| Greenwich 2018-19 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 1188 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| TBA | V Boys Alpine Skiing | RACE | Away - Mt Southington | 4:00 p.m. | 1:30 EARLY DISMISSAL | |
| TBA | JV Baseball | Southington | Away - Baseball JV Field [Directions] | TBA | ||
| TBA | JV Baseball | Fairfield Prep | Away - Owen Fish Park [Directions] | TBA | ||
| TBA | JV Baseball | Brien McMahon | Away - Roton Field [Directions] | TBA | ||
| TBA | JV Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:15 p.m. | ||
| TBA | JV Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | TBA | ||
| TBA | FR Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | TBA | 2:45 EARLY DISMISSAL | |
| TBA | FR Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | TBA | 2:45 EARLY DISMISSAL | |
| TBA | JV Boys Lacrosse | Trinity Catholic | Away - Trinity Catholic Alumni Field | Cancelled | Cancelled | 2:30 EARLY DISMISSAL |
| TBA | FR Boys Lacrosse | TBA | Home [Directions] | TBA | ||
| TBA | FR Boys Soccer | Fairfield Warde | Away - Fairfield Warde Grass Utility Field [Directions] | TBA | 2:45 early dismissal | |
| TBA | FR Boys Soccer | New Canaan | Home - Cos Cob Park Benvenuto Field [Directions] | TBA | ||
| TBA | JV Boys Tennis | Byram Hills (NY) | Home - Central MS [Directions] | 4:30 p.m. | ||
| TBA | JV Boys Tennis | Horace Greeley (NY) | Home - Central MS [Directions] | 4:30 p.m. | freshman | |
| TBA | JV Boys Tennis | Fairfield Warde | Away - Fairfield Warde HS [Directions] | TBA | junior varsity | |
| TBA | JV Boys Tennis | Wilton | Home - Central MS [Directions] | TBA | junior varsity | |
| TBA | V Girls Alpine Skiing | RACE | Away - Mt Southington | 4:00 p.m. | 1:30 EARLY RELEASE | |
| TBA | JV Girls Basketball | Brien McMahon | Home - GHS Gymnasium [Directions] | TBA | ||
| TBA | JV Girls Basketball | New Canaan | Home - GHS Gymnasium [Directions] | TBA | ||
| TBA | FR Girls Basketball | New Canaan | Home - GHS Gymnasium [Directions] | TBA | ||
| TBA | FR Girls Basketball | Staples | Away - Staples H.S. Gym [Directions] | TBA | 2:30 EARLY DISMISSAL | |
| TBA | JV Girls Soccer | Staples | Away - Wakeman Field E (grass) [Directions] | 4:30 p.m. | 2:30 early dismissal | |
| TBA | FR Girls Soccer | Staples | Home - Cos Cob Park Benvenuto Field [Directions] | TBA | ||
| TBA | FR Girls Soccer | Fairfield Warde | Home - GHS Field 3 [Directions] | TBA | ||
| TBA | V Softball | Joel Barlow (Scrim.) | Away - Field E (Softball) [Directions] | TBA | ||
| TBA | JV Softball | Fairfield Ludlowe | Away - Tom Hayden field [Directions] | 2:00 p.m. | ||
| TBA | JV Softball | New Canaan | Away - Waveny Park [Directions] | 4:00 p.m. | ||
| TBA | JV Softball | Bridgeport Central | Away - Luis Marin Field #2 [Directions] | 4:30 p.m. | ||
| TBA | JV Softball | New Fairfield (Scrim.) | Away - NFHS Middle Field [Directions] | TBA | ||
| TBA | FR Softball | Danbury | Away - Danbury HS Junior Varsity Softball Field [Directions] | TBA | 3:00 EARLY DISMISSAL | |
| TBA | FR Softball | Newtown | Home - GHS Softball Field [Directions] | TBA | ||
| TBA | JV Girls Tennis | Fairfield Warde | Away - Fairfield Woods MS [Directions] | 4:30 p.m. | FR | |
| TBA | JV Girls Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | TBA | 3:00 EARLY DISMISSAL - FR | |
| TBA | JV Girls Tennis | New Canaan | Home - Binney Park [Directions] | TBA | FR | |
| Wed., 7/4 | School Holidays and Closings | Independence Day | ||||
| Sat., 8/25 | V Boys Water Polo | Wison | Away - Wilson HS | 8:00 a.m. | ||
| Tue., 8/28 | JV Field Hockey | Scrimmage | Away - Greenwich Academy | 5:30 p.m. | ||
| Wed., 8/29 | V Boys Soccer | Scrimmage | Home - Cardinal Stadium [Directions] | 5:00 p.m. | ||
| Thu., 8/30 | FR Football | Darien (Scrim.) | Home - GHS Field 7 [Directions] | 4:30 p.m. | ||
| Thu., 8/30 | V Girls Soccer | Scrimmage | Away - Convent of Sacred Heart | 4:00 p.m. | ||
| Thu., 8/30 | JV Girls Soccer | Scrimmage | Away - Convent of Sacred Heart | 4:00 p.m. | ||
| Thu., 8/30 | V Girls Volleyball | Greenwich Academy (Scrim.) | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 8/30 | JV Girls Volleyball | Greenwich Academy | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 8/30 | FR Girls Volleyball | Greenwich Academy | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 8/31 | V Boys Soccer | Notre Dame-West Haven (Scrim.) | Home - Cardinal Stadium [Directions] | 4:30 p.m. | ||
| Fri., 8/31 | JV Boys Soccer | Notre Dame-West Haven (Scrim.) | Home - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | ||
| Sat., 9/1 | JV Football | Stepinac (NY) (Scrim.) | Away - Stepinac HS | 10:00 a.m. | ||
| Sat., 9/1 | FR Football | Scrimmage | Home - Cardinal Stadium [Directions] | 9:00 a.m. | ||
| Sat., 9/1 | V Field Hockey | Scrimmage | Away - Glastonbury HS | 9:00 a.m. | ||
| Sat., 9/1 | V Girls Volleyball | Scrimmage | Away - Stamford HS | 9:00 a.m. | ||
| Mon., 9/3 | School Holidays and Closings | Labor Day | ||||
| Tue., 9/4 | V Field Hockey | Scrimmage | Away - Greenwich Academy | 4:00 p.m. | 3:00 EARLY DISMISSAL | |
| Wed., 9/5 | V Boys Soccer | Brunswick School (Scrim.) | Away - Brunswick School | 4:30 p.m. | ||
| Wed., 9/5 | V Girls Soccer | Scrimmage | Away - Greenwich Academy | 4:15 p.m. | 3:00 early dismissal | |
| Wed., 9/5 | JV Girls Soccer | Greenwich Academy (Scrim.) | Home - Cos Cob Park Benvenuto Field [Directions] | 4:15 p.m. | one way | |
| Wed., 9/5 | V Girls Volleyball | Scrimmage | Home - GHS Gymnasium [Directions] | 3:45 p.m. | ||
| Fri., 9/7 | FR Football | Scrimmage | Home - GHS Field 7 [Directions] | 5:30 p.m. | ||
| Fri., 9/7 | V Girls Soccer | Brien McMahon | Home - Cardinal Stadium [Directions] | 4:30 p.m. | L 1-0 | |
| Fri., 9/7 | JV Girls Soccer | Brien McMahon | Home - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | ||
| Fri., 9/7 | V Girls Volleyball | St. Joseph | Home - GHS Gymnasium [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 9/7 | JV Girls Volleyball | St. Joseph | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Sat., 9/8 | V Football | Trumbull | Home - Cardinal Stadium [Directions] | 4:00 p.m. | W 42-7 | |
| Sat., 9/8 | SO Football | Bronxville (NY) | Home - Cardinal Stadium [Directions] | 10:00 a.m. | ||
| Sat., 9/8 | V Boys Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | 11:00 a.m. | T 1-1 | |
| Sat., 9/8 | JV Boys Soccer | Brien McMahon | Away - Pride Field (BMHS) [Directions] | 10:00 a.m. | ||
| Sat., 9/8 | FR Boys Soccer | Brien McMahon | Home - GHS Field 3 [Directions] | 10:00 a.m. | ||
| Sat., 9/8 | V Boys Water Polo | Battle of the Beltway | Away - USNA | 9:00 a.m. | ||
| Sat., 9/8 | JV Boys Water Polo | Battle of the Beltway | Away - USNA | 9:00 a.m. | ||
| Sun., 9/9 | School Holidays and Closings | Rosh Hashana begins at sundown | ||||
| Mon., 9/10 | School Holidays and Closings | Rosh Hashana | ||||
| Tue., 9/11 | V Boys Cross Country | Fairfield Ludlowe, Fairfield Warde, Norwalk | Away - Taft Field [Directions] | 4:00 p.m. | 2:00 early dismissal | |
| Tue., 9/11 | JV Football | Trumbull | Away - McDougall Stadium [Directions] | 6:30 p.m. | ||
| Tue., 9/11 | V Girls Cross Country | Fairfield Ludlowe, Fairfield Warde, Norwalk | Away - Taft Field [Directions] | 4:00 p.m. | 2:00 early dismissal | |
| Tue., 9/11 | V Field Hockey | New Canaan | Away - Dunning Stadium [Directions] | 4:00 p.m. | L 0-1 | 2:30 early dismissal |
| Tue., 9/11 | JV Field Hockey | New Canaan | Away - Dunning Stadium [Directions] | 5:30 p.m. | 2:30 early dismissal | |
| Tue., 9/11 | V Girls Soccer | New Canaan | Home - Cardinal Stadium [Directions] | 4:30 p.m. | L 0-3 | |
| Tue., 9/11 | JV Girls Soccer | New Canaan | Home - GHS Field 3 [Directions] | 4:30 p.m. | ||
| Tue., 9/11 | V Girls Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 4:15 p.m. | L 2-3 | 2:15 early dismissal |
| Tue., 9/11 | JV Girls Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 5:30 p.m. | 2:30 early dismissal | |
| Tue., 9/11 | School Holidays and Closings | Rosh Hashana | ||||
| Wed., 9/12 | SO Football | Darien | Away - DHS Stadium East Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 9/12 | V Boys Soccer | New Canaan | Away - Dunning Stadium [Directions] | 6:30 p.m. | T 1-1 | 4:45 early dismissal |
| Wed., 9/12 | JV Boys Soccer | New Canaan | Away - Saxe MS Field [Directions] | TBA | 2:30 early dismissal | |
| Wed., 9/12 | V Boys Water Polo | USMA | Away - West Point | 5:00 p.m. | ||
| Wed., 9/12 | V Girls Swimming and Diving | Danbury | Away - O'Neil Center @ Western Connecticut State University [Directions] | 4:00 p.m. | 2:00 early dismissal | |
| Thu., 9/13 | V Field Hockey | St. Joseph | Home - Cardinal Stadium [Directions] | 4:30 p.m. | W 6-0 | |
| Thu., 9/13 | JV Field Hockey | St. Joseph | Home - Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Thu., 9/13 | V Girls Soccer | Darien | Away - DHS Center Oval Turf Field [Directions] | 4:30 p.m. | L 2-0 | 3:00 early dismissal |
| Thu., 9/13 | JV Girls Soccer | Darien | Away - DHS Upper Oval Turf Field [Directions] | 4:30 p.m. | 3:00 early dismissal | |
| Thu., 9/13 | FR Girls Soccer | Darien | Home - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | ||
| Fri., 9/14 | V Boys Soccer | Darien | Home - Cardinal Stadium [Directions] | 5:00 p.m. | L 0-2 | |
| Fri., 9/14 | JV Boys Soccer | Darien | Home - Cos Cob Park Benvenuto Field [Directions] | 5:00 p.m. | ||
| Fri., 9/14 | FR Boys Soccer | Darien | Away - DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | 2:45 early dismissal | |
| Fri., 9/14 | V Boys Water Polo | Brunswick School | Away - Brunswick | 5:00 p.m. | ||
| Fri., 9/14 | JV Boys Water Polo | Brunswick School | Away - Brunswick | 5:00 p.m. | ||
| Fri., 9/14 | V Field Hockey | Westhill | Away - Westhill Stadium [Directions] | 4:00 p.m. | W 2-0 | 2:30 early dismissal |
| Fri., 9/14 | JV Field Hockey | Westhill | Away - Westhill Stadium [Directions] | 5:30 p.m. | 2:30 early dismissal | |
| Fri., 9/14 | V Girls Volleyball | Brien McMahon | Home - GHS Gymnasium [Directions] | 5:45 p.m. | W 3-0 | |
| Fri., 9/14 | JV Girls Volleyball | Brien McMahon | Home - GHS Gymnasium [Directions] | 4:30 p.m. | ||
| Sat., 9/15 | V Boys Cross Country | Wilton Invitational | Away - Allen Meadow | 9:00 a.m. | ||
| Sat., 9/15 | V Football | Trinity Catholic | Home - Cardinal Stadium [Directions] | 4:00 p.m. | W 56-0 | |
| Sat., 9/15 | V Girls Cross Country | Wilton Invitational | Away - Allen Meadow | 9:00 a.m. | ||
| Sat., 9/15 | V Field Hockey | Mamaroneck (NY) | Home - GHS Field 3 [Directions] | 3:00 p.m. | L 0-3 | |
| Sat., 9/15 | JV Field Hockey | Mamaroneck (NY) | Home - GHS Field 3 [Directions] | 4:30 p.m. | ||
| Sat., 9/15 | FR Field Hockey | Westhill | Home - GHS Field 3 [Directions] | 10:00 a.m. | ||
| Sat., 9/15 | V Girls Soccer | Fairfield Ludlowe | Away - Taft Field [Directions] | 10:00 a.m. | T 0-0 | |
| Sat., 9/15 | JV Girls Soccer | Fairfield Ludlowe | Away - Sturges Park [Directions] | 10:00 a.m. | ||
| Sat., 9/15 | FR Girls Soccer | Fairfield Ludlowe | Home - GHS Field 7 [Directions] | 10:00 a.m. | ||
| Sat., 9/15 | V Girls Swimming and Diving | Glastonbury | Home - GHS Pool [Directions] | 11:00 a.m. | ||
| Mon., 9/17 | V Boys Cross Country | New Canaan, St. Joseph, Westhill | Away - Waveny Park [Directions] | 4:00 p.m. | 2:30 early dismissal | |
| Mon., 9/17 | JV Football | Wilton | Away - Fujitani Field - Turf [Directions] | 6:00 p.m. | ||
| Mon., 9/17 | V Boys Soccer | Fairfield Ludlowe | Home - Cardinal Stadium [Directions] | 5:00 p.m. | W 2-1 | |
| Mon., 9/17 | JV Boys Soccer | Fairfield Ludlowe | Home - GHS Field 3 [Directions] | 5:00 p.m. | ||
| Mon., 9/17 | FR Boys Soccer | Fairfield Ludlowe | Away - Roger Ludlowe MS [Directions] | 4:30 p.m. | 2:45 early dismissal | |
| Mon., 9/17 | V Girls Cross Country | New Canaan, St. Joseph, Westhill | Away - Waveny Park [Directions] | 4:00 p.m. | 2:30 early dismissal | |
| Mon., 9/17 | V Field Hockey | Trumbull | Away - McDougall Stadium [Directions] | 7:00 p.m. | W 4-1 | |
| Mon., 9/17 | JV Field Hockey | Trumbull | Away - McDougall Stadium [Directions] | 5:30 p.m. | ||
| Mon., 9/17 | FR Field Hockey | Trumbull | Home - Cos Cob Park Benvenuto Field [Directions] | 5:15 p.m. | ||
| Mon., 9/17 | V Girls Swimming and Diving | Wilton | Home - GHS Pool [Directions] | 4:30 p.m. | ||
| Mon., 9/17 | V Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 5:30 p.m. | W 3-0 | 2:30 early dismissal |
| Mon., 9/17 | JV Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | 2:30 early dismissal | |
| Mon., 9/17 | FR Girls Volleyball | New Canaan | Home - GHS Gymnasium [Directions] | 4:30 p.m. | ||
| Tue., 9/18 | V Boys Water Polo | Staples | Home - GHS Pool [Directions] | 4:00 p.m. | ||
| Tue., 9/18 | JV Boys Water Polo | Staples | Home - GHS Pool [Directions] | 4:00 p.m. | ||
| Tue., 9/18 | School Holidays and Closings | Yom Kippur begins at sundown | ||||
| Wed., 9/19 | School Holidays and Closings | Yom Kippur | ||||
| Thu., 9/20 | FR Football | Daniel Hand | Home - GHS Field 7 [Directions] | 4:30 p.m. | ||
| Thu., 9/20 | V Girls Soccer | St. Joseph | Home - Cardinal Stadium [Directions] | 4:30 p.m. | L 1-7 | |
| Thu., 9/20 | JV Girls Soccer | St. Joseph | Home - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | ||
| Thu., 9/20 | V Girls Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 6:00 p.m. | L 1-3 | 2:30 early dismissal |
| Thu., 9/20 | JV Girls Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 4:30 p.m. | 2:30 early dismissal | |
| Fri., 9/21 | SO Football | New Canaan | Home - Cardinal Stadium [Directions] | 4:30 p.m. | ||
| Fri., 9/21 | V Boys Soccer | St. Joseph | Away - St. Joseph HS [Directions] | 4:30 p.m. | W 3-0 | 2:30 early dismissal |
| Fri., 9/21 | JV Boys Soccer | St. Joseph | Away - St. Catherines, Trumbull, CT [Directions] | 4:30 p.m. | 2:30 early dismissal | |
| Fri., 9/21 | V Field Hockey | Staples | Away - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | L 1-2 | 2:00 early dismissal |
| Fri., 9/21 | JV Field Hockey | Staples | Away - Ginny Parker Field - Staples [Directions] | 5:15 p.m. | ||
| Fri., 9/21 | FR Field Hockey | Staples | Home - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | ||
| Fri., 9/21 | V Girls Swimming and Diving | Norwalk/McMahon | Home - GHS Pool [Directions] | 4:30 p.m. | ||
| Fri., 9/21 | JV Girls Swimming and Diving | Ridgefield | Home - GHS Pool [Directions] | 7:00 p.m. | ||
| Fri., 9/21 | V Girls Volleyball | Darien | Home - GHS Gymnasium [Directions] | 4:30 p.m. | W 3-2 | |
| Fri., 9/21 | JV Girls Volleyball | Darien | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 9/21 | FR Girls Volleyball | Darien | Away - DHS Main Gym [Directions] | 4:00 p.m. | 2:45 early dismissal | |
| Sat., 9/22 | V Girls Soccer | Ridgefield | Home - Cardinal Stadium [Directions] | 12:00 p.m. | L 0-2 | |
| Sat., 9/22 | JV Girls Soccer | Ridgefield | Home - GHS Field 3 [Directions] | 12:00 p.m. | ||
| Mon., 9/24 | JV Football | Brunswick School | Away - Brunswick School | 4:30 p.m. | 2:45 early dismissal | |
| Mon., 9/24 | V Boys Soccer | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 6:00 p.m. | W 3-1 | |
| Mon., 9/24 | JV Boys Soccer | Ridgefield | Away - Lower Grass Field [Directions] | 4:30 p.m. | 3:00 early dismissal | |
| Mon., 9/24 | V Field Hockey | Stamford | Home - Cardinal Stadium [Directions] | 4:30 p.m. | W 4-0 | |
| Mon., 9/24 | JV Field Hockey | Stamford | Home - Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Mon., 9/24 | FR Field Hockey | New Canaan | Home - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | ||
| Mon., 9/24 | V Girls Volleyball | Fairfield Ludlowe | Home - GHS Gymnasium [Directions] | 4:30 p.m. | W 3-2 | |
