| 2016-17 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 379 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| TBA | JV Baseball | New Canaan | Away - Mead Park [Directions] | 4:00 p.m. | ||
| TBA | JV Baseball | Fairfield Ludlowe | Home - Barrett Field @ Belltown Park | TBA | ||
| TBA | FR Baseball | New Canaan | Home - Trinity Catholic's Lione Field | 4:00 p.m. | ||
| TBA | FR Baseball | Fairfield Ludlowe | Away - Kiwanis Field [Directions] | 4:00 p.m. | ||
| TBA | JV Softball | New Canaan | Home - Boccuzzi Park/Southfield | 4:00 p.m. | ||
| TBA | JV Softball | St. Joseph | Away - St. Joseph HS [Directions] | Cancelled | Cancelled | |
| Mon., 8/29 | V Girls Soccer | Brien McMahon (Scrim.) | Away - Brien McMahon HS [Directions] | 6:30 p.m. | ||
| Tue., 8/30 | V Boys Soccer | King and Low-Heywood Thomas (Scrim.) | Home - King & Low-Heywood Field | 3:30 p.m. | ||
| Wed., 8/31 | V Girls Soccer | King and Low-Heywood Thomas (Scrim.) | Away | 3:30 p.m. | ||
| Fri., 9/2 | V Boys Soccer | St. Lukes (Scrim.) | Away - St. Lukes Field | 3:30 p.m. | ||
| Tue., 9/6 | V Boys Soccer | Bassick (Scrim.) | Away - Went Field [Directions] | 4:00 p.m. | ||
| Tue., 9/6 | V Boys Soccer | Bassick (Scrim.) | Away - Went Field [Directions] | 4:00 p.m. | ||
| Tue., 9/6 | V Girls Soccer | St. Lukes (Scrim.) | Away | 4:30 p.m. | ||
| Fri., 9/9 | V Boys Soccer | Staples | Away - Staples High [Directions] | 4:00 p.m. | L 0-6 | |
| Fri., 9/9 | V Girls Volleyball | Foran | Home - Stamford HS | 4:00 p.m. | L 1-3 | |
| Sat., 9/10 | V Football | New Canaan | Away - New Canaan Dunning Stadium [Directions] | 3:00 p.m. | L 6-20 | |
| Sat., 9/10 | V Girls Soccer | Staples | Away - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | L 1-12 | |
| Sat., 9/10 | V Girls Volleyball | Shelton | Home - Stamford HS | 4:00 p.m. | L 0-3 | |
| Mon., 9/12 | V Boys Soccer | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | L 0-6 | |
| Mon., 9/12 | V Girls Volleyball | New Canaan | Home - Walsh Court | 5:30 p.m. | W 3-0 | |
| Mon., 9/12 | JV Girls Volleyball | New Canaan | Home - Walsh Court | 4:00 p.m. | ||
| Tue., 9/13 | V Boys Cross Country | New Canaan, St. Joseph, Fairfield Ludlowe | Away [Directions] | 4:00 p.m. | ||
| Tue., 9/13 | V Girls Cross Country | New Canaan, St. Joseph, Fairfield Ludlowe | Away [Directions] | 4:00 p.m. | ||
| Tue., 9/13 | V Girls Soccer | St. Joseph | Away - St, Josephs Field [Directions] | 4:00 p.m. | L 0-6 | |
| Wed., 9/14 | V Boys Soccer | Norwalk | Away - Testa Field, NHS [Directions] | 4:00 p.m. | L 0-6 | |
| Thu., 9/15 | V Girls Soccer | Norwalk | Away - Testa Field, NHS [Directions] | 7:00 p.m. | L 0-6 | |
| Fri., 9/16 | V Boys Soccer | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 4:00 p.m. | L 0-6 | |
| Fri., 9/16 | V Girls Volleyball | Staples | Home - Walsh Court | 5:30 p.m. | L 0-3 | |
| Fri., 9/16 | JV Girls Volleyball | Staples | Home - Walsh Court | 4:00 p.m. | ||
| Sat., 9/17 | V Football | Greenwich | Away - Cardinal Stadium [Directions] | 4:00 p.m. | L 20-41 | |
| Mon., 9/19 | V Girls Soccer | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 6:00 p.m. | L 0-7 | |
| Mon., 9/19 | V Girls Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | 5:30 p.m. | L 0-3 | |
| Mon., 9/19 | JV Girls Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | ||
| Tue., 9/20 | V Boys Cross Country | New Canaan, Staples, Wilton, Stamford | Away - Waveny Park [Directions] | 4:00 p.m. | ||
| Tue., 9/20 | V Girls Cross Country | New Canaan, Staples, Wilton, Stamford | Away - Waveny Park [Directions] | 4:00 p.m. | ||
| Wed., 9/21 | V Girls Volleyball | Norwalk | Away - Norwalk High Gym [Directions] | 4:00 p.m. | W 3-1 | |
| Wed., 9/21 | JV Girls Volleyball | Norwalk | Away - Norwalk High Gym [Directions] | 5:30 p.m. | ||
| Thu., 9/22 | FR Football | Norwalk | Away - Nathan Hale M.S. Lower [Directions] | 4:00 p.m. | ||
| Thu., 9/22 | V Boys Soccer | New Canaan | Away - Conner Field [Directions] | 4:00 p.m. | L 0-9 | |
| Fri., 9/23 | V Girls Soccer | New Canaan | Home - Gaglio Field | 4:00 p.m. | L 0-7 | |
| Fri., 9/23 | V Girls Volleyball | Fairfield Warde | Home - Walsh Court | 5:30 p.m. | L 2-3 | |
| Fri., 9/23 | JV Girls Volleyball | Fairfield Warde | Home - Walsh Court | 4:00 p.m. | ||
| Sat., 9/24 | V Football | Norwalk | Home - Gaglio Field | 1:00 p.m. | W 52-28 | |
| Mon., 9/26 | V Boys Soccer | Westhill | Home - Gaglio Field | 4:00 p.m. | L 1-10 | |
| Mon., 9/26 | V Girls Soccer | Westhill | Away - Westhill Front Turf Field [Directions] | 4:00 p.m. | L 1-7 | |
| Tue., 9/27 | V Boys Cross Country | New Canaan, Trumbull, Ridgefield, Danbury | Away - Waveny Park [Directions] | 4:00 p.m. | ||
