| Greenwich 2016-17 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 1153 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| TBA | JV Baseball | Ridgefield | Away - East Ridge MS [Directions] | TBA | 2:30 | |
| TBA | JV Baseball | New Canaan | Home - Julian Curtiss School [Directions] | TBA | ||
| TBA | FR Baseball | Xavier | Home - Havemeyer Field [Directions] | TBA | ||
| TBA | FR Baseball | Ridgefield | Home - GHS Baseball Field [Directions] | TBA | ||
| TBA | JV Boys Golf | Ridgefield | Away - Ridgefield Public GC (DHLY Ridge) [Directions] | Cancelled | ||
| TBA | V Boys Ice Hockey | CIAC State Tournament | Away | TBA | ||
| TBA | JV Boys Ice Hockey | Wilton | Away - Dorothy Hamill Ice Rink [Directions] | TBA | Yes | |
| TBA | JV Boys Lacrosse | St. Anthonys (NY) (Scrim.) | Home [Directions] | TBA | ||
| TBA | FR Boys Lacrosse | Darien | Home - GHS Field 7 [Directions] | 4:00 p.m. | ||
| TBA | V Boys Rugby | Amoskeag | Home - Cardinal Stadium [Directions] | TBA | ||
| TBA | V Boys Rugby | Amoskeag | Home - Cardinal Stadium [Directions] | TBA | Varsity B | |
| TBA | V Boys Sailing | REGATTA | Away - Pequot Yacht Club | TBA | ||
| TBA | JV Boys Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | Cancelled | 3:30 p.m. | |
| TBA | FR Boys Soccer | Ridgefield | Home - GHS Field 3 [Directions] | TBA | ||
| TBA | V Boys Tennis | Brunswick School (Scrim.) | Away - Brunswick School | TBA | 2:30 | |
| TBA | JV Boys Tennis | Fairfield Ludlowe | Home - Central MS [Directions] | TBA | freshman | |
| TBA | V Wrestling | Shelton Invitational | Away - Shelton HS | TBA | 8:00 am | |
| TBA | V Bowling | MATCH | Away - Nutmeg Lanes | 3:00 p.m. | 2:00 pm | 2:00 early dismissal |
| TBA | V Girls Basketball | CIAC Class LL Tournament | Away | TBA | ||
| TBA | V Girls Gymnastics | Tournament Game - Opponent Not Known | Away | TBA | Yes | |
| TBA | JV Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Dorothy Hamill Ice Rink [Directions] | 7:00 p.m. | ||
| TBA | JV Girls Ice Hockey | Stamford/Westhill/Staples (Scrim.) | Away - Terry Conners Ice Rink [Directions] | TBA | 10:00 am | |
| TBA | FR Girls Lacrosse | Darien | Away - DHS Stadium Field [Directions] | 4:00 p.m. | 2:30 | |
| TBA | V Girls Sailing | REGATTA | Away - Pequot Yacht Club | TBA | ||
| TBA | JV Softball | Brookfield | Away - PTAK Softball Field [Directions] | TBA | ||
| TBA | JV Softball | Wilton | Home - Julian Curtiss School [Directions] | TBA | ||
| TBA | FR Softball | Norwalk | Home - GHS Softball Field [Directions] | TBA | ||
| TBA | FR Softball | Norwalk | Away - Naramake School [Directions] | TBA | 2:30 | |
| TBA | JV Girls Tennis | Trumbull | Home - Binney Park [Directions] | TBA | freshman | |
| TBA | JV Girls Tennis | Fairfield Ludlowe | Away - Tomlinson MS [Directions] | TBA | 2:30 | freshman |
| Sat., 8/27 | V Boys Water Polo | Navy Tournament | Away - United States Naval Academy | 10:00 a.m. | ||
| Sat., 8/27 | JV Boys Water Polo | Navy Tournament | Away - United States Naval Academy | 10:00 a.m. | ||
| Mon., 8/29 | V Football | Practice | Away - Brunswick School | 2:30 p.m. | 1:30 p.m. | |
| Tue., 8/30 | V Field Hockey | Scrimmage | Away - Greenwich Academy | 3:30 p.m. | 2:30 p.m. | |
| Tue., 8/30 | JV Field Hockey | Scrimmage | Away - Greenwich Academy | 4:30 p.m. | share with varsity | |
| Wed., 8/31 | V Girls Soccer | Albertus Magnus | Home - GHS Field 3 [Directions] | 4:00 p.m. | ||
| Thu., 9/1 | V Boys Soccer | Notre Dame-West Haven (Scrim.) | Home - Cardinal Stadium [Directions] | 4:30 p.m. | ||
| Thu., 9/1 | JV Boys Soccer | Notre Dame-West Haven (Scrim.) | Home - GHS Field 3 [Directions] | 4:30 p.m. | ||
| Thu., 9/1 | V Girls Volleyball | Scrimmage | Away - Greenwich Academy | 3:30 p.m. | 2:30 p.m. | |
| Thu., 9/1 | JV Girls Volleyball | Scrimmage | Away - Greenwich Academy | 3:30 p.m. | share with varsity | |
| Thu., 9/1 | FR Girls Volleyball | Scrimmage | Away - Greenwich Academy | 3:30 p.m. | share with varsity | |
| Sat., 9/3 | V Football | Scrimmage | Away - Iona Prep School | 12:00 p.m. | 10:00 a.m. | 2 buses |
| Sat., 9/3 | SO Football | Scrimmage | Away - Stepinac HS | 9:00 a.m. | 7:30 a.m. | |
| Sat., 9/3 | JV Football | Iona Prep (NY) (Scrim.) | Away - Iona Prep School | 10:00 a.m. | 8:30 p.m. | |
| Sat., 9/3 | FR Football | Scrimmage | Away - Stepinac HS | 12:30 p.m. | 11:30 a.m. | 2 buses |
| Sat., 9/3 | V Field Hockey | Scrimmage | Away - Glastonbury HS | 9:00 a.m. | 6:30 a.m. | |
| Mon., 9/5 | V Field Hockey | Lauralton Hall (Scrim.) | Home - Cardinal Stadium [Directions] | 10:00 a.m. | Yes | |
| Tue., 9/6 | V Boys Soccer | Fairfield Ludlowe (Scrim.) | Away - Taft Field [Directions] | 5:30 p.m. | 3:30 p.m. | |
| Tue., 9/6 | V Girls Volleyball | Stamford (Scrim.) | Home - GHS Gymnasium [Directions] | 3:30 p.m. | ||
| Tue., 9/6 | JV Girls Volleyball | Stamford (Scrim.) | Home - GHS Gymnasium [Directions] | 3:30 p.m. | ||
| Tue., 9/6 | FR Girls Volleyball | Stamford (Scrim.) | Home - GHS Gymnasium [Directions] | 3:30 p.m. | ||
| Wed., 9/7 | V Boys Soccer | Brunswick School (Scrim.) | Away - Brunswick School | 5:00 p.m. | 3:30 p.m. | |
| Wed., 9/7 | JV Boys Soccer | Brunswick School (Scrim.) | Away - Brunswick School | 5:00 p.m. | 3:30 p.m. | |
| Wed., 9/7 | V Girls Soccer | Greenwich Academy (Scrim.) | Away - Greenwich Academy | 3:30 p.m. | 2:30 p.m. | |
| Wed., 9/7 | JV Girls Soccer | Greenwich Academy (Scrim.) | Home - GHS Field 3 [Directions] | 3:30 p.m. | ||
| Thu., 9/8 | V Boys Water Polo | NYAC | Away - New York Athletic Club | 6:45 p.m. | 4:45 | |
| Thu., 9/8 | JV Boys Water Polo | NYAC | Away - New York Athletic Club | 6:45 p.m. | share with varsity | |
| Fri., 9/9 | V Boys Soccer | Darien | Home - Cardinal Stadium [Directions] | W 2-0 | ||
| Fri., 9/9 | JV Boys Soccer | Darien | Home - GHS Field 3 [Directions] | 5:00 p.m. | ||
| Fri., 9/9 | FR Boys Soccer | Darien | Away - DHS Field #1 -Turf [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Fri., 9/9 | V Girls Volleyball | St. Joseph | Home - GHS Gymnasium [Directions] | W 3-0 | ||
| Fri., 9/9 | JV Girls Volleyball | St. Joseph | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Sat., 9/10 | V Football | Westhill | Away - Westhill Football Field [Directions] | W 22-16 | 12:30 p.m. | 2 buses |
| Sat., 9/10 | FR Football | Iona Prep (NY) | Home - Cardinal Stadium [Directions] | 10:00 a.m. | ||
| Sat., 9/10 | FR Boys Soccer | New Canaan | Home - GHS Field 7 [Directions] | 10:00 a.m. | ||
| Sat., 9/10 | V Boys Water Polo | Battle of Beltway | Away - United States Naval Academy | 10:00 a.m. | ||
| Sat., 9/10 | JV Boys Water Polo | Battle of Beltway | Away - United States Naval Academy | 10:00 a.m. | ||
| Sat., 9/10 | V Field Hockey | Staples | Away - Ginny Parker Field - Staples [Directions] | L 0-6 | 2:00 p.m. | |
| Sat., 9/10 | JV Field Hockey | Staples | Away - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | share with varsity | |
| Sat., 9/10 | FR Field Hockey | Staples | Home - Cardinal Stadium [Directions] | 10:00 a.m. | ||
| Sat., 9/10 | V Girls Soccer | Darien | Away - DHS Turf #2 [Directions] | L 1-6 | 12:30 p.m. | |
| Sat., 9/10 | JV Girls Soccer | Darien | Away - DHS Field #1 -Turf [Directions] | 2:00 p.m. | share with varsity | |
| Mon., 9/12 | JV Football | Westhill | Away - Westhill Football Field [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Mon., 9/12 | V Boys Soccer | New Canaan | Away - Conner Field [Directions] | W 2-0 | 2:30 p.m. | |
| Mon., 9/12 | JV Boys Soccer | New Canaan | Away - Saxe MS Field [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Mon., 9/12 | V Girls Soccer | New Canaan | Home - Cardinal Stadium [Directions] | T 0-0 | ||
| Mon., 9/12 | JV Girls Soccer | New Canaan | Home - GHS Field 3 [Directions] | 4:00 p.m. | ||
| Mon., 9/12 | FR Girls Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Tue., 9/13 | V Boys Cross Country | Ridgefield, Stamford, Westhill | Away - RHS Upper Grass Field [Directions] | 4:00 p.m. | 2:00 p.m. | early dismissal 2:00 p.m. |
| Tue., 9/13 | V Girls Cross Country | Ridgefield, Stamford, Westhill | Away - RHS Upper Grass Field [Directions] | 4:00 p.m. | 2:00 p.m. | early dismissal 2:00 p.m. |
| Tue., 9/13 | V Field Hockey | Stamford | Home - Cardinal Stadium [Directions] | W 7-0 | ||
| Tue., 9/13 | JV Field Hockey | Stamford | Home - Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Tue., 9/13 | FR Girls Soccer | New Canaan | Away - Saxe MS Field [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Wed., 9/14 | V Boys Soccer | St. Joseph | Away - St. Joseph HS [Directions] | W 7-2 | 2:20 p.m. | |
| Wed., 9/14 | JV Boys Soccer | St. Joseph | Away - St. Catherines, Trumbull, CT [Directions] | 4:30 p.m. | 2:30 p.m. | |
| Wed., 9/14 | V Boys Water Polo | Brunswick School | Home - GHS Gymnasium [Directions] | 4:45 p.m. | ||
| Wed., 9/14 | JV Boys Water Polo | Brunswick School | Home - GHS Gymnasium [Directions] | 6:00 p.m. | ||
| Wed., 9/14 | V Girls Soccer | St. Joseph | Home - Cardinal Stadium [Directions] | L 0-3 | ||
| Wed., 9/14 | JV Girls Soccer | St. Joseph | Home - GHS Field 3 [Directions] | 4:00 p.m. | ||
| Thu., 9/15 | FR Football | Westhill | Away - Rippowam Turf Field [Directions] | 4:00 p.m. | 2:30 p.m. | 2 buses |
| Thu., 9/15 | V Boys Water Polo | Army | Away - United States Military Academy | 4:00 p.m. | ||
| Thu., 9/15 | JV Boys Water Polo | Army | Away - United States Military Academy | 4:00 p.m. | ||
| Thu., 9/15 | V Field Hockey | Fairfield Ludlowe | Home - Cardinal Stadium [Directions] | L 2-3 | ||
| Thu., 9/15 | JV Field Hockey | Fairfield Ludlowe | Home - Cardinal Stadium [Directions] | 3:45 p.m. | ||
| Thu., 9/15 | FR Field Hockey | Fairfield Ludlowe | Away - FLHS Front Field [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Fri., 9/16 | V Boys Soccer | Westhill | Home - Cardinal Stadium [Directions] | W 3-2 | ||
| Fri., 9/16 | JV Boys Soccer | Westhill | Home - GHS Field 3 [Directions] | 5:00 p.m. | ||
| Fri., 9/16 | V Boys Water Polo | Chelsea Piers | Away - CPCT | 6:15 p.m. | ||
| Fri., 9/16 | V Girls Swimming and Diving | Staples | Away - Staples HS Pool [Directions] | 4:00 p.m. | 2:00 p.m. | early dismissal 2:00 p.m. |
| Fri., 9/16 | V Girls Volleyball | Darien | Home - GHS Gymnasium [Directions] | W 3-2 | ||
| Fri., 9/16 | JV Girls Volleyball | Darien | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 9/16 | FR Girls Volleyball | Darien | Away - DHS Main Gym [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Sat., 9/17 | V Boys Cross Country | Wilton Invitational | Away - Allens Meadow | 9:00 a.m. | ||
| Sat., 9/17 | V Football | Trinity Catholic | Home - Cardinal Stadium [Directions] | W 41-20 | ||
| Sat., 9/17 | FR Boys Soccer | Westhill | Away - Westhill Front Turf Field [Directions] | 10:00 a.m. | 10:00 a.m. | |
| Sat., 9/17 | V Girls Cross Country | Wilton Invitational | Away - Allens Meadow | 9:00 a.m. | ||
| Sat., 9/17 | V Field Hockey | Danbury | Home - Cardinal Stadium [Directions] | W 8-1 | ||
| Sat., 9/17 | JV Field Hockey | Danbury | Home - Cardinal Stadium [Directions] | 10:30 a.m. | ||
| Sat., 9/17 | V Girls Soccer | Westhill | Away - Westhill Front Turf Field [Directions] | L 0-2 | 11:00 p.m. | |
| Sat., 9/17 | JV Girls Soccer | Westhill | Away - Westhill Front Turf Field [Directions] | 2:30 p.m. | 1:15 p.m. | |
| Sat., 9/17 | V Girls Swimming and Diving | Glastonbury | Home - GHS Pool [Directions] | 12:00 p.m. | ||
| Mon., 9/19 | JV Football | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Mon., 9/19 | V Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | W 3-0 | 2:30 p.m. | |
| Mon., 9/19 | JV Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | share with varsity | |
| Mon., 9/19 | FR Girls Volleyball | New Canaan | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 9/20 | V Boys Cross Country | Trumbull, Norwalk | Away - XC Course [Directions] | 4:00 p.m. | 2:00 p.m. | early dismissal 2:00 p.m. |
| Tue., 9/20 | V Boys Soccer | Wilton | Away - Lilly Field - Turf [Directions] | W 2-1 | 4:00 p.m. | |
| Tue., 9/20 | JV Boys Soccer | Wilton | Away - Allen's Field [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Tue., 9/20 | FR Boys Soccer | Wilton | Home - GHS Field 3 [Directions] | 4:30 p.m. | ||
| Tue., 9/20 | V Girls Cross Country | Trumbull, Norwalk | Away - XC Course [Directions] | 4:00 p.m. | 2:00 p.m. | early dismissal 2:00 p.m. |
| Wed., 9/21 | V Field Hockey | Darien | Away - DHS Stadium Field [Directions] | L 1-8 | 2:30 p.m. | |
| Wed., 9/21 | JV Field Hockey | Darien | Away - DHS Stadium Field [Directions] | 5:30 p.m. | share with varsity | |
| Wed., 9/21 | V Girls Soccer | Wilton | Home - Cardinal Stadium [Directions] | L 0-3 | ||
| Wed., 9/21 | JV Girls Soccer | Wilton | Home - GHS Field 3 [Directions] | 4:00 p.m. | ||
| Wed., 9/21 | FR Girls Soccer | Wilton | Away - Allen's Field [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Wed., 9/21 | V Girls Swimming and Diving | Danbury | Home - GHS Pool [Directions] | 3:30 p.m. | ||
| Wed., 9/21 | JV Girls Swimming and Diving | Darien | Away - Darien YMCA [Directions] | 3:00 p.m. | 1:50 | |
