| New Canaan 2015-16 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 950 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| TBA | FR Baseball | New Milford | Away - New Milford HS [Directions] | 4:15 p.m. | ||
| TBA | JV Boys Ice Hockey | Darien (Scrim.) | Home - Darien Ice Rink [Directions] | Cancelled | ||
| TBA | JV Boys Ice Hockey | Notre Dame-Fairfield | Away - Milford Ice Pavilion [Directions] | TBA | 4:00pm | |
| TBA | JV Boys Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | Cancelled | 3:30pm | |
| TBA | V Boys Swimming and Diving | Danbury | Away - O'Neil Center @ Western Connecticut State University [Directions] | Cancelled | 11:15am | |
| TBA | JV Boys Tennis | Fairfield Warde | Away - FWHS Knapps Courts [Directions] | 4:30 p.m. | 3:30pm | |
| TBA | JV Boys Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | TBA | 2:20pm | |
| TBA | FR Girls Soccer | Greenwich | Away - GHS Field 3 [Directions] | TBA | 2:30pm | |
| TBA | JV Girls Tennis | Greenwich | Away - Binney Park [Directions] | 4:00 p.m. | 2:20pm | |
| TBA | JV Girls Tennis | Darien | Away - Weed Beach [Directions] | 4:00 p.m. | ||
| Mon., 8/31 | V Field Hockey | Mamaroneck (NY) (Scrim.) | Away | 5:30 p.m. | 3:30pm | |
| Mon., 8/31 | JV Field Hockey | Mamaroneck (NY) (Scrim.) | Away | 6:30 p.m. | 4:30pm | |
| Mon., 8/31 | Miscellaneous Events | Football Scrimmage vs Daniel Hand | Away - Surf Club | 6:00 p.m. | 3:30pm | |
| Wed., 9/2 | V Boys Soccer | Rye (NY) (Scrim.) | Away | 3:45 p.m. | 2:15pm | |
| Wed., 9/2 | JV Boys Soccer | Staples (Scrim.) | Home - Saxe MS Field [Directions] | 4:00 p.m. | ||
| Thu., 9/3 | JV Field Hockey | St. Lukes (Scrim.) | Away | W 4-0 | 3:15pm | |
| Thu., 9/3 | V Girls Soccer | Masuk (Scrim.) | Home - Conner Field [Directions] | 4:00 p.m. | ||
| Thu., 9/3 | JV Girls Soccer | Masuk (Scrim.) | Home - Saxe MS Field [Directions] | 4:00 p.m. | ||
| Thu., 9/3 | V Girls Volleyball | Staples Jamboree | Away | 3:30 p.m. | 2:30pm | |
| Sat., 9/5 | JV Football | Stepinac (NY) (Scrim.) | Away | 9:00 a.m. | 7:30am | |
| Sat., 9/5 | JV Football | Stepinac (NY) (Scrim.) | Away | 9:00 a.m. | 7:30am | |
| Sat., 9/5 | FR Football | Stepinac (NY) (Scrim.) | Away | 12:30 p.m. | 2@10:00am | |
| Sat., 9/5 | V Field Hockey | New Fairfield Jamboree | Away | 8:30 a.m. | 7:00am | |
| Tue., 9/8 | V Boys Soccer | Weston (Scrim.) | Home - Conner Field [Directions] | 4:00 p.m. | ||
| Tue., 9/8 | FR Girls Soccer | St. Lukes (Scrim.) | Home - Saxe MS Field [Directions] | W 2-0 | ||
| Wed., 9/9 | V Field Hockey | Stamford (Scrim.) | Home - NCHS Water Tower Turf Field [Directions] | Cancelled | ||
| Thu., 9/10 | V Girls Soccer | Shelton (Scrim.) | Home - Conner Field [Directions] | 4:00 p.m. | ||
| Thu., 9/10 | JV Girls Soccer | St. Lukes (Scrim.) | Home - Saxe MS Field [Directions] | 4:15 p.m. | ||
| Thu., 9/10 | JV Girls Soccer | St. Lukes (Scrim.) | Home - Saxe MS Field [Directions] | 4:15 p.m. | ||
| Fri., 9/11 | V Boys Soccer | Stamford | Away - Stamford High Soccer Field [Directions] | L 2-3 | 2:30pm | |
| Fri., 9/11 | JV Boys Soccer | Stamford | Away - Rippowam Field [Directions] | L 3-1 | 2:30pm | |
| Fri., 9/11 | FR Boys Soccer | Stamford | Home - Saxe MS Field [Directions] | 4:00 p.m. | ||
| Fri., 9/11 | V Field Hockey | Brien McMahon | Home - Dunning Stadium [Directions] | W 7-0 | ||
| Fri., 9/11 | JV Field Hockey | Brien McMahon | Home - Dunning Stadium [Directions] | W 4-0 | ||
| Fri., 9/11 | V Girls Volleyball | Brien McMahon | Away [Directions] | L 0-3 | 3:00pmVar & JV ride together | |
| Fri., 9/11 | JV Girls Volleyball | Brien McMahon | Away [Directions] | W 21 | 3:00pmVar & JV ride together | |
| Sat., 9/12 | V Football | Canterbury (Scrim.) | Home - Dunning Stadium [Directions] | 5:00 p.m. | ||
| Sat., 9/12 | SO Football | Greenwich (Scrim.) | Away - Cardinal Stadium [Directions] | W 10-8 | 8:30am | |
| Sat., 9/12 | V Girls Soccer | Stamford | Home - Conner Field [Directions] | W 4-0 | ||
| Sat., 9/12 | JV Girls Soccer | Stamford | Home - Saxe MS Field [Directions] | 4:00 p.m. | ||
| Sat., 9/12 | V Girls Volleyball | Wilton | Home - NCHS Gymnasium [Directions] | W 3-0 | ||
| Sat., 9/12 | JV Girls Volleyball | Wilton | Home - NCHS Gymnasium [Directions] | W 21 | ||
| Sat., 9/12 | FR Girls Volleyball | Wilton | Home - NCHS Gymnasium [Directions] | L 1-3 | ||
| Tue., 9/15 | V Boys Soccer | Brien McMahon | Home - Conner Field [Directions] | L 1-2 | ||
| Tue., 9/15 | JV Boys Soccer | Brien McMahon | Home - Saxe MS Field [Directions] | L 0-1 | ||
| Tue., 9/15 | V Field Hockey | Ridgefield | Home - Dunning Stadium [Directions] | W 4-2 | ||
| Tue., 9/15 | JV Field Hockey | Ridgefield | Home - Dunning Stadium [Directions] | L 2-0 | ||
| Tue., 9/15 | V Girls Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | W 2-0 | 2:15pm | |
| Tue., 9/15 | FR Girls Soccer | Staples | Away - Wakeman Field E (grass) [Directions] | T 1-1 | 2:30pm | |
| Wed., 9/16 | V Boys Cross Country | Trinity Catholic, Stamford, Trumbull, Brien McMahon | Home - Waveny Park [Directions] | 4:00 p.m. | ||
| Wed., 9/16 | V Girls Cross Country | Trinity Catholic, Stamford, Trumbull, Brien McMahon | Home - Waveny Park [Directions] | 4:00 p.m. | ||
| Wed., 9/16 | FR Field Hockey | Ridgefield | Away - RHS Upper Grass Field [Directions] | 4:00 p.m. | 2:15pm | |
| Wed., 9/16 | V Girls Swimming and Diving | Wilton | Away - Wilton YMCA [Directions] | 4:00 p.m. | 2:05pm | |
| Thu., 9/17 | FR Football | Ridgefield | Home - Dunning Stadium [Directions] | W 32-7 | ||
| Thu., 9/17 | V Boys Soccer | Darien | Away - DHS Turf #2 [Directions] | T 1-1 | 2:45pm | |
| Thu., 9/17 | JV Boys Soccer | Darien | Away - Middlesex Upper Field [Directions] | L 1-3 | 2:45pm | |
| Thu., 9/17 | FR Boys Soccer | Darien | Home - Saxe MS Field [Directions] | 4:00 p.m. | ||
| Fri., 9/18 | V Football | Ridgefield | Away - Tiger Hollow Stadium [Directions] | W 45-17 | 4:00pm -2 buses / 5:30pm - Cheer bus | |
| Fri., 9/18 | V Boys Soccer | Trinity Catholic | Home - Dunning Stadium [Directions] | W 3-0 | ||
| Fri., 9/18 | V Field Hockey | Norwalk | Away - Testa Field, NHS [Directions] | W 2-0 | 6:00pm | |
| Fri., 9/18 | JV Field Hockey | Norwalk | Away - Testa Field, NHS [Directions] | W 3-0 | 4:30pm | |
| Fri., 9/18 | FR Field Hockey | Norwalk | Home - NCHS Water Tower Turf Field [Directions] | 3:45 p.m. | ||
| Fri., 9/18 | V Girls Soccer | Darien | Home - Conner Field [Directions] | W 1-0 | ||
| Fri., 9/18 | JV Girls Soccer | Darien | Home - Saxe MS Field [Directions] | 4:00 p.m. | ||
| Fri., 9/18 | FR Girls Soccer | Darien | Away - Middlesex Lower Field [Directions] | L 2-3 | 2:50pm | |
| Fri., 9/18 | V Girls Volleyball | Westhill | Away - Westhill - Main Gymnasium [Directions] | W 3-0 | 2:45pm Var & JV ride together | |
| Fri., 9/18 | JV Girls Volleyball | Westhill | Away [Directions] | W 21 | 2:45pm Var & JV ride together | |
| Sat., 9/19 | V Boys Cross Country | Wilton Invitational | Away | 9:30 a.m. | 7:30am | |
| Sat., 9/19 | JV Football | Ridgefield | Away - Tiger Hollow Stadium [Directions] | L 13-21 | 2@9:00am | |
| Sat., 9/19 | V Girls Cross Country | Wilton Invitational | Away | 9:30 a.m. | 7:30am | |
| Sat., 9/19 | V Girls Swimming and Diving | JV Meet at Trumbull | Away | 9:30 a.m. | 8:00am | |
| Mon., 9/21 | V Girls Soccer | Trinity Catholic | Home - Conner Field [Directions] | W 6-0 | ||
| Mon., 9/21 | V Girls Swimming and Diving | Fairfield Ludlowe | Home - New Canaan YMCA [Directions] | 3:00 p.m. | ||
| Mon., 9/21 | V Girls Volleyball | Stamford | Away - Stamford HS [Directions] | L 2-3 | 2:45pm Var & JV ride together | |
| Mon., 9/21 | JV Girls Volleyball | Stamford | Away - Stamford HS [Directions] | W 21 | 2:45pm Var & JV ride together | |
| Mon., 9/21 | FR Girls Volleyball | Stamford | Home - NCHS Gymnasium [Directions] | L 1-3 | ||
| Tue., 9/22 | V Boys Cross Country | St. Joseph, Wilton, Ridgefield, Trinity Catholic | Away - St. Joseph HS [Directions] | 4:00 p.m. | 2:20pm | |
| Tue., 9/22 | V Boys Soccer | Trumbull | Home - Conner Field [Directions] | W 3-0 | ||
| Tue., 9/22 | JV Boys Soccer | Trumbull | Home - Saxe MS Field [Directions] | L 1-3 | ||
| Tue., 9/22 | FR Boys Soccer | Trumbull | Away - Varsity Grass Field [Directions] | 3:00 p.m. | 1:15pm | |
| Tue., 9/22 | V Girls Cross Country | St. Joseph, Wilton, Ridgefield, Trinity Catholic | Away [Directions] | 4:00 p.m. | 2:20pm | |
| Tue., 9/22 | V Field Hockey | Darien | Home - Dunning Stadium [Directions] | L 0-4 | ||
| Tue., 9/22 | FR Field Hockey | Darien | Away - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | 2:30pm | |
| Thu., 9/24 | SO Football | Staples | Home - Dunning Stadium [Directions] | Cancelled | ||
| Thu., 9/24 | FR Football | Bridgeport Central | Away - Kennedy Stadium [Directions] | W 36-0 | 2@2:15pm | |
| Thu., 9/24 | FR Boys Soccer | Joel Barlow | Home - Saxe MS Field [Directions] | 4:00 p.m. | ||
| Thu., 9/24 | V Field Hockey | Staples | Away - Ginny Parker Field - Staples [Directions] | T 3-3 | 2:15pm | |
| Thu., 9/24 | JV Field Hockey | Staples | Away - Ginny Parker Field - Staples [Directions] | W 1-0 | 4:00pm | |
| Thu., 9/24 | FR Field Hockey | Staples | Home - NCHS Water Tower Turf Field [Directions] | 3:30 p.m. | ||
| Thu., 9/24 | V Girls Soccer | Trumbull | Away - McDougall Stadium [Directions] | L 2-0 | 2:15pm | |
| Thu., 9/24 | JV Girls Soccer | Trumbull | Away - The Pit [Directions] | 4:00 p.m. | 2:15pm | |
| Thu., 9/24 | FR Girls Soccer | Trumbull | Home - Saxe MS Field [Directions] | W 3-2 | ||
| Thu., 9/24 | V Girls Swimming and Diving | Danbury | Away - O'Neil Center @ Western Connecticut State University [Directions] | 4:00 p.m. | 2:05pm | |
| Fri., 9/25 | V Boys Soccer | Westhill | Home - Conner Field [Directions] | T 2-2 | ||
| Fri., 9/25 | JV Boys Soccer | Westhill | Home - Saxe MS Field [Directions] | L 0-2 | ||
| Fri., 9/25 | V Girls Soccer | Westhill | Away - Westhill Front Turf Field [Directions] | L 1-3 | 2:15pm | |
| Fri., 9/25 | JV Girls Soccer | Westhill | Away - Westhill Front Turf Field [Directions] | 5:30 p.m. | 4:00pm | |
| Fri., 9/25 | V Girls Volleyball | Brien McMahon | Home - NCHS Gymnasium [Directions] | L 0-3 | ||
| Fri., 9/25 | JV Girls Volleyball | Brien McMahon | Home - NCHS Gymnasium [Directions] | W 2-0 | ||
| Sat., 9/26 | V Football | Bridgeport Central | Home - Dunning Stadium [Directions] | W 53-8 | Homecoming | |
| Sat., 9/26 | V Field Hockey | Cheshire | Away - Cheshire High Main Game field [Directions] | W 2-0 | 7:15am | |
| Mon., 9/28 | JV Football | Bridgeport Central | Home - Dunning Stadium [Directions] | Cancelled | ||
| Mon., 9/28 | V Boys Soccer | Norwalk | Away - Testa Field, NHS [Directions] | L 0-2 | 5:30pm | |
| Mon., 9/28 | JV Boys Soccer | Norwalk | Away - Nathan Hale M.S. Lower [Directions] | L 5-0 | 2:45pm | |
| Mon., 9/28 | FR Boys Soccer | Norwalk | Home - Saxe MS Field [Directions] | 4:00 p.m. | Red Team | |
| Mon., 9/28 | V Field Hockey | Danbury | Home - Dunning Stadium [Directions] | W 6-2 | ||
| Mon., 9/28 | JV Field Hockey | Danbury | Home - Dunning Stadium [Directions] | W 3-0 | ||
| Mon., 9/28 | FR Field Hockey | Darien | Away - DHS Baseball Varsity Field [Directions] | 4:15 p.m. | 3:00pm | |
| Mon., 9/28 | V Girls Volleyball | Darien | Away - DHS Main Gym [Directions] | L 0-3 | 2:45pm Var & JV ride together | |
| Mon., 9/28 | JV Girls Volleyball | Darien | Away - DHS Main Gym [Directions] | L 2-0 | 2:45pm Var & JV ride together | |
| Mon., 9/28 | FR Girls Volleyball | Darien | Home - NCHS Gymnasium [Directions] | L 0-3 | ||
| Tue., 9/29 | V Boys Cross Country | Trinity Catholic, Staples, Fairfield Warde, Fairfield Ludlowe | Home - Waveny Park [Directions] | 4:00 p.m. | ||
| Tue., 9/29 | V Girls Cross Country | Trinity Catholic, Staples, Fairfield Warde, Fairfield Ludlowe | Home - Waveny Park [Directions] | 4:00 p.m. | ||
| Tue., 9/29 | V Girls Soccer | Norwalk | Home - Dunning Stadium [Directions] | W 1-0 | ||
| Tue., 9/29 | JV Girls Soccer | Norwalk | Home - Saxe MS Field [Directions] | 4:00 p.m. | ||
| Tue., 9/29 | V Girls Swimming and Diving | Greenwich | Home - New Canaan YMCA [Directions] | 3:00 p.m. | ||
| Wed., 9/30 | V Boys Soccer | Fairfield Ludlowe | Away - Taft Field [Directions] | L 0-1 | 3:00pm | |
| Wed., 9/30 | FR Boys Soccer | Fairfield Ludlowe | Home - Saxe MS Field [Directions] | 4:00 p.m. | Red Team | |
| Wed., 9/30 | V Field Hockey | Stamford | Away - Stamford HS [Directions] | W 2-0 | 2:15pm | |
| Wed., 9/30 | JV Field Hockey | Stamford | Away - Stamford HS [Directions] | W 4-1 | 4:30pm | |
| Wed., 9/30 | V Girls Volleyball | Trinity Catholic | Home - New Canaan HS [Directions] | L 1-3 | ||