| Tue., 9/27 | V Girls Cross Country | New Canaan, Trumbull, Ridgefield, Danbury | Away - Waveny Park [Directions] | 4:00 p.m. | ||
| Wed., 9/28 | V Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 5:30 p.m. | L 1-3 | |
| Wed., 9/28 | JV Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 9/29 | FR Football | Trumbull | Home - Gaglio Field | 4:00 p.m. | ||
| Thu., 9/29 | V Girls Soccer | Stamford | Away - Stamford High Soccer Field [Directions] | 4:00 p.m. | L 0-7 | |
| Fri., 9/30 | V Football | Trumbull | Away - McDougall Stadium [Directions] | 7:00 p.m. | L 14-24 | |
| Fri., 9/30 | V Girls Volleyball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | L 0-3 | |
| Fri., 9/30 | JV Girls Volleyball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 10/1 | V Boys Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | 1:00 p.m. | L 1-11 | |
| Sat., 10/1 | V Girls Volleyball | Jonathan Law | Home - Walsh Court | 4:30 p.m. | L 0-3 | |
| Sat., 10/1 | JV Girls Volleyball | Jonathan Law | Home - Walsh Court | 3:00 p.m. | ||
| Tue., 10/4 | V Boys Cross Country | Greenwich, Fairfield Warde, Darien, New Canaan | Away - Greenwich Point [Directions] | 4:00 p.m. | ||
| Tue., 10/4 | V Girls Cross Country | Greenwich, Fairfield Warde, Darien, New Canaan | Away - Greenwich Point [Directions] | 4:00 p.m. | ||
| Tue., 10/4 | V Girls Soccer | Brien McMahon | Home - Gaglio Field | 4:00 p.m. | L 0-8 | |
| Wed., 10/5 | V Boys Soccer | Wilton | Away - Lilly Field - Turf [Directions] | 4:00 p.m. | L 1-4 | |
| Wed., 10/5 | V Girls Volleyball | Stamford | Home - Walsh Court | 5:30 p.m. | L 0-3 | |
| Wed., 10/5 | JV Girls Volleyball | Stamford | Home - Walsh Court | 4:00 p.m. | ||
| Thu., 10/6 | V Girls Soccer | Wilton | Home - Gaglio Field | 4:30 p.m. | L 0-7 | |
| Fri., 10/7 | V Boys Soccer | Bridgeport Central | Home - Gaglio Field | 4:00 p.m. | L 2-7 | |
| Fri., 10/7 | V Girls Volleyball | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:30 p.m. | L 0-3 | |
| Fri., 10/7 | JV Girls Volleyball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | ||
| Sat., 10/8 | V Boys Soccer | Stamford | Home - Stamford HS | 10:30 a.m. | L 0-6 | |
| Sat., 10/8 | V Girls Soccer | Bridgeport Central | Away - Kennedy Stadium [Directions] | 12:00 p.m. | L 2-8 | |
| Mon., 10/10 | V Boys Cross Country | New Canaan, Brien McMahon, Westhill, Norwalk | Away - Waveny Park [Directions] | 4:00 p.m. | ||
| Mon., 10/10 | V Boys Soccer | Fairfield Ludlowe | Home - Gaglio Field | 4:00 p.m. | L 0-7 | |
| Mon., 10/10 | V Girls Cross Country | New Canaan, Brien McMahon, Westhill, Norwalk | Away - Waveny Park [Directions] | 4:00 p.m. | ||
| Mon., 10/10 | V Girls Soccer | Fairfield Ludlowe | Away - Taft Field [Directions] | 7:00 p.m. | L 0-5 | |
| Thu., 10/13 | FR Football | Ridgefield | Away - Tiger Hollow Turf Field II [Directions] | 4:00 p.m. | ||
| Thu., 10/13 | V Boys Soccer | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 3:30 p.m. | L 0-8 | |
| Thu., 10/13 | V Girls Soccer | Danbury | Home - Gaglio Field | 4:00 p.m. | L 0-4 | |
| Thu., 10/13 | V Girls Volleyball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 4:15 p.m. | W 3-2 | |
| Thu., 10/13 | JV Girls Volleyball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 5:45 p.m. | ||
| Fri., 10/14 | V Boys Soccer | Greenwich | Home - Gaglio Field | 4:00 p.m. | L 0-7 | |
| Fri., 10/14 | V Girls Volleyball | Bridgeport Central | Home - Walsh Court | 5:30 p.m. | W 3-0 | |
| Fri., 10/14 | JV Girls Volleyball | Bridgeport Central | Home - Walsh Court | 4:00 p.m. | ||
| Sat., 10/15 | V Football | Ridgefield | Home - Gaglio Field | 2:00 p.m. | W 38-33 | |
| Mon., 10/17 | V Girls Soccer | Greenwich | Away - Cardinal Stadium [Directions] | 4:00 p.m. | L 0-5 | |
| Mon., 10/17 | V Girls Volleyball | Fairfield Ludlowe | Home - Walsh Court | 5:30 p.m. | L 0-3 | |
| Mon., 10/17 | JV Girls Volleyball | Fairfield Ludlowe | Home - Walsh Court | 4:00 p.m. | ||
| Tue., 10/18 | V Boys Soccer | Trumbull | Away - McDougall Stadium [Directions] | 7:00 p.m. | L 0-6 | |
| Wed., 10/19 | V Girls Soccer | Trumbull | Home - Gaglio Field | 4:00 p.m. | L 0-7 | |
| Wed., 10/19 | V Girls Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 4:00 p.m. | L 0-3 | |
| Wed., 10/19 | JV Girls Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 5:30 p.m. | ||
| Thu., 10/20 | FR Football | Fairfield Ludlowe | Away - Taft Field [Directions] | 5:30 p.m. | ||
| Thu., 10/20 | V Boys Soccer | Darien | Home - Gaglio Field | 4:00 p.m. | L 0-7 | |
| Fri., 10/21 | V Football | Fairfield Ludlowe | Away - Taft Field [Directions] | 7:00 p.m. | W 41-13 | |
| Fri., 10/21 | V Girls Soccer | Darien | Away - DHS Stadium Field [Directions] | 4:00 p.m. | L 0-6 | |
| Fri., 10/21 | V Girls Volleyball | Greenwich | Home - Walsh Court | 5:30 p.m. | L 0-3 | |
