| New Canaan 2021-22 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 534 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| Wed., 8/25 | V Football | West Haven (Scrim.) | Home - New Canaan HS-Dunning Stadium [Directions] | 2:00 p.m. | ||
| Fri., 8/27 | V Football | Scrimmage at Stepinac | Away - Not Listed | 4:00 p.m. | 2:00 PM; 2 Buses | |
| Mon., 8/30 | V Girls Soccer | St. Lukes (Scrim.) | Home - New Canaan HS-Conner Field [Directions] | 3:15 p.m. | TBA | |
| Tue., 8/31 | V Boys Golf | Westhill | Away - EG Brennan Golf Course-E Gaynor Brennan Golf Course [Directions] | New Canaan 147 Westhill 177 | 2:05 PM; 1 Bus | |
| Thu., 9/2 | V Football | Brookfield (Scrim.) | Home - New Canaan HS-Dunning Stadium [Directions] | 4:30 p.m. | ||
| Thu., 9/2 | V Boys Soccer | St. Lukes (Scrim.) | Away - St. Lukes-Class of 2015 Field | 4:00 p.m. | 2:15 PM; 1 Bus | |
| Thu., 9/2 | V Girls Soccer | Greenwich Academy (Scrim.) | Away - Greenwich Academy | 4:00 p.m. | 2:15 PM; 1 Bus | |
| Fri., 9/3 | V Football | Home Scrimmage Fordham Prep | Home - New Canaan HS-Dunning Stadium [Directions] | 6:00 p.m. | ||
| Fri., 9/3 | V Girls Soccer | Sacred Heart of Greenwich (Scrim.) | Away - Sacred Heart | 4:30 p.m. | 2:45 PM; 1 Bus | |
| Sat., 9/4 | V Field Hockey | New Fairfield, Amity, Bethel, Brookfield, Masuk, New Milford, Newtown, Ridgefield, Shepaug Valley | Away - New Fairfield HS-Marty Morgan Field | 9:00 a.m. | 7:00 AM; 1 Bus | |
| Wed., 9/8 | V Boys Golf | Ridgefield | Away - Ridgewood CC [Directions] | New Canaan 163 Ridgefield 185 | 2:05 PM; 1 Bus | |
| Thu., 9/9 | V Boys Golf | St. Joseph, TBA | Away - Tashua Knolls Golf Course [Directions] | St. Joseph 156 New Canaan 158 | 2:05 PM; 1 Van | |
| Thu., 9/9 | V Field Hockey | Stamford | Home - New Canaan HS-Dunning Stadium [Directions] | W 9-0 | ||
| Thu., 9/9 | V Girls Soccer | Danbury | Home - New Canaan HS-Dunning Stadium [Directions] | W 3-0 | ||
| Thu., 9/9 | V Girls Volleyball | St. Lukes (Scrim.) | Away - St. Lukes-Gym | 4:00 p.m. | 2:40 PM; 1 Bus | |
| Fri., 9/10 | V Boys Soccer | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | L 0-1 | 2:10 PM; 1 Bus | |
| Sat., 9/11 | V Football | Bridgeport Central | Away - Bridgeport Central HS-Kennedy Stadium Turf [Directions] | W 49-0 | 5:00 PM; 1 Bus | |
| Mon., 9/13 | V Girls Soccer | Staples | Away - Staples HS-Loeffler Field - Staples HS [Directions] | T 1-1 | 2:10 PM; 1 Bus | |
| Mon., 9/13 | V Girls Swimming and Diving | Norwalk/McMahon | Home - Waveny Park-Waveny Pool [Directions] | 3:30 p.m. | ||
| Tue., 9/14 | V Boys Cross Country | Fairfield Ludlowe, St. Joseph | Home - Waveny Park [Directions] | 4:30 p.m. | ||
| Tue., 9/14 | V Boys Golf | Fairfield Warde, Stamford | Home - CCNC [Directions] | New Canaan 145 Stamford 203 Fairfield Warde 161 | ||
| Tue., 9/14 | V Boys Soccer | Staples | Home - New Canaan HS-Dunning Stadium [Directions] | L 1-2 | ||
| Tue., 9/14 | V Girls Cross Country | Fairfield Ludlowe, St. Joseph | Home - Waveny Park [Directions] | 4:00 p.m. | ||
| Tue., 9/14 | V Field Hockey | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | W 8-0 | 2:10 PM; 1 Bus | |
| Tue., 9/14 | V Girls Volleyball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | W 3-0 | 3:15 PM; 1 Bus | |
| Fri., 9/17 | V Football | Brien McMahon | Home - New Canaan HS-Dunning Stadium [Directions] | W 50-0 | ||
| Fri., 9/17 | V Girls Soccer | Wilton | Home - New Canaan HS-Dunning Stadium [Directions] | T 0-0 | ||
| Fri., 9/17 | V Girls Volleyball | Joel Barlow | Home - New Canaan HS-Main Gym [Directions] | W 3-2 | ||
| Sat., 9/18 | V Boys Soccer | Wilton | Away - Wilton HS-Lilly Field [Directions] | L 1-2 | 8:30 AM; 1 Bus | |
| Sat., 9/18 | V Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | W 6-1 | 8:15 AM; 1 Bus | |
| Tue., 9/21 | V Boys Cross Country | Wilton, Stamford, Staples | Away - Allen's Meadow-XC Course [Directions] | 4:00 p.m. | 2:10 PM; 1 Bus | |
| Tue., 9/21 | V Boys Golf | Brien McMahon | Away - Oak Hills Golf Course [Directions] | New Canaan 149 Brien McMahon 191 | 2:05 PM; 1 Van | |
| Tue., 9/21 | V Girls Cross Country | Wilton, Stamford, Staples | Away - Allen's Meadow-XC Course [Directions] | 4:00 p.m. | 2:10 PM; 1 Bus | |
| Tue., 9/21 | V Field Hockey | Trumbull | Home - New Canaan HS-Dunning Stadium [Directions] | W 3-0 | ||
| Tue., 9/21 | V Girls Soccer | St. Joseph | Home - New Canaan HS-Dunning Stadium [Directions] | L 1-3 | ||
| Wed., 9/22 | V Boys Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | Fairfield Ludlowe 158 New Canaan 165 | 2:05 PM; 1 Van | |
| Wed., 9/22 | V Boys Soccer | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | W 3-2 | 2:10 PM; 1 Bus | |
| Wed., 9/22 | V Girls Swimming and Diving | Ridgefield | Home - New Canaan YMCA-Pool [Directions] | 3:00 p.m. | ||
| Wed., 9/22 | V Girls Volleyball | Ridgefield | Home - New Canaan HS-Main Gym [Directions] | W 3-1 | ||
| Thu., 9/23 | V Boys Golf | Norwalk | Home - CCNC [Directions] | New Canaan 159 Norwalk 212 | ||
| Thu., 9/23 | V Field Hockey | Westhill | Home - New Canaan HS-Dunning Stadium [Directions] | W 9-0 | ||
| Fri., 9/24 | V Football | Daniel Hand | Away - Madison Surf Club-Strong Field [Directions] | W 28-18 | 4:00 PM; 2 Buses | |
| Fri., 9/24 | V Boys Soccer | Ridgefield | Home - New Canaan HS-Dunning Stadium [Directions] | L 0-3 | ||
| Fri., 9/24 | V Girls Soccer | Ridgefield | Away - Ridgefield HS-Tiger Hollow Turf Field II [Directions] | L 0-1 | 2:30 PM; 1 Bus | |
| Fri., 9/24 | V Girls Volleyball | Fairfield Ludlowe | Home - New Canaan HS-Main Gym [Directions] | L 0-3 | ||
| Sat., 9/25 | V Field Hockey | Greenwich | Home - New Canaan HS-Dunning Stadium [Directions] | W 1-0 | ||
| Mon., 9/27 | V Boys Golf | Wilton | Home - CCNC [Directions] | New Canaan 152 Wilton 158 | ||
| Mon., 9/27 | V Girls Soccer | Stamford | Home - New Canaan HS-Dunning Stadium [Directions] | W 2-0 | ||
| Tue., 9/28 | V Boys Golf | Danbury, Norwalk | Away - Richter Park Golf Course [Directions] | New Canaan 157 Danbury 178 | 2:00 PM; 1 Bus | |
| Tue., 9/28 | V Boys Soccer | Stamford | Away - Stamford HS-SHS Upper Soccer Field [Directions] | L 0-4 | 2:30 PM; 1 Bus | |
| Tue., 9/28 | V Field Hockey | St. Joseph | Home - New Canaan HS-Dunning Stadium [Directions] | W 9-0 | ||
| Tue., 9/28 | V Girls Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | W 3-0 | 2:05 PM; 1 Bus | |
| Wed., 9/29 | V Boys Cross Country | Danbury, Ridgefield, Trumbull | Home - Waveny Park [Directions] | 4:30 p.m. | ||
| Wed., 9/29 | V Boys Golf | Greenwich | Home - CCNC [Directions] | New Canaan 151 Greenwich 168 | ||
| Wed., 9/29 | V Girls Cross Country | Danbury, Ridgefield, Trumbull | Home - Waveny Park [Directions] | 4:00 p.m. | ||
| Wed., 9/29 | V Girls Swimming and Diving | Wilton | Home - New Canaan YMCA-Pool [Directions] | 3:00 p.m. | ||
| Thu., 9/30 | V Boys Golf | Staples | Away - Longshore Golf Course [Directions] | New Canaan 142 Staples 147 | 2:05 PM; 1 Van | |
| Thu., 9/30 | V Girls Soccer | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | W 4-1 | 2:45 PM; 1 Bus | |
| Thu., 9/30 | V Girls Volleyball | Staples | Home - New Canaan HS-Main Gym [Directions] | W 3-0 | ||
| Fri., 10/1 | V Football | North Haven | Home - New Canaan HS-Dunning Stadium [Directions] | W 21-7 | ||
| Fri., 10/1 | V Boys Soccer | Greenwich | Home - New Canaan HS-Dunning Stadium [Directions] | L 0-6 | ||
| Fri., 10/1 | V Field Hockey | Wilton | Home - New Canaan HS-WTT #2 [Directions] | W 6-0 | ||
| Sat., 10/2 | V Girls Swimming and Diving | St. Joseph | Away - High Plains Community Cn-Orange Community Center Pool [Directions] | 3:00 p.m. | 6:00 PM; 1 Bus | |
| Sat., 10/2 | V Girls Volleyball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | W 3-2 | 4:15 PM; 1 Bus | |
| Mon., 10/4 | V Boys Golf | Darien | Home - CCNC [Directions] | New Canaan 154 Darien 159 | ||
| Mon., 10/4 | V Girls Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | W 4-1 | 4:00 PM; 1 Bus | |
