| Trumbull 2022-23 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 588 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| Tue., 8/23 | V Boys Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | THS 168 Ludlowe 145 | 1:45 PM, Dismiss 1:30 PM; 1 Bus | |
| Wed., 8/24 | V Boys Golf | Fairfield Prep | Away - Patterson Club [Directions] | THS 178 Fairfield Prep 152 | 1:45 PM, Dismiss 1:30 PM; 1 Bus | |
| Thu., 8/25 | V Boys Golf | Darien | Home - Tashua Knolls Golf Course [Directions] | THS 168 Darien 161 | ||
| Sat., 8/27 | V Football | Hillhouse (Scrim.) | Home - Trumbull HS-McDougall Stadium [Directions] | 10:00 a.m. | ||
| Tue., 8/30 | V Boys Soccer | Amity (Scrim.) | Away - Amity Regional HS-AHS Grass Field # 3 [Directions] | 3:45 p.m. | 2:45 PM; 1 Bus | |
| Tue., 8/30 | V Girls Soccer | Amity (Scrim.) | Home - Trumbull HS-Cork Field [Directions] | 4:00 p.m. | ||
| Wed., 8/31 | V Boys Golf | St. Joseph | Away - Tashua Knolls Golf Course [Directions] | THS 169 St. Joe's 159 | 2:15 PM, Dismiss 2:00 PM; 1 Bus | |
| Thu., 9/1 | V Boys Golf | Norwalk | Home - Tashua Knolls Golf Course [Directions] | THS 159 NHS 196 | 2:15 PM; 1 Bus | |
| Thu., 9/1 | V Boys Soccer | Shelton (Scrim.) | Home - Trumbull HS-Cork Field [Directions] | 4:30 p.m. | ||
| Thu., 9/1 | V Girls Volleyball | Seymour (Scrim.) | Away - Seymour HS-Gym [Directions] | 4:30 p.m. | 2:45 PM; 1 Bus | |
| Fri., 9/2 | V Boys Cross Country | Fairfield Prep (Scrim.) | Home - Trumbull HS-Cross Country Course [Directions] | 4:00 p.m. | ||
| Fri., 9/2 | V Field Hockey | Shelton (Scrim.) | Away - Shelton HS-Finn Stadium [Directions] | 7:00 p.m. | 4:30 PM; 1 Bus | |
| Fri., 9/2 | V Girls Volleyball | Stratford (Scrim.) | Home - Trumbull HS-THS Main Gym [Directions] | 5:45 p.m. | ||
| Sat., 9/3 | V Boys Soccer | Newtown (Scrim.) | Home - Trumbull HS-Cork Field [Directions] | 10:00 a.m. | ||
| Sat., 9/3 | V Girls Volleyball | Brien McMahon (Scrim.) | Away - Northeast Athletic Center [Directions] | 10:00 a.m. | 8:00 AM; 1 Bus | |
| Tue., 9/6 | V Girls Soccer | Jonathan Law (Scrim.) | Away - Jonathan Law HS-New Turf Field [Directions] | 3:45 p.m. | 2:45 PM; 1 Bus | |
| Wed., 9/7 | V Boys Golf | Fairfield Warde | Home - Tashua Knolls Golf Course [Directions] | Trumbull 170 Warde 148 | 2:15 PM; 1 Bus | |
| Thu., 9/8 | V Boys Golf | Greenwich | Home - Tashua Knolls Golf Course [Directions] | THS 172 Greenwich 147 | 2:15 PM; 1 Bus | |
| Thu., 9/8 | V Boys Soccer | Westhill | Home - Trumbull HS-Cork Field [Directions] | W 2-0 | ||
| Thu., 9/8 | V Field Hockey | Pomperaug | Home - Trumbull HS-McDougall Stadium [Directions] | T 2-2 | ||
| Thu., 9/8 | V Girls Swimming and Diving | Greenwich | Away - Greenwich HS-Pool [Directions] | Trumbull - 80 Greenwich - 97 | 2:45 PM; 1 Bus | |
| Thu., 9/8 | V Girls Volleyball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | W 3-0 | 2:45 PM; 1 Bus | |
| Fri., 9/9 | V Football | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | W 49-43 | 4:30 PM; 2 Buses | |
| Fri., 9/9 | V Girls Cross Country | Darien (Scrim.) | Home - Trumbull HS-Cross Country Course [Directions] | 4:15 p.m. | ||
| Fri., 9/9 | V Girls Soccer | Westhill | Away - Westhill HS-Westhill Front Turf Field [Directions] | W 4-0 | 2:15 PM, Dismiss 2:00 PM; 1 Bus | |
| Fri., 9/9 | V Girls Volleyball | Southington | Home - Trumbull HS-THS Main Gym [Directions] | L 2-3 | ||
| Sat., 9/10 | V Boys Soccer | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | W 2-1 | 11:15 AM; 1 Bus | |
| Sat., 9/10 | V Field Hockey | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | W 2-1 | 1:30 PM; 1 Bus | |
| Mon., 9/12 | V Field Hockey | Ridgefield | Home - Trumbull HS-McDougall Stadium [Directions] | L 0-6 | ||
| Mon., 9/12 | V Girls Soccer | Danbury | Home - Trumbull HS-Cork Field [Directions] | W 1-0 | ||
| Mon., 9/12 | V Girls Volleyball | New Canaan | Home - Trumbull HS-THS Main Gym [Directions] | L 2-3 | ||
| Tue., 9/13 | V Boys Cross Country | Brien McMahon, Greenwich, Westhill | Home - Trumbull HS-Cross Country Course [Directions] | 4:00 p.m. | ||
| Tue., 9/13 | V Boys Soccer | Darien | Home - Trumbull HS-Cork Field [Directions] | W 3-1 | ||
| Tue., 9/13 | V Girls Cross Country | Brien McMahon, Greenwich, Westhill | Home - Trumbull HS-Cross Country Course [Directions] | 4:00 p.m. | ||
| Wed., 9/14 | V Boys Golf | Westhill | Away - EG Brennan Golf Course-E Gaynor Brennan Golf Course [Directions] | Trumbull 172 Westhill 167 | 1:30 PM, Dismiss 1:15 PM; 1 Bus | |
| Wed., 9/14 | V Field Hockey | Brien McMahon | Home - Trumbull HS-McDougall Stadium [Directions] | W 6-2 | ||
| Wed., 9/14 | V Girls Soccer | Darien | Away - Darien HS-DHS Center Oval Turf Field [Directions] | T 3-3 | 2:30 PM, Dismiss 2:15 PM; 1 Bus | |
| Wed., 9/14 | V Girls Swimming and Diving | Ridgefield | Away - Barlow Mountain Pool [Directions] | Trumbull - 77 Ridgefield - 98 | 2:00 PM, Dismiss 1:45 PM; 1 Bus | |
| Wed., 9/14 | V Girls Volleyball | Avon | Home - Trumbull HS-THS Main Gym [Directions] | W 3-0 | ||
| Thu., 9/15 | V Field Hockey | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | W 4-1 | 3:15 PM; 1 Bus | |
| Thu., 9/15 | Miscellaneous Events | Back to School Night | Home - Trumbull HS-Stadium [Directions] | 6:00 p.m. | ||
| Fri., 9/16 | V Boys Soccer | Ridgefield | Home - Trumbull HS-Cork Field [Directions] | W 3-0 | ||
| Sat., 9/17 | V Boys Cross Country | Wilton | Away - Allen's Meadow-XC Course [Directions] | 9:30 a.m. | 7:45 AM; 1 Bus | |
| Sat., 9/17 | V Football | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | W 49-7 | 11:15 AM; 2 Buses | |
| Sat., 9/17 | V Girls Cross Country | Wilton | Away - Allen's Meadow-XC Course [Directions] | 9:00 a.m. | 7:15 AM; 1 Bus | |
| Sat., 9/17 | V Girls Soccer | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | L 2-1 | 8:15 AM; 1 Bus | |
| Mon., 9/19 | V Boys Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | W 2-0 | 5:30 PM; 1 Bus | |
| Tue., 9/20 | V Boys Cross Country | New Canaan, Danbury | Away - Waveny Park [Directions] | 4:30 p.m. | 2:45 PM; 1 Bus | |
| Tue., 9/20 | V Girls Cross Country | New Canaan, Danbury | Away - Waveny Park [Directions] | 4:30 p.m. | 2:45 PM; 1 Bus | |
| Tue., 9/20 | V Field Hockey | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | W 2-0 | 2:15 PM, Dismiss 2:00 PM; 1 Bus | |
| Tue., 9/20 | V Girls Soccer | Fairfield Ludlowe | Home - Trumbull HS-Cork Field [Directions] | L 4-1 | ||
| Tue., 9/20 | V Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | L 1-3 | 2:30 PM, Dismiss 2:15 PM; 1 Bus | |
| Wed., 9/21 | V Boys Golf | Stamford | Away - Stamford High-Sterling Farms Golf Course [Directions] | Trumbull 162 Stamford 195 | 1:15 PM, Dismiss 1:00 PM; 1 Bus | |
| Thu., 9/22 | V Boys Soccer | Greenwich | Home - Trumbull HS-Cork Field [Directions] | W 2-0 | ||
| Thu., 9/22 | V Field Hockey | New Canaan | Home - Trumbull HS-McDougall Stadium [Directions] | L 0-9 | ||
| Thu., 9/22 | V Girls Volleyball | Westhill | Home - Trumbull HS-THS Main Gym [Directions] | W 3-1 | ||
| Fri., 9/23 | V Football | East Hartford | Home - Trumbull HS-McDougall Stadium [Directions] | W 47-6 | ||
| Fri., 9/23 | V Girls Soccer | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | L 2-1 | 2:45 PM; 1 Bus | |
| Sat., 9/24 | V Boys Soccer | Farmington | Away - Farmington Sports Arena-Field 7 [Directions] | W 1-0 | 10:00 AM; 1 Bus | |
| Sat., 9/24 | Miscellaneous Events | Band Comp | Home - Trumbull HS-McDougall Stadium [Directions] | 12:00 p.m. | ||
| Tue., 9/27 | V Boys Golf | Staples | Away - Longshore Golf Course [Directions] | Trumbull 160 Staples 145 | 1:30 PM, Dismiss 1:15 PM; 1 Bus | |
| Tue., 9/27 | V Field Hockey | Wilton | Home - Trumbull HS-McDougall Stadium [Directions] | L 1-4 | ||
| Tue., 9/27 | V Girls Soccer | Bridgeport Central | Home - Trumbull HS-Cork Field [Directions] | W 7-0 | ||
| Tue., 9/27 | V Girls Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | W 3-0 | 2:45 PM; 1 Bus | |
| Wed., 9/28 | V Boys Cross Country | Fairfield Ludlowe, Norwalk, Ridgefield | Home - Trumbull HS-Cross Country Course [Directions] | 4:00 p.m. | ||
| Wed., 9/28 | V Boys Golf | Danbury | Away - Richter Park Golf Course [Directions] | Trumbull 165 Danbury 162 | 1:30 PM; 1 Bus | |
| Wed., 9/28 | V Boys Soccer | Bridgeport Central | Away - Bridgeport Central-Kennedy Stadium Turf [Directions] | W 8-0 | 2:45 PM; 1 Bus | |
| Wed., 9/28 | V Girls Cross Country | Fairfield Ludlowe, Norwalk, Ridgefield | Home - Trumbull HS-Cross Country Course [Directions] | 4:00 p.m. | ||
| Wed., 9/28 | V Girls Swimming and Diving | St. Joseph | Home - Bridgeport University-Pool [Directions] | Trumbull - 95 St. Joes - 64 | ||
| Thu., 9/29 | V Boys Golf | Wilton | Home - Tashua Knolls Golf Course [Directions] | Wilton 166 Trumbull 169 | 2:15 PM; 1 Bus | |
| Thu., 9/29 | V Field Hockey | Fairfield Ludlowe | Home - Trumbull HS-McDougall Stadium [Directions] | L 0-3 | ||
