| New Canaan 2022-23 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 932 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| Tue., 8/23 | V Boys Golf | Wilton | Away - Rolling Hills Country Club [Directions] | New Canaan 160 Wilton 161 | 2:00 PM; 1 Van | |
| Wed., 8/24 | V Football | Southington (Scrim.) | Home - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | ||
| Thu., 8/25 | JV Boys Golf | Staples | Away - Longshore Golf Course [Directions] | 3:15 p.m. | 2:00 PM; 1 Van | |
| Tue., 8/30 | V Boys Golf | Westhill | Home - CCNC [Directions] | New Canaan 162 Westhill 167 | ||
| Tue., 8/30 | V Girls Soccer | St. Lukes (Scrim.) | Away - St Lukes School | 3:45 p.m. | 2:45 PM; 1 Bus | |
| Wed., 8/31 | V Boys Golf | Fairfield Ludlowe | Home - CCNC [Directions] | New Canaan 154 Fairfield Ludlowe 167 | ||
| Wed., 8/31 | JV Boys Golf | Fairfield Ludlowe | Home - CCNC [Directions] | 3:00 p.m. | ||
| Wed., 8/31 | V Boys Soccer | Stamford (Scrim.) | Home - New Canaan HS-Dunning Stadium [Directions] | 7:00 p.m. | ||
| Wed., 8/31 | JV Boys Soccer | Stamford (Scrim.) | Home - Saxe MS-Field 1 [Directions] | 4:30 p.m. | ||
| Wed., 8/31 | V Field Hockey | Greenwich Academy (Scrim.) | Home - New Canaan HS-WTT #2 [Directions] | 4:30 p.m. | ||
| Wed., 8/31 | JV Field Hockey | Greenwich Academy (Scrim.) | Home - New Canaan HS-WTT #2 [Directions] | 6:00 p.m. | ||
| Thu., 9/1 | JV Boys Golf | Darien | Home - CCNC [Directions] | 3:00 p.m. | ||
| Thu., 9/1 | V Girls Soccer | Greenwich Academy | Away - Greenwich Academy-2nd Field | 4:30 p.m. | 3:00 PM; 1 Bus (V & JV ride together) | |
| Thu., 9/1 | JV Girls Soccer | Greenwich Academy | Away - Greenwich Academy-Tammaro Field | 4:30 p.m. | 3:00 PM; 1 Bus (JV & V ride together) | |
| Fri., 9/2 | V Boys Soccer | St. Lukes (Scrim.) | Home - Saxe MS-Field 1 [Directions] | 4:30 p.m. | ||
| Fri., 9/2 | JV Boys Soccer | St. Lukes (Scrim.) | Home - Saxe MS-Field #2 [Directions] | 4:30 p.m. | ||
| Sat., 9/3 | FR Football | Iona Prep (NY) (Scrim.) | Away - Iona Preparatory School-Stadium | 10:00 a.m. | 8:00 AM; 2 Buses | |
| Tue., 9/6 | V Boys Soccer | King and Low-Heywood Thomas (Scrim.) | Away - King School-King South Turf | 4:30 p.m. | 3:00 PM; 1 Bus | |
| Tue., 9/6 | V Girls Volleyball | King and Low-Heywood Thomas (Scrim.) | Home - New Canaan HS-Main Gym [Directions] | 4:30 p.m. | TBA | |
| Wed., 9/7 | V Boys Golf | Ridgefield | Home - CCNC [Directions] | New Canaan 150 Ridgefield 174 | ||
| Wed., 9/7 | JV Boys Golf | Ridgefield | Home - CCNC [Directions] | 3:00 p.m. | ||
| Thu., 9/8 | V Girls Volleyball | Westhill | Home - New Canaan HS-Main Gym [Directions] | W 3-1 | ||
| Thu., 9/8 | JV Girls Volleyball | Westhill | Home - New Canaan HS-Main Gym [Directions] | Postponed | ||
| Fri., 9/9 | V Football | Xavier | Away - Xavier HS-Larry McHugh Field [Directions] | W 31-0 | 3:45 PM; 2 Buses | |
| Fri., 9/9 | V Girls Soccer | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | L 1-3 | 2:20 PM; 1 Bus (JV & V ride together) | |
| Fri., 9/9 | JV Girls Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 4:00 p.m. | 2:20 PM; 1 Bus (JV & V ride together) | |
| Fri., 9/9 | FR Girls Soccer | Danbury | Home - Saxe MS-Field 1 [Directions] | 4:30 p.m. | ||
| Sat., 9/10 | JV Football | Xavier | Home - New Canaan HS-Dunning Stadium [Directions] | 10:30 a.m. | ||
| Sat., 9/10 | FR Football | Xavier | Away - Xavier HS-Larry McHugh Field [Directions] | 10:00 a.m. | 7:30 AM; 1 Bus | |
| Sat., 9/10 | V Boys Soccer | Staples | Away - Staples HS-Loeffler Field - Staples HS [Directions] | W 1-0 | 8:45 AM; 1 Bus (JV & V ride together) | |
| Sat., 9/10 | JV Boys Soccer | Staples | Away - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | 8:45 AM; 1 Bus (JV & V ride together) | |
| Sat., 9/10 | FR Boys Soccer | Staples | Home - Saxe MS-Field 1 [Directions] | 10:00 a.m. | ||
| Sat., 9/10 | V Field Hockey | Branford | Home - New Canaan HS-Dunning Stadium [Directions] | W 3-0 | ||
| Sat., 9/10 | JV Field Hockey | Branford | Home - New Canaan HS-Dunning Stadium [Directions] | 3:00 p.m. | ||
| Mon., 9/12 | V Boys Golf | Danbury | Home - CCNC [Directions] | New Canaan 159 Danbury 175 | ||
| Mon., 9/12 | V Field Hockey | Staples | Away - Staples HS-Ginny Parker Field [Directions] | L 1-4 | 2:15 PM; 1 Bus | |
| Mon., 9/12 | JV Field Hockey | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 5:15 p.m. | 3:30 PM; 1 Bus | |
| Mon., 9/12 | FR Field Hockey | Staples | Home - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Mon., 9/12 | V Girls Soccer | Staples | Home - New Canaan HS-Dunning Stadium [Directions] | L 0-4 | ||
| Mon., 9/12 | JV Girls Soccer | Staples | Home - Saxe MS-Field 1 [Directions] | 4:30 p.m. | ||
| Mon., 9/12 | FR Girls Soccer | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Mon., 9/12 | V Girls Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | W 3-2 | 3:00 PM; 1 Bus (V & JV teams ride together.) | |
| Mon., 9/12 | JV Girls Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | 3:00 PM; 1 Bus (V & JV teams ride together) | |
| Tue., 9/13 | V Boys Cross Country | Ridgefield, Fairfield Warde, Staples | Away - Ridgefield HS-Upper Grass Field [Directions] | 4:00 p.m. | 2:35 PM; 1 Bus | |
| Tue., 9/13 | V Boys Golf | Stamford | Away - Stamford High-Sterling Farms Golf Course [Directions] | New Canaan 166 Stamford 204 | 1:30 PM; 1 Van | |
| Tue., 9/13 | JV Boys Golf | Greenwich | Home - CCNC [Directions] | 3:00 p.m. | ||
| Tue., 9/13 | V Boys Soccer | Wilton | Home - New Canaan HS-Dunning Stadium [Directions] | W 3-1 | ||
| Tue., 9/13 | JV Boys Soccer | Wilton | Home - Saxe MS-Field 1 [Directions] | 4:30 p.m. | ||
| Tue., 9/13 | FR Boys Soccer | Wilton | Away - Allen's Meadow-Field #1 [Directions] | 4:30 p.m. | 3:00 PM; 1 Bus | |
| Tue., 9/13 | V Girls Cross Country | Ridgefield, Fairfield Warde, Staples | Away - Ridgefield HS-Upper Grass Field [Directions] | 4:00 p.m. | 2:35 PM; 1 Bus | |
| Wed., 9/14 | JV Boys Golf | Darien | Home - CCNC [Directions] | 3:00 p.m. | ||
| Wed., 9/14 | V Field Hockey | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | W 8-0 | 2:40 PM; 1 Bus (V & JV will ride together) | |
| Wed., 9/14 | JV Field Hockey | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | 2:40 PM; 1 Bus (JV & V together) | |
| Wed., 9/14 | V Girls Soccer | Wilton | Away - Wilton HS-Lilly Field [Directions] | L 0-2 | 5:15 PM; 1 Bus (JV & V ride together.) | |
| Wed., 9/14 | JV Girls Soccer | Wilton | Away - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | 2:40 PM; 1 Bus (JV & V ride together) | |
| Wed., 9/14 | FR Girls Soccer | Wilton | Home - Saxe MS-Field 1 [Directions] | 4:30 p.m. | ||
| Wed., 9/14 | V Girls Swimming and Diving | Fairfield Warde | Away - Fairfield University-Pool [Directions] | New Canaan - 101 Warde - 77 | 4:00 PM; 1 Bus | |
| Wed., 9/14 | V Girls Volleyball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | L 0-3 | 3:00 PM; 1 Bus (V & JV ride together) | |
| Wed., 9/14 | JV Girls Volleyball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 4:30 p.m. | 3:00 PM; 1 Bus (V & JV ride together) | |
| Thu., 9/15 | FR Football | St. Joseph | Home - New Canaan HS-Dunning Stadium [Directions] | 5:30 p.m. | ||
| Thu., 9/15 | V Boys Golf | St. Joseph, Staples | Home - CCNC [Directions] | New Canaan 169 Staples 169 St Joseph 170 | ||
| Thu., 9/15 | JV Boys Golf | Staples | Away - Longshore Golf Course [Directions] | 3:00 p.m. | 2:30 PM; 1 Van | |
| Fri., 9/16 | V Football | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | W 37-14 | 5:15 PM; 2 Buses | |
| Fri., 9/16 | V Boys Soccer | St. Joseph | Home - New Canaan HS-Dunning Stadium [Directions] | W 5-1 | ||
| Fri., 9/16 | FR Girls Soccer | Darien | Home - Saxe MS-Field 1 [Directions] | 4:00 p.m. | ||
| Fri., 9/16 | V Girls Swimming and Diving | Westhill/Stamford | Home - New Canaan YMCA-Pool [Directions] | New Canaan - 98 Westhill - 86 | ||
| Sat., 9/17 | V Boys Cross Country | Wilton | Away - Allen's Meadow-XC Course [Directions] | 9:00 a.m. | 7:00 AM; 1 Bus | |
| Sat., 9/17 | V Girls Cross Country | Wilton | Away - Allen's Meadow-XC Course [Directions] | 9:00 a.m. | 7:30 AM; 1 Bus | |
| Sat., 9/17 | V Field Hockey | Danbury | Home - New Canaan HS-Dunning Stadium [Directions] | W 8-0 | ||
| Sat., 9/17 | JV Field Hockey | Danbury | Home - New Canaan HS-Dunning Stadium [Directions] | 2:00 p.m. | ||
| Sat., 9/17 | V Girls Soccer | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | L 0-2 | 8:30 AM; 1 Bus (V & JV together) | |
| Sat., 9/17 | JV Girls Soccer | St. Joseph | Away - St. Joseph HS-Lower Grass Field [Directions] | 10:00 a.m. | 8:30 AM; 1 Bus (JV & V ride together) | |
| Mon., 9/19 | JV Football | Brien McMahon | Home - New Canaan HS-Dunning Stadium [Directions] | 5:30 p.m. | ||
| Mon., 9/19 | V Boys Soccer | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | L 2-5 | 4:45 PM; 1 Bus | |
| Mon., 9/19 | JV Boys Soccer | Ridgefield | Away - Ridgefield HS-RHS Lower Grass Field [Directions] | 4:00 p.m. | 2:15 PM; 1 Bus | |
| Mon., 9/19 | FR Boys Soccer | Ridgefield | Home - Saxe MS-Field 1 [Directions] | 5:00 p.m. | ||
| Tue., 9/20 | V Boys Cross Country | Danbury, Trumbull | Home - Waveny Park [Directions] | 4:30 p.m. | ||
| Tue., 9/20 | V Boys Golf | Brien McMahon | Home - CCNC [Directions] | New Canaan 165 McMahon 175 | ||
| Tue., 9/20 | JV Boys Golf | Fairfield Prep | Away - Brooklawn Country Club [Directions] | 3:15 p.m. | 1:45 PM; 1 Van | |
| Tue., 9/20 | V Girls Cross Country | Danbury, Trumbull | Home - Waveny Park [Directions] | 4:30 p.m. | ||
| Tue., 9/20 | V Girls Diving | Wilton | Away - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | 2:30 PM (One way) | |
| Tue., 9/20 | V Field Hockey | Fairfield Ludlowe | Home - New Canaan HS-Dunning Stadium [Directions] | W 8-0 | ||
| Tue., 9/20 | JV Field Hockey | Fairfield Ludlowe | Home - New Canaan HS-WTT #2 [Directions] | 6:15 p.m. | ||
| Tue., 9/20 | FR Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Front Field [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Tue., 9/20 | V Girls Soccer | Ridgefield | Home - New Canaan HS-Dunning Stadium [Directions] | L 0-1 | ||
| Tue., 9/20 | JV Girls Soccer | Ridgefield | Home - Saxe MS-Field 1 [Directions] | 5:00 p.m. | ||
| Tue., 9/20 | FR Girls Soccer | Ridgefield | Away - Ridgefield HS-Upper Grass Field [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Wed., 9/21 | JV Boys Golf | Greenwich | Home - CCNC [Directions] | 3:00 p.m. | ||
| Wed., 9/21 | FR Field Hockey | Trumbull | Home - New Canaan HS-WTT #2 [Directions] | 4:30 p.m. | 3:40 PM; 1 Bus | |
| Wed., 9/21 | V Girls Swimming and Diving | Wilton | Away - Wilton YMCA [Directions] | New Canaan - 84 Wilton - 102 | 2:20 PM; 1 Bus | |
| Thu., 9/22 | FR Football | Fairfield Prep | Away - Fairfield University-Rafferty Stadium [Directions] | 4:00 p.m. | 2:20 AM; 1 Bus | |
| Thu., 9/22 | V Boys Soccer | Stamford | Home - New Canaan HS-Dunning Stadium [Directions] | W 1-0 | ||
| Thu., 9/22 | JV Boys Soccer | Stamford | Home - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Thu., 9/22 | FR Boys Soccer | Stamford | Away - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | 3:15 PM; 1 Bus | |
| Thu., 9/22 | V Field Hockey | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | W 9-0 | 3:40 PM; 1 Bus | |
| Thu., 9/22 | JV Field Hockey | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 5:30 p.m. | 3:40 PM; 1 Bus (V & JV ride together) | |
| Thu., 9/22 | V Girls Volleyball | Danbury | Home - New Canaan HS-Main Gym [Directions] | W 3-0 | ||
| Thu., 9/22 | JV Girls Volleyball | Danbury | Home - New Canaan HS-Main Gym [Directions] | 4:30 p.m. | ||
| Thu., 9/22 | FR Girls Volleyball | Danbury | Away - Danbury HS-New Gym [Directions] | 4:30 p.m. | 2:45 PM; 1 Bus | |
| Fri., 9/23 | V Football | Fairfield Prep | Home - New Canaan HS-Dunning Stadium [Directions] | W 14-7 | ||
| Fri., 9/23 | V Girls Soccer | Stamford | Away - Stamford HS-SHS Upper Soccer Field [Directions] | T 1-1 | 2:30 PM; 1 Bus | |
| Fri., 9/23 | JV Girls Soccer | Stamford | Away - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | 3:15 PM; 1 Bus | |
| Sat., 9/24 | V Boys Cross Country | Farmington | Away - Winding Trails-Cross Country Course [Directions] | 9:00 a.m. | 7:00 AM; 1 Bus | |
| Sat., 9/24 | JV Football | Fairfield Prep | Away - Fairfield University-Barlow Field [Directions] | 10:00 a.m. | 8:15 AM; 1 Bus | |
| Sat., 9/24 | V Boys Soccer | Wethersfield | Away - Farmington Sports Arena-Field 6 [Directions] | W 3-0 | 3:00 PM; 1 Bus | |
| Sat., 9/24 | V Field Hockey | Cheshire | Away - Cheshire High Main Game field [Directions] | W 2-0 | 8:30 AM; 1 Bus (V & JV leave together) | |
| Sat., 9/24 | JV Field Hockey | Cheshire | Away - Cheshire HS-Cheshire High School Main Game field [Directions] | 12:00 p.m. | 8:30 AM; 1 Bus (JV & V leave together) | |
| Tue., 9/27 | JV Boys Golf | Ridgefield | Away - Ridgefield Golf Course [Directions] | 3:00 p.m. | 1:45 PM; 1 Van | |
| Tue., 9/27 | V Girls Soccer | Greenwich | Home - New Canaan HS-Dunning Stadium [Directions] | W 1-0 | ||
| Tue., 9/27 | JV Girls Soccer | Greenwich | Home - Saxe MS-Field 1 [Directions] | 4:30 p.m. | ||
| Tue., 9/27 | FR Girls Soccer | Greenwich | Away - Greenwich HS-Cos Cob Park, Benvenuto Field [Directions] | 4:00 p.m. | 2:40 PM; 1 Bus | |
| Tue., 9/27 | V Girls Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | L 2-3 | 2:45 PM; 1 Bus (V & JV ride together) | |
| Tue., 9/27 | JV Girls Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:30 p.m. | 2:45 PM; 1 Bus (V & JV ride together) | |
| Tue., 9/27 | FR Girls Volleyball | Staples | Home - New Canaan HS-Main Gym [Directions] | 4:30 p.m. | ||
| Wed., 9/28 | V Boys Cross Country | Stamford, Westhill, Wilton | Home - Waveny Park [Directions] | 4:30 p.m. | ||
