| New Canaan 2014-15 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 968 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| TBA | JV Baseball | Darien (Scrim.) | Away - DHS Baseball JV Field [Directions] | 3:30 p.m. | ||
| TBA | JV Baseball | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | 2:30 Var & JV ride together | |
| TBA | JV Boys Ice Hockey | Darien | Away - Darien Ice Rink [Directions] | 2:50 p.m. | ||
| TBA | V Boys Indoor Track | SCC Coaches Invitational Meet | Away - Floyd Little Athletic Center | 9:00 a.m. | 7:00am | |
| TBA | V Boys Indoor Track | Qualifier #4 | Away - Wilton | 9:30 a.m. | ||
| TBA | FR Boys Lacrosse | Staples | Home - Saxe Middle School Field [Directions] | 4:00 p.m. | ||
| TBA | FR Boys Lacrosse | Fairfield Ludlowe | Home - NCHS Water Tower Turf Field [Directions] | TBA | ||
| TBA | FR Boys Soccer | Ridgefield | Home - Saxe Middle School Field [Directions] | TBA | Black | |
| TBA | V Boys Tennis | Guilford (Scrim.) | Home - NCHS Tennis Courts [Directions] | TBA | ||
| TBA | JV Boys Tennis | Fairfield Ludlowe | Away - Dwight Elementary School Courts [Directions] | 4:00 p.m. | 3:00pm | |
| TBA | JV Girls Basketball | Greenwich Country Day | Away | 4:30 p.m. | 3:00pm | |
| TBA | V Girls Gymnastics | Staples, Westhill | Away [Directions] | 101.75 | 3:30pm | |
| TBA | JV Girls Lacrosse | Fairfield Warde | Home - NCHS Water Tower Turf Field [Directions] | 4:30 p.m. | ||
| TBA | FR Girls Lacrosse | Greenwich | Home - NCHS Water Tower Turf Field [Directions] | 4:00 p.m. | ||
| TBA | JV Girls Soccer | Harding | Away - Seaside Park [Directions] | 4:00 p.m. | 2:15pm | |
| TBA | JV Girls Soccer | Danbury | Home - Saxe Middle School Field [Directions] | Cancelled | ||
| TBA | FR Girls Soccer | Danbury | Away - Danbury High School Grass Field [Directions] | Cancelled | 2:15pm | |
| Thu., 8/28 | V Girls Soccer | Scarsdale (NY) (Scrim.) | Home - Conner Field [Directions] | 4:00 p.m. | ||
| Thu., 8/28 | JV Girls Soccer | Scarsdale (NY) (Scrim.) | Home - Saxe Middle School Field [Directions] | W 3-1 | ||
| Thu., 8/28 | FR Girls Soccer | Staples (Scrim.) | Home - Saxe Middle School Field [Directions] | 4:00 p.m. | ||
| Fri., 8/29 | V Boys Soccer | Rye Country Day (NY) (Scrim.) | Away | 4:00 p.m. | 2:15pm | |
| Sat., 8/30 | V Football | Jamboree | Home - Dunning Stadium [Directions] | 9:00 a.m. | ||
| Sat., 8/30 | FR Football | Stepinac (NY) (Scrim.) | Away | 12:30 a.m. | 10:30am | |
| Mon., 9/1 | V Field Hockey | Mamaroneck Jamboree | Away - Flint Park, Larchmont, NY | 8:30 a.m. | 7:00am | |
| Tue., 9/2 | V Girls Soccer | Bronxville (NY) (Scrim.) | Home - Conner Field [Directions] | 4:00 p.m. | ||
| Tue., 9/2 | JV Girls Soccer | Bronxville (NY) (Scrim.) | Home - Saxe Middle School Field [Directions] | W 3-0 | ||
| Wed., 9/3 | JV Boys Soccer | Weston (Scrim.) | Home - Saxe Middle School Field [Directions] | 4:00 p.m. | ||
| Thu., 9/4 | V Boys Soccer | St. Lukes (Scrim.) | Home - Conner Field [Directions] | 4:00 p.m. | ||
| Thu., 9/4 | FR Boys Soccer | St. Lukes (Scrim.) | Home - Saxe Middle School Field [Directions] | 4:00 p.m. | ||
| Thu., 9/4 | V Field Hockey | Fairfield Warde (Scrim.) | Home - NCHS Water Tower Turf Field [Directions] | 3:30 p.m. | ||
| Thu., 9/4 | V Girls Soccer | Shelton (Scrim.) | Away - Shelton High School Finn Stadium [Directions] | 4:00 p.m. | 2:20pm Var & JV Ride Together | |
| Thu., 9/4 | JV Girls Soccer | Shelton (Scrim.) | Away - Shelton High School - Upper Field [Directions] | L 6-0 | 2:20pm Var & JV Ride Together | |
| Fri., 9/5 | V Football | MT ST Michaels | Home - Dunning Stadium [Directions] | 4:00 p.m. | ||
| Fri., 9/5 | FR Football | Westhill (Scrim.) | Home - Dunning Stadium [Directions] | 3:00 p.m. | ||
| Fri., 9/5 | JV Field Hockey | New Fairfield Jamboree | Away | 4:00 p.m. | 2:15pm | |
| Sat., 9/6 | V Field Hockey | New Fairfield Jamboree | Away | 9:30 a.m. | 7:45am | |
| Sat., 9/6 | V Girls Volleyball | Staples Tournament | Away | 9:00 a.m. | 7:20am | |
| Tue., 9/9 | V Boys Cross Country | Ridgefield, St. Joseph, Westhill, Trinity Catholic | Home - Waveny Park [Directions] | 4:00 p.m. | ||
| Tue., 9/9 | V Boys Soccer | Brien McMahon | Home - Conner Field [Directions] | T 1-1 | ||
| Tue., 9/9 | JV Boys Soccer | Brien McMahon | Home - Saxe Middle School Field [Directions] | 4:00 p.m. | ||
| Tue., 9/9 | V Girls Cross Country | Ridgefield, St. Joseph, Westhill, Trinity Catholic | Home - Waveny Park [Directions] | 4:00 p.m. | ||
| Tue., 9/9 | V Field Hockey | Wilton | Home - Dunning Stadium [Directions] | L 1-4 | ||
| Tue., 9/9 | JV Field Hockey | Wilton | Home - Dunning Stadium [Directions] | L 2-0 | ||
| Tue., 9/9 | FR Field Hockey | Wilton | Away - Wilton High School - Grass Field [Directions] | 4:00 p.m. | 2:45pm | |
| Wed., 9/10 | V Girls Soccer | St. Joseph | Home - Dunning Stadium [Directions] | L 0-3 | ||
| Wed., 9/10 | JV Girls Soccer | St. Joseph | Home - Conner Field [Directions] | W 2-1 | ||
| Wed., 9/10 | V Girls Volleyball | Norwalk | Away - Norwalk High Gym [Directions] | W 3-0 | 2:45pm Var & JV ride together | |
| Wed., 9/10 | JV Girls Volleyball | Norwalk | Away - Norwalk High Gym [Directions] | W 2-0 | 2:45pm Var & JV ride together | |
| Thu., 9/11 | FR Football | Daniel Hand | Home - Dunning Stadium [Directions] | L 30-13 | ||
| Thu., 9/11 | V Boys Soccer | Norwalk | Home - Conner Field [Directions] | L 0-2 | ||
| Thu., 9/11 | JV Boys Soccer | Norwalk | Home - Saxe Middle School Field [Directions] | 4:00 p.m. | ||
| Thu., 9/11 | FR Boys Soccer | Norwalk | Away - City Hall Field [Directions] | 4:00 p.m. | 2:45pm | Red |
| Thu., 9/11 | FR Girls Soccer | Masuk | Away - Masuk Middle Field [Directions] | 4:15 p.m. | 2:30pm | |
| Fri., 9/12 | V Football | Daniel Hand | Away - Surf Club [Directions] | W 21-14 | 3:00pm 1 Var & 1 Cheer | |
| Fri., 9/12 | V Girls Soccer | Westhill | Home - Conner Field [Directions] | W 2-0 | ||
| Fri., 9/12 | JV Girls Soccer | Westhill | Home - Saxe Middle School Field [Directions] | W 2-1 | ||
| Fri., 9/12 | FR Girls Soccer | Darien | Away - Middlesex Lower Field [Directions] | 4:00 p.m. | 3:00pm | |
| Fri., 9/12 | V Girls Swimming and Diving | Staples, Trumbull | Away - Staples HS Pool [Directions] | 6:00 p.m. | 3:30pm | |
| Fri., 9/12 | V Girls Volleyball | Harding | Home - NCHS Gymnasium [Directions] | W 3-0 | ||
| Fri., 9/12 | JV Girls Volleyball | Harding | Home - NCHS Gymnasium [Directions] | W 2-0 | ||
| Sat., 9/13 | V Boys Cross Country | Wilton Invitational | Away | 8:30 a.m. | 7:45am | |
| Sat., 9/13 | JV Football | Daniel Hand | Away - DHHS Turf Field [Directions] | W 14-12 | 7:45am | |
| Sat., 9/13 | V Girls Cross Country | Wilton Invitational | Away | 8:30 a.m. | 7:45am | |
| Mon., 9/15 | FR Boys Soccer | Wilton | Home - Saxe Middle School Field [Directions] | 4:30 p.m. | Red | |
| Mon., 9/15 | V Field Hockey | Fairfield Ludlowe | Home - Dunning Stadium [Directions] | W 2-0 | ||
| Mon., 9/15 | JV Field Hockey | Fairfield Ludlowe | Home - Dunning Stadium [Directions] | L 1-0 | ||
| Mon., 9/15 | FR Field Hockey | Fairfield Ludlowe | Away - FLHS Front Lawn [Directions] | 4:00 p.m. | 2:30pm | |
| Mon., 9/15 | V Girls Soccer | Ridgefield | Away - Tiger Hollow Stadium [Directions] | L 0-1 | 2:20pm Var & JV Ride Together | |
| Mon., 9/15 | JV Girls Soccer | Ridgefield | Away - RHS Lower Grass Field [Directions] | L 4-1 | 2:20pm Var & JV Ride Together | |
| Mon., 9/15 | FR Girls Soccer | Ridgefield | Home - Saxe Middle School Field [Directions] | 4:00 p.m. | ||
| Mon., 9/15 | V Girls Volleyball | Fairfield Warde | Home - NCHS Gymnasium [Directions] | W 3-2 | ||
| Mon., 9/15 | JV Girls Volleyball | Fairfield Warde | Home [Directions] | L 0-2 | ||
| Mon., 9/15 | FR Girls Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | L 3-0 | 2:30pm | |
| Tue., 9/16 | V Boys Cross Country | Staples, Trinity Catholic, Norwalk, Brien McMahon | Home - Waveny Park [Directions] | 4:00 p.m. | ||
| Tue., 9/16 | V Boys Soccer | Westhill | Away - Westhill Front Turf Field [Directions] | L 0-3 | 3:00pm | |
| Tue., 9/16 | JV Boys Soccer | Westhill | Away - Rippowam Middle School [Directions] | 4:00 p.m. | 2:30pm | |
| Tue., 9/16 | FR Boys Soccer | Westhill | Home - Saxe Middle School Field [Directions] | 4:00 p.m. | Black | |
| Tue., 9/16 | V Girls Cross Country | Staples, Trinity Catholic, Norwalk, Brien McMahon | Home - Waveny Park [Directions] | 4:00 p.m. | ||
| Wed., 9/17 | V Girls Soccer | Staples | Away - Loeffler Field - Staples HS [Directions] | T 1-1 | 2:15pm Var & JV Ride Together | |
| Wed., 9/17 | JV Girls Soccer | Staples | Away - Wakeman Field B (turf) [Directions] | L 2-0 | 2:15pm Var & JV Ride Together | |
| Wed., 9/17 | FR Girls Soccer | Staples | Home - Saxe Middle School Field [Directions] | 4:00 p.m. | ||
| Wed., 9/17 | V Girls Swimming and Diving | St. Joseph | Away - Hillcrest MS, Trumbull, CT [Directions] | 4:00 p.m. | 2:05pm | |
| Wed., 9/17 | V Girls Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | L 0-3 | 2:30pm Var & JV ride together | |
| Wed., 9/17 | JV Girls Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | L 0-2 | 2:30pm Var & JV ride together | |
| Wed., 9/17 | FR Girls Volleyball | Greenwich | Home - NCHS Gymnasium [Directions] | L 3-1 | ||
| Thu., 9/18 | V Field Hockey | Danbury | Away - Danbury High School Stadium [Directions] | W 6-2 | 2:15pm | |
| Thu., 9/18 | JV Field Hockey | Danbury | Away - Danbury High School Grass Field [Directions] | W 4-0 | 3:00pm | |
| Thu., 9/18 | FR Field Hockey | Danbury | Home - NCHS Water Tower Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 9/19 | V Football | Bassick | Home - Dunning Stadium [Directions] | W 43-6 | Youth Football Night | |
| Fri., 9/19 | V Girls Soccer | Greenwich | Home - Conner Field [Directions] | W 3-2 | ||
| Fri., 9/19 | JV Girls Soccer | Greenwich | Home - Saxe Middle School Field [Directions] | L 1-0 | ||
| Fri., 9/19 | V Girls Volleyball | Staples | Away - Staples H.S. Gym [Directions] | L 2-3 | 2:30pm Var & JV ride together | |
| Fri., 9/19 | JV Girls Volleyball | Staples | Away - Staples H.S. Gym [Directions] | L 2-0 | 2:30pm Var & JV ride together | |
| Fri., 9/19 | FR Girls Volleyball | Staples | Home - NCHS Gymnasium [Directions] | L 0-3 | ||
| Sat., 9/20 | V Boys Cross Country | Brewster Bear Classic | Away - Brewster High School | 9:20 a.m. | 7:15am | |
| Sat., 9/20 | V Girls Cross Country | Brewster Bear Classic | Away - Brewster High School | 9:00 a.m. | 7:15am | |
| Mon., 9/22 | JV Football | Bassick | Home [Directions] | Cancelled | ||
| Mon., 9/22 | V Boys Soccer | Darien | Home - Conner Field [Directions] | W 2-0 | ||
| Mon., 9/22 | JV Boys Soccer | Darien | Home - Saxe Middle School Field [Directions] | 4:00 p.m. | ||
| Mon., 9/22 | FR Boys Soccer | Darien | Away - Middlesex Upper Field [Directions] | 4:00 p.m. | 2:45pm | Red |
| Mon., 9/22 | V Field Hockey | Westhill | Away - Westhill Front Turf Field [Directions] | W 4-0 | 2:15pm | |
| Mon., 9/22 | JV Field Hockey | Westhill | Away - Westhill Front Turf Field [Directions] | W 3-1 | 4:00pm | |
| Mon., 9/22 | V Girls Volleyball | Westhill | Home - NCHS Gymnasium [Directions] | W 3-2 | ||
| Mon., 9/22 | JV Girls Volleyball | Westhill | Home - NCHS Gymnasium [Directions] | W 2-1 | ||
| Mon., 9/22 | FR Girls Volleyball | Westhill | Away - Westhill - Main Gymnasium [Directions] | L 1-3 | 2:45pm | |
| Tue., 9/23 | V Boys Cross Country | Wilton, Danbury, Trinity Catholic, Trumbull, Bridgeport Central | Home [Directions] | 4:00 p.m. | ||
| Tue., 9/23 | SO Football | Brunswick School | Away - King Street Greenwich | L 18-19 | 2:30pm | |
| Tue., 9/23 | V Girls Cross Country | Wilton, Danbury, Trinity Catholic, Trumbull, Bridgeport Central | Home [Directions] | 4:00 p.m. | ||
| Tue., 9/23 | FR Field Hockey | Westhill | Home - NCHS Track Field [Directions] | Cancelled | ||
| Tue., 9/23 | V Girls Soccer | Norwalk | Home - Dunning Stadium [Directions] | W 4-0 | ||
| Tue., 9/23 | FR Girls Soccer | Greenwich | Away - GHS Field 7 [Directions] | 4:30 p.m. | 2:15pm | |
| Tue., 9/23 | V Girls Swimming and Diving | Wilton | Home - New Canaan YMCA [Directions] | 3:00 p.m. | ||
| Wed., 9/24 | V Boys Soccer | Harding | Away - Harding-Hedges Field-Bridgeport [Directions] | W 5-0 | 2:15pm | |
| Wed., 9/24 | V Field Hockey | Darien | Home - Dunning Stadium [Directions] | L 3-5 | ||
| Wed., 9/24 | JV Field Hockey | Darien | Home - Dunning Stadium [Directions] | L 3-1 | ||
| Wed., 9/24 | FR Field Hockey | Darien | Away - DHS Baseball Varsity Field [Directions] | 3:00 p.m. | 2:15pm | |
| Wed., 9/24 | V Girls Volleyball | Brien McMahon | Home - NCHS Gymnasium [Directions] | L 1-3 | ||
| Wed., 9/24 | JV Girls Volleyball | Brien McMahon | Home - NCHS Gymnasium [Directions] | Cancelled | ||
| Fri., 9/26 | V Girls Soccer | Fairfield Warde | Home - Conner Field [Directions] | L 0-1 | ||
| Fri., 9/26 | JV Girls Soccer | Fairfield Warde | Home - Saxe Middle School Field [Directions] | L 3-0 | ||
| Fri., 9/26 | FR Girls Soccer | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | 2:30pm | |