| Thu., 9/29 | V Girls Volleyball | Darien | Home - Trumbull HS-THS Main Gym [Directions] | L 0-3 | ||
| Fri., 9/30 | V Football | Staples | Home - Trumbull HS-McDougall Stadium [Directions] | L 29-36 | ||
| Fri., 9/30 | V Boys Soccer | Stamford | Away - Stamford HS-SHS Upper Soccer Field [Directions] | W 3-2 | 2:15 PM, Dismiss 2:00 PM; 1 Bus | |
| Fri., 9/30 | V Girls Swimming and Diving | Westhill/Stamford | Home - Bridgeport Univ Pool-Pool [Directions] | Trumbull - 81 Westhill - 100 | ||
| Sat., 10/1 | V Field Hockey | Norwalk | Home - Trumbull HS-McDougall Stadium [Directions] | L 1-3 | ||
| Sat., 10/1 | V Girls Soccer | Stamford | Home - Trumbull HS-Cork Field [Directions] | W 6-1 | ||
| Sat., 10/1 | Miscellaneous Events | SAT's | Home - Trumbull HS-Aux Gym [Directions] | 8:00 a.m. | ||
| Mon., 10/3 | V Boys Cross Country | Wilton, Fairfield Warde, St. Joseph | Away - Allen's Meadow-XC Course [Directions] | 4:00 p.m. | 2:00 PM; 1 Bus | |
| Mon., 10/3 | V Girls Cross Country | Wilton, Fairfield Warde, Guilford, St. Joseph | Away - Allen's Meadow-XC Course [Directions] | 4:00 p.m. | 2:00 PM; 1 Bus | |
| Mon., 10/3 | V Girls Soccer | New Canaan | Home - Trumbull HS-Cork Field [Directions] | T 2-2 | ||
| Mon., 10/3 | V Girls Volleyball | Ridgefield | Home - Trumbull HS-THS Main Gym [Directions] | W 3-0 | ||
| Thu., 10/6 | V Boys Golf | Staples | Away - Longshore Golf Course [Directions] | TBA | ||
| Thu., 10/6 | V Boys Soccer | Staples | Home - Trumbull HS-Cork Field [Directions] | W 4-1 | ||
| Thu., 10/6 | V Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | L 2-3 | 2:45 PM; 1 Bus | |
| Fri., 10/7 | V Girls Soccer | Staples | Away - Staples HS-Wakeman Field B (turf) [Directions] | L 1-0 | 2:30 PM, Dismiss 2:15 PM; 1 Bus | |
| Sat., 10/8 | V Field Hockey | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | L 1-4 | 7:00 AM; 1 Bus | |
| Sat., 10/8 | V Girls Volleyball | Greenwich | Home - Trumbull HS-THS Main Gym [Directions] | W 3-0 | ||
| Mon., 10/10 | V Boys Soccer | Wilton | Away - Wilton HS-Lilly Field [Directions] | W 3-0 | 3:15 PM; 1 Bus | |
| Mon., 10/10 | V Field Hockey | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | W 2-1 | 2:30 PM, Dismiss 2:15 PM; 1 Bus | |
| Mon., 10/10 | V Girls Volleyball | Bridgeport Central | Away - Bridgeport Central HS-The Barry McLeod Court [Directions] | W 3-0 | 3:00 PM; 1 Bus | |
| Tue., 10/11 | V Boys Cross Country | Staples, Darien, Stamford | Away - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM; 1 Bus | |
| Tue., 10/11 | V Boys Golf | Brien McMahon | Away - Oak Hills Golf Course [Directions] | Trumbull 162 McMahon 174 | 1:30 PM, Dismiss 1:15 PM; 1 Bus | |
| Tue., 10/11 | V Girls Cross Country | Staples, Darien, Stamford | Away - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM; 1 Bus | |
| Tue., 10/11 | V Girls Soccer | Wilton | Home - Trumbull HS-Cork Field [Directions] | T 1-1 | ||
| Wed., 10/12 | V Boys Golf | Ridgefield | Home - Tashua Knolls Golf Course [Directions] | Trumbull 158 Ridgefield 167 | 2:15 PM; 1 Bus | |
| Wed., 10/12 | V Boys Soccer | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | W 5-0 | 3:00 PM; 1 Bus | |
| Wed., 10/12 | V Girls Swimming and Diving | New Canaan | Home - Bridgeport Univ Pool-Pool [Directions] | Trumbull - 77 New Canaan - 103 | ||
| Wed., 10/12 | V Girls Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | W 3-0 | 2:45 PM; 1 Bus | |
| Thu., 10/13 | V Boys Golf | New Canaan | Home - Tashua Knolls Golf Course [Directions] | 3:00 p.m. | 2:15 PM; 1 Bus | |
| Pending change awaiting acceptance by one or more parties involved: Date to 10/12 | ||||||
| Thu., 10/13 | V Field Hockey | Darien | Home - Trumbull HS-McDougall Stadium [Directions] | L 0-6 | ||
| Thu., 10/13 | V Girls Soccer | St. Joseph | Home - Trumbull HS-Cork Field [Directions] | L 3-1 | ||
| Thu., 10/13 | V Girls Volleyball | Staples | Home - Trumbull HS-THS Main Gym [Directions] | W 3-2 | ||
| Fri., 10/14 | V Football | Stamford | Home - Trumbull HS-McDougall Stadium [Directions] | W 42-14 | ||
| Fri., 10/14 | V Boys Soccer | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | W 4-1 | 2:45 PM; 1 Bus | |
| Mon., 10/17 | V Boys Soccer | Brien McMahon | Home - Trumbull HS-Cork Field [Directions] | W 3-0 | ||
| Mon., 10/17 | V Girls Volleyball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | L 1-3 | 3:00 PM; 1 Bus | |
| Tue., 10/18 | V Field Hockey | St. Joseph | Home - Trumbull HS-McDougall Stadium [Directions] | W 5-3 | ||
| Tue., 10/18 | V Girls Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | T 1-1 | 3:00 PM; 1 Bus | |
| Wed., 10/19 | V Boys Cross Country | FCIAC Championship | Away - Waveny Park | 2:15 p.m. | 12:00 PM; 1 Bus | |
| Wed., 10/19 | V Girls Cross Country | FCIAC Championship | Away - Waveny Park | 2:15 p.m. | 12:00 PM; 1 Bus | |
| Wed., 10/19 | V Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | W 3-0 | 3:00 PM; 1 Bus | |
| Thu., 10/20 | V Football | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | L 24-37 | 3:30 PM; 2 Buses | |
| Thu., 10/20 | V Boys Soccer | Fairfield Warde | Home - Trumbull HS-Cork Field [Directions] | W 2-1 | ||
| Thu., 10/20 | V Girls Diving | St. Joseph, TBA, Wilton | Away - New Canaan Y -Diving Only [Directions] | 3:45 p.m. | ||
| Thu., 10/20 | V Girls Soccer | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | L 3-1 | 6:00 PM; 1 Bus | |
| Fri., 10/21 | V Field Hockey | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | L 0- 1 | 2:45 PM; 1 Bus | |
| Fri., 10/21 | V Girls Swimming and Diving | Danbury | Away - WCSU O'Neill Center Pool [Directions] | Trumbull - 84 Danbury - 60 | 2:15 PM, Dismiss 2:00 PM; 1 Bus | |
| Fri., 10/21 | V Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | W 3-2 | 3:00 PM; 1 Bus | |
| Sat., 10/22 | V Girls Swimming and Diving | Norwalk/McMahon | Away - Norwalk HS-Pat Spinola Natatorium [Directions] | Trumbull - 97 Norwalk - 74 | 11:00 AM; 1 Bus | |
| Mon., 10/24 | V Boys Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | L 1-2 | 5:15 PM; 1 Bus | |
| Mon., 10/24 | V Girls Swimming and Diving | Wilton | Away - Wilton YMCA [Directions] | Trumbull - 79 Wilton - 104 | 2:00 PM, Dismiss 1:45 PM; 1 Bus | |
| Mon., 10/24 | V Girls Volleyball | Brien McMahon | Home - Trumbull HS-THS Main Gym [Directions] | W 3-0 | ||
| Tue., 10/25 | V Field Hockey | Staples | Away - Staples HS-Ginny Parker Field [Directions] | L 0-9 | 2:45 PM; 1 Bus | |
| Tue., 10/25 | V Girls Soccer | Norwalk | Home - Trumbull HS-Cork Field [Directions] | W 6-0 | ||
| Wed., 10/26 | V Girls Volleyball | Fairfield Warde | Home - Trumbull HS-THS Main Gym [Directions] | W 3-0 | ||
| Thu., 10/27 | V Boys Soccer | Brien McMahon | Home - Trumbull HS-Cork Field [Directions] | W 6-0 | ||
| Thu., 10/27 | V Girls Cross Country | Danbury | Away - Tarrywile Park [Directions] | 4:30 p.m. | 2:00 PM, Dismiss 1:45 PM; 1 Bus | |
| Thu., 10/27 | V Girls Swimming and Diving | Staples | Away - Staples HS-Staples High School Pool [Directions] | Trumbull - 81 Staples - 96 | 2:30 PM, Dismiss 2:15 PM; 1 Bus | |
| Fri., 10/28 | V Football | Fairfield Ludlowe | Home - Trumbull HS-McDougall Stadium [Directions] | W 39-14 | ||
| Fri., 10/28 | V Girls Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | W 3-0 | 2:45 PM; 1 Bus | |
| Fri., 10/28 | Miscellaneous Events | Middle School CC Meet | Home - Trumbull HS-Cross Country Course [Directions] | 3:45 p.m. | ||
| Sat., 10/29 | V Boys Cross Country | CIAC Class LL Championship | Away - Wickham Park | 10:45 a.m. | ||
| Sat., 10/29 | V Girls Cross Country | CIAC Class LL Championship | Away - Wickham Park | 10:10 a.m. | ||
| Tue., 11/1 | V Boys Golf | CIAC Division I Championship | Away - Stanley GC | 9:00 a.m. | ||
| Tue., 11/1 | V Boys Soccer | Greenwich | Home - Fairfield Ludlowe HS-Taft Field [Directions] | W 5-1 | 5:00 PM; 1 Bus | |
| Tue., 11/1 | V Girls Soccer | Darien (Scrim.) | Away - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | 2:45 PM; 1 Bus | |
| Tue., 11/1 | V Girls Swimming and Diving | TBA, Brien McMahon, Danbury, Fairfield Ludlowe, Fairfield Warde, TBA, New Canaan, Norwalk/McMahon, Ridgefield, St. Joseph, Stamford, Staples, Westhill/Stamford, Wilton | Away - Greenwich HS-Pool | 5:15 p.m. | 2:15 PM; 1 Bus | |
| Tue., 11/1 | V Girls Swimming and Diving | Greenwich, Danbury, Darien, Fairfield Ludlowe, Fairfield Warde, New Canaan, Norwalk/McMahon, Ridgefield, St. Joseph, Staples, Westhill/Stamford, Wilton | Away - Greenwich HS-Pool | 5:15 p.m. | ||
| Tue., 11/1 | V Girls Volleyball | Wilton | Home - Trumbull HS-THS Main Gym [Directions] | W 3-0 | ||
| Wed., 11/2 | V Girls Swimming and Diving | FCIAC Diving Championship | Away - Westhill HS-Westhill Pool | 5:00 p.m. | ||
| Thu., 11/3 | V Boys Soccer | Darien | Home - Norwalk HS-Testa Field, NHS [Directions] | W 4-1 | 5:00 PM; 1 Bus | |
| Thu., 11/3 | V Girls Soccer | Masuk (Scrim.) | Home - Trumbull HS-Cork Field [Directions] | 4:45 p.m. | ||