| Wed., 9/21 | V Girls Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | W 3-1 | 2:00 p.m. | early dismissal 2:00 p.m. |
| Wed., 9/21 | JV Girls Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | share with varsity | early dismissal 2:00 p.m. |
| Wed., 9/21 | FR Girls Volleyball | St. Joseph | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 9/22 | FR Football | Darien | Home - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Thu., 9/22 | V Boys Soccer | Ridgefield | Away - Tiger Hollow Stadium [Directions] | W 2-1 | 2:30 p.m. | |
| Thu., 9/22 | JV Boys Soccer | Ridgefield | Away - RHS Lower Grass Field [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Fri., 9/23 | V Field Hockey | Norwalk | Home - Cardinal Stadium [Directions] | W 5-4(OT) | ||
| Fri., 9/23 | JV Field Hockey | Norwalk | Home - Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Fri., 9/23 | FR Field Hockey | Norwalk | Away - Nathan Hale M.S. Lower [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Fri., 9/23 | FR Girls Soccer | Ridgefield | Away - RHS Lower Grass Field [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Fri., 9/23 | V Girls Volleyball | Westhill | Home - GHS Gymnasium [Directions] | W 3-0 | ||
| Fri., 9/23 | JV Girls Volleyball | Westhill | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 9/23 | FR Girls Volleyball | Westhill | Away - Westhill New Gym [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Sat., 9/24 | V Football | Darien | Away - DHS Stadium Field [Directions] | L 35-42 | 11:30 | 2 buses |
| Sat., 9/24 | V Boys Soccer | Fairfield Warde | Home - Cardinal Stadium [Directions] | W 3-0 | ||
| Sat., 9/24 | V Boys Water Polo | Beast of the East | Away | 10:00 a.m. | ||
| Sat., 9/24 | JV Boys Water Polo | Beast of the East | Away | 10:00 a.m. | ||
| Sat., 9/24 | FR Field Hockey | Darien | Home - GHS Field 3 [Directions] | 10:00 a.m. | ||
| Sat., 9/24 | V Girls Soccer | Ridgefield | Home - Cardinal Stadium [Directions] | L 0-2 | ||
| Sat., 9/24 | JV Girls Soccer | Ridgefield | Home - GHS Field 7 [Directions] | 10:00 a.m. | 9:00 a.m. | |
| Mon., 9/26 | JV Football | Darien | Away - DHS Stadium East Turf Field [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Mon., 9/26 | V Boys Soccer | Staples | Home - Cardinal Stadium [Directions] | T 0-0 | ||
| Mon., 9/26 | JV Boys Soccer | Staples | Home - GHS Field 3 [Directions] | 4:30 p.m. | ||
| Mon., 9/26 | FR Boys Soccer | Staples | Away - Wakeman Field B (turf) [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Mon., 9/26 | V Girls Volleyball | Wilton | Away - Nicholas Zeoli Field House [Directions] | W 3-0 | 2:30 p.m. | |
| Mon., 9/26 | JV Girls Volleyball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 4:15 p.m. | share with varsity | |
| Mon., 9/26 | FR Girls Volleyball | Wilton | Home - GHS Gymnasium [Directions] | 4:30 p.m. | ||
| Tue., 9/27 | V Boys Cross Country | Staples, Brien McMahon, Fairfield Ludlowe | Away - Staples Stadium [Directions] | 4:00 p.m. | 2:00 p.m. | early dismissal 2:00 p.m. |
| Tue., 9/27 | V Girls Cross Country | Staples, Brien McMahon, Fairfield Ludlowe | Away - Staples Stadium [Directions] | 4:00 p.m. | 2:00 p.m. | early dismissal 2:00 p.m. |
| Tue., 9/27 | V Field Hockey | Wilton | Away - Fujitani Field - Turf [Directions] | L 1-4 | 2:30 p.m. | |
| Tue., 9/27 | JV Field Hockey | Wilton | Away - Fujitani Field - Turf [Directions] | 5:30 p.m. | share with varsity | |
| Tue., 9/27 | FR Field Hockey | Wilton | Home - GHS Field 3 [Directions] | 4:30 p.m. | ||
| Tue., 9/27 | V Girls Soccer | Staples | Away - Loeffler Field - Staples HS [Directions] | L 0-9 | 2:00 p.m. | early dismissal 2:00 p.m. |
| Tue., 9/27 | JV Girls Soccer | Staples | Away - Wakeman Field E (grass) [Directions] | 4:00 p.m. | share with varsity | early dismissal 2:00 p.m. |
| Tue., 9/27 | JV Girls Swimming and Diving | Staples, Ridgefield | Home - GHS Pool [Directions] | 7:15 p.m. | ||
| Wed., 9/28 | SO Football | Staples | Away - Staples Stadium [Directions] | 6:00 p.m. | 4:00 p.m. | |
| Wed., 9/28 | FR Girls Soccer | Staples | Home - GHS Field 3 [Directions] | 4:30 p.m. | ||
| Wed., 9/28 | V Girls Swimming and Diving | Fairfield Warde | Home - GHS Pool [Directions] | 3:30 p.m. | ||
| Wed., 9/28 | V Girls Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | W 3-0 | 2:00 p.m. | early dismissal 2:00 p.m. |
| Wed., 9/28 | JV Girls Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | share with varsity | early dismissal 2:00 p.m. |
| Wed., 9/28 | FR Girls Volleyball | Ridgefield | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 9/29 | V Boys Water Polo | Greenwich Aquatics | Away - YMCA | 7:30 p.m. | ||
| Thu., 9/29 | JV Boys Water Polo | Greenwich Aquatics | Away - YMCA | 7:30 p.m. | ||
| Thu., 9/29 | V Field Hockey | Ridgefield | Home - Cardinal Stadium [Directions] | W 5-0 | ||
| Thu., 9/29 | JV Field Hockey | Ridgefield | Home - Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Thu., 9/29 | FR Field Hockey | Ridgefield | Away - RHS Upper Grass Field [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Thu., 9/29 | FR Girls Soccer | Darien | Home - GHS Field 3 [Directions] | 4:00 p.m. | ||
| Fri., 9/30 | V Football | Bridgeport Central | Home - Cardinal Stadium [Directions] | W 49-22 | ||
| Fri., 9/30 | FR Boys Soccer | Trumbull | Home - GHS Field 3 [Directions] | 4:30 p.m. | ||
| Fri., 9/30 | JV Boys Water Polo | Cardinal Novice Tournament | Home - GHS Pool [Directions] | 6:00 p.m. | Friday-Saturday-Sunday | |
| Fri., 9/30 | V Girls Swimming and Diving | Fairfield Ludlowe | Home - GHS Pool [Directions] | 3:30 p.m. | ||
| Fri., 9/30 | V Girls Volleyball | Staples | Home - GHS Gymnasium [Directions] | W 3-0 | ||
| Fri., 9/30 | JV Girls Volleyball | Staples | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 9/30 | FR Girls Volleyball | Staples | Away - Staples H.S. Gym [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Sat., 10/1 | JV Football | Bridgeport Central | Home - Cardinal Stadium [Directions] | 10:00 a.m. | ||
| Tue., 10/4 | V Boys Cross Country | Fairfield Warde, Darien, New Canaan, Trinity Catholic | Home - Greenwich Point [Directions] | 4:00 p.m. | ||
| Tue., 10/4 | V Boys Soccer | Trumbull | Away - McDougall Stadium [Directions] | T 0-0 | 3:30 p.m. | |
| Tue., 10/4 | JV Boys Soccer | Trumbull | Away - Varsity Grass Field [Directions] | 5:30 p.m. | 3:30 p.m. | |
| Tue., 10/4 | V Girls Cross Country | Fairfield Warde, Darien, New Canaan, Trinity Catholic | Home - Greenwich Point [Directions] | 4:00 p.m. | ||
| Tue., 10/4 | V Girls Soccer | Trumbull | Home - Cardinal Stadium [Directions] | L 2-3 | ||
| Tue., 10/4 | JV Girls Soccer | Trumbull | Home - GHS Field 3 [Directions] | 5:00 p.m. | ||
| Tue., 10/4 | FR Girls Soccer | Trumbull | Away - The Pit [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Tue., 10/4 | V Girls Volleyball | Joel Barlow | Home - GHS Gymnasium [Directions] | W 3-0 | ||
| Tue., 10/4 | JV Girls Volleyball | Joel Barlow | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 10/5 | V Boys Soccer | Norwalk | Away - Testa Field, NHS [Directions] | W 4-2 | 5:00 p.m. | |
| Wed., 10/5 | JV Boys Soccer | Norwalk | Away - Testa Field, NHS [Directions] | 5:00 p.m. | 3:30 p.m. | |
| Wed., 10/5 | FR Boys Soccer | Norwalk | Home - GHS Field 3 [Directions] | 4:30 p.m. | ||
| Wed., 10/5 | V Field Hockey | Brien McMahon | Home - Cardinal Stadium [Directions] | W 4-0 | ||
| Wed., 10/5 | JV Field Hockey | Brien McMahon | Home - Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Thu., 10/6 | FR Football | New Canaan | Away - Dunning Stadium [Directions] | 5:00 p.m. | ||
| Thu., 10/6 | V Girls Soccer | Norwalk | Home - Cardinal Stadium [Directions] | W 2-1 | ||
| Thu., 10/6 | JV Girls Soccer | Norwalk | Home - GHS Field 3 [Directions] | 4:00 p.m. | ||
| Thu., 10/6 | FR Girls Soccer | Greenwich Country Day | Away - GCDS | 3:30 p.m. | ||
| Fri., 10/7 | FR Boys Soccer | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Fri., 10/7 | V Boys Water Polo | Skyline Invitational | Away | 6:00 p.m. | Friday-Saturday-Sunday | |
| Fri., 10/7 | V Girls Soccer | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | L 0-3 | 2:00 p.m. | |
| Fri., 10/7 | JV Girls Soccer | Fairfield Warde | Away - Fairfield Warde Grass Soccer Field [Directions] | 4:30 p.m. | share with varsity | |
| Fri., 10/7 | V Girls Swimming and Diving | Ridgefield | Home - GHS Pool [Directions] | 3:30 p.m. | ||
| Fri., 10/7 | JV Girls Swimming and Diving | Trumbull | Home - GHS Pool [Directions] | 6:00 p.m. | ||
| Fri., 10/7 | V Girls Volleyball | Trumbull | Away - THS Main Gym [Directions] | W 3-0 | 2:00 p.m. | early dismissal 2:00 p.m. |
| Fri., 10/7 | JV Girls Volleyball | Trumbull | Away - THS Main Gym [Directions] | 5:30 p.m. | share with varsity | early dismissal 2:00 p.m. |
| Fri., 10/7 | FR Girls Volleyball | Trumbull | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 10/8 | V Boys Cross Country | Wickham Invitational | Away - Wickham Park | 9:00 a.m. | 8:00 a.m. | |
| Sat., 10/8 | SO Football | Darien | Home - Cardinal Stadium [Directions] | 10:00 a.m. | ||
| Sat., 10/8 | V Girls Cross Country | Wickham Invitational | Away - Wickham Park | 9:00 a.m. | 8:00 a.m. | |
| Sat., 10/8 | V Field Hockey | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | L 1-4 | 9:00 a.m. | |
| Sat., 10/8 | JV Field Hockey | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 12:30 p.m. | share with varsity | |
| Sat., 10/8 | FR Girls Soccer | Fairfield Warde | Home - GHS Field 3 [Directions] | 9:00 a.m. | ||
| Sat., 10/8 | V Girls Volleyball | Garden State Challenge | Away | 10:00 a.m. | ||
| Mon., 10/10 | FR Boys Soccer | Stamford | Away - Stamford High Soccer Field [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Mon., 10/10 | V Field Hockey | Pomperaug | Home - Cardinal Stadium [Directions] | W 4-2 | ||
| Tue., 10/11 | V Boys Cross Country | Wilton, Danbury, St. Joseph | Home - Greenwich Point [Directions] | 3:00 p.m. | ||
| Tue., 10/11 | V Girls Cross Country | Wilton, Danbury, St. Joseph | Home - Greenwich Point [Directions] | 3:00 p.m. | ||
| Tue., 10/11 | V Girls Soccer | Stamford | Away - Stamford High Soccer Field [Directions] | W 2-0 | 1:30 p.m. | early dismissal 1:30 p.m. |
| Tue., 10/11 | JV Girls Soccer | Stamford | Away - Rippowam Field [Directions] | 3:00 p.m. | share with varsity | early dismissal 1:30 p.m. |
| Thu., 10/13 | FR Football | Trumbull | Away - McDougall Stadium [Directions] | 4:00 p.m. | 2:30 p.m. | 2 buses |
| Thu., 10/13 | V Boys Soccer | Bridgeport Central | Home - Cardinal Stadium [Directions] | W 3-0 | ||
| Thu., 10/13 | JV Boys Soccer | Bridgeport Central | Home - GHS Field 3 [Directions] | 4:15 p.m. | ||
| Thu., 10/13 | FR Field Hockey | Danbury | Away - Danbury HS Grass Field Hockey Field [Directions] | 6:00 p.m. | 11:30 a.m. | |
| Thu., 10/13 | V Girls Soccer | Bridgeport Central | Away - Kennedy Stadium [Directions] | W 5-0 | 2:00 | early dismissal 2:00 p.m. |
| Thu., 10/13 | JV Girls Swimming and Diving | Darien | Home - GHS Pool [Directions] | 7:15 p.m. | ||
| Thu., 10/13 | V Girls Volleyball | Norwalk | Away - Norwalk High Gym [Directions] | W 3-0 | 2:30 p.m. | |
| Thu., 10/13 | JV Girls Volleyball | Norwalk | Away - Norwalk High Gym [Directions] | 5:45 p.m. | share with varsity | |
| Fri., 10/14 | V Boys Soccer | Trinity Catholic | Away - Gaglio Field | W 7-0 | 2:30 p.m. | |
| Fri., 10/14 | V Boys Water Polo | Cardinal Tournament | Home - GHS Pool [Directions] | 6:00 p.m. | Friday-Saturday-Sunday | |
| Fri., 10/14 | JV Boys Water Polo | Cardinal Tournament | Home - GHS Pool [Directions] | 6:00 p.m. | Friday-Saturday-Sunday | |
| Fri., 10/14 | V Field Hockey | St. Joseph | Home - Cardinal Stadium [Directions] | W 5-0 | ||
| Fri., 10/14 | JV Field Hockey | St. Joseph | Home - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Fri., 10/14 | V Girls Swimming and Diving | Norwalk/McMahon | Home - GHS Pool [Directions] | 3:30 p.m. | ||
| Fri., 10/14 | V Girls Volleyball | Fairfield Warde | Home - GHS Gymnasium [Directions] | W 3-1 | ||
| Fri., 10/14 | JV Girls Volleyball | Fairfield Warde | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 10/14 | FR Girls Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Sat., 10/15 | V Football | Trumbull | Home - Cardinal Stadium [Directions] | W 42-32 | ||
| Mon., 10/17 | JV Football | Trumbull | Home - GHS Field 7 [Directions] | 4:00 p.m. | ||
| Mon., 10/17 | JV Boys Soccer | Fairfield Warde | Home - GHS Field 3 [Directions] | 4:30 p.m. | ||
| Mon., 10/17 | V Field Hockey | New Canaan | Away - Dunning Stadium [Directions] | OT-L 3-4 | 2:30 p.m. | |
| Mon., 10/17 | JV Field Hockey | New Canaan | Away - Dunning Stadium [Directions] | 5:30 p.m. | share with varsity | |
| Mon., 10/17 | V Girls Soccer | Trinity Catholic | Home - Cardinal Stadium [Directions] | W 5-0 | ||
| Mon., 10/17 | V Girls Volleyball | Stamford | Home - GHS Gymnasium [Directions] | L 2-3 | ||
| Mon., 10/17 | JV Girls Volleyball | Stamford | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 10/17 | FR Girls Volleyball | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Tue., 10/18 | V Boys Soccer | Danbury | Home - Cardinal Stadium [Directions] | W 5-0 | ||