| Fri., 10/21 | JV Girls Volleyball | Greenwich | Home - Walsh Court | 4:00 p.m. | ||
| Mon., 10/24 | V Boys Soccer | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 7:00 p.m. | L 0-2 | |
| Mon., 10/24 | V Girls Volleyball | Trumbull | Away - THS Main Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Mon., 10/24 | JV Girls Volleyball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/25 | V Girls Soccer | Ridgefield | Home - Gaglio Field | 4:00 p.m. | L 0-6 | |
| Wed., 10/26 | V Girls Volleyball | Darien | Home - Walsh Court | 5:30 p.m. | L 0-3 | |
| Wed., 10/26 | JV Girls Volleyball | Darien | Home - Walsh Court | 4:00 p.m. | ||
| Fri., 10/28 | FR Football | Westhill | Home - Gaglio Field | 4:00 p.m. | ||
| Fri., 10/28 | V Girls Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 7:00 p.m. | L 0-3 | |
| Fri., 10/28 | JV Girls Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 5:30 p.m. | ||
| Sat., 10/29 | V Football | Westhill | Away - Westhill Football Field [Directions] | 1:30 p.m. | W 28-14 | |
| Thu., 11/3 | FR Football | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | ||
| Sat., 11/5 | V Football | Stamford | Home - Gaglio Field | 2:00 p.m. | W 38-13 | |
| Mon., 11/7 | JV Football | Stamford | Home - Gaglio Field | Cancelled | Cancelled | |
| Thu., 11/10 | FR Football | Stamford | Home - Gaglio Field | 3:15 p.m. | ||
| Thu., 11/10 | FR Football | Bridgeport Central | Away - Kennedy Stadium [Directions] | Cancelled | Cancelled | |
| Sat., 11/12 | V Football | Bridgeport Central | Home - Gaglio Field | 1:00 p.m. | W 48-8 | |
| Thu., 11/17 | FR Football | Wilton | Away - Fujitani Field - Turf [Directions] | 6:00 p.m. | ||
| Thu., 11/24 | V Football | Wilton | Away - Fujitani Field - Turf [Directions] | 10:30 a.m. | L 3-30 | |
| Mon., 12/5 | V Girls Basketball | Joel Barlow (Scrim.) | Away - Joel Barlow HS [Directions] | 3:30 p.m. | ||
| Wed., 12/7 | V Girls Basketball | New Canaan (Scrim.) | Away - NCHS Gymnasium [Directions] | 3:15 p.m. | ||
| Fri., 12/9 | V Boys Basketball | Newtown (Scrim.) | Home - Walsh Court | 4:30 p.m. | ||
| Sat., 12/10 | V Boys Ice Hockey | Westhill/Stamford (Scrim.) | Home - Terry Conners Ice Rink | 4:40 p.m. | ||
| Sat., 12/10 | V Girls Basketball | Hamden (Scrim.) | Away - HHS Gym [Directions] | 10:30 a.m. | ||
| Sun., 12/11 | V Boys Basketball | Berlin (Scrim.) | Home - Walsh Court | 2:00 p.m. | ||
| Mon., 12/12 | V Girls Basketball | Weston | Home - Walsh Court | 5:45 p.m. | L 31-55 | |
| Mon., 12/12 | JV Girls Basketball | Weston | Home - Walsh Court | 4:00 p.m. | ||
| Tue., 12/13 | V Boys Basketball | Brien McMahon (Scrim.) | Home - Walsh Court | 4:30 p.m. | ||
| Wed., 12/14 | V Girls Basketball | Brookfield | Away - BHS Big Gym [Directions] | 5:45 p.m. | L 39-65 | |
| Wed., 12/14 | JV Girls Basketball | Brookfield | Away - BHS Big Gym [Directions] | 4:00 p.m. | ||
| Thu., 12/15 | V Boys Basketball | Shelton (Scrim.) | Away - Shelton HS Gym [Directions] | 3:30 p.m. | ||
| Fri., 12/16 | V Girls Basketball | Bridgeport Central | Away - Fairchild Wheeler Interdistrict Magnet [Directions] | 6:00 p.m. | L 32-35 | |
| Fri., 12/16 | JV Girls Basketball | Bridgeport Central | Away - Fairchild Wheeler Interdistrict Magnet [Directions] | 4:30 p.m. | ||
| Sat., 12/17 | V Boys Ice Hockey | Sheehan | Home - Terry Conners Ice Rink | 6:30 p.m. | W 5-2 | |
| Mon., 12/19 | V Boys Basketball | Prince Tech | Home - Walsh Court | 7:00 p.m. | W 75-51 | |
| Tue., 12/20 | V Girls Basketball | Stamford | Away - Stamford HS [Directions] | 7:00 p.m. | L 11-59 | |
| Tue., 12/20 | JV Girls Basketball | Stamford | Away - Stamford HS [Directions] | 5:30 p.m. | ||
| Wed., 12/21 | V Boys Basketball | Kolbe Cathedral | Home - Walsh Court | 7:00 p.m. | W 69-55 | |
| Thu., 12/22 | V Boys Ice Hockey | Masuk | Away - The Rinks at Shelton [Directions] | 4:30 p.m. | W 6-3 | |
| Fri., 12/23 | V Boys Basketball | Staples | Home - Walsh Court | 7:00 p.m. | W 58-51 | |
| Fri., 12/23 | JV Boys Basketball | Staples | Home - Walsh Court | 5:15 p.m. | ||
| Fri., 12/23 | FR Boys Basketball | Staples | Home - Walsh Court | 3:45 p.m. | ||
| Fri., 12/23 | V Girls Basketball | Staples | Away - Staples H.S. Gym [Directions] | 2:00 p.m. | L 31-46 | |
| Fri., 12/23 | JV Girls Basketball | Staples | Away - Staples H.S. Gym [Directions] | 12:30 p.m. | ||
| Tue., 12/27 | V Boys Ice Hockey | Milford Coop | Away - Milford Ice Pavilion [Directions] | 6:00 p.m. | L 5-6 | |
| Thu., 12/29 | V Girls Basketball | Harding | Away - Fairchild Wheeler HS [Directions] | 11:00 a.m. | W 48-44 | |
| Fri., 12/30 | V Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena [Directions] | 8:00 p.m. | L 0-5 | |