| Wed., 9/30 | JV Girls Volleyball | Trinity Catholic | Home - New Canaan HS [Directions] | W 2-1 | ||
| Thu., 10/1 | FR Football | Westhill | Away - Rippowam Turf Field [Directions] | W 36-15 | 2@2:45pm | |
| Thu., 10/1 | V Girls Soccer | Fairfield Ludlowe | Home - Dunning Stadium [Directions] | L 0-3 | ||
| Thu., 10/1 | JV Girls Soccer | Fairfield Ludlowe | Home - Saxe MS Field [Directions] | 4:00 p.m. | ||
| Thu., 10/1 | FR Girls Soccer | Fairfield Ludlowe | Away - Sturges Park [Directions] | L 1-2 | 2:30pm | |
| Thu., 10/1 | V Girls Swimming and Diving | Darien | Home - New Canaan YMCA [Directions] | 3:00 p.m. | ||
| Fri., 10/2 | V Girls Volleyball | Trumbull | Home - NCHS Gymnasium [Directions] | L 1-3 | ||
| Fri., 10/2 | JV Girls Volleyball | Trumbull | Home - NCHS Gymnasium [Directions] | L 1-2 | ||
| Fri., 10/2 | FR Girls Volleyball | Trumbull | Away - THS Main Gym [Directions] | L 0-3 | 2:30pm | |
| Fri., 10/2 | FR Girls Volleyball | Westhill | Away - Westhill - New Gymnasium [Directions] | W 3-2 | 2:30pm | |
| Sat., 10/3 | V Boys Cross Country | Brewster Invitational | Away - Brewster high School, NY | 10:00 a.m. | 8:00am | |
| Sat., 10/3 | V Girls Cross Country | Brewster Invitational | Away - Brewster HS, NY | 10:00 a.m. | 8:00am | |
| Mon., 10/5 | V Football | Westhill | Home - Dunning Stadium [Directions] | W 55-12 | ||
| Mon., 10/5 | JV Football | Westhill | Home - Dunning Stadium [Directions] | Cancelled | ||
| Mon., 10/5 | V Boys Soccer | Ridgefield | Home - Conner Field [Directions] | L 2-3 | ||
| Mon., 10/5 | JV Boys Soccer | Ridgefield | Home - Saxe MS Field [Directions] | L 0-3 | ||
| Mon., 10/5 | FR Boys Soccer | King and Low-Heywood Thomas | Away | 4:00 p.m. | 2:30pm | Black Team |
| Mon., 10/5 | V Girls Soccer | Ridgefield | Away - Tiger Hollow Stadium [Directions] | L 0-4 | 4:00pm | |
| Mon., 10/5 | JV Girls Soccer | Ridgefield | Away - RHS Lower Grass Field [Directions] | 4:00 p.m. | 2:15pm | |
| Mon., 10/5 | FR Girls Soccer | Ridgefield | Home - Saxe MS Field [Directions] | L 1-2 | ||
| Mon., 10/5 | V Girls Volleyball | Westhill | Home - NCHS Gymnasium [Directions] | W 3-1 | ||
| Mon., 10/5 | JV Girls Volleyball | Westhill | Home - NCHS Gymnasium [Directions] | W 2-0 | ||
| Mon., 10/5 | FR Girls Volleyball | Westhill | Away - Westhill - New Gymnasium [Directions] | L 0-3 | 2:45pm | |
| Tue., 10/6 | V Boys Cross Country | Greenwich, Danbury, Darien, Trinity Catholic | Away - Greenwich Point [Directions] | 4:00 p.m. | 2:20pm | |
| Tue., 10/6 | V Boys Soccer | Fairfield Warde | Home - Conner Field [Directions] | T 0-0 | ||
| Tue., 10/6 | JV Boys Soccer | Fairfield Warde | Home - Saxe MS Field [Directions] | W 1-0 | ||
| Tue., 10/6 | FR Boys Soccer | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | 2:15pm | Red Team |
| Tue., 10/6 | V Girls Cross Country | Greenwich, Danbury, Darien, Trinity Catholic | Away - Greenwich Point [Directions] | 4:00 p.m. | 2:20pm | |
| Tue., 10/6 | V Field Hockey | Fairfield Ludlowe | Home - Dunning Stadium [Directions] | W 3-0 | ||
| Tue., 10/6 | JV Field Hockey | Fairfield Ludlowe | Home - Dunning Stadium [Directions] | W 3-0 | ||
| Tue., 10/6 | FR Field Hockey | Fairfield Ludlowe | Away - FLHS Front Field [Directions] | 4:00 p.m. | 2:15pm | |
| Wed., 10/7 | V Girls Soccer | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | L 0-3 | 4:45pm | |
| Wed., 10/7 | JV Girls Soccer | Fairfield Warde | Away - Fairfield Warde Grass Soccer Field [Directions] | 5:00 p.m. | 3:15pm | |
| Wed., 10/7 | FR Girls Soccer | Fairfield Warde | Home - Saxe MS Field [Directions] | L 0-3 | ||
| Wed., 10/7 | V Girls Swimming and Diving | Norwalk/McMahon | Away - Norwalk High Pool [Directions] | 3:15 p.m. | 2:05pm | |
| Wed., 10/7 | V Girls Volleyball | Norwalk | Away - Norwalk High Gym [Directions] | W 3-1 | 2:45pm Var & JV ride together | |
| Wed., 10/7 | JV Girls Volleyball | Norwalk | Away - Norwalk High Gym [Directions] | W 2-0 | 2:45pm Var & JV ride together | |
| Wed., 10/7 | Miscellaneous Events | Math Team | Away - Wilton HS | 3:00 p.m. | 2:15pm | |
| Thu., 10/8 | SO Football | Fairfield Ludlowe | Home - Dunning Stadium [Directions] | W 40-0 | ||
| Thu., 10/8 | FR Boys Soccer | Ridgefield | Away - RHS Lower Grass Field [Directions] | 4:00 p.m. | 2:15pm | Black Team |
| Thu., 10/8 | V Field Hockey | Trumbull | Away - McDougall Stadium [Directions] | L 1-0 | 4:15pm | |
| Thu., 10/8 | JV Field Hockey | Trumbull | Away - McDougall Stadium [Directions] | W 3-1 | 3:15pm | |
| Thu., 10/8 | FR Field Hockey | Trumbull | Home - NCHS Water Tower Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 10/8 | FR Girls Volleyball | New Canaan Country Day | Away | L 0-2 | 3:00pm | |
| Fri., 10/9 | V Girls Swimming and Diving | St. Joseph | Home - New Canaan YMCA [Directions] | 3:00 p.m. | ||
| Fri., 10/9 | V Girls Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | L 0-3 | 2:45pm Var & JV ride together | |
| Fri., 10/9 | JV Girls Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | L 2-0 | 2:45pm Var & JV ride together | |
| Fri., 10/9 | FR Girls Volleyball | Fairfield Ludlowe | Home - NCHS Gymnasium [Directions] | L 0-3 | ||
| Sat., 10/10 | V Boys Cross Country | Wickham Invitational | Away | 10:20 a.m. | 8:00am | |
| Sat., 10/10 | V Field Hockey | Westhill | Away - Westhill Front Turf Field [Directions] | W 4-0 | 1:15pm | |
| Sat., 10/10 | JV Field Hockey | Westhill | Away - Westhill Front Turf Field [Directions] | W 3-0 | 3:30pm | |
| Sat., 10/10 | FR Field Hockey | Westhill | Home - NCHS Track Field [Directions] | Cancelled | ||
| Mon., 10/12 | V Boys Soccer | Staples | Home - Conner Field [Directions] | T 0-0 | ||
| Mon., 10/12 | JV Boys Soccer | Staples | Home - Saxe MS Field [Directions] | L 5-1 | ||
| Mon., 10/12 | FR Boys Soccer | Staples | Away - Wakeman Field B (turf) [Directions] | 4:00 p.m. | 2:15pm | Red Team |
| Mon., 10/12 | V Girls Swimming and Diving | JV Meet at Greenwich | Away | 6:00 p.m. | 4:30pm | |
| Tue., 10/13 | V Boys Cross Country | Trinity Catholic, Westhill, Norwalk, Bridgeport Central | Home - Waveny Park [Directions] | 4:00 p.m. | ||
| Tue., 10/13 | V Girls Cross Country | Trinity Catholic, Westhill, Norwalk, Bridgeport Central | Home - Waveny Park [Directions] | 4:00 p.m. | ||
| Tue., 10/13 | V Girls Soccer | Staples | Away - Loeffler Field - Staples HS [Directions] | L 1-4 | 2:15pm Var & JV Ride Together | |
| Tue., 10/13 | JV Girls Soccer | Staples | Away - Wakeman Field E (grass) [Directions] | 4:00 p.m. | 2:15pm Var & JV Ride Together | |
| Tue., 10/13 | FR Girls Soccer | Staples | Home - Saxe MS Field [Directions] | W 1-0 | ||
| Tue., 10/13 | V Girls Volleyball | Ridgefield | Home - NCHS Gymnasium [Directions] | L 0-3 | ||
| Tue., 10/13 | JV Girls Volleyball | Ridgefield | Home - NCHS Gymnasium [Directions] | W 2-0 | ||
| Tue., 10/13 | FR Girls Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | L 1-3 | 2:30pm | |
| Wed., 10/14 | V Boys Soccer | St. Joseph | Away - St. Joseph HS [Directions] | W 2-1 | 2:15pm | |
| Wed., 10/14 | JV Boys Soccer | St. Joseph | Away - St. Catherines, Trumbull, CT [Directions] | W 2-1 | 2:15pm | |
| Wed., 10/14 | V Field Hockey | Greenwich | Away - Cardinal Stadium [Directions] | L 0-1 | 2:15pm | |
| Wed., 10/14 | JV Field Hockey | Greenwich | Away - Cardinal Stadium [Directions] | W 1-0 | 4:00pm | |
| Wed., 10/14 | FR Field Hockey | Greenwich | Home - NCHS Water Tower Turf Field [Directions] | 3:30 p.m. | ||
| Wed., 10/14 | V Girls Swimming and Diving | Fairfield Warde | Home - New Canaan YMCA [Directions] | 3:00 p.m. | ||
| Wed., 10/14 | V Girls Volleyball | Fairfield Warde | Home [Directions] | L 0-3 | ||
| Wed., 10/14 | JV Girls Volleyball | Fairfield Warde | Home - NCHS Gymnasium [Directions] | W 2-0 | ||
| Wed., 10/14 | FR Girls Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | L 0-3 | 2:30pm | |
| Thu., 10/15 | SO Football | Darien (Scrim.) | Away - DHS Baseball JV Field [Directions] | L 24-34 | 2:30pm | |
| Thu., 10/15 | FR Football | Danbury | Home - Dunning Stadium [Directions] | W 45-12 | ||
| Thu., 10/15 | V Girls Soccer | St. Joseph | Home - Conner Field [Directions] | L 2-6 | ||
| Thu., 10/15 | JV Girls Soccer | St. Joseph | Home - Saxe MS Field [Directions] | 4:00 p.m. | ||
| Fri., 10/16 | V Boys Soccer | Bridgeport Central | Home - Conner Field [Directions] | T 2-2 | ||
| Fri., 10/16 | JV Boys Soccer | Bridgeport Central | Home - Saxe MS Field [Directions] | T 0-0 | ||
| Fri., 10/16 | V Field Hockey | Wilton | Home - Dunning Stadium [Directions] | W 2-1 | ||
| Fri., 10/16 | JV Field Hockey | Wilton | Home - Dunning Stadium [Directions] | L 3-0 | ||
| Fri., 10/16 | FR Field Hockey | Wilton | Away - Wilton HS - Grass Field [Directions] | 4:00 p.m. | 2:30pm | |
| Sat., 10/17 | V Football | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | W 48-7 | 10:30am - 2 buses; 12:00pm - cheer | |
| Sat., 10/17 | FR Boys Soccer | Greenwich Country Day | Away | 9:00 a.m. | 7:15am | Black Team |
| Sat., 10/17 | FR Field Hockey | Greenwich Country Day | Away | 12:00 p.m. | 10:30am | |
| Sat., 10/17 | V Girls Soccer | Bridgeport Central | Away - Kennedy Stadium [Directions] | W 7-0 | 2:15pm | |
| Sat., 10/17 | FR Girls Soccer | Greenwich Country Day | Away | W 1-0 | 10:15pm | |
| Mon., 10/19 | JV Football | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | W 28-20 | 4:00pm | |
| Mon., 10/19 | V Boys Soccer | Wilton | Away - Lilly Field - Turf [Directions] | L 1-2 | 5:00pm | |
| Mon., 10/19 | JV Boys Soccer | Wilton | Away - Allen's Field [Directions] | L 1-0 | 2:45pm | |
| Mon., 10/19 | FR Boys Soccer | Wilton | Home - Saxe MS Field [Directions] | 4:30 p.m. | Red Team | |
| Mon., 10/19 | V Field Hockey | St. Joseph | Away - St. Joseph HS [Directions] | W 6-0 | 2:15pm | |
| Mon., 10/19 | JV Field Hockey | St. Joseph | Away - St. Catherines, Trumbull, CT [Directions] | W 3-0 | 2:15pm | |
| Mon., 10/19 | V Girls Volleyball | Staples | Home [Directions] | L 1-3 | ||
| Mon., 10/19 | JV Girls Volleyball | Staples | Home - NCHS Gymnasium [Directions] | W 2-1 | ||
| Mon., 10/19 | FR Girls Volleyball | Staples | Away - Staples H.S. Gym [Directions] | L 2-3 | 2:30pm | |
| Tue., 10/20 | V Girls Soccer | Wilton | Home - Conner Field [Directions] | W 1-0 | ||
| Tue., 10/20 | JV Girls Soccer | Wilton | Home - Saxe MS Field [Directions] | 4:30 p.m. | ||
| Tue., 10/20 | FR Girls Soccer | Wilton | Away - Allen's Field [Directions] | T 0-0 | 3:00pm | |
| Wed., 10/21 | V Boys Cross Country | FCIAC's | Home - Waveny Park [Directions] | 2:00 p.m. | ||
| Wed., 10/21 | SO Football | Brien McMahon | Away - Brien McMahon HS [Directions] | W 9-6 | 3:30pm | |
| Wed., 10/21 | V Boys Soccer | Danbury | Home - Dunning Stadium [Directions] | 7:00 p.m. | Senior Night | |
| Wed., 10/21 | JV Boys Soccer | Danbury | Home - Saxe MS Field [Directions] | L 4-1 | ||
| Wed., 10/21 | FR Boys Soccer | Danbury | Away - Danbury HS Grass Soccer Field [Directions] | 4:00 p.m. | 2:15pm | Black Team |
| Wed., 10/21 | V Girls Cross Country | FCIAC's | Home - Waveny Park [Directions] | 2:00 p.m. | ||
| Wed., 10/21 | V Girls Swimming and Diving | Staples | Home - New Canaan YMCA [Directions] | 3:00 p.m. | ||
| Wed., 10/21 | V Girls Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | L 0-3 | 2:30pm Var & JV ride together | |
| Wed., 10/21 | JV Girls Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | L 2-1 | 2:30pm Var & JV ride together | |
| Wed., 10/21 | FR Girls Volleyball | St. Joseph | Home - NCHS Gymnasium [Directions] | L 0-3 | ||
| Thu., 10/22 | FR Football | Greenwich | Home - Dunning Stadium [Directions] | W 34-14 | ||
| Thu., 10/22 | FR Field Hockey | New Canaan Country Day | Away | 3:45 p.m. | 2:45pm | |
| Thu., 10/22 | V Girls Soccer | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | W 2-0 | 4:15pm | |
| Thu., 10/22 | JV Girls Soccer | Danbury | Away - Danbury HS Grass Soccer Field [Directions] | 6:30 p.m.. | 4:15pm | |
| Thu., 10/22 | FR Girls Soccer | Danbury | Home - Saxe MS Field [Directions] | W 1-0 | ||
| Fri., 10/23 | JV Boys Soccer | Fairfield Ludlowe | Away - Roger Ludlowe MS [Directions] | Cancelled | 2:30pm | |
| Fri., 10/23 | V Girls Volleyball | Bridgeport Central | Home - NCHS Gymnasium [Directions] | W 3-0 | ||
| Fri., 10/23 | JV Girls Volleyball | Bridgeport Central | Home - NCHS Gymnasium [Directions] | W 2-0 | ||
| Sat., 10/24 | V Football | Greenwich | Away - Cardinal Stadium [Directions] | W 24-14 | 12:30pm - 2 buses | |
| Sat., 10/24 | FR Boys Soccer | Westhill | Away - Westhill Front Turf Field [Directions] | 10:00 a.m. | 8:45am | Red Team |
| Sat., 10/24 | V Field Hockey | New Milford | Home - Dunning Stadium [Directions] | W 1-0 | ||