| Mon., 9/24 | JV Girls Volleyball | Fairfield Ludlowe | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 9/24 | FR Girls Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 4:30 p.m. | 3:00 early dismissal | |
| Wed., 9/26 | V Boys Soccer | Staples | Home - Cardinal Stadium [Directions] | 5:00 p.m. | W 2-0 | |
| Wed., 9/26 | JV Boys Soccer | Staples | Home - GHS Field 3 [Directions] | 5:00 p.m. | ||
| Wed., 9/26 | V Boys Water Polo | Greenwich Aquatics | Away - Greenwich YMCA | 6:15 p.m. | ||
| Wed., 9/26 | JV Boys Water Polo | Greenwich Aquatics | Away - Greenwich YMCA | 6:15 p.m. | ||
| Wed., 9/26 | V Girls Soccer | Staples | Away - Wakeman Field B (turf) [Directions] | 4:30 p.m. | L 0-3 | 2:30 early dismissal |
| Wed., 9/26 | V Girls Swimming and Diving | Ridgefield | Home - GHS Pool [Directions] | 4:30 p.m. | ||
| Wed., 9/26 | JV Girls Swimming and Diving | Darien | Home - GHS Pool [Directions] | 7:00 p.m. | ||
| Wed., 9/26 | V Girls Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | 5:30 p.m. | L 0-3 | 2:00 early dismissal |
| Wed., 9/26 | JV Girls Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | 2:00 early dismissal | |
| Wed., 9/26 | FR Girls Volleyball | St. Joseph | Home - GHS Gymnasium [Directions] | 4:30 p.m. | ||
| Thu., 9/27 | V Boys Cross Country | Trumbull, Brien McMahon, Darien | Away - Greenwich Point [Directions] | 4:00 p.m. | 2:00 early dismissal | |
| Thu., 9/27 | FR Boys Soccer | Ridgefield | Home - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | ||
| Thu., 9/27 | V Girls Cross Country | Trumbull, Brien McMahon, Darien | Away - Greenwich Point [Directions] | 4:00 p.m. | 2:00 early dismissal | |
| Thu., 9/27 | V Field Hockey | Fairfield Ludlowe | Home - Cardinal Stadium [Directions] | 4:30 p.m. | W 7-1 | |
| Thu., 9/27 | JV Field Hockey | Fairfield Ludlowe | Home - Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Thu., 9/27 | V Girls Soccer | Stamford | Away - Stamford High Soccer Field [Directions] | 4:00 p.m. | W 2-1 | 2:30 early dismissal |
| Thu., 9/27 | JV Girls Soccer | Stamford | Away - Rippowam Field [Directions] | 4:00 p.m. | 2:30 early dismissal | |
| Thu., 9/27 | FR Girls Soccer | Ridgefield | Away - Lower Grass Field [Directions] | 4:00 p.m. | ||
| Fri., 9/28 | V Football | Norwalk | Away - Testa Field, NHS [Directions] | 7:00 p.m. | W 55-0 | |
| Fri., 9/28 | V Boys Soccer | Stamford | Home - Cardinal Stadium [Directions] | 5:00 p.m. | T 1-1 | |
| Fri., 9/28 | JV Boys Soccer | Stamford | Home - Cos Cob Park Benvenuto Field [Directions] | 5:00 p.m. | ||
| Fri., 9/28 | FR Boys Soccer | Stamford | Away [Directions] | 4:00 p.m. | 2:45 early dismissal | |
| Fri., 9/28 | V Boys Water Polo | Beast of the East | Away - Wilson HS | 6:00 p.m. | 3:00 early dismissal | |
| Fri., 9/28 | FR Field Hockey | Fairfield Ludlowe | Away - FLHS Front Field [Directions] | 4:00 p.m. | 2:45 early dismissal | |
| Fri., 9/28 | V Girls Swimming and Diving | Darien | Home - GHS Pool [Directions] | Cancelled | Cancelled | |
| Fri., 9/28 | FR Girls Volleyball | Ridgefield | Home - GHS Gymnasium [Directions] | 4:30 p.m. | ||
| Sat., 9/29 | JV Football | Norwalk | Home - GHS Field 7 [Directions] | 12:00 p.m. | ||
| Sat., 9/29 | FR Football | Norwalk | Home - GHS Field 7 [Directions] | 9:00 a.m. | ||
| Sat., 9/29 | V Girls Soccer | Norwalk | Home - Cardinal Stadium [Directions] | 12:00 p.m. | W 6-0 | |
| Sat., 9/29 | JV Girls Soccer | Norwalk | Home - GHS Field 3 [Directions] | 12:00 p.m. | ||
| Sat., 9/29 | V Girls Swimming and Diving | St. Joseph | Home - GHS Pool [Directions] | 11:00 a.m. | ||
| Mon., 10/1 | V Girls Soccer | Trumbull | Home - Cardinal Stadium [Directions] | 4:30 p.m. | L 2-3 | |
| Mon., 10/1 | JV Girls Soccer | Trumbull | Home - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | ||
| Mon., 10/1 | V Girls Volleyball | Staples | Home - GHS Gymnasium [Directions] | 4:30 p.m. | W 3-0 | |
| Mon., 10/1 | JV Girls Volleyball | Staples | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 10/1 | FR Girls Volleyball | Staples | Away - Staples H.S. Gym [Directions] | 4:00 p.m. | 2:45 early dismissal | |
| Tue., 10/2 | V Boys Cross Country | Danbury, Staples, Ridgefield | Home - Greenwich Point [Directions] | 4:00 p.m. | 2:30 early dismissal | |
| Tue., 10/2 | JV Boys Soccer | Norwalk | Away - Callahan Complex at Nathan Hale Lower [Directions] | 5:00 p.m. | ||
| Tue., 10/2 | FR Boys Soccer | Norwalk | Home - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | ||
| Tue., 10/2 | V Girls Cross Country | Danbury, Staples, Ridgefield | Home - Greenwich Point [Directions] | 4:00 p.m. | 2:30 early dismissal | |
| Tue., 10/2 | V Field Hockey | Danbury | Home - Cardinal Stadium [Directions] | 4:30 p.m. | W 5-0 | |
| Tue., 10/2 | JV Field Hockey | Danbury | Home - Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Tue., 10/2 | FR Field Hockey | Danbury | Away - Danbury HS Grass Field Hockey Field [Directions] | 4:00 p.m. | 2:45 early dismissal | |
| Wed., 10/3 | SO Football | Darien | Home - Cardinal Stadium [Directions] | Cancelled | Cancelled | |
| Wed., 10/3 | V Girls Swimming and Diving | Trumbull | Away - Hillcrest MS [Directions] | 4:00 p.m. | 2:00 early dismissal | |
| Wed., 10/3 | V Girls Volleyball | Stamford | Home - GHS Gymnasium [Directions] | 4:30 p.m. | W 3-0 | |
| Wed., 10/3 | JV Girls Volleyball | Stamford | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 10/3 | FR Girls Volleyball | Stamford | Away [Directions] | 4:00 p.m. | 2:45 early dismissal | |
| Thu., 10/4 | FR Football | New Canaan | Home - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Thu., 10/4 | V Boys Soccer | Trumbull | Away - New Turf Field [Directions] | 5:30 p.m. | W 1-0 | |
| Thu., 10/4 | FR Boys Soccer | Trumbull | Home - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | ||
| Thu., 10/4 | V Field Hockey | Darien | Away - DHS Stadium Field [Directions] | 4:00 p.m. | L 2-7 | 2:30 early dismissal |
| Thu., 10/4 | JV Field Hockey | Darien | Away - DHS Stadium Field [Directions] | 5:30 p.m. | 2:30 early dismissal | |
| Thu., 10/4 | V Girls Volleyball | Norwalk | Away - Scarso Gymnasium [Directions] | 4:30 p.m. | W 3-0 | 2:45 early dismissal |
| Thu., 10/4 | JV Girls Volleyball | Norwalk | Away - Scarso Gymnasium [Directions] | 5:30 p.m. | 2:45 early dismissal | |
| Fri., 10/5 | JV Boys Soccer | Trumbull | Away - The Pit [Directions] | 4:30 p.m. | 2:45 early dismissal | |
| Fri., 10/5 | V Boys Water Polo | CPCT | Away - Chelsea Piers | 6:30 p.m. | ||
| Fri., 10/5 | FR Field Hockey | Darien | Home - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | ||
| Fri., 10/5 | V Girls Soccer | Westhill | Away - Westhill Front Turf Field [Directions] | 4:30 p.m. | L 0-2 | 2:45 early dismissal |
| Fri., 10/5 | JV Girls Soccer | Westhill | Away - Rippowam MS - Turf Field [Directions] | 4:30 p.m. | 2:45 early dismissal | |
| Fri., 10/5 | FR Girls Soccer | Trumbull | Away - JV Grass Field [Directions] | 4:30 p.m. | 2:45 early dismissal | |
| Fri., 10/5 | V Girls Swimming and Diving | Staples | Away - Staples HS Pool [Directions] | 4:00 p.m. | 2:00 early dismissal | |
| Sat., 10/6 | V Boys Cross Country | Wickham Invitational | Away - Wickham Park | 9:00 a.m. | ||
| Sat., 10/6 | V Football | New Canaan | Away - Dunning Stadium [Directions] | 7:00 p.m. | W 42-14 | |
| Sat., 10/6 | V Boys Water Polo | Suffield Academy | Away - Suffield Academy | 2:00 p.m. | ||
| Sat., 10/6 | JV Boys Water Polo | Suffield Academy | Away - Suffield Academy | 2:00 p.m. | ||
| Sat., 10/6 | V Girls Cross Country | Wickham Invitational | Away - Wickham Park | 9:00 a.m. | ||
| Sat., 10/6 | JV Girls Swimming and Diving | New Canaan | Home - GHS Pool [Directions] | 8:30 a.m. | ||
| Mon., 10/8 | SO Football | Darien | Away - DHS Stadium East Turf Field [Directions] | 4:00 p.m. | 3:00 early dismissal | |
| Mon., 10/8 | V Boys Soccer | Westhill | Home - Cardinal Stadium [Directions] | 4:30 p.m. | T 2-2 | |
| Mon., 10/8 | JV Boys Soccer | Westhill | Home - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | ||
| Mon., 10/8 | FR Boys Soccer | Westhill | Away - Westhill Front Turf Field [Directions] | 4:30 p.m. | 2:45 early dismissal | |
| Mon., 10/8 | V Field Hockey | Norwalk | Home - GHS Field 3 [Directions] | 4:00 p.m. | W 5-4(OT) | |
| Mon., 10/8 | JV Field Hockey | Norwalk | Home - GHS Field 3 [Directions] | 5:00 p.m. | ||
| Mon., 10/8 | FR Field Hockey | Norwalk | Away - Testa Field, NHS [Directions] | 5:30 p.m. | ||
| Mon., 10/8 | School Holidays and Closings | Columbus Day | ||||
| Tue., 10/9 | V Boys Cross Country | Wilton, Stamford, Trinity Catholic | Home - Greenwich Point [Directions] | 4:00 p.m. | 2:30 early dismissal | |
| Tue., 10/9 | FR Boys Soccer | Wilton | Home - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | ||
| Tue., 10/9 | V Girls Cross Country | Wilton, Stamford, Trinity Catholic | Home - Greenwich Point [Directions] | 4:00 p.m. | 2:30 early dismissal | |
| Tue., 10/9 | FR Girls Soccer | Wilton | Away - Allen's Field [Directions] | 4:00 p.m. | 2:45 early dismissal | |
| Wed., 10/10 | FR Football | Brunswick School | Away - Brunswick School | 4:00 p.m. | 2:45 early dismissal | |
| Wed., 10/10 | V Boys Soccer | Wilton | Away - Lilly Field - Turf [Directions] | 5:00 p.m. | W 5-0 | |
| Wed., 10/10 | JV Boys Soccer | Wilton | Away - Allen's Field [Directions] | 4:00 p.m. | 2:30 early dismissal | |
| Wed., 10/10 | V Field Hockey | Wilton | Away - Fujitani Field - Turf [Directions] | 5:30 p.m. | W 6-2 | |
| Wed., 10/10 | JV Field Hockey | Wilton | Away - Fujitani Field - Turf [Directions] | 4:00 p.m. | 2:30 early dismissal | |
| Wed., 10/10 | V Girls Soccer | Wilton | Home - Cardinal Stadium [Directions] | 6:00 p.m. | L 0-2 | |
| Wed., 10/10 | JV Girls Soccer | Wilton | Home - GHS Field 3 [Directions] | 4:30 p.m. | ||
| Wed., 10/10 | V Girls Volleyball | Trumbull | Home - Greenwich Gymnasium [Directions] | 4:00 p.m. | L 2-3 | 2:00 early dismissal |
| Wed., 10/10 | JV Girls Volleyball | Trumbull | Home - Greenwich Gymnasium [Directions] | 5:30 p.m. | 2:00 early dismissal | |
| Thu., 10/11 | FR Girls Volleyball | Trumbull | Home - GHS Gymnasium [Directions] | 4:30 p.m. | ||
| Fri., 10/12 | V Boys Soccer | Bridgeport Central | Home - Cardinal Stadium [Directions] | 6:00 p.m. | W 6-0 | |
| Fri., 10/12 | JV Boys Soccer | Bridgeport Central | Home - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | ||
| Fri., 10/12 | V Boys Water Polo | Cardinal Tournament | Home - GHS Pool [Directions] | 6:00 p.m. | Friday through Sunday | |
| Fri., 10/12 | V Girls Soccer | Bridgeport Central | Home - GHS Field 3 [Directions] | 4:30 p.m. | W 7-0 | 2:00 early dismissal |
| Fri., 10/12 | V Girls Swimming and Diving | New Canaan | Away - New Canaan YMCA [Directions] | 3:00 p.m. | 1:15 early dismissal | |
| Fri., 10/12 | V Girls Volleyball | Westhill | Home - GHS Gymnasium [Directions] | 4:30 p.m. | L 2-3 | |
| Fri., 10/12 | JV Girls Volleyball | Westhill | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 10/12 | FR Girls Volleyball | Westhill | Away - Westhill - New Gymnasium [Directions] | 4:30 p.m. | 3:00 early dismissal | |
| Sat., 10/13 | SO Football | New Rochelle (NY) | Home - GHS Field 7 [Directions] | 12:00 p.m. | ||
| Sat., 10/13 | V Field Hockey | Ridgefield | Home - Cardinal Stadium [Directions] | 3:00 p.m. | W 2-0 | |
| Sat., 10/13 | JV Field Hockey | Ridgefield | Home - Cardinal Stadium [Directions] | 1:30 p.m. | ||
| Sat., 10/13 | FR Field Hockey | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 10:00 a.m. | ||
| Sat., 10/13 | JV Girls Soccer | Fairfield Warde | Away - Fairfield Warde Grass Soccer Field [Directions] | 10:00 a.m. | ||
| Sat., 10/13 | FR Girls Soccer | Greenwich Country Day | Away - Greenwich Country Day School | 1:15 p.m. | ||
| Sat., 10/13 | V Girls Volleyball | Connecticut Fall Brawl | Away - RHAM HS | 9:00 a.m. | ||
| Mon., 10/15 | JV Football | New Canaan | Away - NCHS Water Tower Turf Field [Directions] | 4:00 p.m. | 2:45 early dismissal | |
| Mon., 10/15 | V Boys Soccer | Fairfield Warde | Home - Cardinal Stadium [Directions] | 4:30 p.m. | L 0-1 | |
| Mon., 10/15 | JV Boys Soccer | Fairfield Warde | Home - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | ||
| Mon., 10/15 | V Girls Volleyball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 5:30 p.m. | W 3-0 | 2:30 early dismissal |
| Mon., 10/15 | JV Girls Volleyball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 4:00 p.m. | 2:30 early dismissal | |
| Mon., 10/15 | FR Girls Volleyball | Wilton | Home - GHS Gymnasium [Directions] | 4:30 p.m. | ||
| Tue., 10/16 | V Field Hockey | Rye (NY) | Home - Cardinal Stadium [Directions] | 4:00 p.m. | W 4-0 | |
| Tue., 10/16 | JV Field Hockey | Rye (NY) | Home - Cardinal Stadium [Directions] | 5:00 p.m. | ||
| Tue., 10/16 | V Girls Soccer | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 6:00 p.m. | W 1-0 | |
| Tue., 10/16 | FR Girls Soccer | Danbury | Home - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | ||
| Wed., 10/17 | V Boys Soccer | Norwalk | Away - Testa Field, NHS [Directions] | 7:00 p.m. | L 3-0 | |
| Wed., 10/17 | JV Girls Soccer | Danbury | Away - Danbury HS Grass Soccer Field [Directions] | 4:30 p.m. | 2:30 early dismissal | |
| Wed., 10/17 | JV Girls Swimming and Diving | Ridgefield | Home - GHS Pool [Directions] | 6:30 p.m. | ||
| Wed., 10/17 | V Girls Volleyball | Bridgeport Central | Home - GHS Gymnasium [Directions] | 4:30 p.m. | W 3-0 | |
| Wed., 10/17 | JV Girls Volleyball | Bridgeport Central | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 10/18 | V Boys Cross Country | FCIAC Championships | Away - Waveny Park | 2:00 p.m. | ||
| Thu., 10/18 | V Boys Soccer | Danbury | Home - Cardinal Stadium [Directions] | 4:15 p.m. | W 2-0 | |
| Thu., 10/18 | JV Boys Soccer | Danbury | Home - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | ||
| Thu., 10/18 | FR Boys Soccer | Danbury | Away - Danbury HS Grass Soccer Field [Directions] | 4:00 p.m. | 2:45 early dismissal | |
| Thu., 10/18 | V Girls Cross Country | FCIAC Championships | Away - Waveny Park | 2:00 p.m. | ||
| Thu., 10/18 | FR Field Hockey | Wilton | Home - GHS Field 3 [Directions] | 4:30 p.m. | ||
| Thu., 10/18 | V Girls Soccer | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 5:30 p.m. | T 2-2 | |
| Thu., 10/18 | FR Girls Soccer | New Canaan | Away - Saxe MS Field [Directions] | 4:00 p.m. | 2:45 early dismissal | |
| Fri., 10/19 | V Boys Water Polo | Steve Pal Tournament | Away | 6:00 p.m. | ||
| Fri., 10/19 | V Field Hockey | Brien McMahon | Home - Cardinal Stadium [Directions] | 6:00 p.m. | W 2-1 | |
| Fri., 10/19 | JV Field Hockey | Brien McMahon | Home - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Fri., 10/19 | V Girls Volleyball | Fairfield Warde | Home - GHS Gymnasium [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 10/19 | JV Girls Volleyball | Fairfield Warde | Home - GHS Gymnasium [Directions] | 4:30 p.m. | ||
| Fri., 10/19 | FR Girls Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | 2:45 early dismissal | |
| Sat., 10/20 | V Football | Westhill | Away - J. Walter Kennedy Stadium [Directions] | 2:00 p.m. | W 53-0 | |
| Sat., 10/20 | FR Football | Westhill | Home - Cardinal Stadium [Directions] | 9:00 a.m. | ||
| Sat., 10/20 | V Boys Soccer | Trinity Catholic | Away - Gaglio Field | 2:15 p.m. | W 7-0 | |
| Sat., 10/20 | JV Boys Water Polo | Brunswick School | Away - Brunswick School | 9:00 a.m. | ||
| Sat., 10/20 | V Girls Soccer | Trinity Catholic | Home - Cardinal Stadium [Directions] | 12:00 p.m. | W 5-0 | |
| Sat., 10/20 | V Girls Swimming and Diving | Westhill/Stamford | Home - GHS Pool [Directions] | 12:00 p.m. | ||
| Sat., 10/20 | JV Girls Swimming and Diving | Darien | Home - GHS Pool [Directions] | 8:30 a.m. | ||