| Fri., 12/30 | V Girls Basketball | Bassick | Away - Fairchild Wheeler [Directions] | 1:00 p.m. | L 23-45 | |
| Tue., 1/3 | V Boys Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 7:00 p.m. | W 79-51 | |
| Tue., 1/3 | JV Boys Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 5:15 p.m. | ||
| Tue., 1/3 | FR Boys Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | ||
| Tue., 1/3 | V Girls Basketball | St. Joseph | Home - Walsh Court | 5:30 p.m. | L 38-51 | |
| Tue., 1/3 | JV Girls Basketball | St. Joseph | Home - Walsh Court | 4:00 p.m. | ||
| Wed., 1/4 | V Boys Ice Hockey | Norwalk | Home - Terry Conners Ice Rink | 6:10 p.m. | L 3-4 | |
| Fri., 1/6 | V Boys Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 7:00 p.m. | L 50-65 | |
| Fri., 1/6 | JV Boys Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/6 | FR Boys Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/6 | V Girls Basketball | Ridgefield | Home - Walsh Court | 5:45 p.m. | L 20-79 | |
| Fri., 1/6 | JV Girls Basketball | Ridgefield | Home - Walsh Court | 4:00 p.m. | ||
| Mon., 1/9 | V Boys Ice Hockey | New Canaan | Away - Darien Ice House [Directions] | 6:00 p.m. | L 0-8 | |
| Tue., 1/10 | V Boys Basketball | Darien | Home - Walsh Court | 7:00 p.m. | L 59-66 | |
| Tue., 1/10 | JV Boys Basketball | Darien | Home - Walsh Court | 5:15 p.m. | ||
| Tue., 1/10 | FR Boys Basketball | Darien | Home - Walsh Court | 4:00 p.m. | ||
| Tue., 1/10 | V Girls Basketball | Darien | Away - DHS Main Gym [Directions] | 5:30 p.m. | L 28-50 | |
| Tue., 1/10 | JV Girls Basketball | Darien | Away - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/13 | V Boys Basketball | Norwalk | Away - Norwalk High Gym [Directions] | 5:30 p.m. | W 74-44 | |
| Fri., 1/13 | JV Boys Basketball | Norwalk | Away - Norwalk High Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/13 | V Boys Ice Hockey | Ridgefield | Home - Terry Conners Ice Rink | 8:00 p.m. | L 1-8 | |
| Fri., 1/13 | V Girls Basketball | Norwalk | Home - Walsh Court | 4:00 p.m. | L 36-78 | |
| Fri., 1/13 | JV Girls Basketball | Norwalk | Home - Walsh Court | 5:45 p.m. | ||
| Sat., 1/14 | FR Boys Basketball | Norwalk | Home - Trinity Catholic Gym | 10:00 a.m. | ||
| Tue., 1/17 | V Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 7:00 p.m. | L 57-64 | |
| Tue., 1/17 | JV Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 5:00 p.m. | ||
| Tue., 1/17 | FR Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 3:45 p.m. | ||
| Tue., 1/17 | V Girls Basketball | New Canaan | Home - Walsh Court | 5:45 p.m. | L 17-38 | |
| Tue., 1/17 | JV Girls Basketball | New Canaan | Home - Walsh Court | 4:00 p.m. | ||
| Wed., 1/18 | V Boys Ice Hockey | St. Joseph | Home - Terry Conners Ice Rink | 6:20 p.m. | L 4-5(OT) | |
| Fri., 1/20 | V Boys Basketball | Westhill | Home - Walsh Court | 7:00 p.m. | W 62-54 | |
| Fri., 1/20 | JV Boys Basketball | Westhill | Home - Walsh Court | 5:15 p.m. | ||
| Fri., 1/20 | FR Boys Basketball | Westhill | Home - Walsh Court | 3:45 p.m. | ||
| Fri., 1/20 | V Girls Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | L 26-40 | |
| Fri., 1/20 | JV Girls Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/24 | V Boys Basketball | Fairfield Ludlowe | Home - Walsh Court | 7:00 p.m. | W 56-51 | |
| Tue., 1/24 | JV Boys Basketball | Fairfield Ludlowe | Home - Walsh Court | 5:15 p.m. | ||
| Tue., 1/24 | FR Boys Basketball | Fairfield Ludlowe | Home - Walsh Court | 4:00 p.m. | ||
| Tue., 1/24 | V Girls Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 5:45 p.m. | L 46-57 | |
| Tue., 1/24 | JV Girls Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/25 | V Boys Ice Hockey | Westhill/Stamford | Away - Terry Connors [Directions] | 6:20 p.m. | L 3-9 | |
| Fri., 1/27 | V Boys Basketball | Wilton | Away [Directions] | 7:00 p.m. | W 69-55 | |
| Fri., 1/27 | JV Boys Basketball | Wilton | Away [Directions] | 5:15 p.m. | ||
| Fri., 1/27 | FR Boys Basketball | Wilton | Away [Directions] | 4:00 p.m. | ||
| Fri., 1/27 | V Girls Basketball | Wilton | Home - Walsh Court | 6:00 p.m. | L 18-59 | |
| Fri., 1/27 | JV Girls Basketball | Wilton | Home - Walsh Court | 4:30 p.m. | ||
| Sat., 1/28 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland Of Ice [Directions] | 7:30 p.m. | L 2-11 | |
| Sun., 1/29 | V Boys Basketball | Pope Francis (MA) | Away - Holyoke CC | 1:00 p.m. | W 80-49 | |
| Wed., 2/1 | V Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 7:00 p.m. | L 62-74 | |
| Wed., 2/1 | JV Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:00 p.m. | ||
| Wed., 2/1 | FR Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 3:45 p.m. | ||
| Wed., 2/1 | V Boys Ice Hockey | Norwalk | Away - SoNo Ice House [Directions] | 8:00 p.m. | W 3-2(OT) | |
