| New Canaan 2023-24 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 946 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Thu., 8/24 | V Boys Golf | Danbury | Away - Richter Park Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 8/24 | JV Boys Golf | Danbury | Away - Richter Park Golf Course [Directions] | 3:00 p.m. | ||
| Sun., 8/27 | V Football | Stepinac (NY) (Scrim.) | Home - New Canaan HS-Dunning Stadium [Directions] | 1:00 p.m. | ||
| Tue., 8/29 | V Boys Soccer | Stamford (Scrim.) | Home - Saxe MS-Field 1 [Directions] | 4:30 p.m. | L 0-3 | |
| Tue., 8/29 | JV Boys Soccer | Stamford (Scrim.) | Home - Saxe MS-Field 2 [Directions] | 4:30 p.m. | ||
| Tue., 8/29 | V Girls Soccer | Weston (Scrim.) | Away - Weston HS-WHS Stadium Field [Directions] | 6:30 p.m. | ||
| Thu., 8/31 | V Boys Golf | Brien McMahon | Away - Oak Hills Golf Course [Directions] | 3:30 p.m. | ||
| Thu., 8/31 | JV Boys Golf | Darien | Home - New Canaan HS-CCNC [Directions] | 3:15 p.m. | ||
| Thu., 8/31 | JV Boys Golf | Brien McMahon | Away - Oak Hills Golf Course [Directions] | 3:30 p.m. | ||
| Thu., 8/31 | V Field Hockey | Greenwich Academy (Scrim.) | Home - New Canaan HS-WTT #2 [Directions] | 3:30 p.m. | ||
| Thu., 8/31 | JV Field Hockey | Greenwich Academy (Scrim.) | Home - New Canaan HS-WTT #2 [Directions] | 5:00 p.m. | ||
| Thu., 8/31 | V Girls Soccer | Newtown (Scrim.) | Home - New Canaan HS-Dunning Stadium [Directions] | 4:30 p.m. | ||
| Thu., 8/31 | JV Girls Soccer | Newtown (Scrim.) | Home - Saxe MS-Field 2 [Directions] | 4:30 p.m. | ||
| Thu., 8/31 | V Girls Volleyball | King and Low-Heywood Thomas (Scrim.) | Away - King School-Upper School Gym | 4:00 p.m. | ||
| Fri., 9/1 | V Football | Greenwich (Scrim.) | Home - New Canaan HS-Dunning Stadium [Directions] | 6:00 p.m. | ||
| Fri., 9/1 | FR Football | Greenwich (Scrim.) | Home - New Canaan HS-WTT #1 [Directions] | 4:00 p.m. | ||
| Fri., 9/1 | V Boys Soccer | St. Lukes (Scrim.) | Away - St. Lukes-Class of 2015 Field | 3:00 p.m. | W 1-0 | |
| Fri., 9/1 | JV Boys Soccer | St. Lukes (Scrim.) | Away - St. Lukes-Class of 2015 Field | 4:30 p.m. | ||
| Sat., 9/2 | V Field Hockey | Field Hockey Play Day | Away - Sacred Heart Greenwich-Chambers Field | 9:00 a.m. | ||
| Tue., 9/5 | V Boys Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 2:50 p.m. | ||
| Tue., 9/5 | JV Boys Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 2:50 p.m. | ||
| Tue., 9/5 | V Field Hockey | St. Joseph (Scrim.) | Home - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Tue., 9/5 | V Girls Soccer | St. Lukes (Scrim.) | Away - St. Lukes-Class of 2015 Field | 4:00 p.m. | ||
| Tue., 9/5 | V Girls Volleyball | Weston (Scrim.) | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 9/7 | V Field Hockey | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 7:30 p.m. | L 4-2 | |
| Thu., 9/7 | JV Field Hockey | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | Postponed | ||
| Fri., 9/8 | V Football | Shelton | Away - Shelton HS-Finn Stadium [Directions] | 7:00 p.m. | L 23-26 | |
| Fri., 9/8 | V Boys Soccer | Danbury | Away - Mill Ridge Int. School-Turf Field [Directions] | 6:30 p.m. | T 2-2 | |
| Fri., 9/8 | JV Boys Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 5:15 p.m. | ||
| Fri., 9/8 | FR Field Hockey | Ridgefield | Home - New Canaan HS-WTT #2 [Directions] | Postponed | ||
| Fri., 9/8 | V Girls Swimming and Diving | Wilton | Home - Waveny Park-Waveny Pool [Directions] | Postponed | ||
| Sat., 9/9 | V Boys Cross Country | Wilton | Home - Waveny Park [Directions] | 9:30 a.m. | ||
| Sat., 9/9 | JV Football | Shelton | Home - New Canaan HS-Dunning Stadium [Directions] | 10:00 a.m. | ||
| Sat., 9/9 | FR Football | Stamford | Home - New Canaan HS-Dunning Stadium [Directions] | 12:00 p.m. | ||
| Sat., 9/9 | V Girls Cross Country | Wilton | Home - Waveny Park [Directions] | 9:30 a.m. | ||
| Sat., 9/9 | V Field Hockey | Branford | Away - Branford HS-Athletic Turf Field [Directions] | 11:30 a.m. | OT-L 1-0 | |
| Sat., 9/9 | JV Field Hockey | Branford | Away - Branford HS-Athletic Turf Field [Directions] | 10:00 a.m. | ||
| Sat., 9/9 | V Girls Volleyball | CIAC Girls' Volleyball Invitational | Away - CT Volleyball Center Woodbridge | 7:30 a.m. | ||
| Mon., 9/11 | V Girls Soccer | Staples | Away - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | L 3-0 | |
| Mon., 9/11 | JV Girls Soccer | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Mon., 9/11 | FR Girls Soccer | Staples | Home - Saxe MS-Field 1 [Directions] | 4:00 p.m. | ||
| Mon., 9/11 | V Girls Volleyball | Jonathan Law | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | W 3-2 | |
| Mon., 9/11 | JV Girls Volleyball | Jonathan Law | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 9/12 | V Boys Cross Country | Danbury, Bridgeport Central, Brien McMahon | Away - Tarrywile Park [Directions] | 4:00 p.m. | ||
| Tue., 9/12 | V Boys Golf | Norwalk | Home - CCNC [Directions] | 3:30 p.m. | ||
| Tue., 9/12 | V Boys Soccer | Staples | Home - New Canaan HS-Dunning Stadium [Directions] | 6:30 p.m. | L 0-2 | |
| Tue., 9/12 | JV Boys Soccer | Staples | Home - Saxe MS-Field 1 [Directions] | 4:00 p.m. | ||
| Tue., 9/12 | FR Boys Soccer | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Tue., 9/12 | V Girls Cross Country | Danbury, Brien McMahon, TBA | Away - Tarrywile Park [Directions] | 4:00 p.m. | ||
| Tue., 9/12 | V Field Hockey | Norwalk | Home - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | L 6-2 | |
| Tue., 9/12 | JV Field Hockey | Norwalk | Home - New Canaan HS-WTT #2 [Directions] | 5:30 p.m. | ||
| Tue., 9/12 | FR Field Hockey | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | 4:00 p.m. | ||
| Wed., 9/13 | JV Boys Golf | St. Joseph | Away - Tashua Knolls Golf Course-Tashua Glen [Directions] | 3:15 p.m. | ||
| Wed., 9/13 | JV Boys Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | 3:30 p.m. | ||
| Wed., 9/13 | V Girls Soccer | Norwalk | Home - New Canaan HS-Dunning Stadium [Directions] | 6:30 p.m. | W 5-0 | |
| Wed., 9/13 | JV Girls Soccer | Norwalk | Home - Saxe MS-Field 1 [Directions] | 4:00 p.m. | ||
| Thu., 9/14 | V Football | Fairfield Warde | Home - New Canaan HS-Dunning Stadium [Directions] | 6:30 p.m. | W 47-0 | |
| Thu., 9/14 | FR Football | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 7:00 p.m. | ||
| Thu., 9/14 | V Boys Golf | Fairfield Prep | Home - CCNC [Directions] | 3:15 p.m. | ||
| Thu., 9/14 | V Boys Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 6:30 p.m. | L 3-4 | |
| Thu., 9/14 | JV Boys Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 4:30 p.m. | ||
| Thu., 9/14 | FR Boys Soccer | Norwalk | Home - Saxe MS-Field 1 [Directions] | 4:00 p.m. | ||
| Thu., 9/14 | V Field Hockey | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 7:00 p.m. | L 3-1 | |
| Thu., 9/14 | JV Field Hockey | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Thu., 9/14 | FR Field Hockey | Darien | Home - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Thu., 9/14 | V Girls Swimming and Diving | Norwalk/McMahon | Away - Norwalk HS-Pat Spinola Natatorium [Directions] | 4:00 p.m. | ||
| Thu., 9/14 | V Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | L 0-3 | |
| Thu., 9/14 | JV Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 9/18 | JV Football | Fairfield Prep | Home - New Canaan HS-Dunning Stadium [Directions] | 6:30 p.m. | ||
| Mon., 9/18 | JV Football | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | Canceled | Cancelled | |
| Mon., 9/18 | V Boys Golf | Wilton | Home - CCNC [Directions] | Postponed | ||
| Mon., 9/18 | JV Boys Golf | Wilton | Home - CCNC [Directions] | Postponed | ||
| Mon., 9/18 | V Girls Soccer | Fairfield Ludlowe | Home - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | L 3-0 | |
| Tue., 9/19 | V Boys Cross Country | Fairfield Ludlowe, Norwalk, Wilton | Home - Waveny Park [Directions] | 4:00 p.m. | ||
| Tue., 9/19 | V Boys Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 7:00 p.m. | W 2-1 | |
| Tue., 9/19 | JV Boys Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | 4:00 p.m. | ||
| Tue., 9/19 | FR Boys Soccer | Fairfield Ludlowe | Home - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Tue., 9/19 | V Girls Cross Country | Fairfield Ludlowe, Norwalk, Wilton | Home - Waveny Park [Directions] | 4:00 p.m. | ||
| Tue., 9/19 | V Field Hockey | Staples | Home - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | L 4-1 | |
| Tue., 9/19 | JV Field Hockey | Staples | Home - New Canaan HS-Dunning Stadium [Directions] | 5:30 p.m. | ||
| Tue., 9/19 | FR Field Hockey | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Wed., 9/20 | V Boys Golf | Staples | Away - Longshore Golf Course [Directions] | 3:15 p.m. | ||
| Wed., 9/20 | JV Boys Golf | Staples | Away - Longshore Golf Course [Directions] | 3:15 p.m. | ||
| Wed., 9/20 | V Girls Soccer | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 5:30 p.m. | W 1-0 | |
| Wed., 9/20 | JV Girls Soccer | Fairfield Warde | Away - Fairfield Warde HS-Grass Utility Field [Directions] | 4:30 p.m. | ||
| Wed., 9/20 | FR Girls Soccer | Fairfield Warde | Home - Saxe MS-Field 1 [Directions] | 4:00 p.m. | ||
| Wed., 9/20 | V Girls Volleyball | Stamford | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 9/20 | JV Girls Volleyball | Stamford | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 9/21 | V Boys Soccer | Fairfield Warde | Home - New Canaan HS-Dunning Stadium [Directions] | 6:30 p.m. | T 2-2 | |
| Thu., 9/21 | JV Boys Soccer | Fairfield Warde | Home - Saxe MS-Field 1 [Directions] | 4:00 p.m. | ||
| Thu., 9/21 | FR Boys Soccer | Fairfield Warde | Away - Fairfield Warde HS-Grass Utility Field [Directions] | 4:30 p.m. | ||
| Fri., 9/22 | V Field Hockey | Cheshire | Home - New Canaan HS-Dunning Stadium [Directions] | 7:00 p.m. | W 3-1 | |
| Fri., 9/22 | V Girls Soccer | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:30 p.m. | L 2-1 | |
| Fri., 9/22 | JV Girls Soccer | Greenwich | Away - Greenwich HS-Field 3 [Directions] | 4:45 p.m. | ||
| Fri., 9/22 | FR Girls Soccer | Greenwich | Home - Saxe MS-Field 1 [Directions] | 4:00 p.m. | ||
| Fri., 9/22 | V Girls Swimming and Diving | Staples | Home - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Fri., 9/22 | V Girls Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 4:30 p.m. | W 3-0 | |
| Fri., 9/22 | JV Girls Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 6:00 p.m. | ||
| Fri., 9/22 | FR Girls Volleyball | Danbury | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/23 | V Football | Windsor | Home - New Canaan HS-Dunning Stadium [Directions] | 2:00 p.m. | W 33-12 | |
| Sat., 9/23 | V Boys Soccer | Greenwich | Home - New Canaan HS-Dunning Stadium [Directions] | 10:00 a.m. | L 1-7 | |
| Sat., 9/23 | JV Boys Soccer | Greenwich | Away - Greenwich HS-Field 3 [Directions] | 10:00 a.m. | ||
| Sat., 9/23 | FR Boys Soccer | Greenwich | Away - Greenwich HS-Field 7 [Directions] | 10:00 a.m. | ||
| Sat., 9/23 | FR Field Hockey | Greenwich | Away - Greenwich HS-Field 4 [Directions] | 10:00 a.m. | ||
| Tue., 9/26 | JV Boys Golf | Darien | Away - Country Club of Darien [Directions] | 3:00 p.m. | ||
| Tue., 9/26 | V Boys Soccer | Stamford | Away - West Beach Field [Directions] | 3:45 p.m. | L 0-3 | |
| Tue., 9/26 | JV Boys Soccer | Stamford | Away - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | ||
| Tue., 9/26 | V Field Hockey | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 4:30 p.m. | W 5-0 | |
| Tue., 9/26 | JV Field Hockey | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 6:00 p.m. | ||
| Tue., 9/26 | V Girls Swimming and Diving | Fairfield Ludlowe | Away - Fairfield University-Pool [Directions] | 4:00 p.m. | ||
| Wed., 9/27 | V Boys Cross Country | Staples, Trumbull, Westhill | Home - Waveny Park [Directions] | 4:00 p.m. | ||
| Wed., 9/27 | V Boys Golf | St. Joseph | Away - Tashua Knolls Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 9/27 | V Girls Cross Country | Staples, Trumbull, Westhill | Home - Waveny Park [Directions] | 4:00 p.m. | ||
| Wed., 9/27 | V Girls Soccer | Wilton | Home - New Canaan HS-Dunning Stadium [Directions] | 6:30 p.m. | T 1-1 | |
| Wed., 9/27 | JV Girls Soccer | Wilton | Home - Conner Field, New Cannan [Directions] | 4:00 p.m. | ||
| Wed., 9/27 | FR Girls Soccer | Wilton | Away - Allen's Meadow-3A [Directions] | 4:30 p.m. | ||
| Wed., 9/27 | V Girls Volleyball | Staples | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Wed., 9/27 | JV Girls Volleyball | Staples | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 9/28 | FR Football | Staples | Away - Staples HS-Staples Stadium [Directions] | 6:00 p.m. | ||
| Thu., 9/28 | V Boys Golf | Ridgefield | Away - Silver Spring Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 9/28 | JV Boys Golf | Fairfield Ludlowe | Home - CCNC [Directions] | 3:00 p.m. | ||
