| Trumbull 2021-22 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 987 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Wed., 8/25 | V Football | Amity (Scrim.) | Home - Trumbull HS-McDougall Stadium [Directions] | 3:30 p.m. | ||
| Wed., 8/25 | FR Football | Norwalk (Scrim.) | Away - Norwalk HS-Testa Field [Directions] | 4:00 p.m. | ||
| Sat., 8/28 | V Football | Hillhouse (Scrim.) | Home - Trumbull HS-McDougall Stadium [Directions] | 11:00 a.m. | ||
| Tue., 8/31 | V Boys Soccer | Amity (Scrim.) | Home - Trumbull HS-Cork Field [Directions] | 4:00 p.m. | ||
| Tue., 8/31 | JV Boys Soccer | Amity (Scrim.) | Home - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Thu., 9/2 | FR Football | Masuk (Scrim.) | Away - Masuk HS-Masuk High School Upper Field [Directions] | 5:00 p.m. | ||
| Thu., 9/2 | V Boys Soccer | Shelton (Scrim.) | Home - Trumbull HS-Cork Field [Directions] | 5:30 p.m. | ||
| Thu., 9/2 | V Field Hockey | Amity (Scrim.) | Home - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | ||
| Thu., 9/2 | V Girls Soccer | Shelton (Scrim.) | Home - Trumbull HS-Cork Field [Directions] | 3:30 p.m. | ||
| Thu., 9/2 | JV Girls Soccer | Greens Farms Academy (Scrim.) | Away - Greens Farms Academy-Greens Farms Academy - Turf Blue | 3:30 p.m. | ||
| Thu., 9/2 | FR Girls Soccer | TBA | Home - Trumbull HS-JV Grass Field [Directions] | Canceled | Cancelled | |
| Fri., 9/3 | V Field Hockey | Shelton (Scrim.) | Home - Trumbull HS-McDougall Stadium [Directions] | 3:30 p.m. | ||
| Fri., 9/3 | V Girls Volleyball | Stratford (Scrim.) | Away - Stratford HS-Gym [Directions] | 5:00 p.m. | ||
| Fri., 9/3 | JV Girls Volleyball | Stratford (Scrim.) | Away - Stratford HS-Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/4 | V Boys Soccer | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | 10:30 a.m. | ||
| Sat., 9/4 | V Boys Soccer | Farmington | Home - Naugatuck HS-Veterans Field [Directions] | 11:15 a.m. | ||
| Sat., 9/4 | V Girls Soccer | Milford Jamboree | Away - Jonathan Law HS-Lawmen Stadium | 8:30 a.m. | ||
| Mon., 9/6 | V Girls Soccer | Amity (Scrim.) | Away - Amity Regional HS-William Johnson Stadium Field [Directions] | 11:00 a.m. | ||
| Mon., 9/6 | JV Girls Soccer | Amity (Scrim.) | Away - Amity Regional HS-Amity High School - Field # 3 [Directions] | 11:00 a.m. | ||
| Wed., 9/8 | V Boys Golf | Danbury, Westhill | Home - Tashua Knolls Golf Course [Directions] | 3:30 p.m. | Westhill - 191 Danbury - 197 Trumbull - Forfeit | |
| Thu., 9/9 | FR Football | Staples | Away - Saugatuck Elementary School-PJ Romano Field [Directions] | 4:00 p.m. | ||
| Thu., 9/9 | V Boys Golf | Fairfield Warde | Away - Brooklawn Country Club [Directions] | 3:00 p.m. | Warde 169 Trumbull 180 | |
| Thu., 9/9 | V Field Hockey | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 5:45 p.m. | W 6-1 | |
| Thu., 9/9 | JV Field Hockey | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 7:00 p.m. | ||
| Thu., 9/9 | V Girls Soccer | Westhill | Home - Trumbull HS-Cork Field [Directions] | 4:00 p.m. | W 6-0 | |
| Fri., 9/10 | V Football | Staples | Away - Staples HS-Staples Stadium [Directions] | 7:00 p.m. | L 20-27 | |
| Fri., 9/10 | V Boys Soccer | Westhill | Away - Westhill HS-Westhill Front Turf Field [Directions] | 4:00 p.m. | L 0-1 | |
| Fri., 9/10 | JV Boys Soccer | Westhill | Away - Westhill HS-Front Turf [Directions] | 6:00 p.m. | ||
| Fri., 9/10 | FR Girls Soccer | Darien | Home - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Fri., 9/10 | V Girls Volleyball | Southington | Away - Southington HS-Gym West [Directions] | 6:00 p.m. | W 3-1 | |
| Fri., 9/10 | JV Girls Volleyball | Southington | Away - Southington HS-Gym West [Directions] | 5:00 p.m. | ||
| Fri., 9/10 | FR Girls Volleyball | Southington | Away - Southington HS-Gym East [Directions] | 5:00 p.m. | ||
| Sat., 9/11 | JV Football | Staples | Home - Trumbull HS-McDougall Stadium [Directions] | 10:30 a.m. | ||
| Sat., 9/11 | JV Boys Soccer | Danbury | Home - Trumbull HS-Cork Field [Directions] | 12:00 p.m. | ||
| Sat., 9/11 | FR Boys Soccer | Greenwich | Away - Greenwich HS-Field 7 [Directions] | 9:00 a.m. | ||
| Sat., 9/11 | V Field Hockey | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 4:00 p.m. | L 1-2 | |
| Sat., 9/11 | FR Field Hockey | Greenwich | Home - Trumbull HS-Cork Field [Directions] | 10:00 a.m. | ||
| Sat., 9/11 | V Girls Swimming and Diving | Danbury | Home - Orange Town Pool [Directions] | 3:00 p.m. | ||
| Sat., 9/11 | FR Girls Volleyball | Westhill | Home - Trumbull HS-THS Main Gym [Directions] | 10:00 a.m. | ||
| Mon., 9/13 | V Boys Golf | Darien | Away - Wee Burn CC [Directions] | 3:15 p.m. | Darien 157 Trumbull 205 | |
| Mon., 9/13 | JV Boys Golf | Darien | Away - Wee Burn CC [Directions] | 3:15 p.m. | ||
| Mon., 9/13 | V Girls Soccer | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 3:45 p.m. | L 1-2 | |
| Mon., 9/13 | JV Girls Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 3:45 p.m. | ||
| Mon., 9/13 | V Girls Volleyball | Masuk | Home - Trumbull HS-THS Main Gym [Directions] | 5:45 p.m. | W 3-0 | |
| Mon., 9/13 | JV Girls Volleyball | Masuk | Home - Trumbull HS-THS Main Gym [Directions] | 4:45 p.m. | ||
| Mon., 9/13 | FR Girls Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 3:30 p.m. | ||
| Tue., 9/14 | V Boys Cross Country | Brien McMahon, Fairfield Warde, Wilton | Home - Trumbull HS-Cross Country Course [Directions] | 4:00 p.m. | ||
| Tue., 9/14 | FR Football | Westhill | Home - Trumbull HS-McDougall Stadium [Directions] | 3:30 p.m. | ||
| Tue., 9/14 | V Boys Golf | Staples | Home - Tashua Knolls Golf Course [Directions] | 3:30 p.m. | Staples 161 Trumbull 181 | |
| Tue., 9/14 | JV Boys Golf | Staples | Home - Tashua Knolls Golf Course [Directions] | Canceled | Cancelled | |
| Tue., 9/14 | V Boys Soccer | Danbury | Home - Trumbull HS-Cork Field [Directions] | 6:00 p.m. | T 0-0 | |
| Tue., 9/14 | V Girls Cross Country | Brien McMahon, Fairfield Warde, Wilton | Home - Trumbull HS-Cross Country Course [Directions] | 4:00 p.m. | ||
| Tue., 9/14 | V Field Hockey | Fairfield Warde | Home - Trumbull HS-McDougall Stadium [Directions] | 7:00 p.m. | W 3-0 | |
| Tue., 9/14 | JV Field Hockey | Fairfield Warde | Home - Trumbull HS-McDougall Stadium [Directions] | 5:30 p.m. | ||
| Tue., 9/14 | FR Girls Soccer | Fairfield Warde | Away - Tunxis [Directions] | 4:00 p.m. | ||
| Wed., 9/15 | FR Boys Soccer | Staples | Home - Trumbull HS-The Pit [Directions] | 3:00 p.m. | ||
| Wed., 9/15 | JV Girls Soccer | Westhill | Home - Trumbull HS-JV Field [Directions] | Canceled | Cancelled | |
| Wed., 9/15 | V Girls Volleyball | Greenwich | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | L 0-3 | |
| Fri., 9/17 | V Girls Soccer | Darien | Home - Trumbull HS-Cork Field [Directions] | 4:00 p.m. | T 2-2 | |
| Fri., 9/17 | JV Girls Soccer | Darien | Home - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Sat., 9/18 | V Boys Soccer | Darien | Away - Darien HS-DHS Center Oval Turf Field [Directions] | 1:00 p.m. | L 0-5 | |
| Sat., 9/18 | JV Boys Soccer | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 1:00 p.m. | ||
| Sat., 9/18 | FR Boys Soccer | Newtown | Home - Trumbull HS-Cork Field [Directions] | 10:00 a.m. | ||
| Sat., 9/18 | V Field Hockey | Westhill | Home - Trumbull HS-McDougall Stadium [Directions] | 11:00 a.m. | W 4-0 | |
| Sat., 9/18 | JV Field Hockey | Westhill | Home - Trumbull HS-McDougall Stadium [Directions] | 9:30 a.m. | ||
| Sat., 9/18 | FR Field Hockey | Danbury | Away - Danbury HS-Grass Field Hockey Field [Directions] | 11:00 a.m. | ||
| Sat., 9/18 | FR Girls Soccer | Westhill | Home - Trumbull HS-Cork Field [Directions] | 12:00 p.m. | ||
| Sat., 9/18 | FR Girls Volleyball | Greenwich | Home - Trumbull HS-THS Main Gym [Directions] | 11:00 a.m. | ||
| Sat., 9/18 | Miscellaneous Events | Class of 2022 | Home - Trumbull HS [Directions] | 2:00 p.m. | ||
| Mon., 9/20 | V Boys Golf | Fairfield Ludlowe | Home - Tashua Knolls Golf Course [Directions] | 3:30 p.m. | Ludlowe 159 Trumbull 186 | |
| Mon., 9/20 | JV Boys Golf | Fairfield Ludlowe | Home - Tashua Knolls Golf Course [Directions] | 3:30 p.m. | ||
| Mon., 9/20 | FR Field Hockey | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Tue., 9/21 | V Boys Cross Country | Greenwich, Norwalk | Home - Trumbull HS-Cross Country Course [Directions] | 4:00 p.m. | ||
| Tue., 9/21 | V Boys Golf | Ridgefield | Away - Silver Spring Golf Course [Directions] | 3:15 p.m. | Ridgefield 166 Trumbull 189 | |
| Tue., 9/21 | V Girls Cross Country | Greenwich, Norwalk | Home - Trumbull HS-Cross Country Course [Directions] | 4:00 p.m. | ||
| Tue., 9/21 | V Field Hockey | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | L 0-3 | |
| Tue., 9/21 | JV Field Hockey | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 5:30 p.m. | ||
| Tue., 9/21 | FR Field Hockey | Wilton | Home - Trumbull HS-McDougall Stadium [Directions] | 6:30 p.m. | ||
| Tue., 9/21 | V Girls Soccer | Ridgefield | Home - Trumbull HS-Cork Field [Directions] | 6:00 p.m. | L 1-3 | |
| Tue., 9/21 | JV Girls Soccer | Ridgefield | Home - Trumbull HS-Cork Field [Directions] | 4:00 p.m. | ||
| Wed., 9/22 | FR Football | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:45 p.m. | ||
| Wed., 9/22 | V Boys Golf | Stamford | Home - Tashua Knolls Golf Course [Directions] | 3:30 p.m. | Stamford 206 Trumbull 175 | |
| Wed., 9/22 | V Boys Soccer | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 7:00 p.m. | L 1-2 | |
| Wed., 9/22 | JV Boys Soccer | Ridgefield | Away - Ridgefield HS-RHS Lower Grass Field [Directions] | 4:30 p.m. | ||
| Wed., 9/22 | FR Girls Soccer | Wilton | Away - Allen's Meadow-3A [Directions] | 4:15 p.m. | ||
| Thu., 9/23 | V Field Hockey | Wilton | Home - Trumbull HS-McDougall Stadium [Directions] | 7:30 p.m. | T 0-0 | |
| Thu., 9/23 | JV Field Hockey | Wilton | Home - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | ||
| Thu., 9/23 | V Girls Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 7:00 p.m. | L 1-2 | |
| Thu., 9/23 | JV Girls Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 4:00 p.m. | ||
| Fri., 9/24 | V Football | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 6:00 p.m. | W 29-28 | |
| Fri., 9/24 | V Boys Soccer | Fairfield Ludlowe | Home - Trumbull HS-Cork Field [Directions] | 6:00 p.m. | T 0-0 | |
| Fri., 9/24 | JV Boys Soccer | Fairfield Ludlowe | Home - Trumbull HS-Cork Field [Directions] | 4:00 p.m. | ||
| Fri., 9/24 | V Girls Swimming and Diving | Westhill/Stamford | Away - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Fri., 9/24 | V Girls Volleyball | Avon | Away - Avon HS-Large Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 9/24 | JV Girls Volleyball | Avon | Away - Avon HS-Large Gym [Directions] | 4:30 p.m. | ||
| Fri., 9/24 | FR Girls Volleyball | Avon | Away - Avon HS-Small gym [Directions] | 4:30 p.m. | ||
| Sat., 9/25 | JV Football | Fairfield Ludlowe | Home - Trumbull HS-McDougall Stadium [Directions] | 10:30 a.m. | ||
| Sat., 9/25 | V Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 10:00 a.m. | W 1-0 | |
| Sat., 9/25 | JV Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 11:30 a.m. | ||
| Sat., 9/25 | FR Field Hockey | New Canaan | Home - Trumbull HS-Cork Field [Directions] | 10:00 a.m. | ||
| Sat., 9/25 | FR Girls Soccer | Staples | Away - Staples HS-Wakeman Field B (turf) [Directions] | 10:00 a.m. | ||
| Sat., 9/25 | V Girls Swimming and Diving | St. Joseph | Away - High Plains Community Cn-Orange Community Center Pool [Directions] | 3:00 p.m. | ||
| Sat., 9/25 | FR Girls Volleyball | Stamford | Home - Trumbull HS-THS Main Gym [Directions] | 11:00 a.m. | ||
| Sat., 9/25 | Miscellaneous Events | Band Comp | Home - Trumbull HS-McDougall Stadium [Directions] | 12:00 p.m. | ||
| Mon., 9/27 | FR Boys Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | 4:00 p.m. | ||
| Mon., 9/27 | FR Boys Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 4:00 p.m. | ||
| Mon., 9/27 | V Girls Soccer | Greenwich | Home - Trumbull HS-Cork Field [Directions] | 5:30 p.m. | T 5-5 | |
| Mon., 9/27 | JV Girls Soccer | Greenwich | Home - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Tue., 9/28 | V Boys Golf | Wilton | Away - Rolling Hills Country Club [Directions] | 3:15 p.m. | Wilton 167 Trumbull 183 | |
| Tue., 9/28 | JV Boys Golf | Wilton | Away - Rolling Hills Country Club [Directions] | 3:15 p.m. | ||
| Tue., 9/28 | V Boys Soccer | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:45 p.m. | L 1-4 | |
| Tue., 9/28 | JV Boys Soccer | Greenwich | Away - Cos Cob Park-Binney Park [Directions] | 4:45 p.m. | ||
| Tue., 9/28 | V Field Hockey | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 7:30 p.m. | T 2-2 | |
| Tue., 9/28 | JV Field Hockey | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 6:00 p.m. | ||
| Tue., 9/28 | V Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Tue., 9/28 | JV Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 9/28 | FR Girls Volleyball | Fairfield Warde | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 9/29 | V Boys Cross Country | New Canaan, Danbury, Ridgefield | Away - Waveny Park [Directions] | 4:30 p.m. | ||
| Wed., 9/29 | JV Boys Golf | Ridgefield | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Wed., 9/29 | FR Boys Soccer | Stamford | Home - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | ||
| Wed., 9/29 | V Girls Cross Country | New Canaan, Danbury, Ridgefield | Away - Waveny Park [Directions] | 4:00 p.m. | ||
| Wed., 9/29 | FR Girls Soccer | Fairfield Warde | Home - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Thu., 9/30 | FR Football | Shelton | Away - Shelton HS-Finn Stadium [Directions] | 4:30 p.m. | ||
| Thu., 9/30 | FR Field Hockey | Ridgefield | Home - Trumbull HS-Cork Field [Directions] | 5:30 p.m. | ||
| Thu., 9/30 | V Girls Soccer | Bridgeport Central | Away - Bridgeport Central HS-Kennedy Stadium Turf [Directions] | 4:00 p.m. | W 8-0 | |
