| Trumbull 2023-24 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 947 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Wed., 8/23 | V Football | Brien McMahon (Scrim.) | Home - Trumbull HS-McDougall Stadium [Directions] | 3:30 p.m. | ||
| Thu., 8/24 | V Boys Golf | Ridgefield | Away - Ridgefield Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 8/24 | JV Boys Golf | Ridgefield | Away - Silver Spring Golf Course [Directions] | Canceled | Cancelled | |
| Mon., 8/28 | V Football | New Milford (Scrim.) | Home - Trumbull HS-McDougall Stadium [Directions] | 4:00 p.m. | ||
| Tue., 8/29 | V Boys Golf | Fairfield Ludlowe | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 8/29 | JV Boys Golf | Fairfield Ludlowe | Home - Tashua Knolls Golf Course-Tashua Glen [Directions] | 3:15 p.m. | ||
| Tue., 8/29 | V Boys Soccer | Amity (Scrim.) | Home - Trumbull HS-Cork Field [Directions] | 4:00 p.m. | ||
| Tue., 8/29 | JV Boys Soccer | Amity (Scrim.) | Home - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | ||
| Wed., 8/30 | V Girls Soccer | Shelton (Scrim.) | Home - Trumbull HS-Cork Field [Directions] | 5:30 p.m. | ||
| Wed., 8/30 | JV Girls Soccer | Shelton (Scrim.) | Home - Trumbull HS-JV Grass Field [Directions] | Postponed | ||
| Wed., 8/30 | FR Girls Soccer | Shelton (Scrim.) | Home - Trumbull HS-The Pit [Directions] | Postponed | ||
| Wed., 8/30 | V Girls Volleyball | Newtown, Amity, John Jay (NY) (Scrim.) | Away - Newtown HS-Gym [Directions] | 3:30 p.m. | ||
| Thu., 8/31 | V Football | Darien (Scrim.) | Away - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Thu., 8/31 | FR Football | Darien (Scrim.) | Home - Trumbull HS-Field 14 [Directions] | 4:00 p.m. | ||
| Thu., 8/31 | V Boys Golf | Westhill | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Thu., 8/31 | V Boys Soccer | Shelton (Scrim.) | Home - Trumbull HS-Cork Field [Directions] | 4:00 p.m. | ||
| Thu., 8/31 | JV Boys Soccer | Shelton (Scrim.) | Home - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | ||
| Thu., 8/31 | V Girls Soccer | Amity (Scrim.) | Away - Amity Regional HS-William Johnson Stadium Field [Directions] | 3:45 p.m. | ||
| Thu., 8/31 | JV Girls Soccer | Amity (Scrim.) | Away - Amity Regional HS-AHS Grass Field # 2 [Directions] | 3:45 p.m. | ||
| Thu., 8/31 | V Girls Volleyball | Seymour (Scrim.) | Home - Trumbull HS-THS Main Gym [Directions] | 4:30 p.m. | ||
| Thu., 8/31 | JV Girls Volleyball | Seymour (Scrim.) | Home - Trumbull HS-THS Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 9/1 | V Field Hockey | Shelton (Scrim.) | Away - Shelton HS-Finn Stadium [Directions] | 7:00 p.m. | ||
| Fri., 9/1 | JV Field Hockey | Shelton (Scrim.) | Away - Shelton HS-Finn Stadium [Directions] | 5:30 p.m. | ||
| Sat., 9/2 | V Boys Soccer | Weston (Scrim.) | Home - Trumbull HS-Cork Field [Directions] | 10:00 a.m. | ||
| Sat., 9/2 | JV Boys Soccer | Weston (Scrim.) | Home - Trumbull HS-JV Grass Field [Directions] | 10:00 a.m. | ||
| Sat., 9/2 | V Field Hockey | Fox Lane (NY) (Scrim.) | Home - Trumbull HS-McDougall Stadium [Directions] | 11:00 a.m. | ||
| Sat., 9/2 | JV Field Hockey | Fox Lane (NY) (Scrim.) | Home - Trumbull HS-McDougall Stadium [Directions] | 12:30 p.m. | ||
| Sat., 9/2 | V Girls Volleyball | TBA | Away - Northeast Athletic Center | 9:30 a.m. | ||
| Mon., 9/4 | V Girls Soccer | Joel Barlow (Scrim.) | Away - Joel Barlow HS-Field J (Competition Field) [Directions] | 4:30 p.m. | ||
| Tue., 9/5 | V Boys Golf | Fairfield Warde | Away - Smith Richardson Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 9/5 | JV Boys Golf | Fairfield Warde | Away - Smith Richardson Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 9/6 | V Boys Golf | St. Joseph | Home - Tashua Knolls Golf Course [Directions] | Postponed | ||
| Wed., 9/6 | JV Boys Golf | St. Joseph | Home - Tashua Knolls Golf Course [Directions] | Postponed | ||
| Thu., 9/7 | V Boys Golf | Staples | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Thu., 9/7 | JV Boys Golf | Staples | Home - Tashua Knolls Golf Course-Tashua Glen [Directions] | 3:15 p.m. | ||
| Thu., 9/7 | V Field Hockey | Staples | Home - Trumbull HS-McDougall Stadium [Directions] | 7:00 p.m. | L 2-6 | |
| Thu., 9/7 | JV Field Hockey | Staples | Home - Trumbull HS-McDougall Stadium [Directions] | Postponed | ||
| Thu., 9/7 | FR Field Hockey | Staples | Away - Staples HS-Ginny Parker Field [Directions] | Canceled | Cancelled | |
| Thu., 9/7 | V Girls Soccer | Westhill | Home - Trumbull HS-Cork Field [Directions] | 7:00 p.m. | W 8-0 | |
| Fri., 9/8 | V Football | Hamden | Away - Hamden HS-HHS Turf #1 [Directions] | 6:00 p.m. | L 46-47 (OT) | |
| Fri., 9/8 | V Girls Swimming and Diving | Danbury | Home - University of Bridgeport-Pool [Directions] | 4:00 p.m. | ||
| Fri., 9/8 | V Girls Volleyball | Southington | Away - Southington HS-Gym West [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 9/8 | JV Girls Volleyball | Southington | Away - Southington HS-Gym West [Directions] | 5:00 p.m. | ||
| Fri., 9/8 | FR Girls Volleyball | Southington | Away - Southington HS-Gym East [Directions] | 5:00 p.m. | ||
| Sat., 9/9 | JV Football | Hamden | Home - Trumbull HS-McDougall Stadium [Directions] | 10:30 a.m. | ||
| Sat., 9/9 | FR Football | Hamden | Away - Hamden HS-HHS Turf #1 [Directions] | 10:00 a.m. | ||
| Sat., 9/9 | JV Boys Soccer | Westhill | Away - Westhill HS-Front Turf [Directions] | 10:30 a.m. | ||
| Sat., 9/9 | FR Boys Soccer | Westhill | Home - Trumbull HS-JV Grass Field [Directions] | 11:00 a.m. | ||
| Sat., 9/9 | V Girls Cross Country | Wilton Invitation | Away - Wilton HS | TBA | ||
| Sat., 9/9 | V Field Hockey | Bethel | Home - Trumbull HS-Cork Field [Directions] | 10:00 a.m. | W 7-0 | |
| Sat., 9/9 | JV Field Hockey | Bethel | Home - Trumbull HS-Cork Field [Directions] | 11:30 a.m. | ||
| Sat., 9/9 | V Girls Volleyball | Masuk | Home - Trumbull HS-THS Main Gym [Directions] | 12:00 p.m. | W 3-0 | |
| Sat., 9/9 | JV Girls Volleyball | Masuk | Home - Trumbull HS-THS Main Gym [Directions] | 10:30 a.m. | ||
| Sat., 9/9 | FR Girls Volleyball | Masuk | Home - Trumbull HS-THS Main Gym [Directions] | 9:00 a.m. | ||
| Sun., 9/10 | Miscellaneous Events | Lead the Way Fund Lax Tournament | Home - Trumbull HS-McDougall Stadium [Directions] | 1:00 p.m. | ||
| Mon., 9/11 | JV Boys Soccer | Danbury | Home - Trumbull HS-JV Grass Field [Directions] | Postponed | ||
| Mon., 9/11 | V Field Hockey | Stamford | Home - Trumbull HS-McDougall Stadium [Directions] | 7:00 p.m. | W 3-0 | |
| Mon., 9/11 | JV Field Hockey | Stamford | Home - Trumbull HS-McDougall Stadium [Directions] | 5:30 p.m. | ||
| Mon., 9/11 | JV Girls Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 4:00 p.m. | ||
| Mon., 9/11 | V Girls Volleyball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | 6:00 p.m. | W 3-1 | |
| Mon., 9/11 | JV Girls Volleyball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | 4:30 p.m. | ||
| Mon., 9/11 | FR Girls Volleyball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | 3:30 p.m. | ||
| Tue., 9/12 | V Boys Cross Country | Darien, St. Joseph, Wilton | Home - Trumbull HS-Cross Country Course [Directions] | 4:00 p.m. | ||
| Tue., 9/12 | V Boys Golf | Darien | Away - Wee Burn CC [Directions] | 3:00 p.m. | ||
| Tue., 9/12 | V Boys Soccer | Danbury | Home - Trumbull HS-Cork Field [Directions] | 5:30 p.m. | T 1-1 | |
| Tue., 9/12 | FR Boys Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 4:00 p.m. | ||
| Tue., 9/12 | V Girls Cross Country | Darien, St. Joseph, Wilton | Home - Trumbull HS-Cross Country Course [Directions] | 4:15 p.m. | ||
| Wed., 9/13 | V Girls Soccer | Fairfield Warde | Home - Trumbull HS-Cork Field [Directions] | 5:30 p.m. | W 3-1 | |
| Wed., 9/13 | FR Girls Soccer | Fairfield Warde | Away - Tunxis [Directions] | 4:00 p.m. | ||
| Wed., 9/13 | V Girls Swimming and Diving | Westhill/Stamford | Away - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Wed., 9/13 | V Girls Volleyball | Bristol Eastern | Away - Bristol Eastern HS-Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Wed., 9/13 | JV Girls Volleyball | Bristol Eastern | Away - Bristol Eastern HS-Gym [Directions] | 5:00 p.m. | ||
| Wed., 9/13 | FR Girls Volleyball | Bristol Eastern | Away - Bristol Eastern HS-Gym 2 [Directions] | 5:00 p.m. | ||
| Thu., 9/14 | V Football | Danbury | Home - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | W 28-20 | |
| Thu., 9/14 | FR Football | Staples | Home - Trumbull HS-Cork Field [Directions] | 3:30 p.m. | ||
| Thu., 9/14 | V Boys Golf | St. Joseph | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Thu., 9/14 | JV Boys Golf | St. Joseph | Home - Tashua Knolls Golf Course-Tashua Glen [Directions] | 3:15 p.m. | ||
| Thu., 9/14 | V Boys Soccer | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 5:30 p.m. | W 1-0 | |
| Thu., 9/14 | JV Boys Soccer | Fairfield Warde | Away - Fairfield Warde HS-Grass Utility Field [Directions] | 4:00 p.m. | ||
| Thu., 9/14 | FR Boys Soccer | Fairfield Warde | Home - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | ||
| Thu., 9/14 | V Girls Volleyball | RHAM | Away - RHAM HS-Gym [Directions] | 5:00 p.m. | W 3-2 | |
| Thu., 9/14 | JV Girls Volleyball | RHAM | Away - RHAM HS-Gym [Directions] | Canceled | Cancelled | |
| Fri., 9/15 | JV Football | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 3:30 p.m. | ||
| Fri., 9/15 | V Field Hockey | Newtown | Away - Treadwell Park-Newtown Treadwell Park [Directions] | 4:00 p.m. | W 1-0 | |
| Fri., 9/15 | JV Girls Soccer | Fairfield Warde | Home - Trumbull HS-JV Grass Field [Directions] | Postponed | ||
| Mon., 9/18 | V Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 4:00 p.m. | L 0-2 | |
| Mon., 9/18 | JV Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 5:45 p.m. | ||
| Mon., 9/18 | V Girls Soccer | Brien McMahon | Home - Trumbull HS-Cork Field [Directions] | 5:45 p.m. | T 2-2 | |
| Mon., 9/18 | JV Girls Soccer | Brien McMahon | Home - Trumbull HS-JV Grass Field [Directions] | 3:45 p.m. | ||
| Tue., 9/19 | V Boys Cross Country | Bridgeport Central, Ridgefield, Stamford | Home - Trumbull HS-Cross Country Course [Directions] | 4:00 p.m. | ||
| Tue., 9/19 | V Girls Cross Country | Bridgeport Central, Ridgefield, Stamford | Home - Trumbull HS-Cross Country Course [Directions] | 4:00 p.m. | ||
| Tue., 9/19 | V Field Hockey | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 4:00 p.m. | L 0-4 | |
| Tue., 9/19 | JV Field Hockey | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 5:30 p.m. | ||
| Tue., 9/19 | FR Field Hockey | Ridgefield | Away - Scotts Ridge MS-SRMS Turf [Directions] | Canceled | Cancelled | |
| Wed., 9/20 | FR Boys Soccer | Brien McMahon | Home - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | ||
| Wed., 9/20 | V Girls Soccer | Wilton | Away - Wilton HS-Lilly Field [Directions] | 6:30 p.m. | W 1-0 | |
| Wed., 9/20 | JV Girls Soccer | Wilton | Away - Allen's Meadow-Field 2 [Directions] | 4:15 p.m. | ||
| Wed., 9/20 | FR Girls Soccer | Wilton | Home - Trumbull HS-JV Grass Field [Directions] | 5:00 p.m. | ||
| Thu., 9/21 | FR Football | Newtown | Away - Treadwell Park-Newtown Treadwell Park [Directions] | 4:00 p.m. | ||
| Thu., 9/21 | V Boys Golf | Stamford | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Thu., 9/21 | V Boys Soccer | Wilton | Home - Trumbull HS-Cork Field [Directions] | 4:00 p.m. | W 3-1 | |
| Thu., 9/21 | JV Boys Soccer | Wilton | Home - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Thu., 9/21 | FR Boys Soccer | Wilton | Away - Allen's Meadow-Field 2 [Directions] | 4:30 p.m. | ||
| Thu., 9/21 | V Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | L 0-4 | |
| Thu., 9/21 | JV Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 5:30 p.m. | ||
| Fri., 9/22 | V Football | Newtown | Home - Trumbull HS-McDougall Stadium [Directions] | 7:00 p.m. | L 14-21 | |
| Fri., 9/22 | V Girls Soccer | Bridgeport Central | Away - Bridgeport Central-Kennedy Stadium Turf [Directions] | 4:00 p.m. | W 7-0 | |
| Fri., 9/22 | FR Girls Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | 4:00 p.m. | ||
| Fri., 9/22 | V Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 6:00 p.m. | W 3-2 | |
| Fri., 9/22 | JV Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:30 p.m. | ||
| Sat., 9/23 | JV Football | Newtown | Home - Trumbull HS-McDougall Stadium [Directions] | 10:30 a.m. | ||
| Sat., 9/23 | V Boys Soccer | Bridgeport Central | Home - Trumbull HS-Cork Field [Directions] | 12:00 p.m. | W 3-0 | |
| Sat., 9/23 | JV Boys Soccer | Bridgeport Central | Home - Trumbull HS-Cork Field [Directions] | 10:00 a.m. | ||
| Sat., 9/23 | FR Girls Soccer | Danbury | Home - Trumbull HS-McDougall Stadium [Directions] | 1:00 p.m. | ||
| Sat., 9/23 | V Girls Swimming and Diving | St. Joseph | Away - FLOOD MS [Directions] | 2:00 p.m. | ||
| Sat., 9/23 | FR Girls Volleyball | Westhill | Home - Trumbull HS-THS Main Gym [Directions] | Postponed | ||
| Tue., 9/26 | V Boys Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | 3:30 p.m. | ||
| Tue., 9/26 | V Boys Soccer | Westhill | Away - Westhill HS-Westhill Front Turf Field [Directions] | 4:00 p.m. | W 3-0 | |
