| Greenwich 2023-24 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 944 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Wed., 8/23 | V Boys Golf | Norwalk | Away - Oak Hills Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 8/23 | V Boys Golf | Brien McMahon | Away - Oak Hills Golf Course [Directions] | 3:00 p.m. | ||
| Sun., 8/27 | V Football | Iona Prep (NY) (Scrim.) | Home - Greenwich HS-Cardinal Stadium [Directions] | 1:00 p.m. | ||
| Sun., 8/27 | JV Football | Iona Prep (NY) (Scrim.) | Home - Greenwich HS-Cardinal Stadium [Directions] | 11:00 a.m. | ||
| Mon., 8/28 | V Girls Soccer | Sacred Heart of Greenwich (Scrim.) | Home - Greenwich HS-Cardinal Stadium [Directions] | 9:00 a.m. | ||
| Mon., 8/28 | JV Girls Soccer | Sacred Heart of Greenwich (Scrim.) | Home - Greenwich HS-Field 7 [Directions] | 9:00 a.m. | ||
| Tue., 8/29 | V Boys Golf | Westhill | Home - Griffith E Harris Golf Course [Directions] | 3:30 p.m. | ||
| Tue., 8/29 | V Boys Soccer | Brunswick School (Scrim.) | Home - Greenwich HS-Cardinal Stadium [Directions] | 4:30 p.m. | ||
| Tue., 8/29 | JV Boys Soccer | Brunswick School (Scrim.) | Home - Greenwich HS-Cardinal Stadium [Directions] | Canceled | Cancelled | |
| Wed., 8/30 | V Field Hockey | Rye (NY) (Scrim.) | Away - Rye HS-Field | 4:00 p.m. | ||
| Wed., 8/30 | JV Field Hockey | Rye (NY) (Scrim.) | Away - Rye HS-Field | 5:30 p.m. | ||
| Wed., 8/30 | V Girls Soccer | Greenwich Academy (Scrim.) | Away - Greenwich Academy-Tammaro Field | 2:00 p.m. | ||
| Wed., 8/30 | JV Girls Soccer | Greenwich Academy (Scrim.) | Away - Greenwich Academy-2nd Field | 2:00 p.m. | ||
| Fri., 9/1 | V Football | New Canaan (Scrim.) | Away - New Canaan HS-Dunning Stadium [Directions] | 6:00 p.m. | ||
| Fri., 9/1 | FR Football | New Canaan (Scrim.) | Away - New Canaan HS-WTT #1 [Directions] | 4:00 p.m. | ||
| Sat., 9/2 | V Boys Soccer | Notre Dame-West Haven (Scrim.) | Away - Notre Dame HS-Side Turf [Directions] | 10:00 a.m. | ||
| Sat., 9/2 | JV Boys Soccer | Notre Dame-West Haven (Scrim.) | Away - Notre Dame HS-Side Turf [Directions] | 12:00 p.m. | ||
| Sat., 9/2 | V Field Hockey | Glastonbury (Scrim.) | Away - Glastonbury HS-Turf Field [Directions] | 9:00 a.m. | ||
| Sat., 9/2 | V Girls Soccer | Bethel (Scrim.) | Home - Greenwich HS-Cardinal Stadium [Directions] | 9:30 a.m. | ||
| Sat., 9/2 | JV Girls Soccer | Bethel (Scrim.) | Home - Greenwich HS-Field 3 [Directions] | 9:30 a.m. | ||
| Sat., 9/2 | V Girls Volleyball | Playday at The NAC Northeast Volleyball Preseason Scrimmage Jamboree | Away - Northeast Athletic Center | 9:00 a.m. | Playday at The NAC Northeast Volleyball Preseason Scrimmage Jamboree | |
| Wed., 9/6 | V Field Hockey | Greenwich Academy (Scrim.) | Away - Greenwich Academy-Turf field | 4:30 p.m. | ||
| Wed., 9/6 | JV Field Hockey | Greenwich Academy (Scrim.) | Away - Greenwich Academy-Turf field | 5:45 p.m. | ||
| Wed., 9/6 | V Girls Volleyball | Stamford (Scrim.) | Home - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | JV will scrimmage on a different court at the same time | |
| Thu., 9/7 | JV Boys Golf | Fairfield Prep | Home - Griffith E Harris Golf Course [Directions] | 3:30 p.m. | ||
| Thu., 9/7 | V Boys Soccer | Brien McMahon | Home - Greenwich HS-Cardinal Stadium [Directions] | 5:15 p.m. | W 2-1 | |
| Thu., 9/7 | JV Boys Soccer | Brien McMahon | Home - Greenwich HS-Field 3 [Directions] | 5:15 p.m. | ||
| Thu., 9/7 | FR Field Hockey | Danbury | Away - Danbury HS-Grass Field Hockey Field [Directions] | Postponed | ||
| Thu., 9/7 | V Girls Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 6:15 p.m. | W 2-0 | |
| Thu., 9/7 | JV Girls Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | Canceled | Cancelled | |
| Fri., 9/8 | JV Football | Fairfield Prep | Away - Fairfield University-Barlow Field [Directions] | 4:00 p.m. | ||
| Fri., 9/8 | FR Football | Fairfield Prep | Away - Fairfield University-Rafferty Stadium [Directions] | 6:00 p.m. | ||
| Fri., 9/8 | V Field Hockey | Danbury | Home - Greenwich HS-Cardinal Stadium [Directions] | 4:30 p.m. | W 9-0 | |
| Fri., 9/8 | JV Field Hockey | Danbury | Home - Greenwich HS-Field 3 [Directions] | Postponed | ||
| Sat., 9/9 | V Football | Fairfield Prep | Home - Greenwich HS-Cardinal Stadium [Directions] | 2:00 p.m. | W 35-21 | |
| Sat., 9/9 | FR Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 9:00 a.m. | ||
| Sat., 9/9 | V Boys Water Polo | Battle of the Beltways Naval Academy | Away - Not Listed | TBA | Battle of the Beltways Naval Academy | |
| Sat., 9/9 | JV Boys Water Polo | Battle of the Beltways Naval Academy | Away - Not Listed | TBA | Battle of the Beltways Naval Academy | |
| Sat., 9/9 | V Girls Volleyball | Lauralton Hall | Away - Lauralton Hall-Gym [Directions] | 11:30 a.m. | W 3-0 | |
| Sat., 9/9 | JV Girls Volleyball | Lauralton Hall | Away - Lauralton Hall-Gym [Directions] | 10:00 a.m. | W 2-0 | |
| Mon., 9/11 | V Field Hockey | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | L 0-2 | |
| Mon., 9/11 | JV Field Hockey | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Mon., 9/11 | FR Field Hockey | Darien | Home - Greenwich HS-Field 4 [Directions] | Postponed | ||
| Mon., 9/11 | FR Girls Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | 5:30 p.m. | ||
| Mon., 9/11 | V Girls Volleyball | Daniel Hand | Home - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | W 3-0 | |
| Mon., 9/11 | JV Girls Volleyball | Daniel Hand | Home - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | W 2-0 | |
| Tue., 9/12 | V Boys Cross Country | Ridgefield, Fairfield Ludlowe, Staples | Away - Ridgefield HS-Upper Grass Field [Directions] | 4:00 p.m. | ||
| Tue., 9/12 | JV Boys Golf | Fairfield Ludlowe | Home - Griffith E Harris Golf Course [Directions] | 3:10 p.m. | ||
| Tue., 9/12 | V Boys Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 7:00 p.m. | W 6-2 | |
| Tue., 9/12 | JV Boys Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | 4:00 p.m. | ||
| Tue., 9/12 | FR Boys Soccer | Fairfield Ludlowe | Home - Greenwich HS-Field 3 [Directions] | 5:00 p.m. | ||
| Tue., 9/12 | V Girls Cross Country | Ridgefield, Fairfield Ludlowe, Staples | Away - Ridgefield HS-Upper Grass Field [Directions] | 4:00 p.m. | ||
| Tue., 9/12 | V Girls Volleyball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 9/12 | JV Girls Volleyball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 4:30 p.m. | W 2-1 | |
| Wed., 9/13 | V Boys Golf | Fairfield Warde | Away - Brooklawn Country Club [Directions] | 3:00 p.m. | ||
| Wed., 9/13 | JV Boys Golf | New Canaan | Home - Griffith E Harris Golf Course [Directions] | 3:30 p.m. | ||
| Wed., 9/13 | V Boys Water Polo | Staples | Away - Staples HS-Staples High School Pool [Directions] | Postponed | ||
| Wed., 9/13 | V Girls Soccer | St. Joseph | Home - Greenwich HS-Cardinal Stadium [Directions] | 4:30 p.m. | L 0-7 | |
| Wed., 9/13 | JV Girls Soccer | St. Joseph | Home - Greenwich HS-Field 3 [Directions] | 5:00 p.m. | ||
| Thu., 9/14 | V Football | Stamford | Home - Greenwich HS-Cardinal Stadium [Directions] | 6:00 p.m. | W 28-14 | GYFL Night |
| Thu., 9/14 | FR Football | Ridgefield | Away - Ridgefield HS-Tiger Hollow Turf Field II [Directions] | 4:00 p.m. | ||
| Thu., 9/14 | V Boys Soccer | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 4:00 p.m. | W 3-0 | |
| Thu., 9/14 | V Field Hockey | Norwalk | Home - Greenwich HS-Field 3 [Directions] | 4:00 p.m. | W 6-1 | |
| Thu., 9/14 | JV Field Hockey | Norwalk | Home - Greenwich HS-Field 3 [Directions] | 5:15 p.m. | ||
| Thu., 9/14 | FR Field Hockey | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | 6:30 p.m. | ||
| Thu., 9/14 | V Girls Volleyball | New Canaan | Home - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | W 3-0 | |
| Thu., 9/14 | JV Girls Volleyball | New Canaan | Home - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | W 2-0 | |
| Mon., 9/18 | JV Football | Fairfield Ludlowe | Home - Greenwich HS-Field 7 [Directions] | 5:00 p.m. | Sophomore | |
| Mon., 9/18 | V Boys Golf | Ridgefield | Away - Ridgefield Golf Course [Directions] | Postponed | ||
| Mon., 9/18 | JV Field Hockey | Greenwich Academy | Away - Greenwich Academy-Turf field | 4:30 p.m. | ||
| Mon., 9/18 | JV Girls Soccer | Wilton | Away - Wilton HS-Lilly Field [Directions] | 4:15 p.m. | ||
| Mon., 9/18 | FR Girls Soccer | Wilton | Home - Greenwich HS-Field 3 [Directions] | 4:45 p.m. | ||
| Tue., 9/19 | V Boys Cross Country | Westhill, Brien McMahon, Darien | Away - Scofield Magnet MS-Cross Country Course [Directions] | 4:00 p.m. | ||
| Tue., 9/19 | V Boys Golf | Stamford | Home - Griffith E Harris Golf Course [Directions] | 3:30 p.m. | ||
| Tue., 9/19 | V Boys Soccer | Wilton | Home - Greenwich HS-Cardinal Stadium [Directions] | 4:30 p.m. | W 3-0 | |
| Tue., 9/19 | JV Boys Soccer | Wilton | Home - Greenwich HS-Field 3 [Directions] | 5:00 p.m. | ||
| Tue., 9/19 | FR Boys Soccer | Wilton | Away - Allen's Meadow-Field 2 [Directions] | 4:30 p.m. | ||
| Tue., 9/19 | V Girls Cross Country | Westhill, Brien McMahon, Darien | Away - Scofield Magnet MS-Cross Country Course [Directions] | 4:00 p.m. | ||
| Tue., 9/19 | FR Field Hockey | Wilton | Home - Cos Cob Park, Benvenuto Field-Benvenuto Field [Directions] | 4:45 p.m. | ||
| Tue., 9/19 | V Girls Soccer | Wilton | Away - Wilton HS-Lilly Field [Directions] | 6:00 p.m. | T 0-0 | |
| Tue., 9/19 | V Girls Volleyball | St. Joseph | Home - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | W 3-0 | |
| Tue., 9/19 | JV Girls Volleyball | St. Joseph | Home - Greenwich HS-Gymnasium [Directions] | 5:45 p.m. | W 2-0 | |
| Tue., 9/19 | FR Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:30 p.m. | ||
| Wed., 9/20 | V Boys Golf | Darien | Away - Wee Burn CC [Directions] | 3:15 p.m. | ||
| Wed., 9/20 | JV Boys Golf | Darien | Home - Greenwich Country Club [Directions] | 3:30 p.m. | ||
| Wed., 9/20 | V Field Hockey | Wilton | Away - Wilton HS-Fuijitani Field -Turf [Directions] | 6:45 p.m. | W 4-1 | |
| Wed., 9/20 | JV Field Hockey | Wilton | Away - Wilton HS-Fuijitani Field -Turf [Directions] | 5:30 p.m. | ||
| Wed., 9/20 | V Girls Soccer | Bridgeport Central | Away - Bridgeport Central-Kennedy Stadium Turf [Directions] | 4:00 p.m. | W 10-0 | |
| Wed., 9/20 | JV Girls Soccer | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | Canceled | Cancelled | |
| Wed., 9/20 | V Girls Swimming and Diving | Norwalk/McMahon | Home - Greenwich HS-Pool [Directions] | 4:00 p.m. | Win: 102-76 (1-0) | |
| Thu., 9/21 | FR Football | Maloney | Away - Falcon Field (Meriden, CT)-Football Field [Directions] | 5:00 p.m. | ||
| Thu., 9/21 | V Boys Golf | Ridgefield, Wilton | Away - Silver Spring Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 9/21 | V Boys Soccer | Bridgeport Central | Home - Greenwich HS-Cardinal Stadium [Directions] | 5:00 p.m. | W 6-1 | |
| Thu., 9/21 | JV Boys Soccer | Bridgeport Central | Home - Greenwich HS-Field 3 [Directions] | 5:00 p.m. | ||
| Fri., 9/22 | V Football | Maloney | Away - Falcon Field (Meriden, CT)-Football Field [Directions] | 6:30 p.m. | W 30-28 | |
| Fri., 9/22 | V Boys Water Polo | Beast of the East | Away - Not Listed | TBA | Beast of the East | |
| Fri., 9/22 | V Girls Soccer | New Canaan | Home - Greenwich HS-Cardinal Stadium [Directions] | 4:30 p.m. | W 2-1 | |
| Fri., 9/22 | JV Girls Soccer | New Canaan | Home - Greenwich HS-Field 3 [Directions] | 4:45 p.m. | ||
| Fri., 9/22 | FR Girls Soccer | New Canaan | Away - Saxe MS-Field 1 [Directions] | 4:00 p.m. | ||
| Fri., 9/22 | V Girls Volleyball | Brien McMahon | Home - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | W 3-0 | |
| Fri., 9/22 | JV Girls Volleyball | Brien McMahon | Home - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | W 2-0 | |
| Sat., 9/23 | JV Football | Norwalk | Home - Greenwich HS-Field 7 [Directions] | Postponed | ||
| Sat., 9/23 | JV Football | Maloney | Home - Greenwich HS-Field 7 [Directions] | 1:00 p.m. | ||
| Sat., 9/23 | V Boys Soccer | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 10:00 a.m. | W 7-1 | |
| Sat., 9/23 | JV Boys Soccer | New Canaan | Home - Greenwich HS-Field 3 [Directions] | 10:00 a.m. | ||
| Sat., 9/23 | FR Boys Soccer | New Canaan | Home - Greenwich HS-Field 7 [Directions] | 10:00 a.m. | ||
| Sat., 9/23 | V Boys Water Polo | Beast of the East | Away - Not Listed | TBA | Beast of the East | |
| Sat., 9/23 | FR Field Hockey | New Canaan | Home - Greenwich HS-Field 4 [Directions] | 10:00 a.m. | ||
| Sat., 9/23 | V Girls Swimming and Diving | Amity, Glastonbury | Away - High Plains Community Cn [Directions] | 3:45 p.m. | Win vs. Glastonbury: 114-67 Win vs. Amity: 111-70 (3-0) | |
| Sat., 9/23 | FR Girls Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 9:30 a.m. | ||
| Tue., 9/26 | V Boys Cross Country | Bridgeport Central, Fairfield Warde, Wilton | Home - Greenwich Point [Directions] | 4:00 p.m. | ||
| Tue., 9/26 | V Boys Golf | Trumbull | Home - Griffith E Harris Golf Course [Directions] | 3:30 p.m. | ||
| Tue., 9/26 | JV Boys Golf | Fairfield Prep | Away - Fairchild Wheeler Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 9/26 | V Boys Water Polo | Staples | Home - Greenwich HS-Pool [Directions] | 4:00 p.m. | ||
| Tue., 9/26 | JV Boys Water Polo | Staples | Home - Greenwich HS-Pool [Directions] | 5:00 p.m. | ||
