| New Canaan 2020-21 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 586 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| Tue., 9/29 | V Girls Volleyball | Westhill (Scrim.) | Home - New Canaan HS-Main Gym [Directions] | 4:30 p.m. | ||
| Thu., 10/1 | V Boys Cross Country | Darien | Away - Darien HS-DHS Stadium East [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Thu., 10/1 | V Boys Soccer | Darien | Home - New Canaan HS-Dunning Stadium [Directions] | L 0-1 | ||
| Thu., 10/1 | V Girls Cross Country | Darien | Away - Darien HS-DHS Stadium East [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Thu., 10/1 | V Field Hockey | Darien | Away - Darien HS-DHS Stadium Field [Directions] | W 3-2 OT | 2:30 PM; 1 Bus | |
| Thu., 10/1 | V Girls Soccer | Darien | Away - Darien HS-DHS Center Oval Turf Field [Directions] | L 1-2 | 2:45 PM; 1 Bus | |
| Thu., 10/1 | V Girls Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | L 1-3 | 3:00 PM; 1 Bus | |
| Fri., 10/2 | V Football | Darien | Home - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | ||
| Sat., 10/3 | FR Boys Soccer | Darien | Home - Saxe MS-Field 1 [Directions] | 10:00 a.m. | ||
| Sat., 10/3 | V Field Hockey | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | W 4-0 | 1:30 PM; 1 Bus | |
| Sat., 10/3 | FR Field Hockey | Greenwich | Home - New Canaan HS-Dunning Stadium [Directions] | 9:00 a.m. | 8:30 AM; 1 Bus | |
| Sat., 10/3 | V Girls Soccer | Greenwich | Away - Greenwich HS-Field 7 [Directions] | W 3-2 | 2:30 PM; 1 Bus | |
| Sat., 10/3 | JV Girls Soccer | Darien | Away - Darien HS-DHS Center Oval Turf Field [Directions] | 9:30 a.m. | 8:30 AM; 1 Bus | |
| Sat., 10/3 | FR Girls Soccer | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 9:30 a.m. | ||
| Sat., 10/3 | V Girls Swimming and Diving | Darien | Home - New Canaan YMCA-Pool [Directions] | Postponed | ||
| Sat., 10/3 | JV Girls Volleyball | Darien | Home - New Canaan HS-Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 10/3 | FR Girls Volleyball | Darien | Home - New Canaan HS-Aux Gym [Directions] | 10:00 a.m. | ||
| Mon., 10/5 | JV Football | Darien | Home - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | ||
| Mon., 10/5 | V Boys Soccer | Darien | Away - Darien HS-DHS Center Oval Turf Field [Directions] | L 1-2 | 2:30 PM; 1 Bus | |
| Tue., 10/6 | V Boys Cross Country | Wright Tech | Home - Waveny Park [Directions] | 4:00 p.m. | ||
| Tue., 10/6 | V Girls Cross Country | Wright Tech | Home - Waveny Park [Directions] | 4:00 p.m. | ||
| Tue., 10/6 | V Girls Volleyball | Darien | Home - New Canaan HS-Main Gym [Directions] | L 1-3 | ||
| Wed., 10/7 | V Boys Soccer | Greenwich | Home - New Canaan HS-Dunning Stadium [Directions] | L 0-2 | ||
| Wed., 10/7 | JV Boys Soccer | Darien | Home - Conner Field, New Cannan [Directions] | 4:00 p.m. | ||
| Wed., 10/7 | JV Field Hockey | Greenwich | Home - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Thu., 10/8 | FR Football | Darien | Away - Darien HS-DHS Stadium East [Directions] | 4:00 p.m. | 2:45 PM; 1 Bus | |
| Thu., 10/8 | V Girls Soccer | Westhill | Home - New Canaan HS-Dunning Stadium [Directions] | W 5-0 | ||
| Thu., 10/8 | V Girls Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | W 3-0 | 2:45 PM; 1 Bus | |
| Fri., 10/9 | V Football | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:15 p.m. | 2:45 PM; 1 Bus | |
| Fri., 10/9 | V Field Hockey | Westhill | Home - New Canaan HS-Dunning Stadium [Directions] | W 4-0 | ||
| Fri., 10/9 | V Girls Swimming and Diving | Greenwich | Away - Greenwich HS-Pool [Directions] | 4:10 p.m. | 3:45 PM; 1 Bus, 1 Van (Bus will take Swimmers and Van will take Divers.) | |
| Sat., 10/10 | JV Football | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 1:30 p.m. | 11:45 AM; 1 Bus | |
| Sat., 10/10 | JV Field Hockey | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 9:30 a.m. | 8:15 AM; 1 Bus | |
| Sat., 10/10 | FR Field Hockey | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 11:00 a.m. | 9:45 AM; 1 Bus | |
| Sat., 10/10 | JV Girls Soccer | JV vs Freshman Girls Soccer | Home - Saxe MS-Field 1 [Directions] | 12:00 p.m. | ||
| Sat., 10/10 | V Girls Swimming and Diving | Westhill/Stamford | Home - New Canaan YMCA-Pool [Directions] | 4:00 p.m. | ||
| Sat., 10/10 | JV Girls Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 10:15 a.m. | 9:00 AM; 1 Bus | |
| Sat., 10/10 | FR Girls Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 9:00 a.m. | 7:45 AM; 1 Bus | |
| Mon., 10/12 | V Boys Soccer | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | L 0-6 | ||
| Tue., 10/13 | V Boys Cross Country | Greenwich | Home - Waveny Park [Directions] | 4:00 p.m. | ||
| Tue., 10/13 | V Girls Cross Country | Greenwich | Home - Waveny Park [Directions] | 4:00 p.m. | ||
| Tue., 10/13 | V Girls Soccer | Stamford | Home - New Canaan HS-Dunning Stadium [Directions] | W 5-0 | ||
| Tue., 10/13 | V Girls Volleyball | Stamford | Home - New Canaan HS-Main Gym [Directions] | W 3-0 | ||
| Wed., 10/14 | V Boys Soccer | Wright Tech | Home - New Canaan HS-Dunning Stadium [Directions] | W 6-0 | ||
| Wed., 10/14 | V Field Hockey | Stamford | Home - New Canaan HS-Dunning Stadium [Directions] | W 7-0 | ||
| Thu., 10/15 | V Girls Soccer | Darien | Home - New Canaan HS-Dunning Stadium [Directions] | L 0-1 | ||
| Thu., 10/15 | V Girls Volleyball | Wright Tech | Home - New Canaan HS-Main Gym [Directions] | W 3-0 | ||
| Sat., 10/17 | JV Boys Soccer | Westhill | Home - Conner Field, New Cannan [Directions] | 12:00 p.m. | ||
| Sat., 10/17 | FR Boys Soccer | Westhill | Home - Saxe MS-Field 1 [Directions] | 12:00 p.m. | ||
| Sat., 10/17 | JV Field Hockey | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 9:00 a.m. | 8:30 AM; 1 Bus | |
| Sat., 10/17 | JV Girls Soccer | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 12:00 p.m. | 10:30 AM; 1 Bus | |
| Sat., 10/17 | FR Girls Soccer | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 10:00 a.m. | 8:30 AM; 1 Bus | |
| Sun., 10/18 | V Girls Swimming and Diving | Darien | Home - New Canaan YMCA-Pool [Directions] | 3:00 p.m. | ||
| Mon., 10/19 | V Boys Soccer | Wright Tech | Away - Scalzi Park [Directions] | W 7-0 | 2:15 PM; 1 Bus | |
| Mon., 10/19 | V Field Hockey | Darien | Home - New Canaan HS-Dunning Stadium [Directions] | L 1-3 | ||
| Tue., 10/20 | V Boys Cross Country | Stamford | Home - Waveny Park [Directions] | 4:00 p.m. | ||
| Tue., 10/20 | V Girls Cross Country | Stamford | Home - Waveny Park [Directions] | 4:00 p.m. | ||
| Tue., 10/20 | V Girls Soccer | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | T 1-1 | 2:30 PM; 1 Bus | |
| Tue., 10/20 | V Girls Swimming and Diving | Darien | Away - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | 12:00 PM | |
| Tue., 10/20 | V Girls Volleyball | Wright Tech | Away - J M Wright Tech School-Thomas R. Good Gymnasium [Directions] | W 3-0 | 2:50 PM; 1 Bus | |
| Wed., 10/21 | V Boys Soccer | Greenwich | Home - New Canaan HS-Dunning Stadium [Directions] | L 0-3 | ||
| Wed., 10/21 | V Field Hockey | Greenwich | Home - New Canaan HS-Dunning Stadium [Directions] | T 2-2 OT | ||
| Wed., 10/21 | V Girls Swimming and Diving | Darien | Away - Darien YMCA [Directions] | 3:00 p.m. | 2:05 PM; 1 Bus | |
| Wed., 10/21 | V Girls Swimming and Diving | St. Joseph | Away - Hillcrest MS-Pool [Directions] | 8:00 p.m. | ||
| Thu., 10/22 | V Girls Volleyball | Greenwich | Home - New Canaan HS-Main Gym [Directions] | L 0-3 | ||
| Fri., 10/23 | V Football | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Fri., 10/23 | FR Football | Stamford | Home - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | ||
| Sat., 10/24 | JV Boys Soccer | Stamford | Home - Conner Field, New Cannan [Directions] | 10:00 a.m. | ||
| Sat., 10/24 | FR Boys Soccer | Stamford | Home - Saxe MS-Field 1 [Directions] | 12:00 p.m. | ||
| Sat., 10/24 | JV Field Hockey | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 11:45 a.m. | 8:30 AM; 1 Bus | |
| Sat., 10/24 | FR Field Hockey | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 10:00 a.m. | 8:45 AM; 1 Bus | |
| Sat., 10/24 | JV Girls Soccer | Stamford | Away - Stamford HS-SHS Upper Soccer Field [Directions] | 10:00 a.m. | 8:30 AM; 1 Bus | |
| Sat., 10/24 | V Girls Swimming and Diving | Trumbull | Away - Hillcrest MS-Pool [Directions] | 8:00 a.m. | ||