| Wed., 2/1 | V Girls Basketball | Brien McMahon | Home - Walsh Court | 5:45 p.m. | W 46-34 | |
| Wed., 2/1 | JV Girls Basketball | Brien McMahon | Home - Walsh Court | 4:00 p.m. | ||
| Thu., 2/2 | V Boys Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | 8:00 p.m. | L 0-9 | |
| Fri., 2/3 | V Boys Basketball | Fairfield Warde | Home - Walsh Court | 7:00 p.m. | L 60-67 | |
| Fri., 2/3 | JV Boys Basketball | Fairfield Warde | Home - Walsh Court | 5:15 p.m. | ||
| Fri., 2/3 | FR Boys Basketball | Fairfield Warde | Home - Walsh Court | 4:00 p.m. | ||
| Fri., 2/3 | V Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 6:00 p.m. | L 42-72 | |
| Fri., 2/3 | JV Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:15 p.m. | ||
| Mon., 2/6 | V Boys Ice Hockey | Staples | Home - Wonderland Bridgeport | 4:45 p.m. | W 7-6(OT) | |
| Tue., 2/7 | V Boys Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 7:00 p.m. | W 60-52 | |
| Tue., 2/7 | JV Boys Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 5:15 p.m. | ||
| Tue., 2/7 | FR Boys Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 4:00 p.m. | ||
| Tue., 2/7 | V Girls Basketball | Danbury | Home - Walsh Court | 5:45 p.m. | L 19-55 | |
| Tue., 2/7 | JV Girls Basketball | Danbury | Home - Walsh Court | 4:00 p.m. | ||
| Wed., 2/8 | V Boys Ice Hockey | Milford Coop | Home - Terry Conners Ice Rink | 6:20 p.m. | W 9-4 | |
| Thu., 2/9 | JV Boys Basketball | Bassick | Home - Walsh Court | 5:15 p.m. | ||
| Thu., 2/9 | FR Boys Basketball | Bassick | Home - Walsh Court | 4:00 p.m. | ||
| Sat., 2/11 | V Boys Ice Hockey | Wilton | Home - Terry Conners Ice Rink | 6:10 p.m. | W 6-1 | |
| Mon., 2/13 | V Boys Basketball | Greenwich | Home - Walsh Court | 7:00 p.m. | W 73-65 | |
| Mon., 2/13 | JV Boys Basketball | Greenwich | Home - Walsh Court | 5:15 p.m. | ||
| Mon., 2/13 | FR Boys Basketball | Greenwich | Home - Walsh Court | 4:00 p.m. | ||
| Mon., 2/13 | V Boys Ice Hockey | Guilford | Home - Terry Conners Ice Rink | 5:10 p.m. | L 2-9 | |
| Mon., 2/13 | V Girls Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 5:30 p.m. | L 22-69 | |
| Mon., 2/13 | JV Girls Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 2/15 | V Boys Basketball | Trumbull | Away - THS Main Gym [Directions] | 7:00 p.m. | W 71-66 | |
| Wed., 2/15 | JV Boys Basketball | Trumbull | Away - THS Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 2/15 | FR Boys Basketball | Trumbull | Away - THS Main Gym [Directions] | 3:45 p.m. | ||
| Wed., 2/15 | V Boys Ice Hockey | Trumbull | Away - Shelton Rinks [Directions] | 7:30 p.m. | L 1-4 | |
| Wed., 2/15 | V Girls Basketball | Trumbull | Home - Walsh Court | 5:45 p.m. | L 25-50 | |
| Wed., 2/15 | JV Girls Basketball | Trumbull | Home - Walsh Court | 4:00 p.m. | ||
| Fri., 2/17 | V Boys Ice Hockey | Wilton | Away - Winter Garden Rink-Ridgefield [Directions] | 4:00 p.m. | L 1-2 | |
| Sat., 2/18 | V Boys Basketball | Bassick | Home - Walsh Court | 5:00 p.m. | W 90-85 | |
| Sat., 2/18 | V Boys Ice Hockey | Darien | Away - Darien Ice Rink [Directions] | 7:00 p.m. | L 0-6 | |
| Mon., 2/20 | V Boys Basketball | Bridgeport Central | Home - Walsh Court | 7:00 p.m. | W 92-88(OT) | |
| Mon., 2/20 | JV Boys Basketball | Bridgeport Central | Home - Walsh Court | 5:15 p.m. | ||
| Mon., 2/20 | FR Boys Basketball | Bridgeport Central | Home - Walsh Court | 4:00 p.m. | ||
| Wed., 2/22 | V Boys Basketball | Stamford | Home - Walsh Court | 7:00 p.m. | W 75-70 | |
| Wed., 2/22 | JV Boys Basketball | Stamford | Home - Walsh Court | 5:15 p.m. | ||
| Wed., 2/22 | FR Boys Basketball | Stamford | Home - Walsh Court | 4:00 p.m. | ||
| Wed., 2/22 | V Boys Ice Hockey | Amity | Away - Bennett Rink - West Haven [Directions] | 4:00 p.m. | W 6-3 | |
| Sat., 3/25 | V Boys Lacrosse | Westhill (Scrim.) | Away - West Hill HS [Directions] | 12:00 p.m. | ||
| Wed., 3/29 | V Baseball | Norwalk (Scrim.) | Away - Nathan Hale M.S. Upper [Directions] | 3:30 p.m. | ||
| Wed., 3/29 | V Girls Tennis | Brien McMahon (Scrim.) | Away - Brian McMahon HS [Directions] | 4:00 p.m. | ||
| Thu., 3/30 | V Softball | King and Low-Heywood Thomas (Scrim.) | Away - King Field | 4:00 p.m. | ||
| Thu., 3/30 | V Girls Tennis | Stamford (Scrim.) | Home - Scalzi Park | 2:45 p.m. | ||
| Sat., 4/1 | V Boys Lacrosse | Notre Dame-Fairfield | Home - Trinity Gaglio Field | 12:00 p.m. | L 6-11 | |
| Mon., 4/3 | V Baseball | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | L 1-6 | |
| Mon., 4/3 | FR Baseball | Darien | Away - DHS Baseball JV Field [Directions] | 3:45 p.m. | ||
| Mon., 4/3 | V Boys Tennis | Staples | Home - Scalzi Park | 4:00 p.m. | L 0-7 | |
| Mon., 4/3 | V Softball | Weston | Away - Hurlbutt El. School, Weston [Directions] | 4:15 p.m. | L 4-6 | |