| Tue., 9/26 | V Girls Cross Country | Fairfield Warde, Wilton | Home - Greenwich Point [Directions] | 4:00 p.m. | ||
| Wed., 9/27 | V Boys Golf | Fairfield Prep | Away - Brooklawn Country Club [Directions] | 3:00 p.m. | ||
| Wed., 9/27 | V Field Hockey | Ridgefield | Home - Greenwich HS-Cardinal Stadium [Directions] | 6:00 p.m. | OT-L 1-2 | |
| Wed., 9/27 | JV Field Hockey | Ridgefield | Home - Greenwich HS-Field 3 [Directions] | 5:45 p.m. | ||
| Wed., 9/27 | FR Field Hockey | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 6:15 p.m. | ||
| Wed., 9/27 | V Girls Soccer | Staples | Home - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | T 2-2 | |
| Wed., 9/27 | JV Girls Soccer | Staples | Home - Greenwich HS-Field 3 [Directions] | 4:00 p.m. | ||
| Wed., 9/27 | FR Girls Soccer | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Wed., 9/27 | V Girls Swimming and Diving | Ridgefield | Home - Greenwich HS-Pool [Directions] | 4:00 p.m. | Win: 97-87 (4-0) | |
| Wed., 9/27 | V Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 9/27 | JV Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:30 p.m. | W 2-0 | |
| Wed., 9/27 | FR Girls Volleyball | Fairfield Ludlowe | Home - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 9/28 | FR Football | Wilton | Away - Wilton HS-Fuijitani Field -Turf [Directions] | 4:30 p.m. | ||
| Thu., 9/28 | V Boys Golf | Fairfield Ludlowe | Home - Griffith E Harris Golf Course [Directions] | 3:30 p.m. | ||
| Thu., 9/28 | V Boys Soccer | Staples | Away - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | L 0-2 | |
| Thu., 9/28 | JV Boys Soccer | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Thu., 9/28 | FR Boys Soccer | Staples | Home - Cos Cob Park, Benvenuto Field-Benvenuto Field [Directions] | 5:00 p.m. | ||
| Fri., 9/29 | V Girls Swimming and Diving | Westhill/Stamford | Home - Greenwich HS-Pool [Directions] | 4:00 p.m. | Win: 100-70 (5-0) | |
| Sat., 9/30 | JV Football | Danbury | Home - Greenwich HS-Field 7 [Directions] | Postponed | ||
| Sat., 9/30 | JV Football | Brien McMahon | Home - Greenwich HS-Field 7 [Directions] | 12:30 p.m. | Sophomore Game | |
| Sat., 9/30 | V Boys Soccer | Trumbull | Home - Greenwich HS-Cardinal Stadium [Directions] | 2:15 p.m. | W 3-2 | |
| Sat., 9/30 | JV Boys Soccer | Trumbull | Home - Greenwich HS-Field 3 [Directions] | 12:30 p.m. | ||
| Sat., 9/30 | FR Boys Soccer | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 11:30 a.m. | ||
| Sat., 9/30 | V Field Hockey | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 1:00 p.m. | L 1-2 | |
| Sat., 9/30 | JV Field Hockey | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 2:30 p.m. | ||
| Sat., 9/30 | V Girls Soccer | Trumbull | Away - Trumbull HS-Cork Field [Directions] | 11:30 a.m. | T 0-0 | |
| Sat., 9/30 | JV Girls Soccer | Trumbull | Away - Trumbull HS-Cork Field [Directions] | 1:30 p.m. | ||
| Mon., 10/2 | V Football | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 6:00 p.m. | W 36-0 | |
| Mon., 10/2 | V Boys Golf | New Canaan | Away - CCNC [Directions] | 3:30 p.m. | ||
| Mon., 10/2 | JV Boys Golf | New Canaan | Away - CCNC [Directions] | 3:30 p.m. | ||
| Tue., 10/3 | V Boys Cross Country | New Canaan, St. Joseph, Stamford | Away - Waveny Park [Directions] | 4:00 p.m. | ||
| Tue., 10/3 | V Boys Golf | Staples | Home - Round Hill Country Club [Directions] | 3:00 p.m. | ||
| Tue., 10/3 | JV Boys Golf | Darien | Away - Country Club of Darien [Directions] | 3:00 p.m. | ||
| Tue., 10/3 | V Girls Cross Country | New Canaan, St. Joseph, Stamford | Away - Waveny Park [Directions] | 4:00 p.m. | ||
| Tue., 10/3 | V Field Hockey | St. Joseph | Home - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | W 9-1 | |
| Tue., 10/3 | JV Field Hockey | St. Joseph | Home - Greenwich HS-Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Tue., 10/3 | V Girls Soccer | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 5:00 p.m. | W 2-0 | |
| Tue., 10/3 | JV Girls Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 5:00 p.m. | ||
| Tue., 10/3 | FR Girls Soccer | Danbury | Home - Greenwich HS-Field 3 [Directions] | 4:15 p.m. | ||
| Tue., 10/3 | V Girls Swimming and Diving | Danbury | Away - WCSU O'Neill Center Pool [Directions] | 3:45 p.m. | Win: 74-56 (6-0) | |
| Tue., 10/3 | V Girls Volleyball | Wilton | Home - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | W 3-0 | |
| Tue., 10/3 | JV Girls Volleyball | Wilton | Home - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | W 2-0 | |
| Tue., 10/3 | FR Girls Volleyball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Wed., 10/4 | V Boys Soccer | Danbury | Home - Greenwich HS-Cardinal Stadium [Directions] | 5:00 p.m. | W 2-1 | |
| Wed., 10/4 | JV Boys Soccer | Danbury | Home - Greenwich HS-Field 3 [Directions] | 4:45 p.m. | ||
| Wed., 10/4 | FR Boys Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 4:30 p.m. | ||
| Wed., 10/4 | V Field Hockey | Mamaroneck (NY) | Away - Mamaroneck HS-Field | 5:00 p.m. | L 1-3 | |
| Wed., 10/4 | JV Field Hockey | Mamaroneck (NY) | Away - Mamaroneck HS-Field | 6:30 p.m. | ||
| Wed., 10/4 | FR Girls Soccer | Trumbull | Home - Eastern MS [Directions] | 4:30 p.m. | ||
| Wed., 10/4 | V Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:30 p.m. | L 0-3 | |
| Wed., 10/4 | JV Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 6:00 p.m. | W 2-0 | |
| Wed., 10/4 | FR Girls Volleyball | St. Joseph | Home - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 10/5 | V Boys Golf | Chappa | Away - . | TBA | Chappa at Longshore | |
| Thu., 10/5 | FR Girls Soccer | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 10/5 | V Girls Swimming and Diving | Trumbull | Away - University of Bridgeport-Pool [Directions] | 4:00 p.m. | Win: 95-70 (7-0) | |
| Thu., 10/5 | V Girls Volleyball | Bridgeport Central | Home - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | W 3-0 | |
| Thu., 10/5 | JV Girls Volleyball | Bridgeport Central | Home - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | W 2-0 | |
| Fri., 10/6 | V Boys Soccer | Darien | Away - Darien HS-DHS Center Oval - Turf [Directions] | 4:30 p.m. | L 0-1 | |
| Fri., 10/6 | JV Boys Soccer | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 10/6 | FR Boys Soccer | Darien | Home - Greenwich HS-Field 3 [Directions] | 4:00 p.m. | ||
| Fri., 10/6 | V Girls Soccer | Darien | Home - Greenwich HS-Cardinal Stadium [Directions] | 6:30 p.m. | W 5-2 | |
| Fri., 10/6 | JV Girls Soccer | Darien | Home - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Sat., 10/7 | V Field Hockey | Hall | Away - Hall HS-Stadium (Turf Field) [Directions] | 4:30 p.m. | W 6-0 | |
| Sat., 10/7 | V Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 2:30 p.m. | W 3-0 | |
| Sat., 10/7 | JV Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 1:00 p.m. | W 2-0 | |
| Sat., 10/7 | FR Girls Volleyball | New Canaan | Home - Greenwich HS-Gymnasium [Directions] | 10:00 a.m. | ||
| Mon., 10/9 | V Boys Golf | St. Joseph | Home - Griffith E Harris Golf Course [Directions] | 3:30 p.m. | ||
| Mon., 10/9 | V Field Hockey | Brien McMahon | Home - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | W 6-0 | |
| Mon., 10/9 | JV Field Hockey | Brien McMahon | Home - Greenwich HS-Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Mon., 10/9 | V Girls Soccer | Stamford | Home - Greenwich HS-Field 3 [Directions] | 4:30 p.m. | W 1-0 | |
| Mon., 10/9 | JV Girls Soccer | Stamford | Home - Greenwich HS-Cos Cob Park, Benvenuto Field [Directions] | 4:30 p.m. | ||
| Mon., 10/9 | V Girls Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Mon., 10/9 | JV Girls Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:00 p.m. | W 2-0 | |
| Mon., 10/9 | FR Girls Volleyball | Staples | Home - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 10/10 | V Boys Cross Country | Danbury, Norwalk, Trumbull | Home - Greenwich Point [Directions] | 4:00 p.m. | Senior Night | |
| Tue., 10/10 | V Boys Golf | Wilton | Away - Rolling Hills Country Club [Directions] | 3:30 p.m. | ||
| Tue., 10/10 | JV Boys Golf | Wilton | Away - Rolling Hills Country Club [Directions] | 3:30 p.m. | ||
| Tue., 10/10 | V Boys Soccer | Stamford | Home - Greenwich HS-Cardinal Stadium [Directions] | 4:30 p.m. | T 0-0 | |
| Tue., 10/10 | JV Boys Soccer | Stamford | Away - Trinity Catholic-Alumni Field [Directions] | 4:30 p.m. | ||
| Tue., 10/10 | FR Boys Soccer | Stamford | Home - Greenwich HS-Cos Cob Park, Benvenuto Field [Directions] | 4:30 p.m. | ||
| Tue., 10/10 | V Girls Cross Country | Danbury, Norwalk, Trumbull | Home - Greenwich Point [Directions] | 4:00 p.m. | Senior Night | |
| Tue., 10/10 | V Girls Diving | Darien | Away - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Wed., 10/11 | V Boys Golf | Danbury | Home - Griffith E Harris Golf Course [Directions] | 3:30 p.m. | ||
| Wed., 10/11 | V Girls Swimming and Diving | Darien | Away - Darien YMCA [Directions] | 3:00 p.m. | Win: 97-81 (8-0) | |
| Wed., 10/11 | V Girls Volleyball | Trumbull | Home - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | L 1-3 | |
| Wed., 10/11 | JV Girls Volleyball | Trumbull | Home - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | W 2-0 | |
| Wed., 10/11 | FR Girls Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/12 | FR Football | St. Joseph | Home - Greenwich HS-Field 7 [Directions] | 4:00 p.m. | ||
| Thu., 10/12 | JV Boys Golf | Darien | Away - Woodway Country Club [Directions] | 3:10 p.m. | ||
| Thu., 10/12 | V Field Hockey | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 7:00 p.m. | W 9-0 | |
| Thu., 10/12 | JV Field Hockey | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 5:30 p.m. | ||
| Thu., 10/12 | FR Field Hockey | Trumbull | Home - Cos Cob Park, Benvenuto Field-Benvenuto Field [Directions] | Canceled | Cancelled | |
| Thu., 10/12 | V Girls Soccer | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 6:00 p.m. | T 0-0 | |
| Thu., 10/12 | JV Girls Soccer | Ridgefield | Away - Ridgefield HS-RHS Lower Grass Field [Directions] | 4:30 p.m. | ||
| Thu., 10/12 | FR Girls Soccer | Ridgefield | Home - Greenwich HS-Field 3 [Directions] | Postponed | ||
| Fri., 10/13 | V Boys Soccer | Ridgefield | Home - Greenwich HS-Cardinal Stadium [Directions] | 4:30 p.m. | W 3-0 | |
| Fri., 10/13 | JV Boys Soccer | Ridgefield | Home - Greenwich HS-Field 3 [Directions] | 4:30 p.m. | ||
| Fri., 10/13 | FR Boys Soccer | Ridgefield | Away - Ridgefield HS-RHS Lower Grass Field [Directions] | 4:00 p.m. | ||
| Fri., 10/13 | V Girls Volleyball | Danbury | Home - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | W 3-0 | |
| Fri., 10/13 | JV Girls Volleyball | Danbury | Home - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | W 2-0 | |
| Fri., 10/13 | FR Girls Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/14 | V Football | Darien | Home - Greenwich HS-Cardinal Stadium [Directions] | 2:00 p.m. | W 30-14 | Homecoming |
| Sat., 10/14 | V Competitive Cheerleading | Darien | Home - Greenwich HS [Directions] | 2:00 p.m. | ||
| Sat., 10/14 | JV Field Hockey | Staples | Away - Staples HS-Ginny Parker Field [Directions] | Postponed | ||
| Sat., 10/14 | FR Field Hockey | Staples | Home - Greenwich HS-Field 3 [Directions] | 10:00 a.m. | ||
| Mon., 10/16 | JV Football | Darien | Away - Darien HS-DHS Stadium East [Directions] | 4:00 p.m. | ||
| Mon., 10/16 | V Boys Soccer | Norwalk | Home - Greenwich HS-Cardinal Stadium [Directions] | 6:30 p.m. | W 3-1 | Senior Night |
| Mon., 10/16 | JV Boys Soccer | Norwalk | Home - Greenwich HS-Field 3 [Directions] | 4:30 p.m. | ||
| Mon., 10/16 | JV Field Hockey | Darien | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Mon., 10/16 | FR Field Hockey | Darien | Home - Greenwich HS-Cos Cob Park, Benvenuto Field [Directions] | 4:30 p.m. | ||
| Mon., 10/16 | V Girls Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 6:00 p.m. | W 5-1 | |
| Mon., 10/16 | JV Girls Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | Canceled | Cancelled | |
| Mon., 10/16 | V Girls Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | L 2-3 | |
| Mon., 10/16 | JV Girls Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | W 2-1 | |
| Mon., 10/16 | FR Girls Volleyball | Darien | Home - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 10/17 | V Boys Golf | Holahan | Away - . | 12:30 p.m. | Holahan at Woodway CC | |
| Tue., 10/17 | FR Boys Soccer | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 4:30 p.m. | ||
| Tue., 10/17 | V Field Hockey | Stamford | Home - Greenwich HS-Cardinal Stadium [Directions] | 6:00 p.m. | W 1-0 | |
| Tue., 10/17 | JV Field Hockey | Stamford | Home - Greenwich HS-Field 3 [Directions] | 4:00 p.m. | ||
| Wed., 10/18 | V Boys Cross Country | FCIAC Championship | Away - Waveny Park | 2:15 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Not Listed-Waveny Park | ||||||
| Wed., 10/18 | V Girls Cross Country | FCIAC Championship | Away - Waveny Park | 2:15 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Not Listed-Waveny Park | ||||||
| Wed., 10/18 | V Girls Soccer | Westhill | Home - Greenwich HS-Cardinal Stadium [Directions] | 4:30 p.m. | W 3-1 | |
| Wed., 10/18 | JV Girls Soccer | Westhill | Home - Greenwich HS-Field 3 [Directions] | 4:45 p.m. | ||