| Tue., 10/18 | JV Boys Soccer | Danbury | Home - GHS Field 3 [Directions] | 4:15 p.m. | ||
| Tue., 10/18 | FR Boys Soccer | Danbury | Away - Danbury HS Grass Soccer Field [Directions] | 4:30 p.m. | 2:30 p.m. | |
| Tue., 10/18 | V Boys Water Polo | Greenwich Aquatics | Away - YMCA | 7:30 p.m. | ||
| Tue., 10/18 | JV Boys Water Polo | Greenwich Aquatics | Away - YMCA | 7:30 p.m. | ||
| Tue., 10/18 | V Girls Swimming and Diving | Darien | Home - GHS Pool [Directions] | 3:30 p.m. | ||
| Tue., 10/18 | JV Girls Swimming and Diving | Ridgefield | Home - GHS Pool [Directions] | 6:00 p.m. | ||
| Wed., 10/19 | V Boys Cross Country | FCIAC Championship | Away - Waveny Park | 2:00 p.m. | 12:30 p.m. | early dismissal 12:15 p.m. |
| Wed., 10/19 | SO Football | Trumbull | Home - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Wed., 10/19 | V Boys Water Polo | Staples | Home - GHS Pool [Directions] | 4:00 p.m. | ||
| Wed., 10/19 | JV Boys Water Polo | Staples | Home - GHS Pool [Directions] | 4:00 p.m. | ||
| Wed., 10/19 | V Girls Cross Country | FCIAC Championships | Away - Waveny Park | 2:00 p.m. | 12:30 p.m. | early dismissal 12:00 p.m. |
| Wed., 10/19 | V Field Hockey | Trumbull | Away - McDougall Stadium [Directions] | W 2-1 | 2:00p.m. | early dismissal 2:00 p.m. |
| Wed., 10/19 | JV Field Hockey | Trumbull | Away - McDougall Stadium [Directions] | 5:30 p.m. | share with varsity | early dismissal 2:00 p.m. |
| Wed., 10/19 | FR Field Hockey | Trumbull | Home - GHS Field 3 [Directions] | 4:30 p.m. | ||
| Wed., 10/19 | V Girls Soccer | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | L 0-1 | 2:00 p.m. | early dismissal 2:00 p.m. |
| Wed., 10/19 | JV Girls Soccer | Danbury | Away - Danbury HS Grass Soccer Field [Directions] | 4:00 p.m. | share with varsity | early dismissal 2:00 p.m. |
| Wed., 10/19 | V Girls Volleyball | Bridgeport Central | Home - GHS Gymnasium [Directions] | W 3-0 | ||
| Wed., 10/19 | JV Girls Volleyball | Bridgeport Central | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 10/20 | V Boys Soccer | Fairfield Ludlowe | Home - Cardinal Stadium [Directions] | W 1-0 | ||
| Thu., 10/20 | JV Boys Soccer | Fairfield Ludlowe | Home - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Thu., 10/20 | FR Boys Soccer | Fairfield Ludlowe | Away - RLMS [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Thu., 10/20 | FR Girls Soccer | Danbury | Home - GHS Field 3 [Directions] | 4:30 p.m. | ||
| Thu., 10/20 | V Girls Swimming and Diving | Westhill/Stamford | Home - GHS Pool [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Thu., 10/20 | JV Girls Swimming and Diving | Darien | Home - GHS Pool [Directions] | 6:00 p.m. | ||
| Fri., 10/21 | V Football | New Canaan | Away - Dunning Stadium [Directions] | L 16-40 | 4:00 p.m. | 2 buses |
| Fri., 10/21 | FR Girls Soccer | Fairfield Ludlowe | Home - GHS Field 3 [Directions] | 4:30 p.m. | ||
| Fri., 10/21 | V Girls Volleyball | Trinity Catholic | Away - Walsh Court | W 3-0 | 2:30 p.m. | |
| Fri., 10/21 | JV Girls Volleyball | Trinity Catholic | Away - Walsh Court | 4:00 p.m. | share with varsity | |
| Sat., 10/22 | FR Football | New Canaan | Home - Cardinal Stadium [Directions] | 10:00 a.m. | ||
| Sat., 10/22 | V Boys Soccer | Stamford | Home - Cardinal Stadium [Directions] | W 3-1 | ||
| Sat., 10/22 | JV Boys Soccer | Stamford | Home - GHS Field 3 [Directions] | 3:00 p.m. | ||
| Sat., 10/22 | V Boys Water Polo | Annapolis Classic | Away | 10:00 a.m. | ||
| Sat., 10/22 | JV Boys Water Polo | Annapolis Classic | Away | 10:00 a.m. | ||
| Sat., 10/22 | FR Field Hockey | New Canaan | Home - GHS Field 3 [Directions] | 10:00 a.m. | ||
| Sat., 10/22 | V Girls Soccer | Fairfield Ludlowe | Away - Taft Field [Directions] | L 0-1 | 11:00 a.m. | |
| Sat., 10/22 | JV Girls Soccer | Fairfield Ludlowe | Away - Sturges Park [Directions] | 4:00 p.m. | share with varsity | |
| Mon., 10/24 | JV Football | New Canaan | Away - Dunning Stadium [Directions] | 3:30 p.m. | 5:30 p.m. | |
| Mon., 10/24 | V Boys Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | T 2-2 | 5:00 p.m. | |
| Mon., 10/24 | V Girls Volleyball | Danbury | Home - GHS Gymnasium [Directions] | W 3-0 | ||
| Mon., 10/24 | JV Girls Volleyball | Danbury | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 10/24 | FR Girls Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Tue., 10/25 | V Girls Soccer | Brien McMahon | Home - Cardinal Stadium [Directions] | T 3-3 | ||
| Tue., 10/25 | JV Girls Soccer | Brien McMahon | Home - GHS Field 3 [Directions] | 4:00 p.m. | ||
| Wed., 10/26 | SO Football | Darien | Away - DHS Stadium East Turf Field [Directions] | 3:30 p.m. | 2:30 p.m. | |
| Wed., 10/26 | V Field Hockey | Westhill | Away - Westhill Front Turf Field [Directions] | W 3-1 | 2:00 p.m. | early dismissal 2:00 p.m. |
| Wed., 10/26 | JV Field Hockey | Westhill | Away - Westhill Front Turf Field [Directions] | 4:45 p.m. | share with varsity | early dismissal 2:00 p.m. |
| Wed., 10/26 | FR Field Hockey | Westhill | Home - GHS Field 3 [Directions] | 4:30 p.m. | ||
| Wed., 10/26 | V Girls Swimming and Diving | Trumbull | Away - Hillcrest MS [Directions] | 3:30 p.m. | 2:00 p.m. | early dismissal 2:00 p.m. |
| Wed., 10/26 | V Girls Volleyball | Fairfield Ludlowe | Home - GHS Gymnasium [Directions] | W 3-0 | ||
| Wed., 10/26 | JV Girls Volleyball | Fairfield Ludlowe | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 10/26 | FR Girls Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 4:00 p.m. | 2:30 p.m. | |
| Thu., 10/27 | FR Football | Fairfield Ludlowe | Away - Taft Field [Directions] | 6:00 p.m. | 4:00 p.m. | 2 buses |
| Fri., 10/28 | V Football | Fairfield Ludlowe | Home - Cardinal Stadium [Directions] | W 61-27 | ||
| Fri., 10/28 | V Boys Soccer | FCIAC Tournament | Home - Cardinal Stadium [Directions] | 3:30 p.m. | ||
| Fri., 10/28 | V Boys Water Polo | Brunswick School | Away - Brunswick | 5:00 p.m. | 4;00 p.m. | |
| Fri., 10/28 | JV Boys Water Polo | Brunswick School | Away - Brunswick | 5:00 p.m. | share with varsity | |
| Fri., 10/28 | V Field Hockey | FCIAC Tournament | Away - Darien HS | 3:30 p.m. | ||
| Fri., 10/28 | V Girls Volleyball | Brien McMahon | Away - Brien McMahon HS [Directions] | W 3-1 | 2:30 p.m. | |
| Fri., 10/28 | JV Girls Volleyball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | share with varsity | |
| Sat., 10/29 | V Boys Cross Country | CIAC Class LL Championships | Away - Wickham Park | 3:00 p.m. | 12:30 p.m. | early dismissal 12:00 p.m. |
| Sat., 10/29 | JV Football | Fairfield Ludlowe | Home - Cardinal Stadium [Directions] | 10:00 a.m. | ||
| Sat., 10/29 | V Girls Cross Country | CIAC Class LL Championships | Away - Wickham Park | 3:00 p.m. | 12:30 p.m. | early dismissal 12:00 p.m. |
| Sat., 10/29 | JV Girls Swimming and Diving | JV FCIAC Championships | Home - TBA [Directions] | 1:30 p.m. | ||
| Sat., 10/29 | JV Girls Volleyball | JV Invitational | Away - Fairfield Warde HS | 9:00 a.m. | ||
| Tue., 11/1 | V Boys Soccer | FCIAC Tournament | Away - Fairfield Ludlowe HS | 7:00 p.m. | ||
| Tue., 11/1 | V Girls Swimming and Diving | FCIAC Trials | Home - GHS Pool [Directions] | 4:00 p.m. | ||
| Tue., 11/1 | V Girls Volleyball | FCIAC Tournament | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 11/2 | V Girls Swimming and Diving | FCIAC Diving Championships | Away - Westhill HS | 4:30 p.m. | ||
| Thu., 11/3 | SO Football | New Canaan | Home - Cardinal Stadium [Directions] | 3:30 p.m. | ||
| Thu., 11/3 | V Girls Swimming and Diving | FCIAC Championships | Home - GHS Pool [Directions] | 6:30 p.m. | ||
| Fri., 11/4 | V Boys Cross Country | CIAC State Open Championships | Away | 2:00 p.m. | 11:30 a.m. | early dismissal 11:00 a.m. |
| Fri., 11/4 | V Football | Norwalk | Away - Testa Field, NHS [Directions] | W 62-34 | 5:00 p.m. | 2 buses |
| Fri., 11/4 | V Girls Cross Country | CIAC State Open | Away - Wickham Park | 2:00 p.m. | 11:30 p.m. | early dismissal 11:00 p.m. |
| Sat., 11/5 | JV Football | Norwalk | Away - Testa Field, NHS [Directions] | Cancelled | 1:30 p.m. | |
| Sat., 11/5 | FR Football | Norwalk | Home - Cardinal Stadium [Directions] | 10:00 a.m. | ||
| Sat., 11/5 | V Boys Water Polo | Chelsea Pier | Away - CPCT | 3:00 p.m. | ||
| Mon., 11/7 | Unified Sports Soccer | Tournament | Away - Staples HS | 3:00 p.m. | ||
| Tue., 11/8 | V Boys Soccer | CIAC Class LL Tournament | Home - Cardinal Stadium [Directions] | 2:00 p.m. | ||
| Wed., 11/9 | SO Football | New Canaan | Away - Dunning Stadium [Directions] | 5:00 p.m. | 3:00 p.m. | |
| Wed., 11/9 | V Field Hockey | CIAC Class L Tournament | Away - Norwalk HS | 6:00 p.m. | ||
| Thu., 11/10 | V Boys Soccer | CIAC State Tournament | Home - Cardinal Stadium [Directions] | 2:00 p.m. | ||
| Thu., 11/10 | V Girls Swimming and Diving | CIAC Class LL Diving Championships | Away | 5:25 p.m. | ||
| Thu., 11/10 | V Girls Volleyball | Class LL State Tournament | Home - GHS Gymnasium [Directions] | 5:00 p.m. | ||
| Fri., 11/11 | V Football | Ridgefield | Away - Tiger Hollow Stadium [Directions] | L 21-30 | 4:30 p.m. | 2 buses |
| Sat., 11/12 | JV Football | Ridgefield | Home - GHS Field 7 [Directions] | 11:00 a.m. | ||
| Sat., 11/12 | FR Football | Ridgefield | Home - GHS Field 7 [Directions] | 9:00 a.m. | ||
| Sat., 11/12 | V Boys Soccer | CIAC State Tournament | Home - Cardinal Stadium [Directions] | 11:00 a.m. | ||
| Sat., 11/12 | V Girls Swimming and Diving | CIAC Class LL Trials | Away - East Hartford HS | 6:00 p.m. | ||
| Sat., 11/12 | V Girls Volleyball | Class LL State Tournament | Home - GHS Gymnasium [Directions] | 2:00 p.m. | ||
| Mon., 11/14 | SO Football | Norwalk | Away - Testa Field, NHS [Directions] | 4:00 p.m. | ||
| Wed., 11/16 | V Girls Swimming and Diving | CIAC Class LL Championships | Away - Southern Connecticut State University | 6:00 p.m. | ||
| Wed., 11/16 | V Girls Volleyball | Class LL State Tournament | Away - Norwalk HS | 6:00 p.m. | ||
| Thu., 11/17 | FR Football | Staples | Away - Staples Stadium [Directions] | 6:00 p.m. | 2:30 p.m. | 2 buses |
| Fri., 11/18 | JV Football | Staples | Home - Cardinal Stadium [Directions] | 3:00 p.m. | ||
| Fri., 11/18 | V Girls Swimming and Diving | CIAC State Open Diving Championships | Away - Bulkeley HS | 5:30 p.m. | ||
| Sat., 11/19 | V Girls Swimming and Diving | CIAC State Open Championships | Away - Yale University | 12:00 p.m. | ||
| Thu., 11/24 | V Football | Staples | Home - Cardinal Stadium [Directions] | W 37-10 | ||
| Tue., 11/29 | V Football | Class LL State Playoffs | Away - Boyle Stadium | 6:30 p.m. | ||
| Tue., 11/29 | V Bowling | MATCH | Away - Nutmeg Lanes | 3:00 p.m. | 2:00 pm | 2:00 early dismissal |
| Sat., 12/3 | V Girls Basketball | Hillhouse (Scrim.) | Away - Hillhouse HS Gym [Directions] | 10:30 a.m. | 9:00 am | |
| Sat., 12/3 | V Girls Ice Hockey | Shelton Jamboree | Away | TBA | TBA | |
| Mon., 12/5 | V Girls Ice Hockey | Rye Country Day (NY) (Scrim.) | Away - RCDS | 3:30 p.m. | 2:30 pm | |
| Tue., 12/6 | V Bowling | MATCH | Away - Nutmeg Lanes | 3:00 p.m. | 2:00 pm | 2:00 early dismissal |
| Tue., 12/6 | V Girls Basketball | East Haven (Scrim.) | Away - East Haven HS [Directions] | 4:00 p.m. | 2:30 pm | |
| Wed., 12/7 | V Girls Basketball | Weston (Scrim.) | Away - WHS Gymnasium [Directions] | 3:45 p.m. | 2:30 pm | |
| Sat., 12/10 | V Boys Ice Hockey | Milford Coop (Scrim.) | Away - Milford Ice Pavilion [Directions] | 1:00 p.m. | 11:00 am | |
| Sat., 12/10 | V Wrestling | Westhill (Scrim.) | Away - Westhill HS [Directions] | 10:00 a.m. | ||
| Sat., 12/10 | V Girls Ice Hockey | Hamden Coop | Away - Lou Astorino Ice Rink [Directions] | T 1-1 | 9:00 am | |
| Sun., 12/11 | V Boys Basketball | Spring Valley (NY) (Scrim.) | Away - Spring Valley HS | 12:00 p.m. | 10:00 am | |
| Mon., 12/12 | V Boys Fencing | Greens Farms Academy | Away - Greens Farms Academy | W 14-13 | share with girls | |
| Mon., 12/12 | V Girls Basketball | New Fairfield | Home - GHS Gymnasium [Directions] | L 33-40 | ||
| Mon., 12/12 | JV Girls Basketball | New Fairfield | Home - GHS Gymnasium [Directions] | 4:30 p.m. | ||
| Mon., 12/12 | V Girls Fencing | Greens Farms Academy | Away - Greens Farms Academy | W 11-4 | 3:30 pm | |
| Tue., 12/13 | V Bowling | MATCH | Away - Nutmeg Lanes | 3:00 p.m. | 2:00 pm | 2:00 early dismissal |
| Wed., 12/14 | V Boys Basketball | Wilbur Cross (Scrim.) | Away - Wilbur Cross Gym [Directions] | 4:30 p.m. | 2:45 PM | |
| Wed., 12/14 | V Boys Fencing | Brunswick School | Away - Greenwich Academy | W 20-7 | share with girls | |
| Wed., 12/14 | V Boys Ice Hockey | Fairfield Warde/Ludlowe (Scrim.) | Away - Wonderland Of Ice [Directions] | 8:00 p.m. | 6:00 pm | |
| Wed., 12/14 | V Girls Fencing | Greenwich Academy | Away - Greenwich Academy | L 7-20 | 2:30 pm | |
| Wed., 12/14 | JV Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Conners Ice Rink [Directions] | 6:50 p.m. | 5:15 pm | |
| Thu., 12/15 | JV Wrestling | Fairfield Warde | Away - Fairfield Warde Small Gym [Directions] | 4:30 p.m. | 2:30 pm | |
| Fri., 12/16 | V Wrestling | New Rochelle (NY) | Away - New Rochelle HS | 4:30 p.m. | ||
