] | Cancelled | |||
| Mon., 4/27 | V Girls Tennis | Norwalk | Home - Trumbull HS-Tennis Courts [Directions] | Cancelled | |||
| Tue., 4/28 | V Boys Golf | St. Joseph, TBA, Stamford | Away - Tashua Knolls Golf Course [Directions] | Cancelled | |||
| Tue., 4/28 | V Boys Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | Cancelled | |||
| Tue., 4/28 | JV Boys Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | Cancelled | |||
| Tue., 4/28 | V Boys Tennis | Trinity Catholic | Away - Scalzi Park | Cancelled | |||
| Tue., 4/28 | V Girls Lacrosse | Westhill | Home - Trumbull HS-McDougall Stadium [Directions] | Cancelled | |||
| Tue., 4/28 | JV Girls Lacrosse | Westhill | Home - Trumbull HS-New Turf Field [Directions] | Cancelled | |||
| Tue., 4/28 | V Girls Tennis | Trinity Catholic | Home - Trumbull HS-Tennis Courts [Directions] | Cancelled | |||
| Wed., 4/29 | V Baseball | Westhill | Home - Trumbull HS-Varsity Baseball Field [Directions] | Cancelled | |||
| Wed., 4/29 | JV Baseball | Westhill | Home - Trumbull HS-JV Baseball Field [Directions] | Cancelled | |||
| Wed., 4/29 | FR Baseball | Westhill | Away - Westhill HS-Varsity Baseball Field [Directions] | Cancelled | |||
| Wed., 4/29 | V Boys Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | Cancelled | |||
| Wed., 4/29 | FR Boys Lacrosse | Stamford | Away - Stamford HS-Upper Lacrosse Field [Directions] | Cancelled | |||
| Wed., 4/29 | V Boys Volleyball | St. Joseph | Home - Trumbull HS-THS Main Gym [Directions] | Cancelled | |||
| Wed., 4/29 | JV Boys Volleyball | St. Joseph | Home - Trumbull HS-THS Main Gym [Directions] | Cancelled | |||
| Wed., 4/29 | V Girls Golf | St. Joseph | Away - Tashua Knolls Golf Course [Directions] | Cancelled | |||
| Wed., 4/29 | V Softball | Westhill | Away - Westhill HS-Varsity Softball Field [Directions] | Cancelled | |||
| Wed., 4/29 | JV Softball | Westhill | Away - Roxbury Elementary School-Softball Field [Directions] | Cancelled | |||
| Thu., 4/30 | V Boys Golf | Fairfield Warde | Home - Tashua Knolls Golf Course [Directions] | Cancelled | |||
| Thu., 4/30 | JV Boys Golf | Fairfield Warde | Home - Tashua Knolls Golf Course [Directions] | Cancelled | |||
| Thu., 4/30 | V Boys Tennis | St. Joseph | Away - St. Joseph HS-Tennis Courts [Directions] | Cancelled | |||
| Thu., 4/30 | V Girls Lacrosse | Greenwich | Home - Trumbull HS-McDougall Stadium [Directions] | Cancelled | |||
| Thu., 4/30 | JV Girls Lacrosse | Greenwich | Home - Trumbull HS-New Turf Field [Directions] | Cancelled | |||
| Thu., 4/30 | FR Girls Lacrosse | Greenwich | Home - Trumbull HS-JV Grass Field [Directions] | Cancelled | |||
| Thu., 4/30 | V Girls Tennis | St. Joseph | Home - Trumbull HS-Tennis Courts [Directions] | Cancelled | |||
| Fri., 5/1 | V Baseball | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | Cancelled | |||
| Fri., 5/1 | JV Baseball | Norwalk | Away - City Hall Field [Directions] | Cancelled | |||
| Fri., 5/1 | FR Baseball | Norwalk | Home - Trumbull HS-Varsity Baseball Field [Directions] | Cancelled | |||
| Fri., 5/1 | FR Boys Lacrosse | Wilton | Home - Trumbull HS-The Pit [Directions] | Cancelled | |||