| Thu., 9/28 | V Boys Soccer | Wilton | Away - Wilton HS-Lilly Field [Directions] | 4:30 p.m. | L 2-4 | |
| Thu., 9/28 | JV Boys Soccer | Wilton | Away - Allen's Meadow-Field 2 [Directions] | 4:15 p.m. | ||
| Thu., 9/28 | FR Boys Soccer | Wilton | Home - Conner Field, New Cannan [Directions] | 4:30 p.m. | ||
| Thu., 9/28 | V Field Hockey | St. Joseph | Home - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | W 6-0 | |
| Thu., 9/28 | JV Field Hockey | St. Joseph | Home - New Canaan HS-Dunning Stadium [Directions] | 5:30 p.m. | ||
| Thu., 9/28 | FR Field Hockey | Danbury | Home - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Thu., 9/28 | FR Girls Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/29 | V Football | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 3:45 p.m. | W 43-0 | |
| Fri., 9/29 | JV Girls Soccer | Stamford | Home - New Canaan HS-WTT #2 [Directions] | Postponed | ||
| Fri., 9/29 | V Girls Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:00 p.m. | W 3-1 | |
| Fri., 9/29 | JV Girls Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 9/29 | FR Girls Volleyball | Norwalk | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/30 | JV Football | Fairfield Ludlowe | Home - New Canaan HS-Dunning Stadium [Directions] | 10:00 a.m. | ||
| Sat., 9/30 | FR Boys Soccer | Stamford | Home - Saxe MS-Field 1 [Directions] | Postponed | ||
| Sat., 9/30 | V Field Hockey | Greenwich | Home - New Canaan HS-Dunning Stadium [Directions] | 1:00 p.m. | W 2-1 | |
| Sat., 9/30 | JV Field Hockey | Greenwich | Home - New Canaan HS-Dunning Stadium [Directions] | 2:30 p.m. | ||
| Mon., 10/2 | V Boys Golf | Greenwich | Home - CCNC [Directions] | 3:30 p.m. | ||
| Mon., 10/2 | JV Boys Golf | Greenwich | Home - CCNC [Directions] | 3:30 p.m. | ||
| Mon., 10/2 | FR Boys Soccer | Danbury | Home - Conner Field, New Cannan [Directions] | 4:00 p.m. | ||
| Mon., 10/2 | V Field Hockey | Westhill | Home - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | W 4-0 | |
| Mon., 10/2 | JV Field Hockey | Westhill | Home - New Canaan HS-Dunning Stadium [Directions] | 5:30 p.m. | ||
| Tue., 10/3 | V Boys Cross Country | Greenwich, St. Joseph, Stamford | Home - Waveny Park [Directions] | 4:00 p.m. | ||
| Tue., 10/3 | V Boys Golf | Stamford | Home - CCNC [Directions] | 3:15 p.m. | ||
| Tue., 10/3 | JV Boys Golf | Fairfield Prep | Home - CCNC [Directions] | 3:15 p.m. | ||
| Tue., 10/3 | V Girls Cross Country | Greenwich, St. Joseph, Stamford | Home - Waveny Park [Directions] | 4:00 p.m. | ||
| Tue., 10/3 | V Girls Diving | Darien | Away - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Tue., 10/3 | V Girls Soccer | Darien | Away - Darien HS-[CIAC] Willow Brook Park [Directions] | 4:00 p.m. | L 4-1 | |
| Tue., 10/3 | JV Girls Soccer | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 10/3 | FR Girls Soccer | Darien | Home - Conner Field, New Cannan [Directions] | 3:45 p.m. | ||
| Tue., 10/3 | V Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Tue., 10/3 | JV Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 10/3 | FR Girls Volleyball | Fairfield Ludlowe | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/4 | V Boys Golf | Fairfield Warde | Home - CCNC [Directions] | 3:30 p.m. | ||
| Wed., 10/4 | JV Boys Golf | Fairfield Warde | Home - CCNC [Directions] | 3:30 p.m. | ||
| Wed., 10/4 | V Boys Soccer | Darien | Home - New Canaan HS-Dunning Stadium [Directions] | 6:30 p.m. | T 1-1 | |
| Wed., 10/4 | JV Boys Soccer | Darien | Home - Conner Field, New Cannan [Directions] | 4:00 p.m. | ||
| Wed., 10/4 | FR Boys Soccer | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 10/4 | V Field Hockey | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | W 5-1 | |
| Wed., 10/4 | JV Field Hockey | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 5:15 p.m. | ||
| Wed., 10/4 | V Girls Swimming and Diving | Darien | Away - Darien YMCA [Directions] | 3:00 p.m. | ||
| Thu., 10/5 | V Field Hockey | Stamford | Home - New Canaan HS-Dunning Stadium [Directions] | 4:30 p.m. | W 4-0 | |
| Thu., 10/5 | JV Field Hockey | Stamford | Home - New Canaan HS-Dunning Stadium [Directions] | 6:00 p.m. | ||
| Thu., 10/5 | V Girls Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 4:15 p.m. | W 2-1 | |
| Thu., 10/5 | JV Girls Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 6:00 p.m. | ||
| Thu., 10/5 | V Girls Volleyball | Fairfield Warde | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Thu., 10/5 | JV Girls Volleyball | Fairfield Warde | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/5 | FR Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:30 p.m. | ||
| Fri., 10/6 | V Boys Soccer | Brien McMahon | Home - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | L 1-2 | |
| Fri., 10/6 | JV Boys Soccer | Brien McMahon | Home - Saxe MS-Field 1 [Directions] | 4:00 p.m. | ||
| Fri., 10/6 | FR Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 5:30 p.m. | ||
| Fri., 10/6 | V Girls Swimming and Diving | Wilton | Away - Wilton YMCA [Directions] | 3:40 p.m. | ||
| Sat., 10/7 | V Football | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 1:30 p.m. | W 45-7 | |
| Sat., 10/7 | V Girls Soccer | Stamford | Home - New Canaan HS-Dunning Stadium [Directions] | 1:00 p.m. | W 3-0 | |
| Sat., 10/7 | V Girls Swimming and Diving | St. Joseph | Away - FLOOD MS [Directions] | Canceled | Cancelled | |
| Sat., 10/7 | V Girls Volleyball | Greenwich | Home - New Canaan HS-Main Gym [Directions] | 2:30 p.m. | L 0-3 | |
| Sat., 10/7 | JV Girls Volleyball | Greenwich | Home - New Canaan HS-Main Gym [Directions] | 1:00 p.m. | ||
| Sat., 10/7 | FR Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 10:00 a.m. | ||
| Mon., 10/9 | JV Football | St. Joseph | Home - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | ||
| Mon., 10/9 | V Boys Golf | Wilton | Away - Rolling Hills Country Club [Directions] | 3:15 p.m. | ||
| Mon., 10/9 | JV Boys Golf | Wilton | Away - Rolling Hills Country Club [Directions] | 3:15 p.m. | ||
| Mon., 10/9 | V Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | W 2-1 | |
| Mon., 10/9 | JV Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 5:30 p.m. | ||
| Mon., 10/9 | FR Field Hockey | Fairfield Ludlowe | Home - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Mon., 10/9 | V Girls Soccer | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | W 4-0 | |
| Mon., 10/9 | JV Girls Soccer | Westhill | Away - Rippowan MS-Rippowam Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 10/9 | V Girls Volleyball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:45 p.m. | L 0-3 | |
| Mon., 10/9 | JV Girls Volleyball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Mon., 10/9 | FR Girls Volleyball | Wilton | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/10 | V Boys Cross Country | Darien, Fairfield Warde, Ridgefield | Away - Darien HS-DHS Stadium East [Directions] | 4:00 p.m. | ||
| Tue., 10/10 | V Boys Golf | Westhill | Away - EG Brennan Golf Course-E Gaynor Brennan Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 10/10 | JV Boys Golf | Staples | Home - CCNC [Directions] | 3:15 p.m. | ||
| Tue., 10/10 | V Boys Soccer | Westhill | Home - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | W 2-1 | |
| Tue., 10/10 | JV Boys Soccer | Westhill | Home - Saxe MS-Field 1 [Directions] | 4:00 p.m. | ||
| Tue., 10/10 | V Girls Cross Country | Darien, Fairfield Warde, Ridgefield | Away - Darien HS-DHS Stadium East [Directions] | 4:00 p.m. | ||
| Wed., 10/11 | V Boys Golf | Darien | Home - CCNC [Directions] | 3:30 p.m. | ||
| Wed., 10/11 | JV Boys Golf | Darien | Home - CCNC [Directions] | 3:30 p.m. | ||
| Wed., 10/11 | FR Boys Soccer | Westhill | Away - Rippowan MS-Rippowam Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 10/11 | V Field Hockey | Wilton | Away - Wilton HS-Fuijitani Field -Turf [Directions] | 3:30 p.m. | L 4-3 | |
| Wed., 10/11 | JV Field Hockey | Wilton | Away - Wilton HS-Fuijitani Field -Turf [Directions] | 5:00 p.m. | ||
| Wed., 10/11 | FR Field Hockey | Wilton | Home - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Wed., 10/11 | JV Girls Soccer | Fairfield Ludlowe | Home - Saxe MS-Field 1 [Directions] | 4:00 p.m. | ||
| Wed., 10/11 | FR Girls Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | 4:30 p.m. | ||
| Wed., 10/11 | V Girls Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | L 0-3 | |
| Wed., 10/11 | JV Girls Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 10/11 | FR Girls Volleyball | Stamford | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/12 | FR Football | Trumbull | Home - New Canaan HS-Dunning Stadium [Directions] | 7:00 p.m. | ||
| Thu., 10/12 | V Boys Golf | Trumbull | Home - CCNC [Directions] | 3:30 p.m. | ||
| Thu., 10/12 | JV Boys Golf | Trumbull | Home - CCNC [Directions] | 3:30 p.m. | ||
| Thu., 10/12 | V Girls Soccer | Bridgeport Central | Home - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | W 8-0 | |
| Thu., 10/12 | JV Girls Soccer | Bridgeport Central | Home - Saxe MS-Field 1 [Directions] | 4:00 p.m. | ||
| Fri., 10/13 | V Boys Soccer | Bridgeport Central | Away - Bridgeport Central-Kennedy Stadium Turf [Directions] | 6:15 p.m. | W 2-1 | |
| Fri., 10/13 | JV Boys Soccer | Bridgeport Central | Away - Kennedy Stadium (Bridgeport) [Directions] | 4:30 p.m. | ||
| Fri., 10/13 | FR Field Hockey | Fairfield Warde | Home - New Canaan HS-WTT #2 [Directions] | Canceled | Cancelled | |
| Fri., 10/13 | FR Girls Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 6:00 p.m. | ||
| Fri., 10/13 | V Girls Swimming and Diving | Ridgefield, St. Joseph | Home - New Canaan YMCA-Pool [Directions] | 3:00 p.m. | ||
| Fri., 10/13 | V Girls Volleyball | Darien | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Fri., 10/13 | JV Girls Volleyball | Darien | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/13 | FR Girls Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/14 | V Boys Soccer | New Milford | Home - New Canaan HS-Dunning Stadium [Directions] | 10:00 a.m. | L 0-3 | |
| Mon., 10/16 | V Girls Soccer | St. Joseph | Home - New Canaan HS-Dunning Stadium [Directions] | 7:00 p.m. | L 5-0 | |
| Mon., 10/16 | JV Girls Soccer | St. Joseph | Home - Saxe MS-Field 1 [Directions] | 4:00 p.m. | ||
| Mon., 10/16 | V Girls Volleyball | Brien McMahon | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | W 3-1 | |
| Mon., 10/16 | JV Girls Volleyball | Brien McMahon | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 10/16 | FR Girls Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:30 p.m. | ||
| Tue., 10/17 | V Boys Soccer | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 4:00 p.m. | W 1-0 | |
| Wed., 10/18 | V Boys Cross Country | FCIAC Championship | Away - Waveny Park | 2:15 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Not Listed-Waveny Park | ||||||
| Wed., 10/18 | V Girls Cross Country | FCIAC Championship | Away - Waveny Park | 2:15 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Not Listed-Waveny Park | ||||||
| Wed., 10/18 | V Girls Soccer | Trumbull | Home - New Canaan HS-Dunning Stadium [Directions] | 7:00 p.m. | T 1-1 | |
| Wed., 10/18 | JV Girls Soccer | Trumbull | Home - Saxe MS-Field 1 [Directions] | 4:00 p.m. | ||
| Wed., 10/18 | FR Girls Soccer | Trumbull | Away - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Wed., 10/18 | V Girls Volleyball | Westhill | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Wed., 10/18 | JV Girls Volleyball | Westhill | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/18 | FR Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/19 | FR Football | Greenwich | Away - Greenwich HS-Field 7 [Directions] | 4:30 p.m. | ||
| Thu., 10/19 | V Boys Soccer | Trumbull | Away - Trumbull HS-Cork Field [Directions] | 5:30 p.m. | L 0-3 | |
| Thu., 10/19 | JV Boys Soccer | Trumbull | Away - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Thu., 10/19 | FR Boys Soccer | Trumbull | Home - Saxe MS-Field 1 [Directions] | 4:00 p.m. | ||
| Thu., 10/19 | V Field Hockey | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 5:00 p.m. | W 7-1 | |
| Thu., 10/19 | JV Field Hockey | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 6:30 p.m. | ||
| Fri., 10/20 | V Girls Soccer | Danbury | Home - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | W 5-1 | |
| Fri., 10/20 | JV Girls Soccer | Danbury | Home - Saxe MS-Field 1 [Directions] | 4:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to New Canaan HS-WTT #2 | ||||||
| Fri., 10/20 | V Girls Swimming and Diving | Fairfield Warde | Home - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Fri., 10/20 | V Girls Volleyball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 10/20 | JV Girls Volleyball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | 4:00 p.m. | ||