| Fri., 12/16 | V Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | W 53-47 | 4:00 pm | |
| Fri., 12/16 | JV Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 5:15 p.m. | share with varsity | |
| Fri., 12/16 | FR Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | 2:30 pm | |
| Fri., 12/16 | V Girls Ice Hockey | East Catholic Coop | Away - Newington Ice Rink [Directions] | T 2-2 | 5:30 pm | |
| Sat., 12/17 | V Boys Basketball | Notre Dame-West Haven | Home - Trinity College [Directions] | L 61-80 | ||
| Sat., 12/17 | V Boys Ice Hockey | Xavier | Home - Dorothy Hamill Ice Rink [Directions] | L 4-5 | ||
| Sat., 12/17 | V Boys Indoor Track | MEET | Away - Staples HS | Cancelled | 9:00 am | |
| Sat., 12/17 | V Boys Indoor Track | New Haven Invitational | Away - New Haven Athletic Center | Cancelled | ||
| Sat., 12/17 | V Girls Indoor Track | MEET | Away - Staples HS | 10:00 a.m. | 9:00 am | |
| Sat., 12/17 | V Girls Indoor Track | New Haven Invitational | Away - New Haven Athletic Center | 4:00 p.m. | ||
| Mon., 12/19 | V Boys Ice Hockey | St. Joseph | Away - Shelton Rinks [Directions] | W 3-1 | 2:30 pm | |
| Tue., 12/20 | V Boys Basketball | East Hartford | Away [Directions] | L 61-64 | Yes | |
| Tue., 12/20 | V Bowling | MATCH | Away - Nutmeg Lanes | 3:00 p.m. | 2:00 pm | 2:00 early dismissal |
| Tue., 12/20 | FR Girls Basketball | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | 2:30 pm | |
| Tue., 12/20 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Dorothy Hamill Ice Rink [Directions] | W 8-0 | ||
| Wed., 12/21 | JV Boys Basketball | Notre Dame-West Haven | Away - Notre Dame HS [Directions] | 5:00 p.m. | share with freshman | |
| Wed., 12/21 | FR Boys Basketball | Notre Dame-West Haven | Away - Notre Dame HS [Directions] | 6:45 p.m. | 3:00pm | |
| Wed., 12/21 | V Wrestling | Trumbull | Home - GHS Gymnasium [Directions] | 5:00 p.m. | ||
| Thu., 12/22 | V Boys Basketball | Darien | Home - GHS Gymnasium [Directions] | W 61-38 | ||
| Thu., 12/22 | JV Boys Basketball | Darien | Home - GHS Gymnasium [Directions] | 5:15 p.m. | ||
| Thu., 12/22 | FR Boys Basketball | Darien | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 12/22 | JV Boys Ice Hockey | Darien | Away - Stamford Twin Rinks [Directions] | 4:00 p.m. | 2:30 pm | |
| Thu., 12/22 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Home - GHS Pool [Directions] | 3:30 p.m. | ||
| Thu., 12/22 | V Wrestling | Fairfield Warde, Wilton | Away - Fairfield Warde HS [Directions] | 4:00 p.m. | 2:45 pm | |
| Thu., 12/22 | V Girls Basketball | Darien | Away - DHS Main Gym [Directions] | W 59-44 | 3:00 pm | |
| Thu., 12/22 | JV Girls Basketball | Darien | Away - DHS Main Gym [Directions] | 4:00 p.m. | share with varsity | |
| Thu., 12/22 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Conners Ice Rink [Directions] | W 7-0 | 4:50 pm | |
| Tue., 12/27 | V Boys Basketball | Scarborough (ME) | Away - Portland Expo | W 67-59 | ||
| Tue., 12/27 | V Boys Ice Hockey | Hamden | Home - Dorothy Hamill Ice Rink [Directions] | L 4-7 | ||
| Tue., 12/27 | V Wrestling | Danbury Tournament | Away - Danbury HS | 9:15 a.m. | 6:45 am | |
| Tue., 12/27 | V Girls Basketball | Platt | Away - North Haven HS [Directions] | W 63-47 | 2:30 pm | |
| Tue., 12/27 | V Girls Indoor Track | Rhode Island Classic | Away - Providence Career and Technical School | 9:00 a.m. | ||
| Wed., 12/28 | V Boys Basketball | Portland (ME) | Away - Portland Expo | L 63-68 | ||
| Wed., 12/28 | V Boys Indoor Track | Wilton Wright Invitational | Away - Southern Connecticut State University | 12:00 p.m. | Yes | |
| Wed., 12/28 | V Girls Gymnastics | Joel Barlow, Staples | Home - Greenwich YWCA [Directions] | 128.7 [Detailed Results] | ||
| Wed., 12/28 | JV Girls Ice Hockey | New Canaan | Home - Dorothy Hamill Ice Rink [Directions] | 5:15 p.m. | ||
| Wed., 12/28 | V Girls Indoor Track | Wilton Wright Invitational | Away - Southern Connecticut State University | 12:00 p.m. | ||
| Thu., 12/29 | V Boys Ice Hockey | Darien | Away - Darien Ice Rink [Directions] | L 3-4 | 4:00 pm | |
| Thu., 12/29 | V Wrestling | Wilton, Brien McMahon, Danbury | Away - Nicholas Zeoli Field House [Directions] | 11:00 a.m. | 9:30 am | |
| Thu., 12/29 | V Girls Basketball | North Haven | Away - Fred Kelly Gymnasium [Directions] | W 58-33 | 2:00 | |
| Fri., 12/30 | JV Boys Ice Hockey | Norwalk | Away [Directions] | 6:00 p.m. | 4:30 | |
| Fri., 12/30 | V Boys Indoor Track | Wintergreen Invitational | Away - Southern Connecticut State University | 9:00 a.m. | Yes | |
| Fri., 12/30 | V Girls Indoor Track | Wintergreen Invitational | Away - Southern Connecticut State University | 9:00 a.m. | ||
| Sat., 12/31 | V Girls Ice Hockey | Hall/Conard | Away - Veteran's Memorial Rink [Directions] | L 0-3 | 10:15 am | |
| Tue., 1/3 | V Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | L 47-50 | 4:00 pm | |
| Tue., 1/3 | JV Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 5:00 p.m. | share with varsity | |
| Tue., 1/3 | FR Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 3:45 p.m. | 2:30 pm | |
| Tue., 1/3 | V Bowling | MATCH | Away - Nutmeg Lanes | 3:00 p.m. | 2:00 pm | 2:00 early dismissal |
| Tue., 1/3 | V Girls Basketball | New Canaan | Home - GHS Gymnasium [Directions] | W 53-33 | ||
| Tue., 1/3 | JV Girls Basketball | New Canaan | Home - GHS Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/3 | FR Girls Basketball | New Canaan | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/3 | V Girls Ice Hockey | Darien | Home - Dorothy Hamill Ice Rink [Directions] | W 3-1 | ||
| Wed., 1/4 | V Boys Ice Hockey | Rye Country Day (NY) | Away - RCDS | W 4-3 | 2:45 pm | |
| Wed., 1/4 | V Boys Swimming and Diving | Trumbull | Away - Hillcrest MS [Directions] | 4:00 p.m. | 2:00 pm | 2:00 early dismissal |
| Wed., 1/4 | V Wrestling | New Canaan | Away - NCHS Gymnasium [Directions] | 7:00 p.m. | 5:00 pm | |
| Thu., 1/5 | V Boys Alpine Skiing | RACE | Away - Mt Southington | 3:00 p.m. | 1:45 | 1:45 early dismissal |
| Thu., 1/5 | V Girls Alpine Skiing | RACE | Away - Mt Southington | 3:00 p.m. | 1:45 | 1:45 early dismissal |
| Thu., 1/5 | V Girls Gymnastics | Trumbull | Home - Greenwich YWCA [Directions] | 124.0 | ||
| Thu., 1/5 | JV Girls Ice Hockey | Greenwich Country Day | Away - GCDS | 3:30 p.m. | ||
| Fri., 1/6 | V Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | W 72-68 | 4:00 pm | |
| Fri., 1/6 | JV Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:00 p.m. | share with varsity | |
| Fri., 1/6 | FR Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 3:45 p.m. | 2:30 pm | |
| Fri., 1/6 | JV Boys Ice Hockey | Pelham Memorial (NY) | Home - Dorothy Hamill Ice Rink [Directions] | 9:15 p.m. | ||
| Fri., 1/6 | V Boys Indoor Track | Elm City Coaches Invitational | Away - New Haven Athletic Center | 4:00 p.m. | ||
| Fri., 1/6 | V Boys Swimming and Diving | Ridgefield | Away - Pool at Barlow Mountain School [Directions] | 4:00 p.m. | 2:00 pm | 2:00 early dismissal |
| Fri., 1/6 | JV Wrestling | Shoreline Tournament | Away - New Rochelle Tournament | 4:30 p.m. | 3:00 pm | |
| Fri., 1/6 | V Girls Basketball | Brien McMahon | Home - GHS Gymnasium [Directions] | W 56-43 | ||
| Fri., 1/6 | JV Girls Basketball | Brien McMahon | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/6 | FR Girls Basketball | Greenwich Country Day | Away - GCDS | 6:00 p.m. | ||
| Fri., 1/6 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Dorothy Hamill Ice Rink [Directions] | W 7-0 | ||
| Fri., 1/6 | V Girls Indoor Track | Elm City Coaches Invitational | Away - New Haven Athletic Center | 4:00 p.m. | ||
| Sat., 1/7 | V Boys Indoor Track | James Barber Invitational | Away - Southern Connecticut State University | 10:00 a.m. | ||
| Sat., 1/7 | V Boys Indoor Track | MEET | Away - Wilton HS | 9:30 a.m. | 8:30 am | |
| Sat., 1/7 | V Wrestling | Shoreline Tournament | Away - New Rochelle High school | 9:00 a.m. | 6:45 am | |
| Sat., 1/7 | JV Wrestling | Norwalk Tournament | Away - Norwalk HS | 9:00 a.m. | 7:00 am | |
| Sat., 1/7 | V Girls Indoor Track | James Barber Invitational | Away - Southern Connecticut State University | 10:00 a.m. | ||
| Sat., 1/7 | V Girls Indoor Track | MEET | Away - Wilton HS | 9:30 a.m. | 8:30 am | |
| Tue., 1/10 | V Boys Basketball | Fairfield Ludlowe | Home - GHS Gymnasium [Directions] | W 63-53 | ||
| Tue., 1/10 | JV Boys Basketball | Fairfield Ludlowe | Home - GHS Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/10 | FR Boys Basketball | Fairfield Ludlowe | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/10 | V Boys Ice Hockey | Ridgefield | Away - Winter Garden Ice Arena [Directions] | L 1-4 | 6:30 pm | |
| Tue., 1/10 | V Boys Swimming and Diving | Danbury | Away - O'Neil Center @ Western Connecticut State University [Directions] | 5:30 p.m. | 3:30 pm | |
| Tue., 1/10 | V Bowling | MATCH | Away - Nutmeg Lanes | 3:00 p.m. | 2:00 pm | 2:00 early dismissal |
| Tue., 1/10 | V Girls Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | W 54-51 | 3:00 pm | |
| Tue., 1/10 | JV Girls Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 5:15 p.m. | share with varsity | |
| Tue., 1/10 | FR Girls Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 3:45 p.m. | 2:30 pm | |
| Wed., 1/11 | V Boys Alpine Skiing | RACE | Away - Mt Southington | 3:00 p.m. | 1:45 | 1:45 early dismissal |
| Wed., 1/11 | JV Boys Ice Hockey | Brunswick School | Away - Brunswick School | 5:00 p.m. | 3:00 pm | |
| Wed., 1/11 | V Girls Alpine Skiing | RACE | Away - Mt Southington | 3:00 p.m. | 1:45 | 1:45 early dismissal |
| Wed., 1/11 | V Girls Ice Hockey | New Canaan | Away - Darien Ice House [Directions] | T 2-2(OT) | 6:10 pm | |
| Thu., 1/12 | V Boys Ice Hockey | Wilton | Home - Dorothy Hamill Ice Rink [Directions] | W 6-1 | ||
| Thu., 1/12 | V Boys Swimming and Diving | Staples | Home - GHS Pool [Directions] | 3:30 p.m. | ||
| Thu., 1/12 | V Girls Gymnastics | Wilton | Away - Wilton HS Aux. Gym [Directions] | 136.5 | 2:00 pm | 2:00 pm early dismissal |
| Fri., 1/13 | V Boys Basketball | St. Joseph | Away - St. Joseph HS [Directions] | L 49-60 | 4:00 pm | |
| Fri., 1/13 | JV Boys Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 5:15 p.m. | share with varsity | |
| Fri., 1/13 | FR Boys Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | 2:30 pm | |
| Fri., 1/13 | JV Boys Ice Hockey | Rye (NY) | Home - Dorothy Hamill Ice Rink [Directions] | 9:15 p.m. | ||
| Fri., 1/13 | V Girls Basketball | St. Joseph | Home - GHS Gymnasium [Directions] | W 43-40(OT) | ||
| Fri., 1/13 | JV Girls Basketball | St. Joseph | Home - GHS Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/13 | FR Girls Basketball | St. Joseph | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/13 | V Girls Ice Hockey | Simsbury | Away - ISCC [Directions] | W 1-0 | ||
| Sat., 1/14 | V Boys Indoor Track | MEET | Away - Staples HS | 10:00 a.m. | 9:00 am | |
| Sat., 1/14 | V Wrestling | Brien McMahon, Staples, Weston | Away - Staples HS [Directions] | 10:00 a.m. | 8:00 am | |
| Sat., 1/14 | JV Wrestling | Trumbull Duals | Away - Trumbull HS | 9:15 a.m. | 7:00 am | |
| Sat., 1/14 | Winter Dance Team | Dance in Woods | Away - Woodland Regional HS | 4:00 p.m. | 12:30 pm | |
| Sat., 1/14 | V Girls Indoor Track | MEET | Away - Staples HS | 10:00 a.m. | 9:00 am | |
| Mon., 1/16 | V Boys Ice Hockey | Northwest Catholic | Away - International Skating Center of Connecticut [Directions] | L 3-9 | TBA | |
| Mon., 1/16 | JV Boys Ice Hockey | Norwalk | Home - Dorothy Hamill Ice Rink [Directions] | 3:30 p.m. | ||
| Mon., 1/16 | JV Girls Ice Hockey | New Canaan (Scrim.) | Away - Darien Ice House [Directions] | 9:30 a.m. | 8:00 am | |
| Tue., 1/17 | V Boys Basketball | Ridgefield | Away - RHS Main Gym [Directions] | L 55-63 | 4:00 pm | |
| Tue., 1/17 | JV Boys Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 5:15 p.m. | share with varsity | |
| Tue., 1/17 | FR Boys Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | 2:30 pm | |
| Tue., 1/17 | V Bowling | MATCH | Away - Nutmeg Lanes | 3:00 p.m. | 2:00 pm | 2:00 early dismissal |
| Tue., 1/17 | V Girls Basketball | Ridgefield | Home - GHS Gymnasium [Directions] | L 51-63 | ||
| Tue., 1/17 | JV Girls Basketball | Ridgefield | Home - GHS Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/17 | FR Girls Basketball | Ridgefield | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 1/18 | V Boys Ice Hockey | New Canaan | Away - Darien Ice House [Directions] | L 4-7 | 4:00 pm | |
| Wed., 1/18 | V Boys Swimming and Diving | Darien | Away - Darien YMCA [Directions] | 3:00 p.m. | 1:00 pm | 1:00 early dismissal |
| Wed., 1/18 | V Wrestling | Stamford | Away - SHS Aux Gym [Directions] | 6:00 p.m. | 4:30 pm | |
| Wed., 1/18 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice [Directions] | W 3-2 | 1:30 pm | 1:30 pm early dismissal |
| Thu., 1/19 | V Boys Ice Hockey | Trumbull | Home - Dorothy Hamill Ice Rink [Directions] | W 6-3 | ||
| Thu., 1/19 | V Girls Basketball | Staples | Away - Staples H.S. Gym [Directions] | L 42-52 | 2:00 pm | early dismissal 2:00 |
| Thu., 1/19 | JV Girls Basketball | Staples | Away - Staples H.S. Gym [Directions] | 4:00 p.m. | share with varsity | early dismissal 2:00 |