| Mon., 10/4 | V Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | L 0-3 | 3:30 PM; 1 Bus | |
| Tue., 10/5 | V Boys Cross Country | Greenwich, Darien, Fairfield Warde | Away - Greenwich Point [Directions] | 4:00 p.m. | 2:15 PM; 1 Bus | |
| Tue., 10/5 | V Boys Golf | Trumbull | Home - CCNC [Directions] | New Canaan 157 Trumbull 186 | ||
| Tue., 10/5 | V Boys Soccer | Brien McMahon | Home - New Canaan HS-Dunning Stadium [Directions] | L 0-2 | ||
| Tue., 10/5 | V Girls Cross Country | Greenwich, Darien, Fairfield Warde | Away - Greenwich Point [Directions] | 4:00 p.m. | 2:15 PM; 1 Bus | |
| Tue., 10/5 | V Field Hockey | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | W 9-0 | 2:05 PM; 1 Bus | |
| Wed., 10/6 | V Girls Soccer | Bridgeport Central | Home - New Canaan HS-Dunning Stadium [Directions] | W 6-0 | ||
| Thu., 10/7 | V Boys Soccer | Bridgeport Central | Away - Bridgeport Central HS-Kennedy Stadium Turf [Directions] | W 3-0 | 2:00 PM; 1 Bus | |
| Thu., 10/7 | V Field Hockey | New Milford | Away - New Milford HS-Joe Wiser Stadium - NMHS [Directions] | W 6-0 | 1:00 PM; 1 Bus | |
| Thu., 10/7 | V Girls Soccer | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | L 0-1 | 2:00 PM; 1 Bus | |
| Thu., 10/7 | V Girls Swimming and Diving | Fairfield Ludlowe | Away - Fairfield University-Pool [Directions] | 4:00 p.m. | 2:15 PM; 1 Bus | |
| Sat., 10/9 | V Boys Soccer | Fairfield Warde | Home - New Canaan HS-Dunning Stadium [Directions] | L 0-2 | ||
| Sat., 10/9 | V Field Hockey | Cheshire | Home - New Canaan HS-Dunning Stadium [Directions] | W 5-0 | ||
| Sat., 10/9 | V Girls Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | W 3-1 | 4:15 PM; 1 Bus | |
| Mon., 10/11 | V Field Hockey | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | W 6-0 | 3:00 PM; 1 Bus | |
| Mon., 10/11 | V Girls Volleyball | Greenwich | Home - New Canaan HS-Main Gym [Directions] | L 0-3 | ||
| Tue., 10/12 | V Boys Cross Country | Brien McMahon, Norwalk, Westhill | Home - Waveny Park [Directions] | 4:30 p.m. | ||
| Tue., 10/12 | V Girls Cross Country | Brien McMahon, Norwalk, Westhill | Home - Waveny Park [Directions] | 4:00 p.m. | ||
| Tue., 10/12 | V Girls Diving | Darien | Away - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Tue., 10/12 | V Girls Soccer | Darien | Away - Darien HS-DHS Center Oval Turf Field [Directions] | W 2-1 | 2:40 PM; 1 Bus | |
| Wed., 10/13 | V Boys Soccer | Darien | Home - New Canaan HS-Dunning Stadium [Directions] | T 1-1 | ||
| Wed., 10/13 | V Girls Swimming and Diving | Darien | Away - Darien YMCA [Directions] | 3:00 p.m. | 2:10 PM; 1 Bus | |
| Wed., 10/13 | V Girls Volleyball | Brien McMahon | Home - New Canaan HS-Main Gym [Directions] | L 3-2 | ||
| Thu., 10/14 | V Field Hockey | Ridgefield | Away - Ridgefield HS-Tiger Hollow Turf Field II [Directions] | W 3-0 | 2:10 PM; 1 Bus | |
| Thu., 10/14 | V Girls Soccer | Trumbull | Home - New Canaan HS-Dunning Stadium [Directions] | T 0-0 | ||
| Fri., 10/15 | V Boys Soccer | Trumbull | Away - Trumbull HS-Cork Field [Directions] | L 0-1 | 2:10 PM; 1 Bus | |
| Fri., 10/15 | V Girls Swimming and Diving | Westhill/Stamford | Away - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | 2:15 PM; 1 Bus | |
| Fri., 10/15 | V Girls Volleyball | Bridgeport Central | Away - Bridgeport Central HS-Barry McLeod Court [Directions] | W 3-0 | 3:30 PM; 1 Bus | |
| Sun., 10/17 | V Football | Norwalk | Away - Norwalk HS-Testa Field [Directions] | W 17-14 | 5:00 PM; 2 Buses | |
| Mon., 10/18 | V Boys Golf | CIAC Fall Division I Boys Golf Championship | Away - Chippanee GC | 8:30 a.m. | ||
| Mon., 10/18 | V Girls Soccer | Fairfield Ludlowe | Home - New Canaan HS-Dunning Stadium [Directions] | W 2-1 | ||
| Mon., 10/18 | V Girls Volleyball | Fairfield Warde | Home - New Canaan HS-Main Gym [Directions] | L 2-3 | ||
| Tue., 10/19 | V Boys Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | W 5-2 | 5:00 PM; 1 Bus | |
| Tue., 10/19 | V Field Hockey | Norwalk | Home - New Canaan HS-Dunning Stadium [Directions] | W 8-0 | ||
| Wed., 10/20 | V Boys Cross Country | FCIAC Cross Country Championships | Home - Waveny Park [Directions] | 3:00 p.m. | ||
| Wed., 10/20 | V Girls Cross Country | FCIAC Cross Country Championships | Home - Waveny Park [Directions] | 3:00 p.m. | ||
| Wed., 10/20 | V Girls Swimming and Diving | Trumbull | Home - New Canaan YMCA-Pool [Directions] | 3:00 p.m. | ||
| Wed., 10/20 | V Girls Volleyball | Darien | Home - New Canaan HS-Main Gym [Directions] | L 3-0 | ||
| Fri., 10/22 | V Boys Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | L 2-4 | 4:30 PM; 1 Bus | |
| Fri., 10/22 | V Field Hockey | Darien | Away - Darien HS-DHS Stadium Field [Directions] | W 2-1 | 2:40 PM; 1 Bus | |
| Fri., 10/22 | V Girls Soccer | Norwalk | Home - New Canaan HS-Dunning Stadium [Directions] | W 4-0 | ||
| Fri., 10/22 | V Girls Swimming and Diving | Fairfield Warde | Home - New Canaan YMCA-Pool [Directions] | 3:00 p.m. | ||
| Sat., 10/23 | V Football | Wilton | Home - New Canaan HS-Dunning Stadium [Directions] | L 17-20 | ||
| Sat., 10/23 | V Girls Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | L 0-3 | 4:30 PM; 1 Bus | |
| Mon., 10/25 | V Girls Soccer | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | W 8-0 | 2:20 PM; 1 Bus | |
| Tue., 10/26 | V Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | L 1-3 | 3:30 PM; 1 Bus | |
| Wed., 10/27 | V Boys Soccer | Westhill | Home - New Canaan HS-Dunning Stadium [Directions] | L 0-1 | ||
| Thu., 10/28 | V Field Hockey | Staples | Home - New Canaan HS-Dunning Stadium [Directions] | W 2-1 | ||
| Thu., 10/28 | V Girls Soccer | Staples | Away - Staples HS-Wakeman Field B (turf) [Directions] | L 1-3 | 1:15 PM; 1 Bus | |
| Thu., 10/28 | V Girls Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | W 3-0 | 2:45 PM; 1 Bus | |
| Sat., 10/30 | V Football | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | W 14-7 | 1:00 PM; 2 Buses | |
| Sat., 10/30 | V Field Hockey | Fairfield Ludlowe | Home - New Canaan HS-Dunning Stadium [Directions] | 10:00 a.m. | ||
| Sat., 10/30 | V Girls Volleyball | Westhill | Home - New Canaan HS-Main Gym [Directions] | W 3-1 | ||
| Mon., 11/1 | V Boys Cross Country | CIAC Boys Cross Country Class L Championship | Away - Wickham Park | 11:25 a.m. | ||
| Mon., 11/1 | V Girls Cross Country | CIAC Girls Cross Country Class L Championship | Away - Wickham Park | 11:55 a.m. | ||
| Tue., 11/2 | V Field Hockey | Ridgefield | Home - Brien McMahon HS-Pride Field [Directions] | 6:00 p.m. | 4:15 PM; 1 Bus | |
| Wed., 11/3 | V Girls Swimming and Diving | FCIAC Girls Swim Trials | Away - Greenwich HS | 5:00 p.m. | ||
| Thu., 11/4 | V Girls Soccer | Greenwich (Scrim.) | Home - New Canaan HS-WTT #1 [Directions] | 4:00 p.m. | ||
| Thu., 11/4 | V Girls Swimming and Diving | FCIAC Girls Diving Finals | Away - Fairfield County Interscholastic Athletic Conferen-Westhill HS | 5:00 p.m. | ||
| Fri., 11/5 | V Boys Cross Country | CIAC Boys Cross Country Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Fri., 11/5 | V Football | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | W 33-6 | 4:00 PM; 2 Buses | |
| Fri., 11/5 | V Girls Cross Country | CIAC Girls Cross Country Open Championship | Away - Wickham Park | 2:45 p.m. | 11:00 AM; 1 Van | |
| Fri., 11/5 | V Girls Volleyball | Brien McMahon (Scrim.) | Home - New Canaan HS-Main Gym [Directions] | Cancelled | ||
| Sat., 11/6 | V Girls Swimming and Diving | FCIAC Girls Swim Finals | Away - Fairfield County Interscholastic Athletic Conferen-Greenwich HS | 4:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Greenwich HS | ||||||
| Mon., 11/8 | V Girls Soccer | Middletown | Home - New Canaan HS-Dunning Stadium [Directions] | W 5-0 | ||
| Mon., 11/8 | V Girls Volleyball | East Hartford | Away - East Hartford HS [Directions] | 6:00 p.m. | 3:00 PM; 1 Bus | |
| Wed., 11/10 | V Field Hockey | Norwalk | Home - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | ||
| Wed., 11/10 | V Girls Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | L 3-2 | 2:10 PM; 1 Bus | |
