| New Canaan 2019-20 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 223 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Sat., 8/31 | V Football | TBA | Home - Conner Field, New Cannan [Directions] | 10:00 a.m. | ||
| Sat., 8/31 | FR Football | Stepinac (NY) | Away - Stepinac HS-Turf Field | 12:30 p.m. | ||
| Wed., 9/4 | V Girls Soccer | St. Lukes (Scrim.) | Away - St. Lukes | 4:00 p.m. | ||
| Thu., 9/5 | V Football | Greenwich (Scrim.) | Home - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | ||
| Fri., 9/6 | FR Football | Greenwich | Home - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | ||
| Fri., 9/6 | V Boys Soccer | St. Lukes (Scrim.) | Home - Saxe MS-Field 1 [Directions] | 5:30 p.m. | L 0-2 | |
| Fri., 9/6 | JV Boys Soccer | St. Lukes (Scrim.) | Home - Saxe MS-Field 1 [Directions] | 4:00 p.m. | ||
| Fri., 9/6 | V Girls Volleyball | St. Lukes (Scrim.) | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/7 | SO Football | Greenwich (Scrim.) | Away - Greenwich HS-Cardinal Stadium [Directions] | 10:00 a.m. | ||
| Tue., 9/10 | V Boys Cross Country | St. Joseph, Staples, Westhill | Home - Waveny Park [Directions] | 4:00 p.m. | ||
| Tue., 9/10 | V Boys Cross Country | St. Joseph | Home - Waveny Park [Directions] | 4:30 p.m. | ||
| Tue., 9/10 | V Girls Cross Country | St. Joseph, Staples, Westhill | Home - Waveny Park [Directions] | 4:00 p.m. | ||
| Tue., 9/10 | V Girls Cross Country | St. Joseph | Home - Waveny Park [Directions] | 4:00 p.m. | ||
| Wed., 9/11 | V Girls Soccer | Joel Barlow (Scrim.) | Away - Joel Barlow HS-Field J [Directions] | 4:00 p.m. | ||
| Wed., 9/11 | JV Girls Soccer | Joel Barlow (Scrim.) | Away - Joel Barlow HS-Field E (Softball) [Directions] | 4:00 p.m. | ||
| Thu., 9/12 | FR Football | Norwalk | Home - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | ||
| Thu., 9/12 | V Girls Volleyball | Greenwich Academy (Scrim.) | Away - Greenwich Academy-Gym | 4:00 p.m. | ||
| Fri., 9/13 | V Boys Soccer | Trinity Catholic | Away - Trinity Catholic-Gaglio Field | 4:00 p.m. | W 6-0 | |
| Fri., 9/13 | V Girls Volleyball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 9/13 | JV Girls Volleyball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/13 | FR Girls Volleyball | Brookfield | Away - Brookfield HS-BHS Small Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/14 | V Boys Cross Country | Wilton | Away - Wilton HS-Allen Meadow [Directions] | 9:00 a.m. | ||
| Sat., 9/14 | V Football | New London | Away - New London HS- Pat Cannamela Field [Directions] | 12:00 p.m. | W 32-6 | |
| Sat., 9/14 | V Girls Cross Country | Wilton | Away - Wilton HS-Allen Meadow [Directions] | 9:00 a.m. | ||
| Sat., 9/14 | V Girls Soccer | Trinity Catholic | Home - Conner Field, New Cannan [Directions] | 4:00 p.m. | W 6-0 | |
| Sat., 9/14 | V Girls Volleyball | Amity, Avon, Darien, East Haven, Fairfield Ludlowe, Glastonbury, Joel Barlow, New Britain, North Haven, Seymour, Simsbury, SMSA, St. Joseph, St. Paul Catholic, Suffield, Trinity Catholic, Trumbull, Woodland | Away - Connecticut Sports Center | 8:30 a.m. | ||
| Mon., 9/16 | V Boys Soccer | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 5:00 p.m. | L 0-5 | |
| Mon., 9/16 | JV Boys Soccer | Greenwich | Away - Cos Cob Park-Benvenuto Field [Directions] | 5:00 p.m. | ||