| Wed., 10/18 | V Girls Swimming and Diving | Staples | Away - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | Win: 87-85 (9-0) | |
| Wed., 10/18 | V Girls Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 10/18 | JV Girls Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | W 2-0 | |
| Wed., 10/18 | FR Girls Volleyball | Stamford | Home - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 10/19 | FR Football | New Canaan | Home - Greenwich HS-Field 7 [Directions] | 4:30 p.m. | ||
| Thu., 10/19 | V Boys Golf | FCIAC | Away - TBA | 10:00 a.m. | FCIAC at Tashua Knolls | |
| Thu., 10/19 | V Boys Soccer | Westhill | Away - Westhill HS-Front Turf [Directions] | 4:00 p.m. | W 2-1 | |
| Thu., 10/19 | JV Boys Soccer | Westhill | Home - Greenwich HS-Field 3 [Directions] | 4:45 p.m. | ||
| Thu., 10/19 | FR Boys Soccer | Westhill | Home - Greenwich HS-Cos Cob Park, Benvenuto Field [Directions] | 4:45 p.m. | ||
| Thu., 10/19 | V Field Hockey | Fairfield Ludlowe | Home - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | W 3-1 | |
| Thu., 10/19 | JV Field Hockey | Fairfield Ludlowe | Home - Greenwich HS-Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Fri., 10/20 | V Football | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 7:00 p.m. | W 42-0 | |
| Fri., 10/20 | V Field Hockey | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 3:45 p.m. | OT-L 1-2 | |
| Fri., 10/20 | FR Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Front Field [Directions] | 4:00 p.m. | ||
| Pending changes awaiting acceptance by one or more parties involved: Date to 10/24, Time to 4:30 p.m. | ||||||
| Fri., 10/20 | V Girls Soccer | Fairfield Ludlowe | Home - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | W 4-2 | |
| Fri., 10/20 | V Girls Volleyball | Ridgefield | Home - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | W 3-0 | |
| Fri., 10/20 | JV Girls Volleyball | Ridgefield | Home - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | W 2-0 | |
| Fri., 10/20 | FR Girls Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/21 | JV Football | Trumbull | Home - Greenwich HS-Field 7 [Directions] | 10:00 a.m. | ||
| Mon., 10/23 | V Field Hockey | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | W 4-0 | |
| Mon., 10/23 | JV Field Hockey | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | ||
| Mon., 10/23 | FR Field Hockey | Westhill | Home - Greenwich HS-Field 4 [Directions] | 4:00 p.m. | ||
| Mon., 10/23 | V Girls Soccer | Fairfield Warde | Home - Greenwich HS-Cardinal Stadium [Directions] | 4:30 p.m. | W 2-0 | |
| Mon., 10/23 | JV Girls Soccer | Fairfield Warde | Home - Greenwich HS-Field 3 [Directions] | 4:30 p.m. | ||
| Mon., 10/23 | FR Girls Soccer | Fairfield Warde | Away - Tunxis [Directions] | 4:00 p.m. | ||
| Mon., 10/23 | V Girls Volleyball | Norwalk | Home - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | W 3-0 | |
| Mon., 10/23 | JV Girls Volleyball | Norwalk | Home - Greenwich HS-Gymnasium [Directions] | 4:15 p.m. | W 2-0 | |
| Mon., 10/23 | FR Girls Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:30 p.m. | ||
| Tue., 10/24 | V Boys Golf | CIAC Division I Fall Championship | Away - Stanley GC | 8:30 a.m. | ||
| Tue., 10/24 | V Boys Soccer | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 7:00 p.m. | T 0-0 | |
| Tue., 10/24 | JV Boys Soccer | Fairfield Warde | Away - Fairfield Warde HS-Grass Utility Field [Directions] | 4:00 p.m. | ||
| Tue., 10/24 | FR Boys Soccer | Fairfield Warde | Home - Greenwich HS-Field 3 [Directions] | 4:15 p.m. | ||
| Tue., 10/24 | V Field Hockey | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | W 6-0 | |
| Tue., 10/24 | JV Field Hockey | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 5:15 p.m. | ||
| Tue., 10/24 | FR Field Hockey | Fairfield Warde | Home - Greenwich HS-Field 4 [Directions] | Canceled | Cancelled | |
| Wed., 10/25 | JV Girls Soccer | Fairfield Ludlowe | Home - Greenwich HS-Field 3 [Directions] | 4:00 p.m. | ||
| Wed., 10/25 | V Girls Swimming and Diving | New Canaan | Home - Greenwich HS-Pool [Directions] | 4:00 p.m. | Win: 95-75 (10-0) | |
| Wed., 10/25 | V Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:30 p.m. | L 0-3 | |
| Wed., 10/25 | JV Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 3:00 p.m. | W 2-1 | |
| Wed., 10/25 | FR Girls Volleyball | Westhill | Home - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 10/26 | FR Football | Darien | Away - Darien HS-DHS Stadium East [Directions] | 4:00 p.m. | ||
| Thu., 10/26 | JV Field Hockey | Greenwich Academy | Home - Greenwich HS-Cardinal Stadium [Directions] | 5:00 p.m. | ||
| Thu., 10/26 | V Girls Soccer | Darien | Home - Greenwich HS-Cardinal Stadium [Directions] | 3:30 p.m. | L 0-2 | |
| Fri., 10/27 | V Boys Soccer | Danbury | Home - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | W 2-1 | FCIAC 1/4 Finals |
| Fri., 10/27 | V Field Hockey | Wilton | Home - Greenwich HS-Cardinal Stadium [Directions] | 2:00 p.m. | W 7-0 | FCIAC 1/4 Finals |
| Fri., 10/27 | V Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 6:00 p.m. | W 3-1 | |
| Fri., 10/27 | JV Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:30 p.m. | ||
| Fri., 10/27 | FR Girls Volleyball | Fairfield Warde | Home - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 10/28 | V Football | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 1:30 p.m. | W 23-9 | |
| Sat., 10/28 | V Girls Swimming and Diving | Danbury, Darien, Fairfield Ludlowe, New Canaan, Norwalk/McMahon, Ridgefield, St. Joseph, Staples, Trumbull, Westhill/Stamford, Wilton | Home - Greenwich HS-Pool [Directions] | 9:30 a.m. | JV Tournament | |
| Sat., 10/28 | JV Girls Volleyball | Fairfield Warde, Brien McMahon, Darien, Fairfield Ludlowe, Greenwich Country Day, Shelton, Stamford, Trumbull, Weston | Away - Fairfield Warde HS-Large Gym | 9:00 a.m. | ||
| Mon., 10/30 | JV Football | St. Joseph | Home - Greenwich HS-Field 7 [Directions] | 4:00 p.m. | ||
| Mon., 10/30 | V Boys Soccer | Trumbull | Home - Fairfield Ludlowe HS-Taft Field [Directions] | 7:00 p.m. | L 4-5 | FCIAC Semi-Finals |
| Mon., 10/30 | V Field Hockey | Darien | Away - Brien McMahon HS-Casagrande Field [Directions] | 5:00 p.m. | Cancelled | FCIAC Semi-Finals |
| Mon., 10/30 | V Girls Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 5:00 p.m. | L 1-3 | FCIAC 1/4 Finals |
| Tue., 10/31 | V Boys Cross Country | CIAC Class LL Championship | Away - Wickham Park | 3:15 p.m. | ||
| Tue., 10/31 | V Girls Cross Country | CIAC Class LL Championship | Away - Wickham Park | 2:30 p.m. | ||
| Wed., 11/1 | V Field Hockey | Darien | Away - Brien McMahon HS-Casagrande Field [Directions] | 5:00 p.m. | L 2-3 | |
| Wed., 11/1 | V Girls Swimming and Diving | Danbury, Darien, Fairfield Ludlowe, Fairfield Warde, New Canaan, Norwalk/McMahon, Ridgefield, St. Joseph, Staples, Trumbull, Westhill/Stamford, Wilton | Home - Greenwich HS-Pool [Directions] | 5:30 p.m. | FCIAC Trials | |
| Thu., 11/2 | FR Football | Trumbull | Home - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Thu., 11/2 | V Girls Swimming and Diving | FCIAC Diving Finals | Away - . | 5:00 p.m. | FCIAC Diving Finals | |
| Sat., 11/4 | V Football | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 1:00 p.m. | W 43-8 | |
| Sat., 11/4 | V Girls Swimming and Diving | Danbury, Darien, Fairfield Ludlowe, Fairfield Warde, New Canaan, Norwalk/McMahon, Ridgefield, St. Joseph, Staples, Trumbull, Westhill/Stamford, Wilton | Home - Greenwich HS-Pool [Directions] | 3:30 p.m. | FCIAC Champions | FCIAC Finals |
| Mon., 11/6 | V Boys Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Mon., 11/6 | JV Football | Westhill | Home - Greenwich HS-Field 7 [Directions] | 3:30 p.m. | ||
| Mon., 11/6 | V Girls Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Mon., 11/6 | V Girls Soccer | West Haven | Home - Greenwich HS-Cardinal Stadium [Directions] | 2:00 p.m. | W 5-0 | |
| Mon., 11/6 | V Girls Volleyball | Ridgefield | Home - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | W 3-0 | |
| Tue., 11/7 | V Boys Soccer | Bristol Central | Home - Greenwich HS-Cardinal Stadium [Directions] | 2:00 p.m. | W 7-1 | |
| Wed., 11/8 | SO Football | Darien | Home - Greenwich HS-Field 7 [Directions] | 3:30 p.m. | ||
| Wed., 11/8 | V Field Hockey | Newtown | Home - Greenwich HS-Cardinal Stadium [Directions] | 2:00 p.m. | W 3-0 | |
| Wed., 11/8 | V Girls Soccer | Southington | Home - Greenwich HS-Cardinal Stadium [Directions] | 4:15 p.m. | CIAC LL Second Round | |
| Thu., 11/9 | FR Football | Staples | Home - Greenwich HS-Field 7 [Directions] | 3:30 p.m. | ||
| Thu., 11/9 | V Boys Soccer | Shelton | Home - Greenwich HS-Cardinal Stadium [Directions] | 2:30 p.m. | W 2-1 | CIAC LL Second Round |
| Thu., 11/9 | V Girls Swimming and Diving | CIAC Class LL Diving Championship | Away - Sheehan | 5:30 p.m. | ||
| Thu., 11/9 | V Girls Volleyball | Newtown | Away - Newtown HS-Gym [Directions] | 5:00 p.m. | W 3-1 | |
| Fri., 11/10 | V Football | Ridgefield | Home - Greenwich HS-Cardinal Stadium [Directions] | 7:00 p.m. | W 35-0 | |
| Fri., 11/10 | V Field Hockey | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 2:00 p.m. | L 1-2 | |
| Fri., 11/10 | V Girls Soccer | Staples | Away - Staples HS-Wakeman Field B (turf) [Directions] | 2:00 p.m. | ||
| Sat., 11/11 | JV Football | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 10:30 a.m. | ||
| Sat., 11/11 | V Boys Soccer | Glastonbury | Home - Greenwich HS-Cardinal Stadium [Directions] | 2:00 p.m. | W 2-1 | CIAC LL 1/4 Finals |
| Sat., 11/11 | V Girls Swimming and Diving | CIAC Class LL Qualifying Meet | Away - Cornerstone Pool | 4:30 p.m. | ||
| Sat., 11/11 | V Girls Volleyball | Southington | Away - Southington HS-Gym West [Directions] | 6:00 p.m. | L 2-3 | |
| Tue., 11/14 | V Girls Swimming and Diving | CIAC Class LL Finals | Away - Wesleyan | 6:00 p.m. | Class LL Champions | |
| Wed., 11/15 | SO Football | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 4:30 p.m. | ||
| Wed., 11/15 | V Boys Soccer | Stamford | Home - Norwalk HS - Ray Barry Field-Stadium [Directions] | 6:00 p.m. | L 0-3 | CIAC LL Semi Finals |
| Thu., 11/16 | V Girls Swimming and Diving | CIAC State Open Diving | Away - Middletown | 5:30 p.m. | ||
| Sun., 11/19 | V Girls Swimming and Diving | CIAC State Open Swimming | Away - Yale | 1:00 p.m. | ||
| Mon., 11/20 | JV Football | Staples | Away - Staples HS-Staples Stadium [Directions] | 6:30 p.m. | ||
| Thu., 11/23 | V Football | Staples | Home - Greenwich HS-Cardinal Stadium [Directions] | 10:00 a.m. | L 13-24 | |
| Tue., 11/28 | V Football | CIAC Quarterfinals | Away - Higher Seed | 6:30 p.m. | ||
| Tue., 11/28 | V Football | Stamford | Home - Greenwich HS-Cardinal Stadium [Directions] | 6:30 p.m. | W 47-21 | |
| Tue., 11/28 | V Girls Ice Hockey | Stamford/Westhill/Staples (Scrim.) | Home - Greenwich - Dorothy Hamill-Rink [Directions] | 5:15 p.m. | ||
| Sat., 12/2 | V Girls Basketball | Derby (Scrim.) | Away - Derby HS-DHS Vitello Gym [Directions] | 11:00 a.m. | ||
| Sun., 12/3 | V Football | CIAC Semifinals | Away - Higher Seed | 12:30 p.m. | ||
| Sun., 12/3 | V Football | West Haven | Home - Greenwich HS-Cardinal Stadium [Directions] | 12:30 p.m. | L 13-26 | |
| Wed., 12/6 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 3:30 p.m. | T 3-3 | |
| Thu., 12/7 | V Boys Ice Hockey | North Haven (Scrim.) | Home - Greenwich - Dorothy Hamill-Rink [Directions] | 8:00 p.m. | ||
| Sat., 12/9 | V Football | CIAC Championship Games | Away - Site TBA | TBA | ||
| Sat., 12/9 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 2:00 p.m. | L 1-7 | |
| Mon., 12/11 | V Boys Basketball | Notre Dame-Fairfield (Scrim.) | Home - Greenwich HS-Gymnasium [Directions] | 7:00 p.m. | Scrimmage | |
| Mon., 12/11 | JV Boys Basketball | Notre Dame-Fairfield (Scrim.) | Home - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | Scrimmage | |
| Mon., 12/11 | V Boys Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | 6:00 p.m. | L 4-1 | |
| Tue., 12/12 | V Girls Basketball | Wright Tech | Away - J M Wright Tech School-Thomas R. Good Gymnasium [Directions] | 4:30 p.m. | W 49-19 | |
| Thu., 12/14 | V Boys Diving | Darien, Wilton | Away - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Thu., 12/14 | V Wrestling | Wilton | Away - Wilton HS-Nicholas Zeoli Fieldhouse [Directions] | 6:00 p.m. | Greenwich 48 Wilton 33 | |
| Thu., 12/14 | V Girls Ice Hockey | West Haven/SHA | Home - Greenwich - Dorothy Hamill-Rink [Directions] | 8:00 p.m. | L 2-5 | |
| Fri., 12/15 | V Boys Basketball | Fairfield Prep | Home - Greenwich HS-Gymnasium [Directions] | 7:00 p.m. | W 59-48 | |
| Fri., 12/15 | JV Boys Basketball | Fairfield Prep | Home - Greenwich HS-Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 12/15 | FR Boys Basketball | Fairfield Prep | Home - Greenwich HS-Gymnasium [Directions] | 3:45 p.m. | ||
| Fri., 12/15 | V Boys Swimming and Diving | Darien | Away - Darien YMCA [Directions] | 3:00 p.m. | ||
| Fri., 12/15 | V Co-ed Fencing | North Haven | Away - North Haven HS-Auxiliary Gymnasium [Directions] | 6:30 p.m. | ||
| Sat., 12/16 | JV Boys Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | 7:30 p.m. | ||
| Sat., 12/16 | V Boys Indoor Track | Staples, Stamford, Trumbull, Westhill | Away - Staples HS-Field House [Directions] | 1:00 p.m. | ||