| Sat., 10/24 | V Girls Swimming and Diving | Greenwich | Home - New Canaan YMCA-Pool [Directions] | 4:00 p.m. | ||
| Sat., 10/24 | JV Girls Volleyball | Greenwich | Home - New Canaan HS-Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 10/24 | FR Girls Volleyball | Greenwich | Home - New Canaan HS-Main Gym [Directions] | 12:00 p.m. | ||
| Mon., 10/26 | SO Football | Greenwich | Home - New Canaan HS-Dunning Stadium [Directions] | 4:15 p.m. | ||
| Tue., 10/27 | V Boys Cross Country | Westhill | Home - Waveny Park [Directions] | 4:00 p.m. | ||
| Tue., 10/27 | V Girls Cross Country | Westhill | Home - Waveny Park [Directions] | 4:00 p.m. | ||
| Tue., 10/27 | V Girls Soccer | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 3:45 p.m. | 2:30 PM; 1 Bus | |
| Tue., 10/27 | V Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | L 0-3 | 3:30 PM; 1 Bus | |
| Wed., 10/28 | V Boys Soccer | Westhill | Away - Westhill HS-Westhill Front Turf Field [Directions] | T 0-0 | 2:45 PM; 1 Bus | |
| Wed., 10/28 | V Field Hockey | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | W 5-0 | 2:30 PM; 1 Bus | |
| Thu., 10/29 | V Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | L 2-3 | 3:00 PM; 1 Bus | |
| Fri., 10/30 | V Football | Greenwich | Home - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | ||
| Fri., 10/30 | SO Football | Greenwich | Home - New Canaan HS-WTT #1 [Directions] | 4:00 p.m. | ||
| Fri., 10/30 | FR Football | Greenwich | Home - New Canaan HS-WTT #1 [Directions] | 4:00 p.m. | ||
| Fri., 10/30 | V Boys Soccer | Stamford | Home - New Canaan HS-Dunning Stadium [Directions] | L 0-2 | 2:30 PM; 1 Bus | |
| Fri., 10/30 | V Field Hockey | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | W 9-0 | 2:20 PM; 1 Bus | |
| Fri., 10/30 | V Girls Soccer | Stamford | Away - Stamford HS-SHS Upper Soccer Field [Directions] | W 4-0 | 2:30 PM; 1 Bus | |
| Fri., 10/30 | V Girls Swimming and Diving | Westhill/Stamford | Away - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | 2:15 PM; 1 Bus | |
| Sat., 10/31 | JV Boys Soccer | Greenwich | Away - Greenwich HS-Field 7 [Directions] | 9:00 a.m. | 7:20 AM; 1 Bus | |
| Sat., 10/31 | FR Boys Soccer | Greenwich | Away - Greenwich HS-Field 3 [Directions] | 9:00 a.m. | 7:20 AM; 1 Bus | |
| Sat., 10/31 | JV Girls Soccer | Greenwich | Home - New Canaan HS-Dunning Stadium [Directions] | 9:00 a.m. | ||
| Sat., 10/31 | FR Girls Soccer | Greenwich | Home - New Canaan HS-Dunning Stadium [Directions] | 11:00 a.m. | ||
| Sat., 10/31 | JV Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 11:30 a.m. | 10:15 AM; 1 Bus | |
| Sat., 10/31 | FR Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 10:00 a.m. | 8:45 AM; 1 Bus | |
| Mon., 11/2 | V Boys Soccer | Westhill | Home - New Canaan HS-Dunning Stadium [Directions] | 4:30 p.m. | ||
| Tue., 11/3 | V Field Hockey | Darien | Away - Darien HS-DHS Stadium Field [Directions] | W 3-2 | 2:30 PM; 1 Bus | |
| Tue., 11/3 | V Girls Soccer | Darien | Away - Darien HS-DHS Center Oval Turf Field [Directions] | L 2-3 | 4:00 PM; 1 Bus | |
| Tue., 11/3 | V Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | L 1-3 | ||
| Wed., 11/4 | V Boys Soccer | Stamford | Home - New Canaan HS-Dunning Stadium [Directions] | W 1-1(PK) | ||
| Thu., 11/5 | V Field Hockey | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | W 2-0 | 2:15 PM; 1 Bus | |
| Thu., 11/5 | V Girls Soccer | Greenwich | Home - New Canaan HS-Dunning Stadium [Directions] | L 2-3 | 2:15 PM; 1 Bus | |
| Thu., 11/5 | V Girls Volleyball | Stamford | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 11/6 | V Boys Soccer | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | L 0-2 | 12:15 PM; 1 Bus | |
| Fri., 11/6 | JV Girls Volleyball | Darien | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | 9:45 AM; 1 Bus | |
| Fri., 11/6 | FR Girls Volleyball | Darien | Home - New Canaan HS-Main Gym [Directions] | 3:30 p.m. | 11:15 AM; 1 Bus | |
| Sat., 11/7 | JV Boys Soccer | Darien | Away - Darien HS-DHS Center Oval Turf Field [Directions] | 12:30 p.m. | 11:15 AM; 1 Bus | |
| Sat., 11/7 | FR Boys Soccer | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 12:30 p.m. | 11:15 AM; 1 Bus | |
| Sat., 11/7 | JV Field Hockey | Greenwich | Home - New Canaan HS-Dunning Stadium [Directions] | 10:30 a.m. | ||
| Sat., 11/7 | JV Field Hockey | Darien | Home - New Canaan HS-Dunning Stadium [Directions] | 9:00 a.m. | ||
| Sat., 11/7 | FR Field Hockey | Greenwich | Home - New Canaan HS-WTT #2 [Directions] | 10:30 a.m. | ||
| Sat., 11/7 | FR Field Hockey | Darien | Home - New Canaan HS-WTT #2 [Directions] | 9:00 a.m. | ||
| Sat., 11/7 | JV Girls Soccer | Greenwich | Home - Conner Field, New Cannan [Directions] | 10:30 a.m. | ||
| Sat., 11/7 | JV Girls Soccer | Darien | Home - Conner Field, New Cannan [Directions] | 9:00 a.m. | ||
| Sat., 11/7 | FR Girls Soccer | Greenwich | Home - Saxe MS-Field 1 [Directions] | 10:30 a.m. | ||
| Sat., 11/7 | FR Girls Soccer | Darien | Home - Saxe MS-Field 1 [Directions] | 9:00 a.m. | ||
| Tue., 11/10 | V Girls Soccer | Greenwich | Home - New Canaan HS-Dunning Stadium [Directions] | 6:30 p.m. | ||
| Thu., 11/12 | V Girls Soccer | Darien | Away - Darien HS-DHS Center Oval Turf Field [Directions] | 2:00 p.m. | ||
| Wed., 2/3 | V Girls Ice Hockey | Greenwich (Scrim.) | Home - Darien Ice House-Ice Rink [Directions] | 3:30 p.m. | ||
| Thu., 2/4 | V Boys Basketball | Greenwich (Scrim.) | Away - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | 3:15 PM; 1 Bus | |
| Thu., 2/4 | V Girls Basketball | Greenwich (Scrim.) | Home - New Canaan HS-Main Gym [Directions] | 4:35 p.m. | ||
| Sat., 2/6 | V Boys Ice Hockey | Fairfield Warde/Ludlowe (Scrim.) | Away - Wonderland of Ice-Stadium [Directions] | 12:00 p.m. | 10:45 AM; 1 Bus | |
| Mon., 2/8 | V Boys Ice Hockey | Fairfield Prep | Home - Darien Ice House-Ice Rink [Directions] | W 2-1 | ||
| Wed., 2/10 | V Boys Basketball | Fairfield Ludlowe | Home - New Canaan HS-Main Gym [Directions] | W 52-47 | ||
| Wed., 2/10 | V Boys Ice Hockey | Notre Dame-West Haven | Away - West Haven HS-Bennett Rink [Directions] | L 2-3 | 2:10 PM; 1 Bus | |
| Wed., 2/10 | V Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | L 24-41 | 3:15 PM; 1 Bus | |
| Wed., 2/10 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Darien Ice House-Ice Rink [Directions] | W 5-1 | ||
| Fri., 2/12 | V Boys Basketball | Greenwich | Home - New Canaan HS-Main Gym [Directions] | W 50-41 | ||
| Fri., 2/12 | JV Boys Ice Hockey | Ridgefield | Home - Darien Ice House-Ice Rink [Directions] | 8:20 p.m. | ||
| Fri., 2/12 | V Girls Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | W 43-40 | 3:20 PM; 1 Bus | |
| Fri., 2/12 | JV Girls Ice Hockey | Greenwich | Home - Stamford Twin Rinks-East [Directions] | 8:45 p.m. | ||
| Sat., 2/13 | JV Boys Basketball | Fairfield Ludlowe | Home - New Canaan HS-Main Gym [Directions] | 11:15 a.m. | ||
| Sat., 2/13 | FR Boys Basketball | Fairfield Ludlowe | Home - New Canaan HS-Main Gym [Directions] | 9:30 a.m. | ||
| Sat., 2/13 | V Boys Ice Hockey | Ridgefield | Home - Darien Ice House-Ice Rink [Directions] | W 5-1 | ||
| Sat., 2/13 | JV Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 10:30 a.m. | 9:15 AM; 1 Bus | |
| Sat., 2/13 | FR Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 9:00 a.m. | 7:45 AM; 1 Bus | |
| Sat., 2/13 | V Girls Ice Hockey | Darien | Home - Darien Ice House-Ice Rink [Directions] | L 1-2 | ||
| Sun., 2/14 | V Girls Gymnastics | Fairfield Warde | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 1:00 p.m. | ||
| Mon., 2/15 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Conners - Stamford-Ice Rink [Directions] | W 8-0 | 1:45 PM; 1 Bus | |
| Tue., 2/16 | V Boys Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | W 55-36 | 3:00 PM; 1 Bus | |
| Tue., 2/16 | JV Boys Ice Hockey | Darien | Away - Stamford Twin Rinks-West [Directions] | 2:30 p.m. | 1:15 PM; 1 Bus | |
| Tue., 2/16 | V Girls Basketball | Trumbull | Home - New Canaan HS-Main Gym [Directions] | L 24-46 | ||
| Wed., 2/17 | V Boys Ice Hockey | Darien | Home - Darien Ice House-Ice Rink [Directions] | T 4-4(OT) | ||
| Wed., 2/17 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Darien Ice House-Ice Rink [Directions] | W 8-1 | ||
| Thu., 2/18 | V Boys Basketball | Bassick | Away - Bassick HS-Gym [Directions] | Cancelled | 3:00 PM; 1 Bus | |