| Thu., 9/30 | V Girls Volleyball | Danbury | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Thu., 9/30 | JV Girls Volleyball | Danbury | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/1 | V Football | Shelton | Home - Trumbull HS-McDougall Stadium [Directions] | 7:00 p.m. | W 41-7 | |
| Fri., 10/1 | V Boys Soccer | Bridgeport Central | Home - Trumbull HS-Cork Field [Directions] | 4:30 p.m. | W 2-0 | |
| Fri., 10/1 | JV Boys Soccer | Bridgeport Central | Home - Trumbull HS-The Pit [Directions] | 4:30 p.m. | ||
| Sat., 10/2 | JV Football | Shelton | Away - Shelton HS-Finn Stadium [Directions] | 10:00 a.m. | ||
| Sat., 10/2 | FR Boys Soccer | Westhill | Home - Trumbull HS-Cork Field [Directions] | 5:00 p.m. | ||
| Sat., 10/2 | V Field Hockey | Greenwich | Home - Trumbull HS-McDougall Stadium [Directions] | 5:30 p.m. | L 0-1 | |
| Sat., 10/2 | JV Field Hockey | Greenwich | Home - Trumbull HS-McDougall Stadium [Directions] | 7:00 p.m. | ||
| Sat., 10/2 | FR Field Hockey | Darien | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 2:00 p.m. | ||
| Sat., 10/2 | V Girls Soccer | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 3:00 p.m. | W 1-0 | |
| Sat., 10/2 | JV Girls Soccer | Masuk | Away - Masuk HS-Masuk High School Middle Field [Directions] | Postponed | ||
| Sat., 10/2 | FR Girls Soccer | Ridgefield | Home - Trumbull HS-Cork Field [Directions] | 7:00 p.m. | ||
| Sat., 10/2 | V Girls Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 2:00 p.m. | L 0-3 | |
| Sat., 10/2 | JV Girls Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 3:30 p.m. | ||
| Sat., 10/2 | FR Girls Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 9:00 a.m. | ||
| Mon., 10/4 | V Boys Golf | Greenwich | Away - Round Hill Country Club [Directions] | 3:30 p.m. | Greenwich 157 Trumbull 190 | |
| Mon., 10/4 | V Girls Soccer | Stamford | Away - Stamford HS-SHS Upper Soccer Field [Directions] | 4:00 p.m. | W 2-1 | |
| Mon., 10/4 | JV Girls Soccer | Stamford | Away - Rippowam MS-Upper Soccer/Footballl Field [Directions] | 4:00 p.m. | ||
| Tue., 10/5 | V Boys Cross Country | St. Joseph, TBA, Staples, Westhill | Away - St. Joseph HS-Trail [Directions] | 4:00 p.m. | ||
| Tue., 10/5 | V Boys Golf | New Canaan | Away - CCNC [Directions] | 3:15 p.m. | New Canaan 157 Trumbull 186 | |
| Tue., 10/5 | V Boys Soccer | Stamford | Home - Trumbull HS-Cork Field [Directions] | 5:30 p.m. | W 4-0 | |
| Tue., 10/5 | JV Boys Soccer | Stamford | Home - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Tue., 10/5 | V Girls Cross Country | St. Joseph, TBA, Staples, Westhill | Away - St. Joseph HS-Trail [Directions] | 4:00 p.m. | ||
| Tue., 10/5 | V Field Hockey | Danbury | Home - Trumbull HS-McDougall Stadium [Directions] | 7:00 p.m. | W 3-0 | |
| Tue., 10/5 | JV Field Hockey | Danbury | Home - Trumbull HS-McDougall Stadium [Directions] | 5:30 p.m. | ||
| Tue., 10/5 | V Girls Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Tue., 10/5 | JV Girls Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/6 | SO Football | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Wed., 10/6 | V Boys Golf | Norwalk | Away - Oak Hills Golf Course [Directions] | 3:30 p.m. | Norwalk 177 Trumbull 185 | |
| Wed., 10/6 | FR Boys Soccer | Darien | Home - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | ||
| Wed., 10/6 | FR Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Front Field [Directions] | 4:00 p.m. | ||
| Wed., 10/6 | V Girls Soccer | Staples | Home - Trumbull HS-Cork Field [Directions] | 6:00 p.m. | L 0-1 | |
| Wed., 10/6 | JV Girls Soccer | Staples | Home - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Wed., 10/6 | V Girls Swimming and Diving | Greenwich | Away - Greenwich HS-Pool [Directions] | 4:30 p.m. | ||
| Wed., 10/6 | FR Girls Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:00 p.m. | ||
| Thu., 10/7 | V Boys Golf | The Chappa Memorial | Away - Longshore Golf Course | 3:15 p.m. | ||
| Thu., 10/7 | V Boys Golf | The Chappa Memorial | Away - Longshore Golf Course | TBA | ||
| Thu., 10/7 | V Boys Soccer | Staples | Away - Staples HS-Loeffler Field - Staples HS [Directions] | 4:00 p.m. | L 2-6 | |
| Thu., 10/7 | JV Boys Soccer | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Thu., 10/7 | V Field Hockey | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | L 1-5 | |
| Thu., 10/7 | JV Field Hockey | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Thu., 10/7 | FR Girls Soccer | Masuk | Home - Trumbull HS-The Pit [Directions] | 5:00 p.m. | ||
| Thu., 10/7 | V Girls Volleyball | Fairfield Ludlowe | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Thu., 10/7 | JV Girls Volleyball | Fairfield Ludlowe | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/7 | FR Girls Volleyball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | 5:00 p.m. | ||
| Fri., 10/8 | JV Boys Soccer | Wilton | Home - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Fri., 10/8 | FR Field Hockey | Norwalk | Home - Trumbull HS-McDougall Stadium [Directions] | 5:30 p.m. | ||
| Fri., 10/8 | V Girls Soccer | Wilton | Away - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | L 0-2 | |
| Fri., 10/8 | JV Girls Soccer | Wilton | Away - Allen's Meadow-2A [Directions] | 4:00 p.m. | ||
| Sat., 10/9 | V Football | Westhill | Home - Trumbull HS-McDougall Stadium [Directions] | 12:00 p.m. | W 44-0 | |
| Sat., 10/9 | V Boys Soccer | Wilton | Home - Trumbull HS-Cork Field [Directions] | 10:00 a.m. | T 2-2 | |
| Sat., 10/9 | FR Boys Soccer | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 9:00 a.m. | ||
| Sat., 10/9 | FR Girls Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 10:00 a.m. | ||
| Sat., 10/9 | V Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 12:00 p.m. | L 0-3 | |
| Sat., 10/9 | JV Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 10:30 a.m. | ||
| Sat., 10/9 | FR Girls Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 9:00 a.m. | ||
| Mon., 10/11 | JV Football | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 10:00 a.m. | ||
| Mon., 10/11 | V Field Hockey | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 4:00 p.m. | W 5-0 | |
| Mon., 10/11 | JV Field Hockey | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 5:30 p.m. | ||
| Tue., 10/12 | V Boys Cross Country | Fairfield Ludlowe, Darien, Stamford | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | ||
| Tue., 10/12 | V Boys Golf | Brien McMahon | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | McMahon 191 Trumbull 168 | |
| Tue., 10/12 | V Girls Cross Country | Fairfield Ludlowe, Darien, Stamford | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | ||
| Tue., 10/12 | V Girls Diving | Wilton, St. Joseph | Away - New Canaan YMCA-Pool [Directions] | 4:00 p.m. | ||
| Tue., 10/12 | V Girls Soccer | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 4:00 p.m. | L 2-3 | |
| Tue., 10/12 | JV Girls Soccer | St. Joseph | Away - St. Joseph HS-Lower Grass Field [Directions] | 4:00 p.m. | ||
| Tue., 10/12 | V Girls Volleyball | Bridgeport Central | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Tue., 10/12 | JV Girls Volleyball | Bridgeport Central | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/13 | V Boys Golf | St. Joseph | Home - Tashua Knolls Golf Course [Directions] | 3:30 p.m. | St. Joseph 157 Trumbull 169 | |
| Wed., 10/13 | JV Boys Golf | St. Joseph | Home - Tashua Knolls Golf Course [Directions] | 3:30 p.m. | ||
| Wed., 10/13 | V Boys Soccer | St. Joseph | Home - Trumbull HS-Cork Field [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 10/13 | FR Boys Soccer | Fairfield Warde | Home - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | ||
| Wed., 10/13 | V Field Hockey | Staples | Home - Trumbull HS-McDougall Stadium [Directions] | 7:00 p.m. | L 0-7 | |
| Wed., 10/13 | JV Field Hockey | Staples | Home - Trumbull HS-McDougall Stadium [Directions] | 5:30 p.m. | ||
| Wed., 10/13 | FR Girls Soccer | Weston | Away - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 10/13 | V Girls Swimming and Diving | Wilton | Away - Wilton YMCA [Directions] | 4:00 p.m. | ||
| Wed., 10/13 | V Girls Volleyball | Stamford | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 10/13 | JV Girls Volleyball | Stamford | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/14 | FR Football | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Thu., 10/14 | FR Field Hockey | Fairfield Warde | Home - Trumbull HS-Cork Field [Directions] | 5:30 p.m. | ||
| Thu., 10/14 | V Girls Soccer | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 6:30 p.m. | T 0-0 | |
| Thu., 10/14 | JV Girls Soccer | New Canaan | Away - Conner Field, New Cannan [Directions] | 4:00 p.m. | ||
| Thu., 10/14 | FR Girls Volleyball | St. Joseph | Home - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | ||
| Fri., 10/15 | V Boys Soccer | New Canaan | Home - Trumbull HS-Cork Field [Directions] | 4:00 p.m. | W 1-0 | |
| Fri., 10/15 | JV Boys Soccer | New Canaan | Home - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Fri., 10/15 | V Field Hockey | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 3:30 p.m. | W 6-2 | |
| Fri., 10/15 | V Girls Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:00 p.m. | W 3-2 | |
| Fri., 10/15 | JV Girls Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Sat., 10/16 | V Football | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 12:00 p.m. | W 48-0 | |
| Sat., 10/16 | FR Boys Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 11:00 a.m. | ||
| Sat., 10/16 | FR Field Hockey | Westhill | Away - Westhill HS-Westhill Front Turf Field [Directions] | 9:00 a.m. | ||
| Sat., 10/16 | V Girls Swimming and Diving | Norwalk/McMahon | Home - Orange Town Pool [Directions] | 5:00 p.m. | ||
| Sat., 10/16 | FR Girls Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 10:30 a.m. | ||
| Mon., 10/18 | V Boys Golf | CIAC Fall Division I Boys Golf Championship | Away - Chippanee GC | 8:30 a.m. | ||
| Mon., 10/18 | V Field Hockey | Stamford | Home - Trumbull HS-McDougall Stadium [Directions] | 7:30 p.m. | W 4-2 | |
| Mon., 10/18 | JV Field Hockey | Stamford | Home - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | ||
| Mon., 10/18 | V Girls Soccer | Brien McMahon | Home - Trumbull HS-Cork Field [Directions] | 5:30 p.m. | W 4-1 | |
| Mon., 10/18 | JV Girls Soccer | Brien McMahon | Home - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Mon., 10/18 | V Girls Volleyball | Wilton | Home - Trumbull HS-THS Main Gym [Directions] | 6:30 p.m. | W 3-1 | |
| Mon., 10/18 | JV Girls Volleyball | Wilton | Home - Trumbull HS-THS Main Gym [Directions] | 5:00 p.m. | ||
| Tue., 10/19 | V Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 5:45 p.m. | L 2-3 | |
| Tue., 10/19 | JV Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 4:00 p.m. | ||
| Tue., 10/19 | FR Boys Soccer | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 4:30 p.m. | ||
| Tue., 10/19 | FR Field Hockey | Staples | Home - Trumbull HS-Cork Field [Directions] | 5:30 p.m. | ||
| Wed., 10/20 | V Boys Cross Country | FCIAC Championship @ Waveny Park | Away - Waveny Park, Coppo Field | 2:15 p.m. | ||
| Wed., 10/20 | V Girls Cross Country | FCIAC Championship @ Waveny Park | Away - Trumbull HS-Cross Country Course | 5:00 a.m. | ||
| Wed., 10/20 | V Girls Soccer | Fairfield Warde | Home - Trumbull HS-Cork Field [Directions] | 5:30 p.m. | W 3-1 | |
| Wed., 10/20 | JV Girls Soccer | Fairfield Warde | Home - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Wed., 10/20 | V Girls Swimming and Diving | New Canaan | Away - New Canaan YMCA-Pool [Directions] | 3:00 p.m. | ||
| Wed., 10/20 | V Girls Volleyball | St. Joseph | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 10/20 | JV Girls Volleyball | St. Joseph | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/21 | FR Football | Greenwich | Home - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | ||
| Thu., 10/21 | FR Field Hockey | Greenwich | Away - Cos Cob Park-Binney Park [Directions] | 4:30 p.m. | ||
| Thu., 10/21 | FR Girls Volleyball | Fairfield Ludlowe | Home - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | ||
| Fri., 10/22 | V Football | Greenwich | Home - Trumbull HS-McDougall Stadium [Directions] | 7:00 p.m. | L 12-44 | |
| Fri., 10/22 | V Boys Soccer | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 7:00 p.m. | T 1-1 | |
| Fri., 10/22 | JV Boys Soccer | Fairfield Warde | Away - Fairfield Warde HS-Varsity Grass Soccer Field [Directions] | 4:00 p.m. | ||
| Fri., 10/22 | FR Boys Soccer | New Milford | Home - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | ||
| Fri., 10/22 | V Girls Swimming and Diving | Ridgefield | Away - Barlow Mountain Pool [Directions] | 4:00 p.m. | ||
| Sat., 10/23 | JV Football | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 10:00 a.m. | ||
| Sat., 10/23 | FR Boys Soccer | Fairfield Ludlowe | Home - Trumbull HS-Cork Field [Directions] | 12:00 p.m. | ||
| Sat., 10/23 | FR Girls Soccer | Danbury | Home - Trumbull HS-Cork Field [Directions] | 10:00 a.m. | ||
| Sat., 10/23 | V Girls Volleyball | New Canaan | Home - Trumbull HS-THS Main Gym [Directions] | 11:30 a.m. | W 3-0 | |
| Sat., 10/23 | JV Girls Volleyball | New Canaan | Home - Trumbull HS-THS Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 10/23 | FR Girls Volleyball | Darien | Home - Trumbull HS-THS Main Gym [Directions] | 2:00 p.m. | ||
| Mon., 10/25 | V Field Hockey | Ridgefield | Away - Ridgefield HS-Tiger Hollow Turf Field II [Directions] | 7:00 p.m. | L 2-7 | |
| Mon., 10/25 | JV Field Hockey | Ridgefield | Away - Ridgefield HS-Tiger Hollow Turf Field II [Directions] | 5:15 p.m. | ||
| Mon., 10/25 | V Girls Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 7:00 p.m. | T 2-2 | |
| Mon., 10/25 | JV Girls Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 5:00 p.m. | ||