| Wed., 11/10 | V Girls Swimming and Diving | CIAC Class L Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Thu., 11/11 | V Girls Volleyball | Cheshire | Away - Cheshire HS-Gym West [Directions] | 6:00 p.m. | 2:30 PM; 1 Bus | |
| Fri., 11/12 | V Football | Fairfield Warde | Home - New Canaan HS-Dunning Stadium [Directions] | W 27-7 | ||
| Sat., 11/13 | V Field Hockey | Greenwich | Home - New Canaan HS-Dunning Stadium [Directions] | 12:00 p.m. | ||
| Sat., 11/13 | V Girls Swimming and Diving | CIAC Class L Qualifying Meet | Away - Cornerstone Pool | 3:15 p.m. | ||
| Tue., 11/16 | V Field Hockey | Glastonbury | Home - Pomperaug HS-Stadium [Directions] | 6:00 p.m. | 3:15 PM; 1 Bus | |
| Tue., 11/16 | V Girls Swimming and Diving | CIAC Class L Swimming Championships | Away - SCSU | 6:00 p.m. | 3:00 PM; 1 Bus | |
| Thu., 11/18 | V Girls Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 11/20 | V Field Hockey | Wilton | Home - Wethersfield HS-Cottone Field [Directions] | 12:00 p.m. | ||
| Sun., 11/21 | V Girls Swimming and Diving | CIAC State Open Swimming Championships | Away - Cornerstone Pool | 2:00 p.m. | ||
| Thu., 11/25 | V Football | Darien | Home - New Canaan HS-Dunning Stadium [Directions] | W 12-7 | ||
| Tue., 11/30 | V Football | Southington | Home - New Canaan HS-Dunning Stadium [Directions] | 6:30 p.m. | ||
| Sat., 12/4 | V Girls Basketball | Bridgeport Central (Scrim.) | Home - Danbury HS-G gym (freshman academy gym) [Directions] | 12:00 p.m. | ||
| Sat., 12/4 | V Girls Basketball | New Fairfield | Home - Danbury HS-New Gym [Directions] | 12:30 p.m. | ||
| Sat., 12/4 | V Girls Basketball | Bethel (Scrim.) | Home - Danbury HS-G gym (freshman academy gym) [Directions] | 1:30 p.m. | ||
| Sat., 12/4 | V Girls Basketball | Capital Prep Harbor (Scrim.) | Home - Danbury HS-Main Gym [Directions] | 2:00 p.m. | ||
| Sat., 12/4 | V Girls Basketball | Fairfield Warde (Scrim.) | Home - Danbury HS-New Gym [Directions] | 3:00 p.m. | ||
| Sat., 12/4 | V Girls Basketball | Brookfield (Scrim.) | Home - Danbury HS-New Gym [Directions] | 3:30 p.m. | ||
| Sat., 12/4 | V Girls Basketball | Stamford (Scrim.) | Home - Danbury HS-G gym (freshman academy gym) [Directions] | 4:30 p.m. | ||
| Sun., 12/5 | V Football | Darien | Home - New Canaan HS-Dunning Stadium [Directions] | 12:30 p.m. | ||
| Mon., 12/6 | V Girls Ice Hockey | Greenwich Academy | Home - Darien Ice House-Ice Rink [Directions] | W 4-3 | ||
| Wed., 12/8 | V Boys Basketball | Weston (Scrim.) | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 12/8 | V Boys Ice Hockey | Fairfield Warde/Ludlowe (Scrim.) | Home - Darien Ice House-Ice Rink [Directions] | 7:50 p.m. | ||
| Thu., 12/9 | V Girls Basketball | Westhill (Scrim.) | Home - New Canaan HS-Main Gym [Directions] | 3:00 p.m. | ||
| Sat., 12/11 | V Boys Basketball | Bethel (Scrim.) | Away - Bethel HS-BHS gym [Directions] | 11:30 a.m. | 9:30 AM; 1 Bus | |
| Sat., 12/11 | V Girls Ice Hockey | Greenwich | Home - Darien Ice House-Ice Rink [Directions] | W 5-2 | ||
| Mon., 12/13 | V Boys Basketball | Joel Barlow (Scrim.) | Away - Joel Barlow HS-Lower Gym [Directions] | 6:00 p.m. | 3:45 PM; 1 Bus | |
| Mon., 12/13 | V Boys Ice Hockey | West Haven Coop | Home - Darien Ice House-Ice Rink [Directions] | W 4-0 | ||
| Wed., 12/15 | V Girls Basketball | Bassick | Away - Bassick HS-Gym [Directions] | W 44-5 | 3:20 PM; 1 Bus | |
| Wed., 12/15 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | W 10-1 | 6:30 PM; 1 Bus | |
| Thu., 12/16 | V Boys Basketball | Pomperaug | Home - New Canaan HS-Main Gym [Directions] | W 65-61 | ||
| Sat., 12/18 | V Boys Ice Hockey | Fairfield Prep | Away - Wonderland of Ice-Stadium [Directions] | W 4-1 | 2:00 PM; 1 Bus | |
| Sat., 12/18 | V Boys Indoor Track | Wilton, Wilton, Danbury, Norwalk | Away - Wilton HS [Directions] | 8:30 a.m. | 7:30 AM; 1 Bus | |
| Sat., 12/18 | V Wrestling | Pomperaug Quads | Away - Pomperaug HS-Auxiliary Gym | Pomperaug 45 New Canaan 30 New Canaan 47 Portland 30 New Canaan 66 Terryville/thomaston 18 New Canaan 64 Nonnewaug 12 New Canaan 54 Bacon Acad 27 | 7:00 AM; 1 Bus | |
| Sat., 12/18 | V Girls Ice Hockey | Stamford/Westhill/Staples | Home - Darien Ice House-Ice Rink [Directions] | W 8-1 | ||
| Sat., 12/18 | V Girls Indoor Track | Danbury, Norwalk, Wilton, Wilton | Home - Wilton HS-Wilton Field House [Directions] | 8:30 a.m. | ||
| Mon., 12/20 | V Boys Ice Hockey | Simsbury | Home - Darien Ice House-Ice Rink [Directions] | T 2-2 | ||
| Wed., 12/22 | V Boys Basketball | Wright Tech | Away - J M Wright Tech School-Thomas R. Good Gymnasium [Directions] | W 62-13 | 3:00 PM; 1 Bus (V & JV ride together) | |
| Wed., 12/22 | V Girls Basketball | Norwalk | Home - New Canaan HS-Main Gym [Directions] | L 31-45 | ||
| Wed., 12/22 | V Girls Ice Hockey | Simsbury | Home - Darien Ice House-Ice Rink [Directions] | W 3-1 | ||
| Thu., 12/23 | V Boys Ice Hockey | Notre Dame-West Haven | Home - Darien Ice House-Ice Rink [Directions] | W 4-3(OT) | ||
| Thu., 12/23 | V Wrestling | Greenwich, St. Joseph, Staples | Away - Greenwich HS-Gymnasium [Directions] | 3:00 p.m. | 1:00 PM; 1 Bus | |
| Tue., 12/28 | V Boys Basketball | Southington | Away - Shelton HS-Murray Gymnasium [Directions] | W 43-40 | ||
| Tue., 12/28 | V Girls Basketball | Kolbe Cathedral | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 33-28 | ||
| Wed., 12/29 | V Wrestling | Danbury, Bristol Eastern, Brookfield, Coventry (RI), Enfield, Abbott Tech, TBA, TBA, TBA, TBA, New Fairfield, New Milford, Norwalk, Staples, Wilton | Away - Danbury HS-Main Gym | Cancelled | 6:30 AM; 1 Bus | |
| Thu., 12/30 | V Boys Basketball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | W 45-40 | ||
| Thu., 12/30 | V Girls Basketball | Darien | Home - New Canaan HS-Main Gym [Directions] | W 29-19 | ||
| Tue., 1/4 | V Girls Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | L 34-40 | 3:20 PM; 1 Bus (V & JV ride together) | |
| Wed., 1/5 | V Boys Ice Hockey | Greenwich | Away - Greenwich - Dorothy Hamill-Rink [Directions] | W 7-1 | 3:30 PM; 1 Bus | |
| Wed., 1/5 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Home - New Canaan YMCA-Pool [Directions] | 3:00 p.m. | ||
| Wed., 1/5 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice-New [Directions] | W 8-0 | 2:45 PM; 1 Bus | |
| Thu., 1/6 | V Wrestling | Danbury | Away - Danbury HS-New gym [Directions] | Danbury 75 New Canaan 3 | 2:30 PM; 1 Bus | |
| Sat., 1/8 | V Boys Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | L 39-50 | 9:40 AM; 1 Bus (V & JV ride together) | |
| Sat., 1/8 | V Boys Ice Hockey | Ridgefield | Home - Darien Ice House-Ice Rink [Directions] | T 1-1 | ||
| Sat., 1/8 | V Boys Indoor Track | Qualifying Meet #2A | Away - Wilton HS-Wilton Field House | 8:30 a.m. | ||
| Sat., 1/8 | V Wrestling | East Islip (NY) | Away - East Islip HS-Gym | 4:00 p.m. | 11:30 AM; 1 Bus | |
| Sat., 1/8 | V Girls Basketball | Danbury | Home - New Canaan HS-Main Gym [Directions] | L 30-62 | ||
| Sat., 1/8 | V Girls Gymnastics | Darien, Wilton | Away - Darien YMCA [Directions] | 57.7 | 1:30 PM; 1 Van | |
| Sat., 1/8 | V Girls Ice Hockey | LaSalle Academy (RI) | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 5-1 | 11:00 AM; 1 Bus | |
| Sat., 1/8 | V Girls Indoor Track | Qualifying Meet #2A | Away - Wilton HS-Wilton Field House | 8:30 a.m. | ||
| Mon., 1/10 | V Girls Ice Hockey | Darien | Away - Darien Ice House-Ice Rink [Directions] | W 3-1 | 2:20 PM; 1 Bus | |
| Tue., 1/11 | V Boys Basketball | Staples | Home - New Canaan HS-Main Gym [Directions] | L 47-54 | ||
| Tue., 1/11 | V Girls Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | L 31-36 | 3:30 PM; 1 Bus (V & JV ride together) | |
| Tue., 1/11 | V Girls Gymnastics | Greenwich | Away - Greenwich YWCA [Directions] | 6:30 p.m. | 5:15 PM; 1 Van | |
| Wed., 1/12 | V Boys Ice Hockey | Darien | Home - Darien Ice House-Ice Rink [Directions] | L 1-2(OT) | ||
| Wed., 1/12 | V Boys Swimming and Diving | Westhill/Stamford | Away - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | 2:15 PM; 1 Bus | |