| Sat., 9/27 | V Football | Greenwich | Home - Dunning Stadium [Directions] | W 35-20 | Homecoming | |
| Sat., 9/27 | FR Football | Greenwich | Away - GHS Field 7 [Directions] | W 14-0 | 7:15am | |
| Sat., 9/27 | V Boys Soccer | Danbury | Home - Conner Field [Directions] | L 1-5 | Homecoming Game | |
| Sat., 9/27 | JV Boys Soccer | Danbury | Home - Dunning Stadium [Directions] | 10:00 a.m. | ||
| Sat., 9/27 | FR Boys Soccer | Danbury | Away - Danbury High School Stadium [Directions] | 11:00 a.m. | 9:00am | Red |
| Sat., 9/27 | V Field Hockey | Stamford | Away - Stamford High School [Directions] | W 7-0 | 8:30am | |
| Sat., 9/27 | JV Field Hockey | Stamford | Away - Stamford High School [Directions] | W 6-0 | 10:00am | |
| Mon., 9/29 | JV Football | Greenwich | Home - NCHS Water Tower Turf Field [Directions] | W 21-13 | ||
| Mon., 9/29 | FR Boys Soccer | Greenwich | Home - Saxe Middle School Field [Directions] | 4:00 p.m. | Black | |
| Mon., 9/29 | V Field Hockey | Trumbull | Home - Dunning Stadium [Directions] | W 4-1 | ||
| Mon., 9/29 | JV Field Hockey | Trumbull | Home - Dunning Stadium [Directions] | T 0-0 | ||
| Mon., 9/29 | FR Field Hockey | Trumbull | Away - Field Hockey Grass Field [Directions] | 4:00 p.m. | 2:15pm | |
| Mon., 9/29 | V Girls Volleyball | Danbury | Away - Danbury High School - MAIN gym [Directions] | W 3-1 | 2:15pm Var & JV ride together | |
| Mon., 9/29 | JV Girls Volleyball | Danbury | Away - Danbury High School - MAIN gym [Directions] | L 0-2 | 2:15pm Var & JV ride together | |
| Mon., 9/29 | FR Girls Volleyball | Danbury | Home - NCHS Gymnasium [Directions] | L 0-3 | ||
| Tue., 9/30 | V Boys Cross Country | Greenwich, Stamford, Trinity Catholic, Darien | Away - Greenwich Point [Directions] | 4:00 p.m. | 2:45pm | |
| Tue., 9/30 | V Boys Soccer | Staples | Away - Loeffler Field - Staples HS [Directions] | T 1-1 | 2:15pm | |
| Tue., 9/30 | JV Boys Soccer | Staples | Away - Wakeman Field E (grass) [Directions] | 4:00 p.m. | 2:30pm | |
| Tue., 9/30 | FR Boys Soccer | Staples | Home - Saxe Middle School Field [Directions] | 4:00 p.m. | Red | |
| Tue., 9/30 | V Girls Cross Country | Greenwich, Stamford, Trinity Catholic, Darien | Away - Greenwich Point [Directions] | 4:00 p.m. | 2:15pm | |
| Tue., 9/30 | FR Girls Soccer | Greenwich | Home - Saxe Middle School Field [Directions] | 4:00 p.m. | ||
| Wed., 10/1 | V Girls Soccer | Trinity Catholic | Away - Trinity Catholic Soccer Field | W 7-0 | 2:15pm | |
| Wed., 10/1 | V Girls Swimming and Diving | Fairfield Ludlowe | Away - Fairfield University Rec Plex Pool [Directions] | 3:30 p.m. | 2:05pm | |
| Wed., 10/1 | V Girls Volleyball | Bridgeport Central | Away - Central H.S. Gym [Directions] | W 3-0 | 2:15pm Var & JV ride together | |
| Wed., 10/1 | JV Girls Volleyball | Bridgeport Central | Away - Central H.S. Gym [Directions] | W 2-0 | 2:15pm Var & JV ride together | |
| Thu., 10/2 | V Football | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | W 35-14 | 2@3:15pm Cheer bus - 4:15pm | |
| Thu., 10/2 | FR Football | Fairfield Warde | Home - NCHS Water Tower Turf Field [Directions] | W 29-16 | ||
| Thu., 10/2 | V Boys Soccer | Trinity Catholic | Home - Dunning Stadium [Directions] | W 3-0 | ||
| Thu., 10/2 | V Field Hockey | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | T 1-1 | 2:15pm | |
| Thu., 10/2 | JV Field Hockey | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | Cancelled | 3:15pm | |
| Thu., 10/2 | V Girls Volleyball | Bassick | Home - NCHS Gymnasium [Directions] | W 3-0 | ||
| Thu., 10/2 | JV Girls Volleyball | Bassick | Home [Directions] | W 2-0 | ||
| Fri., 10/3 | SO Football | Greenwich | Home - Dunning Stadium [Directions] | W 34-26 | ||
| Fri., 10/3 | V Girls Soccer | Darien | Away - DHS Turf #2 [Directions] | T 0-0 | 2:15pm Var & JV Ride Together | |
| Fri., 10/3 | JV Girls Soccer | Darien | Away - Middlesex Upper Field [Directions] | L 2-1 | 2:15pm Var & JV Ride Together | |
| Fri., 10/3 | FR Girls Soccer | Darien | Home - Saxe Middle School Field [Directions] | 3:30 p.m. | ||
| Fri., 10/3 | V Girls Swimming and Diving | Danbury | Home - New Canaan YMCA [Directions] | 3:00 p.m. | ||
| Mon., 10/6 | JV Football | Fairfield Warde | Away [Directions] | L 14-30 | 2:15pm | |
| Mon., 10/6 | V Boys Soccer | Trumbull | Away - McDougall Stadium [Directions] | T 0-0 | 4:30pm | |
| Mon., 10/6 | JV Boys Soccer | Trumbull | Away - Varsity Grass Field [Directions] | 5:00 p.m. | 2:45pm | |
| Mon., 10/6 | FR Boys Soccer | Trumbull | Home - Saxe Middle School Field [Directions] | 4:00 p.m. | Red | |
| Mon., 10/6 | V Field Hockey | Ridgefield | Away - Tiger Hollow Stadium [Directions] | W 1-0 | 4:00pm | |
| Mon., 10/6 | JV Field Hockey | Ridgefield | Away - Tiger Hollow Stadium [Directions] | T 1-1 | 2:15pm | |
| Mon., 10/6 | FR Field Hockey | Ridgefield | Home - NCHS Track Field [Directions] | 4:00 p.m. | ||
| Mon., 10/6 | V Girls Volleyball | Darien | Home - NCHS Gymnasium [Directions] | L 0-3 | ||
| Mon., 10/6 | JV Girls Volleyball | Darien | Home - NCHS Gymnasium [Directions] | L 2-0 | ||
| Mon., 10/6 | FR Girls Volleyball | Darien | Away - DHS Main Gym [Directions] | L 0-3 | 3:00pm | |
| Tue., 10/7 | V Boys Cross Country | Fairfield Ludlowe, Fairfield Warde, Bassick, Harding, Trinity Catholic | Away [Directions] | 4:00 p.m. | 2:30pm | |
| Tue., 10/7 | V Girls Cross Country | Fairfield Ludlowe, Fairfield Warde, Bassick, Harding, Trinity Catholic | Away [Directions] | 4:00 p.m. | 2:15pm | |
| Tue., 10/7 | V Girls Soccer | Wilton | Away - Lilly Field - Turf [Directions] | T 1-1 | 2:30pm Var & JV Ride Together | |
| Tue., 10/7 | JV Girls Soccer | Wilton | Away - Allen's Field #2 [Directions] | L 4-1 | 2:30pm Var & JV Ride Together | |
| Tue., 10/7 | FR Girls Soccer | Wilton | Home - Saxe Middle School Field [Directions] | 4:00 p.m. | ||
| Wed., 10/8 | V Boys Soccer | Ridgefield | Home - Dunning Stadium [Directions] | L 0-1 | ||
| Wed., 10/8 | JV Boys Soccer | Ridgefield | Home - Saxe Middle School Field [Directions] | 4:00 p.m. | ||
| Wed., 10/8 | FR Boys Soccer | Ridgefield | Away - RHS Lower Grass Field [Directions] | 4:00 p.m. | 2:15pm | Black |
| Wed., 10/8 | V Girls Swimming and Diving | Darien | Away - Darien YMCA [Directions] | 3:00 p.m. | 1:30pm | |
| Wed., 10/8 | V Girls Volleyball | Wilton | Away - Wilton High School Field House [Directions] | W 3-1 | 2:45pm Var & JV ride together | |
| Wed., 10/8 | JV Girls Volleyball | Wilton | Away - Wilton High School Field House [Directions] | L 2-1 | 2:45pm Var & JV ride together | |
| Thu., 10/9 | V Field Hockey | Norwalk | Home - Dunning Stadium [Directions] | W 2-1 | ||
| Thu., 10/9 | JV Field Hockey | Norwalk | Home - Dunning Stadium [Directions] | W 2-0 | ||
| Thu., 10/9 | FR Field Hockey | Norwalk | Away - NHS Grass Field [Directions] | 4:00 p.m. | 2:45pm | |
| Thu., 10/9 | V Girls Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | W 3-1 | 5:15pm | |
| Thu., 10/9 | JV Girls Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:15 p.m. | 3:45pm | |
| Thu., 10/9 | FR Girls Soccer | Staples | Away - Wakeman Field E (grass) [Directions] | 4:00 p.m. | 2:30pm | |
| Fri., 10/10 | V Football | Danbury | Away - Danbury High School Stadium [Directions] | W 42-14 | 2@3:45pm Cheer bus-4:45pm | |
| Fri., 10/10 | FR Football | Danbury | Home - Dunning Stadium [Directions] | W 22-6 | ||
| Fri., 10/10 | V Boys Soccer | Greenwich | Away - Cardinal Stadium [Directions] | L 0-6 | 2:45pm | |
| Fri., 10/10 | JV Boys Soccer | Greenwich | Away - GHS Field 7 [Directions] | 4:00 p.m. | 2:30pm | |
| Fri., 10/10 | FR Boys Soccer | Greenwich | Home - Saxe Middle School Field [Directions] | 4:00 p.m. | Red | |
| Fri., 10/10 | V Girls Swimming and Diving | Norwalk/McMahon | Home - New Canaan YMCA [Directions] | 3:00 p.m. | ||
| Fri., 10/10 | V Girls Volleyball | Trumbull | Away - THS Main Gym [Directions] | L 2-3 | 2:15pm Var & JV ride together | |
| Fri., 10/10 | JV Girls Volleyball | Trumbull | Away - THS Main Gym [Directions] | L 0-2 | 2:15pm Var & JV ride together | |
| Fri., 10/10 | FR Girls Volleyball | Trumbull | Home - NCHS Gymnasium [Directions] | L 0-3 | ||
| Sat., 10/11 | V Boys Cross Country | Wickham Invitational | Away | 9:30 a.m. | 7:00am | |
| Sat., 10/11 | V Field Hockey | Cheshire | Home - Dunning Stadium [Directions] | L 1-3 | ||
| Sat., 10/11 | V Girls Swimming and Diving | JV Meet VS Greenwich | Away | 9:00 a.m. | ||
| Mon., 10/13 | JV Football | Danbury | Away - Danbury High School Stadium [Directions] | W 19-12 | 2:15pm | |
| Mon., 10/13 | V Boys Soccer | Wilton | Home - Dunning Stadium [Directions] | W 1-0 | ||
| Mon., 10/13 | JV Boys Soccer | Wilton | Home - Saxe Middle School Field [Directions] | 4:00 p.m. | ||
| Tue., 10/14 | V Field Hockey | Stamford | Home - Dunning Stadium [Directions] | W 6-0 | ||
| Tue., 10/14 | JV Field Hockey | Stamford | Home - Dunning Stadium [Directions] | W 5-0 | ||
| Tue., 10/14 | FR Field Hockey | Stamford | Away [Directions] | 4:00 p.m. | 2:45pm | |
| Tue., 10/14 | V Girls Soccer | Trumbull | Away - McDougall Stadium [Directions] | L 0-1 | 4:30pm | |
| Tue., 10/14 | JV Girls Soccer | Trumbull | Away - Varsity Grass Field [Directions] | 5:00 p.m. | 2:30pm | |
| Tue., 10/14 | FR Girls Soccer | Trumbull | Home - Saxe Middle School Field [Directions] | 4:00 p.m. | ||
| Tue., 10/14 | V Girls Volleyball | Trinity Catholic | Home - NCHS Gymnasium [Directions] | W 3-0 | ||
| Tue., 10/14 | JV Girls Volleyball | Trinity Catholic | Home - NCHS Gymnasium [Directions] | L 1-2 | ||
| Wed., 10/15 | SO Football | St. Lukes | Home - Dunning Stadium [Directions] | Cancelled | ||
| Wed., 10/15 | V Boys Soccer | Bassick | Away [Directions] | W 4-1 | 2:15pm | Went Field - Bridgeport |
| Wed., 10/15 | FR Boys Soccer | Wilton | Away - Allen's Field #2 [Directions] | 4:00 p.m. | 2:45pm | Black |
| Wed., 10/15 | V Girls Volleyball | Stamford | Home - NCHS Gymnasium [Directions] | L 1-3 | ||
| Wed., 10/15 | JV Girls Volleyball | Stamford | Home [Directions] | L 0-2 | ||
| Wed., 10/15 | FR Girls Volleyball | Stamford | Away - Stamford High School [Directions] | L 0-3 | 2:45pm | |
| Thu., 10/16 | V Girls Soccer | Danbury | Home - Dunning Stadium [Directions] | W 2-0 | ||
| Fri., 10/17 | JV Boys Soccer | St. Joseph | Away - St. Catherines, Trumbull, CT [Directions] | 4:00 p.m. | 2:15pm | |
| Fri., 10/17 | V Field Hockey | Staples | Home - Dunning Stadium [Directions] | L 0-1 | ||
| Fri., 10/17 | JV Field Hockey | Staples | Home - Dunning Stadium [Directions] | W 3-0 | ||
| Fri., 10/17 | FR Field Hockey | Staples | Away - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | 2:30pm | |
| Fri., 10/17 | V Girls Swimming and Diving | Fairfield Warde | Home - New Canaan YMCA [Directions] | 3:00 p.m. | ||
| Fri., 10/17 | V Girls Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | L 0-3 | 2:30pm Var & JV ride together | |
| Fri., 10/17 | JV Girls Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | W 2-1 | 2:30pm Var & JV ride together | |
| Fri., 10/17 | FR Girls Volleyball | Fairfield Ludlowe | Home - NCHS Gymnasium [Directions] | L 1-3 | ||
| Sat., 10/18 | V Boys Soccer | St. Joseph | Away - St. Joseph High School [Directions] | T 1-1 | 11:45am | |
| Sat., 10/18 | FR Field Hockey | New Canaan Country Day | Away | 11:30 a.m. | 10:15am | |
| Sat., 10/18 | V Girls Soccer | Bridgeport Central | Home - Dunning Stadium [Directions] | W 7-0 | ||
| Sat., 10/18 | JV Girls Soccer | Bassick | Home - Saxe Middle School Field [Directions] | 4:00 p.m. | ||
| Mon., 10/20 | V Boys Cross Country | FCIAC's | Home - Waveny Park [Directions] | 2:00 p.m. | ||
| Mon., 10/20 | JV Football | CT Juvenile Training School | Away - 1225 Silver St., Middletown, CT | 4:30 p.m. | 2:05pm | |
| Mon., 10/20 | V Boys Soccer | Fairfield Ludlowe | Away - Taft Field [Directions] | L 1-3 | 3:30pm | |
| Mon., 10/20 | JV Boys Soccer | Fairfield Ludlowe | Away - Sturges Park [Directions] | 4:00 p.m. | 2:30pm | |
| Mon., 10/20 | FR Boys Soccer | Fairfield Ludlowe | Home - Saxe Middle School Field [Directions] | 4:00 p.m. | Black | |
| Mon., 10/20 | V Girls Cross Country | FCIAC's | Home - Waveny Park [Directions] | 2:00 p.m. | ||
| Mon., 10/20 | V Field Hockey | Greenwich | Away - Cardinal Stadium [Directions] | W 4-1 | 4:00pm | |
| Mon., 10/20 | JV Field Hockey | Greenwich | Away - Cardinal Stadium [Directions] | L 1-0 | 2:30pm | |
| Mon., 10/20 | FR Field Hockey | Greenwich | Home - NCHS Track Field [Directions] | 4:00 p.m. | ||
| Mon., 10/20 | V Girls Volleyball | St. Joseph | Away - St. Joseph High School [Directions] | L 1-3 | 2:30pm | |
| Mon., 10/20 | JV Girls Volleyball | St. Joseph | Away - St. Joseph High School [Directions] | W 2-1 | 2:30pm | |
| Tue., 10/21 | V Girls Soccer | Fairfield Ludlowe | Away - Taft Field [Directions] | L 0-1 | 4:00pm | |
| Tue., 10/21 | JV Girls Soccer | Fairfield Ludlowe | Away - Sturges Park [Directions] | 4:00 p.m. | 2:30pm | |
| Tue., 10/21 | FR Girls Soccer | Fairfield Ludlowe | Home - Saxe Middle School Field [Directions] | 4:00 p.m. | ||
| Wed., 10/22 | V Boys Soccer | Stamford | Home - Dunning Stadium [Directions] | L 3-4 | Senior Night | |