| Sat., 10/21 | V Football | Wilton | Home - New Canaan HS-Dunning Stadium [Directions] | 2:00 p.m. | W 20-13 | |
| Sat., 10/21 | FR Girls Soccer | Staples, Trumbull | Home - Conner Field, New Cannan [Directions] | Postponed | ||
| Mon., 10/23 | JV Football | Wilton | Away - Wilton HS-Fuijitani Field -Turf [Directions] | 4:15 p.m. | ||
| Mon., 10/23 | V Field Hockey | Trumbull | Home - New Canaan HS-Dunning Stadium [Directions] | 5:30 p.m. | W 2-1 | |
| Mon., 10/23 | JV Field Hockey | Trumbull | Home - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Mon., 10/23 | FR Field Hockey | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | Canceled | Cancelled | |
| Mon., 10/23 | V Girls Soccer | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 4:00 p.m. | T 1-1 | |
| Mon., 10/23 | JV Girls Soccer | Ridgefield | Away - Ridgefield HS-RHS Lower Grass Field [Directions] | 4:30 p.m. | ||
| Mon., 10/23 | FR Girls Soccer | Ridgefield | Home - Saxe MS-Field 1 [Directions] | Postponed | ||
| Mon., 10/23 | V Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Mon., 10/23 | JV Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:00 p.m. | ||
| Mon., 10/23 | FR Girls Volleyball | St. Joseph | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/24 | V Boys Golf | CIAC Division I Fall Championship | Away - Stanley GC | 8:30 a.m. | ||
| Tue., 10/24 | V Boys Soccer | Ridgefield | Home - New Canaan HS-Dunning Stadium [Directions] | 6:30 p.m. | T 1-1 | |
| Tue., 10/24 | JV Boys Soccer | Ridgefield | Home - Saxe MS-Field 1 [Directions] | 4:00 p.m. | ||
| Tue., 10/24 | FR Boys Soccer | Ridgefield | Away - Ridgefield HS-RHS Lower Grass Field [Directions] | 4:00 p.m. | ||
| Wed., 10/25 | V Girls Swimming and Diving | Greenwich | Away - Greenwich HS-Pool [Directions] | 4:00 p.m. | ||
| Wed., 10/25 | V Girls Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Wed., 10/25 | JV Girls Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/25 | FR Girls Volleyball | Trumbull | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/26 | FR Football | Wilton | Home - New Canaan HS-Dunning Stadium [Directions] | 5:00 p.m. | ||
| Thu., 10/26 | V Girls Soccer | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 2:30 p.m. | ||
| Fri., 10/27 | V Football | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 7:00 p.m. | W 51-8 | |
| Fri., 10/27 | V Field Hockey | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 3:30 p.m. | ||
| Fri., 10/27 | V Girls Volleyball | Ridgefield | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | L 1-3 | |
| Fri., 10/27 | JV Girls Volleyball | Ridgefield | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/27 | FR Girls Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:30 p.m. | ||
| Sat., 10/28 | V Boys Cross Country | CIAC Class L Championship | Away - Wickham Park | 2:40 p.m. | ||
| Sat., 10/28 | JV Football | Norwalk | Home - New Canaan HS-Dunning Stadium [Directions] | 10:00 a.m. | ||
| Sat., 10/28 | V Girls Cross Country | CIAC Class L Championship | Away - Wickham Park | 2:05 p.m. | ||
| Sat., 10/28 | FR Girls Soccer | Trumbull | Home - Ridgefield HS-Tiger Hollow Stadium [Directions] | 10:00 a.m. | ||
| Sat., 10/28 | JV Girls Swimming and Diving | Greenwich, Danbury, Darien, Fairfield Ludlowe, Norwalk/McMahon, Ridgefield, St. Joseph, Staples, Trumbull, Westhill/Stamford, Wilton | Away - Greenwich HS-Pool | 9:30 a.m. | ||
| Tue., 10/31 | V Boys Soccer | Darien (Scrim.) | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 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 | 5:30 p.m. | ||
| Thu., 11/2 | FR Football | Ridgefield | Away - Ridgefield HS-Tiger Hollow Turf Field II [Directions] | 6:30 p.m. | ||
| Thu., 11/2 | V Girls Soccer | Brien McMahon (Scrim.) | Home - New Canaan HS-WTT #1 [Directions] | Canceled | Cancelled | |
| Fri., 11/3 | V Field Hockey | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | 3:45 p.m. | ||
| Sat., 11/4 | V Football | Bridgeport Central | Away - Bridgeport Central-Kennedy Stadium Turf [Directions] | 11:00 a.m. | W 42-6 | |
| Sat., 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 | 3:30 p.m. | ||
| Mon., 11/6 | V Boys Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Mon., 11/6 | JV Football | Bridgeport Central | Home - New Canaan HS-Dunning Stadium [Directions] | Canceled | Cancelled | |
| Mon., 11/6 | V Girls Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Mon., 11/6 | V Girls Soccer | Amity | Home - New Canaan HS-Dunning Stadium [Directions] | 5:00 p.m. | ||
| Tue., 11/7 | V Field Hockey | Avon | Home - New Canaan HS-Dunning Stadium [Directions] | 5:00 p.m. | ||
| Wed., 11/8 | V Girls Soccer | Northwest Catholic | Away - Northwest Catholic HS (Primary)-Neil J. Brewer Field [Directions] | 2:00 p.m. | ||
| Wed., 11/8 | V Girls Swimming and Diving | CIAC Class L Diving Championship | Away - Middletown | 5:30 p.m. | ||
| Thu., 11/9 | V Field Hockey | Pomperaug | Away - Pomperaug HS-Stadium [Directions] | 4:00 p.m. | ||
| Fri., 11/10 | V Football | Brien McMahon | Home - New Canaan HS-Dunning Stadium [Directions] | 7:00 p.m. | W 42-6 | |
| Fri., 11/10 | V Girls Soccer | Bethel | Away - Bethel HS-MS Turf Soccer Field [Directions] | 4:00 p.m. | ||
| Sat., 11/11 | JV Football | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 10:30 a.m. | ||
| Sat., 11/11 | V Girls Swimming and Diving | CIAC Class L Qualifying Meet | Away - Cornerstone Pool | 11:15 a.m. | ||
| Tue., 11/14 | V Field Hockey | Guilford | Away - Amity Regional HS-Field Hockey Field [Directions] | 6:30 p.m. | ||
| Tue., 11/14 | V Girls Swimming and Diving | CIAC Class L Finals | Away - Cornerstone Pool | 6:00 p.m. | ||
| Thu., 11/16 | FR Football | Darien | Home - New Canaan HS-Dunning Stadium [Directions] | 5:00 p.m. | ||
| Thu., 11/16 | V Girls Swimming and Diving | CIAC State Open Diving | Away - Middletown | 5:30 p.m. | ||
| Fri., 11/17 | JV Football | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 4:30 p.m. | ||
| Sat., 11/18 | V Field Hockey | Daniel Hand | Away - Wethersfield HS-Cottone Field [Directions] | 3:30 p.m. | ||
| Sun., 11/19 | V Girls Swimming and Diving | CIAC State Open Swimming | Away - Yale | 1:00 p.m. | ||
| Thu., 11/23 | V Football | Darien | Home - New Canaan HS-Dunning Stadium [Directions] | 10:00 a.m. | W 31-17 | |
| Thu., 11/23 | V Competitive Cheerleading | Darien | Home - New Canaan HS [Directions] | 10:00 a.m. | ||
| Tue., 11/28 | V Football | CIAC Quarterfinals | Away - Higher Seed | 6:30 p.m. | ||
| Tue., 11/28 | V Football | Killingly | Home - New Canaan HS-Dunning Stadium [Directions] | 6:30 p.m. | W 49-14 | |
| Sat., 12/2 | V Girls Ice Hockey | Darien (Scrim.) | Home - Darien Ice House-Ice Rink [Directions] | 6:30 p.m. | T 0-0 | |
| Sun., 12/3 | V Football | Maloney | Home - New Canaan HS-Dunning Stadium [Directions] | 12:30 p.m. | W 11-8 | |
| Sun., 12/3 | V Football | CIAC Semifinals | Away - Higher Seed | 12:30 p.m. | ||
| Mon., 12/4 | V Boys Ice Hockey | Delbarton (NJ) (Scrim.) | Home - Darien Ice House-Ice Rink [Directions] | 6:00 p.m. | ||
| Wed., 12/6 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:30 p.m. | W 8-2 | |
| Thu., 12/7 | V Boys Basketball | Jonathan Law (Scrim.) | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | Cancelled | |
| Thu., 12/7 | V Boys Ice Hockey | King and Low-Heywood Thomas (Scrim.) | Away - Stamford Twin Rinks-West | 3:50 p.m. | Cancelled | |
| Thu., 12/7 | V Girls Ice Hockey | Mamaroneck (NY) | Home - Darien Ice House-Ice Rink [Directions] | 8:00 p.m. | W 3-0 | |
| Sat., 12/9 | V Boys Basketball | Masuk (Scrim.) | Home - New Canaan HS-Main Gym [Directions] | 2:00 p.m. | ||
| Sat., 12/9 | V Football | Darien | Away - Rentschler Field [Directions] | 1:30 p.m. | W 28-21 | |
| Sat., 12/9 | V Football | CIAC Championship Games | Away - Site TBA | TBA | ||
| Sat., 12/9 | JV Boys Ice Hockey | Darien (Scrim.) | Away - Darien Ice House-Ice Rink [Directions] | 7:40 p.m. | ||
| Sat., 12/9 | V Competitive Cheerleading | Darien | Home - Rentschler Field [Directions] | 1:30 p.m. | ||
| Sat., 12/9 | V Girls Ice Hockey | Mercy/NW Catholic/East Hampton | Home - Darien Ice House-Ice Rink [Directions] | 4:15 p.m. | W 7-0 | |
| Mon., 12/11 | V Boys Basketball | Harding (Scrim.) | Away - Warren Harding HS-Gym [Directions] | 5:30 p.m. | ||
| Mon., 12/11 | V Boys Ice Hockey | Greenwich | Home - Darien Ice House-Ice Rink [Directions] | 6:00 p.m. | W 4-1 | |
| Mon., 12/11 | V Girls Basketball | Pomperaug | Home - New Canaan HS-Main Gym [Directions] | 7:00 p.m. | L 51-49 | |
| Mon., 12/11 | JV Girls Basketball | Pomperaug | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 12/11 | FR Girls Basketball | Pomperaug | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 12/13 | V Girls Basketball | Joel Barlow | Home - New Canaan HS-Main Gym [Directions] | 7:00 p.m. | W 27-25 | |
| Wed., 12/13 | JV Girls Basketball | Joel Barlow | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 12/13 | FR Girls Basketball | Joel Barlow | Home - New Canaan HS-Main Gym [Directions] | Canceled | Cancelled | |
| Wed., 12/13 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Darien Ice House-Ice Rink [Directions] | 7:15 p.m. | W 5-0 | |
| Thu., 12/14 | V Wrestling | Danbury | Home - New Canaan HS-Main Gym [Directions] | 7:00 p.m. | ||
| Fri., 12/15 | V Boys Ice Hockey | Fairfield Prep | Home - Darien Ice House-Ice Rink [Directions] | 4:00 p.m. | W 4-1 | |
| Sat., 12/16 | V Boys Basketball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 2:00 p.m. | L 66-59 | |
| Sat., 12/16 | JV Boys Basketball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 12:15 p.m. | ||
| Sat., 12/16 | FR Boys Basketball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 10:30 a.m. | ||
| Sat., 12/16 | JV Boys Ice Hockey | Greenwich | Home - Darien Ice House-Ice Rink [Directions] | 7:30 p.m. | ||
| Sat., 12/16 | V Boys Indoor Track | Wilton, Danbury, Norwalk | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:30 a.m. | ||
| Sat., 12/16 | V Wrestling | Nonnewaug | Home - New Canaan HS-Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 12/16 | V Girls Basketball | Weston | Away - Weston HS-Gym (New) [Directions] | 12:15 p.m. | W 42-32 | |
| Sat., 12/16 | JV Girls Basketball | Weston | Away - Weston HS-Gym (New) [Directions] | 10:30 a.m. | ||
| Sat., 12/16 | V Girls Ice Hockey | Southington Coop | Home - Darien Ice House-Ice Rink [Directions] | 4:15 p.m. | W 2-0 | |
| Sat., 12/16 | V Girls Indoor Track | Wilton, Danbury, Norwalk | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:30 a.m. | ||
| Sun., 12/17 | JV Boys Ice Hockey | Notre Dame-West Haven | Away - West Haven HS-Bennett Rink [Directions] | 5:00 p.m. | ||
| Mon., 12/18 | V Girls Ice Hockey | Stamford/Westhill/Staples | Home - Darien Ice House-Ice Rink [Directions] | 7:00 p.m. | W 3-0 | |
| Wed., 12/20 | V Boys Ice Hockey | Simsbury | Home - Darien Ice House-Ice Rink [Directions] | 6:00 p.m. | W 3-0 | |
| Wed., 12/20 | V Wrestling | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 6:00 p.m. | ||
| Wed., 12/20 | V Girls Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | W 31-16 | |
| Wed., 12/20 | JV Girls Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 12/21 | V Boys Basketball | Weston | Home - New Canaan HS-Main Gym [Directions] | 7:00 p.m. | W 51-44 | |
| Thu., 12/21 | JV Boys Basketball | Weston | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 12/21 | FR Boys Basketball | Weston | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 12/22 | V Girls Basketball | Trumbull | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | W 45-34 | |
| Fri., 12/22 | JV Girls Basketball | Trumbull | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 12/22 | FR Girls Basketball | Trumbull | Home - New Canaan HS-Main Gym [Directions] | Canceled | Cancelled | |
| Fri., 12/22 | V Girls Ice Hockey | South Kingstown (RI) | Home - Darien Ice House-Ice Rink [Directions] | 6:30 p.m. | W 2-0 | |
| Sat., 12/23 | V Boys Ice Hockey | Notre Dame-West Haven | Away - West Haven HS-Bennett Rink [Directions] | 3:00 p.m. | L 5-1 | |
| Sat., 12/23 | V Boys Indoor Track | North Shore Invite | Away - The Armory | 9:30 a.m. | ||
| Sat., 12/23 | V Wrestling | Wilton, North Haven, Stamford | Away - Wilton HS-Nicholas Zeoli Fieldhouse [Directions] | 9:00 a.m. | ||
| Wed., 12/27 | V Boys Basketball | Bethel | Away - New Milford HS-Main Gym - NMHS [Directions] | 5:00 p.m. | W 48-31 | |
| Wed., 12/27 | JV Boys Ice Hockey | Ridgefield | Home - Darien Ice House-Ice Rink [Directions] | 7:00 p.m. | ||
| Wed., 12/27 | V Wrestling | Danbury, Brookfield/Shepaug, Enfield, TBA, TBA, TBA, New Fairfield, New Milford, RHAM, Southington | Away - Danbury HS-Main Gym | 9:30 a.m. | ||