| Fri., 5/1 | V Boys Volleyball | New Canaan | Home - Trumbull HS-THS Main Gym [Directions] | Cancelled | |||
| Fri., 5/1 | JV Boys Volleyball | New Canaan | Home - Trumbull HS-THS Main Gym [Directions] | Cancelled | |||
| Fri., 5/1 | FR Girls Lacrosse | Wilton | Away - Wilton HS-Allen Meadow [Directions] | Cancelled | |||
| Fri., 5/1 | V Softball | Norwalk | Home - Trumbull HS-Varsity Softball Diamond [Directions] | Cancelled | |||
| Fri., 5/1 | JV Softball | Norwalk | Home - Trumbull HS-JV Softball Diamond [Directions] | Cancelled | |||
| Sat., 5/2 | V Girls Lacrosse | South Windsor | Away - South Windsor HS-Multi-purpose field [Directions] | Cancelled | |||
| Sat., 5/2 | JV Girls Lacrosse | South Windsor | Away - South Windsor HS-Multi-purpose field [Directions] | Cancelled | |||
| Mon., 5/4 | V Baseball | Trinity Catholic | Away - Trinity Catholic-Lione | Cancelled | |||
| Mon., 5/4 | V Boys Golf | Darien | Home - Tashua Knolls Golf Course [Directions] | Cancelled | |||
| Mon., 5/4 | JV Boys Golf | Darien | Home - Tashua Knolls Golf Course [Directions] | Cancelled | |||
| Mon., 5/4 | FR Boys Lacrosse | Greenwich | Home - Trumbull HS-The Pit [Directions] | Cancelled | |||
| Mon., 5/4 | V Boys Outdoor Track | Bassick, Norwalk, Harding | Home - Trumbull HS-McDougall Stadium [Directions] | Cancelled | |||
| Mon., 5/4 | V Boys Tennis | Fairfield Warde | Home - Trumbull HS-Tennis Courts [Directions] | Cancelled | |||
| Mon., 5/4 | JV Boys Tennis | Fairfield Warde | Home - Unity Park [Directions] | Cancelled | |||
| Mon., 5/4 | V Boys Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | Cancelled | |||
| Mon., 5/4 | JV Boys Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | Cancelled | |||
| Mon., 5/4 | FR Girls Lacrosse | Greenwich | Away - Cos Cob Park-Benvenuto Field [Directions] | Cancelled | |||
| Mon., 5/4 | V Girls Outdoor Track | Bassick, Norwalk, Harding | Home - Trumbull HS-McDougall Stadium [Directions] | Cancelled | |||
| Mon., 5/4 | V Girls Tennis | Fairfield Warde | Away - Fairfield Warde HS-Blake Courts [Directions] | Cancelled | |||
| Mon., 5/4 | JV Girls Tennis | Fairfield Warde | Away - Fairfield Woods [Directions] | Cancelled | 12:00 PM | ||
| Tue., 5/5 | V Boys Golf | Wilton | Away - Rolling Hills Country Club [Directions] | Cancelled | |||
| Tue., 5/5 | JV Boys Golf | Wilton | Away - Rolling Hills Country Club [Directions] | Cancelled | |||
| Tue., 5/5 | V Boys Lacrosse | Greenwich | Home - Trumbull HS-McDougall Stadium [Directions] | Cancelled | |||
| Tue., 5/5 | JV Boys Lacrosse | Greenwich | Home - Trumbull HS-New Turf Field [Directions] | Cancelled | |||
| Tue., 5/5 | V Boys Tennis | Wilton | Away - Wilton HS-Wilton Varsity Tennis Courts [Directions] | Cancelled | |||
| Tue., 5/5 | JV Boys Tennis | Wilton | Away - Wilton Middlebrook School-JV Tennis Courts [Directions] | Cancelled | |||
| Tue., 5/5 | V Softball | Ridgefield | Away - Ridgefield HS-Varsity Field [Directions] | Cancelled | |||
| Tue., 5/5 | JV Softball | Ridgefield | Away - Ridgefield HS-JV Field [Directions] | Cancelled | |||
| Tue., 5/5 | V Girls Tennis | Wilton | Home - Trumbull HS-Tennis Courts [Directions] | Cancelled | |||