| Mon., 4/3 | V Girls Tennis | Staples | Away - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Tue., 4/4 | V Boys Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 4:00 p.m. | L 4-14 | |
| Wed., 4/5 | V Boys Tennis | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | L 2-5 | |
| Wed., 4/5 | V Girls Tennis | St. Joseph | Home - Scalzi Park | 4:00 p.m. | L 1-6 | |
| Fri., 4/7 | V Baseball | Stratford | Away - Penders Field [Directions] | 4:00 p.m. | L 2-9 | |
| Fri., 4/7 | V Boys Lacrosse | Westhill | Home - Trinity Gaglio Field | 7:30 p.m.p.m. | L 6-11 | |
| Sat., 4/8 | V Baseball | Career Magnet | Home - Barrett Field @ Belltown Park | 12:00 p.m. | L 1-6 | |
| Sat., 4/8 | V Softball | Weston | Away - Hurlbutt El. School, Weston [Directions] | 3:00 p.m. | W 19-5 | |
| Mon., 4/10 | V Baseball | Staples | Away - Staples HS Baseball Field [Directions] | 1:00 p.m. | L 0-7 | |
| Mon., 4/10 | JV Baseball | Staples | Home - Rippowam | 1:00 p.m. | ||
| Mon., 4/10 | FR Baseball | Staples | Away - Wakeman Field [Directions] | 1:00 p.m. | ||
| Mon., 4/10 | V Boys Tennis | Darien | Home - Scalzi Park | 10:30 a.m. | L 1-6 | |
| Mon., 4/10 | V Softball | Staples | Away - Wakeman Field [Directions] | 1:00 p.m. | L 1-8 | |
| Mon., 4/10 | JV Softball | Staples | Away - Staples HS - Softball Field [Directions] | 1:00 p.m. | ||
| Mon., 4/10 | V Girls Tennis | Darien | Away - DHS Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Tue., 4/11 | V Baseball | Platt Tech | Away - Platt Tech baseball field [Directions] | 3:45 p.m. | L 2-3 | |
| Tue., 4/11 | V Boys Lacrosse | Staples | Home - Trinity Gaglio Field | 4:00 p.m. | L 1-18 | |
| Wed., 4/12 | V Baseball | St. Joseph | Away - St. Joseph HS [Directions] | 1:00 p.m. | L 1-12 | |
| Wed., 4/12 | JV Baseball | St. Joseph | Away - Madison MS, Trumbull [Directions] | 1:00 p.m. | ||
| Wed., 4/12 | FR Baseball | St. Joseph | Home - Barrett Field @ Belltown Park | 1:00 p.m. | ||
| Wed., 4/12 | V Softball | St. Joseph | Home - Boccuzzi Park/Southfield | 1:00 p.m. | L 0-18 | |
| Thu., 4/13 | V Baseball | Ridgefield | Away - Governor's Park Field (aka Ciuccoli or Old HS) [Directions] | 12:00 p.m. | L 9-12 | |
| Thu., 4/13 | JV Baseball | Ridgefield | Away - East Ridge MS [Directions] | 12:00 p.m. | ||
| Thu., 4/13 | FR Baseball | Ridgefield | Away - Branchville Civic (Playground Field) [Directions] | 12:30 p.m. | ||
| Thu., 4/13 | V Boys Lacrosse | King and Low-Heywood Thomas | Home - Trinity Gaglio Field | 4:00 p.m. | L 6-10 | |
| Thu., 4/13 | V Softball | Ridgefield | Home - Stamford HS | 4:00 p.m. | L 1-16 | |
| Thu., 4/13 | JV Softball | Ridgefield | Home - Boccuzzi Park/Southfield | 4:00 p.m. | ||
| Sat., 4/15 | V Softball | Darien | Away - DHS Softball Varsity Field [Directions] | 11:00 a.m. | L 0-10 | |
| Mon., 4/17 | V Baseball | Darien | Home - Trinity Catholic's Lione Field | 4:00 p.m. | L 1-10 | |
| Mon., 4/17 | JV Baseball | Darien | Home - Barrett Field @ Belltown Park | 4:00 p.m. | ||
| Mon., 4/17 | FR Baseball | Darien | Away - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Mon., 4/17 | V Boys Tennis | Norwalk | Home - Scalzi Park | 4:00 p.m. | L 0-7 | |
| Mon., 4/17 | V Softball | West Haven | Away - Frank Biondi Field [Directions] | 3:30 p.m. | L 3-14 | |
| Mon., 4/17 | V Girls Tennis | Norwalk | Home - Scalzi Park | 4:00 p.m. | W 4-3 | |
| Tue., 4/18 | V Boys Golf | Ridgefield | Home - Sterling Farms | 3:15 p.m. | Trinity 203 Quinn Thompson 47 Mike Hennessey 54 Sydney Bardsley 51 Connor Scanlan 55 Adam Pate 60 | |
| Tue., 4/18 | V Boys Lacrosse | Ridgefield | Away - Tiger Hollow Turf Field II [Directions] | 5:00 p.m. | L 3-18 | |
| Tue., 4/18 | V Boys Tennis | New Canaan | Away - NCHS Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Wed., 4/19 | V Baseball | Norwalk | Away - Nathan Hale M.S. Upper [Directions] | 4:00 p.m. | L 0-15 | Varsity with JV Same Bus |
| Wed., 4/19 | JV Baseball | Norwalk | Away - City Hall Field [Directions] | 4:00 p.m. | Varsity with JV Same Bus | |
| Wed., 4/19 | FR Baseball | Norwalk | Home - Trinity Catholic's Lione Field | 4:00 p.m. | ||
| Wed., 4/19 | V Softball | Norwalk | Home - Jewish Community Center | 4:00 p.m. | L 11-15 | |
| Wed., 4/19 | JV Softball | Norwalk | Home - Boccuzzi Park/Southfield | Cancelled | Cancelled | |
| Wed., 4/19 | V Girls Tennis | New Canaan | Home - Scalzi Park | 4:00 p.m. | L 0-7 | |
| Thu., 4/20 | V Baseball | New Canaan | Away - Conner Field [Directions] | 4:00 p.m. | L 2-24 | |
| Thu., 4/20 | V Softball | New Canaan | Home - Jewish Community Center | 4:00 p.m. | L 0-16 | |
| Sat., 4/22 | V Boys Lacrosse | Stratford | Away - Penders Field [Directions] | 1:00 p.m. | L 6-10 | |