| Fri., 12/29 | V Boys Basketball | Shelton | Away - New Milford HS-Main Gym - NMHS [Directions] | 7:00 p.m. | W 54-45 | |
| Fri., 12/29 | V Boys Ice Hockey | Barrington (RI) | Away - Barrington Public Schools | 1:45 p.m. | W 5-1 | |
| Fri., 12/29 | JV Wrestling | Trumbull, Brien McMahon, Darien, Fairfield Warde, Greenwich, Masuk, TBA, New Fairfield, New Milford, Newtown, Ridgefield, Simsbury, Stamford, Staples, Xavier | Away - Trumbull HS-THS Main Gym | 9:00 a.m. | ||
| Tue., 1/2 | V Boys Indoor Track | Wilton Wright Invite | Away - Southern CT State University | 4:00 p.m. | ||
| Tue., 1/2 | V Girls Indoor Track | Wilton Wright Invite | Away - Southern CT State University | 4:00 p.m. | ||
| Wed., 1/3 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Home - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Wed., 1/3 | V Wrestling | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Aux Gym [Directions] | 5:00 p.m. | ||
| Wed., 1/3 | V Girls Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 7:00 p.m. | L 42-29 | |
| Wed., 1/3 | JV Girls Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/3 | FR Girls Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/3 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Away - Hamden-Lou Astorino Ice Rink [Directions] | 7:00 p.m. | W 6-1 | |
| Thu., 1/4 | V Girls Indoor Track | Wintergreen Invite | Away - Southern CT State University | 4:00 p.m. | ||
| Fri., 1/5 | V Boys Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 7:00 p.m. | L 64-51 | |
| Fri., 1/5 | JV Boys Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/5 | FR Boys Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/5 | JV Boys Ice Hockey | Greenwich | Away - Greenwich - Dorothy Hamill-Rink [Directions] | 5:15 p.m. | ||
| Fri., 1/5 | V Boys Swimming and Diving | Staples | Away - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Fri., 1/5 | V Girls Basketball | Danbury | Home - New Canaan HS-Main Gym [Directions] | 7:00 p.m. | W 43-35 | |
| Fri., 1/5 | JV Girls Basketball | Danbury | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/5 | FR Girls Basketball | Danbury | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/5 | V Girls Ice Hockey | Greenwich | Home - Darien Ice House-Ice Rink [Directions] | 8:15 p.m. | W 8-0 | |
| Sat., 1/6 | V Boys Ice Hockey | Greenwich | Away - Greenwich - Dorothy Hamill-Rink [Directions] | 5:45 p.m. | W 8-1 | |
| Sat., 1/6 | V Boys Indoor Track | Wilton, Darien, Ridgefield | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:30 a.m. | ||
| Sat., 1/6 | V Wrestling | Amity Duals | Away - Amity Regional HS-Paul D. Mengold Gymnasium | 9:00 a.m. | ||
| Sat., 1/6 | V Girls Indoor Track | Wilton, Darien, Ridgefield | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:30 a.m. | ||
| Mon., 1/8 | V Boys Ice Hockey | Ridgefield | Home - Darien Ice House-Ice Rink [Directions] | 6:00 p.m. | W 3-1 | |
| Tue., 1/9 | V Boys Basketball | Staples | Home - New Canaan HS-Main Gym [Directions] | 5:15 p.m. | L 53-45 | |
| Tue., 1/9 | JV Boys Basketball | Staples | Home - New Canaan HS-Main Gym [Directions] | 3:45 p.m. | ||
| Tue., 1/9 | FR Boys Basketball | Staples | Home - New Canaan HS-Main Gym [Directions] | Postponed | ||
| Tue., 1/9 | V Girls Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 5:15 p.m. | W 55-50(OT) | |
| Tue., 1/9 | JV Girls Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 3:45 p.m. | ||
| Tue., 1/9 | FR Girls Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | Postponed | ||
| Wed., 1/10 | V Boys Indoor Track | James Barber Invite | Away - Southern CT State University | 4:00 p.m. | ||
| Wed., 1/10 | V Wrestling | Staples | Home - New Canaan HS-Main Gym [Directions] | 7:00 p.m. | ||
| Wed., 1/10 | V Girls Gymnastics | Norwalk | Away - Westport YMCA [Directions] | 7:30 p.m. | 83.3 | |
| Wed., 1/10 | V Girls Gymnastics | Staples, Foran | Away - Staples HS-Westport YMCA [Directions] | 7:30 p.m. | 83.3 | |
| Wed., 1/10 | V Girls Ice Hockey | Darien | Away - Darien Ice House-Ice Rink [Directions] | 8:00 p.m. | L 0-1 | |
| Wed., 1/10 | V Girls Indoor Track | James Barber Invite | Away - Southern CT State University | 4:00 p.m. | ||
| Fri., 1/12 | V Boys Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 7:00 p.m. | L 53-43 | |
| Fri., 1/12 | JV Boys Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/12 | FR Boys Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/12 | JV Boys Ice Hockey | Darien | Home - New Canaan Winter Club-Rink [Directions] | 6:00 p.m. | ||
| Fri., 1/12 | V Boys Indoor Track | Yale Invite Relays | Away - Yale University New Haven CT | 1:00 p.m. | ||
| Fri., 1/12 | V Girls Basketball | Norwalk | Home - New Canaan HS-Main Gym [Directions] | 6:00 p.m. | W 46-34 | |
| Fri., 1/12 | JV Girls Basketball | Norwalk | Home - New Canaan HS-Main Gym [Directions] | 4:30 p.m. | ||
| Fri., 1/12 | V Girls Indoor Track | Yale Invite Relays | Away - Yale University New Haven CT | 4:00 p.m. | ||
| Sat., 1/13 | V Boys Ice Hockey | Darien | Home - Darien Ice House-Ice Rink [Directions] | 4:15 p.m. | L 4-3(OT) | |
| Sat., 1/13 | V Boys Indoor Track | Wilton, Brien McMahon, Fairfield Ludlowe, Fairfield Warde, Norwalk, Ridgefield, Trumbull | Away - Wilton HS-Nicholas Zeoli Field House | 9:30 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 9:00 a.m. | ||||||
| Sat., 1/13 | V Wrestling | Notre Dame-West Haven, Fitch, Glastonbury, St. Joseph | Away - Notre Dame HS-Gym [Directions] | 10:00 a.m. | ||
| Sat., 1/13 | V Girls Indoor Track | Wilton, Brien McMahon, Fairfield Ludlowe, Fairfield Warde, Norwalk, Ridgefield | Away - Wilton HS-Nicholas Zeoli Field House | 9:30 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 9:00 a.m. | ||||||
| Mon., 1/15 | FR Boys Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 2:45 p.m. | ||
| Mon., 1/15 | V Girls Ice Hockey | LaSalle Academy (RI) | Home - Darien Ice House-Ice Rink [Directions] | 1:30 p.m. | W 6-0 | |
| Wed., 1/17 | V Boys Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 7:00 p.m. | L 63-36 | |
| Wed., 1/17 | JV Boys Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/17 | FR Boys Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/17 | JV Boys Ice Hockey | Fairfield Prep | Away - Wonderland of Ice-Stadium [Directions] | 6:00 p.m. | ||
| Wed., 1/17 | V Boys Swimming and Diving | Wilton | Home - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Wed., 1/17 | V Wrestling | Darien | Away - Darien HS-DHS South Gym [Directions] | 5:00 p.m. | ||
| Wed., 1/17 | V Girls Basketball | Fairfield Ludlowe | Home - New Canaan HS-Main Gym [Directions] | 7:00 p.m. | L 57-43 | |
| Wed., 1/17 | JV Girls Basketball | Fairfield Ludlowe | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/17 | FR Girls Basketball | Fairfield Ludlowe | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/17 | V Girls Gymnastics | Westhill, Stamford | Away - Westhill HS-New Gym [Directions] | 6:00 p.m. | 71.5 | |
| Wed., 1/17 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 3:30 p.m. | W 6-1 | |
| Fri., 1/19 | V Boys Basketball | Fairfield Warde | Home - New Canaan HS-Main Gym [Directions] | 7:00 p.m. | L 66-62(OT) | |
| Fri., 1/19 | JV Boys Basketball | Fairfield Warde | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/19 | FR Boys Basketball | Fairfield Warde | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/19 | V Boys Ice Hockey | Prout (RI) | Home - Darien Ice House-Ice Rink [Directions] | 6:00 p.m. | W 7-0 | |
| Fri., 1/19 | V Boys Swimming and Diving | Darien | Home - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Fri., 1/19 | V Wrestling | Fairfield Warde, Foran, Shelton | Away - Fairfield Warde HS-Small Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/19 | V Girls Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 7:00 p.m. | L 35-33 | |
| Fri., 1/19 | JV Girls Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/19 | FR Girls Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:00 p.m. | ||
| Sat., 1/20 | V Boys Indoor Track | Wilton, Bridgeport Central, Brien McMahon, Danbury, Greenwich, St. Joseph, Stamford | Away - Wilton HS-Nicholas Zeoli Field House | 9:30 a.m. | ||
| Sat., 1/20 | JV Wrestling | Danbury, Enfield, Fairfield Ludlowe, Fairfield Warde, New Fairfield, Newtown, Norwalk, Ridgefield, Simsbury, Southington, Stamford, Trumbull, Weston | Away - Danbury HS-Main Gym | 9:30 a.m. | ||
| Sat., 1/20 | V Girls Gymnastics | Darien, Stamford, Westhill | Away - Darien YMCA [Directions] | 2:30 p.m. | 60.6 | |
| Sat., 1/20 | V Girls Ice Hockey | West Haven/SHA | Away - West Haven HS-Bennett Rink [Directions] | 1:00 p.m. | W 3-0 | |
| Sat., 1/20 | V Girls Indoor Track | Wilton, Bridgeport Central, Brien McMahon, Danbury, Greenwich, St. Joseph, Stamford | Away - Wilton HS-Nicholas Zeoli Field House | 9:30 a.m. | ||
| Mon., 1/22 | V Girls Gymnastics | Fairfield Ludlowe, Fairfield Warde, Greenwich | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:30 p.m. | 57.35 | |
| Mon., 1/22 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Sacred Heart University-Martire Arena [Directions] | 5:15 p.m. | W 7-0 | |
| Tue., 1/23 | V Boys Basketball | Greenwich | Home - New Canaan HS-Main Gym [Directions] | 7:00 p.m. | W 57-44 | |
| Tue., 1/23 | JV Boys Basketball | Greenwich | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/23 | FR Boys Basketball | Greenwich | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/23 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Sacred Heart University-Martire Arena [Directions] | 6:00 p.m. | W 8-1 | |
| Tue., 1/23 | JV Boys Ice Hockey | Ridgefield | Away - Danbury Ice Arena-TBA [Directions] | 8:00 p.m. | ||
| Tue., 1/23 | V Girls Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 7:00 p.m. | L 40-35 | |
| Tue., 1/23 | JV Girls Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/23 | FR Girls Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 1/24 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Home - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Wed., 1/24 | V Wrestling | Brien McMahon | Home - New Canaan HS-Main Gym [Directions] | 7:00 p.m. | ||
| Wed., 1/24 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Conners - Stamford-Ice Rink [Directions] | 7:30 p.m. | W 2-0 | |
| Fri., 1/26 | V Boys Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 7:00 p.m. | L 46-38 | |
| Fri., 1/26 | JV Boys Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:15 p.m. | ||
| Fri., 1/26 | FR Boys Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Fri., 1/26 | V Boys Ice Hockey | Westhill/Stamford | Home - Darien Ice House-Ice Rink [Directions] | 8:15 p.m. | W 7-1 | |
| Fri., 1/26 | V Boys Swimming and Diving | Greenwich | Away - Greenwich HS-Pool [Directions] | 4:15 p.m. | ||
| Fri., 1/26 | V Girls Basketball | Wilton | Home - New Canaan HS-Main Gym [Directions] | 6:00 p.m. | W 36-29 | |
| Fri., 1/26 | JV Girls Basketball | Wilton | Home - New Canaan HS-Main Gym [Directions] | 4:30 p.m. | ||
| Sat., 1/27 | JV Boys Ice Hockey | Fairfield Prep | Home - Darien Ice House-Ice Rink [Directions] | 8:00 p.m. | ||
| Sat., 1/27 | V Wrestling | Brookfield Invitational | Away - Brookfield HS-BHS Small & Big Gym | 9:30 a.m. | ||
| Sat., 1/27 | JV Wrestling | Norwalk, Brien McMahon, Darien, Fairfield Prep, Fairfield Ludlowe, Fairfield Warde, Greenwich, New Milford, St. Joseph, Stamford, Staples, Trumbull, Westhill, Weston, Wilton | Away - Norwalk HS-Tom Scarso Gymnasium | 8:00 a.m. | ||
| Mon., 1/29 | V Boys Ice Hockey | Woodstock Academy | Home - Darien Ice House-Ice Rink [Directions] | 6:00 p.m. | W 3-1 | |
| Mon., 1/29 | V Girls Ice Hockey | Greenwich | Away - Greenwich - Dorothy Hamill-Rink [Directions] | 4:30 p.m. | W 5-0 | |
| Tue., 1/30 | V Boys Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 7:00 p.m. | L 51-39 | |
| Tue., 1/30 | JV Boys Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/30 | FR Boys Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/30 | V Girls Basketball | Stamford | Home - New Canaan HS-Main Gym [Directions] | 7:00 p.m. | L 48-33 | |
| Tue., 1/30 | JV Girls Basketball | Stamford | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/30 | FR Girls Basketball | Stamford | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/31 | JV Boys Ice Hockey | Xavier | Home - Darien Ice House-Ice Rink [Directions] | 7:15 p.m. | ||
| Wed., 1/31 | V Boys Swimming and Diving | Westhill/Stamford | Away - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Wed., 1/31 | V Wrestling | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 6:30 p.m. | ||
| Thu., 2/1 | V Boys Ice Hockey | St. Joseph | Away - Sports Center of Connecticut-Lower [Directions] | 6:30 p.m. | W 16-1 | |
| Thu., 2/1 | V Boys Indoor Track | FCIAC Championships | Away - Not Listed | 4:00 p.m. | ||