| Mon., 10/25 | FR Girls Soccer | New Canaan | Home - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Wed., 10/27 | V Boys Soccer | Norwalk | Home - Trumbull HS-Cork Field [Directions] | 6:00 p.m. | L 1-2 | |
| Wed., 10/27 | JV Boys Soccer | Norwalk | Home - Trumbull HS-Cork Field [Directions] | 4:00 p.m. | ||
| Wed., 10/27 | FR Boys Soccer | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | Postponed | ||
| Pending changes awaiting acceptance by one or more parties involved: Date to 10/29, Time to 3:45 p.m. | ||||||
| Wed., 10/27 | FR Girls Soccer | Masuk | Away - Great Hollow Lake Field-Soccer Field [Directions] | Canceled | Cancelled | |
| Wed., 10/27 | V Girls Swimming and Diving | Staples | Away - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Wed., 10/27 | V Girls Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 10/27 | JV Girls Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 10/27 | FR Girls Volleyball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Wed., 10/27 | Miscellaneous Events | Park and Rec. | Home - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | ||
| Thu., 10/28 | V Boys Cross Country | Danbury | Away - Tarrywile Park [Directions] | 4:00 p.m. | ||
| Thu., 10/28 | SO Football | New Canaan | Home - Trumbull HS-Cork Field [Directions] | 5:30 p.m. | ||
| Thu., 10/28 | FR Football | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | ||
| Thu., 10/28 | V Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Thu., 10/28 | JV Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/29 | V Football | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 7:00 p.m. | W 42-6 | |
| Fri., 10/29 | V Field Hockey | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 3:45 p.m. | ||
| Fri., 10/29 | JV Girls Swimming and Diving | Greenwich | Away - Greenwich HS-Pool [Directions] | 6:00 p.m. | ||
| Sat., 10/30 | JV Football | Fairfield Warde | Home - Trumbull HS-McDougall Stadium [Directions] | 10:30 a.m. | ||
| Sat., 10/30 | V Girls Volleyball | Norwalk | Home - Trumbull HS-THS Main Gym [Directions] | 11:30 a.m. | W 3-0 | |
| Sat., 10/30 | JV Girls Volleyball | Norwalk | Home - Trumbull HS-THS Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 10/30 | FR Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 10:00 a.m. | ||
| Mon., 11/1 | V Boys Cross Country | CIAC Boys Cross Country Class LL Championship | Away - Wickham Park | 1:00 p.m. | ||
| Mon., 11/1 | V Girls Cross Country | CIAC Girls Cross Country Class LL Championship | Away - Wickham Park | 1:30 p.m. | ||
| Tue., 11/2 | V Boys Soccer | Foran (Scrim.) | Home - Trumbull HS-Cork Field [Directions] | 3:30 p.m. | ||
| Tue., 11/2 | V Girls Volleyball | Wilton | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 11/3 | MS Boys Cross Country | Madison Invitational | Home - Madison MS-Cross Country Course [Directions] | 4:00 p.m. | ||
| Wed., 11/3 | MS Girls Cross Country | Madison Invitational | Home - Madison MS-Cross Country Course [Directions] | 4:00 p.m. | ||
| Wed., 11/3 | V Girls Soccer | Darien (Scrim.) | Away - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 11/3 | V Girls Swimming and Diving | FCIAC Girls Swim Trials | Away - Greenwich HS | 5:00 p.m. | ||
| Thu., 11/4 | FR Football | Ridgefield | Away - Ridgefield HS-Tiger Hollow Turf Field II [Directions] | 4:00 p.m. | ||
| Thu., 11/4 | V Boys Soccer | Masuk (Scrim.) | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 4:15 p.m. | ||
| Thu., 11/4 | V Field Hockey | Lauralton Hall (Scrim.) | Away - Lauralton Hall-Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 11/4 | V Girls Swimming and Diving | FCIAC Girls Diving Finals | Away - Fairfield County Interscholastic Athletic Conferen-Westhill HS | 5:00 p.m. | ||
| Thu., 11/4 | V Girls Volleyball | Greenwich | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:00 p.m. | ||
| Fri., 11/5 | V Boys Cross Country | CIAC Boys Cross Country Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Fri., 11/5 | V Football | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 7:00 p.m. | W 28-14 | |
| Fri., 11/5 | V Girls Cross Country | CIAC Girls Cross Country Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Sat., 11/6 | JV Football | Ridgefield | Home - Trumbull HS-McDougall Stadium [Directions] | 10:30 a.m. | ||
| Sat., 11/6 | V Girls Swimming and Diving | FCIAC Girls Swim Finals | Away - Fairfield County Interscholastic Athletic Conferen-Greenwich HS | 4:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Greenwich HS | ||||||
| Mon., 11/8 | V Girls Soccer | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 5:30 p.m. | ||
| Mon., 11/8 | V Girls Volleyball | Westhill | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 11/9 | SO Football | Greenwich | Home - Trumbull HS-Cork Field [Directions] | 5:30 p.m. | ||
| Tue., 11/9 | V Boys Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 6:00 p.m. | L 1-3 (OT) | |
| Wed., 11/10 | V Field Hockey | Hall | Away - Hall HS-Stadium (Turf Field) [Directions] | 6:00 p.m. | ||
| Thu., 11/11 | FR Football | Danbury | Home - Trumbull HS-McDougall Stadium [Directions] | 5:30 p.m. | ||
| Thu., 11/11 | V Girls Swimming and Diving | CIAC Class LL Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Thu., 11/11 | V Girls Volleyball | Conard | Away - Conard HS-Main Gym [Directions] | 6:00 p.m. | ||
| Fri., 11/12 | V Football | Danbury | Home - Trumbull HS-McDougall Stadium [Directions] | 7:00 p.m. | W 40-12 | |
| Sat., 11/13 | JV Football | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | Canceled | Cancelled | |
| Sat., 11/13 | V Girls Swimming and Diving | CIAC Class LL Qualifying Meet | Away - East Hartford | 11:30 a.m. | ||
| Wed., 11/17 | SO Football | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 4:30 p.m. | ||
| Wed., 11/17 | V Girls Swimming and Diving | CIAC Class LL Swimming Championships | Away - SCSU | 6:00 p.m. | ||
| Thu., 11/18 | FR Football | St. Joseph | Home - Trumbull HS-McDougall Stadium [Directions] | 4:00 p.m. | ||
| Thu., 11/18 | V Girls Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 11/20 | Miscellaneous Events | Powder Puff | Home - Trumbull HS [Directions] | 10:00 a.m. | ||
| Sun., 11/21 | V Girls Swimming and Diving | CIAC State Open Swimming Championships | Away - Cornerstone Pool | 2:00 p.m. | ||
| Mon., 11/22 | JV Football | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 3:00 p.m. | ||
| Thu., 11/25 | V Football | St. Joseph | Home - Trumbull HS-McDougall Stadium [Directions] | 10:00 a.m. | L 7-35 | |
| Sat., 12/4 | V Boys Ice Hockey | Lyman Hall (Scrim.) | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 3:15 p.m. | ||
| Sat., 12/4 | V Girls Basketball | Daniel Hand (Scrim.) | Away - Daniel Hand HS-DHHS Gym [Directions] | 11:00 a.m. | ||
| Sat., 12/4 | V Girls Ice Hockey | Guilford Coop (Scrim.) | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 5:15 p.m. | ||
| Tue., 12/7 | V Boys Basketball | Shelton (Scrim.) | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 12/8 | V Boys Ice Hockey | Newington Coop (Scrim.) | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 6:30 p.m. | ||
| Wed., 12/8 | V Girls Basketball | Newtown (Scrim.) | Away - Newtown HS-Gym [Directions] | 5:30 p.m. | ||
| Wed., 12/8 | V Girls Basketball | Newtown (Scrim.) | Away - Newtown HS [Directions] | 5:30 p.m. | ||
| Wed., 12/8 | V Girls Ice Hockey | Masuk Coop | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | W 4-3(OT) | |
| Thu., 12/9 | V Boys Basketball | Bunnell (Scrim.) | Home - Trumbull HS-THS Main Gym [Directions] | 3:00 p.m. | ||
| Fri., 12/10 | V Girls Basketball | Pomperaug (Scrim.) | Home - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | ||
| Sun., 12/12 | JV Girls Ice Hockey | West Haven/SHA | Away - West Haven HS-Bennett Rink [Directions] | 6:25 p.m. | ||
| Mon., 12/13 | V Girls Ice Hockey | Hamden Coop | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 5:00 p.m. | W 3-0 | |
| Wed., 12/15 | V Boys Ice Hockey | Watertown-Pomperaug | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 8:30 p.m. | W 5-4 | |
| Wed., 12/15 | V Wrestling | Stamford | Home - Trumbull HS-Aux Gym [Directions] | 7:00 p.m. | ||
| Wed., 12/15 | V Girls Basketball | Hamden | Away - Hamden HS-HHS Gym [Directions] | 7:00 p.m. | L 37-45 | |
| Wed., 12/15 | JV Girls Basketball | Hamden | Away - Hamden HS-HHS Gym [Directions] | 5:15 p.m. | ||
| Wed., 12/15 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice-New [Directions] | 5:00 p.m. | W 6-2 | |
| Thu., 12/16 | V Boys Basketball | Masuk | Home - Trumbull HS-THS Main Gym [Directions] | 7:00 p.m. | W 60-49 | |
| Thu., 12/16 | JV Boys Basketball | Masuk | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 12/16 | FR Boys Basketball | Masuk | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 12/16 | V Boys Swimming and Diving | Staples, St. Joseph | Away - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Thu., 12/16 | JV Wrestling | Fairfield Warde | Home - Trumbull HS-Aux Gym [Directions] | 4:00 p.m. | ||
| Sat., 12/18 | V Boys Basketball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 5:00 p.m. | L 52-59 | |
| Sat., 12/18 | JV Boys Basketball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 3:00 p.m. | ||
| Sat., 12/18 | V Boys Ice Hockey | North Branford | Away - Northford Ice Pavilion-Red [Directions] | 2:30 p.m. | L 1-3 | |
| Sat., 12/18 | V Boys Indoor Track | Staples, Greenwich, Stamford, Westhill | Away - Staples HS-Field House [Directions] | 12:30 p.m. | ||
| Sat., 12/18 | V Wrestling | Manchester, Bristol Central, East Hartford, Glastonbury, TBA, TBA, RHAM, South Windsor | Away - Manchester HS-Gym | 9:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 9:30 a.m. | ||||||
| Sat., 12/18 | V Girls Indoor Track | Staples, Greenwich, Stamford, Westhill | Away - Staples HS-Field House [Directions] | 12:30 p.m. | ||
| Tue., 12/21 | FR Boys Basketball | Harding | Home - Trumbull HS-THS Main Gym [Directions] | 7:00 p.m. | ||
| Wed., 12/22 | V Boys Basketball | Harding | Home - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | W 66-45 | |
| Wed., 12/22 | JV Boys Basketball | Harding | Home - Trumbull HS-THS Main Gym [Directions] | Postponed | ||
| Wed., 12/22 | V Boys Ice Hockey | Guilford | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 6:30 p.m. | W 5-1 | |
| Wed., 12/22 | V Girls Ice Hockey | Conard | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 5:00 p.m. | L 1-2 | |
| Thu., 12/23 | V Girls Basketball | Fairfield Warde | Home - Trumbull HS-THS Main Gym [Directions] | 3:30 p.m. | W 54-32 | |
| Thu., 12/23 | JV Girls Basketball | Fairfield Warde | Home - Trumbull HS-THS Main Gym [Directions] | 2:00 p.m. | ||
| Thu., 12/23 | JV Girls Ice Hockey | Masuk Coop | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 5:00 p.m. | ||
| Mon., 12/27 | V Boys Ice Hockey | Keene Regional (NH) | Away - University of New Hampshire - Durham Campus | 6:00 p.m. | W 3-1 | |
| Mon., 12/27 | JV Wrestling | Brien McMahon, Bristol Eastern, Fairfield Ludlowe, Fairfield Warde, TBA, New Milford, Norwalk, Staples | Home - Trumbull HS-Aux Gym [Directions] | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to TBA | ||||||
| Mon., 12/27 | V Girls Basketball | Bethel | Home - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 4:45 p.m. | W 40-24 | |
| Tue., 12/28 | V Boys Ice Hockey | Portsmouth (NH) | Away - TBA | 7:00 p.m. | T 5-5 | |
| Tue., 12/28 | JV Girls Ice Hockey | Masuk Coop | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | 6:00 p.m. | ||
| Tue., 12/28 | JV Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 7:45 p.m. | ||
| Wed., 12/29 | V Boys Basketball | Stratford | Away - Stratford HS-Gym [Directions] | 5:00 p.m. | W 59-56 | |
| Wed., 12/29 | V Boys Ice Hockey | Oyster River (NH) | Away - University of New Hampshire - Durham Campus-University of New Hampshire - Durham Campus - Whittemore Center | 3:30 p.m. | W 3-2 | |
| Wed., 12/29 | V Girls Basketball | Amity | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 6:30 p.m. | W 41-26 | |
| Wed., 12/29 | JV Girls Ice Hockey | West Haven/SHA | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | Postponed | ||
| Thu., 12/30 | V Wrestling | Trumbull Duals | Home - Trumbull HS-THS Main Gym [Directions] | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to 9:00 a.m. | ||||||
| Mon., 1/3 | JV Boys Ice Hockey | Fairfield Warde/Ludlowe | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 4:00 p.m. | ||
| Wed., 1/5 | V Wrestling | Fairfield Warde | Home - Trumbull HS-Aux Gym [Directions] | Postponed | ||
| Sat., 1/8 | V Boys Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 5:30 p.m. | L 52-70 | |
| Sat., 1/8 | JV Boys Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 1/8 | FR Boys Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 2:30 p.m. | ||
| Sat., 1/8 | V Boys Ice Hockey | Brien McMahon/Norwalk | Away - Sono Ice House-Main Rink [Directions] | 7:50 p.m. | W 8-1 | |
| Sat., 1/8 | V Boys Indoor Track | FCIAC, Bridgeport Central, Brien McMahon, Westhill | Away - Staples HS-Field House | 12:30 p.m. | ||
| Sat., 1/8 | V Wrestling | Guilford, Ledyard, Middletown | Away - Guilford HS-Main gym at GHS [Directions] | 10:00 a.m. | ||
| Sat., 1/8 | JV Wrestling | JV Duals | Home - Trumbull HS-Aux Gym [Directions] | Postponed | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 8:30 a.m. | ||||||
| Sat., 1/8 | V Girls Basketball | Newington | Home - Trumbull HS-THS Main Gym [Directions] | 6:30 p.m. | L 37-49 | |
| Sat., 1/8 | JV Girls Basketball | Newington | Home - Trumbull HS-THS Main Gym [Directions] | 5:00 p.m. | ||
| Sat., 1/8 | V Girls Indoor Track | FCIAC, Brien McMahon, Westhill | Away - Staples HS-Field House | 12:30 p.m. | ||
| Sun., 1/9 | Miscellaneous Events | Southside Wrestling | Home - Trumbull HS-Gym [Directions] | 8:00 a.m. | ||
| Tue., 1/11 | V Boys Basketball | Danbury | Home - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | W 55-50 | |