| Sat., 12/16 | V Wrestling | Guilford Wrestling Invitational | Away - Guilford HS-Main gym at GHS | 9:00 a.m. | ||
| Sat., 12/16 | V Girls Basketball | Joel Barlow | Home - Greenwich HS-Gymnasium [Directions] | 12:00 p.m. | W 38-35 | |
| Sat., 12/16 | JV Girls Basketball | Joel Barlow | Home - Greenwich HS-Gymnasium [Directions] | 10:00 a.m. | ||
| Sat., 12/16 | V Girls Indoor Track | Staples, Stamford, Trumbull, Westhill | Away - Staples HS-Field House [Directions] | 1:00 p.m. | ||
| Sun., 12/17 | JV Girls Ice Hockey | Trumbull/St. Joseph, Fairfield Ludlowe/Warde, Ridgefield/Danbury/Immaculate, Wilton/Norwalk/McMahon (Scrim.) | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 2:00 p.m. | ||
| Tue., 12/19 | V Boys Swimming and Diving | Staples | Home - Greenwich HS-Pool [Directions] | 4:15 p.m. | ||
| Tue., 12/19 | V Bowling | Fairfield Warde | Away - Nutmeg Bowling Alley [Directions] | 3:00 p.m. | ||
| Wed., 12/20 | V Boys Ice Hockey | Xavier | Home - Greenwich - Dorothy Hamill-Rink [Directions] | 8:15 p.m. | L 2-0 | |
| Wed., 12/20 | V Wrestling | New Canaan | Home - Greenwich HS-Gymnasium [Directions] | 6:00 p.m. | New Canaan 43 Greenwich 24 | |
| Wed., 12/20 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Conners - Stamford-Ice Rink [Directions] | 7:30 p.m. | L 1-4 | |
| Thu., 12/21 | V Co-ed Fencing | GHS vs CGS | Away - . | 6:00 p.m. | GHS vs CGS | |
| Fri., 12/22 | V Girls Basketball | Westhill | Home - Greenwich HS-Gymnasium [Directions] | 7:00 p.m. | W 53-17 | |
| Fri., 12/22 | JV Girls Basketball | Westhill | Home - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 12/22 | FR Girls Basketball | Westhill | Home - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 12/22 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Greenwich - Dorothy Hamill-Rink [Directions] | 5:15 p.m. | L 2-9 | |
| Sat., 12/23 | V Boys Ice Hockey | North Haven | Away - Northford-Red [Directions] | 5:00 p.m. | L 2-1 | |
| Sat., 12/23 | JV Boys Ice Hockey | Notre Dame-West Haven | Home - Greenwich - Dorothy Hamill-Rink [Directions] | 4:30 p.m. | ||
| Sat., 12/23 | V Wrestling | Danbury, Fairfield Ludlowe, St. Joseph | Home - Greenwich HS-Gymnasium [Directions] | 12:00 p.m. | Fairfield Ludlowe 58 Greenwich 18 St Joe's 30 Greenwich 51 Danbury 71 Greenwich 6 | |
| Wed., 12/27 | V Boys Basketball | Bassick | Away - Bassick HS-Gym [Directions] | 7:00 p.m. | W 66-48 | |
| Wed., 12/27 | V Girls Basketball | New Britain | Home - Bethel HS-BHS gym [Directions] | 3:00 p.m. | W 43-41 | |
| Thu., 12/28 | V Boys Basketball | Bunnell | Away - Bassick HS-Gym [Directions] | 7:00 p.m. | L 62-66 | |
| Fri., 12/29 | V Boys Ice Hockey | Darien | Home - Greenwich Skating Club-Ice Rink [Directions] | 4:00 p.m. | L 5-3 | |
| Fri., 12/29 | JV Boys Ice Hockey | Darien | Home - Greenwich Skating Club-Ice Rink [Directions] | 10:00 a.m. | ||
| Fri., 12/29 | JV Wrestling | Trumbull, Brien McMahon, Darien, Fairfield Warde, Masuk, TBA, New Canaan, New Fairfield, New Milford, Newtown, Ridgefield, Simsbury, Stamford, Staples, Xavier | Away - Trumbull HS-THS Main Gym | 9:00 a.m. | ||
| Fri., 12/29 | V Girls Basketball | Bethel | Away - Bethel HS-BHS gym [Directions] | 5:00 p.m. | L 33-46 | |
| Fri., 12/29 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Greenwich Skating Club-Ice Rink [Directions] | 1:00 p.m. | W 8-6 | |
| Sat., 12/30 | V Wrestling | Trumbull Duals | Away - Trumbull HS-McDougall Stadium | 9:00 a.m. | Fairfield Prep 43 Greenwich 42 Manchester 34 Greenwich 45 Foran 66 Greenwich 15 JV All Stars 30 Greenwich 51 Stratford 44 Greenwich 36 | |
| Tue., 1/2 | V Wrestling | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 7:00 p.m. | Norwalk 60 Greenwich 24 | |
| Wed., 1/3 | V Girls Basketball | Fairfield Warde | Home - Greenwich HS-Gymnasium [Directions] | 7:00 p.m. | W 42-41 | |
| Wed., 1/3 | JV Girls Basketball | Fairfield Warde | Home - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 1/3 | FR Girls Basketball | Fairfield Warde | Home - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 1/4 | V Girls Gymnastics | Norwalk, Staples | Home - Greenwich YWCA [Directions] | 6:00 p.m. | Staples 136.2 Greenwich 123.15 Norwalk 107.15 | |
| Thu., 1/4 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Sacred Heart University-Martire Arena [Directions] | 6:00 p.m. | W 4-1 | |
| Fri., 1/5 | V Boys Basketball | Brien McMahon | Home - Greenwich HS-Gymnasium [Directions] | 7:00 p.m. | L 60-61 | |
| Fri., 1/5 | JV Boys Basketball | Brien McMahon | Home - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/5 | FR Boys Basketball | Brien McMahon | Home - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/5 | JV Boys Ice Hockey | New Canaan | Home - Greenwich - Dorothy Hamill-Rink [Directions] | 5:15 p.m. | ||
| Fri., 1/5 | V Boys Swimming and Diving | Ridgefield | Away - Barlow Mountain Pool [Directions] | 4:00 p.m. | ||
| Fri., 1/5 | V Girls Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 5:30 p.m. | L 38-42 | |
| Fri., 1/5 | JV Girls Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/5 | V Girls Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | 8:15 p.m. | L 0-8 | |
| Sat., 1/6 | V Boys Basketball | Newtown | Home - Greenwich HS-Gymnasium [Directions] | 1:00 p.m. | L 58-70 | |
| Sat., 1/6 | JV Boys Basketball | Newtown | Home - Greenwich HS-Gymnasium [Directions] | 11:30 a.m. | ||
| Sat., 1/6 | FR Boys Basketball | Newtown | Home - Greenwich HS-Gymnasium [Directions] | 10:00 a.m. | ||
| Sat., 1/6 | V Boys Ice Hockey | New Canaan | Home - Greenwich - Dorothy Hamill-Rink [Directions] | 5:45 p.m. | L 8-1 | |
| Sat., 1/6 | V Boys Indoor Track | Staples, Brien McMahon, Stamford, Westhill | Away - Staples HS-Field House [Directions] | 1:00 p.m. | ||
| Sat., 1/6 | V Wrestling | SHS WRESTLING TOURNAMENT | Away - Southington HS-Gym West | 8:00 a.m. | Daniel Hand 30 Greenwich 54 Maloney 58 Greenwich 24 Fairfield Prep 52 Greenwich 24 Southington 63 Greenwich 13 | |
| Sat., 1/6 | V Girls Indoor Track | Staples, Brien McMahon, Stamford, Westhill | Away - Staples HS-Field House [Directions] | 1:00 p.m. | ||
| Tue., 1/9 | V Boys Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:30 p.m. | L 40-55 | |
| Tue., 1/9 | JV Boys Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/9 | FR Boys Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | Postponed | ||
| Tue., 1/9 | V Girls Basketball | Fairfield Ludlowe | Home - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | W 44-38 | |
| Tue., 1/9 | JV Girls Basketball | Fairfield Ludlowe | Home - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/9 | FR Girls Basketball | Fairfield Ludlowe | Home - Greenwich HS-Gymnasium [Directions] | Postponed | ||
| Tue., 1/9 | V Girls Ice Hockey | Simsbury | Home - Greenwich - Dorothy Hamill-Rink [Directions] | 4:30 p.m. | L 1-4 | |
| Wed., 1/10 | V Boys Ice Hockey | Fairfield Prep | Away - Wonderland of Ice-Stadium [Directions] | 5:00 p.m. | L 6-1 | |
| Wed., 1/10 | V Girls Gymnastics | St. Joseph, Trumbull | Home - Greenwich YWCA [Directions] | 7:00 p.m. | Greenwich 121.75 Trumbull 144.05 St. Joe's 63.05 | |
| Fri., 1/12 | V Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 7:00 p.m. | L 54-57 OT | |
| Fri., 1/12 | JV Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/12 | FR Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/12 | V Co-ed Fencing | Fairfield Warde | Home - Central MS-Gym 1 [Directions] | 5:30 p.m. | ||
| Fri., 1/12 | V Girls Basketball | St. Joseph | Home - Greenwich HS-Gymnasium [Directions] | 7:00 p.m. | L 37-59 | |
| Fri., 1/12 | JV Girls Basketball | St. Joseph | Home - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/12 | FR Girls Basketball | St. Joseph | Home - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/12 | V Girls Gymnastics | Wilton | Away - Wilton HS-Aux Gym [Directions] | 4:30 p.m. | Greenwich 131.75 Wilton 138.55 | |
| Sat., 1/13 | V Boys Ice Hockey | St. Joseph | Home - Greenwich - Dorothy Hamill-Rink [Directions] | 5:45 p.m. | W 5-0 | |
| Sat., 1/13 | V Boys Indoor Track | Staples, Bridgeport Central, Danbury, Darien, St. Joseph, Stamford, Westhill | Away - Staples HS-Field House | 10:00 a.m. | ||
| Sat., 1/13 | V Wrestling | Greater Hartford Invitational | Away - Hall HS-Robinson Gym | 9:00 a.m. | ||
| Sat., 1/13 | V Wrestling | Trumbull, Danbury, Fairfield Warde, New Fairfield, Norwalk, Simsbury, Xavier | Away - Trumbull HS-THS Main Gym | 9:00 a.m. | ||
| Sat., 1/13 | V Girls Indoor Track | Staples, Bridgeport Central, Danbury, Darien, St. Joseph, Stamford, Westhill | Away - Staples HS-Field House | 10:00 a.m. | ||
| Sun., 1/14 | JV Boys Ice Hockey | Notre Dame-West Haven | Away - West Haven HS-Bennett Rink [Directions] | 5:30 p.m. | ||
| Wed., 1/17 | V Boys Basketball | Wilton | Home - Greenwich HS-Gymnasium [Directions] | 7:00 p.m. | L 47-59 | |
| Wed., 1/17 | JV Boys Basketball | Wilton | Home - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 1/17 | FR Boys Basketball | Wilton | Home - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 1/17 | V Wrestling | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 7:00 p.m. | Brien McMahon 15 Greenwich 60 | |
| Wed., 1/17 | V Girls Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:15 p.m. | L 30-42 | |
| Wed., 1/17 | JV Girls Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:45 p.m. | ||
| Thu., 1/18 | V Boys Swimming and Diving | Trumbull | Away - Univ of Bridgeport Pool [Directions] | 4:00 p.m. | ||
| Fri., 1/19 | V Boys Basketball | Bridgeport Central | Home - Greenwich HS-Gymnasium [Directions] | 7:00 p.m. | W 50-39 | |
| Fri., 1/19 | JV Boys Basketball | Bridgeport Central | Home - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/19 | FR Boys Basketball | Bridgeport Central | Home - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/19 | V Boys Ice Hockey | Ridgefield | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:00 p.m. | L 6-1 | |
| Fri., 1/19 | JV Boys Ice Hockey | Darien | Away - Stamford Twin Rinks-West [Directions] | 8:30 p.m. | ||
| Fri., 1/19 | V Co-ed Fencing | Guilford | Home - Central MS-Gym 1 [Directions] | 6:30 p.m. | ||
| Fri., 1/19 | V Girls Basketball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | 7:00 p.m. | W 60-44 | |
| Fri., 1/19 | JV Girls Basketball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | 5:30 p.m. | ||
| Fri., 1/19 | FR Girls Basketball | Bridgeport Central | Away - Bridgeport Central HS-The Barry McLeod Court [Directions] | 4:00 p.m. | ||
| Sat., 1/20 | V Boys Ice Hockey | Northwest Catholic | Away - Simsbury - ISCC-NHL [Directions] | 5:30 p.m. | L 2-1 | |
| Sat., 1/20 | V Boys Indoor Track | Wilton, Bridgeport Central, Brien McMahon, Danbury, New Canaan, St. Joseph, Stamford | Away - Wilton HS-Nicholas Zeoli Field House | 9:30 a.m. | ||
| Sat., 1/20 | V Boys Swimming and Diving | Fairfield Prep | Home - Greenwich HS-Pool [Directions] | 7:30 p.m. | ||
| Sat., 1/20 | V Wrestling | Brunswick School | Away - Brunswick-Edwards Campus-Gym | 9:00 a.m. | Brunswick Invitational | |
| Sat., 1/20 | V Girls Basketball | Hall | Away - Hall HS-Robinson Gym [Directions] | 2:30 p.m. | W 64-37 | |
| Sat., 1/20 | JV Girls Basketball | Hall | Away - Hall HS-Robinson Gym [Directions] | 1:00 p.m. | ||
| Sat., 1/20 | Winter Dance Team | Woodlands | Away - . | 2:00 p.m. | Woodlands | |
| Sat., 1/20 | V Girls Ice Hockey | Greenwich Country Day | Away - Chelsea Piers - Connecticut-North Rink | 3:20 p.m. | ||
| Sat., 1/20 | V Girls Indoor Track | Wilton, Bridgeport Central, Brien McMahon, Danbury, New Canaan, St. Joseph, Stamford | Away - Wilton HS-Nicholas Zeoli Field House | 9:30 a.m. | ||
| Mon., 1/22 | V Girls Gymnastics | Fairfield Ludlowe, Fairfield Warde, New Canaan | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:30 p.m. | Greenwich 120.95 Ludlowe 133.55 Warde 119.70 | |
| Mon., 1/22 | V Girls Ice Hockey | Darien | Home - Greenwich - Dorothy Hamill-Rink [Directions] | 5:15 p.m. | L 1-9 | |
| Tue., 1/23 | V Boys Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 7:00 p.m. | L 44-57 | |
| Tue., 1/23 | JV Boys Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/23 | FR Boys Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/23 | V Boys Ice Hockey | LaSalle Academy (RI) | Home - Greenwich - Dorothy Hamill-Rink [Directions] | 4:00 p.m. | L 2-1 | |
| Tue., 1/23 | V Girls Basketball | New Canaan | Home - Greenwich HS-Gymnasium [Directions] | 7:00 p.m. | W 40-35 | |
| Tue., 1/23 | JV Girls Basketball | New Canaan | Home - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/23 | FR Girls Basketball | New Canaan | Home - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 1/24 | V Boys Ice Hockey | Trumbull | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | 8:00 p.m. | W 6-4 | |
| Wed., 1/24 | JV Boys Ice Hockey | Fairfield Prep | Away - Wonderland of Ice-Stadium [Directions] | 6:00 p.m. | ||
| Wed., 1/24 | V Boys Swimming and Diving | Wilton | Away - Wilton YMCA [Directions] | 3:30 p.m. | ||
| Wed., 1/24 | V Boys Swimming and Diving | Danbury | Home - Greenwich HS-Pool [Directions] | 5:30 p.m. | ||
| Wed., 1/24 | V Wrestling | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 7:00 p.m. | Stamford 45 Greenwich 21 | |