| Thu., 2/1 | V Girls Indoor Track | FCIAC Championships | Away - Not Listed | 4:00 p.m. | ||
| Fri., 2/2 | V Boys Basketball | Darien | Home - New Canaan HS-Main Gym [Directions] | 7:00 p.m. | W 49-47 | |
| Fri., 2/2 | JV Boys Ice Hockey | Darien | Away - Stamford Twin Rinks-West [Directions] | 8:30 p.m. | ||
| Fri., 2/2 | V Girls Basketball | Darien | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | W 41-21 | |
| Fri., 2/2 | JV Girls Basketball | Darien | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 2/2 | FR Girls Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 2/3 | JV Boys Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 11:30 a.m. | ||
| Sat., 2/3 | FR Boys Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 2/3 | V Boys Ice Hockey | St. Joseph | Home - Darien Ice House-Ice Rink [Directions] | 6:30 p.m. | W 5-1 | |
| Sat., 2/3 | V Competitive Cheerleading | FCIAC Cheer Championship | Away - Trumbull HS-THS Main Gym | 10:00 a.m. | ||
| Sat., 2/3 | V Girls Ice Hockey | East Catholic Coop | Away - Newington-Red Rink [Directions] | 7:00 p.m. | W 5-0 | |
| Sun., 2/4 | JV Boys Ice Hockey | Notre Dame-West Haven | Home - Darien Ice House-Ice Rink [Directions] | 7:30 p.m. | ||
| Mon., 2/5 | V Girls Basketball | Harding | Home - New Canaan HS-Main Gym [Directions] | 6:00 p.m. | W 48-19 | |
| Mon., 2/5 | JV Girls Basketball | Harding | Home - New Canaan HS-Main Gym [Directions] | 4:30 p.m. | ||
| Tue., 2/6 | V Boys Basketball | Brien McMahon | Home - New Canaan HS-Main Gym [Directions] | 7:00 p.m. | L 43-37 | |
| Tue., 2/6 | JV Boys Basketball | Brien McMahon | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/6 | FR Boys Basketball | Brien McMahon | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/6 | V Girls Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 5:30 p.m. | W 41-25 | |
| Tue., 2/6 | JV Girls Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 2/7 | V Boys Ice Hockey | Notre Dame-Fairfield | Away - Sacred Heart University-Martire Arena [Directions] | 7:30 p.m. | W 7-1 | |
| Wed., 2/7 | V Wrestling | St. Joseph | Home - New Canaan HS-Main Gym [Directions] | 7:00 p.m. | ||
| Thu., 2/8 | V Boys Basketball | Westhill | Home - New Canaan HS-Main Gym [Directions] | 7:00 p.m. | W 56-53 | |
| Thu., 2/8 | JV Boys Basketball | Westhill | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 2/8 | FR Boys Basketball | Westhill | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 2/8 | V Girls Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 7:00 p.m. | W 57-12 | |
| Thu., 2/8 | JV Girls Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 2/8 | FR Girls Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 2/8 | V Girls Gymnastics | Greenwich | Away - Greenwich YWCA [Directions] | 6:30 p.m. | 98.68 | |
| Fri., 2/9 | V Boys Swimming and Diving | Danbury | Home - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Fri., 2/9 | 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] | 4:30 p.m. | ||
| Sat., 2/10 | V Boys Basketball | Ledyard | Away - Ledyard HS-Judy Standish Gymnasium [Directions] | 1:30 p.m. | W 60-33 | |
| Sat., 2/10 | JV Boys Basketball | Ledyard | Away - Ledyard HS-Judy Standish Gymnasium [Directions] | 12:00 p.m. | ||
| Sat., 2/10 | V Boys Ice Hockey | Ridgefield | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:30 p.m. | W 5-0 | |
| Sat., 2/10 | JV Boys Ice Hockey | Xavier | Away - Wesleyan University-Freeman Athletic Center [Directions] | 10:00 a.m. | ||
| Sat., 2/10 | V Boys Indoor Track | Class L Championships | Away - Not Listed | 10:00 a.m. | ||
| Sat., 2/10 | V Boys Indoor Track | CIAC L Divisional Championship | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Sat., 2/10 | V Wrestling | FCIAC | Home - New Canaan HS-Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 2/10 | V Girls Ice Hockey | Darien | Home - Darien Ice House-Ice Rink [Directions] | 6:30 p.m. | L 0-1 | |
| Sat., 2/10 | V Girls Indoor Track | Class L Championships | Away - Not Listed | 10:00 a.m. | ||
| Sat., 2/10 | V Girls Indoor Track | CIAC L Divisional Championship | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Mon., 2/12 | V Boys Basketball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | 7:00 p.m. | W 56-38 | |
| Mon., 2/12 | JV Boys Basketball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | 5:30 p.m. | ||
| Mon., 2/12 | FR Boys Basketball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | 4:00 p.m. | ||
| Mon., 2/12 | V Boys Swimming and Diving | Trumbull | Away - Univ of Bridgeport Pool [Directions] | 4:00 p.m. | ||
| Mon., 2/12 | V Girls Basketball | Bridgeport Central | Home - New Canaan HS-Main Gym [Directions] | 7:00 p.m. | W 51-38 | |
| Mon., 2/12 | JV Girls Basketball | Bridgeport Central | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/12 | FR Girls Basketball | Bridgeport Central | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/14 | V Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 7:00 p.m. | L 62-57 | |
| Wed., 2/14 | JV Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/14 | FR Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/14 | V Boys Ice Hockey | Darien | Away - Darien Ice House-Ice Rink [Directions] | 4:00 p.m. | W 4-3(OT) | |
| Wed., 2/14 | V Boys Swimming and Diving | Ridgefield | Away - Barlow Mountain Pool [Directions] | 4:00 p.m. | ||
| Wed., 2/14 | V Girls Basketball | St. Joseph | Home - New Canaan HS-Main Gym [Directions] | 7:00 p.m. | L 42-35 | |
| Wed., 2/14 | JV Girls Basketball | St. Joseph | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/14 | FR Girls Basketball | St. Joseph | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/14 | V Girls Ice Hockey | Greenwich Academy | Away - Chelsea Piers - -Chelsea Piers - North Rink | 3:30 p.m. | W 5-2 | |
| Fri., 2/16 | JV Boys Ice Hockey | Darien | Away - Stamford Twin Rinks-West [Directions] | 8:30 p.m. | ||
| Fri., 2/16 | V Wrestling | CIAC L Divisional Championship | Away - Wilton | TBA | ||
| Fri., 2/16 | V Girls Ice Hockey | Suffield Coop | Home - Darien Ice House-Ice Rink [Directions] | 8:15 p.m. | W 5-0 | |
| Sat., 2/17 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Home - Darien Ice House-Ice Rink [Directions] | 7:45 p.m. | W 6-1 | |
| Sat., 2/17 | V Boys Indoor Track | CIAC State Open Divisional Championship | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/17 | V Boys Indoor Track | State Open | Away - Not Listed | 12:00 p.m. | ||
| Sat., 2/17 | V Girls Basketball | Stamford | Away - Staples HS-Staples Gym [Directions] | 12:45 p.m. | ||
| Sat., 2/17 | V Girls Indoor Track | State Open | Away - Not Listed | 12:00 p.m. | ||
| Sat., 2/17 | V Girls Indoor Track | CIAC State Open Championship | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Mon., 2/19 | V Boys Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 7:00 p.m. | L 75-52 | |
| Mon., 2/19 | JV Boys Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/19 | FR Boys Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 2/19 | V Boys Ice Hockey | Xavier | Away - Wesleyan University-Freeman Athletic Center [Directions] | 12:00 p.m. | W 5-0 | |
| Tue., 2/20 | V Girls Basketball | Ridgefield | Away - Trumbull HS-Gym [Directions] | 7:45 p.m. | ||
| Wed., 2/21 | V Boys Basketball | Ridgefield | Home - New Canaan HS-Main Gym [Directions] | 7:00 p.m. | L 56-47 | |
| Wed., 2/21 | JV Boys Basketball | Ridgefield | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/21 | FR Boys Basketball | Ridgefield | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/21 | V Boys Ice Hockey | Fairfield Prep | Away - Wonderland of Ice-Stadium [Directions] | 6:00 p.m. | W 5-2 | |
| Wed., 2/21 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Darien Ice House-Ice Rink [Directions] | 6:00 p.m. | ||
| Thu., 2/22 | V Girls Basketball | St. Joseph | Away - Trumbull HS-Gym [Directions] | 7:00 p.m. | ||
| Fri., 2/23 | V Wrestling | CIAC State Open & Girls Championship | Away - Floyd Little Athletic Center | TBA | ||
| Sat., 2/24 | V Girls Ice Hockey | Darien | Home - Darien Ice House-Ice Rink [Directions] | 3:00 p.m. | ||
| Tue., 2/27 | JV Boys Ice Hockey | Ridgefield | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 3:45 p.m. | ||
| Tue., 2/27 | V Girls Basketball | Guilford | Home - New Canaan HS-Main Gym [Directions] | 6:30 p.m. | W 62-41 | |
| Wed., 2/28 | V Boys Ice Hockey | Greenwich | Home - Darien Ice House-Ice Rink [Directions] | 5:00 p.m. | ||
| Thu., 2/29 | V Boys Basketball | Harding (Scrim.) | Home - New Canaan HS-Main Gym [Directions] | 4:45 p.m. | ||
| Thu., 2/29 | V Girls Ice Hockey | Suffield Coop | Home - Darien Ice House-Ice Rink [Directions] | 7:30 p.m. | ||
| Fri., 3/1 | JV Boys Ice Hockey | Darien | Away - Stamford Twin Rinks-West [Directions] | 8:30 p.m. | ||
| Fri., 3/1 | V Girls Basketball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 6:30 p.m. | L 32-40 | |
| Sat., 3/2 | V Boys Ice Hockey | Ridgefield | Home - Danbury Ice Arena-Colonial Rink [Directions] | 12:00 p.m. | ||
| Sat., 3/2 | V Girls Ice Hockey | East Catholic Coop | Home - Shelton - Sports Center of CT-Lower Rink [Directions] | 7:40 p.m. | ||
| Tue., 3/5 | V Boys Basketball | Bunnell | Away - Bunnell HS-David Johnson Gymnasium [Directions] | 6:30 p.m. | L 47-62 | |
| Wed., 3/6 | V Boys Ice Hockey | CIAC Div I First Round | Away - Higher Seed | TBA | ||
| Wed., 3/6 | V Boys Swimming and Diving | CIAC Class L Diving Championship | Away - Middletown | 5:30 p.m. | ||
| Wed., 3/6 | V Girls Ice Hockey | Stamford/Westhill/Staples | Home - Quinnipiac University-TD Bank Sports Center [Directions] | 7:00 p.m. | ||
| Sat., 3/9 | V Boys Ice Hockey | Greenwich | Home - Terry Conners - Stamford-Ice Rink [Directions] | 7:30 p.m. | W 7-0 | |
| Sat., 3/9 | V Boys Ice Hockey | CIAC Div I Quarterfinal | Away - Site TBA | TBA | ||
| Sat., 3/9 | V Boys Swimming and Diving | CIAC Class L Qualifying Meet | Away - Cornerstone Pool | 11:15 a.m. | ||
| Tue., 3/12 | V Boys Swimming and Diving | CIAC Class L Finals | Away - Cornerstone Pool | 6:00 p.m. | ||
| Wed., 3/13 | V Boys Ice Hockey | Darien | Home - Quinnipiac University-TD Bank Sports Center [Directions] | 5:30 p.m. | W 6-1 | |
| Wed., 3/13 | V Boys Ice Hockey | CIAC Div I Semifinal | Away - Site TBA | TBA | ||
| Thu., 3/14 | V Boys Swimming and Diving | CIAC State Open Diving | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/16 | V Boys Swimming and Diving | CIAC State Open Swimming | Away - Yale | 1:00 p.m. | ||
| Tue., 3/19 | V Boys Ice Hockey | Notre Dame-West Haven | Home - Quinnipiac University-TD Bank Sports Center [Directions] | 7:00 p.m. | L 1-4 | |
| Tue., 3/19 | V Boys Ice Hockey | CIAC Div I Final | Away - Site TBA | TBA | ||
| Wed., 3/20 | V Baseball | Wilton (Scrim.) | Away - Wilton HS-Varsity Baseball Field [Directions] | 4:15 p.m. | ||
| Wed., 3/20 | JV Baseball | TBA | Away - TBA | Canceled | Cancelled | |
| Sat., 3/23 | V Boys Volleyball | Joel Barlow, Farmington, Glastonbury, Iona Prep (NY), Pomperaug, Simsbury, Trumbull | Away - Joel Barlow HS-Lower Gym | 8:30 a.m. | ||
| Sat., 3/23 | V Boys Volleyball | Joel Barlow (Scrim.) | Away - Joel Barlow HS-Lower Gym [Directions] | 1:00 p.m. | ||
| Sat., 3/23 | V Girls Lacrosse | Wilton (Scrim.) | Away - Wilton HS-Lilly Field [Directions] | Canceled | Cancelled | |
| Sat., 3/23 | JV Girls Lacrosse | Wilton (Scrim.) | Away - Wilton HS-Lilly Field [Directions] | Canceled | Cancelled | |
| Sun., 3/24 | V Baseball | Greenwich (Scrim.) | Home - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 2:30 p.m. | ||
| Sun., 3/24 | V Baseball | Norwalk (Scrim.) | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 4:30 p.m. | ||
| Mon., 3/25 | V Girls Lacrosse | Sacred Heart of Greenwich (Scrim.) | Away - Sacred Heart Greenwich-Sheehan Turf Field | 4:30 p.m. | ||
| Tue., 3/26 | V Boys Lacrosse | Rye (NY) (Scrim.) | Home - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | ||
| Tue., 3/26 | V Boys Volleyball | Westhill (Scrim.) | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 3/26 | V Softball | St. Lukes (Scrim.) | Home - Waveny Park-Orchard Field [Directions] | 4:15 p.m. | ||
| Wed., 3/27 | V Baseball | Stamford (Scrim.) | Home - Mead Park-Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 3/27 | JV Baseball | Stamford (Scrim.) | Home - Waveny Park-Coppo Field [Directions] | 4:00 p.m. | ||
| Wed., 3/27 | V Boys Tennis | Brunswick School (Scrim.) | Home - New Canaan HS-NCHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 3/28 | V Boys Volleyball | Joel Barlow (Scrim.) | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 3/28 | JV Boys Volleyball | Joel Barlow (Scrim.) | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | ||
| Sat., 3/30 | V Baseball | Abbott Tech | Home - Mead Park-Baseball Field [Directions] | 12:00 p.m. | W 12-0 | |