| Tue., 9/26 | V Field Hockey | Fairfield Warde | Home - Trumbull HS-McDougall Stadium [Directions] | 7:00 p.m. | W 4-1 | |
| Tue., 9/26 | JV Field Hockey | Fairfield Warde | Home - Trumbull HS-McDougall Stadium [Directions] | 5:30 p.m. | ||
| Tue., 9/26 | FR Field Hockey | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | Canceled | Cancelled | |
| Wed., 9/27 | V Boys Cross Country | New Canaan, Staples, Westhill | Away - Waveny Park [Directions] | 4:00 p.m. | ||
| Wed., 9/27 | V Girls Cross Country | New Canaan, Staples, Westhill | Away - Waveny Park [Directions] | 4:00 p.m. | ||
| Wed., 9/27 | V Girls Soccer | Darien | Home - Trumbull HS-Cork Field [Directions] | 5:30 p.m. | W 4-1 | |
| Wed., 9/27 | JV Girls Soccer | Darien | Home - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | ||
| Wed., 9/27 | FR Girls Soccer | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 9/27 | V Girls Swimming and Diving | Fairfield Warde | Home - University of Bridgeport-Pool [Directions] | 4:00 p.m. | ||
| Wed., 9/27 | V Girls Volleyball | Danbury | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 9/27 | JV Girls Volleyball | Danbury | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 9/28 | FR Football | Darien | Away - Royle School Field [Directions] | 4:00 p.m. | ||
| Thu., 9/28 | V Boys Golf | Norwalk | Away - Oak Hills Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 9/28 | V Boys Soccer | Darien | Away - Darien HS-[CIAC] Willow Brook Park [Directions] | 4:00 p.m. | W 2-0 | |
| Thu., 9/28 | JV Boys Soccer | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 9/28 | FR Boys Soccer | Darien | Home - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | ||
| Thu., 9/28 | V Field Hockey | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 6:30 p.m. | W 3-2 | |
| Thu., 9/28 | JV Field Hockey | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 5:00 p.m. | ||
| Thu., 9/28 | FR Girls Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 5:00 p.m. | ||
| Fri., 9/29 | V Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Fri., 9/29 | JV Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:30 p.m. | ||
| Fri., 9/29 | FR Girls Volleyball | Fairfield Warde | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/30 | V Football | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 2:00 p.m. | W 42-21 | |
| Sat., 9/30 | V Boys Soccer | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 2:15 p.m. | L 2-3 | |
| Sat., 9/30 | JV Boys Soccer | Greenwich | Away - Greenwich HS-Field 3 [Directions] | 12:30 p.m. | ||
| Sat., 9/30 | FR Boys Soccer | Greenwich | Home - Trumbull HS-McDougall Stadium [Directions] | 11:30 a.m. | ||
| Sat., 9/30 | V Girls Cross Country | Festival of Champions - Belfast Maine | Away - Troy Howard MS | TBA | ||
| Sat., 9/30 | FR Field Hockey | Norwalk | Home - Trumbull HS-Cork Field [Directions] | 9:30 a.m. | ||
| Sat., 9/30 | V Girls Soccer | Greenwich | Home - Trumbull HS-Cork Field [Directions] | 11:30 a.m. | T 2-2 | |
| Sat., 9/30 | JV Girls Soccer | Greenwich | Home - Trumbull HS-Cork Field [Directions] | 1:30 p.m. | ||
| Mon., 10/2 | V Boys Cross Country | Fairfield Ludlowe, Brien McMahon, Fairfield Warde | Away - Hoyden's Hill Open Space-Cross Country Course [Directions] | 4:00 p.m. | ||
| Mon., 10/2 | JV Football | Ridgefield | Home - Trumbull HS-McDougall Stadium [Directions] | 4:00 p.m. | ||
| Mon., 10/2 | V Girls Cross Country | Fairfield Ludlowe, Brien McMahon, Fairfield Warde | Away - Hoyden's Hill Open Space-Cross Country Course [Directions] | 4:00 p.m. | ||
| Mon., 10/2 | V Field Hockey | Wilton | Away - Wilton HS-Fuijitani Field -Turf [Directions] | 6:30 p.m. | L 1-8 | |
| Mon., 10/2 | JV Field Hockey | Wilton | Away - Wilton HS-Fuijitani Field -Turf [Directions] | 5:00 p.m. | ||
| Tue., 10/3 | V Boys Golf | Danbury | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 10/3 | JV Boys Golf | Danbury | Home - Tashua Knolls Golf Course-Tashua Glen [Directions] | 3:15 p.m. | ||
| Tue., 10/3 | V Girls Soccer | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 4:00 p.m. | L 6-0 | |
| Tue., 10/3 | JV Girls Soccer | St. Joseph | Home - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | ||
| Tue., 10/3 | V Girls Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:00 p.m. | W 3-0 | |
| Tue., 10/3 | JV Girls Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 10/3 | FR Girls Volleyball | Brien McMahon | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/4 | V Boys Golf | Wilton | Away - Rolling Hills Country Club [Directions] | 3:30 p.m. | ||
| Wed., 10/4 | JV Boys Golf | Wilton | Away - Rolling Hills Country Club [Directions] | 3:30 p.m. | ||
| Wed., 10/4 | V Boys Soccer | St. Joseph | Home - Trumbull HS-Cork Field [Directions] | 5:30 p.m. | W 7-0 | |
| Wed., 10/4 | FR Girls Soccer | Greenwich | Away - Eastern MS [Directions] | 4:30 p.m. | ||
| Wed., 10/4 | FR Girls Volleyball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Thu., 10/5 | V Field Hockey | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 5:00 p.m. | W 4-0 | |
| Thu., 10/5 | JV Field Hockey | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 6:30 p.m. | ||
| Thu., 10/5 | V Girls Soccer | Stamford | Home - Trumbull HS-Cork Field [Directions] | 5:30 p.m. | T 0-0 | |
| Thu., 10/5 | JV Girls Soccer | Stamford | Home - Trumbull HS-JV Grass Field [Directions] | 4:30 p.m. | ||
| Thu., 10/5 | V Girls Swimming and Diving | Greenwich | Home - University of Bridgeport-Pool [Directions] | 4:00 p.m. | ||
| Thu., 10/5 | V Girls Volleyball | Wilton | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Thu., 10/5 | JV Girls Volleyball | Wilton | Home - Trumbull HS-THS Main Gym [Directions] | 4:30 p.m. | ||
| Fri., 10/6 | V Boys Soccer | Stamford | Home - Trumbull HS-Cork Field [Directions] | 5:30 p.m. | W 2-1 | |
| Fri., 10/6 | JV Boys Soccer | Stamford | Home - Trumbull HS-JV Grass Field [Directions] | 4:30 p.m. | ||
| Fri., 10/6 | FR Boys Soccer | Stamford | Away - Rippowam MS-Upper Soccer/Footballl Field [Directions] | 4:00 p.m. | ||
| Fri., 10/6 | V Girls Volleyball | Bridgeport Central | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 10/6 | JV Girls Volleyball | Bridgeport Central | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/7 | V Boys Cross Country | Wickham Invitational - RI | Away - Wickham Park | TBA | ||
| Sat., 10/7 | V Girls Cross Country | Wickham Invitational | Away - Wickham Park | TBA | ||
| Sat., 10/7 | FR Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 10:00 a.m. | ||
| Sat., 10/7 | V Girls Soccer | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 5:00 p.m. | W 6-0 | |
| Sat., 10/7 | Miscellaneous Events | Rugby Clinic | Home - Trumbull HS-McDougall Stadium [Directions] | 1:00 p.m. | ||
| Mon., 10/9 | V Girls Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 6:00 p.m. | W 5-2 | |
| Mon., 10/9 | JV Girls Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | Canceled | Cancelled | |
| Mon., 10/9 | V Girls Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Mon., 10/9 | JV Girls Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/10 | V Boys Cross Country | Greenwich, Danbury, Norwalk | Away - Greenwich Point [Directions] | 4:00 p.m. | ||
| Tue., 10/10 | V Boys Golf | Brien McMahon | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 10/10 | V Boys Soccer | Norwalk | Home - Trumbull HS-Cork Field [Directions] | 5:30 p.m. | W 3-1 | |
| Tue., 10/10 | JV Boys Soccer | Norwalk | Home - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | ||
| Tue., 10/10 | FR Boys Soccer | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 4:00 p.m. | ||
| Tue., 10/10 | V Girls Cross Country | Greenwich, Danbury, Norwalk | Away - Greenwich Point [Directions] | 4:00 p.m. | ||
| Tue., 10/10 | V Field Hockey | Westhill | Home - Trumbull HS-McDougall Stadium [Directions] | 7:00 p.m. | W 3-1 | |
| Tue., 10/10 | JV Field Hockey | Westhill | Home - Trumbull HS-McDougall Stadium [Directions] | 5:30 p.m. | ||
| Tue., 10/10 | FR Field Hockey | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | Canceled | Cancelled | |
| Tue., 10/10 | FR Girls Volleyball | Darien | Home - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | ||
| Wed., 10/11 | V Boys Golf | Fairfield Prep | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Wed., 10/11 | JV Boys Golf | Fairfield Prep | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Wed., 10/11 | V Girls Swimming and Diving | Norwalk/McMahon | Home - University of Bridgeport-Pool [Directions] | 4:00 p.m. | ||
| Wed., 10/11 | V Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | W 3-1 | |
| Wed., 10/11 | JV Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 10/11 | FR Girls Volleyball | Greenwich | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/12 | FR Football | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 7:00 p.m. | ||
| Thu., 10/12 | V Boys Golf | New Canaan | Away - CCNC [Directions] | 3:30 p.m. | ||
| Thu., 10/12 | JV Boys Golf | New Canaan | Away - CCNC [Directions] | 3:30 p.m. | ||
| Thu., 10/12 | V Field Hockey | Greenwich | Home - Trumbull HS-McDougall Stadium [Directions] | 7:00 p.m. | L 0-9 | |
| Thu., 10/12 | JV Field Hockey | Greenwich | Home - Trumbull HS-McDougall Stadium [Directions] | 5:30 p.m. | ||
| Thu., 10/12 | FR Field Hockey | Greenwich | Away - Cos Cob Park, Benvenuto Field-Benvenuto Field [Directions] | Canceled | Cancelled | |
| Thu., 10/12 | V Girls Soccer | Staples | Home - Trumbull HS-Cork Field [Directions] | 5:30 p.m. | L 2-1 | |
| Thu., 10/12 | JV Girls Soccer | Staples | Home - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | ||
| Thu., 10/12 | FR Girls Soccer | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Fri., 10/13 | V Football | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 6:00 p.m. | W 35-13 | |
| Fri., 10/13 | FR Boys Soccer | Staples | Home - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | ||
| Fri., 10/13 | V Girls Swimming and Diving | Wilton | Home - University of Bridgeport-Pool [Directions] | 4:00 p.m. | ||
| Fri., 10/13 | V Girls Volleyball | St. Joseph | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | W 3-1 | |
| Fri., 10/13 | JV Girls Volleyball | St. Joseph | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/13 | FR Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/14 | JV Football | Fairfield Warde | Home - Trumbull HS-McDougall Stadium [Directions] | 10:30 a.m. | ||
| Sat., 10/14 | V Boys Soccer | Staples | Away - Staples HS-Wakeman Field B (turf) [Directions] | 10:30 a.m. | L 0-1 | |
| Sat., 10/14 | JV Boys Soccer | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | 10:30 a.m. | ||
| Sat., 10/14 | V Field Hockey | Danbury | Home - Trumbull HS-Cork Field [Directions] | 10:30 a.m. | W 3-0 | |
| Sat., 10/14 | JV Field Hockey | Danbury | Home - Trumbull HS-Cork Field [Directions] | 12:00 p.m. | ||
| Sat., 10/14 | FR Field Hockey | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | Canceled | Cancelled | |
| Mon., 10/16 | V Girls Soccer | Ridgefield | Home - Trumbull HS-Cork Field [Directions] | 5:30 p.m. | L 1-0 | |
| Mon., 10/16 | JV Girls Soccer | Ridgefield | Home - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Mon., 10/16 | FR Girls Soccer | Ridgefield | Away - Ridgefield HS-RHS Lower Grass Field [Directions] | 4:30 p.m. | ||
| Mon., 10/16 | V Girls Volleyball | Stamford | Home - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Mon., 10/16 | JV Girls Volleyball | Stamford | Home - Trumbull HS-THS Main Gym [Directions] | 4:30 p.m. | ||
| Mon., 10/16 | FR Girls Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 10/17 | V Boys Soccer | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 7:00 p.m. | W 3-0 | |
| Tue., 10/17 | JV Boys Soccer | Ridgefield | Away - Ridgefield HS-RHS Lower Grass Field [Directions] | 4:00 p.m. | ||
| Tue., 10/17 | FR Boys Soccer | Ridgefield | Home - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Wed., 10/18 | V Boys Cross Country | FCIAC Championship | Away - Waveny Park | 2:15 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Not Listed-Waveny Park | ||||||
| Wed., 10/18 | FR Football | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 5:30 p.m. | ||
| Wed., 10/18 | V Girls Cross Country | FCIAC Championship | Away - Waveny Park | 2:15 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Not Listed-Waveny Park | ||||||
| Wed., 10/18 | V Field Hockey | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | L 2-10 | |
| Wed., 10/18 | JV Field Hockey | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Wed., 10/18 | FR Field Hockey | Darien | Home - Trumbull HS-McDougall Stadium [Directions] | Canceled | Cancelled | |
| Wed., 10/18 | V Girls Soccer | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 7:00 p.m. | T 1-1 | |
| Wed., 10/18 | JV Girls Soccer | New Canaan | Away - Saxe MS-Field 1 [Directions] | 4:00 p.m. | ||