| Wed., 10/22 | JV Boys Soccer | Stamford | Home - Saxe Middle School Field [Directions] | 4:00 p.m. | ||
| Wed., 10/22 | FR Boys Soccer | Stamford | Away - Stamford High Soccer Field [Directions] | 4:00 p.m. | 2:45pm | Red |
| Wed., 10/22 | V Field Hockey | New Milford | Away - Danbury Sports Dome [Directions] | T 2-2 | 2:15pm | |
| Wed., 10/22 | V Girls Swimming and Diving | Greenwich | Away - GHS Pool [Directions] | 3:30 p.m. | 2:05pm | |
| Wed., 10/22 | V Girls Volleyball | Ridgefield | Home - NCHS Gymnasium [Directions] | L 0-3 | Senior Night | |
| Wed., 10/22 | JV Girls Volleyball | Ridgefield | Home - NCHS Gymnasium [Directions] | L 0-2 | ||
| Wed., 10/22 | FR Girls Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | L 1-3 | 2:30pm | |
| Thu., 10/23 | V Boys Cross Country | Hatter Freshman Invitational | Away - Tarrywile Park Danbury | 4:30 p.m. | 2:15pm | |
| Thu., 10/23 | SO Football | Staples | Home - NCHS Water Tower Turf Field [Directions] | Cancelled | ||
| Thu., 10/23 | FR Football | Staples | Away - Staples Stadium [Directions] | W 13-10 | 3:45pm | |
| Thu., 10/23 | V Field Hockey | Brien McMahon | Away - Brien McMahon HS [Directions] | W 4-1 | 5:30pm | |
| Thu., 10/23 | JV Field Hockey | Brien McMahon | Away - Brien McMahon HS [Directions] | W 3-0 | 4:30pm | |
| Thu., 10/23 | V Girls Soccer | Stamford | Home - Dunning Stadium [Directions] | W 4-0 | Senior Night | |
| Thu., 10/23 | JV Girls Soccer | Stamford | Home - NCHS Water Tower Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 10/24 | V Football | Staples | Home - Dunning Stadium [Directions] | W 35-2 | ||
| Fri., 10/24 | V Boys Soccer | FCIAC Playdowns | Away | Cancelled | Rain Date 10/25 | |
| Fri., 10/24 | FR Girls Volleyball | Wilton | Away - Wilton [Directions] | L 0-3 | 2:45pm | |
| Sat., 10/25 | V Boys Cross Country | CIAC Class L Championship | Away - Wickham Park - East Hartford [Directions] | 12:00 p.m. | 7:45am - 1 bus for Boys/Girls | |
| Sat., 10/25 | FR Boys Soccer | Greenwich Country Day | Away | 9:00 a.m. | 7:30am | Black |
| Sat., 10/25 | V Girls Cross Country | CIAC Class L Championship | Away - Wickham Park - East Hartford [Directions] | 11:25 a.m. | 7:45am - 1 bus for Boys/Girls | |
| Sat., 10/25 | V Field Hockey | Fairfield Warde | Home - Dunning Stadium [Directions] | 6:00 p.m. | Rain Date - 10/26 | |
| Sat., 10/25 | FR Field Hockey | Greenwich Country Day | Away | 12:00 p.m. | 10:15am | |
| Sat., 10/25 | V Girls Soccer | St. Joseph | Away - Indian Ledge Park Field [Directions] | W 1-0 | 4:45pm | Rain Date - 10/26 |
| Sat., 10/25 | FR Girls Soccer | Greenwich Country Day | Away | 12:00 p.m. | 10:00am | |
| Sat., 10/25 | V Girls Swimming and Diving | JV FCIAC's @ Greenwich | Away [Directions] | 4:00 p.m. | 2:00pm | |
| Mon., 10/27 | JV Football | Staples | Home - Dunning Stadium [Directions] | W 14-12 | ||
| Mon., 10/27 | V Boys Soccer | FCIAC Semi Finals | Away - Fairfield Ludlowe [Directions] | Cancelled | ||
| Mon., 10/27 | V Girls Soccer | Staples | Away - Wilton [Directions] | 5:00 p.m. | 3:15pm | |
| Mon., 10/27 | V Girls Volleyball | FCIAC Playdowns | Away | Cancelled | ||
| Tue., 10/28 | FR Boys Soccer | New Canaan Country Day | Away | 3:30 p.m. | 2:30pm | Black |
| Tue., 10/28 | V Field Hockey | Wilton | Away - Brien McMahon [Directions] | 5:00 p.m. | 3:30pm | |
| Tue., 10/28 | V Girls Swimming and Diving | FCIAC Trials | Away - Greenwich [Directions] | 4:30 p.m. | 1:30pm | |
| Wed., 10/29 | SO Football | Darien | Away - DHS Baseball Varsity Field [Directions] | L 14-28 | 2:15pm | |
| Wed., 10/29 | V Boys Soccer | Brien McMahon (Scrim.) | Home - Conner Field [Directions] | 3:30 p.m. | ||
| Wed., 10/29 | V Boys Soccer | FCIAC Finals | Away - Norwalk | Cancelled | ||
| Wed., 10/29 | V Girls Soccer | FCIAC Finals | Away - Norwalk | Cancelled | ||
| Wed., 10/29 | V Girls Swimming and Diving | FCIAC Diving | Away | 4:00 p.m. | ||
| Wed., 10/29 | V Girls Volleyball | FCIAC Semi-Finals | Away - Fairfield Ludlowe [Directions] | Cancelled | ||
| Thu., 10/30 | FR Football | St. Joseph | Home - Dunning Stadium [Directions] | W 18-13 | ||
| Thu., 10/30 | V Field Hockey | Darien | Away - Brien McMahon [Directions] | 7:00 p.m. | 5:15pm | |
| Thu., 10/30 | V Girls Swimming and Diving | FCIAC Finals | Away - Greenwich [Directions] | 4:30 p.m. | 1:30pm | |
| Fri., 10/31 | V Boys Cross Country | CIAC Open Championship | Away - Wickham Park - East Hartford [Directions] | 2:45 p.m. | ||
| Fri., 10/31 | V Girls Cross Country | CIAC Open Championship | Away - Wickham Park - East Hartford [Directions] | 2:00 p.m. | ||
| Fri., 10/31 | V Girls Volleyball | Stamford (Scrim.) | Away [Directions] | 3:15 p.m. | 2:30pm | |
| Sat., 11/1 | V Football | St. Joseph | Away - St. Joseph High School [Directions] | W 41-14 | 2@10:45am Cheer bus -11:45am | |
| Sat., 11/1 | V Girls Volleyball | FCIAC Finals | Away - Fairfield Ludlowe | Cancelled | ||
| Mon., 11/3 | JV Football | St. Joseph | Away - St. Joseph High School [Directions] | L 7-14 | 2:15pm | |
| Mon., 11/3 | V Boys Soccer | Platt Tech | Away - Platt Tech soccer field [Directions] | 2:00 p.m. | 11:30am | |
| Mon., 11/3 | V Girls Volleyball | Avon | Away - Avon High School [Directions] | 6:00 p.m. | 3:15pm | |
| Mon., 11/3 | Miscellaneous Events | Unified Sports | Away - Staples | 3:30 p.m. | 2:05pm | |
| Tue., 11/4 | V Field Hockey | Bethel | Away [Directions] | 5:00 p.m. | 2:30pm | |
| Tue., 11/4 | V Girls Soccer | Daniel Hand | Away - DHHS Turf Field [Directions] | W 1-0 | 1:15pm | |
| Wed., 11/5 | SO Football | Greenwich | Away - Cardinal Stadium [Directions] | L 7-14 | 2:15pm | |
| Wed., 11/5 | V Boys Soccer | Guilford | Away - Bittner Park - Guilford [Directions] | 5:00 p.m. | 2:00pm | |
| Wed., 11/5 | V Girls Swimming and Diving | CIAC Class L Diving Trials/Finals | Away - Middletown HS [Directions] | 5:30 p.m. | 2:00pm | |
| Thu., 11/6 | FR Football | Wilton | Home - NCHS Water Tower Turf Field [Directions] | L 21-15 | ||
| Thu., 11/6 | V Girls Soccer | East Lyme | Away [Directions] | W 2-1 | 1:00pm | |
| Fri., 11/7 | V Football | Wilton | Home - Dunning Stadium [Directions] | W 47-7 | ||
| Fri., 11/7 | V Field Hockey | Daniel Hand | Away - DHHS Turf Field [Directions] | 4:00 p.m. | 1:00pm | |
| Sat., 11/8 | V Boys Cross Country | New England Championship | Away - Wickham Park - East Hartford [Directions] | TBA | ||
| Sat., 11/8 | V Girls Cross Country | New England Championship | Away - Wickham Park - East Hartford [Directions] | TBA | ||
| Sat., 11/8 | V Girls Soccer | Mercy | Away - Mercy [Directions] | 2:00 p.m. | 11:30am | |
| Sat., 11/8 | V Girls Swimming and Diving | CIAC Class L Qualifying | Away - Cornerstone Pool [Directions] | 6:15 p.m. | 2:30pm | |
| Mon., 11/10 | JV Football | Wilton | Home - Dunning Stadium [Directions] | Cancelled | ||
| Wed., 11/12 | SO Football | Staples | Away - Staples Stadium [Directions] | T 14-14 | 4:15pm | |
| Wed., 11/12 | V Girls Swimming and Diving | CIAC Class L Finals | Away - SCSU [Directions] | 6:00 p.m. | 2:05pm | |
| Thu., 11/13 | FR Football | Trinity Catholic | Home - Dunning Stadium [Directions] | W 20-16 | ||
| Thu., 11/13 | V Girls Swimming and Diving | CIAC Open Diving | Away - Middletown HS [Directions] | 5:30 p.m. | ||
| Sat., 11/15 | V Football | Trinity Catholic | Away - Trinity Catholic Alumni Field | W 47-16 | 2@10:45am Cheer bus-11:30am | |
| Sat., 11/15 | V Girls Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 7:30 p.m. | 4:00pm | |
| Tue., 11/18 | SO Football | Greenwich | Home - NCHS Water Tower Turf Field [Directions] | W 28-14 | ||
| Tue., 11/18 | SO Football | Greenwich | Home - NCHS Water Tower Turf Field [Directions] | Cancelled | ||
| Thu., 11/20 | FR Football | Darien | Home - Dunning Stadium [Directions] | L 22-0 | ||
| Sat., 11/22 | JV Football | Darien | Away - DHS Stadium Field [Directions] | L 14-21 | 9:15am | |
| Thu., 11/27 | V Football | Darien | Away - Boyle Stadium/Stamford [Directions] | L 21-28 (OT) | 2@8:15am Cheer bus-9:00am | |
| Tue., 12/2 | V Girls Basketball | Greens Farms Academy (Scrim.) | Home - NCHS Gymnasium [Directions] | 5:00 p.m. | ||
| Thu., 12/4 | V Boys Ice Hockey | East Haven Coop (Scrim.) | Away - DiLungo Rink [Directions] | 3:30 p.m. | 2:05pm | |
| Thu., 12/4 | V Girls Basketball | Trinity Catholic (Scrim.) | Home - NCHS Gymnasium [Directions] | 3:00 p.m. | ||
| Sat., 12/6 | V Football | Wethersfield | Home - Dunning Stadium [Directions] | 2:00 p.m. | ||
| Sat., 12/6 | V Girls Basketball | Weston (Scrim.) | Away - WHS Gymnasium [Directions] | 3:00 p.m. | 2:00pm | |
| Sat., 12/6 | V Girls Ice Hockey | Jamboree | Away - Shelton Rinks | 1:00 p.m. | ||
| Mon., 12/8 | V Boys Basketball | Stratford (Scrim.) | Home - NCHS Gymnasium [Directions] | 3:00 p.m. | ||
| Wed., 12/10 | V Boys Ice Hockey | Greenwich (Scrim.) | Away - Dorothy Hamill Ice Rink [Directions] | 8:30 p.m. | 7:00pm | |
| Wed., 12/10 | V Girls Basketball | St. Joseph | Away - St. Joseph High School [Directions] | L 17-56 | 3:15pm Var & JV ride together | |
| Wed., 12/10 | JV Girls Basketball | St. Joseph | Away - St. Joseph High School [Directions] | 5:15 p.m. | 3:15pm Var & JV ride together | |
| Wed., 12/10 | FR Girls Basketball | St. Joseph | Away - St. Joseph High School [Directions] | L 2-48 | 2:30pm | |
| Fri., 12/12 | V Girls Basketball | Stamford | Home - NCHS Gymnasium [Directions] | L 42-69 | ||
| Fri., 12/12 | JV Girls Basketball | Stamford | Home - NCHS Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 12/12 | FR Girls Basketball | Stamford | Home - NCHS Gymnasium [Directions] | L 14-19 | ||
| Sat., 12/13 | V Boys Basketball | St. Anthonys (NY) (Scrim.) | Home - NCHS Gymnasium [Directions] | 10:00 a.m. | ||
| Sat., 12/13 | V Football | Darien | Away - West Haven [Directions] | 10:30 a.m. | 7:15am | |
| Sat., 12/13 | V Boys Ice Hockey | Jamboree | Away - Terry Connors Ice Rink | TBA | ||
| Mon., 12/15 | V Boys Basketball | Joel Barlow (Scrim.) | Home - NCHS Gymnasium [Directions] | 5:00 p.m. | ||
| Mon., 12/15 | JV Boys Ice Hockey | Darien | Away - Stamford Twin Rinks [Directions] | 3:00 p.m. | ||
| Mon., 12/15 | V Girls Ice Hockey | Darien | Away [Directions] | L 3-8 | ||
| Wed., 12/17 | V Boys Basketball | Trumbull | Away - THS Main Gym [Directions] | L 40-73 | 3:30pm Var & JV Ride Together | |
| Wed., 12/17 | JV Boys Basketball | Trumbull | Away - THS Main Gym [Directions] | 5:15 p.m. | 3:30pm Var & JV Ride Together | |
| Wed., 12/17 | FR Boys Basketball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | 2:05pm | |
| Wed., 12/17 | V Boys Ice Hockey | Notre Dame-West Haven | Home - Darien Ice Rink [Directions] | W 4-3(OT) | ||
| Wed., 12/17 | V Boys Swimming and Diving | Trumbull | Away - Hillcrest Middle School [Directions] | 4:00 p.m. | 2:05pm | |
| Wed., 12/17 | V Wrestling | Fairfield Warde | Away - Fairfield Warde Small Gym [Directions] | Loss NC 6 Warde 78 | 2:30pm | |
| Wed., 12/17 | V Girls Basketball | Trumbull | Home - NCHS Gymnasium [Directions] | L 19-52 | ||
| Wed., 12/17 | JV Girls Basketball | Trumbull | Home - NCHS Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 12/17 | FR Girls Basketball | Trumbull | Home - NCHS Gymnasium [Directions] | L 10-30 | ||
| Fri., 12/19 | V Boys Basketball | Brien McMahon | Home - NCHS Gymnasium [Directions] | L 53-72 | ||
| Fri., 12/19 | JV Boys Basketball | Brien McMahon | Home - NCHS Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 12/19 | FR Boys Basketball | Brien McMahon | Home - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 12/19 | V Boys Indoor Track | New Haven Varsity Invitational | Away - Hillhouse | 4:30 p.m. | 2:05pm | |
| Fri., 12/19 | V Boys Indoor Track | New Haven Varsity Invitational | Away - Hillhouse | 4:30 p.m. | 2:05pm | |
| Fri., 12/19 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Home - New Canaan YMCA [Directions] | 3:00 p.m. | ||
| Fri., 12/19 | V Girls Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | W 41-31 | 2:30pm Var & JV ride together | |
| Fri., 12/19 | JV Girls Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | 2:30pm Var & JV ride together | |
| Sat., 12/20 | V Boys Ice Hockey | Hamden | Away - Lou Astorino Ice Rink [Directions] | L 4-7 | 12:00pm | |
| Sat., 12/20 | V Boys Indoor Track | Qualifier #1 | Away - Staples | 10:00 a.m. | 1@8:30am | |
| Sat., 12/20 | V Wrestling | Pomperaug Tournament | Away [Directions] | 9:00 a.m. | 6:45am | |
| Sat., 12/20 | JV Wrestling | Trumbull JV Tournament | Away [Directions] | 9:00 a.m. | 7:30am | |
| Sat., 12/20 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away [Directions] | W 4-3 | 5:30pm | |
| Sat., 12/20 | JV Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - Sono Ice Rink [Directions] | 11:50 a.m. | 10:30am | |
| Sat., 12/20 | V Girls Indoor Track | Qualifier #1 | Away - Staples | 10:00 a.m. | 1@8:30am | |
| Mon., 12/22 | V Boys Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | L 59-70 | 3:30pm Var & JV Ride Together | |
| Mon., 12/22 | JV Boys Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 5:15 p.m. | 3:30pm Var & JV Ride Together | |