| Sat., 3/30 | V Boys Lacrosse | Mamaroneck (NY) | Home - New Canaan HS-Dunning Stadium [Directions] | 1:00 p.m. | W 8-4 | |
| Sat., 3/30 | JV Boys Lacrosse | Mamaroneck (NY) | Home - New Canaan HS-Dunning Stadium [Directions] | 3:30 p.m. | ||
| Sat., 3/30 | V Boys Volleyball | CIAC Boys' Volleyball Invitational | Away - CT Volleyball Center Woodbridge | 8:00 a.m. | ||
| Sat., 3/30 | V Girls Lacrosse | Greenwich Academy (Scrim.) | Home - New Canaan HS-Dunning Stadium [Directions] | 10:00 a.m. | ||
| Sat., 3/30 | V Softball | Foran | Away - Foran HS -Danielle Kemp Memorial Field [Directions] | 11:00 a.m. | L 1-0 | |
| Sat., 3/30 | JV Softball | Foran | Away - Foran HS -Danielle Kemp Memorial Field [Directions] | 12:30 p.m. | ||
| Mon., 4/1 | V Boys Volleyball | Shelton | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | W 3-1 | |
| Mon., 4/1 | JV Boys Volleyball | Shelton | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 4/1 | V Softball | Brookfield | Home - Waveny Park-Orchard Field [Directions] | 4:30 p.m. | L 2-1 | |
| Mon., 4/1 | JV Softball | Brookfield | Home - Waveny Park-Orchard Field [Directions] | 4:00 p.m. | ||
| Tue., 4/2 | V Boys Lacrosse | Cheshire | Home - New Canaan HS-Dunning Stadium [Directions] | 6:30 p.m. | W 14-8 | |
| Tue., 4/2 | JV Boys Lacrosse | Cheshire | Home - New Canaan HS-WTT #2 [Directions] | 4:30 p.m. | ||
| Tue., 4/2 | V Boys Tennis | Fairfield Prep (Scrim.) | Home - New Canaan HS-NCHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/2 | FR Girls Lacrosse | Ridgefield | Home - New Canaan HS-WTT #1 [Directions] | 4:00 p.m. | ||
| Wed., 4/3 | V Boys Volleyball | Greenwich | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | W 3-1 | |
| Thu., 4/4 | V Boys Lacrosse | Pleasantville (NY) | Home - New Canaan HS-Dunning Stadium [Directions] | 6:30 p.m. | W 14-5 | |
| Thu., 4/4 | JV Boys Lacrosse | Pleasantville (NY) | Home - New Canaan HS-WTT #2 [Directions] | 5:00 p.m. | ||
| Thu., 4/4 | FR Boys Lacrosse | Wilton | Home - New Canaan HS-WTT #2 [Directions] | Postponed | ||
| Thu., 4/4 | JV Boys Tennis | Fairfield Warde | Away - Fairfield Warde HS-Knapps Courts [Directions] | 4:00 p.m. | ||
| Thu., 4/4 | V Boys Volleyball | Newtown | Home - New Canaan HS-Main Gym [Directions] | 4:15 p.m. | W 3-2 | |
| Thu., 4/4 | JV Boys Volleyball | Newtown | Home - New Canaan HS-Main Gym [Directions] | 5:45 p.m. | ||
| Thu., 4/4 | FR Girls Lacrosse | Wilton | Away - Wilton HS-Allen Meadow [Directions] | 3:30 p.m. | ||
| Thu., 4/4 | JV Girls Tennis | Fairfield Warde | Away - Fairfield Woods-Tennis Courts [Directions] | 4:00 p.m. | W 7-1 | |
| Fri., 4/5 | V Boys Tennis | St. Lukes (Scrim.) | Home - New Canaan HS-NCHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 4/5 | FR Girls Lacrosse | Greenwich Academy | Home - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Sat., 4/6 | V Baseball | Jonathan Law | Home - Mead Park-Baseball Field [Directions] | 2:00 p.m. | ||
| Sat., 4/6 | V Boys Lacrosse | Glastonbury | Away - Glastonbury HS-Field 1 [Directions] | 11:00 a.m. | W 7-3 | |
| Sat., 4/6 | JV Boys Lacrosse | Glastonbury | Away - Glastonbury HS-Field 11 [Directions] | 11:00 a.m. | ||
| Sat., 4/6 | V Girls Lacrosse | Westhampton Beach (NY) | Home - New Canaan HS-Dunning Stadium [Directions] | 3:00 p.m. | ||
| Mon., 4/8 | FR Baseball | Darien | Away - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | ||
| Mon., 4/8 | V Boys Tennis | Danbury | Away - Danbury HS-DHS Tennis Courts [Directions] | 5:00 p.m. | W 7-0 [Detailed Results] | |
| Mon., 4/8 | JV Boys Tennis | Greenwich | Away - Central MS [Directions] | 5:00 p.m. | ||
| Mon., 4/8 | V Girls Golf | St. Joseph | Home - CCNC [Directions] | 3:30 p.m. | ||
| Mon., 4/8 | FR Girls Lacrosse | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 4/8 | V Softball | Ridgefield | Away - Ridgefield HS-Varsity Softball Field [Directions] | 5:00 p.m. | L 1-0 | |
| Mon., 4/8 | V Girls Tennis | Danbury | Home - New Canaan HS-NCHS Tennis Courts [Directions] | 5:00 p.m. | W 7-0 [Detailed Results] | |
| Mon., 4/8 | JV Girls Tennis | Greenwich | Away - Binney Park [Directions] | 5:00 p.m. | L 7-1 | |
| Tue., 4/9 | V Baseball | Westhill | Home - Mead Park-Baseball Field [Directions] | 4:00 p.m. | ||
| Tue., 4/9 | V Boys Lacrosse | Trumbull | Home - New Canaan HS-Dunning Stadium [Directions] | 4:30 p.m. | W 16-0 | |
| Tue., 4/9 | JV Boys Lacrosse | Trumbull | Home - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Tue., 4/9 | V Boys Outdoor Track | Bridgeport Central | Home - New Canaan HS-NCHS Track [Directions] | 4:00 p.m. | ||
| Tue., 4/9 | V Boys Tennis | Staples | Home - New Canaan HS-NCHS Tennis Courts [Directions] | 4:00 p.m. | W 6-1 [Detailed Results] | |
| Tue., 4/9 | JV Boys Tennis | Staples | Away - Staples HS-Town Farms Tennis Courts [Directions] | Postponed | ||
| Tue., 4/9 | V Girls Lacrosse | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | ||
| Tue., 4/9 | JV Girls Lacrosse | Trumbull | Away - Trumbull HS-Cork Field [Directions] | 4:15 p.m. | ||
| Tue., 4/9 | V Girls Outdoor Track | Bridgeport Central | Home - New Canaan HS-NCHS Track [Directions] | 4:00 p.m. | ||
| Tue., 4/9 | V Softball | New Milford | Away - New Milford HS-Softball Varsity Field - NMHS [Directions] | 4:15 p.m. | L 0-7 | |
| Tue., 4/9 | V Girls Tennis | Staples | Away - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | W 6-1 [Detailed Results] | |
| Tue., 4/9 | JV Girls Tennis | Staples | Away - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | L 6-2 | |
| Wed., 4/10 | JV Baseball | Westhill | Home - Waveny Park-Coppo Field [Directions] | 4:00 p.m. | ||
| Wed., 4/10 | FR Baseball | Westhill | Home - New Canaan HS-Connor Field [Directions] | 4:00 p.m. | ||
| Wed., 4/10 | FR Boys Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Turf [Directions] | 4:00 p.m. | ||
| Wed., 4/10 | V Boys Outdoor Track | Wilton | Away - Wilton HS-Track [Directions] | 4:00 p.m. | ||
| Wed., 4/10 | JV Girls Golf | Darien | Away - Wee Burn CC [Directions] | 3:00 p.m. | ||
| Wed., 4/10 | FR Girls Lacrosse | Fairfield Ludlowe | Home - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Wed., 4/10 | V Girls Outdoor Track | Wilton | Away - Wilton HS-Track [Directions] | 4:00 p.m. | ||
| Wed., 4/10 | V Softball | Wilton | Home - New Canaan HS-Orchard Field [Directions] | 6:45 p.m. | W 3-1 | |
| Thu., 4/11 | V Baseball | New Fairfield | Away - New Fairfield HS-Baseball Field [Directions] | Suspended | ||
| Thu., 4/11 | JV Boys Tennis | Fairfield Ludlowe | Away - Tomlinson MS-Tennis Courts [Directions] | Postponed | ||
| Thu., 4/11 | V Girls Golf | Darien | Home - CCNC [Directions] | 3:30 p.m. | ||
| Thu., 4/11 | JV Girls Golf | Darien | Home - CCNC [Directions] | 3:30 p.m. | ||
| Thu., 4/11 | V Girls Lacrosse | Ridgefield | Home - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | ||
| Thu., 4/11 | JV Girls Lacrosse | Ridgefield | Home - New Canaan HS-Dunning Stadium [Directions] | 5:30 p.m. | ||
| Thu., 4/11 | JV Girls Tennis | Fairfield Ludlowe | Away - Dwight Elementary School-Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 4/12 | V Boys Volleyball | Darien | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 4/12 | JV Boys Volleyball | Darien | Home - New Canaan HS-Main Gym [Directions] | 6:00 p.m. | ||
| Fri., 4/12 | FR Girls Lacrosse | Norwalk | Home - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Sat., 4/13 | V Baseball | Danbury | Home - Mead Park-Baseball Field [Directions] | Rainout | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 4:00 p.m. | ||||||
| Sat., 4/13 | JV Baseball | Danbury | Home - Waveny Park-Coppo Field [Directions] | Rainout | ||
| Sat., 4/13 | V Boys Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 4:00 p.m. | W 10-9 | |
| Sat., 4/13 | JV Boys Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 2:00 p.m. | ||
| Sat., 4/13 | FR Boys Lacrosse | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 9:00 a.m. | ||
| Sat., 4/13 | V Boys Tennis | Norwalk | Away - Grassroots Tennis and Education-Grassroots Tennis Courts [Directions] | 10:00 a.m. | W 6-1 [Detailed Results] | |
| Sat., 4/13 | V Girls Lacrosse | St. Anthonys (NY) | Away - St. Anthony's HS-Stadium | 12:00 p.m. | ||
| Sat., 4/13 | JV Girls Lacrosse | St. Anthonys (NY) | Away - St. Anthony's HS (Front Field) | 1:30 p.m. | ||
| Sat., 4/13 | V Girls Tennis | Norwalk | Home - New Canaan HS-NCHS Tennis Courts [Directions] | 10:00 a.m. | W 7-0 [Detailed Results] | |
| Mon., 4/15 | V Baseball | Staples | Away - Staples HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Mon., 4/15 | JV Baseball | Staples | Away - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | ||
| Mon., 4/15 | FR Baseball | Staples | Home - New Canaan HS-Coppo Field [Directions] | 4:00 p.m. | ||
| Mon., 4/15 | FR Boys Lacrosse | Wilton | Away - Wilton HS-Fujitani Field - Turf [Directions] | 4:15 p.m. | ||
| Mon., 4/15 | V Boys Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Tennis Courts [Directions] | 11:00 a.m. | W 6-1 [Detailed Results] | |
| Mon., 4/15 | JV Boys Tennis | Fairfield Ludlowe | Away - Tomlinson MS-Tennis Courts [Directions] | Postponed | ||
| Mon., 4/15 | V Boys Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 4/15 | JV Boys Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 4/15 | V Girls Lacrosse | Rumson-Fair Haven (NJ) | Away - MM - Rumson-Fair Haven HS-Stadium | 6:00 p.m. | ||
| Mon., 4/15 | JV Girls Lacrosse | Rumson-Fair Haven (NJ) | Away - Rumson Fair Haven HS | 4:30 p.m. | ||
| Mon., 4/15 | V Softball | Staples | Home - Waveny Park-Orchard Field [Directions] | 4:00 p.m. | W 5-4 | |
| Mon., 4/15 | V Girls Tennis | Fairfield Ludlowe | Home - New Canaan HS-NCHS Tennis Courts [Directions] | 11:00 a.m. | W 4-3 [Detailed Results] | |
| Mon., 4/15 | JV Girls Tennis | Fairfield Ludlowe | Away - Dwight Elementary School-Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/16 | V Baseball | Danbury | Home - Mead Park-Baseball Field [Directions] | 11:00 a.m. | ||
| Tue., 4/16 | JV Baseball | Danbury | Home - Waveny Park-Coppo Field [Directions] | 11:00 a.m. | ||
| Tue., 4/16 | FR Baseball | Danbury | Away - Danbury HS-V Baseball Field [Directions] | 11:00 a.m. | ||
| Tue., 4/16 | V Boys Lacrosse | Seton Hall Prep (NJ) | Away - Seton Hall Prep-Tevlin Field, West Orange | 4:30 p.m. | W 12-9 | |
| Tue., 4/16 | JV Boys Lacrosse | Seton Hall Prep (NJ) | Away - Seton Hall Prep-Kelly Athletic Complex | 6:30 p.m. | ||
| Tue., 4/16 | V Boys Tennis | Fairfield Warde | Home - New Canaan HS-NCHS Tennis Courts [Directions] | 4:00 p.m. | W 6-1 [Detailed Results] | |
| Tue., 4/16 | V Softball | Danbury | Away - Danbury HS-V Softball field [Directions] | 11:00 a.m. | W 6-1 | |
| Tue., 4/16 | JV Softball | Danbury | Away - Danbury HS-JV Softball Field [Directions] | 12:45 p.m. | ||
| Tue., 4/16 | JV Softball | Staples | Home - Waveny Park-Orchard Field [Directions] | Postponed | ||
| Tue., 4/16 | V Girls Tennis | Fairfield Warde | Away - Fairfield Warde HS-Blake Courts [Directions] | 3:00 p.m. | W 7-0 [Detailed Results] | |
| Wed., 4/17 | V Baseball | Norwalk | Home - Mead Park-Baseball Field [Directions] | 2:00 p.m. | ||
| Wed., 4/17 | JV Baseball | Norwalk | Home - Waveny Park-Coppo Field [Directions] | 2:00 p.m. | ||
| Wed., 4/17 | FR Baseball | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 4:00 p.m. | ||
| Wed., 4/17 | V Boys Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Wed., 4/17 | JV Boys Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Wed., 4/17 | V Softball | Norwalk | Away - Brien McMahon HS-Softball Diamond [Directions] | 4:00 p.m. | W 3-2 | |
| Wed., 4/17 | JV Softball | Norwalk | Away - Naramake School Field [Directions] | 4:00 p.m. | ||
| Thu., 4/18 | V Boys Lacrosse | Greenwich | Home - New Canaan HS-Dunning Stadium [Directions] | 12:00 p.m. | ||
| Thu., 4/18 | JV Boys Lacrosse | Greenwich | Home - New Canaan HS-Dunning Stadium [Directions] | 3:30 p.m. | ||
| Thu., 4/18 | V Girls Lacrosse | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Thu., 4/18 | JV Girls Lacrosse | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | Postponed | ||
| Pending changes awaiting acceptance by one or more parties involved: Date to 4/30, Time to 5:00 p.m. | ||||||
| Fri., 4/19 | FR Baseball | Fairfield Ludlowe | Away - Kiwanis Field-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Fri., 4/19 | FR Boys Lacrosse | Darien | Home - New Canaan HS-Dunning Stadium [Directions] | 12:00 p.m. | ||
| Fri., 4/19 | V Boys Volleyball | Fairfield Warde | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 4/19 | JV Boys Volleyball | Fairfield Warde | Home - New Canaan HS-Main Gym [Directions] | 6:00 p.m. | ||
| Fri., 4/19 | V Softball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 2:00 p.m. | L 2-3 | |