| Wed., 10/18 | FR Girls Soccer | New Canaan | Home - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Wed., 10/18 | V Girls Volleyball | Norwalk | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 10/18 | JV Girls Volleyball | Norwalk | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/18 | FR Girls Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:30 p.m. | ||
| Thu., 10/19 | V Boys Golf | FCIAC's | Away - Fairchild Wheeler Golf Course | TBA | ||
| Thu., 10/19 | V Boys Soccer | New Canaan | Home - Trumbull HS-Cork Field [Directions] | 5:30 p.m. | W 3-0 | |
| Thu., 10/19 | JV Boys Soccer | New Canaan | Home - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Thu., 10/19 | FR Boys Soccer | New Canaan | Away - Saxe MS-Field 1 [Directions] | 4:00 p.m. | ||
| Thu., 10/19 | V Girls Swimming and Diving | Fairfield Ludlowe | Away - Fairfield University-Pool [Directions] | 4:00 p.m. | ||
| Thu., 10/19 | V Girls Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 5:30 p.m. | W 3-1 | |
| Thu., 10/19 | JV Girls Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/19 | FR Girls Volleyball | Staples | Home - Trumbull HS-THS Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 10/20 | V Football | Greenwich | Home - Trumbull HS-McDougall Stadium [Directions] | 7:00 p.m. | L 0-42 | |
| Sat., 10/21 | JV Football | Greenwich | Away - Greenwich HS-Field 7 [Directions] | 10:00 a.m. | ||
| Sat., 10/21 | V Boys Soccer | Glastonbury | Home - Trumbull HS-Cork Field [Directions] | 2:00 p.m. | L 0-1 | |
| Sat., 10/21 | V Field Hockey | St. Joseph | Home - Trumbull HS-McDougall Stadium [Directions] | 11:00 a.m. | W 5-0 | |
| Sat., 10/21 | JV Field Hockey | St. Joseph | Home - Trumbull HS-McDougall Stadium [Directions] | 9:30 a.m. | ||
| Sat., 10/21 | JV Girls Soccer | Westhill | Home - Trumbull HS-Cork Field [Directions] | 11:00 a.m. | ||
| Sat., 10/21 | FR Girls Soccer | New Canaan, Staples | Away - Conner Field, New Cannan [Directions] | Postponed | ||
| Mon., 10/23 | V Field Hockey | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 5:30 p.m. | L 1-2 | |
| Mon., 10/23 | JV Field Hockey | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Mon., 10/23 | FR Field Hockey | New Canaan | Home - Trumbull HS-McDougall Stadium [Directions] | Canceled | Cancelled | |
| Mon., 10/23 | V Girls Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 7:00 p.m. | L 1-0 | |
| Mon., 10/23 | JV Girls Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | 4:00 p.m. | ||
| Mon., 10/23 | FR Girls Soccer | Fairfield Ludlowe | Home - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Mon., 10/23 | V Girls Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Mon., 10/23 | JV Girls Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 10/23 | FR Girls Volleyball | Ridgefield | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/24 | V Boys Golf | CIAC Division I Fall Championship | Away - Stanley GC | 8:30 a.m. | ||
| Tue., 10/24 | V Boys Soccer | Fairfield Ludlowe | Home - Trumbull HS-Cork Field [Directions] | 5:30 p.m. | L 1-4 | |
| Tue., 10/24 | JV Boys Soccer | Fairfield Ludlowe | Home - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | ||
| Tue., 10/24 | FR Boys Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | 4:00 p.m. | ||
| Wed., 10/25 | V Girls Swimming and Diving | Staples | Away - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Wed., 10/25 | V Girls Volleyball | New Canaan | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 10/25 | JV Girls Volleyball | New Canaan | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/25 | FR Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/26 | FR Boys Cross Country | Hatter Freshman Invitational | Away - Danbury HS | 4:00 p.m. | ||
| Thu., 10/26 | FR Boys Cross Country | Hatter Freshman Invitational | Away - Danbury HS | 4:00 p.m. | ||
| Thu., 10/26 | FR Football | Ridgefield | Home - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | ||
| Thu., 10/26 | V Girls Cross Country | Hatter Freshman Invitational | Away - Danbury HS | 4:00 p.m. | ||
| Thu., 10/26 | V Girls Soccer | Staples | Away - Staples HS-Wakeman Field B (turf) [Directions] | 3:30 p.m. | L 4-2 | |
| Fri., 10/27 | V Boys Soccer | Brien McMahon | Home - Trumbull HS-Cork Field [Directions] | 5:00 p.m. | W 1-0 | |
| Fri., 10/27 | V Girls Volleyball | Fairfield Ludlowe | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 10/27 | JV Girls Volleyball | Fairfield Ludlowe | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/27 | FR Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/28 | V Football | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 1:00 p.m. | L 14-34 | |
| Sat., 10/28 | FR Girls Soccer | New Canaan | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 10:00 a.m. | ||
| Sat., 10/28 | JV Girls Swimming and Diving | Greenwich, Danbury, Darien, Fairfield Ludlowe, New Canaan, Norwalk/McMahon, Ridgefield, St. Joseph, Staples, Westhill/Stamford, Wilton | Away - Greenwich HS-Pool | 9:30 a.m. | ||
| Sat., 10/28 | JV Girls Volleyball | Fairfield Warde, Brien McMahon, Darien, Fairfield Ludlowe, Greenwich Country Day, Greenwich, Shelton, Stamford, Weston | Away - Fairfield Warde HS-Large Gym | 9:00 a.m. | ||
| Mon., 10/30 | JV Football | Stamford | Home - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | ||
| Mon., 10/30 | V Boys Soccer | Greenwich | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 7:00 p.m. | W 5-4 | |
| Mon., 10/30 | V Girls Volleyball | Greenwich | Home - Trumbull HS-THS Main Gym [Directions] | 5:00 p.m. | W 3-1 | |
| Tue., 10/31 | V Boys Cross Country | CIAC Class LL Championship | Away - Wickham Park | 3:15 p.m. | ||
| Tue., 10/31 | V Girls Cross Country | CIAC Class LL Championship | Away - Wickham Park | 2:30 p.m. | ||
| Wed., 11/1 | V Girls Soccer | Rye Country Day (NY) (Scrim.) | Away - Rye Country Day School | 4:00 p.m. | ||
| Wed., 11/1 | V Girls Swimming and Diving | Greenwich, Danbury, Darien, Fairfield Ludlowe, Fairfield Warde, New Canaan, Norwalk/McMahon, Ridgefield, St. Joseph, Staples, Westhill/Stamford, Wilton | Away - Greenwich HS-Pool | 5:30 p.m. | ||
| Thu., 11/2 | FR Football | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Thu., 11/2 | V Boys Soccer | Stamford | Home - Norwalk HS-Testa Field [Directions] | 7:00 p.m. | W 3-2 (OT) | |
| Thu., 11/2 | V Field Hockey | Lauralton Hall (Scrim.) | Away - Lauralton Hall-Turf Field [Directions] | 3:15 p.m. | ||
| Thu., 11/2 | V Girls Volleyball | Fairfield Warde | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 7:00 p.m. | W 3-0 | |
| Fri., 11/3 | V Football | Staples | Away - Staples HS-Staples Stadium [Directions] | 7:00 p.m. | L 18-35 | |
| Sat., 11/4 | JV Football | Staples | Home - Trumbull HS-McDougall Stadium [Directions] | 10:30 a.m. | ||
| Sat., 11/4 | V Girls Swimming and Diving | Greenwich, Danbury, Darien, Fairfield Ludlowe, Fairfield Warde, New Canaan, Norwalk/McMahon, Ridgefield, St. Joseph, Staples, Westhill/Stamford, Wilton | Away - Greenwich HS-Pool | 3:30 p.m. | ||
| Sat., 11/4 | V Girls Volleyball | Darien | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 3:30 p.m. | ||
| Mon., 11/6 | V Boys Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Mon., 11/6 | V Girls Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Mon., 11/6 | V Girls Soccer | Enfield | Home - Trumbull HS-Cork Field [Directions] | 2:00 p.m. | W 1-0 | |
| Tue., 11/7 | V Boys Soccer | Fairfield Warde | Home - Trumbull HS-Cork Field [Directions] | 5:00 p.m. | W 2-0 | |
| Wed., 11/8 | V Field Hockey | Glastonbury | Away - Glastonbury HS-Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 11/8 | V Girls Soccer | Norwich Free Academy | Away - Norwich Free Academy-Turf Field [Directions] | 6:00 p.m. | L 3-1 | |
| Wed., 11/8 | Miscellaneous Events | Underage Drinking Forum | Home - Trumbull HS-Gym [Directions] | 6:00 p.m. | ||
| Thu., 11/9 | FR Football | St. Joseph | Home - Trumbull HS-McDougall Stadium [Directions] | 5:30 p.m. | ||
| Thu., 11/9 | V Boys Soccer | Glastonbury | Away - Glastonbury HS-Turf Field [Directions] | 2:00 p.m. | L 2-3 (OT) | |
| Thu., 11/9 | V Girls Swimming and Diving | CIAC Class LL Diving Championship | Away - Sheehan | 5:30 p.m. | ||
| Thu., 11/9 | V Girls Volleyball | Naugatuck | Home - Trumbull HS-THS Main Gym [Directions] | 5:00 p.m. | ||
| Fri., 11/10 | V Football | Westhill | Home - Trumbull HS-McDougall Stadium [Directions] | 7:00 p.m. | W 49-14 | |
| Sat., 11/11 | JV Football | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | Canceled | Cancelled | |
| Sat., 11/11 | V Girls Cross Country | New England Championship - ME | Away - Troy Howard MS | TBA | ||
| Sat., 11/11 | V Girls Swimming and Diving | CIAC Class LL Qualifying Meet | Away - Cornerstone Pool | 4:30 p.m. | ||
| Sat., 11/11 | V Girls Volleyball | Fairfield Warde | Home - Trumbull HS-THS Main Gym [Directions] | 12:00 p.m. | ||
| Tue., 11/14 | V Girls Swimming and Diving | CIAC Class LL Finals | Away - Wesleyan | 6:00 p.m. | ||
| Wed., 11/15 | V Girls Volleyball | Darien | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 6:00 p.m. | ||
| Thu., 11/16 | V Girls Swimming and Diving | CIAC State Open Diving | Away - Middletown | 5:30 p.m. | ||
| Sat., 11/18 | JV Football | St. Joseph | Home - Trumbull HS-McDougall Stadium [Directions] | 10:00 a.m. | ||
| Sun., 11/19 | V Girls Swimming and Diving | CIAC State Open Swimming | Away - Yale | 1:00 p.m. | ||
| Mon., 11/20 | Miscellaneous Events | Powder Puff | Home - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | ||
| Tue., 11/21 | Miscellaneous Events | CEU | Home - Trumbull HS-Gym [Directions] | 5:00 p.m. | ||
| Thu., 11/23 | V Football | St. Joseph | Home - Trumbull HS-McDougall Stadium [Directions] | 10:00 a.m. | L 7-16 | |
| Tue., 11/28 | V Football | CIAC Quarterfinals | Away - Higher Seed | 6:30 p.m. | ||
| Sat., 12/2 | V Boys Ice Hockey | Lyman Hall (Scrim.) | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 12:45 p.m. | ||
| Sat., 12/2 | V Girls Basketball | Daniel Hand (Scrim.) | Away - Daniel Hand HS-DHHS Gym [Directions] | 11:00 a.m. | ||
| Sun., 12/3 | V Football | CIAC Semifinals | Away - Higher Seed | 12:30 p.m. | ||
| Tue., 12/5 | V Girls Ice Hockey | West Haven/SHA | Away - West Haven HS-Bennett Rink [Directions] | 5:30 p.m. | W 5-4 | |
| Wed., 12/6 | V Boys Basketball | Bassick (Scrim.) | Home - Trumbull HS-THS Main Gym [Directions] | 3:15 p.m. | ||
| Wed., 12/6 | V Boys Ice Hockey | Newington Coop (Scrim.) | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 8:30 p.m. | ||
| Wed., 12/6 | V Girls Basketball | Newtown (Scrim.) | Away - Newtown HS-Gym [Directions] | 5:30 p.m. | ||
| Fri., 12/8 | V Boys Basketball | Shelton (Scrim.) | Home - Newtown HS-Gym [Directions] | 4:00 p.m. | ||
| Fri., 12/8 | V Girls Basketball | Sacred Heart Academy (Scrim.) | Away - Sacred Heart Academy-Gym [Directions] | 4:45 p.m. | Cancelled | |
| Sat., 12/9 | V Football | CIAC Championship Games | Away - Site TBA | TBA | ||
| Sat., 12/9 | V Girls Ice Hockey | Greenwich | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 2:00 p.m. | W 7-1 | |
| Tue., 12/12 | V Boys Basketball | Fairfield Prep (Scrim.) | Away - Fairfield University-Leo D. Mahoney Arena [Directions] | 5:00 p.m. | ||
| Tue., 12/12 | FR Boys Basketball | Fairfield Prep (Scrim.) | Away - Fairfield University-Leo D. Mahoney Arena [Directions] | 3:30 p.m. | ||
| Tue., 12/12 | V Girls Basketball | New Milford | Home - Trumbull HS-THS Main Gym [Directions] | 6:30 p.m. | W 52-41 | |
| Tue., 12/12 | JV Girls Basketball | New Milford | Home - Trumbull HS-THS Main Gym [Directions] | 5:00 p.m. | ||
| Tue., 12/12 | FR Girls Basketball | New Milford | Home - Trumbull HS-THS Main Gym [Directions] | Canceled | Cancelled | |
| Wed., 12/13 | V Wrestling | Darien | Home - Trumbull HS-Aux Gym [Directions] | 6:00 p.m. | Trumbull 83 Darien 0 | |
| Wed., 12/13 | V Girls Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | 7:15 p.m. | L 5-0 | |
| Thu., 12/14 | JV Wrestling | Fairfield Warde | Away - Fairfield Warde HS-Small Gym [Directions] | 4:00 p.m. | ||
| Fri., 12/15 | V Boys Basketball | Masuk | Home - Trumbull HS-THS Main Gym [Directions] | 7:00 p.m. | W 60-40 | |
| Fri., 12/15 | JV Boys Basketball | Masuk | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 12/15 | FR Boys Basketball | Masuk | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 12/15 | V Boys Swimming and Diving | Staples | Away - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Sat., 12/16 | V Boys Ice Hockey | North Branford | Away - Northford-Red [Directions] | 5:00 p.m. | L 3-5 | |
| Sat., 12/16 | V Boys Indoor Track | Staples, Greenwich, Stamford, Westhill | Away - Staples HS-Field House [Directions] | 1:00 p.m. | ||
| Sat., 12/16 | V Girls Basketball | Glastonbury | Home - Trumbull HS-THS Main Gym [Directions] | 12:30 p.m. | L 35-38 | |
| Sat., 12/16 | JV Girls Basketball | Glastonbury | Home - Trumbull HS-THS Main Gym [Directions] | 11:00 a.m. | ||
| Sat., 12/16 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Sacred Heart University-Martire Arena [Directions] | 3:15 p.m. | W 5-1 | |
| Sat., 12/16 | V Girls Indoor Track | Staples, Greenwich, Stamford, Westhill | Away - Staples HS-Field House [Directions] | 1:00 p.m. | ||