| Thu., 2/18 | V Girls Basketball | Bassick | Home - New Canaan HS-Main Gym [Directions] | Cancelled | ||
| Fri., 2/19 | JV Boys Ice Hockey | Notre Dame-West Haven | Home - Darien Ice House-Ice Rink [Directions] | 8:20 p.m. | ||
| Fri., 2/19 | JV Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | Postponed | 2:40 PM; 1 Bus | |
| Sat., 2/20 | JV Boys Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 10:30 a.m. | 10:05 AM; 1 Bus | |
| Sat., 2/20 | FR Boys Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 9:00 a.m. | 8:35 AM; 1 Bus | |
| Sat., 2/20 | V Boys Ice Hockey | St. Joseph | Home - Darien Ice House-Ice Rink [Directions] | W 5-2 | ||
| Sat., 2/20 | V Boys Swimming and Diving | Staples | Home - New Canaan YMCA-Pool [Directions] | 4:00 p.m. | ||
| Sat., 2/20 | V Girls Basketball | Wilton | Home - New Canaan HS-Main Gym [Directions] | W 57-23 | ||
| Sat., 2/20 | JV Girls Basketball | Westhill | Home - New Canaan HS-Main Gym [Directions] | 11:15 a.m. | ||
| Sat., 2/20 | FR Girls Basketball | Westhill | Home - New Canaan HS-Main Gym [Directions] | 9:30 a.m. | ||
| Sat., 2/20 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | W 9-0 | 2:40 PM; 1 Bus | |
| Mon., 2/22 | V Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | L 40-48 | 3:15 PM; 1 Bus | |
| Mon., 2/22 | V Girls Basketball | Brien McMahon | Home - New Canaan HS-Main Gym [Directions] | W 53-18 | ||
| Tue., 2/23 | V Girls Gymnastics | Wilton, Stamford, Westhill | Away - Wilton HS-Aux Gym [Directions] | 3:45 p.m. | ||
| Tue., 2/23 | V Girls Ice Hockey | Greenwich | Away - Greenwich - Dorothy Hamill-Rink [Directions] | W 2-0 | 3:40 PM; 1 Bus | |
| Wed., 2/24 | JV Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 6:00 p.m. | 4:30 PM; 1 Bus | |
| Wed., 2/24 | FR Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:30 p.m. | 3:00 PM; 1 Bus | |
| Wed., 2/24 | V Boys Ice Hockey | Greenwich | Away - DontUse-Dorothy Hamill Ice Rink-Dorothy Hamill Ice Rink [Directions] | L 0-1 | 3:15 PM; 1 Bus | |
| Wed., 2/24 | JV Girls Basketball | Ridgefield | Home - New Canaan HS-Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 2/24 | FR Girls Basketball | Ridgefield | Home - New Canaan HS-Main Gym [Directions] | 3:30 p.m. | ||
| Wed., 2/24 | V Girls Gymnastics | Wilton | Home - Chelsea Piers - -Gym [Directions] | 74.7 | ||
| Thu., 2/25 | V Boys Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | W 56-34 | 3:00 PM; 1 Bus | |
| Fri., 2/26 | JV Boys Ice Hockey | Greenwich | Home - Darien Ice House-Ice Rink [Directions] | 6:30 p.m. | ||
| Fri., 2/26 | V Girls Basketball | Bassick | Home - New Canaan HS-Main Gym [Directions] | W 57-44 | ||
| Fri., 2/26 | JV Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Stamford Twin Rinks-East [Directions] | 8:45 p.m. | ||
| Sat., 2/27 | V Boys Basketball | Darien | Home - New Canaan HS-Main Gym [Directions] | W 55-51 | ||
| Sat., 2/27 | JV Boys Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 11:00 a.m. | 9:30 AM; 1 Bus | |
| Sat., 2/27 | FR Boys Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 9:30 a.m. | 8:00 AM; 1 Bus | |
| Sat., 2/27 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland of Ice-Stadium [Directions] | L 5-7 | 6:40 PM; 1 Bus | |
| Sat., 2/27 | V Girls Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | L 26-29 | 9:15 AM; 1 Bus | |
| Sat., 2/27 | JV Girls Basketball | St. Joseph | Home - New Canaan HS-Main Gym [Directions] | 11:15 a.m. | ||
| Sat., 2/27 | FR Girls Basketball | St. Joseph | Home - New Canaan HS-Main Gym [Directions] | 9:30 a.m. | ||
| Sat., 2/27 | V Girls Ice Hockey | Greenwich | Home - Darien Ice House-Ice Rink [Directions] | W 2-0 | ||
| Sat., 2/27 | JV Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice-New [Directions] | 6:30 p.m. | 4:45 PM; 1 Bus | |
| Sun., 2/28 | JV Boys Ice Hockey | Darien | Home - Darien Ice House-Ice Rink [Directions] | 5:20 p.m. | ||
| Mon., 3/1 | V Boys Swimming and Diving | Darien | Away - Darien YMCA [Directions] | 3:00 p.m. | 1:45 PM; 1 Bus | |
| Tue., 3/2 | V Boys Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | W 59-50 | 3:30 PM; 1 Bus | |
| Tue., 3/2 | V Girls Basketball | Staples | Home - New Canaan HS-Main Gym [Directions] | L 30-33 | ||
| Wed., 3/3 | V Boys Basketball | Ridgefield | Home - New Canaan HS-Main Gym [Directions] | W 64-59 2OT | ||
| Wed., 3/3 | V Boys Ice Hockey | Greenwich | Home - Darien Ice House-Ice Rink [Directions] | L 2-3 | ||
| Wed., 3/3 | JV Boys Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | 5:30 p.m. | 4:10 PM; 1 Bus | |
| Wed., 3/3 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Away - Norwalk HS-Pat Spinola Natatorium [Directions] | 5:00 p.m. | 3:30 PM; 1 Bus | |
| Wed., 3/3 | V Girls Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | L 36-48 | 3:30 PM; 1 Bus | |
| Wed., 3/3 | JV Girls Basketball | Ridgefield | Away - Ridgefield HS [Directions] | 5:00 p.m. | 3:30 PM; 1 Bus | |
| Wed., 3/3 | V Girls Gymnastics | Staples | Home - Chelsea Piers - -Gym [Directions] | 89.25 | ||
| Fri., 3/5 | V Boys Basketball | Wilton | Home - New Canaan HS-Main Gym [Directions] | L 37-35 | ||
| Fri., 3/5 | V Girls Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | W 29-26 | 3:40 PM; 1 Bus | |
| Fri., 3/5 | V Girls Gymnastics | Greenwich, Stamford, Westhill | Away - Greenwich YWCA [Directions] | 6:30 p.m. | ||
| Fri., 3/5 | V Girls Gymnastics | Darien | Home - Chelsea Piers - -Gym [Directions] | 7:30 p.m. | ||
| Fri., 3/5 | JV Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Stamford Twin Rinks-East [Directions] | 8:45 p.m. | ||
| Sat., 3/6 | JV Boys Basketball | Staples | Home - New Canaan HS-Main Gym [Directions] | 11:15 a.m. | ||
| Sat., 3/6 | FR Boys Basketball | Staples | Home - New Canaan HS-Main Gym [Directions] | 9:30 a.m. | ||
| Sat., 3/6 | V Boys Ice Hockey | St. Joseph | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | W 6-2 | 4:30 PM; 1 Bus | |
| Sat., 3/6 | V Boys Swimming and Diving | Greenwich | Home - New Canaan YMCA-Pool [Directions] | 4:00 p.m. | ||
| Sat., 3/6 | JV Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 10:30 a.m. | 8:30 AM; 1 Bus | |
| Sat., 3/6 | FR Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 9:00 a.m. | 7:30 AM; 1 Bus | |
| Sat., 3/6 | V Girls Ice Hockey | Darien | Away - Darien Ice House-Ice Rink [Directions] | W 4-3 | ||
| Sat., 3/6 | JV Girls Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | 6:45 p.m. | 6:45 PM; 1 Bus | |
| Mon., 3/8 | V Boys Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | W 40-28 | 3:15 PM; 1 Bus | |
| Mon., 3/8 | V Girls Basketball | Norwalk | Home - New Canaan HS-Main Gym [Directions] | Cancelled | ||
| Tue., 3/9 | JV Boys Ice Hockey | Darien | Away - Stamford Twin Rinks-West [Directions] | 3:00 p.m. | 3:10 PM; 1 Bus | |
| Tue., 3/9 | V Girls Ice Hockey | Darien | Home - Darien Ice House-Ice Rink [Directions] | W 1-0 | ||
| Wed., 3/10 | V Boys Ice Hockey | Ridgefield | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | W 1-0 | 2:05 PM; 1 Bus | |
| Wed., 3/10 | V Boys Swimming and Diving | Trumbull | Away - Hillcrest MS-Pool [Directions] | 3:30 p.m. | 2:10 PM; 1 Bus | |
| Wed., 3/10 | JV Girls Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 5:30 p.m. | 4:00 PM; 1 Bus | |
| Wed., 3/10 | FR Girls Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Wed., 3/10 | V Girls Gymnastics | Trumbull | Home - Chelsea Piers - -Gym [Directions] | 86.65 | ||
| Wed., 3/10 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Darien Ice House-Ice Rink [Directions] | 6:00 p.m. | ||
| Wed., 3/10 | V Girls Indoor Track | Darien | Away - Darien HS-DHS Track [Directions] | 3:00 p.m. | 2:15 PM; 1 Bus | |
| Thu., 3/11 | V Boys Basketball | Stamford | Home - New Canaan HS-Main Gym [Directions] | W 56-44 | ||
| Thu., 3/11 | JV Boys Ice Hockey | Notre Dame-West Haven | Away - West Haven HS-Bennett Rink [Directions] | 3:40 p.m. | 2:00 PM; 1 Bus | |
| Thu., 3/11 | V Girls Basketball | Stamford | Away - Stamford HS-Kuzco Gymnasium [Directions] | L 33-34 | 3:30 PM; 1 Bus | |
| Thu., 3/11 | V Girls Gymnastics | Greenwich | Home - Chelsea Piers - -Gym [Directions] | 7:30 p.m. | ||
| Fri., 3/12 | V Girls Basketball | Danbury | Home - New Canaan HS-Main Gym [Directions] | L 42-62 | ||
| Fri., 3/12 | JV Girls Ice Hockey | Greenwich | Home - Stamford Twin Rinks-East [Directions] | 8:45 p.m. | ||
| Sat., 3/13 | V Boys Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | L 35-60 | 2:00 PM; 1 Bus | |