| Thu., 1/25 | V Girls Gymnastics | Darien | Home - Greenwich YWCA [Directions] | 6:30 p.m. | Greenwich 114.35 Darien 132.4 | |
| Fri., 1/26 | V Boys Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 7:00 p.m. | L 49-57 | |
| Fri., 1/26 | JV Boys Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/26 | FR Boys Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/26 | V Boys Swimming and Diving | New Canaan | Home - Greenwich HS-Pool [Directions] | 4:15 p.m. | ||
| Fri., 1/26 | V Girls Basketball | Staples | Home - Greenwich HS-Gymnasium [Directions] | 7:00 p.m. | L 31-48 | |
| Fri., 1/26 | JV Girls Basketball | Staples | Home - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/26 | FR Girls Basketball | Staples | Home - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 1/27 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Sacred Heart University-Martire Arena [Directions] | 11:30 a.m. | L 5-2 | |
| Sat., 1/27 | V Boys Indoor Track | FCIAC West Divisionals | Away - Staples HS-Field House | 10:00 a.m. | ||
| Sat., 1/27 | V Wrestling | 2024 Gary Tiger Ridgefield Challenge | Away - Ridgefield HS-Main Gym | 9:00 a.m. | ||
| Sat., 1/27 | JV Wrestling | Norwalk, Brien McMahon, Darien, Fairfield Prep, Fairfield Ludlowe, Fairfield Warde, New Canaan, New Milford, St. Joseph, Stamford, Staples, Trumbull, Westhill, Weston, Wilton | Away - Norwalk HS-Tom Scarso Gymnasium | 8:00 a.m. | ||
| Sat., 1/27 | V Girls Ice Hockey | Stamford/Westhill/Staples | Home - Greenwich - Dorothy Hamill-Rink [Directions] | 5:30 p.m. | L 2-7 | |
| Sat., 1/27 | V Girls Indoor Track | FCIAC West Divisionals | Away - Staples HS-Field House | 10:00 a.m. | ||
| Mon., 1/29 | V Boys Ice Hockey | Cheshire | Away - Hamden-Lou Astorino Ice Rink [Directions] | 3:45 p.m. | L 4-1 | |
| Mon., 1/29 | V Girls Ice Hockey | New Canaan | Home - Greenwich - Dorothy Hamill-Rink [Directions] | 4:30 p.m. | L 0-5 | |
| Tue., 1/30 | V Boys Basketball | Trumbull | Home - Greenwich HS-Gymnasium [Directions] | 7:00 p.m. | L 66-75 | |
| Tue., 1/30 | JV Boys Basketball | Trumbull | Home - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/30 | FR Boys Basketball | Trumbull | Home - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/30 | JV Boys Ice Hockey | Ridgefield | Home - Greenwich - Dorothy Hamill-Rink [Directions] | 4:00 p.m. | ||
| Tue., 1/30 | V Girls Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 6:30 p.m. | L 35-45 | |
| Tue., 1/30 | JV Girls Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 5:00 p.m. | ||
| Tue., 1/30 | FR Girls Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | Canceled | Cancelled | |
| Wed., 1/31 | V Wrestling | Westhill | Home - Greenwich HS-Gymnasium [Directions] | 6:00 p.m. | Westhill 28 Greenwich 43 | |
| Thu., 2/1 | V Girls Gymnastics | Stamford, Westhill | Home - Greenwich YWCA [Directions] | 6:30 p.m. | Greenwich 115.55 Westhill 89.75 Stamford 78.8 | |
| Fri., 2/2 | V Boys Basketball | Danbury | Home - Greenwich HS-Gymnasium [Directions] | 7:00 p.m. | W 45-44 | |
| Fri., 2/2 | JV Boys Basketball | Danbury | Home - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 2/2 | FR Boys Basketball | Danbury | Home - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 2/2 | V Boys Swimming and Diving | Westhill/Stamford | Home - Greenwich HS-Pool [Directions] | 4:15 p.m. | ||
| Fri., 2/2 | V Wrestling | Fairfield Warde, Notre Dame-West Haven, Trumbull | Away - Fairfield Warde HS-Small Gym [Directions] | 4:00 p.m. | ||
| Fri., 2/2 | V Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 7:00 p.m. | L 42-52 | |
| Fri., 2/2 | JV Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/2 | FR Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 2/3 | JV Wrestling | Ludlowe JV Tournament | Away - Fairfield Ludlowe HS-Main Gym | TBA | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 9:30 a.m. | ||||||
| Sat., 2/3 | V Competitive Cheerleading | FCIAC Cheer Championship | Away - Trumbull HS-THS Main Gym | 10:00 a.m. | ||
| Sat., 2/3 | V Girls Ice Hockey | Darien | Away - Darien Ice House-Ice Rink [Directions] | 8:40 p.m. | L 0-9 | |
| Mon., 2/5 | V Girls Ice Hockey | Woodstock Academy Coop | Home - Greenwich - Dorothy Hamill-Rink [Directions] | 4:00 p.m. | L 1-4 | |
| Tue., 2/6 | V Boys Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 7:00 p.m. | L 60-68 | |
| Tue., 2/6 | JV Boys Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/6 | FR Boys Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/6 | V Boys Ice Hockey | Ridgefield | Home - Greenwich - Dorothy Hamill-Rink [Directions] | 4:30 p.m. | L 2-1 | |
| Tue., 2/6 | JV Boys Ice Hockey | Ridgefield | Away - Danbury Ice Arena-TBA [Directions] | Postponed | ||
| Tue., 2/6 | V Girls Basketball | Darien | Home - Greenwich HS-Gymnasium [Directions] | 7:00 p.m. | W 54-28 | |
| Tue., 2/6 | JV Girls Basketball | Darien | Home - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 2/6 | FR Girls Basketball | Darien | Home - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 2/7 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Home - Greenwich HS-Pool [Directions] | 4:15 p.m. | ||
| Wed., 2/7 | JV Wrestling | Fairfield Warde, St. Joseph | Away - Fairfield Warde HS-Small Gym [Directions] | 5:00 p.m. | ||
| Thu., 2/8 | V Boys Indoor Track | CIAC LL Divisional Championship | Away - Floyd Little Athletic Center | 4:30 p.m. | ||
| Thu., 2/8 | V Girls Gymnastics | New Canaan | Home - Greenwich YWCA [Directions] | 6:30 p.m. | Greenwich 121.4 New Canaan 97.85 | |
| Thu., 2/8 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Greenwich - Dorothy Hamill-Rink [Directions] | 7:00 p.m. | L 3-4 (OT) | Senior Night |
| Thu., 2/8 | V Girls Indoor Track | CIAC LL Divisional Championship | Away - Floyd Little Athletic Center | 4:30 p.m. | ||
| Fri., 2/9 | V Boys Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 7:00 p.m. | W 45-39 | |
| Fri., 2/9 | JV Boys Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 2/9 | FR Boys Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 2/9 | JV Boys Ice Hockey | Rye (NY) | Home - Greenwich - Dorothy Hamill-Rink [Directions] | 5:15 p.m. | ||
| Fri., 2/9 | V Wrestling | New Canaan, Bridgeport Central, Brien McMahon, Danbury, Darien, FCIAC, Fairfield Ludlowe, Fairfield Warde, Norwalk, Ridgefield, St. Joseph, Stamford, Staples, Trumbull, Westhill, Wilton | Away - New Canaan HS-Main Gym | 4:30 p.m. | ||
| Fri., 2/9 | V Girls Basketball | Stamford | Home - Greenwich HS-Gymnasium [Directions] | 7:00 p.m. | L 39-51 | |
| Fri., 2/9 | JV Girls Basketball | Stamford | Home - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 2/9 | FR Girls Basketball | Stamford | Home - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 2/10 | V Boys Ice Hockey | Darien | Away - Darien Ice House-Ice Rink [Directions] | 4:20 p.m. | L 5-0 | |
| Sat., 2/10 | Winter Dance Team | Warde Dance Jam | Away - . | 9:00 a.m. | Warde Dance Jam | |
| Sat., 2/10 | V Girls Gymnastics | FCIAC | Home - TBA [Directions] | TBA | 108.25 | FCIAC |
| Sat., 2/10 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Greenwich - Dorothy Hamill-Rink [Directions] | 5:45 p.m. | W 7-3 | |
| Mon., 2/12 | V Boys Basketball | Ridgefield | Home - Greenwich HS-Gymnasium [Directions] | 7:00 p.m. | L 43-51 | |
| Mon., 2/12 | JV Boys Basketball | Ridgefield | Home - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 2/12 | FR Boys Basketball | Ridgefield | Home - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 2/12 | V Girls Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 7:00 p.m. | L 42-57 | |
| Mon., 2/12 | JV Girls Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/12 | FR Girls Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | Postponed | ||
| Tue., 2/13 | V Bowling | Fairfield Warde | Away - Nutmeg Bowling Alley [Directions] | Postponed | ||
| Wed., 2/14 | V Boys Basketball | Norwalk | Home - Greenwich HS-Gymnasium [Directions] | 7:00 p.m. | L 50-56 | |
| Wed., 2/14 | JV Boys Basketball | Norwalk | Home - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 2/14 | FR Boys Basketball | Norwalk | Home - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 2/14 | JV Boys Ice Hockey | Rye (NY) | Away - Rye HS-Rye Playland Ice | 7:45 p.m. | ||
| Wed., 2/14 | V Girls Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 6:15 p.m. | L 46-72 | |
| Wed., 2/14 | JV Girls Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | Postponed | ||
| Thu., 2/15 | V Boys Basketball | Bassick | Home - Greenwich HS-Gymnasium [Directions] | 6:00 p.m. | W 74-58 | |
| Thu., 2/15 | JV Boys Basketball | Bassick | Home - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 2/15 | FR Boys Basketball | Bassick | Home - Greenwich HS-Gymnasium [Directions] | 2:45 p.m. | ||
| Thu., 2/15 | V Boys Ice Hockey | Notre Dame-West Haven | Home - Greenwich - Dorothy Hamill-Rink [Directions] | 7:15 p.m. | L 7-2 | |
| Fri., 2/16 | V Wrestling | CIAC LL Divisional Championship | Away - Trumbull | TBA | ||
| Sat., 2/17 | V Boys Indoor Track | CIAC State Open Divisional Championship | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/17 | V Girls Indoor Track | CIAC State Open Championship | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Mon., 2/19 | V Boys Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 5:30 p.m. | W 57-46 | |
| Mon., 2/19 | JV Boys Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 2/19 | FR Boys Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 2:30 p.m. | ||
| Tue., 2/20 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Home - Greenwich - Dorothy Hamill-Rink [Directions] | 4:30 p.m. | L 5-1 | |
| Wed., 2/21 | V Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 7:00 p.m. | W 59-49 | |
| Wed., 2/21 | JV Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/21 | FR Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/21 | V Boys Ice Hockey | Notre Dame-Fairfield | Away - Sacred Heart University-Martire Arena [Directions] | 6:30 p.m. | W 6-4 | |
| Wed., 2/21 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Home - Greenwich HS-Pool [Directions] | 4:15 p.m. | ||
| Wed., 2/21 | V Girls Ice Hockey | Hall/Conard | Home - Greenwich - Dorothy Hamill-Rink [Directions] | 8:15 p.m. | L 1-5 | |
| Thu., 2/22 | V Boys Ice Hockey | St. Joseph | Away - Sports Center of Connecticut-Lower [Directions] | 2:00 p.m. | W 2-1 | |
| Fri., 2/23 | V Wrestling | CIAC State Open & Girls Championship | Away - Floyd Little Athletic Center | TBA | ||
| Sat., 2/24 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Sacred Heart University-Martire Arena [Directions] | 1:00 p.m. | W 4-3 | |
| Sat., 2/24 | Winter Dance Team | States @ Hamden | Away - . | 9:00 a.m. | States @ Hamden | |
| Sat., 2/24 | V Girls Gymnastics | CIAC Class L Divisional Championship | Away - Jonathan Law | 1:00 p.m. | ||
| Mon., 2/26 | JV Boys Ice Hockey | Darien | Home - Greenwich - Dorothy Hamill-Rink [Directions] | 4:00 p.m. | ||
| Mon., 2/26 | V Co-ed Fencing | Fairfield Warde | Away - Holy Family Church [Directions] | 7:00 p.m. | ||
| Mon., 2/26 | V Girls Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 6:00 p.m. | L 36-44 | |
| Tue., 2/27 | V Boys Swimming and Diving | Darien, TBA | Home - Greenwich HS-Pool [Directions] | 5:15 p.m. | ||
| Wed., 2/28 | V Boys Diving | FCIAC Diving Finals @ Westhill | Away - . | 5:00 p.m. | FCIAC Diving Finals @ Westhill | |
| Wed., 2/28 | V Boys Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | 5:00 p.m. | ||
| Thu., 2/29 | Unified Sports Basketball | Stamford | Home - Greenwich HS-Gymnasium [Directions] | 3:30 p.m. | ||
| Fri., 3/1 | V Boys Basketball | Fairfield Prep | Home - Greenwich HS-Gymnasium [Directions] | 6:00 p.m. | W 60-47 | |
| Sat., 3/2 | JV Boys Basketball | JV Tournament Fairfield Warde HS | Away - . | 9:00 a.m. | ||
| Sat., 3/2 | V Girls Gymnastics | State Open | Home - TBA [Directions] | TBA | State Open | |
| Wed., 3/6 | V Boys Ice Hockey | Fairfield Prep | Away - Wonderland of Ice-Stadium [Directions] | 6:00 p.m. | W 4-3 | |
| Wed., 3/6 | V Boys Ice Hockey | CIAC Div I First Round | Away - Higher Seed | TBA | ||
| Thu., 3/7 | V Boys Basketball | Notre Dame-West Haven | Away - Notre Dame HS-Gym [Directions] | 6:30 p.m. | L 34-70 | |
| Thu., 3/7 | V Boys Swimming and Diving | CIAC Class LL Diving Championship | Away - Sheehan | 5:30 p.m. | ||
| Sat., 3/9 | V Boys Ice Hockey | New Canaan | Away - Terry Conners - Stamford-Ice Rink [Directions] | 7:30 p.m. | L 0-7 | |
| Sat., 3/9 | V Boys Ice Hockey | CIAC Div I Quarterfinal | Away - Site TBA | TBA | ||
| Sat., 3/9 | V Boys Swimming and Diving | CIAC Class LL Qualifying Meet | Away - Cornerstone Pool | 4:30 p.m. | ||
| Tue., 3/12 | V Boys Swimming and Diving | CIAC Class LL Finals | Away - Wesleyan | 6:00 p.m. | ||
| Wed., 3/13 | V Boys Ice Hockey | CIAC Div I Semifinal | Away - Site TBA | TBA | ||
| Thu., 3/14 | V Boys Swimming and Diving | CIAC State Open Diving | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/16 | V Boys Swimming and Diving | CIAC State Open Championship Yale | Away - . | 1:00 p.m. | CIAC State Open Championship Yale | |
| Tue., 3/19 | V Boys Ice Hockey | CIAC Div I Final | Away - Site TBA | TBA | ||
| Thu., 3/21 | V Boys Lacrosse | Somers (NY) (Scrim.) | Away - Somers HS-Turf 1 | 4:30 p.m. | ||