| Wed., 9/28 | V Boys Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | Greenwich 145 New Canaan 155 | 2:00 PM; 1 Van | |
| Wed., 9/28 | JV Boys Golf | Fairfield Warde | Home - CCNC [Directions] | 3:00 p.m. | ||
| Wed., 9/28 | V Boys Soccer | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | L 1-3 | 3:00 PM; 1 Bus | |
| Wed., 9/28 | JV Boys Soccer | Greenwich | Away - Central MS [Directions] | 4:45 p.m. | 3:00 PM; 1 Bus | |
| Wed., 9/28 | FR Boys Soccer | Greenwich | Home - Saxe MS-Field 1 [Directions] | 4:30 p.m. | ||
| Wed., 9/28 | V Girls Cross Country | Stamford, Westhill, Wilton | Home - Waveny Park [Directions] | 4:30 p.m. | ||
| Wed., 9/28 | V Field Hockey | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | W 10-0 | 3:00 PM; 1 Bus (V & JV together) | |
| Wed., 9/28 | JV Field Hockey | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | 3:00 PM; 1 Bus (JV & V together) | |
| Wed., 9/28 | V Girls Swimming and Diving | Norwalk/McMahon | Away - Norwalk HS-Pat Spinola Natatorium [Directions] | New Canaan - 99 Norwalk - 85 | 2:30 PM; 1 Bus | |
| Thu., 9/29 | FR Football | Staples | Home - New Canaan HS-Dunning Stadium [Directions] | 4:30 p.m. | ||
| Thu., 9/29 | V Boys Golf | Fairfield Warde | Away - Brooklawn Country Club [Directions] | New Canaan 151 Fairfield Warde 163 | 1:00 PM; 1 Van | |
| Thu., 9/29 | JV Boys Golf | St. Joseph | Home - CCNC [Directions] | 3:00 p.m. | ||
| Thu., 9/29 | V Field Hockey | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | W 3-2 | 2:45 PM; 1 Bus | |
| Thu., 9/29 | JV Field Hockey | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 5:30 p.m. | 2:45 PM; 1 Bus (JV & V together) | |
| Thu., 9/29 | FR Field Hockey | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 5:30 p.m. | 3:45 PM; 1 Bus | |
| Thu., 9/29 | V Girls Soccer | Brien McMahon | Home - New Canaan HS-Dunning Stadium [Directions] | L 2-0 | ||
| Thu., 9/29 | JV Girls Soccer | Brien McMahon | Home - Saxe MS-Field 1 [Directions] | 4:30 p.m. | ||
| Thu., 9/29 | V Girls Volleyball | Wilton | Home - New Canaan HS-Main Gym [Directions] | W 3-2 | ||
| Thu., 9/29 | JV Girls Volleyball | Wilton | Home - New Canaan HS-Main Gym [Directions] | 4:30 p.m. | ||
| Thu., 9/29 | FR Girls Volleyball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:15 p.m. | 3:00 PM; 1 Bus | |
| Fri., 9/30 | V Football | Bridgeport Central | Home - New Canaan HS-Dunning Stadium [Directions] | W 37-0 | ||
| Fri., 9/30 | V Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | L 0-2 | 2:30 PM; 1 Bus | |
| Fri., 9/30 | JV Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 5:45 p.m. | 4:30 PM; 1 Bus | |
| Fri., 9/30 | FR Boys Soccer | Brien McMahon | Home - Saxe MS-Field 1 [Directions] | 4:30 p.m. | ||
| Fri., 9/30 | V Girls Swimming and Diving | Ridgefield | Away - Barlow Mountain Pool [Directions] | New Canaan - 81.5 Ridgefield - 104.5 | 2:15 PM; 1 Bus | |
| Fri., 9/30 | FR Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 5:00 p.m. | 3:00 PM; 1 Bus | |
| Sat., 10/1 | V Boys Cross Country | Brewster (NY) | Away - Brewster HS | 9:00 a.m. | 7:00 AM; 1 Bus | |
| Sat., 10/1 | V Girls Volleyball | St. Joseph | Home - New Canaan HS-Main Gym [Directions] | W 3-0 | ||
| Sat., 10/1 | JV Girls Volleyball | St. Joseph | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 10/3 | V Boys Cross Country | Greenwich, Darien, Fairfield Ludlowe | Away - Greenwich Point [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Mon., 10/3 | V Boys Golf | Norwalk | Away - Oak Hills Golf Course [Directions] | New Canaan 147 Norwalk 198 | 1:45 PM; 1 Van | |
| Mon., 10/3 | V Boys Soccer | Danbury | Home - New Canaan HS-Dunning Stadium [Directions] | W 3-1 | ||
| Mon., 10/3 | FR Boys Soccer | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 6:00 p.m. | 4:15 PM; 1 Bus | |
| Mon., 10/3 | V Girls Cross Country | Greenwich, Darien, Fairfield Ludlowe | Away - Greenwich Point [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Mon., 10/3 | V Field Hockey | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | W 10-0 | 2:30 PM; 1 Bus (V & JV together) | |
| Mon., 10/3 | JV Field Hockey | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 5:30 p.m. | 2:30 PM; 1 Bus (JV & V together) | |
| Mon., 10/3 | V Girls Soccer | Trumbull | Away - Trumbull HS-Cork Field [Directions] | T 2-2 | 3:15 PM; 1 Bus | |
| Mon., 10/3 | JV Girls Soccer | Trumbull | Away - Trumbull HS-The Pit [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Tue., 10/4 | JV Boys Soccer | Danbury | Home - New Canaan HS-WTT #1 [Directions] | 4:30 p.m. | ||
| Tue., 10/4 | JV Boys Soccer | Danbury | Home - New Canaan HS-WTT #1 [Directions] | 4:30 p.m. | ||
| Thu., 10/6 | JV Boys Golf | Darien | Away - Woodway Country Club [Directions] | 3:15 p.m. | 2:15 PM; 1 Van | |
| Thu., 10/6 | V Boys Soccer | Bridgeport Central | Home - New Canaan HS-Dunning Stadium [Directions] | W 3-1 | ||
| Thu., 10/6 | JV Boys Soccer | Bridgeport Central | Home - Saxe MS-Field 1 [Directions] | Postponed | ||
| Thu., 10/6 | V Field Hockey | Wilton | Home - New Canaan HS-Dunning Stadium [Directions] | L 2-1 | ||
| Thu., 10/6 | JV Field Hockey | Wilton | Home - New Canaan HS-WTT #2 [Directions] | 6:00 p.m. | ||
| Thu., 10/6 | FR Girls Volleyball | Ridgefield | Home - New Canaan HS-Main Gym [Directions] | 4:30 p.m. | ||
| Fri., 10/7 | V Girls Soccer | Bridgeport Central | Away - Bridgeport Central-Kennedy Stadium Turf [Directions] | W 7-0 | 2:20 PM; 1 Bus | |
| Fri., 10/7 | V Girls Swimming and Diving | St. Joseph | Home - New Canaan YMCA-Pool [Directions] | New Canaan - 96 St. Joe's - 83 | ||
| Sat., 10/8 | V Boys Cross Country | Avon | Away - Wickham Park [Directions] | 9:00 a.m. | 7:00 AM; 1 Bus | |
| Sat., 10/8 | V Girls Volleyball | Stamford | Home - New Canaan HS-Main Gym [Directions] | W 3-0 | ||
| Sat., 10/8 | JV Girls Volleyball | Stamford | Home - New Canaan HS-Main Gym [Directions] | 2:00 p.m. | ||
| Mon., 10/10 | JV Football | Iona Prep (NY) | Home - New Canaan HS-WTT #1 [Directions] | 4:30 p.m. | ||
| Mon., 10/10 | V Boys Soccer | Fairfield Warde | Away - Fairfield Warde HS-Varsity Grass Soccer Field [Directions] | W 1-0 | 3:45 PM; 1 Bus | |
| Mon., 10/10 | JV Boys Soccer | Fairfield Warde | Away - Fairfield Warde HS-Fairfield Warde Grass Utility Field [Directions] | 4:00 p.m. | 2:15 PM; 1 Bus | |
| Mon., 10/10 | FR Boys Soccer | Fairfield Warde | Home - Saxe MS-Field 1 [Directions] | 4:30 p.m. | ||
| Mon., 10/10 | V Field Hockey | Fairfield Warde | Home - New Canaan HS-Dunning Stadium [Directions] | W 9-0 | ||
| Mon., 10/10 | JV Field Hockey | Fairfield Warde | Home - New Canaan HS-Dunning Stadium [Directions] | 6:00 p.m. | ||
| Mon., 10/10 | FR Field Hockey | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | Cancelled | 2:30 PM; 1 Bus | |
| Mon., 10/10 | V Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | W 3-2 | 3:00 PM; 1 Bus (V & JV will travel together) | |
| Mon., 10/10 | JV Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | 3:00 PM; 1 Bus (V & JV will travel together) | |
| Mon., 10/10 | FR Girls Volleyball | Greenwich | Home - New Canaan HS-Main Gym [Directions] | 4:30 p.m. | ||
| Tue., 10/11 | V Boys Cross Country | Brien McMahon, Norwalk, St. Joseph | Home - Waveny Park [Directions] | 4:30 p.m. | ||
| Tue., 10/11 | V Boys Golf | Fairfield Prep | Away - Patterson Club [Directions] | Fairfield Prep 150 New Canaan 166 | 1:45 PM; 1 Van | |
| Tue., 10/11 | JV Boys Golf | St. Joseph | Away - Tashua Knolls Golf Course-Tashua Glen [Directions] | 3:15 p.m. | 1:00 PM; 1 Van | |
| Tue., 10/11 | V Girls Cross Country | Brien McMahon, Norwalk, St. Joseph | Home - Waveny Park [Directions] | 4:30 p.m. | ||
| Tue., 10/11 | V Girls Soccer | Fairfield Warde | Home - New Canaan HS-Dunning Stadium [Directions] | L 4-2 | ||
| Tue., 10/11 | JV Girls Soccer | Fairfield Warde | Home - Saxe MS-Field 1 [Directions] | 4:30 p.m. | ||
| Tue., 10/11 | FR Girls Soccer | Fairfield Warde | Away - Tunxis [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Wed., 10/12 | FR Football | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | 4:00 PM; 1 Bus | |
| Wed., 10/12 | V Boys Soccer | Darien | Away - Darien HS-DHS Center Oval Turf Field [Directions] | L 0-4 | 2:45 PM; 1 Bus (V & JV will ride together) | |
| Wed., 10/12 | JV Boys Soccer | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | 2:45 PM; 1 Bus (V & JV will ride together) | |
| Wed., 10/12 | FR Boys Soccer | Darien | Home - Saxe MS-Field 1 [Directions] | 4:30 p.m. | ||
| Wed., 10/12 | FR Field Hockey | Darien | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:30 p.m. | 3:30 PM; 1 Bus | |
| Wed., 10/12 | V Girls Swimming and Diving | Trumbull | Away - Bridgeport Univ Pool-Pool [Directions] | New Canaan - 103 Trumbull - 77 | 2:15 PM; 1 Bus | |
| Wed., 10/12 | V Girls Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | W 3-2 | 3:00 PM; 1 Bus (V & JV ride together) | |
| Wed., 10/12 | JV Girls Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 6:00 p.m. | 3:00 PM; 1 Bus (V & JV ride together) | |
| Wed., 10/12 | FR Girls Volleyball | Brien McMahon | Home - New Canaan HS-Main Gym [Directions] | 4:30 p.m. | ||
| Thu., 10/13 | V Boys Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | Trumbull 158 New Canaan 159 | 4:45 PM; 1 Bus | |
| Pending change awaiting acceptance by one or more parties involved: Date to 10/12 | ||||||
| Thu., 10/13 | V Boys Golf | Darien, Danbury | Away - Wee Burn CC [Directions] | New Canaan 156 Darien 163 | ||
| Thu., 10/13 | V Girls Soccer | Darien | Home - New Canaan HS-Dunning Stadium [Directions] | L 2-0 | ||
| Thu., 10/13 | JV Girls Soccer | Darien | Home - Saxe MS-Field 1 [Directions] | 4:30 p.m. | ||
| Thu., 10/13 | FR Girls Soccer | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | 3:00 PM; 1 Bus | |
| Fri., 10/14 | V Boys Soccer | Trumbull | Home - New Canaan HS-WTT #2 [Directions] | L 1-4 | ||
| Fri., 10/14 | JV Boys Soccer | Trumbull | Home - Saxe MS-Field 1 [Directions] | 4:30 p.m. | ||
| Fri., 10/14 | FR Boys Soccer | Trumbull | Away - Trumbull HS-The Pit [Directions] | 4:45 p.m. | 2:45 PM; 1 Bus | |
| Fri., 10/14 | V Field Hockey | Darien | Home - New Canaan HS-Dunning Stadium [Directions] | L 3-0 | ||
| Fri., 10/14 | JV Field Hockey | Darien | Home - New Canaan HS-Dunning Stadium [Directions] | 6:00 p.m. | ||
| Fri., 10/14 | V Girls Swimming and Diving | Fairfield Ludlowe | Home - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Fri., 10/14 | V Girls Volleyball | Bridgeport Central | Home - New Canaan HS-Main Gym [Directions] | W 3-0 | ||
| Fri., 10/14 | JV Girls Volleyball | Bridgeport Central | Home - New Canaan HS-Main Gym [Directions] | 4:30 p.m. | ||
| Sat., 10/15 | V Football | Norwalk | Home - New Canaan HS-Dunning Stadium [Directions] | W 45-0 | ||
| Sat., 10/15 | FR Girls Soccer | Trumbull | Home - Saxe MS-Field 1 [Directions] | 10:00 a.m. | ||
| Sat., 10/15 | FR Girls Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 10:00 a.m. | 8:45 AM; 1 Bus | |
| Mon., 10/17 | JV Football | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | 5:00 p.m. | 3:15 PM; 1 Bus | |
| Mon., 10/17 | V Boys Soccer | Fairfield Ludlowe | Home - New Canaan HS-Dunning Stadium [Directions] | L 1-3 | ||
| Mon., 10/17 | JV Boys Soccer | Fairfield Ludlowe | Home - Saxe MS-Field 1 [Directions] | 4:30 p.m. | ||
| Mon., 10/17 | FR Boys Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Mon., 10/17 | V Field Hockey | Brien McMahon | Home - New Canaan HS-Dunning Stadium [Directions] | W 8-0 | ||
| Mon., 10/17 | JV Field Hockey | Brien McMahon | Home - New Canaan HS-WTT #2 [Directions] | 6:00 p.m. | ||
| Mon., 10/17 | V Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | W 3-1 | 2:30 PM; 1 Bus (V & JV ride together) | |
| Mon., 10/17 | JV Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:30 p.m. | 2:30 PM; 1 Bus (V & JV ride together) | |
| Mon., 10/17 | FR Girls Volleyball | Fairfield Warde | Home - New Canaan HS-Main Gym [Directions] | 4:30 p.m. | ||
| Tue., 10/18 | FR Field Hockey | Wilton | Away - Wilton HS-Fuijitani Field -Turf [Directions] | 5:30 p.m. | 3:45 PM; 1 Bus | |
| Tue., 10/18 | V Girls Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | L 2-0 | 4:30 PM; 1 Bus | |
| Tue., 10/18 | JV Girls Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Tue., 10/18 | FR Girls Soccer | Fairfield Ludlowe | Home - Saxe MS-Field 1 [Directions] | 4:30 p.m. | ||
| Wed., 10/19 | V Boys Cross Country | FCIAC Championship | Home - Waveny Park [Directions] | 2:15 p.m. | ||
| Wed., 10/19 | V Girls Cross Country | FCIAC Championship | Home - Waveny Park [Directions] | 2:15 p.m. | ||
| Wed., 10/19 | V Girls Swimming and Diving | Darien | Home - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Wed., 10/19 | V Girls Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | L 3-0 | 2:45 PM; 1 Bus (V & JV ride together) | |
| Wed., 10/19 | JV Girls Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | 2:45 PM; 1 Bus (V & JV ride together) | |
| Wed., 10/19 | FR Girls Volleyball | Darien | Home - New Canaan HS-Main Gym [Directions] | 4:30 p.m. | ||
| Thu., 10/20 | FR Football | Greenwich | Away - Greenwich HS-Field 7 [Directions] | 4:15 p.m. | 2:40 PM; 1 Bus | |
| Thu., 10/20 | V Boys Soccer | Norwalk | Home - New Canaan HS-Dunning Stadium [Directions] | L 1-6 | ||
| Thu., 10/20 | JV Boys Soccer | Norwalk | Home - Saxe MS-Field 1 [Directions] | 4:30 p.m. | ||
| Thu., 10/20 | FR Boys Soccer | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 5:00 p.m. | 2:30 PM; 1 Bus | |
| Thu., 10/20 | V Field Hockey | Norwalk | Away - Norwalk HS-Testa Field [Directions] | W 5-1 | 3:30 PM; 1 Bus (V & JV ride together.) | |
| Thu., 10/20 | JV Field Hockey | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 5:00 p.m. | 3:30 PM; 1 Bus (V & JV ride together) | |
| Thu., 10/20 | FR Field Hockey | Norwalk | Home - New Canaan HS-WTT #2 [Directions] | 4:30 p.m. | ||