| Tue., 1/11 | JV Boys Basketball | Danbury | Home - Trumbull HS-THS Main Gym [Directions] | 4:30 p.m. | ||
| Tue., 1/11 | V Boys Swimming and Diving | Danbury, St. Joseph | Away - WCSU O'Neill Center - Blue Gym-O'Neill Center [Directions] | 7:00 p.m. | ||
| Tue., 1/11 | V Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 6:00 p.m. | W 60-47 | |
| Tue., 1/11 | JV Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 4:30 p.m. | ||
| Wed., 1/12 | FR Boys Basketball | Danbury | Home - Trumbull HS-THS Main Gym [Directions] | 7:15 p.m. | ||
| Wed., 1/12 | V Boys Ice Hockey | Staples | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 8:00 p.m. | W 6-3 | |
| Wed., 1/12 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee, St. Joseph | Away - Fairfield University-Pool [Directions] | 6:30 p.m. | ||
| Wed., 1/12 | V Wrestling | Danbury | Home - Trumbull HS-Aux Gym [Directions] | 5:00 p.m. | ||
| Thu., 1/13 | V Girls Gymnastics | Westhill, St. Joseph, Stamford | Away - Westhill HS-New Gym [Directions] | 6:00 p.m. | ||
| Fri., 1/14 | V Boys Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | L 49-60 | |
| Fri., 1/14 | JV Boys Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/14 | V Boys Swimming and Diving | New Canaan, St. Joseph | Away - New Canaan YMCA-Pool [Directions] | 3:00 p.m. | ||
| Sat., 1/15 | FR Boys Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 1:00 p.m. | ||
| Sat., 1/15 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 8:00 p.m. | L 0-8 | |
| Sat., 1/15 | V Boys Indoor Track | FCIAC, Fairfield Warde, St. Joseph, Westhill | Away - Wilton HS-Wilton Field House | 11:00 a.m. | ||
| Sat., 1/15 | V Wrestling | Enfield, East Longmeadow (MA), Longmeadow (MA), Maloney, TBA, TBA, Nonnewaug, Rockville, Rocky Hill | Away - Enfield HS-EHS GYM - MAIN | 10:00 a.m. | ||
| Sat., 1/15 | V Wrestling | Norwalk, Danbury, Fairfield Warde, Greens Farms Academy, TBA, New Milford, Simsbury | Away - Norwalk HS-Tom Scarso Gymnasium | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to 9:30 a.m. | ||||||
| Sat., 1/15 | JV Wrestling | Norwalk, Fairfield Warde | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 8:30 a.m. | ||
| Sat., 1/15 | V Girls Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | 5:50 p.m. | L 1-6 | |
| Sat., 1/15 | V Girls Indoor Track | FCIAC, Fairfield Ludlowe, St. Joseph, Westhill | Away - Wilton HS-Wilton Field House | 11:00 a.m. | ||
| Mon., 1/17 | V Girls Gymnastics | Darien, New Canaan, St. Joseph | Home - Next Dimension Gymnastics-Next Dimension [Directions] | 1:00 p.m. | Trumbull-136.2 ; Darien-126.35 ; New Canaan-52.3 | |
| Mon., 1/17 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 3:30 p.m. | W 6-2 | |
| Tue., 1/18 | V Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 7:00 p.m. | L 48-77 | |
| Tue., 1/18 | JV Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/18 | FR Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/18 | V Girls Basketball | Ridgefield | Home - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | L 33-45 | |
| Tue., 1/18 | JV Girls Basketball | Ridgefield | Home - Trumbull HS-THS Main Gym [Directions] | 4:30 p.m. | ||
| Wed., 1/19 | V Boys Ice Hockey | Branford | Away - Northford Ice Pavilion-Red [Directions] | 3:50 p.m. | W 4-1 | |
| Wed., 1/19 | V Boys Swimming and Diving | Greenwich, St. Joseph | Away - Greenwich HS-Pool [Directions] | 4:00 p.m. | ||
| Wed., 1/19 | V Wrestling | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 6:30 p.m. | ||
| Fri., 1/21 | V Boys Swimming and Diving | Westhill/Stamford, St. Joseph | Away - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Fri., 1/21 | V Girls Basketball | Darien | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | W 54-21 | |
| Fri., 1/21 | JV Girls Basketball | Darien | Home - Trumbull HS-THS Main Gym [Directions] | Postponed | ||
| Fri., 1/21 | V Girls Ice Hockey | Masuk Coop | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | W 2-0 | |
| Sat., 1/22 | V Boys Basketball | Fairfield Ludlowe | Home - Trumbull HS-THS Main Gym [Directions] | 3:00 p.m. | W 51-50 | |
| Sat., 1/22 | JV Boys Basketball | Fairfield Ludlowe | Home - Trumbull HS-THS Main Gym [Directions] | 1:30 p.m. | ||
| Sat., 1/22 | FR Boys Basketball | Fairfield Ludlowe | Home - Trumbull HS-THS Main Gym [Directions] | 12:00 p.m. | ||
| Sat., 1/22 | V Boys Ice Hockey | Greenwich | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 7:30 p.m. | L 2-3 | |
| Sat., 1/22 | V Boys Indoor Track | FCIAC, Fairfield Warde, Ridgefield, Westhill | Away - Staples HS-Field House | 12:30 p.m. | ||
| Sat., 1/22 | V Wrestling | Xavier, Bristol Central, Bristol Eastern, Burlington (MA), Cheshire, Fitch, Guilford, Joel Barlow, TBA, Pomperaug, Ridgefield, Simsbury, Hall, Xaverian Brothers (MA) | Away - Xavier HS-Gym | 9:00 a.m. | ||
| Sat., 1/22 | JV Wrestling | Danbury, Bristol Central, Bunnell, Fairfield Warde, TBA, TBA, TBA, New Fairfield, Norwalk, Simsbury, Staples | Away - Danbury HS-Main Gym | 9:30 a.m. | ||
| Sat., 1/22 | V Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 6:00 p.m. | L 22-50 | |
| Sat., 1/22 | JV Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | Postponed | ||
| Sat., 1/22 | V Girls Gymnastics | Foran, St. Joseph, Wilton | Home - Next Dimension Gymnastics-Next Dimension [Directions] | 6:00 p.m. | Trumbull-137.45 ; Wilton-123.55 ; Foran-113.6 | |
| Sat., 1/22 | V Girls Ice Hockey | Darien | Away - Darien Ice House-Ice Rink [Directions] | 6:00 p.m. | L 0-3 | |
| Sat., 1/22 | V Girls Indoor Track | FCIAC, Fairfield Warde, Ridgefield, Westhill | Away - Staples HS-Field House | 12:30 p.m. | ||
| Sun., 1/23 | V Girls Ice Hockey | Greenwich | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 2:00 p.m. | L 1-4 | |
| Mon., 1/24 | V Boys Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 6:00 p.m. | L 43-60 | |
| Mon., 1/24 | JV Boys Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | ||
| Mon., 1/24 | V Girls Basketball | Greenwich | Home - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | L 59-63 | |
| Mon., 1/24 | JV Girls Basketball | Greenwich | Home - Trumbull HS-THS Main Gym [Directions] | 4:30 p.m. | ||
| Mon., 1/24 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 7:15 p.m. | W 4-1 | |
| Tue., 1/25 | V Girls Basketball | Westhill | Home - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | W 59-37 | |
| Tue., 1/25 | JV Girls Basketball | Westhill | Home - Trumbull HS-THS Main Gym [Directions] | 4:30 p.m. | ||
| Wed., 1/26 | V Boys Ice Hockey | Ridgefield | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:30 p.m. | L 1-3 | |
| Wed., 1/26 | V Wrestling | Brien McMahon | Home - Trumbull HS-Aux Gym [Directions] | 5:00 p.m. | ||
| Wed., 1/26 | V Girls Gymnastics | Fairfield Warde, St. Joseph | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:30 p.m. | ||
| Wed., 1/26 | V Girls Gymnastics | Fairfield Ludlowe, St. Joseph | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:30 p.m. | Trumbull- 136.4 ; Ludlowe- 137.3 ; Warde- 136.8 | |
| Thu., 1/27 | V Boys Basketball | Norwalk | Home - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | L 40-47 | |
| Thu., 1/27 | JV Boys Basketball | Norwalk | Home - Trumbull HS-THS Main Gym [Directions] | 4:30 p.m. | ||
| Thu., 1/27 | JV Boys Ice Hockey | St. Joseph | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 4:00 p.m. | ||
| Thu., 1/27 | V Girls Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 6:15 p.m. | W 34-30 | |
| Thu., 1/27 | JV Girls Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:30 p.m. | ||
| Fri., 1/28 | FR Boys Basketball | Norwalk | Home - Trumbull HS-THS Main Gym [Directions] | 7:15 p.m. | ||
| Fri., 1/28 | V Girls Ice Hockey | New Canaan | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 5:30 p.m. | L 0-5 | |
| Sat., 1/29 | V Wrestling | SOUTHINGTON CHALLENGE | Away - Southington HS-Gym West | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to 7:00 a.m. | ||||||
| Sat., 1/29 | V Wrestling | Norwalk, Brien McMahon, Darien, Fairfield Ludlowe, Fairfield Warde, Greens Farms Academy, Greenwich, TBA, TBA, TBA, Notre Dame-Fairfield, Ridgefield, St. Joseph, Staples, Weston | Away - Norwalk HS-Tom Scarso Gymnasium | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to 9:00 a.m. | ||||||
| Mon., 1/31 | JV Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena-Patriot Rink [Directions] | 5:00 p.m. | ||
| Tue., 2/1 | V Boys Basketball | Stamford | Home - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | L 43-56 | |
| Tue., 2/1 | JV Boys Basketball | Stamford | Home - Trumbull HS-THS Main Gym [Directions] | 4:30 p.m. | ||
| Tue., 2/1 | V Girls Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 6:00 p.m. | L 41-59 | |
| Tue., 2/1 | JV Girls Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | ||
| Tue., 2/1 | V Girls Ice Hockey | Daniel Hand Coop | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 8:30 p.m. | W 3-1 | |
| Wed., 2/2 | FR Boys Basketball | Stamford | Home - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | ||
| Wed., 2/2 | V Boys Ice Hockey | St. Joseph | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 6:30 p.m. | W 2-1 | |
| Wed., 2/2 | V Wrestling | Staples | Away - Staples HS-Staples Gym [Directions] | 7:00 p.m. | ||
| Wed., 2/2 | V Girls Basketball | Bridgeport Central | Away - Bridgeport Central HS-Barry McLeod Court [Directions] | 6:00 p.m. | W 52-7 | |
| Wed., 2/2 | JV Girls Basketball | Bridgeport Central | Away - Bridgeport Central HS-Barry McLeod Court [Directions] | 4:30 p.m. | ||
| Wed., 2/2 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | W 8-2 | |
| Thu., 2/3 | V Boys Indoor Track | FCIAC Indoor Track Championships | Away - Floyd Little Athletic Center-Field House | 4:30 p.m. | ||
| Thu., 2/3 | V Girls Gymnastics | Greenwich, St. Joseph | Away - Greenwich YWCA [Directions] | 6:30 p.m. | Trumbull- 137.75; Greenwich- 129.25 | |
| Thu., 2/3 | JV Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 8:00 p.m. | ||
| Thu., 2/3 | V Girls Indoor Track | FCIAC Indoor Track Championships | Away - Floyd Little Athletic Center-Field House | 4:30 p.m. | ||
| Fri., 2/4 | JV Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland of Ice-Stadium [Directions] | Postponed | ||
| Fri., 2/4 | JV Girls Basketball | Staples | Home - Trumbull HS-THS Main Gym [Directions] | Canceled | Cancelled | |
| Fri., 2/4 | Miscellaneous Events | Unified | Home - Trumbull HS-THS Main Gym [Directions] | 6:30 p.m. | ||
| Sat., 2/5 | V Boys Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 1:00 p.m. | L 63-71 | |
| Sat., 2/5 | JV Boys Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 11:15 a.m. | ||
| Sat., 2/5 | FR Boys Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 10:00 a.m. | ||
| Sat., 2/5 | V Wrestling | Ridgefield, Westhill, Wilton | Away - Ridgefield HS-Aux Gym [Directions] | 11:00 a.m. | ||
| Sat., 2/5 | JV Wrestling | Fairfield Ludlowe, Fairfield Warde | Away - Fairfield Ludlowe HS-Main Gym [Directions] | Canceled | Cancelled | |
| Sat., 2/5 | V Girls Basketball | Staples | Home - Trumbull HS-THS Main Gym [Directions] | 5:00 p.m. | L 23-35 | |
| Sat., 2/5 | JV Girls Basketball | E.O. Smith | Away - E.O. Smith HS-Front Gym [Directions] | Canceled | Cancelled | |
| Sat., 2/5 | JV Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice-New [Directions] | Postponed | ||
| Sat., 2/5 | Miscellaneous Events | FCIAC Cheer | Home - Trumbull HS-Gym [Directions] | 12:00 p.m. | ||
| Sun., 2/6 | JV Girls Ice Hockey | Masuk Coop | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:45 p.m. | ||
| Mon., 2/7 | V Boys Ice Hockey | Westhill/Stamford | Away - Terry Conners - Stamford-Ice Rink [Directions] | 1:00 p.m. | L 1-5 | |
| Mon., 2/7 | JV Boys Ice Hockey | Darien | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | Canceled | Cancelled | |
| Mon., 2/7 | V Wrestling | Greenwich | Home - Trumbull HS-Aux Gym [Directions] | 5:00 p.m. | ||
| Mon., 2/7 | V Girls Ice Hockey | Greenwich | Away - Greenwich - Dorothy Hamill-Rink [Directions] | 4:30 p.m. | L 3-5 | |
| Tue., 2/8 | V Boys Basketball | Wilton | Home - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | L 52-69 | |
| Tue., 2/8 | JV Boys Basketball | Wilton | Home - Trumbull HS-THS Main Gym [Directions] | 4:30 p.m. | ||
| Tue., 2/8 | JV Boys Ice Hockey | St. Joseph | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | 3:00 p.m. | ||
| Tue., 2/8 | V Wrestling | Darien | Away - Darien HS-DHS South Gym [Directions] | 6:00 p.m. | ||
| Tue., 2/8 | V Girls Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:15 p.m. | L 24-61 | |
| Tue., 2/8 | JV Girls Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Tue., 2/8 | V Girls Gymnastics | Staples, Norwalk, St. Joseph | Away - Westport YMCA [Directions] | 6:30 p.m. | Trumbull- 130.5; Staples- 132.6; Norwalk- 81.2 | |
| Wed., 2/9 | FR Boys Basketball | Wilton | Home - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | ||
| Wed., 2/9 | V Boys Ice Hockey | Brien McMahon/Norwalk | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 6:30 p.m. | W 8-1 | |
| Wed., 2/9 | V Boys Swimming and Diving | Wilton, St. Joseph | Away - Wilton YMCA [Directions] | 3:40 p.m. | ||
| Wed., 2/9 | V Girls Basketball | E.O. Smith | Away - E.O. Smith HS-Front Gym [Directions] | 4:00 p.m. | L 43-44 | |
| Wed., 2/9 | V Girls Gymnastics | St. Joseph, Stamford, Westhill | Home - Westhill HS-New Gym [Directions] | 6:00 p.m. | Trumbull- 127; Stamford- 118.45; Westhill- 77.95 | |
| Wed., 2/9 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Conners - Stamford-Ice Rink [Directions] | 5:30 p.m. | L 2-5 | |
| Thu., 2/10 | JV Boys Ice Hockey | Masuk | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 4:00 p.m. | ||
| Fri., 2/11 | V Boys Basketball | St. Joseph | Home - Trumbull HS-THS Main Gym [Directions] | 7:30 p.m. | L 61-68 | |