| Mon., 4/24 | V Baseball | Westhill | Home - Trinity Catholic's Lione Field | 4:00 p.m. | L 1-5 | |
| Mon., 4/24 | JV Baseball | Westhill | Home - Rippowam | 4:00 p.m. | ||
| Mon., 4/24 | FR Baseball | Westhill | Away - Westhill Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/24 | V Boys Golf | New Canaan | Away - Country Club of New Canaan [Directions] | 3:30 p.m. | Trinity 203 Quinn Thompson 53 Mike Hennessey 57 Sydney Bardsley 51 Connor Scanlan 60 Adam Pate 62 | |
| Mon., 4/24 | V Boys Tennis | Fairfield Ludlowe | Home - Scalzi Park | 4:00 p.m. | L 1-6 | |
| Mon., 4/24 | V Softball | Westhill | Away - Westhill Varsity Softball Field [Directions] | 4:00 p.m. | L 1-13 | |
| Mon., 4/24 | JV Softball | Westhill | Away - Roxbury Elementary School [Directions] | 4:00 p.m. | ||
| Mon., 4/24 | V Girls Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Tue., 4/25 | V Boys Lacrosse | Brien McMahon | Home - Trinity Gaglio Field | 5:00 p.m. | L 6-15 | |
| Wed., 4/26 | V Boys Golf | Greenwich | Home - Sterling Farms | 3:15 p.m. | Trinity 203 Quinn Thompson 54 Mike Hennessey 58 Sydney Bardsley 45 Connor Scanlan 50 Adam Pate 54 Greenwich 148 Jake Moses 36 Jackson Fretty 34 Billy Nail 37 Ben Ropiaic 41 Chris Magliocci 42 | |
| Wed., 4/26 | V Boys Golf | Staples | Home - Sterling Farms | 3:15 p.m. | Trinity 203 Quinn Thompson 54 Mike Hennessey 58 Sydney Bardsley 45 Connor Scanlan 50 Adam Pate 54 Staples 165 Peter Taets 41 Tristan Hochangh 39 Colin Cusa 42 Noah Lomnitz 43 Mitchell Schwab 43 | |
| Thu., 4/27 | V Boys Tennis | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | L 2-5 | |
| Thu., 4/27 | V Girls Tennis | Brien McMahon | Home - Scalzi Park | 4:00 p.m. | L 2-5 | |
| Fri., 4/28 | V Baseball | Wilton | Away - WHS Varsity Baseball Field [Directions] | 4:30 p.m. | L 2-6 | |
| Fri., 4/28 | JV Baseball | Wilton | Away - JV Baseball Field [Directions] | 4:30 p.m. | ||
| Fri., 4/28 | FR Baseball | Wilton | Home - Trinity Catholic's Lione Field | 4:30 p.m. | ||
| Fri., 4/28 | V Softball | Wilton | Home - Jewish Community Center | 4:30 p.m. | L 3-10 | |
| Fri., 4/28 | JV Softball | Wilton | Home - BoccuzziPark/Southfield | 4:30 p.m. | ||
| Sat., 4/29 | V Baseball | Fairfield Ludlowe | Home - Trinity Catholic's Lione Field | 12:00 p.m. | L 0-11 | |
| Sat., 4/29 | V Boys Lacrosse | Wilton | Away - Fujitani Field - Turf [Directions] | 4:00 p.m. | L 3-18 | |
| Sat., 4/29 | V Softball | Fairfield Ludlowe | Away - Sturges Park [Directions] | 2:00 p.m. | L 0-8 | |
| Sat., 4/29 | JV Softball | Fairfield Ludlowe | Away - Tom Hayden field [Directions] | Cancelled | Cancelled | |
| Mon., 5/1 | V Baseball | Brien McMahon | Away - Nathan Hale MS [Directions] | 4:30 p.m. | L 0-6 | |
| Mon., 5/1 | JV Baseball | Brien McMahon | Away - Roton [Directions] | 4:00 p.m. | ||
| Mon., 5/1 | V Boys Tennis | Fairfield Warde | Home - Scalzi Park | 4:00 p.m. | L 0-7 | |
| Mon., 5/1 | V Softball | Brien McMahon | Home - Jewish Community Center | 4:00 p.m. | W 15-0 | |
| Mon., 5/1 | JV Softball | Brien McMahon | Home - Boccuzzi Park/Southfield | 4:00 p.m. | ||
| Mon., 5/1 | V Girls Tennis | Fairfield Warde | Away - FWHS Blake Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Tue., 5/2 | V Boys Golf | Fairfield Warde | Home - Sterling Farms | 3:15 p.m. | Trinity Catholic 205 Fairfield Warde | |
| Tue., 5/2 | V Boys Lacrosse | Fairfield Warde | Home - Trinity Gaglio Field | 4:30 p.m. | L 9-20 | |
| Tue., 5/2 | V Softball | Stratford | Home - Boccuzzi Park/Southfield | 4:15 p.m. | W 13-7 | |
| Wed., 5/3 | V Baseball | Fairfield Warde | Home - Trinity Catholic's Lione Field | 4:00 p.m. | L 4-16 | |
| Wed., 5/3 | JV Baseball | Fairfield Warde | Home - Rippowam | 4:00 p.m. | ||
| Wed., 5/3 | FR Baseball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 4:00 p.m. | ||
| Wed., 5/3 | V Boys Tennis | Danbury | Away - WCSU Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Wed., 5/3 | V Softball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 4:00 p.m. | L 0-15 | |
| Wed., 5/3 | V Girls Tennis | Danbury | Home - Scalzi Park | 4:00 p.m. | L 3-4 | |
| Thu., 5/4 | V Baseball | Danbury | Away - Danbury HS Varsity Baseball Field [Directions] | 4:00 p.m. | L 8-19 | |
| Thu., 5/4 | JV Baseball | Danbury | Away - Westerner Baseball Field, Rogers Park [Directions] | 3:45 p.m. | ||
| Thu., 5/4 | FR Baseball | Danbury | Home - Trinity Catholic's Lione Field | 4:00 p.m. | ||
| Thu., 5/4 | V Boys Golf | Stamford, Westhill | Home - Sterling Farms [Directions] | 3:15 p.m. | Stamford. 176 Westhill. 178 Trinity. 205 | |
| Thu., 5/4 | V Boys Lacrosse | Stamford | Away - Stamford HS [Directions] | 7:00 p.m. | L 3-13 | |
| Thu., 5/4 | V Softball | Danbury | Home - Boccuzzi Park/Southfiled | 4:00 p.m. | L 5-12 | |