| Mon., 9/16 | FR Boys Soccer | Greenwich | Home - Saxe MS-Field 1 [Directions] | 4:00 p.m. | ||
| Mon., 9/16 | V Girls Volleyball | Trinity Catholic | Away - Trinity Catholic-Gym | 4:00 p.m. | W 3-0 | |
| Tue., 9/17 | V Boys Cross Country | Brien McMahon, Norwalk, Ridgefield | Home - Waveny Park [Directions] | 4:30 p.m. | ||
| Tue., 9/17 | V Girls Cross Country | Brien McMahon, Norwalk, Ridgefield | Home - Waveny Park [Directions] | 4:00 p.m. | ||
| Tue., 9/17 | V Girls Soccer | Greenwich | Home - New Canaan HS-Dunning Stadium [Directions] | 6:30 p.m. | W 1-0 | |
| Tue., 9/17 | JV Girls Soccer | Greenwich | Home - Saxe MS-Field 1 [Directions] | 4:00 p.m. | ||
| Tue., 9/17 | FR Girls Soccer | Greenwich | Away - Cos Cob Park-Benvenuto Field [Directions] | 4:30 p.m. | ||
| Wed., 9/18 | V Boys Soccer | Danbury | Home - Conner Field, New Cannan [Directions] | 4:00 p.m. | L 0-1 | |
| Wed., 9/18 | JV Boys Soccer | Danbury | Home - Saxe MS-Field 1 [Directions] | 4:00 p.m. | ||
| Wed., 9/18 | FR Boys Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 4:00 p.m. | ||
| Wed., 9/18 | V Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | L 3-0 | |
| Wed., 9/18 | JV Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 9/18 | FR Girls Volleyball | Greenwich | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 9/19 | FR Football | Ridgefield | Home - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | ||
| Thu., 9/19 | V Girls Soccer | Danbury | Away - Mill Ridge Int. School-Turf Field [Directions] | 4:00 p.m. | W 1-0 | |
| Thu., 9/19 | JV Girls Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 4:00 p.m. | ||
| Fri., 9/20 | V Football | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 7:00 p.m. | L 14-17 | |
| Fri., 9/20 | V Boys Soccer | Fairfield Warde | Home - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | L 0-4 | |
| Fri., 9/20 | JV Boys Soccer | Fairfield Warde | Home - Saxe MS-Field 1 [Directions] | 4:00 p.m. | ||
| Fri., 9/20 | FR Boys Soccer | Fairfield Warde | Away - Tunxis [Directions] | 4:00 p.m. | ||
| Fri., 9/20 | V Girls Volleyball | Danbury | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | W 3-1 | |
| Fri., 9/20 | JV Girls Volleyball | Danbury | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/20 | FR Girls Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/21 | V Boys Cross Country | Farmington | Away - Winding Trails-Cross Country Course [Directions] | 8:00 a.m. | ||
| Sat., 9/21 | V Girls Soccer | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 11:00 a.m. | W 2-1 | |
| Sat., 9/21 | JV Girls Soccer | Fairfield Warde | Away - Fairfield Warde HS-Varsity Grass Soccer Field [Directions] | 11:00 a.m. | ||
| Sat., 9/21 | FR Girls Soccer | Fairfield Warde | Home - Saxe MS-Field 1 [Directions] | 11:00 a.m. | ||
| Mon., 9/23 | JV Football | Ridgefield | Home - New Canaan HS-Dunning Stadium [Directions] | 5:00 p.m. | ||
| Mon., 9/23 | JV Girls Soccer | Wilton | Home - Saxe MS-Field 1 [Directions] | 4:00 p.m. | ||
| Mon., 9/23 | FR Girls Soccer | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Tue., 9/24 | V Boys Cross Country | Danbury, Trumbull, Wilton | Home - Waveny Park [Directions] | 4:00 p.m. | ||
| Tue., 9/24 | V Boys Soccer | Stamford | Away - Stamford HS-SHS Upper Soccer Field [Directions] | 4:00 p.m. | W 3-2 | |