| Fri., 4/19 | JV Softball | Fairfield Ludlowe | Away - Sturges Park (Ludlowe HS)-Softball Diamond [Directions] | 4:00 p.m. | ||
| Sat., 4/20 | V Boys Lacrosse | Rumson-Fair Haven (NJ) | Away - MM - Rumson-Fair Haven HS-Stadium | 12:00 p.m. | ||
| Mon., 4/22 | V Baseball | Fairfield Warde | Away - Fairfield Warde HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Mon., 4/22 | JV Baseball | Fairfield Warde | Away - Tunxis [Directions] | 4:00 p.m. | ||
| Mon., 4/22 | FR Baseball | Fairfield Warde | Home - New Canaan HS-Coppo Field [Directions] | 4:00 p.m. | ||
| Mon., 4/22 | FR Boys Lacrosse | Greenwich | Home - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Mon., 4/22 | V Boys Tennis | Wilton | Away - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | W 6-1 [Detailed Results] | |
| Mon., 4/22 | JV Boys Tennis | Wilton | Away - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 4/22 | V Girls Golf | Wilton | Away - Silvermine Golf Club [Directions] | 3:30 p.m. | ||
| Mon., 4/22 | JV Girls Lacrosse | Sacred Heart of Greenwich | Away - Sacred Heart Greenwich-Magnetti Turf Field | 4:30 p.m. | ||
| Mon., 4/22 | V Softball | Fairfield Warde | Home - Waveny Park-Orchard Field [Directions] | 4:00 p.m. | W 3-2 | |
| Mon., 4/22 | JV Softball | Fairfield Warde | Home - Waveny Park-Orchard Field [Directions] | 4:00 p.m. | ||
| Mon., 4/22 | V Girls Tennis | Wilton | Home - New Canaan HS-NCHS Tennis Courts [Directions] | 4:00 p.m. | W 6-1 [Detailed Results] | |
| Mon., 4/22 | JV Girls Tennis | Wilton | Away - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | W 6-2 | |
| Tue., 4/23 | V Baseball | Fairfield Ludlowe | Home - Mead Park-Baseball Field [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | JV Baseball | Fairfield Ludlowe | Home - Waveny Park-Coppo Field [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | V Boys Lacrosse | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | JV Boys Lacrosse | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | ||
| Tue., 4/23 | V Boys Outdoor Track | Ridgefield | Home - New Canaan HS-NCHS Track [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | V Boys Tennis | Stamford | Away - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Tue., 4/23 | V Boys Volleyball | Westhill | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | JV Boys Volleyball | Westhill | Home - New Canaan HS-Main Gym [Directions] | 6:00 p.m. | ||
| Tue., 4/23 | V Girls Golf | Greenwich | Home - CCNC [Directions] | 3:30 p.m. | ||
| Tue., 4/23 | JV Girls Golf | Greenwich | Home - CCNC [Directions] | 3:30 p.m. | ||
| Tue., 4/23 | V Girls Lacrosse | Westhill | Home - New Canaan HS-Dunning Stadium [Directions] | 6:00 p.m. | ||
| Tue., 4/23 | JV Girls Lacrosse | Westhill | Home - New Canaan HS-Dunning Stadium [Directions] | 4:30 p.m. | ||
| Tue., 4/23 | V Girls Outdoor Track | Ridgefield | Home - New Canaan HS-NCHS Track [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | V Girls Tennis | Stamford | Home - New Canaan HS-NCHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Wed., 4/24 | V Baseball | Greenwich | Away - Havemeyer Field-Havermeyer Field [Directions] | 4:30 p.m. | ||
| Wed., 4/24 | JV Baseball | Greenwich | Away - Julian Curtiss School [Directions] | 4:30 p.m. | ||
| Wed., 4/24 | FR Baseball | Greenwich | Home - New Canaan HS-Coppo Field [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | FR Boys Lacrosse | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | 4:30 p.m. | ||
| Wed., 4/24 | V Boys Tennis | Greenwich | Home - New Canaan HS-NCHS Tennis Courts [Directions] | 4:00 p.m. | L 3-4 [Detailed Results] | |
| Wed., 4/24 | FR Girls Lacrosse | Staples | Home - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | V Softball | Greenwich | Home - Waveny Park-Orchard Field [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | JV Softball | Greenwich | Home - Waveny Park-Orchard Field [Directions] | 4:00 p.m. | ||
| Thu., 4/25 | V Boys Lacrosse | Fairfield Prep | Away - Fairfield University-Rafferty Stadium [Directions] | 6:00 p.m. | ||
| Thu., 4/25 | JV Boys Lacrosse | Fairfield Prep | Away - Fairfield University-Barlow Field [Directions] | 4:00 p.m. | ||
| Thu., 4/25 | V Boys Tennis | Darien | Home - New Canaan HS-NCHS Tennis Courts [Directions] | 4:00 p.m. | L 3-4 [Detailed Results] | |
| Thu., 4/25 | JV Boys Tennis | Darien | Away - Cherry Lawn Park- Darien [Directions] | 4:00 p.m. | ||
| Thu., 4/25 | V Boys Volleyball | Bridgeport Central | Away - Bridgeport Central HS-The Barry McLeod Court [Directions] | 6:00 p.m. | ||
| Thu., 4/25 | JV Boys Volleyball | Bridgeport Central | Away - Bridgeport Central HS-The Barry McLeod Court [Directions] | 4:30 p.m. | ||
| Thu., 4/25 | V Girls Lacrosse | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Thu., 4/25 | JV Girls Lacrosse | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Thu., 4/25 | V Girls Tennis | Darien | Away - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 5-2 [Detailed Results] | |
| Thu., 4/25 | JV Girls Tennis | Darien | Away - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | L 6-2 | |
| Fri., 4/26 | V Baseball | Wilton | Home - Mead Park-Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 4/26 | JV Baseball | Wilton | Home - Waveny Park-Coppo Field [Directions] | 4:00 p.m. | ||
| Fri., 4/26 | FR Baseball | Wilton | Away - Allen's Meadow-Baseball Diamond [Directions] | 4:15 p.m. | ||
| Fri., 4/26 | V Boys Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 4/26 | JV Boys Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 4/26 | V Softball | Wilton | Away - Wilton HS-Varsity Softball Field [Directions] | 6:00 p.m. | ||
| Fri., 4/26 | JV Softball | Wilton | Away - Wilton HS-JV Softball Field [Directions] | 4:15 p.m. | ||
| Fri., 4/26 | V Girls Tennis | Greenwich | Away - Greenwich HS-Tennis Courts [Directions] | 4:00 p.m. | L 4-3 [Detailed Results] | |
| Sat., 4/27 | V Boys Lacrosse | Darien | Home - New Canaan HS-Dunning Stadium [Directions] | 1:30 p.m. | ||
| Sat., 4/27 | JV Boys Lacrosse | Darien | Home - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | ||
| Sat., 4/27 | V Boys Outdoor Track | O'Grady Relays | Away - Danbury HS-Danbury HS Stadium | 9:00 a.m. | ||
| Sat., 4/27 | V Boys Outdoor Track | Danbury | Away - Danbury HS-Stadium Track [Directions] | 9:00 a.m. | ||
| Sat., 4/27 | V Girls Lacrosse | Warde Melville (NY) | Away - Cold Spring Harbor HS-Major Field | 1:00 p.m. | ||
| Sat., 4/27 | V Girls Outdoor Track | Danbury | Away - Danbury HS-Stadium Track [Directions] | 9:00 a.m. | ||
| Sat., 4/27 | JV Softball | Westhill | Home - Wilton HS-JV Softball Field [Directions] | 11:00 a.m. | ||
| Sat., 4/27 | JV Softball | Norwalk | Home - Wilton HS-JV Softball Field [Directions] | 9:00 a.m. | ||
| Mon., 4/29 | V Baseball | Stamford | Home - Mead Park-Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | JV Baseball | Stamford | Home - Waveny Park-Coppo Field [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | FR Baseball | Stamford | Away - Belltown Park-Barrett Field, Belltown Park [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | V Boys Outdoor Track | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | V Boys Tennis | Brien McMahon | Home - New Canaan HS-NCHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Mon., 4/29 | V Girls Lacrosse | Rye (NY) | Away - Rye HS-Turf | 5:00 p.m. | ||
| Mon., 4/29 | JV Girls Lacrosse | Rye (NY) | Away - Rye HS-Turf | 6:30 p.m. | ||
| Mon., 4/29 | FR Girls Lacrosse | Ridgefield | Away - Scotts Ridge MS-SRMS Turf [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | V Girls Outdoor Track | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | V Softball | Stamford | Away - Troy Complex-Diamond 1 [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | JV Softball | Stamford | Away - Troy Complex-Diamond 2 [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | V Girls Tennis | Brien McMahon | Away - Brien McMahon HS-Tennis Courts [Directions] | 4:00 p.m. | W 6-1 [Detailed Results] | |
| Mon., 4/29 | JV Girls Tennis | Wilton | Away - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | L 7-1 | |
| Tue., 4/30 | V Boys Tennis | Westhill | Home - New Canaan HS-NCHS Tennis Courts [Directions] | 4:00 p.m. | W 5-2 [Detailed Results] | |
| Tue., 4/30 | JV Boys Tennis | Trumbull | Away - Tashua Knolls Golf Course-Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/30 | V Boys Volleyball | Stamford | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 4/30 | JV Boys Volleyball | Wilton | Home - New Canaan HS-Main Gym [Directions] | 6:00 p.m. | ||
| Tue., 4/30 | V Girls Golf | Danbury | Away - Richter Park Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 4/30 | V Girls Lacrosse | IMGAcademyFL | Home - New Canaan HS-Dunning Stadium [Directions] | 6:00 p.m. | ||
| Tue., 4/30 | JV Girls Lacrosse | Greenwich Academy | Home - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/30 | V Girls Tennis | Westhill | Away - Westhill HS-Westhill Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Tue., 4/30 | JV Girls Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | W 8-0 | |
| Wed., 5/1 | V Baseball | Darien | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | JV Baseball | Darien | Away - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | FR Baseball | Darien | Home - New Canaan HS-Coppo Field [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | FR Boys Lacrosse | St. Joseph | Home - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | JV Girls Golf | Darien | Away - Woodway Country Club [Directions] | 3:00 p.m. | ||
| Wed., 5/1 | FR Girls Lacrosse | Trumbull | Away - Trumbull HS-The Pit [Directions] | Postponed | ||
| Wed., 5/1 | V Softball | Darien | Home - Waveny Park-Orchard Field [Directions] | 4:00 p.m. | ||
| Thu., 5/2 | V Baseball | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 6:00 p.m. | ||
| Thu., 5/2 | JV Baseball | Brien McMahon | Away - Roton MS [Directions] | 4:00 p.m. | ||
| Thu., 5/2 | V Boys Lacrosse | Staples | Away - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Thu., 5/2 | JV Boys Lacrosse | Staples | Away - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Thu., 5/2 | V Boys Tennis | Bridgeport Central | Away - Bridgeport Central HS-Central High School Tennis Courts [Directions] | 5:00 p.m. | W 7-0 [Detailed Results] | |
| Thu., 5/2 | V Boys Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:45 p.m. | ||
| Thu., 5/2 | JV Boys Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:30 p.m. | ||
| Thu., 5/2 | V Girls Lacrosse | Staples | Home - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | ||
| Thu., 5/2 | JV Girls Lacrosse | Staples | Home - New Canaan HS-Dunning Stadium [Directions] | 5:30 p.m. | ||
| Thu., 5/2 | V Softball | Brien McMahon | Home - Waveny Park-Orchard Field [Directions] | 6:30 p.m. | ||
| Thu., 5/2 | JV Softball | Brien McMahon | Home - Waveny Park-Orchard Field [Directions] | 4:00 p.m. | ||
| Thu., 5/2 | V Girls Tennis | Bridgeport Central | Home - New Canaan HS-NCHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Fri., 5/3 | FR Girls Lacrosse | Wilton | Home - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Sat., 5/4 | V Baseball | Newtown | Home - Mead Park-Baseball Field [Directions] | 2:00 p.m. | ||
| Sat., 5/4 | JV Baseball | Newtown | Home - Waveny Park-Coppo Field [Directions] | 2:00 p.m. | ||
| Sat., 5/4 | V Boys Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 11:00 a.m. | ||
| Sat., 5/4 | JV Boys Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 12:00 p.m. | ||
| Sat., 5/4 | V Girls Lacrosse | Sacred Heart-Hempstead (NY) | Home - New Canaan HS-Dunning Stadium [Directions] | 2:00 p.m. | ||
| Sat., 5/4 | V Girls Outdoor Track | Middletown | Away - Middletown HS-MHS Stadium [Directions] | 12:00 p.m. | ||
| Mon., 5/6 | V Baseball | Westhill | Away - Cubeta Stadium [Directions] | 7:00 p.m. | ||
| Mon., 5/6 | FR Boys Lacrosse | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 5:00 p.m. | ||
| Mon., 5/6 | V Boys Tennis | St. Joseph | Away - St. Joseph HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Mon., 5/6 | JV Boys Tennis | Staples | Away - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | V Boys Volleyball | St. Joseph | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | JV Boys Volleyball | St. Joseph | Home - New Canaan HS-Main Gym [Directions] | 6:00 p.m. | ||
| Mon., 5/6 | FR Girls Lacrosse | Darien | Home - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | V Softball | Westhill | Home - Waveny Park-Orchard Field [Directions] | 6:00 p.m. | ||
| Mon., 5/6 | JV Softball | Westhill | Home - Waveny Park-Orchard Field [Directions] | Canceled | Cancelled | |