| Thu., 3/21 | V Girls Lacrosse | Harrison (NY) (Scrim.) | Home - Greenwich HS-Field 3 [Directions] | 4:00 p.m. | Scrimmage | |
| Thu., 3/21 | JV Girls Lacrosse | Harrison (NY) (Scrim.) | Home - Greenwich HS-Field 3 [Directions] | 5:15 p.m. | ||
| Thu., 3/21 | V Softball | Wilton (Scrim.) | Away - Wilton HS-Varsity Softball Field [Directions] | 4:15 p.m. | ||
| Thu., 3/21 | JV Softball | Wilton (Scrim.) | Away - Wilton HS-JV Softball Field [Directions] | 4:15 p.m. | ||
| Fri., 3/22 | V Baseball | Darien (Scrim.) | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:15 p.m. | ||
| Fri., 3/22 | JV Baseball | Darien (Scrim.) | Away - Darien HS-DHS Baseball - JV Field [Directions] | 4:15 p.m. | ||
| Sat., 3/23 | V Girls Lacrosse | GIRLS LAX PLAY DAY | Away - Staples HS-Ginny Parker Field | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to 8:00 a.m. | ||||||
| Sat., 3/23 | V Softball | TBA | Away - TBA | 10:00 a.m. | Cancelled | |
| Sun., 3/24 | V Baseball | Norwalk (Scrim.) | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 12:00 p.m. | ||
| Sun., 3/24 | V Baseball | New Canaan (Scrim.) | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 2:30 p.m. | ||
| Mon., 3/25 | V Boys Lacrosse | Iona Prep (NY) (Scrim.) | Home - Greenwich HS-Field 3 [Directions] | 3:45 p.m. | ||
| Mon., 3/25 | V Boys Lacrosse | Wilton (Scrim.) | Home - Greenwich HS-Field 3 [Directions] | 5:45 p.m. | ||
| Mon., 3/25 | JV Boys Lacrosse | Iona Prep (NY) (Scrim.) | Away - Iona Preparatory School-Stadium | 4:00 p.m. | ||
| Mon., 3/25 | V Girls Lacrosse | Greens Farms Academy (Scrim.) | Away - Greens Farms Academy-Stadium Turf | 4:30 p.m. | ||
| Tue., 3/26 | V Baseball | Stamford (Scrim.) | Away - Cubeta Stadium [Directions] | 5:15 p.m. | Scrimmage | |
| Tue., 3/26 | V Boys Tennis | Brunswick School (Scrim.) | Away - Brunswick School | 3:30 p.m. | ||
| Tue., 3/26 | V Softball | Darien (Scrim.) | Away - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | ||
| Tue., 3/26 | V Girls Tennis | Sacred Heart of Greenwich (Scrim.) | Home - Greenwich HS-Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Tue., 3/26 | JV Girls Tennis | Sacred Heart of Greenwich (Scrim.) | Away - Sacred Heart of Greenwich | 4:15 p.m. | ||
| Tue., 3/26 | V Girls Water Polo | Staples | Home - Greenwich HS-Pool [Directions] | 5:00 p.m. | ||
| Wed., 3/27 | V Baseball | Fairfield Warde (Scrim.) | Away - Fairfield Warde HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 3/27 | V Boys Lacrosse | Fairfield Prep (Scrim.) | Away - Fairfield University-Rafferty Stadium [Directions] | 6:00 p.m. | ||
| Wed., 3/27 | JV Boys Lacrosse | Fairfield Prep (Scrim.) | Home - Greenwich HS-Field 3 [Directions] | 4:00 p.m. | ||
| Wed., 3/27 | FR Boys Lacrosse | Fairfield Prep (Scrim.) | Home - Greenwich HS-Field 3 [Directions] | 5:15 p.m. | ||
| Wed., 3/27 | V Boys Tennis | Greenwich Country Day (Scrim.) | Home - Greenwich HS-Tennis Courts [Directions] | 4:15 p.m. | ||
| Wed., 3/27 | V Boys Volleyball | Stamford (Scrim.) | Away - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | ||
| Wed., 3/27 | V Co-ed Sailing | Darien, Fairfield Ludlowe | Home - Grass Island [Directions] | 4:00 p.m. | ||
| Wed., 3/27 | V Girls Water Polo | Greenwich Academy | Home - Greenwich HS-Pool [Directions] | 4:00 p.m. | ||
| Thu., 3/28 | V Boys Rugby | Staples | Home - Greenwich HS-Cardinal Stadium [Directions] | 5:00 p.m. | ||
| Thu., 3/28 | JV Boys Rugby | Staples | Home - Greenwich HS-Cardinal Stadium [Directions] | 6:30 p.m. | ||
| Thu., 3/28 | FM Boys Rugby | Staples | Home - Greenwich HS-Field 7 [Directions] | 5:00 p.m. | ||
| Sat., 3/30 | V Baseball | West Haven | Home - Havemeyer Field-Havermeyer Field [Directions] | 1:00 p.m. | W 2-0 | |
| Sat., 3/30 | V Girls Lacrosse | Nyack (NY) | Home - Greenwich HS-Cardinal Stadium [Directions] | 11:00 a.m. | ||
| Sat., 3/30 | JV Girls Lacrosse | Nyack (NY) | Home - Greenwich HS-Cardinal Stadium [Directions] | 12:30 p.m. | ||
| Sat., 3/30 | V Softball | New Fairfield | Home - Greenwich HS-Softball Field [Directions] | 11:00 a.m. | L 0-15 | |
| Mon., 4/1 | V Boys Volleyball | Westhill | Home - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | L 0-3 | |
| Mon., 4/1 | JV Boys Volleyball | Westhill | Home - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | L 0-2 | |
| Mon., 4/1 | V Girls Lacrosse | Bronxville (NY) | Home - Greenwich HS-Cardinal Stadium [Directions] | 5:00 p.m. | ||
| Mon., 4/1 | V Girls Tennis | Greenwich Academy (Scrim.) | Away - Greenwich Academy | 4:30 p.m. | Cancelled | |
| Mon., 4/1 | JV Girls Tennis | Greenwich Academy (Scrim.) | Home - Binney Park [Directions] | Canceled | Cancelled | JV A |
| Tue., 4/2 | V Boys Lacrosse | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 4:30 p.m. | W 9-8 | |
| Tue., 4/2 | JV Boys Lacrosse | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 6:00 p.m. | ||
| Tue., 4/2 | FR Boys Lacrosse | Staples | Home - Greenwich HS-Field 3 [Directions] | 4:30 p.m. | ||
| Tue., 4/2 | V Girls Rugby | Southington | Home - Greenwich HS-Cardinal Stadium [Directions] | 5:00 p.m. | ||
| Tue., 4/2 | V Girls Water Polo | Greenwich Aquatics | Home - Greenwich HS-Pool [Directions] | 4:30 p.m. | Greenwich Aquatics | |
| Wed., 4/3 | V Boys Rugby | Simsbury | Home - Greenwich HS-Cardinal Stadium [Directions] | 6:00 p.m. | ||
| Wed., 4/3 | V Boys Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | L 1-3 | |
| Wed., 4/3 | V Girls Golf | Greenwich Country Day (Scrim.) | Home - Griffith E Harris Golf Course [Directions] | Rainout | ||
| Wed., 4/3 | JV Girls Tennis | Fairfield Warde | Away - Fairfield Warde HS-Knapps Courts [Directions] | Canceled | Cancelled | |
| Thu., 4/4 | FR Boys Lacrosse | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 4/4 | V Boys Outdoor Track | Westhill | Home - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Thu., 4/4 | V Co-ed Sailing | Darien | Home - Grass Island [Directions] | 3:00 p.m. | ||
| Thu., 4/4 | V Girls Golf | Fairfield Warde | Home - Fairview Country Club [Directions] | 3:00 p.m. | ||
| Thu., 4/4 | V Girls Outdoor Track | Westhill | Home - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | W 80.5-63.5 | |
| Thu., 4/4 | V Girls Water Polo | Fenwick Tournament in Chicago | Away - . | TBA | Fenwick Tournament in Chicago | |
| Fri., 4/5 | V Baseball | Staples | Away - Staples HS-Baseball Diamond [Directions] | 4:30 p.m. | L 0-12 F5 | |
| Fri., 4/5 | JV Baseball | Staples | Away - Staples HS-Wakeman Field [Directions] | 4:30 p.m. | ||
| Fri., 4/5 | FR Baseball | Staples | Home - Julian Curtiss School [Directions] | 4:30 p.m. | ||
| Fri., 4/5 | V Boys Rugby | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 4:30 p.m. | ||
| Fri., 4/5 | V Softball | Weston | Away - Weston HS-Softball - North House Field (Hurlbutt El. School) [Directions] | 4:15 p.m. | L 8-9 | |
| Fri., 4/5 | V Girls Water Polo | Fenwick Tournament in Chicago | Away - . | TBA | Fenwick Tournament in Chicago | |
| Sat., 4/6 | V Baseball | St. Bernard | Home - Havemeyer Field-Havermeyer Field [Directions] | 1:00 p.m. | L 0-8 | |
| Sat., 4/6 | V Boys Lacrosse | Mamaroneck (NY) | Away - Mamaroneck HS-Field | 1:00 p.m. | L 10-9 | |
| Sat., 4/6 | JV Boys Lacrosse | Mamaroneck (NY) | Away - Mamaroneck HS-Field | 3:00 p.m. | ||
| Sat., 4/6 | FM Boys Rugby | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 2:30 p.m. | ||
| Sat., 4/6 | V Girls Lacrosse | Litchfield Coop | Away - Plumb Hill Field Complex-Varsity Soccer Field [Directions] | 12:00 p.m. | ||
| Sat., 4/6 | JV Girls Lacrosse | Litchfield Coop | Away - Plumb Hill Field Complex-Softball Field [Directions] | 1:45 p.m. | ||
| Sat., 4/6 | V Girls Water Polo | Fenwick Tournament in Chicago | Away - . | TBA | Fenwick Tournament in Chicago | |
| Sun., 4/7 | V Softball | Stratford | Home - Greenwich HS-Softball Field [Directions] | 1:15 p.m. | L 1-9 | |
| Sun., 4/7 | V Girls Water Polo | Fenwick Tournament in Chicago | Away - . | TBA | Fenwick Tournament in Chicago | |
| Mon., 4/8 | V Boys Outdoor Track | Stamford | Home - Greenwich HS-Cardinal Stadium [Directions] | 5:00 p.m. | ||
| Mon., 4/8 | JV Boys Rugby | Darien | Home - Greenwich HS-Field 7 [Directions] | 5:00 p.m. | ||
| Mon., 4/8 | V Boys Tennis | Brien McMahon | Home - Greenwich HS-Tennis Courts [Directions] | 5:00 p.m. | W 7-0 [Detailed Results] | |
| Mon., 4/8 | JV Boys Tennis | New Canaan | Home - Central MS [Directions] | 5:00 p.m. | JV A | |
| Mon., 4/8 | V Girls Outdoor Track | Stamford | Home - Greenwich HS-Cardinal Stadium [Directions] | 5:00 p.m. | W 108-33 | |
| Mon., 4/8 | V Softball | Bridgeport Central | Away - Bridgeport Central HS-Softball Diamond [Directions] | 5:00 p.m. | W 18-0 | |
| Mon., 4/8 | JV Softball | Bridgeport Central | Away - Bridgeport Central HS-Softball Diamond 2 [Directions] | 5:00 p.m. | ||
| Mon., 4/8 | V Girls Tennis | Brien McMahon | Away - Brien McMahon HS-Tennis Courts [Directions] | 5:00 p.m. | W 7-0 [Detailed Results] | |
| Mon., 4/8 | JV Girls Tennis | New Canaan | Home - Binney Park [Directions] | 5:00 p.m. | JV A | |
| Tue., 4/9 | V Baseball | Fairfield Ludlowe | Away - Kiwanis Field-Baseball Diamond [Directions] | 4:30 p.m. | L 1-11 F6 | |
| Tue., 4/9 | JV Baseball | Fairfield Ludlowe | Away - Owen Fish Park-Owen Fish [Directions] | 4:00 p.m. | ||
| Tue., 4/9 | FR Baseball | Fairfield Ludlowe | Home - Julian Curtiss School [Directions] | 4:30 p.m. | ||
| Tue., 4/9 | V Boys Lacrosse | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | W 12-6 | |
| Tue., 4/9 | JV Boys Lacrosse | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/9 | V Boys Rugby | Rye (NY) | Home - Greenwich HS-Field 7 [Directions] | 4:30 p.m. | ||
| Tue., 4/9 | FM Boys Rugby | Rye (NY) | Home - Greenwich HS-Field 7 [Directions] | 6:00 p.m. | ||
| Tue., 4/9 | V Boys Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Tue., 4/9 | JV Boys Tennis | Fairfield Ludlowe | Away - Tomlinson MS-Tennis Courts [Directions] | 4:00 p.m. | JV B | |
| Tue., 4/9 | V Girls Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 4/9 | V Girls Lacrosse | Stamford | Home - Greenwich HS-Cardinal Stadium [Directions] | 5:10 p.m. | ||
| Tue., 4/9 | JV Girls Lacrosse | Stamford | Home - Greenwich HS-Field 3 [Directions] | Postponed | ||
| Tue., 4/9 | V Girls Tennis | Fairfield Ludlowe | Home - Greenwich HS-Tennis Courts [Directions] | 4:15 p.m. | W 6-1 [Detailed Results] | |
| Tue., 4/9 | JV Girls Tennis | Fairfield Ludlowe | Home - Binney Park [Directions] | 4:15 p.m. | JV A | |
| Tue., 4/9 | V Girls Water Polo | Sacred Heart of Greenwich | Home - Greenwich HS-Pool [Directions] | 4:30 p.m. | ||
| Wed., 4/10 | FR Baseball | Darien | Away - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | ||
| Wed., 4/10 | V Softball | Westhill | Home - Greenwich HS-Softball Field [Directions] | 4:30 p.m. | L 0-1 | |
| Thu., 4/11 | V Boys Lacrosse | Notre Dame-West Haven | Home - Greenwich HS-Cardinal Stadium [Directions] | 5:15 p.m. | W 21-11 | |
| Thu., 4/11 | V Girls Golf | Danbury | Home - Fairview Country Club [Directions] | 3:30 p.m. | ||
| Fri., 4/12 | V Baseball | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 4:30 p.m. | W 8-3 | |
| Fri., 4/12 | FR Boys Lacrosse | Fairfield Prep | Home - Greenwich HS-Field 3 [Directions] | 4:30 p.m. | ||
| Fri., 4/12 | V Boys Volleyball | Fairfield Ludlowe | Home - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | ||
| Fri., 4/12 | JV Boys Volleyball | Fairfield Ludlowe | Home - Greenwich HS-Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 4/12 | V Girls Lacrosse | Weston | Away - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | ||
| Fri., 4/12 | JV Girls Lacrosse | Weston | Away - Weston HS-WHS Lower Turf Field [Directions] | 4:30 p.m. | ||
| Fri., 4/12 | JV Girls Tennis | St. Joseph | Home - Binney Park [Directions] | Postponed | JV B | |
| Sat., 4/13 | V Boys Lacrosse | Wilton | Away - Wilton HS-Veterans Memorial Stadium [Directions] | 3:30 p.m. | L 8-6 | |
| Sat., 4/13 | JV Boys Lacrosse | Wilton | Away - Wilton HS-Veterans Memorial Stadium [Directions] | 12:00 p.m. | ||
| Sat., 4/13 | V Boys Rugby | BC High | Away - . | 1:30 p.m. | BC High Boston - 150 Morrissey Blvd in Boston, 02186 | |
| Sat., 4/13 | JV Boys Rugby | Midstate | Away - . | 11:00 a.m. | Midstate Peckham Park - 161 Strickland Rd. Middlefield | |
| Sat., 4/13 | V Girls Lacrosse | Wilton | Away - Wilton HS-Lilly Field [Directions] | 2:00 p.m. | ||
| Sat., 4/13 | JV Girls Lacrosse | Wilton | Away - Wilton HS-Lilly Field [Directions] | 12:00 p.m. | ||
| Sat., 4/13 | V Girls Water Polo | Navy | Away - . | TBA | Navy | |
| Sun., 4/14 | V Baseball | Immaculate | Home - Havemeyer Field-Havermeyer Field [Directions] | 1:15 p.m. | L 4-5 F8 | |
| Mon., 4/15 | V Baseball | Fairfield Ludlowe | Home - Havemeyer Field-Havermeyer Field [Directions] | 11:00 a.m. | L 1-4 | |
| Mon., 4/15 | JV Baseball | Fairfield Ludlowe | Home - Julian Curtiss School [Directions] | 11:00 a.m. | ||
| Mon., 4/15 | FR Baseball | Fairfield Ludlowe | Away - Kiwanis Field-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Mon., 4/15 | V Boys Tennis | Wilton | Home - Greenwich HS-Tennis Courts [Directions] | 4:15 p.m. | W 5-2 [Detailed Results] | |
| Mon., 4/15 | V Boys Volleyball | Staples | Home - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | ||