| Sat., 3/13 | JV Boys Basketball | Wilton | Home - New Canaan HS-Main Gym [Directions] | 11:15 a.m. | ||
| Sat., 3/13 | FR Boys Basketball | Wilton | Home - New Canaan HS-Main Gym [Directions] | 9:30 a.m. | ||
| Sat., 3/13 | V Boys Ice Hockey | Darien | Away - Darien Ice House-Ice Rink [Directions] | L 1-4 | ||
| Sat., 3/13 | V Boys Swimming and Diving | Ridgefield | Home - New Canaan YMCA-Pool [Directions] | 4:00 p.m. | ||
| Sat., 3/13 | JV Girls Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 11:30 a.m. | 10:00 AM; 1 Bus | |
| Sat., 3/13 | FR Girls Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 10:00 a.m. | 8:30 AM; 1 Bus | |
| Sun., 3/14 | JV Boys Ice Hockey | Ridgefield | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:10 p.m. | 6:45 PM; 1 Bus | |
| Sun., 3/14 | V Girls Gymnastics | Fairfield Ludlowe | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 1:00 p.m. | ||
| Sun., 3/14 | V Girls Gymnastics | Fairfield Warde | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 1:00 p.m. | ||
| Mon., 3/15 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Darien Ice House-Ice Rink [Directions] | 8:15 p.m. | ||
| Tue., 3/16 | V Boys Basketball | Norwalk | Home - New Canaan HS-Main Gym [Directions] | W 41-33 | ||
| Wed., 3/17 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Home - Darien Ice House-Ice Rink [Directions] | L 2-6 | ||
| Wed., 3/17 | V Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | L 39-52 | 3:00 PM; 1 Bus | |
| Thu., 3/18 | JV Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 5:15 p.m. | 3:30 PM; 1 Bus | |
| Thu., 3/18 | FR Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 3:45 p.m. | 2:10 PM; 1 Bus | |
| Thu., 3/18 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Darien Ice House-Ice Rink [Directions] | 7:15 p.m. | ||
| Fri., 3/19 | V Boys Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | W 57-48 | 3:45 PM; 1 Bus | |
| Sat., 3/20 | JV Boys Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 10:30 a.m. | 9:50 AM; 1 Bus | |
| Sat., 3/20 | FR Boys Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 9:00 a.m. | 8:00 AM; 1 Bus | |
| Sat., 3/20 | JV Girls Basketball | Darien | Home - New Canaan HS-Main Gym [Directions] | 11:30 a.m. | ||
| Sat., 3/20 | FR Girls Basketball | Darien | Home - New Canaan HS-Main Gym [Directions] | 9:30 a.m. | ||
| Sat., 3/20 | V Girls Ice Hockey | Darien | Away - Darien Ice House-Ice Rink [Directions] | 4:00 p.m. | ||
| Sat., 3/20 | V Girls Indoor Track | Staples | Away - Staples HS-Field House [Directions] | 11:00 a.m. | 9:45 AM; 1 Bus | |
| Sun., 3/21 | JV Boys Ice Hockey | St. Joseph | Home - Darien Ice House-Ice Rink [Directions] | 6:10 p.m. | ||
| Mon., 3/22 | V Boys Ice Hockey | Ridgefield | Home - Darien Ice House-Ice Rink [Directions] | W 2-1 | ||
| Tue., 3/23 | V Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | L 49-62 | 5:00 PM; 1 Bus | |
| Tue., 3/23 | V Boys Swimming and Diving | Wilton | Away - Wilton YMCA [Directions] | 3:30 p.m. | 1:45 PM; 1 Bus | |
| Tue., 3/23 | V Girls Gymnastics | Fairfield Ludlowe | Home - Chelsea Piers - -Gym [Directions] | 7:30 p.m. | ||
| Thu., 3/25 | V Boys Ice Hockey | Darien | Away - Darien Ice House-Ice Rink [Directions] | W 2-1 | ||
| Sat., 3/27 | V Boys Ice Hockey | Greenwich | Away - Greenwich - Dorothy Hamill-Rink [Directions] | W 3-1 | ||
| Sat., 4/3 | V Baseball | Weston (Scrim.) | Away - Weston HS-Revson #1 (Varsity) [Directions] | 12:00 p.m. | 10:30 AM; 1 Bus | |
| Mon., 4/5 | V Baseball | Wilton (Scrim.) | Away - Wilton HS-Varsity Baseball Field [Directions] | 2:00 p.m. | 12:45 PM; 1 Bus | |
| Mon., 4/5 | JV Baseball | Wilton (Scrim.) | Away - Wilton HS-JV Baseball Field [Directions] | W 7-6 | 12:45 PM; 1 Bus | |
| Mon., 4/5 | V Softball | Brien McMahon (Scrim.) | Away - Brien McMahon HS-Softball Diamond [Directions] | 4:30 p.m. | ||
| Mon., 4/5 | V Softball | TBA | Away - TBA-Grandville HS | Cancelled | 3:10 PM; 1 Bus | |
| Wed., 4/7 | V Baseball | St. Lukes (Scrim.) | Home - Mead Park-Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 4/7 | V Boys Lacrosse | Greenwich (Scrim.) | Away - Greenwich HS-Cardinal Stadium [Directions] | Cancelled | 3:15 PM; 1 Bus | |
| Wed., 4/7 | V Girls Lacrosse | Greenwich Academy (Scrim.) | Away - Greenwich Academy-Stadium | 3:30 p.m. | 2:15 PM; 1 Bus | |
| Wed., 4/7 | JV Girls Lacrosse | Greenwich Academy (Scrim.) | Away - Greenwich Academy-2nd Field | 5:00 p.m. | ||
| Wed., 4/7 | V Softball | Joel Barlow (Scrim.) | Home - Waveny Park-Orchard Field [Directions] | 4:00 p.m. | ||
| Thu., 4/8 | V Baseball | Greenwich (Scrim.) | Away - Greenwich HS-Baseball Field [Directions] | Cancelled | 2:30 PM; 1 Bus | |
| Thu., 4/8 | V Boys Volleyball | Joel Barlow (Scrim.) | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 4/10 | V Baseball | Stamford | Away - Stamford HS-SHS Baseball Diamond [Directions] | W 7-0 | 11:45 AM; 1 Bus | |
| Sat., 4/10 | JV Baseball | Stamford | Home - Mead Park-Baseball Field [Directions] | W 11-5 | ||
| Sat., 4/10 | FR Baseball | Fairfield Ludlowe | Home - New Canaan HS-Coppo Field [Directions] | 10:30 a.m. | ||
| Sat., 4/10 | FR Baseball | Fairfield Ludlowe | Home - New Canaan HS-Coppo Field [Directions] | 12:30 p.m. | ||
| Sat., 4/10 | V Boys Lacrosse | Staples | Away - Staples HS-Staples Stadium [Directions] | L 3-7 | 1:15 PM; 1 Bus | |
| Sat., 4/10 | JV Boys Lacrosse | Staples | Away - Staples HS-Staples Stadium [Directions] | 12:30 p.m. | 11:00 AM; 1 Bus | |
| Sat., 4/10 | V Boys Tennis | Danbury | Home - New Canaan HS-NCHS Tennis Courts [Directions] | W 7-0 [Detailed Results] | ||
| Sat., 4/10 | V Boys Volleyball | Staples | Home - New Canaan HS-Main Gym [Directions] | W 3-0 | ||
| Sat., 4/10 | JV Boys Volleyball | Staples | Home - New Canaan HS-Main Gym [Directions] | 1:00 p.m. | ||
| Sat., 4/10 | V Softball | Wilton | Home - Waveny Park-Orchard Field [Directions] | W 10-0 | ||
| Sat., 4/10 | JV Softball | Wilton | Away - Wilton HS-JV Softball Field [Directions] | Postponed | 2:45 PM; 1 Bus | |
| Sat., 4/10 | V Girls Tennis | Danbury | Away - Danbury HS-DHS Tennis Courts [Directions] | W 7-0 | 9:20 AM; 1 Bus | |
| Mon., 4/12 | JV Softball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | Postponed | 2:30 PM; 1 Bus | |
| Tue., 4/13 | V Baseball | Fairfield Ludlowe | Away - Kiwanis Field-Baseball Diamond [Directions] | L 8-9 | 2:30 PM; 1 Bus | |
| Tue., 4/13 | JV Baseball | Fairfield Ludlowe | Home - Mead Park-Baseball Field [Directions] | L 4-10 | ||
| Tue., 4/13 | V Boys Lacrosse | Fairfield Ludlowe | Home - New Canaan HS-Dunning Stadium [Directions] | W 13-9 | ||
| Tue., 4/13 | JV Boys Lacrosse | Fairfield Ludlowe | Home - New Canaan HS-Dunning Stadium [Directions] | 6:00 p.m. | ||
| Tue., 4/13 | V Boys Outdoor Track | Brien McMahon | Home - New Canaan HS-NCHS Track [Directions] | 4:00 p.m. | ||
| Tue., 4/13 | V Boys Tennis | Wilton | Home - New Canaan HS-NCHS Tennis Courts [Directions] | L 4-3 [Detailed Results] | ||
| Tue., 4/13 | V Boys Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Gym [Directions] | W 3-0 | 3:00 PM; 1 Bus | |
| Tue., 4/13 | JV Boys Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Gym [Directions] | 4:30 p.m. | 4:15 PM; 1 Bus | |
| Tue., 4/13 | V Girls Outdoor Track | Brien McMahon | Home - New Canaan HS-NCHS Track [Directions] | 4:00 p.m. | ||
| Tue., 4/13 | V Softball | Fairfield Ludlowe | Home - Waveny Park-Orchard Field [Directions] | L 0-19 | ||
| Tue., 4/13 | V Girls Tennis | Wilton | Away - Wilton HS-Wilton Varsity Tennis Courts [Directions] | W 4-3 | 2:45 PM; 1 Bus | |
| Tue., 4/13 | JV Girls Tennis | Wilton | Away - Wilton Middlebrook School-JV Tennis Courts [Directions] | L 1-8 | 2:40 PM; 1 Bus | |
| Wed., 4/14 | V Baseball | Norwalk | Home - Mead Park-Baseball Field [Directions] | L 0-11 | ||
| Wed., 4/14 | JV Baseball | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | W 8-6 | 3:00 PM; 1 Bus | |
| Wed., 4/14 | FR Boys Lacrosse | Greenwich | Home - New Canaan HS-WTT #2 [Directions] | 4:30 p.m. | ||
| Wed., 4/14 | V Boys Tennis | Staples | Away - Staples HS-Staples Tennis Courts [Directions] | L 6-1 [Detailed Results] | 2:30 PM; 1 Bus | |
| Wed., 4/14 | V Boys Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | W 3-0 | 2:50 PM; 1 Bus | |
| Wed., 4/14 | JV Boys Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 5:30 p.m. | 4:00 PM; 1 Bus | |