| Wed., 1/12 | V Wrestling | Ridgefield | Away - Ridgefield HS-Aux Gym [Directions] | Ridgefield 51 New Canaan 30 | 4:00 PM; 1 Bus | |
| Wed., 1/12 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | W 8-1 | 2:10 PM; 1 Bus | |
| Thu., 1/13 | V Boys Ice Hockey | St. Joseph | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | W 3-2 | 5:15 PM; 1 Bus | |
| Thu., 1/13 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Away - Hamden-Lou Astorino Ice Rink [Directions] | W 8-0 | 2:10 PM; 1 Bus | |
| Fri., 1/14 | V Boys Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | L 40-63 | 3:50 PM; 1 Bus (V & JV ride together) | |
| Fri., 1/14 | V Boys Swimming and Diving | St. Joseph, Trumbull | Home - New Canaan YMCA-Pool [Directions] | 3:00 p.m. | ||
| Fri., 1/14 | V Girls Basketball | Wilton | Home - New Canaan HS-Main Gym [Directions] | L 31-34 | ||
| Sat., 1/15 | V Boys Indoor Track | FCIAC, Norwalk, Ridgefield, Wilton | Away - Wilton HS-Wilton Field House | 8:30 a.m. | ||
| Sat., 1/15 | V Wrestling | Notre Dame-West Haven, Fitch, Stratford | Away - Notre Dame HS-Gym [Directions] | Stratford 48 New Canaan 32 New Canaan 48 Fitch 22 Notre Dame/WH 45 NC 31 | 1:00 PM; 1 Bus | |
| Sat., 1/15 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Darien Ice House-Ice Rink [Directions] | W 6-1 | ||
| Sat., 1/15 | V Girls Indoor Track | FCIAC, Norwalk, Ridgefield, Wilton | Away - Wilton HS-Wilton Field House | 8:30 a.m. | ||
| Mon., 1/17 | V Boys Ice Hockey | Barrington (RI) | Home - Darien Ice House-Ice Rink [Directions] | T 2-2(OT) | ||
| Mon., 1/17 | V Girls Gymnastics | Trumbull, Darien, St. Joseph | Away - Next Dimension Gymnastics-Next Dimension [Directions] | 52.3 | 12:00 PM; 1 Van | |
| Mon., 1/17 | V Girls Ice Hockey | Suffield Coop | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 5-0 | ||
| Tue., 1/18 | V Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | L 40-60 | 2:30 PM; 1 Bus (V & JV ride together) | |
| Tue., 1/18 | V Girls Basketball | St. Joseph | Home - New Canaan HS-Main Gym [Directions] | L 28-55 | ||
| Wed., 1/19 | V Boys Ice Hockey | Hamden | Away - Hamden-Lou Astorino Ice Rink [Directions] | W 5-1 | 5:30 PM; 1 Bus | |
| Wed., 1/19 | V Boys Swimming and Diving | Wilton | Home - New Canaan YMCA-Pool [Directions] | 3:00 p.m. | ||
| Wed., 1/19 | V Wrestling | Fairfield Ludlowe | Home - New Canaan HS-Main Gym [Directions] | NC 51 Ludlowe 24 | ||
| Thu., 1/20 | V Boys Basketball | Ridgefield | Home - New Canaan HS-Main Gym [Directions] | L 49-63 | ||
| Thu., 1/20 | V Girls Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | L 17-40 | 3:30 PM; 1 Bus (V & JV ride together) | |
| Thu., 1/20 | V Girls Gymnastics | Greenwich | Away - Greenwich YWCA [Directions] | 70.95 | 5:15 PM; 1 Van | |
| Thu., 1/20 | V Girls Ice Hockey | Greenwich | Away - Greenwich - Dorothy Hamill-Rink [Directions] | W 2-0 | 6:00 PM; 1 Bus | |
| Fri., 1/21 | V Boys Swimming and Diving | Darien | Home - New Canaan YMCA-Pool [Directions] | 3:00 p.m. | ||
| Sat., 1/22 | V Boys Ice Hockey | LaSalle Academy (RI) | Away - La Salle Academy | L 1-5 | ||
| Sat., 1/22 | V Boys Indoor Track | FCIAC, Norwalk, Stamford, Staples | Away - Staples HS-Field House | 10:00 a.m. | 8:30 AM; 1 Bus (B/G ride together) | |
| Sat., 1/22 | V Wrestling | 2022 Shoreline Scuffle Wrestling Tournament | Away - Branford HS-Gym | Cancelled | 7:00 AM; 1 Bus | |
| Sat., 1/22 | V Girls Ice Hockey | West Haven/SHA | Away - West Haven HS-Bennett Rink [Directions] | W 4-0 | 10:00 AM; 1 Bus | |
| Sat., 1/22 | V Girls Indoor Track | FCIAC, Norwalk, Stamford, Staples | Away - Staples HS-Field House | 10:00 a.m. | 8:30 AM; 1 Bus (B/G ride together) | |
| Mon., 1/24 | V Boys Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | L 50-63 | 3:00 PM; 1 Bus (V & JV ride together) | |
| Mon., 1/24 | V Boys Ice Hockey | Westhill/Stamford | Home - Darien Ice House-Ice Rink [Directions] | W 5-2 | ||
| Mon., 1/24 | V Girls Basketball | Stamford | Home - New Canaan HS-Main Gym [Directions] | L 26-56 | ||
| Mon., 1/24 | V Girls Gymnastics | Fairfield Warde | Away - Gymnastics and Cheerleading Academy at Connecticut [Directions] | 6:30 p.m. | 5:00 PM; 1 Van | |
| Wed., 1/26 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Home - New Canaan YMCA-Pool [Directions] | 3:00 p.m. | ||
| Wed., 1/26 | V Wrestling | Wilton | Home - New Canaan HS-Main Gym [Directions] | New Canaan 75 Wilton 0 | ||
| Fri., 1/28 | V Boys Basketball | Westhill | Home - New Canaan HS-Main Gym [Directions] | L 36-54 | ||
| Fri., 1/28 | V Boys Swimming and Diving | Greenwich | Away - Greenwich HS-Pool [Directions] | 4:30 p.m. | 2:30 PM; 1 Bus | |
| Fri., 1/28 | V Girls Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | L 34-40 | 4:15 PM; 1 Bus (V & JV ride together) | |
| Fri., 1/28 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | W 5-0 | 2:30 PM; 1 Bus | |
| Sat., 1/29 | V Wrestling | Brookfield, Bethel, Canton, Danbury, Darien, Joel Barlow, Montville, Newtown, Pomperaug, Stratford, Harding, Wilton | Away - Brookfield HS-BHS Small & Big Gym | Cancelled | ||
| Pending changes awaiting acceptance by one or more parties involved: Date to 1/30, Time to 11:00 a.m. | ||||||
| Sun., 1/30 | V Girls Ice Hockey | Guilford Coop | Home - Darien Ice House-Ice Rink [Directions] | W 6-2 | ||
| Mon., 1/31 | V Boys Ice Hockey | St. Joseph | Home - Darien Ice House-Ice Rink [Directions] | W 5-1 | ||
| Mon., 1/31 | V Wrestling | Norwalk | Home - New Canaan HS-Main Gym [Directions] | Norwalk 48 NC 34 | ||
| Tue., 2/1 | V Boys Basketball | Brien McMahon | Home - New Canaan HS-Main Gym [Directions] | W 50-41 | ||
| Tue., 2/1 | V Girls Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | W 38-20 | 2:40 PM; 1 Bus (V & JV ride together) | |
| Wed., 2/2 | V Boys Swimming and Diving | Danbury | Home - New Canaan YMCA-Pool [Directions] | 3:00 p.m. | ||
| Wed., 2/2 | V Girls Ice Hockey | Simsbury | Away - Simsbury Farms Ice Rink-Ice Rink [Directions] | T 1-1 | 1:30 PM; 1 Bus | |
| Thu., 2/3 | V Boys Indoor Track | FCIAC Indoor Track Championships | Away - Floyd Little Athletic Center-Field House | 4:30 p.m. | ||
| Thu., 2/3 | V Girls Basketball | Bridgeport Central | Home - New Canaan HS-Main Gym [Directions] | W 60-25 | ||
| Thu., 2/3 | V Girls Gymnastics | Staples | Away - Westport YMCA [Directions] | 88.3 | 5:00 PM; 1 Van | |
| Thu., 2/3 | V Girls Gymnastics | Norwalk | Away - Westport YMCA [Directions] | TBA | ||
| Thu., 2/3 | V Girls Indoor Track | FCIAC Indoor Track Championships | Away - Floyd Little Athletic Center-Field House | 4:30 p.m. | 2:30 PM; 1 Bus (B/G riding together) | |
| Sat., 2/5 | V Boys Ice Hockey | Xavier | Away - Champions Skating Rink - Cromwell-Upper Rink [Directions] | L 1-4 | 5:15 PM; 1 Bus | |
| Sat., 2/5 | V Girls Basketball | Weston | Away - Weston HS-Gym (New) [Directions] | W 32-28 | 11:15 AM; 1 Bus (V & JV ride together) | |
| Sat., 2/5 | V Competitive Cheerleading | FCIAC Cheer Championships | Away - Not Listed-Trumbull | 11:00 a.m. | 8:40 AM; 1 Bus | |
| Sat., 2/5 | V Girls Ice Hockey | Avon | Home - Darien Ice House-Ice Rink [Directions] | W 5-2 | ||
| Mon., 2/7 | V Boys Basketball | Bridgeport Central | Away - Bridgeport Central HS-Barry McLeod Court [Directions] | W 59-40 | 3:30 PM; 1 Bus (V & JV ride together) | |
| Mon., 2/7 | V Boys Ice Hockey | Greenwich | Home - Darien Ice House-Ice Rink [Directions] | W 4-1 | ||
| Mon., 2/7 | V Girls Basketball | Harding | Home - New Canaan HS-Main Gym [Directions] | W 45-23 | ||
| Tue., 2/8 | V Boys Basketball | Fairfield Warde | Home - New Canaan HS-Main Gym [Directions] | L 43-57 | ||
| Tue., 2/8 | V Boys Swimming and Diving | Ridgefield | Away - Barlow Mountain Pool [Directions] | 4:00 p.m. | 2:10 PM; 1 Bus | |
| Tue., 2/8 | V Girls Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | L 34-46 | 2:45 PM; 1 Bus (V & JV ride together) | |
| Wed., 2/9 | V Boys Ice Hockey | Ridgefield | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | W 3-1 | 6:30 PM; 1 Bus | |