| Sat., 10/24 | JV Field Hockey | New Milford | Home - Dunning Stadium [Directions] | T 0-0 | ||
| Sat., 10/24 | V Girls Swimming and Diving | JV Meet at Staples | Away | 9:00 a.m. | 7:45am | |
| Mon., 10/26 | JV Football | Greenwich | Home - Dunning Stadium [Directions] | W 40-12 | ||
| Mon., 10/26 | FR Boys Soccer | Greenwich | Home - Saxe MS Field [Directions] | 4:00 p.m. | Red Team | |
| Mon., 10/26 | FR Girls Soccer | New Canaan Country Day | Away | W 2-1 | 2:45pm | |
| Mon., 10/26 | V Girls Volleyball | Wilton | Away - Nicholas Zeoli Field House [Directions] | W 3-0 | 3:30pm Var & JV ride together | |
| Mon., 10/26 | JV Girls Volleyball | Wilton | Away - Nicholas Zeoli Field House [Directions] | W 0-2 | 3:30pm Var & JV ride together | |
| Mon., 10/26 | FR Girls Volleyball | Wilton | Home - NCHS Gymnasium [Directions] | L 0-3 | ||
| Tue., 10/27 | V Boys Soccer | Greenwich | Away - Cardinal Stadium [Directions] | 6:00 p.m. | 4:15pm | |
| Tue., 10/27 | JV Boys Soccer | Greenwich | Away - GHS Field 3 [Directions] | L 3-0 | 2:15pm | |
| Tue., 10/27 | V Field Hockey | Fairfield Warde | Home - Dunning Stadium [Directions] | W 5-0 | ||
| Tue., 10/27 | JV Field Hockey | Fairfield Warde | Home - Dunning Stadium [Directions] | W 3-0 | ||
| Tue., 10/27 | V Girls Soccer | Greenwich | Home - Dunning Stadium [Directions] | L 0-2 | Senior Night | |
| Tue., 10/27 | JV Girls Soccer | Greenwich | Home - Saxe MS Field [Directions] | 4:00 p.m. | ||
| Wed., 10/28 | V Girls Volleyball | Danbury | Home - NCHS Gymnasium [Directions] | W 3-1 | ||
| Wed., 10/28 | JV Girls Volleyball | Danbury | Home - NCHS Gymnasium [Directions] | L 1-2 | ||
| Wed., 10/28 | FR Girls Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | L 0-3 | 2:30pm | |
| Wed., 10/28 | FR Girls Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | L 0-3 | 2:15pm | |
| Thu., 10/29 | V Boys Cross Country | Freshman Invitational | Away - Tarrywile Park, Danbury | 4:30 p.m. | 2:05pm | |
| Thu., 10/29 | FR Football | Norwalk | Home - Dunning Stadium [Directions] | W 35-6 | ||
| Fri., 10/30 | V Football | Norwalk | Away - Testa Field, NHS [Directions] | W 52-14 | 4:30pm - 2 buses; 5:45pm - cheerleading bus | |
| Fri., 10/30 | JV Field Hockey | Darien | Away - DHS Stadium Field [Directions] | L 3-0 | 3:30pm | |
| Fri., 10/30 | V Girls Volleyball | Greenwich | Home - NCHS Gymnasium [Directions] | L 0-3 | Senior Night | |
| Fri., 10/30 | JV Girls Volleyball | Greenwich | Home - NCHS Gymnasium [Directions] | L 1-2 | ||
| Fri., 10/30 | FR Girls Volleyball | Greenwich | Away - Greenwich [Directions] | L 1-3 | 2:15pm | |
| Sat., 10/31 | V Boys Cross Country | CIAC Class L Championship | Away - Wickham Park - East Hartford [Directions] | 9:50 a.m. | 6:15am | |
| Sat., 10/31 | JV Football | Norwalk | Away - Nathan Hale M.S. Lower [Directions] | L 6-20 | 9:00am | |
| Sat., 10/31 | V Girls Cross Country | CIAC Class L Championship | Away - Wickham Park - East Hartford [Directions] | 9:15 a.m. | 6:15am | |
| Sat., 10/31 | V Field Hockey | FCIAC Playoffs | Home - Dunning Stadium [Directions] | 10:00 a.m. | ||
| Sat., 10/31 | V Girls Swimming and Diving | JV FCIAC's | Away - Greenwich | 1:00 p.m. | 10:45am | |
| Sat., 10/31 | JV Girls Volleyball | JV Tournament at Fairfield Warde | Away | 9:00 a.m. | 7:15am | |
| Mon., 11/2 | Miscellaneous Events | Unified Sports | Away - Staples HS | 3:00 p.m. | 2:05pm | |
| Tue., 11/3 | V Field Hockey | Darien | Home - Dunning Stadium [Directions] | 5:00 p.m. | ||
| Tue., 11/3 | V Girls Swimming and Diving | FCIAC Trails | Away - Greenwich | 4:00 p.m. | 1:15pm | |
| Wed., 11/4 | V Girls Swimming and Diving | FCIAC Diving | Away - Westhill | 4:00 p.m. | ||
| Wed., 11/4 | Miscellaneous Events | Math Team | Away - Wilton HS | 3:00 p.m. | 2:15pm | |
| Thu., 11/5 | SO Football | Darien | Home - Dunning Stadium [Directions] | L 13-32 | ||
| Thu., 11/5 | FR Football | Trumbull | Away - McDougall Stadium [Directions] | W 20-14 | 2@2:15pm | |
| Thu., 11/5 | V Girls Swimming and Diving | FCIAC Finals | Away - Greenwich | 4:30 p.m. | 1:15pm | |
| Fri., 11/6 | V Boys Cross Country | CIAC Open Championship | Away - Wickham Park - East Hartford [Directions] | 2:45 p.m. | ||
| Fri., 11/6 | V Football | Trumbull | Home - Dunning Stadium [Directions] | W 69-26 | Youth Football Night | |
| Fri., 11/6 | V Girls Cross Country | CIAC Open Championship | Away - Wickham Park - East Hartford [Directions] | 2:00 p.m. | ||
| Mon., 11/9 | JV Football | Trumbull | Home - Dunning Stadium [Directions] | W 54-0 | ||
| Mon., 11/9 | V Girls Soccer | Amity | Away - Amity HS [Directions] | W 2-1 | 11:30am | |
| Tue., 11/10 | V Field Hockey | Branford | Home - Dunning Stadium [Directions] | 6:00 p.m. | ||
| Wed., 11/11 | V Girls Soccer | Middletown | Away - Middletown H.S. [Directions] | W 1-0 | 11:15am | |
| Thu., 11/12 | SO Football | Greenwich | Home - Dunning Stadium [Directions] | T 14-14 | ||
| Thu., 11/12 | FR Football | Fairfield Ludlowe | Away - Taft Field [Directions] | W 31-14 | 2:15pm | |
| Thu., 11/12 | V Field Hockey | East Lyme | Away - ELHS Turf Field [Directions] | 5:00 p.m. | 1:30pm | |
| Thu., 11/12 | V Girls Swimming and Diving | CIAC Class L Diving Trials/Finals | Away - Middletown HS [Directions] | 5:30 p.m. | 1:30pm | |
| Fri., 11/13 | V Football | Fairfield Ludlowe | Home - Dunning Stadium [Directions] | W 42-7 | ||
| Fri., 11/13 | V Girls Soccer | Wilton | Away - Lilly Field - Turf [Directions] | W 1-0 | 1:15pm | |
| Sat., 11/14 | V Boys Cross Country | New England Championship | Away - Thetford Academy (VT) [Directions] | TBA | ||
| Sat., 11/14 | V Girls Cross Country | New England Championship | Away - Thetford Academy (VT) [Directions] | TBA | ||
| Sat., 11/14 | V Girls Swimming and Diving | CIAC Class L Qualifying | Away - East Hartford [Directions] | 6:00 p.m. | 1:30pm | |
| Mon., 11/16 | JV Football | Darien | Away - DHS Stadium Field [Directions] | L 13-30 | 2:30pm | |
| Mon., 11/16 | V Girls Soccer | Ridgefield | Away - Fairfield Ludlowe [Directions] | L 3-1 | 4:30pm | |
| Tue., 11/17 | V Field Hockey | Lauralton Hall | Away - Weston H.S. [Directions] | 5:00 p.m. | 3:00pm | |
| Tue., 11/17 | V Field Hockey | Lauralton Hall | Away - Weston H.S. [Directions] | 5:00 p.m. | 3:00pm | |
| Tue., 11/17 | V Field Hockey | Lauralton Hall | Away - Weston H.S. [Directions] | 5:00 p.m. | ||
| Wed., 11/18 | V Girls Swimming and Diving | CIAC Class L Finals | Away - Wesleyan Univ. [Directions] | 7:00 p.m. | 2:45pm | |
| Thu., 11/19 | FR Football | Darien | Home - Dunning Stadium [Directions] | W 23-12 | ||
| Thu., 11/19 | V Girls Swimming and Diving | CIAC Open Diving | Away - Middletown HS [Directions] | 5:30 p.m. | 2:00pm | |
| Fri., 11/20 | JV Boys Soccer | Weston (Scrim.) | Home - Saxe MS Field [Directions] | 3:30 p.m. | ||
| Sat., 11/21 | V Field Hockey | Joel Barlow | Away - Wethersfield H.S [Directions] | 10:00 a.m. | ||
| Sat., 11/21 | V Field Hockey | Joel Barlow | Away - Wethersfield H.S [Directions] | 10:00 a.m. | 7:00am | |
| Sat., 11/21 | V Girls Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 12:00 p.m. | 8:30am | |
| Thu., 11/26 | V Football | Darien | Away - Boyle Stadium in Stamford [Directions] | L 21-28 | 8:30am - 2 buses, Cheer bus @ 9am | |
| Tue., 12/1 | V Football | Windsor | Away - Windsor HS [Directions] | 6:30 p.m. | 2:30pm | |
| Wed., 12/2 | Miscellaneous Events | Math Team | Away - Wilton HS | 3:00 p.m. | 2:15pm | |
| Fri., 12/4 | V Girls Basketball | Weston (Scrim.) | Away - WHS Gymnasium [Directions] | 3:30 p.m. | 2:30pm | |
| Sat., 12/5 | V Girls Basketball | Trinity Catholic (Scrim.) | Away - Walsh Court | 2:00 p.m. | 1:15pm | |
| Sat., 12/5 | V Girls Ice Hockey | FCIAC Jamboree | Away - Shelton Rinks | 4:30 p.m. | 3:00pm | |
| Mon., 12/7 | V Football | Notre Dame-West Haven | Home - Dunning Stadium [Directions] | 6:30 p.m. | ||
| Wed., 12/9 | V Boys Ice Hockey | E.Haven Coop (Scrim.) | Away - DiLungo Rink [Directions] | 3:30 p.m. | 2:00pm | |
| Thu., 12/10 | V Boys Basketball | Bassick (Scrim.) | Home - NCHS Gymnasium [Directions] | 4:30 p.m. | ||
| Sat., 12/12 | V Boys Ice Hockey | West Haven Coop (Scrim.) | Away - Bennett Rink [Directions] | 1:45 p.m. | 11:45am | |
| Sun., 12/13 | JV Girls Ice Hockey | Stamford/Westhill/Staples | Home - Darien Ice Rink [Directions] | W 7-0 | ||
| Mon., 12/14 | V Boys Basketball | Stratford (Scrim.) | Away - Needham Memorial Gymnasium [Directions] | 6:30 p.m. | 4:30pm | |
| Mon., 12/14 | V Girls Ice Hockey | Guilford Coop | Home - Darien Ice Rink [Directions] | W 9-2 | ||
| Tue., 12/15 | V Girls Basketball | Brien McMahon | Home - NCHS Gymnasium [Directions] | L 23-25 | ||
| Tue., 12/15 | JV Girls Basketball | Brien McMahon | Home - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 12/15 | JV Girls Ice Hockey | New Canaan Country Day | Away - New Canaan Winter Club | L 0-6 | 2:15pm | |
| Wed., 12/16 | V Boys Ice Hockey | Greenwich (Scrim.) | Away - Dorothy Hamill Ice Rink [Directions] | 5:15 p.m. | 4:00pm | |
| Wed., 12/16 | V Wrestling | Trumbull | Away - Auxiliary gym [Directions] | Loss Trumbull 71 NC 6 | 2:15pm | |
| Wed., 12/16 | V Girls Ice Hockey | Hamden Coop | Away - Lou Astorino Ice Rink [Directions] | W 6-2 | 4:00pm | |
| Thu., 12/17 | V Boys Basketball | Abbott Tech (Scrim.) | Away - Daniel A. Garamella Memorial Gymnasium [Directions] | 3:30 p.m. | 2:30pm | |
| Thu., 12/17 | V Girls Basketball | Staples | Home - NCHS Gymnasium [Directions] | L 25-38 | ||
| Thu., 12/17 | JV Girls Basketball | Staples | Home - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 12/18 | JV Boys Ice Hockey | Trumbull (Scrim.) | Away - Shelton Rinks [Directions] | 5:30 p.m. | 3:45pm | |
| Sat., 12/19 | V Wrestling | Pomperaug Tournament | Away | 9:00 a.m. | 6:45am | |
| Sat., 12/19 | V Wrestling | Trumbull JV Tournament | Away | 9:00 a.m. | 7:30am | |
| Sat., 12/19 | JV Girls Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 11:30 a.m. | 8:30am FR & JV ride together | |
| Sat., 12/19 | FR Girls Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 10:00 a.m. | 8:30am FR & JV ride together | |
| Sat., 12/19 | V Girls Ice Hockey | Stamford/Westhill/Staples | Home - Darien Ice Rink [Directions] | W 6-0 | ||
| Sun., 12/20 | JV Girls Ice Hockey | Greenwich | Home - Darien Ice Rink [Directions] | W 4-2 | ||
| Mon., 12/21 | V Boys Ice Hockey | Notre Dame-West Haven | Away - Bennett Rink [Directions] | L 2-4 | 3:30pm | |
| Mon., 12/21 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Away - Norwalk High Pool [Directions] | 3:15 p.m. | 2:05pm | |
| Mon., 12/21 | V Girls Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | L 28-39 | 2:30pm | |
| Mon., 12/21 | V Girls Ice Hockey | Greenwich | Home - Darien Ice Rink [Directions] | W 3-0 | ||
| Tue., 12/22 | V Boys Basketball | Trumbull | Away - THS Main Gym [Directions] | L 59-71 | 5:15pm | |
| Wed., 12/23 | V Boys Basketball | Staples | Away - Trumbull HS [Directions] | L 23-48 | 3:30pm | |
| Wed., 12/23 | V Boys Ice Hockey | Hamden | Home - Darien Ice Rink [Directions] | L 2-6 | ||
| Wed., 12/23 | V Girls Basketball | Greenwich | Home - NCHS Gymnasium [Directions] | L 31-58 | ||
| Wed., 12/23 | JV Girls Basketball | Greenwich | Home - NCHS Gymnasium [Directions] | W 38-17 | ||
| Wed., 12/23 | FR Girls Basketball | Greenwich | Home - NCHS Gymnasium [Directions] | 2:00 p.m. | ||
| Sat., 12/26 | V Girls Indoor Track | North Shore Invite | Away - Armory, NYC | 9:00 a.m. | 6:30am | |
| Mon., 12/28 | V Boys Basketball | Berlin | Away - Shelton HS [Directions] | W 52-26 | 3:00pm | |
| Mon., 12/28 | JV Boys Ice Hockey | Greenwich | Home - Darien Ice Rink [Directions] | 4:30 p.m. | ||
| Mon., 12/28 | V Girls Basketball | Darien | Away - DHS Main Gym [Directions] | L 31-46 | 10:00am Var & JV ride together | |
| Mon., 12/28 | JV Girls Basketball | Darien | Away - DHS Main Gym [Directions] | L 31-37 | 10:00am Var & JV ride together | |
| Tue., 12/29 | V Boys Ice Hockey | Darien | Away - Darien Ice Rink [Directions] | L 0-8 | ||
| Wed., 12/30 | V Boys Basketball | Shelton | Away - Shelton HS [Directions] | L 48-54 | 5:00pm | |
| Wed., 12/30 | V Boys Ice Hockey | Staples | Home - Darien Ice Rink [Directions] | W 4-3 | ||
| Wed., 12/30 | V Boys Indoor Track | Danbury, Trumbull, Darien, Weshill, Warde, Norwalk | Away - Wilton HS | 10:00 a.m. | ||
| Wed., 12/30 | V Wrestling | Brien McMahon, Ridgefield, Stamford | Home - NCHS Gymnasium [Directions] | Loss Stamford 67 NC 18 Loss Ridgefield 60 NC 24 Loss McMahon 60 NC 24 | ||
| Wed., 12/30 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - So No Icehouse - Norwalk [Directions] | W 7-0 | 3:30pm | |