| Sun., 12/17 | JV Girls Ice Hockey | Fairfield Ludlowe/Warde, Greenwich, Ridgefield/Danbury/Immaculate, Wilton/Norwalk/McMahon (Scrim.) | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 2:00 p.m. | ||
| Wed., 12/20 | V Boys Ice Hockey | Branford | Away - Northford-Red [Directions] | 8:30 p.m. | T 2-2 | |
| Wed., 12/20 | V Wrestling | Wilton | Away - Wilton HS-Nicholas Zeoli Fieldhouse [Directions] | 6:00 p.m. | Trumbull 69 Wilton 9 | |
| Wed., 12/20 | V Girls Basketball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 7:00 p.m. | W 47-40 | |
| Wed., 12/20 | JV Girls Basketball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 12/20 | FR Girls Basketball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | Canceled | Cancelled | |
| Thu., 12/21 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Away - Norwalk HS-Pat Spinola Natatorium [Directions] | 4:00 p.m. | ||
| Thu., 12/21 | V Girls Ice Hockey | Darien | Away - Darien Ice House-Ice Rink [Directions] | 7:10 p.m. | L 6-0 | |
| Fri., 12/22 | V Boys Basketball | Amistad | Home - Trumbull HS-THS Main Gym [Directions] | 3:00 p.m. | W 75-41 | |
| Fri., 12/22 | JV Boys Basketball | Amistad | Home - Trumbull HS-THS Main Gym [Directions] | 1:30 p.m. | ||
| Fri., 12/22 | V Girls Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | L 34-45 | |
| Fri., 12/22 | JV Girls Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 12/22 | FR Girls Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | Canceled | Cancelled | |
| Sat., 12/23 | V Boys Ice Hockey | Amity | Away - West Haven HS-Bennett Rink [Directions] | 7:00 p.m. | L 0-7 | |
| Sat., 12/23 | V Wrestling | Brookfield/Shepaug, Conard, Ridgefield, Staples, Westhill | Home - Trumbull HS-THS Main Gym [Directions] | 9:00 a.m. | Trumbull 65 Westhill 15 Trumbull 60 Brookfield/Shepaug 24 Trumbull 60 Conard 24 Trumbull 60 Staples 21 Trumbull 33 Ridgefield 48 | |
| Wed., 12/27 | V Boys Basketball | Joel Barlow | Away - Stratford HS-Gym [Directions] | 5:00 p.m. | W 65-34 | |
| Wed., 12/27 | FR Boys Basketball | Stratford | Home - Trumbull HS-THS Main Gym [Directions] | 11:00 a.m. | ||
| Wed., 12/27 | V Girls Basketball | Notre Dame-Fairfield | Away - North Haven HS-Fred Kelly Gymnasium [Directions] | 5:00 p.m. | W 45-42 | |
| Thu., 12/28 | V Boys Basketball | Jonathan Law | Away - Stratford HS-Gym [Directions] | 7:00 p.m. | W 68-38 | |
| Thu., 12/28 | V Boys Ice Hockey | Oyster River (NH) | Away - University of New Hampshire - Durham Campus | 8:30 p.m. | L 2-5 | |
| Fri., 12/29 | V Boys Ice Hockey | Keene Regional (NH) | Away - University of New Hampshire - Durham Campus | 5:00 p.m. | L 0-4 | |
| Fri., 12/29 | V Boys Indoor Track | Marine Corps Invitational - Armory | Away - Armory Track (168th Street Armory, NYC) | 10:00 a.m. | ||
| Fri., 12/29 | JV Wrestling | Brien McMahon, Darien, Fairfield Warde, Greenwich, Masuk, TBA, New Canaan, New Fairfield, New Milford, Newtown, Ridgefield, Simsbury, Stamford, Staples, Xavier | Home - Trumbull HS-THS Main Gym [Directions] | 9:00 a.m. | ||
| Fri., 12/29 | V Girls Basketball | North Haven | Away - North Haven HS-Fred Kelly Gymnasium [Directions] | 7:00 p.m. | L 51-56 | |
| Fri., 12/29 | V Girls Indoor Track | Marine Corps Invitational - Armory | Away - Armory Track (168th Street Armory, NYC) | 10:00 a.m. | ||
| Sat., 12/30 | V Boys Ice Hockey | Portsmouth (NH) | Away - Portsmouth NH HS-portsmouth field | 3:30 p.m. | L 2-3 | |
| Sat., 12/30 | V Wrestling | Trumbull Duals | Home - Trumbull HS-McDougall Stadium [Directions] | 9:00 a.m. | Trumbull 67 Pomperaug Co-Op 15 Trumbull 67 Manchester 9 Trumbull 40 NFA 39 Trumbull 53 Berlin 24 Trumbull 37 Foran 33 | |
| Wed., 1/3 | V Boys Basketball | Harding | Home - Trumbull HS-THS Main Gym [Directions] | 7:00 p.m. | W 74-37 | |
| Wed., 1/3 | JV Boys Basketball | Harding | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/3 | FR Boys Basketball | Harding | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/3 | V Boys Swimming and Diving | Westhill/Stamford | Away - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Wed., 1/3 | V Wrestling | E.O. Smith, Bloomfield Weaver | Away - E.O. Smith HS-Front Gym [Directions] | 4:00 p.m. | Trumbull 84 EO Smith 0 | |
| Wed., 1/3 | V Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 7:00 p.m. | L 51-60 | |
| Wed., 1/3 | JV Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/3 | FR Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | Canceled | Cancelled | |
| Fri., 1/5 | V Boys Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 7:00 p.m. | W 69-49 | |
| Fri., 1/5 | JV Boys Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/5 | FR Boys Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/5 | V Boys Swimming and Diving | Danbury | Home - University of Bridgeport-Pool [Directions] | 4:00 p.m. | ||
| Fri., 1/5 | V Girls Basketball | Westhill | Home - Trumbull HS-THS Main Gym [Directions] | 6:30 p.m. | W 44-16 | |
| Fri., 1/5 | JV Girls Basketball | Westhill | Home - Trumbull HS-THS Main Gym [Directions] | 5:00 p.m. | ||
| Fri., 1/5 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 3:30 p.m. | L 5-3 | |
| Sat., 1/6 | V Boys Ice Hockey | Wilton | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 3:00 p.m. | L 2-4 | |
| Sat., 1/6 | V Boys Indoor Track | Staples, Bridgeport Central, St. Joseph | Away - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/6 | V Boys Indoor Track | Hispanic Games Invitational - Armory | Away - Armory Track (168th Street Armory, NYC) | 8:30 a.m. | ||
| Sat., 1/6 | V Wrestling | East Haven, Glastonbury, Stratford, Waterford | Away - East Haven HS-Gym [Directions] | 9:00 a.m. | Trumbull 64 East Haven 15 Trumbull 68 Waterford 10 Trumbull 58 Glastonbury 18 Trumbull 61 Stratford 18 | |
| Sat., 1/6 | V Girls Gymnastics | TBA, Darien | Away - TBA-Albermale Field | 4:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Next Dimension Gymnastics-Next Dimension | ||||||
| Sat., 1/6 | V Girls Indoor Track | Staples, Bridgeport Central, St. Joseph | Away - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/6 | V Girls Indoor Track | Hispanic Games Invitational - Armory | Away - Armory Track (168th Street Armory, NYC) | 8:30 a.m. | ||
| Mon., 1/8 | V Boys Ice Hockey | Brien McMahon/Norwalk | Away - Sono Ice House-Main Rink [Directions] | 8:20 p.m. | L 3-5 | |
| Mon., 1/8 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 8:00 p.m. | W 4-1 | |
| Tue., 1/9 | FR Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | Canceled | Cancelled | |
| Wed., 1/10 | V Wrestling | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 6:00 p.m. | Trumbull 75 McMahon 6 | |
| Wed., 1/10 | V Girls Gymnastics | Greenwich, St. Joseph | Away - Greenwich YWCA [Directions] | 7:00 p.m. | 144.05 | |
| Thu., 1/11 | V Boys Basketball | Danbury | Home - Trumbull HS-THS Main Gym [Directions] | 7:00 p.m. | W 58-38 | |
| Thu., 1/11 | JV Boys Basketball | Danbury | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 1/11 | FR Boys Basketball | Danbury | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 1/11 | V Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 6:00 p.m. | W 46-30 | |
| Thu., 1/11 | JV Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | Canceled | Cancelled | |
| Thu., 1/11 | JV Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 4:30 p.m. | ||
| Thu., 1/11 | V Girls Ice Hockey | Stamford/Westhill/Staples | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 8:00 p.m. | L 3-1 | |
| Fri., 1/12 | V Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 7:00 p.m. | L 64-68 | |
| Fri., 1/12 | JV Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/12 | FR Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/12 | V Boys Indoor Track | Yale Track Classic | Away - Yale University | 2:00 p.m. | ||
| Fri., 1/12 | V Girls Basketball | Fairfield Warde | Home - Trumbull HS-THS Main Gym [Directions] | 6:30 p.m. | L 33-36 | |
| Fri., 1/12 | JV Girls Basketball | Fairfield Warde | Home - Trumbull HS-THS Main Gym [Directions] | 5:00 p.m. | ||
| Fri., 1/12 | FR Girls Basketball | Fairfield Warde | Home - Trumbull HS-THS Main Gym [Directions] | Canceled | Cancelled | |
| Fri., 1/12 | V Girls Indoor Track | Yale Track Classic | Away - Yale University | 2:00 p.m. | ||
| Sat., 1/13 | V Boys Ice Hockey | Staples | Away - Milford Ice Pavillion-Ice Rink [Directions] | 6:00 p.m. | W 4-3 | |
| Sat., 1/13 | V Boys Indoor Track | Yale Track Classic | Away - Yale University | 9:00 a.m. | ||
| Sat., 1/13 | V Boys Indoor Track | Wilton Developmental Meet | Away - Wilton HS | 9:30 a.m. | ||
| Sat., 1/13 | V Boys Indoor Track | Wilton, Brien McMahon, Fairfield Ludlowe, Fairfield Warde, New Canaan, Norwalk, Ridgefield | Away - Wilton HS-Nicholas Zeoli Field House | 9:30 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 9:00 a.m. | ||||||
| Sat., 1/13 | V Wrestling | Enfield, Farmington, Ledyard, Longmeadow (MA), Rockville, Rocky Hill | Away - Enfield HS-EHS GYM - MAIN | 10:00 a.m. | Trumbull 78 Longmeadow MA 21 Trumbull 64 Farmington 16 Trumbull 54 Enfield 27 Trumbull 54 Ledyard 30 Trumbull 62 Rockville 18 Trumbull 72 Rocky Hill 12 | |
| Sat., 1/13 | JV Wrestling | Danbury, Fairfield Warde, Greenwich, New Fairfield, Norwalk, Simsbury, Xavier | Home - Trumbull HS-THS Main Gym [Directions] | 9:00 a.m. | ||
| Sat., 1/13 | V Girls Gymnastics | Norwalk, Staples | Home - Next Dimension Gymnastics-Next Dimension [Directions] | 4:30 p.m. | 141.7 | |
| Sat., 1/13 | V Girls Indoor Track | Yale Track Classic | Away - Yale University | 9:00 a.m. | ||
| Sat., 1/13 | V Girls Indoor Track | Wilton Developmental Meet | Away - Wilton HS | 9:30 a.m. | ||
| Mon., 1/15 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Away - Fairfield University-Pool [Directions] | 6:00 p.m. | ||
| Mon., 1/15 | V Girls Gymnastics | Darien, St. Joseph | Home - Next Dimension Gymnastics-Next Dimension [Directions] | 7:00 p.m. | 146.95 | |
| Mon., 1/15 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 9:00 a.m. | L 4-3 | |
| Tue., 1/16 | JV Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | Postponed | ||
| Tue., 1/16 | FR Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | Postponed | ||
| Wed., 1/17 | V Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:00 p.m. | W 64-42 | |
| Wed., 1/17 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 8:30 p.m. | L 1-11 | |
| Wed., 1/17 | V Wrestling | Danbury | Home - Trumbull HS-Aux Gym [Directions] | 6:00 p.m. | Danbury 45 Trumbull 27 | |
| Wed., 1/17 | V Girls Basketball | Brien McMahon | Home - Trumbull HS-THS Main Gym [Directions] | 6:30 p.m. | W 43-26 | |
| Wed., 1/17 | JV Girls Basketball | Brien McMahon | Home - Trumbull HS-THS Main Gym [Directions] | 5:00 p.m. | ||
| Wed., 1/17 | V Girls Gymnastics | Fairfield Warde, Fairfield Ludlowe, Jonathan Law, St. Joseph | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:00 p.m. | 143.55 | |
| Wed., 1/17 | V Girls Ice Hockey | Daniel Hand Coop | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | W 3-1 | |
| Thu., 1/18 | V Boys Swimming and Diving | Greenwich | Home - Univ of Bridgeport Pool [Directions] | 4:00 p.m. | ||
| Fri., 1/19 | V Boys Basketball | Wilton | Home - Trumbull HS-THS Main Gym [Directions] | 7:00 p.m. | W 76-51 | |
| Fri., 1/19 | JV Boys Basketball | Wilton | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/19 | FR Boys Basketball | Wilton | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/19 | V Girls Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:00 p.m. | W 41-35 | |
| Fri., 1/19 | JV Girls Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Sat., 1/20 | V Boys Ice Hockey | St. Joseph | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 12:00 p.m. | L 0-2 | |
| Sat., 1/20 | V Boys Indoor Track | Staples, Darien, Fairfield Ludlowe, Fairfield Warde, Norwalk, Ridgefield, Westhill | Away - Staples HS-Field House | 10:00 a.m. | ||
| Sat., 1/20 | V Boys Indoor Track | Officials Hall of Fame Invitational - Armory | Away - Armory Track (168th Street Armory, NYC) | 8:30 a.m. | ||
| Sat., 1/20 | V Wrestling | Colter Abely Midseason Classic | Away - Mercy HS-Gym | 9:00 a.m. | 175.5 | |
| Sat., 1/20 | JV Wrestling | Danbury, Enfield, Fairfield Ludlowe, Fairfield Warde, New Canaan, New Fairfield, Newtown, Norwalk, Ridgefield, Simsbury, Southington, Stamford, Weston | Away - Danbury HS-Main Gym | 9:30 a.m. | ||
| Sat., 1/20 | V Girls Indoor Track | Staples, Darien, Fairfield Ludlowe, Fairfield Warde, Norwalk, Ridgefield, Westhill | Away - Staples HS-Field House | 10:00 a.m. | ||
| Sat., 1/20 | V Girls Indoor Track | Officials Hall of Fame Invitational - Armory | Away - Armory Track (168th Street Armory, NYC) | 8:30 a.m. | ||
| Sat., 1/20 | Miscellaneous Events | Hillcrest vs. Madison Girls Basketball | Home - Trumbull HS-THS Main Gym [Directions] | 3:00 p.m. | ||
| Sat., 1/20 | Miscellaneous Events | Hillcrest vs. Madison Boys Basketball | Home - Trumbull HS-THS Main Gym [Directions] | 4:30 p.m. | ||
| Sun., 1/21 | V Girls Ice Hockey | Mamaroneck (NY) (Scrim.) | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 6:30 p.m. | ||