| Fri., 2/11 | V Boys Indoor Track | Class LL Championship | Away - Floyd Little Athletic Center | 4:00 p.m. | ||
| Fri., 2/11 | V Wrestling | FCIAC, Danbury, Darien, Fairfield Ludlowe, Fairfield Warde, Greenwich, TBA, New Canaan, Norwalk, Ridgefield, St. Joseph, Stamford, Staples, Westhill, Wilton | Away - New Canaan HS-Main Gym | 4:30 p.m. | ||
| Fri., 2/11 | V Girls Basketball | St. Joseph | Home - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | L 22-44 | |
| Fri., 2/11 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 5:30 p.m. | W 3-2 | |
| Fri., 2/11 | V Girls Indoor Track | Class LL Championship | Away - Floyd Little Athletic Center | 4:00 p.m. | ||
| Sat., 2/12 | JV Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 9:30 a.m. | ||
| Sat., 2/12 | V Boys Ice Hockey | Staples | Away - Milford Ice Pavillion-Ice Rink [Directions] | 4:30 p.m. | W 6-1 | |
| Sat., 2/12 | V Boys Swimming and Diving | Darien | Home - Orange Town Pool [Directions] | 3:00 p.m. | ||
| Sat., 2/12 | V Wrestling | FCIAC Wrestling Championships Wrestlebacks | Away - New Canaan HS-Main Gym | 10:00 a.m. | ||
| Sat., 2/12 | JV Girls Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 11:00 a.m. | ||
| Sat., 2/12 | V Girls Gymnastics | FCIAC Gymnastics Championships | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 | 11:00 a.m. | 134.1 | |
| Sun., 2/13 | JV Girls Ice Hockey | West Haven/SHA | Away - West Haven HS-Bennett Rink [Directions] | 1:00 p.m. | ||
| Mon., 2/14 | V Boys Basketball | New Canaan | Home - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | W 47-36 | |
| Mon., 2/14 | JV Boys Basketball | New Canaan | Home - Trumbull HS-THS Main Gym [Directions] | 4:30 p.m. | ||
| Mon., 2/14 | V Boys Ice Hockey | Masuk | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 4:00 p.m. | L 1-6 | |
| Mon., 2/14 | V Girls Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 6:15 p.m. | W 58-49 | |
| Mon., 2/14 | JV Girls Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:30 p.m. | ||
| Mon., 2/14 | V Girls Ice Hockey | Darien | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 7:15 p.m. | L 1-3 | |
| Tue., 2/15 | FR Boys Basketball | New Canaan | Home - Trumbull HS-THS Main Gym [Directions] | 7:15 p.m. | ||
| Tue., 2/15 | V Boys Swimming and Diving | Ridgefield, St. Joseph | Away - Barlow Mountain Pool [Directions] | 4:00 p.m. | ||
| Tue., 2/15 | JV Wrestling | Fairfield Ludlowe, Southington, Stratford | Home - Trumbull HS-Aux Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/15 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 6:00 p.m. | W 5-1 | |
| Wed., 2/16 | V Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 7:00 p.m. | W 61-50 | |
| Wed., 2/16 | JV Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 2/16 | FR Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 2/16 | V Boys Swimming and Diving | Norwalk/Brien McMahon, St. Joseph | Away - Norwalk HS-Pat Spinola Natatorium [Directions] | 4:00 p.m. | ||
| Wed., 2/16 | V Girls Basketball | Brien McMahon | Home - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | W 55-28 | |
| Wed., 2/16 | JV Girls Basketball | Brien McMahon | Home - Trumbull HS-THS Main Gym [Directions] | 4:30 p.m. | ||
| Wed., 2/16 | JV Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 3:45 p.m. | ||
| Wed., 2/16 | Miscellaneous Events | Unified | Home - Trumbull HS-Gym [Directions] | 6:30 p.m. | ||
| Thu., 2/17 | V Boys Basketball | Joel Barlow | Home - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | L 42-44 | |
| Thu., 2/17 | V Boys Ice Hockey | Westhill/Stamford | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 7:30 p.m. | L 1-2 | |
| Fri., 2/18 | V Wrestling | TBA | Home - Trumbull HS-THS Main Gym [Directions] | 1:45 p.m. | ||
| Fri., 2/18 | V Wrestling | Class LL Championship - Day 1 | Away - Trumbull | 1:45 p.m. | ||
| Fri., 2/18 | V Girls Ice Hockey | Stamford/Westhill/Staples | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 5:30 p.m. | L 2-5 | |
| Sat., 2/19 | JV Boys Ice Hockey | Darien | Away - Stamford Twin Rinks-West [Directions] | 8:25 p.m. | ||
| Sat., 2/19 | V Boys Indoor Track | State Open | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/19 | V Wrestling | Class LL Championship - Day 2 | Away - Trumbull | 12:00 p.m. | ||
| Sat., 2/19 | V Wrestling | TBA | Home - Trumbull HS-THS Main Gym [Directions] | 12:00 p.m. | ||
| Sat., 2/19 | V Girls Basketball | St. Joseph | Away - Staples HS-Staples Gym [Directions] | 7:00 p.m. | ||
| Sat., 2/19 | V Girls Gymnastics | St. Joseph | Home - Next Dimension Gymnastics-Next Dimension [Directions] | 6:00 p.m. | 130.35 | |
| Sat., 2/19 | V Girls Indoor Track | State Open | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Mon., 2/21 | V Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 7:00 p.m. | L 56-68 | |
| Mon., 2/21 | JV Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 5:15 p.m. | ||
| Mon., 2/21 | FR Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 3:45 p.m. | ||
| Mon., 2/21 | JV Boys Ice Hockey | Newtown/New Fairfield | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 4:00 p.m. | ||
| Mon., 2/21 | JV Wrestling | Simsbury, Avon, Berlin, Bristol Central, Bristol Eastern, Conard, East Hartford, East Haven, Enfield, Farmington, Maloney, Manchester, New Britain, New Fairfield, New Milford, Platt, Rocky Hill, South Windsor, Wethersfield, Windsor, Hall | Away - Simsbury HS-Simsbury / Main Gym | 9:30 a.m. | ||
| Tue., 2/22 | Miscellaneous Events | FCIAC G. Hoops Semi-Finals | Home - Trumbull HS-Gym [Directions] | 6:00 p.m. | ||
| Wed., 2/23 | V Boys Basketball | Bridgeport Central | Home - Trumbull HS-THS Main Gym [Directions] | 7:00 p.m. | W 63-53 | |
| Wed., 2/23 | JV Boys Basketball | Bridgeport Central | Home - Trumbull HS-THS Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 2/23 | FR Boys Basketball | Bridgeport Central | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/23 | V Boys Ice Hockey | Cheshire | Away - Hamden-Lou Astorino Ice Rink [Directions] | 8:00 p.m. | W 5-1 | |
| Wed., 2/23 | V Girls Basketball | North Haven (Scrim.) | Away - North Haven HS-Fred Kelly Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 2/24 | Miscellaneous Events | FCIAC G. Hoops Finals | Home - Trumbull HS-THS Main Gym [Directions] | 7:00 p.m. | ||
| Sat., 2/26 | V Boys Ice Hockey | Darien | Away - Darien Ice House-Ice Rink [Directions] | 7:30 p.m. | ||
| Sat., 2/26 | V Wrestling | State Open - Day 1 | Away - Floyd Little Athletic Center | 12:45 p.m. | ||
| Sat., 2/26 | V Girls Basketball | Pomperaug (Scrim.) | Away - Pomperaug HS-Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 2/26 | V Girls Gymnastics | CIAC Class L Divisional Championship | Away - Richetelli Gymnasium @Jonathan Law | 2:00 p.m. | ||
| Sat., 2/26 | Miscellaneous Events | Band Show | Home - Trumbull HS-THS Main Gym [Directions] | 9:00 a.m. | ||
| Sun., 2/27 | V Wrestling | State Open - Day 2 | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Sun., 2/27 | Miscellaneous Events | Babe Ruth | Home - Trumbull HS-THS Main Gym [Directions] | 1:00 p.m. | ||
| Mon., 2/28 | V Girls Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:30 p.m. | ||
| Mon., 2/28 | V Girls Ice Hockey | East Catholic Coop | Away - Newington Ice Arena-Red Rink [Directions] | 6:40 p.m. | ||
| Tue., 3/1 | V Boys Swimming and Diving | FCIAC Boys' Swim Trials | Away - Greenwich HS | 5:30 p.m. | ||
| Wed., 3/2 | FR Boys Basketball | St. Joseph | Home - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | ||
| Wed., 3/2 | V Boys Ice Hockey | Immaculate | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 4:00 p.m. | L 3-4 | |
| Wed., 3/2 | V Boys Swimming and Diving | FCIAC Diving Finals | Away - Westhill High-Westhill HS | 5:00 p.m. | ||
| Thu., 3/3 | V Boys Basketball | Bassick (Scrim.) | Home - Trumbull HS-THS Main Gym [Directions] | 3:00 p.m. | ||
| Thu., 3/3 | V Boys Swimming and Diving | FCIAC Boys' Swim Finals | Away - Greenwich HS | 6:30 p.m. | ||
| Sat., 3/5 | V Girls Gymnastics | State Open | Away - New Milford | 10:00 a.m. | ||
| Sat., 3/5 | Miscellaneous Events | Band Show | Home - Trumbull HS-THS Main Gym [Directions] | 9:00 a.m. | ||
| Sat., 3/5 | Miscellaneous Events | Unified Cheer | Home - Floyd Little Athletic Center-Field House [Directions] | TBA | ||
| Sun., 3/6 | Miscellaneous Events | Babe Ruth | Home - Trumbull HS-THS Main Gym [Directions] | 1:00 p.m. | ||
| Tue., 3/8 | V Boys Basketball | West Haven | Away - West Haven HS-Gym [Directions] | 6:30 p.m. | ||
| Tue., 3/8 | V Boys Ice Hockey | Woodstock Academy | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 6:30 p.m. | ||
| Sun., 3/13 | V Boys Swimming and Diving | CIAC Class LL Qualifying Meet | Away - Cornerstone Pool | 5:30 p.m. | ||
| Mon., 3/14 | V Boys Swimming and Diving | CIAC Class LL Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Wed., 3/16 | V Boys Swimming and Diving | CIAC Class LL Swimming Championships | Away - Cornerstone Pool | 1:30 p.m. | ||
| Thu., 3/17 | V Boys Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/19 | V Boys Swimming and Diving | CIAC State Open Swimming Championships | Away - Cornerstone Pool | 3:15 p.m. | ||
| Wed., 3/23 | V Boys Lacrosse | Notre Dame-West Haven (Scrim.) | Home - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | ||
| Wed., 3/23 | V Softball | Amity (Scrim.) | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 4:00 p.m. | ||
| Fri., 3/25 | V Baseball | Staples (Scrim.) | Away - Staples HS-Baseball Diamond [Directions] | Canceled | Cancelled | |
| Fri., 3/25 | JV Baseball | Staples (Scrim.) | Home - Trumbull HS-Varsity Baseball Field [Directions] | Canceled | Cancelled | |
| Fri., 3/25 | V Softball | New Milford (Scrim.) | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 4:00 p.m. | Cancelled | |
| Sat., 3/26 | V Baseball | Bunnell (Scrim.) | Away - Bunnell HS-Bunnell Baseball Field [Directions] | 11:00 a.m. | ||
| Sat., 3/26 | JV Baseball | Bunnell (Scrim.) | Home - Trumbull HS-JV Baseball Field [Directions] | Canceled | Cancelled | |
| Sat., 3/26 | V Boys Lacrosse | Brookfield (Scrim.) | Home - Trumbull HS-McDougall Stadium [Directions] | 10:00 a.m. | ||
| Sat., 3/26 | JV Boys Lacrosse | Brookfield (Scrim.) | Home - Trumbull HS-The Pit [Directions] | Canceled | Cancelled | |
| Sat., 3/26 | V Softball | Maloney (Scrim.) | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 10:30 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 10:15 a.m. | ||||||
| Sat., 3/26 | V Softball | Naugatuck (Scrim.) | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 1:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 1:15 p.m. | ||||||
| Sat., 3/26 | Miscellaneous Events | G. Lax Scrimmage at Stratford Penders Field | Home - Stratford HS-Penders Field [Directions] | 3:00 p.m. | ||
| Mon., 3/28 | V Baseball | Notre Dame-Fairfield (Scrim.) | Away - Notre Dame - Fairfield -Fabbri Field [Directions] | 3:30 p.m. | Cancelled | |
| Tue., 3/29 | V Baseball | Newtown (Scrim.) | Home - Trumbull HS-Varsity Baseball Field [Directions] | Canceled | Cancelled | |
| Tue., 3/29 | JV Baseball | Newtown (Scrim.) | Home - Trumbull HS-JV Baseball Field [Directions] | Canceled | Cancelled | |
| Tue., 3/29 | V Boys Lacrosse | Cheshire (Scrim.) | Home - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | ||
| Tue., 3/29 | JV Boys Lacrosse | Cheshire (Scrim.) | Home - Trumbull HS-Cork Field [Directions] | 4:00 p.m. | ||
| Tue., 3/29 | V Boys Volleyball | Shelton (Scrim.) | Away - Shelton HS-Murray Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 3/29 | JV Boys Volleyball | Shelton (Scrim.) | Away - Shelton HS-Murray Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 3/30 | V Baseball | Seymour (Scrim.) | Home - Trumbull HS-Varsity Baseball Field [Directions] | 4:45 p.m. | ||
| Wed., 3/30 | JV Baseball | Seymour (Scrim.) | Home - Trumbull HS-JV Baseball Field [Directions] | Canceled | Cancelled | |
| Wed., 3/30 | V Boys Volleyball | Joel Barlow (Scrim.) | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 3/31 | V Softball | Amity (Scrim.) | Away - Amity Regional HS-Amity HS - Softball Field [Directions] | 4:00 p.m. | ||
| Fri., 4/1 | V Boys Rugby | Simsbury | Away - Holden Field-Simsbury 2 [Directions] | 6:00 p.m. | ||
| Fri., 4/1 | V Girls Lacrosse | Norwalk (Scrim.) | Away - Norwalk HS-Testa Field [Directions] | 5:30 p.m. | W 11-10 | |
| Fri., 4/1 | V Softball | Woodland (Scrim.) | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 4:00 p.m. | Cancelled | |
| Sat., 4/2 | V Baseball | Masuk | Home - Trumbull HS-Varsity Baseball Field [Directions] | 11:00 a.m. | W 10-2 | |
| Sat., 4/2 | JV Baseball | Masuk | Home - Trumbull HS-JV Baseball Field [Directions] | 11:00 a.m. | ||
| Sat., 4/2 | V Boys Lacrosse | Conard | Away - Conard HS-McKee Stadium [Directions] | 10:00 a.m. | L 2-7 | |
| Sat., 4/2 | JV Boys Lacrosse | Conard | Away - Conard HS-North Field [Directions] | 10:00 a.m. | ||
| Sat., 4/2 | V Boys Volleyball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 10:45 a.m. | W 3-0 | |
| Sat., 4/2 | JV Boys Volleyball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 9:30 a.m. | ||
| Mon., 4/4 | V Baseball | Conard | Away - Conard HS-Baseball Diamond [Directions] | 4:15 p.m. | L 3-2 | |
| Mon., 4/4 | V Boys Outdoor Track | Norwalk | Home - Trumbull HS-McDougall Stadium [Directions] | 4:00 p.m. | ||
| Mon., 4/4 | V Boys Volleyball | Newtown | Away - Newtown HS-Gym [Directions] | 5:45 p.m. | W 3-0 | |
| Mon., 4/4 | JV Boys Volleyball | Newtown | Away - Newtown HS-Gym [Directions] | 4:30 p.m. | ||
| Mon., 4/4 | V Girls Outdoor Track | Norwalk | Home - Trumbull HS-McDougall Stadium [Directions] | 4:00 p.m. | ||
| Mon., 4/4 | V Softball | Pomperaug | Away - Community House Park-Softball Field [Directions] | 4:15 p.m. | W 6-5 | |
| Tue., 4/5 | V Boys Lacrosse | Masuk | Home - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | W 6-4 | |