| Fri., 10/21 | V Football | Wilton | Away - Wilton HS-Fujitani Field - Turf [Directions] | W 45-0 | 5:15 PM; 1 Bus | |
| Fri., 10/21 | V Girls Volleyball | Trumbull | Home - New Canaan HS-Main Gym [Directions] | L 3-2 | ||
| Fri., 10/21 | JV Girls Volleyball | Trumbull | Home - New Canaan HS-Main Gym [Directions] | 4:30 p.m. | ||
| Fri., 10/21 | FR Girls Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 4:30 p.m. | 2:30 PM; 1 Bus | |
| Sat., 10/22 | JV Football | Wilton | Home - New Canaan HS-Dunning Stadium [Directions] | 10:00 a.m. | ||
| Sat., 10/22 | FR Field Hockey | Danbury | Home - New Canaan HS-WTT #2 [Directions] | Cancelled | ||
| Sat., 10/22 | V Girls Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | W 7-0 | 4:30 PM; 1 Bus | |
| Sat., 10/22 | JV Girls Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Sat., 10/22 | V Girls Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | W 3-0 | 11:15 AM; 1 Bus (V & JV ride together) | |
| Sat., 10/22 | JV Girls Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 2:30 p.m. | 11:15 AM; 1 Bus (V & JV ride together) | |
| Mon., 10/24 | V Boys Soccer | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | W 2-1 | 2:30 PM; 1 Bus | |
| Mon., 10/24 | JV Boys Soccer | Westhill | Away - Rippowan MS-Rippowam Turf Field [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Mon., 10/24 | FR Boys Soccer | Westhill | Home - Saxe MS-Field 1 [Directions] | 4:30 p.m. | ||
| Mon., 10/24 | V Girls Volleyball | Fairfield Ludlowe | Home - New Canaan HS-Main Gym [Directions] | W 3-2 | ||
| Mon., 10/24 | JV Girls Volleyball | Fairfield Ludlowe | Home - New Canaan HS-Main Gym [Directions] | 4:30 p.m. | ||
| Mon., 10/24 | FR Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:30 p.m. | 2:45 PM; 1 Bus | |
| Tue., 10/25 | FR Field Hockey | Ridgefield | Away - Ridgefield HS-Tiger Hollow Turf Field II [Directions] | 6:30 p.m. | 4:30 PM; 1 Bus | |
| Tue., 10/25 | V Girls Soccer | Westhill | Home - New Canaan HS-Dunning Stadium [Directions] | W 4-1 | ||
| Tue., 10/25 | JV Girls Soccer | Westhill | Home - Saxe MS-Field 1 [Directions] | 4:30 p.m. | ||
| Wed., 10/26 | V Field Hockey | Ridgefield | Home - New Canaan HS-Dunning Stadium [Directions] | W 2-1 | ||
| Wed., 10/26 | JV Field Hockey | Ridgefield | Home - New Canaan HS-Dunning Stadium [Directions] | 5:30 p.m. | ||
| Wed., 10/26 | FR Field Hockey | Greenwich | Home - New Canaan HS-WTT #2 [Directions] | 4:30 p.m. | 12:00 PM | |
| Wed., 10/26 | V Girls Volleyball | Norwalk | Home - New Canaan HS-Main Gym [Directions] | W 3-0 | ||
| Wed., 10/26 | JV Girls Volleyball | Norwalk | Home - New Canaan HS-Main Gym [Directions] | 4:30 p.m. | ||
| Thu., 10/27 | FR Football | Wilton | Away - Wilton HS-Fuijitani Field -Turf [Directions] | 6:00 p.m. | 4:30 PM; 1 Bus | |
| Thu., 10/27 | V Boys Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 6:30 p.m. | 4:30 PM; 1 Bus | |
| Thu., 10/27 | V Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | W 3-0 | 3:00 PM; 1 Bus (V & JV ride together.) | |
| Thu., 10/27 | JV Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:30 p.m. | 3:00 PM; 1 Bus (V & JV ride together.) | |
| Thu., 10/27 | FR Girls Volleyball | Norwalk | Home - New Canaan HS-Main Gym [Directions] | 4:30 p.m. | 3:15 PM; 1 Bus | |
| Fri., 10/28 | V Football | St. Joseph | Home - New Canaan HS-Dunning Stadium [Directions] | L 14-27 | ||
| Fri., 10/28 | FR Girls Volleyball | Westhill | Home - New Canaan HS-Main Gym [Directions] | 4:30 p.m. | ||
| Sat., 10/29 | V Boys Cross Country | CIAC Class L Championship | Away - Wickham Park | 9:35 a.m. | ||
| Sat., 10/29 | V Girls Cross Country | CIAC Class L Championship | Away - Wickham Park | 9:00 a.m. | ||
| Sat., 10/29 | V Field Hockey | Ridgefield | Home - New Canaan HS-Dunning Stadium [Directions] | W 3-2 | ||
| Sat., 10/29 | JV Girls Swimming and Diving | Greenwich, Brien McMahon, Danbury, Darien, Fairfield Ludlowe, Fairfield Warde, Norwalk/McMahon, Ridgefield, St. Joseph, Stamford, Staples, Trumbull, Westhill/Stamford, Wilton | Away - Greenwich HS-Pool | 10:15 a.m. | 8:00 AM; 1 Bus | |
| Mon., 10/31 | JV Football | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | Cancelled | 2:15 PM; 1 Bus | |
| Tue., 11/1 | V Boys Golf | CIAC Division I Championship | Away - Stanley GC | 9:00 a.m. | ||
| Tue., 11/1 | V Field Hockey | Darien | Home - Brien McMahon HS-Casagrande Field [Directions] | L 2-0 | 4:15 PM; 1 Bus | |
| Tue., 11/1 | V Girls Swimming and Diving | TBA, Brien McMahon, Danbury, Fairfield Ludlowe, Fairfield Warde, TBA, Norwalk/McMahon, Ridgefield, St. Joseph, Stamford, Staples, Trumbull, Westhill/Stamford, Wilton | Away - Greenwich HS-Pool | 5:15 p.m. | 2:30 PM; 1 Bus | |
| Tue., 11/1 | V Girls Swimming and Diving | Greenwich, Danbury, Darien, Fairfield Ludlowe, Fairfield Warde, Norwalk/McMahon, Ridgefield, St. Joseph, Staples, Trumbull, Westhill/Stamford, Wilton | Away - Greenwich HS-Pool | 5:15 p.m. | ||
| Tue., 11/1 | V Girls Volleyball | Westhill | Home - New Canaan HS-Main Gym [Directions] | 4:30 p.m. | ||
| Wed., 11/2 | V Girls Swimming and Diving | FCIAC Diving Championship | Away - Westhill HS-Westhill Pool | 5:00 p.m. | ||
| Thu., 11/3 | FR Football | Ridgefield | Home - New Canaan HS-Dunning Stadium [Directions] | 5:00 p.m. | ||
| Thu., 11/3 | V Girls Volleyball | Trumbull | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 7:00 p.m. | 4:30 PM; 1 Bus | |
| Fri., 11/4 | V Boys Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Fri., 11/4 | V Football | Fairfield Ludlowe | Home - New Canaan HS-Dunning Stadium [Directions] | W 42-20 | ||
| Fri., 11/4 | V Girls Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Fri., 11/4 | V Girls Swimming and Diving | TBA, Brien McMahon, Danbury, Fairfield Ludlowe, Fairfield Warde, TBA, Norwalk/McMahon, Ridgefield, St. Joseph, Stamford, Staples, Trumbull, Westhill/Stamford, Wilton | Away - Greenwich HS-Pool | 6:30 p.m. | 4:30 PM; 1 Bus | |
| Fri., 11/4 | V Girls Swimming and Diving | Greenwich, Danbury, Darien, Fairfield Ludlowe, Fairfield Warde, Norwalk/McMahon, Ridgefield, St. Joseph, Staples, Trumbull, Westhill/Stamford, Wilton | Away - Greenwich HS-Pool | 6:30 p.m. | ||
| Sat., 11/5 | JV Football | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 10:00 a.m. | 8:00 AM; 1 Bus | |
| Mon., 11/7 | V Boys Soccer | Norwich Free Academy | Away - Norwich Free Academy-Turf Field [Directions] | 2:00 p.m. | 10:45 AM; 1 Bus | |
| Mon., 11/7 | V Girls Volleyball | Brien McMahon | Home - New Canaan HS-Main Gym [Directions] | 3:30 p.m. | ||
| Wed., 11/9 | V Field Hockey | Staples | Home - New Canaan HS-Dunning Stadium [Directions] | W 2-1 | ||
| Wed., 11/9 | V Girls Swimming and Diving | CIAC Class L Diving Championships | Away - Middletown | 5:30 p.m. | 2:00 PM; 1 Van | |
| Thu., 11/10 | FR Football | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | 2:45 PM; 1 Bus | |
| Fri., 11/11 | V Field Hockey | Southington | Away - Southington HS-3 TURF FIELD [Directions] | W 3-0 | ||
| Sat., 11/12 | V Football | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | W 41-14 | 4:45 PM; 2 Buses | |
| Sat., 11/12 | JV Football | Fairfield Warde | Home - New Canaan HS-Dunning Stadium [Directions] | Cancelled | ||
| Sat., 11/12 | V Girls Swimming and Diving | CIAC Class L Trials | Away - Cornerstone Pool | 4:30 p.m. | ||
| Tue., 11/15 | V Field Hockey | Wilton | Away - Norwalk HS-Testa Field [Directions] | 6:00 p.m. | 4:00 PM; 1 Bus | |
| Tue., 11/15 | V Girls Swimming and Diving | CIAC Class L Final | Away | 6:00 p.m. | ||
| Thu., 11/17 | V Girls Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 11/19 | JV Football | Darien | Home - New Canaan HS-Dunning Stadium [Directions] | 10:30 a.m. | ||
| Sun., 11/20 | V Girls Swimming and Diving | CIAC State Open Swimming Championship | Away - Yale | 2:00 p.m. | ||
| Thu., 11/24 | V Football | Darien | Away - Darien HS-DHS Stadium Field [Directions] | W 13-10 | 8:00 AM; 2 Buses | |
| Tue., 11/29 | V Football | Naugatuck | Home - New Canaan HS-Dunning Stadium [Directions] | 6:30 p.m. | ||
| Wed., 11/30 | V Girls Ice Hockey | Greenwich Country Day | Away - Chelsea Piers - Field Side-South Rink | 3:15 p.m. | 2:40 PM; 1 Bus | |
| Sat., 12/3 | V Girls Ice Hockey | Greenwich (Scrim.) | Home - Darien Ice House-Ice Rink [Directions] | 6:40 p.m. | ||
| Tue., 12/6 | V Girls Basketball | Brien McMahon (Scrim.) | Home - New Canaan HS-Main Gym [Directions] | 3:30 p.m. | ||
| Wed., 12/7 | V Boys Ice Hockey | Fairfield Warde/Ludlowe (Scrim.) | Away - Wonderland of Ice-Stadium [Directions] | 8:45 p.m. | 6:45 PM; 1 Bus | |
| Thu., 12/8 | V Boys Basketball | Bethel (Scrim.) | Home - New Canaan HS-Main Gym [Directions] | 5:00 p.m. | ||
| Thu., 12/8 | V Girls Ice Hockey | West Haven/SHA | Home - Darien Ice House-Ice Rink [Directions] | W 6-3 | ||
| Sat., 12/10 | V Boys Basketball | Jonathan Law (Scrim.) | Away - Jonathan Law HS-James L. Richetelli Memorial Gymnasium [Directions] | 2:00 p.m. | 12:00 PM; 1 Bus | |
| Sat., 12/10 | V Football | Maloney | Away - Central Connecticut State University-Arute Field [Directions] | 2:00 p.m. | 10:00 AM; 2 Buses | |
| Sat., 12/10 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Darien Ice House-Ice Rink [Directions] | W 9-1 | ||
| Mon., 12/12 | V Boys Basketball | Crosby (Scrim.) | Away - Crosby HS-CHS - Augelli Court [Directions] | 4:30 p.m. | 2:40 PM; 1 Bus | |
| Mon., 12/12 | V Boys Ice Hockey | West Haven Coop | Away - West Haven HS-Bennett Rink [Directions] | W 7-0 | 2:45 PM; 1 Bus | |
| Wed., 12/14 | V Girls Ice Hockey | Darien | Home - Darien Ice House-Ice Rink [Directions] | L 0-7 | ||
| Thu., 12/15 | V Girls Basketball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | W 38-24 | 2:45 PM; 1 Bus (JV/V ride together) | |
| Thu., 12/15 | JV Girls Basketball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 4:30 p.m. | 2:45 PM; 1 Bus (JV/V ride together) | |
| Fri., 12/16 | V Boys Basketball | Wright Tech | Home - New Canaan HS-Main Gym [Directions] | W 74-37 | ||
| Fri., 12/16 | JV Boys Basketball | Wright Tech | Home - New Canaan HS-Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 12/16 | V Boys Ice Hockey | Fairfield Prep | Home - Darien Ice House-Ice Rink [Directions] | L 4-5(OT) | ||
| Fri., 12/16 | JV Boys Ice Hockey | St. Joseph | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | 8:00 p.m. | 5:40 PM; 1 Bus | |
| Fri., 12/16 | V Girls Ice Hockey | Greenwich | Away - Greenwich - Dorothy Hamill-Rink [Directions] | W 7-2 | 3:30 PM; 1 Bus | |
| Sat., 12/17 | V Boys Indoor Track | Wilton, Danbury, Norwalk | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:00 a.m. | ||
| Sat., 12/17 | V Wrestling | Pomperaug, Bacon Academy, Nonnewaug, Portland, Wethersfield | Away - Pomperaug HS-Auxiliary Gym | 9:00 a.m. | 6:30 AM; 1 Bus | |
| Sat., 12/17 | V Girls Basketball | Weston | Home - New Canaan HS-Main Gym [Directions] | W 38-29 | ||
| Sat., 12/17 | JV Girls Basketball | Weston | Home - New Canaan HS-Main Gym [Directions] | 1:00 p.m. | ||
| Sat., 12/17 | JV Girls Basketball | Weston | Home - New Canaan HS-Main Gym [Directions] | 2:00 p.m. | ||
| Sat., 12/17 | V Girls Indoor Track | Wilton, Danbury, Norwalk | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:00 a.m. | ||
| Sun., 12/18 | JV Boys Ice Hockey | Darien | Home - Darien Ice House-Ice Rink [Directions] | 6:40 p.m. | ||
| Mon., 12/19 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Darien Ice House-Ice Rink [Directions] | W 10-3 | ||
| Tue., 12/20 | FR Boys Basketball | Newtown | Away - Newtown HS-Gym [Directions] | 5:00 p.m. | 3:15 PM; 1 Bus | |
| Wed., 12/21 | V Boys Ice Hockey | Simsbury | Away - Simsbury - ISCC-Olympic [Directions] | W 8-3 | 4:15 PM; 1 Bus | |
| Wed., 12/21 | V Wrestling | Stamford | Away - Stamford HS-SHS Aux Gym [Directions] | 5:30 p.m. | 3:45 PM; 1 Bus | |
| Wed., 12/21 | V Girls Basketball | Bassick | Home - New Canaan HS-Main Gym [Directions] | W 53-9 | ||
| Wed., 12/21 | JV Girls Basketball | Bassick | Home - New Canaan HS-Main Gym [Directions] | 4:30 p.m. | ||
| Wed., 12/21 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | W 7-2 | 2:00 PM; 1 Bus | |
| Sat., 12/24 | V Wrestling | Norwalk, Fairfield Ludlowe, Westhill | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 9:00 a.m. | 12:15 PM; 1 Bus | |
| Mon., 12/26 | JV Wrestling | Greenwich, Norwalk, Trumbull | Home - New Canaan HS-Main Gym [Directions] | 9:15 a.m. | ||
| Wed., 12/28 | V Boys Basketball | New Milford | Home - New Canaan HS-Main Gym [Directions] | W 42-25 | ||
| Wed., 12/28 | JV Boys Ice Hockey | Xavier | Away - Cromwell-Upper Rink [Directions] | 4:20 p.m. | 1:45 PM; 1 Bus | |
| Thu., 12/29 | V Girls Basketball | Darien | Home - New Canaan HS-Main Gym [Directions] | W 49-30 | ||
| Thu., 12/29 | V Girls Ice Hockey | Simsbury | Home - Darien Ice House-Ice Rink [Directions] | Postponed | ||
| Fri., 12/30 | V Boys Basketball | Southington | Home - New Canaan HS-Main Gym [Directions] | W 54-51 | ||
| Sat., 12/31 | V Girls Ice Hockey | LaSalle Academy (RI) | Home - Darien Ice House-Ice Rink [Directions] | W 5-1 | ||
| Tue., 1/3 | V Boys Ice Hockey | Greenwich | Away - Greenwich - Dorothy Hamill-Rink [Directions] | W 6-2 | 2:30 PM; 1 Bus | |
| Tue., 1/3 | V Girls Basketball | Greenwich | Home - New Canaan HS-Main Gym [Directions] | W 43-42 | ||
| Tue., 1/3 | JV Girls Basketball | Greenwich | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/3 | FR Girls Basketball | Greenwich | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/4 | V Wrestling | Ridgefield | Home - New Canaan HS-Main Gym [Directions] | 7:00 p.m. | ||
| Wed., 1/4 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Conners - Stamford-Ice Rink [Directions] | L 2-3 | TBA; 1 Bus | |
| Thu., 1/5 | V Girls Gymnastics | Westhill, Darien, Stamford | Away - Westhill HS-New Gym [Directions] | 75.35 | 4:45 PM; 1 Van | |