| Thu., 11/3 | V Girls Volleyball | New Canaan | Home - Fairfield Ludlowe HS-Main Gym [Directions] | W 3-1 | 4:30 PM; 1 Bus | |
| Fri., 11/4 | V Boys Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Fri., 11/4 | V Football | Ridgefield | Home - Trumbull HS-McDougall Stadium [Directions] | W 28-13 | ||
| Fri., 11/4 | V Girls Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Fri., 11/4 | V Field Hockey | Lauralton Hall (Scrim.) | Home - Trumbull HS-Aux Gym [Directions] | 4:00 p.m. | ||
| Fri., 11/4 | V Girls Swimming and Diving | TBA, Brien McMahon, Danbury, Fairfield Ludlowe, Fairfield Warde, TBA, New Canaan, Norwalk/McMahon, Ridgefield, St. Joseph, Stamford, Staples, Westhill/Stamford, Wilton | Away - Greenwich HS-Pool | 6:30 p.m. | 3:30 PM; 1 Bus | |
| Fri., 11/4 | V Girls Swimming and Diving | Greenwich, Danbury, Darien, Fairfield Ludlowe, Fairfield Warde, New Canaan, Norwalk/McMahon, Ridgefield, St. Joseph, Staples, Westhill/Stamford, Wilton | Away - Greenwich HS-Pool | 6:30 p.m. | ||
| Sat., 11/5 | V Girls Volleyball | Darien | Away - Fairfield Ludlowe HS-Main Gym [Directions] | L 2-3 | 1:00 PM | |
| Sat., 11/5 | Miscellaneous Events | SAT's | Home - Trumbull HS-Aux Gym [Directions] | 8:00 a.m. | ||
| Mon., 11/7 | V Boys Soccer | Amity | Home - Trumbull HS-Cork Field [Directions] | W 1-0 | ||
| Mon., 11/7 | V Field Hockey | Newington | Away - Newington HS-Clem Lemire Turf Field (150 New Britain Ave) [Directions] | 2:00 p.m. | ||
| Tue., 11/8 | V Girls Soccer | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 5:00 p.m. | ||
| Tue., 11/8 | V Girls Volleyball | West Haven | Home - Trumbull HS-THS Main Gym [Directions] | W 3-0 | ||
| Wed., 11/9 | V Boys Soccer | Greenwich | Home - Trumbull HS-Cork Field [Directions] | L 0-1 (3-4 PK) | ||
| Wed., 11/9 | V Field Hockey | Wilton | Away - Wilton HS-Fuijitani Field -Turf [Directions] | 6:30 p.m. | ||
| Wed., 11/9 | Miscellaneous Events | Underage Drinking Forum | Home - Trumbull HS-THS Main Gym [Directions] | 3:00 p.m. | ||
| Thu., 11/10 | V Girls Soccer | Southington | Away - Southington HS-3 TURF FIELD [Directions] | 3:30 p.m. | 1:00 PM; 1 Bus | |
| Thu., 11/10 | V Girls Swimming and Diving | CIAC Class LL Diving Championships | Away - Sheehan | 5:30 p.m. | ||
| Thu., 11/10 | V Girls Volleyball | Simsbury | Away - Simsbury HS-Simsbury / Main Gym [Directions] | W 3-1 | ||
| Sat., 11/12 | V Football | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | W 42-7 | 3:45 PM; 2 Buses | |
| Sat., 11/12 | V Girls Swimming and Diving | CIAC Class LL Trials | Away - Cornerstone Pool | 11:15 a.m. | 7:30 AM; 1 Bus | |
| Sat., 11/12 | V Girls Volleyball | Brien McMahon | Home - Trumbull HS-THS Main Gym [Directions] | W 3-0 | ||
| Tue., 11/15 | Miscellaneous Events | CIAC Field Hockey State Semi-Finals | Home - Trumbull HS-McDougall Stadium [Directions] | 6:30 p.m. | ||
| Wed., 11/16 | V Girls Swimming and Diving | CIAC Class LL Final | Away - Cornerstone Pool | 6:00 p.m. | ||
| Wed., 11/16 | V Girls Volleyball | Amity | Away - Jonathan Law HS-James L. Richetelli Memorial Gymnasium [Directions] | 6:00 p.m. | 4:15 PM; 1 Bus | |
| Thu., 11/17 | V Girls Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 11/19 | V Girls Volleyball | Darien | Away - East Haven HS-Gym [Directions] | 10:00 a.m. | 8:00 AM; 1 Bus | |
| Sun., 11/20 | V Girls Swimming and Diving | CIAC State Open Swimming Championship | Away - Yale | 2:00 p.m. | ||
| Thu., 11/24 | V Football | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | L 17-20 | 8:00 AM; 2 Buses | |
| Tue., 11/29 | V Football | Southington | Away - Southington HS-3 TURF FIELD [Directions] | 6:30 p.m. | ||
| Sat., 12/3 | V Girls Basketball | Daniel Hand (Scrim.) | Away - Daniel Hand HS-DHHS Gym [Directions] | 10:00 a.m. | 8:15 AM; 1 Bus | |
| Sat., 12/3 | V Girls Ice Hockey | Woodstock Academy Coop (Scrim.) | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 6:00 p.m. | ||
| Sat., 12/3 | V Girls Ice Hockey | Hamden Coop | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 7:45 p.m. | ||
| Sat., 12/3 | V Girls Ice Hockey | West Haven/SHA (Scrim.) | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 9:15 p.m. | ||
| Sun., 12/4 | V Football | Fairfield Prep | Away - Fairfield University-Rafferty Stadium [Directions] | 12:30 p.m. | 10:00 AM; 2 Buses | |
| Wed., 12/7 | V Boys Basketball | Bunnell (Scrim.) | Away - Bunnell HS-David Johnson Gymnasium [Directions] | 4:30 p.m. | 2:45 PM; 1 Bus | |
| Wed., 12/7 | V Boys Ice Hockey | Newington Coop (Scrim.) | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 8:00 p.m. | ||
| Wed., 12/7 | V Girls Basketball | Simsbury (Scrim.) | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 12/9 | V Boys Basketball | Shelton (Scrim.) | Away - Shelton HS-Murray Gymnasium [Directions] | 3:30 p.m. | 2:45 PM; 1 Bus | |
| Fri., 12/9 | V Girls Basketball | Pomperaug (Scrim.) | Away - Pomperaug HS-Main Gym [Directions] | 5:00 p.m. | 3:15 PM; 1 Bus | |
| Fri., 12/9 | V Girls Ice Hockey | Daniel Hand Coop | Away - Northford-Red [Directions] | L 4-5 | 2:15 PM, Dismiss 1:30 PM; 1 Bus | |
| Sat., 12/10 | V Boys Ice Hockey | Jamboree 2 The Rinks | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | TBA | ||
| Sat., 12/10 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Away - Hamden-Lou Astorino Ice Rink [Directions] | W 7-3 | 4:45 PM; 1 Bus | |
| Mon., 12/12 | V Boys Basketball | Fairfield Prep (Scrim.) | Home - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | ||
| Tue., 12/13 | V Girls Basketball | Hamden | Home - Trumbull HS-THS Main Gym [Directions] | L 41-43 | ||
| Wed., 12/14 | V Boys Ice Hockey | Watertown-Pomperaug | Away - Taft School-Mays [Directions] | W 4-3 | 6:00 PM; 1 Bus | |
| Wed., 12/14 | V Wrestling | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 7:00 p.m. | 5:15 PM; 1 Bus | |
| Wed., 12/14 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | L 1-4 | ||
| Thu., 12/15 | V Boys Basketball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | L 48-51 | 4:15 PM; 1 Bus | |
| Fri., 12/16 | V Girls Basketball | New Milford | Away - New Milford HS-Main Gym - NMHS [Directions] | L 28-38 | 2:45 PM; 1 Bus | |
| Sat., 12/17 | V Boys Basketball | Amity | Home - Trumbull HS-THS Main Gym [Directions] | W 71-49 | ||
| Sat., 12/17 | V Boys Ice Hockey | North Branford | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | L 1-3 | ||
| Sat., 12/17 | V Boys Indoor Track | Staples, Greenwich, Stamford, Westhill | Away - Staples HS-Field House [Directions] | 1:30 p.m. | 12:00 PM; 1 Bus | |
| Sat., 12/17 | V Wrestling | Manchester, East Hartford, Glastonbury, New Britain, RHAM, South Windsor, West Springfield (MA) | Away - Manchester HS-Gym | Cancelled | 6:00 AM; 1 Bus | |
| Sat., 12/17 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | L 2-1 | ||
| Sat., 12/17 | V Girls Indoor Track | Staples, Greenwich, Stamford, Westhill | Away - Staples HS-Field House [Directions] | 1:30 p.m. | 12:00 PM; 1 Bus | |
| Tue., 12/20 | V Girls Ice Hockey | West Haven/SHA | Away - West Haven HS-Bennett Rink [Directions] | L 1-2 | ||
| Wed., 12/21 | V Wrestling | Greenwich | Home - Trumbull HS-Aux Gym [Directions] | 6:00 p.m. | ||
| Wed., 12/21 | V Girls Basketball | Glastonbury | Away - Glastonbury HS-Gym [Directions] | L 25-34 | 3:15 PM; 1 Bus | |
| Wed., 12/21 | V Girls Ice Hockey | New Canaan | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | L 2-7 | ||
| Fri., 12/23 | V Wrestling | New Milford | Home - Trumbull HS-Aux Gym [Directions] | Postponed | ||
| Mon., 12/26 | V Boys Indoor Track | Northshore Invitational @ The Armory | Away - Armory Track (168th Street Armory, NYC) | 9:00 a.m. | 6:30 AM; 1 Bus | |
| Mon., 12/26 | V Wrestling | New Canaan, Greenwich, Norwalk | Away - New Canaan HS-Main Gym [Directions] | 9:15 a.m. | ||
| Mon., 12/26 | V Girls Indoor Track | Northshore Invitational @ The Armory | Away - Armory Track (168th Street Armory, NYC) | 9:00 a.m. | 6:30 AM; 1 Bus | |
| Tue., 12/27 | V Boys Basketball | Morgan | Home - Stratford HS-Gym [Directions] | W 58-52 | ||
| Tue., 12/27 | V Wrestling | Brien McMahon, St. Joseph, Wilton | Home - Trumbull HS-THS Main Gym [Directions] | 9:00 a.m. | ||
| Tue., 12/27 | V Girls Basketball | Amity | Home - Trumbull HS-Gym [Directions] | W 49-38 | ||
| Wed., 12/28 | V Boys Basketball | Stratford | Away - Stratford HS-Gym [Directions] | W 54-37 | ||
| Wed., 12/28 | V Boys Ice Hockey | Oyster River (NH) | Away - University of New Hampshire - Durham Campus-University of New Hampshire - Durham Campus - Whittemore Center | L 1-4 | ||
| Wed., 12/28 | V Wrestling | Branford | Home - Trumbull HS-Aux Gym [Directions] | 11:00 a.m. | ||
| Thu., 12/29 | V Boys Ice Hockey | Marshwood (ME) | Away - University of New Hampshire - Durham Campus-University of New Hampshire - Durham Campus - Whittemore Center | L 1-2 | ||
| Thu., 12/29 | V Girls Basketball | Masuk | Home - Trumbull HS-Gym [Directions] | W 31-26 | ||