| Fri., 1/20 | V Boys Basketball | Staples | Home - GHS Gymnasium [Directions] | W 77-71(OT) | ||
| Fri., 1/20 | JV Boys Basketball | Staples | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/20 | JV Boys Ice Hockey | New Canaan | Home - Dorothy Hamill Ice Rink [Directions] | 9:15 p.m. | ||
| Fri., 1/20 | V Boys Indoor Track | Yale Indoor Classic | Away - Coxe Cage | 1:00 p.m. | ||
| Fri., 1/20 | V Boys Swimming and Diving | Wilton | Home - GHS Pool [Directions] | 3:30 p.m. | ||
| Fri., 1/20 | V Girls Indoor Track | Yale Indoor Classic | Away - Coxe Cage | 1:00 p.m. | ||
| Sat., 1/21 | FR Boys Basketball | Staples | Home - GHS Gymnasium [Directions] | 9:00 a.m. | ||
| Sat., 1/21 | V Boys Fencing | Fairfield - Guilford - Hopkins | Away - Hopkins School | 10:00 a.m. | share with girls | |
| Sat., 1/21 | V Boys Indoor Track | MEET | Away - Staples HS | 10:00 a.m. | 9:00 am | |
| Sat., 1/21 | V Boys Indoor Track | SCC Coaches Invitational | Away - New Haven Athletic Center | 10:00 a.m. | ||
| Sat., 1/21 | V Wrestling | Walkill Duals | Away - Walkill HS | 9:30 a.m. | 6:00 am | |
| Sat., 1/21 | V Competitive Cheerleading | COMPETITION | Away - Seymour HS | 9:00 p.m. | ||
| Sat., 1/21 | FR Girls Basketball | Staples | Home - GHS Gymnasium [Directions] | 10:30 a.m. | 2:30 pm | |
| Sat., 1/21 | V Girls Fencing | Fairfield -Guilford - Hopkins | Away - Hopkins School | 10:00 a.m. | 8:00 am | |
| Sat., 1/21 | V Girls Gymnastics | Darien | Away - Darien YMCA [Directions] | 140.15 | 12:45 pm | |
| Sat., 1/21 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Dorothy Hamill Ice Rink [Directions] | W 6-2 | ||
| Sat., 1/21 | V Girls Indoor Track | MEET | Away - Staples HS | 10:00 a.m. | 9:00 am | |
| Sat., 1/21 | V Girls Indoor Track | SCC Coaches Invitational | Away - New Haven Athletic Center | 10:00 a.m. | ||
| Tue., 1/24 | V Boys Basketball | Stamford | Home - GHS Gymnasium [Directions] | W 59-50 | ||
| Tue., 1/24 | JV Boys Basketball | Stamford | Home - GHS Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/24 | FR Boys Basketball | Stamford | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/24 | V Girls Basketball | Stamford | Away - Stamford HS [Directions] | L 33-64 | 3:45 pm | |
| Tue., 1/24 | JV Girls Basketball | Stamford | Away - Stamford HS [Directions] | 5:15 p.m. | share with varsity | |
| Tue., 1/24 | FR Girls Basketball | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | 2:30 pm | |
| Wed., 1/25 | V Boys Alpine Skiing | RACE | Away - Mt Southington | 3:00 p.m. | 1:45 | 1:45 early dismissal |
| Wed., 1/25 | V Boys Ice Hockey | Notre Dame-Fairfield | Away - Milford Ice Pavilion [Directions] | L 0-6 | 4:00 pm | |
| Wed., 1/25 | V Wrestling | Fairfield Ludlowe | Home - GHS Gymnasium [Directions] | 5:00 p.m. | ||
| Wed., 1/25 | V Girls Alpine Skiing | RACE | Away - Mt Southington | 3:00 p.m. | 1:45 | 1:45 early dismissal |
| Wed., 1/25 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Winter Garden Ice Arena [Directions] | W 6-0 | 1:30 pm | 1:30 pm early dismissal |
| Thu., 1/26 | V Girls Gymnastics | Westhill, New Canaan | Home - Greenwich YWCA [Directions] | 139.6 | ||
| Thu., 1/26 | V Girls Ice Hockey | Stamford/Westhill/Staples | Home - Dorothy Hamill Ice Rink [Directions] | W 8-0 | ||
| Fri., 1/27 | V Boys Basketball | Norwalk | Away - Norwalk High Gym [Directions] | W 78-61 | 4:00 pm | |
| Fri., 1/27 | JV Boys Basketball | Norwalk | Away - Norwalk High Gym [Directions] | 5:00 p.m. | share with varsity | |
| Fri., 1/27 | FR Boys Basketball | Norwalk | Away - Norwalk High Gym [Directions] | 3:45 p.m. | 2:30 pm | |
| Fri., 1/27 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Away - Norwalk High Pool [Directions] | 3:15 p.m. | 1:15 pm | 1:15 early dismissal |
| Fri., 1/27 | V Girls Basketball | Norwalk | Home - GHS Gymnasium [Directions] | L 46-54 | ||
| Fri., 1/27 | JV Girls Basketball | Norwalk | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 1/28 | V Boys Ice Hockey | Notre Dame-West Haven | Home - Dorothy Hamill Ice Rink [Directions] | L 0-5 | ||
| Sat., 1/28 | V Boys Indoor Track | FCIAC Western Division Championships | Away - Staples HS | 10:00 a.m. | 8:00 am | |
| Sat., 1/28 | V Boys Swimming and Diving | Fairfield Prep | Home - GHS Pool [Directions] | 2:30 p.m. | ||
| Sat., 1/28 | V Wrestling | Ridgefield Challenge | Away - Ridgefield HS | 9:30 a.m. | 7:00 am | |
| Sat., 1/28 | V Girls Indoor Track | FCIAC Western Division Championships | Away - Staples HS | 10:00 a.m. | 8:00 am | |
| Wed., 2/1 | V Boys Basketball | Trumbull | Away - THS Main Gym [Directions] | L 59-66 | 4:00 pm | |
| Wed., 2/1 | JV Boys Basketball | Trumbull | Away - THS Main Gym [Directions] | 5:15 p.m. | share with varsity | |
| Wed., 2/1 | FR Boys Basketball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | 2:30 pm | |
| Wed., 2/1 | V Wrestling | Westhill | Home - GHS Gymnasium [Directions] | 4:30 p.m. | ||
| Wed., 2/1 | V Girls Basketball | Trumbull | Home - GHS Gymnasium [Directions] | L 29-42 | ||
| Wed., 2/1 | JV Girls Basketball | Trumbull | Home - GHS Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 2/1 | FR Girls Basketball | Trumbull | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 2/1 | V Girls Ice Hockey | Darien | Away - Darien Ice Rink [Directions] | L 1-3 | 5:20 pm | |
| Thu., 2/2 | V Boys Alpine Skiing | RACE | Away - Mt Southington | 3:00 p.m. | 1:45 | 1:45 early dismissal |
| Thu., 2/2 | FR Boys Basketball | Greenwich Country Day | Away - GCDS | 4:15 p.m. | ||
| Thu., 2/2 | V Boys Ice Hockey | Trinity Catholic | Home - Dorothy Hamill Ice Rink [Directions] | W 9-0 | ||
| Thu., 2/2 | V Boys Indoor Track | FCIAC Championships | Away - New Haven Athletic Center | 4:30 p.m. | 2:30 pm | |
| Thu., 2/2 | JV Wrestling | Brunswick School | Away - Brunswick School | 4:00 p.m. | 2:30 | |
| Thu., 2/2 | V Bowling | MATCH | Away - Nutmeg Lanes | 3:00 p.m. | 2:00 pm | 2:00 early dismissal |
| Thu., 2/2 | V Girls Alpine Skiing | RACE | Away - Mt Southington | 3:00 p.m. | 1:45 | 1:45 early dismissal |
| Thu., 2/2 | V Girls Gymnastics | Fairfield Ludlowe, Fairfield Warde | Home - Greenwich YWCA [Directions] | 142.15 | ||
| Thu., 2/2 | V Girls Indoor Track | FCIAC Championships | Away - New Haven Athletic Center | 4:30 p.m. | 2:30 pm | |
| Fri., 2/3 | V Boys Basketball | Westhill | Home - GHS Gymnasium [Directions] | L 60-65 | ||
| Fri., 2/3 | JV Boys Basketball | Westhill | Home - GHS Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 2/3 | FR Boys Basketball | Westhill | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 2/3 | V Boys Fencing | Brunswick School | Home - GHS Gymnasium [Directions] | 3:15 p.m. | ||
| Fri., 2/3 | JV Boys Ice Hockey | New Canaan | Away - Sono Veterans Park [Directions] | 3:30 p.m. | 2:30 pm | |
| Fri., 2/3 | V Girls Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | W 69-54 | 3:45 pm | |
| Fri., 2/3 | JV Girls Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | share with varsity | |
| Fri., 2/3 | V Girls Fencing | Greenwich Academy | Home - GHS Gymnasium [Directions] | 3:15 p.m. | ||
| Sat., 2/4 | JV Boys Fencing | Novice Tournament | Away - North Haven HS | 9:00 a.m. | 6:30 a.m. | |
| Sat., 2/4 | V Boys Swimming and Diving | New Canaan | Home - GHS Pool [Directions] | 7:00 p.m. | ||
| Sat., 2/4 | JV Wrestling | World Tournament | Away - Fairfield Ludlowe HS | 9:30 a.m. | 7:30 am | |
| Sat., 2/4 | V Competitive Cheerleading | FCIAC Championships | Away - Wilton HS | 10:00 a.m. | ||
| Sat., 2/4 | JV Girls Fencing | Novice Tournament | Away - North Haven HS | 9:00 a.m. | 6:30 am | |
| Sat., 2/4 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - So No Icehouse - Norwalk [Directions] | W 8-1 | 7:15 pm | |
| Sun., 2/5 | V Boys Ice Hockey | Iona Prep (NY) | Away - Ice Hutch | W 7-2 | Yes | |
| Mon., 2/6 | FR Boys Basketball | Brunswick School | Away - Brunswick School | 4:00 p.m. | 2:30 pm | |
| Mon., 2/6 | JV Boys Ice Hockey | Greenwich Country Day | Away - GCDS | 3:45 p.m. | ||
| Mon., 2/6 | V Wrestling | Brunswick School | Home - GHS Gymnasium [Directions] | 6:00 p.m. | ||
| Mon., 2/6 | FR Girls Basketball | New Canaan | Away - Saxe M.S. Gym [Directions] | 4:20 p.m. | ||
| Mon., 2/6 | V Girls Ice Hockey | New Canaan | Home - Dorothy Hamill Ice Rink [Directions] | T 2-2 | ||
| Tue., 2/7 | V Boys Basketball | Bridgeport Central | Home - GHS Gymnasium [Directions] | W 61-45 | ||
| Tue., 2/7 | JV Boys Basketball | Bridgeport Central | Home - GHS Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 2/7 | FR Boys Basketball | Bridgeport Central | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 2/7 | V Boys Ice Hockey | Staples | Home - Dorothy Hamill Ice Rink [Directions] | W 7-0 | ||
| Tue., 2/7 | V Boys Swimming and Diving | Westhill/Stamford | Home - GHS Pool [Directions] | 3:30 p.m. | ||
| Tue., 2/7 | V Wrestling | Ridgefield | Home - GHS Gymnasium [Directions] | 4:30 p.m. | ||
| Tue., 2/7 | V Bowling | MATCH | Away - Nutmeg Lanes | 3:00 p.m. | 2:00 pm | 2:00 early dismissal |
| Tue., 2/7 | V Girls Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | W 56-36 | 2:30 pm | |
| Tue., 2/7 | JV Girls Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 4:00 p.m. | share with varsity | |
| Wed., 2/8 | V Girls Gymnastics | Staples | Home - Greenwich YWCA [Directions] | 133.0 | ||
| Fri., 2/10 | V Boys Basketball | Wilton | Away [Directions] | L 41-61 | 3:00 pm | |
| Fri., 2/10 | JV Boys Basketball | Wilton | Away [Directions] | Cancelled | Yes | |
| Fri., 2/10 | FR Boys Basketball | Wilton | Away [Directions] | Cancelled | Yes | |
| Fri., 2/10 | V Girls Basketball | Wilton | Home - GHS Gymnasium [Directions] | W 53-49 | ||
| Fri., 2/10 | JV Girls Basketball | Wilton | Home - GHS Gymnasium [Directions] | Cancelled | ||
| Fri., 2/10 | FR Girls Basketball | Wilton | Home - GHS Gymnasium [Directions] | Cancelled | ||
| Sat., 2/11 | V Boys Fencing | Hopkins - North Haven | Away - Hopkins School | 10:00 a.m. | share with girls | |
| Sat., 2/11 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland Of Ice [Directions] | T 2-2(OT) | 5:30 pm | |
| Sat., 2/11 | V Wrestling | FCIAC Championships | Away - New Canaan HS | 9:00 a.m. | Yes | |
| Sat., 2/11 | V Girls Fencing | Hopkins - North Haven | Away - Hopkins School | 10:00 a.m. | 8:00 am | |
| Sat., 2/11 | V Girls Gymnastics | FCIAC Championships | Away - Jonathan Law HS | 143.25 | 8:30 am | |
| Sat., 2/11 | V Girls Ice Hockey | Hall/Conard | Home - Dorothy Hamill Ice Rink [Directions] | W 2-1 | ||
| Sun., 2/12 | JV Girls Ice Hockey | Wilton/Norwalk/McMahon (Scrim.) | Away - So No Icehouse - Norwalk [Directions] | 3:00 p.m. | 1:45 pm | |
| Mon., 2/13 | V Boys Basketball | Trinity Catholic | Away - Walsh Court | L 65-73 | 4:00 pm | |
| Mon., 2/13 | JV Boys Basketball | Trinity Catholic | Away - Walsh Court | 5:15 p.m. | share with varsity | |
| Mon., 2/13 | FR Boys Basketball | Trinity Catholic | Away - Walsh Court | 4:00 p.m. | 2:30 pm | |
| Mon., 2/13 | V Boys Ice Hockey | St. Joseph | Home - Dorothy Hamill Ice Rink [Directions] | L 1-5 | ||
| Mon., 2/13 | V Girls Basketball | Trinity Catholic | Home - GHS Gymnasium [Directions] | W 69-22 | ||
| Mon., 2/13 | JV Girls Basketball | Trinity Catholic | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 2/14 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Dorothy Hamill Ice Rink [Directions] | T 0-0(OT) | ||
| Wed., 2/15 | V Boys Basketball | Danbury | Home - GHS Gymnasium [Directions] | W 68-58 | ||
| Wed., 2/15 | JV Boys Basketball | Danbury | Home - GHS Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 2/15 | FR Boys Basketball | Danbury | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 2/15 | V Boys Indoor Track | CIAC Class LL Championships | Away - New Haven Athletic Center [Directions] | 4:00 p.m. | Yes | |
| Wed., 2/15 | V Girls Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | L 37-45 | 3:00 pm | |
| Wed., 2/15 | JV Girls Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 5:15 p.m. | share with varsity | |
| Wed., 2/15 | FR Girls Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 3:45 p.m. | 2:30 pm | |
| Wed., 2/15 | V Girls Indoor Track | CIAC Class LL Championships | Away - New Haven Athletic Center [Directions] | 4:00 p.m. | Yes | |
| Thu., 2/16 | V Girls Gymnastics | New Canaan | Home - Greenwich YWCA [Directions] | Cancelled | ||
| Thu., 2/16 | V Girls Ice Hockey | Simsbury | Home - Dorothy Hamill Ice Rink [Directions] | L 1-2 | ||
| Fri., 2/17 | V Wrestling | CIAC Class LL Championships | Away - Trumbull HS [Directions] | 4:00 p.m. | 2:00 pm | 2:00 early dismissal |
| Fri., 2/17 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton Rinks [Directions] | W 8-3 | 1:30 pm | |
| Sat., 2/18 | V Boys Ice Hockey | Norwalk | Away - SoNo Ice House [Directions] | W 7-0 | 5:00 pm | |
| Sat., 2/18 | V Wrestling | CIAC Class LL Championships | Away - Trumbull HS [Directions] | 9:00 a.m. | 7:00 am | |
| Sat., 2/18 | V Girls Basketball | FCIAC Tournament | Away - Ridgefield HS | 6:45 p.m. | ||
| Mon., 2/20 | V Boys Basketball | Fairfield Warde | Home - GHS Gymnasium [Directions] | L 60-61 | ||