| Fri., 1/6 | V Boys Basketball | Danbury | Home - New Canaan HS-Main Gym [Directions] | L 57-60(2OT) | ||
| Fri., 1/6 | JV Boys Basketball | Danbury | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/6 | FR Boys Basketball | Danbury | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/6 | V Boys Swimming and Diving | Danbury | Away - WCSU O'Neill Center Pool [Directions] | 4:00 p.m. | 2:15 PM; 1 Bus | |
| Fri., 1/6 | V Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | W 34-29 | 4:00 PM; 1 Bus (JV/V ride together) | |
| Fri., 1/6 | JV Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 5:30 p.m. | 4:00 PM; 1 Bus (JV/V ride together) | |
| Fri., 1/6 | FR Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Fri., 1/6 | V Girls Ice Hockey | Suffield Coop | Away - Simsbury - ISCC-Olympic [Directions] | W 7-1 | 2:30 PM; 1 Bus | |
| Sat., 1/7 | V Boys Ice Hockey | Ridgefield | Home - Darien Ice House-Ice Rink [Directions] | W 6-1 | ||
| Sat., 1/7 | V Boys Indoor Track | Wilton, Darien, Ridgefield | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:00 a.m. | ||
| Sat., 1/7 | V Wrestling | Amity, Newington, North Haven, New Haven Wrestling | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 9:00 a.m. | 6:30 AM; 1 Bus | |
| Sat., 1/7 | V Girls Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | L 26-29 | 12:30 PM; 1 Bus (JV/V ride together) | |
| Sat., 1/7 | JV Girls Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 2:00 p.m. | 12:30 PM; 1 Bus (JV & V ride together) | |
| Sat., 1/7 | FR Girls Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 12:30 p.m. | 10:30 AM; 1 Bus | |
| Sat., 1/7 | V Girls Indoor Track | Wilton, Darien, Ridgefield | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:00 a.m. | ||
| Sun., 1/8 | JV Boys Ice Hockey | Darien | Home - Darien Ice House-Ice Rink [Directions] | 6:40 p.m. | ||
| Mon., 1/9 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Home - Darien Ice House-Ice Rink [Directions] | W 7-1 | ||
| Tue., 1/10 | V Boys Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | L 67-68(OT) | 3:15 PM; 1 Bus (JV/V ride together) | |
| Tue., 1/10 | JV Boys Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 5:30 p.m. | 3:15 PM; 1 Bus (JV/V ride together) | |
| Tue., 1/10 | FR Boys Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:00 p.m. | 2:35 PM; 1 Bus | |
| Tue., 1/10 | V Girls Basketball | Staples | Home - New Canaan HS-Main Gym [Directions] | W 45-37 | ||
| Tue., 1/10 | JV Girls Basketball | Staples | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/10 | FR Girls Basketball | Staples | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/10 | V Girls Gymnastics | Wilton, Darien | Away - Wilton HS-Aux Gym [Directions] | 97.25 | 3:00 PM; 1 Van | |
| Wed., 1/11 | V Boys Ice Hockey | Darien | Home - Darien Ice House-Ice Rink [Directions] | T 3-3(OT) | ||
| Wed., 1/11 | V Boys Swimming and Diving | Ridgefield | Home - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Wed., 1/11 | V Wrestling | Darien | Home - New Canaan HS-Main Gym [Directions] | 7:00 p.m. | ||
| Wed., 1/11 | V Girls Gymnastics | Fairfield Ludlowe, Nonnewaug | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:30 p.m. | 4:30 PM; 1 Van | |
| Thu., 1/12 | V Boys Ice Hockey | St. Joseph | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | W 7-2 | 6:00 PM; 1 Bus | |
| Fri., 1/13 | V Boys Basketball | Wilton | Home - New Canaan HS-Main Gym [Directions] | W 59-56(2OT) | ||
| Fri., 1/13 | JV Boys Basketball | Wilton | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/13 | FR Boys Basketball | Wilton | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/13 | V Girls Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | L 39-41(OT) | 3:15 PM; 1 Bus (JV/V teams ride together) | |
| Fri., 1/13 | JV Girls Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | 3:15 PM; 1 Bus (JV/V teams ride together) | |
| Fri., 1/13 | JV Girls Ice Hockey | Greenwich | Home - New Canaan Winter Club-Rink [Directions] | 5:40 p.m. | ||
| Sat., 1/14 | JV Boys Ice Hockey | Notre Dame-West Haven | Away - West Haven HS-Bennett Rink [Directions] | 1:00 p.m. | 11:00 AM; 1 Bus | |
| Sat., 1/14 | V Boys Indoor Track | Wilton, Brien McMahon, Ridgefield | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:00 a.m. | ||
| Sat., 1/14 | V Wrestling | Notre Dame-West Haven, Fitch, St. Joseph, Stratford | Away - Notre Dame HS-Gym [Directions] | 9:00 a.m. | 6:30 AM; 1 Bus | |
| Sat., 1/14 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Darien Ice House-Ice Rink [Directions] | W 8-0 | ||
| Sat., 1/14 | V Girls Indoor Track | Wilton, Brien McMahon, Ridgefield | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:00 a.m. | ||
| Mon., 1/16 | V Boys Ice Hockey | Barrington (RI) | Home - Darien Ice House-Ice Rink [Directions] | W 6-1 | ||
| Mon., 1/16 | V Wrestling | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:00 p.m. | 3:00 PM; 1 Bus | |
| Mon., 1/16 | V Girls Ice Hockey | Simsbury | Home - Darien Ice House-Ice Rink [Directions] | W 2-1 | ||
| Tue., 1/17 | V Boys Basketball | St. Joseph | Home - New Canaan HS-Main Gym [Directions] | W 58-51 | ||
| Tue., 1/17 | JV Boys Basketball | St. Joseph | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/17 | FR Boys Basketball | St. Joseph | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/17 | V Girls Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | L 42-56 | 3:15 PM; 1 Bus (JV/V ride together) | |
| Tue., 1/17 | JV Girls Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 5:30 p.m. | 4:00 PM; 1 Bus (JV/V ride together) | |
| Tue., 1/17 | FR Girls Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:00 p.m. | 2:35 PM; 1 Bus | |
| Wed., 1/18 | V Boys Ice Hockey | Hamden | Home - Darien Ice House-Ice Rink [Directions] | W 6-0 | ||
| Wed., 1/18 | JV Boys Ice Hockey | Greenwich | Away - Greenwich - Dorothy Hamill-Rink [Directions] | 7:00 p.m. | 5:00 PM; 1 Bus | |
| Wed., 1/18 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Home - New Canaan YMCA-Pool [Directions] | 2:00 p.m. | 3:45 PM; 1 Bus | |
| Wed., 1/18 | V Wrestling | Trumbull | Home - New Canaan HS-Main Gym [Directions] | 7:00 p.m. | ||
| Thu., 1/19 | V Girls Gymnastics | Greenwich | Away - Greenwich YWCA [Directions] | 108.25 | 4:30 PM; 1 Van | |
| Fri., 1/20 | V Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | L 28-36 | 3:00 PM; 1 Bus (JV/V ride together) | |
| Fri., 1/20 | JV Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 5:30 p.m. | 3:00 PM; 1 Bus (JV/V ride together) | |
| Fri., 1/20 | FR Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:00 p.m. | 2:35 PM; 1 Bus | |
| Fri., 1/20 | V Wrestling | Fairfield Warde, Foran, Shelton | Away - Fairfield Warde HS-Small Gym [Directions] | 4:00 p.m. | 2:00 PM; 1 Bus | |
| Fri., 1/20 | V Girls Basketball | Fairfield Warde | Home - New Canaan HS-Main Gym [Directions] | W 51-49(2OT) | ||
| Fri., 1/20 | JV Girls Basketball | Fairfield Warde | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/20 | FR Girls Basketball | Fairfield Warde | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 1/21 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland of Ice-Stadium [Directions] | L 1-3 | 4:45 PM; 1 Bus | |
| Sat., 1/21 | V Boys Indoor Track | Wilton, Brien McMahon, St. Joseph | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:00 a.m. | ||
| Sat., 1/21 | JV Wrestling | Patton JV Tournament | Away - Danbury HS-Main Gym | 9:30 a.m. | 7:15 AM; 1 Bus | |
| Sat., 1/21 | V Girls Indoor Track | Wilton, Brien McMahon, St. Joseph | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:00 a.m. | ||
| Sun., 1/22 | JV Boys Ice Hockey | Fairfield Prep | Home - Darien Ice House-Ice Rink [Directions] | Postponed | ||
| Mon., 1/23 | V Girls Ice Hockey | Greenwich | Home - Darien Ice House-Ice Rink [Directions] | W 6-0 | ||
| Tue., 1/24 | V Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | L 45-49 | 3:30 PM; 1 Bus (JV/V ride together) | |
| Tue., 1/24 | JV Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:30 p.m. | 3:30 PM; 1 Bus (JV/V ride together) | |
| Tue., 1/24 | FR Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:00 p.m. | 2:35 PM; 1 Bus | |
| Tue., 1/24 | V Girls Basketball | Ridgefield | Home - New Canaan HS-Main Gym [Directions] | W 50-45 | ||
| Tue., 1/24 | JV Girls Basketball | Ridgefield | Home - New Canaan HS-Main Gym [Directions] | 4:30 p.m. | ||
| Wed., 1/25 | V Boys Ice Hockey | Westhill/Stamford | Away - Terry Conners - Stamford-Ice Rink [Directions] | W 6-3 | 6:40 PM; 1 Bus | |
| Wed., 1/25 | V Boys Swimming and Diving | Westhill/Stamford | Home - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Wed., 1/25 | V Wrestling | Brien McMahon | Home - New Canaan HS-Main Gym [Directions] | 7:00 p.m. | ||
| Fri., 1/27 | V Boys Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | W 72-26 | 4:00 PM; 1 Bus (JV/V ride together) | |
| Fri., 1/27 | JV Boys Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 5:30 p.m. | 4:00 PM; 1 Bus (JV/V ride together) | |
| Fri., 1/27 | FR Boys Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:00 p.m. | 2:35 PM; 1 Bus | |
| Fri., 1/27 | V Boys Swimming and Diving | Trumbull | Home - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Fri., 1/27 | V Girls Basketball | Westhill | Home - New Canaan HS-Main Gym [Directions] | W 45-19 | ||
| Fri., 1/27 | JV Girls Basketball | Westhill | Home - New Canaan HS-Main Gym [Directions] | 4:30 p.m. | ||
| Sat., 1/28 | V Boys Ice Hockey | Greenwich | Home - Darien Ice House-Ice Rink [Directions] | W 4-0 | ||
| Sat., 1/28 | V Boys Indoor Track | Wilton, Brien McMahon, St. Joseph | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:00 a.m. | ||
| Sat., 1/28 | V Wrestling | Brookfield Wrestling Tournament | Away - Brookfield HS-BHS Small Gym | 9:30 a.m. | 6:45 AM; 1 Bus | |
| Sat., 1/28 | V Girls Gymnastics | Trumbull | Away - Next Dimension Gymnastics-Next Dimension [Directions] | 81.2 | 3:30 PM; 1 Van | |
| Sat., 1/28 | V Girls Gymnastics | St. Joseph | Away - St. Joseph HS-Next Dimensions [Directions] | 81.2 | ||
| Sat., 1/28 | V Girls Ice Hockey | Stamford/Westhill/Staples | Home - Darien Ice House-Ice Rink [Directions] | W 6-0 | ||
| Sat., 1/28 | V Girls Indoor Track | Wilton, Brien McMahon, St. Joseph | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:00 a.m. | ||
| Sun., 1/29 | JV Boys Ice Hockey | St. Joseph | Home - Darien Ice House-Ice Rink [Directions] | 7:35 p.m. | ||
| Mon., 1/30 | V Boys Ice Hockey | St. Joseph | Home - Darien Ice House-Ice Rink [Directions] | W 4-1 | ||
| Tue., 1/31 | V Boys Basketball | Stamford | Home - New Canaan HS-Main Gym [Directions] | L 25-36 | ||
| Tue., 1/31 | JV Boys Basketball | Stamford | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/31 | FR Boys Basketball | Stamford | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/31 | V Boys Indoor Track | Senior Meet | Away - Bethel HS-Track and Field Training Center | 4:00 p.m. | ||
| Tue., 1/31 | V Girls Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | L 27-34 | 4:30 PM; 1 Bus | |
| Tue., 1/31 | JV Girls Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | 4:30 PM; 1 Bus (JV/V ride together.) | |
| Tue., 1/31 | FR Girls Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | 2:45 PM; 1 Bus | |
| Tue., 1/31 | V Girls Indoor Track | Senior Meet | Away - Bethel HS-Track and Field Training Center | 4:00 p.m. | ||
| Wed., 2/1 | JV Boys Ice Hockey | Fairfield Prep | Away - Wonderland of Ice-Stadium [Directions] | 6:00 p.m. | 4:10 PM; 1 Bus | |
| Wed., 2/1 | V Boys Swimming and Diving | Wilton | Away - Wilton YMCA [Directions] | 3:40 p.m. | 2:35 PM; 1 Bus | |
| Wed., 2/1 | V Wrestling | Wilton | Away - Wilton HS-Nicholas Zeoli Fieldhouse [Directions] | 6:00 p.m. | 4:00 PM; 1 Bus | |
| Thu., 2/2 | V Boys Indoor Track | FCIAC Championships | Away - Floyd Little Athletic Center-Field House | 5:00 p.m. | 2:35 PM; 1 Bus (B/G ride together.) | |
| Pending change awaiting acceptance by one or more parties involved: Facility to Not Listed-Floyd Little Athletic Center | ||||||
| Thu., 2/2 | V Girls Indoor Track | FCIAC, Bridgeport Central, Brien McMahon, Danbury, Darien, Fairfield Ludlowe, Fairfield Warde, Greenwich, Norwalk, Ridgefield, St. Joseph, Stamford, Staples, Trumbull, Westhill, Wilton | Away - Floyd Little Athletic Center-Field House | 5:00 p.m. | 2:35 PM; 1 Bus (B/G ride together.) | |
| Pending change awaiting acceptance by one or more parties involved: Facility to Not Listed-Floyd Little Athletic Center | ||||||
| Fri., 2/3 | V Boys Basketball | Norwalk | Home - New Canaan HS-Main Gym [Directions] | W 62-32 | ||
| Fri., 2/3 | JV Boys Basketball | Norwalk | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/3 | FR Boys Basketball | Norwalk | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 2/3 | V Boys Swimming and Diving | Darien | Away - Darien YMCA [Directions] | 3:00 p.m. | 2:00 PM; 1 Bus | |
| Fri., 2/3 | V Girls Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | L 45-50 | 3:45 PM; 1 Bus (JV/V ride together) | |
| Fri., 2/3 | JV Girls Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:30 p.m. | 3:45 PM; 1 Bus (JV/V ride together) | |
| Sat., 2/4 | V Boys Basketball | Harding | Home - New Canaan HS-Main Gym [Directions] | W 66-23 | ||
| Sat., 2/4 | JV Boys Basketball | Harding | Home - New Canaan HS-Main Gym [Directions] | 1:30 p.m. | ||
| Sat., 2/4 | FR Boys Basketball | Harding | Home - New Canaan HS-Main Gym [Directions] | 12:00 p.m. | ||
| Sat., 2/4 | V Boys Ice Hockey | Notre Dame-West Haven | Away - West Haven HS-Bennett Rink [Directions] | L 0-2 | 3:30 PM; 1 Bus | |
| Sat., 2/4 | V Girls Ice Hockey | Darien | Away - Darien Ice House-Ice Rink [Directions] | L 1-3 | ||
| Sun., 2/5 | JV Boys Ice Hockey | Trumbull | Home - Darien Ice House-Ice Rink [Directions] | 7:35 p.m. | ||