| Fri., 12/30 | V Boys Ice Hockey | Portsmouth (NH) | Away - Wentworth / Alumni - Portsmouth Varsity | W 5-3 | ||
| Fri., 12/30 | V Wrestling | Amity, Berlin, Greenwich, Foran, Manchester, Masuk, Minnechaug (MA), TBA, Pomperaug, Stratford | Home - Trumbull HS-Aux Gym [Directions] | 8:00 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 9:00 a.m. | ||||||
| Tue., 1/3 | V Girls Basketball | Bridgeport Central | Home - Trumbull HS-THS Main Gym [Directions] | W 52-20 | ||
| Wed., 1/4 | V Boys Ice Hockey | Wilton | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | W 6-1 | ||
| Wed., 1/4 | V Boys Swimming and Diving | Darien, St. Joseph | Away - Darien YMCA [Directions] | 3:00 p.m. | 1:45 PM, Dismiss 1:30 PM; 1 Bus | |
| Wed., 1/4 | V Wrestling | Danbury | Away - Danbury HS-New gym [Directions] | 5:00 p.m. | 3:00 PM; 1 Bus | |
| Wed., 1/4 | V Girls Ice Hockey | Darien | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | L 1-5 | ||
| Thu., 1/5 | V Boys Basketball | Westhill | Home - Trumbull HS-THS Main Gym [Directions] | W 64-41 | ||
| Thu., 1/5 | V Girls Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | W 48-18 | 2:45 PM; 1 Bus | |
| Thu., 1/5 | V Girls Ice Hockey | Greenwich | Away - Greenwich - Dorothy Hamill-Rink [Directions] | L 1-3 | 6:15 PM; 1 Bus | |
| Fri., 1/6 | V Boys Swimming and Diving | Wilton | Home - Univ of Bridgeport Pool [Directions] | 4:00 p.m. | ||
| Sat., 1/7 | V Boys Ice Hockey | Brien McMahon/Norwalk | Away - Sono Ice House-Main Rink [Directions] | W 3-2 | 5:30 PM; 1 Bus | |
| Sat., 1/7 | V Wrestling | East Haven, Glastonbury, Stratford, Waterford | Away - East Haven HS-Gym [Directions] | 9:30 a.m. | 7:30 AM; 1 Bus | |
| Sat., 1/7 | V Girls Basketball | New Canaan | Home - Trumbull HS-THS Main Gym [Directions] | W 29-26 | ||
| Sat., 1/7 | V Girls Gymnastics | Fairfield Ludlowe | Home - Next Dimension Gymnastics-Next Dimension [Directions] | Trumbull 129.95: Ludlowe 131.65 | ||
| Tue., 1/10 | V Boys Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | L 51-58 | 3:45 PM; 1 Bus | |
| Tue., 1/10 | V Wrestling | Harding/Bassick/Bridgeport Central | Home - Trumbull HS-Aux Gym [Directions] | 5:00 p.m. | ||
| Tue., 1/10 | V Girls Basketball | Danbury | Home - Trumbull HS-THS Main Gym [Directions] | W 43-28 | ||
| Wed., 1/11 | V Boys Ice Hockey | Staples | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | W 6-1 | ||
| Wed., 1/11 | V Boys Swimming and Diving | Staples | Home - Univ of Bridgeport Pool [Directions] | 4:00 p.m. | ||
| Wed., 1/11 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Conners - Stamford-Ice Rink [Directions] | L 1-3 | 6:30 PM; 1 Bus | |
| Thu., 1/12 | V Girls Gymnastics | Staples, St. Joseph | Away - Staples HS-Westport YMCA [Directions] | Trumbull 123.6; Staples 127.85 | 5:30 PM; 1 Bus | |
| Thu., 1/12 | V Girls Gymnastics | Norwalk, St. Joseph | Away - Staples HS-Westport YMCA [Directions] | TBA | ||
| Thu., 1/12 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | W 3-2 | ||
| Fri., 1/13 | V Boys Basketball | Darien | Home - Trumbull HS-THS Main Gym [Directions] | W 56-47 | ||
| Fri., 1/13 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Home - Univ of Bridgeport Pool [Directions] | 4:00 p.m. | ||
| Fri., 1/13 | V Girls Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | W 41-20 | 4:00 PM; 1 Bus | |
| Sat., 1/14 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland of Ice-Stadium [Directions] | L 0-4 | 4:45 PM; 1 Bus | |
| Sat., 1/14 | V Boys Indoor Track | Wilton, Fairfield Warde, Norwalk, Westhill | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 12:00 p.m. | 10:30 AM; 1 Bus | |
| Sat., 1/14 | V Wrestling | Enfield Duals | Away - Enfield HS-EHS GYM - MAIN | 10:00 a.m. | 7:00 AM; 1 Bus | |
| Sat., 1/14 | V Girls Gymnastics | Darien, St. Joseph | Away - Darien YMCA [Directions] | Trumbull 120.5; Darien 130.25 | 1:00 PM; 1 Bus | |
| Sat., 1/14 | V Girls Indoor Track | Wilton, Fairfield Warde, Norwalk, Westhill | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 12:00 p.m. | 10:30 AM; 1 Bus | |
| Mon., 1/16 | V Boys Ice Hockey | St. Joseph | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | L 4-6 | ||
| Mon., 1/16 | V Girls Gymnastics | Greenwich | Home - Next Dimension Gymnastics-Next Dimension [Directions] | trumbull 124.35; Greenwich 121.0 | ||
| Tue., 1/17 | V Boys Basketball | Ridgefield | Home - Trumbull HS-THS Main Gym [Directions] | L 53-54 | ||
| Tue., 1/17 | V Girls Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | L 56-59 | 3:30 PM; 1 Bus | |
| Wed., 1/18 | V Boys Ice Hockey | Branford | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | W 6-5 | ||
| Wed., 1/18 | V Boys Swimming and Diving | Westhill/Stamford | Home - Univ of Bridgeport Pool [Directions] | 4:00 p.m. | ||
| Wed., 1/18 | V Wrestling | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 7:00 p.m. | 5:00 PM; 1 Bus | |
| Wed., 1/18 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice-New [Directions] | W 5-1 | 6:30 PM; 1 Bus | |
| Fri., 1/20 | V Boys Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | L 67-70 | 3:45 PM; 1 Bus | |
| Fri., 1/20 | V Boys Swimming and Diving | Danbury | Away - WCSU O'Neill Center Pool [Directions] | Cancelled | 3:15 PM; 1 Bus | |
| Fri., 1/20 | V Girls Basketball | Wilton | Home - Trumbull HS-THS Main Gym [Directions] | W 32-27 | ||
| Sat., 1/21 | V Boys Ice Hockey | Greenwich | Away - Greenwich - Dorothy Hamill-Rink [Directions] | L 0-1 | 3:45 PM; 1 Bus | |
| Sat., 1/21 | V Boys Indoor Track | Staples, Fairfield Warde, Ridgefield, Westhill | Away - Staples HS-Field House [Directions] | 1:30 p.m. | 12:00 PM; 1 Bus | |
| Sat., 1/21 | V Wrestling | Colter Abely Wrestling Tournament | Away - Mercy HS-Gym | 8:00 a.m. | 6:00 AM; 1 Bus | |
| Sat., 1/21 | V Girls Gymnastics | Stamford, Westhill | Home - Next Dimension Gymnastics-Next Dimension [Directions] | Trumbull 127.25; Stamford 55.95; Westhill 30.2 | ||
| Sat., 1/21 | V Girls Ice Hockey | Hall/Conard | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | L 3-5 | ||
| Sat., 1/21 | V Girls Indoor Track | Staples, Fairfield Warde, Ridgefield, Westhill | Away - Staples HS-Field House [Directions] | 1:30 a.m. | 12:00 PM; 1 Bus | |
| Pending change awaiting acceptance by one or more parties involved: Time to 1:30 p.m. | ||||||
| Sat., 1/21 | Miscellaneous Events | Hillcrest/Madison Double Header | Home - Trumbull HS-THS Main Gym [Directions] | 5:00 p.m. | ||
| Tue., 1/24 | V Boys Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | W 59-51 | 4:00 PM; 1 Bus | |
| Tue., 1/24 | V Boys Ice Hockey | Ridgefield | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | L 1-3 | ||
| Tue., 1/24 | V Girls Basketball | Fairfield Ludlowe | Home - Trumbull HS-THS Main Gym [Directions] | L 58-29 | ||
| Wed., 1/25 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Home - Univ of Bridgeport Pool [Directions] | 4:00 p.m. | ||
| Wed., 1/25 | V Wrestling | Staples | Home - Trumbull HS-Aux Gym [Directions] | 6:00 p.m. | ||
| Thu., 1/26 | V Boys Ice Hockey | JBWA | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | L 1-2 | ||
| Fri., 1/27 | V Boys Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | W 62-45 | 3:45 PM; 1 Bus | |
| Fri., 1/27 | V Boys Swimming and Diving | New Canaan | Away - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | 2:00 PM; 1 Bus | |
| Fri., 1/27 | V Girls Basketball | Norwalk | Home - Trumbull HS-THS Main Gym [Directions] | W 40-27 | ||
| Sat., 1/28 | V Boys Ice Hockey | Westhill/Stamford | Away - Terry Conners - Stamford-Ice Rink [Directions] | L 0-4 | 6:00 PM; 1 Bus | |
| Sat., 1/28 | V Boys Indoor Track | FCIAC Western Divisional Championships | Home - Trumbull HS-THS Main Gym [Directions] | 10:00 a.m. | 8:30 AM; 1 Bus | |
| Sat., 1/28 | V Wrestling | CONNECTICUT CHALLENGE WRESTLING | Away - Southington HS-Gym West | 9:00 a.m. | 6:30 PM; 1 Bus | |
| Sat., 1/28 | V Girls Gymnastics | New Canaan | Home - Next Dimension Gymnastics-Next Dimension [Directions] | Trumbull 129.2; New Canaan 81.4 | ||
| Sat., 1/28 | V Girls Indoor Track | FCIAC Western Divisional Championships | Home - Trumbull HS-THS Main Gym [Directions] | 10:00 a.m. | 8:30 AM; 1 Bus | |
| Mon., 1/30 | V Girls Ice Hockey | Greenwich | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | W 5-3 | ||
| Tue., 1/31 | V Boys Basketball | Greenwich | Home - Trumbull HS-THS Main Gym [Directions] | W 62-45 | ||
| Tue., 1/31 | V Girls Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | W 40-37 | 3:30 PM; 1 Bus | |
| Tue., 1/31 | V Girls Ice Hockey | Masuk Coop | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | W 2-1 | ||
| Wed., 2/1 | V Boys Ice Hockey | Wilton | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | W 6-3 | 6:30 PM; 1 Bus | |
| Wed., 2/1 | V Wrestling | Westhill | Away - Westhill HS-Main Gym [Directions] | 6:00 p.m. | 3:45 PM; 1 Bus | |