| Mon., 4/15 | JV Boys Volleyball | Staples | Home - Greenwich HS-Gymnasium [Directions] | 5:15 p.m. | ||
| Mon., 4/15 | V Softball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 2:00 p.m. | L 2-16 | |
| Mon., 4/15 | JV Softball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 4:00 p.m. | ||
| Mon., 4/15 | V Girls Tennis | Wilton | Away - Wilton HS-Tennis Courts [Directions] | 11:00 a.m. | W 6-1 [Detailed Results] | |
| Tue., 4/16 | JV Baseball | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 4:00 p.m. | ||
| Tue., 4/16 | V Boys Lacrosse | Horace Greeley (NY) | Home - Greenwich HS-Field 3 [Directions] | 5:00 p.m. | W 13-11 | |
| Tue., 4/16 | JV Boys Lacrosse | Greenwich Country Day | Away - GCDS Old church Fields | 4:30 p.m. | Offit Field on Cardinal Road. | |
| Tue., 4/16 | V Boys Tennis | Bridgeport Central | Home - Greenwich HS-Tennis Courts [Directions] | 4:15 p.m. | W 7-0 [Detailed Results] | |
| Tue., 4/16 | V Girls Lacrosse | Horace Greeley (NY) | Home - Greenwich HS-Cardinal Stadium [Directions] | 5:00 p.m. | ||
| Tue., 4/16 | V Softball | Brien McMahon | Home - Greenwich HS-Softball Field [Directions] | 4:00 p.m. | W 5-3 | |
| Tue., 4/16 | JV Softball | Brien McMahon | Home - Julian Curtiss School [Directions] | 4:00 p.m. | ||
| Tue., 4/16 | V Girls Tennis | Bridgeport Central | Away - Bridgeport Central HS-Central High School Tennis Courts [Directions] | 5:00 p.m. | W 7-0 [Detailed Results] | |
| Wed., 4/17 | V Baseball | St. Joseph | Home - Havemeyer Field-Havermeyer Field [Directions] | 3:30 p.m. | W 6-3 | |
| Wed., 4/17 | JV Baseball | St. Joseph | Home - Julian Curtiss School [Directions] | 3:30 p.m. | ||
| Wed., 4/17 | FR Baseball | St. Joseph | Away - St. Joseph HS-Baseball Diamond [Directions] | 3:30 p.m. | ||
| Wed., 4/17 | FR Boys Lacrosse | St. Joseph | Home - Greenwich HS-Field 3 [Directions] | 4:00 p.m. | ||
| Wed., 4/17 | V Boys Volleyball | Bridgeport Central | Home - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | ||
| Wed., 4/17 | JV Boys Volleyball | Bridgeport Central | Home - Greenwich HS-Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 4/17 | V Softball | St. Joseph | Away - St. Joseph HS-Softball Diamond [Directions] | 4:00 p.m. | L 0-10 | |
| Wed., 4/17 | JV Softball | St. Joseph | Away - St. Joseph HS-Long Hill, Admin Field [Directions] | 4:00 p.m. | ||
| Thu., 4/18 | V Boys Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 12:00 p.m. | L 4-9 | |
| Thu., 4/18 | JV Boys Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 3:30 p.m. | ||
| Thu., 4/18 | V Boys Volleyball | Stamford | Home - Greenwich HS-Gymnasium [Directions] | 11:00 a.m. | ||
| Thu., 4/18 | JV Boys Volleyball | Stamford | Home - Greenwich HS-Gymnasium [Directions] | 12:30 p.m. | ||
| Thu., 4/18 | V Girls Lacrosse | New Canaan | Home - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Thu., 4/18 | JV Girls Lacrosse | New Canaan | Home - Greenwich HS-Cardinal Stadium [Directions] | Postponed | ||
| Pending changes awaiting acceptance by one or more parties involved: Date to 4/30, Time to 5:00 p.m. | ||||||
| Fri., 4/19 | V Baseball | Wilton | Away - Wilton HS-Varsity Baseball Field [Directions] | 4:15 p.m. | W 6-4 | |
| Fri., 4/19 | JV Baseball | Wilton | Away - Wilton HS-JV Baseball Field [Directions] | 4:15 p.m. | ||
| Fri., 4/19 | FR Baseball | Wilton | Home - Havemeyer Field-Havermeyer Field [Directions] | 4:30 p.m. | ||
| Fri., 4/19 | V Boys Tennis | St. Joseph | Away - St. Joseph HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Fri., 4/19 | V Softball | Wilton | Home - Greenwich HS-Softball Field [Directions] | 4:00 p.m. | W 3-2 | |
| Fri., 4/19 | JV Softball | Wilton | Home - Julian Curtiss School [Directions] | Postponed | ||
| Fri., 4/19 | V Girls Tennis | St. Joseph | Home - Greenwich HS-Tennis Courts [Directions] | 4:15 p.m. | W 7-0 [Detailed Results] | |
| Sat., 4/20 | V Boys Lacrosse | Bronxville (NY) | Home - Greenwich HS-Cardinal Stadium [Directions] | 12:00 p.m. | L 12-11 | |
| Sat., 4/20 | JV Boys Lacrosse | Bronxville (NY) | Home - Greenwich HS-Field 3 [Directions] | 12:00 p.m. | ||
| Sat., 4/20 | JV Boys Rugby | Home - Greenwich HS-Cardinal Stadium [Directions] | 5:00 p.m. | |||
| Mon., 4/22 | FR Boys Lacrosse | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Mon., 4/22 | V Boys Outdoor Track | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 3:30 p.m. | ||
| Mon., 4/22 | V Boys Tennis | Staples | Away - Staples HS-Staples Tennis Courts [Directions] | 3:30 p.m. | W 6-1 [Detailed Results] | |
| Mon., 4/22 | JV Boys Tennis | Staples | Away - Staples HS-Town Farms Tennis Courts [Directions] | Postponed | JV A | |
| Mon., 4/22 | V Girls Outdoor Track | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 3:30 p.m. | ||
| Mon., 4/22 | V Softball | Bridgeport Central | Home - Byram Park CT.-Teufel Park Ct. [Directions] | 6:30 p.m. | W 15-0 | |
| Mon., 4/22 | JV Softball | Bridgeport Central | Home - Byram Park CT.-Teufel Park Ct. [Directions] | 4:30 p.m. | ||
| Mon., 4/22 | V Girls Tennis | Staples | Home - Greenwich HS-Tennis Courts [Directions] | 3:30 p.m. | W 6-1 [Detailed Results] | |
| Mon., 4/22 | JV Girls Tennis | Staples | Home - Binney Park [Directions] | Postponed | JV A | |
| Tue., 4/23 | V Baseball | Bridgeport Central | Away - Bridgeport Central HS-Baseball Diamond [Directions] | 4:30 p.m. | W 21-6 | |
| Tue., 4/23 | JV Baseball | Kolbe Cathedral | Away - Seaside Park #10 [Directions] | 4:30 p.m. | ||
| Tue., 4/23 | V Boys Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 6:00 p.m. | ||
| Tue., 4/23 | JV Boys Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | V Boys Tennis | Trumbull | Home - Greenwich HS-Tennis Courts [Directions] | 4:15 p.m. | W 5-2 [Detailed Results] | |
| Tue., 4/23 | JV Boys Tennis | Trumbull | Home - Eastern MS [Directions] | 4:30 p.m. | JV B | |
| Tue., 4/23 | V Boys Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | V Girls Golf | New Canaan | Away - CCNC [Directions] | 3:30 p.m. | ||
| Tue., 4/23 | JV Girls Golf | New Canaan | Away - CCNC [Directions] | 3:30 p.m. | ||
| Tue., 4/23 | V Girls Lacrosse | Fairfield Ludlowe | Home - Greenwich HS-Cardinal Stadium [Directions] | 5:00 p.m. | ||
| Tue., 4/23 | JV Girls Lacrosse | Fairfield Ludlowe | Home - Greenwich HS-Field 3 [Directions] | 6:15 p.m. | ||
| Tue., 4/23 | V Girls Tennis | Trumbull | Away - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Tue., 4/23 | JV Girls Tennis | Trumbull | Away - Tashua Knolls Golf Course-Tennis Courts [Directions] | 4:00 p.m. | JV B | |
| Tue., 4/23 | V Girls Water Polo | Staples | Home - Greenwich HS-Pool [Directions] | 5:00 p.m. | ||
| Wed., 4/24 | V Baseball | New Canaan | Home - Havemeyer Field-Havermeyer Field [Directions] | 4:30 p.m. | W 7-5 | |
| Wed., 4/24 | JV Baseball | New Canaan | Home - Julian Curtiss School [Directions] | 4:30 p.m. | ||
| Wed., 4/24 | FR Baseball | New Canaan | Away - New Canaan HS-Coppo Field [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | FR Boys Lacrosse | Wilton | Home - Greenwich HS-Field 4 [Directions] | 5:00 p.m. | ||
| Wed., 4/24 | FM Boys Rugby | Trumbull | Away - Trumbull HS-Cork Field [Directions] | 6:30 p.m. | ||
| Wed., 4/24 | V Boys Tennis | New Canaan | Away - New Canaan HS-NCHS Tennis Courts [Directions] | 4:00 p.m. | W 4-3 [Detailed Results] | |
| Wed., 4/24 | V Softball | New Canaan | Away - Waveny Park-Orchard Field [Directions] | 4:00 p.m. | L 2-3 | |
| Wed., 4/24 | JV Softball | New Canaan | Away - Waveny Park-Orchard Field [Directions] | 4:00 p.m. | ||
| Thu., 4/25 | V Boys Lacrosse | Weston | Away - Weston HS-WHS Lower Turf Field [Directions] | 6:00 p.m. | ||
| Thu., 4/25 | JV Boys Lacrosse | Weston | Away - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 4/25 | V Boys Tennis | Danbury | Home - Greenwich HS-Tennis Courts [Directions] | 4:15 p.m. | W 7-0 [Detailed Results] | |
| Thu., 4/25 | JV Boys Tennis | Trumbull | Away - Tashua Knolls Golf Course-Tennis Courts [Directions] | 4:00 p.m. | JV B | |
| Thu., 4/25 | V Boys Volleyball | Trumbull | Home - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | ||
| Thu., 4/25 | JV Boys Volleyball | Trumbull | Home - Greenwich HS-Gymnasium [Directions] | 5:15 p.m. | ||
| Thu., 4/25 | V Girls Golf | Wilton | Home - Fairview Country Club [Directions] | 3:30 p.m. | ||
| Thu., 4/25 | V Girls Lacrosse | East Lyme | Away - East Lyme HS-Dick North Turf Field [Directions] | 6:30 p.m. | ||
| Thu., 4/25 | JV Girls Lacrosse | East Lyme | Away - East Lyme HS-Dick North Turf Field [Directions] | 5:00 p.m. | ||
| Thu., 4/25 | V Girls Tennis | Danbury | Away - Danbury HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 6-1 [Detailed Results] | |
| Fri., 4/26 | V Baseball | Staples | Home - Havemeyer Field-Havermeyer Field [Directions] | 4:30 p.m. | L 0-5 | |
| Fri., 4/26 | JV Baseball | Staples | Home - Julian Curtiss School [Directions] | 4:30 p.m. | ||
| Fri., 4/26 | FR Baseball | Staples | Away - Staples HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Fri., 4/26 | FR Boys Lacrosse | Trumbull | Away - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | ||
| Fri., 4/26 | V Girls Rugby | Trumbull | Away - Trumbull HS-Cork Field [Directions] | 6:00 p.m. | ||
| Fri., 4/26 | V Softball | Staples | Away - Greens Farms Elementary School-Softball Field [Directions] | 7:00 p.m. | L 0-5 | |
| Fri., 4/26 | JV Softball | Staples | Away - Staples HS-Staples Softball Field [Directions] | Postponed | ||
| Fri., 4/26 | V Girls Tennis | New Canaan | Home - Greenwich HS-Tennis Courts [Directions] | 4:00 p.m. | W 4-3 [Detailed Results] | |
| Fri., 4/26 | V Girls Water Polo | Greenwich Academy | Home - Greenwich HS-Pool [Directions] | 4:30 p.m. | Senior Night | |
| Sat., 4/27 | V Boys Lacrosse | Staples | Home - Greenwich HS-Cardinal Stadium [Directions] | 11:00 a.m. | ||
| Sat., 4/27 | JV Boys Lacrosse | Staples | Home - Greenwich HS-Field 4 [Directions] | 11:00 a.m. | ||
| Sat., 4/27 | V Boys Outdoor Track | O'Grady Relays | Away - Danbury HS-Danbury HS Stadium | 9:00 a.m. | ||
| Sat., 4/27 | V Boys Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 11:00 a.m. | ||
| Sat., 4/27 | JV Boys Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 12:30 p.m. | ||
| Sat., 4/27 | V Girls Lacrosse | Staples | Away - Staples HS-Staples Stadium [Directions] | 12:00 p.m. | ||
| Sat., 4/27 | JV Girls Lacrosse | Staples | Away - Staples HS-Staples Stadium [Directions] | 1:30 p.m. | ||
| Sat., 4/27 | V Girls Water Polo | Williston | Away - . | 4:30 p.m. | Williston | |
| Mon., 4/29 | V Baseball | Trumbull | Away - Trumbull HS-Varsity Baseball Field [Directions] | 4:30 p.m. | W 4-3 | |
| Mon., 4/29 | JV Baseball | Trumbull | Away - Trumbull HS-JV Baseball Field [Directions] | 4:30 p.m. | ||
| Mon., 4/29 | FR Baseball | Trumbull | Home - Havemeyer Field-Havermeyer Field [Directions] | 4:30 p.m. | ||
| Mon., 4/29 | FR Boys Lacrosse | Staples | Away - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Mon., 4/29 | V Girls Golf | Trumbull | Home - Griffith E Harris Golf Course [Directions] | 3:30 p.m. | ||
| Mon., 4/29 | V Softball | Trumbull | Home - Greenwich HS-Softball Field [Directions] | 4:30 p.m. | L 1-5 | |
| Mon., 4/29 | JV Softball | Trumbull | Home - Julian Curtiss School [Directions] | 4:30 p.m. | ||
| Mon., 4/29 | V Girls Tennis | Darien | Home - Greenwich HS-Tennis Courts [Directions] | 4:15 p.m. | W 6-0 [Detailed Results] | |
| Mon., 4/29 | JV Girls Tennis | Darien | Home - Binney Park [Directions] | 4:15 p.m. | JV A | |
| Tue., 4/30 | V Boys Outdoor Track | Danbury | Away - Danbury HS-Stadium Track [Directions] | 4:00 p.m. | ||
| Tue., 4/30 | V Boys Tennis | Stamford | Away - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Tue., 4/30 | V Boys Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 4/30 | JV Boys Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 4/30 | V Girls Golf | Staples | Away - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 4/30 | JV Girls Golf | Staples | Away - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 4/30 | V Girls Outdoor Track | Danbury | Away - Danbury HS-Stadium Track [Directions] | 4:00 p.m. | ||
| Tue., 4/30 | V Girls Tennis | Stamford | Home - Greenwich HS-Tennis Courts [Directions] | 4:15 p.m. | W 7-0 [Detailed Results] | |
| Tue., 4/30 | JV Girls Tennis | Wilton | Away - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/30 | V Girls Water Polo | Greenwich Aquatics | Away - . | 4:30 p.m. | Greenwich Aquatics | |
| Wed., 5/1 | V Baseball | Danbury | Away - Danbury HS-V Baseball Field [Directions] | 4:30 p.m. | W 5-1 | |
| Wed., 5/1 | JV Baseball | Danbury | Away - Danbury HS-JV Baseball Field [Directions] | 4:30 p.m. | ||
| Wed., 5/1 | FR Baseball | Danbury | Home - Havemeyer Field-Havermeyer Field [Directions] | 4:30 p.m. | ||
| Wed., 5/1 | FR Boys Lacrosse | Westhill | Home - Greenwich HS-Field 4 [Directions] | Canceled | Cancelled | |
| Wed., 5/1 | FM Boys Rugby | Aviator Sports & Events Center 3258-3264 Flatbush Ave, Brooklyn, NY 11234 | Away - Xavier HS | 6:30 p.m. | Aviator Sports & Events Center 3258-3264 Flatbush Ave, Brooklyn, NY 11234 | |
| Wed., 5/1 | V Girls Golf | Darien | Home - Griffith E Harris Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 5/1 | V Softball | Danbury | Home - Greenwich HS-Softball Field [Directions] | 4:30 p.m. | W 3-2 | |