| Mon., 2/20 | JV Boys Basketball | Fairfield Warde | Home - GHS Gymnasium [Directions] | 3:30 p.m. | ||
| Mon., 2/20 | FR Boys Basketball | Fairfield Warde | Home - GHS Gymnasium [Directions] | 2:00 p.m. | ||
| Mon., 2/20 | V Boys Ice Hockey | Darien | Home - Dorothy Hamill Ice Rink [Directions] | W 3-1 | ||
| Mon., 2/20 | V Boys Indoor Track | CIAC Open Championship | Away - New Haven Athletic Center [Directions] | 4:00 p.m. | ||
| Mon., 2/20 | V Girls Indoor Track | CIAC Open Championship | Away - New Haven Athletic Center [Directions] | 4:00 p.m. | ||
| Tue., 2/21 | V Boys Ice Hockey | Westhill/Stamford | Home - Dorothy Hamill Ice Rink [Directions] | L 0-5 | ||
| Tue., 2/21 | V Bowling | MATCH | Away - Nutmeg Lanes | 3:00 p.m. | 2:00 pm | 2:00 early dismissal |
| Tue., 2/21 | V Girls Basketball | Rye Country Day (NY) (Scrim.) | Away - RCDS | 4:00 p.m. | 3:00 | |
| Wed., 2/22 | V Boys Fencing | Rye Country Day (NY) | Away - RCDS | 4:30 p.m. | share with girls | |
| Wed., 2/22 | V Girls Fencing | Rye Country Day (NY) | Away - RCDS | 4:30 p.m. | 3:00 pm | |
| Wed., 2/22 | V Girls Ice Hockey | FCIAC Tournament | Away - Darien Ice Rink | 7:40 p.m. | ||
| Thu., 2/23 | JV Boys Ice Hockey | Brunswick School | Away - Brunswick School | 5:00 p.m. | 3:00 pm | |
| Fri., 2/24 | JV Boys Ice Hockey | Darien | Home - Dorothy Hamill Ice Rink [Directions] | 9:15 p.m. | ||
| Fri., 2/24 | V Wrestling | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:00 p.m. | ||
| Sat., 2/25 | V Boys Ice Hockey | FCIAC Tournament | Away - Terry Connors Rink | 2:30 p.m. | ||
| Sat., 2/25 | V Wrestling | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 9:00 a.m. | ||
| Sat., 2/25 | V Competitive Cheerleading | NECA Competition | Away - East Haven HS | 11:00 a.m. | ||
| Sat., 2/25 | Winter Dance Team | State Competition | Away - Shelton HS | 10:00 a.m. | ||
| Sat., 2/25 | V Girls Gymnastics | CIAC Class L State Championships | Away - Pomperaug HS | 9:00 a.m. | ||
| Sat., 2/25 | V Girls Ice Hockey | FCIAC Championship | Away - Terry Connors | 12:30 p.m. | ||
| Mon., 2/27 | V Boys Alpine Skiing | RACE | Away - Mt Southington | 3:00 p.m. | 1:45 | 1:45 early dismissal |
| Mon., 2/27 | V Girls Alpine Skiing | RACE | Away - Mt Southington | 3:00 p.m. | 1:45 | 1:45 early dismissal |
| Mon., 2/27 | V Girls Ice Hockey | State Tournament | Away - Olympic Ice Rink | 4:30 p.m. | ||
| Tue., 2/28 | V Boys Swimming and Diving | FCIAC Trials | Home - GHS Pool [Directions] | 4:30 p.m. | ||
| Tue., 2/28 | V Bowling | MATCH | Away - Nutmeg Lanes | 3:00 p.m. | 2:00 pm | 2:00 early dismissal |
| Tue., 2/28 | V Girls Basketball | CIAC Class LL Tournament | Away - Conard HS | 6:00 p.m. | ||
| Wed., 3/1 | V Boys Basketball | Fairfield Ludlowe (Scrim.) | Away - Fairfield Ludlowe HS [Directions] | 4:00 p.m. | 2:45 | |
| Wed., 3/1 | V Boys Ice Hockey | FCIAC Tournament | Away - Terry Connors Rink | 8:00 p.m. | ||
| Wed., 3/1 | V Boys Swimming and Diving | FCIAC Diving Championships | Away - Westhill HS | 4:30 p.m. | ||
| Thu., 3/2 | V Boys Alpine Skiing | State Championships | Away - Mt Southington | 3:00 p.m. | ||
| Thu., 3/2 | V Boys Swimming and Diving | FCIAC Championships | Home - GHS Pool [Directions] | 6:30 p.m. | ||
| Thu., 3/2 | V Girls Alpine Skiing | State Championships | Away - Mt Southington | 3:00 p.m. | ||
| Thu., 3/2 | V Girls Ice Hockey | State Tournament | Away - Shelton Rink | 5:30 p.m. | ||
| Fri., 3/3 | V Boys Basketball | Trinity Catholic (Scrim.) | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 3/3 | V Wrestling | New England Championships | Away - Providence Career and Technical Center [Directions] | 4:00 p.m. | ||
| Sat., 3/4 | V Boys Fencing | State Individual Championships | Away - Hopkins School | 8:00 a.m. | share with girls | |
| Sat., 3/4 | V Boys Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | TBA | ||
| Sat., 3/4 | V Wrestling | New England Championships | Away - Providence Career and Technical Center [Directions] | 9:00 a.m. | ||
| Sat., 3/4 | V Competitive Cheerleading | CIAC Championships | Away - New Haven Athletic Center | 10:00 a.m. | ||
| Sat., 3/4 | FR Girls Basketball | FCIAC Tournament | Away - St Joseph School | 9:00 a.m. | ||
| Sat., 3/4 | V Girls Fencing | State Individual Championships | Away - Hopkins School | 8:00 a.m. | 6:00 am | |
| Sat., 3/4 | V Girls Gymnastics | CIAC State Open Championships | Away | 10:00 a.m. | ||
| Sat., 3/4 | V Girls Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | TBA | ||
| Mon., 3/6 | V Boys Basketball | CIAC Class LL Tournament | Away - Trumbull HS | 6:00 p.m. | ||
| Wed., 3/8 | V Boys Ice Hockey | State Tournament | Away - Darien Ice Rink | 6:00 p.m. | ||
| Thu., 3/9 | V Boys Swimming and Diving | CIAC Class LL Diving Championships | Away - Hamden HS | 5:30 p.m. | ||
| Sat., 3/11 | V Boys Fencing | State Team Championships | Away - Waterford HS | 8:00 a.m. | share with girls | |
| Sat., 3/11 | V Boys Swimming and Diving | CIAC Class LL State Trials | Away - East Hartford HS | 3:30 p.m. | 11:30 am | |
| Sat., 3/11 | V Girls Fencing | State Team Championships | Away - Waterford HS | 8:00 a.m. | 6:00 am | |
| Sat., 3/11 | V Girls Gymnastics | New England Championships | Away | 10:00 a.m. | ||
| Mon., 3/13 | V Boys Swimming and Diving | CIAC Class LL State Championships | Away - Wesleyan University | 6:00 p.m. | 2:00 pm | 2:00 pm early dismissal |
| Fri., 3/17 | V Boys Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown HS [Directions] | 5:30 p.m. | ||
| Sat., 3/18 | V Boys Swimming and Diving | CIAC State Open Championships | Away - Yale University | 2:30 p.m. | 10:30 am | |
| Wed., 3/22 | V Boys Rugby | Fordham Prep (NY) | Home - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Wed., 3/22 | V Boys Rugby | Fordham Prep (NY) | Home - Cardinal Stadium [Directions] | 5:30 p.m. | Varsity B | |
| Thu., 3/23 | V Boys Lacrosse | Fordham Prep (NY) (Scrim.) | Home - Cardinal Stadium [Directions] | 4:30 p.m. | ||
| Thu., 3/23 | V Boys Tennis | Harrison (NY) (Scrim.) | Home - GHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 3/24 | V Girls Water Polo | Wilson | Away - Wilson School | 3:30 p.m. | ||
| Sat., 3/25 | V Boys Lacrosse | Scrimmage | Away - Darien HS | 9:00 a.m. | ||
| Wed., 3/29 | V Boys Lacrosse | Brunswick School (Scrim.) | Away - Brunswick School | 3:30 p.m. | 2:30 | |
| Wed., 3/29 | V Boys Sailing | REGATTA | Home - Grass Island [Directions] | 3:00 p.m. | ||
| Wed., 3/29 | V Girls Sailing | REGATTA | Home - Grass Island [Directions] | 3:00 p.m. | ||
| Thu., 3/30 | V Softball | New Milford (Scrim.) | Away - New Milford HS [Directions] | 4:15 p.m. | 2:30 | |
| Thu., 3/30 | V Girls Water Polo | Greenwich Aquatics | Home - GHS Pool [Directions] | 4:30 p.m. | ||
| Fri., 3/31 | JV Boys Rugby | Cheshire | Home - GHS Field 7 [Directions] | 4:30 p.m. | ||
| Sat., 4/1 | V Boys Lacrosse | St. Anthonys (NY) | Home - Cardinal Stadium [Directions] | W Forfeit | ||
| Sat., 4/1 | V Boys Rugby | USARUGBY | Home - GHS Field 7 [Directions] | 9:30 a.m. | ||
| Sat., 4/1 | FR Boys Rugby | USARUGBY | Home - GHS Field 7 [Directions] | 11:00 a.m. | ||
| Sat., 4/1 | V Boys Sailing | Greenwich 8X | Home - Grass Island [Directions] | 9:00 a.m. | ||
| Sat., 4/1 | V Girls Lacrosse | Scrimmage | Away - Greenwich Academy | 10:00 a.m. | 8:30 | |
| Sat., 4/1 | V Girls Sailing | Greenwich 8X | Home - Grass Island [Directions] | 9:00 a.m. | ||
| Mon., 4/3 | V Baseball | New Canaan | Home - GHS Baseball Field [Directions] | L 3-8 | ||
| Mon., 4/3 | V Boys Rugby | Simsbury | Home - GHS Field 7 [Directions] | 5:30 p.m. | ||
| Mon., 4/3 | V Boys Tennis | Darien | Home - GHS Tennis Courts [Directions] | W 4-3 | ||
| Mon., 4/3 | JV Boys Tennis | Darien | Home - Central MS [Directions] | 4:30 p.m. | junior varsity | |
| Mon., 4/3 | V Boys Volleyball | Ridgefield | Home - GHS Gymnasium [Directions] | L 0-3 | ||
| Mon., 4/3 | JV Boys Volleyball | Ridgefield | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 4/3 | V Girls Outdoor Track | Darien | Home - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Mon., 4/3 | V Softball | Brookfield | Away - PTAK Softball Field [Directions] | W 9-8 | 2:00 | early dismissal |
| Mon., 4/3 | V Girls Tennis | Darien | Away - DHS Tennis Courts [Directions] | L 0-7 | 2:30 | |
| Mon., 4/3 | Unified Sports Basketball | Tournament | Away - Fairfield Ludlowe HS | 3:30 p.m. | ||
| Tue., 4/4 | JV Boys Rugby | Aspetuck | Home - GHS Field 7 [Directions] | 4:45 p.m. | ||
| Tue., 4/4 | V Girls Water Polo | Greenwich Academy | Away - Greenwich Academy | 3:00 p.m. | 2:00 | early dismissal |
| Wed., 4/5 | V Boys Outdoor Track | Darien | Away - DHS Stadium Field [Directions] | 4:00 p.m. | 2:30 | |
| Wed., 4/5 | V Boys Sailing | REGATTA | Home - Grass Island [Directions] | 3:00 p.m. | ||
| Wed., 4/5 | V Boys Tennis | New Canaan | Away - NCHS Tennis Courts [Directions] | W 4-3 | 2:30 | |
| Wed., 4/5 | JV Boys Tennis | New Canaan | Home - Central MS [Directions] | 4:30 p.m. | freshman | |
| Wed., 4/5 | V Boys Volleyball | New Canaan | Home - GHS Gymnasium [Directions] | L 0-3 | ||
| Wed., 4/5 | JV Boys Volleyball | New Canaan | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 4/5 | V Girls Golf | Wilton | Home - Griffith E Harris Golf Course [Directions] | GHS: 200 WHS: 216 | ||
| Wed., 4/5 | V Girls Lacrosse | Fairfield Ludlowe | Home - Cardinal Stadium [Directions] | W 18-10 | ||
| Wed., 4/5 | JV Girls Lacrosse | Fairfield Ludlowe | Home - Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Wed., 4/5 | FR Girls Lacrosse | New Canaan | Home - GHS Field 3 [Directions] | 4:30 p.m. | ||
| Wed., 4/5 | V Girls Sailing | REGATTA | Home - Grass Island [Directions] | 3:00 p.m. | ||
| Wed., 4/5 | V Softball | Bethel | Home - Bruce Park Field [Directions] | W 6-4 | ||
| Wed., 4/5 | V Girls Tennis | New Canaan | Home - GHS Tennis Courts [Directions] | W 4-3 | ||
| Wed., 4/5 | JV Girls Tennis | Darien | Away - Weed Beach [Directions] | 4:00 p.m. | 2:30 | freshman |
| Wed., 4/5 | JV Girls Tennis | New Canaan | Home - Binney Park [Directions] | 4:00 p.m. | freshman | |
| Thu., 4/6 | V Boys Lacrosse | Stamford | Away - Stamford High Soccer Field [Directions] | W 12-3 | 2:30 | |
| Thu., 4/6 | JV Boys Lacrosse | Stamford | Away - Stamford High Soccer Field [Directions] | 5:30 p.m. | 4:00 | |
| Thu., 4/6 | V Boys Rugby | Fairfield | Home - Cardinal Stadium [Directions] | 4:00 p.m. | Varsity B | |
| Thu., 4/6 | V Boys Rugby | Fairfield | Home - Cardinal Stadium [Directions] | 6:00 p.m. | ||
| Thu., 4/6 | JV Girls Tennis | Greenwich Country Day | Away | 3:30 p.m. | junior varsity | |
| Thu., 4/6 | V Girls Water Polo | Staples | Home - GHS Pool [Directions] | 3:00 p.m. | ||
| Fri., 4/7 | V Boys Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | W 3-1 | 2:00 | early dismissal |
| Fri., 4/7 | JV Boys Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | 5:30 p.m. | share with varsity | early dismissal |
| Fri., 4/7 | V Girls Lacrosse | Danbury | Home - Cardinal Stadium [Directions] | W 18-8 | ||
| Fri., 4/7 | JV Girls Lacrosse | Danbury | Home - Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Fri., 4/7 | FR Girls Lacrosse | Trumbull | Away - McDougall Stadium [Directions] | 4:00 p.m. | 2:30 | |
| Sat., 4/8 | V Baseball | Xavier | Home - Julian Curtiss School [Directions] | L 2-5 | ||
| Sat., 4/8 | JV Baseball | Xavier | Home - Strazza Field [Directions] | 3:00 p.m. | ||
| Sat., 4/8 | V Boys Lacrosse | Somers (NY) | Away - Somers HS | W 7-5 | 1:00 | |
| Sat., 4/8 | JV Boys Lacrosse | Darien Scrimmage Day | Away - Darien HS | 3:00 p.m. | 1:30 p.m. | |
| Sat., 4/8 | JV Boys Rugby | Fairfield Prep | Home - GHS Field 7 [Directions] | 10:30 a.m. | ||
| Sat., 4/8 | FR Boys Rugby | Fairfield Prep | Home - GHS Field 7 [Directions] | 9:00 a.m. | ||
| Sat., 4/8 | V Boys Sailing | Greenwich 8X | Home - Grass Island [Directions] | 9:00 a.m. | ||
| Sat., 4/8 | V Girls Sailing | Greenwich 8X | Home - Grass Island [Directions] | 9:00 a.m. | ||
| Sat., 4/8 | V Softball | New Fairfield | Home - Bruce Park Field [Directions] | L 5-11 | 10:00 | |
| Mon., 4/10 | V Baseball | Darien | Home - GHS Baseball Field [Directions] | L 1-11 | ||
| Mon., 4/10 | JV Baseball | Darien | Home - Julian Curtiss School [Directions] | 1:00 p.m. | ||
| Mon., 4/10 | FR Baseball | Darien | Away - DHS Baseball Varsity Field [Directions] | 1:00 p.m. | 11:30 | |
| Mon., 4/10 | FR Boys Lacrosse | Wilton | Away - Allen's Field [Directions] | 4:00 p.m. | 2:00 | |
| Mon., 4/10 | V Boys Tennis | Fairfield Ludlowe | Home - GHS Tennis Courts [Directions] | W 6-1 | ||
| Mon., 4/10 | V Softball | Darien | Away - DHS Softball Varsity Field [Directions] | L 1-4 | 2:30 | |
| Mon., 4/10 | JV Softball | Darien | Away - DHS Softball JV Field [Directions] | Cancelled | share with varsity | |
| Mon., 4/10 | V Girls Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe Tennis Courts [Directions] | W 7-0 | 2:00 | early dismissal |
| Tue., 4/11 | V Boys Lacrosse | Ridgefield | Home - Cardinal Stadium [Directions] | W 8=7(OT) | ||
| Tue., 4/11 | JV Boys Lacrosse | Ridgefield | Home - GHS Field 7 [Directions] | 2:00 p.m. | ||