| Tue., 5/5 | JV Girls Tennis | Wilton | Home - Unity Park [Directions] | Cancelled | |||
| Wed., 5/6 | V Baseball | St. Joseph | Away - St. Joseph HS-Baseball Diamond [Directions] | Cancelled | |||
| Wed., 5/6 | JV Baseball | St. Joseph | Away - Unity Park [Directions] | Cancelled | |||
| Wed., 5/6 | FR Baseball | St. Joseph | Home - Trumbull HS-Varsity Baseball Field [Directions] | Cancelled | |||
| Wed., 5/6 | V Boys Volleyball | Ridgefield | Home - Trumbull HS-THS Main Gym [Directions] | Cancelled | |||
| Wed., 5/6 | JV Boys Volleyball | Ridgefield | Home - Trumbull HS-THS Main Gym [Directions] | Cancelled | |||
| Wed., 5/6 | V Girls Golf | Staples | Away - Staples HS-Longshore Golf Course [Directions] | Cancelled | |||
| Wed., 5/6 | JV Girls Golf | Staples | Away - Staples HS-Longshore Golf Course [Directions] | Cancelled | |||
| Wed., 5/6 | V Softball | St. Joseph | Home - Trumbull HS-Varsity Softball Diamond [Directions] | Cancelled | |||
| Wed., 5/6 | JV Softball | St. Joseph | Home - Trumbull HS-JV Softball Diamond [Directions] | Cancelled | |||
| Thu., 5/7 | V Boys Golf | Ridgefield | Away - Silver Spring Golf Course [Directions] | Cancelled | |||
| Thu., 5/7 | JV Boys Golf | Ridgefield | Away - Silver Spring Golf Course [Directions] | Cancelled | |||
| Thu., 5/7 | V Boys Lacrosse | Staples | Away - Staples HS-Staples Stadium [Directions] | Cancelled | |||
| Thu., 5/7 | JV Boys Lacrosse | Staples | Away - Staples HS-Wakeman Field B (turf) [Directions] | Cancelled | |||
| Thu., 5/7 | V Boys Tennis | Danbury | Home - Trumbull HS-Tennis Courts [Directions] | Cancelled | |||
| Thu., 5/7 | V Girls Golf | Ridgefield | Home - Tashua Knolls Golf Course [Directions] | Cancelled | |||
| Thu., 5/7 | JV Girls Golf | Ridgefield | Home - Tashua Knolls Golf Course [Directions] | Cancelled | |||
| Thu., 5/7 | V Girls Lacrosse | Weston | Away - Weston HS-WHS Lower Turf Field [Directions] | Cancelled | |||
| Thu., 5/7 | JV Girls Lacrosse | Weston | Away - Weston HS-WHS Lower Turf Field [Directions] | Cancelled | |||
| Thu., 5/7 | V Girls Tennis | Danbury | Away - Danbury HS-DHS Tennis Courts [Directions] | Cancelled | |||
| Fri., 5/8 | V Baseball | Fairfield Warde | Home - Trumbull HS-Varsity Baseball Field [Directions] | Cancelled | |||
| Fri., 5/8 | JV Baseball | Fairfield Warde | Home - Trumbull HS-JV Baseball Field [Directions] | Cancelled | |||
| Fri., 5/8 | FR Baseball | Fairfield Warde | Away - Fairfield Warde HS-Baseball Diamond [Directions] | Cancelled | |||
| Fri., 5/8 | V Boys Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | Cancelled | |||
| Fri., 5/8 | JV Boys Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | Cancelled | |||
| Fri., 5/8 | V Softball | Fairfield Warde | Away - Fairfield Warde HS-Softball Diamond [Directions] | Cancelled | |||
| Fri., 5/8 | JV Softball | Fairfield Warde | Away - Melville Park [Directions] | Cancelled | |||
| Sat., 5/9 | V Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | Cancelled | |||
| Sat., 5/9 | JV Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | Cancelled | |||