| Mon., 2/6 | V Girls Ice Hockey | Simsbury | Away - Simsbury Farms Ice Rink-Ice Rink [Directions] | W 5-0 | 1:45 PM; 1 Bus | |
| Tue., 2/7 | V Boys Basketball | Bridgeport Central | Home - New Canaan HS-Main Gym [Directions] | W 42-35 | ||
| Tue., 2/7 | JV Boys Basketball | Bridgeport Central | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/7 | FR Boys Basketball | Bridgeport Central | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/7 | V Girls Basketball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | W 71-34 | 3:30 PM; 1 Bus (JV/V ride together) | |
| Tue., 2/7 | JV Girls Basketball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | 5:30 p.m. | 3:45 PM; 1 Bus (JV/V ride together) | |
| Tue., 2/7 | FR Girls Basketball | Bridgeport Central | Away - Bridgeport Central HS-The Barry McLeod Court [Directions] | 4:00 p.m. | 2:35 PM; 1 Bus | |
| Wed., 2/8 | V Boys Ice Hockey | Ridgefield | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | W 1-0 | 4:30 PM; 1 Bus | |
| Wed., 2/8 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Away - Norwalk HS-Pat Spinola Natatorium [Directions] | 4:00 p.m. | 2:35 PM; 1 Bus | |
| Wed., 2/8 | V Wrestling | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:00 p.m. | 2:00 PM; 1 Bus | |
| Wed., 2/8 | V Girls Ice Hockey | Avon | Away - Newington-Red Rink [Directions] | W 2-1 | 2:00 PM; 1 Bus | |
| Thu., 2/9 | JV Boys Basketball | Darien | Home - New Canaan HS-Main Gym [Directions] | 7:00 p.m. | 12:00 PM | |
| Thu., 2/9 | FR Boys Basketball | Darien | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 2/9 | V Girls Basketball | Harding | Away - Warren Harding HS-Gym [Directions] | W 62-19 | 3:45 PM; 1 Bus (JV/V ride together) | |
| Thu., 2/9 | JV Girls Basketball | Harding | Away - Warren Harding HS-Gym [Directions] | 5:30 p.m. | 3:45 PM; 1 Bus (JV/V ride together) | |
| Thu., 2/9 | FR Girls Basketball | Darien | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 2/9 | V Girls Gymnastics | Staples, Greenwich, Norwalk | Away - Staples HS-Westport YMCA [Directions] | 80.95 | 5:00 PM; 1 Van | |
| Fri., 2/10 | V Boys Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | W 47-35 | 5:15 PM; 1 Bus | |
| Fri., 2/10 | JV Boys Ice Hockey | Notre Dame-West Haven | Home - Sono Ice House-Main Rink [Directions] | 8:50 p.m. | ||
| Fri., 2/10 | V Boys Indoor Track | CIAC Class L Championships | Away - Floyd Little Athletic Center | 4:30 p.m. | ||
| Fri., 2/10 | V Boys Swimming and Diving | Greenwich | Home - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Fri., 2/10 | V Wrestling | Bridgeport Central, Brien McMahon, Danbury, Darien, FCIAC, Fairfield Ludlowe, Fairfield Warde, Greenwich, Norwalk, Ridgefield, St. Joseph, Stamford, Staples, Trumbull, Westhill, Wilton | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 2/10 | V Girls Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | W 36-25 | 2:45 PM; 1 Bus | |
| Fri., 2/10 | JV Girls Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | 2:45 PM; 1 Bus (JV/V ride together) | |
| Fri., 2/10 | FR Girls Basketball | Harding | Away - Warren Harding HS-Gym [Directions] | Cancelled | 2:40 PM; 1 Bus | |
| Fri., 2/10 | V Girls Ice Hockey | Guilford Coop | Away - East Haven HS-Veterans Rink [Directions] | W 3-0 | 5:30 PM; 1 Bus | |
| Fri., 2/10 | V Girls Indoor Track | CIAC Class L Championships | Away - Floyd Little Athletic Center | 4:30 p.m. | ||
| Sat., 2/11 | V Boys Ice Hockey | Darien | Away - Darien Ice House-Ice Rink [Directions] | W 4-1 | ||
| Sat., 2/11 | V Wrestling | FCIAC | Away - New Canaan HS-Main Gym | 8:00 a.m. | ||
| Mon., 2/13 | V Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | L 31-34 | 3:45 PM; 1 Bus (JV/V ride together) | |
| Mon., 2/13 | JV Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 5:30 p.m. | 3:45 PM; 1 Bus (JV/V ride together) | |
| Mon., 2/13 | FR Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:00 p.m. | 2:40 PM; 1 Bus | |
| Mon., 2/13 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Home - Darien Ice House-Ice Rink [Directions] | L 1-2 | ||
| Mon., 2/13 | JV Boys Ice Hockey | Trumbull | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | Cancelled | 6:50 PM; 1 Bus | |
| Mon., 2/13 | V Girls Basketball | Brien McMahon | Home - New Canaan HS-Main Gym [Directions] | W 42-29 | ||
| Mon., 2/13 | JV Girls Basketball | Brien McMahon | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/15 | V Boys Basketball | Fairfield Ludlowe | Home - New Canaan HS-Main Gym [Directions] | W 62-30 | ||
| Wed., 2/15 | JV Boys Basketball | Fairfield Ludlowe | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/15 | FR Boys Basketball | Fairfield Ludlowe | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/15 | JV Boys Ice Hockey | Fairfield Prep | Home - Terry Conners - Stamford-Ice Rink [Directions] | 8:00 p.m. | ||
| Wed., 2/15 | V Boys Swimming and Diving | Staples | Home - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Wed., 2/15 | V Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | L 29-45 | 3:45 PM; 1 Bus (JV/V ride together) | |
| Wed., 2/15 | JV Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:30 p.m. | 3:45 PM; 1 Bus (JV/V ride together) | |
| Wed., 2/15 | FR Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:00 p.m. | 2:35 PM; 1 Bus | |
| Wed., 2/15 | V Girls Ice Hockey | Greenwich Academy | Away - Chelsea Piers - Field Side-North Rink | T 2-2 | 2:15 PM; 1 Bus | |
| Fri., 2/17 | V Wrestling | CIAC L Championship | Away - Guilford | 4:00 p.m. | ||
| Sat., 2/18 | V Boys Basketball | Ledyard | Away - Ledyard HS-Judy Standish Gymnasium [Directions] | W 66-48 | 12:30 PM; 1 Bus (JV/V ride together) | |
| Sat., 2/18 | JV Boys Basketball | Ledyard | Away - Ledyard HS-Judy Standish Gymnasium [Directions] | 3:30 p.m. | 12:30 PM; 1 Bus (JV/V ride together) | |
| Sat., 2/18 | V Boys Ice Hockey | Notre Dame-Fairfield | Home - Darien Ice House-Ice Rink [Directions] | W 8-1 | ||
| Sat., 2/18 | V Boys Indoor Track | CIAC State Open Championships | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/18 | V Wrestling | CIAC L Championship | Away - Guilford | 10:30 a.m. | ||
| Sat., 2/18 | V Girls Basketball | Fairfield Warde | Away - Staples HS-Staples Gym [Directions] | 1:00 p.m. | 11:30 AM; 1 Bus | |
| Sat., 2/18 | V Girls Ice Hockey | East Catholic Coop | Home - Darien Ice House-Ice Rink [Directions] | W 4-0 | ||
| Sat., 2/18 | V Girls Indoor Track | CIAC State Open Championships | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sun., 2/19 | JV Boys Ice Hockey | Ridgefield | Away - Danbury Ice Arena-TBA [Directions] | 6:00 p.m. | 4:15 PM; 1 Bus | |
| Mon., 2/20 | V Boys Basketball | Trumbull | Home - New Canaan HS-Main Gym [Directions] | L 40-42 | ||
| Mon., 2/20 | JV Boys Basketball | Trumbull | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/20 | FR Boys Basketball | Trumbull | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 2/20 | V Boys Ice Hockey | Xavier | Home - Darien Ice House-Ice Rink [Directions] | T 2-2 | ||
| Tue., 2/21 | JV Boys Ice Hockey | Xavier | Home - Terry Conners - Stamford-Ice Rink [Directions] | 2:00 p.m. | ||
| Tue., 2/21 | JV Girls Ice Hockey | New Canaan Country Day | Away - New Canaan Winter Club-Rink | Cancelled | 12:00 PM | |
| Wed., 2/22 | V Boys Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | W 64-52 | 3:30 PM; 1 Bus (JV/V ride together) | |
| Wed., 2/22 | JV Boys Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | 3:30 PM; 1 Bus (JV/V ride together) | |
| Wed., 2/22 | FR Boys Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | 2:35 PM; 1 Bus | |
| Wed., 2/22 | V Girls Ice Hockey | Stamford/Westhill/Staples | Home - Darien Ice House-Ice Rink [Directions] | 7:40 p.m. | ||
| Thu., 2/23 | V Boys Ice Hockey | LaSalle Academy (RI) | Away - La Salle Academy-Smithfield Ice Arena | L 1-3 | 12:00 PM; 1 Bus | |
| Fri., 2/24 | V Wrestling | CIAC State Open | Away - Floyd Little Athletic Center | 12:45 p.m. | ||
| Sat., 2/25 | V Boys Basketball | Ridgefield | Away - Fairfield Warde HS-Gym [Directions] | 7:00 p.m. | ||
| Sat., 2/25 | V Boys Ice Hockey | St. Joseph | Home - Darien Ice House-Ice Rink [Directions] | 2:00 p.m. | ||
| Sat., 2/25 | JV Boys Ice Hockey | Darien | Away - Stamford Twin Rinks-East [Directions] | 8:05 p.m. | 7:10 PM; 1 Bus (Per Coaches - No Bus to this location.) | |
| Sat., 2/25 | V Wrestling | CIAC State Open | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Sat., 2/25 | V Girls Gymnastics | CIAC Divisional Championships | Away - Jonathan Law | TBA | ||
| Sat., 2/25 | V Girls Ice Hockey | Darien | Away - Darien Ice House-Ice Rink [Directions] | 4:30 p.m. | ||
| Mon., 2/27 | V Girls Basketball | WCA | Home - New Canaan HS-Main Gym [Directions] | 4:30 p.m. | ||
| Tue., 2/28 | V Boys Swimming and Diving | FCIAC Swim Trial Boys | Away - Greenwich HS-Pool | 5:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 3/1 | ||||||
| Wed., 3/1 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland of Ice-Stadium [Directions] | 7:00 p.m. | 4:40 PM; 1 Bus | |
| Wed., 3/1 | JV Boys Ice Hockey | Greenwich | Home - Blake Field - New Haven-Walker Rink [Directions] | 6:30 p.m. | 4:15 PM; 1 Bus | |
| Thu., 3/2 | V Girls Basketball | New Milford | Away - New Milford HS-Main Gym - NMHS [Directions] | 6:30 p.m. | 4:15 PM; 1 Bus | |
| Thu., 3/2 | V Girls Ice Hockey | Mercy/NW Catholic/East Hampton | Home - Darien Ice House-Ice Rink [Directions] | 8:00 p.m. | ||
| Fri., 3/3 | JV Boys Ice Hockey | Darien | Home - Blake Field - New Haven-Walker Rink [Directions] | 6:30 p.m. | 4:00 PM; 1 Bus | |
| Fri., 3/3 | V Boys Swimming and Diving | Greenwich, Danbury, Darien, Farfield Ludlowe/Warde, Fairfield Warde, TBA, Norwalk/Brien McMahon, Ridgefield, St. Joseph, Staples, Trumbull, Westhill/Stamford, Wilton | Away - Greenwich HS-Pool | 6:30 p.m. | 3:15 PM; 1 Bus | |
| Pending change awaiting acceptance by one or more parties involved: Time to 5:30 p.m. | ||||||
| Sat., 3/4 | V Girls Gymnastics | CIAC State Open | Away - New Milford | 4:00 p.m. | ||
| Sat., 3/4 | V Girls Ice Hockey | Avon | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | 7:50 p.m. | 5:15 PM; 1 Bus | |
| Tue., 3/7 | V Boys Basketball | Hamden | Home - New Canaan HS-Main Gym [Directions] | 6:30 p.m. | ||
| Wed., 3/8 | V Boys Ice Hockey | Hamden | Home - Darien Ice House-Ice Rink [Directions] | 5:00 p.m. | ||
| Thu., 3/9 | V Boys Basketball | St. Bernard | Away - St. Bernard School-Powers Gym [Directions] | 6:00 p.m. | 12:00 PM | |
| Thu., 3/9 | V Boys Swimming and Diving | CIAC Class L Diving Championships | Away - Sheehan | 5:30 p.m. | ||
| Sat., 3/11 | V Boys Ice Hockey | Darien | Home - Sacred Heart University-Martire Arena [Directions] | 1:00 p.m. | ||
| Sun., 3/12 | V Boys Swimming and Diving | CIAC Class L Trials | Away - Cornerstone Pool | 3:15 p.m. | ||
| Thu., 3/16 | V Boys Ice Hockey | Notre Dame-West Haven | Away - Quinnipiac University-TD Bank Sports Center [Directions] | 8:00 p.m. | 5:00 PM; 1 Bus | |
| Thu., 3/16 | V Boys Swimming and Diving | CIAC Class L Finals | Away - Cornerstone Pool | 6:00 p.m. | ||
| Fri., 3/17 | V Boys Swimming and Diving | CIAC Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/18 | V Boys Swimming and Diving | CIAC State Open Championship | Away - Yale | 1:00 p.m. | ||
| Fri., 3/24 | V Girls Lacrosse | Morristown (NJ) (Scrim.) | Home - New Canaan HS-Dunning Stadium [Directions] | 6:00 p.m. | ||
| Sat., 3/25 | V Boys Lacrosse | Niskayuna (NY) (Scrim.) | Home - New Canaan HS-Dunning Stadium [Directions] | 2:00 p.m. | ||
| Sat., 3/25 | V Boys Volleyball | Joel Barlow, Fairfield Ludlowe, Glastonbury, Iona Prep (NY), Pomperaug, Simsbury, Staples, Trumbull | Away - Joel Barlow HS-Lower Gym | 10:00 a.m. | 8:15 AM; 1 Bus | |
| Sat., 3/25 | V Girls Lacrosse | Play Day - Girls Lax | Away - Staples HS-Ginny Parker Field | 9:00 a.m. | 7:30 AM; 1 Bus | |
| Sun., 3/26 | V Baseball | Greenwich (Scrim.) | Away - Norwalk HS-Callahan Complex at Nathan Hale Upper [Directions] | 1:30 p.m. | 9:15 AM; 1 Bus | |
| Sun., 3/26 | V Baseball | Norwalk (Scrim.) | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 4:00 p.m. | 9:15 AM; 1 Bus | |
| Mon., 3/27 | V Boys Lacrosse | Rye (NY) (Scrim.) | Away - Rye HS-Turf | 5:00 p.m. | 2:45 PM; 1 Bus | |
| Tue., 3/28 | V Baseball | Newtown (Scrim.) | Away - Newtown HS-Nighthawk Ball Park [Directions] | 4:15 p.m. | 2:35 PM; 1 Bus | |
| Tue., 3/28 | V Softball | St. Lukes (Scrim.) | Away - St Lukes School-upper field #1 | 4:30 p.m. | ||
| Wed., 3/29 | V Baseball | Wilton (Scrim.) | Home - Mead Park-Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 3/29 | V Softball | Westhill (Scrim.) | Home - Waveny Park-Orchard Field [Directions] | 4:00 p.m. | ||
| Thu., 3/30 | V Boys Tennis | Brunswick School (Scrim.) | Away - Brunswick School | TBA | 2:45 PM, Dismiss TBA; 1 Bus | |
| Thu., 3/30 | V Softball | Staples (Scrim.) | Away - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Sat., 4/1 | V Boys Lacrosse | Mamaroneck (NY) | Away - Mamaroneck HS-Field | W 14-9 | 10:45 AM; 1 Bus | |
| Sat., 4/1 | JV Boys Lacrosse | Mamaroneck (NY) | Away - Mamaroneck HS-Field | 11:00 a.m. | 9:00 AM; 1 Bus | |
| Sat., 4/1 | V Boys Volleyball | Pre-Season Boys Volleyball | Away - Connecticut Sports Center | 8:00 a.m. | 6:30 AM; 1 Bus | |
| Mon., 4/3 | V Baseball | Weston | Away - Weston HS-Revson #1 (Varsity) [Directions] | W 13-2 | 2:30 PM; 1 Bus (JV/V ride together.) | |
| Mon., 4/3 | JV Baseball | Weston | Away - Weston HS-Revson #2 (JV) [Directions] | W 19-1 | 2:30 PM; 1 Bus (JV/V ride together.) | |
| Mon., 4/3 | V Boys Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | W 3-0 | 2:40 PM; 1 Bus (JV/V ride together) | |
| Mon., 4/3 | JV Boys Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | 2:40 PM; 1 Bus (JV/V ride together) | |