| Mon., 10/22 | JV Football | Westhill | Home - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Mon., 10/22 | FR Boys Soccer | Trumbull | Home - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | ||
| Mon., 10/22 | V Girls Volleyball | Danbury | Home - GHS Gymnasium [Directions] | 4:30 p.m. | W 3-0 | |
| Mon., 10/22 | JV Girls Volleyball | Danbury | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 10/22 | FR Girls Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 4:00 p.m. | 2:45 early dismissal | |
| Tue., 10/23 | FR Boys Soccer | Staples | Away - Wakeman Field B (turf) [Directions] | 4:00 p.m. | 2:30 early dismissal | |
| Tue., 10/23 | V Field Hockey | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 6:00 p.m. | W 6-0 | |
| Tue., 10/23 | JV Field Hockey | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 4:30 p.m. | 3:00 early dismissal | |
| Wed., 10/24 | V Girls Volleyball | Trinity Catholic | Away - Walsh Court | 5:30 p.m. | W 3-0 | 2:30 early dismissal |
| Wed., 10/24 | JV Girls Volleyball | Trinity Catholic | Away - Walsh Court | 4:00 p.m. | 2:30 early dismissal | |
| Thu., 10/25 | V Football | Fairfield Ludlowe | Home - Cardinal Stadium [Directions] | 6:00 p.m. | W 56-7 | |
| Thu., 10/25 | SO Football | New Canaan | Home - GHS Field 7 [Directions] | 4:00 p.m. | ||
| Thu., 10/25 | FR Football | Fairfield Ludlowe | Away - Taft Field [Directions] | 5:30 p.m. | 2:55 EARLY DISMISSAL | |
| Thu., 10/25 | V Boys Water Polo | CPCT | Home - GHS Pool [Directions] | 4:30 p.m. | ||
| Fri., 10/26 | V Boys Cross Country | Class LL State Championships | Away - Wickham Park | 10:20 a.m. | ||
| Fri., 10/26 | JV Football | Fairfield Ludlowe | Home - Field 7 [Directions] | 4:00 p.m. | 2:45 early dismissal | |
| Fri., 10/26 | V Boys Soccer | FCIAC Tournament | Away - Staples HS | 3:00 p.m. | 1:00 EARLY DISMISSAL | |
| Fri., 10/26 | V Girls Cross Country | Class LL State Championships | Away - Wickham Park | 10:50 a.m. | ||
| Fri., 10/26 | V Field Hockey | FCIAC Tournament | Home - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Sat., 10/27 | JV Girls Swimming and Diving | FCIAC Championships | Home - GHS Pool [Directions] | 2:30 p.m. | ||
| Sat., 10/27 | JV Girls Volleyball | Jamboree | Away - Fairfield Warde HS | 9:00 a.m. | ||
| Mon., 10/29 | V Field Hockey | FCIAC SemiFinal | Away - Brien McMahon | 7:30 p.m. | ||
| Mon., 10/29 | V Girls Swimming and Diving | FCIAC Diving Championships | Away - Westhill HS | 5:00 p.m. | ||
| Tue., 10/30 | V Girls Swimming and Diving | FCIAC Trials | Home - GHS Pool [Directions] | 5:30 p.m. | ||
| Tue., 10/30 | V Girls Volleyball | FCIAC Tournament | Home - GHS Gymnasium [Directions] | 4:30 p.m. | ||
| Wed., 10/31 | JV Boys Water Polo | Greenwich Aquatics | Home - GHS Pool [Directions] | 6:30 p.m. | ||
| Wed., 10/31 | School Holidays and Closings | Halloween | ||||
| Thu., 11/1 | V Boys Cross Country | State Open Championships | Away - Wickham Park | 2:00 p.m. | ||
| Thu., 11/1 | V Girls Cross Country | State Open Championships | Away - Waveny Park | 2:00 p.m. | ||
| Thu., 11/1 | V Girls Swimming and Diving | FCIAC Championships | Home - GHS Pool [Directions] | 6:30 p.m. | ||
| Fri., 11/2 | V Football | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 7:00 p.m. | W 33-3 | |
| Fri., 11/2 | JV Boys Water Polo | Cardinal Cup | Home - GHS Pool [Directions] | 6:00 p.m. | Friday through Saturday | |
| Fri., 11/2 | V Girls Volleyball | Scrimmage | Home - GHS Gymnasium [Directions] | 3:45 p.m. | ||
| Sat., 11/3 | JV Football | Ridgefield | Home - Cardinal Stadium [Directions] | 10:00 a.m. | ||
| Sat., 11/3 | FR Football | Ridgefield | Home - GHS Field 7 [Directions] | 10:00 a.m. | ||
| Mon., 11/5 | V Girls Volleyball | State Tournament | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 11/6 | School Holidays and Closings | Election Day | ||||
| Wed., 11/7 | SO Football | New Canaan | Away - WTT1 [Directions] | 4:00 p.m. | 300 early dismissal | |
| Wed., 11/7 | V Boys Soccer | State Tournament | Home - Cardinal Stadium [Directions] | 2:00 p.m. | ||
| Wed., 11/7 | V Boys Water Polo | West Point | Away - United States Military Academy | 4:30 p.m. | 2:45 EARLY DISMISSAL | |
| Wed., 11/7 | V Field Hockey | FCIAC Tournament | Away - Amity HS | 2:00 p.m. | ||
| Wed., 11/7 | V Girls Swimming and Diving | Class LL Diving Championships | Away - Middletown HS | 5:30 p.m. | ||
| Thu., 11/8 | V Girls Volleyball | State Tournament | Away - Fairfield Ludlowe HS | 5:00 p.m. | ||
| Fri., 11/9 | V Football | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 5:00 p.m. | W 42-3 | |
| Sat., 11/10 | FR Football | Danbury | Home - GHS Field 7 [Directions] | 10:00 a.m. | ||
| Sat., 11/10 | V Boys Soccer | State Tournament | Away - Glastonbury HS | 2:00 p.m. | ||
| Sat., 11/10 | V Boys Water Polo | Mid Atlantic Championships | Away | 9:00 a.m. | ||
| Sat., 11/10 | V Girls Swimming and Diving | Class LL Trials | Away - East Hartford HS | 11:30 a.m. | ||
| Sat., 11/10 | V Girls Volleyball | State Tournament | Away - Westhill HS | 5:00 p.m. | ||
| Sun., 11/11 | School Holidays and Closings | Veterans Day | ||||
| Mon., 11/12 | JV Football | Danbury | Away - Danbury HS Stadium [Directions] | 4:30 p.m. | ||
| Mon., 11/12 | School Holidays and Closings | Veterans Day observed | ||||
| Wed., 11/14 | V Football | Xavier | Home - Cardinal Stadium [Directions] | 6:00 p.m. | W 38-7 | |
| Wed., 11/14 | SO Football | New Canaan | Away - WTT1 [Directions] | 4:30 p.m. | ||
| Wed., 11/14 | FR Football | Staples | Away - Staples Stadium [Directions] | 5:00 p.m. | ||
| Wed., 11/14 | V Girls Swimming and Diving | Class LL State Championships | Away - Southern Connecticut State University | 6:00 p.m. | ||
| Fri., 11/16 | V Girls Swimming and Diving | State Open Diving Championships | Away - Middletown HS | 5:30 p.m. | ||
| Sat., 11/17 | JV Football | Staples | Home - Cardinal Stadium [Directions] | 10:00 a.m. | ||
| Sat., 11/17 | V Girls Swimming and Diving | State Open Championships | Away - Yale University | 12:00 p.m. | ||
| Tue., 11/20 | V Bowling | MATCH | Away - Nutmeg Lanes | 3:00 p.m. | 2:00 EARLY DISMISSAL | |
| Thu., 11/22 | V Football | Staples | Home - Cardinal Stadium [Directions] | 10:00 a.m. | W 29-0 | |
| Thu., 11/22 | School Holidays and Closings | Thanksgiving Day | ||||
| Tue., 11/27 | V Football | State QuarterFinal | Home - Cardinal Stadium [Directions] | 6:30 p.m. | ||
| Tue., 11/27 | V Bowling | MATCH | Away - Nutmeg Lanes | 3:00 p.m. | 2:00 EARLY DISMISSAL | |
| Fri., 11/30 | V Girls Basketball | Weston (Scrim.) | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 11/30 | JV Girls Basketball | Weston (Scrim.) | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 12/1 | V Boys Ice Hockey | Fairfield Warde/Ludlowe (Scrim.) | Home - Dorothy Hamill Ice Rink [Directions] | 6:30 p.m. | ||
| Sun., 12/2 | V Football | State SemiFinal | Home - Cardinal Stadium [Directions] | 12:30 p.m. | ||
| Mon., 12/3 | School Holidays and Closings | First day of Chanukah | ||||
| Tue., 12/4 | V Bowling | MATCH | Away - Nutmeg Lanes | 3:00 p.m. | 2:00 EARLY DISMISSAL | |
| Tue., 12/4 | V Girls Ice Hockey | Rye Country Day (NY) (Scrim.) | Away - RCDS | 5:00 p.m. | 3:00 EARLY DISMISSAL | |
| Wed., 12/5 | V Boys Basketball | Wright Tech (Scrim.) | Away - Wright Tech [Directions] | 5:15 p.m. | ||
| Wed., 12/5 | JV Boys Basketball | Wright Tech (Scrim.) | Away - Thomas R. Good Gymnasium [Directions] | 5:15 p.m. | 2:45 EARLY DISMISSAL | |
| Wed., 12/5 | FR Boys Basketball | Wright Tech (Scrim.) | Away - Thomas R. Good Gymnasium [Directions] | 4:15 p.m. | 3:00 EARLY DISMISSAL | |
| Wed., 12/5 | V Boys Ice Hockey | North Haven (Scrim.) | Away - Northford Ice Pavilion [Directions] | 4:00 p.m. | 2:00 EARLY DISMISSAL | |
| Wed., 12/5 | V Girls Basketball | Naugatuck (Scrim.) | Away - Naugatuck HS [Directions] | 4:30 p.m. | 3:00 EARLY DISMISSAL | |
| Fri., 12/7 | V Boys Basketball | Abbott Tech (Scrim.) | Home - GHS Gymnasium [Directions] | 5:00 p.m. | ||
| Sat., 12/8 | V Football | State Championship | Away | 10:00 a.m. | ||
| Sat., 12/8 | V Girls Basketball | Fairfield Ludlowe (Scrim.) | Home - GHS Gymnasium [Directions] | 12:00 p.m. | ||
| Mon., 12/10 | V Boys Basketball | Fairfield Prep (Scrim.) | Away - Alumni Hall, Fairfield University [Directions] | 4:00 p.m. | 3:00 EARLY DISMISSAL | |
| Mon., 12/10 | School Holidays and Closings | Last day of Chanukah | ||||
| Tue., 12/11 | V Bowling | MATCH | Away - Nutmeg Lanes | 3:00 p.m. | 2:00 EARLY DISMISSAL | |
| Wed., 12/12 | V Wrestling | Wilton | Home - GHS Gymnasium [Directions] | 5:00 p.m. | Greenwich HS 70 Wilton HS 9 | |
| Wed., 12/12 | V Girls Basketball | Trinity Catholic | Home - GHS Gymnasium [Directions] | 6:00 p.m. | L 46-62 | |
| Wed., 12/12 | JV Girls Basketball | Trinity Catholic | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 12/12 | JV Girls Ice Hockey | Greenwich Country Day | Away - Greenwich Skating Club | 4:00 p.m. | ||
| Thu., 12/13 | V Boys Fencing | Rye Country Day (NY) | Away - Moorehouse Fencing Club | 4:30 p.m. | ||
| Thu., 12/13 | FR Girls Basketball | Scrimmage | Away - Western MS | 4:00 p.m. | ||
| Thu., 12/13 | V Girls Fencing | Rye Country Day (NY) | Away - Morehouse Fencing Club | 4:30 p.m. | ||
| Thu., 12/13 | V Girls Ice Hockey | Morristown-Beard (NJ) | Home - Dorothy Hamill Ice Rink [Directions] | 8:00 p.m. | W 8-6 | |
| Fri., 12/14 | JV Boys Ice Hockey | Ridgefield | Home - Dorothy Hamill Ice Rink [Directions] | 9:15 p.m. | ||
| Fri., 12/14 | V Girls Basketball | Rye (NY) | Away - Rye HS | 7:00 p.m. | L 30-51 | |
| Fri., 12/14 | JV Girls Basketball | Wright Tech | Away - Wright Tech [Directions] | 5:15 p.m. | 2:45 EARLY DISMISSAL | |
| Fri., 12/14 | FR Girls Basketball | Wright Tech | Away - Wright Tech [Directions] | 4:00 p.m. | ||
| Sat., 12/15 | V Boys Ice Hockey | Immaculate | Away - Danbury Ice Arena [Directions] | 7:00 p.m. | T 2-2(OT) | |
| Sat., 12/15 | V Boys Indoor Track | MEET | Away - Staples HS | 10:00 a.m. | ||
| Sat., 12/15 | V Boys Indoor Track | ATT Coaches Hall of Fame | Away - New York Armory | 1:30 p.m. | ||
| Sat., 12/15 | V Wrestling | Fairfield Ludlowe Tournament | Away - Fairifeld Ludlowe HS | 9:00 a.m. | ||
| Sat., 12/15 | JV Wrestling | Ludlowe Invitational | Away - Fairfeild Ludlowe HS | 9:00 a.m. | ||
| Sat., 12/15 | V Girls Basketball | East Rampo (NY) | Away - Rye HS | TBA | W 60-46 | |
| Sat., 12/15 | V Girls Indoor Track | MEET | Away - Staples HS | 10:00 a.m. | ||
| Sun., 12/16 | JV Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Conners [Directions] | 8:30 p.m. | ||
| Mon., 12/17 | JV Boys Ice Hockey | Darien | Away - Stamford Twin Rinks [Directions] | 8:40 p.m. | ||
| Mon., 12/17 | V Boys Swimming and Diving | Darien | Away - Darien YMCA [Directions] | 3:00 p.m. | 1:00 EARLY DISMISSAL | |
| Mon., 12/17 | V Wrestling | New Canaan | Home - GHS Gymnasium [Directions] | 5:00 p.m. | Greenwich HS 49 New Canaan HS 27 | |
| Tue., 12/18 | V Bowling | MATCH | Away - Nutmeg Lanes | 3:00 p.m. | 2:00 EARLY DISMISSAL | |
| Tue., 12/18 | FR Girls Basketball | Greenwich Country Day | Away - GCDS | 4:30 p.m. | ||
| Wed., 12/19 | V Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 7:00 p.m. | W 56-53 | |
| Wed., 12/19 | V Boys Ice Hockey | New Canaan | Home - Hamill Rink [Directions] | 5:15 p.m. | W 3-1 | |
| Wed., 12/19 | V Boys Swimming and Diving | Wilton | Home - GHS Pool [Directions] | 4:30 p.m. | ||
| Wed., 12/19 | V Wrestling | Fairfield Ludlowe | Away - FLHS Aux Gym [Directions] | 6:00 p.m. | Greenwich 45 Fairfield-Ludlowe 27 | |
| Wed., 12/19 | V Girls Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:00 p.m. | L 40-48 | |
| Wed., 12/19 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice [Directions] | 4:00 p.m. | W 3-0 | 2:00 EARLY DISMISSAL |
| Fri., 12/21 | V Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 7:00 p.m. | L 45-66 | |
| Fri., 12/21 | JV Boys Ice Hockey | St. Joseph | Away - Shelton Rinks [Directions] | 8:30 p.m. | ||
| Fri., 12/21 | V Girls Basketball | New Canaan | Away - New Canaan HS [Directions] | 5:00 p.m. | W 43-39 | |
| Fri., 12/21 | V Girls Gymnastics | Staples | Home - Greenwich YWCA [Directions] | 5:00 p.m. | 137.65 | |
| Sat., 12/22 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Dorothy Hamill Ice Rink [Directions] | 4:15 p.m. | W 9-3 | |
| Mon., 12/24 | School Holidays and Closings | Christmas Eve | ||||
| Tue., 12/25 | School Holidays and Closings | Christmas Day | ||||
| Wed., 12/26 | V Boys Indoor Track | North Shore Invitational | Away - New York Armory | 9:00 a.m. | ||
| Thu., 12/27 | V Boys Basketball | South Windsor | Away - Bristol Central HS [Directions] | 6:00 p.m. | W 86-79(2OT) | |
| Thu., 12/27 | V Girls Basketball | SMSA | Away - Plainville HS [Directions] | 12:30 p.m. | L 34-44 | |
| Fri., 12/28 | JV Boys Basketball | Stamford | Away - Kuzco Gymnasium at Stamford HS [Directions] | 4:00 p.m. | ||
| Fri., 12/28 | FR Boys Basketball | Wright Tech | Away - Wright Tech [Directions] | 10:00 a.m. | ||
| Fri., 12/28 | JV Boys Ice Hockey | New Canaan | Home - Dorothy Hamill Ice Rink [Directions] | 5:30 p.m. | ||
| Fri., 12/28 | V Girls Basketball | Amistad | Away - Plainville HS [Directions] | 4:00 p.m. | W 55-43 | |
| Fri., 12/28 | JV Girls Ice Hockey | New Canaan | Away - Darien Ice Rink [Directions] | 2:10 p.m. | ||
| Sat., 12/29 | V Boys Basketball | Wolcott | Away - Bristol Central HS [Directions] | TBA | W 76-47 | |
| Sat., 12/29 | V Boys Ice Hockey | Darien | Home - Greenwich Skating Club [Directions] | 4:00 p.m. | W 3-0 | |
| Sat., 12/29 | V Girls Ice Hockey | New Canaan | Home - Greenwich Skating Club [Directions] | 12:30 p.m. | W 3-2 | |
| Mon., 12/31 | School Holidays and Closings | New Years Eve | ||||
| Tue., 1/1 | School Holidays and Closings | New Years Day | ||||
| Wed., 1/2 | V Boys Ice Hockey | Hamden | Home - Dorothy Hamill Ice Rink [Directions] | 5:15 p.m. | L 3-8 | |
| Wed., 1/2 | V Wrestling | Staples | Away - Staples H.S. Gym [Directions] | 6:00 p.m. | Greenwich 38 staples 36 | |
| Wed., 1/2 | JV Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - Winter Garden Rink-Ridgefield [Directions] | 8:30 p.m. | ||
| Thu., 1/3 | V Wrestling | Stamford | Away - Stamford High Aux Gym [Directions] | 6:30 p.m. | Stamford 18 Greenwich 60 | |
| Thu., 1/3 | V Girls Basketball | Darien | Away - DHS Main Gym [Directions] | 7:00 p.m. | L 34-50 | |
| Thu., 1/3 | JV Girls Basketball | Darien | Away - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 1/3 | FR Girls Basketball | Darien | Away - DHS Main Gym [Directions] | 4:00 p.m. | 2:45 EARLY DISMISSAL | |
| Fri., 1/4 | V Boys Basketball | Darien | Home - Brien McMahon HS [Directions] | 7:00 p.m. | W 67-51 | |
| Fri., 1/4 | JV Boys Ice Hockey | St. Joseph | Home - Dorothy Hamill Ice Rink [Directions] | 9:15 p.m. | ||
| Fri., 1/4 | V Girls Gymnastics | Wilton | Away - Wilton HS Aux. Gym [Directions] | 5:30 p.m. | Greenwich 129.8
Wilton 129.55 [Detailed Results] | |
| Sat., 1/5 | JV Boys Basketball | Darien | Home - Central MS [Directions] | 10:30 a.m. | ||
| Sat., 1/5 | FR Boys Basketball | Darien | Home - Central MS [Directions] | 9:00 a.m. | ||
| Sat., 1/5 | JV Boys Ice Hockey | Mamaroneck (NY) | Away - Hommocks School | 8:30 p.m. | ||
| Sat., 1/5 | V Boys Indoor Track | MEET | Away - Staples HS | 10:00 a.m. | ||
| Sat., 1/5 | V Boys Indoor Track | Ocean Breeze Freedom Games | Away - Ocean Breeze Center | 9:00 a.m. | ||
| Sat., 1/5 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Winter Garden Ice Arena [Directions] | 8:50 p.m. | L 1-2 | |
| Sat., 1/5 | V Girls Indoor Track | MEET | Away - Staples HS | 10:00 a.m. | ||