| Wed., 4/14 | V Softball | Norwalk | Away - Norwalk HS-Ray Barry Field [Directions] | L 3-6 | 2:50 PM; 1 Bus | |
| Wed., 4/14 | JV Softball | Norwalk | Home - Waveny Park-Orchard Field [Directions] | Cancelled | ||
| Wed., 4/14 | V Girls Tennis | Staples | Home - New Canaan HS-NCHS Tennis Courts [Directions] | L 2-5 | ||
| Thu., 4/15 | V Boys Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | L 10-9 | 2:10 PM; 1 Bus | |
| Thu., 4/15 | JV Boys Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Turf Field II [Directions] | 6:00 p.m. | 4:00 PM; 1 Bus | |
| Fri., 4/16 | V Baseball | Trumbull | Home - Mead Park-Baseball Field [Directions] | W 3-0 | ||
| Fri., 4/16 | FR Boys Lacrosse | Ridgefield | Away - Ridgefield HS-RHS Lower Grass Field [Directions] | 6:00 p.m. | 2:20 PM; 1 Bus | |
| Fri., 4/16 | JV Boys Tennis | Wilton | Home - New Canaan HS-NCHS Tennis Courts [Directions] | Postponed | ||
| Sat., 4/17 | FR Baseball | Trumbull | Away - Trumbull HS-Varsity Baseball Field [Directions] | 10:00 a.m. | 8:30 AM; 1 Bus | |
| Sat., 4/17 | FR Baseball | Trumbull | Away - Trumbull HS-Varsity Baseball Field [Directions] | 12:00 p.m. | 10:15 AM; 1 Bus | |
| Sat., 4/17 | JV Softball | Trumbull | Home - Waveny Park-Orchard Field [Directions] | 11:00 a.m. | ||
| Mon., 4/19 | V Baseball | St. Joseph | Away - St. Joseph HS-Baseball Diamond [Directions] | W 3-2 | 2:10 PM; 1 Bus | |
| Mon., 4/19 | JV Baseball | St. Joseph | Home - Mead Park-Baseball Field [Directions] | W 6-5 | ||
| Mon., 4/19 | JV Boys Golf | Darien | Home - New Canaan HS-CCNC [Directions] | 3:15 p.m. | ||
| Mon., 4/19 | V Boys Lacrosse | Fairfield Prep | Home - New Canaan HS-Dunning Stadium [Directions] | W 10-8 | ||
| Mon., 4/19 | JV Boys Lacrosse | Fairfield Prep | Home - New Canaan HS-Dunning Stadium [Directions] | Postponed | ||
| Mon., 4/19 | V Boys Outdoor Track | Harding, Bassick, Bridgeport Central | Away - Warren Harding HS-Lewis Field [Directions] | 4:00 p.m. | 2:05 PM; 1 Bus | |
| Mon., 4/19 | V Girls Golf | Greenwich | Away - Millbrook Country Club [Directions] | NC-177 Greenwich-206 | 2:20 PM, Dismiss TBA; 1 Bus | |
| Mon., 4/19 | V Girls Outdoor Track | Harding, Bassick, Bridgeport Central | Away - Warren Harding HS-Lewis Field [Directions] | 4:00 p.m. | 2:05 PM; 1 Bus | |
| Mon., 4/19 | V Softball | St. Joseph | Home - Waveny Park-Orchard Field [Directions] | L 1-23 | ||
| Mon., 4/19 | JV Softball | St. Joseph | Away - St. Joseph HS-Softball Diamond [Directions] | 4:00 p.m. | 2:15 PM; 1 Bus | |
| Pending changes awaiting acceptance by one or more parties involved: Date to 4/20, Time to 3:30 p.m. | ||||||
| Mon., 4/19 | V Girls Tennis | Ridgefield | Home - New Canaan HS-NCHS Tennis Courts [Directions] | W 6-1 | ||
| Tue., 4/20 | JV Baseball | Trumbull | Away - Trumbull HS-Varsity Baseball Field [Directions] | L 2-5 | 2:20 PM; 1 Bus | |
| Tue., 4/20 | V Boys Golf | Trumbull | Home - CCNC [Directions] | New Canaan 156 Trumbull 189 | ||
| Tue., 4/20 | V Boys Tennis | Stamford | Home - New Canaan HS-NCHS Tennis Courts [Directions] | W 6-1 [Detailed Results] | ||
| Tue., 4/20 | V Boys Volleyball | Darien | Home - New Canaan HS-Main Gym [Directions] | L 1-3 | ||
| Tue., 4/20 | JV Boys Volleyball | Darien | Home - New Canaan HS-Main Gym [Directions] | 6:00 p.m. | ||
| Tue., 4/20 | JV Girls Golf | Fairfield Warde | Away - Carl Dickman Par 3-Golf Course [Directions] | 3:15 p.m. | 12:00 PM | |
| Tue., 4/20 | JV Girls Golf | Fairfield Ludlowe | Away - Carl Dickman Par 3 [Directions] | 3:15 p.m. | 2:10 PM; 1 Bus | |
| Tue., 4/20 | V Softball | Trumbull | Away - Trumbull HS-Varsity Softball Diamond [Directions] | L 1-13 | 2:20 PM; 1 Bus | |
| Tue., 4/20 | V Girls Tennis | Stamford | Away - Stamford HS-SHS Tennis Courts [Directions] | W 6-1 | 2:40 PM; 1 Bus | |
| Tue., 4/20 | JV Girls Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | W 8-1 | 2:15 PM; 1 Bus | |
| Wed., 4/21 | V Boys Lacrosse | Wilton | Away - Wilton HS-Veterans Memorial Stadium [Directions] | W 6-4 | 5:30 PM; 1 Bus | |
| Wed., 4/21 | FR Boys Lacrosse | Fairfield Ludlowe | Home - New Canaan HS-WTT #2 [Directions] | Postponed | ||
| Thu., 4/22 | V Baseball | Fairfield Warde | Home - Mead Park-Baseball Field [Directions] | L 0-11 | ||
| Thu., 4/22 | JV Baseball | Fairfield Warde | Away - Fairfield Warde HS-Baseball Diamond [Directions] | L 1-7 | 2:15 PM; 1 Bus | |
| Thu., 4/22 | V Boys Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | Ludlowe 170 New Canaan 172 | 1:30 PM; 1 Bus | |
| Thu., 4/22 | V Boys Tennis | Greenwich | Away - Greenwich HS-Tennis Courts [Directions] | W 4-3 [Detailed Results] | 2:45 PM; 1 Bus | |
| Thu., 4/22 | JV Boys Tennis | Greenwich | Away - Central MS [Directions] | 4:30 p.m. | 2:45 PM; 1 Bus | |
| Thu., 4/22 | V Boys Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | W 3-0 | 2:40 PM; 1 Bus | |
| Thu., 4/22 | JV Boys Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | 4:15 PM; 1 Bus | |
| Thu., 4/22 | V Girls Golf | Danbury | Away - Richter Park Golf Course [Directions] | 3:15 p.m. | 2:00 PM; 1 Bus | |
| Thu., 4/22 | V Girls Golf | Wilton | Away - Silvermine Golf Club [Directions] | NC-173 Wilton-Forfeit | 2:30 PM, Dismiss TBA; 1 Bus | |
| Thu., 4/22 | V Girls Lacrosse | Darien | Home - New Canaan HS-Dunning Stadium [Directions] | W 7-5 | ||
| Thu., 4/22 | V Softball | Fairfield Warde | Away - Fairfield Warde HS-Softball Diamond [Directions] | L 0-8 | 2:15 PM; 1 Bus | |
| Thu., 4/22 | JV Softball | Fairfield Warde | Home - Waveny Park-Orchard Field [Directions] | Postponed | ||
| Thu., 4/22 | V Girls Tennis | Greenwich | Home - New Canaan HS-NCHS Tennis Courts [Directions] | W 4-3 | ||
| Fri., 4/23 | V Baseball | Danbury | Away - Danbury HS-V Baseball Field [Directions] | W 13-3 | 2:10 PM; 1 Bus | |
| Fri., 4/23 | JV Baseball | Danbury | Home - Mead Park-Baseball Field [Directions] | W 13-10 | ||
| Fri., 4/23 | FR Boys Lacrosse | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | 2:45 PM; 1 Bus | |
| Fri., 4/23 | V Boys Tennis | Ridgefield | Away - Ridgefield HS-RHS Tennis Courts [Directions] | W 4-3 [Detailed Results] | 2:50 PM; 1 Bus | |
| Fri., 4/23 | JV Boys Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | 2:20 PM; 1 Bus | |
| Fri., 4/23 | V Softball | Danbury | Home - Waveny Park-Orchard Field [Directions] | L 3-17 | ||
| Fri., 4/23 | JV Softball | Danbury | Away - Danbury HS-V Softball field [Directions] | Cancelled | 2:10 PM; 1 Bus | |
| Fri., 4/23 | JV Girls Tennis | St. Joseph | Away - St. Joseph HS-Tennis Courts [Directions] | W 9-0 | 2:10 PM; 1 Bus | |
| Sat., 4/24 | FR Baseball | Darien | Home - New Canaan HS-Coppo Field [Directions] | 10:30 a.m. | ||
| Sat., 4/24 | FR Baseball | Darien | Home - New Canaan HS-Coppo Field [Directions] | 12:30 p.m. | ||
| Sat., 4/24 | V Boys Lacrosse | Darien | Away - Darien HS-DHS Stadium Field [Directions] | L 6-15 | 1:40 PM; 1 Bus | |
| Sat., 4/24 | JV Boys Lacrosse | Darien | Away - Darien HS-DHS Stadium Field [Directions] | Postponed | 4:15 PM; 1 Bus | |
| Sat., 4/24 | V Boys Tennis | St. Joseph | Home - New Canaan HS-NCHS Tennis Courts [Directions] | W 6-1 [Detailed Results] | ||
| Sat., 4/24 | V Girls Lacrosse | Greenwich | Home - New Canaan HS-Dunning Stadium [Directions] | W 15-8 | ||
| Sat., 4/24 | V Girls Tennis | St. Joseph | Away - St. Joseph HS-Tennis Courts [Directions] | W 7-0 | 2:15 PM; 1 Bus | |
| Mon., 4/26 | FR Boys Lacrosse | Staples | Away - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | 3:45 PM; 1 Bus | |
| Mon., 4/26 | V Boys Tennis | Brien McMahon | Away - Brien McMahon HS-Tennis Courts [Directions] | W 6-1 [Detailed Results] | 3:20 PM; 1 Bus | |
| Mon., 4/26 | JV Boys Volleyball | Fairfield Ludlowe | Home - New Canaan HS-Main Gym [Directions] | Cancelled | ||
| Mon., 4/26 | V Girls Golf | Ridgefield | Away - Ridgefield Golf Course [Directions] | NC-178 Ridgefield-210 | 2:00 PM, Dismiss TBA; 1 Bus | |
| Mon., 4/26 | JV Girls Golf | Ridgefield | Away - Ridgefield Golf Course [Directions] | 2:30 p.m. | 2:00 PM; 1 Bus (JV/V riding together.) | |
| Mon., 4/26 | V Girls Lacrosse | Wilton | Home - New Canaan HS-Dunning Stadium [Directions] | W 8-6 | ||
| Mon., 4/26 | V Girls Tennis | Brien McMahon | Home - New Canaan HS-NCHS Tennis Courts [Directions] | W 7-0 | ||
| Mon., 4/26 | JV Girls Tennis | Greenwich | Home - New Canaan HS-NCHS Tennis Courts [Directions] | W 9-0 | ||