| Tue., 4/11 | FR Boys Lacrosse | New Canaan | Away - Dunning Stadium [Directions] | 10:00 a.m. | 8:30 a.m. | |
| Tue., 4/11 | V Girls Lacrosse | Fairfield Warde | Home - Cardinal Stadium [Directions] | W 12-9 | ||
| Tue., 4/11 | JV Girls Lacrosse | Fairfield Warde | Home - GHS Field 3 [Directions] | 1:30 p.m. | ||
| Tue., 4/11 | FR Girls Lacrosse | Wilton | Home - GHS Field 3 [Directions] | 3:00 p.m. | ||
| Wed., 4/12 | V Baseball | New Canaan | Away - Mead Park [Directions] | L 5-8 | 11:30 | |
| Wed., 4/12 | JV Baseball | New Canaan | Away - Conner Field [Directions] | 1:00 p.m. | share with varsity | |
| Wed., 4/12 | FR Baseball | New Canaan | Home - GHS Baseball Field [Directions] | 1:00 p.m. | ||
| Wed., 4/12 | FR Boys Rugby | Harvey School (NY) | Home - GHS Field 7 [Directions] | 4:00 p.m. | ||
| Wed., 4/12 | V Boys Volleyball | Darien | Home - GHS Gymnasium [Directions] | L 0-3 | ||
| Wed., 4/12 | JV Boys Volleyball | Darien | Home - GHS Gymnasium [Directions] | 11:30 a.m. | ||
| Wed., 4/12 | V Softball | New Canaan | Home - GHS Softball Field [Directions] | L 0-13 | ||
| Wed., 4/12 | JV Softball | New Canaan | Home - Julian Curtiss School [Directions] | 4:00 p.m. | ||
| Thu., 4/13 | V Baseball | Brien McMahon | Away - Nathan Hale MS [Directions] | W 11-0 | 2:30 | |
| Thu., 4/13 | JV Baseball | Brien McMahon | Away - Roton [Directions] | 4:00 p.m. | 2:30 | |
| Thu., 4/13 | V Boys Lacrosse | Westhill | Away - Westhill Football Field [Directions] | W 14-2 | 3:45 | |
| Thu., 4/13 | JV Boys Lacrosse | Westhill | Away - Westhill Football Field [Directions] | 3:30 p.m. | 2:00pm | |
| Thu., 4/13 | FR Boys Lacrosse | Staples | Home - Cardinal Stadium [Directions] | 10:00 a.m. | ||
| Thu., 4/13 | V Girls Lacrosse | Wilton | Away - Lilly Field - Turf [Directions] | L 7-8 | 4:00 | |
| Thu., 4/13 | JV Girls Lacrosse | Wilton | Away - Lilly Field - Turf [Directions] | 4:00 p.m. | 2:30 | |
| Thu., 4/13 | V Softball | Brien McMahon | Home - GHS Softball Field [Directions] | W 16-2 | ||
| Thu., 4/13 | JV Softball | Brien McMahon | Home - Julian Curtiss School [Directions] | 4:00 p.m. | ||
| Sat., 4/15 | V Boys Lacrosse | Wilton | Away - Fujitani Field - Turf [Directions] | L 7-8(OT) | 2:00 | |
| Sat., 4/15 | JV Boys Lacrosse | Wilton | Away - Fujitani Field - Turf [Directions] | 3:00 p.m. | 1:30 | |
| Sat., 4/15 | FR Boys Lacrosse | Fairfield Prep | Away - Barlow Field, Fairfield University [Directions] | 11:00 a.m. | 9:30 | |
| Sat., 4/15 | V Girls Water Polo | Choate Invitational | Away - Choate Rosemary Hall | 9:00 a.m. | Yes | |
| Mon., 4/17 | V Baseball | Fairfield Ludlowe | Home - GHS Baseball Field [Directions] | W 8-1 | ||
| Mon., 4/17 | JV Baseball | Fairfield Ludlowe | Home - Julian Curtiss School [Directions] | 4:00 p.m. | ||
| Mon., 4/17 | FR Baseball | Fairfield Ludlowe | Away - Kiwanis Field [Directions] | 4:00 p.m. | 2:30 | |
| Mon., 4/17 | V Boys Golf | Fairfield Warde | Home - Griffith E Harris Golf Course [Directions] | Greenwich 167 Warde 205 | ||
| Mon., 4/17 | JV Boys Golf | Fairfield Ludlowe, Fairfield Warde | Away - Smith Richardson Golf Course [Directions] | 3:00 p.m. | ||
| Mon., 4/17 | V Boys Outdoor Track | New Canaan | Home - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Mon., 4/17 | V Boys Tennis | St. Joseph | Away - St. Joseph HS [Directions] | W 6-1 | 2:00 | early dismissal |
| Mon., 4/17 | JV Boys Tennis | New Canaan | Home - Central MS [Directions] | 4:30 p.m. | freshman | |
| Mon., 4/17 | V Softball | Fairfield Ludlowe | Away - Sturges Park [Directions] | L 1-3 | 2:30 | |
| Mon., 4/17 | JV Softball | Fairfield Ludlowe | Away - Tom Hayden field [Directions] | 4:30 p.m. | share with varsity | |
| Mon., 4/17 | V Girls Tennis | St. Joseph | Home - GHS Tennis Courts [Directions] | W 7-0 | ||
| Mon., 4/17 | JV Girls Tennis | Wilton | Away - Wilton Tennis Courts [Directions] | 4:00 p.m. | 2:30 | freshman |
| Tue., 4/18 | V Boys Golf | Westhill | Home - Griffith E Harris Golf Course [Directions] | Greenwich 157 Westhill 192 | ||
| Tue., 4/18 | JV Boys Golf | New Canaan | Away - Innis Arden Golf Course [Directions] | 3:30 p.m. | ||
| Tue., 4/18 | V Boys Lacrosse | Staples | Home - Cardinal Stadium [Directions] | W 7-6 | ||
| Tue., 4/18 | JV Boys Lacrosse | Staples | Home - GHS Field 7 [Directions] | 4:00 p.m. | ||
| Tue., 4/18 | V Boys Rugby | Fairfield Prep | Away - Fairfield University [Directions] | 4:00 p.m. | 2:30 | |
| Tue., 4/18 | V Boys Rugby | Fairfield Prep | Away - Fairfield University [Directions] | 5:30 p.m. | 2:30 | Varsity B |
| Tue., 4/18 | V Boys Tennis | Ridgefield | Away - RHS Tennis Courts [Directions] | W 5-2 | 2:00 | early dismissal |
| Tue., 4/18 | JV Boys Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | share with varsity | junior varsity |
| Tue., 4/18 | V Boys Volleyball | Newtown | Home - GHS Gymnasium [Directions] | L 2-3 | ||
| Tue., 4/18 | JV Boys Volleyball | Newtown | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 4/18 | V Girls Golf | Fairfield Warde | Away - Smith Richardson [Directions] | GHS 191 FWHS 191 | ||
| Tue., 4/18 | V Girls Lacrosse | Glastonbury | Away - GHS Field #12 [Directions] | W 11-8 | 2:00 | early dismissal |
| Tue., 4/18 | JV Girls Lacrosse | Glastonbury | Away - GHS Field #12 [Directions] | 6:00 p.m. | share with varsity | early dismissal |
| Tue., 4/18 | V Girls Outdoor Track | New Canaan | Away - NCHS Track Field [Directions] | 4:00 p.m. | 2:30 | |
| Tue., 4/18 | V Softball | Bacon Academy | Home - GHS Softball Field [Directions] | W 16-4 | ||
| Tue., 4/18 | V Girls Tennis | Ridgefield | Home - GHS Tennis Courts [Directions] | W 7-0 | ||
| Tue., 4/18 | JV Girls Tennis | Ridgefield | Home - Binney Park [Directions] | 4:00 p.m. | junior varsity | |
| Tue., 4/18 | V Girls Water Polo | Greenwich Aquatiics | Away - Greenwich YMCA | 7:30 p.m. | ||
| Wed., 4/19 | V Baseball | St. Joseph | Away - St. Joseph HS [Directions] | L 2-14 | 2:00 | early dismissal |
| Wed., 4/19 | JV Baseball | St. Joseph | Away - Madison MS, Trumbull [Directions] | 4:00 p.m. | share with varsity | early dismissal |
| Wed., 4/19 | FR Baseball | St. Joseph | Home - GHS Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 4/19 | V Boys Sailing | REGATTA | Away - Cedar Point Yacht Club | 3:00 p.m. | ||
| Wed., 4/19 | V Boys Volleyball | Danbury | Home - GHS Gymnasium [Directions] | L 0-3 | ||
| Wed., 4/19 | JV Boys Volleyball | Danbury | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 4/19 | V Girls Golf | Darien | Home - Griffith E Harris Golf Course [Directions] | GHS 191 DHS 209 | ||
| Wed., 4/19 | FR Girls Lacrosse | Darien | Home - GHS Field 3 [Directions] | 4:30 p.m. | ||
| Wed., 4/19 | V Girls Sailing | REGATTA | Away - Cedar Point Yacht Club | 3:00 p.m. | ||
| Wed., 4/19 | V Softball | St. Joseph | Home - GHS Softball Field [Directions] | L 2-18 | ||
| Wed., 4/19 | JV Softball | St. Joseph | Home - Julian Curtiss School [Directions] | 4:00 p.m. | ||
| Wed., 4/19 | JV Girls Tennis | New Canaan | Home - Binney Park [Directions] | 4:00 p.m. | junior varsity | |
| Thu., 4/20 | V Boys Golf | Stamford | Away - EG Brennan [Directions] | Greenwich 164 Stamford 203 | ||
| Thu., 4/20 | JV Boys Golf | Darien | Home - Griffith E Harris Golf Course [Directions] | 3:15 p.m. | ||
| Thu., 4/20 | V Boys Tennis | Staples | Home - GHS Tennis Courts [Directions] | L 1-6 | ||
| Thu., 4/20 | JV Boys Tennis | Greenwich Country Day | Away | 3:30 p.m. | freshman | |
| Thu., 4/20 | JV Boys Tennis | Staples | Home - Central MS [Directions] | 4:30 p.m. | junior varsity | |
| Thu., 4/20 | V Girls Golf | Staples | Home - Griffith E Harris Golf Course [Directions] | GHS 186 SHS 198 | ||
| Thu., 4/20 | V Girls Lacrosse | Trumbull | Home - Cardinal Stadium [Directions] | W 18-7 | ||
| Thu., 4/20 | JV Girls Lacrosse | Trumbull | Home - Cardinal Stadium [Directions] | 6:30 p.m. | ||
| Thu., 4/20 | FR Softball | Newtown | Away - Newtown HS Softball Field [Directions] | 4:15 p.m. | 2:30 | |
| Thu., 4/20 | V Girls Tennis | Staples | Away - Staples HS-Tennis Courts [Directions] | L 0-7 | 2:00 | early dismissal |
| Thu., 4/20 | JV Girls Tennis | Staples | Away - Town Farms Tennis Courts [Directions] | 4:00 p.m. | share with varsity | junior varsity |
| Fri., 4/21 | V Boys Outdoor Track | Harrison Twilight | Away - Harrison HS | 6:00 p.m. | ||
| Fri., 4/21 | JV Boys Rugby | Southington | Away - Southington HS [Directions] | 5:00 p.m. | ||
| Fri., 4/21 | FR Girls Lacrosse | Ridgefield | Away - RHS Lower Grass Field [Directions] | 4:00 p.m. | 2:30 | |
| Fri., 4/21 | V Girls Outdoor Track | New York Relays | Away - Icahn Stadium | 4:00 p.m. | ||
| Sat., 4/22 | V Baseball | Ridgefield | Away - Governor's Park Field (aka Ciuccoli or Old HS) [Directions] | L 2-10 | 2:00 | early dismissal |
| Sat., 4/22 | V Boys Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | W 12-7 | 11:00 | |
| Sat., 4/22 | JV Boys Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | 11:00 a.m. | 9:30pm | |
| Sat., 4/22 | FR Boys Lacrosse | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 9:00 a.m. | 7:30 | |
| Sat., 4/22 | V Boys Rugby | Jesuit Tournament | Away | TBA | ||
| Sat., 4/22 | V Boys Sailing | O'Day Qualifier | Away - Hotchkiss School | 8:30 a.m. | ||
| Sat., 4/22 | V Girls Lacrosse | Stamford | Home - Cardinal Stadium [Directions] | W 20-3 | ||
| Sat., 4/22 | JV Girls Lacrosse | Stamford | Home - Cardinal Stadium [Directions] | 11:00 a.m. | ||
| Sat., 4/22 | V Girls Sailing | O'Day Qualifier | Away - Hotchkiss School | 8:30 a.m. | ||
| Sun., 4/23 | V Boys Sailing | O'Day NESSA Championships | Away - Connecticut College | 8:30 a.m. | ||
| Sun., 4/23 | V Girls Sailing | O'Day NESSA Championships | Away - Connecticut College | 8:30 a.m. | ||
| Mon., 4/24 | V Baseball | Staples | Home - GHS Baseball Field [Directions] | L 2-14 | ||
| Mon., 4/24 | JV Baseball | Staples | Home - Julian Curtiss School [Directions] | 4:00 p.m. | ||
| Mon., 4/24 | FR Baseball | Staples | Away - Staples HS Baseball Field [Directions] | 4:00 p.m. | 2:30 | |
| Mon., 4/24 | V Boys Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | Greenwich 155 Fairfield Ludlowe 168 | ||
| Mon., 4/24 | JV Boys Golf | Brunswick School | Away | 3:00 p.m. | ||
| Mon., 4/24 | FR Boys Lacrosse | Stamford | Away - Stamford High Soccer Field [Directions] | 5:00 p.m. | 3:30 | |
| Mon., 4/24 | V Boys Outdoor Track | Bridgeport Central, Ridgefield | Home - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Mon., 4/24 | V Boys Tennis | Stamford | Home - GHS Tennis Courts [Directions] | W 7-0 | ||
| Mon., 4/24 | JV Boys Tennis | Brunswick School | Away - Brunswick School | 4:00 p.m. | 2:30 | junior varsity |
| Mon., 4/24 | JV Boys Tennis | Horace Greeley (NY) | Home - Central MS [Directions] | 4:30 p.m. | freshman | |
| Mon., 4/24 | V Boys Volleyball | Trumbull | Away - THS Main Gym [Directions] | L 1-3 | 2:00 | early dismissal |
| Mon., 4/24 | JV Boys Volleyball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | share with varsity | early dismissal |
| Mon., 4/24 | V Girls Golf | New Canaan | Home - Griffith E Harris Golf Course [Directions] | GHS 176 NCHS 185 | ||
| Mon., 4/24 | JV Girls Lacrosse | Greenwich Academy | Away - Greenwich Academy | 4:00 p.m. | 2:30 | |
| Mon., 4/24 | V Girls Outdoor Track | Ridgefield, Bridgeport Central | Home - Greenwich HS [Directions] | 4:00 p.m. | 2:00 | |
| Mon., 4/24 | V Softball | Staples | Away - Wakeman Field [Directions] | L 1-8 | 2:00 | early dismissal |
| Mon., 4/24 | JV Softball | Staples | Away - Staples HS - Softball Field [Directions] | 4:00 p.m. | share with varsity | early dismissal |
| Mon., 4/24 | V Girls Tennis | Stamford | Away [Directions] | W 6-1 | 2:30 | |
| Tue., 4/25 | V Boys Lacrosse | Fairfield Warde | Home - Cardinal Stadium [Directions] | W 21-8 | ||
| Tue., 4/25 | V Girls Lacrosse | Westhill | Away - Westhill Front Turf Field [Directions] | W 22-5 | 2:30 | |
| Tue., 4/25 | JV Girls Lacrosse | Westhill | Away - Westhill Front Turf Field [Directions] | 5:30 p.m. | share with varsity | |
| Tue., 4/25 | V Girls Water Polo | Hopkins School | Away - Hopkins School | 4:30 p.m. | 2:00 | early dismissal |
| Wed., 4/26 | V Baseball | Stamford | Home - Julian Curtiss School [Directions] | W 7-2 | ||
| Wed., 4/26 | V Boys Golf | Trinity Catholic | Away - Sterling Farms | Greenwich 148 Trinity Catholic 202 | ||
| Wed., 4/26 | FR Boys Lacrosse | Ridgefield | Home - GHS Field 7 [Directions] | 4:30 p.m. | ||
| Wed., 4/26 | V Boys Sailing | REGATTA | Home - Grass Island [Directions] | 3:00 p.m. | ||
| Wed., 4/26 | JV Boys Tennis | Greenwich Country Day | Home - Central MS [Directions] | 4:00 p.m. | freshman | |
| Wed., 4/26 | V Boys Volleyball | Staples | Home - GHS Gymnasium [Directions] | L 0-3 | ||
| Wed., 4/26 | JV Boys Volleyball | Staples | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 4/26 | V Girls Golf | Danbury | Home - Innis Arden GC [Directions] | GHS 179 DHS 240 played from green tees | ||
| Wed., 4/26 | V Girls Sailing | REGATTA | Home - Grass Island [Directions] | 3:00 p.m. | ||
| Thu., 4/27 | FR Baseball | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | 2:30 | |