| Mon., 1/7 | V Boys Basketball | Fairfield Ludlowe | Home - Brunswick School [Directions] | 6:00 p.m. | L 43-47 | |
| Mon., 1/7 | V Girls Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 7:00 p.m. | L 22-55 | |
| Mon., 1/7 | JV Girls Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 1/7 | FR Girls Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 4:00 p.m. | 2:30 EARLY DISMISSAL | |
| Mon., 1/7 | V Girls Ice Hockey | Simsbury | Home - Dorothy Hamill Ice Rink [Directions] | 5:00 p.m. | L 3-5 | |
| Tue., 1/8 | JV Boys Ice Hockey | Ridgefield | Away - Danbury Ice Arena [Directions] | 8:00 p.m. | ||
| Tue., 1/8 | V Bowling | MATCH | Away - Nutmeg Lanes | 3:00 p.m. | 2:00 EARLY DISMISSAL | |
| Wed., 1/9 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland Of Ice [Directions] | 8:00 p.m. | T 5-5(OT) | |
| Wed., 1/9 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Away - Pat Spinola Natatorium [Directions] | 3:30 p.m. | 1:30 EARLY DISMISSAL | |
| Wed., 1/9 | V Wrestling | Trumbull | Home - GHS Gymnasium [Directions] | 5:00 p.m. | Trumbull 42 Greenwich 33 | |
| Wed., 1/9 | V Girls Ice Hockey | Stamford/Westhill/Staples | Home - Dorothy Hamill Ice Rink [Directions] | 8:15 p.m. | W 8-0 | |
| Thu., 1/10 | V Boys Alpine Skiing | RACE | Away - Mt Southington | 4:00 p.m. | 1:30 EARLY DISMISSAL | |
| Thu., 1/10 | V Boys Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 7:00 p.m. | L 42-65 | |
| Thu., 1/10 | JV Boys Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 5:15 p.m. | ||
| Thu., 1/10 | FR Boys Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | 2:30 EARLY DISMISSAL | |
| Thu., 1/10 | V Boys Fencing | Brunswick School | Away - Brunswick School | 4:30 p.m. | ||
| Thu., 1/10 | V Boys Ice Hockey | Westhill/Stamford | Home - Dorothy Hamill Ice Rink [Directions] | 8:00 p.m. | L 5-8 | |
| Thu., 1/10 | V Girls Alpine Skiing | RACE | Away - Mt Southington | 4:00 p.m. | 1:30 EARLY RELEASE | |
| Thu., 1/10 | V Girls Basketball | St. Joseph | Home - Scofield Magnet MS [Directions] | 5:00 p.m. | L 39-55 | |
| Fri., 1/11 | JV Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland Of Ice [Directions] | 4:50 p.m. | 3:00 EARLY DISMISSAL | |
| Fri., 1/11 | V Boys Indoor Track | Yale Invitational | Away - Yale University | 1:00 p.m. | ||
| Fri., 1/11 | V Boys Swimming and Diving | New Canaan | Home - GHS Pool [Directions] | 4:30 p.m. | ||
| Sat., 1/12 | JV Boys Basketball | Fairfield Ludlowe | Home - Central MS [Directions] | 10:30 a.m. | ||
| Sat., 1/12 | FR Boys Basketball | Fairfield Ludlowe | Home - Central MS [Directions] | 9:00 a.m. | ||
| Sat., 1/12 | V Boys Fencing | Morgan Penta Meet | Away - Morgan School | 9:00 a.m. | ||
| Sat., 1/12 | V Boys Ice Hockey | Bishop Hendricken (RI) | Home - Dorothy Hamill Ice Rink [Directions] | 4:15 p.m. | L 0-5 | |
| Sat., 1/12 | V Boys Indoor Track | MEET | Away - Wilton HS | 10:00 a.m. | ||
| Sat., 1/12 | V Boys Indoor Track | Molloy Stanner Games | Away - New York Armory | 9:00 a.m. | ||
| Sat., 1/12 | V Wrestling | Greater Hartford Tournament | Away - Hall HS | 9:00 a.m. | ||
| Sat., 1/12 | JV Wrestling | Trumbull Duals | Away - Trumbull HS | 9:00 a.m. | ||
| Sat., 1/12 | V Competitive Cheerleading | Hatterfest | Away - Danbury HS | 9:00 a.m. | ||
| Sat., 1/12 | JV Girls Basketball | St. Joseph | Home - Western MS [Directions] | 10:30 a.m. | ||
| Sat., 1/12 | FR Girls Basketball | St. Joseph | Home - Western MS [Directions] | 9:00 a.m. | ||
| Sat., 1/12 | Winter Dance Team | Dancing in the Woods | Away - Woodlands HS | 2:00 p.m. | ||
| Sat., 1/12 | V Girls Fencing | Morgan Penta Meet | Away - Morgan School | 9:00 a.m. | ||
| Sat., 1/12 | V Girls Gymnastics | Darien | Away - Darien YMCA [Directions] | 2:30 p.m. | 123.45 | |
| Sat., 1/12 | V Girls Ice Hockey | Darien | Away - Darien Ice Rink [Directions] | 7:10 p.m. | L 0-2 | |
| Sat., 1/12 | V Girls Indoor Track | MEET | Away - Wilton HS | 10:00 a.m. | ||
| Mon., 1/14 | V Boys Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 7:00 p.m. | L 36-49 | |
| Mon., 1/14 | JV Boys Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 1/14 | FR Boys Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | 2:30 EARLY DISMISSAL | |
| Mon., 1/14 | V Girls Basketball | Ridgefield | Home - Scofield Magnet MS [Directions] | 5:00 p.m. | L 35-49 | |
| Mon., 1/14 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - So No Icehouse - Norwalk [Directions] | 8:40 p.m. | W 6-1 | |
| Mon., 1/14 | JV Girls Ice Hockey | Greenwich Country Day | Home - Dorothy Hamill Ice Rink [Directions] | 4:00 p.m. | ||
| Tue., 1/15 | FR Boys Basketball | Greenwich Country Day | Away - GCDS | 4:30 p.m. | ||
| Tue., 1/15 | V Bowling | MATCH | Away - Nutmeg Lanes | 3:00 p.m. | 2:00 EARLY DISMISSAL | |
| Wed., 1/16 | V Boys Ice Hockey | Northwest Catholic | Away - International Skating Center of Connecticut [Directions] | 3:20 p.m. | L 0-7 | |
| Wed., 1/16 | V Wrestling | Ridgefield, Brien McMahon | Home - GHS Gymnasium [Directions] | 5:00 p.m. | Greenwich 48 Ridgefield 31 Greenwich 60 Brien McMahon 21 | |
| Thu., 1/17 | V Boys Basketball | Staples | Home - GHS Gymnasium [Directions] | 5:30 p.m. | W 61-49 | |
| Thu., 1/17 | JV Boys Basketball | Staples | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 1/17 | V Boys Ice Hockey | Wilton | Home - Dorothy Hamill Ice Rink [Directions] | 8:00 p.m. | W 7-1 | |
| Thu., 1/17 | JV Wrestling | Fairfield Warde, Amity | Away - Fairfield Warde Small Gym [Directions] | 5:00 p.m. | 3:00 EARLY DISMISSAL | |
| Thu., 1/17 | V Girls Basketball | Staples | Away - Staples H.S. Gym [Directions] | 5:00 p.m. | L 34-48 | |
| Thu., 1/17 | JV Girls Basketball | Staples | Away - Staples H.S. Gym [Directions] | 3:30 p.m. | ||
| Fri., 1/18 | JV Boys Ice Hockey | Darien | Home - Dorothy Hamill Ice Rink [Directions] | 9:15 p.m. | ||
| Fri., 1/18 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Home - GHS Pool [Directions] | 4:00 p.m. | ||
| Fri., 1/18 | V Girls Gymnastics | Fairfield Ludlowe | Home - Greenwich YWCA [Directions] | 6:00 p.m. | 135.0 | |
| Fri., 1/18 | V Girls Ice Hockey | New Canaan | Away - Darien Ice Rink [Directions] | 8:20 p.m. | L 2-3 | |
| Sat., 1/19 | FR Boys Basketball | Staples | Home - Central MS [Directions] | 9:00 a.m. | ||
| Sat., 1/19 | V Boys Indoor Track | MEET | Away - Staples HS | 10:00 a.m. | ||
| Sat., 1/19 | V Boys Indoor Track | SCC Coaches Invitational | Away - New Haven Athletic Center | 9:00 a.m. | ||
| Sat., 1/19 | V Boys Indoor Track | New Balance Games | Away - New York Armory | 9:00 a.m. | ||
| Sat., 1/19 | V Boys Swimming and Diving | Fairfield Prep | Home - GHS Pool [Directions] | 1:00 p.m. | ||
| Sat., 1/19 | V Wrestling | Brunswick Tournament | Away - Brunswick School | 9:00 a.m. | ||
| Sat., 1/19 | JV Wrestling | Brunswick Invitational | Away - Brunswick School | 9:00 a.m. | ||
| Sat., 1/19 | V Competitive Cheerleading | Wildcat Open | Away - Seymour MS | 9:00 a.m. | ||
| Sat., 1/19 | JV Girls Basketball | Ridgefield | Home - Western MS [Directions] | 10:30 a.m. | ||
| Sat., 1/19 | FR Girls Basketball | Ridgefield | Home - Western MS [Directions] | 9:00 a.m. | ||
| Sat., 1/19 | V Girls Indoor Track | MEET | Away - Staples HS | 10:00 a.m. | ||
| Mon., 1/21 | V Boys Ice Hockey | Xavier | Home - Dorothy Hamill Ice Rink [Directions] | 2:45 p.m. | L 1-4 | |
| Mon., 1/21 | School Holidays and Closings | Martin Luther King Day | ||||
| Tue., 1/22 | V Boys Basketball | Stamford | Home - GHS Gymnasium [Directions] | 7:00 p.m. | L 60-66 | |
| Tue., 1/22 | JV Boys Basketball | Stamford | Home - GHS Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/22 | FR Boys Basketball | Stamford | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/22 | V Boys Ice Hockey | Trumbull | Home - Dorothy Hamill Ice Rink [Directions] | 4:30 p.m. | W 4-2 | |
| Tue., 1/22 | V Bowling | MATCH | Away - Nutmeg Lanes | 3:00 p.m. | 2:00 EARLY DISMISSAL | |
| Tue., 1/22 | V Girls Basketball | Stamford | Away - Kuzco Gymnasium at Stamford HS [Directions] | 7:00 p.m. | L 29-34 | |
| Tue., 1/22 | JV Girls Basketball | Stamford | Away - Kuzco Gymnasium at Stamford HS [Directions] | 5:15 p.m. | ||
| Tue., 1/22 | FR Girls Basketball | Stamford | Away - Kuzco Gymnasium at Stamford HS [Directions] | 4:00 p.m. | 2:45 EARLY DISMISSAL | |
| Tue., 1/22 | V Girls Ice Hockey | Hall/Conard | Away - Veteran's Memorial Rink [Directions] | 7:20 p.m. | W 3-0 | |
| Wed., 1/23 | V Boys Swimming and Diving | Westhill/Stamford | Home - GHS Pool [Directions] | 4:10 p.m. | ||
| Wed., 1/23 | V Wrestling | Westhill | Home - GHS Gymnasium [Directions] | 5:00 p.m. | Greenwich 36 Westhill 29 | |
| Thu., 1/24 | FR Boys Basketball | Brunswick School | Away - Brunswick School | 4:15 p.m. | 3:00 EARLY DISMISSAL | |
| Thu., 1/24 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Dorothy Hamill Ice Rink [Directions] | 8:00 p.m. | W 6-3 | |
| Fri., 1/25 | V Boys Basketball | Norwalk | Away - Scarso Gymnasium [Directions] | 7:00 p.m. | W 67-56 | |
| Fri., 1/25 | JV Boys Basketball | Norwalk | Away - Scarso Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/25 | FR Boys Basketball | Norwalk | Away - Scarso Gymnasium [Directions] | 4:00 p.m. | 2:45 EARLY DISMISSAL | |
| Fri., 1/25 | V Boys Ice Hockey | Ridgefield | Away - Winter Garden Ice Arena [Directions] | 4:30 p.m. | L 2-5 | |
| Fri., 1/25 | V Girls Basketball | Norwalk | Home - GHS Gymnasium [Directions] | 5:30 p.m. | L 36-82 | |
| Fri., 1/25 | JV Girls Basketball | Norwalk | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/25 | V Girls Ice Hockey | East Catholic Coop | Away - Newington Arena [Directions] | 8:20 p.m. | W 3-0 | |
| Sat., 1/26 | JV Boys Fencing | Novice Tournament | Away - Guilford HS | 8:30 a.m. | ||
| Sat., 1/26 | V Boys Indoor Track | Western Division Championship | Away - Staples HS | 10:00 a.m. | ||
| Sat., 1/26 | V Wrestling | Ridgefield Challenge | Away - Ridgefield HS | 9:00 a.m. | ||
| Sat., 1/26 | JV Wrestling | Godleski Tournament | Away - Norwalk HS | 9:00 a.m. | ||
| Sat., 1/26 | FR Girls Basketball | GCDS Tournament | Away - Greenwich Country Day School | Cancelled | Cancelled | |
| Sat., 1/26 | JV Girls Fencing | Novice Tournament | Away - Guilford HS | 8:30 a.m. | ||
| Sat., 1/26 | V Girls Gymnastics | Trumbull | Away - Next Dimension Gymnastics [Directions] | 6:30 p.m. | Greenwich 137.8 Trumbull 134.85 | |
| Sat., 1/26 | V Girls Indoor Track | Western Division Championship | Away - Staples HS | 10:00 a.m. | ||
| Sun., 1/27 | JV Girls Ice Hockey | New Canaan | Home - Dorothy Hamill Ice Rink [Directions] | 5:30 p.m. | ||
| Mon., 1/28 | V Boys Ice Hockey | Trinity Catholic | Home - Dorothy Hamill Ice Rink [Directions] | 5:15 p.m. | W 7-0 | |
| Mon., 1/28 | JV Boys Ice Hockey | Rye (NY) | Away - Playland Ice Rink | 5:00 p.m. | ||
| Mon., 1/28 | V Boys Swimming and Diving | Danbury | Away - O'Neil Center @ Western Connecticut State University [Directions] | 4:30 p.m. | 2:30 EARLY DISMISSAL | |
| Tue., 1/29 | V Bowling | MATCH | Away - Nutmeg Lanes | 3:00 p.m. | 2:00 EARLY DISMISSAL | |
| Thu., 1/31 | V Boys Alpine Skiing | RACE | Away - Mt Southington | 4:00 p.m. | 1:30 EARLY DISMISSAL | |
| Thu., 1/31 | V Boys Basketball | Trumbull | Away - THS Main Gym [Directions] | 7:00 p.m. | L 52-62 | |
| Thu., 1/31 | JV Boys Basketball | Trumbull | Away - THS Main Gym [Directions] | 5:15 p.m. | ||
| Thu., 1/31 | FR Boys Basketball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | 2:30 EARLY DISMISSAL | |
| Thu., 1/31 | V Boys Ice Hockey | Notre Dame-West Haven | Away - Bennett Rink [Directions] | 6:00 p.m. | L 1-4 | 2:00 EARLY DISMISSAL |
| Thu., 1/31 | V Boys Indoor Track | FCIAC Championships | Away - New Haven Athletic Center | 4:30 p.m. | 2:00 EARLY DISMISSAL | |
| Thu., 1/31 | V Boys Swimming and Diving | Staples | Home - GHS Pool [Directions] | 4:30 p.m. | ||
| Thu., 1/31 | V Wrestling | Darien, Fairfield Prep, Fairfield Warde, Norwalk | Away - Fairfield Warde HS [Directions] | 4:00 p.m. | Greenwich 78 Darien 6 Greenwich 54 Fairfield Prep 21 Greenwich 31 Fairfield Warde 35 Greenwich 60 Norwalk 21 | 2:00 EARLY DISMISSAL |
| Thu., 1/31 | V Girls Alpine Skiing | RACE | Away - Mt Southington | 4:00 p.m. | 1:30 EARLY RELEASE | |
| Thu., 1/31 | V Girls Basketball | Trumbull | Home - GHS Gymnasium [Directions] | 7:00 p.m. | L 35-48 | |
| Thu., 1/31 | JV Girls Basketball | Trumbull | Home - GHS Gymnasium [Directions] | 5:15 p.m. | ||
| Thu., 1/31 | FR Girls Basketball | Trumbull | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 1/31 | V Girls Gymnastics | New Canaan, Westhill | Home - Greenwich YWCA [Directions] | 6:00 p.m. | Greenwich 133.45 New Canaan 117.3 Westhill 115.45 | |
| Thu., 1/31 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Dorothy Hamill Ice Rink [Directions] | 8:00 p.m. | W 8-2 | |
| Thu., 1/31 | V Girls Indoor Track | FCIAC Championships | Away - New Haven Athletic Center | 4:30 p.m. | 2:00 EARLY DISMISSAL | |
| Fri., 2/1 | V Boys Basketball | Westhill | Home - GHS Gymnasium [Directions] | 7:00 p.m. | W 58-55 | |
| Fri., 2/1 | JV Boys Basketball | Westhill | Home - GHS Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 2/1 | FR Boys Basketball | Westhill | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 2/1 | V Boys Ice Hockey | Brien McMahon/Norwalk | Away - SoNo Ice House [Directions] | 7:20 p.m. | W 4-1 | |
| Fri., 2/1 | V Boys Swimming and Diving | Trumbull | Away - Hillcrest MS [Directions] | 4:00 p.m. | 2:00 EARLY DISMISSAL | |
| Fri., 2/1 | V Girls Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | W 54-47 | |
| Fri., 2/1 | JV Girls Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 2/1 | FR Girls Basketball | Greenwich Country Day | Away - GCDS | 6:00 p.m. | ||
| Sat., 2/2 | V Boys Fencing | Hopkins Meet | Away - Hopkins School | 9:30 a.m. | ||
| Sat., 2/2 | V Wrestling | Foran Duels | Away - Foran HS | 9:00 a.m. | Greenwich 27 Killingly 42 Greenwich 31 Foran 41 Greenwich 48 Amity 21 Greenwich 56 Notre Dame West Haven 21 Greenwich 57 Oxford 15 | |
| Sat., 2/2 | JV Wrestling | Ludlowe Southern CT Championships | Away - Fairfield Ludlowe HS | 9:00 a.m. | ||
| Sat., 2/2 | V Competitive Cheerleading | FCIAC Championships | Away - Wilton HS | 11:00 a.m. | ||
| Sat., 2/2 | V Girls Fencing | Hopkins Meet | Away - Hopkins School | 9:30 a.m. | ||
| Mon., 2/4 | V Boys Basketball | Weston | Home - GHS Gymnasium [Directions] | 7:00 p.m. | W 68-58 | |
| Mon., 2/4 | JV Boys Basketball | Weston | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 2/4 | FR Boys Basketball | Weston | Away - WHS Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 2/4 | V Boys Ice Hockey | New Canaan | Away - Darien Ice Rink [Directions] | 6:00 p.m. | L 1-6 | |
| Mon., 2/4 | V Girls Ice Hockey | Simsbury | Away - Simsbury Farms CC [Directions] | 4:00 p.m. | W 5-1 | 1:30 EARLY DISMISSAL |
| Tue., 2/5 | V Boys Basketball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 7:00 p.m. | L 49-81 | |
| Tue., 2/5 | JV Boys Basketball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 5:15 p.m. | ||
| Tue., 2/5 | FR Boys Basketball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 4:00 p.m. | 2:30 EARLY DISMISSAL | |
| Tue., 2/5 | V Wrestling | Danbury | Away - Danbury HS - NEW gym [Directions] | 5:00 p.m. | 2:30 EARLY DISMISSAL | |
| Tue., 2/5 | V Bowling | MATCH | Away - Nutmeg Lanes | 3:00 p.m. | 2:00 EARLY DISMISSAL | |
| Tue., 2/5 | V Girls Basketball | Wilton | Home - GHS Gymnasium [Directions] | 5:30 p.m. | W 44-35 | |
| Tue., 2/5 | JV Girls Basketball | Wilton | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 2/5 | JV Girls Ice Hockey | Stamford/Westhill/Staples | Home - Dorothy Hamill Ice Rink [Directions] | Cancelled | Cancelled | |
| Wed., 2/6 | V Boys Alpine Skiing | RACE | Away - Mt Southington | 4:00 p.m. | 1:30 EARLY DISMISSAL | |