| Wed., 2/9 | V Wrestling | Stamford | Home - New Canaan HS-Main Gym [Directions] | New Canaan 71 Stamford 12 | ||
| Thu., 2/10 | V Boys Basketball | Darien | Home - New Canaan HS-Main Gym [Directions] | W 60-47 | ||
| Fri., 2/11 | V Wrestling | FCIAC, Danbury, Darien, Fairfield Ludlowe, Fairfield Warde, Greenwich, TBA, Norwalk, Ridgefield, St. Joseph, Stamford, Staples, Trumbull, Westhill, Wilton | Away - New Canaan HS-Main Gym | 4:30 p.m. | ||
| Fri., 2/11 | V Girls Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | L 27-29 | 4:30 PM; 1 Bus (V & JV travel together) | |
| Sat., 2/12 | V Boys Ice Hockey | Darien | Away - Darien Ice House-Ice Rink [Directions] | L 2-3 | ||
| Sat., 2/12 | V Boys Indoor Track | Class L Championship | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Sat., 2/12 | V Wrestling | FCIAC Wrestling Championships Wrestlebacks | Away - New Canaan HS-Main Gym | 10:00 a.m. | ||
| Sat., 2/12 | V Girls Gymnastics | FCIAC Gymnastics Championships | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 | 11:00 a.m. | ||
| Sat., 2/12 | V Girls Ice Hockey | Darien | Home - Darien Ice House-Ice Rink [Directions] | W 5-0 | ||
| Sat., 2/12 | V Girls Indoor Track | Class L Championship | Away - Floyd Little Athletic Center | 10:00 a.m. | 7:30 AM; 1 Bus (B/G ride together) | |
| Mon., 2/14 | V Boys Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | L 36-47 | 3:30 PM; 1 Bus (V & JV Travel together) | |
| Mon., 2/14 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Home - Darien Ice House-Ice Rink [Directions] | W 4-1 | ||
| Mon., 2/14 | V Boys Swimming and Diving | Staples | Away - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | 2:15 PM; 1 Bus | |
| Mon., 2/14 | V Girls Basketball | Trumbull | Home - New Canaan HS-Main Gym [Directions] | L 49-58 | ||
| Wed., 2/16 | V Boys Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | W 44-40 | 3:00 PM; 1 Bus (V & JV ride together) | |
| Wed., 2/16 | V Girls Basketball | Fairfield Ludlowe | Home - New Canaan HS-Main Gym [Directions] | L 39-63 | ||
| Fri., 2/18 | V Boys Basketball | Harding | Away - Warren Harding HS-Gym [Directions] | W 55-18 | 3:45 PM; 1 Bus | |
| Fri., 2/18 | V Wrestling | Class L Championship - Day 1 | Away - Wilton | 3:00 p.m. | ||
| Sat., 2/19 | V Boys Ice Hockey | Notre Dame-Fairfield | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | W 4-2 | 5:20 PM; 1 Bus | |
| Sat., 2/19 | V Boys Indoor Track | State Open | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/19 | V Wrestling | Class L Championship - Day 2 | Away - Wilton | 9:00 a.m. | ||
| Sat., 2/19 | V Girls Ice Hockey | East Catholic Coop | Away - Newington Ice Arena-Blue Rink [Directions] | W 4-0 | 9:00 AM; 1 Bus | |
| Sat., 2/19 | V Girls Indoor Track | State Open | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Mon., 2/21 | V Boys Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | L 33-43 | 3:30 PM; 1 Bus (V & JV ride together) | |
| Mon., 2/21 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland of Ice-Stadium [Directions] | L 2-4 | 6:40 PM; 1 Bus | |
| Wed., 2/23 | V Boys Basketball | Greenwich | Home - New Canaan HS-Main Gym [Directions] | L 41-63 | ||
| Wed., 2/23 | V Girls Ice Hockey | Greenwich | Home - Darien Ice House-Ice Rink [Directions] | W 2-0 | ||
| Sat., 2/26 | V Boys Ice Hockey | St. Joseph | Home - Darien Ice House-Ice Rink [Directions] | 5:00 p.m. | ||
| Sat., 2/26 | V Wrestling | State Open - Day 1 | Away - Floyd Little Athletic Center | 12:45 p.m. | ||
| Sat., 2/26 | V Girls Ice Hockey | Stamford/Westhill/Staples | Home - Darien Ice House-Ice Rink [Directions] | W 5-1 | ||
| Sun., 2/27 | V Wrestling | State Open - Day 2 | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Mon., 2/28 | V Girls Basketball | West Haven | Away - West Haven HS-Gym [Directions] | 6:30 p.m. | 4:00 PM; 1 Bus | |
| Tue., 3/1 | V Boys Swimming and Diving | FCIAC Boys' Swim Trials | Away - Greenwich HS | 5:30 p.m. | 3:40 PM; 1 Bus | |
| Wed., 3/2 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland of Ice-Stadium [Directions] | 7:30 p.m. | 5:45 PM; 1 Bus | |
| Wed., 3/2 | V Boys Swimming and Diving | FCIAC Diving Finals | Away - Westhill High-Westhill HS | 5:00 p.m. | ||
| Thu., 3/3 | V Boys Swimming and Diving | FCIAC Boys' Swim Finals | Away - Greenwich HS | 6:30 p.m. | 4:00 PM; 1 Bus | |
| Thu., 3/3 | V Girls Ice Hockey | Guilford Coop | Home - Darien Ice House-Ice Rink [Directions] | 5:30 p.m. | ||
| Sat., 3/5 | V Girls Gymnastics | State Open | Away - New Milford | 10:00 a.m. | ||
| Sat., 3/5 | V Girls Ice Hockey | East Catholic Coop | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 6:00 p.m. | ||
| Tue., 3/8 | V Boys Basketball | Hillhouse | Away - Hillhouse HS-Gym [Directions] | 6:30 p.m. | 3:45 PM; 1 Bus | |
| Tue., 3/8 | V Boys Ice Hockey | St. Joseph | Home - Darien Ice House-Ice Rink [Directions] | 7:00 p.m. | ||
| Wed., 3/9 | V Girls Ice Hockey | Darien | Home - Darien Ice House-Ice Rink [Directions] | 5:30 p.m. | 3:45 PM; 1 Bus | |
| Thu., 3/10 | V Boys Swimming and Diving | CIAC Class L Diving Championships | Away - Sheehan | 6:30 p.m. | ||
| Fri., 3/11 | V Boys Swimming and Diving | CIAC Class L Qualifying Meet | Away - Cornerstone Pool | 6:30 p.m. | ||
| Sat., 3/12 | V Boys Ice Hockey | Fairfield Prep | Home - West Haven HS-Bennett Rink [Directions] | 1:00 p.m. | ||
| Tue., 3/15 | V Boys Swimming and Diving | CIAC Class L Swimming Championships | Away - Cornerstone Pool | 1:30 p.m. | ||
| Wed., 3/16 | V Boys Ice Hockey | Notre Dame-West Haven | Away - Terry Conners - Stamford-Ice Rink [Directions] | 6:30 p.m. | 5:15 PM; 1 Bus | |
| Thu., 3/17 | V Boys Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/19 | V Boys Swimming and Diving | CIAC State Open Swimming Championships | Away - Cornerstone Pool | 3:15 p.m. | ||
| Thu., 3/24 | V Softball | St. Lukes (Scrim.) | Away - St Lukes School-upper field #1 | Cancelled | 3:00 PM; 1 Bus | |
| Fri., 3/25 | V Girls Lacrosse | Yorktown (NY) (Scrim.) | Home - New Canaan HS-Dunning Stadium [Directions] | 4:30 p.m. | ||
| Sat., 3/26 | V Baseball | Stamford (Scrim.) | Away - Stamford HS-SHS Baseball Diamond [Directions] | 11:00 a.m. | 9:45 AM; 1 Bus | |
| Sat., 3/26 | V Boys Lacrosse | Niskayuna (NY) (Scrim.) | Away - Union College-Bailey Field-Bailey Field | 3:45 p.m. | 11:30 AM; 1 Bus | Location: Union College - Frank Bailey Field - Alexander Lane, Schenectady, NY 12308 |
| Sat., 3/26 | V Girls Lacrosse | Staples, Bishop Guertin (NH), Fairfield Ludlowe, Greenwich Academy, Greenwich, Guilford, TBA, Sacred Heart of Greenwich, St. Joseph, Weston | Away - Staples HS-Staples Stadium | 9:00 a.m. | ||
| Mon., 3/28 | V Baseball | Newtown (Scrim.) | Away - Newtown HS-Nighthawk Ball Park [Directions] | Cancelled | 2:15 PM; 1 Bus | |
| Tue., 3/29 | V Baseball | Greenwich (Scrim.) | Away - Greenwich HS-Baseball Field [Directions] | 4:30 p.m. | 2:30 PM; 1 Bus | |
| Wed., 3/30 | V Boys Volleyball | Masuk (Scrim.) | Home - New Canaan HS-Main Gym [Directions] | 5:15 p.m. | ||
| Thu., 3/31 | V Baseball | Brunswick School (Scrim.) | Away - Brunswick School-Stadium | 4:00 p.m. | 2:15 PM; 1 Bus | |
| Thu., 3/31 | V Boys Lacrosse | Greenwich (Scrim.) | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:30 p.m. | 2:15 PM; 1 Bus | |
| Thu., 3/31 | V Boys Volleyball | Joel Barlow, Fairfield Warde, Greenwich, Newington, Newtown, Simsbury, Staples | Away - Joel Barlow HS-Lower Gym | 3:30 p.m. | 2:10 PM; 1 Bus | |
| Thu., 3/31 | V Girls Lacrosse | Greenwich Academy (Scrim.) | Home - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | ||
| Fri., 4/1 | V Softball | Joel Barlow (Scrim.) | Home - Waveny Park-Orchard Field [Directions] | 4:00 p.m. | ||
| Sat., 4/2 | V Baseball | Lyman Hall | Home - Mead Park-Baseball Field [Directions] | W 8-4 | ||
| Sat., 4/2 | V Boys Lacrosse | Mamaroneck (NY) | Home - New Canaan HS-Dunning Stadium [Directions] | W 12-3 | ||
| Sat., 4/2 | V Boys Tennis | Weston (Scrim.) | Home - New Canaan HS-NCHS Tennis Courts [Directions] | 1:00 p.m. | ||