| Tue., 1/23 | V Boys Basketball | Bridgeport Central | Home - Trumbull HS-THS Main Gym [Directions] | 7:00 p.m. | W 67-44 | |
| Tue., 1/23 | JV Boys Basketball | Bridgeport Central | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/23 | FR Boys Basketball | Bridgeport Central | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/24 | V Boys Ice Hockey | Greenwich | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 8:00 p.m. | L 4-6 | |
| Wed., 1/24 | V Wrestling | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 7:00 p.m. | Trumbull 48 Norwalk 30 | |
| Wed., 1/24 | V Girls Basketball | Bridgeport Central | Home - Trumbull HS-THS Main Gym [Directions] | 7:00 p.m. | W 68-34 | |
| Wed., 1/24 | JV Girls Basketball | Bridgeport Central | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/24 | V Girls Ice Hockey | Masuk Coop | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | W 4-3 | |
| Fri., 1/26 | V Boys Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 7:00 p.m. | W 91-63 | |
| Fri., 1/26 | JV Boys Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/26 | FR Boys Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/26 | V Girls Basketball | Darien | Home - Trumbull HS-THS Main Gym [Directions] | 6:30 p.m. | W 55-33 | |
| Fri., 1/26 | JV Girls Basketball | Darien | Home - Trumbull HS-THS Main Gym [Directions] | 5:00 p.m. | ||
| Fri., 1/26 | FR Girls Basketball | Darien | Home - Trumbull HS-THS Main Gym [Directions] | Canceled | Cancelled | |
| Sat., 1/27 | V Boys Ice Hockey | Ridgefield | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 8:30 p.m. | L 0-8 | |
| Sat., 1/27 | V Boys Indoor Track | FCIAC West Divisionals | Away - Staples HS-Field House | 10:00 a.m. | ||
| Sat., 1/27 | V Wrestling | SHS WRESTLING TOURNAMENT | Away - Southington HS-Gym West | 8:00 a.m. | 132 | |
| Sat., 1/27 | JV Wrestling | Norwalk, Brien McMahon, Darien, Fairfield Prep, Fairfield Ludlowe, Fairfield Warde, Greenwich, New Canaan, New Milford, St. Joseph, Stamford, Staples, Westhill, Weston, Wilton | Away - Norwalk HS-Tom Scarso Gymnasium | 8:00 a.m. | ||
| Sat., 1/27 | V Girls Gymnastics | Wilton | Home - Next Dimension Gymnastics-Next Dimension [Directions] | 4:30 p.m. | 145.3 | |
| Sat., 1/27 | V Girls Ice Hockey | Woodstock Academy Coop | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 8:15 p.m. | W 6-0 | |
| Sat., 1/27 | V Girls Indoor Track | FCIAC West Divisionals | Away - Staples HS-Field House | 10:00 a.m. | ||
| Mon., 1/29 | V Girls Gymnastics | Westhill, St. Joseph, Stamford | Away - Westhill HS-New Gym [Directions] | 6:00 p.m. | 142.85 | |
| Tue., 1/30 | V Boys Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 7:00 p.m. | W 75-66 | |
| Tue., 1/30 | JV Boys Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/30 | FR Boys Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/30 | V Girls Basketball | Greenwich | Home - Trumbull HS-THS Main Gym [Directions] | 6:30 p.m. | W 45-35 | |
| Tue., 1/30 | JV Girls Basketball | Greenwich | Home - Trumbull HS-THS Main Gym [Directions] | 5:00 p.m. | ||
| Tue., 1/30 | FR Girls Basketball | Greenwich | Home - Trumbull HS-THS Main Gym [Directions] | Canceled | Cancelled | |
| Wed., 1/31 | V Boys Ice Hockey | Westhill/Stamford | Away - Terry Conners - Stamford-Ice Rink [Directions] | 7:50 p.m. | L 0-7 | |
| Wed., 1/31 | V Wrestling | Stamford | Home - Trumbull HS-Aux Gym [Directions] | 6:00 p.m. | Trumbull 65 Stamford 18 | |
| Wed., 1/31 | V Girls Ice Hockey | Guilford Coop | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | W 3-2 | |
| Thu., 2/1 | V Boys Indoor Track | FCIAC Championship @ Floyd Little Athletic Center | Away - Floyd Little Athletic Center-Field House | 5:30 p.m. | ||
| Thu., 2/1 | V Girls Outdoor Track | FCIAC Championship @ Floyd Little Athletic Center | Away - Floyd Little Athletic Center-Field House | 5:30 p.m. | ||
| Fri., 2/2 | V Boys Basketball | St. Joseph | Home - Trumbull HS-THS Main Gym [Directions] | 7:30 p.m. | W 88-62 | |
| Fri., 2/2 | FR Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 3:15 p.m. | ||
| Fri., 2/2 | V Boys Swimming and Diving | Ridgefield | Home - Univ of Bridgeport Pool [Directions] | 4:00 p.m. | ||
| Fri., 2/2 | V Wrestling | Fairfield Warde, Greenwich, Notre Dame-West Haven | Away - Fairfield Warde HS-Small Gym [Directions] | 4:00 p.m. | Trumbull 55 Notre Dame-West Haven 23 Warde 60 Trumbull 17 Trumbull 65 Greenwich 12 | |
| Fri., 2/2 | V Girls Basketball | St. Joseph | Home - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | W 38 - 27 | |
| Fri., 2/2 | FR Girls Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | Canceled | Cancelled | |
| Sat., 2/3 | JV Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 10:30 a.m. | ||
| Sat., 2/3 | V Boys Ice Hockey | Wilton | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:00 p.m. | L 1-3 | |
| Sat., 2/3 | JV Girls Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 9:00 a.m. | ||
| Sat., 2/3 | V Competitive Cheerleading | FCIAC Cheer Championship | Home - Trumbull HS-THS Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 2/3 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 12:15 p.m. | W 6-2 | |
| Mon., 2/5 | V Boys Swimming and Diving | Wilton | Away - Wilton YMCA [Directions] | 3:40 p.m. | ||
| Mon., 2/5 | V Girls Ice Hockey | Masuk Coop | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 8:30 p.m. | L 6-0 | |
| Tue., 2/6 | V Boys Basketball | Stamford | Home - Trumbull HS-THS Main Gym [Directions] | 7:00 p.m. | L 59-62 | |
| Tue., 2/6 | JV Boys Basketball | Stamford | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/6 | FR Boys Basketball | Stamford | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/6 | V Girls Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 6:00 p.m. | L 31 - 33 | |
| Tue., 2/6 | JV Girls Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 2/7 | V Boys Swimming and Diving | Darien | Home - Univ of Bridgeport Pool [Directions] | 4:00 p.m. | ||
| Wed., 2/7 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 3:45 p.m. | W 3-1 | |
| Thu., 2/8 | V Boys Indoor Track | CIAC LL Divisional Championship | Away - Floyd Little Athletic Center | 4:30 p.m. | ||
| Thu., 2/8 | V Girls Ice Hockey | Greenwich | Away - Greenwich - Dorothy Hamill-Rink [Directions] | 7:00 p.m. | W 4-3 | |
| Thu., 2/8 | V Girls Indoor Track | CIAC LL Divisional Championship | Away - Floyd Little Athletic Center | 4:30 p.m. | ||
| Fri., 2/9 | V Boys Basketball | Norwalk | Home - Trumbull HS-THS Main Gym [Directions] | 7:00 p.m. | W 90-74 | |
| Fri., 2/9 | JV Boys Basketball | Norwalk | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/9 | FR Boys Basketball | Norwalk | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 2/9 | V Wrestling | New Canaan, Bridgeport Central, Brien McMahon, Danbury, Darien, FCIAC, Fairfield Ludlowe, Fairfield Warde, Greenwich, Norwalk, Ridgefield, St. Joseph, Stamford, Staples, Westhill, Wilton | Away - New Canaan HS-Main Gym | 4:30 p.m. | ||
| Fri., 2/9 | V Girls Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 6:15 p.m. | W 37 - 23 | |
| Fri., 2/9 | JV Girls Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:30 p.m. | ||
| Sat., 2/10 | V Boys Ice Hockey | Brien McMahon/Norwalk | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 7:30 p.m. | W 2-0 | |
| Sat., 2/10 | V Girls Gymnastics | FCIAC Championship Meet | Away - Gymnastics and Cheerleading Academy at Connecticut | 2:00 p.m. | 141.9 | |
| Mon., 2/12 | V Boys Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 7:00 p.m. | W 55-39 | |
| Mon., 2/12 | JV Boys Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/12 | FR Boys Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Mon., 2/12 | V Boys Swimming and Diving | New Canaan | Home - Univ of Bridgeport Pool [Directions] | 4:00 p.m. | ||
| Mon., 2/12 | V Girls Basketball | Staples | Home - Trumbull HS-THS Main Gym [Directions] | 6:30 p.m. | L 44 - 50 | |
| Mon., 2/12 | JV Girls Basketball | Staples | Home - Trumbull HS-THS Main Gym [Directions] | 5:00 p.m. | ||
| Mon., 2/12 | FR Girls Basketball | Staples | Home - Trumbull HS-THS Main Gym [Directions] | Canceled | Cancelled | |
| Mon., 2/12 | V Girls Ice Hockey | West Haven/SHA | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 8:15 p.m. | L 2-0 | |
| Wed., 2/14 | V Boys Ice Hockey | Staples | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 8:30 p.m. | L 2-3 (OT) | |
| Wed., 2/14 | V Girls Basketball | Ridgefield | Home - Trumbull HS-THS Main Gym [Directions] | 7:00 p.m. | W 53 - 51 | |
| Wed., 2/14 | JV Girls Basketball | Ridgefield | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/14 | FR Girls Basketball | Ridgefield | Home - Trumbull HS-THS Main Gym [Directions] | Canceled | Cancelled | |
| Thu., 2/15 | V Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 7:00 p.m. | L 66-74 | |
| Thu., 2/15 | JV Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 2/15 | FR Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 2/16 | V Wrestling | CIAC LL Divisional Championship | Away - Trumbull | TBA | ||
| Fri., 2/16 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | L 4-3 | |
| Fri., 2/16 | Miscellaneous Events | LL Wrestling State Championship | Home - Trumbull HS-THS Main Gym [Directions] | TBA | ||
| Sat., 2/17 | V Boys Ice Hockey | Westhill/Stamford | Home - Total Mortgage Arena - Harbor Yard-Ice Rink [Directions] | 12:30 p.m. | L 1-3 | |
| Sat., 2/17 | V Boys Indoor Track | CIAC State Open Divisional Championship | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/17 | V Girls Basketball | Fairfield Warde | Away - Staples HS-Staples Gym [Directions] | 2:30 p.m. | ||
| Sat., 2/17 | V Girls Gymnastics | St. Joseph | Away - Next Dimension Gymnastics-Next Dimension [Directions] | 4:30 p.m. | 145.75 | |
| Sat., 2/17 | V Girls Indoor Track | CIAC State Open Championship | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/17 | Miscellaneous Events | LL Wrestling State Championship | Home - Trumbull HS-THS Main Gym [Directions] | TBA | ||
| Mon., 2/19 | V Boys Basketball | New Canaan | Home - Trumbull HS-THS Main Gym [Directions] | 7:00 p.m. | W 75-52 | |
| Mon., 2/19 | JV Boys Basketball | New Canaan | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/19 | FR Boys Basketball | New Canaan | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 2/19 | JV Wrestling | Simsbury, Danbury, Glastonbury, Wethersfield | Away - Simsbury HS-Gym 2 [Directions] | 9:30 a.m. | ||
| Tue., 2/20 | Miscellaneous Events | FCIAC Girls Basketball Semi-finals | Home - Trumbull HS-THS Main Gym [Directions] | TBA | ||
| Wed., 2/21 | V Boys Basketball | Fairfield Ludlowe | Home - Trumbull HS-THS Main Gym [Directions] | 7:00 p.m. | W 56-52 | |
| Wed., 2/21 | JV Boys Basketball | Fairfield Ludlowe | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/21 | FR Boys Basketball | Fairfield Ludlowe | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/21 | V Boys Ice Hockey | East Haven Coop | Away - East Haven HS-Patsy DiLungo Rink [Directions] | 5:00 p.m. | L 0-5 | |
| Wed., 2/21 | V Girls Basketball | Newtown, Masuk (Scrim.) | Away - Newtown HS-Gym [Directions] | 5:00 p.m. | ||
| Thu., 2/22 | Miscellaneous Events | FCIAC Girls Basketball Finals | Home - Trumbull HS-THS Main Gym [Directions] | 7:00 p.m. | ||
| Fri., 2/23 | V Wrestling | CIAC State Open & Girls Championship | Away - Floyd Little Athletic Center | TBA | ||
| Sat., 2/24 | V Boys Basketball | Fairfield Warde | Home - Fairfield Warde HS-Gym [Directions] | 2:00 p.m. | ||
| Sat., 2/24 | V Boys Ice Hockey | Cheshire | Away - Hamden-Lou Astorino Ice Rink [Directions] | 5:00 p.m. | L 0-5 | |
| Sat., 2/24 | V Girls Gymnastics | CIAC Class L Divisional Championship | Away - Jonathan Law | 1:00 p.m. | ||
| Mon., 2/26 | V Girls Basketball | Kennedy | Home - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | W 57-23 | |
| Tue., 2/27 | V Boys Basketball | Danbury | Home - Wilton HS-Wilton Field House [Directions] | 5:30 p.m. | ||
| Thu., 2/29 | V Boys Basketball | Staples | Home - Wilton HS-Wilton Field House [Directions] | 7:00 p.m. | ||
| Thu., 2/29 | V Girls Basketball | Hamden | Away - Hamden HS-HHS Gym [Directions] | 6:00 p.m. | L 40-55 | |
| Sat., 3/2 | V Competitive Cheerleading | Brookfield | Home - Trumbull HS-THS Main Gym [Directions] | 5:00 p.m. | ||
| Sat., 3/2 | V Girls Gymnastics | CIAC State Open | Away - New Milford | 12:00 p.m. | ||
| Tue., 3/5 | V Boys Ice Hockey | CIAC Div II First Round | Away - Higher Seed | TBA | ||
| Wed., 3/6 | V Boys Basketball | Fairfield Warde | Home - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | L 49-56 | |
| Thu., 3/7 | V Boys Swimming and Diving | CIAC Class LL Diving Championship | Away - Sheehan | 5:30 p.m. | ||
| Fri., 3/8 | V Boys Ice Hockey | CIAC Div II Quarterfinal | Away - Site TBA | TBA | ||
| Sat., 3/9 | V Boys Swimming and Diving | CIAC Class LL Qualifying Meet | Away - Cornerstone Pool | 4:30 p.m. | ||
| Tue., 3/12 | V Boys Ice Hockey | CIAC Div II Semifinal | Away - Site TBA | TBA | ||