| Wed., 12/30 | V Girls Indoor Track | Danbury, Trumbull, Darien, Weshill, Warde, Norwalk | Away - Wilton HS | 10:00 a.m. | ||
| Sat., 1/2 | V Boys Ice Hockey | Greenwich | Home - Darien Ice Rink [Directions] | L 1-3 | ||
| Sat., 1/2 | V Wrestling | Norwalk JV Tournament | Away | 9:00 a.m. | 7:30am | |
| Sat., 1/2 | V Girls Indoor Track | Wintergreen Invite | Away - SCSU, New Haven | 8:00 a.m. | 6:30am | |
| Sun., 1/3 | JV Boys Ice Hockey | Darien (Scrim.) | Home - Darien Ice Rink [Directions] | 9:00 p.m. | ||
| Sun., 1/3 | JV Girls Ice Hockey | Masuk Coop | Away - The Rinks at Shelton [Directions] | W 7-1 | 4:30pm | |
| Tue., 1/5 | V Boys Basketball | Stamford | Away - Stamford HS [Directions] | L 35-52 | 4:00pm JV & Var ride together | |
| Tue., 1/5 | JV Boys Basketball | Stamford | Away - Stamford HS [Directions] | 5:15 p.m. | 4:00pm JV & Var ride together | |
| Tue., 1/5 | FR Boys Basketball | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | 2:45pm | |
| Tue., 1/5 | JV Boys Ice Hockey | New Canaan Country Day | Away - Winter Club | 4:15 p.m. | ||
| Tue., 1/5 | V Girls Basketball | Stamford | Home - NCHS Gymnasium [Directions] | L 16-36 | ||
| Tue., 1/5 | JV Girls Basketball | Stamford | Home - NCHS Gymnasium [Directions] | L 11-23 | ||
| Tue., 1/5 | FR Girls Basketball | Stamford | Home - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 1/6 | V Boys Ice Hockey | Ridgefield | Home - Darien Ice Rink [Directions] | W 3-2 | ||
| Wed., 1/6 | V Wrestling | Portland | Away - Portland HS [Directions] | Win NC 57 Portland 18 | 3:30pm | |
| Wed., 1/6 | V Girls Gymnastics | Westhill, Staples | Away - Westhill [Directions] | New Canaan - 116.30 Staples - 117.6 Westhill - 93.4 | 3:30pm | |
| Wed., 1/6 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Winter Garden Ice Arena [Directions] | W 6-1 | 2:10pm | |
| Wed., 1/6 | Miscellaneous Events | Math Team | Away - Wilton HS | 2:15 p.m. | 2:15pm | |
| Fri., 1/8 | V Boys Basketball | Brien McMahon | Home - NCHS Gymnasium [Directions] | L 55-68 | ||
| Fri., 1/8 | JV Boys Basketball | Brien McMahon | Home - NCHS Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/8 | FR Boys Basketball | Brien McMahon | Home - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/8 | JV Boys Ice Hockey | Notre Dame-West Haven | Home - Sono Ice House [Directions] | 5:00 p.m. | ||
| Fri., 1/8 | V Girls Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | W 51-24 | 3:00pm Var & JV ride together | |
| Fri., 1/8 | JV Girls Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | W 39-32 | 3:00pm Var & JV ride together | |
| Sat., 1/9 | V Boys Ice Hockey | Notre Dame-Fairfield | Home - Darien Ice Rink [Directions] | L 1-3 | ||
| Sat., 1/9 | V Boys Indoor Track | Freedom Games | Away - Ocean Breeze, Staten Island | 9:00 a.m. | 6:30am- Boys & Girls Ride together | |
| Sat., 1/9 | V Boys Indoor Track | Freedom Games | Away - Ocean Breeze, Staten Island | 9:00 a.m. | 6:30am- Boys & Girls Ride together | |
| Sat., 1/9 | V Boys Indoor Track | Ludlowe, Ridgefield, Danbury, Warde, Stamford, Norwalk | Away - Wilton HS | 9:30 a.m. | ||
| Sat., 1/9 | V Wrestling | Darien, Wolcott Tech, Bunnell, Platt Tech | Away - DHS Main Gym [Directions] | Win NC 60 Darien 21 Win NC 60 Wolcott Tech 19 Win NC 72 Platt Tech 9 Win NC 58 Bunnell 18 | 8:30am | |
| Sat., 1/9 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton Rinks [Directions] | W 5-0 | 6:20pm | |
| Sat., 1/9 | V Girls Indoor Track | Freedom Games | Away - Ocean Breeze, Staten Island | 9:00 a.m. | 6:30am - Boys & Girls Ride together | |
| Sat., 1/9 | V Girls Indoor Track | Ludlowe, Ridgefield, Danbury, Warde, Stamford, Norwalk | Away - Wilton HS | 9:30 a.m. | ||
| Mon., 1/11 | V Boys Basketball | Darien | Away - DHS Main Gym [Directions] | W 46-43 | 4:00pm JV & Var ride together | |
| Mon., 1/11 | JV Boys Basketball | Darien | Away - DHS Main Gym [Directions] | 5:15 p.m. | 4:00pm JV & Var ride together | |
| Mon., 1/11 | FR Boys Basketball | Darien | Away - DHS Main Gym [Directions] | 3:45 p.m. | 2:45pm | |
| Mon., 1/11 | V Boys Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | L 3-6 | 3:15pm | |
| Mon., 1/11 | V Girls Basketball | Darien | Home - NCHS Gymnasium [Directions] | L 23-28 | ||
| Mon., 1/11 | JV Girls Basketball | Darien | Home - NCHS Gymnasium [Directions] | W 32-16 | ||
| Mon., 1/11 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Darien Ice Rink [Directions] | W 8-2 | ||
| Wed., 1/13 | V Boys Swimming and Diving | Farfield Ludlowe/Warde | Home - New Canaan YMCA [Directions] | 3:00 p.m. | ||
| Wed., 1/13 | V Wrestling | Norwalk | Away - Norwalk High Gym [Directions] | Win NC 40 Norwalk 39 | 5:30pm | |
| Wed., 1/13 | V Girls Basketball | Harding | Away - Harding-Miska Gymnasium [Directions] | W 37-17 | 2:30pm Var & JV ride together | |
| Wed., 1/13 | JV Girls Basketball | Harding | Away - Harding-Miska Gymnasium [Directions] | W 38-16 | 2:30pm Var & JV ride together | |
| Fri., 1/15 | V Boys Basketball | Trinity Catholic | Away - Walsh Court | L 46-54 | 4:00pm JV & Var ride together | |
| Fri., 1/15 | JV Boys Basketball | Trinity Catholic | Away - Walsh Court | 5:15 p.m. | 4:00pm JV & Var ride together | |
| Fri., 1/15 | FR Boys Basketball | Trinity Catholic | Away - Walsh Court | 4:00 p.m. | 2:45pm | |
| Fri., 1/15 | V Boys Swimming and Diving | Darien | Away - Darien YMCA [Directions] | 3:00 p.m. | 1:30pm | |
| Fri., 1/15 | V Girls Basketball | Trinity Catholic | Home - NCHS Gymnasium [Directions] | W 33-28 | ||
| Fri., 1/15 | JV Girls Basketball | Trinity Catholic | Home - NCHS Gymnasium [Directions] | W 23-17 | ||
| Fri., 1/15 | V Girls Gymnastics | Fairfield Ludlowe, Fairfield Warde | Away [Directions] | Cancelled | 4:30pm | |
| Fri., 1/15 | V Girls Indoor Track | Yale Invite | Away - Coxe Cage, Yale | TBA | 11:00am | |
| Sat., 1/16 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland Of Ice [Directions] | L 1-3 | 4:45pm | |
| Sat., 1/16 | V Boys Indoor Track | Ridgefield, Norwalk, Trumbull, Warde, Westhill, Stamford | Away - Staples HS | 10:00 a.m. | 8:00am | |
| Sat., 1/16 | V Wrestling | Jonathan Law | Away [Directions] | Loss Law 41 NC 36 Win NC 45 Harding 25 Win NC 66 Platt Tech 18 Win NC 42 Masuk 33 | 6:45am | |
| Sat., 1/16 | V Girls Gymnastics | Westhill, Trumbull | Away - Westhill [Directions] | Cancelled | 3:30pm | |
| Sat., 1/16 | V Girls Ice Hockey | Darien | Away - Darien Ice Rink [Directions] | L 2-3 | ||
| Sat., 1/16 | V Girls Indoor Track | Ridgefield, Norwalk, Trumbull, Warde, Westhill, Stamford | Away - Staples HS | 10:00 a.m. | 8:00am | |
| Sat., 1/16 | V Girls Indoor Track | Yale Invite | Away - Coxe Cage, Yale | TBA | ||
| Mon., 1/18 | V Boys Ice Hockey | Xavier | Home - Darien Ice Rink [Directions] | W 5-1 | ||
| Mon., 1/18 | JV Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - Terry Connors Ice Rink [Directions] | W 4-0 | 10:50am | |
| Tue., 1/19 | V Boys Basketball | Trumbull | Home - NCHS Gymnasium [Directions] | L 61-67 | ||
| Tue., 1/19 | JV Boys Basketball | Trumbull | Home - NCHS Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/19 | FR Boys Basketball | Trumbull | Home - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/19 | V Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | L 13-51 | 3:30pm Var & JV ride together | |
| Tue., 1/19 | JV Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | L 13-53 | 3:30pm Var & JV ride together | |
| Tue., 1/19 | FR Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | 2:15pm | |
| Wed., 1/20 | V Boys Ice Hockey | Ridgefield | Away - Winter Garden Ice Arena [Directions] | L 0-1 | 6:30pm | |
| Wed., 1/20 | V Boys Swimming and Diving | Westhill/Stamford | Home - New Canaan YMCA [Directions] | 3:00 p.m. | ||
| Wed., 1/20 | V Wrestling | Fairfield Warde | Home - NCHS Gymnasium [Directions] | Loss Warde 65 NC 15 | ||
| Wed., 1/20 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away [Directions] | W 3-0 | 3:45pm | |
| Thu., 1/21 | V Girls Gymnastics | New Milford, Westhill | Away - New Milford HS [Directions] | New Canaan - 123.95 New Milford - 134.75 Westhill - 110.85 | 2:45pm | |
| Fri., 1/22 | V Boys Basketball | Westhill | Home - NCHS Gymnasium [Directions] | L 52-58(OT) | ||
| Fri., 1/22 | JV Boys Basketball | Westhill | Home - NCHS Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/22 | FR Boys Basketball | Westhill | Home - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/22 | JV Boys Ice Hockey | Notre Dame-Fairfield | Home - Sono Ice House [Directions] | 5:30 p.m. | ||
| Fri., 1/22 | V Boys Swimming and Diving | Ridgefield | Away - Pool at Barlow Mountain School [Directions] | 3:30 p.m. | 2:05pm | |
| Fri., 1/22 | V Girls Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | L 29-43 | 3:15pm Var & JV ride together | |
| Fri., 1/22 | JV Girls Basketball | Westhill | Away [Directions] | W 38-36 | 3:15pm Var & JV ride together | |
| Fri., 1/22 | FR Girls Basketball | Westhill | Away [Directions] | Cancelled | 2:45pm | |
| Fri., 1/22 | V Girls Ice Hockey | East Catholic Coop | Away - Newington Ice Rink [Directions] | W 4-2 | 5:45pm | |
| Sat., 1/23 | V Wrestling | Holy Cross, Platt Tech, New Haven Wrestling | Home - NCHS Gymnasium [Directions] | Cancelled | ||
| Sat., 1/23 | V Girls Indoor Track | SCC Coaches Invite | Away - Hillhouse HS, New Haven | Cancelled | ||
| Mon., 1/25 | V Boys Ice Hockey | Trumbull | Home - Darien Ice Rink [Directions] | W 5-1 | ||
| Mon., 1/25 | JV Girls Ice Hockey | New Canaan Country Day | Home - Stamford Twin Rinks West [Directions] | T 4-4 | 2:15pm | |
| Tue., 1/26 | V Boys Basketball | Norwalk | Away - Norwalk High Gym [Directions] | L 58-73 | 4:00pm JV & Var ride together | |
| Tue., 1/26 | JV Boys Basketball | Norwalk | Away - Norwalk High Gym [Directions] | 5:15 p.m. | 4:00pm JV & Var ride together | |
| Tue., 1/26 | FR Boys Basketball | Norwalk | Away - Norwalk High Gym [Directions] | 4:00 p.m. | 2:45pm | |
| Tue., 1/26 | JV Boys Ice Hockey | Ridgefield | Away - Danbury Ice Arena [Directions] | 8:00 p.m. | 6:00pm | |
| Tue., 1/26 | V Girls Basketball | Norwalk | Home - NCHS Gymnasium [Directions] | L 32-46 | ||
| Tue., 1/26 | JV Girls Basketball | Norwalk | Home - NCHS Gymnasium [Directions] | L 23-37 | ||
| Tue., 1/26 | FR Girls Basketball | Fairfield Ludlowe | Home - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 1/27 | V Wrestling | Westhill | Home - NCHS Gymnasium [Directions] | Loss Westhill 42 NC 31 | ||
| Wed., 1/27 | V Girls Gymnastics | Greenwich, Westhill, Trumbull | Away - Westhill [Directions] | Westhill - 99.3 New Canaan - 117.65 Greenwich - 138.9 | 3:30pm | |
| Wed., 1/27 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Darien Ice Rink [Directions] | W 9-0 | ||
| Thu., 1/28 | V Boys Indoor Track | Ludlowe, Darien, Ridgefield, McMahon, Trumbull, Warde | Away - Wilton HS | 5:30 p.m. | 4:00pm | Last Chance Qualifier Meet |
| Thu., 1/28 | V Girls Indoor Track | Ludlowe, Darien, Ridgefield, McMahon, Trumbull, Warde | Away - Wilton HS | 5:30 p.m. | 4:00pm | Last Chance Qualifier Meet |
| Fri., 1/29 | V Boys Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | L 39-51 | 3:45pm JV & Var ride together | |
| Fri., 1/29 | JV Boys Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 5:15 p.m. | 3:45pm JV & Var ride together | |
| Fri., 1/29 | FR Boys Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 4:00 p.m. | 2:30pm | |
| Fri., 1/29 | V Boys Swimming and Diving | Wilton | Away - Wilton YMCA [Directions] | 3:40 p.m. | 2:05pm | |
| Fri., 1/29 | V Girls Basketball | Fairfield Ludlowe | Home - NCHS Gymnasium [Directions] | L 28-44 | ||
| Fri., 1/29 | JV Girls Basketball | Fairfield Ludlowe | Home - NCHS Gymnasium [Directions] | L 18-37 | ||
| Fri., 1/29 | FR Girls Basketball | Fairfield Ludlowe | Home - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/29 | V Girls Ice Hockey | Darien | Home - Darien Ice Rink [Directions] | L 1-3 | ||
| Sat., 1/30 | V Boys Ice Hockey | Darien | Home - Darien Ice Rink [Directions] | L 3-4 | ||
| Sat., 1/30 | V Boys Indoor Track | FCIAC East | Away - Wilton HS | 9:30 a.m. | ||
| Sat., 1/30 | V Wrestling | Brandford Duals | Away [Directions] | 9:00 a.m. | 6:30am | |
| Sat., 1/30 | V Girls Indoor Track | FCIAC East | Away - Wilton HS | 9:30 a.m. | ||
| Sun., 1/31 | JV Boys Ice Hockey | Westhill-Stamford (Scrim.) | Home - Darien Ice Rink [Directions] | Cancelled | ||
| Mon., 2/1 | V Boys Basketball | Ridgefield | Home - NCHS Gymnasium [Directions] | L 44-56 | ||
| Mon., 2/1 | JV Boys Basketball | Ridgefield | Home - NCHS Gymnasium [Directions] | 5:15 p.m. | ||
| Mon., 2/1 | FR Boys Basketball | Ridgefield | Home - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 2/1 | V Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | L 23-63 | 3:30pm Var & JV ride together | |