| Thu., 2/2 | V Boys Indoor Track | FCIAC Championships | Away - Floyd Little Athletic Center-Field House | 5:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Not Listed-Floyd Little Athletic Center | ||||||
| Thu., 2/2 | V Boys Swimming and Diving | Greenwich, Danbury | Away - Greenwich HS-Pool [Directions] | 4:15 p.m. | 2:45 PM; 1 Bus | |
| Thu., 2/2 | V Girls Indoor Track | FCIAC, Bridgeport Central, Brien McMahon, Danbury, Darien, Fairfield Ludlowe, Fairfield Warde, Greenwich, New Canaan, Norwalk, Ridgefield, St. Joseph, Stamford, Staples, Westhill, Wilton | Away - Floyd Little Athletic Center-Field House | 5:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Not Listed-Floyd Little Athletic Center | ||||||
| Fri., 2/3 | V Boys Basketball | Fairfield Warde | Home - Trumbull HS-THS Main Gym [Directions] | L 48-53 | ||
| Fri., 2/3 | V Wrestling | Fairfield Warde, Fitch | Away - Fairfield Warde HS-Small Gym [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Fri., 2/3 | V Girls Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | L 29-40 | 3:45 PM; 1 Bus | |
| Sat., 2/4 | V Boys Ice Hockey | Cheshire | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | L 0-3 | ||
| Sat., 2/4 | V Competitive Cheerleading | FCIAC Cheer Championship | Home - Trumbull HS-THS Main Gym [Directions] | 11:00 a.m. | ||
| Sat., 2/4 | V Girls Gymnastics | Wilton, St. Joseph | Away - Wilton HS-Aux Gym [Directions] | Trumbull 128.65; Wilton 135.05 | 2:45 PM; 1 Bus | |
| Sat., 2/4 | V Girls Ice Hockey | West Haven/SHA | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | L 4-2 | ||
| Mon., 2/6 | V Boys Swimming and Diving | Ridgefield, St. Joseph | Away - Barlow Mountain Pool [Directions] | 4:00 p.m. | 2:00 PM; 1 Bus | |
| Tue., 2/7 | V Boys Basketball | Staples | Home - Trumbull HS-THS Main Gym [Directions] | L 45-50 | ||
| Tue., 2/7 | V Wrestling | Norwalk | Home - Trumbull HS-Aux Gym [Directions] | 6:00 p.m. | ||
| Tue., 2/7 | V Girls Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | W 58-38 | 3:45 PM; 1 Bus | |
| Wed., 2/8 | V Boys Ice Hockey | Brien McMahon/Norwalk | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | W 4-0 | ||
| Thu., 2/9 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | W 6-3 | 1:45 PM; 1 Bus | |
| Fri., 2/10 | V Boys Basketball | St. Joseph | Home - Trumbull HS-THS Main Gym [Directions] | W 65-56 | ||
| Fri., 2/10 | V Wrestling | New Canaan, Bridgeport Central, Brien McMahon, Danbury, Darien, FCIAC, Fairfield Ludlowe, Fairfield Warde, Greenwich, Norwalk, Ridgefield, St. Joseph, Stamford, Staples, Westhill, Wilton | Away - New Canaan HS-Main Gym | 4:00 p.m. | ||
| Fri., 2/10 | V Girls Basketball | St. Joseph | Home - Trumbull HS-THS Main Gym [Directions] | L 44-31 | ||
| Sat., 2/11 | V Boys Ice Hockey | Staples | Away - Milford Ice Pavillion-Ice Rink [Directions] | W 4-3 | 4:30 PM; 1 Bus | |
| Sat., 2/11 | V Boys Indoor Track | CIAC Class LL Championships | Away - Floyd Little Athletic Center | 4:00 p.m. | ||
| Sat., 2/11 | V Girls Gymnastics | FCIAC Gymnastics | Away - Gymnastics and Cheerleading Academy at Connecticut | 126.825 | 8:00 AM; 1 Bus | |
| Sat., 2/11 | V Girls Ice Hockey | Masuk Coop | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | W 6-1 | ||
| Sat., 2/11 | V Girls Indoor Track | CIAC Class LL Championships | Away - Floyd Little Athletic Center | 4:00 p.m. | ||
| Mon., 2/13 | V Boys Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | L 72-75(2OT) | 3:30 PM; 1 Bus | |
| Mon., 2/13 | V Girls Basketball | Stamford | Home - Trumbull HS-THS Main Gym [Directions] | W 40-24 | ||
| Mon., 2/13 | V Girls Ice Hockey | Woodstock Academy Coop | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | W 4-1 | ||
| Wed., 2/15 | V Boys Basketball | Brien McMahon | Home - Trumbull HS-THS Main Gym [Directions] | W 54-47 | ||
| Wed., 2/15 | V Boys Ice Hockey | Westhill/Stamford | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | L 4-5 | ||
| Wed., 2/15 | V Girls Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | W 49-22 | 2:45 PM; 1 Bus | |
| Wed., 2/15 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | L 0-3 | 2:15 PM; 1 Bus | |
| Fri., 2/17 | V Boys Basketball | Harding | Away - Warren Harding HS-Gym [Directions] | L 75-66 | 4:00 PM; 1 Bus | |
| Fri., 2/17 | V Wrestling | CIAC LL Championship | Away - Trumbull | 4:00 p.m. | ||
| Fri., 2/17 | Miscellaneous Events | LL Wrestling Championships | Home - Trumbull HS-Gym [Directions] | 12:00 p.m. | ||
| Sat., 2/18 | V Boys Indoor Track | CIAC State Open Championships | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/18 | V Wrestling | CIAC LL Championship | Away - Trumbull | 10:30 a.m. | ||
| Sat., 2/18 | V Girls Basketball | Ridgefield | Away - Staples HS [Directions] | 5:00 p.m. | ||
| Sat., 2/18 | V Girls Gymnastics | St. Joseph | Home - Next Dimension Gymnastics-Next Dimension [Directions] | Cancelled | ||
| Sat., 2/18 | V Girls Ice Hockey | Hamden Coop | Away - Hamden-Lou Astorino Ice Rink [Directions] | L 0-6 | 2:30 PM; 1 Bus | |
| Sat., 2/18 | V Girls Indoor Track | CIAC State Open Championships | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Mon., 2/20 | V Boys Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | W 40-42 | 3:45 PM; 1 Bus | |
| Tue., 2/21 | V Girls Basketball | Fairfield Ludlowe | Away - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | ||
| Wed., 2/22 | V Boys Basketball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | W 76-68 | 4:00 PM; 1 Bus | |
| Fri., 2/24 | V Wrestling | CIAC State Open | Away - Floyd Little Athletic Center | 12:45 p.m. | ||
| Fri., 2/24 | V Girls Basketball | Newtown (Scrim.) | Away - Newtown HS-Gym [Directions] | 3:00 p.m. | 2:15 PM; 1 Bus | |
| Sat., 2/25 | V Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | W 76-70 | ||
| Sat., 2/25 | V Wrestling | CIAC State Open | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Sat., 2/25 | V Girls Gymnastics | CIAC Divisional Championships | Away - Jonathan Law | TBA | ||
| Mon., 2/27 | V Girls Basketball | Southington | Home - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/28 | V Boys Swimming and Diving | FCIAC Swim Trial Boys | Away - Greenwich HS-Pool | 5:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 3/1 | ||||||
| Wed., 3/1 | V Boys Basketball | Danbury | Home - Wilton HS-Wilton Field House [Directions] | L 52-50 | 3:30 PM; 1 Bus | |
| Thu., 3/2 | V Boys Ice Hockey | Staples | Home - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | ||
| Fri., 3/3 | V Boys Swimming and Diving | FCIAC Championships @ Greenwich | Home - Hillcrest MS-Pool [Directions] | 5:30 p.m. | 2:30 PM; 1 Bus | |
| Fri., 3/3 | V Boys Swimming and Diving | Greenwich, Danbury, Darien, Farfield Ludlowe/Warde, Fairfield Warde, TBA, New Canaan, Norwalk/Brien McMahon, Ridgefield, St. Joseph, Staples, Westhill/Stamford, Wilton | Away - Greenwich HS-Pool | 6:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 5:30 p.m. | ||||||
| Fri., 3/3 | V Girls Basketball | Glastonbury | Away - Glastonbury HS-Gym [Directions] | 5:00 p.m. | 2:30 PM | |
| Sat., 3/4 | V Boys Ice Hockey | Westhill/Stamford | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 8:30 p.m. | ||
| Sat., 3/4 | V Competitive Cheerleading | State Championship Comp | Home - Trumbull HS-THS Main Gym [Directions] | 11:00 a.m. | 6:45 AM; 1 Bus | |
| Sat., 3/4 | V Girls Gymnastics | CIAC State Open | Away - New Milford | 4:00 p.m. | ||
| Tue., 3/7 | V Boys Basketball | Glastonbury | Away - Glastonbury HS-Gym [Directions] | W 59-55 OT | 2:45 PM, Dismiss 2:15 PM; 1 Bus | |
| Tue., 3/7 | V Boys Ice Hockey | Cheshire | Away - Hamden-Lou Astorino Ice Rink [Directions] | 3:45 p.m. | 2:00 PM; 1 Bus | |
| Thu., 3/9 | V Boys Basketball | Windsor | Away - Windsor HS-WHS Main Gym [Directions] | 6:30 p.m. | 3:45 PM; 1 Bus | |
| Thu., 3/9 | V Boys Swimming and Diving | CIAC Class LL Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Fri., 3/10 | V Boys Ice Hockey | Branford | Away - West Haven HS-Bennett Rink [Directions] | 5:00 p.m. | 3:00 PM; 1 Bus | |
| Sat., 3/11 | V Boys Swimming and Diving | CIAC Class LL Trials | Away - Cornerstone Pool | 4:30 p.m. | 1:00 PM; 1 Bus | |
| Mon., 3/13 | V | CIAC Basketball Tourney | Away - East Haven HS-Gym | 3:30 p.m. | ||
| Thu., 3/16 | V Boys Swimming and Diving | CIAC Class LL Finals | Away - Cornerstone Pool | 1:30 p.m. | ||
| Fri., 3/17 | V Boys Swimming and Diving | CIAC Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/18 | V Boys Swimming and Diving | CIAC State Open Championship | Away - Yale | 1:00 p.m. | ||
| Wed., 3/22 | V Softball | Amity (Scrim.) | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 4:00 p.m. | ||
| Fri., 3/24 | V Softball | Maloney (Scrim.) | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 4:00 p.m. | ||
| Sat., 3/25 | V Boys Lacrosse | Bethel (Scrim.) | Home - Trumbull HS-Cork Field [Directions] | 2:00 p.m. | ||