| Tue., 4/27 | V Boys Golf | Wilton | Away - Rolling Hills Country Club [Directions] | New Canaan 162 Wilton 179 | ||
| Tue., 4/27 | JV Boys Golf | Wilton | Away - Rolling Hills Country Club [Directions] | 3:15 p.m. | 2:10 PM; 1 Bus | |
| Tue., 4/27 | V Boys Outdoor Track | Norwalk | Home - New Canaan HS-NCHS Track [Directions] | 4:00 p.m. | ||
| Tue., 4/27 | V Boys Tennis | Bridgeport Central | Home - New Canaan HS-NCHS Tennis Courts [Directions] | W 7-0 [Detailed Results] | ||
| Tue., 4/27 | JV Boys Tennis | Fairfield Ludlowe | Home - New Canaan HS-NCHS Tennis Courts [Directions] | 5:00 p.m. | ||
| Tue., 4/27 | V Boys Volleyball | Fairfield Ludlowe | Home - New Canaan HS-Main Gym [Directions] | W 3-0 | ||
| Tue., 4/27 | V Girls Outdoor Track | Norwalk | Home - New Canaan HS-NCHS Track [Directions] | 4:00 p.m. | ||
| Tue., 4/27 | V Girls Tennis | Bridgeport Central | Away - Bridgeport Central HS-Central High School Tennis Courts [Directions] | W 7-0 | 2:15 PM; 1 Bus | |
| Wed., 4/28 | V Baseball | Stamford | Home - Mead Park-Baseball Field [Directions] | W 3-1 | ||
| Wed., 4/28 | JV Baseball | Stamford | Away - Stamford HS-SHS Baseball Diamond [Directions] | L 5-6 | 2:40 PM; 1 Bus | |
| Wed., 4/28 | V Boys Golf | Ridgefield | Home - CCNC [Directions] | New Canaan 157 Ridgefield 187 | ||
| Wed., 4/28 | JV Boys Tennis | Staples | Away - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Wed., 4/28 | V Boys Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | W 3-0 | 2:10 PM; 1 Bus | |
| Wed., 4/28 | V Girls Lacrosse | Daniel Hand | Away - Madison Surf Club-Strong Field [Directions] | W 19-9 | 9:30 AM; 1 Bus | |
| Wed., 4/28 | V Softball | Stamford | Away - Stamford HS-SHS Softball Diamond [Directions] | L 1-2 | 2:40 PM; 1 Bus | |
| Wed., 4/28 | JV Softball | Stamford | Home - Waveny Park-Orchard Field [Directions] | Cancelled | ||
| Thu., 4/29 | V Boys Golf | Fairfield Warde | Away - Brooklawn Country Club [Directions] | New Canaan 156 Fairfield Warde 164 | 2:00 PM; 1 Bus | |
| Thu., 4/29 | V Boys Lacrosse | Stamford | Home - New Canaan HS-Dunning Stadium [Directions] | W 18-3 | ||
| Thu., 4/29 | JV Boys Lacrosse | Stamford | Home - New Canaan HS-Dunning Stadium [Directions] | Postponed | ||
| Thu., 4/29 | V Girls Golf | Fairfield Warde | Home - New Canaan HS-CCNC [Directions] | NC-172 Warde-209 | ||
| Thu., 4/29 | V Girls Lacrosse | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | W 16-4 | 2:30 PM; 1 Bus | |
| Fri., 4/30 | V Baseball | Ridgefield | Away - Governor Field [Directions] | W 11-10 | 2:15 PM; 1 Bus | |
| Fri., 4/30 | JV Baseball | Ridgefield | Home - Mead Park-Baseball Field [Directions] | L 7-10 | ||
| Fri., 4/30 | FR Boys Lacrosse | Fairfield Prep | Home - New Canaan HS-Dunning Stadium [Directions] | 5:00 p.m. | ||
| Fri., 4/30 | V Boys Tennis | Fairfield Warde | Away - Fairfield Warde HS-Blake Courts [Directions] | W 4-3 [Detailed Results] | 2:30 PM; 1 Bus | |
| Fri., 4/30 | JV Boys Tennis | Fairfield Warde | Away - Fairfield Warde HS-Knapps Courts [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Fri., 4/30 | V Boys Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | W 3-2 | 3:30 PM; 1 Bus | |
| Fri., 4/30 | JV Boys Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | 2:15 PM; 1 Bus | |
| Fri., 4/30 | V Softball | Ridgefield | Home - Waveny Park-Orchard Field [Directions] | W 9-8 | ||
| Fri., 4/30 | JV Softball | Ridgefield | Home - Waveny Park-Orchard Field [Directions] | 4:00 p.m. | 2:15 PM; 1 Bus | |
| Fri., 4/30 | V Girls Tennis | Fairfield Warde | Home - New Canaan HS-NCHS Tennis Courts [Directions] | W 7-0 | ||
| Sat., 5/1 | FR Baseball | Westhill | Home - New Canaan HS-Coppo Field [Directions] | 10:30 a.m. | ||
| Sat., 5/1 | FR Baseball | Westhill | Away - Westhill HS-Varsity Baseball Field [Directions] | Cancelled | 2:00 PM; 1 Bus | |
| Sat., 5/1 | V Girls Lacrosse | Cheshire | Home - New Canaan HS-Dunning Stadium [Directions] | W 15-5 | ||
| Mon., 5/3 | V Baseball | Harding | Home - Mead Park-Baseball Field [Directions] | W 14-0 | ||
| Mon., 5/3 | V Boys Golf | Norwalk | Away - Oak Hills Golf Course [Directions] | New Canaan 166 Norwalk 192 | 2:10 PM; 1 Bus | |
| Mon., 5/3 | FR Boys Lacrosse | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | Cancelled | 4:10 PM; 1 Bus | |
| Mon., 5/3 | V Boys Outdoor Track | Fairfield Warde | Home - New Canaan HS-NCHS Track [Directions] | 4:00 p.m. | ||
| Mon., 5/3 | V Boys Tennis | Darien | Away - Darien HS-DHS Tennis Courts [Directions] | L 0-6 [Detailed Results] | 3:30 PM; 1 Bus | |
| Mon., 5/3 | JV Boys Tennis | Darien | Away - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | 3:00 PM; 1 Bus | |
| Mon., 5/3 | V Girls Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | NC-169 Ludlowe-186 | 2:10 PM; 1 Bus | |
| Mon., 5/3 | V Girls Lacrosse | Darien | Away - Darien HS-DHS Stadium Field [Directions] | W 10-9 | 2:40 PM; 1 Bus | |
| Mon., 5/3 | V Girls Outdoor Track | Fairfield Warde | Home - New Canaan HS-NCHS Track [Directions] | 4:00 p.m. | ||
| Mon., 5/3 | V Softball | Harding | Away - Warren Harding HS-Luis Munoz Marin School-Boston Ave/Pembroke St. [Directions] | W 17-1 | 2:15 PM; 1 Bus | |
| Mon., 5/3 | V Girls Tennis | Darien | Home - New Canaan HS-NCHS Tennis Courts [Directions] | L 2-5 | ||
| Tue., 5/4 | JV Boys Golf | Fairfield Warde | Away - Smith Richardson Golf Course [Directions] | 3:30 p.m. | 2:10 PM; 1 Bus | |
| Tue., 5/4 | V Boys Lacrosse | Brien McMahon | Home - New Canaan HS-Dunning Stadium [Directions] | W 15-4 | ||
| Tue., 5/4 | JV Boys Lacrosse | Brien McMahon | Home - New Canaan HS-Dunning Stadium [Directions] | 6:00 p.m. | ||
| Tue., 5/4 | V Boys Tennis | Trumbull | Home - New Canaan HS-NCHS Tennis Courts [Directions] | W 7-0 [Detailed Results] | ||
| Tue., 5/4 | V Boys Volleyball | Greenwich | Home - New Canaan HS-Main Gym [Directions] | W 3-0 | ||
| Tue., 5/4 | JV Boys Volleyball | Greenwich | Home - New Canaan HS-Main Gym [Directions] | 6:30 p.m. | ||
| Tue., 5/4 | V Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | W 18-4 | 3:50 PM; 1 Bus | |
| Tue., 5/4 | V Girls Tennis | Trumbull | Away - Trumbull HS-Tennis Courts [Directions] | W 7-0 | 2:15 PM; 1 Bus | |
| Tue., 5/4 | JV Girls Tennis | Trumbull | Away - Unity Park [Directions] | W 8-0 | 2:15 PM; 1 Bus | |
| Wed., 5/5 | V Boys Golf | Danbury | Home - CCNC [Directions] | New Canaan 165 Danbury 208 | ||
| Wed., 5/5 | FR Boys Lacrosse | Wilton | Home - New Canaan HS-WTT #2 [Directions] | 4:30 p.m. | ||
| Wed., 5/5 | V Boys Volleyball | Danbury | Home - New Canaan HS-Main Gym [Directions] | W 3-0 | ||
| Wed., 5/5 | JV Boys Volleyball | Danbury | Home - New Canaan HS-Main Gym [Directions] | 6:00 p.m. | ||
| Wed., 5/5 | JV Softball | Brien McMahon | Away - Brien McMahon HS-Softball Diamond [Directions] | Cancelled | 3:15 PM; 1 Bus | |
| Pending changes awaiting acceptance by one or more parties involved: Time to 4:30 p.m., Facility to Waveny Park-Orchard Field | ||||||
| Thu., 5/6 | V Baseball | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | L 5-7 | 3:00 PM; 1 Bus | |
| Thu., 5/6 | JV Baseball | Brien McMahon | Home - Mead Park-Baseball Field [Directions] | W 10-4 | ||
| Thu., 5/6 | JV Boys Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 3:15 p.m. | 2:05 PM; 1 Bus | |
| Thu., 5/6 | V Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | W 14-6 | 2:30 PM; 1 Bus | |
| Thu., 5/6 | JV Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 6:30 p.m. | 4:30 PM; 1 Bus | |
| Thu., 5/6 | V Boys Tennis | Fairfield Ludlowe | Home - New Canaan HS-NCHS Tennis Courts [Directions] | W 6-1 [Detailed Results] | ||
| Thu., 5/6 | JV Boys Tennis | Greenwich | Away - Central MS [Directions] | 4:30 p.m. | 3:00 PM; 1 Bus | |
| Thu., 5/6 | V Girls Golf | Staples | Home - New Canaan HS-CCNC [Directions] | NC-189 Staples-205 | ||
| Thu., 5/6 | JV Girls Golf | Staples | Away - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | 2:10 PM; 1 Bus | |
| Thu., 5/6 | V Softball | Brien McMahon | Home - Waveny Park-Orchard Field [Directions] | L 19-4 | ||
| Thu., 5/6 | V Girls Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Tennis Courts [Directions] | W 5-2 | 2:15 PM; 1 Bus | |
| Thu., 5/6 | JV Girls Tennis | Fairfield Ludlowe | Away - Dwight Elementary School-Tennis Courts [Directions] | L 1-7 | 2:15 PM; 1 Bus | |