| Mon., 5/6 | V Girls Tennis | St. Joseph | Home - New Canaan HS-NCHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | JV Girls Tennis | Staples | Away - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | V Baseball | Bridgeport Central | Home - Mead Park-Baseball Field [Directions] | 4:30 p.m. | ||
| Tue., 5/7 | JV Baseball | Westhill | Away - Rippowan MS-Rippowam Baseball Field [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | FR Baseball | Westhill | Home - New Canaan HS-Coppo Field [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | V Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | JV Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 5:30 p.m. | ||
| Tue., 5/7 | V Boys Outdoor Track | St. Joseph | Home - New Canaan HS-NCHS Track [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | V Boys Tennis | Trumbull | Away - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | W 5-2 [Detailed Results] | |
| Tue., 5/7 | JV Boys Tennis | Trumbull | Away - Tashua Knolls Golf Course-Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | V Girls Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 5/7 | JV Girls Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 5/7 | V Girls Lacrosse | Fairfield Warde | Home - New Canaan HS-Dunning Stadium [Directions] | 6:00 p.m. | ||
| Tue., 5/7 | JV Girls Lacrosse | Fairfield Warde | Home - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | V Girls Outdoor Track | St. Joseph | Home - New Canaan HS-NCHS Track [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | V Softball | Bridgeport Central | Away - Bridgeport Central-Varsity Softball Field [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | JV Softball | Bridgeport Central | Away - Bridgeport Central HS-Softball Diamond 2 [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | V Girls Tennis | Trumbull | Home - New Canaan HS-NCHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | JV Girls Tennis | Trumbull | Home - New Canaan HS-NCHS Tennis Courts [Directions] | 5:30 p.m. | ||
| Wed., 5/8 | FR Boys Lacrosse | Trumbull | Away - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | JV Boys Tennis | Greenwich | Away - Eastern MS [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | V Boys Volleyball | Trumbull | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | JV Boys Volleyball | Trumbull | Home - New Canaan HS-Main Gym [Directions] | 6:00 p.m. | ||
| Wed., 5/8 | V Girls Golf | Trumbull | Home - CCNC [Directions] | 3:30 p.m. | ||
| Wed., 5/8 | JV Girls Golf | Fairfield Ludlowe | Away - Carl Dickman Par 3 [Directions] | Canceled | Cancelled | |
| Wed., 5/8 | FR Girls Lacrosse | Fairfield Warde | Home - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Thu., 5/9 | V Baseball | St. Joseph | Home - Mead Park-Baseball Field [Directions] | 4:00 p.m. | ||
| Thu., 5/9 | JV Baseball | St. Joseph | Home - Waveny Park-Coppo Field [Directions] | 4:00 p.m. | ||
| Thu., 5/9 | V Boys Lacrosse | Wilton | Home - New Canaan HS-Dunning Stadium [Directions] | 6:30 p.m. | ||
| Thu., 5/9 | JV Boys Lacrosse | Wilton | Home - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Thu., 5/9 | V Boys Tennis | Ridgefield | Home - New Canaan HS-NCHS Tennis Courts [Directions] | 4:00 p.m. | W 4-3 [Detailed Results] | |
| Thu., 5/9 | V Girls Golf | Darien | Away - Wee Burn CC [Directions] | 3:00 p.m. | ||
| Thu., 5/9 | V Girls Lacrosse | Wilton | Away - Wilton HS-Lilly Field [Directions] | 6:00 p.m. | ||
| Thu., 5/9 | JV Girls Lacrosse | Wilton | Away - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | ||
| Thu., 5/9 | V Girls Tennis | Ridgefield | Away - Ridgefield HS-RHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/9 | JV Girls Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 5/10 | FR Baseball | St. Joseph | Away - St. Joseph HS-Baseball Diamond [Directions] | Rainout | ||
| Fri., 5/10 | FR Boys Lacrosse | Greenwich | Away - Greenwich HS-Field 4 [Directions] | 4:00 p.m. | ||
| Fri., 5/10 | V Boys Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Aux Gym [Directions] | 4:00 p.m. | ||
| Fri., 5/10 | JV Boys Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Aux Gym [Directions] | 5:30 p.m. | ||
| Fri., 5/10 | JV Softball | St. Joseph | Away - St. Joseph HS-Long Hill, Admin Field [Directions] | Canceled | Cancelled | |
| Fri., 5/10 | JV Girls Tennis | Greenwich | Away - Binney Park [Directions] | Canceled | Cancelled | |
| Sat., 5/11 | V Baseball | New Fairfield | Away - New Fairfield HS-Baseball Field [Directions] | 3:00 p.m. | ||
| Sat., 5/11 | V Girls Lacrosse | Notre Dame Academy-Worcester (MA) | Home - New Canaan HS-Dunning Stadium [Directions] | 1:00 p.m. | ||
| Sat., 5/11 | V Softball | St. Joseph | Away - St. Joseph HS-Softball Diamond [Directions] | 1:00 p.m. | ||
| Mon., 5/13 | V Baseball | Trumbull | Home - Mead Park-Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | JV Baseball | Trumbull | Home - Waveny Park-Coppo Field [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | FR Baseball | Trumbull | Away - Trumbull HS-Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | V Boys Outdoor Track | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | V Boys Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 6:00 p.m. | ||
| Mon., 5/13 | V Girls Golf | Fairfield Ludlowe | Home - CCNC [Directions] | 3:30 p.m. | ||
| Mon., 5/13 | FR Girls Lacrosse | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | V Girls Outdoor Track | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | V Softball | Trumbull | Away - Trumbull HS-Varsity Softball Diamond [Directions] | 6:00 p.m. | ||
| Mon., 5/13 | JV Softball | Trumbull | Away - Trumbull HS-JV Softball Diamond [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | V Girls Tennis | Fairfield Warde | Home - New Canaan HS-NCHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | V Baseball | Ridgefield | Away - Governor Field [Directions] | 4:30 p.m. | ||
| Tue., 5/14 | JV Baseball | Ridgefield | Away - East Ridge MS-Baseball Field [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | V Boys Lacrosse | Don Bosco (NJ) | Away - Don Bosco Prep School-Stadium Turf | 6:30 p.m. | ||
| Tue., 5/14 | JV Boys Lacrosse | Don Bosco (NJ) | Away - Don Bosco Prep School-Stadium Turf | 4:30 p.m. | ||
| Tue., 5/14 | FR Boys Lacrosse | Wilton | Home - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | V Boys Tennis | Ridgefield | Home - New Canaan HS-NCHS Tennis Courts [Directions] | 4:00 p.m. | W 4-3 [Detailed Results] | |
| Tue., 5/14 | JV Boys Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | V Girls Golf | Staples | Away - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 5/14 | JV Girls Golf | Staples | Away - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 5/14 | V Softball | Ridgefield | Home - Waveny Park-Orchard Field [Directions] | 6:30 p.m. | ||
| Wed., 5/15 | FR Boys Lacrosse | Staples | Home - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | V Boys Volleyball | Norwalk | Home - New Canaan HS-Main Gym [Directions] | 6:00 p.m. | ||
| Wed., 5/15 | JV Boys Volleyball | Norwalk | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | V Girls Tennis | Darien | Home - New Canaan HS-NCRC [Directions] | 5:00 p.m. | ||
| Thu., 5/16 | JV Boys Lacrosse | Staples | Home - New Canaan HS-WTT #2 [Directions] | 4:30 p.m. | ||
| Thu., 5/16 | V Boys Tennis | Staples | Home - New Canaan HS-NCHS Tennis Courts [Directions] | 4:30 p.m. | W 4-1 [Detailed Results] | |
| Thu., 5/16 | V Girls Golf | Fairfield Warde | Away - Smith Richardson Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 5/16 | V Girls Lacrosse | Norwalk | Home - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | ||
| Thu., 5/16 | V Softball | Ridgefield | Away - Ridgefield HS-Varsity Softball Field [Directions] | 4:30 p.m. | ||
| Thu., 5/16 | JV Softball | Westhill | Away - Westhill HS-Varsity Softball Field [Directions] | Postponed | ||
| Fri., 5/17 | FR Baseball | Ridgefield | Home - Mead Park-Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 5/17 | V Boys Lacrosse | Fairfield Ludlowe | Home - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | ||
| Sat., 5/18 | V Boys Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 1:00 p.m. | ||
| Sat., 5/18 | JV Boys Volleyball | Fairfield Ludlowe, Fairfield Warde, Greenwich, Ridgefield, Shelton, Staples | Away - Fairfield Ludlowe HS-Main Gym | 8:45 a.m. | ||
| Mon., 5/20 | V Boys Tennis | Greenwich | Away - Wilton HS-Tennis Courts [Directions] | 4:30 p.m. | ||
| Mon., 5/20 | V Boys Volleyball | Ridgefield | Away - Stamford HS-Kuczo Gymnasium [Directions] | 6:30 p.m. | ||
| Mon., 5/20 | V Girls Golf | Greenwich | Away - The Milbrook Club-Millbrook Country Club [Directions] | 3:30 p.m. | ||
| Mon., 5/20 | JV Girls Golf | Greenwich | Away - The Milbrook Club-Millbrook Country Club [Directions] | 4:00 p.m. | ||
| Mon., 5/20 | V Girls Lacrosse | Greenwich | Home - Brien McMahon HS-Casagrande Field [Directions] | 5:00 p.m. | ||
| Mon., 5/20 | V Girls Tennis | Greenwich | Away - Wilton HS-Tennis Courts [Directions] | 2:00 p.m. | ||
| Tue., 5/21 | V Boys Lacrosse | Staples | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 4:30 p.m. | ||
| Tue., 5/21 | V Boys Outdoor Track | FCIAC Championship | Away - Danbury HS-Danbury HS Stadium | 4:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 2:30 p.m. | ||||||
| Tue., 5/21 | V Girls Golf | Wilton | Home - CCNC [Directions] | 3:30 p.m. | ||
| Tue., 5/21 | V Girls Outdoor Track | FCIAC Championship | Away - Danbury HS-Danbury HS Stadium | 2:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 2:30 p.m. | ||||||
| Wed., 5/22 | V Baseball | St. Joseph (Scrim.) | Away - St. Joseph HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 5/22 | V Girls Golf | Ridgefield | Away - Ridgefield Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 5/22 | V Girls Lacrosse | Darien | Home - Brien McMahon HS-Casagrande Field [Directions] | 7:00 p.m. | ||
| Wed., 5/22 | V Softball | Darien (Scrim.) | Away - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | ||
| Fri., 5/24 | V Boys Tennis | Guilford | Home - New Canaan HS-NCHS Tennis Courts [Directions] | 4:30 p.m. | ||
| Fri., 5/24 | V Softball | Westhill (Scrim.) | Home - Waveny Park-Orchard Field [Directions] | 4:00 p.m. | ||
| Sat., 5/25 | V Girls Tennis | Avon | Home - New Canaan HS-NCHS Tennis Courts [Directions] | 10:00 a.m. | ||
| Tue., 5/28 | V Baseball | Darien | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 3:30 p.m. | ||
| Tue., 5/28 | V Boys Tennis | Masuk | Home - New Canaan HS-NCHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/28 | V Girls Lacrosse | Norwich Free Academy | Home - New Canaan HS-Dunning Stadium [Directions] | 5:00 p.m. | ||
| Tue., 5/28 | V Softball | Norwich Free Academy | Away - Rec Fields-DePina 1 [Directions] | 4:00 p.m. | ||
| Tue., 5/28 | V Girls Tennis | North Haven | Home - New Canaan HS-NCHS Tennis Courts [Directions] | 2:15 p.m. | ||
| Wed., 5/29 | V Baseball | Shelton | Away - Shelton HS-Baseball Diamond - N Constitution Blvd [Directions] | 3:30 p.m. | ||
| Wed., 5/29 | V Boys Lacrosse | Bristol Coop | Home - New Canaan HS-Dunning Stadium [Directions] | 4:30 p.m. | ||
| Wed., 5/29 | V Boys Tennis | Amity | Away - Amity Regional HS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/29 | V Boys Volleyball | South Windsor | Away - South Windsor HS-Gym [Directions] | 4:30 p.m. | ||
| Wed., 5/29 | V Softball | Cheshire | Away - Cheshire HS-Softball Diamond [Directions] | 4:15 p.m. | ||
| Wed., 5/29 | V Girls Tennis | Farmington | Home - New Canaan HS-NCHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/30 | V Boys Outdoor Track | CIAC Class L Track Championships | Away - Willowbrook Park | 3:00 p.m. | ||
| Thu., 5/30 | V Boys Tennis | Wilton | Home - Joel Barlow HS-Tennis Courts [Directions] | 3:30 p.m. | ||
| Thu., 5/30 | V Girls Lacrosse | Conard | Home - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | ||
| Thu., 5/30 | V Girls Outdoor Track | CIAC Class L Track Championships | Away - Willowbrook Park | 3:00 p.m. | ||
| Thu., 5/30 | V Girls Tennis | Guilford | Away - Joel Barlow HS-Tennis Courts [Directions] | 1:00 p.m. | ||
| Fri., 5/31 | V Boys Volleyball | Farmington | Away - Farmington HS [Directions] | 5:00 p.m. | ||
| Sat., 6/1 | V Baseball | Amity | Away - Amity Regional HS-John Janenda Field [Directions] | 1:30 p.m. | ||
| Sat., 6/1 | V Boys Lacrosse | Greenwich | Home - New Canaan HS-Dunning Stadium [Directions] | 3:00 p.m. | ||
| Tue., 6/4 | V Girls Lacrosse | Wilton | Home - Fairfield University-Stadium [Directions] | 7:00 p.m. | ||
| Wed., 6/5 | V Boys Lacrosse | Darien | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Sat., 6/8 | V Girls Lacrosse | Darien | Away - Sacred Heart University-Turf Field [Directions] | 2:00 p.m. | ||