| Mon., 2/1 | JV Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | L 18-38 | 3:30pm Var & JV ride together | |
| Mon., 2/1 | FR Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | 2:30pm | |
| Mon., 2/1 | V Girls Gymnastics | Wilton | Away - Wilton HS Aux. Gym [Directions] | New Canaan - 121.2 Wilton - 137 | 2:45pm | |
| Mon., 2/1 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Darien Ice Rink [Directions] | W 7-0 | ||
| Tue., 2/2 | V Wrestling | Wilton | Home - NCHS Gymnasium [Directions] | 7:00 p.m. | ||
| Wed., 2/3 | V Boys Basketball | Fairfield Warde | Home - NCHS Gymnasium [Directions] | L 61-69 | ||
| Wed., 2/3 | JV Boys Basketball | Fairfield Warde | Home - NCHS Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 2/3 | FR Boys Basketball | Fairfield Warde | Home - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 2/3 | V Boys Ice Hockey | Wilton | Home - Darien Ice Rink [Directions] | W 8-1 | ||
| Wed., 2/3 | V Boys Swimming and Diving | Greenwich | Home - New Canaan YMCA [Directions] | 3:00 p.m. | ||
| Wed., 2/3 | V Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | L 32-65 | 3:30pm Var & JV ride together | |
| Wed., 2/3 | JV Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | L 43-50 | 3:30pm Var & JV ride together | |
| Wed., 2/3 | FR Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | 2:45pm | |
| Wed., 2/3 | V Girls Gymnastics | Darien, Westhill | Away [Directions] | New Canaan - 116.90 Darien - 136.7 | 3:45pm | |
| Wed., 2/3 | Miscellaneous Events | Math Team | Away - Wilton HS | 3:00 p.m. | 2:15pm | |
| Thu., 2/4 | V Boys Indoor Track | FCIAC Championship | Away - Hillhouse | TBA | 1:45pm | |
| Thu., 2/4 | V Girls Indoor Track | FCIAC Championship | Away - Hillhouse | 4:00 p.m. | 1:45pm | |
| Fri., 2/5 | FR Girls Basketball | Weston | Away [Directions] | Cancelled | 2:30pm | |
| Sat., 2/6 | V Boys Ice Hockey | St. Joseph | Away - Shelton Rinks [Directions] | W 4-1 | 6:00pm | |
| Sat., 2/6 | V Wrestling | Fairfield Ludlowe JV Tournament | Away | 9:30 a.m. | 7:30am | |
| Sat., 2/6 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Darien Ice Rink [Directions] | W 5-0 | Senior Night | |
| Mon., 2/8 | FR Girls Basketball | Weston | Away - WHS Gymnasium [Directions] | Cancelled | 2:30pm | |
| Tue., 2/9 | V Boys Basketball | Staples | Home - NCHS Gymnasium [Directions] | W 57-55 | ||
| Tue., 2/9 | JV Boys Basketball | Staples | Home - NCHS Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 2/9 | FR Boys Basketball | Staples | Home - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 2/9 | V Girls Basketball | Staples | Away - Staples H.S. Gym [Directions] | W 49-45 | 3:30pm Var & JV ride together | |
| Tue., 2/9 | JV Girls Basketball | Staples | Away - Staples H.S. Gym [Directions] | L 23-35 | 3:30pm Var & JV ride together | |
| Tue., 2/9 | FR Girls Basketball | Staples | Away - Staples H.S. Gym [Directions] | 4:00 p.m. | 2:45pm | |
| Tue., 2/9 | V Girls Gymnastics | Fairfield Ludlowe, Fairfield Warde, Westhill | Away - Gymnastics Cheer Academy [Directions] | Ludlowe - 135.5 New Canaan - 123.65 Westhill - 101.45 Warde - 64.30 | 4:30pm | |
| Wed., 2/10 | V Boys Ice Hockey | Norwalk | Home - Darien Ice Rink [Directions] | W 6-0 | ||
| Wed., 2/10 | V Wrestling | Fairfield Ludlowe | Home - NCHS Gymnasium [Directions] | 7:00 p.m. | ||
| Thu., 2/11 | V Boys Basketball | St. Joseph | Away - St. Joseph HS [Directions] | L 53-63 | 3:45pm JV & Var ride together | |
| Thu., 2/11 | JV Boys Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 5:15 p.m. | 3:45pm JV & Var ride together | |
| Thu., 2/11 | FR Boys Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | 2:30pm | |
| Thu., 2/11 | V Girls Basketball | St. Joseph | Home - NCHS Gymnasium [Directions] | L 27-45 | ||
| Thu., 2/11 | JV Girls Basketball | St. Joseph | Home - NCHS Gymnasium [Directions] | 5:15 p.m. | ||
| Thu., 2/11 | FR Girls Basketball | St. Joseph | Home - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 2/11 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice [Directions] | W 8-1 | 3:15pm | |
| Fri., 2/12 | V Boys Swimming and Diving | Staples | Home - New Canaan YMCA [Directions] | 3:00 p.m. | ||
| Fri., 2/12 | V Wrestling | FCIAC's | Home - NCHS Gymnasium [Directions] | 4:30 p.m. | ||
| Fri., 2/12 | V Girls Ice Hockey | Hall/Conard | Away - Veteran's Memorial Rink [Directions] | W 4-1 | 5:30pm | |
| Sat., 2/13 | V Boys Ice Hockey | Westhill-Stamford | Home - Darien Ice Rink [Directions] | W 3-0 | ||
| Sat., 2/13 | V Boys Indoor Track | CIAC Class L Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 10:00 a.m. | 7:30am Boys & Girls ride together | |
| Sat., 2/13 | V Boys Indoor Track | CIAC Class L Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 10:00 a.m. | ||
| Sat., 2/13 | V Wrestling | FCIAC's | Home - NCHS Gymnasium [Directions] | 10:00 a.m. | ||
| Sat., 2/13 | V Girls Gymnastics | FCIAC's | Away - Jonathan Law HS | 119.90 | 8:30am | |
| Sat., 2/13 | V Girls Indoor Track | CIAC Class L Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 10:00 a.m. | 7:30am Both Boys & Girls ride together | |
| Sun., 2/14 | JV Boys Ice Hockey | Westhill-Stamford | Home - Darien Ice Rink [Directions] | Cancelled | ||
| Mon., 2/15 | V Boys Basketball | Bridgeport Central | Home - NCHS Gymnasium [Directions] | W 80-34 | ||
| Mon., 2/15 | JV Boys Basketball | Bridgeport Central | Home - NCHS Gymnasium [Directions] | Cancelled | ||
| Mon., 2/15 | FR Boys Basketball | Bridgeport Central | Home - NCHS Gymnasium [Directions] | 12:00 p.m. | ||
| Mon., 2/15 | V Boys Ice Hockey | Xavier | Away - Freeman Athletic Center, Wesleyan University [Directions] | L 0-4 | 10:30am | |
| Mon., 2/15 | V Girls Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | W 31-15 | 2:30pm Var & JV ride together | |
| Mon., 2/15 | JV Girls Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 2:00 p.m. | 2:30pm Var & JV ride together | |
| Mon., 2/15 | V Girls Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | W 2-0 | 12:20pm | |
| Mon., 2/15 | JV Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Darien Ice Rink [Directions] | W 3-2 | ||
| Tue., 2/16 | JV Girls Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | W 4-1 | 3:30pm | |
| Wed., 2/17 | V Boys Basketball | Wilton | Away - Nicholas Zeoli Field House [Directions] | L 47-62 | 4:00pm JV & Var ride together | |
| Wed., 2/17 | JV Boys Basketball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 5:15 p.m. | 4:00pm JV & Var ride together | |
| Wed., 2/17 | FR Boys Basketball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 4:00 p.m. | 2:45pm | |
| Wed., 2/17 | V Boys Swimming and Diving | Trumbull | Home - New Canaan YMCA [Directions] | 3:00 p.m. | ||
| Wed., 2/17 | V Girls Basketball | Wilton | Home - NCHS Gymnasium [Directions] | L 30-42 | Senior Night | |
| Wed., 2/17 | JV Girls Basketball | Wilton | Home - NCHS Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 2/17 | V Girls Ice Hockey | Simsbury | Away - ISCC [Directions] | W 4-1 | 12:15pm | |
| Fri., 2/19 | JV Boys Ice Hockey | Ridgefield | Home - Sono Ice House [Directions] | 5:00 p.m. | ||
| Fri., 2/19 | V Wrestling | CIAC Class L | Away - Bristol Central | TBA | ||
| Fri., 2/19 | JV Girls Ice Hockey | Stamford/Westhill/Staples | Home - Stamford Twin Rinks West [Directions] | Cancelled | 2:10pm | |
| Sat., 2/20 | V Boys Ice Hockey | Trinity Catholic | Away - Terry Conners Ice Rink | W 7-1 | 4:00pm | |
| Sat., 2/20 | V Boys Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | ||
| Sat., 2/20 | V Boys Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | ||
| Sat., 2/20 | V Wrestling | CIAC Class L | Away - Bristol Central | TBA | ||
| Sat., 2/20 | V Girls Gymnastics | Ro Carlucci Invitational | Away - Westhill [Directions] | 11:00 a.m. | 9:30am | |
| Sat., 2/20 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Away - The Rinks at Shelton [Directions] | W 3-0 | 6:30pm | |
| Sat., 2/20 | V Girls Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | 9:30am | |
| Sun., 2/21 | JV Boys Ice Hockey | Darien (Scrim.) | Home - Darien Ice Rink [Directions] | 9:00 p.m. | ||
| Sun., 2/21 | V Girls Gymnastics | Trumbull, Foran | Away - Next Dimension Gymnastics [Directions] | 118.80 | 1:15pm | |
| Sun., 2/21 | JV Girls Ice Hockey | Masuk Coop | Away - The Rinks at Shelton [Directions] | Cancelled | 4:20pm | |
| Mon., 2/22 | V Boys Basketball | Danbury | Home - NCHS Gymnasium [Directions] | L 43-63 | ||
| Mon., 2/22 | JV Boys Basketball | Danbury | Home - NCHS Gymnasium [Directions] | 5:15 p.m. | ||
| Mon., 2/22 | FR Boys Basketball | Danbury | Home - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 2/22 | V Boys Ice Hockey | St. Joseph | Home - Darien Ice Rink [Directions] | W 2-1 | ||
| Mon., 2/22 | V Boys Swimming and Diving | FCIAC Trials | Away - Greenwich | 4:30 p.m. | 1:45pm | |
| Wed., 2/24 | V Boys Basketball | Greenwich | Away - GHS Gymnasium [Directions] | L 44-57 | 3:45pm JV & Var ride together | |
| Wed., 2/24 | JV Boys Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 5:15 p.m. | 3:45pm JV & Var ride together | |
| Wed., 2/24 | FR Boys Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 4:00 p.m. | 2:30pm | |
| Wed., 2/24 | JV Boys Ice Hockey | Darien | Away - Darien Ice Rink [Directions] | 2:50 p.m. | ||
| Wed., 2/24 | V Boys Swimming and Diving | Diving FCIAC's | Away - Westhill | 4:00 p.m. | ||
| Wed., 2/24 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Darien Ice Rink [Directions] | W 5-0 | ||
| Fri., 2/26 | V Boys Swimming and Diving | FCIAC Finals | Away - Greenwich | 6:00 p.m. | 3:15pm | |
| Sat., 2/27 | V Boys Ice Hockey | Ridgefield | Away - Terry Connors Ice Rink [Directions] | 3:00 p.m. | 1:00pm | |
| Sat., 2/27 | V Girls Gymnastics | States | Away | TBA | ||
| Sat., 2/27 | V Girls Ice Hockey | Darien | Away - Terry Connors Ice Rink [Directions] | L 0-2 | ||
| Sun., 2/28 | V Boys Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | TBA | ||
| Sun., 2/28 | V Boys Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | TBA | ||
| Sun., 2/28 | V Girls Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | TBA | ||
| Mon., 2/29 | V Girls Ice Hockey | Hall/Conard | Home - Darien Ice Rink [Directions] | W 3-2 | ||
| Mon., 2/29 | Miscellaneous Events | Unified Sports | Away - St Lukes | 3:00 p.m. | 2:10pm | |
| Wed., 3/2 | V Girls Ice Hockey | East Catholic Coop | Away - Shelton [Directions] | L 1-2 | 5:00pm | |
| Wed., 3/2 | Miscellaneous Events | Math Team | Away - Wilton HS | 3:00 p.m. | 2:15pm | |
| Sat., 3/5 | V Girls Ice Hockey | CIAC Finals | Away | TBA | ||
| Sun., 3/6 | V Girls Ice Hockey | CIAC Finals | Away | TBA | ||
| Wed., 3/9 | V Boys Ice Hockey | Darien | Away - Terry Connors Rink [Directions] | 6:00 p.m. | 3:45pm | |
| Thu., 3/10 | V Boys Swimming and Diving | CIAC Class L Diving Trials/Finals | Away - Middletown HS [Directions] | 5:30 p.m. | 2:15pm | |
| Sat., 3/12 | V Boys Swimming and Diving | CIAC Class L Qualifying | Away - Kennedy HS [Directions] | 4:30 p.m. | 11:45am J&R Tours - 32 pass | |
| Mon., 3/14 | Miscellaneous Events | Unified Sports | Away - Ludlowe | 3:00 p.m. | 2:10pm | |
| Wed., 3/16 | V Boys Swimming and Diving | CIAC Class L Finals | Away - Wesleyan Univ. [Directions] | 6:00 p.m. | ||
| Thu., 3/17 | V Boys Swimming and Diving | CIAC Open Diving | Away - Bulkeley [Directions] | 5:30 p.m. | ||
| Sat., 3/19 | V Boys Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 2:30 p.m. | ||
| Wed., 3/23 | V Softball | Darien (Scrim.) | Away - DHS Softball Varsity Field [Directions] | 3:45 p.m. | ||
| Sat., 3/26 | V Boys Lacrosse | Niskayuna (NY) (Scrim.) | Away - Union College | 2:00 p.m. | 9:00am | |
| Sat., 3/26 | V Girls Lacrosse | Wilton Play Day | Away | 9:00 a.m. | 7:30am | |
| Tue., 3/29 | JV Baseball | St. Lukes (Scrim.) | Home [Directions] | 4:00 p.m. | ||
| Tue., 3/29 | V Girls Lacrosse | Staples (Scrim.) | Away - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | 2:30pm Var & JV ride together | |
| Tue., 3/29 | JV Girls Lacrosse | Staples (Scrim.) | Away - Ginny Parker Field - Staples [Directions] | 5:15 p.m. | 2:30pm Var & JV ride together | |
| Tue., 3/29 | V Softball | St. Lukes (Scrim.) | Home - Waveny Park - Orchard Field [Directions] | 4:00 p.m. | ||
| Tue., 3/29 | V Softball | St. Lukes (Scrim.) | Home - Waveny Park - Orchard Field [Directions] | 4:00 p.m. | ||
| Wed., 3/30 | V Baseball | Greenwich (Scrim.) | Home - Mead Park [Directions] | 4:00 p.m. | ||
| Wed., 3/30 | V Baseball | Greenwich (Scrim.) | Home - Mead Park [Directions] | 4:00 p.m. | ||
| Wed., 3/30 | V Boys Lacrosse | Joel Barlow (Scrim.) | Home - Dunning Stadium [Directions] | 4:30 p.m. | ||