| Thu., 5/4 | JV Softball | Darien | Away - DHS Softball JV Field [Directions] | 3:30 p.m. | ||
| Fri., 5/5 | JV Softball | Danbury | Home - Boccuzzi Park/Southfield | Cancelled | Cancelled | |
| Sat., 5/6 | V Boys Lacrosse | St. Joseph | Home - Trinity Gaglio Field | 4:00 p.m. | L 3-18 | |
| Mon., 5/8 | V Boys Tennis | Greenwich | Home - Scalzi Park | 4:00 p.m. | L 1-6 | |
| Mon., 5/8 | V Girls Tennis | Greenwich | Away - GHS Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Tue., 5/9 | V Boys Lacrosse | New Canaan | Away - Dunning Stadium [Directions] | 4:00 p.m. | L 0-19 | |
| Tue., 5/9 | V Boys Tennis | Trumbull | Away - THS Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Tue., 5/9 | V Girls Tennis | Trumbull | Home - Scalzi Park | 4:00 p.m. | L 0-7 | |
| Wed., 5/10 | V Baseball | Greenwich | Home - Trinity Catholic's Lione Field | 4:30 p.m. | L 1-10 | |
| Wed., 5/10 | JV Baseball | Greenwich | Home - Barrett Field @ Belltown Park | 4:30 p.m. | ||
| Wed., 5/10 | FR Baseball | Greenwich | Away - GHS Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/10 | V Boys Golf | St. Joseph | Home - Sterling Farms | 3:15 p.m. | St. Joseph 166 Vs Trinity 214 | |
| Wed., 5/10 | V Boys Tennis | Ridgefield | Away - RHS Tennis Courts [Directions] | 4:00 p.m. | L 1-6 | |
| Wed., 5/10 | V Softball | Greenwich | Away - GHS Softball Field [Directions] | 4:00 p.m. | L 3-4 | |
| Wed., 5/10 | JV Softball | Greenwich | Away - Julian Curtiss School [Directions] | 4:00 p.m. | ||
| Wed., 5/10 | V Girls Tennis | Ridgefield | Home - Scalzi Park | 4:00 p.m. | L 0-7 | |
| Thu., 5/11 | V Boys Lacrosse | Darien | Home - Trinity Gaglio Field | 4:00 p.m. | L 4-21 | |
| Thu., 5/11 | V Boys Tennis | Bridgeport Central | Home - Scalzi Park | 4:00 p.m. | W 5-2 | |
| Thu., 5/11 | V Girls Tennis | Bridgeport Central | Away [Directions] | 4:00 p.m. | W 7-0 | |
| Fri., 5/12 | V Baseball | Trumbull | Away - Varsity Baseball Field [Directions] | 4:00 p.m. | L 0-16 | |
| Fri., 5/12 | JV Baseball | Trumbull | Away - JV Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 5/12 | FR Baseball | Trumbull | Home - Trinity Catholic's Lione Field | 4:00 p.m. | ||
| Fri., 5/12 | V Boys Tennis | Westhill | Home - Scalzi Park | 4:00 p.m. | L 3-4 | |
| Fri., 5/12 | V Softball | Trumbull | Home - Jewish Community Center | 4:15 p.m. | L 0-20(5) | |
| Fri., 5/12 | JV Softball | Trumbull | Home - Boccuzzi Park/Southfield | 4:00 p.m. | ||
| Fri., 5/12 | V Girls Tennis | Westhill | Away [Directions] | 4:00 p.m. | L 0-7 | |
| Sat., 5/13 | V Boys Tennis | Wilton | Away - Four Seasons - Indoor Courts [Directions] | 1:00 p.m. | L Forfeit | |
| Mon., 5/15 | V Baseball | Bridgeport Central | Home - Trinity Catholic's Lione Field | 4:00 p.m. | W 11-3 | |
| Mon., 5/15 | JV Baseball | Bridgeport Central | Home - Rippowam | 4:00 p.m. | ||
| Mon., 5/15 | V Boys Golf | Danbury | Away - Richter Park Golf Course [Directions] | 3:15 p.m. | Danbury 193 Vs Trinity 218 | |
| Mon., 5/15 | V Boys Tennis | Stamford | Home - Scalzi Park | 4:00 p.m. | L 3-4 | |
| Mon., 5/15 | V Softball | Bridgeport Central | Away - Central H.S. Junior Varsity Softball Field [Directions] | 4:00 p.m. | L 5-7 | |
| Mon., 5/15 | JV Softball | Bridgeport Central | Away - Ripken Field [Directions] | 4:00 p.m. | ||
| Mon., 5/15 | V Girls Tennis | Stamford | Away [Directions] | 4:00 p.m. | L 1-6 | |
| Tue., 5/16 | V Boys Golf | Trumbull | Home - Sterling Farms | 3:15 p.m. | Trumbull 158 Vs Trinity 197 | |
| Tue., 5/16 | JV Softball | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | ||
| Tue., 5/16 | V Girls Tennis | Wilton | Home - Scalzi Park | 4:00 p.m. | L 0-7 | |
| Wed., 5/17 | V Baseball | Stamford | Home - Trinity Catholic's Lione Field | 4:00 p.m. | L 5-8 | |
| Wed., 5/17 | JV Baseball | Stamford | Away - Barrett Field @ Belltown Park [Directions] | 4:00 p.m. | ||
| Wed., 5/17 | FR Baseball | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | ||
| Wed., 5/17 | V Boys Golf | Fairfield Ludlowe | Home - Sterling Farms | 3:15 p.m. | Trinity 200 vs Fairfield Ludlowe 173 | |
| Wed., 5/17 | V Boys Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | 7:00 p.m. | L 1-16 | |
| Wed., 5/17 | V Softball | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | L 0-16 | |
| Sat., 5/20 | V Boys Lacrosse | Stratford | Home - Trinity Gaglio Field | 7:00 p.m. | L 9-11 | |
| Mon., 5/22 | V Boys Golf | Brien McMahon | Home - Sterling Farms | 3:15 p.m. | Trinity 205 Vs Brien McMahon 234 | |
| Tue., 5/23 | V Boys Golf | Norwalk | Away - Oak Hills G.C. [Directions] | 3:15 p.m. | Trinity 195 vs Norwalk 198 | |
| Wed., 5/24 | V Boys Golf | Darien, Wilton | Home - Sterling Farms | 3:15 p.m. | Darien 162 Wilton - 178 Trinity - 190 | |