| Mon., 12/22 | FR Boys Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 4:00 p.m. | 2:05pm | |
| Mon., 12/22 | V Girls Basketball | Bridgeport Central | Home - NCHS Gymnasium [Directions] | W 36-34 | ||
| Mon., 12/22 | JV Girls Basketball | Bridgeport Central | Home - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 12/22 | V Girls Ice Hockey | Simsbury | Home - Darien Ice Rink [Directions] | L 0-2 | ||
| Tue., 12/23 | V Boys Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | L 2-3(OT) | 2:05pm | |
| Tue., 12/23 | V Girls Ice Hockey | Hall/Conard | Home - Darien Ice Rink [Directions] | W 4-0 | ||
| Sat., 12/27 | V Boys Basketball | Litchfield | Away - Litchfield High School [Directions] | W 53-44 | 4:30pm | Snow Date-Dec 29 |
| Sat., 12/27 | V Boys Ice Hockey | Darien | Home - Darien Ice Rink [Directions] | L 3-6 | ||
| Sat., 12/27 | V Boys Indoor Track | Hillhouse Christmas Relays | Away | 10:00 a.m. | 7:45am | |
| Sat., 12/27 | V Girls Basketball | Staples | Home - NCHS Gymnasium [Directions] | L 26-39 | ||
| Mon., 12/29 | V Boys Basketball | Cromwell | Away - Litchfield High School [Directions] | W 39-24 | 4:00pm | |
| Mon., 12/29 | V Girls Basketball | Darien | Away - DHS Main Gym [Directions] | W 35-23 | 10:00am | Consolations will be at 11:00am, finals at 1:00. |
| Tue., 12/30 | V Wrestling | Danbury, Fairfield Ludlowe, Staples | Away - Danbury High School - MAIN gym [Directions] | Loss NC 0 Danbury 82 Loss NC 6 Ludlowe 60 Loss NC 33 Staples 34 | 6:45am | |
| Tue., 12/30 | V Girls Ice Hockey | Greenwich | Home - Darien Ice Rink [Directions] | W 6-2 | ||
| Fri., 1/2 | JV Boys Ice Hockey | Greenwich | Home - Darien Ice Rink [Directions] | 11:00 a.m. | ||
| Fri., 1/2 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton Rinks [Directions] | W 9-2 | 3:00pm | |
| Fri., 1/2 | JV Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Darien Ice Rink [Directions] | 9:40 a.m. | ||
| Sat., 1/3 | JV Boys Ice Hockey | Darien | Home - Darien Ice Rink [Directions] | Cancelled | ||
| Sat., 1/3 | JV Wrestling | Norwalk JV Tournament | Away [Directions] | 9:00 a.m. | 7:30am | |
| Mon., 1/5 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Home - Darien Ice Rink [Directions] | W 6-2 | ||
| Wed., 1/7 | V Boys Ice Hockey | Notre Dame-West Haven | Away - Bennett Rink [Directions] | W 2-1 | 2:05pm | |
| Wed., 1/7 | V Wrestling | Norwalk | Home - NCHS Gymnasium [Directions] | Loss 42-29 | ||
| Wed., 1/7 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Darien Ice Rink [Directions] | W 6-3 | ||
| Thu., 1/8 | V Girls Gymnastics | Wilton, Westhill | Home - Westhill [Directions] | Wilton - 126.35; New Canaan - 87.7; Westhill - 76.55; Stamford - 55.65 | 3:30pm | |
| Fri., 1/9 | V Boys Basketball | Norwalk | Home - NCHS Gymnasium [Directions] | L 56-72 | ||
| Fri., 1/9 | JV Boys Basketball | Norwalk | Home - NCHS Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/9 | FR Boys Basketball | Norwalk | Home - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/9 | V Girls Basketball | Norwalk | Away - Norwalk High Gym [Directions] | L 30-44 | 2:30pm Var & JV ride together | |
| Fri., 1/9 | JV Girls Basketball | Norwalk | Away - Norwalk High Gym [Directions] | 5:30 p.m. | 2:30pm Var & JV ride together | |
| Fri., 1/9 | FR Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | L 4-31 | 2:30pm | |
| Fri., 1/9 | V Girls Ice Hockey | Guilford Coop | Away - East Haven [Directions] | W 9-3 | 2:30pm | |
| Sat., 1/10 | V Boys Ice Hockey | Staples | Away - Milford Ice Pavilion [Directions] | W 6-1 | 6:00pm | |
| Sat., 1/10 | V Boys Indoor Track | Elm City Invitational | Away - Floyd Little Athletic Center | 9:00 a.m. | 7:00am | |
| Sat., 1/10 | V Boys Indoor Track | Qualifier #2 | Away - Wilton | 9:30 a.m. | ||
| Sat., 1/10 | V Wrestling | Darien, Platt Tech, Fairfield Prep, Bunnell | Away - DHS Main Gym [Directions] | Win NC 54 Darien 21 Win NC 42 Platt Tech 36 Win NC 57 Bunnell 18 Loss NC 25 Fairfield Prep 51 | 8:30am | |
| Sat., 1/10 | V Girls Ice Hockey | Glastonbury | Home - Shelton Ice Rinks [Directions] | L 3-5 | ||
| Sat., 1/10 | V Girls Indoor Track | Qualifier #2 | Away - Wilton | 9:30 a.m. | ||
| Sun., 1/11 | JV Boys Ice Hockey | Stamford (Scrim.) | Home - Darien Ice Rink [Directions] | 9:00 p.m. | ||
| Sun., 1/11 | JV Girls Ice Hockey | Masuk Coop | Away - Shelton Ice Rink [Directions] | 4:30 p.m. | 3:00pm | |
| Tue., 1/13 | V Boys Basketball | Westhill | Home - NCHS Gymnasium [Directions] | L 52-69 | ||
| Tue., 1/13 | JV Boys Basketball | Westhill | Home - NCHS Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/13 | FR Boys Basketball | Westhill | Home - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/13 | V Girls Basketball | Westhill | Away [Directions] | W 37-34 | 4:00pm Var & JV ride together | |
| Tue., 1/13 | JV Girls Basketball | Westhill | Away [Directions] | 5:15 p.m. | 4:00pm Var & JV ride together | |
| Tue., 1/13 | FR Girls Basketball | Westhill | Away [Directions] | L 22-34 | 2:15pm | |
| Wed., 1/14 | V Boys Ice Hockey | Trumbull | Away - Shelton Rinks [Directions] | W 7-2 | 4:15pm | |
| Wed., 1/14 | V Wrestling | Brien McMahon | Home - NCHS Gymnasium [Directions] | Loss NC 18 McMahon 57 | ||
| Wed., 1/14 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Connors Ice Rink [Directions] | L 3-7 | 3:45pm | |
| Thu., 1/15 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Away - Fairfield University Rec Plex Pool [Directions] | 6:00 p.m. | 4:00pm | |
| Fri., 1/16 | V Boys Basketball | Fairfield Warde | Away [Directions] | W 55-54 | 4:00pm Var & JV Ride Together | |
| Fri., 1/16 | JV Boys Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 5:15 p.m. | 4:00pm Var & JV Ride Together | |
| Fri., 1/16 | FR Boys Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 3:45 p.m. | 2:15pm | |
| Fri., 1/16 | V Girls Basketball | Fairfield Warde | Home - NCHS Gymnasium [Directions] | L 34-64 | ||
| Fri., 1/16 | JV Girls Basketball | Fairfield Warde | Home - NCHS Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/16 | FR Girls Basketball | Fairfield Warde | Home - NCHS Gymnasium [Directions] | W 35-32 | ||
| Fri., 1/16 | V Girls Gymnastics | New Milford, Westhill | Away - New Milford High School [Directions] | New Milford - 133.68 New Canaan - 105.05 Westhill - 86.90 Stamford - 76.90 | 2:45pm | |
| Fri., 1/16 | V Girls Indoor Track | Yale Invitational | Away - Yale University | 1:40 p.m. | 12:00pm | |
| Sat., 1/17 | V Boys Ice Hockey | Darien | Away - Darien Ice Rink [Directions] | L 2-4 | ||
| Sat., 1/17 | JV Boys Ice Hockey | Darien | Home - Darien Ice Rink [Directions] | 8:50 p.m. | ||
| Sat., 1/17 | V Boys Indoor Track | Qualifier #3 | Away - Staples | 10:00 a.m. | 1@8:30am | |
| Sat., 1/17 | V Wrestling | Jonathan Law | Away [Directions] | Win NC 40 Law 39 Loss NC 29 Masuk 48 NC 37 New Britain 36 Criteria Loss NC 36 Harding 40 | 7:45am | |
| Sat., 1/17 | V Girls Ice Hockey | Greenwich | Away - Dorothy Hamill Rink [Directions] | T 3-3 | 5:00pm | |
| Sat., 1/17 | V Girls Indoor Track | Qualifier #3 | Away - Staples | 10:00 a.m. | 2@8:30am | |
| Mon., 1/19 | V Boys Ice Hockey | Xavier | Away - Freeman Athletic Center, Wesleyan University [Directions] | T 2-2 | 1:00pm | |
| Mon., 1/19 | V Boys Swimming and Diving | Ridgefield | Home - New Canaan YMCA [Directions] | 3:00 p.m. | ||
| Mon., 1/19 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Darien Ice Rink [Directions] | W 9-2 | ||
| Tue., 1/20 | V Boys Basketball | Ridgefield | Away - RHS Main Gym [Directions] | L 36-40 | 3:30pm Var & JV Ride Together | |
| Tue., 1/20 | JV Boys Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 5:15 p.m. | 3:30pm Var & JV Ride Together | |
| Tue., 1/20 | FR Boys Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | 2:15pm | |
| Tue., 1/20 | JV Boys Ice Hockey | New Canaan Country Day | Away - NC Winter Club | 4:15 p.m. | ||
| Tue., 1/20 | V Girls Basketball | Ridgefield | Home - NCHS Gymnasium [Directions] | L 31-74 | ||
| Tue., 1/20 | JV Girls Basketball | Ridgefield | Home - NCHS Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/20 | FR Girls Basketball | Ridgefield | Home - NCHS Gymnasium [Directions] | L 12-52 | ||
| Wed., 1/21 | V Boys Ice Hockey | Wilton | Away - Winter Garden Rink-Ridgefield [Directions] | W 8-0 | 6:15pm | |
| Wed., 1/21 | V Boys Swimming and Diving | Westhill/Stamford | Away [Directions] | 3:15 p.m. | 2:05pm | |
| Wed., 1/21 | V Wrestling | Bridgeport Central | Home - NCHS Gymnasium [Directions] | Win NC 54 BC 18 | ||
| Fri., 1/23 | V Boys Basketball | Harding | Away - Harding-Miska Gymnasium [Directions] | L 48-79 | 3:30pm Var & JV Ride Together | |
| Fri., 1/23 | JV Boys Basketball | Harding | Away - Harding-Miska Gymnasium [Directions] | 5:15 p.m. | 3:30pm Var & JV Ride Together | |
| Fri., 1/23 | FR Boys Basketball | Harding | Away - Harding-Miska Gymnasium [Directions] | 4:00 p.m. | 2:05pm | |
| Fri., 1/23 | V Girls Basketball | Harding | Home - NCHS Gymnasium [Directions] | W 61-46 | ||
| Fri., 1/23 | JV Girls Basketball | Harding | Home - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/23 | FR Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | Cancelled | 2:30pm | |
| Sat., 1/24 | V Wrestling | Oxford Invitational | Away [Directions] | Cancelled | 6:45am | |
| Sun., 1/25 | JV Boys Ice Hockey | Darien (Scrim.) | Home - Darien Ice Rink [Directions] | 9:00 p.m. | ||
| Wed., 1/28 | V Boys Basketball | Danbury | Away - Danbury High School - MAIN gym [Directions] | L 45-55 | 3:30pm Var & JV Ride Together | |
| Wed., 1/28 | JV Boys Basketball | Danbury | Away - Danbury High School - MAIN gym [Directions] | 5:15 p.m. | 3:30pm Var & JV Ride Together | |
| Wed., 1/28 | FR Boys Basketball | Danbury | Away - Danbury High School - MAIN gym [Directions] | 4:00 p.m. | 2:15pm | |
| Wed., 1/28 | V Boys Ice Hockey | Norwalk | Away - SoNo Ice House [Directions] | W 6-1 | 6:10pm | |
| Wed., 1/28 | V Boys Swimming and Diving | Fairfield Warde | Home - New Canaan YMCA [Directions] | 3:00 p.m. | ||
| Wed., 1/28 | V Girls Basketball | Danbury | Home - NCHS Gymnasium [Directions] | W 53-46 | ||
| Wed., 1/28 | JV Girls Basketball | Danbury | Home - NCHS Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 1/28 | FR Girls Basketball | Danbury | Home - NCHS Gymnasium [Directions] | L 18-62 | ||
| Wed., 1/28 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Darien Ice Rink [Directions] | W 4-3 | ||
| Wed., 1/28 | V Girls Indoor Track | Qualifier #4 | Away - Wilton | 5:30 p.m. | ||
| Thu., 1/29 | FR Boys Basketball | Greenwich Country Day | Away | 4:30 p.m. | 3:00pm | |
| Thu., 1/29 | V Wrestling | Harding/Bassick/Bridgeport Central | Home - NCHS Gymnasium [Directions] | Win NC 48 Harding 33 | ||
| Thu., 1/29 | V Competitive Cheerleading | FCIAC's | Away - Fairfield Ludlowe [Directions] | 5:00 p.m. | 3:30pm | |
| Thu., 1/29 | V Girls Gymnastics | Greenwich, Westhill | Away - Greenwich YWCA [Directions] | Greenwich-126.80 New Canaan-93.45 Westhill-88.85 | 4:30pm | |
| Fri., 1/30 | V Boys Basketball | Fairfield Ludlowe | Home - NCHS Gymnasium [Directions] | L 36-49 | ||
| Fri., 1/30 | JV Boys Basketball | Fairfield Ludlowe | Home - NCHS Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/30 | FR Boys Basketball | Fairfield Ludlowe | Home - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/30 | V Boys Indoor Track | FCIAC East Championship | Away - Wilton | 5:30 p.m. | 3:30pm | |
| Fri., 1/30 | V Boys Swimming and Diving | Wilton | Home - New Canaan YMCA [Directions] | 3:00 p.m. | ||
| Fri., 1/30 | V Girls Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | L 19-52 | 4:30pm | |
| Fri., 1/30 | JV Girls Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 5:15 p.m. | 2:45pm FR & JV ride together | |
| Fri., 1/30 | FR Girls Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | L 15-42 | 2:45pm FR & JV ride together | |
| Fri., 1/30 | V Girls Indoor Track | FCIAC East Championship | Away - Wilton | 5:30 p.m. | 3:30pm | |
| Sat., 1/31 | V Boys Ice Hockey | Stamford | Away - Terry Conners Ice Rink [Directions] | W 6-1 | 4:15pm | |
| Sat., 1/31 | V Wrestling | Haddam-Killingworth, Branford | Home - NCHS Gymnasium [Directions] | Loss NC 18 Branford 63 Loss NC 33 Haddam 34 | ||
| Sat., 1/31 | V Girls Gymnastics | Trumbull, Westhill | Away - Next Dimension Gymnastics [Directions] | Trumbull-130.45 New Canaan-97.1 Westhill-82.15 | 4:00pm | |
| Sat., 1/31 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Darien Ice Rink [Directions] | W 9-1 | ||
| Tue., 2/3 | V Boys Basketball | Bassick | Home - NCHS Gymnasium [Directions] | L 40-47 | ||
| Tue., 2/3 | JV Boys Basketball | Bassick | Home - NCHS Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 2/3 | FR Boys Basketball | Bassick | Home - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 2/3 | V Girls Basketball | Bassick | Away [Directions] | W 57-32 | 2:15pm Var & JV ride together | |
| Tue., 2/3 | JV Girls Basketball | Bassick | Away [Directions] | Cancelled | 2:15pm Var & JV ride together | |
| Wed., 2/4 | V Boys Ice Hockey | Westhill/Stamford | Home - Darien Ice Rink [Directions] | T 1-1 | ||