| Tue., 4/5 | JV Boys Lacrosse | Masuk | Home - Trumbull HS-Cork Field [Directions] | Canceled | Cancelled | |
| Tue., 4/5 | JV Boys Lacrosse | Weston | Home - Trumbull HS-Cork Field [Directions] | 4:00 p.m. | ||
| Tue., 4/5 | V Girls Golf | St. Joseph | Away - Tashua Knolls Golf Course [Directions] | 3:00 p.m. | THS 197; St. Joseph 232 | |
| Tue., 4/5 | JV Girls Golf | St. Joseph | Home - Tashua Knolls Golf Course-Tashua Glen [Directions] | 3:15 p.m. | ||
| Tue., 4/5 | V Girls Lacrosse | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 6:30 p.m. | L 7-20 | |
| Tue., 4/5 | JV Girls Lacrosse | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 5:00 p.m. | ||
| Tue., 4/5 | V Softball | Westhill | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 4:15 p.m. | W 15-4 | |
| Tue., 4/5 | JV Softball | Westhill | Home - Trumbull HS-JV Softball Diamond [Directions] | 6:00 p.m. | ||
| Wed., 4/6 | FR Boys Lacrosse | Wilton | Away - Wilton HS-Veterans Memorial Stadium [Directions] | Canceled | Cancelled | |
| Wed., 4/6 | FR Girls Lacrosse | Wilton | Home - Trumbull HS-The Pit [Directions] | 4:30 p.m. | ||
| Wed., 4/6 | V Girls Rugby | Staples | Away - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Thu., 4/7 | V Boys Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Thu., 4/7 | JV Boys Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 5:30 p.m. | ||
| Fri., 4/8 | FR Boys Lacrosse | Stamford | Away - Stamford HS-Upper Lacrosse Field [Directions] | Postponed | ||
| Fri., 4/8 | V Boys Outdoor Track | Staples | Away - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Fri., 4/8 | V Boys Rugby | Staples | Home - Trumbull HS-Cork Field [Directions] | 7:00 p.m. | ||
| Fri., 4/8 | JV Boys Rugby | Staples | Home - Trumbull HS-McDougall Stadium [Directions] | 5:00 p.m. | ||
| Fri., 4/8 | FR Girls Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 3:45 p.m. | ||
| Fri., 4/8 | V Girls Outdoor Track | Staples | Away - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Fri., 4/8 | JV Softball | Greenwich | Away - Greenwich HS-Softball Field [Directions] | Postponed | ||
| Sat., 4/9 | FR Baseball | Masuk | Away - Masuk HS-John Giampaolo Baseball Field @ Masuk HS [Directions] | Postponed | ||
| Sat., 4/9 | V Boys Lacrosse | Staples | Home - Trumbull HS-McDougall Stadium [Directions] | 12:00 p.m. | L 3-22 | |
| Sat., 4/9 | JV Boys Lacrosse | Staples | Home - Trumbull HS-McDougall Stadium [Directions] | 10:00 a.m. | ||
| Sat., 4/9 | JV Boys Tennis | Greenwich | Away - Central MS [Directions] | Postponed | ||
| Sat., 4/9 | V Softball | Ledyard | Away - Ledyard HS-Ellen Mahoney Softball Complex [Directions] | 12:00 p.m. | W 8-2 | |
| Sat., 4/9 | JV Softball | Ledyard | Away - Ledyard HS-Ellen Mahoney Softball Complex [Directions] | Canceled | Cancelled | |
| Mon., 4/11 | V Baseball | Amity | Away - Amity Regional HS-John Janenda Field [Directions] | 4:00 p.m. | L 6-5 | |
| Mon., 4/11 | V Boys Outdoor Track | Brien McMahon | Home - Trumbull HS-McDougall Stadium [Directions] | 4:00 p.m. | ||
| Mon., 4/11 | V Boys Tennis | Westhill | Away - Westhill HS-Westhill Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Mon., 4/11 | V Boys Volleyball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 5:30 p.m. | W 3-0 | |
| Mon., 4/11 | JV Boys Volleyball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 4/11 | FR Girls Lacrosse | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 4/11 | V Girls Outdoor Track | Brien McMahon | Home - Trumbull HS-McDougall Stadium [Directions] | 4:00 p.m. | ||
| Mon., 4/11 | V Girls Tennis | Westhill | Home - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Mon., 4/11 | JV Girls Tennis | Wilton | Away - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/12 | FR Baseball | Amity | Away - Amity Regional HS-John Janenda Field [Directions] | 4:00 p.m. | ||
| Tue., 4/12 | V Boys Tennis | Danbury | Home - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 4/12 | V Girls Golf | Danbury | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | THS 187; DHS 232 | |
| Tue., 4/12 | JV Girls Golf | Danbury | Home - Tashua Knolls Golf Course-Tashua Glen [Directions] | 3:15 p.m. | ||
| Tue., 4/12 | V Girls Lacrosse | Weston | Home - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | L 9-21 | |
| Tue., 4/12 | JV Girls Lacrosse | Weston | Home - Trumbull HS-Cork Field [Directions] | 4:00 p.m. | ||
| Tue., 4/12 | V Softball | Westhill | Away - Westhill HS-Varsity Softball Field [Directions] | 4:30 p.m. | W 14-0 | |
| Tue., 4/12 | JV Softball | Westhill | Away - Westhill HS-Varsity Softball Field [Directions] | 6:00 p.m. | ||
| Tue., 4/12 | V Girls Tennis | Danbury | Away - Danbury HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Tue., 4/12 | JV Girls Tennis | Darien | Away - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/13 | V Baseball | Harding | Home - Trumbull HS-Varsity Baseball Field [Directions] | 4:00 p.m. | W 15-0 | |
| Wed., 4/13 | FR Boys Lacrosse | Westhill | Home - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Wed., 4/13 | V Boys Volleyball | Newington | Home - Trumbull HS-THS Main Gym [Directions] | 5:45 p.m. | W 3-0 | |
| Wed., 4/13 | JV Boys Volleyball | Newington | Home - Trumbull HS-THS Main Gym [Directions] | 4:30 p.m. | ||
| Wed., 4/13 | V Girls Golf | Lauralton Hall | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | THS 188; LH 239 | |
| Wed., 4/13 | JV Girls Golf | Lauralton Hall | Home - Tashua Knolls Golf Course-Tashua Glen [Directions] | 3:15 p.m. | ||
| Wed., 4/13 | FR Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 6:00 p.m. | ||
| Thu., 4/14 | V Baseball | Westhill | Home - Trumbull HS-Varsity Baseball Field [Directions] | 3:30 p.m. | L 7-1 | |
| Thu., 4/14 | JV Baseball | Westhill | Home - Trumbull HS-JV Baseball Field [Directions] | 3:30 p.m. | ||
| Thu., 4/14 | FR Baseball | Westhill | Away - Westhill HS-Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Thu., 4/14 | V Boys Lacrosse | Fairfield Warde | Home - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | L 9-15 | |
| Thu., 4/14 | JV Boys Lacrosse | Fairfield Warde | Home - Trumbull HS-Cork Field [Directions] | 4:00 p.m. | ||
| Thu., 4/14 | FR Boys Lacrosse | Fairfield Ludlowe | Home - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Thu., 4/14 | V Boys Tennis | Darien | Away - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | L 1-6 | |
| Thu., 4/14 | V Girls Golf | Wilton | Away - Silvermine Golf Club [Directions] | 3:30 p.m. | THS 171; Wilton 195 | |
| Thu., 4/14 | V Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 5:30 p.m. | W 14-13 | |
| Thu., 4/14 | JV Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | ||
| Thu., 4/14 | V Softball | Shelton | Away - Shelton HS-Softball Diamond [Directions] | 4:15 p.m. | L 7-13 | |
| Thu., 4/14 | JV Softball | Shelton | Away - Shelton HS-Upper Field [Directions] | Canceled | Cancelled | |
| Thu., 4/14 | V Girls Tennis | Darien | Home - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Thu., 4/14 | JV Girls Tennis | Darien | Home - Tashua Knolls Golf Course-Tennis Courts [Directions] | 4:00 p.m. | ||
| Sat., 4/16 | V Baseball | Fairfield Prep | Away - Fairfield University-Alumni Diamond [Directions] | 11:00 a.m. | W 8-7 | |
| Sat., 4/16 | JV Baseball | Fairfield Prep | Home - Trumbull HS-Varsity Baseball Field [Directions] | 12:00 p.m. | ||
| Sat., 4/16 | FR Baseball | Fairfield Prep | Home - Trumbull HS-JV Baseball Field [Directions] | 12:00 p.m. | ||
| Sat., 4/16 | V Boys Lacrosse | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 11:00 a.m. | W 19-4 | |
| Sat., 4/16 | JV Boys Lacrosse | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | Canceled | Cancelled | |
| Sat., 4/16 | V Boys Volleyball | New Canaan | Home - Trumbull HS-THS Main Gym [Directions] | 12:00 p.m. | W 3-1 | |
| Sat., 4/16 | JV Boys Volleyball | New Canaan | Home - Trumbull HS-THS Main Gym [Directions] | 10:30 a.m. | ||
| Sat., 4/16 | V Girls Lacrosse | Danbury | Home - Trumbull HS-McDougall Stadium [Directions] | 12:00 p.m. | W 13-3 | |
| Sat., 4/16 | JV Girls Lacrosse | Danbury | Home - Trumbull HS-McDougall Stadium [Directions] | 10:15 a.m. | ||
| Sat., 4/16 | V Softball | Staples | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 12:00 p.m. | W 5-4 | |
| Sat., 4/16 | JV Softball | Staples | Home - Trumbull HS-JV Softball Diamond [Directions] | 10:00 a.m. | ||
| Mon., 4/18 | V Baseball | Danbury | Away - Danbury HS-V Baseball Field [Directions] | 11:00 a.m. | L 1-0 | |
| Mon., 4/18 | JV Baseball | Danbury | Away - Danbury HS-JV Baseball Field [Directions] | 11:00 a.m. | ||
| Mon., 4/18 | FR Baseball | Danbury | Home - Trumbull HS-Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/18 | V Boys Tennis | Ridgefield | Away - Ridgefield HS-RHS Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Mon., 4/18 | JV Boys Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 4/18 | V Boys Volleyball | Staples | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | W 3-2 | |
| Mon., 4/18 | JV Boys Volleyball | Staples | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 4/18 | V Softball | Danbury | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 2:00 p.m. | L 4-8 | |
| Mon., 4/18 | JV Softball | Danbury | Home - Trumbull HS-JV Softball Diamond [Directions] | 4:00 p.m. | ||
| Mon., 4/18 | V Girls Tennis | Ridgefield | Home - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Mon., 4/18 | JV Girls Tennis | Ridgefield | Home - Trumbull HS-Tennis Courts [Directions] | 3:00 p.m. | ||
| Mon., 4/18 | Miscellaneous Events | Football Camp | Home - Trumbull HS [Directions] | 8:00 a.m. | ||
| Tue., 4/19 | V Boys Lacrosse | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 5:00 p.m. | L 6-19 | |
| Tue., 4/19 | JV Boys Lacrosse | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 6:30 p.m. | ||
| Tue., 4/19 | V Boys Tennis | Fairfield Ludlowe | Home - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | L 3-4 | |
| Tue., 4/19 | JV Boys Tennis | Fairfield Ludlowe | Home - Tashua Knolls Golf Course-Tennis Courts [Directions] | Postponed | ||
| Tue., 4/19 | V Girls Lacrosse | Brien McMahon | Home - Trumbull HS-McDougall Stadium [Directions] | 5:30 p.m. | W 14-9 | |
| Tue., 4/19 | JV Girls Lacrosse | Brien McMahon | Home - Trumbull HS-McDougall Stadium [Directions] | Canceled | Cancelled | |
| Tue., 4/19 | V Girls Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Tennis Courts [Directions] | 11:00 a.m. | L 0-7 | |
| Tue., 4/19 | JV Girls Tennis | Fairfield Ludlowe | Away - Dwight Elementary School-Tennis Courts [Directions] | 11:00 a.m. | ||
| Tue., 4/19 | Miscellaneous Events | Football Camp | Home - Trumbull HS [Directions] | 8:00 a.m. | ||
| Wed., 4/20 | V Baseball | Darien | Home - Trumbull HS-Varsity Baseball Field [Directions] | 4:00 p.m. | W 6-3 | |
| Wed., 4/20 | JV Baseball | Darien | Home - Trumbull HS-JV Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 4/20 | FR Baseball | Darien | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 4/20 | FR Boys Lacrosse | Staples | Home - Trumbull HS-The Pit [Directions] | Postponed | ||
| Wed., 4/20 | V Boys Volleyball | Westhill | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | W 3-1 | |
| Wed., 4/20 | JV Boys Volleyball | Westhill | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 4/20 | V Softball | Darien | Away - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | W 12-1 | |
| Wed., 4/20 | Miscellaneous Events | Outside Group | Home - Trumbull HS-McDougall Stadium [Directions] | 12:00 p.m. | ||
| Thu., 4/21 | V Boys Lacrosse | Fairfield Ludlowe | Home - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | L 4-17 | |
| Thu., 4/21 | JV Boys Lacrosse | Fairfield Ludlowe | Home - Trumbull HS-Cork Field [Directions] | 4:00 p.m. | ||
| Thu., 4/21 | V Boys Tennis | Greenwich | Away - Greenwich HS-Tennis Courts [Directions] | 11:00 a.m. | L 1-6 | |
| Thu., 4/21 | V Girls Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 5:30 p.m. | L 4-10 | |
| Thu., 4/21 | JV Girls Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | ||
| Thu., 4/21 | V Girls Rugby | Darien | Away - Royle School Field [Directions] | 5:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 5/23 | ||||||
| Thu., 4/21 | V Softball | Ridgefield | Away - Ridgefield HS-Varsity Field [Directions] | 4:00 p.m. | W 15-2 | |
| Thu., 4/21 | JV Softball | Ridgefield | Away - Ridgefield HS-JV Field [Directions] | 5:30 p.m. | ||
| Thu., 4/21 | V Girls Tennis | Greenwich | Home - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Fri., 4/22 | V Baseball | Ridgefield | Home - Trumbull HS-Varsity Baseball Field [Directions] | 4:00 p.m. | W 7-0 | |
| Fri., 4/22 | JV Baseball | Ridgefield | Home - Trumbull HS-JV Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 4/22 | FR Baseball | Ridgefield | Away - Governor Field [Directions] | 4:00 p.m. | ||
| Fri., 4/22 | FR Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Fairfield Warde Grass Utility Field [Directions] | Postponed | ||
| Fri., 4/22 | V Boys Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Fri., 4/22 | JV Boys Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 4/23 | V Boys Lacrosse | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 12:00 p.m. | L 8-17 | |
| Sat., 4/23 | JV Boys Lacrosse | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 1:30 p.m. | ||
| Sat., 4/23 | V Girls Lacrosse | St. Joseph | Home - Trumbull HS-McDougall Stadium [Directions] | 12:00 p.m. | L 5-19 | |
| Sat., 4/23 | JV Girls Lacrosse | St. Joseph | Home - Trumbull HS-McDougall Stadium [Directions] | 10:15 a.m. | ||
| Mon., 4/25 | V Baseball | Fairfield Ludlowe | Away - Kiwanis Field-Baseball Diamond [Directions] | 4:00 p.m. | W 8-2 | |
| Mon., 4/25 | JV Baseball | Fairfield Ludlowe | Away - Owen Fish Park-Owen Fish [Directions] | 4:00 p.m. | ||