| Wed., 2/6 | V Girls Alpine Skiing | RACE | Away - Mt Southington | 4:00 p.m. | 1:30 EARLY RELEASE | |
| Wed., 2/6 | V Girls Gymnastics | Staples | Home - Greenwich YWCA [Directions] | 6:00 p.m. | 132.25 | |
| Wed., 2/6 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Conners Ice Rink [Directions] | 7:40 p.m. | W 5-0 | |
| Thu., 2/7 | V Boys Alpine Skiing | RACE | Away - Mt Southington | 4:00 p.m. | 1:30 EARLY DISMISSAL | |
| Thu., 2/7 | V Boys Ice Hockey | Staples | Home - Dorothy Hamill Ice Rink [Directions] | 8:00 p.m. | W 6-0 | |
| Thu., 2/7 | V Boys Swimming and Diving | Ridgefield | Away - Pool at Barlow Mountain School [Directions] | 4:00 p.m. | 2:00 EARLY DISMISSAL | |
| Thu., 2/7 | V Girls Alpine Skiing | RACE | Away - Mt Southington | 4:00 p.m. | 1:30 EARLY RELEASE | |
| Fri., 2/8 | V Boys Basketball | Bridgeport Central | Home - GHS Gymnasium [Directions] | 7:00 p.m. | W 82-74(OT) | |
| Fri., 2/8 | JV Boys Basketball | Bridgeport Central | Home - GHS Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 2/8 | FR Boys Basketball | Bridgeport Central | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 2/8 | JV Boys Ice Hockey | Fairfield Warde/Ludlowe | Home - Dorothy Hamill Ice Rink [Directions] | 9:15 p.m. | ||
| Fri., 2/8 | V Wrestling | FCIAC Championships | Away - New Canaan HS | 4:00 p.m. | ||
| Fri., 2/8 | V Girls Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 5:30 p.m. | W 67-33 | |
| Fri., 2/8 | JV Girls Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 4:00 p.m. | ||
| Fri., 2/8 | V Girls Ice Hockey | Trumbull/St. Joseph | Away [Directions] | 4:00 p.m. | W 5-0 | 2:00 EARLY DISMISSAL |
| Sat., 2/9 | V Boys Ice Hockey | LaSalle Academy (RI) | Away - Providence College | 6:00 p.m. | W 3-2(OT) | |
| Sat., 2/9 | V Boys Indoor Track | State Championships | Away - New Haven Athletic Center | 4:00 p.m. | ||
| Sat., 2/9 | V Wrestling | FCIAC Championships | Away - New Canaan HS | 9:00 a.m. | ||
| Sat., 2/9 | Winter Dance Team | Warde Dance Jam | Away - Fairfield Warde HS | 4:00 p.m. | ||
| Sat., 2/9 | V Girls Gymnastics | FCIAC Championships | Away - Westhill HS | 10:00 a.m. | 135.1 | |
| Sat., 2/9 | V Girls Ice Hockey | Darien | Home - Dorothy Hamill Ice Rink [Directions] | 6:30 p.m. | L 0-1 | |
| Sat., 2/9 | V Girls Indoor Track | State Championships | Away - New Haven Athletic Center | 4:00 p.m. | ||
| Sun., 2/10 | JV Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Dorothy Hamill Ice Rink [Directions] | 12:15 p.m. | ||
| Mon., 2/11 | V Boys Basketball | Fairfield Warde | Home - GHS Gymnasium [Directions] | 7:00 p.m. | L 66-68 | |
| Mon., 2/11 | JV Boys Basketball | Fairfield Warde | Home - GHS Gymnasium [Directions] | 5:15 p.m. | ||
| Mon., 2/11 | FR Boys Basketball | Fairfield Warde | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 2/11 | JV Boys Ice Hockey | Greenwich Country Day | Away - Greenwich Skating Club | 3:45 p.m. | ||
| Mon., 2/11 | V Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 7:00 p.m. | L 29-52 | |
| Mon., 2/11 | JV Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 5:15 p.m. | ||
| Mon., 2/11 | FR Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | 2:30 EARLY DISMISSAL | |
| Wed., 2/13 | V Boys Basketball | Danbury | Home - GHS Gymnasium [Directions] | 7:00 p.m. | W 58-40 | |
| Wed., 2/13 | JV Boys Basketball | Danbury | Home - GHS Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 2/13 | FR Boys Basketball | Danbury | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 2/13 | V Boys Ice Hockey | St. Joseph | Away - Shelton Rinks [Directions] | 8:30 p.m. | W 6-2 | |
| Wed., 2/13 | JV Boys Ice Hockey | Mamaroneck (NY) | Home - Dorothy Hamill Ice Rink [Directions] | 8:30 p.m. | ||
| Wed., 2/13 | V Girls Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 7:00 p.m. | L 42-58 | |
| Wed., 2/13 | JV Girls Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 5:15 p.m. | ||
| Wed., 2/13 | FR Girls Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 4:00 p.m. | 2:30 EARLY DISMISSAL | |
| Wed., 2/13 | V Girls Gymnastics | Carlucci Meet | Away - Westhill HS | Cancelled | Cancelled | |
| Fri., 2/15 | V Wrestling | Class LL State Championships | Away - Trumbull HS | 4:00 p.m. | ||
| Sat., 2/16 | V Boys Indoor Track | State Open Championships | Away - New Haven Athletic Center | 12:00 p.m. | ||
| Sat., 2/16 | V Wrestling | Class LL State Championships | Away - Trumbull HS | 9:00 a.m. | ||
| Sat., 2/16 | V Girls Indoor Track | State Open Championships | Away - New Haven Athletic Center | 12:00 p.m. | ||
| Sun., 2/17 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Dorothy Hamill Ice Rink [Directions] | 7:00 p.m. | W 8-1 | |
| Mon., 2/18 | V Boys Basketball | Trinity Catholic | Away - Walsh Court | 7:00 p.m. | W 55-54 | |
| Mon., 2/18 | JV Boys Basketball | Trinity Catholic | Away - Walsh Court | 5:15 p.m. | ||
| Mon., 2/18 | FR Boys Basketball | Trinity Catholic | Away - Walsh Court | 4:00 p.m. | 2:45 EARLY DISMISSAL | |
| Mon., 2/18 | V Boys Ice Hockey | Darien | Home - Dorothy Hamill Ice Rink [Directions] | 4:30 p.m. | L 2-4 | |
| Mon., 2/18 | School Holidays and Closings | Washingtons Birthday | ||||
| Tue., 2/19 | V Boys Fencing | Milford | Home - GHS Gymnasium [Directions] | 7:00 p.m. | ||
| Tue., 2/19 | V Bowling | MATCH | Away - Nutmeg Lanes | 3:00 p.m. | 2:00 EARLY DISMISSAL | |
| Tue., 2/19 | V Girls Fencing | Milford | Home - GHS Gymnasium [Directions] | 7:00 p.m. | ||
| Wed., 2/20 | V Girls Ice Hockey | FCIAC Tournament | Away - Darien Ice House | 7:40 p.m. | ||
| Fri., 2/22 | V Wrestling | State Open Championships | Away - New Haven Athletic Center | 4:00 p.m. | ||
| Sat., 2/23 | V Boys Basketball | Achievement First | Away - AF [Directions] | 2:00 p.m. | W 65-36 | |
| Sat., 2/23 | JV Boys Basketball | Achievement First | Away - AF [Directions] | 12:30 p.m. | ||
| Sat., 2/23 | JV Boys Fencing | North Haven Tournament | Away - North Haven HS | 8:30 a.m. | ||
| Sat., 2/23 | V Boys Ice Hockey | FCIAC Tournament | Away - Darien Ice House | 8:00 p.m. | ||
| Sat., 2/23 | V Wrestling | State Open Championships | Away - New Haven Athletic Center | 9:00 a.m. | ||
| Sat., 2/23 | V Competitive Cheerleading | East Haven Competition | Away - East Haven HS | 12:00 p.m. | ||
| Sat., 2/23 | FR Girls Basketball | TOURNAMENT | Away - St Joseph HS | 10:00 a.m. | ||
| Sat., 2/23 | Winter Dance Team | State Championships | Away - Hamden HS | TBA | ||
| Sat., 2/23 | JV Girls Fencing | North Haven Tournament | Away - North Haven HS | 8:30 a.m. | ||
| Sat., 2/23 | V Girls Gymnastics | Class L State Championships | Away | TBA | ||
| Sat., 2/23 | V Girls Ice Hockey | FCIAC Championship | Away - Darien Ice House | 4:00 p.m. | ||
| Sat., 2/23 | V Girls Indoor Track | New England Championships | Away | 12:00 p.m. | ||
| Tue., 2/26 | V Boys Fencing | Brunswick School | Home - GHS Gymnasium [Directions] | 7:00 p.m. | ||
| Tue., 2/26 | V Boys Swimming and Diving | FCIAC Swimming Trials | Home - GHS Pool [Directions] | 5:15 p.m. | ||
| Tue., 2/26 | V Bowling | MATCH | Away - Nutmeg Lanes | 3:00 p.m. | 2:00 EARLY DISMISSAL | |
| Tue., 2/26 | V Girls Basketball | State Tournament | Away - Norwalk HS | 6:00 p.m. | ||
| Wed., 2/27 | V Boys Ice Hockey | FCIAC Tournament | Away - Darien Ice House | 4:00 p.m. | ||
| Wed., 2/27 | V Boys Swimming and Diving | FCIAC Diving Championships | Away - Westhill HS | 4:30 p.m. | ||
| Wed., 2/27 | V Girls Ice Hockey | State Tournament | Home - Dorothy Hamill Ice Rink [Directions] | 6:45 p.m. | ||
| Thu., 2/28 | V Boys Swimming and Diving | FCIAC Championships | Home - GHS Pool [Directions] | 6:30 p.m. | ||
| Fri., 3/1 | V Wrestling | New England Championships | Away | 4:00 p.m. | ||
| Sat., 3/2 | V Boys Fencing | State Individual Championships | Away - Mohegan Sun | 8:30 a.m. | ||
| Sat., 3/2 | V Boys Ice Hockey | FCIAC Championship | Home - Dorothy Hamill Ice Rink [Directions] | 6:00 p.m. | ||
| Sat., 3/2 | V Girls Fencing | State Individual Championships | Away - Mohegan Sun | 8:30 a.m. | ||
| Sat., 3/2 | V Girls Ice Hockey | State Tournament | Away - Darien Ice House | 4:00 p.m. | ||
| Sun., 3/3 | V Competitive Cheerleading | State Championships | Away - New Haven Athletic Center | 4:00 p.m. | ||
| Tue., 3/5 | V Boys Alpine Skiing | State Open Championships | Away - Mt Southington | 2:00 p.m. | 11:30 EARLY DISMISSAL | |
| Tue., 3/5 | V Boys Basketball | State Tournament | Home - GHS Gymnasium [Directions] | 6:00 p.m. | ||
| Tue., 3/5 | V Boys Ice Hockey | State Tournament | Away - Darien Ice House | 7:30 p.m. | ||
| Tue., 3/5 | V Bowling | MATCH | Away - Nutmeg Lanes | 3:00 p.m. | 2:00 EARLY DISMISSAL | |
| Tue., 3/5 | V Girls Alpine Skiing | State Open Championships | Away - Mt Southington | 2:00 p.m. | 11:30 EARLY DISMISSAL | |
| Wed., 3/6 | V Girls Gymnastics | State Open Championships | Away - New Milford HS | 4:00 p.m. | ||
| Thu., 3/7 | V Boys Swimming and Diving | Diving State Championships | Away - Middletown HS | 5:30 p.m. | ||
| Thu., 3/7 | V Bowling | MATCH | Away - Nutmeg Lanes | 3:00 p.m. | 2:00 EARLY DISMISSAL | |
| Sat., 3/9 | V Boys Swimming and Diving | State Trials | Away - East Hartford HS | 6:00 p.m. | ||
| Sat., 3/9 | V Bowling | State Championships | Away - Newington Bowl-A-Rama | 10:00 a.m. | ||
| Sat., 3/9 | V Competitive Cheerleading | State Open Championships | Away - New Haven Athletic Center | 4:00 p.m. | ||
| Sat., 3/9 | V Girls Fencing | State Individual Championships | Away - Guilford HS | 8:30 a.m. | ||
| Sun., 3/10 | V Boys Fencing | State Individual Championships | Away - Guilford HS | 8:30 a.m. | ||
| Mon., 3/11 | V Boys Swimming and Diving | State Championships | Away - Southern Connecticut State University | 1:30 p.m. | ||
| Tue., 3/12 | V Boys Swimming and Diving | State Open Diving Championships | Away - Bulkeley HS | 5:30 p.m. | ||
| Tue., 3/12 | V Bowling | MATCH | Away - Nutmeg Lanes | 3:00 p.m. | ||
| Thu., 3/14 | V Boys Swimming and Diving | State Open Championships | Away - Yale University | 7:00 p.m. | ||
| Sat., 3/16 | V Boys Fencing | State Championships | Away - Fitch HS | 8:30 a.m. | ||
| Sat., 3/16 | V Boys Rugby | Southington | Home - Cardinal Stadium [Directions] | 1:00 p.m. | ||
| Sat., 3/16 | V Girls Fencing | State Championships | Away - Fitch HS | 8:30 a.m. | ||
| Thu., 3/21 | V Boys Lacrosse | Rye (NY) (Scrim.) | Home - Cardinal Stadium [Directions] | 5:00 p.m. | ||
| Fri., 3/22 | V Girls Water Polo | Staples | Home - GHS Pool [Directions] | 4:30 p.m. | ||
| Sat., 3/23 | V Baseball | SCRIMMAGE | Away - Darien HS | TBA | ||
| Sat., 3/23 | V Boys Lacrosse | SCRIMMAGE | Away - Darien HS | 9:00 a.m. | ||
| Sat., 3/23 | JV Boys Lacrosse | SCRIMMAGE | Home - GHS Field 7 [Directions] | 9:00 a.m. | ||
| Sat., 3/23 | V Boys Rugby | Fairfield Prep | Away - Fairfield University [Directions] | 12:00 p.m. | ||
| Sat., 3/23 | JV Boys Rugby | Fairfield Prep | Away [Directions] | TBA | ||
| Sat., 3/23 | V Softball | Round Robbin | Away - Darien HS | 10:00 a.m. | ||
| Sun., 3/24 | V Girls Lacrosse | SCRIMMAGE | Home - Cardinal Stadium [Directions] | 10:00 a.m. | ||
| Tue., 3/26 | V Baseball | Brunswick School (Scrim.) | Away - Brunswick School | 4:00 p.m. | ||
| Tue., 3/26 | V Boys Lacrosse | Pleasantville (NY) (Scrim.) | Away - Pleasantville HS | 5:00 p.m. | ||
| Tue., 3/26 | V Boys Volleyball | New Canaan (Scrim.) | Away - NCHS Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 3/26 | V Softball | New Milford (Scrim.) | Home - GHS Softball Field [Directions] | 4:15 p.m. | ||
| Wed., 3/27 | V Boys Sailing | Regatta | Home - Grass Island [Directions] | 4:00 p.m. | ||
| Wed., 3/27 | V Boys Volleyball | Westhill (Scrim.) | Away - Westhill - Main Gymnasium [Directions] | 4:30 p.m. | ||
| Wed., 3/27 | V Girls Rugby | Southington | Home - Cardinal Stadium [Directions] | 5:00 p.m. | ||
| Wed., 3/27 | V Girls Sailing | Regatta | Home - Grass Island [Directions] | 4:00 p.m. | ||
| Thu., 3/28 | V Baseball | Stamford (Scrim.) | Away - SHS Baseball Field [Directions] | 4:00 p.m. | ||
| Thu., 3/28 | JV Baseball | Stamford (Scrim.) | Away - Belltown Field [Directions] | 4:15 p.m. | ||
| Thu., 3/28 | V Boys Lacrosse | Fairfield Prep (Scrim.) | Home - Cardinal Stadium [Directions] | 5:00 p.m. | ||
| Thu., 3/28 | V Boys Tennis | Horace Greeley (NY) (Scrim.) | Away - Horace Greeley HS | 4:00 p.m. | T 5-5 | |
| Thu., 3/28 | V Girls Tennis | Daniel Hand (Scrim.) | Home - GHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 3/28 | V Girls Water Polo | Greenwich Aqautics | Home - GHS Pool [Directions] | 5:30 p.m. | ||
| Fri., 3/29 | V Girls Lacrosse | Convent of Sacred Heart (Scrim.) | Home - Cardinal Stadium [Directions] | 4:30 p.m. | ||
| Fri., 3/29 | V Girls Tennis | Greenwich Academy (Scrim.) | Away | 4:00 p.m. | ||
| Sat., 3/30 | V Baseball | Simsbury | Home - GHS Baseball Field [Directions] | 1:00 p.m. | W 6-4 | |
| Sat., 3/30 | V Boys Rugby | Simsbury | Home - Cardinal Stadium [Directions] | 3:00 p.m. | ||
| Sat., 3/30 | JV Boys Rugby | Simsbury | Home - GHS Field 7 [Directions] | 2:45 p.m. | ||
| Sat., 3/30 | FR Boys Rugby | Fairfield Prep | Home - GHS Field 7 [Directions] | 10:00 a.m. | ||
| Sat., 3/30 | V Boys Sailing | Regatta | Home - Grass Island [Directions] | 9:00 a.m. | ||
| Sat., 3/30 | V Boys Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 12:00 p.m. | L 0-3 | |
| Sat., 3/30 | JV Boys Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 10:30 a.m. | ||
| Sat., 3/30 | V Girls Sailing | Regatta | Home - Grass Island [Directions] | 3:00 p.m. | ||
| Sat., 3/30 | V Softball | New Fairfield | Away - NFHS Softball Field [Directions] | 11:00 a.m. | W 20-3 | |
| Mon., 4/1 | V Boys Lacrosse | Trumbull | Home - Cardinal Stadium [Directions] | 4:30 p.m. | W 10-4 | |
| Mon., 4/1 | JV Boys Lacrosse | Trumbull | Home - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | ||
| Mon., 4/1 | V Boys Tennis | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | 2:30 EARLY DISMISSAL |
| Mon., 4/1 | V Boys Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | L 0-3 | 2:30 EARLY DISMISSAL |
| Mon., 4/1 | JV Boys Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 4/1 | V Softball | New Canaan | Away - Waveny Park - Orchard Field [Directions] | 4:00 p.m. | W 14-2 | 2:30 EARLY DISMISSAL |
| Mon., 4/1 | V Girls Tennis | Brien McMahon | Home - GHS Tennis Courts [Directions] | 4:30 p.m. | W 7-0 | |
| Tue., 4/2 | V Baseball | Fairfield Prep | Away - Alumni Diamond, Fairfield University [Directions] | 4:00 p.m. | L 8-9 | 2:00 EARLY DISMISSAL |
| Tue., 4/2 | V Boys Tennis | New Canaan | Away - NCHS Tennis Courts [Directions] | 4:00 p.m. | L 2-5 | 2:30 EARLY DISMISSAL |
| Tue., 4/2 | JV Boys Tennis | New Canaan | Away - NCHS Tennis Courts [Directions] | 5:45 p.m. | junior varsity | |
| Tue., 4/2 | V Girls Lacrosse | Staples | Home - Cardinal Stadium [Directions] | 4:30 p.m. | L 10-16 | |
| Tue., 4/2 | JV Girls Lacrosse | Staples | Home - Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Tue., 4/2 | V Softball | Brookfield | Away - BHS Softball Field [Directions] | 4:30 p.m. | L 12-13 | 2:30 EARLY DISMISSAL |
| Tue., 4/2 | V Girls Tennis | New Canaan | Home - GHS Tennis Courts [Directions] | 4:30 p.m. | W 6-1 | |
| Tue., 4/2 | JV Girls Tennis | New Canaan | Home - Binney Park [Directions] | 4:00 p.m. | ||
| Tue., 4/2 | V Girls Water Polo | Greenwich Academy | Home - GHS Pool [Directions] | 4:15 p.m. | ||
| Wed., 4/3 | JV Baseball | Stamford (Scrim.) | Away - Belltown Field [Directions] | Cancelled | Cancelled | |
| Wed., 4/3 | FR Boys Lacrosse | Stamford | Home - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | ||
| Wed., 4/3 | FR Boys Rugby | Xavier (NY) | Home - GHS Field 7 [Directions] | 5:00 p.m. | ||