| Wed., 2/4 | V Boys Swimming and Diving | Greenwich | Away - GHS Pool [Directions] | 3:30 p.m. | 2:05pm | |
| Wed., 2/4 | V Wrestling | Greenwich | Away - GHS Gymnasium [Directions] | Loss NC 21 Greenwich 54 | 3:00pm | |
| Thu., 2/5 | V Boys Indoor Track | FCIAC Championships | Away - Hillhouse | 4:30 p.m. | 1:45pm Boys & Girls ride together | |
| Thu., 2/5 | V Girls Gymnastics | Fairfield Ludlowe, Fairfield Warde, Westhill | Home - Greenwich YWCA [Directions] | 87.7 | 4:00pm | |
| Thu., 2/5 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice [Directions] | L 4-6 | 3:15pm | |
| Thu., 2/5 | V Girls Indoor Track | FCIAC Championship | Away - Hillhouse | 4:30 p.m. | 1:45pm Boys & Girls ride together | |
| Fri., 2/6 | V Boys Basketball | Staples | Away - Staples H.S. Gym [Directions] | L 40-53 | 3:45pm Var & JV Ride Together | |
| Fri., 2/6 | JV Boys Basketball | Staples | Away - Staples H.S. Gym [Directions] | 5:15 p.m. | 3:45pm Var & JV Ride Together | |
| Fri., 2/6 | FR Boys Basketball | Staples | Away - Staples H.S. Gym [Directions] | 4:00 p.m. | 2:30pm | |
| Fri., 2/6 | V Girls Basketball | Staples | Home - NCHS Gymnasium [Directions] | W 40-37 | ||
| Fri., 2/6 | JV Girls Basketball | Staples | Home - NCHS Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 2/6 | FR Girls Basketball | Staples | Home - NCHS Gymnasium [Directions] | L 24-40 | ||
| Sat., 2/7 | V Boys Ice Hockey | Trinity Catholic | Home - Darien Ice Rink [Directions] | W 3-0 | ||
| Sat., 2/7 | V Boys Indoor Track | FCIAC JV Invitational | Away - Staples | 10:00 a.m. | 8:15am | |
| Sat., 2/7 | JV Wrestling | Fairfield Ludlowe JV Tournament | Away [Directions] | 9:30 a.m. | 7:30am | |
| Sat., 2/7 | V Girls Gymnastics | Darien, Westhill | Away - Darien YMCA [Directions] | 111.3 | 12:45pm | |
| Sat., 2/7 | V Girls Indoor Track | FCIAC JV Invitational | Away - Staples | 10:00 a.m. | 8:15am | |
| Sun., 2/8 | JV Boys Ice Hockey | Stamford (Scrim.) | Home - Darien Ice Rink [Directions] | 9:00 p.m. | ||
| Tue., 2/10 | V Boys Basketball | Greenwich | Home - NCHS Gymnasium [Directions] | L 58-63 | ||
| Tue., 2/10 | JV Boys Basketball | Greenwich | Home - NCHS Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 2/10 | FR Boys Basketball | Greenwich | Home - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 2/10 | JV Boys Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | 3:15 p.m. | 2:05pm | |
| Tue., 2/10 | V Boys Swimming and Diving | Darien | Home - New Canaan YMCA [Directions] | 3:00 p.m. | ||
| Tue., 2/10 | V Wrestling | Wilton | Away - Wilton High School Field House [Directions] | Win NC 42 Wilton 36 | 5:30pm | |
| Tue., 2/10 | V Girls Basketball | Greenwich | Away - GHS Gymnasium [Directions] | L 36-58 | 3:30pm Var & JV ride together | |
| Tue., 2/10 | JV Girls Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 5:15 p.m. | 3:30pm Var & JV ride together | |
| Tue., 2/10 | FR Girls Basketball | Greenwich | Away - GHS Gymnasium [Directions] | L 27-30 | 2:30pm | |
| Tue., 2/10 | V Girls Ice Hockey | Darien | Home - Darien Ice Rink [Directions] | L 3-4 | ||
| Wed., 2/11 | V Boys Swimming and Diving | Danbury | Home - New Canaan YMCA [Directions] | 3:00 p.m. | ||
| Wed., 2/11 | V Girls Ice Hockey | Stamford/Westhill/Staples | Home - Darien Ice Rink [Directions] | W 5-1 | ||
| Thu., 2/12 | V Girls Basketball | Wilton | Home - NCHS Gymnasium [Directions] | L 29-69 | Senior Day | |
| Thu., 2/12 | JV Girls Basketball | Wilton | Home - NCHS Gymnasium [Directions] | 5:15 p.m. | ||
| Thu., 2/12 | FR Girls Basketball | Wilton | Home - NCHS Gymnasium [Directions] | L 14-42 | ||
| Fri., 2/13 | V Boys Basketball | Wilton | Away - Wilton High School Field House [Directions] | L 60-61 | 4:00pm Var & JV Ride Together | |
| Fri., 2/13 | JV Boys Basketball | Wilton | Away - Wilton High School Field House [Directions] | 5:15 p.m. | 4:00pm Var & JV Ride Together | |
| Fri., 2/13 | FR Boys Basketball | Wilton | Away - Wilton High School Field House [Directions] | 4:00 p.m. | 2:45pm | |
| Fri., 2/13 | V Boys Indoor Track | CIAC Class L Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | 1:30pm | |
| Fri., 2/13 | V Boys Swimming and Diving | Staples | Away - Staples HS Pool [Directions] | 4:00 p.m. | 2:05pm | |
| Fri., 2/13 | V Wrestling | FCIAC's | Home - NCHS Gymnasium [Directions] | 4:30 p.m. | ||
| Fri., 2/13 | JV Girls Ice Hockey | Masuk Coop | Away - Shelton Ice Rink [Directions] | 4:15 p.m. | 2:30pm | |
| Fri., 2/13 | V Girls Indoor Track | CIAC Class L Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | 1:30pm | |
| Sat., 2/14 | V Boys Ice Hockey | Greenwich | Home - Darien Ice Rink [Directions] | T 2-2 | ||
| Sat., 2/14 | V Wrestling | FCIAC's | Home - NCHS Gymnasium [Directions] | 10:00 a.m. | ||
| Sat., 2/14 | V Girls Gymnastics | FCIAC's | Away - Jonathan Law | 97.9 | 8:15am | |
| Sat., 2/14 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - Sono Ice Rink [Directions] | W 9-1 | 10:20am | |
| Sun., 2/15 | JV Boys Ice Hockey | Darien (Scrim.) | Home - Darien Ice Rink [Directions] | Cancelled | ||
| Mon., 2/16 | V Boys Basketball | Trinity Catholic | Home - NCHS Gymnasium [Directions] | W 71-57 | ||
| Mon., 2/16 | JV Boys Basketball | Trinity Catholic | Home - NCHS Gymnasium [Directions] | 5:15 p.m. | ||
| Mon., 2/16 | FR Boys Basketball | Trinity Catholic | Home - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 2/16 | V Boys Ice Hockey | Xavier | Home - Darien Ice Rink [Directions] | L 0-1 | ||
| Mon., 2/16 | V Girls Basketball | Trinity Catholic | Away - Walsh Court | W 53-49 | 2:30pm Var & JV ride together | |
| Mon., 2/16 | JV Girls Basketball | Trinity Catholic | Away - Walsh Court | 4:00 p.m. | 2:30pm Var & JV ride together | |
| Mon., 2/16 | V Girls Ice Hockey | Hamden Coop | Home - Darien Ice Rink [Directions] | L 0-2 | ||
| Wed., 2/18 | V Boys Basketball | Darien | Home - NCHS Gymnasium [Directions] | W 54-47 | ||
| Wed., 2/18 | JV Boys Basketball | Darien | Home - NCHS Gymnasium [Directions] | 3:30 p.m. | ||
| Wed., 2/18 | FR Boys Basketball | Darien | Home - NCHS Gymnasium [Directions] | 2:00 p.m. | ||
| Wed., 2/18 | V Boys Ice Hockey | St. Joseph | Home - Darien Ice Rink [Directions] | W 6-2 | ||
| Wed., 2/18 | V Girls Basketball | Darien | Away - DHS Main Gym [Directions] | L 48-61 | 4:15pm Var & JV ride together | |
| Wed., 2/18 | JV Girls Basketball | Darien | Away - DHS Main Gym [Directions] | 5:15 p.m. | 4:15pm Var & JV ride together | |
| Wed., 2/18 | JV Girls Ice Hockey | New Canaan Country Day | Away - New Canaan Winter Club | 2:15 p.m. | ||
| Fri., 2/20 | V Wrestling | CIAC Class L Championships | Away - Bristol Central HS [Directions] | 4:00 p.m. | ||
| Sat., 2/21 | V Boys Ice Hockey | Notre Dame-Fairfield | Away - Milford Ice Pavilion [Directions] | L 2-6 | 2:15pm | |
| Sat., 2/21 | V Boys Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 10:00 a.m. | 7:45am | |
| Sat., 2/21 | V Boys Swimming and Diving | JV FCIAC's | Away - Greenwich HS | 1:30 p.m. | 11:00am | |
| Sat., 2/21 | V Wrestling | CIAC Class L Championships | Away - Bristol Central HS [Directions] | 9:00 a.m. | ||
| Sat., 2/21 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Home - Darien Ice Rink [Directions] | W 4-3 | Senior Night | |
| Sat., 2/21 | V Girls Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | TBA | |
| Mon., 2/23 | V Boys Basketball | St. Joseph | Home - NCHS Gymnasium [Directions] | L 44-51 | ||
| Mon., 2/23 | JV Boys Basketball | St. Joseph | Home - NCHS Gymnasium [Directions] | 5:15 p.m. | ||
| Mon., 2/23 | FR Boys Basketball | St. Joseph | Home - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 2/23 | V Boys Ice Hockey | Ridgefield | Home - Darien Ice Rink [Directions] | W 7-3 | ||
| Mon., 2/23 | Miscellaneous Events | Unified Basketball Tournament | Away - St Lukes, New Canaan | 3:00 p.m. | 2:05pm | |
| Tue., 2/24 | V Boys Swimming and Diving | FCIAC Trials | Away - Greenwich HS | 4:30 p.m. | 2:05pm | |
| Wed., 2/25 | V Boys Basketball | Stamford | Away [Directions] | L 23-64 | 4:00pm Var & JV Ride Together | |
| Wed., 2/25 | JV Boys Basketball | Stamford | Away [Directions] | 5:15 p.m. | 4:00pm Var & JV Ride Together | |
| Wed., 2/25 | FR Boys Basketball | Stamford | Away - Stamford High School [Directions] | 4:00 p.m. | 2:45pm | |
| Wed., 2/25 | V Boys Swimming and Diving | FCIAC Diving | Away - Westhill | 4:30 p.m. | ||
| Wed., 2/25 | V Girls Basketball | Darien | Home - NCHS Gymnasium [Directions] | 3:30 p.m. | ||
| Wed., 2/25 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Darien Ice Rink [Directions] | 6:00 p.m. | ||
| Thu., 2/26 | V Boys Swimming and Diving | FCIAC Finals | Away - Greenwich HS | 6:30 p.m. | 3:30pm | |
| Fri., 2/27 | V Boys Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | 4:30 p.m. | ||
| Fri., 2/27 | V Wrestling | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | ||
| Fri., 2/27 | V Girls Basketball | Fairfield Ludlowe | Away [Directions] | 3:00 p.m. | 2:15pm | |
| Fri., 2/27 | V Girls Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | 4:30 p.m. | ||
| Sat., 2/28 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Home - Terry Connors Ice Rink [Directions] | W 3-2 | 2:30pm | |
| Sat., 2/28 | V Wrestling | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 9:00 a.m. | ||
| Sat., 2/28 | V Girls Gymnastics | CIAC Championship | Away | TBA | ||
| Mon., 3/2 | V Girls Basketball | Bacon Academy | Away - BA Gym [Directions] | 6:00 p.m. | 2:45pm | |
| Mon., 3/2 | V Girls Ice Hockey | Glastonbury | Away - Newington Rinks [Directions] | 4:45 p.m. | 2:05pm | |
| Wed., 3/4 | V Boys Ice Hockey | Darien | Away - Terry Connors Ice Rink [Directions] | L 0-2 | 2:05pm | |
| Fri., 3/6 | V Wrestling | New England Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | ||
| Sat., 3/7 | V Boys Ice Hockey | FCIAC Finals | Away | Cancelled | ||
| Sat., 3/7 | V Wrestling | New England Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 9:00 a.m. | ||
| Sun., 3/8 | V Girls Gymnastics | Ro Carlucci Invitational | Away - GCA of Fairfield | 4:00 p.m. | 2:15pm | |
| Wed., 3/11 | V Boys Ice Hockey | Notre Dame-Fairfield | Away - Milford Ice Pavilion [Directions] | 7:30 p.m. | 4:30pm | |
| Wed., 3/11 | V Boys Swimming and Diving | CIAC Class L Diving Trials/Finals | Away - Middletown HS [Directions] | 5:30 p.m. | 2:05pm - Hoyt | |
| Sat., 3/14 | V Boys Ice Hockey | CIAC 1/4 Finals | Away | TBA | ||
| Sat., 3/14 | V Boys Swimming and Diving | CIAC Class L Qualifying | Away - Kennedy HS -Waterbury [Directions] | 4:30 p.m. | 12:15am | |
| Tue., 3/17 | V Boys Swimming and Diving | CIAC Class L Finals | Away - Wesleyan Univ. [Directions] | 1:30 p.m. | 10:00am | |
| Wed., 3/18 | V Boys Ice Hockey | CIAC Semi-Finals | Away | TBA | ||
| Wed., 3/18 | Miscellaneous Events | Unified Sports | Away - Ludlowe | 3:00 p.m. | ||
| Wed., 3/18 | Miscellaneous Events | Unified Sports | Away - Fairfield Ludlowe | 3:30 p.m. | 2:05pm | |
| Thu., 3/19 | V Boys Swimming and Diving | CIAC Open Diving | Away - Middletown [Directions] | 5:30 p.m. | ||
| Sat., 3/21 | V Boys Ice Hockey | CIAC Finals | Away | TBA | ||
| Sat., 3/21 | V Boys Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 2:30 p.m. | Yes | |
| Sat., 3/28 | V Baseball | Darien (Scrim.) | Away [Directions] | 9:30 a.m. | 8:15am | |
| Sat., 3/28 | V Boys Lacrosse | Niskayuna (NY) (Scrim.) | Home - Dunning Stadium [Directions] | 2:00 p.m. | ||
| Sat., 3/28 | V Boys Volleyball | Darien (Scrim.) | Away [Directions] | 8:30 a.m. | 7:30am | |
| Sat., 3/28 | V Boys Volleyball | Darien (Scrim.) | Away [Directions] | TBA | ||
| Sat., 3/28 | V Girls Lacrosse | Wilton Play Day | Away | 8:30 a.m. | 7:00am | |
| Wed., 4/1 | V Baseball | Brien McMahon (Scrim.) | Away [Directions] | 4:00 p.m. | 2:45pm | |
| Wed., 4/1 | V Boys Lacrosse | Staples (Scrim.) | Home - Dunning Stadium [Directions] | 4:00 p.m. | ||
| Thu., 4/2 | V Baseball | Darien (Scrim.) | Away - DHS Baseball Varsity Field [Directions] | 3:30 p.m. | 3:00pm | |
| Thu., 4/2 | V Boys Tennis | Weston (Scrim.) | Home - NCHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 4/2 | V Softball | Brien McMahon (Scrim.) | Away - Brookside school [Directions] | 3:30 p.m. | 2:20pm | |
| Sat., 4/4 | V Baseball | Westhill (Scrim.) | Home - Mead Park [Directions] | 11:00 a.m. | ||
| Sat., 4/4 | V Boys Lacrosse | Ridgefield (Scrim.) | Away - Tiger Hollow Stadium [Directions] | 4:00 p.m. | 2:00pm | |
| Sat., 4/4 | V Girls Lacrosse | New Canaan Play Day | Home - Dunning Stadium [Directions] | 9:00 a.m. | ||
| Mon., 4/6 | V Boys Tennis | Fairfield Prep (Scrim.) | Home - NCHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 4/6 | V Softball | Darien (Scrim.) | Away - DHS Softball Varsity Field [Directions] | 3:15 p.m. | 2:15pm | |
| Mon., 4/6 | V Softball | Darien (Scrim.) | Away [Directions] | 3:15 p.m. | 2:15pm | |
| Wed., 4/8 | V Boys Lacrosse | St. Joseph | Home - Dunning Stadium [Directions] | W 17-5 | ||
| Wed., 4/8 | JV Boys Lacrosse | St. Joseph | Home - Dunning Stadium [Directions] | 6:30 p.m. | ||
| Wed., 4/8 | FR Boys Lacrosse | Greenwich | Away - GHS Field 7 [Directions] | 4:30 p.m. | 2:45pm | |