| Fri., 5/7 | V Baseball | Greenwich | Home - Mead Park-Baseball Field [Directions] | L 1-6 | ||
| Fri., 5/7 | JV Baseball | Greenwich | Away - Greenwich HS-Baseball Field [Directions] | L 3-5 | 3:00 PM; 1 Bus | |
| Fri., 5/7 | FR Boys Lacrosse | Trumbull | Home - New Canaan HS-WTT #2 [Directions] | 4:30 p.m. | ||
| Fri., 5/7 | V Boys Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | W 3-0 | 2:30 PM; 1 Bus | |
| Fri., 5/7 | V Girls Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | W 11-7 | 2:15 PM; 1 Bus | |
| Fri., 5/7 | V Softball | Greenwich | Away - Greenwich HS-Softball Field [Directions] | W 8-5 | 3:00 PM; 1 Bus | |
| Sat., 5/8 | FR Baseball | Greenwich | Away - Julian Curtiss School [Directions] | 10:00 a.m. | 8:30 AM; 1 Bus | |
| Sat., 5/8 | FR Baseball | Greenwich | Away - Julian Curtiss School [Directions] | 12:00 p.m. | ||
| Sat., 5/8 | V Boys Lacrosse | Ridgefield | Home - New Canaan HS-Dunning Stadium [Directions] | W 11-8 | ||
| Sat., 5/8 | JV Boys Lacrosse | Ridgefield | Home - New Canaan HS-Dunning Stadium [Directions] | 4:30 p.m. | ||
| Sat., 5/8 | V Girls Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | W 11-5 | 12:45 PM; 1 Bus | |
| Sat., 5/8 | JV Softball | Danbury | Away - Danbury HS-JV Softball Field [Directions] | 10:00 a.m. | 8:15 AM; 1 Bus | |
| Mon., 5/10 | V Boys Golf | Stamford | Away - Stamford High-Sterling Farms Golf Course [Directions] | New Canaan 161 Stamford 256 | 2:05 PM; 1 Bus | |
| Mon., 5/10 | JV Boys Golf | Ridgefield | Away - Ridgefield Golf Course [Directions] | 3:15 p.m. | 1:30 PM; 1 Bus | |
| Mon., 5/10 | FR Boys Lacrosse | Ridgefield | Home - New Canaan HS-WTT #2 [Directions] | 4:30 p.m. | ||
| Mon., 5/10 | V Boys Outdoor Track | Wilton | Home - New Canaan HS-NCHS Track [Directions] | 4:00 p.m. | ||
| Mon., 5/10 | V Boys Tennis | Norwalk | Home - New Canaan HS-NCHS Tennis Courts [Directions] | W 6-1 [Detailed Results] | ||
| Mon., 5/10 | V Boys Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | L 1-3 | 2:50 PM; 1 Bus | |
| Mon., 5/10 | JV Boys Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | 4:20 PM; 1 Bus | |
| Mon., 5/10 | V Girls Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | NC-175 Trumbull-196 | 2:00 PM; 1 Bus | |
| Mon., 5/10 | JV Girls Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | 2:00 PM; 1 Bus | |
| Mon., 5/10 | V Girls Tennis | Norwalk | Away - Norwalk HS-Tennis Courts [Directions] | W 7-0 | 2:30 PM; 1 Bus | |
| Tue., 5/11 | V Boys Lacrosse | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | W 13-6 | 2:10 PM; 1 Bus | |
| Tue., 5/11 | JV Boys Lacrosse | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 5:30 p.m. | 3:30 PM; 1 Bus | |
| Tue., 5/11 | V Boys Tennis | Westhill | Away - Westhill HS-Westhill Tennis Courts [Directions] | W 4-3 | 3:00 PM; 1 Bus | |
| Tue., 5/11 | V Girls Lacrosse | St. Joseph | Home - New Canaan HS-Dunning Stadium [Directions] | W 14-3 | ||
| Tue., 5/11 | V Girls Outdoor Track | Wilton | Home - New Canaan HS-NCHS Track [Directions] | 4:00 p.m. | ||
| Tue., 5/11 | V Girls Tennis | Westhill | Home - New Canaan HS-NCHS Tennis Courts [Directions] | W 4-3 | ||
| Wed., 5/12 | V Baseball | Darien | Home - Mead Park-Baseball Field [Directions] | W 13-3 | ||
| Wed., 5/12 | JV Baseball | Darien | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | L 1-2 | 3:00 PM; 1 Bus | |
| Wed., 5/12 | FR Boys Lacrosse | Greenwich | Away - Greenwich HS-Cos Cob Park, Benvenuto Field [Directions] | 4:30 p.m. | 2:40 PM; 1 Bus | |
| Wed., 5/12 | V Girls Golf | Danbury | Away - Richter Park Golf Course [Directions] | NC-171 Danbury-242 | 1:00 PM; 1 Bus | |
| Wed., 5/12 | V Softball | Darien | Away - Darien HS-DHS Softball - Varsity Field [Directions] | L 1-8 | 2:45 PM; 1 Bus | |
| Thu., 5/13 | V Boys Golf | St. Joseph | Away - Tashua Knolls Golf Course [Directions] | St. Joseph 159 New Canaan 159 | 1:45 PM; 1 Bus | |
| Thu., 5/13 | V Boys Lacrosse | Brunswick School | Away - Brunswick Cosby Turf Field | 4:30 p.m. | 2:40 PM; 1 Bus | |
| Thu., 5/13 | V Boys Tennis | St. Joseph | Home - New Canaan HS-NCHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/13 | V Boys Volleyball | Fairfield Warde | Home - New Canaan HS-Main Gym [Directions] | W 3-0 | ||
| Thu., 5/13 | JV Boys Volleyball | Fairfield Warde | Home - New Canaan HS-Main Gym [Directions] | 6:00 p.m. | ||
| Thu., 5/13 | V Girls Golf | Darien | Away - Woodway Country Club [Directions] | NC-169 Darien-222 | 2:15 PM; 1 Bus | |
| Thu., 5/13 | JV Girls Golf | Darien | Away - Woodway Country Club [Directions] | 3:30 p.m. | 2:40 PM; 1 Bus | |
| Fri., 5/14 | V Baseball | Wilton | Home - Mead Park-Baseball Field [Directions] | L 0-13 | ||
| Fri., 5/14 | JV Baseball | Wilton | Away - Wilton HS-JV Baseball Field [Directions] | W 9-0 | 11:00 AM; 1 Bus | |
| Fri., 5/14 | FR Boys Lacrosse | Staples | Home - New Canaan HS-WTT #2 [Directions] | 4:30 p.m. | ||
| Fri., 5/14 | V Boys Volleyball | Ridgefield | Home - New Canaan HS-Main Gym [Directions] | L 2-3 | ||
| Fri., 5/14 | JV Boys Volleyball | Ridgefield | Home - New Canaan HS-Main Gym [Directions] | 6:30 p.m. | ||
| Fri., 5/14 | V Softball | Wilton | Away - Wilton HS-Varsity Softball Field [Directions] | W 3-0 | 2:45 PM; 1 Bus | |
| Fri., 5/14 | V Girls Tennis | Danbury | Home - New Canaan HS-NCHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Sat., 5/15 | V Baseball | Bridgeport Central | Away - Bridgeport Central HS-Baseball Diamond [Directions] | W 17-2 | 2:10 PM; 1 Bus | |
| Sat., 5/15 | FR Baseball | Norwalk | Home - New Canaan HS-Coppo Field [Directions] | 10:30 a.m. | ||
| Sat., 5/15 | FR Baseball | Norwalk | Home - New Canaan HS-Coppo Field [Directions] | 12:30 p.m. | ||
| Sat., 5/15 | V Boys Lacrosse | Glastonbury | Home - New Canaan HS-Dunning Stadium [Directions] | W 11-7 | ||
| Sat., 5/15 | JV Boys Lacrosse | Glastonbury | Home - New Canaan HS-Dunning Stadium [Directions] | 4:30 p.m. | ||
| Sat., 5/15 | V Boys Outdoor Track | Fairfield Ludlowe | Home - New Canaan HS-NCHS Track [Directions] | 10:00 a.m. | ||
| Sat., 5/15 | V Boys Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | W 3-1 | 3:40 PM; 1 Bus | |
| Sat., 5/15 | JV Boys Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | Cancelled | 2:30 PM; 1 Bus | |
| Sat., 5/15 | V Girls Lacrosse | Glastonbury | Home - New Canaan HS-Dunning Stadium [Directions] | W 18-5 | ||
| Sat., 5/15 | V Girls Outdoor Track | Fairfield Ludlowe | Home - New Canaan HS-NCHS Track [Directions] | 10:00 a.m. | ||
| Sat., 5/15 | JV Softball | Darien | Home - Waveny Park-Orchard Field [Directions] | 11:00 a.m. | ||
| Mon., 5/17 | V Baseball | Staples | Away - Staples HS-Baseball Diamond [Directions] | L 1-2 | 2:15 PM; 1 Bus | |
| Mon., 5/17 | JV Baseball | Staples | Home - Mead Park-Baseball Field [Directions] | L 8-23 | ||
| Mon., 5/17 | V Boys Golf | Darien | Away - Wee Burn CC [Directions] | New Canaan 160 Darien 162 | 2:15 PM; 1 Bus | |
| Mon., 5/17 | JV Boys Golf | Fairfield Warde | Away - Smith Richardson Golf Course [Directions] | 3:30 p.m. | 2:10 PM; 1 Bus | |
| Mon., 5/17 | FR Boys Lacrosse | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | 3:00 PM; 1 Bus | |
| Mon., 5/17 | V Boys Outdoor Track | Darien | Home - New Canaan HS-NCHS Track [Directions] | 4:00 p.m. | ||
| Mon., 5/17 | V Boys Tennis | Fairfield Warde | Home - New Canaan HS-NCHS Tennis Courts [Directions] | 4:30 p.m. | ||
| Mon., 5/17 | V Softball | Staples | Home - Waveny Park-Orchard Field [Directions] | L 15-2 | ||
| Tue., 5/18 | V Boys Lacrosse | Norwalk | Away - Norwalk HS-Testa Field [Directions] | W 18-0 | 5:15 PM; 1 Bus | |
| Tue., 5/18 | JV Boys Lacrosse | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 5:00 p.m. | 3:30 PM; 1 Bus | |
| Tue., 5/18 | V Boys Volleyball | Stamford | Home - New Canaan HS-Main Gym [Directions] | W 3-1 | ||
| Tue., 5/18 | JV Boys Volleyball | Stamford | Home - New Canaan HS-Main Gym [Directions] | 6:00 p.m. | ||
| Tue., 5/18 | V Girls Golf | Ridgefield | Home - New Canaan HS-CCNC [Directions] | NC-176 Ridgefield-209 | ||
| Tue., 5/18 | JV Girls Golf | Ridgefield | Home - CCNC [Directions] | 3:45 p.m. | ||
| Tue., 5/18 | V Girls Lacrosse | Norwalk | Home - New Canaan HS-Dunning Stadium [Directions] | W 20-0 | ||
| Tue., 5/18 | V Girls Outdoor Track | Darien | Home - New Canaan HS-NCHS Track [Directions] | 4:00 p.m. | ||