| Wed., 4/3 | JV Boys Tennis | Brunswick School | Home - Central MS [Directions] | 4:00 p.m. | junior varsity | |
| Wed., 4/3 | V Boys Volleyball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | L 0-3 | 2:00 EARLY DISMISSAL |
| Wed., 4/3 | JV Boys Volleyball | Trumbull | Away - THS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 4/3 | V Girls Rugby | Fairfield | Home - Cardinal Stadium [Directions] | 4:30 p.m. | ||
| Thu., 4/4 | V Boys Lacrosse | Westhill | Away - J. Walter Kennedy Stadium [Directions] | 4:30 p.m. | W 17-3 | 3:00 EARLY DISMISSAL |
| Thu., 4/4 | V Boys Tennis | Darien | Home - GHS Tennis Courts [Directions] | 4:30 p.m. | L 3-4 | |
| Thu., 4/4 | JV Boys Tennis | Darien | Home - Central MS [Directions] | 4:30 p.m. | freshman | |
| Thu., 4/4 | V Girls Golf | Wilton | Away - Silver Mine CC [Directions] | 3:45 p.m. | GHS: 173 WHS: 204 | |
| Thu., 4/4 | V Girls Lacrosse | Ridgewood (NJ) | Home - Cardinal Stadium [Directions] | 4:30 p.m. | L 4-13 | |
| Thu., 4/4 | JV Girls Lacrosse | Ridgewood (NJ) | Home - GHS Field 3 [Directions] | 5:30 p.m. | ||
| Thu., 4/4 | FR Girls Lacrosse | Ridgewood (NJ) | Away | 4:30 p.m. | ||
| Thu., 4/4 | V Girls Tennis | Darien | Away - DHS Tennis Courts [Directions] | 4:00 p.m. | L 3-4 | 2:30 EARLY DISMISSAL |
| Thu., 4/4 | JV Girls Tennis | Darien | Away - Weed Beach [Directions] | 4:00 p.m. | 3:00 EARLY DISMISSAL - JV | |
| Thu., 4/4 | V Girls Water Polo | Choate Rosemary Hall | Away - Choate Rosemary Hall School | 4:30 p.m. | ||
| Fri., 4/5 | JV Boys Lacrosse | Westhill | Away - J. Walter Kennedy Stadium [Directions] | 5:00 p.m. | ||
| Fri., 4/5 | FR Boys Lacrosse | Staples | Away - Wakeman Field E (grass) [Directions] | 4:30 p.m. | 2:45 EARLY DISMISSAL | |
| Fri., 4/5 | V Boys Volleyball | Staples | Home - GHS Gymnasium [Directions] | 5:30 p.m. | L 0-3 | |
| Fri., 4/5 | JV Boys Volleyball | Staples | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 4/5 | FR Girls Lacrosse | Staples | Home - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | ||
| Sat., 4/6 | FR Baseball | Fairfield Prep | Away - Owen Fish Park [Directions] | 12:00 p.m. | L 7-1 | |
| Sat., 4/6 | V Boys Lacrosse | Wilton | Away - Fujitani Field - Turf [Directions] | 7:00 p.m. | W 7-6(OT) | |
| Sat., 4/6 | JV Boys Lacrosse | Wilton | Away - Fujitani Field - Turf [Directions] | 4:30 p.m. | ||
| Sat., 4/6 | V Boys Rugby | West Hartford | Home - GHS Field 7 [Directions] | 12:00 p.m. | B SIDE GAME | |
| Sat., 4/6 | V Boys Rugby | Xavier (NY) | Away | TBA | ||
| Sat., 4/6 | JV Boys Rugby | Xavier (NY) | Away | TBA | ||
| Sat., 4/6 | V Boys Sailing | Regatta | Home - Grass Island [Directions] | 3:00 p.m. | ||
| Sat., 4/6 | V Girls Lacrosse | Massapequa (NY) | Away - Massapequa HS | 11:00 a.m. | L 6-8 | |
| Sat., 4/6 | JV Girls Lacrosse | Massapequa (NY) | Away | 11:00 a.m. | ||
| Sat., 4/6 | V Girls Sailing | Regatta | Home - Grass Island [Directions] | 9:00 a.m. | ||
| Mon., 4/8 | V Baseball | Brien McMahon | Away - Pride Field (BMHS) [Directions] | 4:00 p.m. | L 3-6 | 2:30 EARLY DISMISSAL |
| Mon., 4/8 | FR Baseball | Brien McMahon | Home - Julian Curtiss School [Directions] | 4:30 p.m. | W 4-1 | |
| Mon., 4/8 | V Boys Tennis | Fairfield Ludlowe | Home - GHS Tennis Courts [Directions] | 4:30 p.m. | W 7-0 | |
| Mon., 4/8 | V Boys Volleyball | Westhill | Home - GHS Gymnasium [Directions] | 4:30 p.m. | W 3-0 | |
| Mon., 4/8 | JV Boys Volleyball | Westhill | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 4/8 | FR Girls Lacrosse | Darien | Home - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | ||
| Mon., 4/8 | V Softball | Brien McMahon | Home - GHS Softball Field [Directions] | 4:30 p.m. | W 10-3 | |
| Mon., 4/8 | V Girls Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | 2:15 EARLY DISMISSAL |
| Mon., 4/8 | JV Girls Tennis | Fairfield Ludlowe | Away - Dwight Elementary School Courts [Directions] | 4:00 p.m. | 2:45 EARLY DISMISSAL - JV | |
| Tue., 4/9 | FR Boys Lacrosse | Darien | Home - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | ||
| Tue., 4/9 | V Boys Outdoor Track | Bridgeport Central, Danbury | Home - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/9 | V Boys Sailing | Regatta | Away - Pequot Yacht Club | 4:00 p.m. | ||
| Tue., 4/9 | V Boys Tennis | St. Joseph | Away [Directions] | 4:00 p.m. | W 6-1 | 2:00 EARLY DISMISSAL |
| Tue., 4/9 | V Girls Golf | Wilton | Home - Griffith E Harris Golf Course [Directions] | 3:45 p.m. | GHS: 185 WHS: 235 | |
| Tue., 4/9 | V Girls Outdoor Track | Danbury, Bridgeport Central | Home - Greenwich HS Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/9 | V Girls Sailing | Regatta | Away - Pequot Yacht Club | 4:00 p.m. | ||
| Tue., 4/9 | V Softball | Wilton | Away - WHS Varsity Softball Field [Directions] | 4:30 p.m. | W 17-2(6) | 2:30 EARLY DISMISSAL |
| Tue., 4/9 | V Girls Tennis | St. Joseph | Home - GHS Tennis Courts [Directions] | 4:30 p.m. | W 6-1 | |
| Tue., 4/9 | JV Girls Tennis | Greenwich Country Day | Home - Binney Park [Directions] | 4:00 p.m. | FR | |
| Wed., 4/10 | V Baseball | New Canaan | Away - Mead Park [Directions] | 4:00 p.m. | W 9-0 | 2:30 EARLY DISMISSAL |
| Wed., 4/10 | JV Baseball | New Canaan | Away - Waveny Park - Coppo Field [Directions] | 4:00 p.m. | ||
| Wed., 4/10 | FR Baseball | New Canaan | Home - GHS Baseball Field [Directions] | 4:30 p.m. | W 5-1 | |
| Wed., 4/10 | V Boys Golf | Trinity Catholic | Away | 3:15 p.m. | Greenwich 150 Trinity 255 | Sterling Farms GC |
| Wed., 4/10 | JV Boys Golf | New Canaan | Away - Country Club of New Canaan [Directions] | 3:00 p.m. | ||
| Wed., 4/10 | V Boys Lacrosse | Ridgefield | Home - Cardinal Stadium [Directions] | 4:30 p.m. | L 7-10 | |
| Wed., 4/10 | JV Boys Lacrosse | Ridgefield | Home - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | ||
| Wed., 4/10 | V Boys Rugby | Darien | Home - GHS Field 7 [Directions] | 4:30 p.m. | B | |
| Wed., 4/10 | JV Boys Rugby | Harvey School (NY) | Away | 4:45 p.m. | ||
| Wed., 4/10 | V Boys Sailing | Regatta | Home - Grass Island [Directions] | 4:00 p.m. | ||
| Wed., 4/10 | JV Boys Tennis | Fairfield Ludlowe | Away - Tomlinson MS Tennis Courts [Directions] | 4:30 p.m. | junior varsity | |
| Wed., 4/10 | JV Boys Tennis | Fairfield Warde | Home - Central MS [Directions] | 4:30 p.m. | freshman | |
| Wed., 4/10 | V Boys Volleyball | Danbury | Home - GHS Gymnasium [Directions] | 4:30 p.m. | L 0-3 | |
| Wed., 4/10 | JV Boys Volleyball | Danbury | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 4/10 | V Girls Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:45 p.m. | GHS: 177 THS: 223 | |
| Wed., 4/10 | V Girls Sailing | Regatta | Home - Grass Island [Directions] | 4:00 p.m. | ||
| Wed., 4/10 | V Softball | New Canaan | Home - GHS Softball Field [Directions] | 4:30 p.m. | W 12-2 | |
| Wed., 4/10 | JV Girls Tennis | Fairfield Warde | Home - Binney Park [Directions] | 4:00 p.m. | JV | |
| Thu., 4/11 | V Boys Golf | Danbury | Home - Griffith E Harris Golf Course [Directions] | 2:00 p.m. | Greenwich 160 Danbury 203 | |
| Thu., 4/11 | JV Boys Golf | Brunswick School | Away | 4:00 p.m. | ||
| Thu., 4/11 | V Boys Tennis | Ridgefield | Away - RHS Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | 2:00 EARLY DISMISSAL |
| Thu., 4/11 | JV Boys Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | 2:45 EARLY DISMISSAL/freshman | |
| Thu., 4/11 | V Girls Lacrosse | Cheshire | Away - Cheshire High Main Game field [Directions] | 6:00 p.m. | W 13-12 | |
| Thu., 4/11 | JV Girls Lacrosse | Cheshire | Away - Bartlem park [Directions] | 4:00 p.m. | 2:00 EARLY DISMISSAL | |
| Thu., 4/11 | V Girls Rugby | North Haven | Home - Cardinal Stadium [Directions] | 5:00 p.m. | ||
| Thu., 4/11 | V Girls Tennis | Ridgefield | Home - GHS Tennis Courts [Directions] | 4:30 p.m. | W 7-0 | |
| Thu., 4/11 | JV Girls Tennis | Ridgefield | Home - Binney Park [Directions] | 4:00 p.m. | JV | |
| Thu., 4/11 | V Girls Water Polo | Greenwich Aquatics | Home - GHS Pool [Directions] | 5:30 p.m. | ||
| Fri., 4/12 | V Baseball | Darien | Home - GHS Baseball Field [Directions] | 4:30 p.m. | L 0-10 | |
| Fri., 4/12 | JV Baseball | Darien | Home - Julian Curtiss School [Directions] | 4:00 p.m. | ||
| Fri., 4/12 | FR Baseball | Darien | Away - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | W 7-3 | 3:00 EARLY DISMISSAL |
| Fri., 4/12 | FR Boys Lacrosse | Wilton | Home - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | ||
| Fri., 4/12 | V Boys Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | W 3-0 | 2:00 EARLY DISMISSAL |
| Fri., 4/12 | JV Boys Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | 5:30 p.m. | ||
| Fri., 4/12 | FR Girls Lacrosse | Wilton | Away - Allen's Field [Directions] | 4:00 p.m. | 2:45 EARLY DISMISSAL | |
| Fri., 4/12 | V Softball | Darien | Away - DHS Softball Varsity Field [Directions] | 4:00 p.m. | W 16-4 | 2:30 EARLY DISMISSAL |
| Sat., 4/13 | V Baseball | Southington | Away - Baseball Varsity Field [Directions] | 2:00 p.m. | L 2-12(6) | |
| Sat., 4/13 | V Boys Lacrosse | St. Joseph | Home - Cardinal Stadium [Directions] | 4:00 p.m. | L 6-12 | |
| Sat., 4/13 | JV Boys Lacrosse | St. Joseph | Home - GHS Field 7 [Directions] | 4:00 p.m. | ||
| Sat., 4/13 | V Boys Rugby | Gonzaga Tournament | Away - Morven Park Athletic Complex | 10:00 a.m. | ||
| Sat., 4/13 | V Boys Sailing | O'Day Qualifier | Away - Indian Harbor Yacht Club | 9:00 a.m. | ||
| Sat., 4/13 | V Girls Lacrosse | Danbury | Home - Cardinal Stadium [Directions] | 2:00 p.m. | W 20-1 | |
| Sat., 4/13 | JV Girls Lacrosse | Danbury | Home - Cardinal Stadium [Directions] | 12:00 p.m. | ||
| Sat., 4/13 | V Girls Sailing | O'Day Qualifier | Away - Indian Harbor Yacht Club | 9:00 a.m. | ||
| Sun., 4/14 | V Boys Sailing | O'Day Finals | Away - Lake Wononscopomuc | 9:00 a.m. | ||
| Sun., 4/14 | V Girls Sailing | O'Day Finals | Away - Lake Wononscopomuc | 9:00 a.m. | ||
| Mon., 4/15 | FR Boys Lacrosse | Fairfield Ludlowe | Away - Tomlinson MS [Directions] | 4:00 p.m. | ||
| Mon., 4/15 | V Girls Lacrosse | Longmeadow (MA) | Home - Cardinal Stadium [Directions] | 4:30 p.m. | W 16-11 | |
| Mon., 4/15 | JV Girls Lacrosse | Greenwich Academy | Home - Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Tue., 4/16 | V Baseball | Fairfield Ludlowe | Home - Julian Curtiss School [Directions] | 11:00 a.m. | L 2-4 | |
| Tue., 4/16 | V Baseball | Fairfield Ludlowe | Home - Julian Curtiss School [Directions] | 1:00 p.m. | L 1-6 | |
| Tue., 4/16 | JV Baseball | Fairfield Ludlowe | Home - Julian Curtiss School [Directions] | 4:00 p.m. | ||
| Tue., 4/16 | FR Baseball | Fairfield Ludlowe | Away - Kiwanis Field [Directions] | 4:00 p.m. | W 7-4 | 2:45 EARLY DISMISSAL |
| Tue., 4/16 | V Boys Lacrosse | Staples | Home - Cardinal Stadium [Directions] | 1:00 p.m. | L 7-10 | |
| Tue., 4/16 | JV Boys Lacrosse | Staples | Home - GHS Field 7 [Directions] | 1:00 p.m. | ||
| Tue., 4/16 | V Boys Tennis | Stamford | Home - GHS Tennis Courts [Directions] | 10:00 a.m. | W 7-0 | |
| Tue., 4/16 | V Softball | Fairfield Ludlowe | Away - Dougiello Field [Directions] | 2:00 p.m. | L 2-9 | |
| Tue., 4/16 | V Girls Tennis | Stamford | Away - Stamford HS [Directions] | 10:00 a.m. | W 6-1 | |
| Wed., 4/17 | JV Baseball | St. Joseph | Away - Unity Park, Trumbull [Directions] | 4:00 p.m. | ||
| Wed., 4/17 | FR Baseball | St. Joseph | Home - GHS Baseball Field [Directions] | 4:30 p.m. | W 10-0 | |
| Wed., 4/17 | FR Boys Lacrosse | New Canaan | Home - Cardinal Stadium [Directions] | 4:30 p.m. | ||
| Wed., 4/17 | V Girls Lacrosse | Wilton | Away - Lilly Field - Turf [Directions] | 6:00 p.m. | L 7-16 | |
| Wed., 4/17 | JV Girls Lacrosse | Wilton | Away - Lilly Field - Turf [Directions] | 10:00 a.m. | ||
| Wed., 4/17 | V Softball | St. Joseph | Home - GHS Softball Field [Directions] | 2:00 p.m. | L 0-8 | |
| Wed., 4/17 | JV Softball | St. Joseph | Home - Julian Curtiss School [Directions] | 2:00 p.m. | ||
| Thu., 4/18 | V Baseball | Ridgefield | Away - Governor's Park Field (aka Ciuccoli or Old HS) [Directions] | 4:00 p.m. | L 2-3 | |
| Thu., 4/18 | JV Baseball | Ridgefield | Away - East Ridge MS [Directions] | 4:00 p.m. | ||
| Thu., 4/18 | FR Baseball | Ridgefield | Home - GHS Baseball Field [Directions] | 4:30 p.m. | W 3-2 | |
| Thu., 4/18 | V Boys Outdoor Track | Connecticut Distance Festival | Away - Xavier HS | 5:00 p.m. | ||
| Thu., 4/18 | V Boys Rugby | Boston College HS (MA) | Home - Cardinal Stadium [Directions] | 3:00 p.m. | ||
| Thu., 4/18 | V Girls Lacrosse | Greenwich Academy (Scrim.) | Home - GHS Field 3 [Directions] | 4:30 p.m. | ||
| Thu., 4/18 | V Girls Outdoor Track | Red Raider Relays | Away - North Rockland HS | 10:00 a.m. | ||
| Thu., 4/18 | V Softball | Ridgefield | Home - GHS Softball Field [Directions] | 4:30 p.m. | L 8-15 | |
| Thu., 4/18 | JV Softball | Ridgefield | Home - Julian Curtiss School [Directions] | 2:00 p.m. | ||
| Fri., 4/19 | School Holidays and Closings | Good Friday, Passover begins at sundown | ||||
| Sat., 4/20 | V Boys Lacrosse | Niskayuna (NY) | Away - Niskayuna HS | 2:00 p.m. | L 8-14 | |
| Sat., 4/20 | FR Boys Lacrosse | Ridgefield | Away - Tiger Hollow Turf Field II [Directions] | Cancelled | Cancelled | |
| Sat., 4/20 | V Boys Outdoor Track | Hillhouse Invitational | Away - New Haven Athletic Center | 10:00 a.m. | ||
| Sat., 4/20 | FR Boys Rugby | Fairfield Prep | Home - GHS Field 7 [Directions] | 9:00 a.m. | ||
| Sat., 4/20 | V Girls Outdoor Track | Hillhouse Invitational | Away - New Haven Athletic Center | 10:00 a.m. | ||
| Sat., 4/20 | School Holidays and Closings | First day of Passover | ||||
| Sun., 4/21 | School Holidays and Closings | Easter Sunday | ||||
| Mon., 4/22 | FR Boys Lacrosse | Westhill | Home - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | ||
| Mon., 4/22 | JV Boys Tennis | Horace Greeley (NY) | Away | 4:30 p.m. | 2:45 EARLY DISMISSAL/freshman | |
| Mon., 4/22 | V Boys Volleyball | New Canaan | Home - GHS Gymnasium [Directions] | 4:30 p.m. | L 2-3 | |
| Mon., 4/22 | JV Boys Volleyball | New Canaan | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 4/22 | V Girls Lacrosse | Bronxville (NY) | Away - Bronxville HS | 4:45 p.m. | L 12-14 | |
| Mon., 4/22 | JV Girls Lacrosse | Bronxville (NY) | Away - Bronxville HS | 5:45 p.m. | ||
| Mon., 4/22 | V Girls Outdoor Track | Trumbull, Westhill | Home - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | V Baseball | Staples | Home - Julian Curtiss School [Directions] | 4:30 p.m. | L 5-7 | |
| Tue., 4/23 | JV Baseball | Staples | Home - Havemeyer Field [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | FR Baseball | Staples | Away - Staples HS Baseball Field [Directions] | 4:00 p.m. | W 8-7 | 2:45 EARLY DISMISSAL |
| Tue., 4/23 | V Boys Golf | Brien McMahon, Norwalk | Home - Innis Arden Country Club [Directions] | 3:30 p.m. | Greenwich 150 Norwalk 195 | McMahon did not play rescheduled 5/9 |
| Tue., 4/23 | V Boys Lacrosse | Stamford | Away - Upper Lacrosse field at SHS [Directions] | 4:00 p.m. | W 16-2 | 2:30 EARLY DISMISSAL |
| Tue., 4/23 | JV Boys Lacrosse | Stamford | Away - Upper Lacrosse field at SHS [Directions] | 5:30 p.m. | ||
| Tue., 4/23 | V Boys Outdoor Track | Trumbull, Westhill | Away - McDougall Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | V Boys Rugby | Fairfield | Home - Cardinal Stadium [Directions] | 4:30 p.m. | ||
| Tue., 4/23 | V Boys Tennis | Trumbull | Away - THS Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | 2:00 EARLY DISMISSAL |
| Tue., 4/23 | JV Boys Tennis | Brunswick School | Away - Brunswick School | 4:00 p.m. | junior varsity | |
| Tue., 4/23 | JV Boys Tennis | Staples | Home - Central MS [Directions] | 4:30 p.m. | junior varsity | |