| Mon., 4/25 | FR Baseball | Fairfield Ludlowe | Home - Trumbull HS-Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/25 | FR Boys Lacrosse | Wilton | Home - Trumbull HS-The Pit [Directions] | Postponed | ||
| Mon., 4/25 | V Boys Outdoor Track | Greenwich | Home - Trumbull HS-McDougall Stadium [Directions] | 4:00 p.m. | ||
| Mon., 4/25 | V Boys Tennis | Bridgeport Central | Home - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Mon., 4/25 | JV Boys Tennis | Fairfield Warde | Away - Fairfield Warde HS-Knapps Courts [Directions] | 4:00 p.m. | ||
| Mon., 4/25 | V Boys Volleyball | Stamford | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Mon., 4/25 | JV Boys Volleyball | Stamford | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 4/25 | FR Girls Lacrosse | Wilton | Away - Wilton HS-Allen Meadow [Directions] | 4:00 p.m. | ||
| Mon., 4/25 | V Girls Outdoor Track | Greenwich | Home - Trumbull HS-McDougall Stadium [Directions] | 4:00 p.m. | ||
| Mon., 4/25 | V Softball | Fairfield Ludlowe | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 4:15 p.m. | L 1-8 | |
| Mon., 4/25 | JV Softball | Fairfield Ludlowe | Home - Trumbull HS-JV Softball Diamond [Directions] | 6:00 p.m. | ||
| Mon., 4/25 | V Girls Tennis | Bridgeport Central | Away - Bridgeport Central HS-Central High School Tennis Courts [Directions] | 4:00 p.m. | W 4-3 | |
| Tue., 4/26 | V Boys Lacrosse | Ridgefield | Home - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | L 2-18 | |
| Tue., 4/26 | JV Boys Lacrosse | Ridgefield | Home - Trumbull HS-Cork Field [Directions] | 4:00 p.m. | ||
| Tue., 4/26 | V Girls Golf | Newtown | Away - Newtown Country Club [Directions] | 2:30 p.m. | THS 196; NHS 192 | |
| Tue., 4/26 | V Girls Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 4:30 p.m. | L 3-17 | |
| Tue., 4/26 | JV Girls Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 6:00 p.m. | ||
| Tue., 4/26 | JV Girls Tennis | Greenwich | Home - Tashua Knolls Golf Course-Tennis Courts [Directions] | Postponed | ||
| Wed., 4/27 | V Baseball | Greenwich | Home - Trumbull HS-Varsity Baseball Field [Directions] | 4:30 p.m. | W 10-4 | |
| Wed., 4/27 | JV Baseball | Greenwich | Home - Trumbull HS-JV Baseball Field [Directions] | 4:30 p.m. | ||
| Wed., 4/27 | FR Baseball | Greenwich | Away - Greenwich HS-Baseball Field [Directions] | 4:30 p.m. | ||
| Wed., 4/27 | FR Boys Lacrosse | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | ||
| Wed., 4/27 | V Boys Tennis | Stamford | Home - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Wed., 4/27 | V Boys Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 4/27 | JV Boys Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 4/27 | V Girls Golf | Fairfield Warde | Away - Smith Richardson Golf Course [Directions] | 3:00 p.m. | THS 191; FWHS 250 | |
| Wed., 4/27 | FR Girls Lacrosse | Fairfield Warde | Home - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Wed., 4/27 | V Softball | Greenwich | Away - Greenwich HS-Softball Field [Directions] | 4:15 p.m. | W 21-2 | |
| Wed., 4/27 | V Girls Tennis | Stamford | Away - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Thu., 4/28 | V Boys Tennis | Staples | Away - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Thu., 4/28 | JV Boys Tennis | Staples | Away - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 4/28 | V Boys Volleyball | St. Joseph | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Thu., 4/28 | JV Boys Volleyball | St. Joseph | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 4/28 | V Girls Golf | New Canaan | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | THS 194; NCHS 180 | |
| Thu., 4/28 | JV Girls Golf | New Canaan | Home - Tashua Knolls Golf Course-Tashua Glen [Directions] | 3:15 p.m. | ||
| Thu., 4/28 | V Girls Lacrosse | Lauralton Hall | Home - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | L 8-9 | |
| Thu., 4/28 | JV Girls Lacrosse | Lauralton Hall | Home - Trumbull HS-McDougall Stadium [Directions] | 4:00 p.m. | ||
| Thu., 4/28 | V Girls Tennis | Staples | Home - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Thu., 4/28 | JV Girls Tennis | Staples | Home - Tashua Knolls Golf Course-Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 4/29 | V Baseball | Bridgeport Central | Away - Bridgeport Central HS-Baseball Diamond [Directions] | 4:00 p.m. | W 11-1 | |
| Fri., 4/29 | JV Baseball | Bassick | Away - Bassick HS-Went Field [Directions] | Postponed | ||
| Fri., 4/29 | FR Boys Lacrosse | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Fri., 4/29 | V Boys Outdoor Track | O'Grady Relays | Away - Danbury HS-Danbury HS Stadium | 5:00 p.m. | ||
| Fri., 4/29 | FR Girls Lacrosse | New Canaan | Home - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Fri., 4/29 | V Girls Outdoor Track | O'Grady Relays | Away - Danbury HS-Danbury HS Stadium | 5:00 p.m. | ||
| Fri., 4/29 | V Girls Rugby | Southington | Home - Trumbull HS-Cork Field [Directions] | 7:00 p.m. | ||
| Fri., 4/29 | V Softball | Bridgeport Central | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 4:15 p.m. | W 12-0 | |
| Fri., 4/29 | JV Softball | Bridgeport Central | Home - Trumbull HS-JV Softball Diamond [Directions] | Canceled | Cancelled | |
| Fri., 4/29 | JV Girls Tennis | Fairfield Warde | Home - Tashua Knolls Golf Course-Tennis Courts [Directions] | 4:00 p.m. | ||
| Sat., 4/30 | V Boys Lacrosse | Bunnell-Stratford | Home - Trumbull HS-McDougall Stadium [Directions] | 12:00 p.m. | W 16-5 | |
| Sat., 4/30 | JV Boys Lacrosse | Bunnell-Stratford | Home - Trumbull HS-McDougall Stadium [Directions] | 10:00 a.m. | ||
| Sat., 4/30 | V Boys Rugby | Pelham Memorial (NY) | Home - Trumbull HS-Cork Field [Directions] | 11:00 a.m. | ||
| Sat., 4/30 | JV Boys Rugby | Pelham Memorial (NY) | Home - Trumbull HS-Cork Field [Directions] | 12:45 p.m. | ||
| Sat., 4/30 | V Girls Lacrosse | Staples | Away - Staples HS-Staples Stadium [Directions] | 7:00 p.m. | L 8-19 | |
| Sat., 4/30 | JV Girls Lacrosse | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 5:00 p.m. | ||
| Mon., 5/2 | FR Boys Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 4:00 p.m. | ||
| Mon., 5/2 | V Boys Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Mon., 5/2 | JV Boys Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Gym [Directions] | 4:00 p.m. | ||
| Mon., 5/2 | FR Girls Lacrosse | Fairfield Ludlowe | Home - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Tue., 5/3 | V Baseball | Stamford | Away - Stamford HS-SHS Baseball Diamond [Directions] | 4:30 p.m. | W 6-1 | |
| Tue., 5/3 | JV Baseball | Stamford | Away - Belltown Park-Barrett Field, Belltown Park [Directions] | 4:30 p.m. | ||
| Tue., 5/3 | FR Baseball | Stamford | Home - Trumbull HS-Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Tue., 5/3 | V Boys Outdoor Track | Danbury | Away - Danbury HS-Stadium Track [Directions] | 4:00 p.m. | ||
| Tue., 5/3 | V Boys Tennis | St. Joseph | Home - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 5/3 | V Girls Golf | Amity | Away - Race Brook C.C. [Directions] | 3:30 p.m. | THS 195; Amity 190 | |
| Tue., 5/3 | V Girls Outdoor Track | Danbury | Away - Danbury HS-Stadium Track [Directions] | 4:00 p.m. | ||
| Tue., 5/3 | V Softball | Stamford | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 4:15 p.m. | W 7-4 | |
| Tue., 5/3 | JV Softball | Stamford | Home - Trumbull HS-JV Softball Diamond [Directions] | 6:15 p.m. | ||
| Tue., 5/3 | V Girls Tennis | St. Joseph | Away - St. Joseph HS-Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Wed., 5/4 | FR Boys Lacrosse | Ridgefield | Home - Trumbull HS-The Pit [Directions] | Canceled | Cancelled | |
| Wed., 5/4 | JV Boys Tennis | Darien | Home - Tashua Knolls Golf Course-Tennis Courts [Directions] | Postponed | ||
| Wed., 5/4 | V Boys Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 4:30 p.m. | W 3-0 | |
| Wed., 5/4 | JV Boys Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | Canceled | Cancelled | |
| Thu., 5/5 | V Baseball | Staples | Home - Trumbull HS-Varsity Baseball Field [Directions] | 4:30 p.m. | W 5-1 | |
| Thu., 5/5 | JV Baseball | Staples | Home - Trumbull HS-JV Baseball Field [Directions] | 4:30 p.m. | ||
| Thu., 5/5 | FR Baseball | Staples | Away - Staples HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Thu., 5/5 | V Boys Lacrosse | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 5:00 p.m. | L 0-15 | |
| Thu., 5/5 | JV Boys Lacrosse | Greenwich | Away - Greenwich HS-Field 4 [Directions] | 5:00 p.m. | ||
| Thu., 5/5 | V Boys Tennis | New Canaan | Home - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | W 4-3 | |
| Thu., 5/5 | JV Boys Tennis | New Canaan | Home - Tashua Knolls Golf Course-Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/5 | V Boys Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 5:00 p.m. | W 3-0 | |
| Thu., 5/5 | JV Boys Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 6:30 p.m. | ||
| Thu., 5/5 | V Girls Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | 3:30 p.m. | THS 197; GHS 176 | |
| Thu., 5/5 | V Girls Lacrosse | Greenwich | Home - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | L 6-20 | |
| Thu., 5/5 | JV Girls Lacrosse | Greenwich | Home - Trumbull HS-Cork Field [Directions] | 4:00 p.m. | ||
| Thu., 5/5 | V Softball | Wilton | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 4:30 p.m. | W 5-4 | |
| Thu., 5/5 | JV Softball | Wilton | Home - Trumbull HS-JV Softball Diamond [Directions] | Postponed | ||
| Thu., 5/5 | V Girls Tennis | New Canaan | Away - New Canaan HS-NCHS Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Fri., 5/6 | V Boys Rugby | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 6:30 p.m. | ||
| Fri., 5/6 | JV Boys Rugby | Ridgefield | Away - Ridgefield HS-Tiger Hollow Turf Field II [Directions] | 4:30 p.m. | ||
| Fri., 5/6 | FR Girls Lacrosse | Darien | Home - Trumbull HS-Cork Field [Directions] | 4:00 p.m. | ||
| Sat., 5/7 | V Boys Lacrosse | Westhill | Home - Trumbull HS-McDougall Stadium [Directions] | 12:00 p.m. | L 10-11 | |
| Sat., 5/7 | JV Boys Lacrosse | Westhill | Home - Trumbull HS-McDougall Stadium [Directions] | 2:00 p.m. | ||
| Sat., 5/7 | V Girls Lacrosse | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 3:00 p.m. | W 13-5 | |
| Sat., 5/7 | JV Girls Lacrosse | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:30 p.m. | ||
| Mon., 5/9 | V Baseball | St. Joseph | Away - St. Joseph HS-Baseball Diamond [Directions] | 4:00 p.m. | W 6-5 (9) | |
| Mon., 5/9 | JV Baseball | St. Joseph | Away - Unity Park-Field 1 [Directions] | 4:00 p.m. | ||
| Mon., 5/9 | FR Baseball | St. Joseph | Home - Trumbull HS-Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/9 | FR Boys Lacrosse | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | Postponed | ||
| Mon., 5/9 | V Boys Outdoor Track | Bassick, Bridgeport Central | Home - Trumbull HS-McDougall Stadium [Directions] | 4:30 p.m. | ||
| Mon., 5/9 | V Boys Tennis | Brien McMahon | Away - Brien McMahon HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Mon., 5/9 | JV Boys Tennis | Staples | Home - Tashua Knolls Golf Course-Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 5/9 | V Boys Volleyball | Norwalk | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Mon., 5/9 | JV Boys Volleyball | Norwalk | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 5/9 | FR Girls Lacrosse | Staples | Home - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Mon., 5/9 | V Girls Outdoor Track | Bassick, Bridgeport Central, Harding | Home - Trumbull HS-McDougall Stadium [Directions] | 4:30 p.m. | ||
| Mon., 5/9 | V Softball | St. Joseph | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 4:45 p.m. | L 2-8 | |
| Mon., 5/9 | JV Softball | St. Joseph | Home - Trumbull HS-JV Softball Diamond [Directions] | 6:30 p.m. | ||
| Mon., 5/9 | V Girls Tennis | Brien McMahon | Home - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | L 2-5 | |
| Mon., 5/9 | JV Girls Tennis | Staples | Away - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/10 | V Boys Tennis | Fairfield Warde | Away - Fairfield Warde HS-Blake Courts [Directions] | 4:00 p.m. | L 1-6 | |
| Tue., 5/10 | JV Boys Tennis | Fairfield Warde | Away - Fairfield Warde HS-Knapps Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/10 | V Girls Golf | Staples | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | THS 199; SHS 187 | |
| Tue., 5/10 | JV Girls Golf | Staples | Home - Tashua Knolls Golf Course-Tashua Glen [Directions] | 3:15 p.m. | ||
| Tue., 5/10 | V Girls Lacrosse | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 5:30 p.m. | L 8-15 | |
| Tue., 5/10 | JV Girls Lacrosse | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 4:00 p.m. | ||
| Tue., 5/10 | V Softball | Staples | Away - Staples HS-Wakeman Field [Directions] | 4:15 p.m. | W 6-2 | |
| Tue., 5/10 | JV Softball | Staples | Away - Staples HS-Staples Softball Field [Directions] | 6:00 p.m. | ||
| Tue., 5/10 | V Girls Tennis | Fairfield Warde | Home - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Tue., 5/10 | JV Girls Tennis | Fairfield Warde | Home - Tashua Knolls Golf Course-Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/11 | V Baseball | New Canaan | Away - Mead Park-Baseball Field [Directions] | 4:00 p.m. | L 3-2 | |
| Wed., 5/11 | JV Baseball | New Canaan | Away - Waveny Park-Coppo Field [Directions] | 4:00 p.m. | ||
| Wed., 5/11 | FR Baseball | New Canaan | Home - Trumbull HS-Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/11 | V Boys Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Wed., 5/11 | JV Boys Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | Postponed | ||
| Wed., 5/11 | FR Girls Lacrosse | Wilton | Away - Wilton HS-Lilly Field [Directions] | 7:30 p.m. | ||
| Wed., 5/11 | V Girls Rugby | Darien | Away - Royle School Field [Directions] | Postponed | ||
| Wed., 5/11 | V Softball | New Canaan | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 4:15 p.m. | W 14-2 | |