| Mon., 4/3 | V Softball | Jonathan Law | Home - Waveny Park-Orchard Field [Directions] | L 1-12 | ||
| Tue., 4/4 | V Boys Lacrosse | Cheshire | Away - Cheshire HS-Cheshire High School Main Game field [Directions] | W 7-6 | 3:15 PM; 1 Bus | |
| Tue., 4/4 | JV Boys Lacrosse | Cheshire | Away - Cheshire HS-Grass Fields [Directions] | 4:30 p.m. | 2:30 PM; 1 Bus | |
| Tue., 4/4 | FR Boys Lacrosse | Greenwich | Home - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Tue., 4/4 | V Boys Outdoor Track | Harding, Bassick, Bridgeport Central | Away - Warren Harding HS-Lewis Field [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus (B/G together) | |
| Tue., 4/4 | V Girls Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | W 18-4 | 2:30 PM; 1 Bus | |
| Tue., 4/4 | JV Girls Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 5:30 p.m. | 4:00 PM; 1 Bus | |
| Tue., 4/4 | FR Girls Lacrosse | Westhill | Home - New Canaan HS-WTT #2 [Directions] | Cancelled | ||
| Tue., 4/4 | V Girls Outdoor Track | Harding, Bassick, Bridgeport Central | Away - Warren Harding HS-Lewis Field [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Wed., 4/5 | V Baseball | New Fairfield | Home - Mead Park-Baseball Field [Directions] | W 5-4 | ||
| Wed., 4/5 | JV Baseball | New Fairfield | Home - Waveny Park-Coppo Field [Directions] | L 6-16 | ||
| Wed., 4/5 | V Boys Volleyball | Joel Barlow | Home - New Canaan HS-Main Gym [Directions] | L 0-3 | ||
| Wed., 4/5 | JV Girls Lacrosse | Wilton | Away - Wilton HS-Lilly Field [Directions] | 4:30 p.m. | 3:15 PM; 1 Bus | |
| Wed., 4/5 | V Softball | Brookfield | Away - Brookfield HS-BHS Softball Field [Directions] | W 9-2 | 2:35 PM; 1 Bus | |
| Thu., 4/6 | FR Boys Lacrosse | Trumbull | Away - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Thu., 4/6 | V Boys Tennis | Fairfield Prep (Scrim.) | Home - New Canaan HS-NCHS Tennis Courts [Directions] | 4:15 p.m. | ||
| Thu., 4/6 | FR Girls Lacrosse | Trumbull | Home - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Sat., 4/8 | V Baseball | Lyman Hall | Away - Pat Wall Field-Baseball Field [Directions] | L 5-6 (8 inn) | 9:00 AM; 1 Bus | |
| Sat., 4/8 | V Boys Lacrosse | Rumson-Fair Haven (NJ) | Home - New Canaan HS-Dunning Stadium [Directions] | W 7-6 | TBA | |
| Sat., 4/8 | FR Boys Lacrosse | Chaminade (NY) | Home - New Canaan HS-Dunning Stadium [Directions] | 1:30 p.m. | ||
| Mon., 4/10 | FR Baseball | Darien | Home - New Canaan HS-Coppo Field [Directions] | L 9-2 | ||
| Mon., 4/10 | FR Boys Lacrosse | Westhill | Home - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Mon., 4/10 | V Boys Tennis | Danbury | Home - New Canaan HS-NCHS Tennis Courts [Directions] | W 7-0 [Detailed Results] | ||
| Mon., 4/10 | V Girls Tennis | Danbury | Away - Danbury HS-DHS Tennis Courts [Directions] | W 7-0 | 10:30 AM; 1 Bus | |
| Tue., 4/11 | V Baseball | Abbott Tech | Home - Mead Park-Baseball Field [Directions] | W 8-5 | ||
| Tue., 4/11 | V Boys Lacrosse | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | W 17-2 | 3:45 PM; 1 Bus | |
| Tue., 4/11 | JV Boys Lacrosse | Trumbull | Away - Trumbull HS-Cork Field [Directions] | 4:15 p.m. | 2:30 PM; 1 Bus | |
| Tue., 4/11 | V Boys Tennis | Staples | Away - Staples HS-Staples Tennis Courts [Directions] | L 3-4 [Detailed Results] | 2:30 PM; 1 Bus | |
| Tue., 4/11 | JV Boys Tennis | Staples | Away - Staples HS-Town Farms Tennis Courts [Directions] | Postponed | 2:30 PM; 1 Bus | |
| Tue., 4/11 | V Girls Lacrosse | Trumbull | Home - New Canaan HS-Dunning Stadium [Directions] | W 16-0 | ||
| Tue., 4/11 | JV Girls Lacrosse | Trumbull | Home - New Canaan HS-Dunning Stadium [Directions] | 1:30 p.m. | ||
| Tue., 4/11 | V Softball | Daniel Hand | Home - Waveny Park-Orchard Field [Directions] | W 8-3 | ||
| Tue., 4/11 | V Girls Tennis | Staples | Home - New Canaan HS-NCHS Tennis Courts [Directions] | W 7-0 [Detailed Results] | ||
| Wed., 4/12 | V Boys Lacrosse | Glastonbury | Home - New Canaan HS-Dunning Stadium [Directions] | W 11-3 | ||
| Wed., 4/12 | JV Boys Lacrosse | Glastonbury | Home - New Canaan HS-Dunning Stadium [Directions] | 3:00 p.m. | ||
| Wed., 4/12 | FR Boys Lacrosse | Staples | Home - New Canaan HS-Dunning Stadium [Directions] | 12:00 p.m. | ||
| Wed., 4/12 | V Softball | Wilton | Away - Wilton HS-Varsity Softball Field [Directions] | L 0-1 | 3:15 PM; 1 Bus | |
| Thu., 4/13 | V Baseball | New Milford | Home - Mead Park-Baseball Field [Directions] | L 7-11 | ||
| Thu., 4/13 | V Boys Tennis | Wilton | Home - New Canaan HS-NCHS Tennis Courts [Directions] | L 1-6 [Detailed Results] | ||
| Thu., 4/13 | V Girls Lacrosse | Westhampton Beach (NY) | Home - New Canaan HS [Directions] | W 13-4 | 10:30 AM; 1 Bus | |
| Thu., 4/13 | JV Softball | Wilton | Away - Wilton HS-JV Softball Field [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Thu., 4/13 | V Girls Tennis | Wilton | Away - Wilton HS-Tennis Courts [Directions] | W 7-0 [Detailed Results] | 10:45 AM; 1 Bus | |
| Fri., 4/14 | V Baseball | Danbury | Away - Danbury HS-V Baseball Field [Directions] | L 2-3 | 10:00 AM; 1 Bus (JV/V ride together.) | |
| Fri., 4/14 | JV Baseball | Danbury | Away - Danbury HS-JV Baseball Field [Directions] | W 17-3 | 10:00 AM; 1 Bus (JV/V ride together.) | |
| Fri., 4/14 | FR Baseball | Danbury | Home - New Canaan HS-Coppo Field [Directions] | W 10-6 | ||
| Fri., 4/14 | FR Boys Lacrosse | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 12:00 p.m. | 10:30 AM; 1 Bus | |
| Fri., 4/14 | V Boys Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | L 0-3 | 10:00 AM; 1 Bus (JV/V ride together.) | |
| Fri., 4/14 | JV Boys Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | Cancelled | 10:00 AM; 1 Bus (JV/V ride together.) | |
| Fri., 4/14 | V Softball | Danbury | Home - Waveny Park-Orchard Field [Directions] | L 6-9 | ||
| Fri., 4/14 | JV Softball | Danbury | Home - Waveny Park-Orchard Field [Directions] | 4:00 p.m. | ||
| Fri., 4/14 | Miscellaneous Events | Pomperaug Distance challenge | Home - TBA [Directions] | 4:00 p.m. | Parents will Bring Athletes | |
| Sat., 4/15 | V Boys Lacrosse | Ridgefield | Home - New Canaan HS-Dunning Stadium [Directions] | W 10-4 | ||
| Sat., 4/15 | JV Boys Lacrosse | Ridgefield | Home - New Canaan HS-WTT #2 [Directions] | 5:30 p.m. | ||
| Sat., 4/15 | V Girls Lacrosse | Rye (NY) | Home - New Canaan HS-Dunning Stadium [Directions] | W 17-7 | ||
| Sat., 4/15 | JV Girls Lacrosse | Rye (NY) | Home - New Canaan HS-WTT #2 [Directions] | 3:30 p.m. | ||
| Sat., 4/15 | V Softball | Ridgefield | Home - Waveny Park-Orchard Field [Directions] | L 0-2 (9 innings) | ||
| Mon., 4/17 | V Baseball | Staples | Home - Mead Park-Baseball Field [Directions] | L 0-1 | ||
| Mon., 4/17 | JV Baseball | Staples | Home - Waveny Park-Coppo Field [Directions] | L 0-10 | ||
| Mon., 4/17 | FR Baseball | Staples | Away - Staples HS-Baseball Diamond [Directions] | L 16-2 | 2:35 PM; 1 Bus | |
| Mon., 4/17 | FR Boys Lacrosse | Wilton | Away - Allen's Meadow-Lacrosse Field #1 [Directions] | 4:30 p.m. | 3:00 PM; 1 Bus | |
| Mon., 4/17 | V Boys Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | L 1-3 | 2:45 PM; 1 Bus (JV/V ride together) | |
| Mon., 4/17 | JV Boys Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 6:00 p.m. | 2:45 PM; 1 Bus (JV/V ride together) | |
| Mon., 4/17 | V Girls Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | Greenwich 175 New Canaan 195 | 2:30 PM; 1 Bus (V & JV Ride together) | |
| Mon., 4/17 | JV Girls Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus (JV & V ride together) | |
| Mon., 4/17 | FR Girls Lacrosse | Wilton | Away - Wilton HS-Allen Meadow [Directions] | 4:45 p.m. | 4:00 PM; 1 Bus | |
| Mon., 4/17 | V Softball | Staples | Away - Staples HS-Wakeman Field [Directions] | W 10-9 | 2:30 PM; 1 Bus | |
| Tue., 4/18 | V Boys Lacrosse | Bronxville (NY) | Away - Bronxville HS-N:Turf | W 12-3 | 2:30 PM; 1 Bus | |
| Tue., 4/18 | JV Boys Lacrosse | Bronxville (NY) | Home - New Canaan HS-WTT #2 [Directions] | Cancelled | ||
| Tue., 4/18 | V Boys Outdoor Track | St. Joseph, Lauralton Hall | Away - St. Joseph HS-Track [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Tue., 4/18 | V Boys Tennis | Ridgefield | Away - Ridgefield HS-RHS Tennis Courts [Directions] | W 4-3 [Detailed Results] | 2:30 PM; 1 Bus | |
| Tue., 4/18 | JV Boys Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | 2:40 PM; 1 Bus | |
| Tue., 4/18 | V Girls Golf | St. Joseph | Away - Tashua Knolls Golf Course [Directions] | New Canaan 187 St. Joeseph's 238 | 2:00 PM; 1 Bus (JV/V will ride together) | |
| Tue., 4/18 | JV Girls Golf | St. Joseph | Away - Tashua Knolls Golf Course-Tashua Glen [Directions] | 3:00 p.m. | 2:00 PM | |
| Tue., 4/18 | V Girls Lacrosse | Somers (NY) | Home - New Canaan HS-Dunning Stadium [Directions] | W 12-2 | ||
| Tue., 4/18 | JV Girls Lacrosse | Somers (NY) | Home - New Canaan HS-Dunning Stadium [Directions] | 7:00 p.m. | ||
| Tue., 4/18 | V Girls Outdoor Track | St. Joseph, Lauralton Hall | Away - St. Joseph HS-Track [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Tue., 4/18 | JV Softball | Staples | Away - Staples HS-Staples Softball Field [Directions] | Cancelled | 2:30 PM; 1 Bus (JV/V ride together) | |
| Tue., 4/18 | V Girls Tennis | Ridgefield | Home - New Canaan HS-NCHS Tennis Courts [Directions] | W 7-0 | ||
| Wed., 4/19 | V Baseball | Wilton | Away - Wilton HS-Varsity Baseball Field [Directions] | L 2-3 | 2:45 PM; 1 Bus (JV/V ride together) | |
| Wed., 4/19 | JV Baseball | Wilton | Away - Wilton HS-JV Baseball Field [Directions] | L 5-6 | 2:45 PM; 1 Bus (JV & V ride together) | |
| Wed., 4/19 | FR Baseball | Wilton | Home - New Canaan HS-Coppo Field [Directions] | 4:00 p.m. | ||
| Wed., 4/19 | FR Boys Lacrosse | Fairfield Warde | Home - New Canaan HS-WTT #2 [Directions] | 4:30 p.m. | ||
| Wed., 4/19 | V Boys Tennis | St. Joseph | Home - New Canaan HS-NCHS Tennis Courts [Directions] | W 6-1 [Detailed Results] | ||
| Wed., 4/19 | JV Boys Tennis | Staples | Home - New Canaan HS-NCHS Tennis Courts [Directions] | 5:30 p.m. | ||
| Wed., 4/19 | V Boys Volleyball | Staples | Home - New Canaan HS-Main Gym [Directions] | W 3-1 | ||
| Wed., 4/19 | JV Boys Volleyball | Staples | Home - New Canaan HS-Main Gym [Directions] | 6:00 p.m. | ||
| Wed., 4/19 | V Girls Golf | Darien | Away - Wee Burn CC [Directions] | 3:00 p.m. | 2:30 PM; 1 Bus | |
| Wed., 4/19 | FR Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Fairfield Warde Grass Utility Field [Directions] | 4:00 p.m. | 2:45 PM; 1 Bus | |
| Wed., 4/19 | V Softball | Wilton | Home - Waveny Park-Orchard Field [Directions] | L 5-11 | ||
| Wed., 4/19 | V Girls Tennis | St. Joseph | Away - St. Joseph HS-Tennis Courts [Directions] | W 7-0 | 2:30 PM; 1 Bus | |
| Wed., 4/19 | JV Girls Tennis | Greenwich | Away - Binney Park [Directions] | 4:30 p.m. | 2:40 PM; 1 Bus | |
| Thu., 4/20 | V Baseball | St. Joseph | Away - St. Joseph HS-Baseball Diamond [Directions] | W 5-1 | 2:30 PM; 1 Bus | |
| Thu., 4/20 | JV Baseball | St. Joseph | Away - Unity Park-Field 1 [Directions] | L 10-20 | 2:30 PM; 1 Bus | |
| Thu., 4/20 | V Boys Lacrosse | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | W 14-6 | 2:30 PM; 1 Bus | |
| Thu., 4/20 | JV Boys Lacrosse | Greenwich | Away - Greenwich HS-Field 4 [Directions] | 5:00 p.m. | 2:45 PM; 1 Bus | |
| Thu., 4/20 | V Boys Tennis | Stamford | Home - New Canaan HS-NCHS Tennis Courts [Directions] | W 5-2 [Detailed Results] | ||
| Thu., 4/20 | JV Boys Tennis | Darien | Away - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | 3:00 PM; 1 Bus | |
| Thu., 4/20 | V Girls Lacrosse | Greenwich | Home - New Canaan HS-Dunning Stadium [Directions] | W 14-6 | ||
| Thu., 4/20 | JV Girls Lacrosse | Greenwich | Home - New Canaan HS-Dunning Stadium [Directions] | 6:00 p.m. | ||
| Thu., 4/20 | V Softball | St. Joseph | Home - Waveny Park-Orchard Field [Directions] | L 7-17 | ||
| Thu., 4/20 | V Girls Tennis | Stamford | Away - Stamford HS-SHS Tennis Courts [Directions] | W 7-0 | 2:40 PM; 1 Bus | |
| Thu., 4/20 | JV Girls Tennis | Fairfield Warde | Away - Fairfield Woods-Tennis Courts [Directions] | 4:00 p.m. | 2:40 PM; 1 Bus | |
| Fri., 4/21 | FR Baseball | St. Joseph | Home - New Canaan HS-Coppo Field [Directions] | 4:00 p.m. | ||
| Fri., 4/21 | FR Boys Lacrosse | Greenwich | Away - Cos Cob Park, Benvenuto Field-Benvenuto Field [Directions] | 4:30 p.m. | 2:40 PM; 1 Bus | |
| Fri., 4/21 | JV Softball | St. Joseph | Home - Waveny Park-Orchard Field [Directions] | 4:00 p.m. | ||
| Sat., 4/22 | V Boys Lacrosse | Stepinac (NY) | Away - ArchBishop Stepinac HS | L 9-12 | 11:30 AM | |
| Sat., 4/22 | JV Boys Lacrosse | Stepinac (NY) | Away - Stepinac HS-Field | 3:30 p.m. | 1:30 PM; 1 Bus | |
| Sat., 4/22 | V Boys Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | W 3-0 | 8:30 AM; 1 Bus (JV/V ride together.) | |
| Sat., 4/22 | JV Boys Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 10:00 a.m. | 8:30 AM; 1 Bus (JV/V ride together.) | |
| Sat., 4/22 | V Girls Lacrosse | Longmeadow (MA) | Home - New Canaan HS-Dunning Stadium [Directions] | W 18-5 | ||
| Sat., 4/22 | JV Girls Lacrosse | Longmeadow (MA) | Home - New Canaan HS-Dunning Stadium [Directions] | 1:00 p.m. | ||
| Mon., 4/24 | V Baseball | Ridgefield | Home - Mead Park-Baseball Field [Directions] | W 7-4 | ||
| Mon., 4/24 | JV Baseball | Ridgefield | Home - Waveny Park-Coppo Field [Directions] | W 4-1 | ||
| Mon., 4/24 | FR Baseball | Ridgefield | Away - Governor Field [Directions] | 4:00 p.m. | 2:35 PM; 1 Bus | |
| Mon., 4/24 | FR Boys Lacrosse | Stamford | Home - New Canaan HS-WTT #2 [Directions] | 4:30 p.m. | ||
| Mon., 4/24 | V Boys Tennis | Greenwich | Away - Greenwich HS-Tennis Courts [Directions] | L 6-1 [Detailed Results] | 2:40 PM; 1 Bus | |
| Mon., 4/24 | JV Boys Tennis | Greenwich | Away - Central MS [Directions] | 4:30 p.m. | 3:00 PM; 1 Bus | |