| Tue., 4/23 | V Girls Golf | New Canaan | Away - Country Club of New Canaan [Directions] | 3:45 p.m. | GHS 176 NCHS 171 | |
| Tue., 4/23 | V Softball | Staples | Away - Wakeman Field [Directions] | 4:00 p.m. | L 11-12 | 2:00 EARLY DISMISSAL |
| Tue., 4/23 | JV Softball | Staples | Away - Staples HS - Softball Field [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | V Girls Tennis | Trumbull | Home - GHS Tennis Courts [Directions] | 4:30 p.m. | W 7-0 | |
| Tue., 4/23 | JV Girls Tennis | Staples | Away - Town Farms Tennis Courts [Directions] | 4:00 p.m. | 2:45 EARLY DISMISSAL - FR | |
| Tue., 4/23 | JV Girls Tennis | New Canaan | Home - Binney Park [Directions] | 4:00 p.m. | JV | |
| Wed., 4/24 | V Baseball | Stamford | Home - GHS Baseball Field [Directions] | 4:30 p.m. | W 10-4 | |
| Wed., 4/24 | JV Baseball | Stamford | Home - Julian Curtiss School [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | FR Baseball | Stamford | Away - SHS Baseball Field [Directions] | 4:00 p.m. | W 9-5 | 3:00 EARLY DISMISSAL |
| Wed., 4/24 | V Boys Golf | Fairfield Prep | Away - Country Club of Fairfield [Directions] | 1:00 p.m. | Greenwich 150 Fairfield Prep 164 | |
| Wed., 4/24 | FR Boys Lacrosse | Staples | Home - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | ||
| Wed., 4/24 | V Boys Sailing | Regatta | Home - Grass Island [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | V Boys Tennis | Staples | Home - GHS Tennis Courts [Directions] | 4:30 p.m. | W 4-3 | |
| Wed., 4/24 | JV Boys Tennis | Fairfield Ludlowe | Away - Tomlinson MS Tennis Courts [Directions] | 3:30 p.m. | 2:45 EARLY DISMISSAL/junior varsity | |
| Wed., 4/24 | JV Boys Tennis | New Canaan | Home - Central MS [Directions] | 4:30 p.m. | freshman | |
| Wed., 4/24 | V Boys Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | 2:00 EARLY DISMISSAL |
| Wed., 4/24 | JV Boys Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 4/24 | V Girls Golf | St. Joseph | Away [Directions] | 3:15 p.m. | GHS:183 SJHS: 211 | |
| Wed., 4/24 | JV Girls Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Wed., 4/24 | V Girls Sailing | Regatta | Home - Grass Island [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | V Softball | Stamford | Away - SHS Softball Field [Directions] | 4:00 p.m. | L 10-11 | 2:30 EARLY DISMISSAL |
| Wed., 4/24 | JV Softball | Stamford | Away - Cummings Park Field #4 [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | FR Softball | Greenwich Country Day | Away - Greenwich Country Day School | 4:00 p.m. | ||
| Wed., 4/24 | V Girls Tennis | Staples | Away - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Wed., 4/24 | JV Girls Tennis | Fairfield Ludlowe | Home - Binney Park [Directions] | 4:00 p.m. | JV | |
| Thu., 4/25 | V Boys Golf | Brunswick Invitational | Away - Round Hill Country Club | TBA | Greenwich 166 | |
| Thu., 4/25 | V Boys Lacrosse | New Canaan | Away - Dunning Stadium [Directions] | 6:30 p.m. | L 4-12 | |
| Thu., 4/25 | JV Boys Lacrosse | New Canaan | Away - NCHS Water Tower Turf Field [Directions] | 4:30 p.m. | 3:00 EARLY DISMISSAL | |
| Thu., 4/25 | JV Boys Rugby | Fordham Prep (NY) | Away | TBA | ||
| Thu., 4/25 | V Boys Tennis | Westhill | Home - GHS Tennis Courts [Directions] | 4:30 p.m. | W 7-0 | |
| Thu., 4/25 | JV Boys Tennis | Trumbull | Home - Central MS [Directions] | 4:30 p.m. | freshman | |
| Thu., 4/25 | V Girls Lacrosse | Trumbull | Home - Cardinal Stadium [Directions] | 4:30 p.m. | W 16-6 | |
| Thu., 4/25 | JV Girls Lacrosse | Trumbull | Home - Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Thu., 4/25 | FR Softball | Norwalk | Away - Naramake School [Directions] | 4:30 p.m. | 3:00 EARLY DISMISSAL | |
| Thu., 4/25 | V Girls Tennis | Westhill | Away [Directions] | 4:30 p.m. | L 3-4 | 2:30 EARLY DISMISSAL |
| Thu., 4/25 | JV Girls Tennis | Trumbull | Home - Binney Park [Directions] | 4:00 p.m. | JV | |
| Fri., 4/26 | V Boys Outdoor Track | O'Grady Relays | Away - Bethel HS | 5:00 p.m. | ||
| Fri., 4/26 | JV Boys Volleyball | Norwalk | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 4/26 | V Girls Outdoor Track | O'Grady Relays | Away - Bethel HS | 5:00 p.m. | ||
| Sat., 4/27 | V Boys Lacrosse | Bronxville (NY) | Home - Cardinal Stadium [Directions] | 12:00 p.m. | L 9-11 | |
| Sat., 4/27 | JV Boys Lacrosse | Bronxville (NY) | Home - GHS Field 7 [Directions] | 12:00 p.m. | ||
| Sat., 4/27 | FR Boys Lacrosse | Fairfield Prep | Home - Cardinal Stadium [Directions] | 9:00 a.m. | ||
| Sat., 4/27 | JV Boys Rugby | Bishop Hendricken (RI) | Home - GHS Field 7 [Directions] | 3:00 p.m. | ||
| Sat., 4/27 | FR Boys Rugby | Fairfield | Home - GHS Field 7 [Directions] | 9:00 a.m. | ||
| Sat., 4/27 | V Boys Sailing | State Championships | Away - Sail Black Rock | 9:00 a.m. | ||
| Sat., 4/27 | V Girls Lacrosse | Oak Knoll (NJ) | Away - Oak Knoll School | 12:00 p.m. | L 4-16 | |
| Sat., 4/27 | JV Girls Lacrosse | Oak Knoll (NJ) | Away - Oak Knoll School | 10:00 a.m. | ||
| Sat., 4/27 | V Girls Sailing | State Championships | Away - Sail Black Rock | 9:00 a.m. | ||
| Sat., 4/27 | School Holidays and Closings | Last day of Passover | ||||
| Sat., 4/27 | School Holidays and Closings | Junior Prom | ||||
| Sun., 4/28 | V Boys Sailing | Herreshoff Qualifier | Away - The Waterfront Center | 9:00 a.m. | ||
| Sun., 4/28 | V Girls Sailing | Herreshoff Qualifier | Away - The Waterfront Center | 9:00 a.m. | ||
| Mon., 4/29 | V Baseball | Trumbull | Away - Varsity Baseball Field [Directions] | 4:00 p.m. | L 4-9 | 2:00 EARLY DISMISSAL |
| Mon., 4/29 | JV Baseball | Trumbull | Away - JV Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | FR Baseball | Trumbull | Home - GHS Baseball Field [Directions] | 4:30 p.m. | L 15-2 | |
| Mon., 4/29 | V Boys Golf | Wilton | Away - Rolling Hills CC [Directions] | 3:15 p.m. | Greenwich 145 Wilton 174 | |
| Mon., 4/29 | JV Boys Golf | Wilton | Away - Rolling Hills CC [Directions] | 3:15 p.m. | ||
| Mon., 4/29 | FR Boys Lacrosse | Trumbull | Away - The Pit [Directions] | 4:00 p.m. | 2:45 EARLY DISMISSAL | |
| Mon., 4/29 | V Boys Tennis | Wilton | Away - Wilton Tennis Courts [Directions] | 4:00 p.m. | L 3-4 | 2:00 EARLY DISMISSAL |
| Mon., 4/29 | JV Boys Tennis | Wilton | Away - Middlebrook School [Directions] | 4:00 p.m. | 2:45 EARLY DISMISSAL/freshman | |
| Mon., 4/29 | V Boys Volleyball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 4:30 p.m. | W 3-0 | 2:30 EARLY DISMISSAL |
| Mon., 4/29 | JV Boys Volleyball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 6:00 p.m. | ||
| Mon., 4/29 | FR Girls Lacrosse | Trumbull | Away - JV Grass Field [Directions] | 4:00 p.m. | 2:45 EARLY DISMISSAL | |
| Mon., 4/29 | V Girls Outdoor Track | Ridgefield, Stamford | Home - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | V Softball | Trumbull | Home - GHS Softball Field [Directions] | 4:30 p.m. | L 0-1 | |
| Mon., 4/29 | JV Softball | Trumbull | Home - Julian Curtiss School [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | FR Softball | Newtown | Away - Newtown HS Softball Field [Directions] | 4:30 p.m. | 2:45 EARLY DISMISSAL | |
| Mon., 4/29 | V Girls Tennis | Wilton | Home - GHS Tennis Courts [Directions] | 4:00 p.m. | L 3-4 | |
| Mon., 4/29 | JV Girls Tennis | Wilton | Home - Binney Park [Directions] | 4:00 p.m. | FR | |
| Tue., 4/30 | V Boys Golf | Westhill, Stamford | Away - E. Gaynor Brennan Golf Course [Directions] | 3:15 p.m. | Greenwich 156 Westhill 166 Stamford 194 | |
| Tue., 4/30 | V Boys Outdoor Track | Ridgefield, Stamford | Away - Tiger Hollow Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/30 | V Boys Tennis | Bridgeport Central | Home - GHS Tennis Courts [Directions] | 4:30 p.m. | W 7-0 | |
| Tue., 4/30 | V Girls Golf | Darien | Home - Griffith E Harris Golf Course [Directions] | 3:45 p.m. | GHS: 188 DHS: 223 | |
| Tue., 4/30 | V Girls Lacrosse | Westhill | Away - J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | W 19-2 | 2:30 EARLY DISMISSAL |
| Tue., 4/30 | JV Girls Lacrosse | Westhill | Away - J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | ||
| Tue., 4/30 | FR Girls Lacrosse | Ridgefield | Home - GHS Field 3 [Directions] | 4:30 p.m. | ||
| Tue., 4/30 | V Softball | Norwalk | Home - GHS Softball Field [Directions] | 4:30 p.m. | W 7-5 | |
| Tue., 4/30 | JV Softball | Norwalk | Home - Julian Curtiss School [Directions] | 4:00 p.m. | ||
| Tue., 4/30 | V Girls Tennis | Bridgeport Central | Away [Directions] | 4:00 p.m. | W 7-0 | 2:15 EARLY DISMISSAL |
| Wed., 5/1 | V Baseball | Westhill | Home - GHS Baseball Field [Directions] | 4:30 p.m. | L 3-7 | |
| Wed., 5/1 | JV Baseball | Westhill | Home - Julian Curtiss School [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | FR Baseball | Westhill | Away - Westhill Baseball Field [Directions] | 4:30 p.m. | W 7-6 | 3:00 EARLY DISMISSAL |
| Wed., 5/1 | FR Boys Lacrosse | Wilton | Away - Allen's Field [Directions] | 4:30 p.m. | 2:45 EARLY DISMISSAL | |
| Wed., 5/1 | V Boys Rugby | MidState | Away | 5:00 p.m. | ||
| Wed., 5/1 | FR Boys Rugby | Aspetuck | Away | 6:00 p.m. | ||
| Wed., 5/1 | V Boys Sailing | Regatta | Home - Grass Island [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | V Boys Tennis | Norwalk | Away - Norwalk HS [Directions] | 4:00 p.m. | W 5-2 | 2:30 EARLY DISMISSAL |
| Wed., 5/1 | JV Boys Tennis | Greenwich Country Day | Away - Greenwich Country Day School | 4:00 p.m. | freshman | |
| Wed., 5/1 | V Boys Volleyball | Trumbull | Home - GHS Gymnasium [Directions] | 4:30 p.m. | L 1-3 | |
| Wed., 5/1 | JV Boys Volleyball | Trumbull | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 5/1 | V Girls Golf | Trumbull | Home - Griffith E Harris Golf Course [Directions] | 3:45 p.m. | GHS: 199 THS: 227 | |
| Wed., 5/1 | FR Girls Lacrosse | Wilton | Home - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | ||
| Wed., 5/1 | V Girls Outdoor Track | Wilton | Away - WHS Track [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | JV Girls Rugby | Fairfield | Home - Cardinal Stadium [Directions] | 5:00 p.m. | ||
| Wed., 5/1 | V Girls Sailing | Regatta | Home - Grass Island [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | V Softball | Westhill | Away - Westhill Softball Field [Directions] | 4:30 p.m. | W 25-2 | 2:30 EARLY DISMISSAL |
| Wed., 5/1 | JV Softball | Westhill | Away - Roxbury Elementary School [Directions] | 4:30 p.m. | ||
| Wed., 5/1 | V Girls Tennis | Norwalk | Home - GHS Tennis Courts [Directions] | 4:30 p.m. | W 7-0 | |
| Thu., 5/2 | V Baseball | Norwalk | Away - Callahan Complex at Nathan Hale Upper [Directions] | 4:30 p.m. | L 4-8 | 2:30 EARLY DISMISSAL |
| Thu., 5/2 | V Boys Golf | Greenwich Invitational | Home - Stanwich Country Club [Directions] | TBA | Greenwich 162 | |
| Thu., 5/2 | V Boys Lacrosse | Danbury | Home - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | W 14-3 | |
| Thu., 5/2 | V Boys Outdoor Track | Wilton | Home - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Thu., 5/2 | V Boys Tennis | Fairfield Warde | Home - GHS Tennis Courts [Directions] | 4:30 p.m. | W 7-0 | |
| Thu., 5/2 | JV Boys Tennis | Fairfield Warde | Home - Central MS [Directions] | 4:30 p.m. | junior varsity | |
| Thu., 5/2 | V Girls Golf | Ridgefield | Away - Ridgefield Public GC (DHLY Ridge) [Directions] | 3:45 p.m. | GHS: 189 RHS: 187 | |
| Thu., 5/2 | JV Girls Golf | Darien | Home - Milbrook Country Club [Directions] | 3:30 p.m. | ||
| Thu., 5/2 | V Girls Lacrosse | Stamford | Home - GHS Field 3 [Directions] | 4:30 p.m. | W 17-4 | |
| Thu., 5/2 | JV Girls Lacrosse | Stamford | Home - GHS Field 3 [Directions] | 5:30 p.m. | ||
| Thu., 5/2 | FR Softball | Danbury | Home - Julian Curtiss School [Directions] | 4:30 p.m. | ||
| Fri., 5/3 | V Baseball | Wilton | Away - WHS Varsity Baseball Field [Directions] | 4:15 p.m. | W 14-4 | 2:00 EARLY DISMISSAL |
| Fri., 5/3 | JV Baseball | Wilton | Away - JV Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 5/3 | FR Baseball | Wilton | Home - GHS Baseball Field [Directions] | 4:30 p.m. | W 9-5 | |
| Fri., 5/3 | JV Boys Tennis | New Canaan | Home - Central MS [Directions] | 4:30 p.m. | junior varsity | |
| Fri., 5/3 | V Boys Volleyball | Darien | Away - DHS Main Gym [Directions] | 4:00 p.m. | L 0-3 | 2:30 EARLY DISMISSAL |
| Fri., 5/3 | JV Boys Volleyball | Darien | Away - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 5/3 | FR Girls Lacrosse | New Canaan | Away - WTT2 [Directions] | 4:30 p.m. | ||
| Fri., 5/3 | V Softball | Wilton | Home - GHS Softball Field [Directions] | 4:30 p.m. | W 12-2 | |
| Sat., 5/4 | JV Baseball | Norwalk | Away - Callahan Complex at Nathan Hale Upper [Directions] | 12:00 p.m. | ||
| Sat., 5/4 | FR Baseball | Norwalk | Away - Callahan Complex at Nathan Hale Upper [Directions] | 10:00 a.m. | W 2-0 | |
| Sat., 5/4 | V Boys Lacrosse | Darien | Home - Cardinal Stadium [Directions] | 2:00 p.m. | L 0-15 | |
| Sat., 5/4 | JV Boys Lacrosse | Darien | Home - GHS Field 7 [Directions] | 2:00 p.m. | ||
| Sat., 5/4 | V Boys Outdoor Track | Middletown Invitational | Away - Middletown HS | 10:00 a.m. | ||
| Sat., 5/4 | V Boys Rugby | Aspetuck | Home - Cardinal Stadium [Directions] | 4:30 p.m. | ||
| Sat., 5/4 | V Girls Outdoor Track | Middletown Invitational | Away - Middletown HS | 1:00 p.m. | ||
| Sat., 5/4 | V Girls Rugby | Simsbury | Away - Simsbury HS [Directions] | 1:30 p.m. | ||
| Mon., 5/6 | V Baseball | Bridgeport Central | Home - Julian Curtiss School [Directions] | 4:30 p.m. | W 5-4 | |
| Mon., 5/6 | V Boys Lacrosse | Somers (NY) | Home - Cardinal Stadium [Directions] | 5:00 p.m. | W 15-10 | |
| Mon., 5/6 | JV Boys Lacrosse | Somers (NY) | Home - Cos Cob Park Benvenuto Field [Directions] | 5:00 p.m. | ||
| Mon., 5/6 | FR Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde Grass Utility Field [Directions] | 5:00 p.m. | 3:00 EARLY DISMISSAL | |
| Mon., 5/6 | V Boys Tennis | Danbury | Home - GHS Tennis Courts [Directions] | 3:30 p.m. | W 7-0 | |
| Mon., 5/6 | JV Boys Tennis | Darien | Away - Cherry Lawn Park [Directions] | 4:30 p.m. | 3:00 EARLY DISMISSAL/junior varsity | |
| Mon., 5/6 | V Boys Volleyball | Fairfield Warde | Home - GHS Gymnasium [Directions] | 6:00 p.m. | L 0-3 | |
| Mon., 5/6 | JV Boys Volleyball | Fairfield Warde | Home - GHS Gymnasium [Directions] | 4:30 p.m. | ||
| Mon., 5/6 | V Girls Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 2:50 p.m. | GHS: 191 FLHS: 182 | |
| Mon., 5/6 | FR Girls Lacrosse | Fairfield Ludlowe | Away - Sturges Park [Directions] | 4:00 p.m. | 2:45 EARLY DISMISSAL | |
| Mon., 5/6 | V Girls Outdoor Track | St. Joseph | Away [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | V Softball | Bridgeport Central | Away - Luis Marin Field #2 [Directions] | 4:30 p.m. | W 15-1 | 2:00 EARLY DISMISSAL |
| Mon., 5/6 | V Girls Tennis | Danbury | Home - Greenwich HS [Directions] | 5:00 p.m. | W 7-0 | |
| Mon., 5/6 | JV Girls Tennis | Darien | Home - Binney Park [Directions] | 4:30 p.m. | JV | |
| Mon., 5/6 | V Girls Water Polo | Hopkins School | Home - GHS Pool [Directions] | 4:45 p.m. | ||
| Tue., 5/7 | V Baseball | St. Joseph | Away - St. Joseph HS [Directions] | 5:45 p.m. | W 10-7 | |
| Tue., 5/7 | V Boys Golf | Ridgefield | Away - Ridgewood Country Club [Directions] | 3:15 p.m. | Greenwich 152 Ridgefield 163 | |
| Tue., 5/7 | JV Boys Golf | Brunswick School | Home - Burning Tree Country Club [Directions] | 3:30 p.m. | ||
| Tue., 5/7 | V Boys Outdoor Track | St. Joseph | Home - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | V Boys Tennis | Trinity Catholic | Away | 4:00 p.m. | W 7-0 | 2:30 EARLY DISMISSAL |
| Tue., 5/7 | V Girls Lacrosse | Darien | Away - DHS Center Oval Turf Field [Directions] | 4:00 p.m. | L 8-21 | 3:00 EARLY DISMISSAL |