| Wed., 4/8 | V Girls Lacrosse | St. Joseph | Away - St. Joseph High School [Directions] | W 17-0 | 2:15pm Var & JV Ride Together | |
| Wed., 4/8 | JV Girls Lacrosse | St. Joseph | Away - St. Joseph High School [Directions] | 5:30 p.m. | 2:15pm Var & JV Ride Together | |
| Wed., 4/8 | V Girls Tennis | Danbury | Home - NCHS Tennis Courts [Directions] | W 7-0 | ||
| Thu., 4/9 | V Baseball | New Milford | Away - New Milford High School [Directions] | W 4-10 | 2:15pm Var & JV ride together | |
| Thu., 4/9 | JV Baseball | New Milford | Away - New Milford High School [Directions] | L 7-3 | 2:15pm Var & JV ride together | |
| Thu., 4/9 | V Boys Tennis | Trumbull | Home - NCHS Tennis Courts [Directions] | W 7-0 | ||
| Thu., 4/9 | V Girls Lacrosse | Fox Lane (NY) | Home - Dunning Stadium [Directions] | W 14-5 | ||
| Thu., 4/9 | JV Girls Lacrosse | Fox Lane (NY) | Home - Dunning Stadium [Directions] | 6:00 p.m. | ||
| Thu., 4/9 | V Softball | Stamford | Away - Stamford High School [Directions] | L 2-12 | 2:45pm | |
| Thu., 4/9 | V Girls Tennis | Trumbull | Away - THS Tennis Courts [Directions] | W 6-1 | 2:20pm | |
| Fri., 4/10 | V Baseball | Trumbull | Away - Varsity Baseball Field [Directions] | W 1-0 | 2:15pm Var & JV ride together | |
| Fri., 4/10 | JV Baseball | Trumbull | Away - JV Baseball Field [Directions] | L 7-2 | 2:15pm Var & JV ride together | |
| Fri., 4/10 | FR Baseball | Trumbull | Home - Waveny Park - Coppo Field [Directions] | 4:00 p.m. | ||
| Fri., 4/10 | FR Boys Lacrosse | Ridgefield | Home - Dunning Stadium [Directions] | 6:30 p.m. | ||
| Fri., 4/10 | V Boys Volleyball | Harding | Home - NCHS Gymnasium [Directions] | W 3-0 | ||
| Fri., 4/10 | FR Girls Lacrosse | Ridgefield | Away - Scotts Ridge MS Turf [Directions] | 4:00 p.m. | 2:30pm | |
| Fri., 4/10 | V Softball | Trumbull | Home - Waveny Park - Orchard Field [Directions] | L 2-15 | ||
| Mon., 4/13 | V Baseball | Brien McMahon | Home - Mead Park [Directions] | W 6-1 | ||
| Mon., 4/13 | FR Baseball | Brien McMahon | Home - Conner Field [Directions] | 4:00 p.m. | ||
| Mon., 4/13 | JV Boys Golf | Darien | Home - Country Club of New Canaan [Directions] | 3:15 p.m. | ||
| Mon., 4/13 | V Boys Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe Tennis Courts [Directions] | W 6-1 | 2:20pm | |
| Mon., 4/13 | V Boys Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | W 3-1 | 2:30pm Var & JV ride together | |
| Mon., 4/13 | JV Boys Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | W 2-1 | 2:30pm Var & JV ride together | |
| Mon., 4/13 | V Softball | Brien McMahon | Away - Brien McMahon HS [Directions] | W 10-0 | 2:15pm | |
| Mon., 4/13 | V Girls Tennis | Fairfield Ludlowe | Home - NCHS Tennis Courts [Directions] | L 1-6 | ||
| Tue., 4/14 | JV Baseball | Brien McMahon | Away - Roton [Directions] | W 9-5 | 2:45pm | |
| Tue., 4/14 | V Boys Lacrosse | Trumbull | Away - McDougall Stadium [Directions] | W 17-6 | 3:00pm | |
| Tue., 4/14 | JV Boys Lacrosse | Trumbull | Away - Indian Ledge Turf Field [Directions] | 6:00 p.m. | 3:45pm | |
| Tue., 4/14 | FR Boys Lacrosse | St. Joseph | Away - St. Joseph High School [Directions] | 4:00 p.m. | 2:30pm | |
| Tue., 4/14 | V Boys Tennis | Stamford | Home - NCHS Tennis Courts [Directions] | W 7-0 | ||
| Tue., 4/14 | V Girls Lacrosse | Danbury | Home - Dunning Stadium [Directions] | W 18-6 | ||
| Tue., 4/14 | JV Girls Lacrosse | Danbury | Home - Dunning Stadium [Directions] | 5:30 p.m. | ||
| Tue., 4/14 | FR Girls Lacrosse | Trumbull | Home - NCHS Water Tower Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 4/14 | V Girls Tennis | Stamford | Away [Directions] | W 7-0 | 2:20pm | |
| Wed., 4/15 | V Baseball | Bridgeport Central | Away - Central H.S. Baseball Field [Directions] | W 0-7 | 2:15pm Var & JV ride together | |
| Wed., 4/15 | JV Baseball | Bridgeport Central | Away - Seaside Park Diamond 10 [Directions] | W 15-1 (5 inn) | 2:15pm Var & JV ride together | |
| Wed., 4/15 | V Boys Volleyball | Fairfield Warde | Home - NCHS Gymnasium [Directions] | W 3-0 | ||
| Wed., 4/15 | JV Boys Volleyball | Fairfield Warde | Home - NCHS Gymnasium [Directions] | L 1-2 | ||
| Wed., 4/15 | JV Girls Lacrosse | Wilton | Away - Lilly Field - Turf [Directions] | 4:00 p.m. | 2:45pm | |
| Wed., 4/15 | FR Girls Lacrosse | Greenwich Country Day | Home - NCHS Water Tower Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 4/15 | V Softball | Bridgeport Central | Home - Waveny Park - Orchard Field [Directions] | W 13-6 | ||
| Thu., 4/16 | V Boys Lacrosse | Brunswick School | Home - Dunning Stadium [Directions] | L 7-9 | ||
| Thu., 4/16 | JV Boys Lacrosse | Brunswick School | Home - NCHS Water Tower Turf Field [Directions] | 4:30 p.m. | ||
| Thu., 4/16 | FR Boys Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 4:00 p.m. | 2:45pm | |
| Thu., 4/16 | V Girls Lacrosse | Wilton | Home - Dunning Stadium [Directions] | W 12-6 | ||
| Thu., 4/16 | FR Girls Lacrosse | Darien | Away - DHS Turf #2 [Directions] | 4:00 p.m. | 3:00pm | |
| Fri., 4/17 | JV Baseball | St. Lukes | Home - Waveny Park - Coppo Field [Directions] | W 24-0 (6 inn) | ||
| Fri., 4/17 | V Boys Tennis | St. Lukes | Home - NCHS Tennis Courts [Directions] | W 6-1 | ||
| Fri., 4/17 | V Boys Volleyball | Bassick | Away - Bassick Gymnasium [Directions] | W 3-0 | 2:15pm Var & JV ride together | |
| Fri., 4/17 | JV Boys Volleyball | Bassick | Away - Bassick Gymnasium [Directions] | L 1-2 | 2:15pm Var & JV ride together | |
| Sat., 4/18 | V Baseball | New Fairfield | Away - NFHS Baseball Field [Directions] | L 4-6 | 11:00am Var & JV ride together | |
| Sat., 4/18 | V Boys Outdoor Track | Fresh/Soph Meet | Away - Amity High School | 10:00 a.m. | 8:00am | |
| Sat., 4/18 | V Girls Lacrosse | Eastport-South Manor (NY) | Home - Dunning Stadium [Directions] | L 9-11 | ||
| Sat., 4/18 | V Softball | Woodland | Home - Waveny Park - Orchard Field [Directions] | W 8-1 | ||
| Mon., 4/20 | V Boys Volleyball | Darien | Home - NCHS Gymnasium [Directions] | L 1-3 | ||
| Mon., 4/20 | JV Boys Volleyball | Darien | Home - NCHS Gymnasium [Directions] | L 0-2 | ||
| Tue., 4/21 | V Boys Golf | Ridgefield | Away - Ridgefield Public GC (DHLY Ridge) [Directions] | Ridgefield 158 New Canaan 166 | 1:30pm | |
| Tue., 4/21 | V Boys Lacrosse | Ridgewood (NJ) | Away | W 14-6 | 2:30pm | |
| Tue., 4/21 | V Boys Outdoor Track | Westhill, St. Joseph | Home - NCHS Track Field [Directions] | 4:00 p.m. | ||
| Tue., 4/21 | V Boys Tennis | Ridgefield | Away - RHS Tennis Courts [Directions] | W 4-3 | 2:20pm | |
| Tue., 4/21 | JV Boys Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | 3:00pm | |
| Tue., 4/21 | V Girls Golf | Danbury | Away - Richter Park Golf Course [Directions] | NC-228 Dan-203 | 1:30pm | |
| Tue., 4/21 | V Girls Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | W 19-3 | 3:00pm Var & JV Ride Together | |
| Tue., 4/21 | JV Girls Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 6:00 p.m. | 3:00pm Var & JV Ride Together | |
| Tue., 4/21 | FR Girls Lacrosse | Convent of Sacred Heart | Away - Convent of Sacred Heart | 4:30 p.m. | 2:30pm | |
| Tue., 4/21 | V Softball | Norwalk | Away - Waveny Park - Orchard Field [Directions] | L 10-13 | 2:30pm | |
| Tue., 4/21 | V Girls Tennis | Ridgefield | Home [Directions] | W 5-2 | ||
| Wed., 4/22 | V Boys Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | Trumbull 163 New Canaan 167 | 2:05pm | |
| Wed., 4/22 | V Boys Volleyball | Staples | Home - NCHS Gymnasium [Directions] | W 3-1 | ||
| Wed., 4/22 | JV Boys Volleyball | Staples | Home - NCHS Gymnasium [Directions] | L 1-2 | ||
| Wed., 4/22 | V Girls Golf | Darien | Away - Weeburn Country Club [Directions] | NC-243 Dar-207 | 2:05pm | |
| Wed., 4/22 | JV Softball | Westhill | Away - Roxbury Elementary School [Directions] | Cancelled | ||
| Wed., 4/22 | V Girls Tennis | St. Joseph | Away - St. Joseph High School [Directions] | W 5-0 | 2:15pm | |
| Thu., 4/23 | V Baseball | Westhill | Home - Mead Park [Directions] | W 9-8 | ||
| Thu., 4/23 | JV Baseball | Westhill | Home - Waveny Park - Coppo Field [Directions] | W 5-4 | ||
| Thu., 4/23 | FR Baseball | Westhill | Away - Westhill Baseball Field [Directions] | 4:00 p.m. | 2:45pm | |
| Thu., 4/23 | V Boys Lacrosse | Wilton | Home - Dunning Stadium [Directions] | W 14-3 | ||
| Thu., 4/23 | JV Boys Lacrosse | Wilton | Home - NCHS Water Tower Turf Field [Directions] | 4:30 p.m. | ||
| Thu., 4/23 | V Boys Tennis | Norwalk | Home - NCHS Tennis Courts [Directions] | W 6-1 | ||
| Thu., 4/23 | JV Boys Tennis | Greenwich | Away - Central Middle School [Directions] | 4:30 p.m. | 3:00pm | |
| Thu., 4/23 | V Boys Volleyball | Danbury | Home - NCHS Gymnasium [Directions] | W 3-0 | ||
| Thu., 4/23 | JV Boys Volleyball | Danbury | Home - NCHS Gymnasium [Directions] | W 2-0 | ||
| Thu., 4/23 | V Girls Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | NC-212 Trum-199 | 2:05pm | |
| Thu., 4/23 | V Girls Lacrosse | Fairfield Warde | Home - Dunning Stadium [Directions] | W 16-1 | ||
| Thu., 4/23 | FR Girls Lacrosse | Staples | Away - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | 2:30pm | |
| Thu., 4/23 | V Girls Outdoor Track | Westhill | Home - NCHS Track Field [Directions] | 4:00 p.m. | ||
| Thu., 4/23 | V Girls Tennis | Norwalk | Away - Norwalk High School [Directions] | W 7-0 | 2:30pm | |
| Fri., 4/24 | V Baseball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | W 6-0 | 1:30 | |
| Fri., 4/24 | FR Baseball | Fairfield Warde | Home - Waveny Park - Coppo Field [Directions] | 4:00 p.m. | ||
| Fri., 4/24 | FR Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde Grass Utility Field [Directions] | 4:00 p.m. | 2:30pm | |
| Fri., 4/24 | V Boys Outdoor Track | O'Grady Relays | Away - Danbury High School | 5:30 p.m. | 3:30pm | |
| Fri., 4/24 | V Boys Tennis | St. Joseph | Home - NCHS Tennis Courts [Directions] | W 5-2 | ||
| Fri., 4/24 | V Softball | Fairfield Warde | Home - Waveny Park - Orchard Field [Directions] | L 3-4 | ||
| Fri., 4/24 | JV Girls Tennis | Greenwich | Away - Binney Park [Directions] | 4:00 p.m. | 2:30pm | |
| Sat., 4/25 | V Boys Lacrosse | Greenwich | Home - Dunning Stadium [Directions] | L 10-13 | ||
| Sat., 4/25 | JV Boys Lacrosse | Greenwich | Home - Dunning Stadium [Directions] | 12:00 p.m. | ||
| Sat., 4/25 | V Boys Outdoor Track | O'Grady Relays | Away - Danbury High School | 9:00 a.m. | 7:00am | |
| Sat., 4/25 | V Boys Tennis | Danbury | Away - Danbury High School Tennis Courts [Directions] | W 6-1 | 12:30pm | |
| Sat., 4/25 | V Girls Outdoor Track | O'Grady Relays | Away - Danbury HS | 9:00 a.m. | 7:00am | |
| Mon., 4/27 | V Baseball | Ridgefield | Away - Governor's Park Field (aka Ciuccoli or Old High School) [Directions] | L 7-10 | 2:15pm Var & JV ride together | |
| Mon., 4/27 | JV Baseball | Ridgefield | Away - East Ridge Middle School - South [Directions] | L 4-1 | 2:15pm Var & JV ride together | |
| Mon., 4/27 | FR Baseball | Ridgefield | Home - Waveny Park - Coppo Field [Directions] | 4:00 p.m. | ||
| Mon., 4/27 | V Boys Tennis | Greenwich | Away - GHS Tennis Courts [Directions] | L 3-4 | 2:20pm | |
| Mon., 4/27 | JV Boys Tennis | Greenwich | Away - Central Middle School [Directions] | 4:30 p.m. | 3:00pm | |
| Mon., 4/27 | V Boys Volleyball | Harding | Away - Harding-Miska Gymnasium [Directions] | W 3-0 | 2:15pm Var & JV ride together | |
| Mon., 4/27 | V Girls Golf | Fairfield Warde | Away - Smith Richardson [Directions] | NC-228 FW-210 | 2:00pm | |
| Mon., 4/27 | V Girls Lacrosse | Glastonbury | Home - Dunning Stadium [Directions] | W 12-11 | ||
| Mon., 4/27 | JV Girls Lacrosse | Glastonbury | Home - Dunning Stadium [Directions] | 4:30 p.m. | ||
| Mon., 4/27 | V Girls Outdoor Track | Darien, Harding | Away - DHS Track [Directions] | 4:00 p.m. | 2:05pm | |
| Mon., 4/27 | V Softball | Ridgefield | Home - Waveny Park - Orchard Field [Directions] | L 3-6 | ||
| Mon., 4/27 | V Girls Tennis | Greenwich | Home - NCHS Tennis Courts [Directions] | L 1-6 | ||
| Mon., 4/27 | JV Girls Tennis | Greenwich | Away - Binney Park [Directions] | 4:00 p.m. | 2:20pm | |
| Tue., 4/28 | V Baseball | Norwalk | Home - Mead Park [Directions] | W 2-1 | ||
| Tue., 4/28 | JV Baseball | Norwalk | Home - Waveny Park - Coppo Field [Directions] | W 4-1 | ||
| Tue., 4/28 | FR Baseball | Norwalk | Away - City Hall Field [Directions] | 4:00 p.m. | 2:45pm | |
| Tue., 4/28 | V Boys Golf | Danbury | Away - Richter Park [Directions] | New Canaan 172 Danbury 187 | 1:30pm | |
| Tue., 4/28 | JV Boys Golf | Ridgefield | Away - Ridgefield Public GC (DHLY Ridge) [Directions] | 3:15 p.m. | 1:45pm | |
| Tue., 4/28 | V Boys Lacrosse | Norwalk | Home - Dunning Stadium [Directions] | W 14-4 | ||
| Tue., 4/28 | JV Boys Lacrosse | Norwalk | Home - Dunning Stadium [Directions] | 4:30 p.m. | ||
| Tue., 4/28 | V Boys Tennis | Bridgeport Central | Away - Central H.S. Tennis Courts [Directions] | W 7-0 | 2:20pm | |
| Tue., 4/28 | V Girls Golf | Wilton | Away - Silver Mine CC [Directions] | NC-183 Wil-191 | 2:05pm | |