| Tue., 9/24 | JV Boys Soccer | Stamford | Away - Rippowam MS-Upper Soccer/Footballl Field [Directions] | 4:00 p.m. | ||
| Tue., 9/24 | FR Boys Soccer | Stamford | Home - Saxe MS-Field 1 [Directions] | 4:00 p.m. | ||
| Tue., 9/24 | V Girls Cross Country | Danbury, Trumbull, Wilton | Home - Waveny Park [Directions] | 4:00 p.m. | ||
| Tue., 9/24 | V Girls Volleyball | Fairfield Warde | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | W 3-1 | |
| Tue., 9/24 | JV Girls Volleyball | Fairfield Warde | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 9/24 | FR Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:00 p.m. | ||
| Wed., 9/25 | SO Football | Greenwich | Away - Greenwich HS-Field 7 [Directions] | 5:00 p.m. | ||
| Wed., 9/25 | V Girls Soccer | Stamford | Home - Conner Field, New Cannan [Directions] | 4:00 p.m. | W 7-0 | |
| Wed., 9/25 | JV Girls Soccer | Stamford | Home - Saxe MS-Field 1 [Directions] | 4:00 p.m. | ||
| Wed., 9/25 | FR Girls Soccer | Wilton | Home - Saxe MS-Field #2 [Directions] | 6:05 p.m. | ||
| Thu., 9/26 | FR Football | Stamford | Home - New Canaan HS-Dunning Stadium [Directions] | 6:00 p.m. | ||
| Thu., 9/26 | V Girls Volleyball | Stamford | Away - Stamford HS-Kuzco Gymnasium [Directions] | 4:00 p.m. | W 3-1 | |
| Thu., 9/26 | JV Girls Volleyball | Stamford | Away - Stamford HS-Kuzco Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 9/26 | FR Girls Volleyball | Stamford | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/27 | V Boys Soccer | Wilton | Away - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | L 0-2 | |
| Fri., 9/27 | JV Boys Soccer | Wilton | Away - Allen's Meadow-2A [Directions] | 4:00 p.m. | ||
| Fri., 9/27 | FR Boys Soccer | Wilton | Home - Saxe MS-Field 1 [Directions] | 4:00 p.m. | ||
| Fri., 9/27 | V Girls Soccer | Wilton | Home - New Canaan HS-Dunning Stadium [Directions] | 6:30 p.m. | W 2-0 | |
| Fri., 9/27 | FR Girls Soccer | Wilton | Away - Allen's Meadow-3B [Directions] | 4:00 p.m. | ||
| Sat., 9/28 | V Football | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 1:00 p.m. | W 54-7 | |
| Tue., 10/1 | V Boys Soccer | Trumbull | Home - New Canaan HS-Dunning Stadium [Directions] | 6:30 p.m. | L 0-6 | |
| Tue., 10/1 | JV Boys Soccer | Trumbull | Home - Conner Field, New Cannan [Directions] | 4:00 p.m. | ||
| Tue., 10/1 | FR Boys Soccer | Trumbull | Away - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | ||
| Tue., 10/1 | FR Girls Soccer | Darien | Home - Saxe MS-Field 1 [Directions] | 4:00 p.m. | ||
| Tue., 10/1 | V Girls Volleyball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:30 p.m. | W 3-1 | |
| Tue., 10/1 | JV Girls Volleyball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Tue., 10/1 | FR Girls Volleyball | Wilton | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/2 | V Boys Cross Country | Greenwich, Darien, Stamford | Away - Greenwich Point [Directions] | 4:00 p.m. | ||
| Wed., 10/2 | V Girls Cross Country | Greenwich, Darien, Stamford | Away - Greenwich Point [Directions] | 4:00 p.m. | ||
| Wed., 10/2 | V Girls Soccer | Trumbull | Away - Trumbull HS-New Turf Field [Directions] | 5:30 p.m. | W 2-0 | |
| Wed., 10/2 | JV Girls Soccer | Trumbull | Away - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Wed., 10/2 | FR Girls Soccer | Trumbull | Home - Saxe MS-Field 1 [Directions] | 4:00 p.m. | ||
| Thu., 10/3 | FR Football | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 4:00 p.m. | ||