| Thu., 3/31 | V Boys Volleyball | Greenwich (Scrim.) | Home - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 4/1 | V Girls Lacrosse | Bronxville/West Hamptom Beach | Home - Dunning Stadium [Directions] | 4:30 p.m. | ||
| Sat., 4/2 | V Boys Lacrosse | Loyola Blakefield (MD) | Away | W 9-8(OT) | 8:00am | |
| Sat., 4/2 | V Girls Lacrosse | Westhill | Home - Dunning Stadium [Directions] | W 16-1 | ||
| Sat., 4/2 | JV Girls Lacrosse | Westhill | Home - Dunning Stadium [Directions] | 5:30 p.m. | ||
| Tue., 4/5 | V Girls Lacrosse | John Jay (NY) | Home - Dunning Stadium [Directions] | W 13-4 | ||
| Tue., 4/5 | JV Girls Lacrosse | John Jay (NY) | Home - Dunning Stadium [Directions] | 6:00 p.m. | ||
| Wed., 4/6 | V Baseball | Trinity Catholic | Home - Mead Park [Directions] | W 3-0 | ||
| Wed., 4/6 | FR Baseball | Darien | Home - Waveny Park - Coppo Field [Directions] | 4:00 p.m. | ||
| Wed., 4/6 | V Boys Lacrosse | Fairfield Prep | Home - Dunning Stadium [Directions] | W 8-7 | ||
| Wed., 4/6 | JV Boys Lacrosse | Fairfield Prep | Home - Dunning Stadium [Directions] | 6:30 p.m. | ||
| Wed., 4/6 | V Boys Tennis | Stamford | Away - Stamford HS [Directions] | W 7-0 | 2:20pm | |
| Wed., 4/6 | V Boys Volleyball | Darien | Away - DHS Main Gym [Directions] | L 0-3 | ||
| Wed., 4/6 | JV Boys Volleyball | Darien | Away - DHS Main Gym [Directions] | L 1-2 | ||
| Wed., 4/6 | V Girls Golf | Wilton | Away - Silver Mine CC [Directions] | NC-165 Wilton-174 | ||
| Wed., 4/6 | FR Girls Lacrosse | Greenwich | Away - GHS Field 3 [Directions] | 4:00 p.m. | 2:30pm | |
| Wed., 4/6 | V Girls Tennis | Stamford | Home - NCHS Tennis Courts [Directions] | W 7-0 | ||
| Thu., 4/7 | V Girls Lacrosse | St. Joseph | Home - Dunning Stadium [Directions] | W 15-5 | ||
| Thu., 4/7 | JV Girls Lacrosse | St. Joseph | Home - Dunning Stadium [Directions] | 5:30 p.m. | ||
| Fri., 4/8 | V Baseball | New Milford | Home - Mead Park [Directions] | L 0-2 | ||
| Fri., 4/8 | JV Baseball | New Milford | Home - Waveny Park - Coppo Field [Directions] | 4:15 p.m. | ||
| Fri., 4/8 | V Boys Tennis | Brien McMahon | Home - NCHS Tennis Courts [Directions] | W 7-0 | ||
| Fri., 4/8 | JV Boys Tennis | Darien | Away - Cherry Lawn Park [Directions] | 3:30 p.m. | ||
| Fri., 4/8 | FR Girls Lacrosse | Ridgefield | Home - NCHS Water Tower Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 4/8 | V Softball | Greenwich | Away - GHS Softball Field [Directions] | W 15-3 | 2:20pm | |
| Fri., 4/8 | V Girls Tennis | Brien McMahon | Away - Brien McMahon HS [Directions] | W 6-1 | ||
| Sat., 4/9 | FR Baseball | Sheehan | Home - Waveny Park - Coppo Field [Directions] | 11:00 a.m. | ||
| Sat., 4/9 | FR Boys Lacrosse | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 11:00 a.m. | ||
| Sat., 4/9 | V Girls Lacrosse | Glastonbury | Away - GHS Turf Field [Directions] | W 16-12 | 1:00pm Var & JV ride together | |
| Sat., 4/9 | JV Girls Lacrosse | Glastonbury | Away - GHS Field #12 [Directions] | 3:30 p.m. | 1:00pm Var & JV ride together | |
| Sat., 4/9 | V Softball | New Milford | Home - Waveny Park - Orchard Field [Directions] | L 1-19 | ||
| Sun., 4/10 | V Baseball | Sheehan | Away - Sheehan HS Neubauer Field [Directions] | L 3-19 | ||
| Sun., 4/10 | JV Baseball | Sheehan | Away - Lyman Hall - Pat Wall Field [Directions] | 2:00 p.m. | ||
| Mon., 4/11 | V Baseball | Stamford | Away - Stamford HS [Directions] | L 0-4 | 2:30p | |
| Mon., 4/11 | JV Baseball | Stamford | Away [Directions] | 4:00 p.m. | 2:30p | |
| Mon., 4/11 | FR Baseball | Stamford | Home - Conner Field [Directions] | 4:00 p.m. | ||
| Mon., 4/11 | V Boys Tennis | Darien | Away - DHS Tennis Courts [Directions] | W 5-2 | 2:20pm | |
| Mon., 4/11 | V Softball | Stamford | Home - Waveny Park - Orchard Field [Directions] | W 10-4 | ||
| Mon., 4/11 | JV Softball | Stamford | Home - Waveny Park - Orchard Field [Directions] | Cancelled | ||
| Mon., 4/11 | V Girls Tennis | Darien | Home - NCHS Tennis Courts [Directions] | L 2-5 | ||
| Tue., 4/12 | V Boys Lacrosse | Wilton | Away - Fujitani Field - Turf [Directions] | W 11-2 | 5:00pm | |
| Tue., 4/12 | JV Boys Lacrosse | Wilton | Away - Whitten Field [Directions] | 5:00 p.m. | ||
| Tue., 4/12 | FR Boys Lacrosse | St. Joseph | Home - NCHS Water Tower Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 4/12 | V Girls Lacrosse | Greenwich | Home - Dunning Stadium [Directions] | W 14-10 | ||
| Tue., 4/12 | JV Girls Lacrosse | Greenwich | Home - Dunning Stadium [Directions] | 5:30 p.m. | ||
| Tue., 4/12 | FR Girls Lacrosse | Trumbull | Away - McDougall Stadium [Directions] | 4:00 p.m. | 2:30pm | |
| Tue., 4/12 | JV Girls Tennis | Ridgefield | Away - Yannity [Directions] | Cancelled | ||
| Wed., 4/13 | V Baseball | Brien McMahon | Home - Mead Park [Directions] | W 7-3 | ||
| Wed., 4/13 | JV Baseball | Brien McMahon | Home - Waveny Park - Coppo Field [Directions] | 4:00 p.m. | ||
| Wed., 4/13 | V Boys Tennis | Brunswick School (Scrim.) | Away | 4:00 p.m. | ||
| Wed., 4/13 | V Boys Volleyball | Danbury | Home - NCHS Gymnasium [Directions] | W 3-0 | ||
| Wed., 4/13 | JV Boys Volleyball | Danbury | Home - NCHS Gymnasium [Directions] | W 2-0 | ||
| Wed., 4/13 | FR Girls Lacrosse | Darien | Home - NCHS Water Tower Turf Field [Directions] | 2:00 p.m. | ||
| Wed., 4/13 | V Softball | Brien McMahon | Away - Brien McMahon HS [Directions] | W 15-1 | 9:45am | |
| Wed., 4/13 | JV Softball | Brien McMahon | Away - Brien McMahon HS [Directions] | 1:00 p.m. | 9:45 am | |
| Wed., 4/13 | V Girls Tennis | Trinity Catholic | Home - NCHS Tennis Courts [Directions] | W 7-0 | ||
| Thu., 4/14 | V Boys Lacrosse | Stamford | Home - Dunning Stadium [Directions] | W 15-3 | ||
| Thu., 4/14 | JV Boys Lacrosse | Stamford | Home - Saxe MS Field [Directions] | 4:00 p.m. | ||
| Thu., 4/14 | V Boys Tennis | Trinity Catholic | Away - Scalzi Park | W 7-0 | 2:20pm | |
| Thu., 4/14 | V Girls Lacrosse | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | W 16-4 | 2:30pm | |
| Thu., 4/14 | JV Girls Lacrosse | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 6:00 p.m. | 4:00pm | |
| Fri., 4/15 | V Baseball | Darien | Away - DHS Baseball Varsity Field [Directions] | L 0-8 | 2:45pm | Pick up from Mead Park |
| Fri., 4/15 | JV Baseball | Darien | Away - DHS Baseball JV Field [Directions] | 4:00 p.m. | JV travel with V | |
| Fri., 4/15 | FR Baseball | Darien | Home - Waveny Park - Coppo Field [Directions] | 4:00 p.m. | ||
| Fri., 4/15 | V Boys Volleyball | Ridgefield | Home - NCHS Gymnasium [Directions] | L 1-3 | ||
| Fri., 4/15 | JV Boys Volleyball | Ridgefield | Home - NCHS Gymnasium [Directions] | L 0-2 | ||
| Fri., 4/15 | V Softball | Darien | Home - Waveny Park - Orchard Field [Directions] | L 1-14 | ||
| Fri., 4/15 | JV Softball | Darien | Home - Waveny Park - Orchard Field [Directions] | Cancelled | ||
| Sat., 4/16 | V Boys Lacrosse | Brunswick School | Away | W 13-8 | 5:00pm | |
| Sat., 4/16 | JV Boys Lacrosse | Brunswick School | Away | 4:45 p.m. | 3:00pm | |
| Sat., 4/16 | V Girls Lacrosse | Middle Country (NY) | Away - Cold Spring Harbor HS | L 10-13 | 10:00am | |
| Sat., 4/16 | V Girls Outdoor Track | Monica Hargrove Frosh/Soph Invite | Away | 10:00 a.m. | 7:45am | |
| Sat., 4/16 | V Softball | Trumbull | Away - Varsity Softball Field [Directions] | L 3-8 | 11:00 am | |
| Mon., 4/18 | V Baseball | Trinity Catholic | Away - Cubeta Stadium | W 7-2 | 2:30pm | |
| Mon., 4/18 | JV Baseball | Trinity Catholic | Away - Rippowam | 4:00 p.m. | JV travel with V | |
| Mon., 4/18 | V Boys Golf | Trumbull, Stamford | Home - Country Club of New Canaan [Directions] | New Canaan 154 Trumbull 163 Stamford 213 | ||
| Mon., 4/18 | FR Boys Lacrosse | Staples | Away - Staples Stadium [Directions] | 4:00 p.m. | 2:30pm | |
| Mon., 4/18 | V Boys Tennis | Trumbull | Home - NCHS Tennis Courts [Directions] | W 6-1 | ||
| Mon., 4/18 | V Boys Volleyball | Trumbull | Away - THS Main Gym [Directions] | L 2-3 | 2:15pm | |
| Mon., 4/18 | JV Boys Volleyball | Trumbull | Away - THS Main Gym [Directions] | L 1-2 | JV travel with V | |
| Mon., 4/18 | V Softball | Trinity Catholic | Home - Waveny Park - Orchard Field [Directions] | W 12-3 | ||
| Mon., 4/18 | V Girls Tennis | Trumbull | Away - THS Tennis Courts [Directions] | W 6-1 | 2:20pm | |
| Mon., 4/18 | JV Girls Tennis | Greenwich | Away - Binney Park [Directions] | 4:00 p.m. | 2:20pm | |
| Tue., 4/19 | V Boys Golf | Norwalk | Away - Oak Hills G.C. [Directions] | New Canaan 156 Norwalk 208 | 2p | |
| Tue., 4/19 | V Boys Outdoor Track | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 4:00 p.m. | 2@2:20pm | |
| Tue., 4/19 | V Boys Tennis | Westhill | Home - NCHS Tennis Courts [Directions] | W 5-2 | ||
| Tue., 4/19 | V Girls Golf | Trumbull | Home - Country Club of New Canaan [Directions] | NC-202 Trumbull-234 Played back 9 at CCNC | ||
| Tue., 4/19 | V Girls Lacrosse | Wilton | Away - Lilly Field - Turf [Directions] | W 14-10 | 2:30pm Var & JV ride together | |
| Tue., 4/19 | JV Girls Lacrosse | Wilton | Away - Lilly Field - Turf [Directions] | 4:30 p.m. | 2:30pm Var & JV ride together | |
| Tue., 4/19 | V Girls Outdoor Track | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 4:00 p.m. | 2@2:20pm | |
| Tue., 4/19 | JV Softball | Trumbull | Away - JV Softball Field [Directions] | 4:15 p.m. | 2:20 pm | |
| Tue., 4/19 | V Girls Tennis | Westhill | Away - Westhill Tennis Courts [Directions] | W 6-1 | 2:20pm | |
| Wed., 4/20 | V Baseball | Trumbull | Home - Mead Park [Directions] | L 6-10 | ||
| Wed., 4/20 | JV Baseball | Trumbull | Home - Waveny Park - Coppo Field [Directions] | 4:00 p.m. | ||
| Wed., 4/20 | FR Baseball | Trumbull | Away - Varsity Baseball Field [Directions] | 4:00 p.m. | 2:15pm | |
| Wed., 4/20 | V Boys Golf | Fairfield Warde | Home - Country Club of New Canaan [Directions] | New Canaan 165 Fairfield Warde 183 | ||
| Wed., 4/20 | V Boys Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | W 10-6 | 3:00pm | |
| Wed., 4/20 | JV Boys Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 4:30 p.m. | 2:30pm | |
| Wed., 4/20 | FR Boys Lacrosse | Fairfield Ludlowe | Away - Sturges Park [Directions] | 5:00 p.m. | 3:00pm | |
| Wed., 4/20 | V Boys Volleyball | Staples | Home - NCHS Gymnasium [Directions] | L 0-3 | ||
| Wed., 4/20 | JV Boys Volleyball | Staples | Home - NCHS Gymnasium [Directions] | L 1-2 | ||
| Wed., 4/20 | V Softball | Trumbull | Away - Varsity Softball Field [Directions] | W 2-0 | 2:20pm | |
| Thu., 4/21 | V Baseball | Westhill | Home - Mead Park [Directions] | W 2-1 | ||
| Thu., 4/21 | JV Baseball | Westhill | Home - Conner Field [Directions] | 4:00 p.m. | ||
| Thu., 4/21 | FR Baseball | Westhill | Away - Westhill Baseball Field [Directions] | 4:00 p.m. | 2:20pm | |
| Thu., 4/21 | V Boys Lacrosse | Greenwich | Away - Cardinal Stadium [Directions] | W 8-6 | 2:15pm | |
| Thu., 4/21 | JV Boys Lacrosse | Greenwich | Away - GHS Field 7 [Directions] | 4:00 p.m. | 2:15pm | |
| Thu., 4/21 | V Boys Outdoor Track | Greenwich | Home - NCHS Track Field [Directions] | 4:00 p.m. | ||
| Thu., 4/21 | V Boys Tennis | Norwalk | Away - Norwalk HS [Directions] | W 5-2 | 2:20pm | |
| Thu., 4/21 | V Boys Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | W 3-0 | 2:30pm | |
| Thu., 4/21 | JV Boys Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | W 2-0 | JV travel with V | |
| Thu., 4/21 | V Girls Golf | Darien | Home - Country Club of New Canaan [Directions] | NC-196 Darien-203 | ||
| Thu., 4/21 | JV Girls Lacrosse | Norwalk | Home - Dunning Stadium [Directions] | 5:30 p.m. | ||
| Thu., 4/21 | V Girls Outdoor Track | Greenwich | Home - NCHS Track Field [Directions] | 4:00 p.m. | ||
| Thu., 4/21 | V Softball | Westhill | Away - Westhill Varsity Softball Field [Directions] | L 4-11 | 2:20pm | |
| Thu., 4/21 | V Girls Tennis | Norwalk | Home - NCHS Tennis Courts [Directions] | W 7-0 | ||
| Fri., 4/22 | FR Boys Lacrosse | Fairfield Warde | Home - Saxe MS Field [Directions] | 4:00 p.m. | ||
| Fri., 4/22 | FR Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde Grass Utility Field [Directions] | 4:00 p.m. | 2:30pm | |
| Fri., 4/22 | JV Softball | Westhill | Away - Roxbury Elementary School [Directions] | 4:00 p.m. | 2:20 pm | |
| Sat., 4/23 | V Boys Lacrosse | St. Joseph | Away - St. Joseph HS [Directions] | W 11-4 | 10:00am | |
| Sat., 4/23 | JV Boys Lacrosse | St. Joseph | Away - St. Joseph HS [Directions] | 2:00 p.m. | 12:00pm | |
| Mon., 4/25 | V Baseball | Norwalk | Away - Nathan Hale M.S. Upper [Directions] | L 0-5 | 2:30pm | |
| Mon., 4/25 | JV Baseball | Norwalk | Away - City Hall Field [Directions] | 4:00 p.m. | JV travels with V | |