| Tue., 5/7 | JV Girls Lacrosse | Darien | Away - DHS Center Oval Turf Field [Directions] | 5:30 p.m. | ||
| Tue., 5/7 | V Girls Rugby | Harvey School (NY) | Away - Harvey School | 4:30 p.m. | ||
| Tue., 5/7 | FR Softball | Norwalk | Home - GHS Softball Field [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | V Girls Tennis | Trinity Catholic | Home - GHS Tennis Courts [Directions] | 4:30 p.m. | W 7-0 | |
| Tue., 5/7 | JV Girls Tennis | Wilton | Away - Wilton HS [Directions] | 4:30 p.m. | 3:00 EARLY DISMISSAL - FR | |
| Wed., 5/8 | V Baseball | Fairfield Warde | Home - GHS Baseball Field [Directions] | 4:30 p.m. | L 5-8 | |
| Wed., 5/8 | JV Baseball | Fairfield Warde | Home - Julian Curtiss School [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | FR Baseball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 4:00 p.m. | L 0-10 | 3:00 EARLY DISMISSAL |
| Wed., 5/8 | V Boys Golf | Fairfield Ludlowe | Home - Round Hill Country Club [Directions] | 3:30 p.m. | Greenwich 155 Ludlowe 167 | |
| Wed., 5/8 | V Boys Lacrosse | Brien McMahon | Home - Cardinal Stadium [Directions] | 6:00 p.m. | W 16-9 | |
| Wed., 5/8 | JV Boys Lacrosse | Brien McMahon | Home - Cos Cob Park Benvenuto Field [Directions] | Cancelled | Cancelled | |
| Wed., 5/8 | FR Boys Lacrosse | Darien | Away - DHS Center Oval Turf Field [Directions] | 5:00 p.m. | 3:00 EARLY DISMISSAL | |
| Wed., 5/8 | JV Boys Rugby | New Rochelle (NY) | Home - GHS Field 7 [Directions] | 5:00 p.m. | ||
| Wed., 5/8 | V Boys Sailing | Regatta | Home - Grass Island [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | V Boys Volleyball | Staples | Away - Staples H.S. Gym [Directions] | 4:00 p.m. | L 0-3 | 2:00 EARLY DISMISSAL |
| Wed., 5/8 | JV Boys Volleyball | Staples | Away - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Wed., 5/8 | V Girls Golf | Fairfield Ludlowe | Home - Griffith E Harris Golf Course [Directions] | 3:45 p.m. | GHS: 192 FLHS: 183 | |
| Wed., 5/8 | FR Girls Lacrosse | Darien | Away - DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | 3:00 EARLY DISMISSAL | |
| Wed., 5/8 | V Girls Sailing | Regatta | Home - Grass Island [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | V Softball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 4:00 p.m. | W 4-3 | 2:00 EARLY DISMISSAL |
| Wed., 5/8 | JV Softball | Fairfield Warde | Away - Melville Park [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | FR Softball | Greenwich Country Day | Home - GHS Softball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | V Girls Tennis | Fairfield Warde | Away - FWHS Blake Courts [Directions] | 4:00 p.m. | W 6-1 | 2:15 EARLY DISMISSAL |
| Wed., 5/8 | JV Girls Tennis | Fairfield Warde | Away - Fairfield Woods MS [Directions] | 4:00 p.m. | 2:45 EARLY DISMISSAL - JV | |
| Wed., 5/8 | V Girls Water Polo | Convent of Sacred Heart | Home - GHS Pool [Directions] | 4:30 p.m. | ||
| Thu., 5/9 | V Boys Golf | Brien McMahon | Home - Griffith E Harris Golf Course [Directions] | 3:30 p.m. | ||
| Thu., 5/9 | JV Boys Lacrosse | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 4:30 p.m. | 3:00 EARLY DISMISSAL | |
| Thu., 5/9 | V Boys Rugby | Staples | Away - Staples HS [Directions] | 5:30 p.m. | ||
| Thu., 5/9 | JV Girls Golf | Staples | Home - Milbrook Country Club [Directions] | 3:30 p.m. | ||
| Thu., 5/9 | V Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS [Directions] | 7:00 p.m. | W 19-10 | |
| Thu., 5/9 | JV Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:00 p.m. | 2:30 EARLY DISMISSAL | |
| Thu., 5/9 | V Girls Rugby | MidState | Away | 4:30 p.m. | ||
| Thu., 5/9 | JV Girls Tennis | Greenwich Country Day | Away - Greenwich Country Day School | 4:00 p.m. | JV | |
| Fri., 5/10 | V Baseball | Danbury | Home - GHS Baseball Field [Directions] | 4:30 p.m. | W 3-2 | |
| Fri., 5/10 | JV Baseball | Danbury | Home - Julian Curtiss School [Directions] | 4:00 p.m. | ||
| Fri., 5/10 | FR Baseball | Danbury | Away - Danbury HS Varsity Baseball Field [Directions] | 4:00 p.m. | W 11-0 | 2:45 EARLY DISMISSAL |
| Fri., 5/10 | FR Boys Lacrosse | New Canaan | Away - NCHS Water Tower Turf Field [Directions] | 6:00 p.m. | 3:00 EARLY DISMISSAL | |
| Fri., 5/10 | JV Boys Tennis | Horace Greeley (NY) | Away - Horace Greeley HS | 4:30 p.m. | ||
| Fri., 5/10 | V Boys Volleyball | Stamford | Home - GHS Gymnasium [Directions] | 4:30 p.m. | W 3-0 | |
| Fri., 5/10 | JV Boys Volleyball | Stamford | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 5/10 | FR Girls Lacrosse | New Canaan | Away - Water Tower #2 [Directions] | 4:30 p.m. | 3:00 EARLY DISMISSAL | |
| Fri., 5/10 | V Softball | Danbury | Away - Danbury HS Varsity Softball Field [Directions] | 4:30 p.m. | W 10-6 | |
| Fri., 5/10 | JV Softball | Danbury | Away - Danbury HS Junior Varsity Softball Field [Directions] | 4:30 p.m. | 3:00 EARLY DISMISSAL | |
| Fri., 5/10 | V Girls Water Polo | Cardinal Tournament | Home - GHS Pool [Directions] | 4:00 p.m. | ||
| Sat., 5/11 | V Boys Lacrosse | Iona Prep (NY) | Home - Cardinal Stadium [Directions] | 12:00 p.m. | W 10-8 | |
| Sat., 5/11 | JV Boys Lacrosse | Iona Prep (NY) | Away - Iona Prep | 12:00 p.m. | ||
| Sat., 5/11 | V Boys Outdoor Track | Greater Hartford Invitational | Away - East Hartford HS | 9:00 a.m. | ||
| Sat., 5/11 | FR Boys Rugby | Xavier (NY) | Home - GHS Field 7 [Directions] | 10:00 a.m. | ||
| Sat., 5/11 | V Boys Sailing | Mallory Championship | Away - Sail Sand Point | 9:00 a.m. | ||
| Sat., 5/11 | V Girls Lacrosse | New Canaan | Away - Dunning Stadium [Directions] | 12:00 p.m. | L 2-10 | |
| Sat., 5/11 | JV Girls Lacrosse | New Canaan | Away - Dunning Stadium [Directions] | 10:00 a.m. | ||
| Sat., 5/11 | V Girls Outdoor Track | Greater Hartford Invitational | Away - East Hartford HS | 9:00 a.m. | ||
| Sat., 5/11 | V Girls Sailing | Mallory Championships | Away - Sail Sand Point | 9:00 a.m. | ||
| Sun., 5/12 | V Boys Sailing | Herreshoff Finals | Away - Sail Maine | 9:00 a.m. | ||
| Sun., 5/12 | V Girls Sailing | Herreshoff Finals | Away - Sail Maine | 9:00 a.m. | ||
| Sun., 5/12 | School Holidays and Closings | Mothers Day | ||||
| Mon., 5/13 | V Boys Rugby | Ridgefield | Away - Ridgefield HS [Directions] | 5:30 p.m. | ||
| Mon., 5/13 | V Boys Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 4:00 p.m. | L 2-3 | 2:00 EARLY DISMISSAL |
| Mon., 5/13 | JV Boys Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 5:30 p.m. | ||
| Tue., 5/14 | V Boys Golf | St. Joseph, Trumbull | Away [Directions] | 3:15 p.m. | Greenwich 155 Trumbull 161 St. Joe's 186 | |
| Tue., 5/14 | V Boys Lacrosse | Chaminade (NY) | Away - Chaminade School | Cancelled | Cancelled | 2:30 EARLY DISMISSAL |
| Tue., 5/14 | JV Boys Lacrosse | Staples | Away - Wakeman Field B (turf) [Directions] | 4:30 p.m. | ||
| Tue., 5/14 | JV Boys Lacrosse | Chaminade (NY) | Away | Cancelled | Cancelled | 2:30 EARLY DISMISSAL |
| Tue., 5/14 | V Boys Sailing | Silver Cup | Home - Grass Island [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | JV Boys Tennis | Staples | Away - Town Farms Tennis Courts [Directions] | 4:00 p.m. | 2:45 EARLY DISMISSAL | |
| Tue., 5/14 | JV Boys Tennis | Horace Greeley (NY) | Away - Horace Greeley HS | Cancelled | Cancelled | 3:00 EARLY DISMISSAL/freshman |
| Tue., 5/14 | V Girls Golf | Danbury | Home - Griffith E Harris Golf Course [Directions] | 3:45 p.m. | GHS:190 DHS: 259 | |
| Tue., 5/14 | V Girls Lacrosse | St. Joseph | Home - Cardinal Stadium [Directions] | 4:30 p.m. | W 16-9 | |
| Tue., 5/14 | JV Girls Lacrosse | St. Joseph | Home - Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Tue., 5/14 | FR Girls Lacrosse | Fairfield Warde | Home - GHS Field 3 [Directions] | 4:30 p.m. | ||
| Tue., 5/14 | V Girls Sailing | Silver Cup | Home - Grass Island [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | V Softball | Trinity Catholic | Home - Bruce Park Softball Field [Directions] | 4:30 p.m. | W 8-2 | |
| Tue., 5/14 | V Girls Tennis | FCIAC Tournament | Home - GHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | V Boys Golf | Staples | Home - Burning Tree Country Club [Directions] | 3:30 p.m. | Greenwich 150 Staples 171 | |
| Wed., 5/15 | JV Boys Golf | New Canaan | Home - Griffith E Harris Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 5/15 | JV Boys Golf | Staples | Away [Directions] | Cancelled | Cancelled | |
| Wed., 5/15 | V Boys Sailing | Gold Cup | Home - Grass Island [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | V Boys Tennis | Ridgefield | Home - TBA [Directions] | 4:30 p.m. | W 4-1 | |
| Wed., 5/15 | JV Boys Tennis | Greenwich Country Day | Away - Greenwich Country Day School | 4:00 p.m. | junior varsity | |
| Wed., 5/15 | JV Boys Tennis | Ridgefield | Home - Central MS [Directions] | 4:30 p.m. | freshman | |
| Wed., 5/15 | V Boys Volleyball | Stamford | Away - Kuzco Gymnasium at Stamford HS [Directions] | 4:00 p.m. | W 3-0 | 2:30 EARLY DISMISSAL |
| Wed., 5/15 | JV Boys Volleyball | Stamford | Away - Kuzco Gymnasium at Stamford HS [Directions] | 5:30 p.m. | ||
| Wed., 5/15 | V Girls Golf | Staples | Away - Longshore [Directions] | 3:00 p.m. | GHS: 177 SHS: 188 | |
| Wed., 5/15 | JV Girls Golf | Fairfield | Away - South Pine Creek Golf Course | 3:45 p.m. | ||
| Wed., 5/15 | FR Girls Lacrosse | Greenwich Country Day | Away - Greenwich Country Day School | Cancelled | Cancelled | |
| Wed., 5/15 | V Girls Sailing | Gold Cup | Home - Grass Island [Directions] | 4:00 p.m. | ||
| Thu., 5/16 | V Baseball | Trinity Catholic | Away - Trinity Catholic's Lione Field | 5:00 p.m. | W 9-1 | 2:30 EARLY DISMISSAL |
| Thu., 5/16 | V Boys Golf | New Canaan | Away - Country Club of New Canaan [Directions] | 4:00 p.m. | Greenwich 150 NC 160 | |
| Thu., 5/16 | JV Boys Golf | Darien | Away - Woodway CC [Directions] | 3:15 p.m. | ||
| Thu., 5/16 | FR Boys Lacrosse | Ridgefield | Home - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | ||
| Thu., 5/16 | V Boys Outdoor Track | Staples | Home - Greenwich HS [Directions] | 4:00 p.m. | ||
| Thu., 5/16 | V Boys Rugby | National Championships | Away | TBA | ||
| Thu., 5/16 | V Girls Lacrosse | FCIAC Tournament | Away - New Canaan HS | 6:30 p.m. | ||
| Thu., 5/16 | FR Girls Lacrosse | Norwalk | Away - Callahan Complex at Nathan Hale Lower [Directions] | 4:30 p.m. | ||
| Thu., 5/16 | V Girls Outdoor Track | Staples | Home - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Thu., 5/16 | V Girls Rugby | State Tournament | Away - Simsbury HS | 5:00 p.m. | ||
| Fri., 5/17 | V Boys Rugby | National Championships | Away | TBA | ||
| Fri., 5/17 | V Boys Volleyball | Ridgefield | Home - GHS Gymnasium [Directions] | 4:30 p.m. | L 1-3 | |
| Fri., 5/17 | JV Boys Volleyball | Ridgefield | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Sat., 5/18 | FR Boys Lacrosse | Fairfield Prep | Away - Barlow Field, Fairfield University [Directions] | 10:00 a.m. | ||
| Sat., 5/18 | V Boys Rugby | National Championships | Away | TBA | ||
| Sat., 5/18 | V Boys Sailing | President Trophy | Away - Sail Maine | 9:00 a.m. | ||
| Sat., 5/18 | V Girls Sailing | NESSA Championships | Away - Sail Maine | 9:00 a.m. | ||
| Sat., 5/18 | V Softball | FCIAC Tournament | Away - Trumbull HS | 11:00 a.m. | ||
| Sun., 5/19 | V Boys Sailing | Regatta | Away - The Waterfront Center | 9:00 a.m. | ||
| Sun., 5/19 | V Girls Sailing | NESSA Championships | Away | 9:00 a.m. | ||
| Mon., 5/20 | V Boys Golf | Fairfield Warde | Home - Stanwich Country Club [Directions] | 3:30 p.m. | Greenwich 165 Warde 172 | |
| Mon., 5/20 | JV Boys Rugby | Staples | Away [Directions] | 4:30 p.m. | ||
| Mon., 5/20 | FR Boys Rugby | Staples | Home - GHS Field 7 [Directions] | 5:00 p.m. | ||
| Tue., 5/21 | V Boys Outdoor Track | FCIAC Championships | Away - Southern Connecticut State University | 2:00 p.m. | ||
| Tue., 5/21 | V Boys Tennis | Staples | Away - Staples HS [Directions] | 4:00 p.m. | L 0-4 | 2:00 EARLY DISMISSAL |
| Tue., 5/21 | V Girls Golf | Fairfield Warde | Home - Griffith E Harris Golf Course [Directions] | 3:45 p.m. | GHS: 183 FWHS: 186 | |
| Tue., 5/21 | V Girls Outdoor Track | FCIAC Championships | Away - Southern Connecticut State University | 2:00 p.m. | ||
| Wed., 5/22 | V Baseball | SCRIMMAGE | Home - GHS Baseball Field [Directions] | 4:15 p.m. | ||
| Wed., 5/22 | V Boys Golf | Darien | Home - Round Hill Country Club [Directions] | 3:30 p.m. | Greenwich 146 Darien 147 | |
| Wed., 5/22 | V Boys Lacrosse | SCRIMMAGE | Away - Fairfield Ludlowe HS | 5:00 p.m. | ||
| Wed., 5/22 | V Boys Tennis | FCIAC Championship | Away - Wilton HS | 4:00 p.m. | ||
| Wed., 5/22 | JV Co-ed Sailing | REGATTA | Home - Grass Island [Directions] | 4:00 p.m. | ||
| Wed., 5/22 | V Softball | SCRIMMAGE | Away - Norwalk HS | 4:00 p.m. | ||
| Thu., 5/23 | JV Boys Rugby | Ridgefield | Away - Ridgefield [Directions] | 4:30 p.m. | ||
| Thu., 5/23 | V Girls Golf | Amity | Away [Directions] | TBA | GHS: 180 AHS: 191 Played back 9 | |
| Fri., 5/24 | V Boys Rugby | State Tournament | Home - Cardinal Stadium [Directions] | 5:00 p.m. | ||
| Fri., 5/24 | V Boys Tennis | State Tournament | Away - William Hall HS | 8:30 a.m. | ||
| Fri., 5/24 | V Girls Lacrosse | State Tournament | Away - Brien McMahon HS | 7:30 p.m. | ||
| Fri., 5/24 | V Girls Tennis | State Tournament | Home - GHS Tennis Courts [Directions] | 3:00 p.m. | ||
| Sat., 5/25 | V Baseball | State Tournament | Away | 6:00 p.m. | ||
| Sat., 5/25 | V Boys Lacrosse | State Tournament | Away - Shelton HS | 11:00 a.m. | ||
| Sat., 5/25 | V Boys Tennis | State Tournament | Away - William Hall HS | 9:00 a.m. | ||
| Sat., 5/25 | V Girls Tennis | State Tournament | Away - Wilton HS | 2:30 p.m. | ||
| Sun., 5/26 | V Boys Rugby | State Championship | Away - Ridgefield HS | 5:00 p.m. | ||
| Mon., 5/27 | School Holidays and Closings | Memorial Day | ||||
| Tue., 5/28 | V Girls Golf | Darien, Fairfield Warde | Away - Fairchild Wheeler [Directions] | 2:45 p.m. | GHS: 182 DHS: 197 FWHS: 167 | |
| Tue., 5/28 | V Girls Lacrosse | State Tournament | Away - Cheshire HS | 5:00 p.m. | ||
| Wed., 5/29 | V Boys Tennis | State Tournament | Away - Amity HS | 3:30 p.m. | ||
| Wed., 5/29 | JV Girls Golf | Tournament | Away - South Pine Creek Golf Course | 3:00 p.m. | ||
| Wed., 5/29 | V Softball | State Tournament | Home - GHS Softball Field [Directions] | 3:30 p.m. | ||
| Thu., 5/30 | V Boys Golf | FCIAC Championship | Away - Fairchild Wheeler Golf Course | 12:30 p.m. | ||
| Thu., 5/30 | V Boys Lacrosse | State Tournament | Away - Fairfield University | 4:00 p.m. | 2:00 EARLY DISMISSAL | |
| Thu., 5/30 | V Boys Outdoor Track | State Championships | Away - Willowbrook Park | 12:00 p.m. | 9:00 EARLY DISMISSAL | |
| Thu., 5/30 | V Boys Tennis | State Tournament | Away - Wesleyan University | 2:30 p.m. | ||
| Thu., 5/30 | V Girls Golf | FCIAC Championships | Away - Fairchild Wheeler | 8:30 a.m. | ||
| Thu., 5/30 | V Girls Outdoor Track | State Championships | Away - Willowbrook Park | 12:00 p.m. | 9:00 EARLY DISMISSAL | |
| Fri., 5/31 | V Boys Tennis | State Tournament | Away - Wesleyan University | 3:30 p.m. | ||
| Sat., 6/1 | V Boys Sailing | Regatta | Away - The Waterfront Center | 9:00 a.m. | ||
| Sat., 6/1 | V Girls Sailing | Regatta | Away - The Waterfront Center | 9:00 a.m. | ||
| Sat., 6/1 | School Holidays and Closings | Senior Prom | ||||
| Mon., 6/3 | V Boys Golf | State Championship | Away - Timberlin Golf Course | 8:00 a.m. | ||
| Mon., 6/3 | V Boys Outdoor Track | State Open Championships | Away - Willowbrook Park | 1:30 p.m. | ||
| Mon., 6/3 | V Girls Outdoor Track | State Open Championships | Away - Willowbrook Park | 1:30 p.m. | ||
| Tue., 6/4 | V Girls Golf | State Championship | Away - Tashua Knoll Golf Course | 8:30 a.m. | ||
| Sun., 6/16 | School Holidays and Closings | Fathers Day | ||||