| Thu., 10/3 | V Boys Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 7:00 p.m. | T 2-2 | |
| Thu., 10/3 | FR Boys Soccer | Fairfield Ludlowe | Home - Saxe MS-Field 1 [Directions] | 4:00 p.m. | ||
| Thu., 10/3 | V Girls Volleyball | Trumbull | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Thu., 10/3 | JV Girls Volleyball | Trumbull | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/3 | FR Girls Volleyball | Trumbull | Away - Trumbull HS-Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/4 | V Football | St. Joseph | Home - New Canaan HS-Dunning Stadium [Directions] | 7:00 p.m. | L 14-58 | |
| Fri., 10/4 | JV Boys Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | 4:00 p.m. | ||
| Fri., 10/4 | V Girls Soccer | Fairfield Ludlowe | Home - New Canaan HS-WTT #1 [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 10/4 | JV Girls Soccer | Fairfield Ludlowe | Home - Conner Field, New Cannan [Directions] | 4:00 p.m. | ||
| Fri., 10/4 | FR Girls Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 4:00 p.m. | ||
| Sat., 10/5 | V Boys Cross Country | Brewster (NY) | Away - Brewster HS | 10:20 a.m. | ||
| Sat., 10/5 | JV Football | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 10:30 a.m. | ||
| Sat., 10/5 | V Boys Soccer | Ridgefield | Home - Conner Field, New Cannan [Directions] | 4:00 p.m. | W 1-0 | |
| Sat., 10/5 | JV Boys Soccer | Ridgefield | Home - Saxe MS-Field 1 [Directions] | 3:00 p.m. | ||
| Sat., 10/5 | FR Boys Soccer | Ridgefield | Away - Ridgefield HS-RHS Lower Grass Field [Directions] | 4:00 p.m. | ||
| Sat., 10/5 | V Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:30 p.m. | L 3-2 | |
| Sat., 10/5 | JV Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 6:00 p.m. | ||
| Sat., 10/5 | FR Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 10/7 | V Boys Cross Country | Fairfield Ludlowe, Fairfield Warde, Trinity Catholic | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | ||
| Mon., 10/7 | JV Football | Stamford | Home - New Canaan HS-WTT #1 [Directions] | 4:00 p.m. | ||
| Mon., 10/7 | V Girls Cross Country | Fairfield Ludlowe, Fairfield Warde, Trinity Catholic | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | ||
| Mon., 10/7 | V Girls Soccer | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 7:00 p.m. | T 2-2 | |
| Mon., 10/7 | JV Girls Soccer | Ridgefield | Away - Ridgefield HS-RHS Lower Grass Field [Directions] | 4:00 p.m. | ||
| Mon., 10/7 | FR Girls Soccer | Ridgefield | Home - Saxe MS-Field 1 [Directions] | 4:00 p.m. | ||
| Mon., 10/7 | V Girls Volleyball | Ridgefield | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Mon., 10/7 | JV Girls Volleyball | Ridgefield | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 10/7 | FR Girls Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/10 | V Boys Soccer | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 4:00 p.m. | T 2-2 | |
| Thu., 10/10 | JV Boys Soccer | St. Joseph | Away - St. Joseph HS-Lower Grass Field [Directions] | 4:00 p.m. | ||
| Fri., 10/11 | V Girls Soccer | St. Joseph | Home - New Canaan HS-Dunning Stadium [Directions] | 6:30 p.m. | L 1-2 | |
| Fri., 10/11 | JV Girls Soccer | St. Joseph | Home - Conner Field, New Cannan [Directions] | 4:00 p.m. | ||
| Fri., 10/11 | V Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 5:30 p.m. | W 3-2 | |