| Sat., 3/25 | V Boys Rugby | New Rochelle HS | Home - Trumbull HS-Aux Gym [Directions] | 10:00 a.m. | ||
| Sat., 3/25 | V Boys Volleyball | Joel Barlow, Fairfield Ludlowe, Glastonbury, Iona Prep (NY), New Canaan, Pomperaug, Simsbury, Staples | Away - Joel Barlow HS-Lower Gym | 10:00 a.m. | 8:45 AM; 1 Bus | |
| Sat., 3/25 | V Softball | Naugatuck (Scrim.) | Home - Trumbull HS-Varsity Softball Diamond [Directions] | Cancelled | ||
| Sun., 3/26 | V Baseball | Bunnell (Scrim.) | Away - Bunnell HS-Bunnell Baseball Field [Directions] | 1:00 p.m. | 11:30 AM; 1 Bus | |
| Mon., 3/27 | V Baseball | Staples (Scrim.) | Home - Trumbull HS-Varsity Baseball Field [Directions] | 3:45 p.m. | ||
| Mon., 3/27 | V Softball | Woodland (Scrim.) | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 4:00 p.m. | ||
| Tue., 3/28 | V Baseball | Notre Dame-Fairfield (Scrim.) | Home - Trumbull HS-Varsity Baseball Field [Directions] | 3:45 p.m. | ||
| Tue., 3/28 | V Boys Tennis | Newtown (Scrim.) | Home - Trumbull HS-Tennis Courts [Directions] | 4:30 p.m. | ||
| Tue., 3/28 | V Softball | Foran (Scrim.) | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 3/29 | V Baseball | Seymour (Scrim.) | Home - Trumbull HS-Varsity Baseball Field [Directions] | 3:45 p.m. | ||
| Wed., 3/29 | V Girls Lacrosse | Amity (Scrim.) | Away - Amity Regional HS-William Johnson Stadium Field [Directions] | 3:45 p.m. | 2:15 PM, Dismiss 2:00 PM; 1 Bus | |
| Wed., 3/29 | V Softball | New Milford (Scrim.) | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 4:00 p.m. | ||
| Thu., 3/30 | V Baseball | Newtown (Scrim.) | Away - Newtown HS-Nighthawk Ball Park [Directions] | Cancelled | 2:45 PM; 1 Bus | |
| Thu., 3/30 | V Boys Lacrosse | Greens Farms Academy (Scrim.) | Away - Greens Farms Academy-Stadium Turf | 4:00 p.m. | 2:45 PM; 1 Bus | |
| Thu., 3/30 | V Boys Tennis | Fairfield Prep (Scrim.) | Home - Trumbull HS-Tennis Courts [Directions] | Cancelled | ||
| Thu., 3/30 | V Boys Volleyball | Shelton (Scrim.) | Away - Shelton HS-Murray Gymnasium [Directions] | 3:45 p.m. | 2:45 PM; 1 Bus | |
| Fri., 3/31 | V Girls Tennis | Seymour (Scrim.) | Home - Trumbull HS-Tennis Courts [Directions] | W 7-0 [Detailed Results] | ||
| Fri., 3/31 | Miscellaneous Events | Sophomore Ring Dance | Home - Trumbull HS-Aux Gym [Directions] | 6:30 p.m. | ||
| Sat., 4/1 | V Boys Rugby | Darien (Scrim.) | Home - Trumbull HS-Aux Gym [Directions] | 10:30 a.m. | ||
| Sat., 4/1 | V Boys Rugby | Fairfield Ludlowe (Scrim.) | Home - Trumbull HS-Aux Gym [Directions] | 10:30 a.m. | ||
| Sat., 4/1 | V Boys Volleyball | Masuk | Home - Trumbull HS-THS Main Gym [Directions] | W 3-1 | ||
| Tue., 4/4 | V Baseball | Shelton | Home - Trumbull HS-Varsity Baseball Field [Directions] | W 8-1 | ||
| Tue., 4/4 | V Boys Outdoor Track | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM; 1 Bus | |
| Tue., 4/4 | V Girls Lacrosse | New Fairfield | Away - New Fairfield HS-Marty Morgan Field [Directions] | L 0-19 | 2:30 PM, Dismiss 2:15 PM; 1 Bus | |
| Tue., 4/4 | V Girls Outdoor Track | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM; 1 Bus | |
| Tue., 4/4 | V Softball | East Haven | Away - East Haven HS-Softball Diamond [Directions] | W 8-1 | 2:45 PM; 1 Bus | |
| Wed., 4/5 | V Boys Volleyball | Newtown | Away - Newtown HS-Gym [Directions] | W 3-0 | 2:45 PM; 1 Bus | |
| Thu., 4/6 | V Baseball | Fairfield Prep | Home - Trumbull HS-Varsity Baseball Field [Directions] | W 7-3 | ||
| Thu., 4/6 | V Boys Lacrosse | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | W 21-3 | 2:45 PM; 1 Bus | |
| Thu., 4/6 | V Boys Tennis | Weston | Home - Trumbull HS-Tennis Courts [Directions] | W 4-3 [Detailed Results] | ||
| Thu., 4/6 | V Boys Volleyball | Newington | Away - Newington HS-Gym [Directions] | W 3-0 | 2:45 PM; 1 Bus | |
| Thu., 4/6 | V Girls Golf | St. Joseph | Away - Tashua Knolls Golf Course [Directions] | THS 184;St Joes 238 | ||
| Thu., 4/6 | V Girls Lacrosse | Danbury | Home - Trumbull HS-McDougall Stadium [Directions] | L 4-5 | ||
| Thu., 4/6 | V Softball | Shelton | Home - Trumbull HS-Varsity Softball Diamond [Directions] | W 15-1 (5inn) | ||
| Thu., 4/6 | V Girls Tennis | Weston | Away - Weston HS-WHS Tennis Courts [Directions] | L 1-6 [Detailed Results] | 2:45 PM; 1 Bus | |
| Sat., 4/8 | V Baseball | Notre Dame-West Haven | Home - Trumbull HS-Varsity Baseball Field [Directions] | W 2-0 | ||
| Sat., 4/8 | V Boys Lacrosse | Norwalk | Away - Norwalk HS-Testa Field [Directions] | W 15-2 | 9:00 AM; 1 Bus | |
| Sat., 4/8 | V Boys Volleyball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | W 3-0 | 8:00 AM; 1 Bus | |
| Sat., 4/8 | V Girls Lacrosse | Norwalk | Home - Trumbull HS-McDougall Stadium [Directions] | L 3-17 | ||
| Sat., 4/8 | V Softball | Ledyard | Home - Trumbull HS-Varsity Softball Diamond [Directions] | W 11-1 | ||
| Mon., 4/10 | V Boys Tennis | Westhill | Home - Trumbull HS-Tennis Courts [Directions] | L 2-5 [Detailed Results] | ||
| Mon., 4/10 | V Softball | St. Joseph | Home - Trumbull HS-Varsity Softball Diamond [Directions] | W 5-4 | ||
| Mon., 4/10 | V Girls Tennis | Westhill | Away - Westhill HS-Westhill Tennis Courts [Directions] | L 2-5 [Detailed Results] | 2:30 PM; 1 Bus | |
| Tue., 4/11 | V Baseball | Masuk | Away - Masuk HS-John Giampaolo Baseball Field @ Masuk HS [Directions] | W 7-1 | 12:30 PM; 1 Bus | |
| Tue., 4/11 | V Boys Lacrosse | New Canaan | Home - Trumbull HS-McDougall Stadium [Directions] | L 17-2 | ||
| Tue., 4/11 | V Boys Tennis | Danbury | Away - Danbury HS-DHS Tennis Courts [Directions] | W 6-1 [Detailed Results] | 2:45 PM; 1 Bus | |
| Tue., 4/11 | V Girls Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | L 0-16 | 10:30 AM; 1 Bus | |
| Tue., 4/11 | V Girls Tennis | Danbury | Home - Trumbull HS-Tennis Courts [Directions] | W 7-0 [Detailed Results] | ||
| Wed., 4/12 | V Baseball | Amity | Home - Trumbull HS-Varsity Baseball Field [Directions] | W 7-6 | ||
| Wed., 4/12 | V Boys Volleyball | Simsbury | Home - Trumbull HS-THS Main Gym [Directions] | W 3-0 | ||
| Wed., 4/12 | V Softball | Danbury | Home - Trumbull HS-Varsity Softball Diamond [Directions] | L 3-2 | ||
| Thu., 4/13 | V Boys Lacrosse | Westhill | Home - Trumbull HS-McDougall Stadium [Directions] | L 12-7 | ||
| Thu., 4/13 | V Boys Tennis | Darien | Home - Trumbull HS-Tennis Courts [Directions] | L 0-7 [Detailed Results] | ||
| Thu., 4/13 | V Girls Lacrosse | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | L 9-10 | 2:15 PM; 1 Bus | |
| Thu., 4/13 | V Girls Tennis | Darien | Away - Darien HS-DHS Tennis Courts [Directions] | L 0-7 [Detailed Results] | 9:45 AM; 1 Bus | |
| Fri., 4/14 | V Baseball | Westhill | Away - Westhill HS-Varsity Baseball Field [Directions] | W 3-1 | 2:15 PM; 1 Bus | |
| Fri., 4/14 | V Boys Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | W 3-2 | 1:45 PM; 1 Bus | |
| Fri., 4/14 | V Softball | Westhill | Home - Trumbull HS-Varsity Softball Diamond [Directions] | W 15-2 (6inn) | ||
| Mon., 4/17 | V Baseball | Danbury | Home - Trumbull HS-Varsity Baseball Field [Directions] | L 8-6 | ||
| Mon., 4/17 | V Boys Volleyball | Darien | Home - Trumbull HS-THS Main Gym [Directions] | L 0-3 | ||
| Tue., 4/18 | V Boys Lacrosse | Fairfield Warde | Home - Trumbull HS-Cork Field [Directions] | L 6-5 | ||
| Tue., 4/18 | V Boys Outdoor Track | Staples | Home - Trumbull HS-McDougall Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/18 | V Boys Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Tennis Courts [Directions] | W 4-3 [Detailed Results] | 2:45 PM; 1 Bus | |
| Tue., 4/18 | V Girls Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 4/18 | V Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | L 6-7 | 2:30 PM; 1 Bus | |
| Tue., 4/18 | V Girls Outdoor Track | Staples | Home - Trumbull HS-McDougall Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/18 | V Softball | Danbury | Away - Danbury HS-V Softball field [Directions] | W 7-2 | 2:15 PM, Dismiss 2:00 PM; 1 Bus | |
| Tue., 4/18 | V Girls Tennis | Fairfield Ludlowe | Home - Trumbull HS-Tennis Courts [Directions] | L 0-7 [Detailed Results] | ||
| Wed., 4/19 | V Baseball | Darien | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | W 10-0 (5) | 2:30 PM, Dismiss 2:15 PM; 1 Bus | |
| Wed., 4/19 | V Boys Tennis | Ridgefield | Home - Trumbull HS-Tennis Courts [Directions] | W 4-3 [Detailed Results] | ||
| Wed., 4/19 | V Boys Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | W 3-0 | 2:45 PM; 1 Bus | |
| Wed., 4/19 | V Girls Rugby | Southington | Home - Trumbull HS-Aux Gym [Directions] | 6:00 p.m. | ||
| Wed., 4/19 | V Softball | Darien | Home - Trumbull HS-Varsity Softball Diamond [Directions] | W 5-0 | ||
| Wed., 4/19 | V Girls Tennis | Ridgefield | Away - Ridgefield HS-RHS Tennis Courts [Directions] | L 1-6 [Detailed Results] | 2:45 PM; 1 Bus | |
| Thu., 4/20 | V Boys Tennis | Greenwich | Home - Trumbull HS-Tennis Courts [Directions] | L 3-4 [Detailed Results] | ||