| Tue., 3/12 | V Boys Swimming and Diving | CIAC Class LL Finals | Away - Wesleyan | 6:00 p.m. | ||
| Thu., 3/14 | V Boys Swimming and Diving | CIAC State Open Diving | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/16 | V Boys Swimming and Diving | CIAC State Open Swimming | Away - Yale | 1:00 p.m. | ||
| Mon., 3/18 | V Boys Ice Hockey | CIAC Div II Final | Away - Site TBA | TBA | ||
| Thu., 3/21 | V Boys Rugby | Darien (Scrim.) | Away - Royle School Field [Directions] | 4:30 p.m. | ||
| Thu., 3/21 | FM Boys Rugby | Staples (Scrim.) | Away - Staples HS-Staples Stadium [Directions] | 5:15 p.m. | ||
| Fri., 3/22 | V Boys Tennis | Weston (Scrim.) | Home - Trumbull HS-Tennis Courts [Directions] | 4:30 p.m. | W 6-1 | |
| Fri., 3/22 | V Softball | Woodland (Scrim.) | Away - Woodland HS-Softball Diamond [Directions] | 4:00 p.m. | ||
| Sat., 3/23 | V Boys Volleyball | Joel Barlow, Farmington, Glastonbury, Iona Prep (NY), New Canaan, Pomperaug, Simsbury | Away - Joel Barlow HS-Lower Gym | 8:30 a.m. | ||
| Sat., 3/23 | V Softball | Maloney (Scrim.) | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 11:00 a.m. | Cancelled | |
| Sat., 3/23 | V Softball | Maloney (Scrim.) | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 1:00 p.m. | Cancelled | |
| Sun., 3/24 | V Baseball | Bunnell (Scrim.) | Away - Bunnell HS-Bunnell Baseball Field [Directions] | Canceled | Cancelled | |
| Sun., 3/24 | V Boys Lacrosse | Bethel (Scrim.) | Away - Bethel HS-MS turf lacrosse field [Directions] | 12:30 p.m. | ||
| Sun., 3/24 | V Girls Lacrosse | New Milford Jamboree | Away - New Milford HS-Joe Wiser Stadium - NMHS | 8:00 a.m. | ||
| Mon., 3/25 | V Baseball | Staples (Scrim.) | Away - Staples HS-Baseball Diamond [Directions] | 3:45 p.m. | ||
| Mon., 3/25 | V Boys Volleyball | Southington (Scrim.) | Away - Southington HS-Gym West [Directions] | 4:00 p.m. | ||
| Mon., 3/25 | V Softball | Jonathan Law (Scrim.) | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 4:00 p.m. | ||
| Tue., 3/26 | V Baseball | Notre Dame-Fairfield (Scrim.) | Home - Trumbull HS-Varsity Baseball Field [Directions] | 4:15 p.m. | ||
| Tue., 3/26 | V Boys Lacrosse | Brookfield (Scrim.) | Home - Trumbull HS-Cork Field [Directions] | 4:00 p.m. | ||
| Tue., 3/26 | FM Boys Rugby | Fairfield Ludlowe (Scrim.) | Away - Veteran's Park - Bridgeport-Rugby Field [Directions] | 4:00 p.m. | ||
| Tue., 3/26 | V Girls Tennis | Seymour (Scrim.) | Home - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 3/27 | V Baseball | Seymour (Scrim.) | Home - Trumbull HS-Varsity Baseball Field [Directions] | 3:45 p.m. | ||
| Wed., 3/27 | JV Baseball | Seymour (Scrim.) | Home - Trumbull HS-JV Baseball Field [Directions] | 3:45 p.m. | ||
| Wed., 3/27 | V Boys Tennis | Masuk (Scrim.) | Away - Wolfe Park-Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Wed., 3/27 | V Softball | Amity (Scrim.) | Away - Amity Regional HS-Amity HS - Softball Field [Directions] | 4:00 p.m. | ||
| Wed., 3/27 | V Girls Tennis | Shelton (Scrim.) | Away - Shelton HS-Tennis Courts [Directions] | 3:45 p.m. | ||
| Thu., 3/28 | V Baseball | Newtown (Scrim.) | Away - Newtown HS-Nighthawk Ball Park [Directions] | Canceled | Cancelled | |
| Thu., 3/28 | V Boys Lacrosse | Joel Barlow (Scrim.) | Away - Joel Barlow HS-Field J [Directions] | 5:00 p.m. | ||
| Thu., 3/28 | V Boys Volleyball | Newtown (Scrim.) | Home - Trumbull HS-THS Main Gym [Directions] | 5:00 p.m. | ||
| Thu., 3/28 | JV Boys Volleyball | Newtown (Scrim.) | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 3/28 | V Softball | Foran (Scrim.) | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 4:00 p.m. | Cancelled | |
| Sat., 3/30 | V Baseball | Masuk | Home - Trumbull HS-Varsity Baseball Field [Directions] | 12:00 p.m. | ||
| Sat., 3/30 | JV Baseball | Masuk | Home - Trumbull HS-JV Baseball Field [Directions] | 12:00 p.m. | ||
| Sat., 3/30 | V Boys Volleyball | CIAC Boys' Volleyball Invitational | Away - CT Volleyball Center Woodbridge | 8:00 a.m. | ||
| Sat., 3/30 | V Softball | Newtown | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 12:00 p.m. | W 1-0 | |
| Sat., 3/30 | JV Softball | Newtown | Home - Trumbull HS-JV Softball Diamond [Directions] | Postponed | ||
| Sat., 3/30 | JV Softball | Staples | Away - Staples HS-Wakeman Field [Directions] | 1:30 p.m. | ||
| Mon., 4/1 | V Baseball | Amity | Away - Amity Regional HS-John Janenda Field [Directions] | 3:45 p.m. | ||
| Mon., 4/1 | V Boys Outdoor Track | Stamford | Home - Trumbull HS-McDougall Stadium [Directions] | 4:00 p.m. | ||
| Mon., 4/1 | V Boys Volleyball | Joel Barlow | Home - Trumbull HS-THS Main Gym [Directions] | 4:30 p.m. | L 2-3 | |
| Mon., 4/1 | JV Boys Volleyball | Joel Barlow | Home - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | ||
| Mon., 4/1 | V Girls Outdoor Track | Stamford | Home - Trumbull HS-McDougall Stadium [Directions] | 4:00 p.m. | ||
| Mon., 4/1 | V Girls Tennis | Joel Barlow (Scrim.) | Home - Trumbull HS-Tennis Courts [Directions] | 4:30 p.m. | ||
| Tue., 4/2 | FR Baseball | Amity | Away - Amity Regional HS-John Janenda Field [Directions] | Postponed | ||
| Tue., 4/2 | V Boys Lacrosse | New Fairfield | Home - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | L 5-9 | |
| Tue., 4/2 | JV Boys Lacrosse | New Fairfield | Home - Trumbull HS-McDougall Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/2 | FR Boys Lacrosse | Westhill | Home - Trumbull HS-Cork Field [Directions] | 4:00 p.m. | ||
| Tue., 4/2 | V Girls Lacrosse | Stratford/Bunnell | Away - Penders Field-Penders Field - Stratford [Directions] | 6:30 p.m. | W 16-0 | |
| Tue., 4/2 | JV Girls Lacrosse | Stratford/Bunnell | Away - Penders Field-Penders Field - Stratford [Directions] | 5:00 p.m. | ||
| Tue., 4/2 | FR Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Fairfield Warde Grass Utility Field [Directions] | Postponed | ||
| Wed., 4/3 | FR Baseball | Ridgefield | Home - Trumbull HS-Varsity Baseball Field [Directions] | Postponed | ||
| Wed., 4/3 | V Boys Volleyball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | 6:00 p.m. | W 3-1 | |
| Wed., 4/3 | JV Boys Volleyball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | 4:30 p.m. | ||
| Wed., 4/3 | V Girls Rugby | vs. Aspetuck | Home - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | ||
| Thu., 4/4 | V Boys Lacrosse | Danbury | Home - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | W 14-0 | |
| Thu., 4/4 | JV Boys Lacrosse | Danbury | Home - Trumbull HS-Cork Field [Directions] | 4:00 p.m. | ||
| Thu., 4/4 | V Girls Lacrosse | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 4:30 p.m. | W 14-2 | |
| Thu., 4/4 | JV Girls Lacrosse | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 6:00 p.m. | ||
| Fri., 4/5 | V Baseball | Ridgefield | Away - Governor Field [Directions] | 4:00 p.m. | ||
| Fri., 4/5 | JV Baseball | Ridgefield | Away - East Ridge MS-Baseball Field [Directions] | Postponed | ||
| Fri., 4/5 | V Boys Rugby | Staples | Home - Trumbull HS-Cork Field [Directions] | 6:00 p.m. | ||
| Fri., 4/5 | V Boys Tennis | Cheshire | Away - Cheshire HS-Tennis Courts [Directions] | 3:00 p.m. | W 4-3 | |
| Fri., 4/5 | V Boys Volleyball | Simsbury | Away - Simsbury HS-Simsbury / Main Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Fri., 4/5 | JV Boys Volleyball | Simsbury | Away - Simsbury HS-Simsbury / Main Gym [Directions] | 4:30 p.m. | ||
| Fri., 4/5 | FR Girls Lacrosse | Fairfield Ludlowe | Home - Trumbull HS-Stump Field [Directions] | 4:00 p.m. | ||
| Fri., 4/5 | V Softball | West Haven | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 4:15 p.m. | W 11-3 | |
| Fri., 4/5 | JV Softball | West Haven | Home - Trumbull HS-JV Softball Diamond [Directions] | 4:15 p.m. | ||
| Sat., 4/6 | V Baseball | Notre Dame-West Haven | Away - Quigley Stadium-Baseball Field [Directions] | 2:00 p.m. | ||
| Sat., 4/6 | FR Baseball | Westhill | Away - Westhill HS-Varsity Baseball Field [Directions] | 11:00 a.m. | ||
| Sat., 4/6 | V Boys Lacrosse | Norwalk | Home - Trumbull HS-McDougall Stadium [Directions] | 12:00 p.m. | W 13-3 | |
| Sat., 4/6 | JV Boys Lacrosse | Norwalk | Home - Trumbull HS-McDougall Stadium [Directions] | 10:00 a.m. | ||
| Sat., 4/6 | V Girls Lacrosse | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | 12:00 p.m. | L 6-11 | |
| Sat., 4/6 | JV Girls Lacrosse | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | 10:30 a.m. | ||
| Sat., 4/6 | V Softball | Norwich Free Academy | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 12:00 p.m. | W 12-10 | |
| Sat., 4/6 | JV Softball | Norwich Free Academy | Home - Trumbull HS-JV Softball Diamond [Directions] | 12:00 p.m. | ||
| Mon., 4/8 | V Baseball | Fairfield Prep | Away - Fairfield University-Alumni Diamond [Directions] | 4:30 p.m. | ||
| Mon., 4/8 | JV Baseball | Fairfield Prep | Home - Trumbull HS-Varsity Baseball Field [Directions] | 5:00 p.m. | ||
| Mon., 4/8 | FR Baseball | Fairfield Prep | Away - Tunxis Hill Park [Directions] | 5:00 p.m. | ||
| Mon., 4/8 | FR Boys Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | 5:00 p.m. | ||
| Mon., 4/8 | V Boys Tennis | Westhill | Away - Westhill HS-Westhill Tennis Courts [Directions] | 5:00 p.m. | L 1-6 | |
| Mon., 4/8 | FR Girls Lacrosse | Norwalk | Home - Trumbull HS-The Pit [Directions] | Postponed | ||
| Mon., 4/8 | V Girls Tennis | Westhill | Home - Trumbull HS-Tennis Courts [Directions] | 5:00 p.m. | ||
| Tue., 4/9 | JV Baseball | Bunnell | Away - Bunnell HS-Bunnell Baseball Field [Directions] | 4:15 p.m. | ||
| Tue., 4/9 | V Boys Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 4:30 p.m. | L 16-0 | |
| Tue., 4/9 | JV Boys Lacrosse | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Tue., 4/9 | V Boys Tennis | Danbury | Home - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 4/9 | JV Boys Tennis | Ridgefield | Away - Ridgefield HS-RHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/9 | V Girls Lacrosse | New Canaan | Home - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | L 3-19 | |
| Tue., 4/9 | JV Girls Lacrosse | New Canaan | Home - Trumbull HS-Cork Field [Directions] | 4:15 p.m. | ||
| Tue., 4/9 | V Softball | St. Joseph | Away - St. Joseph HS-Softball Diamond [Directions] | 4:30 p.m. | L 3-1 | |
| Tue., 4/9 | JV Softball | St. Joseph | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 4:00 p.m. | ||
| Tue., 4/9 | V Girls Tennis | Danbury | Away - Danbury HS-DHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/9 | JV Girls Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/10 | FR Boys Lacrosse | Wilton | Home - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Wed., 4/10 | V Softball | Danbury | Away - Danbury HS-V Softball field [Directions] | 4:30 p.m. | W 19-6 | |
| Wed., 4/10 | JV Softball | Danbury | Away - Danbury HS-JV Softball Field [Directions] | 4:30 p.m. | ||
| Wed., 4/10 | JV Girls Tennis | St. Joseph | Home - Tashua Knolls Golf Course-Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 4/11 | V Boys Lacrosse | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | W 9-7 | |
| Thu., 4/11 | JV Boys Lacrosse | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:45 p.m. | ||
| Thu., 4/11 | V Girls Lacrosse | Westhill | Home - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | W 14-6 | |
| Thu., 4/11 | JV Girls Lacrosse | Westhill | Home - Trumbull HS-Cork Field [Directions] | 4:15 p.m. | ||
| Fri., 4/12 | V Boys Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:00 p.m. | L 1-3 | |
| Fri., 4/12 | JV Boys Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 4/12 | JV Softball | Westhill | Away - TBA [Directions] | TBA | ||
| Sat., 4/13 | V Boys Lacrosse | Conard | Away - Conard HS-McKee Stadium [Directions] | 10:00 a.m. | L 8-10 | |
| Sat., 4/13 | JV Boys Lacrosse | Conard | Away - Conard HS-North Field [Directions] | 11:30 a.m. | ||
| Sat., 4/13 | V Girls Lacrosse | Lauralton Hall | Home - Trumbull HS-McDougall Stadium [Directions] | 12:00 p.m. | ||
| Sat., 4/13 | JV Girls Lacrosse | Lauralton Hall | Home - Trumbull HS-McDougall Stadium [Directions] | 10:15 a.m. | ||
| Sat., 4/13 | V Softball | Westhill | Away - Westhill HS-Varsity Softball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/15 | V Baseball | Danbury | Away - Danbury HS-V Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/15 | JV Baseball | Danbury | Away - Danbury HS-JV Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/15 | FR Baseball | Danbury | Home - Trumbull HS-Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/15 | V Boys Outdoor Track | St. Joseph, Harding | Home - Trumbull HS-McDougall Stadium [Directions] | 4:00 p.m. | ||
| Mon., 4/15 | V Boys Tennis | Brien McMahon | Away - Brien McMahon HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Mon., 4/15 | V Boys Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 4/15 | JV Boys Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 4/15 | V Girls Outdoor Track | Lauralton Hall, St. Joseph, Harding | Home - Trumbull HS-McDougall Stadium [Directions] | 4:00 p.m. | ||
| Mon., 4/15 | V Softball | Danbury | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 4:15 p.m. | W 3-2 | |