| Fri., 10/11 | JV Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/11 | FR Girls Volleyball | St. Joseph | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/12 | V Boys Soccer | Brien McMahon | Home - New Canaan HS-Dunning Stadium [Directions] | 2:30 p.m. | L 0-1 | |
| Sat., 10/12 | JV Boys Soccer | Brien McMahon | Home - Saxe MS-Field 1 [Directions] | 11:00 a.m. | ||
| Sat., 10/12 | FR Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 10:00 a.m. | ||
| Sat., 10/12 | V Girls Volleyball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 2:30 p.m. | L 3-1 | |
| Sat., 10/12 | JV Girls Volleyball | Joel Barlow | Away - Joel Barlow High-Lower Gym [Directions] | 1:00 p.m. | ||
| Mon., 10/14 | V Girls Soccer | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 6:30 p.m. | L 0-1 | |
| Mon., 10/14 | JV Girls Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 5:00 p.m. | ||
| Tue., 10/15 | V Boys Soccer | Darien | Away - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | T 1-1 | |
| Tue., 10/15 | JV Boys Soccer | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 10/15 | FR Boys Soccer | Darien | Home - Saxe MS-Field 1 [Directions] | 4:00 p.m. | ||
| Tue., 10/15 | V Girls Volleyball | Brien McMahon | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Tue., 10/15 | JV Girls Volleyball | Brien McMahon | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/16 | V Girls Soccer | Darien | Home - New Canaan HS-Dunning Stadium [Directions] | 3:00 p.m. | W 2-0 | |
| Thu., 10/17 | FR Football | Fairfield Warde | Away - Tomlinson MS-Turf Field [Directions] | 4:30 p.m. | ||
| Thu., 10/17 | V Girls Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | L 3-0 | |
| Thu., 10/17 | JV Girls Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/17 | FR Girls Volleyball | Darien | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/19 | V Football | Fairfield Warde | Home - New Canaan HS-Dunning Stadium [Directions] | 2:00 p.m. | W 28-7 | |
| Sat., 10/19 | V Boys Soccer | Westhill | Home - New Canaan HS-WTT #2 [Directions] | 12:30 p.m. | T 0-0 | |
| Sat., 10/19 | FR Boys Soccer | Westhill | Away - Westhill HS-Front Turf [Directions] | 1:00 p.m. | ||
| Mon., 10/21 | JV Football | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 5:00 p.m. | ||
| Mon., 10/21 | JV Boys Soccer | Westhill | Home - Saxe MS-Field 1 [Directions] | 4:00 p.m. | ||
| Mon., 10/21 | V Girls Soccer | Westhill | Away - Westhill HS-Front Turf [Directions] | 4:00 p.m. | W 4-0 | |
| Mon., 10/21 | JV Girls Soccer | Westhill | Away - Rippowan MS-Rippowam Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 10/21 | FR Girls Soccer | Westhill | Home - Saxe MS-Field #2 [Directions] | Canceled | Cancelled | |
| Tue., 10/22 | V Boys Cross Country | Wilton | Away - Allen's Meadow [Directions] | 4:00 p.m. | ||
| Tue., 10/22 | V Boys Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 6:00 p.m. | L 1-6 | |
| Tue., 10/22 | JV Boys Soccer | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | 5:30 p.m. | ||
| Tue., 10/22 | FR Boys Soccer | Norwalk | Home - Saxe MS-Field 1 [Directions] | 4:00 p.m. | ||
| Wed., 10/23 | V Girls Soccer | Norwalk | Home - New Canaan HS-Dunning Stadium [Directions] | 6:30 p.m. | W 8-2 | |
| Wed., 10/23 | V Girls Volleyball | Westhill | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | L 3-1 | |