| Tue., 4/28 | V Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS [Directions] | W 20-3 | 4:30pm Var & JV Ride Together | |
| Tue., 4/28 | JV Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:30 p.m. | 4:30pm Var & JV Ride Together | |
| Tue., 4/28 | FR Girls Lacrosse | Greenwich Country Day | Away | 3:30 p.m. | 2:15pm | |
| Tue., 4/28 | V Softball | Westhill | Away - Westhill Varsity Softball Field [Directions] | L 3-7 | 2:15pm | |
| Tue., 4/28 | V Girls Tennis | Bridgeport Central | Home [Directions] | W 7-0 | ||
| Wed., 4/29 | V Baseball | Harding | Away - Beardsley Park - Baseball [Directions] | W 3-22 | 2:15pm Var & JV ride together | |
| Wed., 4/29 | JV Baseball | Harding | Away - Seaside Park [Directions] | W 20-3 | 2:15pm Var & JV ride together | |
| Wed., 4/29 | V Boys Golf | Stamford | Away - EG Brennan [Directions] | New Canaan 167 Stamford 225 | 2:05pm | |
| Wed., 4/29 | FR Boys Lacrosse | Wilton | Away - Allen's Field [Directions] | 4:00 p.m. | 2:45pm | |
| Wed., 4/29 | V Boys Outdoor Track | Wilton | Away - Allen's Field [Directions] | 4:00 p.m. | 2@ 2:30pm | |
| Wed., 4/29 | V Boys Outdoor Track | Darien, Harding | Home - Wilton High School [Directions] | 4:00 p.m. | ||
| Wed., 4/29 | V Girls Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | NC-226 FL-220 | 2:05pm | |
| Wed., 4/29 | FR Girls Lacrosse | Wilton | Home - NCHS Water Tower Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 4/29 | V Softball | Harding | Home - Waveny Park - Orchard Field [Directions] | W 13-1 | ||
| Wed., 4/29 | JV Softball | Harding | Home - Waveny Park - Orchard Field [Directions] | Cancelled | ||
| Thu., 4/30 | FR Baseball | Darien | Home - Waveny Park - Coppo Field [Directions] | 3:30 p.m. | ||
| Thu., 4/30 | V Boys Golf | Norwalk | Home - Country Club of New Canaan [Directions] | New Canaan 153 Norwalk 199 | ||
| Thu., 4/30 | V Boys Lacrosse | Danbury | Away - Danbury High School Stadium [Directions] | W 14-2 | 2:15pm | |
| Thu., 4/30 | JV Boys Lacrosse | Danbury | Away - Danbury High School Stadium [Directions] | 6:00 p.m. | 3:30pm | |
| Thu., 4/30 | V Boys Tennis | Staples | Home - NCHS Tennis Courts [Directions] | L 3-4 | ||
| Thu., 4/30 | V Girls Outdoor Track | Wilton | Home - NCHS Track Field [Directions] | 4:00 p.m. | ||
| Thu., 4/30 | V Softball | Danbury | Home - Waveny Park - Orchard Field [Directions] | L 3-9 | ||
| Thu., 4/30 | V Girls Tennis | Staples | Away - Staples HS-Tennis Courts [Directions] | L 1-6 | 2:20pm | |
| Thu., 4/30 | JV Girls Tennis | Staples | Away - Town Farms Tennis Courts [Directions] | 4:00 p.m. | 2:20pm | |
| Fri., 5/1 | V Baseball | Danbury | Away - Danbury High School Varsity Baseball Field [Directions] | W 12-3 | 2:15pm Var & JV ride together | |
| Fri., 5/1 | JV Baseball | Danbury | Away - Danbury High School Junior Varsity Baseball Field [Directions] | L 10-1 | 2:15pm Var & JV ride together | |
| Fri., 5/1 | FR Baseball | Danbury | Home - Waveny Park - Coppo Field [Directions] | 4:00 p.m. | ||
| Fri., 5/1 | FR Boys Lacrosse | Darien | Away - DHS Turf #2 [Directions] | 5:30 p.m. | 4:15pm | |
| Fri., 5/1 | JV Boys Tennis | Staples | Away - Town Farms Tennis Courts [Directions] | 4:00 p.m. | 3:00pm | |
| Fri., 5/1 | V Boys Volleyball | Bridgeport Central | Home - NCHS Gymnasium [Directions] | W 3-0 | ||
| Fri., 5/1 | JV Boys Volleyball | Bridgeport Central | Home [Directions] | Cancelled | ||
| Fri., 5/1 | V Girls Lacrosse | Yorktown (NY) | Home - Dunning Stadium [Directions] | L 6-13 | ||
| Fri., 5/1 | JV Girls Lacrosse | Yorktown (NY) | Home - Dunning Stadium [Directions] | 6:30 p.m. | ||
| Fri., 5/1 | FR Girls Lacrosse | Darien | Home - NCHS Water Tower Turf Field [Directions] | 4:00 p.m. | ||
| Sat., 5/2 | V Boys Lacrosse | Fairfield Prep | Away - Rafferty Stadium, Fairfield University [Directions] | W 15-9 | 4:00pm | |
| Sat., 5/2 | JV Boys Lacrosse | Fairfield Prep | Away - University Field, Fairfield University [Directions] | 4:00 p.m. | 2:00pm | |
| Sat., 5/2 | FR Boys Lacrosse | Fairfield Prep | Home - Dunning Stadium [Directions] | 1:00 p.m. | ||
| Mon., 5/4 | V Baseball | Fairfield Ludlowe | Home - Mead Park [Directions] | W 5-1 | ||
| Mon., 5/4 | JV Baseball | Fairfield Ludlowe | Home - Waveny Park - Coppo Field [Directions] | L 4-0 | ||
| Mon., 5/4 | FR Baseball | Fairfield Ludlowe | Away - Kiwanis Field [Directions] | 4:00 p.m. | 2:30pm | |
| Mon., 5/4 | JV Boys Golf | Staples | Away - Longshore [Directions] | 3:00 p.m. | 2:05pm | |
| Mon., 5/4 | V Boys Outdoor Track | Brien McMahon, Bassick | Away - New Canaan High School [Directions] | 4:00 p.m. | ||
| Mon., 5/4 | V Boys Tennis | Brien McMahon | Home - NCHS Tennis Courts [Directions] | W 5-2 | ||
| Mon., 5/4 | JV Boys Tennis | Darien | Away - Cherry Lawn Park [Directions] | 4:00 p.m. | 3:00pm | |
| Mon., 5/4 | V Boys Volleyball | St. Joseph | Away - St. Joseph High School [Directions] | W 3-0 | 2:15pm Var & JV ride together | |
| Mon., 5/4 | JV Boys Volleyball | St. Joseph | Away - St. Joseph High School [Directions] | W 2-0 | 2:15pm Var & JV ride together | |
| Mon., 5/4 | FR Girls Lacrosse | Trumbull | Away - Indian Ledge Turf Field [Directions] | 4:00 p.m. | 2:30pm FR Girls | |
| Mon., 5/4 | V Girls Outdoor Track | Bassick, Brien McMahon | Home - NCHS Track Field [Directions] | 4:00 p.m. | ||
| Mon., 5/4 | V Softball | Fairfield Ludlowe | Away - Sturges Park [Directions] | L 9-17 | 2:40pm | |
| Mon., 5/4 | V Girls Tennis | Brien McMahon | Away - Brien McMahon HS [Directions] | W 7-0 | 2:20pm | |
| Mon., 5/4 | JV Girls Tennis | Darien | Away - Weed Beach [Directions] | 4:00 p.m. | 2:20pm | |
| Tue., 5/5 | V Boys Golf | Wilton | Away - Rolling Hills CC [Directions] | New Canaan 163 Wilton 176 | 2:00pm Var & JV ride together | |
| Tue., 5/5 | JV Boys Golf | Wilton | Away - Rolling Hills CC [Directions] | 3:15 p.m. | 2:00pm Var & JV ride together | |
| Tue., 5/5 | V Boys Lacrosse | Joel Barlow | Away - Field J [Directions] | W 17-5 | 2:15pm | |
| Tue., 5/5 | JV Boys Lacrosse | Joel Barlow | Away - Field J [Directions] | 6:00 p.m. | 4:00pm | |
| Tue., 5/5 | V Boys Tennis | Wilton | Home - NCHS Tennis Courts [Directions] | W 6-1 | ||
| Tue., 5/5 | V Girls Golf | Fairfield Warde | Home - Country Club of New Canaan [Directions] | NC-230 FW-220 | ||
| Tue., 5/5 | JV Girls Golf | Trumbull | Home - Country Club of New Canaan [Directions] | 3:30 p.m. | ||
| Tue., 5/5 | V Girls Lacrosse | Staples | Home - Dunning Stadium [Directions] | W 14-4 | ||
| Tue., 5/5 | JV Girls Lacrosse | Staples | Home - Dunning Stadium [Directions] | 5:30 p.m. | ||
| Tue., 5/5 | V Girls Tennis | Wilton | Away - Tennis Courts [Directions] | L 5-2 | 2:30pm Var/JV riding together | |
| Tue., 5/5 | JV Girls Tennis | Wilton | Away - Middlebrook School [Directions] | 4:00 p.m. | 2:30pm Var/JV riding together | |
| Wed., 5/6 | V Baseball | Bassick | Home - Mead Park [Directions] | W 18-1 | ||
| Wed., 5/6 | V Boys Golf | Westhill, Brien McMahon | Home - Country Club of New Canaan [Directions] | New Canaan 152 Westhill 182 McMahon 209 | ||
| Wed., 5/6 | JV Boys Golf | Ridgefield | Home - Country Club of New Canaan [Directions] | 3:15 p.m. | ||
| Wed., 5/6 | FR Boys Lacrosse | Greenwich | Home - Dunning Stadium [Directions] | 6:30 p.m. | ||
| Wed., 5/6 | JV Boys Tennis | Wilton | Away - Middlebrook School [Directions] | 4:00 p.m. | 3:00pm | |
| Wed., 5/6 | V Boys Volleyball | Darien | Away - DHS Main Gym [Directions] | L 2-3 | 3:30pm Var & JV ride together | |
| Wed., 5/6 | JV Boys Volleyball | Darien | Away - DHS Main Gym [Directions] | L 0-2 | 3:30pm Var & JV ride together | |
| Wed., 5/6 | V Girls Golf | Greenwich | Home - Country Club of New Canaan [Directions] | NC-233 Gr-182 | ||
| Wed., 5/6 | FR Girls Lacrosse | Greenwich | Away - GHS Field 3 [Directions] | 4:30 p.m. | 3:00pm | |
| Wed., 5/6 | V Softball | Bassick | Away - Went Field, Bridgeport [Directions] | W 18-0 | 2:15pm | |
| Wed., 5/6 | JV Girls Tennis | Fairfield Ludlowe | Away - Tomlinson MS Tennis Courts [Directions] | 4:00 p.m. | 2:20pm | |
| Thu., 5/7 | V Boys Golf | Staples | Away - Longshore [Directions] | Staples 154 New Canaan 157 | 2:05pm | |
| Thu., 5/7 | JV Boys Lacrosse | Bridgeport Central | Home - Saxe Middle School Field [Directions] | 4:00 p.m. | ||
| Thu., 5/7 | V Boys Outdoor Track | The Loucks Games | Away - White Plains High School | 5:00 p.m. | 2:45pm | |
| Thu., 5/7 | V Boys Tennis | Trinity Catholic | Away - Scalzi Park | W 7-0 | 2:20pm | |
| Thu., 5/7 | V Girls Lacrosse | Darien | Home - Dunning Stadium [Directions] | L 9-12 | ||
| Thu., 5/7 | JV Girls Lacrosse | Darien | Home - Dunning Stadium [Directions] | 4:00 p.m. | ||
| Thu., 5/7 | V Girls Tennis | Trinity Catholic | Home - NCHS Tennis Courts [Directions] | W 7-0 | ||
| Fri., 5/8 | V Baseball | Staples | Away - Staples HS Baseball Field [Directions] | L 2-5 | 2:30pm Var & JV ride together | |
| Fri., 5/8 | JV Baseball | Staples | Away - Wakeman Field [Directions] | L 10-7 | 2:30pm Var & JV ride together | |
| Fri., 5/8 | FR Baseball | Staples | Home - Waveny Park - Coppo Field [Directions] | 4:00 p.m. | ||
| Fri., 5/8 | FR Boys Lacrosse | Danbury | Home - Saxe Middle School Field [Directions] | 4:00 p.m. | ||
| Fri., 5/8 | V Boys Outdoor Track | The Loucks Games | Away - White Plains High School | 3:00 p.m. | 1:50pm | |
| Fri., 5/8 | JV Boys Tennis | Ridgefield | Away - RHS Tennis Courts [Directions] | 4:15 p.m. | 3:00pm | |
| Fri., 5/8 | V Boys Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | L 2-3 | 2:30pm Var & JV ride together | |
| Fri., 5/8 | JV Boys Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | L 1-2 | 2:30pm Var & JV ride together | |
| Fri., 5/8 | FR Girls Lacrosse | Ridgefield | Home [Directions] | 4:00 p.m. | ||
| Fri., 5/8 | V Softball | Staples | Home - Waveny Park - Orchard Field [Directions] | L 1-8 | ||
| Fri., 5/8 | JV Girls Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:15 p.m. | 2:15pm | |
| Sat., 5/9 | V Boys Lacrosse | Darien | Home - Dunning Stadium [Directions] | W 9-8 | ||
| Sat., 5/9 | JV Boys Lacrosse | Darien | Home - Dunning Stadium [Directions] | 5:30 p.m. | ||
| Sat., 5/9 | V Boys Outdoor Track | The Loucks Games | Away - White Plains High School | 9:00 a.m. | 7:00am | |
| Sat., 5/9 | V Girls Lacrosse | Longmeadow (MA) | Home - Dunning Stadium [Directions] | W 11-4 | ||
| Sat., 5/9 | JV Girls Lacrosse | Longmeadow (MA) | Home - Dunning Stadium [Directions] | 10:00 a.m. | ||
| Mon., 5/11 | V Baseball | Greenwich | Home - Mead Park [Directions] | W 8-7 | ||
| Mon., 5/11 | JV Baseball | Greenwich | Home - Waveny Park - Coppo Field [Directions] | L 5-4 | ||
| Mon., 5/11 | FR Baseball | Greenwich | Away - GHS Baseball Field [Directions] | 4:00 p.m. | 2:15pm | |
| Mon., 5/11 | V Boys Golf | Harding, Bridgeport Central | Away [Directions] | New Canaan 159 Harding 259 Central DQ Bassick DQ | 2:05pm | |
| Mon., 5/11 | JV Boys Golf | Greenwich | Away [Directions] | Cancelled | 2:05pm | |
| Mon., 5/11 | V Boys Tennis | Fairfield Warde | Away [Directions] | W 6-1 | 2:20pm | |
| Mon., 5/11 | JV Boys Tennis | Fairfield Warde | Away - FWHS Knapps Courts [Directions] | 4:00 p.m. | 3:00pm | |
| Mon., 5/11 | V Boys Volleyball | Bassick | Home - NCHS Gymnasium [Directions] | W 3-0 | ||
| Mon., 5/11 | JV Boys Volleyball | Bassick | Home [Directions] | W 2-0 | ||
| Mon., 5/11 | JV Girls Golf | Darien | Away - Wee Burn CC [Directions] | 3:15 p.m. | 2:05pm | |
| Mon., 5/11 | JV Girls Golf | Darien | Away - Wee Burn CC [Directions] | 3:15 p.m. | 2:05pm | |
| Mon., 5/11 | JV Girls Lacrosse | Wilton | Home - Water Tower Grass Field [Directions] | 4:30 p.m. | ||
| Mon., 5/11 | V Girls Outdoor Track | Staples, Fairfield Ludlowe | Home - NCHS Track Field [Directions] | 4:00 p.m. | ||
| Mon., 5/11 | V Softball | Greenwich | Away - GHS Softball Field [Directions] | L 5-7 | 2:15pm | |
| Mon., 5/11 | V Girls Tennis | Fairfield Warde | Home - NCHS Tennis Courts [Directions] | W 5-2 | ||
| Mon., 5/11 | JV Girls Tennis | Fairfield Warde | Away - Fairfield Woods Middle School Courts [Directions] | 4:00 p.m. | 2:30pm | |
| Tue., 5/12 | V Boys Golf | Darien | Home - Country Club of New Canaan [Directions] | Darien 169 New Canaan 172 | ||
| Tue., 5/12 | V Boys Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | W 11-8 | 4:45pm | |
| Tue., 5/12 | JV Boys Lacrosse | Fairfield Ludlowe | Away - Sturges Park [Directions] | 5:00 p.m. | 3:15pm | |
| Tue., 5/12 | V Boys Outdoor Track | Staples, Fairfield Ludlowe | Away - Staples Stadium [Directions] | 4:00 p.m. | 2@2:15pm | |
| Tue., 5/12 | JV Boys Tennis | Greenwich | Away - Central Middle School [Directions] | 4:30 p.m. | 3:00pm | |
| Tue., 5/12 | V Girls Golf | Fairfield Ludlowe, Lauralton Hall | Home - Country Club of New Canaan [Directions] | NC-220 FL-240 LH-246 | ||
| Tue., 5/12 | V Girls Lacrosse | Greenwich | Away - Cardinal Stadium [Directions] | W 10-9 | 3:15pm Var & JV Ride Together | |
| Tue., 5/12 | JV Girls Lacrosse | Greenwich | Away - Cardinal Stadium [Directions] | 4:30 p.m. | 3:15pm Var & JV Ride Together | |
| Tue., 5/12 | JV Girls Tennis | Greenwich | Away - Binney Park [Directions] | 4:00 p.m. | 2:30pm | |