| Wed., 5/11 | JV Softball | New Canaan | Home - Trumbull HS-JV Softball Diamond [Directions] | 4:15 p.m. | ||
| Thu., 5/12 | V Boys Lacrosse | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 7:00 p.m. | W 11-1 | |
| Thu., 5/12 | JV Boys Lacrosse | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Thu., 5/12 | V Boys Tennis | Norwalk | Home - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Thu., 5/12 | JV Boys Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/12 | V Girls Lacrosse | Stamford | Home - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | L 7-14 | |
| Thu., 5/12 | JV Girls Lacrosse | Stamford | Home - Trumbull HS-Cork Field [Directions] | 4:00 p.m. | ||
| Thu., 5/12 | V Girls Tennis | Norwalk | Away - Norwalk HS-Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Thu., 5/12 | JV Girls Tennis | Ridgefield | Home - Tashua Knolls Golf Course-Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 5/13 | V Baseball | Brien McMahon | Home - Trumbull HS-Varsity Baseball Field [Directions] | 6:00 p.m. | W 4-2 | |
| Fri., 5/13 | JV Baseball | Brien McMahon | Home - Trumbull HS-JV Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 5/13 | JV Boys Tennis | Darien | Away - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 5/13 | V Boys Volleyball | Fairfield Ludlowe | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | W 3-2 | |
| Fri., 5/13 | JV Boys Volleyball | Fairfield Ludlowe | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 5/13 | FR Girls Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 4:30 p.m. | ||
| Fri., 5/13 | V Softball | Brien McMahon | Away - Norwalk HS - Ray Barry Field-Softball Field [Directions] | 4:15 p.m. | W 16-1 | |
| Fri., 5/13 | JV Softball | Brien McMahon | Away - Norwalk HS - Ray Barry Field-Softball Field [Directions] | 5:45 p.m. | ||
| Fri., 5/13 | V Girls Tennis | Wilton | Away - Wilton HS-Tennis Courts [Directions] | 4:30 p.m. | L 0-7 | |
| Fri., 5/13 | JV Girls Tennis | Wilton | Away - Wilton HS-Tennis Courts [Directions] | 4:30 p.m. | ||
| Sat., 5/14 | V Boys Lacrosse | Amity | Home - Trumbull HS-McDougall Stadium [Directions] | 1:00 p.m. | L 6-11 | |
| Sat., 5/14 | JV Boys Lacrosse | Amity | Home - Trumbull HS-McDougall Stadium [Directions] | 3:00 p.m. | ||
| Sat., 5/14 | V Boys Rugby | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 12:00 p.m. | ||
| Sat., 5/14 | V Boys Tennis | Wilton | Home - Trumbull HS-Tennis Courts [Directions] | 11:00 a.m. | L 0-7 | |
| Sat., 5/14 | JV Boys Tennis | Wilton | Home - Trumbull HS-Tennis Courts [Directions] | 12:30 p.m. | ||
| Sat., 5/14 | V Girls Lacrosse | South Windsor | Away - South Windsor HS-SWHS Turf Field [Directions] | 2:30 p.m. | L 9-13 | |
| Sat., 5/14 | JV Girls Lacrosse | South Windsor | Away - South Windsor HS-SWHS Turf Field [Directions] | 4:00 p.m. | ||
| Sat., 5/14 | Miscellaneous Events | Powder Puff | Home - Trumbull HS-McDougall Stadium [Directions] | 10:00 a.m. | ||
| Mon., 5/16 | V Boys Volleyball | Darien | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | L 1-3 | |
| Mon., 5/16 | JV Boys Volleyball | Darien | Home - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 5/16 | V Girls Golf | Darien | Away - Wee Burn CC [Directions] | 3:00 p.m. | THS 206; DHS 228 | |
| Tue., 5/17 | V Baseball | Wilton | Away - Wilton HS-Varsity Baseball Field [Directions] | 4:30 p.m. | W 7-0 | |
| Tue., 5/17 | JV Baseball | Wilton | Away - Wilton HS-JV Baseball Field [Directions] | 4:30 p.m. | ||
| Tue., 5/17 | V Boys Outdoor Track | St. Joseph | Away - St. Joseph HS-Track [Directions] | 4:00 p.m. | ||
| Tue., 5/17 | V Girls Golf | Ridgefield | Away - Ridgefield Golf Course [Directions] | 3:00 p.m. | THS 188; RHS 213 | |
| Tue., 5/17 | JV Girls Golf | Ridgefield | Away - Ridgefield Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 5/17 | V Girls Outdoor Track | St. Joseph | Away - St. Joseph HS-Track [Directions] | 4:00 p.m. | ||
| Tue., 5/17 | V Softball | Fairfield Warde | Away - Fairfield Warde HS-Softball Diamond [Directions] | 4:15 p.m. | L 2-5 | |
| Tue., 5/17 | JV Softball | Fairfield Warde | Away - Fairfield Warde HS-Softball Diamond [Directions] | 5:45 p.m. | ||
| Wed., 5/18 | V Baseball | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 6:00 p.m. | W 4-3 | |
| Wed., 5/18 | JV Baseball | Norwalk | Away - City Hall Field [Directions] | 4:00 p.m. | ||
| Wed., 5/18 | FR Baseball | Norwalk | Home - Trumbull HS-Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/18 | V Boys Lacrosse | Hall | Away - Hall HS-Stadium (Turf Field) [Directions] | 6:00 p.m. | L 6-11 | |
| Wed., 5/18 | JV Boys Lacrosse | Hall | Away - Hall HS-Field 8 [Directions] | 5:30 p.m. | ||
| Wed., 5/18 | V Boys Volleyball | Bridgeport Central | Away - Bridgeport Central HS-The Barry McLeod Court [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 5/18 | JV Boys Volleyball | Bridgeport Central | Away - Bridgeport Central HS-The Barry McLeod Court [Directions] | 4:00 p.m. | ||
| Wed., 5/18 | V Girls Golf | Fairfield Ludlowe | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | THS 182; FLHS 222 | |
| Wed., 5/18 | V Softball | Norwalk | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 4:15 p.m. | W 4-1 | |
| Wed., 5/18 | JV Softball | Norwalk | Home - Trumbull HS-JV Softball Diamond [Directions] | 6:00 p.m. | ||
| Thu., 5/19 | FR Baseball | Fairfield Warde | Away - Fairfield Warde HS-Baseball Diamond [Directions] | Canceled | Cancelled | |
| Thu., 5/19 | FR Boys Lacrosse | Greenwich | Away - Greenwich HS-Field 3 [Directions] | 4:00 p.m. | ||
| Thu., 5/19 | V Girls Rugby | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 5:00 p.m. | ||
| Fri., 5/20 | V Baseball | Fairfield Warde | Home - Trumbull HS-Varsity Baseball Field [Directions] | 3:00 p.m. | L 7-2 | |
| Fri., 5/20 | JV Baseball | Fairfield Warde | Home - Trumbull HS-JV Baseball Field [Directions] | 3:00 p.m. | ||
| Fri., 5/20 | V Boys Rugby | Fairfield Prep | Home - Trumbull HS-McDougall Stadium [Directions] | Canceled | Cancelled | |
| Fri., 5/20 | JV Boys Rugby | Fairfield Prep | Home - Trumbull HS-McDougall Stadium [Directions] | Canceled | Cancelled | |
| Sat., 5/21 | V Baseball | New Canaan | Home - Trumbull HS-Varsity Baseball Field [Directions] | 1:00 p.m. | ||
| Sat., 5/21 | V Baseball | Fairfield Warde | Away - Cubeta Stadium [Directions] | 5:00 p.m. | ||
| Sat., 5/21 | V Baseball | Fairfield Warde | Away - Cubeta Stadium [Directions] | 5:00 p.m. | ||
| Sat., 5/21 | V Boys Lacrosse | New Fairfield | Away - New Fairfield HS-Marty Morgan Field [Directions] | 7:30 p.m. | L 5-9 | |
| Sat., 5/21 | FR Boys Lacrosse | Stamford | Home - Trumbull HS-The Pit [Directions] | Postponed | ||
| Sat., 5/21 | V Boys Rugby | Fairfield Prep | Home - Trumbull HS-Cork Field [Directions] | 10:00 a.m. | ||
| Sat., 5/21 | JV Boys Rugby | Fairfield Prep | Home - Trumbull HS-Cork Field [Directions] | 11:45 p.m. | ||
| Sat., 5/21 | V Boys Volleyball | Staples | Home - Trumbull HS-THS Main Gym [Directions] | 11:00 a.m. | W 3-0 | |
| Sat., 5/21 | V Softball | Fairfield Warde | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 11:00 a.m. | ||
| Sun., 5/22 | Miscellaneous Events | Conny Lacrosse Tournament | Home - Trumbull HS [Directions] | 8:00 a.m. | ||
| Mon., 5/23 | V Baseball | Fairfield Warde | Away - Cubeta Stadium [Directions] | 5:00 p.m. | ||
| Mon., 5/23 | V Girls Golf | New Canaan | Away - CCNC [Directions] | 3:30 p.m. | THS 207; NCHS 173 | |
| Mon., 5/23 | V Girls Outdoor Track | FCIAC Championships | Away - Wilton HS-Fujitani Field - Turf | 3:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Danbury HS-Wilton HS-Fujitani Field - Turf | ||||||
| Mon., 5/23 | V Softball | Fairfield Ludlowe | Away - Sacred Heart University-Pioneer Park [Directions] | 3:00 p.m. | ||
| Tue., 5/24 | FR Baseball | Wilton | Home - Trumbull HS-JV Baseball Field [Directions] | 6:00 p.m. | ||
| Tue., 5/24 | V Boys Lacrosse | Brookfield (Scrim.) | Away - Cadigan Field-Field #1 [Directions] | 4:00 p.m. | ||
| Tue., 5/24 | V Boys Outdoor Track | FCIAC Championships | Away - Danbury HS-Stadium Track | 3:30 p.m. | ||
| Wed., 5/25 | V Boys Volleyball | New Canaan | Home - Fairfield Warde HS-Gym [Directions] | 7:00 p.m. | W 3-0 | |
| Wed., 5/25 | V Girls Golf | Staples | Away - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | THS 197; SHS 172 | |
| Wed., 5/25 | JV Girls Golf | Staples | Away - Staples HS-Longshore Golf Course [Directions] | 3:15 p.m. | ||
| Thu., 5/26 | V Baseball | Shelton (Scrim.) | Away - Shelton HS-Baseball Diamond - N Constitution Blvd [Directions] | 4:00 p.m. | ||
| Thu., 5/26 | V Boys Lacrosse | Jonathan Law (Scrim.) | Home - Trumbull HS-McDougall Stadium [Directions] | 5:00 p.m. | ||
| Thu., 5/26 | V Girls Rugby | Darien | Home - Trumbull HS-Cork Field [Directions] | Postponed | ||
| Fri., 5/27 | V Boys Rugby | Greenwich | Home - Trumbull HS-Cork Field [Directions] | 6:00 p.m. | ||
| Fri., 5/27 | JV Boys Rugby | Greenwich | Home - Trumbull HS-Cork Field [Directions] | 7:45 p.m. | ||
| Fri., 5/27 | V Boys Volleyball | Darien | Away - Fairfield Warde HS-Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Fri., 5/27 | V Softball | St. Joseph (Scrim.) | Away - St. Joseph HS-Softball Diamond [Directions] | 4:00 p.m. | ||
| Tue., 5/31 | V Baseball | Hillhouse/Career | Home - Trumbull HS-Varsity Baseball Field [Directions] | 3:30 p.m. | ||
| Tue., 5/31 | V Boys Outdoor Track | CIAC Class LL Championship | Away - Willow Brook Park | 4:00 p.m. | ||
| Tue., 5/31 | V Boys Rugby | Ridgefield | Home - Ridgefield HS-Tiger Hollow Stadium [Directions] | 7:30 p.m. | ||
| Tue., 5/31 | V Boys Tennis | Enfield/Somers/AAE Coop | Away - Suffield HS-Tennis Courts [Directions] | 3:00 p.m. | ||
| Tue., 5/31 | V Girls Golf | Darien | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | THS 198; DHS 222 | |
| Tue., 5/31 | JV Girls Golf | Darien | Home - Tashua Knolls Golf Course-Tashua Glen [Directions] | 3:15 p.m. | ||
| Tue., 5/31 | V Girls Outdoor Track | CIAC Class LL Championship | Away - Willow Brook Park | 4:00 p.m. | ||
| Tue., 5/31 | V Softball | Stamford | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 4:30 p.m. | ||
| Wed., 6/1 | V Baseball | West Haven | Home - Trumbull HS-Varsity Baseball Field [Directions] | 3:30 p.m. | ||
| Wed., 6/1 | V Boys Volleyball | Norwalk | Home - Trumbull HS-THS Main Gym [Directions] | 5:00 p.m. | W 3-0 | |
| Wed., 6/1 | V Softball | Glastonbury | Away - Glastonbury HS-Field 10 [Directions] | 4:30 p.m. | ||
| Thu., 6/2 | V Girls Golf | FCIAC Championship @ Fairchild Wheeler | Away - Fairchild Wheeler Golf Course | TBA | ||
| Sat., 6/4 | V Baseball | Staples | Home - Trumbull HS-Varsity Baseball Field [Directions] | 2:00 p.m. | ||
| Sat., 6/4 | V Boys Volleyball | Conard | Home - Trumbull HS-THS Main Gym [Directions] | 5:00 p.m. | W 3-0 | |
| Sat., 6/4 | V Softball | Bristol Central | Away - Bristol Central HS-Softball Field [Directions] | 4:00 p.m. | ||
| Sat., 6/4 | Miscellaneous Events | Band Event | Home - Trumbull HS-THS Main Gym [Directions] | 8:00 a.m. | ||
| Sun., 6/5 | Miscellaneous Events | Kids Marathon Final Mile | Home - Trumbull HS-McDougall Stadium [Directions] | 8:00 a.m. | ||
| Mon., 6/6 | V Boys Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/6 | V Boys Rugby | Staples | Away - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Mon., 6/6 | V Boys Tennis | CIAC Individual Invitational - Opening Round, Singles and Doubles | Away - Wesleyan | 10:00 a.m. | ||
| Mon., 6/6 | V Girls Golf | CIAC Division I Championship | Away - Tashua Knolls GC | 8:30 a.m. | ||
| Mon., 6/6 | V Girls Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/6 | V Girls Tennis | CIAC Individual Invitational - Opening Round, Singles and Doubles | Away - Wesleyan | 10:00 a.m. | ||
| Tue., 6/7 | V Baseball | Fairfield Warde | Home - Municipal Stadium-Bob Palmer Diamond (Main Baseball Stadium) [Directions] | 3:30 p.m. | ||
| Tue., 6/7 | V Boys Tennis | CIAC Individual Invitational - Round of 16 | Away - Wesleyan | 9:00 a.m. | ||
| Tue., 6/7 | V Boys Volleyball | Glastonbury | Away - Southington HS-Gym 1 [Directions] | 6:00 p.m. | W 3-1 | |
| Wed., 6/8 | V Boys Tennis | CIAC Individual Invitational - Quarterfinals | Away - Wesleyan | 3:00 p.m. | ||
| Wed., 6/8 | V Girls Tennis | CIAC Individual Invitational - Quarterfinals | Away - Wesleyan | 3:00 p.m. | ||
| Thu., 6/9 | V Boys Tennis | CIAC Individual Invitational - Semifinals | Away - Wesleyan | 3:00 p.m. | ||
| Thu., 6/9 | V Boys Volleyball | Darien | Away - Pomperaug HS-Main Gym [Directions] | 5:00 p.m. | ||
| Thu., 6/9 | V Girls Tennis | CIAC Individual Invitational - Semifinals | Away - Wesleyan | 3:00 p.m. | ||
| Fri., 6/10 | V Boys Tennis | CIAC Individual Invitational - Finals | Away - Wesleyan | 3:00 p.m. | ||
| Fri., 6/10 | V Girls Tennis | CIAC Individual Invitational - Finals | Away - Wesleyan | 3:00 p.m. | ||
| Sat., 6/11 | V Girls Golf | CIAC Girls State Open | Away - Black Hall Club | 1:00 p.m. | ||
| Mon., 6/13 | V Boys Outdoor Track | CIAC Boys Hammer Throw Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Mon., 6/13 | V Girls Outdoor Track | CIAC Girls Hammer Throw Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Tue., 6/14 | V Boys Outdoor Track | CIAC Decathlon Championship Day 1 | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 6/14 | V Girls Outdoor Track | CIAC Heptathlon Championship Day 1 | Away - Willow Brook Park | 10:30 a.m. | ||
| Tue., 6/14 | V Girls Outdoor Track | CIAC Girls Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/15 | V Boys Outdoor Track | CIAC Decathlon Championship Day 2 | Away - Willow Brook Park | 10:00 a.m. | ||
| Wed., 6/15 | V Boys Outdoor Track | CIAC Boys Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/15 | V Girls Outdoor Track | CIAC Heptathlon Championship Day 2 | Away - Willow Brook Park | 10:00 a.m. | ||