| Mon., 4/25 | FR Baseball | Norwalk | Home - Waveny Park - Coppo Field [Directions] | 4:00 p.m. | ||
| Mon., 4/25 | V Boys Golf | Trinity Catholic | Away - Sterling Farms | New Canaan 161 Trinity Catholic 190 | 2p | pick up in lot between Dunning & School |
| Mon., 4/25 | JV Boys Golf | Ridgefield | Home - Country Club of New Canaan [Directions] | NC 167 Ridgefield 178 Staples 174 | ||
| Mon., 4/25 | FR Boys Lacrosse | Norwalk | Home - Saxe MS Field [Directions] | 4:00 p.m. | ||
| Mon., 4/25 | V Boys Outdoor Track | St. Joseph, Brien McMahon | Home - NCHS Track Field [Directions] | 4:00 p.m. | ||
| Mon., 4/25 | V Boys Tennis | Fairfield Ludlowe | Away - FLHS Tennis Courts [Directions] | W 7-0 | 2:20pm | |
| Mon., 4/25 | JV Boys Tennis | Fairfield Ludlowe | Away - Dwight Elementary School Courts [Directions] | 5:00 p.m. | 4:00pm | |
| Mon., 4/25 | V Boys Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | L 1-3 | 2:15pm | |
| Mon., 4/25 | JV Boys Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | L 1-2 | JV travel with V | |
| Mon., 4/25 | V Girls Golf | Staples | Away - Longshore [Directions] | NC-205 Staples-189 | 2p | V & JV will travel together |
| Mon., 4/25 | JV Girls Golf | Staples | Away - Longshore [Directions] | 3:00 p.m. | 2p | |
| Mon., 4/25 | V Girls Lacrosse | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | W 16-5 | 2:30pm Var & JV ride together | |
| Mon., 4/25 | JV Girls Lacrosse | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 5:30 p.m. | 2:30pm Var & JV ride together | |
| Mon., 4/25 | V Girls Outdoor Track | St. Joseph, Brien McMahon | Home - NCHS Track Field [Directions] | 4:00 p.m. | ||
| Mon., 4/25 | V Softball | Norwalk | Home - Waveny Park - Orchard Field [Directions] | W 9-6 | ||
| Mon., 4/25 | JV Softball | Norwalk | Home - Waveny Park - Orchard Field [Directions] | 4:00 p.m. | ||
| Mon., 4/25 | V Girls Tennis | Fairfield Ludlowe | Home - NCHS Tennis Courts [Directions] | W 7-0 | ||
| Mon., 4/25 | JV Girls Tennis | Fairfield Ludlowe | Away - Tomlinson MS Tennis Courts [Directions] | 4:00 p.m. | 2:20pm | |
| Tue., 4/26 | V Boys Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | New Canaan 161 Fairfield Ludlowe 174 | 2p | Pick-up in lot between Dunning & School |
| Tue., 4/26 | V Boys Lacrosse | Staples | Home - Dunning Stadium [Directions] | W 7-4 | ||
| Tue., 4/26 | JV Boys Lacrosse | Staples | Home - Dunning Stadium [Directions] | 4:00 p.m. | ||
| Wed., 4/27 | V Baseball | Fairfield Ludlowe | Away - Kiwanis Field [Directions] | W 13-12 | 2:15pm | |
| Wed., 4/27 | JV Baseball | Fairfield Ludlowe | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | JV travels with V | |
| Wed., 4/27 | FR Baseball | Fairfield Ludlowe | Home - Waveny Park - Coppo Field [Directions] | 4:00 p.m. | ||
| Wed., 4/27 | FR Boys Lacrosse | Wilton | Home - Dunning Stadium [Directions] | 6:30 p.m. | ||
| Wed., 4/27 | V Boys Tennis | Ridgefield | Home - NCHS Tennis Courts [Directions] | W 6-1 | ||
| Wed., 4/27 | V Boys Volleyball | St. Joseph | Home - NCHS Gymnasium [Directions] | W 3-0 | ||
| Wed., 4/27 | JV Boys Volleyball | St. Joseph | Home - NCHS Gymnasium [Directions] | W 2-1 | ||
| Wed., 4/27 | V Girls Golf | Fairfield Ludlowe | Home - Country Club of New Canaan [Directions] | NC-191 Ludlowe-236 | ||
| Wed., 4/27 | JV Girls Golf | Fairfield Ludlowe | Home - Country Club of New Canaan [Directions] | 3:00 p.m. | ||
| Wed., 4/27 | FR Girls Lacrosse | Wilton | Away - Allen's Field [Directions] | 4:00 p.m. | 2:45pm | |
| Wed., 4/27 | V Softball | Fairfield Ludlowe | Home - Waveny Park - Orchard Field [Directions] | L 1-6 | ||
| Wed., 4/27 | JV Softball | Fairfield Ludlowe | Home - Waveny Park - Orchard Field [Directions] | 4:00 p.m. | ||
| Wed., 4/27 | V Girls Tennis | Ridgefield | Away - RHS Tennis Courts [Directions] | W 4-3 | 2:20pm | |
| Wed., 4/27 | JV Girls Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | 2:20pm | |
| Thu., 4/28 | V Boys Golf | Brunswick School | Away - Round Hill Club | New Canaan 155 | ||
| Thu., 4/28 | V Boys Tennis | Fairfield Warde | Home - NCHS Tennis Courts [Directions] | W 7-0 | ||
| Thu., 4/28 | V Girls Lacrosse | Brien McMahon | Home - Dunning Stadium [Directions] | W 21-5 | ||
| Thu., 4/28 | JV Girls Lacrosse | Brien McMahon | Home - Dunning Stadium [Directions] | Cancelled | ||
| Thu., 4/28 | V Girls Outdoor Track | O'Grady Relays | Away - Danbury HS | 6:00 p.m. | 3:45pm | |
| Thu., 4/28 | V Girls Tennis | Fairfield Warde | Away [Directions] | W 6-1 | 2:20pm | |
| Thu., 4/28 | JV Girls Tennis | Fairfield Warde | Away - Fairfield Woods MS Courts [Directions] | 4:00 p.m. | 2:20pm | |
| Fri., 4/29 | V Baseball | Ridgefield | Home - Mead Park [Directions] | L 1-3 | ||
| Fri., 4/29 | JV Baseball | Ridgefield | Home - Waveny Park - Coppo Field [Directions] | 4:00 p.m. | ||
| Fri., 4/29 | FR Baseball | Ridgefield | Away - Governor's Park Field (aka Ciuccoli or Old HS) [Directions] | 4:00 p.m. | 2:15pm | |
| Fri., 4/29 | FR Boys Lacrosse | Darien | Home - Dunning Stadium [Directions] | 6:30 p.m. | ||
| Fri., 4/29 | V Boys Outdoor Track | O'Grady Relays | Away - Danbury | 6:00 p.m. | 3:45pm | |
| Fri., 4/29 | V Boys Volleyball | Darien | Home - NCHS Gymnasium [Directions] | W 3-2 | ||
| Fri., 4/29 | JV Boys Volleyball | Darien | Home - NCHS Gymnasium [Directions] | W 2-1 | ||
| Fri., 4/29 | FR Girls Lacrosse | Darien | Away - DHS Field #1 -Turf [Directions] | 4:00 p.m. | 2:45pm | |
| Fri., 4/29 | V Girls Outdoor Track | O'Grady Relays | Away - Dsnbury HS | 9:00 a.m. | 6:45am | |
| Fri., 4/29 | V Softball | Ridgefield | Away - RHS Upper Grass Field [Directions] | W 4-3 | 2:05pm | |
| Fri., 4/29 | JV Softball | Ridgefield | Away - RHS Upper Grass Field [Directions] | 4:00 p.m. | 2:05 pm | |
| Sat., 4/30 | V Boys Lacrosse | Darien | Away - DHS Stadium Field [Directions] | L 7-10 | 11:15am | |
| Sat., 4/30 | JV Boys Lacrosse | Darien | Away - DHS Turf #2 [Directions] | 10:30 a.m. | 9:00am | |
| Sat., 4/30 | V Boys Outdoor Track | O'Grady Relay | Away - Danbury | 9:00 a.m. | 6:30am | |
| Mon., 5/2 | V Baseball | Fairfield Warde | Home - Mead Park [Directions] | L 0-4 | ||
| Mon., 5/2 | JV Baseball | Fairfield Warde | Home - Waveny Park - Coppo Field [Directions] | 4:00 p.m. | ||
| Mon., 5/2 | FR Baseball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 4:00 p.m. | 2:15pm | |
| Mon., 5/2 | V Boys Golf | Brien McMahon | Away - Brien McMahon HS [Directions] | New Canaan 153 Brien McMahon 231 | 2p | pick-up in lot between Dunning & school |
| Mon., 5/2 | JV Boys Golf | Darien, Brien McMahon | Home - Country Club of New Canaan [Directions] | 4/6/16 NC 156 Staples 170 | ||
| Mon., 5/2 | JV Boys Golf | Darien, Brien McMahon | Home - Country Club of New Canaan [Directions] | NC 172 Darien 179 | ||
| Mon., 5/2 | FR Boys Lacrosse | Trumbull | Home - Saxe MS Field [Directions] | 4:00 p.m. | ||
| Mon., 5/2 | V Girls Outdoor Track | Fairfield Ludlowe, Norwalk | Away - Taft Field [Directions] | 4:00 p.m. | 2@2:20pm | |
| Mon., 5/2 | V Softball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | L 2-7 | 2:20pm | |
| Mon., 5/2 | JV Softball | Fairfield Warde | Away - Melville Park [Directions] | 4:00 p.m. | 2:20 pm | |
| Tue., 5/3 | V Boys Golf | Westhill | Away - Hubbard Brennan Golf Course [Directions] | New Canaan 154 Westhill 168 | 2p | pick-up in lot between Dunning & school |
| Tue., 5/3 | V Boys Lacrosse | Fairfield Ludlowe | Home - Dunning Stadium [Directions] | W 14-4 | ||
| Tue., 5/3 | JV Boys Lacrosse | Fairfield Ludlowe | Home - Saxe MS Field [Directions] | 4:30 p.m. | ||
| Tue., 5/3 | V Boys Outdoor Track | Fairfield Ludlowe, Norwalk | Away - Taft Field [Directions] | 4:00 p.m. | 2@2:20pm | |
| Tue., 5/3 | V Girls Lacrosse | Ridgefield | Home - Dunning Stadium [Directions] | W 15-11 | ||
| Tue., 5/3 | JV Girls Lacrosse | Ridgefield | Home - NCHS Water Tower Turf Field [Directions] | 5:30 p.m. | ||
| Tue., 5/3 | FR Girls Lacrosse | Trumbull | Home - NCHS Water Tower Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 5/4 | V Boys Golf | Wilton | Home - Country Club of New Canaan [Directions] | New Canaan 159 Wilton 182 | ||
| Wed., 5/4 | JV Boys Golf | Wilton | Home - Country Club of New Canaan [Directions] | NC 183 Wilton 210 | ||
| Wed., 5/4 | FR Boys Lacrosse | Greenwich | Away - GHS Field 7 [Directions] | 4:00 p.m. | 2:20pm | |
| Wed., 5/4 | V Boys Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | W 3-1 | 2:10pm | |
| Wed., 5/4 | JV Boys Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | W 2-0 | JV travel with V | |
| Wed., 5/4 | V Girls Golf | Fairfield Ludlowe, Fairfield Warde | Away - Smith Richardson Golf Course [Directions] | NC-202 Warde-178 Ludlowe-231 | 2p | V & JV will ride together. |
| Wed., 5/4 | JV Girls Golf | Fairfield Warde | Away - South Pine Creek- Par 3 [Directions] | 3:12 p.m. | ||
| Wed., 5/4 | V Girls Outdoor Track | Freshman/Sophomore Invite | Away - Darien HS | 4:00 p.m. | 2:20pm | |
| Thu., 5/5 | V Boys Lacrosse | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | W 10-1 | 4:15pm | |
| Thu., 5/5 | JV Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde Grass Utility Field [Directions] | 5:30 p.m. | 3:30pm | |
| Thu., 5/5 | V Boys Tennis | St. Joseph | Away [Directions] | W 7-0 | 2:20pm | |
| Thu., 5/5 | V Girls Golf | Bunnell | Home - Country Club of New Canaan [Directions] | NC-199 Bunnell-272 | ||
| Thu., 5/5 | V Girls Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | W 13-10 | 2:30pm Var & JV ride together | |
| Thu., 5/5 | JV Girls Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | 3:45 p.m. | 2:30pm Var & JV ride together | |
| Thu., 5/5 | FR Girls Lacrosse | Greenwich | Home - Dunning Stadium [Directions] | TBA | ||
| Thu., 5/5 | V Girls Tennis | St. Joseph | Home - NCHS Tennis Courts [Directions] | W 7-0 | ||
| Thu., 5/5 | JV Girls Tennis | Staples | Away - Town Farms Tennis Courts [Directions] | 4:00 p.m. | 2:20pm | |
| Fri., 5/6 | FR Boys Lacrosse | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 4:30 p.m. | 2:15pm | |
| Fri., 5/6 | V Boys Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | L 0-3 | 2:15pm | |
| Fri., 5/6 | JV Boys Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | L 1-2 | JV travel with V | |
| Fri., 5/6 | V Girls Outdoor Track | Yellow Jacket Midnight Invite | Away | Cancelled | 2:45pm | |
| Fri., 5/6 | JV Softball | Staples | Away - Staples HS - Softball Field [Directions] | 4:00 p.m. | 2:20 pm | |
| Sat., 5/7 | V Boys Lacrosse | Brien McMahon | Home - Dunning Stadium [Directions] | W 14-1 | ||
| Sat., 5/7 | JV Boys Lacrosse | Brien McMahon | Home - Dunning Stadium [Directions] | 5:00 p.m. | ||
| Sat., 5/7 | V Girls Lacrosse | Yorktown (NY) | Away | W 13-12 | 1:00pm | |
| Sat., 5/7 | JV Girls Lacrosse | Yorktown (NY) | Away | 5:00 p.m. | 3:00pm | |
| Sat., 5/7 | V Girls Outdoor Track | Middletown Invitational | Away - Middletown HS | 1:00 p.m. | 10:30am | |
| Mon., 5/9 | V Baseball | St. Joseph | Away - St. Joseph HS [Directions] | L 1-3 | 2:15pm | |
| Mon., 5/9 | JV Baseball | St. Joseph | Away - Madison MS, Trumbull [Directions] | 4:00 p.m. | JV travel with V | |
| Mon., 5/9 | FR Baseball | St. Joseph | Home - Conner Field [Directions] | 4:00 p.m. | ||
| Mon., 5/9 | JV Boys Golf | Wilton | Away - Rolling Hills CC [Directions] | NC 183 Wilton 217 | 2p | pick-up at lot between Dunning & School |
| Mon., 5/9 | V Boys Outdoor Track | Wilton | Home - NCHS Track Field [Directions] | 4:00 p.m. | ||
| Mon., 5/9 | V Boys Tennis | Bridgeport Central | Home - NCHS Tennis Courts [Directions] | W 7-0 | ||
| Mon., 5/9 | JV Boys Tennis | Darien | Away - Cherry Lawn Park [Directions] | 5:00 p.m. | 4:00pm | |
| Mon., 5/9 | V Boys Volleyball | Trumbull | Home - NCHS Gymnasium [Directions] | L 1-3 | ||
| Mon., 5/9 | JV Boys Volleyball | Trumbull | Home - NCHS Gymnasium [Directions] | L 1-2 | ||
| Mon., 5/9 | V Girls Golf | Ridgefield | Away - Ridgefield Public GC (DHLY Ridge) [Directions] | NC-191 Ridgefield-194 | ||
| Mon., 5/9 | V Girls Outdoor Track | Wilton | Home - NCHS Track Field [Directions] | 4:00 p.m. | ||
| Mon., 5/9 | V Softball | St. Joseph | Home - Waveny Park - Orchard Field [Directions] | L 3-5 | ||
| Mon., 5/9 | JV Softball | St. Joseph | Home - Waveny Park - Orchard Field [Directions] | 4:00 p.m. | ||
| Mon., 5/9 | V Girls Tennis | Bridgeport Central | Away [Directions] | W 7-0 | 2:20pm | |
| Mon., 5/9 | JV Girls Tennis | Darien | Away - Weed Beach [Directions] | 4:00 p.m. | 2:20pm | |
| Tue., 5/10 | V Baseball | Staples | Home - Mead Park [Directions] | L 0-8 | ||
| Tue., 5/10 | JV Baseball | Staples | Home - Waveny Park - Coppo Field [Directions] | 4:00 p.m. | ||
| Tue., 5/10 | FR Baseball | Staples | Away - Staples HS Baseball Field [Directions] | 4:00 p.m. | 2:30pm | |