| Wed., 10/23 | JV Girls Volleyball | Westhill | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/23 | FR Girls Volleyball | Westhill | Away - Westhill HS-New Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/24 | V Boys Cross Country | Danbury | Away - Tarrywile Park [Directions] | 4:00 p.m. | ||
| Thu., 10/24 | FR Football | Staples | Home - New Canaan HS-Dunning Stadium [Directions] | 7:00 p.m. | ||
| Thu., 10/24 | V Boys Soccer | Staples | Home - New Canaan HS-WTT #1 [Directions] | 4:00 p.m. | L 3-1 | |
| Thu., 10/24 | JV Boys Soccer | Staples | Home - Saxe MS-Field 1 [Directions] | 4:00 p.m. | ||
| Thu., 10/24 | FR Boys Soccer | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Thu., 10/24 | FR Girls Soccer | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 10/25 | V Football | Staples | Away - Staples HS-Staples Stadium [Directions] | 7:00 p.m. | W 41-21 | |
| Fri., 10/25 | V Girls Soccer | Staples | Away - Staples HS-Wakeman Field B (turf) [Directions] | 3:30 p.m. | L 0-1 | |
| Fri., 10/25 | JV Girls Soccer | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | 3:30 p.m. | ||
| Fri., 10/25 | FR Girls Soccer | Staples | Home - Saxe MS-Field 1 [Directions] | 4:00 p.m. | ||
| Fri., 10/25 | V Girls Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 10/25 | JV Girls Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 10/25 | FR Girls Volleyball | Norwalk | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/26 | V Boys Cross Country | CIAC Boys Class L Divisional Championship | Away - Wickham Park | 2:40 p.m. | ||
| Sat., 10/26 | V Girls Cross Country | CIAC Girls Class L Divisional Championship | Away - Wickham Park | 2:05 p.m. | ||
| Mon., 10/28 | JV Football | Staples | Home - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | ||
| Mon., 10/28 | V Boys Soccer | Bridgeport Central | Home - New Canaan HS-Dunning Stadium [Directions] | 7:00 p.m. | L 2-3 | |
| Mon., 10/28 | JV Girls Soccer | Darien | Home - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Tue., 10/29 | V Girls Soccer | Bridgeport Central | Away - Bridgeport Central HS-Kennedy Stadium [Directions] | 4:00 p.m. | W 4-0 | |
| Tue., 10/29 | V Girls Volleyball | Staples | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | W 3-1 | |
| Tue., 10/29 | JV Girls Volleyball | Staples | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/29 | FR Girls Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/30 | JV Boys Soccer | Bridgeport Central | Home - New Canaan HS-WTT #1 [Directions] | 4:00 p.m. | ||
| Thu., 10/31 | SO Football | Greenwich | Home - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | ||
| Thu., 10/31 | FR Football | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | Canceled | Cancelled | |
| Thu., 10/31 | V Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 5:30 p.m. | W 3-2 | |
| Thu., 10/31 | JV Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 11/1 | V Boys Cross Country | CIAC Boys State Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Fri., 11/1 | V Football | Brien McMahon | Home - New Canaan HS-Dunning Stadium [Directions] | 7:00 p.m. | W 42-0 | Youth Football Night |
| Fri., 11/1 | V Girls Cross Country | CIAC Girls State Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Fri., 11/1 | V Girls Soccer | Wilton | Home - New Canaan HS-WTT #1 [Directions] | 4:00 p.m. | ||