| Mon., 4/24 | V Boys Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | W 3-0 | 2:40 PM; 1 Bus (JV/V ride together) | |
| Mon., 4/24 | JV Boys Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 5:30 p.m. | 2:40 PM; 1 Bus (JV/V ride together) | |
| Mon., 4/24 | V Girls Golf | Staples | Home - CCNC [Directions] | 3:30 p.m. | ||
| Mon., 4/24 | V Girls Lacrosse | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | W 17-2 | 2:40 PM; 1 Bus | |
| Mon., 4/24 | JV Girls Lacrosse | Westhill | Away - Westhill HS-Westhill Front Turf Field [Directions] | 5:30 p.m. | 4:15 PM; 1 Bus | |
| Mon., 4/24 | FR Girls Lacrosse | Trumbull | Away - Trumbull HS-The Pit [Directions] | 4:00 p.m. | 3:00 PM; 1 Bus | |
| Mon., 4/24 | V Softball | Ridgefield | Away - Ridgefield HS-Varsity Softball Field [Directions] | L 0-11 | 2:40 PM; 1 Bus (JV/V will ride together 2 vans) | |
| Mon., 4/24 | V Girls Tennis | Greenwich | Home - New Canaan HS-NCHS Tennis Courts [Directions] | L 3-4 | ||
| Tue., 4/25 | V Boys Lacrosse | Westhill | Home - New Canaan HS-Dunning Stadium [Directions] | W 17-3 | ||
| Tue., 4/25 | JV Boys Lacrosse | Westhill | Home - New Canaan HS-WTT #2 [Directions] | Postponed | ||
| Tue., 4/25 | V Boys Outdoor Track | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Tue., 4/25 | V Boys Tennis | Brien McMahon | Away - Brien McMahon HS-Tennis Courts [Directions] | W 6-1 [Detailed Results] | 2:40 PM; 1 Bus | |
| Tue., 4/25 | JV Girls Golf | Darien | Away - Country Club of Darien [Directions] | 3:00 p.m. | 2:30 PM; 1 Van | |
| Tue., 4/25 | V Girls Outdoor Track | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Tue., 4/25 | V Softball | Stamford | Home - Waveny Park-Orchard Field [Directions] | W 3-2 | ||
| Tue., 4/25 | JV Softball | Ridgefield | Away - Ridgefield HS-JV Softball Field [Directions] | Postponed | 2:40 PM; 1 Bus (JV/V will ride together) | |
| Tue., 4/25 | JV Softball | Stamford | Home - Waveny Park-Orchard Field [Directions] | 6:30 p.m. | ||
| Tue., 4/25 | V Girls Tennis | Brien McMahon | Home - New Canaan HS-NCHS Tennis Courts [Directions] | W 7-0 | ||
| Wed., 4/26 | V Boys Volleyball | Bridgeport Central | Home - New Canaan HS-Main Gym [Directions] | W 3-0 | ||
| Wed., 4/26 | JV Boys Volleyball | Bridgeport Central | Home - New Canaan HS-Main Gym [Directions] | 6:00 p.m. | ||
| Wed., 4/26 | V Girls Golf | Danbury | Away - Richter Park Golf Course [Directions] | 3:30 p.m. | 1:45 PM; 1 Bus | |
| Wed., 4/26 | V Girls Lacrosse | Darien | Home - New Canaan HS-Dunning Stadium [Directions] | L 11-6 | ||
| Wed., 4/26 | JV Girls Lacrosse | Darien | Home - New Canaan HS-Dunning Stadium [Directions] | 6:00 p.m. | ||
| Wed., 4/26 | FR Girls Lacrosse | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | 4:30 p.m. | 3:00 PM; 1 Bus | |
| Thu., 4/27 | V Boys Lacrosse | Fairfield Prep | Home - New Canaan HS-Dunning Stadium [Directions] | L 14-6 | ||
| Thu., 4/27 | JV Boys Lacrosse | Fairfield Prep | Home - New Canaan HS-WTT #2 [Directions] | 4:30 p.m. | ||
| Thu., 4/27 | V Girls Golf | Wilton | Away - Silvermine Golf Club [Directions] | 3:30 p.m. | 2:30 PM; 1 Bus | |
| Fri., 4/28 | V Baseball | Greenwich | Home - Mead Park-Baseball Field [Directions] | L 5-7 | ||
| Fri., 4/28 | JV Baseball | Greenwich | Home - Waveny Park-Coppo Field [Directions] | W 12-11 | ||
| Fri., 4/28 | FR Baseball | Greenwich | Away - Greenwich HS-Baseball Field [Directions] | 4:30 p.m. | 3:00 PM; 1 Bus | |
| Fri., 4/28 | FR Boys Lacrosse | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | 4:15 p.m. | 2:40 PM; 1 Bus | |
| Fri., 4/28 | V Boys Tennis | Bridgeport Central | Home - New Canaan HS-NCHS Tennis Courts [Directions] | W 7-0 [Detailed Results] | ||
| Fri., 4/28 | V Boys Volleyball | Darien | Home - New Canaan HS-Main Gym [Directions] | L 0-3 | ||
| Fri., 4/28 | JV Boys Volleyball | Darien | Home - New Canaan HS-Main Gym [Directions] | 6:00 p.m. | ||
| Fri., 4/28 | JV Girls Lacrosse | Greenwich Academy | Home - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Fri., 4/28 | V Softball | Greenwich | Away - Greenwich HS-Softball Field [Directions] | W 15-4 | 2:40 PM; 1 Bus | |
| Fri., 4/28 | V Girls Tennis | Bridgeport Central | Away - Bridgeport Central HS-Central High School Tennis Courts [Directions] | W 7-0 | 2:30 PM; 1 Bus | |
| Sat., 4/29 | V Boys Lacrosse | Darien | Away - Darien HS-DHS Stadium Field [Directions] | L 11-7 | 11:30 AM; 1 Bus | |
| Sat., 4/29 | JV Boys Lacrosse | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 3:30 p.m. | 12:45 PM; 1 Bus | |
| Sat., 4/29 | JV Softball | Greenwich | Away - Greenwich HS-Softball Field [Directions] | Postponed | 9:30 AM; 1 Bus | |
| Sat., 4/29 | Miscellaneous Events | O'Grady Relays | Home - TBA [Directions] | 9:00 a.m. | 6:45 AM; 1 Bus | |
| Mon., 5/1 | V Baseball | Brien McMahon | Home - Mead Park-Baseball Field [Directions] | W 10-0 | ||
| Mon., 5/1 | JV Baseball | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | W 14-1 | 2:45 PM (baseball/Softball will ride together) | |
| Mon., 5/1 | FR Boys Lacrosse | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | 4:20 PM; 1 Bus | |
| Mon., 5/1 | JV Boys Tennis | Fairfield Warde | Away - Fairfield Warde HS-Knapps Courts [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus (JV/V teams will ride together) | |
| Mon., 5/1 | V Boys Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | W 3-0 | 2:40 PM; 1 Bus (JV/V ride together) | |
| Mon., 5/1 | JV Boys Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | 2:40 PM; 1 Bus (JV/V ride together) | |
| Mon., 5/1 | FR Girls Lacrosse | Staples | Home - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Mon., 5/1 | V Softball | Brien McMahon | Away - Brien McMahon HS-Softball Diamond [Directions] | W 4-0 | 2:45 PM; 1 Bus (JV/V will ride together) | |
| Mon., 5/1 | V Girls Tennis | Fairfield Warde | Home - New Canaan HS-NCHS Tennis Courts [Directions] | W 7-0 | ||
| Tue., 5/2 | V Boys Outdoor Track | Wilton | Home - New Canaan HS-NCHS Track [Directions] | 4:00 p.m. | ||
| Tue., 5/2 | V Boys Tennis | Darien | Away - Darien HS-DHS Tennis Courts [Directions] | L 3-4 [Detailed Results] | 2:40 PM; 1 Bus | |
| Tue., 5/2 | JV Girls Golf | Fairfield Ludlowe | Away - Carl Dickman Par 3 [Directions] | 3:15 p.m. | 2:00 PM; 1 Bus | |
| Tue., 5/2 | V Girls Lacrosse | Bronxville (NY) | Home - New Canaan HS-Dunning Stadium [Directions] | W 11-8 | ||
| Tue., 5/2 | JV Girls Lacrosse | Bronxville (NY) | Home - New Canaan HS-Dunning Stadium [Directions] | Cancelled | ||
| Tue., 5/2 | V Girls Outdoor Track | Wilton | Home - New Canaan HS-NCHS Track [Directions] | 4:00 p.m. | ||
| Tue., 5/2 | JV Softball | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 4:30 p.m. | 3:00 PM; 1 Bus (JV/V will ride together) | |
| Tue., 5/2 | V Girls Tennis | Darien | Home - New Canaan HS-NCHS Tennis Courts [Directions] | L 4-3 [Detailed Results] | ||
| Wed., 5/3 | V Baseball | Bridgeport Central | Away - Bridgeport Central HS-Baseball Diamond [Directions] | W 7-4 | 2:30 PM; 1 Bus | |
| Wed., 5/3 | FR Baseball | Bridgeport Central | Home - New Canaan HS-Coppo Field [Directions] | Cancelled | ||
| Wed., 5/3 | FR Boys Lacrosse | Fairfield Prep | Away - Fairfield University - Barlow Field-Barlow Field Fairfield University [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Wed., 5/3 | JV Boys Tennis | Fairfield Ludlowe | Away - Tomlinson MS-Tennis Courts [Directions] | 5:00 p.m. | 4:00 PM; 1 Bus | |
| Wed., 5/3 | V Boys Volleyball | Ridgefield | Home - New Canaan HS-Main Gym [Directions] | L 2-3 | ||
| Wed., 5/3 | JV Boys Volleyball | Ridgefield | Home - New Canaan HS-Main Gym [Directions] | 6:00 p.m. | ||
| Wed., 5/3 | FR Girls Lacrosse | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | 3:00 PM; 1 Bus | |
| Wed., 5/3 | V Softball | Bridgeport Central | Home - Waveny Park-Orchard Field [Directions] | W 17-1 | ||
| Wed., 5/3 | JV Softball | Bridgeport Central | Home - Waveny Park-Orchard Field [Directions] | 4:00 p.m. | ||
| Wed., 5/3 | JV Girls Tennis | Darien | Away - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | 2:50 PM; 1 Van | |
| Thu., 5/4 | V Boys Lacrosse | Staples | Home - New Canaan HS-Dunning Stadium [Directions] | L 6-5 | ||
| Thu., 5/4 | JV Boys Lacrosse | Staples | Home - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | ||
| Thu., 5/4 | V Boys Tennis | Trumbull | Home - New Canaan HS-NCHS Tennis Courts [Directions] | W 4-3 [Detailed Results] | ||
| Thu., 5/4 | V Girls Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 3:15 p.m. | 2:00 PM; 1 Bus | |
| Thu., 5/4 | JV Girls Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | 2:00 PM; 1 Bus | |
| Thu., 5/4 | V Girls Lacrosse | Staples | Away - Staples HS-Ginny Parker Field [Directions] | W 15-2 | 4:00 PM; 1 Bus | |
| Thu., 5/4 | JV Girls Lacrosse | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Thu., 5/4 | JV Girls Tennis | Trumbull | Away - Tashua Knolls Golf Course-Tennis Courts [Directions] | 4:00 p.m. | 2:35 PM; 1 Bus | |
| Fri., 5/5 | V Baseball | Fairfield Warde | Home - Mead Park-Baseball Field [Directions] | L 3-9 | ||
| Fri., 5/5 | JV Baseball | Fairfield Warde | Home - Waveny Park-Coppo Field [Directions] | W 6-1 | ||
| Fri., 5/5 | FR Baseball | Fairfield Warde | Away - Fairfield Warde HS-Baseball Diamond [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Fri., 5/5 | V Boys Tennis | Fairfield Warde | Away - Fairfield Warde HS-Blake Courts [Directions] | L 3-4 [Detailed Results] | 2:30 PM; 1 Bus (V/JV will ride together.) | |
| Fri., 5/5 | JV Boys Tennis | Greenwich | Away - Central MS [Directions] | 4:15 p.m. | 2:40 PM; 1 Bus | |
| Fri., 5/5 | V Boys Volleyball | Greenwich | Home - New Canaan HS-Main Gym [Directions] | W 3-1 | ||
| Fri., 5/5 | JV Boys Volleyball | Greenwich | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 5/5 | V Softball | Fairfield Warde | Away - Fairfield Warde HS-Softball Diamond [Directions] | L 3-4 | 2:40 PM; 1 Bus | |
| Fri., 5/5 | JV Softball | Fairfield Warde | Away - Melville Park [Directions] | Postponed | ||
| Sat., 5/6 | V Baseball | Stamford | Away - Stamford HS-SHS Baseball Diamond [Directions] | L 6-11 | 11:45 AM; 1 Bus | |
| Sat., 5/6 | JV Baseball | Stamford | Away - Belltown Park-Barrett Field, Belltown Park [Directions] | W 26-10 | 8:40 AM; 1 Bus | |
| Sat., 5/6 | FR Baseball | Stamford | Home - New Canaan HS-Coppo Field [Directions] | Postponed | ||
| Sat., 5/6 | FR Boys Lacrosse | Chaminade (NY) | Away - Chaminade-OTT FIELD | 12:00 p.m. | 9:15 AM; 1 Bus | |
| Sat., 5/6 | V Girls Lacrosse | St. Anthonys (NY) | Home - New Canaan HS-Dunning Stadium [Directions] | L 9-8 | ||
| Sat., 5/6 | JV Girls Lacrosse | St. Anthonys (NY) | Home - New Canaan HS-Dunning Stadium [Directions] | 2:30 p.m. | ||
| Sat., 5/6 | V Girls Tennis | Trumbull | Away - Trumbull HS-Tennis Courts [Directions] | W 7-0 | 2:30 PM; 1 Bus | |
| Sat., 5/6 | Miscellaneous Events | Middletown Invitational | Home - TBA [Directions] | 12:00 p.m. | 9:30 AM; 1 Bus | |
| Mon., 5/8 | V Baseball | Darien | Home - Mead Park-Baseball Field [Directions] | W 4-3 | ||
| Mon., 5/8 | JV Baseball | Darien | Home - Waveny Park-Coppo Field [Directions] | L 2-3 | ||
| Mon., 5/8 | FR Baseball | Darien | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | 3:00 PM (Baseball/Softball ride together) | |
| Mon., 5/8 | FR Boys Lacrosse | Fairfield Ludlowe | Home - New Canaan HS-WTT #2 [Directions] | 4:30 p.m. | ||
| Mon., 5/8 | V Boys Tennis | Fairfield Ludlowe | Home - New Canaan HS-NCHS Tennis Courts [Directions] | W 7-0 [Detailed Results] | ||
| Mon., 5/8 | JV Boys Tennis | Darien | Away - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | 3:00 PM; 1 Bus | |
| Mon., 5/8 | V Boys Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | W 3-0 | 2:30 PM; 1 Bus (JV/V ride together.) | |
| Mon., 5/8 | JV Boys Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus (JV/V ride together.) | |
| Mon., 5/8 | V Softball | Darien | Away - Darien HS-DHS Softball - Varsity Field [Directions] | W 5-3 | 3:00 PM (Baseball & Softball ride together.) | |
| Mon., 5/8 | V Girls Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Tennis Courts [Directions] | W 4-3 [Detailed Results] | 2:35 PM; 1 Bus | |
| Mon., 5/8 | JV Girls Tennis | Fairfield Ludlowe | Away - Tomlinson MS-Tennis Courts [Directions] | 4:00 p.m. | 2:35 PM; 1 Bus | |
| Tue., 5/9 | V Boys Lacrosse | Fairfield Warde | Home - New Canaan HS-Dunning Stadium [Directions] | W 16-2 | ||
| Tue., 5/9 | JV Boys Lacrosse | Fairfield Warde | Home - New Canaan HS-Dunning Stadium [Directions] | 4:30 p.m. | ||
| Tue., 5/9 | V Boys Outdoor Track | Brien McMahon | Home - New Canaan HS-NCHS Track [Directions] | 4:00 p.m. | ||
| Tue., 5/9 | V Boys Tennis | Norwalk | Home - New Canaan HS-NCHS Tennis Courts [Directions] | W 7-0 | ||
| Tue., 5/9 | JV Girls Golf | Darien | Away - Country Club of Darien [Directions] | 3:00 p.m. | 2:00 PM; 1 Bus | |
| Tue., 5/9 | V Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | W 17-0 | 2:30 PM; 1 Bus | |
| Tue., 5/9 | JV Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 5:30 p.m. | 3:45 PM; 1 Bus | |
| Tue., 5/9 | FR Girls Lacrosse | Fairfield Warde | Home - New Canaan HS-WTT #2 [Directions] | Postponed | ||
| Tue., 5/9 | V Girls Outdoor Track | Brien McMahon | Home - New Canaan HS-NCHS Track [Directions] | 4:00 p.m. | ||
| Tue., 5/9 | V Girls Tennis | Norwalk | Away - Norwalk HS-Tennis Courts [Directions] | W 7-0 | 2:35 PM; 1 Bus | |
| Tue., 5/9 | JV Girls Tennis | Staples | Away - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | 3:00 PM; 1 Bus | |
| Wed., 5/10 | V Baseball | Trumbull | Away - Trumbull HS-Varsity Baseball Field [Directions] | L 0-5 | 2:30 PM; 1 Bus (V/JV ride together.) | |
| Wed., 5/10 | JV Baseball | Trumbull | Away - Trumbull HS-JV Baseball Field [Directions] | L 0-7 | 2:30 PM; 1 Bus (JV/V ride together) | |