| Mon., 4/15 | JV Softball | Danbury | Home - Trumbull HS-JV Softball Diamond [Directions] | 4:00 p.m. | ||
| Mon., 4/15 | V Girls Tennis | Brien McMahon | Home - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/16 | V Baseball | Westhill | Home - Trumbull HS-Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Tue., 4/16 | JV Baseball | Westhill | Home - Trumbull HS-JV Baseball Field [Directions] | 4:00 p.m. | ||
| Tue., 4/16 | V Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | L 7-2 | |
| Tue., 4/16 | JV Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 5:30 p.m. | ||
| Tue., 4/16 | V Boys Tennis | Wilton | Home - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Tue., 4/16 | JV Boys Tennis | Wilton | Home - Tashua Knolls Golf Course-Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/16 | V Girls Golf | St. Joseph | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 4/16 | V Girls Lacrosse | Fairfield Warde | Home - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | ||
| Tue., 4/16 | JV Girls Lacrosse | Fairfield Warde | Home - Trumbull HS-Cork Field [Directions] | Postponed | ||
| Tue., 4/16 | V Softball | Westhill | Away - Westhill HS-Varsity Softball Field [Directions] | 4:30 p.m. | W 9-1 | |
| Tue., 4/16 | V Girls Tennis | Wilton | Away - Wilton HS-Allen Meadow [Directions] | 4:00 p.m. | ||
| Tue., 4/16 | JV Girls Tennis | Wilton | Away - Wilton Middlebrook School-JV Tennis Courts [Directions] | Postponed | ||
| Wed., 4/17 | FR Boys Lacrosse | Cheshire | Away - Cheshire HS-Grass Fields [Directions] | 4:30 p.m. | ||
| Wed., 4/17 | V Boys Rugby | Fairfield Prep | Home - Trumbull HS-Cork Field [Directions] | 6:30 p.m. | ||
| Wed., 4/17 | JV Boys Rugby | Fairfield Prep | Home - Trumbull HS-Cork Field [Directions] | Canceled | Cancelled | |
| Wed., 4/17 | V Boys Tennis | Fairfield Warde | Away - Fairfield Warde HS-Blake Courts [Directions] | 3:30 p.m. | W 4-0 | |
| Wed., 4/17 | V Boys Volleyball | Fairfield Ludlowe | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 4/17 | JV Boys Volleyball | Fairfield Ludlowe | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 4/17 | V Girls Tennis | Fairfield Warde | Home - Trumbull HS-Tennis Courts [Directions] | 3:00 p.m. | ||
| Thu., 4/18 | V Boys Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:45 p.m. | ||
| Thu., 4/18 | JV Boys Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:30 p.m. | ||
| Thu., 4/18 | V Girls Lacrosse | Shelton | Home - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | ||
| Thu., 4/18 | JV Girls Lacrosse | Shelton | Home - Trumbull HS-Cork Field [Directions] | 4:30 p.m. | ||
| Fri., 4/19 | V Baseball | Brien McMahon | Home - Trumbull HS-Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 4/19 | JV Baseball | Brien McMahon | Home - Trumbull HS-JV Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 4/19 | FR Baseball | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | Canceled | Cancelled | |
| Fri., 4/19 | FR Boys Lacrosse | Staples | Away - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Fri., 4/19 | V Girls Rugby | Southington | Away - Southington HS-3 TURF FIELD [Directions] | 7:15 p.m. | ||
| Fri., 4/19 | V Softball | Brien McMahon | Away - Brien McMahon HS-Softball Diamond [Directions] | 4:00 p.m. | W 14-1 (5inn) | |
| Fri., 4/19 | JV Softball | Brien McMahon | Away - Brookside Elementary School [Directions] | Canceled | Cancelled | |
| Sat., 4/20 | V Baseball | Fairfield Warde | Home - Trumbull HS-Varsity Baseball Field [Directions] | 1:00 p.m. | ||
| Sat., 4/20 | JV Baseball | Fairfield Warde | Home - Trumbull HS-JV Baseball Field [Directions] | 1:00 p.m. | ||
| Sat., 4/20 | FR Baseball | Fairfield Warde | Away - Fairfield Warde HS-Baseball Diamond [Directions] | 12:00 p.m. | ||
| Sat., 4/20 | V Boys Lacrosse | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 12:00 p.m. | L 10-5 | |
| Sat., 4/20 | JV Boys Lacrosse | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 10:00 a.m. | ||
| Sat., 4/20 | V Girls Lacrosse | Stamford | Home - Trumbull HS-McDougall Stadium [Directions] | 12:00 p.m. | ||
| Sat., 4/20 | JV Girls Lacrosse | Stamford | Home - Trumbull HS-McDougall Stadium [Directions] | 10:15 a.m. | ||
| Sat., 4/20 | V Softball | Fairfield Warde | Away - Fairfield Warde HS-Softball Diamond [Directions] | 12:00 p.m. | W 9-8 (8inn) | |
| Sat., 4/20 | JV Softball | Fairfield Warde | Away - Fairfield Warde HS-Softball Diamond [Directions] | 2:00 p.m. | ||
| Mon., 4/22 | V Baseball | Wilton | Away - Wilton HS-Varsity Baseball Field [Directions] | 4:15 p.m. | ||
| Mon., 4/22 | JV Baseball | Wilton | Away - Wilton HS-JV Baseball Field [Directions] | 4:15 p.m. | ||
| Mon., 4/22 | FR Baseball | Wilton | Home - Trumbull HS-Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/22 | FR Boys Lacrosse | Stamford | Home - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | ||
| Mon., 4/22 | V Boys Outdoor Track | Greenwich | Home - Trumbull HS-McDougall Stadium [Directions] | 3:30 p.m. | ||
| Mon., 4/22 | V Boys Tennis | Darien | Away - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 4/22 | JV Boys Tennis | Darien | Away - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 4/22 | FR Girls Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 3:30 p.m. | ||
| Mon., 4/22 | V Girls Outdoor Track | Greenwich | Home - Trumbull HS-McDougall Stadium [Directions] | 3:30 p.m. | ||
| Mon., 4/22 | V Softball | Wilton | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 4:15 p.m. | W 9-1 | |
| Mon., 4/22 | JV Softball | Wilton | Home - Trumbull HS-JV Softball Diamond [Directions] | 4:15 p.m. | ||
| Mon., 4/22 | V Girls Tennis | Darien | Home - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | V Boys Lacrosse | Staples | Home - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | ||
| Tue., 4/23 | JV Boys Lacrosse | Staples | Home - Trumbull HS-Cork Field [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | V Boys Tennis | Greenwich | Away - Greenwich HS-Tennis Courts [Directions] | 4:15 p.m. | ||
| Tue., 4/23 | JV Boys Tennis | Greenwich | Away - Eastern MS [Directions] | 4:30 p.m. | ||
| Tue., 4/23 | V Boys Volleyball | Stamford | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 4/23 | JV Boys Volleyball | Stamford | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | V Girls Golf | Danbury | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 4/23 | V Girls Lacrosse | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | JV Girls Lacrosse | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 5:30 p.m. | ||
| Tue., 4/23 | V Softball | Bridgeport Central | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 4:15 p.m. | W 17-0 (5inn) | |
| Tue., 4/23 | JV Softball | Bridgeport Central | Home - Trumbull HS-JV Softball Diamond [Directions] | 4:15 p.m. | ||
| Tue., 4/23 | V Girls Tennis | Greenwich | Home - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | JV Girls Tennis | Greenwich | Home - Tashua Knolls Golf Course-Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | V Baseball | Bridgeport Central | Away - Bridgeport Central HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | FM Boys Rugby | Greenwich | Home - Trumbull HS-Cork Field [Directions] | 6:30 p.m. | ||
| Wed., 4/24 | V Boys Tennis | Bridgeport Central | Home - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | V Girls Golf | Ridgefield | Away - Ridgefield Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 4/24 | FR Girls Lacrosse | Fairfield Warde | Home - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | V Girls Tennis | Bridgeport Central | Away - Bridgeport Central HS-Central High School Tennis Courts [Directions] | 5:00 p.m. | ||
| Wed., 4/24 | JV Girls Tennis | Darien | Home - Tashua Knolls Golf Course-Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | Miscellaneous Events | Shaun | Home - Trumbull HS-Aux Gym [Directions] | 2:45 p.m. | ||
| Thu., 4/25 | V Boys Lacrosse | Fairfield Ludlowe | Home - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | ||
| Thu., 4/25 | JV Boys Lacrosse | Fairfield Ludlowe | Home - Trumbull HS-Cork Field [Directions] | 4:00 p.m. | ||
| Thu., 4/25 | V Boys Tennis | St. Joseph | Home - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 4/25 | JV Boys Tennis | Greenwich | Home - Tashua Knolls Golf Course-Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 4/25 | V Boys Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | ||
| Thu., 4/25 | JV Boys Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:15 p.m. | ||
| Thu., 4/25 | V Girls Golf | Fairfield Ludlowe | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Thu., 4/25 | JV Girls Golf | Fairfield Ludlowe | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Thu., 4/25 | V Girls Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 6:00 p.m. | ||
| Thu., 4/25 | JV Girls Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | ||
| Thu., 4/25 | V Girls Tennis | St. Joseph | Away - St. Joseph HS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 4/26 | V Baseball | Darien | Home - Trumbull HS-Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 4/26 | JV Baseball | Darien | Home - Trumbull HS-JV Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 4/26 | FR Baseball | Darien | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Fri., 4/26 | FR Boys Lacrosse | Greenwich | Home - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | ||
| Fri., 4/26 | FR Girls Lacrosse | Ridgefield | Away - Scotts Ridge MS-SRMS Turf [Directions] | 4:00 p.m. | ||
| Fri., 4/26 | V Girls Rugby | Greenwich | Home - Trumbull HS-Cork Field [Directions] | 6:00 p.m. | ||
| Fri., 4/26 | V Softball | Darien | Away - Darien HS-DHS Softball - Varsity Field [Directions] | 4:30 p.m. | L 3-0 | |
| Sat., 4/27 | V Boys Lacrosse | Newtown | Home - Trumbull HS-McDougall Stadium [Directions] | 12:00 p.m. | ||
| Sat., 4/27 | JV Boys Lacrosse | Newtown | Home - Trumbull HS-McDougall Stadium [Directions] | 10:00 a.m. | ||
| Sat., 4/27 | V Boys Outdoor Track | O'Grady Relays | Away - Danbury HS-Danbury HS Stadium | 9:00 a.m. | ||
| Sat., 4/27 | V Boys Volleyball | St. Joseph | Home - Trumbull HS-THS Main Gym [Directions] | 12:00 p.m. | ||
| Sat., 4/27 | JV Boys Volleyball | St. Joseph | Home - Trumbull HS-THS Main Gym [Directions] | 10:30 a.m. | ||
| Sat., 4/27 | V Girls Lacrosse | Hamden | Away - Hamden HS-HHS Turf #1 [Directions] | 11:00 a.m. | ||
| Sat., 4/27 | JV Girls Lacrosse | Hamden | Away - Hamden HS-HHS Turf #1 [Directions] | Canceled | Cancelled | |
| Sat., 4/27 | JV Girls Tennis | St. Joseph | Home - Trumbull HS-Tennis Courts [Directions] | 12:00 p.m. | ||
| Mon., 4/29 | V Baseball | Greenwich | Home - Trumbull HS-Varsity Baseball Field [Directions] | 4:30 p.m. | ||
| Mon., 4/29 | JV Baseball | Greenwich | Home - Trumbull HS-JV Baseball Field [Directions] | 4:30 p.m. | ||
| Mon., 4/29 | FR Baseball | Greenwich | Away - Havemeyer Field-Havermeyer Field [Directions] | 4:30 p.m. | ||
| Mon., 4/29 | FR Boys Lacrosse | Newtown | Home - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | V Boys Tennis | Stamford | Home - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | V Girls Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | 3:30 p.m. | ||
| Mon., 4/29 | V Softball | Greenwich | Away - Greenwich HS-Softball Field [Directions] | 4:30 p.m. | W 5-1 | |
| Mon., 4/29 | JV Softball | Greenwich | Away - Julian Curtiss School [Directions] | 4:30 p.m. | ||
| Mon., 4/29 | V Girls Tennis | Stamford | Away - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/30 | V Boys Outdoor Track | Westhill | Home - Trumbull HS-McDougall Stadium [Directions] | 4:30 p.m. | ||
| Tue., 4/30 | V Boys Tennis | Norwalk | Home - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/30 | JV Boys Tennis | New Canaan | Home - Tashua Knolls Golf Course-Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/30 | V Boys Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:00 p.m. | ||
| Tue., 4/30 | JV Boys Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 5:30 p.m. | ||
| Tue., 4/30 | V Girls Golf | Wilton | Away - Silvermine Golf Club [Directions] | 3:30 p.m. | ||
| Tue., 4/30 | V Girls Lacrosse | Joel Barlow | Away - Joel Barlow HS-Field J [Directions] | 4:00 p.m. | ||
| Tue., 4/30 | JV Girls Lacrosse | Joel Barlow | Away - Joel Barlow HS-Field J [Directions] | 5:30 p.m. | ||
| Tue., 4/30 | V Girls Outdoor Track | Westhill | Home - Trumbull HS-McDougall Stadium [Directions] | 4:30 p.m. | ||
| Tue., 4/30 | V Girls Tennis | Norwalk | Away - Grassroots Tennis and Education-Grassroots Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | V Baseball | St. Joseph | Away - St. Joseph HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | JV Baseball | St. Joseph | Away - Unity Park-Field 1 [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | FR Baseball | St. Joseph | Home - Trumbull HS-Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | FR Boys Lacrosse | Ridgefield | Away - Scotts Ridge MS [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | V Girls Golf | Fairfield Warde | Away - Smith Richardson Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 5/1 | FR Girls Lacrosse | New Canaan | Home - Trumbull HS-The Pit [Directions] | Postponed | ||