| Sat., 4/2 | V Boys Volleyball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | L 0-3 | 9:15 AM; 1 Bus | |
| Sat., 4/2 | V Girls Lacrosse | Stamford | Home - New Canaan HS-Dunning Stadium [Directions] | W 18-4 | ||
| Sat., 4/2 | V Softball | Jonathan Law | Away - Jonathan Law HS-Softball Field [Directions] | L 4-2 | 10:15 AM; 1 Bus | |
| Mon., 4/4 | V Baseball | Weston | Home - Mead Park-Baseball Field [Directions] | W 14-5 | ||
| Mon., 4/4 | V Boys Outdoor Track | Wilton | Home - New Canaan HS-NCHS Track [Directions] | 4:00 p.m. | ||
| Mon., 4/4 | V Girls Outdoor Track | Wilton | Home - New Canaan HS-NCHS Track [Directions] | 4:00 p.m. | ||
| Tue., 4/5 | V Baseball | Abbott Tech | Away - Abbott V-T School-Abbott Tech Baseball Field, School Campus [Directions] | W 21-5 | 2:10 PM; 1 Bus | |
| Tue., 4/5 | V Boys Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | L 6-7 | 4:00 PM; 1 Bus | |
| Tue., 4/5 | V Boys Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | W 3-0 | 2:30 PM; 1 Bus (JV & V will ride together.) | |
| Tue., 4/5 | V Girls Lacrosse | Fairfield Ludlowe | Home - New Canaan HS-Dunning Stadium [Directions] | W 16-6 | ||
| Fri., 4/8 | V Girls Lacrosse | Bronxville (NY) | Away - Bronxville HS-N:Turf | W 12-11 | 2:10 PM; 1 Bus | |
| Fri., 4/8 | V Softball | Stamford | Home - Waveny Park-Orchard Field [Directions] | W 10-8 | ||
| Sat., 4/9 | V Boys Lacrosse | Glastonbury | Away - Glastonbury HS-Field 1 [Directions] | W 7-1 | 3:00 PM; 1 Bus | |
| Mon., 4/11 | V Boys Tennis | Danbury | Away - Danbury HS-DHS Tennis Courts [Directions] | W 7-0 [Detailed Results] | 2:15 PM; 1 Bus | |
| Mon., 4/11 | V Girls Lacrosse | Victor (NY) | Home - New Canaan HS-Dunning Stadium [Directions] | L 7-8 | ||
| Mon., 4/11 | V Girls Tennis | Danbury | Home - New Canaan HS-NCHS Tennis Courts [Directions] | W 7-0 | ||
| Tue., 4/12 | V Baseball | Greenwich | Home - Mead Park-Baseball Field [Directions] | L 2-4 | ||
| Tue., 4/12 | V Boys Lacrosse | Radnor (PA) | Home - New Canaan HS-Dunning Stadium [Directions] | L 8-9 | ||
| Tue., 4/12 | V Boys Tennis | Staples | Home - New Canaan HS-NCHS Tennis Courts [Directions] | L 1-6 [Detailed Results] | ||
| Tue., 4/12 | V Softball | New Milford | Away - New Milford HS-Softball Varsity Field - NMHS [Directions] | W 2-1 | 2:10 PM; 1 Bus | |
| Tue., 4/12 | V Girls Tennis | Staples | Away - Staples HS-Staples Tennis Courts [Directions] | L 7-0 | 2:15 PM; 1 Bus | |
| Wed., 4/13 | V Girls Lacrosse | Wilton | Away - Wilton HS-Lilly Field [Directions] | W 14-6 | 4:15 PM; 1 Bus | |
| Thu., 4/14 | V Baseball | Danbury | Home - Mead Park-Baseball Field [Directions] | L 3-6 | ||
| Thu., 4/14 | V Boys Lacrosse | Bronxville (NY) | Home - New Canaan HS-Dunning Stadium [Directions] | W 9-8 | ||
| Thu., 4/14 | V Boys Tennis | Wilton | Away - Wilton HS-Tennis Courts [Directions] | L 0-7 [Detailed Results] | 2:30 PM; 1 Bus | |
| Thu., 4/14 | V Softball | Danbury | Away - Danbury HS-V Softball field [Directions] | L 1-0 | 2:15 PM; 1 Bus (JV & V will ride together) | |
| Sat., 4/16 | V Boys Lacrosse | Darien | Home - New Canaan HS-Dunning Stadium [Directions] | W 11-10 | ||
| Sat., 4/16 | V Boys Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | L 1-3 | 8:45 AM; 1 Bus (JV & V will ride together.) | |
| Sat., 4/16 | V Girls Lacrosse | Longmeadow (MA) | Away - Longmeadow HS-Front Field | W 16-4 | 7:15 AM; 1 Bus | |
| Mon., 4/18 | V Baseball | Staples | Away - Staples HS-Baseball Diamond [Directions] | L 3-7 | 2:30 PM; 1 Bus (JV & V will ride together.) | |
| Mon., 4/18 | V Boys Outdoor Track | Ridgefield | Home - New Canaan HS-NCHS Track [Directions] | 4:00 p.m. | ||
| Mon., 4/18 | V Boys Tennis | St. Joseph | Away - St. Joseph HS-Tennis Courts [Directions] | W 7-0 [Detailed Results] | 2:10 PM; 1 Bus | |
| Mon., 4/18 | V Boys Volleyball | Darien | Home - New Canaan HS-Main Gym [Directions] | L 0-3 | ||
| Mon., 4/18 | V Girls Outdoor Track | Ridgefield | Home - New Canaan HS-NCHS Track [Directions] | 4:00 p.m. | ||
| Mon., 4/18 | V Softball | Staples | Home - Waveny Park-Orchard Field [Directions] | W 5-4 | ||
| Mon., 4/18 | V Girls Tennis | St. Joseph | Home - New Canaan HS-NCHS Tennis Courts [Directions] | W 7-0 | ||
| Tue., 4/19 | V Boys Tennis | Ridgefield | Home - New Canaan HS-NCHS Tennis Courts [Directions] | L 1-6 [Detailed Results] | ||
| Tue., 4/19 | V Girls Golf | Darien | Away - Country Club of Darien [Directions] | NC-189 Darien-246 | 2:10 PM; 1 Van | |
| Tue., 4/19 | V Girls Lacrosse | Darien | Away - Darien HS-DHS Stadium Field [Directions] | L 11-15 | 2:30 PM; 1 Bus | |
| Tue., 4/19 | V Girls Tennis | Ridgefield | Away - Ridgefield HS-RHS Tennis Courts [Directions] | W 6-1 | 2:15 PM; 1 Bus | |
| Wed., 4/20 | V Baseball | Wilton | Home - Mead Park-Baseball Field [Directions] | W 11-1 | ||
| Wed., 4/20 | V Boys Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | W 3-1 | 2:15 PM; 1 Bus (JV & V will ride together.) | |
| Wed., 4/20 | V Girls Golf | Ridgefield | Away - Ridgefield Golf Course [Directions] | NC-183 Ridgefield-237 | 1:00 PM, Dismiss TBA; 2 Vans | |
| Wed., 4/20 | V Softball | Wilton | Away - Wilton HS-Varsity Softball Field [Directions] | W 3-0 | 2:30 PM; 1 Bus (JV & V will ride together) | |
| Thu., 4/21 | V Boys Lacrosse | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | W 18-3 | 2:20 PM; 1 Bus | |
| Thu., 4/21 | V Boys Tennis | Stamford | Away - Stamford HS-SHS Tennis Courts [Directions] | W 4-3 [Detailed Results] | 2:30 PM; 1 Bus | |
| Thu., 4/21 | V Boys Volleyball | Fairfield Warde | Home - New Canaan HS-Main Gym [Directions] | W 3-0 | ||
| Thu., 4/21 | V Girls Lacrosse | Eastport-South Manor (NY) | Home - New Canaan HS-Dunning Stadium [Directions] | W 12-8 | ||
| Thu., 4/21 | V Girls Tennis | Stamford | Home - New Canaan HS-NCHS Tennis Courts [Directions] | W 7-0 | ||
| Fri., 4/22 | V Baseball | St. Joseph | Home - Mead Park-Baseball Field [Directions] | W 9-3 | ||
| Fri., 4/22 | V Softball | St. Joseph | Away - St. Joseph HS-Softball Diamond [Directions] | L 0-4 | 2:15 PM; 1 Bus (JV & V ride together.) | |
| Sat., 4/23 | V Baseball | New Fairfield | Away - New Fairfield HS-Baseball Field [Directions] | L 0-7 | 2:10 PM; 1 Bus | |
| Sat., 4/23 | V Boys Lacrosse | Rumson-Fair Haven (NJ) | Away - Rumson-Fair Haven HS-Stadium | W 10-5 | 9:00 AM; 1 Bus | |
| Sat., 4/23 | V Girls Lacrosse | Northport (NY) | Away - Northport HS-Baseball Diamond | W 12-8 | ||
| Mon., 4/25 | V Baseball | Ridgefield | Away - Governor Field [Directions] | L 1-5 | 2:15 PM; 1 Bus (Jv & V will ride together.) | |
| Mon., 4/25 | V Boys Outdoor Track | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | 2:15 PM; 1 Bus | |
| Mon., 4/25 | V Boys Tennis | Greenwich | Home - New Canaan HS-NCHS Tennis Courts [Directions] | L 6-1 [Detailed Results] | ||
| Mon., 4/25 | V Boys Volleyball | Westhill | Home - New Canaan HS-Main Gym [Directions] | W 3-0 | ||
| Mon., 4/25 | V Girls Outdoor Track | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | 2:15 PM; 1 Bus | |
| Mon., 4/25 | V Softball | Ridgefield | Home - Waveny Park-Orchard Field [Directions] | L 1-3 | ||
| Mon., 4/25 | V Girls Tennis | Greenwich | Away - Greenwich HS-Tennis Courts [Directions] | W 5-2 | 2:30 PM; 1 Bus | |
| Tue., 4/26 | V Boys Lacrosse | Fairfield Prep | Away - Fairfield University-Rafferty Stadium [Directions] | L 5-6 | 3:00 PM; 1 Bus | |
| Tue., 4/26 | V Girls Golf | Danbury | Home - Sterling Farms Golf Course [Directions] | NC-190 Danbur272 | ||
| Wed., 4/27 | V Baseball | Stamford | Home - Mead Park-Baseball Field [Directions] | L 5-8 | ||
| Wed., 4/27 | V Boys Tennis | Brien McMahon | Home - New Canaan HS-NCHS Tennis Courts [Directions] | W 5-2 [Detailed Results] | ||
| Wed., 4/27 | V Boys Volleyball | Bridgeport Central | Away - Bridgeport Central HS-The Barry McLeod Court [Directions] | W 3-0 | 2:15 PM; 1 Bus (JV & V ride together) | |
| Wed., 4/27 | V Softball | Stamford | Away - Stamford HS-SHS Baseball Diamond [Directions] | L 4-2 | 2:30 PM; 1 Bus (JV & V will ride together.) | |