| Wed., 5/10 | FR Baseball | Trumbull | Home - New Canaan HS-Coppo Field [Directions] | 4:00 p.m. | ||
| Wed., 5/10 | FR Boys Lacrosse | Wilton | Home - New Canaan HS-WTT #2 [Directions] | 4:30 p.m. | ||
| Wed., 5/10 | V Boys Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | L 0-3 | 2:30 PM; 1 Bus (JV/V ride together.) | |
| Wed., 5/10 | JV Boys Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus (JV/V ride together.) | |
| Wed., 5/10 | V Girls Golf | Darien | Home - TBA [Directions] | 3:30 p.m. | 2:00 PM, Dismiss TBA; 1 Bus (We are playing at Wee Burn) | |
| Wed., 5/10 | V Softball | Trumbull | Home - Waveny Park-Orchard Field [Directions] | L 2-5 | ||
| Wed., 5/10 | JV Softball | Trumbull | Home - Waveny Park-Orchard Field [Directions] | 4:00 p.m. | ||
| Thu., 5/11 | V Boys Lacrosse | Wilton | Away - Wilton HS-Veterans Memorial Stadium [Directions] | W 8-6 | 5:30 PM; 1 Bus | |
| Thu., 5/11 | JV Boys Lacrosse | Wilton | Away - Wilton HS-Veterans Memorial Stadium [Directions] | 4:30 p.m. | 3:15 PM; 1 Bus | |
| Thu., 5/11 | V Boys Tennis | Westhill | Away - Westhill HS-Westhill Tennis Courts [Directions] | W 4-3 [Detailed Results] | 2:40 PM; 1 Bus | |
| Thu., 5/11 | V Boys Volleyball | Fairfield Ludlowe | Home - New Canaan HS-Main Gym [Directions] | W 3-2 | ||
| Thu., 5/11 | JV Boys Volleyball | Fairfield Ludlowe | Home - New Canaan HS-Main Gym [Directions] | 6:00 p.m. | ||
| Thu., 5/11 | V Girls Golf | Ridgefield | Away - Ridgefield Golf Course [Directions] | 3:00 p.m. | 2:00 PM; 1 Bus (JV/V players ride together) | |
| Thu., 5/11 | JV Girls Golf | Ridgefield | Away - Ridgefield Golf Course [Directions] | 3:00 p.m. | 2:00 PM; 1 Bus | |
| Thu., 5/11 | V Girls Lacrosse | Wilton | Home - New Canaan HS-Dunning Stadium [Directions] | W 13-6 | ||
| Thu., 5/11 | JV Girls Lacrosse | Wilton | Home - New Canaan HS-Dunning Stadium [Directions] | 6:00 p.m. | ||
| Thu., 5/11 | FR Girls Lacrosse | Norwalk | Home - New Canaan HS-WTT #2 [Directions] | Cancelled | ||
| Thu., 5/11 | V Softball | Fairfield Ludlowe | Home - Waveny Park-Orchard Field [Directions] | L 0-16 | ||
| Thu., 5/11 | V Girls Tennis | Westhill | Home - New Canaan HS-NCHS Tennis Courts [Directions] | W 7-0 | ||
| Thu., 5/11 | JV Girls Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | 3:00 PM; 1 Bus | |
| Thu., 5/11 | Miscellaneous Events | Loucks Games | Home - TBA [Directions] | TBA | ||
| Fri., 5/12 | FR Baseball | Fairfield Ludlowe | Home - New Canaan HS-Coppo Field [Directions] | 4:00 p.m. | ||
| Fri., 5/12 | FR Boys Lacrosse | Trumbull | Home - New Canaan HS-WTT #2 [Directions] | 4:30 p.m. | ||
| Fri., 5/12 | JV Girls Lacrosse | Sacred Heart of Greenwich | Away - Sacred Heart Greenwich-Magnetti Turf Field | 4:30 p.m. | 2:40 PM; 1 Bus (Fr/JV will ride together.) | |
| Fri., 5/12 | FR Girls Lacrosse | Sacred Heart of Greenwich | Away - Sacred Heart of Greenwich-Sheehan Turf | 4:30 p.m. | 3:00 PM; 1 Bus (Fr/JV ride together) | |
| Fri., 5/12 | JV Softball | Fairfield Ludlowe | Home - Waveny Park-Orchard Field [Directions] | 4:00 p.m. | ||
| Sat., 5/13 | V Baseball | Fairfield Ludlowe | Away - Kiwanis Field-Baseball Diamond [Directions] | L 1-14 | 10:15 AM; 1 Bus | |
| Sat., 5/13 | JV Baseball | Fairfield Ludlowe | Away - Owen Fish Park-Owen Fish [Directions] | L 4-7 | 10:15 AM; 1 Bus | |
| Sat., 5/13 | JV Softball | Wilton | Home - Waveny Park-Orchard Field [Directions] | 2:30 p.m. | ||
| Sat., 5/13 | Miscellaneous Events | Loucks Games | Home - TBA [Directions] | TBA | ||
| Sun., 5/14 | V Boys Lacrosse | Upper Arlington (OH) | Away - Panzer Stadium-Penn State Lacrosse Field | L 14-11 | 7:00 AM; 1 Bus | |
| Mon., 5/15 | V Baseball | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | L 3-4 | 4:30 PM; 1 Bus | |
| Mon., 5/15 | JV Baseball | Norwalk | Away - City Hall Field [Directions] | W 5-4 | 2:35 PM; 1 Bus | |
| Mon., 5/15 | FR Baseball | Norwalk | Home - New Canaan HS-Coppo Field [Directions] | 4:00 p.m. | ||
| Mon., 5/15 | V Boys Tennis | Wilton | Away - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | 2:40 PM; 1 Bus | |
| Mon., 5/15 | V Boys Volleyball | Danbury | Home - New Canaan HS-Main Gym [Directions] | W 3-1 | ||
| Mon., 5/15 | JV Boys Volleyball | Danbury | Home - New Canaan HS-Main Gym [Directions] | 4:30 p.m. | ||
| Mon., 5/15 | V Girls Golf | Trumbull | Home - CCNC [Directions] | 3:30 p.m. | ||
| Mon., 5/15 | V Softball | Norwalk | Home - Waveny Park-Orchard Field [Directions] | W 8-4 | ||
| Mon., 5/15 | JV Softball | Norwalk | Home - Waveny Park-Orchard Field [Directions] | 4:00 p.m. | ||
| Tue., 5/16 | V Boys Outdoor Track | Darien | Home - New Canaan HS-NCHS Track [Directions] | 4:00 p.m. | ||
| Tue., 5/16 | JV Girls Golf | Fairfield Ludlowe | Away - Carl Dickman Par 3 [Directions] | 3:15 p.m. | 2:00 PM; 1 Bus | |
| Tue., 5/16 | V Girls Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | W 15-5 | 5:00 PM; 1 Bus | |
| Tue., 5/16 | JV Girls Lacrosse | Ridgefield | Away - Scotts Ridge MS-SRMS Turf [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Tue., 5/16 | FR Girls Lacrosse | Wilton | Home - New Canaan HS-WTT #2 [Directions] | 4:30 p.m. | ||
| Tue., 5/16 | V Girls Outdoor Track | Darien | Home - New Canaan HS-NCHS Track [Directions] | 4:00 p.m. | ||
| Tue., 5/16 | V Girls Tennis | Fairfield Warde | Home - New Canaan HS-NCHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/17 | V Baseball | Westhill | Home - Mead Park-Baseball Field [Directions] | W 12-2 | ||
| Wed., 5/17 | JV Baseball | Westhill | Home - Waveny Park-Coppo Field [Directions] | L 0-14 | ||
| Wed., 5/17 | FR Baseball | Westhill | Away - Rippowan MS-Rippowam Baseball Field [Directions] | 4:00 p.m. | 3:00 PM; 1 Bus (Fr Baseball & V Softball will ride together.) | |
| Wed., 5/17 | V Boys Volleyball | Norwalk | Home - New Canaan HS-Main Gym [Directions] | W 3-1 | 2:35 PM; 1 Bus | |
| Wed., 5/17 | JV Boys Volleyball | Norwalk | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | 2:35 PM; 1 Bus | |
| Wed., 5/17 | V Girls Golf | Fairfield Warde | Home - CCNC [Directions] | 3:30 p.m. | ||
| Wed., 5/17 | V Softball | Westhill | Away - Westhill HS-Varsity Softball Field [Directions] | W 9-2 | 3:00 PM; 1 Bus (Fr Baseball & V Softball will ride together.) | |
| Thu., 5/18 | FR Boys Lacrosse | Darien | Home - New Canaan HS-WTT #2 [Directions] | 4:30 p.m. | ||
| Thu., 5/18 | V Girls Lacrosse | Fairfield Ludlowe | Home - New Canaan HS-Dunning Stadium [Directions] | W 14-3 | ||
| Thu., 5/18 | FR Girls Lacrosse | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | 3:00 PM; 1 Bus | |
| Thu., 5/18 | V Girls Tennis | Fairfield Ludlowe | Home - New Canaan HS-NCHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 5/19 | V Softball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | L 3-8 | 11:15 AM; 1 Bus | |
| Sat., 5/20 | V Boys Lacrosse | Greenwich | Home - New Canaan HS-Dunning Stadium [Directions] | W 12-9 | ||
| Sat., 5/20 | V Boys Volleyball | Ridgefield | Home - New Canaan HS-Main Gym [Directions] | L 3-0 | ||
| Mon., 5/22 | JV Girls Golf | Staples | Away - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | 2:00 PM; 1 Bus | |
| Mon., 5/22 | V Girls Lacrosse | Wilton | Home - Greenwich HS-Cardinal Stadium [Directions] | W 10-9 | 2:00 PM; 1 Bus | |
| Tue., 5/23 | V Boys Lacrosse | Staples | Away - Norwalk HS-Testa Field [Directions] | W 9-5 | 2:45 PM; 1 Bus | |
| Tue., 5/23 | V Boys Outdoor Track | FCIAC Track Championship | Away - Danbury HS-Danbury HS Stadium | 2:30 p.m. | 12:00 PM; 1 Bus | |
| Tue., 5/23 | V Girls Golf | Wilton | Home - CCNC [Directions] | 3:30 p.m. | ||
| Tue., 5/23 | V Girls Outdoor Track | FCIAC Track Championship | Away - Danbury HS-DHS Stadium | 2:30 p.m. | 12:00 PM; 1 Bus | |
| Wed., 5/24 | V Baseball | Greenwich (Scrim.) | Home - Mead Park-Baseball Field [Directions] | 4:30 p.m. | ||
| Wed., 5/24 | JV Boys Lacrosse | Staples | Away - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | 3:30 PM; 1 Bus | |
| Wed., 5/24 | V Girls Golf | Ridgefield | Home - CCNC [Directions] | 3:30 p.m. | ||
| Wed., 5/24 | V Girls Lacrosse | Darien | Away - Greenwich HS-Cardinal Stadium [Directions] | L 11-7 | 4:00 PM; 1 Bus | |
| Wed., 5/24 | V Softball | Stamford (Scrim.) | Home - Waveny Park-Orchard Field [Directions] | 4:00 p.m. | ||
| Thu., 5/25 | V Boys Lacrosse | Wilton | Away - Norwalk HS-Testa Field, NHS [Directions] | L 4-8 | 3:30 PM; 1 Bus | |
| Thu., 5/25 | V Girls Golf | Berlin | Away - Timberlin Golf Course [Directions] | 3:00 p.m. | 1:30 PM; 1 Bus | |
| Fri., 5/26 | V Boys Tennis | Shelton | Away - Shelton HS-Tennis Courts [Directions] | 3:00 p.m. | 12:45 PM, Dismiss TBA; 1 Bus | |
| Fri., 5/26 | V Girls Lacrosse | Darien | Home - New Canaan HS-Dunning Stadium [Directions] | 4:30 p.m. | ||
| Sat., 5/27 | V Girls Tennis | Cheshire | Home - New Canaan HS-NCHS Tennis Courts [Directions] | W 5-2 | ||
| Tue., 5/30 | V Baseball | Fairfield Prep | Away - Fairfield University-Alumni Diamond [Directions] | 3:30 p.m. | 1:45 PM; 1 Bus | |
| Tue., 5/30 | V Boys Tennis | Cheshire | Home - New Canaan HS-NCHS Tennis Courts [Directions] | 3:00 p.m. | ||
| Tue., 5/30 | V Girls Lacrosse | Glastonbury | Home - New Canaan HS-Dunning Stadium [Directions] | W 18-0 | ||
| Tue., 5/30 | V Softball | Norwalk | Away - Norwalk HS-Ray Barry Field [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Tue., 5/30 | V Girls Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Tennis Courts [Directions] | 3:00 p.m. | 1:45 PM, Dismiss TBA; 1 Bus | |
| Wed., 5/31 | V Baseball | Maloney | Away - Ceppa Field-Baseball Diamond [Directions] | 3:30 p.m. | 1:15 PM; 1 Bus | |
| Wed., 5/31 | V Boys Lacrosse | Brien McMahon | Home - New Canaan HS-Dunning Stadium [Directions] | W 14-5 | ||
| Wed., 5/31 | V Boys Outdoor Track | CIAC Class L Championships | Away - Willow Brook Park | 4:00 p.m. | ||
| Wed., 5/31 | V Boys Tennis | Amity | Away - Amity Regional HS-Tennis Courts [Directions] | 3:00 p.m. | 12:15 PM; 2 Vans | |
| Wed., 5/31 | V Boys Volleyball | Innovation | Away - Innovation-Gymnasium [Directions] | W 3-0 | 2:15 PM; 1 Bus | |
| Wed., 5/31 | V Girls Outdoor Track | CIAC Class L Championships | Away - Willow Brook Park | 4:00 p.m. | ||
| Wed., 5/31 | V Softball | Ridgefield | Away - Ridgefield HS-Varsity Softball Field [Directions] | 4:00 p.m. | 2:10 PM; 1 Bus | |
| Wed., 5/31 | V Girls Tennis | Darien | Home - New Canaan HS-NCHS Tennis Courts [Directions] | W 4-3 | ||
| Thu., 6/1 | V Boys Tennis | Wilton | Away - Wilton HS-Tennis Courts [Directions] | 1:30 p.m. | 2:15 PM; 1 Bus | |
| Thu., 6/1 | V Girls Golf | FCIAC Girls Golf Championship - Fairfield Wheeler | Home - TBA [Directions] | 12:00 p.m. | 10:30 AM, Dismiss TBA; 1 Bus | |
| Fri., 6/2 | V Boys Volleyball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 5:00 p.m. | 2:40 PM; 1 Bus | |
| Fri., 6/2 | V Girls Lacrosse | Cheshire | Home - New Canaan HS-Dunning Stadium [Directions] | W 20-7 | ||
| Sat., 6/3 | V Baseball | Newington | Away - Newington HS-Alumni Field [Directions] | 2:30 p.m. | 11:00 AM; 1 Bus | |
| Sat., 6/3 | V Boys Lacrosse | Wilton | Home - New Canaan HS-Dunning Stadium [Directions] | W 8-2 | ||
| Mon., 6/5 | V Boys Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/5 | V Boys Tennis | CIAC Individual Invitational Opening Rounds | Away - Wesleyan | 10:00 a.m. | ||
| Mon., 6/5 | V Girls Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/5 | V Girls Tennis | CIAC Individual Invitational Opening Rounds | Away - Wesleyan | 10:00 a.m. | ||
| Tue., 6/6 | V Boys Tennis | CIAC Individual Invitational Round of 16 | Away - Wesleyan | 12:00 p.m. | ||
| Tue., 6/6 | V Boys Tennis | CIAC Individual Invitational Quarterfinals | Away - Wesleyan | 3:30 p.m. | ||
| Tue., 6/6 | V Boys Volleyball | Masuk | Away - Fairfield Warde HS-Gym [Directions] | 7:00 p.m. | 4:45 PM; 1 Bus | |
| Tue., 6/6 | V Girls Tennis | CIAC Individual Invitational Round of 16 | Away - Wesleyan | 12:00 p.m. | ||
| Tue., 6/6 | V Girls Tennis | CIAC Individual Invitational Quarterfinals | Away - Wesleyan | 3:30 p.m. | ||
| Wed., 6/7 | V Boys Tennis | CIAC Individual Invitational Semifinals | Away - Wesleyan | 3:30 p.m. | ||
| Wed., 6/7 | V Girls Golf | CIAC Division I Championship | Away - Timberlin GC | 8:30 a.m. | ||
| Wed., 6/7 | V Girls Tennis | CIAC Individual Invitational Semifinals | Away - Wesleyan | 3:30 p.m. | ||
| Thu., 6/8 | V Boys Tennis | CIAC Individual Invitational Finals | Away - Wesleyan | 3:30 p.m. | ||
| Thu., 6/8 | V Girls Tennis | CIAC Individual Invitational Finals | Away - Wesleyan | 3:30 p.m. | ||
| Fri., 6/9 | V Boys Lacrosse | Fairfield Prep | Away - Fairfield University-Rafferty Stadium [Directions] | 4:00 p.m. | 1:30 PM; 1 Bus | |
| Fri., 6/9 | V Girls Lacrosse | Wilton | Home - New Canaan HS-Dunning Stadium [Directions] | 7:00 p.m. | 2:45 PM; 1 Bus | |
| Sat., 6/10 | V Girls Golf | CIAC State Open Championship | Away - Black Hall Club | 1:00 p.m. | ||
| Mon., 6/12 | V Boys Outdoor Track | CIAC Hammer Throw Championship | Away - Willow Brook Park | 2:00 p.m. | ||
| Mon., 6/12 | V Girls Outdoor Track | CIAC Hammer Throw Championship | Away - Willow Brook Park | 4:00 p.m. | ||
| Tue., 6/13 | V Boys Outdoor Track | CIAC Decathlon Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 6/13 | V Girls Lacrosse | Darien | Away - Sacred Heart University-Campus Field [Directions] | 6:00 p.m. | ||
| Tue., 6/13 | V Girls Outdoor Track | CIAC Heptathlon Championship | Away - Willow Brook Park | 10:30 a.m. | ||
| Tue., 6/13 | V Girls Outdoor Track | CIAC Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/14 | V Boys Outdoor Track | CIAC Decathlon Championship | Away - Willow Brook Park | 8:30 a.m. | ||
| Wed., 6/14 | V Boys Outdoor Track | CIAC Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/14 | V Girls Outdoor Track | CIAC Heptathlon Championship | Away - Willow Brook Park | 8:30 a.m. | ||