| Sat., 5/9 | V Girls Lacrosse | Staples | Away - Staples HS-Ginny Parker Field [Directions] | Cancelled | |||
| Sat., 5/9 | JV Girls Lacrosse | Staples | Away - Staples HS-Ginny Parker Field [Directions] | Cancelled | |||
| Mon., 5/11 | V Baseball | Wilton | Away - Wilton HS-Varsity Baseball Field [Directions] | Cancelled | |||
| Mon., 5/11 | JV Baseball | Wilton | Away - Wilton HS-JV Baseball Field [Directions] | Cancelled | |||
| Mon., 5/11 | FR Baseball | Wilton | Home - Trumbull HS-Varsity Baseball Field [Directions] | Cancelled | |||
| Mon., 5/11 | V Boys Golf | Norwalk | Home - Tashua Knolls Golf Course [Directions] | Cancelled | |||
| Mon., 5/11 | V Boys Outdoor Track | Danbury | Home - Trumbull HS-McDougall Stadium [Directions] | Cancelled | |||
| Mon., 5/11 | V Boys Tennis | Greenwich | Away - Greenwich HS-Tennis Courts [Directions] | Cancelled | |||
| Mon., 5/11 | V Boys Volleyball | Danbury | Home - Trumbull HS-THS Main Gym [Directions] | Cancelled | |||
| Mon., 5/11 | JV Boys Volleyball | Danbury | Home - Trumbull HS-THS Main Gym [Directions] | Cancelled | |||
| Mon., 5/11 | FR Girls Lacrosse | Fairfield Warde | Home - Trumbull HS-The Pit [Directions] | Cancelled | |||
| Mon., 5/11 | V Girls Outdoor Track | Danbury | Home - Trumbull HS-McDougall Stadium [Directions] | Cancelled | |||
| Mon., 5/11 | V Softball | Wilton | Home - Trumbull HS-Varsity Softball Diamond [Directions] | Cancelled | |||
| Mon., 5/11 | V Girls Tennis | Greenwich | Home - Trumbull HS-Tennis Courts [Directions] | Cancelled | |||
| Tue., 5/12 | V Boys Golf | Danbury | Home - Tashua Knolls Golf Course [Directions] | Cancelled | |||
| Tue., 5/12 | V Boys Lacrosse | Brien McMahon | Home - Trumbull HS-New Turf Field [Directions] | Cancelled | |||
| Tue., 5/12 | JV Boys Lacrosse | Brien McMahon | Home - Trumbull HS-New Turf Field [Directions] | Cancelled | |||
| Tue., 5/12 | FR Boys Lacrosse | New Canaan | Away - New Canaan HS-WTT #1 [Directions] | Cancelled | |||
| Tue., 5/12 | V Boys Tennis | Bridgeport Central | Home - Trumbull HS-Tennis Courts [Directions] | Cancelled | |||
| Tue., 5/12 | JV Boys Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | Cancelled | |||
| Tue., 5/12 | V Girls Lacrosse | Fairfield Warde | Home - Trumbull HS-McDougall Stadium [Directions] | Cancelled | |||
| Tue., 5/12 | JV Girls Lacrosse | Fairfield Warde | Home - Trumbull HS-New Turf Field [Directions] | Cancelled | |||
| Tue., 5/12 | FR Girls Lacrosse | New Canaan | Home - Trumbull HS-JV Grass Field [Directions] | Cancelled | |||
| Tue., 5/12 | JV Softball | Wilton | Home - Trumbull HS-JV Softball Diamond [Directions] | Cancelled | |||
| Tue., 5/12 | V Girls Tennis | Bridgeport Central | Away - Bridgeport Central HS-Central High School Tennis Courts [Directions] | Cancelled | |||
| Tue., 5/12 | JV Girls Tennis | Ridgefield | Home - Unity Park [Directions] | Cancelled | |||
| Wed., 5/13 | V Baseball | Danbury | Home - Trumbull HS-Varsity Baseball Field [Directions] | Cancelled | |||
| Wed., 5/13 | JV Baseball | Danbury | Home - Trumbull HS-JV Baseball Field [Directions] | Cancelled | |||
| Wed., 5/13 | FR Baseball | Danbury | Away - Danbury HS-V Baseball Field [Directions] | Cancelled | |||