| Wed., 5/1 | V Softball | St. Joseph | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 4:15 p.m. | L 14-4 | |
| Wed., 5/1 | JV Softball | St. Joseph | Home - Trumbull HS-JV Softball Diamond [Directions] | 4:15 p.m. | ||
| Thu., 5/2 | V Boys Lacrosse | Guilford | Away - Guilford HS-Kavanaugh Turf Field and Track [Directions] | 7:00 p.m. | ||
| Thu., 5/2 | JV Boys Lacrosse | Guilford | Away - Guilford HS-Kavanaugh Turf Field and Track [Directions] | 5:00 p.m. | ||
| Thu., 5/2 | V Boys Tennis | Staples | Away - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/2 | JV Boys Tennis | Staples | Away - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/2 | V Boys Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 4:30 p.m. | ||
| Thu., 5/2 | JV Boys Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 5:45 p.m. | ||
| Thu., 5/2 | V Girls Lacrosse | West Haven | Home - Trumbull HS-Cork Field [Directions] | 4:00 p.m. | ||
| Thu., 5/2 | JV Girls Lacrosse | West Haven | Home - Trumbull HS-Cork Field [Directions] | Canceled | Cancelled | |
| Thu., 5/2 | V Girls Tennis | Staples | Home - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/2 | JV Girls Tennis | Staples | Home - Tashua Knolls Golf Course-Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 5/3 | V Baseball | Stamford | Away - Cubeta Stadium [Directions] | 5:00 p.m. | ||
| Fri., 5/3 | JV Baseball | Stamford | Away - Belltown Park-Barrett Field, Belltown Park [Directions] | 5:00 p.m. | ||
| Fri., 5/3 | FR Baseball | Stamford | Home - Trumbull HS-Varsity Baseball Field [Directions] | 5:15 p.m. | ||
| Fri., 5/3 | FR Boys Lacrosse | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | ||
| Fri., 5/3 | V Softball | Stamford | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 5:15 p.m. | W 8-4 | |
| Fri., 5/3 | JV Softball | Stamford | Home - Trumbull HS-JV Softball Diamond [Directions] | 5:15 p.m. | ||
| Sat., 5/4 | JV Baseball | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 9:00 a.m. | ||
| Sat., 5/4 | FR Baseball | Norwalk | Home - Trumbull HS-Varsity Baseball Field [Directions] | 11:00 a.m. | ||
| Sat., 5/4 | V Boys Lacrosse | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 12:00 p.m. | ||
| Sat., 5/4 | JV Boys Lacrosse | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 10:00 a.m. | ||
| Sat., 5/4 | V Boys Rugby | Greenwich | Home - Trumbull HS-Cork Field [Directions] | 12:00 p.m. | ||
| Sat., 5/4 | JV Boys Rugby | Greenwich | Home - Trumbull HS-Cork Field [Directions] | 10:00 a.m. | ||
| Sat., 5/4 | V Boys Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 11:00 a.m. | ||
| Sat., 5/4 | JV Boys Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 12:30 p.m. | ||
| Sat., 5/4 | V Girls Lacrosse | St. Joseph | Home - Trumbull HS-McDougall Stadium [Directions] | 12:00 p.m. | ||
| Sat., 5/4 | JV Girls Lacrosse | St. Joseph | Home - Trumbull HS-McDougall Stadium [Directions] | 10:30 a.m. | ||
| Sat., 5/4 | FR Girls Lacrosse | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | 4:30 p.m. | ||
| Mon., 5/6 | V Baseball | Norwalk | Away - Dunkin' Park (Hartford, CT)-Yard Goats [Directions] | 6:30 p.m. | ||
| Mon., 5/6 | FR Boys Lacrosse | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | V Boys Outdoor Track | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | V Boys Tennis | Ridgefield | Away - Ridgefield HS-RHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | JV Boys Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | V Boys Volleyball | Norwalk | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 5/6 | JV Boys Volleyball | Norwalk | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | V Girls Outdoor Track | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | V Softball | Norwalk | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 4:15 p.m. | ||
| Mon., 5/6 | JV Softball | Norwalk | Home - Trumbull HS-JV Softball Diamond [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | V Girls Tennis | Ridgefield | Home - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | JV Boys Lacrosse | Amity | Away - Amity Regional HS-AHS Grass Field # 3 [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | V Boys Tennis | New Canaan | Home - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | JV Boys Tennis | New Canaan | Home - Tashua Knolls Golf Course-Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | V Girls Golf | New Canaan | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 5/7 | JV Girls Golf | New Canaan | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 5/7 | V Girls Tennis | New Canaan | Away - New Canaan HS-NCHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | JV Girls Tennis | New Canaan | Away - New Canaan HS-NCHS Tennis Courts [Directions] | 5:30 p.m. | ||
| Wed., 5/8 | V Baseball | Staples | Home - Trumbull HS-Varsity Baseball Field [Directions] | 6:00 p.m. | ||
| Wed., 5/8 | JV Baseball | Staples | Home - Trumbull HS-JV Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | FR Baseball | Staples | Away - Staples HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | FR Boys Lacrosse | New Canaan | Home - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | V Boys Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | JV Boys Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 6:00 p.m. | ||
| Wed., 5/8 | V Girls Golf | New Canaan | Away - CCNC [Directions] | 3:30 p.m. | ||
| Wed., 5/8 | FR Girls Lacrosse | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | V Softball | Staples | Away - Staples HS-Wakeman Field [Directions] | 4:30 p.m. | ||
| Wed., 5/8 | JV Softball | Staples | Away - Staples HS-Staples Softball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | JV Girls Tennis | Ridgefield | Home - Tashua Knolls Golf Course-Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/9 | V Boys Lacrosse | Amity | Away - Amity Regional HS-William Johnson Stadium Field [Directions] | 7:00 p.m. | ||
| Thu., 5/9 | V Boys Tennis | Fairfield Ludlowe | Home - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/9 | JV Boys Tennis | Fairfield Ludlowe | Home - Tashua Knolls Golf Course-Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/9 | V Girls Rugby | Southington | Home - Trumbull HS-Cork Field [Directions] | 6:00 p.m. | ||
| Thu., 5/9 | V Girls Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/9 | JV Girls Tennis | Fairfield Ludlowe | Away - Dwight Elementary School-Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 5/10 | V Baseball | Ridgefield | Home - Trumbull HS-Varsity Baseball Field [Directions] | 6:00 p.m. | ||
| Fri., 5/10 | JV Baseball | Ridgefield | Home - Trumbull HS-JV Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 5/10 | FR Baseball | Ridgefield | Away - Governor Field [Directions] | 4:00 p.m. | ||
| Fri., 5/10 | FR Boys Lacrosse | Fairfield Ludlowe | Home - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | ||
| Fri., 5/10 | JV Boys Tennis | Fairfield Warde | Away - Fairfield Warde HS-Knapps Courts [Directions] | 4:00 p.m. | ||
| Fri., 5/10 | V Boys Volleyball | Westhill | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 5/10 | JV Boys Volleyball | Wilton | Home - Trumbull HS-THS Main Gym [Directions] | 4:30 p.m. | ||
| Fri., 5/10 | FR Girls Lacrosse | Norwalk | Home - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Fri., 5/10 | V Softball | Ridgefield | Away - Ridgefield HS-Varsity Softball Field [Directions] | 4:30 p.m. | ||
| Fri., 5/10 | JV Girls Tennis | Fairfield Warde | Away - Fairfield Woods-Tennis Courts [Directions] | 4:00 p.m. | ||
| Sat., 5/11 | V Boys Lacrosse | Masuk | Home - Trumbull HS-McDougall Stadium [Directions] | 12:00 p.m. | ||
| Sat., 5/11 | V Boys Rugby | Fairfield Ludlowe | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 12:00 p.m. | ||
| Sat., 5/11 | FM Boys Rugby | Fairfield Ludlowe | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 2:00 p.m. | ||
| Mon., 5/13 | V Baseball | New Canaan | Away - Mead Park-Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | JV Baseball | New Canaan | Away - Waveny Park-Coppo Field [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | FR Baseball | New Canaan | Home - Trumbull HS-Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | FR Boys Lacrosse | Stamford | Home - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | FM Boys Rugby | Staples | Away - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Mon., 5/13 | V Boys Volleyball | Darien | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 5/13 | JV Boys Volleyball | Darien | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | V Girls Golf | Greenwich | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Mon., 5/13 | JV Girls Golf | Greenwich | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Mon., 5/13 | V Softball | New Canaan | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 6:00 p.m. | ||
| Mon., 5/13 | JV Softball | New Canaan | Home - Trumbull HS-JV Softball Diamond [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | V Boys Lacrosse | Brien McMahon | Home - Trumbull HS-McDougall Stadium [Directions] | 7:00 p.m. | ||
| Tue., 5/14 | JV Boys Lacrosse | Brien McMahon | Home - Trumbull HS-Cork Field [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | V Girls Golf | Darien | Away - Wee Burn CC [Directions] | 3:00 p.m. | ||
| Tue., 5/14 | V Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 6:30 p.m. | ||
| Tue., 5/14 | JV Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 4:45 p.m. | ||
| Wed., 5/15 | V Baseball | Fairfield Ludlowe | Away - Kiwanis Field-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | JV Baseball | Fairfield Ludlowe | Away - Owen Fish Park-Owen Fish [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | FR Baseball | Fairfield Ludlowe | Home - Trumbull HS-Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | FR Boys Lacrosse | Guilford | Away - Guilford HS-Maturo Field [Directions] | 3:45 p.m. | ||
| Wed., 5/15 | V Boys Outdoor Track | Danbury | Away - Danbury HS-Stadium Track [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | V Boys Rugby | Simsbury | Away - Holden Field-Simsbury 2 [Directions] | 6:15 p.m. | ||
| Wed., 5/15 | V Boys Volleyball | Bridgeport Central | Away - Bridgeport Central HS-The Barry McLeod Court [Directions] | 6:00 p.m. | ||
| Wed., 5/15 | JV Boys Volleyball | Bridgeport Central | Away - Bridgeport Central HS-The Barry McLeod Court [Directions] | 4:30 p.m. | ||
| Wed., 5/15 | FR Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Fairfield Warde Grass Utility Field [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | V Girls Outdoor Track | Danbury | Away - Danbury HS-Stadium Track [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | V Softball | Fairfield Ludlowe | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 6:00 p.m. | ||
| Wed., 5/15 | JV Softball | Fairfield Ludlowe | Home - Trumbull HS-JV Softball Diamond [Directions] | 4:00 p.m. | ||
| Thu., 5/16 | V Girls Golf | Staples | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Thu., 5/16 | JV Girls Golf | Staples | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Thu., 5/16 | FR Girls Lacrosse | Staples | Home - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Thu., 5/16 | V Girls Rugby | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 7:00 p.m. | ||
| Fri., 5/17 | FR Girls Lacrosse | Wilton | Away - Wilton HS-Allen Meadow [Directions] | 4:00 p.m. | ||
| Sun., 5/19 | Miscellaneous Events | Final Mile | Home - Trumbull HS-McDougall Stadium [Directions] | 9:00 a.m. | ||
| Mon., 5/20 | V Boys Tennis | Joel Barlow (Scrim.) | Away - Joel Barlow HS-Tennis Courts [Directions] | 3:45 p.m. | ||
| Mon., 5/20 | V Girls Golf | Amity | Away - Race Brook C.C. [Directions] | 3:15 p.m. | ||
| Tue., 5/21 | V Boys Outdoor Track | FCIAC's @ Danbury | Away - Danbury HS-Stadium Track | 2:30 p.m. | ||
| Tue., 5/21 | V Girls Golf | Amity | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 5/21 | JV Girls Golf | Amity | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 5/21 | V Girls Outdoor Track | FCIAC's @ Danbury | Away - Danbury HS-Stadium Track | 2:30 p.m. | ||
| Wed., 5/22 | FR Boys Rugby | Opponent - Stamford HS | Home - Trumbull HS-Cork Field [Directions] | 4:30 p.m. | ||
| Wed., 5/22 | V Girls Golf | Darien | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Wed., 5/22 | JV Girls Golf | Darien | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Fri., 5/24 | V Boys Rugby | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 5:30 p.m. | ||
| Tue., 5/28 | V Girls Golf | Staples | Away - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 5/28 | JV Girls Golf | Staples | Away - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 5/29 | FM Boys Rugby | Greenwich | Away - Greenwich HS-Field 7 [Directions] | 5:00 p.m. | ||
| Thu., 5/30 | V Girls Golf | FCIAC Tournament | Away - Fairchild Wheeler Golf Course | 3:15 p.m. | ||