| Thu., 4/20 | V Boys Volleyball | Ridgefield | Home - Trumbull HS-THS Main Gym [Directions] | W 3-0 | ||
| Thu., 4/20 | V Girls Tennis | Greenwich | Away - Greenwich HS-Tennis Courts [Directions] | L 0-7 [Detailed Results] | 2:45 PM; 1 Bus | |
| Fri., 4/21 | V Baseball | Ridgefield | Away - Governor Field [Directions] | L 5-0 | 2:00 PM, Dismiss 1:45 PM; 1 Bus | |
| Fri., 4/21 | V Boys Rugby | Simsbury | Home - Trumbull HS-Aux Gym [Directions] | 7:00 p.m. | ||
| Fri., 4/21 | V Softball | Ridgefield | Home - Trumbull HS-Varsity Softball Diamond [Directions] | W 4-3 | ||
| Sat., 4/22 | V Boys Lacrosse | Stamford | Home - Trumbull HS-McDougall Stadium [Directions] | W 9-5 | ||
| Sat., 4/22 | V Girls Lacrosse | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | L 5-14 | 10:30 AM; 1 Bus | |
| Mon., 4/24 | V Baseball | Fairfield Ludlowe | Home - Trumbull HS-Varsity Baseball Field [Directions] | W 1-0 | ||
| Mon., 4/24 | V Boys Lacrosse | Staples | Away - Staples HS-Staples Stadium [Directions] | L 19-2 | 5:00 PM; 1 Bus | |
| Mon., 4/24 | V Boys Tennis | Bridgeport Central | Away - Bridgeport Central HS-Central High School Tennis Courts [Directions] | W 6-1 [Detailed Results] | 3:00 PM; 1 Bus | |
| Mon., 4/24 | V Boys Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | W 3-0 | 2:30 PM, Dismiss 2:15 PM; 1 Bus | |
| Mon., 4/24 | V Softball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | L 2-0 | 2:45 PM; 1 Bus | |
| Mon., 4/24 | V Girls Tennis | Bridgeport Central | Home - Trumbull HS-Tennis Courts [Directions] | W 5-2 [Detailed Results] | ||
| Tue., 4/25 | V Boys Outdoor Track | Danbury | Home - Trumbull HS-McDougall Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/25 | V Boys Tennis | Stamford | Away - Stamford HS-SHS Tennis Courts [Directions] | W 5-2 [Detailed Results] | 2:45 PM; 1 Bus | |
| Tue., 4/25 | V Girls Golf | Danbury | Away - Richter Park Golf Course [Directions] | 3:30 p.m. | ||
| Tue., 4/25 | V Girls Lacrosse | Staples | Home - Trumbull HS-Cork Field [Directions] | L 14-2 | ||
| Tue., 4/25 | V Girls Outdoor Track | Danbury | Home - Trumbull HS-McDougall Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/25 | V Girls Tennis | Stamford | Home - Trumbull HS-Tennis Courts [Directions] | L 2-5 [Detailed Results] | ||
| Wed., 4/26 | V Boys Volleyball | Greenwich | Home - Trumbull HS-THS Main Gym [Directions] | W 3-0 | ||
| Wed., 4/26 | V Girls Golf | Ridgefield | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Wed., 4/26 | V Softball | Greenwich | Home - Trumbull HS-Varsity Softball Diamond [Directions] | W 15-0 (5inn) | ||
| Thu., 4/27 | V Baseball | Greenwich | Away - Greenwich HS-Baseball Field [Directions] | W 11-1 (5) | 2:45 PM; 1 Bus | |
| Thu., 4/27 | V Boys Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | L 12-6 | 4:00 PM; 1 Bus | |
| Thu., 4/27 | V Girls Lacrosse | Fairfield Ludlowe | Home - Trumbull HS-McDougall Stadium [Directions] | L 2-14 | ||
| Thu., 4/27 | V Girls Rugby | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 5:30 p.m. | 3:30 PM; 1 Bus | |
| Fri., 4/28 | V Baseball | Bridgeport Central | Home - Trumbull HS-Varsity Baseball Field [Directions] | W 4-3 | ||
| Fri., 4/28 | V Boys Tennis | Staples | Home - Trumbull HS-Tennis Courts [Directions] | L 2-5 [Detailed Results] | ||
| Fri., 4/28 | V Boys Volleyball | St. Joseph | Home - Trumbull HS-THS Main Gym [Directions] | W 3-0 | 3:00 PM | |
| Fri., 4/28 | V Softball | Bridgeport Central | Away - Bridgeport Central-Varsity Softball Field [Directions] | W 14-0 (5 inn) | 2:45 PM; 1 Bus | |
| Fri., 4/28 | V Girls Tennis | Staples | Away - Staples HS-Staples Tennis Courts [Directions] | L 0-7 [Detailed Results] | 2:45 PM; 1 Bus | |
| Sat., 4/29 | V Boys Lacrosse | New Fairfield | Away - New Fairfield HS-Marty Morgan Field [Directions] | L 13-5 | 9:00 AM; 1 Bus | |
| Sat., 4/29 | V Boys Rugby | Ridgefield | Home - Trumbull HS-Cork Field [Directions] | 9:30 a.m. | ||
| Sat., 4/29 | V Girls Lacrosse | St. Joseph | Home - Trumbull HS-McDougall Stadium [Directions] | L 5-10 | ||
| Sat., 4/29 | Miscellaneous Events | Powder Puff | Home - Trumbull HS-McDougall Stadium [Directions] | 1:30 p.m. | ||
| Mon., 5/1 | V Boys Tennis | Wilton | Away - Wilton HS-Tennis Courts [Directions] | L 1-6 [Detailed Results] | 2:45 PM; 1 Bus | |
| Mon., 5/1 | V Boys Volleyball | Fairfield Warde | Home - Trumbull HS-THS Main Gym [Directions] | W 3-0 | ||
| Mon., 5/1 | V Girls Lacrosse | Fairfield Warde | Home - Trumbull HS-McDougall Stadium [Directions] | L 2-9 | ||
| Mon., 5/1 | V Softball | Stamford | Away - Stamford HS-SHS Softball Diamond [Directions] | W 8-2 | 2:15 PM, Dismiss 2:00 PM; 1 Bus | |
| Mon., 5/1 | V Girls Tennis | Wilton | Home - Trumbull HS-Tennis Courts [Directions] | L 0-7 [Detailed Results] | ||
| Tue., 5/2 | V Boys Lacrosse | Amity | Home - Trumbull HS-Cork Field [Directions] | L 10-5 | ||
| Tue., 5/2 | V Boys Outdoor Track | Westhill | Home - Trumbull HS-McDougall Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/2 | V Girls Golf | Wilton | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 5/2 | V Girls Outdoor Track | Westhill | Home - Trumbull HS-McDougall Stadium [Directions] | 4:00 p.m. | ||
| Wed., 5/3 | V Baseball | Staples | Away - Staples HS-Baseball Diamond [Directions] | L 4-0 | 2:45 PM; 1 Bus | |
| Wed., 5/3 | V Boys Tennis | St. Joseph | Away - St. Joseph HS-Tennis Courts [Directions] | W 7-0 [Detailed Results] | 3:00 PM; 1 Bus | |
| Wed., 5/3 | V Boys Volleyball | Danbury | Home - Trumbull HS-THS Main Gym [Directions] | W 3-0 | ||
| Wed., 5/3 | V Girls Lacrosse | Stratford/Bunnell | Home - Trumbull HS-McDougall Stadium [Directions] | W 14-5 | ||
| Wed., 5/3 | V Softball | Staples | Home - Trumbull HS-Varsity Softball Diamond [Directions] | L 3-1 | ||
| Wed., 5/3 | V Girls Tennis | St. Joseph | Home - Trumbull HS-Tennis Courts [Directions] | L 0-7 [Detailed Results] | ||
| Thu., 5/4 | V Baseball | Stamford | Home - Trumbull HS-Varsity Baseball Field [Directions] | W 7-6 (10) | ||
| Thu., 5/4 | V Boys Rugby | Greenwich | Away - Greenwich HS-Field 7 [Directions] | 4:30 p.m. | 2:45 PM; 1 Bus | |
| Thu., 5/4 | V Boys Tennis | New Canaan | Away - New Canaan HS-NCHS Tennis Courts [Directions] | L 3-4 [Detailed Results] | 2:45 PM; 1 Bus | |
| Thu., 5/4 | V Girls Golf | Fairfield Warde | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Thu., 5/4 | V Girls Rugby | Simsbury | Away - Holden Field-Simsbury 2 [Directions] | 6:30 p.m. | 3:45 PM; 1 Bus | |
| Fri., 5/5 | V Baseball | Wilton | Home - Trumbull HS-Varsity Baseball Field [Directions] | L 10-9 | ||
| Fri., 5/5 | V Boys Volleyball | Staples | Home - Trumbull HS-THS Main Gym [Directions] | W 3-0 | ||
| Fri., 5/5 | V Softball | Wilton | Away - Wilton HS-Varsity Softball Field [Directions] | L 1-0 | 2:30 PM, Dismiss 2:15 PM; 1 Bus | |
| Sat., 5/6 | V Boys Lacrosse | St. Joseph | Home - Trumbull HS-McDougall Stadium [Directions] | L 18-5 | ||
| Sat., 5/6 | V Girls Lacrosse | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | L 1-17 | ||
| Sat., 5/6 | V Girls Tennis | New Canaan | Home - Trumbull HS-Tennis Courts [Directions] | L 0-7 [Detailed Results] | ||
| Mon., 5/8 | V Baseball | St. Joseph | Home - Trumbull HS-Varsity Baseball Field [Directions] | W 5-0 | ||
| Mon., 5/8 | V Boys Tennis | Brien McMahon | Home - Trumbull HS-Tennis Courts [Directions] | W 6-1 [Detailed Results] | ||
| Mon., 5/8 | V Boys Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | W 3-0 | 2:45 PM; 1 Bus | |
| Mon., 5/8 | V Softball | St. Joseph | Away - St. Joseph HS-Softball Diamond [Directions] | L 6-1 | 2:45 PM; 1 Bus | |
| Mon., 5/8 | V Girls Tennis | Brien McMahon | Away - Brien McMahon HS-Tennis Courts [Directions] | L 1-6 [Detailed Results] | 2:45 PM; 1 Bus | |
| Tue., 5/9 | V Boys Lacrosse | Conard | Home - Trumbull HS-McDougall Stadium [Directions] | W 14-10 | ||
| Tue., 5/9 | V Boys Outdoor Track | St. Joseph | Away - St. Joseph HS-Track [Directions] | 4:00 p.m. | 2:45 PM; 1 Bus | |
| Tue., 5/9 | V Boys Tennis | Fairfield Warde | Home - Trumbull HS-Tennis Courts [Directions] | L 3-4 [Detailed Results] | ||
| Tue., 5/9 | V Girls Golf | Lauralton Hall | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 5/9 | V Girls Outdoor Track | St. Joseph | Away - St. Joseph HS-Track [Directions] | 4:00 p.m. | 2:45 PM; 1 Bus | |
| Tue., 5/9 | V Girls Tennis | Fairfield Warde | Away - Fairfield Warde HS-Blake Courts [Directions] | L 0-7 [Detailed Results] | 2:45 PM; 1 Bus | |
| Wed., 5/10 | V Baseball | New Canaan | Home - Trumbull HS-Varsity Baseball Field [Directions] | W 5-0 | ||
| Wed., 5/10 | V Boys Volleyball | New Canaan | Home - Trumbull HS-THS Main Gym [Directions] | W 3-0 | ||
| Wed., 5/10 | V Girls Golf | Lauralton Hall | Away - Lauralton Hall-Oronoque CC [Directions] | 2:30 p.m. | ||
| Wed., 5/10 | V Softball | New Canaan | Away - Waveny Park-Orchard Field [Directions] | W 5-2 | 3:45 PM; 1 Bus | |