| Wed., 5/13 | V Boys Lacrosse | Brien McMahon | Home - Trumbull HS-McDougall Stadium [Directions] | Cancelled | |||
| Wed., 5/13 | JV Boys Lacrosse | Brien McMahon | Home - Trumbull HS-New Turf Field [Directions] | Cancelled | |||
| Wed., 5/13 | V Boys Volleyball | Greenwich | Home - Trumbull HS-THS Main Gym [Directions] | Cancelled | |||
| Wed., 5/13 | JV Boys Volleyball | Greenwich | Home - Trumbull HS-THS Main Gym [Directions] | Cancelled | |||
| Wed., 5/13 | V Girls Golf | Greenwich | Home - Tashua Knolls Golf Course [Directions] | Cancelled | |||
| Wed., 5/13 | JV Girls Golf | Greenwich | Home - Tashua Knolls Golf Course [Directions] | Cancelled | |||
| Wed., 5/13 | V Softball | Danbury | Away - Danbury HS-V Softball field [Directions] | Cancelled | |||
| Wed., 5/13 | JV Softball | Danbury | Away - Danbury HS JV-Softball Diamond [Directions] | Cancelled | |||
| Thu., 5/14 | FR Boys Lacrosse | Stamford | Home - Trumbull HS-The Pit [Directions] | Cancelled | |||
| Thu., 5/14 | V Boys Tennis | Brien McMahon | Away - Brien McMahon HS-Tennis Courts [Directions] | Cancelled | |||
| Thu., 5/14 | V Girls Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | Cancelled | |||
| Thu., 5/14 | JV Girls Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | Cancelled | |||
| Thu., 5/14 | V Girls Tennis | Brien McMahon | Home - Trumbull HS-Tennis Courts [Directions] | Cancelled | |||
| Fri., 5/15 | V Baseball | Greenwich | Away - Greenwich HS-Baseball Field [Directions] | Cancelled | |||
| Fri., 5/15 | JV Baseball | Greenwich | Away - Julian Curtiss School [Directions] | Cancelled | |||
| Fri., 5/15 | FR Baseball | Greenwich | Home - Trumbull HS-Varsity Baseball Field [Directions] | Cancelled | |||
| Fri., 5/15 | V Boys Outdoor Track | Staples | Away - Staples HS-Staples Stadium [Directions] | Cancelled | |||
| Fri., 5/15 | V Boys Volleyball | Fairfield Warde | Home - Trumbull HS-THS Main Gym [Directions] | Cancelled | |||
| Fri., 5/15 | JV Boys Volleyball | Fairfield Warde | Home - Trumbull HS-THS Main Gym [Directions] | Cancelled | |||
| Fri., 5/15 | V Girls Outdoor Track | Staples | Away - Staples HS-Staples Stadium [Directions] | Cancelled | |||
| Fri., 5/15 | V Softball | Greenwich | Home - Trumbull HS-Varsity Softball Diamond [Directions] | Cancelled | Cancelled | ||
| Fri., 5/15 | JV Softball | Greenwich | Home - Trumbull HS-JV Softball Diamond [Directions] | Cancelled | Cancelled | ||
| Sat., 5/16 | V Boys Lacrosse | Cheshire | Away - Cheshire HS-Cheshire High School Main Game field [Directions] | Cancelled | |||
| Sat., 5/16 | JV Boys Lacrosse | Cheshire | Away - Cheshire HS-Grass Fields [Directions] | Cancelled | |||
| Mon., 5/18 | V Baseball | Bridgeport Central | Home - Trumbull HS-Varsity Baseball Field [Directions] | Cancelled | |||
| Mon., 5/18 | JV Baseball | Bridgeport Central | Home - Trumbull HS-JV Baseball Field [Directions] | Cancelled | |||
| Mon., 5/18 | V Boys Golf | Brien McMahon | Away - Oak Hills Golf Course [Directions] | Cancelled | |||
| Mon., 5/18 | FR Boys Lacrosse | Brien McMahon | Home - Trumbull HS-The Pit [Directions] | Cancelled | |||