| Tue., 5/10 | V Boys Golf | Ridgefield | Home - Country Club of New Canaan [Directions] | New Canaan 157 Ridgefield 161 | ||
| Tue., 5/10 | JV Boys Golf | Fairfield Ludlowe | Away [Directions] | NC 169 Warde 204 Ludlowe 181 | 2p | Pick-up at lot between Dunning & school |
| Tue., 5/10 | V Boys Lacrosse | Trinity Catholic | Home - Dunning Stadium [Directions] | W 16-1 | ||
| Tue., 5/10 | V Boys Tennis | Wilton | Away - Wilton Tennis Courts [Directions] | W 5-2 | 2:45pm | |
| Tue., 5/10 | JV Boys Tennis | Wilton | Away - Wilton Tennis Courts [Directions] | 4:00 p.m. | 2:45pm | Varsity & JV ride together |
| Tue., 5/10 | V Girls Golf | Fairfield Warde | Home - Country Club of New Canaan [Directions] | NC-188 Warde-200 | ||
| Tue., 5/10 | JV Girls Golf | Trumbull | Away [Directions] | 3:00 p.m. | 2p | Pick-up in lot between Dunning & School |
| Tue., 5/10 | V Girls Lacrosse | Darien | Away - DHS Stadium Field [Directions] | L 10-20 | 2:45pm Var & JV ride together | |
| Tue., 5/10 | JV Girls Lacrosse | Darien | Away - DHS Stadium Field [Directions] | 5:30 p.m. | 2:45pm Var & JV ride together | |
| Tue., 5/10 | FR Girls Lacrosse | Norwalk | Home - NCHS Water Tower Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 5/10 | V Softball | Staples | Home - Waveny Park - Orchard Field [Directions] | W 9-7 | ||
| Tue., 5/10 | V Girls Tennis | Wilton | Home - NCHS Tennis Courts [Directions] | W 4-3 | ||
| Tue., 5/10 | JV Girls Tennis | Wilton | Away - Wilton Tennis Courts [Directions] | 4:00 p.m. | 2:20pm | |
| Wed., 5/11 | V Baseball | Bridgeport Central | Home - Mead Park [Directions] | W 6-1 | ||
| Wed., 5/11 | JV Baseball | Bridgeport Central | Home - Waveny Park - Coppo Field [Directions] | 4:00 p.m. | ||
| Wed., 5/11 | V Boys Golf | Danbury | Home - Country Club of New Canaan [Directions] | New Canaan 160 Danbury 163 | ||
| Wed., 5/11 | JV Boys Golf | Brien McMahon | Away - Oak Hills [Directions] | Cancelled | 2P | Pick-up at lot between Dunning & school |
| Wed., 5/11 | FR Boys Lacrosse | Greenwich | Home - Saxe MS Field [Directions] | 4:00 p.m. | ||
| Wed., 5/11 | V Boys Tennis | Staples | Home - NCHS Tennis Courts [Directions] | L 0-7 | ||
| Wed., 5/11 | V Boys Volleyball | Staples | Away - Staples H.S. Gym [Directions] | L 1-3 | 2:20pm | |
| Wed., 5/11 | JV Boys Volleyball | Staples | Away - Staples H.S. Gym [Directions] | L 1-2 | JV travel with V | |
| Wed., 5/11 | V Softball | Bridgeport Central | Away - Central H.S. Junior Varsity Softball Field [Directions] | W 2-1 | 2:15pm | |
| Wed., 5/11 | JV Softball | Bridgeport Central | Away - Cal Ripken Field at Longfellow Park on Ocean Terrace, Bridgeport [Directions] | Cancelled | 2:15 pm | |
| Wed., 5/11 | V Girls Tennis | Staples | Away - Staples HS-Tennis Courts [Directions] | L 5-2 | 2:20pm | |
| Thu., 5/12 | JV Baseball | Wilton | Away - JV Baseball Field [Directions] | 4:15 p.m. | 2:30pm | |
| Thu., 5/12 | V Boys Outdoor Track | Loucks Games | Away - White Plains HS | 5:00 p.m. | 3:00p | |
| Thu., 5/12 | V Boys Tennis | Danbury | Home - NCHS Tennis Courts [Directions] | W 7-0 | ||
| Thu., 5/12 | JV Boys Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | Cancelled | ||
| Thu., 5/12 | V Boys Volleyball | Greenwich | Home - NCHS Gymnasium [Directions] | W 3-1 | ||
| Thu., 5/12 | JV Boys Volleyball | Greenwich | Home - NCHS Gymnasium [Directions] | W 2-1 | ||
| Thu., 5/12 | V Girls Golf | Greenwich | Away - Millbrook Country Club [Directions] | NC-210 Greenwich-186 | 1:15p | Pick-up in lot between Dunning & school |
| Thu., 5/12 | V Girls Lacrosse | Norwalk | Home - Dunning Stadium [Directions] | W 15-3 | ||
| Thu., 5/12 | FR Girls Lacrosse | Fairfield Warde | Home - NCHS Water Tower Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 5/12 | V Girls Outdoor Track | Loucks Games | Away - White Plains | 5:00 p.m. | 3:00pm | |
| Thu., 5/12 | V Softball | Wilton | Home - Waveny Park - Orchard Field [Directions] | L 2-6 | ||
| Thu., 5/12 | JV Softball | Wilton | Home - Waveny Park - Orchard Field [Directions] | Cancelled | ||
| Thu., 5/12 | V Girls Tennis | Danbury | Away - Danbury HS Tennis Courts [Directions] | W 7-0 | 2:05pm | |
| Thu., 5/12 | JV Girls Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 3:30 p.m. | 2:15pm | |
| Fri., 5/13 | V Baseball | Wilton | Away - WHS Varsity Baseball Field [Directions] | L 0-1 | 12:45pm | |
| Fri., 5/13 | FR Baseball | Wilton | Home - Waveny Park - Coppo Field [Directions] | Cancelled | ||
| Fri., 5/13 | FR Boys Lacrosse | Wilton | Away - Fujitani Field - Turf [Directions] | 5:00 p.m. | 2:30pm | |
| Fri., 5/13 | V Boys Outdoor Track | Loucks Games | Away | 3:00 p.m. | ||
| Fri., 5/13 | FR Girls Lacrosse | Wilton | Home - NCHS Water Tower Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 5/13 | V Girls Outdoor Track | Loucks Games | Away - White Plains | 3:00 p.m. | ||
| Sat., 5/14 | V Boys Lacrosse | St. Anthonys (NY) | Home - Dunning Stadium [Directions] | L 8-3 | ||
| Sat., 5/14 | V Boys Outdoor Track | Loucks games | Away - White Plains HS | 9:00 a.m. | ||
| Sat., 5/14 | V Girls Outdoor Track | Loucks Games | Away - White Plains | 9:00 a.m. | ||
| Mon., 5/16 | V Baseball | Danbury | Home - Mead Park [Directions] | L 3-7 | ||
| Mon., 5/16 | JV Baseball | Danbury | Home - Waveny Park - Coppo Field [Directions] | 4:00 p.m. | ||
| Mon., 5/16 | FR Baseball | Danbury | Away - Danbury HS Varsity Baseball Field [Directions] | 4:00 p.m. | 2:15pm | |
| Mon., 5/16 | V Boys Golf | Bridgeport Central | Away - Fairchild Wheeler [Directions] | New Canaan 170 Bridgeport Central 226 | ||
| Mon., 5/16 | JV Boys Lacrosse | St. Anthonys (NY) | Home - Dunning Stadium [Directions] | 5:00 p.m. | ||
| Mon., 5/16 | V Boys Tennis | Greenwich | Away - GHS Tennis Courts [Directions] | L 1-6 | 2:20pm | |
| Mon., 5/16 | JV Boys Tennis | Greenwich | Away - Central MS [Directions] | 5:00 p.m. | 4:00pm | |
| Mon., 5/16 | V Boys Volleyball | Fairfield Warde | Home - NCHS Gymnasium [Directions] | L 2-3 | ||
| Mon., 5/16 | JV Boys Volleyball | Fairfield Warde | Home - NCHS Gymnasium [Directions] | W 2-0 | ||
| Mon., 5/16 | V Girls Golf | Darien | Away - Wee Burn CC [Directions] | NC-210 Darien-206 | 2p | V & JV will ride in Van together. |
| Mon., 5/16 | JV Girls Golf | Darien | Away - Wee Burn CC [Directions] | 3:30 p.m. | 2p | |
| Mon., 5/16 | FR Girls Lacrosse | Ridgefield | Away - RHS Lower Grass Field [Directions] | 4:00 p.m. | 2:30pm | |
| Mon., 5/16 | V Girls Outdoor Track | Darien | Away - DHS Stadium Field [Directions] | 4:00 p.m. | 2@2:20pm | |
| Mon., 5/16 | V Softball | Danbury | Away - Danbury HS Varsity Softball Field [Directions] | L 8-9 | 2:05pm | |
| Mon., 5/16 | JV Softball | Danbury | Away - Danbury HS Junior Varsity Softball Field [Directions] | 4:00 p.m. | 2:05 pm | |
| Mon., 5/16 | V Girls Tennis | Greenwich | Home - NCHS Tennis Courts [Directions] | W 4-3 | ||
| Mon., 5/16 | JV Girls Tennis | Greenwich | Away - Binney Park [Directions] | 4:00 p.m. | 2:20pm | |
| Tue., 5/17 | V Boys Golf | Darien | Away - CC of Darien [Directions] | Darien 159 New Canaan 166 | 2p | Pick-up in lot between Dunning & school |
| Tue., 5/17 | V Boys Lacrosse | Ridgefield | Home - Dunning Stadium [Directions] | L 7-3 | ||
| Tue., 5/17 | JV Boys Lacrosse | Ridgefield | Home - Dunning Stadium [Directions] | 4:30 p.m. | ||
| Tue., 5/17 | V Boys Outdoor Track | Darien | Away - DHS Stadium Field [Directions] | 4:00 p.m. | 2@2:20pm | |
| Tue., 5/17 | JV Boys Tennis | Darien | Away - Cherry Lawn Park [Directions] | 5:00 p.m. | 4:00pm | |
| Tue., 5/17 | V Girls Lacrosse | Longmeadow (MA) | Away | L 6-14 | 2:15pm | |
| Tue., 5/17 | V Softball | Staples | Away - Greens Farms Elementary School [Directions] | L 3-8 | 4:30pm | |
| Wed., 5/18 | V Baseball | Greenwich | Away - GHS Baseball Field [Directions] | W 7-1 | 2:15pm | |
| Wed., 5/18 | JV Baseball | Greenwich | Away - Julian Curtiss School [Directions] | 4:00 p.m. | JV travel with V | |
| Wed., 5/18 | FR Baseball | Greenwich | Home - Waveny Park - Coppo Field [Directions] | 4:00 p.m. | ||
| Wed., 5/18 | V Boys Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | Greenwich 155 New Canaan 157 | 2p | pick-up in lot between Dunning & school |
| Wed., 5/18 | JV Boys Golf | Darien | Away - Woodway CC [Directions] | NC 173 Darien 165 | 2p | pick-up in lot between Dunning & school |
| Wed., 5/18 | V Boys Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | W 3-0 | 2:15pm | |
| Wed., 5/18 | JV Boys Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | W 2-0 | JV travel with V | |
| Wed., 5/18 | V Girls Golf | Danbury | Home - Country Club of New Canaan [Directions] | NC-194 Danbury-219 | ||
| Wed., 5/18 | JV Girls Golf | Danbury | Home - Country Club of New Canaan [Directions] | 3:00 p.m. | ||
| Wed., 5/18 | V Softball | Greenwich | Home - Waveny Park - Orchard Field [Directions] | W 6-3 | ||
| Wed., 5/18 | JV Softball | Greenwich | Home - Waveny Park - Orchard Field [Directions] | 4:00 p.m. | ||
| Thu., 5/19 | V Baseball | New Fairfield | Home - Mead Park [Directions] | L 0-6 | ||
| Thu., 5/19 | V Boys Golf | St. Joseph | Away - Tashua Knolls, Trumbull [Directions] | New Canaan 168 St. Joseph 188 | ||
| Thu., 5/19 | FR Boys Lacrosse | Darien | Away - DHS Field #1 -Turf [Directions] | 4:00 p.m. | 2:30pm | |
| Thu., 5/19 | V Boys Tennis | Westhill | Home - NCHS Tennis Courts [Directions] | W 4-0 | ||
| Thu., 5/19 | V Girls Golf | Ridgefield | Home - Country Club of New Canaan [Directions] | NC-192 Ridgefield-213 | ||
| Thu., 5/19 | JV Girls Golf | Greenwich | Away [Directions] | Cancelled | 2p | pick-up in lot between Dunning & school |
| Thu., 5/19 | V Girls Lacrosse | Norwalk | Home - Dunning Stadium [Directions] | 5:00 p.m. | ||
| Thu., 5/19 | FR Girls Lacrosse | New Canaan Country Day | Away | 4:00 p.m. | 2:45pm | |
| Fri., 5/20 | JV Boys Tennis | Staples | Away - Town Farms Tennis Courts [Directions] | 4:00 p.m. | 3:00pm | |
| Fri., 5/20 | FR Girls Lacrosse | Staples | Home - NCHS Water Tower Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 5/20 | V Girls Tennis | Staples | Away [Directions] | L 4-3 | 12:45pm | |
| Sat., 5/21 | V Boys Lacrosse | Wilton | Home - Dunning Stadium [Directions] | W 7-6 | ||
| Sat., 5/21 | V Boys Outdoor Track | Bethel | Away - Bethel [Directions] | 12:00 p.m. | 10:00am | |
| Sat., 5/21 | V Girls Outdoor Track | FCIAC's | Away - Bethel HS | 10:00 a.m. | 10:00am | |
| Mon., 5/23 | JV Boys Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | 3:15 p.m. | 2p | pick-up in lot between Dunning & school |
| Mon., 5/23 | V Boys Tennis | Staples | Away [Directions] | 4:00 p.m. | ||
| Mon., 5/23 | V Girls Lacrosse | Ridgefield | Home - Dunning Stadium [Directions] | 5:00 p.m. | ||
| Tue., 5/24 | V Boys Lacrosse | Ridgefield | Away - Brien McMahon H.S. [Directions] | W 10-7 | ||
| Tue., 5/24 | V Girls Golf | Wilton | Home - Country Club of New Canaan [Directions] | NC-203 Wilton-213 *Wilton player had a hole in one on par 3, 7th hole-153 yards! | ||
| Wed., 5/25 | V Boys Golf | Staples, Brien McMahon | Away - Longshore [Directions] | Staples 146 New Canaan 154 | ||
| Wed., 5/25 | JV Boys Golf | Darien, Greenwich | Home - Country Club of New Canaan [Directions] | 3:15 p.m. | ||
| Wed., 5/25 | JV Girls Golf | JV Championship | Away | 3:00 p.m. | 2p | Pick-up in lot between Dunning & School |
| Wed., 5/25 | V Softball | Ridgefield (Scrim.) | Home [Directions] | 4:00 p.m. | ||
| Thu., 5/26 | JV Boys Golf | Ridgefield | Away - Ridgefield Public GC (DHLY Ridge) [Directions] | 3:15 p.m. | 2p | pick-up in lot between Dunning & school |
| Thu., 5/26 | V Boys Lacrosse | Darien | Away [Directions] | L 9-5 | ||
| Thu., 5/26 | V Girls Lacrosse | Darien | Away [Directions] | 4:00 p.m. | ||
| Thu., 5/26 | V Softball | Norwalk (Scrim.) | Home [Directions] | 4:00 p.m. | ||
| Tue., 5/31 | V Girls Lacrosse | Lauralton Hall | Home - Dunning Stadium [Directions] | W 20-11 | ||
| Tue., 5/31 | V Softball | Bristol Central | Away [Directions] | 4:00 p.m. | ||
| Wed., 6/1 | V Boys Lacrosse | Avon | Home - Dunning Stadium [Directions] | W 17-4 | ||
| Wed., 6/1 | V Boys Volleyball | Rockville | Away - RHS Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 6/2 | V Girls Lacrosse | New Fairfield | Home - Dunning Stadium [Directions] | W 11-8 | ||
| Sat., 6/4 | V Boys Lacrosse | North Haven | Home - Dunning Stadium [Directions] | W 8-2 | ||
| Tue., 6/7 | V Girls Lacrosse | CIAC Semi-Finals | Away | TBA | ||
| Wed., 6/8 | V Boys Lacrosse | CIAC Semi-Finals | Away | TBA | ||
| Sat., 6/11 | V Boys Lacrosse | CIAC Finals | Away | TBA | ||
| Sat., 6/11 | V Girls Lacrosse | CIAC Finals | Away | TBA | ||