| Fri., 11/1 | V Girls Volleyball | Bridgeport Central | Home - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 11/1 | JV Girls Volleyball | Bridgeport Central | Home - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 11/2 | JV Football | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 10:30 a.m. | ||
| Mon., 11/4 | V Girls Soccer | Staples | Away - Wilton HS Varsity Field [Directions] | 5:00 p.m. | ||
| Tue., 11/5 | V Girls Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 11/6 | V Boys Soccer | Stamford (Scrim.) | Home - New Canaan HS-WTT #1 [Directions] | 3:30 p.m. | ||
| Thu., 11/7 | SO Football | Darien | Home - New Canaan HS-Dunning Stadium [Directions] | 5:00 p.m. | ||
| Fri., 11/8 | V Football | Trumbull | Home - New Canaan HS-Dunning Stadium [Directions] | 7:00 p.m. | W 48-28 | |
| Fri., 11/8 | FR Football | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 4:00 p.m. | ||
| Fri., 11/8 | V Girls Volleyball | Stamford (Scrim.) | Home - New Canaan HS-Main Gym [Directions] | 4:30 p.m. | ||
| Mon., 11/11 | JV Football | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 4:00 p.m. | ||
| Mon., 11/11 | V Girls Volleyball | Farmington | Home - New Canaan HS-Main Gym [Directions] | 5:00 p.m. | ||
| Tue., 11/12 | V Girls Soccer | Norwich Free Academy | Home - New Canaan HS-Dunning Stadium [Directions] | 5:00 p.m. | ||
| Wed., 11/13 | V Girls Volleyball | CIAC Round 2 | Home - New Canaan HS-Main Gym [Directions] | TBA | ||
| Thu., 11/14 | SO Football | Greenwich | Home - New Canaan HS-WTT #1 [Directions] | 4:00 p.m. | ||
| Thu., 11/14 | FR Football | Wilton | Away - Wilton HS-Veterans Memorial Stadium [Directions] | 6:00 p.m. | ||
| Thu., 11/14 | V Girls Soccer | Cheshire | Away - Cheshire High Main Game field [Directions] | 2:00 p.m. | ||
| Thu., 11/14 | V Girls Volleyball | Shelton | Away - Shelton HS-High School - Murray Gymnasium [Directions] | 5:00 p.m. | ||
| Fri., 11/15 | V Football | Wilton | Home - New Canaan HS-Dunning Stadium [Directions] | 7:00 p.m. | W 38-20 | |
| Sat., 11/16 | JV Football | Wilton | Away - Wilton HS-Veterans Memorial Stadium [Directions] | 10:30 a.m. | ||
| Sat., 11/16 | V Girls Soccer | Southington | Away - Southington HS-TURF FIELD [Directions] | 2:00 p.m. | ||
| Tue., 11/19 | V Girls Soccer | CIAC Semi Final | Away - Not Listed | TBA | ||
| Wed., 11/20 | V Girls Volleyball | CIAC Semi Finals | Away - Not Listed | TBA | ||
| Thu., 11/21 | SO Football | Greenwich | Home - New Canaan HS-WTT #1 [Directions] | 4:15 p.m. | ||
| Thu., 11/21 | FR Football | Darien | Home - New Canaan HS-Dunning Stadium [Directions] | 5:00 p.m. | ||
| Sat., 11/23 | JV Football | Darien | Home - New Canaan HS-Dunning Stadium [Directions] | 10:30 a.m. | ||
| Sat., 11/23 | JV Football | Darien | Home - New Canaan HS-Dunning Stadium [Directions] | 10:30 a.m. | ||
| Sat., 11/23 | V Girls Soccer | CIAC Final | Away - Not Listed | TBA | ||
| Sat., 11/23 | V Girls Volleyball | CIAC Finals | Away - TBA | TBA | ||
| Thu., 11/28 | V Football | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 10:00 a.m. | W 20-0 | |
| Wed., 12/4 | V Football | Wethersfield | Home - New Canaan HS-Dunning Stadium [Directions] | 6:30 p.m. | ||
| Mon., 12/9 | V Football | St. Joseph | Away - Bunnell HS-Bunnell Turf Field [Directions] | 6:30 p.m. | ||