| Wed., 4/27 | V Girls Tennis | Wilton | Away - Wilton HS-Tennis Courts [Directions] | W 4-3 | ||
| Thu., 4/28 | V Baseball | Greenwich | Away - Greenwich HS-Baseball Field [Directions] | W 2-0 | 2:30 PM; 1 Bus (JV & V will ride together) | |
| Thu., 4/28 | V Boys Lacrosse | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | W 12-2 | 3:15 PM; 1 Bus | |
| Thu., 4/28 | V Boys Tennis | Bridgeport Central | Away - Bridgeport Central HS-Central High School Tennis Courts [Directions] | W 7-0 | 2:15 PM; 1 Bus | |
| Thu., 4/28 | V Boys Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | L 0-3 | 2:45 PM; 1 Bus (JV & V will ride together) | |
| Thu., 4/28 | V Girls Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | NC-180 Trumbull-194 | 2:05 AM; 2 Vans | |
| Thu., 4/28 | V Girls Lacrosse | Brien McMahon | Home - New Canaan HS-Dunning Stadium [Directions] | W 17-1 | ||
| Thu., 4/28 | V Softball | Greenwich | Home - Waveny Park-Orchard Field [Directions] | W 11-0 | ||
| Thu., 4/28 | V Girls Tennis | Bridgeport Central | Home - New Canaan HS-NCHS Tennis Courts [Directions] | W 7-0 | ||
| Sat., 4/30 | V Boys Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | L 5-13 | 4:30 PM; 1 Bus | |
| Sat., 4/30 | V Girls Lacrosse | New Fairfield | Home - New Canaan HS-Dunning Stadium [Directions] | W 14-2 | ||
| Sat., 4/30 | V Softball | Brookfield | Home - Waveny Park-Orchard Field [Directions] | L 0-1 | ||
| Mon., 5/2 | V Baseball | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | W 12-1 | 2:30 PM; 1 Bus (JV & V ride together) | |
| Mon., 5/2 | V Boys Volleyball | Stamford | Home - New Canaan HS-Main Gym [Directions] | W 3-0 | ||
| Mon., 5/2 | V Girls Golf | Fairfield Warde | Away - Smith Richardson Golf Course [Directions] | NC-177 F.Warde-227 | 2:05 PM; 1 Van | |
| Tue., 5/3 | V Baseball | Bridgeport Central | Home - Mead Park-Baseball Field [Directions] | W 22-4 | ||
| Tue., 5/3 | V Boys Lacrosse | St. Joseph | Home - New Canaan HS-Dunning Stadium [Directions] | W 15-5 | ||
| Tue., 5/3 | V Boys Outdoor Track | Stamford | Home - New Canaan HS-NCHS Track [Directions] | 4:00 p.m. | ||
| Tue., 5/3 | V Boys Tennis | Darien | Home - New Canaan HS-NCHS Tennis Courts [Directions] | L 2-5 [Detailed Results] | ||
| Tue., 5/3 | V Girls Golf | Wilton | Home - CCNC [Directions] | NC-160 Wilton-188 | ||
| Tue., 5/3 | V Girls Lacrosse | Ridgefield | Home - New Canaan HS-Dunning Stadium [Directions] | W 16-6 | ||
| Tue., 5/3 | V Girls Outdoor Track | Stamford | Home - New Canaan HS-NCHS Track [Directions] | 4:00 p.m. | ||
| Tue., 5/3 | V Softball | Brien McMahon | Home - Waveny Park-Orchard Field [Directions] | W 7-3 | ||
| Tue., 5/3 | V Softball | Brien McMahon (Scrim.) | Home - Waveny Park-Orchard Field [Directions] | 5:00 p.m. | ||
| Tue., 5/3 | V Girls Tennis | Darien | Away - Darien HS-DHS Tennis Courts [Directions] | L 5-2 | 2:40 PM; 1 Bus | |
| Wed., 5/4 | V Boys Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | W 3-2 | 2:15 PM; 1 Bus | |
| Wed., 5/4 | V Girls Golf | Greenwich | Home - CCNC [Directions] | NC-183 Greenwich-192 | ||
| Wed., 5/4 | V Girls Tennis | Brien McMahon | Away - Brien McMahon HS-Tennis Courts [Directions] | W 7-0 | 2:30 PM; 1 Bus | |
| Thu., 5/5 | V Boys Tennis | Trumbull | Away - Trumbull HS-Tennis Courts [Directions] | L 3-4 [Detailed Results] | 2:15 PM; 1 Bus | |
| Thu., 5/5 | V Girls Lacrosse | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | W 16-4 | 2:10 PM; 1 Bus | |
| Thu., 5/5 | V Softball | Bridgeport Central | Away - Bridgeport Central HS-Varsity Softball Field [Directions] | W 17-0 | 2:15 PM; 1 Bus | |
| Thu., 5/5 | V Girls Tennis | Trumbull | Home - New Canaan HS-NCHS Tennis Courts [Directions] | W 7-0 | ||
| Fri., 5/6 | V Boys Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | W 3-0 | 2:15 PM; 1 Bus | |
| Sat., 5/7 | V Boys Lacrosse | Wilton | Home - New Canaan HS-Dunning Stadium [Directions] | L 4-6 | ||
| Mon., 5/9 | V Baseball | Darien | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | W 12-4 | 2:40 PM; 1 Bus (JV & V ride together) | |
| Mon., 5/9 | V Boys Outdoor Track | Westhill | Home - New Canaan HS-NCHS Track [Directions] | 4:00 p.m. | ||
| Mon., 5/9 | V Boys Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Tennis Courts [Directions] | W 6-1 [Detailed Results] | 2:15 PM; 1 Bus | |
| Mon., 5/9 | V Boys Volleyball | St. Joseph | Home - New Canaan HS-Main Gym [Directions] | W 3-0 | ||
| Mon., 5/9 | V Girls Golf | Staples | Away - Staples HS-Longshore Golf Course [Directions] | NC-188 Staples-191 | 2:05 PM; 1 Van | |
| Mon., 5/9 | V Girls Outdoor Track | Westhill | Home - New Canaan HS-NCHS Track [Directions] | 4:00 p.m. | ||
| Mon., 5/9 | V Softball | Darien | Home - Waveny Park-Orchard Field [Directions] | W 2-0 | ||
| Mon., 5/9 | V Girls Tennis | Fairfield Ludlowe | Home - New Canaan HS-NCHS Tennis Courts [Directions] | W 4-3 | ||
| Tue., 5/10 | V Baseball | Fairfield Warde | Away - Fairfield Warde HS-Baseball Diamond [Directions] | L 0-9 | 2:15 PM; 1 Bus | |
| Tue., 5/10 | V Boys Tennis | Norwalk | Away - Norwalk HS-Tennis Courts [Directions] | W 6-1 [Detailed Results] | 2:15 PM; 1 Bus | |
| Tue., 5/10 | V Girls Golf | Ridgefield | Home - CCNC [Directions] | NC-180 Ridgefield-232 | 2:00 PM; 1 Van | |
| Tue., 5/10 | V Girls Lacrosse | Staples | Home - New Canaan HS-Dunning Stadium [Directions] | W 13-3 | ||
| Tue., 5/10 | V Softball | Fairfield Warde | Home - Waveny Park-Orchard Field [Directions] | L 2-6 | ||
| Tue., 5/10 | V Girls Tennis | Norwalk | Home - New Canaan HS-NCHS Tennis Courts [Directions] | W 6-0 | ||
| Wed., 5/11 | V Baseball | Trumbull | Home - Mead Park-Baseball Field [Directions] | W 3-2 | ||
| Wed., 5/11 | V Boys Tennis | Fairfield Warde | Home - New Canaan HS-NCHS Tennis Courts [Directions] | W 4-3 [Detailed Results] | ||
| Wed., 5/11 | V Boys Volleyball | Trumbull | Home - New Canaan HS-Main Gym [Directions] | L 0-3 | ||
| Wed., 5/11 | V Girls Golf | Darien | Home - CCNC [Directions] | NC-175 Darien-239 | ||
| Wed., 5/11 | V Girls Lacrosse | Norwalk | Away - Norwalk HS-Testa Field [Directions] | W 16-2 | 4:00 PM; 1 Bus | |
| Wed., 5/11 | V Softball | Trumbull | Away - Trumbull HS-Varsity Softball Diamond [Directions] | L 14-2 | 2:15 PM; 1 Bus (JV & V will ride together) | |
| Wed., 5/11 | V Girls Tennis | Fairfield Warde | Away - Fairfield Warde HS-Blake Courts [Directions] | W 7-0 | 2:15 PM; 1 Bus | |
| Thu., 5/12 | V Boys Lacrosse | Norwalk | Home - New Canaan HS-Dunning Stadium [Directions] | W 17-1 | ||
| Thu., 5/12 | V Boys Outdoor Track | Fairfield Ludlowe | Home - New Canaan HS-NCHS Track [Directions] | 4:00 p.m. | 12:00 PM | |
| Thu., 5/12 | V Boys Tennis | Westhill | Home - New Canaan HS-NCHS Tennis Courts [Directions] | L 2-5 [Detailed Results] | ||
| Thu., 5/12 | V Boys Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | W 3-1 | 2:15 PM; 1 Bus | |
| Thu., 5/12 | V Girls Outdoor Track | Fairfield Ludlowe | Home - New Canaan HS-NCHS Track [Directions] | 4:00 p.m. | 12:00 PM | |
| Thu., 5/12 | V Girls Tennis | Westhill | Away - Westhill HS-Westhill Tennis Courts [Directions] | L 4-3 | 2:30 PM; 1 Bus | |
| Sat., 5/14 | V Baseball | Fairfield Ludlowe | Home - Mead Park-Baseball Field [Directions] | W 10-9 | ||
| Sat., 5/14 | V Boys Lacrosse | Staples | Away - Staples HS-Staples Stadium [Directions] | L 3-11 | 1:00 PM; 1 Bus | |
| Sat., 5/14 | V Softball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | L 0-2 | 2:10 PM; 1 Bus (JV & V ride together) | |
| Mon., 5/16 | V Boys Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | W 3-0 | 2:15 PM; 1 Bus (JV & V ride together) | |
| Mon., 5/16 | V Girls Golf | Wilton | Away - Silvermine Golf Club [Directions] | NC-156 Wilton-174 | 2:10 PM; 2 Vans | |
| Tue., 5/17 | V Baseball | Norwalk | Home - Mead Park-Baseball Field [Directions] | L 3-10 | ||
| Tue., 5/17 | V Boys Lacrosse | Fairfield Warde | Home - New Canaan HS-Dunning Stadium [Directions] | W 18-5 | ||