| Tue., 5/18 | V Girls Tennis | Greenwich | Home - New Canaan HS-NCHS Tennis Courts [Directions] | 4:30 p.m. | ||
| Wed., 5/19 | V Baseball | Westhill | Away - Westhill HS-Varsity Baseball Field [Directions] | L 9-11 | 2:30 PM; 1 Bus | |
| Wed., 5/19 | JV Baseball | Westhill | Home - Mead Park-Baseball Field [Directions] | L 4-11 | ||
| Wed., 5/19 | V Boys Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | New Canaan 155 Greenwich 159 | 2:05 PM; 1 Bus | |
| Wed., 5/19 | JV Boys Golf | Greenwich | Home - New Canaan HS-CCNC [Directions] | 3:30 p.m. | ||
| Wed., 5/19 | JV Boys Lacrosse | Wilton | Away - Wilton HS-Whitten Field [Directions] | 6:00 p.m. | 3:15 PM; 1 Bus | |
| Wed., 5/19 | FR Boys Lacrosse | Fairfield Prep | Away - Fairfield University - Barlow Field-Barlow Field Fairfield University [Directions] | 4:00 p.m. | 2:20 PM; 1 Bus | |
| Wed., 5/19 | V Softball | Westhill | Home - Waveny Park-Orchard Field [Directions] | W 7-6 | ||
| Thu., 5/20 | V Boys Golf | Staples | Home - CCNC [Directions] | New Canaan 148 Staples 170 | ||
| Thu., 5/20 | JV Boys Golf | Staples | Away - Longshore Golf Course [Directions] | 3:00 p.m. | 2:05 PM; 1 Bus | |
| Thu., 5/20 | V Boys Lacrosse | Darien | Home - New Canaan HS-Dunning Stadium [Directions] | L 9-10 | ||
| Thu., 5/20 | JV Boys Lacrosse | Darien | Home - New Canaan HS-WTT #2 [Directions] | 6:30 p.m. | ||
| Thu., 5/20 | V Boys Tennis | Staples | Away - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus | |
| Thu., 5/20 | V Boys Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | W 3-1 | 3:30 PM; 1 Bus | |
| Thu., 5/20 | JV Boys Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:00 p.m. | 2:20 PM; 1 Bus | |
| Thu., 5/20 | V Girls Golf | Darien | Home - New Canaan HS-CCNC [Directions] | NC-169 Darien-238 | ||
| Thu., 5/20 | V Girls Lacrosse | Fairfield Warde | Home - New Canaan HS-Dunning Stadium [Directions] | W 17-0 | ||
| Fri., 5/21 | V Baseball | Ridgefield | Away - Governor Field [Directions] | 2:00 p.m. | 12:15 PM; 1 Bus | |
| Fri., 5/21 | FR Boys Lacrosse | Wilton | Away - Wilton HS-Fuijitani Field -Turf [Directions] | 4:30 p.m. | 3:30 PM; 1 Bus | |
| Fri., 5/21 | V Girls Lacrosse | Staples | Away - Staples HS-Ginny Parker Field [Directions] | W 15-2 | 2:15 PM; 1 Bus | |
| Sat., 5/22 | FR Baseball | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | Cancelled | ||
| Sat., 5/22 | FR Baseball | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 9:30 a.m. | 8:20 AM; 1 Bus | |
| Sat., 5/22 | V Boys Lacrosse | Staples | Home - New Canaan HS-Dunning Stadium [Directions] | L 9-12 | ||
| Sat., 5/22 | JV Boys Lacrosse | Staples | Home - New Canaan HS-Dunning Stadium [Directions] | 4:30 p.m. | ||
| Sat., 5/22 | V Softball | Stamford | Away - Stamford HS-SHS Softball Diamond [Directions] | L 0-12 | 12:15 PM; 1 Bus | |
| Mon., 5/24 | V Boys Golf | Westhill | Home - CCNC [Directions] | New Canaan 149 Westhill 199 | ||
| Mon., 5/24 | JV Boys Golf | St. Joseph | Away - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | 2:10 PM; 1 Bus | |
| Mon., 5/24 | V Boys Lacrosse | Wilton | Home - New Canaan HS-Dunning Stadium [Directions] | 5:00 p.m. | ||
| Mon., 5/24 | V Boys Volleyball | Fairfield Ludlowe | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 5/24 | V Girls Lacrosse | St. Joseph | Home - New Canaan HS-Dunning Stadium [Directions] | W 18-7 | ||
| Mon., 5/24 | V Girls Tennis | Staples | Away - Staples HS-Staples Tennis Courts [Directions] | L 2-5 | 2:15 PM; 1 Bus | |
| Tue., 5/25 | V Boys Golf | Brien McMahon | Home - CCNC [Directions] | New Canaan 154 McMahon 200 | ||
| Tue., 5/25 | FR Boys Lacrosse | Stamford | Away - Stamford HS-Upper Lacrosse Field [Directions] | 5:00 p.m. | 3:45 PM; 1 Bus | |
| Tue., 5/25 | V Girls Golf | Trumbull | Home - New Canaan HS-CCNC [Directions] | NC-175 Trumbull-207 | ||
| Tue., 5/25 | JV Softball | Westhill | Home - Waveny Park-Orchard Field [Directions] | 5:30 p.m. | ||
| Wed., 5/26 | V Boys Volleyball | Trumbull | Home - New Canaan HS-Main Gym [Directions] | 6:00 p.m. | ||
| Wed., 5/26 | V Girls Golf | St. Joseph | Away - Tashua Knolls Golf Course [Directions] | NC-165 ST. Joseph's-188 | 2:00 PM; 1 Bus | |
| Thu., 5/27 | V Baseball | Wilton (Scrim.) | Away - Wilton HS-Varsity Baseball Field [Directions] | 4:00 a.m. | 2:45 PM; 1 Bus | |
| Thu., 5/27 | FR Boys Lacrosse | Darien | Home - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Thu., 5/27 | JV Girls Golf | Darien | Home - CCNC [Directions] | 3:00 p.m. | ||
| Thu., 5/27 | V Girls Lacrosse | Fairfield Ludlowe | Home - Wilton HS-Lilly Field [Directions] | W 16-5 | 3:00 PM; 1 Bus | |
| Fri., 5/28 | V Boys Tennis | Guilford | Home - New Canaan HS-NCHS Tennis Courts [Directions] | 1:00 p.m. | ||
| Fri., 5/28 | V Boys Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 5:00 p.m. | 3:15 PM; 1 Bus | |
| Fri., 5/28 | V Girls Tennis | Westhill | Home - New Canaan HS-NCHS Tennis Courts [Directions] | W 5-2 | ||
| Sat., 5/29 | V Boys Lacrosse | Fairfield Ludlowe | Home - New Canaan HS-Dunning Stadium [Directions] | 1:00 p.m. | ||
| Sat., 5/29 | V Girls Lacrosse | Darien | Home - New Canaan HS-Dunning Stadium [Directions] | W 7-4 | ||
| Tue., 6/1 | V Baseball | Staples | Away - Staples HS-Baseball Diamond [Directions] | 3:30 p.m. | ||
| Tue., 6/1 | V Boys Outdoor Track | CIAC Class L Boys Outdoor Track Championship | Away - Willow Brook Park | 4:00 p.m. | ||
| Tue., 6/1 | V Boys Tennis | Xavier | Home - New Canaan HS-NCHS Tennis Courts [Directions] | 3:00 p.m. | ||
| Tue., 6/1 | V Girls Golf | Staples (Scrim.) | Away - Staples HS-Fairfield Wheeler [Directions] | TBA | 1:30 PM, Dismiss TBA; 1 Bus | |
| Tue., 6/1 | V Girls Lacrosse | Ridgefield | Home - New Canaan HS-Dunning Stadium [Directions] | W 15-5 | ||
| Tue., 6/1 | V Girls Outdoor Track | CIAC Class L Girls Outdoor Track Championship | Away - Willow Brook Park | 4:00 p.m. | 12:45 PM; 1 Bus | |
| Tue., 6/1 | V Girls Tennis | Farmington | Away - Farmington HS [Directions] | W 5-2 | ||
| Wed., 6/2 | V Baseball | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 4:30 p.m. | 3:15 PM; 1 Bus | |
| Wed., 6/2 | V Boys Tennis | Darien | Away - Darien HS-DHS Tennis Courts [Directions] | 3:00 p.m. | 1:00 PM; 1 Bus | |
| Wed., 6/2 | V Girls Tennis | Amity | Away - Amity Regional HS-Tennis Courts [Directions] | 3:00 p.m. | 12:45 PM; 1 Bus | |
| Thu., 6/3 | V Girls Lacrosse | CIAC 1/4 Final | Home - TBA [Directions] | TBA | ||
| Fri., 6/4 | V Boys Volleyball | South Windsor | Away - South Windsor HS-Gym [Directions] | 6:00 p.m. | 2:30 PM; 1 Bus | |
| Fri., 6/4 | V Girls Lacrosse | Wilton | Home - New Canaan HS-Dunning Stadium [Directions] | W 12-9 | ||
| Mon., 6/7 | V Boys Golf | CIAC Boys Div. I Golf Championship | Away - Tallwood CC | 8:00 a.m. | ||
| Tue., 6/8 | V Girls Lacrosse | Darien | Home - New Canaan HS-Dunning Stadium [Directions] | L 8-4 | ||
| Wed., 6/9 | V Boys Outdoor Track | CIAC Open Boys Outdoor Track Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Wed., 6/9 | V Girls Golf | CIAC Girls Div. I Golf Championship | Away - Grassy Hill | 8:30 a.m. | ||
| Wed., 6/9 | V Girls Outdoor Track | CIAC Open Girls Outdoor Track Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Sat., 6/12 | V Boys Golf | CIAC State Open Golf Championship | Away - Black Hall Club | 1:00 p.m. | ||
| Sat., 6/12 | V Girls Golf | CIAC State Open Golf Championship | Away - Black Hall Club | 1:00 p.m. | ||
| Sat., 6/12 | V Girls Lacrosse | CIAC Final | Home - TBA [Directions] | TBA | ||
| Mon., 6/14 | V Boys Outdoor Track | CIAC Boys Hammer Throw Championship | Away - Manchester | 3:30 p.m. | ||
| Mon., 6/14 | V Girls Outdoor Track | CIAC Girls Hammer Throw Championship | Away - Manchester | 3:30 p.m. | ||
| Tue., 6/15 | V Boys Outdoor Track | CIAC Boys Decathlon Championship Day 1 | Away - Manchester | 10:00 a.m. | ||
| Tue., 6/15 | V Girls Outdoor Track | CIAC Girls Heptathlon Championship Day 1 | Away - Manchester | 10:30 a.m. | ||
| Tue., 6/15 | V Girls Outdoor Track | CIAC Girls Steeplechase Championship | Away - Manchester | 3:30 p.m. | ||
| Wed., 6/16 | V Boys Outdoor Track | CIAC Boys Decathlon Championship Day 2 | Away - Manchester | 10:00 a.m. | ||
| Wed., 6/16 | V Boys Outdoor Track | CIAC Boys Steeplechase Championship | Away - Manchester | 3:30 p.m. | ||
| Wed., 6/16 | V Girls Outdoor Track | CIAC Girls Heptathlon Championship Day 2 | Away - Manchester | 10:00 a.m. | ||