| Thu., 5/11 | V Boys Lacrosse | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | W 7-6 | 4:45 PM; 1 Bus | |
| Thu., 5/11 | V Boys Tennis | Norwalk | Away - Norwalk HS-Tennis Courts [Directions] | W 7-0 [Detailed Results] | 2:45 PM; 1 Bus | |
| Thu., 5/11 | V Girls Golf | Greenwich | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Thu., 5/11 | V Girls Lacrosse | Joel Barlow | Home - Trumbull HS-McDougall Stadium [Directions] | L 2-14 | ||
| Thu., 5/11 | V Girls Tennis | Norwalk | Home - Trumbull HS-Tennis Courts [Directions] | L 3-4 [Detailed Results] | ||
| Fri., 5/12 | V Baseball | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | W 13-2 (6) | 2:45 PM; 1 Bus | |
| Fri., 5/12 | V Boys Rugby | Fairfield Prep | Away - Fairfield University-Grauert Field [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM; 1 Bus | |
| Fri., 5/12 | V Boys Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | W 3-1 | 2:15 PM, Dismiss 2:00 PM; 1 Bus | |
| Fri., 5/12 | V Softball | Brien McMahon | Home - Trumbull HS-Varsity Softball Diamond [Directions] | W 9-0 | ||
| Sat., 5/13 | V Boys Lacrosse | Norwich Free Academy | Home - Trumbull HS-McDougall Stadium [Directions] | W 9-4 | ||
| Sat., 5/13 | V Girls Lacrosse | Lauralton Hall | Away - Lauralton Hall-Turf Field [Directions] | L 9-11 | 9:00 AM; 1 Bus | |
| Mon., 5/15 | V Baseball | Fairfield Warde | Away - Fairfield Warde HS-Baseball Diamond [Directions] | W 3-2 (8) | 2:30 PM, Dismiss 2:15 PM; 1 Bus | |
| Mon., 5/15 | V Boys Outdoor Track | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | 2:45 PM; 1 Bus | |
| Mon., 5/15 | V Boys Tennis | Greenwich | Away - Greenwich HS-Tennis Courts [Directions] | L 0-4 | 3:30 PM; 1 Bus | |
| Mon., 5/15 | V Boys Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | L 0-3 | 2:30 PM, Dismiss 2:15 PM; 1 Bus | |
| Mon., 5/15 | V Girls Golf | New Canaan | Away - CCNC [Directions] | 3:30 p.m. | ||
| Mon., 5/15 | V Girls Outdoor Track | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | 2:45 PM; 1 Bus | |
| Mon., 5/15 | V Softball | Fairfield Warde | Home - Trumbull HS-Varsity Softball Diamond [Directions] | W 11-3 | ||
| Tue., 5/16 | V Boys Lacrosse | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | L 10-9 | 5:00 PM; 1 Bus | |
| Tue., 5/16 | V Girls Golf | Darien | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 5/16 | V Girls Lacrosse | Brien McMahon | Home - Trumbull HS-McDougall Stadium [Directions] | L 8-10 | ||
| Wed., 5/17 | V Baseball | Norwalk | Home - Trumbull HS-Varsity Baseball Field [Directions] | L 6-5 | ||
| Wed., 5/17 | V Boys Volleyball | Bridgeport Central | Home - Trumbull HS-THS Main Gym [Directions] | W 3-0 | ||
| Wed., 5/17 | V Girls Golf | Staples | Away - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 5/17 | V Softball | Norwalk | Away - Norwalk HS-Ray Barry Field [Directions] | L 4-1 | 2:30 PM, Dismiss 2:15 PM | |
| Thu., 5/18 | V Boys Lacrosse | Guilford | Home - Trumbull HS-McDougall Stadium [Directions] | L 11-2 | ||
| Fri., 5/19 | V Baseball | TBA | Away - TBA | 4:00 p.m. | ||
| Fri., 5/19 | V Baseball | Danbury | Away - Danbury HS-V Baseball Field [Directions] | 4:00 p.m. | 2:00 PM, Dismiss 1:45 PM; 1 Bus | |
| Fri., 5/19 | V Boys Rugby | Staples | Away - Staples HS-Staples Stadium [Directions] | 7:00 p.m. | 5:00 PM; 1 Bus | |
| Fri., 5/19 | V Boys Volleyball | Greenwich | Home - Trumbull HS-THS Main Gym [Directions] | W 3-0 | ||
| Fri., 5/19 | V Girls Rugby | Greenwich | Home - Trumbull HS-Aux Gym [Directions] | 5:30 p.m. | ||
| Fri., 5/19 | V Softball | Wilton | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 4:30 p.m. | ||
| Sun., 5/21 | Miscellaneous Events | Final Mile | Home - Trumbull HS-Aux Gym [Directions] | 8:00 a.m. | ||
| Mon., 5/22 | V Baseball | Westhill | Home - Cubeta Stadium [Directions] | 7:00 p.m. | 4:30 PM; 1 Bus | |
| Mon., 5/22 | V Girls Golf | Amity | Away - Race Brook C.C. [Directions] | 3:15 p.m. | ||
| Mon., 5/22 | V Softball | Fairfield Ludlowe | Away - Fairfield University-Alumni Field [Directions] | 3:00 p.m. | 1:00 PM, Dismiss 12:00 PM; 1 Bus | |
| Tue., 5/23 | V Boys Outdoor Track | FCIAC Track Championship | Away - Danbury HS-Danbury HS Stadium | 2:30 p.m. | 12:30 PM; 1 Bus | |
| Tue., 5/23 | V Girls Golf | Amity | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 5/23 | V Girls Outdoor Track | FCIAC Track Championship | Away - Danbury HS-DHS Stadium | 2:30 p.m. | 12:30 PM; 1 Bus | |
| Wed., 5/24 | V Boys Rugby | Simsbury | Away - Holden Field-Simsbury 2 [Directions] | 5:30 p.m. | ||
| Wed., 5/24 | V Boys Volleyball | Ridgefield | Home - Fairfield Warde HS-Gym [Directions] | W 3-0 | 4:30 PM; 1 Bus | |
| Thu., 5/25 | V Girls Golf | Darien | Away - Wee Burn CC [Directions] | 3:00 p.m. | ||
| Fri., 5/26 | V Boys Tennis | Fairfield Ludlowe | Home - Trumbull HS-Tennis Courts [Directions] | 3:30 p.m. | ||
| Fri., 5/26 | V Boys Volleyball | Darien | Home - Fairfield Warde HS-Large Gym [Directions] | 6:00 p.m. | ||
| Fri., 5/26 | V Softball | Foran (Scrim.) | Away - Foran HS -Danielle Kemp Memorial Field [Directions] | 4:30 p.m. | 2:45 PM; 1 Bus | |
| Sat., 5/27 | V Boys Tennis | Glastonbury | Away - Glastonbury HS-Tennis Courts [Directions] | 11:00 a.m. | ||
| Tue., 5/30 | V Baseball | New Milford | Home - Trumbull HS-Varsity Baseball Field [Directions] | 3:30 p.m. | ||
| Tue., 5/30 | V Girls Golf | Staples | Home - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 5/30 | V Softball | Simsbury | Home - Trumbull HS-Varsity Softball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 5/31 | V Baseball | Southington | Home - Trumbull HS-Varsity Baseball Field [Directions] | 3:30 p.m. | ||
| Wed., 5/31 | V Baseball | Southington | Home - Trumbull HS-Varsity Baseball Field [Directions] | 3:30 p.m. | ||
| Wed., 5/31 | V Boys Outdoor Track | CIAC Class LL Championships | Away - Willow Brook Park | 10:00 a.m. | 7:00 AM; 1 Bus | |
| Wed., 5/31 | V Boys Volleyball | Amity | Home - Trumbull HS-THS Main Gym [Directions] | 5:00 p.m. | ||
| Wed., 5/31 | V Girls Outdoor Track | CIAC Class LL Championships | Away - Willow Brook Park | 10:00 a.m. | 7:00 AM; 1 Bus | |
| Wed., 5/31 | V Softball | Cheshire | Away - Cheshire HS-Softball Diamond [Directions] | 4:30 p.m. | ||
| Sat., 6/3 | V Boys Volleyball | Ridgefield | Home - Trumbull HS-THS Main Gym [Directions] | 2:00 p.m. | ||
| Sat., 6/3 | V Boys Volleyball | Ridgefield | Home - Trumbull HS-THS Main Gym [Directions] | 2:00 p.m. | ||
| Mon., 6/5 | V Boys Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/5 | V Boys Tennis | CIAC Individual Invitational Opening Rounds | Away - Wesleyan | 10:00 a.m. | ||
| Mon., 6/5 | V Girls Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/5 | V Girls Tennis | CIAC Individual Invitational Opening Rounds | Away - Wesleyan | 10:00 a.m. | ||
| Tue., 6/6 | V Boys Tennis | CIAC Individual Invitational Round of 16 | Away - Wesleyan | 12:00 p.m. | ||
| Tue., 6/6 | V Boys Tennis | CIAC Individual Invitational Quarterfinals | Away - Wesleyan | 3:30 p.m. | ||
| Tue., 6/6 | V Boys Volleyball | Southington | Home - Sport and Medical Sciences Academy (SMSA)-Gym [Directions] | 5:00 p.m. | 2:30 PM; 1 Bus | |
| Tue., 6/6 | V Girls Tennis | CIAC Individual Invitational Round of 16 | Away - Wesleyan | 12:00 p.m. | ||
| Tue., 6/6 | V Girls Tennis | CIAC Individual Invitational Quarterfinals | Away - Wesleyan | 3:30 p.m. | ||
| Wed., 6/7 | V Boys Tennis | CIAC Individual Invitational Semifinals | Away - Wesleyan | 3:30 p.m. | ||
| Wed., 6/7 | V Girls Golf | CIAC Division I Championship | Away - Timberlin GC | 8:30 a.m. | ||
| Wed., 6/7 | V Girls Tennis | CIAC Individual Invitational Semifinals | Away - Wesleyan | 3:30 p.m. | ||
| Thu., 6/8 | V Boys Tennis | CIAC Individual Invitational Finals | Away - Wesleyan | 3:30 p.m. | ||
| Thu., 6/8 | V Boys Volleyball | Darien | Away - Newtown HS-Gym [Directions] | 7:00 p.m. | ||
| Thu., 6/8 | V Girls Tennis | CIAC Individual Invitational Finals | Away - Wesleyan | 3:30 p.m. | ||
| Sat., 6/10 | V Girls Golf | CIAC State Open Championship | Away - Black Hall Club | 1:00 p.m. | ||
| Mon., 6/12 | V Boys Outdoor Track | CIAC Hammer Throw Championship | Away - Willow Brook Park | 2:00 p.m. | ||
| Mon., 6/12 | V Girls Outdoor Track | CIAC Hammer Throw Championship | Away - Willow Brook Park | 4:00 p.m. | ||
| Tue., 6/13 | V Boys Outdoor Track | CIAC Decathlon Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 6/13 | V Girls Outdoor Track | CIAC Heptathlon Championship | Away - Willow Brook Park | 10:30 a.m. | ||
| Tue., 6/13 | V Girls Outdoor Track | CIAC Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/14 | V Boys Outdoor Track | CIAC Decathlon Championship | Away - Willow Brook Park | 8:30 a.m. | ||
| Wed., 6/14 | V Boys Outdoor Track | CIAC Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/14 | V Girls Outdoor Track | CIAC Heptathlon Championship | Away - Willow Brook Park | 8:30 a.m. | ||