| Wed., 5/13 | V Baseball | Wilton | Away - WHS Varsity Baseball Field [Directions] | W 2-7 | 5:00pm at Mead | |
| Wed., 5/13 | JV Baseball | Wilton | Away - JV Baseball Field [Directions] | L 5-2 | 2:45pm | |
| Wed., 5/13 | FR Baseball | Wilton | Home - Waveny Park - Coppo Field [Directions] | 4:00 p.m. | ||
| Wed., 5/13 | JV Boys Golf | Staples | Home - Country Club of New Canaan [Directions] | 3:00 p.m. | ||
| Wed., 5/13 | JV Boys Golf | Greenwich, Staples | Home - Country Club of New Canaan [Directions] | 3:15 p.m. | ||
| Wed., 5/13 | FR Boys Lacrosse | Brien McMahon | Home - Saxe Middle School Field [Directions] | 4:00 p.m. | ||
| Wed., 5/13 | V Softball | Wilton | Home - Waveny Park - Orchard Field [Directions] | W 8-7 | ||
| Thu., 5/14 | V Baseball | Trinity Catholic | Home - Mead Park [Directions] | W 9-8 | ||
| Thu., 5/14 | JV Baseball | Trinity Catholic | Home - Waveny Park - Coppo Field [Directions] | L 6-4 | ||
| Thu., 5/14 | FR Baseball | Trinity Catholic | Away - Trinity Catholic's Lione Field | 4:00 p.m. | 2:30pm Softball and Freshman Baseball will ride together | |
| Thu., 5/14 | V Boys Lacrosse | Westhill | Away - Westhill Front Turf Field [Directions] | W 14-0 | 4:00pm | |
| Thu., 5/14 | JV Boys Lacrosse | Westhill | Away - Westhill Front Turf Field [Directions] | 4:00 p.m. | 2:45pm | |
| Thu., 5/14 | V Boys Tennis | Darien | Home - NCHS Tennis Courts [Directions] | W 6-1 | ||
| Thu., 5/14 | JV Boys Tennis | Darien | Away - Cherry Lawn Park [Directions] | 4:00 p.m. | 3:00pm | |
| Thu., 5/14 | V Girls Golf | Staples | Home - Country Club of New Canaan [Directions] | NC-213 Staples-203 | ||
| Thu., 5/14 | V Girls Lacrosse | Fairfield Ludlowe | Home - Dunning Stadium [Directions] | W 15-5 | ||
| Thu., 5/14 | JV Girls Lacrosse | Fairfield Ludlowe | Home - Dunning Stadium [Directions] | 4:00 p.m. | ||
| Thu., 5/14 | FR Girls Lacrosse | New Canaan Country Day | Away | 3:45 p.m. | 3:00pm | |
| Thu., 5/14 | V Girls Outdoor Track | Fresh/Soph Meet | Away - Darien | 3:30 p.m. | 2:15pm | |
| Thu., 5/14 | V Softball | Trinity Catholic | Away - Trinity Catholic's Smith Field | W 10-8 | 2:30pm Softball and Freshman Baseball will ride together | |
| Thu., 5/14 | V Girls Tennis | Darien | Away - DHS Tennis Courts [Directions] | L 7-0 | 2:30pm | |
| Thu., 5/14 | JV Girls Tennis | Darien | Away - Weed Beach [Directions] | 4:00 p.m. | 2:30pm | |
| Fri., 5/15 | FR Boys Lacrosse | Wilton | Home - Dunning Stadium [Directions] | 6:30 p.m. | ||
| Fri., 5/15 | FR Girls Lacrosse | Wilton | Away - Allen's Field [Directions] | 4:00 p.m. | 3:00pm | |
| Fri., 5/15 | JV Girls Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | 2:20pm | |
| Sat., 5/16 | V Boys Lacrosse | St. Anthonys (NY) | Away | L 8-9 | 3:15pm | |
| Sat., 5/16 | JV Boys Lacrosse | St. Anthonys (NY) | Away | 4:30 p.m. | 1:00pm | |
| Mon., 5/18 | V Baseball | Darien | Home - Mead Park [Directions] | L 1-6 | ||
| Mon., 5/18 | JV Baseball | Darien | Home - Waveny Park - Coppo Field [Directions] | L 8-1 | ||
| Mon., 5/18 | FR Baseball | Darien | Away - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | 2:45pm | |
| Mon., 5/18 | V Boys Lacrosse | Trinity Catholic | Home - Dunning Stadium [Directions] | W 18-1 | ||
| Mon., 5/18 | FR Boys Lacrosse | Trumbull | Away - Varsity Grass Field [Directions] | 4:00 p.m. | 2:15pm | |
| Mon., 5/18 | V Boys Tennis | Westhill | Away [Directions] | W 5-2 | 2:20pm | |
| Mon., 5/18 | V Boys Volleyball | Trumbull | Away - THS Main Gym [Directions] | L 2-3 | 2:15pm Var & JV ride together | |
| Mon., 5/18 | JV Boys Volleyball | Trumbull | Away - THS Main Gym [Directions] | L 1-2 | 2:15pm Var & JV ride together | |
| Mon., 5/18 | V Girls Lacrosse | Westhill | Away - Westhill Front Turf Field [Directions] | W 18-4 | 2:45pm Var & JV Ride Together | |
| Mon., 5/18 | JV Girls Lacrosse | Westhill | Away - Westhill Front Field [Directions] | 5:30 p.m. | 2:45pm Var & JV Ride Together | |
| Mon., 5/18 | V Girls Outdoor Track | Fairfield Warde, Stamford | Away [Directions] | 4:00 p.m. | 2@2:30pm | |
| Mon., 5/18 | V Softball | Darien | Away - DHS Softball Varsity Field [Directions] | L 0-9 | 2:15pm | |
| Mon., 5/18 | V Girls Tennis | Westhill | Home - NCHS Tennis Courts [Directions] | W 7-0 | ||
| Tue., 5/19 | V Boys Golf | Fairfield Warde, Norwalk | Away - Smith Richardson [Directions] | New Canaan 155 Fairfield Warde 160 | 2:05pm | |
| Tue., 5/19 | V Boys Lacrosse | Fairfield Warde | Home - Dunning Stadium [Directions] | W 13-8 | ||
| Tue., 5/19 | JV Boys Lacrosse | Fairfield Warde | Home - Dunning Stadium [Directions] | 4:30 p.m. | ||
| Tue., 5/19 | FR Boys Lacrosse | Norwalk | Home - Saxe Middle School Field [Directions] | Cancelled | ||
| Tue., 5/19 | V Boys Outdoor Track | Stamford, Fairfield Warde | Home - NCHS Track Field [Directions] | 4:00 p.m. | ||
| Tue., 5/19 | V Boys Volleyball | St. Joseph | Home - NCHS Gymnasium [Directions] | W 3-2 | ||
| Tue., 5/19 | JV Boys Volleyball | St. Joseph | Home [Directions] | L 1-2 | ||
| Tue., 5/19 | V Girls Golf | Wilton | Home - Country Club of New Canaan [Directions] | NC-221 Wil-220 | ||
| Tue., 5/19 | JV Girls Golf | Staples | Away - Longshore [Directions] | 3:00 p.m. | 2:05pm | |
| Wed., 5/20 | V Baseball | St. Joseph | Home - Mead Park [Directions] | W 10-9 | Senior Night | |
| Wed., 5/20 | JV Baseball | St. Joseph | Home - Waveny Park - Coppo Field [Directions] | W 14-2 | ||
| Wed., 5/20 | FR Baseball | St. Joseph | Away - St. Joseph High School [Directions] | 4:00 p.m. | 2:15pm | |
| Wed., 5/20 | V Boys Golf | Greenwich | Home - Country Club of New Canaan [Directions] | Greenwich 163 New Canaan 165 | ||
| Wed., 5/20 | JV Boys Golf | Greenwich | Away - Griff Harris [Directions] | 3:15 p.m. | 2:05pm | |
| Wed., 5/20 | V Boys Volleyball | Ridgefield | Home - NCHS Gymnasium [Directions] | L 0-3 | Senior Night | |
| Wed., 5/20 | JV Boys Volleyball | Ridgefield | Home [Directions] | L 0-2 | ||
| Wed., 5/20 | V Girls Golf | Ridgefield | Home - CCNC [Directions] | NC-229 R-207 | ||
| Wed., 5/20 | V Softball | St. Joseph | Away - St. Joseph High School [Directions] | L 0-12 | 2:15pm | |
| Wed., 5/20 | JV Softball | St. Joseph | Away - Unity Park, Trumbull [Directions] | Cancelled | ||
| Wed., 5/20 | V Girls Tennis | Darien | Away - Weed Beach [Directions] | 4:00 p.m. | 2:30pm | |
| Thu., 5/21 | FR Baseball | Stamford | Home - Waveny Park - Coppo Field [Directions] | 4:00 p.m. | ||
| Thu., 5/21 | FR Boys Lacrosse | Darien | Home - Dunning Stadium [Directions] | 6:30 p.m. | ||
| Thu., 5/21 | V Boys Tennis | Fairfield Warde | Home - NCHS Tennis Courts [Directions] | W 5-0 | Rain Date - 5/22 | |
| Thu., 5/21 | V Girls Golf | Darien | Home - Country Club of New Canaan [Directions] | NC-214 Dar-220 | ||
| Thu., 5/21 | JV Girls Golf | Darien | Home - Country Club of New Canaan [Directions] | 3:30 p.m. | ||
| Thu., 5/21 | V Girls Outdoor Track | St. Joseph, Westhill | Away - St. Joseph High School [Directions] | Cancelled | 2@2:15pm | |
| Thu., 5/21 | V Girls Outdoor Track | St. Joseph | Away [Directions] | 4:00 p.m. | 2@2:20pm | |
| Fri., 5/22 | V Baseball | Stamford | Away - Stamford High School [Directions] | L 9-1 | 2:30pm Var & JV ride together | |
| Fri., 5/22 | JV Baseball | Stamford | Away - Belltown Field [Directions] | L 1-0 | 2:30pm Var & JV ride together | |
| Fri., 5/22 | V Boys Lacrosse | Wilton | Home - Dunning Stadium [Directions] | W 10-9 | ||
| Fri., 5/22 | V Boys Outdoor Track | Coaches Vs Cancer Meet | Away - Staples High School | 4:00 p.m. | 2:15pm | |
| Fri., 5/22 | V Girls Lacrosse | Ridgefield | Home - Dunning Stadium [Directions] | 7:00 p.m. | ||
| Fri., 5/22 | V Girls Lacrosse | Ridgefield | Home - Dunning Stadium [Directions] | 7:00 p.m. | ||
| Fri., 5/22 | V Softball | Stamford | Home - Waveny Park - Orchard Field [Directions] | L 3-22 | Senior Night | |
| Fri., 5/22 | JV Softball | Stamford | Home - Waveny Park - Orchard Field [Directions] | Cancelled | ||
| Tue., 5/26 | V Baseball | Trinity Catholic | Home - Mead Park [Directions] | 4:00 p.m. | ||
| Tue., 5/26 | JV Boys Golf | Darien | Home - Country Club of New Canaan [Directions] | 3:15 p.m. | ||
| Tue., 5/26 | V Boys Lacrosse | Darien | Away - Brien McMahon [Directions] | L 7-13 | 3:00pm | |
| Tue., 5/26 | V Boys Tennis | Greenwich | Away [Directions] | L 0-4 | Rain Date - 5/27 | |
| Tue., 5/26 | V Girls Lacrosse | Greenwich | Home - Dunning Stadium [Directions] | 5:00 p.m. | ||
| Tue., 5/26 | V Girls Lacrosse | Greenwich | Home - Dunning Stadium [Directions] | W 11-4 | ||
| Tue., 5/26 | V Girls Outdoor Track | FCIAC's | Away - Danbury | TBA | 2@12:45pm | |
| Wed., 5/27 | V Boys Golf | St. Joseph | Home - Country Club of New Canaan [Directions] | 3:15 p.m. | ||
| Wed., 5/27 | V Boys Golf | Fairfield Ludlowe | Home - Country Club of New Canaan [Directions] | New Canaan 160 Fairfield Ludlowe 172 St. Joseph 206 | ||
| Wed., 5/27 | JV Girls Golf | JV Tournament | Away - South Pine Creek Golf Course Fairfield | 3:00 p.m. | 2:15pm | |
| Thu., 5/28 | V Boys Golf | Trinity Catholic | Home - Country Club of New Canaan [Directions] | New Canaan 155 Trinity Catholic 196 | ||
| Thu., 5/28 | V Boys Tennis | FCIAC Finals | Away | Cancelled | ||
| Thu., 5/28 | V Girls Lacrosse | Darien | Away - Brien McMahon [Directions] | 4:00 p.m. | 2:30pm | |
| Sat., 5/30 | V Boys Tennis | CIAC Preliminary Rounds & Early Rounds | Away - Yale | 8:30 a.m. | ||
| Sat., 5/30 | V Boys Tennis | CIAC Preliminary Rounds & Early Rounds | Away - Yale | 8:30 a.m. | 7:00am | |
| Sat., 5/30 | V Girls Tennis | North Haven | Home - NCHS Tennis Courts [Directions] | W 7-0 [Detailed Results] | ||
| Mon., 6/1 | V Boys Volleyball | Daniel Hand | Home - NCHS Gymnasium [Directions] | 6:00 p.m. | ||
| Mon., 6/1 | V Girls Golf | Guimares | Away - Brownson Golf Course | 11:00 a.m. | ||
| Mon., 6/1 | V Girls Lacrosse | CIAC First Round | Home - Dunning Stadium [Directions] | 5:00 p.m. | ||
| Tue., 6/2 | V Boys Tennis | CIAC | Away - Yale | 12:00 p.m. | 9:15am | |
| Wed., 6/3 | V Baseball | Stratford | Home - Mead Park [Directions] | W 11-2 | ||
| Wed., 6/3 | V Boys Lacrosse | Foran | Home - Dunning Stadium [Directions] | W 19-1 | ||
| Wed., 6/3 | V Boys Outdoor Track | CIAC Class L Championship | Away - Willow Brook Park [Directions] | 9:00 a.m. | 12:00pm Boys & Girls on riding on same bus | |
| Wed., 6/3 | V Girls Golf | FCIAC's | Away - Fairchild Wheeler | 9:00 a.m. | ||
| Wed., 6/3 | V Girls Outdoor Track | CIAC Class L Championship | Away - Willow Brook Park [Directions] | 9:00 a.m. | 12:00pm Boys & Girls on riding on same bus | |
| Wed., 6/3 | V Girls Tennis | Southington | Away [Directions] | W 6-1 [Detailed Results] | 9:00am | |
| Wed., 6/3 | V Girls Tennis | Darien | Away - Southington HS [Directions] | L 7-0 [Detailed Results] | ||
| Thu., 6/4 | V Baseball | Windsor | Away - Windsor H.S. [Directions] | 3:30 p.m. | 12:00pm | |
| Thu., 6/4 | V Boys Tennis | Class L State Finals | Away - Conard High School -West Hartford | 3:30 p.m. | 1:15pm | |
| Thu., 6/4 | V Girls Lacrosse | Lauralton Hall | Home - Dunning Stadium [Directions] | W 20-6 | ||
| Thu., 6/4 | V Girls Lacrosse | Lauralton Hall | Home - Dunning Stadium [Directions] | 5:00 p.m. | ||
| Fri., 6/5 | V Boys Volleyball | South Windsor | Away - South Windsor High School [Directions] | 5:00 p.m. | 12:30pm | |
| Sat., 6/6 | V Boys Lacrosse | Guilford | Home - Dunning Stadium [Directions] | W 15-2 | ||
| Mon., 6/8 | V Boys Golf | CIAC Division II Championship | Away - Crestbrook Park Watertown,CT | 12:00 p.m. | 8:30am | |
| Mon., 6/8 | V Boys Outdoor Track | CIAC Open Championship | Away - Willow Brook Park [Directions] | 1:30 p.m. | 11:00am Boys & Girls ride together | |
| Mon., 6/8 | V Girls Outdoor Track | CIAC Open Championship | Away - Willow Brook Park [Directions] | 1:30 p.m. | 11:00am Boys & Girls ride together | |
| Tue., 6/9 | V Boys Volleyball | Newington | Away - Fairfield Warde [Directions] | 6:00 p.m. | 2:45pm | |
| Wed., 6/10 | V Boys Lacrosse | Wilton | Away - Brien McMahon [Directions] | W 11-7 | 5:30pm | |
| Wed., 6/10 | V Girls Lacrosse | New Fairfield | Away - Ridgfield H.S. [Directions] | 6:00 p.m. | 4:00pm | |
| Sat., 6/13 | V Boys Lacrosse | Daniel Hand | Away - Brien McMahon [Directions] | 10:30 a.m. | 8:30am | |
| Sat., 6/13 | V Boys Outdoor Track | New England Championship | Away - Thornton Academy (ME) | TBA | ||
| Sat., 6/13 | V Girls Lacrosse | Daniel Hand | Away - Bunnell HS [Directions] | 2:30 p.m. | 12:00pm | |
| Sat., 6/13 | V Girls Outdoor Track | New England Championship | Away - Thornton Academy (ME) | TBA | ||
| Tue., 6/16 | V Boys Outdoor Track | CIAC Decathlon Champ. | Away - Willow Brook Park [Directions] | 11:00 a.m. | ||
| Tue., 6/16 | V Girls Outdoor Track | CIAC Heptathlon/Hammer/Steeplechase Champ. | Away - Willow Brook Park | 11:30 a.m. | ||
| Wed., 6/17 | V Boys Outdoor Track | CIAC Decathlon/Hammer/Steeplechase Champ. | Away - Willow Brook Park [Directions] | 11:00 a.m. | ||
| Thu., 6/18 | V Girls Outdoor Track | CIAC Heptathlon Champ. | Away - Willow Brook Park [Directions] | 11:00 a.m. | ||