| Mon., 5/18 | V Boys Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | Cancelled | |||
| Mon., 5/18 | JV Boys Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | Cancelled | |||
| Mon., 5/18 | V Girls Golf | Ridgefield | Away - Ridgefield Golf Course [Directions] | Cancelled | |||
| Mon., 5/18 | JV Girls Golf | Ridgefield | Away - Ridgefield Golf Course [Directions] | Cancelled | |||
| Mon., 5/18 | V Girls Lacrosse | Norwalk | Away - Norwalk HS-Testa Field [Directions] | Cancelled | |||
| Mon., 5/18 | JV Girls Lacrosse | Norwalk | Away - Norwalk HS-Testa Field [Directions] | Cancelled | |||
| Mon., 5/18 | FR Girls Lacrosse | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | Cancelled | |||
| Mon., 5/18 | V Softball | Bridgeport Central | Away - Bridgeport Central HS-Varsity Softball Field [Directions] | Cancelled | |||
| Mon., 5/18 | JV Softball | Bridgeport Central | Away - Cal Ripken Field-Longfellow Park [Directions] | Cancelled | |||
| Tue., 5/19 | V Boys Golf | St. Joseph, Westhill | Away - Tashua Knolls Golf Course [Directions] | Cancelled | |||
| Tue., 5/19 | V Boys Outdoor Track | Greenwich | Home - Trumbull HS-McDougall Stadium [Directions] | Cancelled | |||
| Tue., 5/19 | V Girls Outdoor Track | Greenwich | Home - Trumbull HS-McDougall Stadium [Directions] | Cancelled | |||
| Wed., 5/20 | V Baseball | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | Cancelled | |||
| Wed., 5/20 | JV Baseball | Brien McMahon | Away - Roton MS [Directions] | Cancelled | |||
| Wed., 5/20 | FR Baseball | Brien McMahon | Home - Trumbull HS-Varsity Baseball Field [Directions] | Cancelled | |||
| Wed., 5/20 | V Boys Golf | New Canaan | Away - CCNC [Directions] | Cancelled | |||
| Wed., 5/20 | V Boys Volleyball | Stamford | Home - Trumbull HS-THS Main Gym [Directions] | Cancelled | |||
| Wed., 5/20 | JV Boys Volleyball | Stamford | Home - Trumbull HS-THS Main Gym [Directions] | Cancelled | |||
| Wed., 5/20 | V Girls Golf | Fairfield Warde | Home - Tashua Knolls Golf Course [Directions] | Cancelled | |||
| Wed., 5/20 | JV Girls Golf | Fairfield Warde | Home - Tashua Knolls Golf Course [Directions] | Cancelled | |||
| Wed., 5/20 | V Softball | Brien McMahon | Home - Trumbull HS-Varsity Softball Diamond [Directions] | Cancelled | Cancelled | ||
| Wed., 5/20 | JV Softball | Brien McMahon | Home - Trumbull HS-JV Softball Diamond [Directions] | Cancelled | Cancelled | ||
| Thu., 5/21 | FR Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Fairfield Warde Grass Utility Field [Directions] | Cancelled | |||
| Thu., 5/21 | FR Girls Lacrosse | Fairfield Warde | Home - Trumbull HS-The Pit [Directions] | Cancelled | |||
| Tue., 5/26 | V Boys Outdoor Track | FCIAC Track Championships | Away - SCSU-Jess Dow Field | Cancelled | |||
| Tue., 5/26 | V Girls Golf | New Canaan | Away - CCNC [Directions] | Cancelled | |||
| Tue., 5/26 | V Girls Outdoor Track | FCIAC Track Championships | Away - SCSU-Jess Dow Field | Cancelled | |||
| Wed., 5/27 | V Girls Golf | Danbury | Home - Tashua Knolls Golf Course [Directions] | Cancelled | |||
| Wed., 5/27 | JV Girls Golf | Danbury | Home - Tashua Knolls Golf Course [Directions] | Cancelled | |||