| Wed., 5/1 | JV Softball | Danbury | Home - Julian Curtiss School [Directions] | 4:30 p.m. | ||
| Thu., 5/2 | FR Baseball | Darien | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Thu., 5/2 | V Boys Lacrosse | Ridgefield | Home - Greenwich HS-Cardinal Stadium [Directions] | 5:15 p.m. | ||
| Thu., 5/2 | JV Boys Lacrosse | Greenwich Country Day | Home - Greenwich HS-Field 4 [Directions] | 4:00 p.m. | ||
| Thu., 5/2 | V Boys Tennis | Ridgefield | Home - Greenwich HS-Tennis Courts [Directions] | 4:15 p.m. | W 5-2 [Detailed Results] | |
| Thu., 5/2 | JV Boys Tennis | Ridgefield | Home - Central MS [Directions] | 4:30 p.m. | JV A | |
| Thu., 5/2 | V Girls Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 4:30 p.m. | ||
| Thu., 5/2 | JV Girls Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Turf Field II [Directions] | Postponed | ||
| Thu., 5/2 | V Girls Rugby | Southington | Away - Southington HS-7 Rugby/Lacrosse [Directions] | 4:30 p.m. | ||
| Thu., 5/2 | V Girls Rugby | Southington | Away - Southington HS-7 Rugby/Lacrosse [Directions] | 6:00 p.m. | ||
| Thu., 5/2 | V Girls Tennis | Ridgefield | Away - Ridgefield HS-RHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Thu., 5/2 | JV Girls Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | JV B | |
| Fri., 5/3 | V Baseball | Darien | Home - Havemeyer Field-Havermeyer Field [Directions] | 4:30 p.m. | W 6-2 | |
| Fri., 5/3 | JV Baseball | Darien | Home - Julian Curtiss School [Directions] | 4:30 p.m. | ||
| Fri., 5/3 | FR Boys Lacrosse | Darien | Home - Greenwich HS-Cardinal Stadium [Directions] | 5:00 p.m. | ||
| Fri., 5/3 | V Softball | Darien | Away - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | L 1-5 | |
| Sat., 5/4 | V Boys Lacrosse | Fordham Prep (NY) | Home - Greenwich HS-Cardinal Stadium [Directions] | 2:00 p.m. | ||
| Sat., 5/4 | V Boys Rugby | Trumbull | Away - Trumbull HS-Cork Field [Directions] | 12:00 p.m. | ||
| Sat., 5/4 | JV Boys Rugby | Trumbull | Away - Trumbull HS-Cork Field [Directions] | 10:00 a.m. | ||
| Sat., 5/4 | V Boys Volleyball | New Canaan | Home - Greenwich HS-Gymnasium [Directions] | 11:00 a.m. | ||
| Sat., 5/4 | JV Boys Volleyball | New Canaan | Home - Greenwich HS-Gymnasium [Directions] | 12:00 p.m. | ||
| Mon., 5/6 | V Baseball | Stamford | Home - Havemeyer Field-Havermeyer Field [Directions] | 4:30 p.m. | ||
| Mon., 5/6 | JV Baseball | Stamford | Home - Julian Curtiss School [Directions] | 4:30 p.m. | ||
| Mon., 5/6 | FR Baseball | Stamford | Away - Belltown Park-Barrett Field, Belltown Park [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | V Boys Outdoor Track | Staples | Home - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | V Boys Tennis | Norwalk | Home - Greenwich HS-Tennis Courts [Directions] | 4:15 p.m. | ||
| Mon., 5/6 | V Boys Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | JV Boys Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 5/6 | V Girls Golf | 2024 CIAC Spring Girls Classic | Away - [CIAC] Grassy Hills Country Club | 3:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Not Listed-[CIAC] Grassy Hills Country Club | ||||||
| Mon., 5/6 | V Girls Golf | St. Joseph | Home - Fairview Country Club [Directions] | 3:30 p.m. | ||
| Mon., 5/6 | V Girls Outdoor Track | Staples | Home - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | V Softball | Stamford | Away - Troy Complex-Diamond 1 [Directions] | 7:00 p.m. | ||
| Mon., 5/6 | JV Softball | Stamford | Away - Troy Complex-Diamond 1 [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | V Girls Tennis | Norwalk | Away - Grassroots Tennis and Education-Grassroots Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | JV Girls Tennis | St. Joseph | Home - Western MS [Directions] | 4:15 p.m. | JV B | |
| Tue., 5/7 | V Boys Lacrosse | Norwalk | Home - Greenwich HS-Cardinal Stadium [Directions] | 6:00 p.m. | ||
| Tue., 5/7 | JV Boys Lacrosse | Norwalk | Home - Greenwich HS-Field 3 [Directions] | 5:00 p.m. | ||
| Tue., 5/7 | V Boys Tennis | Westhill | Away - Westhill HS-Westhill Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | JV Girls Golf | Fairfield Ludlowe | Away - Carl Dickman Par 3 [Directions] | 3:15 p.m. | ||
| Tue., 5/7 | V Girls Lacrosse | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | 5:30 p.m. | ||
| Tue., 5/7 | JV Girls Lacrosse | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | V Girls Tennis | Westhill | Home - Greenwich HS-Tennis Courts [Directions] | 4:15 p.m. | ||
| Wed., 5/8 | V Baseball | Ridgefield | Away - Governor Field [Directions] | 4:30 p.m. | ||
| Wed., 5/8 | JV Baseball | Ridgefield | Away - East Ridge MS-Baseball Field [Directions] | 4:30 p.m. | ||
| Wed., 5/8 | FR Baseball | Ridgefield | Home - Havemeyer Field-Havermeyer Field [Directions] | 4:30 p.m. | ||
| Wed., 5/8 | FR Boys Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | V Boys Tennis | Darien | Away - Darien HS-DHS Tennis Courts [Directions] | 5:00 p.m. | ||
| Wed., 5/8 | JV Boys Tennis | Darien | Away - Weed Beach Tennis Courts [Directions] | 5:00 p.m. | JV B | |
| Wed., 5/8 | V Boys Volleyball | Norwalk | Home - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | ||
| Wed., 5/8 | JV Boys Volleyball | Norwalk | Home - Greenwich HS-Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 5/8 | JV Girls Golf | Darien | Away - Wee Burn CC [Directions] | 3:00 p.m. | ||
| Wed., 5/8 | V Softball | Ridgefield | Home - Greenwich HS-Softball Field [Directions] | 5:00 p.m. | ||
| Thu., 5/9 | V Boys Tennis | Fairfield Warde | Away - Fairfield Warde HS-Blake Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/9 | JV Boys Tennis | Fairfield Warde | Away - Fairfield Warde HS-Knapps Courts [Directions] | 4:00 p.m. | JV B | |
| Thu., 5/9 | V Girls Lacrosse | Darien | Home - Greenwich HS-Cardinal Stadium [Directions] | 5:00 p.m. | ||
| Thu., 5/9 | JV Girls Lacrosse | Darien | Home - Greenwich HS-Field 3 [Directions] | 5:00 p.m. | ||
| Thu., 5/9 | V Girls Rugby | Aspetuck | Away - Aspetuck Valley Rugby Club-Default Facility | 5:00 p.m. | Aspetuck | |
| Thu., 5/9 | V Girls Tennis | Fairfield Warde | Home - Greenwich HS-Tennis Courts [Directions] | 4:15 p.m. | ||
| Thu., 5/9 | JV Girls Tennis | Fairfield Warde | Home - Binney Park [Directions] | 4:15 p.m. | JV B | |
| Fri., 5/10 | FR Boys Lacrosse | New Canaan | Home - Greenwich HS-Field 4 [Directions] | 5:00 p.m. | ||
| Fri., 5/10 | V Boys Rugby | Fairfield Prep | Away - Fairfield University-Grauert Field [Directions] | 5:30 p.m. | ||
| Fri., 5/10 | V Boys Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Fri., 5/10 | JV Boys Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Fri., 5/10 | JV Girls Tennis | New Canaan | Home - Binney Park [Directions] | 4:15 p.m. | JV A | |
| Sat., 5/11 | V Baseball | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 2:00 p.m. | ||
| Sat., 5/11 | JV Baseball | Norwalk | Away - City Hall Field [Directions] | 2:00 p.m. | ||
| Sat., 5/11 | FR Baseball | Norwalk | Home - Havemeyer Field-Havermeyer Field [Directions] | 12:00 p.m. | ||
| Sat., 5/11 | V Boys Lacrosse | Darien | Home - Greenwich HS-Cardinal Stadium [Directions] | 7:00 p.m. | ||
| Sat., 5/11 | JV Boys Lacrosse | Darien | Home - Greenwich HS-Field 3 [Directions] | 4:00 p.m. | ||
| Sat., 5/11 | V Boys Volleyball | Fairfield Warde | Home - Greenwich HS-Gymnasium [Directions] | 11:30 a.m. | ||
| Pending changes awaiting acceptance by one or more parties involved: Date to 5/9, Time to 4:15 p.m. | ||||||
| Sat., 5/11 | JV Boys Volleyball | Wilton | Home - Greenwich HS-Gymnasium [Directions] | 1:30 p.m. | ||
| Pending changes awaiting acceptance by one or more parties involved: Date to 5/9, Time to 5:30 p.m. | ||||||
| Sat., 5/11 | V Girls Lacrosse | Litchfield Coop | Home - Greenwich HS-Cardinal Stadium [Directions] | 12:00 p.m. | Senior Day | |
| Sat., 5/11 | JV Girls Lacrosse | Litchfield Coop | Home - Greenwich HS-Field 3 [Directions] | 1:00 p.m. | ||
| Sat., 5/11 | V Softball | Norwalk | Home - Greenwich HS-Softball Field [Directions] | 12:00 p.m. | ||
| Sat., 5/11 | JV Softball | Norwalk | Home - Julian Curtiss School [Directions] | 12:00 p.m. | ||
| Mon., 5/13 | V Baseball | Westhill | Home - Havemeyer Field-Havermeyer Field [Directions] | 4:30 p.m. | ||
| Mon., 5/13 | JV Baseball | Westhill | Home - Julian Curtiss School [Directions] | 4:30 p.m. | ||
| Mon., 5/13 | FR Baseball | Westhill | Away - Rippowan MS-Rippowam Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | FR Boys Lacrosse | Ridgefield | Away - Scotts Ridge MS-SRMS Turf [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | JV Boys Tennis | Wilton | Home - Central MS [Directions] | 4:30 p.m. | JV B | |
| Mon., 5/13 | V Boys Volleyball | Ridgefield | Home - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | ||
| Mon., 5/13 | JV Boys Volleyball | Ridgefield | Home - Greenwich HS-Gymnasium [Directions] | 5:15 p.m. | ||
| Mon., 5/13 | V Girls Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Mon., 5/13 | JV Girls Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Mon., 5/13 | V Softball | Westhill | Away - Westhill HS-Varsity Softball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | JV Softball | Westhill | Away - TBA [Directions] | TBA | ||
| Mon., 5/13 | JV Girls Tennis | Wilton | Away - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:15 p.m. | JV A | |
| Tue., 5/14 | V Boys Outdoor Track | Fairfield Ludlowe | Home - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | JV Boys Tennis | Brunswick School | Away - Brunswick School | 4:00 p.m. | JV A | |
| Tue., 5/14 | V Girls Golf | Ridgefield | Away - Ridgefield Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 5/14 | V Girls Lacrosse | Guilford | Away - Guilford HS-Kavanaugh Turf Field and Track [Directions] | 6:00 p.m. | ||
| Tue., 5/14 | JV Girls Lacrosse | Guilford | Away - Guilford HS-Kavanaugh Turf Field and Track [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | V Girls Outdoor Track | Fairfield Ludlowe | Home - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | V Girls Rugby | Darien | Away - MMS Upper Field-MMS Upper [Directions] | 4:30 p.m. | ||
| Wed., 5/15 | V Baseball | Fairfield Warde | Home - Havemeyer Field-Havermeyer Field [Directions] | 4:30 p.m. | ||
| Wed., 5/15 | JV Baseball | Fairfield Warde | Home - Julian Curtiss School [Directions] | 4:30 p.m. | ||
| Wed., 5/15 | FR Baseball | Fairfield Warde | Away - Fairfield Warde HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | V Boys Lacrosse | Carmel (NY) | Away - Carmel HS-N:Turf | 4:30 p.m. | ||
| Wed., 5/15 | JV Boys Lacrosse | Carmel (NY) | Home - Greenwich HS-Field 3 [Directions] | 4:30 p.m. | ||
| Wed., 5/15 | FR Boys Lacrosse | Wilton | Away - Allen's Meadow-Lacrosse Field #1 [Directions] | 4:15 p.m. | ||
| Wed., 5/15 | V Softball | Fairfield Warde | Away - Fairfield Warde HS-Softball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | JV Softball | Fairfield Warde | Away - Melville Park [Directions] | 4:00 p.m. | ||
| Thu., 5/16 | V Boys Rugby | Fairfield Ludlowe | Home - Greenwich HS-Cardinal Stadium [Directions] | 5:00 p.m. | Senior Night | |
| Thu., 5/16 | FM Boys Rugby | Fairfield Ludlowe | Home - Greenwich HS-Field 7 [Directions] | 5:00 p.m. | ||
| Thu., 5/16 | V Boys Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:00 p.m. | ||
| Thu., 5/16 | JV Boys Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 5:30 p.m. | ||
| Thu., 5/16 | V Girls Rugby | Trumbull | Home - Greenwich HS-Cardinal Stadium [Directions] | 7:00 p.m. | Senior Night | |
| Thu., 5/16 | JV Girls Tennis | Wilton | Away - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | JV B | |
| Sat., 5/18 | JV Boys Rugby | West Hartford Chart Oak Academy | Away - Xavier HS | 12:00 p.m. | West Hartford Chart Oak Academy - 425 Oakwood Ave, West Hartford, CT 06110 | |
| Sat., 5/18 | JV Boys Volleyball | JV Jamboree | Away - Fairfield Ludlowe HS-Main Gym | 8:45 a.m. | ||
| Mon., 5/20 | FM Boys Rugby | Staples | Away - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Mon., 5/20 | V Girls Golf | New Canaan | Home - The Milbrook Club-Millbrook Country Club [Directions] | 3:30 p.m. | ||
| Mon., 5/20 | JV Girls Golf | New Canaan | Home - The Milbrook Club-Millbrook Country Club [Directions] | 4:00 p.m. | ||
| Tue., 5/21 | V Girls Golf | St. Joseph | Away - Tashua Knolls Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 5/23 | V Boys Rugby | Nationals Day 1 | Away - . | TBA | Nationals Day 1 | |
| Thu., 5/23 | V Girls Rugby | Championship | Home - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Fri., 5/24 | V Boys Rugby | Nationals Day 2 | Away - . | TBA | Nationals Day 2 | |
| Sat., 5/25 | V Boys Rugby | Nationals Day 3 | Away - . | TBA | Nationals Day 3 | |
| Tue., 5/28 | V Girls Golf | Danbury | Away - Richter Park Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 5/28 | JV Girls Golf | Danbury | Away - Richter Park Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 5/29 | JV Boys Rugby | Cobra | Home - Greenwich HS-Cardinal Stadium [Directions] | 5:00 p.m. | Cobra | |
| Wed., 5/29 | FM Boys Rugby | Trumbull | Home - Greenwich HS-Field 7 [Directions] | 5:00 p.m. | ||
| Sat., 6/8 | FM Boys Rugby | Frosh Tournament | Away - . | TBA | Frosh Tournament | |