| Tue., 5/17 | V Boys Outdoor Track | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Tue., 5/17 | V Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | W 16-2 | 2:15 PM; 1 Bus | |
| Tue., 5/17 | V Girls Outdoor Track | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Tue., 5/17 | V Softball | Norwalk | Away - Norwalk HS-Ray Barry Field [Directions] | L 2-1 | 2:15 PM; 1 Bus | |
| Tue., 5/17 | V Girls Tennis | Fairfield Ludlowe | Home - New Canaan HS-NCHS Tennis Courts [Directions] | W 4-3 | ||
| Wed., 5/18 | V Baseball | Westhill | Away - Westhill HS-Varsity Baseball Field [Directions] | W 20-5 | 2:30 PM; 1 Bus | |
| Wed., 5/18 | V Boys Tennis | Greenwich | Away - Greenwich HS-Tennis Courts [Directions] | L 2-5 | ||
| Wed., 5/18 | V Boys Volleyball | Norwalk | Home - New Canaan HS-Main Gym [Directions] | W 3-0 | ||
| Wed., 5/18 | V Softball | Westhill | Home - Waveny Park-Orchard Field [Directions] | L 4-7 | ||
| Thu., 5/19 | V Girls Golf | St. Joseph | Away - Tashua Knolls Golf Course [Directions] | NC-177 St. Joseph's-215 | ||
| Thu., 5/19 | V Girls Lacrosse | Staples | Home - New Canaan HS-Dunning Stadium [Directions] | 7:00 p.m. | ||
| Thu., 5/19 | V Softball | Pomperaug | Away - Community House Park-Softball Field [Directions] | W 9-5 | 8:30 AM; 1 Bus | |
| Thu., 5/19 | V Girls Tennis | Darien | Away - Darien HS-DHS Tennis Courts [Directions] | L 7-0 [Detailed Results] | ||
| Sat., 5/21 | V Baseball | Trumbull | Away - Trumbull HS-Varsity Baseball Field [Directions] | 1:00 p.m. | ||
| Sat., 5/21 | V Boys Lacrosse | Wilton | Away - Wilton HS-Veterans Memorial Stadium [Directions] | 7:00 p.m. | 5:00 PM; 2 Buses | |
| Sat., 5/21 | V Boys Volleyball | Westhill | Home - New Canaan HS-Main Gym [Directions] | 12:00 p.m. | ||
| Mon., 5/23 | V Girls Golf | Trumbull | Home - CCNC [Directions] | NC-173 Trumbull-207 | ||
| Mon., 5/23 | V Girls Lacrosse | Wilton | Away - Norwalk HS-Testa Field [Directions] | 5:00 p.m. | 3:15 PM; 1 Bus | |
| Mon., 5/23 | V Girls Outdoor Track | FCIAC Championships | Away - Wilton HS-Fujitani Field - Turf | 3:30 p.m. | 1:50 PM; 1 Bus | |
| Pending change awaiting acceptance by one or more parties involved: Facility to Danbury HS-Wilton HS-Fujitani Field - Turf | ||||||
| Tue., 5/24 | V Boys Outdoor Track | FCIAC Championships | Away - Danbury HS-Stadium Track | 3:30 p.m. | 2:10 PM; 1 Bus | |
| Tue., 5/24 | V Boys Tennis | TBA | Home - New Canaan HS-NCHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/25 | V Boys Tennis | Brookfield (Scrim.) | Home - New Canaan HS-NCHS Tennis Courts [Directions] | 3:45 p.m. | ||
| Wed., 5/25 | V Boys Volleyball | Trumbull | Away - Fairfield Warde HS-Gym [Directions] | 7:00 p.m. | 4:45 PM; 1 Bus | |
| Wed., 5/25 | V Girls Golf | Fairfield Ludlowe | Home - CCNC [Directions] | NC-176 F. Ludlowe-246 | ||
| Wed., 5/25 | V Softball | Wilton (Scrim.) | Home - Waveny Park-Orchard Field [Directions] | 5:30 p.m. | ||
| Thu., 5/26 | V Baseball | Wilton (Scrim.) | Away - Wilton HS-Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Thu., 5/26 | V Softball | Brien McMahon (Scrim.) | Home - Waveny Park-Orchard Field [Directions] | 4:00 p.m. | ||
| Tue., 5/31 | V Baseball | Enfield | Home - Mead Park-Baseball Field [Directions] | 3:30 p.m. | ||
| Tue., 5/31 | V Boys Tennis | Farmington | Away - Farmington HS [Directions] | W 5-2 | 12:45 PM; 1 Bus | |
| Tue., 5/31 | V Girls Golf | Staples | Away - Fairchild Wheeler Golf Course [Directions] | NC-177 Staples-184 | 1:20 PM; 1 Bus | |
| Tue., 5/31 | V Girls Lacrosse | Staples | Home - New Canaan HS-Dunning Stadium [Directions] | 5:00 p.m. | ||
| Tue., 5/31 | V Softball | Hall | Away - Hall HS-Varsity Softball [Directions] | 5:00 p.m. | 1:45 AM; 1 Bus | |
| Tue., 5/31 | V Girls Tennis | Fairfield Ludlowe | Home - New Canaan HS-NCHS Tennis Courts [Directions] | W 6-1 | ||
| Wed., 6/1 | V Baseball | Xavier | Away - Palmer Field-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 6/1 | V Boys Lacrosse | Glastonbury | Away - Glastonbury HS-Field 1 [Directions] | 5:00 p.m. | 2:00 PM; 1 Bus | |
| Wed., 6/1 | V Boys Outdoor Track | CIAC Class L Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Wed., 6/1 | V Boys Tennis | Wethersfield | Away - Wethersfield HS-Tennis Courts [Directions] | W 5-2 | ||
| Wed., 6/1 | V Boys Volleyball | Wolcott Tech | Home - New Canaan HS-Main Gym [Directions] | 5:00 p.m. | ||
| Wed., 6/1 | V Girls Outdoor Track | CIAC Class L Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Wed., 6/1 | V Girls Tennis | Amity | Away - Amity Regional HS-Tennis Courts [Directions] | 3:00 p.m. | ||
| Thu., 6/2 | V Girls Lacrosse | South Windsor | Home - New Canaan HS-Dunning Stadium [Directions] | 2:00 p.m. | ||
| Fri., 6/3 | V Boys Tennis | East Lyme | Away - East Lyme HS-Tennis Court 1 [Directions] | W 7-0 | 11:15 AM, Dismiss TBA; 1 Bus | |
| Fri., 6/3 | V Boys Volleyball | Masuk | Home - New Canaan HS-Main Gym [Directions] | 5:15 p.m. | ||
| Sat., 6/4 | V Boys Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 3:00 p.m. | 1:15 PM; 2 Buses | |
| Sat., 6/4 | V Boys Tennis | Darien | Home - Wesleyan-John Wood Memorial Tennis Courts [Directions] | 9:00 a.m. | ||
| Mon., 6/6 | V Boys Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/6 | V Boys Tennis | CIAC Individual Invitational - Opening Round, Singles and Doubles | Away - Wesleyan | 10:00 a.m. | ||
| Mon., 6/6 | V Girls Golf | CIAC Division I Championship | Away - Tashua Knolls GC | 8:30 a.m. | ||
| Mon., 6/6 | V Girls Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/6 | V Girls Tennis | CIAC Individual Invitational - Opening Round, Singles and Doubles | Away - Wesleyan | 10:00 a.m. | ||
| Tue., 6/7 | V Boys Tennis | CIAC Individual Invitational - Round of 16 | Away - Wesleyan | 9:00 a.m. | ||
| Tue., 6/7 | V Boys Volleyball | Farmington | Away - Kennedy HS (Waterbury) [Directions] | 7:00 p.m. | 4:00 PM; 1 Bus | |
| Tue., 6/7 | V Girls Lacrosse | Ridgefield | Home - Greenwich HS-Cardinal Stadium [Directions] | 5:00 p.m. | 3:00 PM; 1 Bus | |
| Tue., 6/7 | V Girls Tennis | CIAC Individual Invitational - Round of 16 | Away - Wesleyan | 9:00 a.m. | ||
| Wed., 6/8 | V Boys Tennis | CIAC Individual Invitational - Quarterfinals | Away - Wesleyan | 3:00 p.m. | ||
| Wed., 6/8 | V Girls Tennis | CIAC Individual Invitational - Quarterfinals | Away - Wesleyan | 3:00 p.m. | ||
| Thu., 6/9 | V Boys Tennis | CIAC Individual Invitational - Semifinals | Away - Wesleyan | 3:00 p.m. | ||
| Thu., 6/9 | V Boys Volleyball | Joel Barlow | Away - Pomperaug HS-Main Gym [Directions] | 7:00 p.m. | 3:15 PM; 1 Bus | |
| Thu., 6/9 | V Girls Tennis | CIAC Individual Invitational - Semifinals | Away - Wesleyan | 3:00 p.m. | ||
| Fri., 6/10 | V Boys Tennis | CIAC Individual Invitational - Finals | Away - Wesleyan | 3:00 p.m. | ||
| Fri., 6/10 | V Girls Tennis | CIAC Individual Invitational - Finals | Away - Wesleyan | 3:00 p.m. | ||
| Sat., 6/11 | V Girls Golf | CIAC Girls State Open | Away - Black Hall Club | 1:00 p.m. | ||
| Sat., 6/11 | V Girls Lacrosse | Darien | Away - Sacred Heart University-Turf Field [Directions] | 2:00 p.m. | 11:30 AM; 1 Bus | |
| Mon., 6/13 | V Boys Outdoor Track | CIAC Boys Hammer Throw Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Mon., 6/13 | V Girls Outdoor Track | CIAC Girls Hammer Throw Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Tue., 6/14 | V Boys Outdoor Track | CIAC Decathlon Championship Day 1 | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 6/14 | V Girls Outdoor Track | CIAC Heptathlon Championship Day 1 | Away - Willow Brook Park | 10:30 a.m. | ||
| Tue., 6/14 | V Girls Outdoor Track | CIAC Girls Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/15 | V Boys Outdoor Track | CIAC Decathlon Championship Day 2 | Away - Willow Brook Park | 10:00 a.m. | ||
| Wed., 6/15 | V Boys Outdoor Track | CIAC Boys Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/15 | V Girls Outdoor Track | CIAC Heptathlon Championship Day 2 | Away - Willow Brook Park | 10:00 a.m. | ||