| Thu., 4/27 | V Boys Golf | Brunswick Invitational | Away - Round Hill Country Club | Greenwich 304 Brunswick 307 Bergen Catholic 317 New Canaan 322 | ||
| Thu., 4/27 | JV Boys Golf | Ridgefield | Home - Griffith E Harris Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 4/27 | V Boys Sailing | REGATTA | Away - Stamford Yacht Club | 2:45 p.m. | ||
| Thu., 4/27 | V Boys Tennis | Trumbull | Away - THS Tennis Courts [Directions] | W 5-2 | 2:00 | early dismissal |
| Thu., 4/27 | JV Boys Tennis | Fairfield Ludlowe | Away - Dwight Elementary School Courts [Directions] | 4:00 p.m. | 2:30 | junior varsity |
| Thu., 4/27 | V Girls Lacrosse | Cheshire | Away - Cheshire High Main Game field [Directions] | W 11-10 OT | 2:30 | |
| Thu., 4/27 | JV Girls Lacrosse | Cheshire | Away - Bartlem park [Directions] | 4:30 p.m. | share with varsity | |
| Thu., 4/27 | V Girls Outdoor Track | Penn Relays | Away - Franklin Field | 4:00 p.m. | ||
| Thu., 4/27 | V Girls Sailing | REGATTA | Away | 2:45 p.m. | ||
| Thu., 4/27 | V Softball | Ridgefield | Home - GHS Softball Field [Directions] | L 1-15 | ||
| Thu., 4/27 | JV Softball | Ridgefield | Home - Julian Curtiss School [Directions] | 4:30 p.m. | ||
| Thu., 4/27 | FR Softball | Newtown | Away - Treadwell Town Park [Directions] | 4:15 p.m. | 2:30 | |
| Thu., 4/27 | V Girls Tennis | Trumbull | Home - GHS Tennis Courts [Directions] | W 7-0 | ||
| Thu., 4/27 | JV Girls Tennis | Fairfield Ludlowe | Home - Binney Park [Directions] | 4:00 p.m. | freshman | |
| Thu., 4/27 | V Girls Water Polo | Staples | Away - Staples HS [Directions] | 3:00 p.m. | Yes | |
| Fri., 4/28 | V Baseball | Norwalk | Away - Nathan Hale M.S. Upper [Directions] | W 3-2 | 2:30 | |
| Fri., 4/28 | JV Baseball | Norwalk | Away - City Hall Field [Directions] | 4:00 p.m. | share with varsity | |
| Fri., 4/28 | FR Baseball | Norwalk | Home - GHS Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 4/28 | V Boys Outdoor Track | O'Grady Relays | Away - Danbury HS | 4:00 p.m. | ||
| Fri., 4/28 | V Boys Tennis | Norwalk | Home - GHS Tennis Courts [Directions] | W 7-0 | 2:30 | |
| Fri., 4/28 | V Boys Volleyball | Fairfield Warde | Home - GHS Gymnasium [Directions] | L 0-3 | ||
| Fri., 4/28 | JV Boys Volleyball | Fairfield Warde | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 4/28 | FR Girls Lacrosse | Trumbull | Home - GHS Field 3 [Directions] | 4:30 p.m. | ||
| Fri., 4/28 | V Girls Outdoor Track | O'Grady Relays | Away - Danbury HS | 4:00 p.m. | ||
| Fri., 4/28 | V Softball | Norwalk | Home - GHS Softball Field [Directions] | L 5-13 | ||
| Fri., 4/28 | JV Softball | Norwalk | Home - Julian Curtiss School [Directions] | 4:00 p.m. | ||
| Fri., 4/28 | V Girls Tennis | Norwalk | Home - GHS Tennis Courts [Directions] | W 7-0 | ||
| Sat., 4/29 | JV Baseball | Stamford | Home - Julian Curtiss School [Directions] | 10:00 a.m. | ||
| Sat., 4/29 | V Boys Lacrosse | Chaminade (NY) | Away - Chaminade HS | L 5-10 | 10:30 | |
| Sat., 4/29 | JV Boys Lacrosse | Chaminade (NY) | Away - Chaminade HS | 11:00 a.m. | 8:00 | |
| Sat., 4/29 | V Boys Rugby | Xavier (NY) | Away | TBA | STA | Varsity B |
| Sat., 4/29 | V Boys Rugby | Xavier (NY) | Away | TBA | Yes | |
| Sat., 4/29 | JV Boys Rugby | Xavier (NY) | Away | TBA | ||
| Sat., 4/29 | FR Boys Rugby | Xavier (NY) | Away | TBA | ||
| Sat., 4/29 | V Boys Sailing | State Championships | Away - United States Coast Guard Academy | 8:30 a.m. | ||
| Sat., 4/29 | V Boys Tennis | Brien McMahon | Away - Brien McMahon HS [Directions] | W 6-1 | 9:00 | |
| Sat., 4/29 | V Girls Lacrosse | Daniel Hand | Away - Surf Club [Directions] | W 15-10 | 8:30 | |
| Sat., 4/29 | JV Girls Lacrosse | Daniel Hand | Away - Surf Club [Directions] | 10:30 a.m. | share with varsity | |
| Sat., 4/29 | V Girls Sailing | Herreschoff Qualifier | Away - United states Coast Guard Academy | 8:30 a.m. | ||
| Sat., 4/29 | FR Softball | Newtown | Home - GHS Softball Field [Directions] | 10:00 a.m. | ||
| Sat., 4/29 | V Girls Tennis | Brien McMahon | Home - GHS Tennis Courts [Directions] | W 6-1 | ||
| Sat., 4/29 | V Girls Water Polo | Deerfield-Hopkins Tournament | Away - Hopkins School | 3:15 p.m. | 1:15 | |
| Sun., 4/30 | V Softball | Stamford | Away - Stamford HS [Directions] | L 1-13 | 2:30 | |
| Mon., 5/1 | V Baseball | Trumbull | Away - Varsity Baseball Field [Directions] | L 105 | 3:30 | |
| Mon., 5/1 | JV Baseball | Trumbull | Away - JV Baseball Field [Directions] | 4:00 p.m. | 2:30 | |
| Mon., 5/1 | FR Baseball | Trumbull | Home - GHS Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/1 | V Boys Golf | Wilton | Away - Rolling Hills CC [Directions] | Greenwich 151 Wilton 182 | ||
| Mon., 5/1 | JV Boys Golf | Wilton | Away - Rolling Hills Country Club [Directions] | 3:00 p.m. | ||
| Mon., 5/1 | V Boys Outdoor Track | Trumbull, Stamford | Away - McDougall Stadium [Directions] | 4:00 p.m. | 2:00 | |
| Mon., 5/1 | V Boys Tennis | Westhill | Home - GHS Tennis Courts [Directions] | W 7-0 | ||
| Mon., 5/1 | V Boys Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | L 1-3 | 2:30 | early dismissal |
| Mon., 5/1 | JV Boys Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 5:30 p.m. | share with varsity | |
| Mon., 5/1 | FR Girls Lacrosse | Fairfield Ludlowe | Away - FLHS Front Field [Directions] | 4:15 p.m. | 2:30 | |
| Mon., 5/1 | V Girls Outdoor Track | Stamford, Trumbull | Home - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Mon., 5/1 | V Softball | Trumbull | Home - GHS Softball Field [Directions] | L 2-13 | ||
| Mon., 5/1 | JV Softball | Trumbull | Home - Julian Curtiss School [Directions] | 5:00 p.m. | ||
| Mon., 5/1 | V Girls Tennis | Westhill | Away [Directions] | W 6-1 | 2:30 | |
| Tue., 5/2 | V Boys Golf | Trumbull | Home - Griffith E Harris Golf Course [Directions] | Greenwich 167 Trumbull 178 | ||
| Tue., 5/2 | FR Boys Lacrosse | Fairfield Prep | Home - Cardinal Stadium [Directions] | 4:30 p.m. | ||
| Tue., 5/2 | V Boys Tennis | Bridgeport Central | Home - GHS Tennis Courts [Directions] | W 7-0 | ||
| Tue., 5/2 | JV Boys Tennis | Fairfield Warde | Home - Central MS [Directions] | 4:30 p.m. | junior varsity | |
| Tue., 5/2 | V Girls Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | GHS 183 FLHS 214 | ||
| Tue., 5/2 | V Girls Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | W 18-7 | 4:00 | |
| Tue., 5/2 | JV Girls Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 4:30 p.m. | 3:00 | |
| Tue., 5/2 | JV Softball | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | share with varsity | |
| Tue., 5/2 | FR Softball | Norwalk | Away - Naramake School [Directions] | 4:00 p.m. | 2:30 | |
| Tue., 5/2 | V Girls Tennis | Bridgeport Central | Away [Directions] | W 7-0 | 2:00 | early dismissal |
| Tue., 5/2 | JV Girls Tennis | Fairfield Warde | Home - Binney Park [Directions] | 4:30 p.m. | junior varsity | |
| Wed., 5/3 | V Baseball | Westhill | Home - GHS Baseball Field [Directions] | L 1-2 | ||
| Wed., 5/3 | JV Baseball | Westhill | Home - Julian Curtiss School [Directions] | 4:00 p.m. | ||
| Wed., 5/3 | FR Baseball | Westhill | Away - Westhill Baseball Field [Directions] | 4:00 p.m. | 2:30 | |
| Wed., 5/3 | V Boys Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | W 15-2 | 5:00 | |
| Wed., 5/3 | JV Boys Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 4:30 p.m. | 3:00 | |
| Wed., 5/3 | FR Boys Lacrosse | New Canaan | Home - GHS Field 7 [Directions] | 4:00 p.m. | ||
| Wed., 5/3 | V Boys Sailing | REGATTA | Home - Grass Island [Directions] | 3:00 p.m. | ||
| Wed., 5/3 | V Boys Volleyball | St. Joseph | Home - GHS Gymnasium [Directions] | W 3-0 | ||
| Wed., 5/3 | JV Boys Volleyball | St. Joseph | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 5/3 | V Girls Golf | New Canaan | Away - Country Club of New Canaan [Directions] | GHS 199 NCHS 191 | ||
| Wed., 5/3 | FR Girls Lacrosse | New Canaan | Away - NCHS Water Tower Turf Field [Directions] | 4:00 p.m. | 2:30 | STA |
| Wed., 5/3 | V Girls Sailing | REGATTA | Home - Grass Island [Directions] | 3:00 p.m. | ||
| Wed., 5/3 | V Softball | Westhill | Away - Westhill Varsity Softball Field [Directions] | L 0-9 | 2:30 | |
| Wed., 5/3 | JV Softball | Westhill | Away - Roxbury Elementary School [Directions] | 4:00 p.m. | share with varsity | |
| Wed., 5/3 | JV Girls Tennis | Staples | Home - Binney Park [Directions] | 4:00 p.m. | junior varsity | |
| Thu., 5/4 | V Baseball | Bridgeport Central | Home - GHS Baseball Field [Directions] | W 9-2 | ||
| Thu., 5/4 | JV Baseball | Bridgeport Central | Home - Julian Curtiss School [Directions] | 4:00 p.m. | ||
| Thu., 5/4 | V Boys Golf | Darien | Home - Griffith E Harris Golf Course [Directions] | Greenwich 156 Darien 167 | ||
| Thu., 5/4 | JV Boys Golf | Fairfield Prep | Away - Brooklawn Country Club, Fairfield, CT [Directions] | 3:00 p.m. | ||
| Thu., 5/4 | JV Boys Rugby | West Hartford | Away | 5:30 p.m. | ||
| Thu., 5/4 | V Boys Tennis | Wilton | Away - Wilton Tennis Courts [Directions] | W 6-1 | 2:30 | |
| Thu., 5/4 | JV Boys Tennis | Wilton | Away - Middlebrook School [Directions] | 4:00 p.m. | share with varsity | junior varsity |
| Thu., 5/4 | JV Boys Tennis | Fairfield Warde | Home - Central MS [Directions] | 4:30 p.m. | freshman | |
| Thu., 5/4 | V Girls Lacrosse | Ridgefield | Away - Tiger Hollow Stadium [Directions] | L 11-10 | 2:00 | early dismissal |
| Thu., 5/4 | JV Girls Lacrosse | Ridgefield | Away - Tiger Hollow Turf Field II [Directions] | 5:30 p.m. | share with varsity | early dismissal |
| Thu., 5/4 | FR Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde Grass Utility Field [Directions] | 5:00 p.m. | 2:30 | |
| Thu., 5/4 | V Softball | Bridgeport Central | Away - Central H.S. Junior Varsity Softball Field [Directions] | W 12-3 | 2:00 | early dismissal |
| Thu., 5/4 | JV Softball | Bridgeport Central | Away - Ripken Field [Directions] | 4:30 p.m. | share with varsity | early dismissal |
| Thu., 5/4 | V Girls Tennis | Wilton | Home - GHS Tennis Courts [Directions] | W 5-2 | ||
| Thu., 5/4 | JV Girls Tennis | Wilton | Home - Binney Park [Directions] | 4:00 p.m. | junior varsity | |
| Fri., 5/5 | V Boys Rugby | Staples | Away - Staples HS [Directions] | 4:00 p.m. | 2:30 | |
| Fri., 5/5 | V Boys Rugby | Staples | Away - Staples HS [Directions] | 5:30 p.m. | 2:30 | Varsity B |
| Fri., 5/5 | FR Boys Rugby | Staples | Away - Staples HS [Directions] | 4:00 p.m. | ||
| Fri., 5/5 | V Boys Volleyball | Darien | Away - DHS Main Gym [Directions] | L 0-3 | 2:30 | |
| Fri., 5/5 | JV Boys Volleyball | Darien | Away - DHS Main Gym [Directions] | 5:30 p.m. | share with varsity | |
| Sat., 5/6 | V Boys Lacrosse | Cold Spring Harbor (NY) | Away | L 6-13 | 3:30 | |
| Sat., 5/6 | JV Boys Lacrosse | Cold Spring Harbor (NY) | Away | 4:00 p.m. | 2:00 | |
| Sat., 5/6 | V Boys Outdoor Track | Away - Willowbrook Park | Cancelled | |||
| Sat., 5/6 | V Boys Sailing | Herreshoff Trophy | Away - Brown University | 2:00 p.m. | ||
| Sat., 5/6 | V Girls Outdoor Track | Irv Black Invitational | Away - Willowbrook Park | 10:00 a.m. | ||
| Sat., 5/6 | V Girls Sailing | Herroschoff Trophy | Away - Brown University | 2:00 p.m. | ||
| Sat., 5/6 | V Girls Water Polo | NYAC | Home - GHS Pool [Directions] | 9:00 a.m. | ||
| Sun., 5/7 | V Boys Sailing | Herreshoff Trophy | Away - Brown University | 9:00 a.m. | ||
| Sun., 5/7 | V Girls Sailing | Herreschoff Trophy | Away - Brown University | 9:00 a.m. | ||
| Mon., 5/8 | V Baseball | Wilton | Away - WHS Varsity Baseball Field [Directions] | L 0-3 | 2:30 | |
| Mon., 5/8 | JV Baseball | Wilton | Away - JV Baseball Field [Directions] | 4:30 p.m. | share with varsity | |
| Mon., 5/8 | FR Baseball | Wilton | Home - GHS Baseball Field [Directions] | 4:30 p.m. | ||
| Mon., 5/8 | JV Boys Golf | Ridgefield, Staples | Away - Ridgefield Public Golf Course [Directions] | 3:00 p.m. | ||
| Mon., 5/8 | FR Boys Lacrosse | Staples | Away - Wakeman Field E (grass) [Directions] | 4:30 p.m. | 3:00 | |
| Mon., 5/8 | V Boys Outdoor Track | Westhill, Danbury | Home - Cardinal Stadium [Directions] | 3:45 p.m. | ||
| Mon., 5/8 | V Boys Tennis | Trinity Catholic | Away - Scalzi Park | W 6-1 | 2:30 | |
| Mon., 5/8 | JV Boys Tennis | Darien | Away - Cherry Lawn Park [Directions] | 4:00 p.m. | 2:30 | freshman |
| Mon., 5/8 | V Boys Volleyball | Kolbe Cathedral | Away [Directions] | W 3-0 | 2:00 | early dismissal |
| Mon., 5/8 | JV Boys Volleyball | Kolbe Cathedral | Away [Directions] | 4:00 p.m. | ||
| Mon., 5/8 | V Girls Golf | Ridgefield | Away - Ridgefield Public GC (DHLY Ridge) [Directions] | GHS 190 RHS 191 | ||
| Mon., 5/8 | V Girls Lacrosse | New Rochelle (NY) | Away - New Rochelle HS | W 19-3 | 2:30 | |
| Mon., 5/8 | JV Girls Lacrosse | New Rochelle (NY) | Away - New Rochelle HS | 6:30 p.m. | share with varsity | |
| Mon., 5/8 | FR Girls Lacrosse | Staples | Home - GHS Field 3 [Directions] | 4:30 p.m. | ||
| Mon., 5/8 | V Girls Outdoor Track | Danbury, Westhill | Away - Danbury HS Stadium [Directions] | 4:00 p.m. | 2:00 | |
| Mon., 5/8 | V Softball | Wilton | Home - GHS Softball Field [Directions] | W 4-3 | ||
| Mon., 5/8 | V Girls Tennis | Trinity Catholic | Home - GHS Tennis Courts [Directions] | W 7-0 | ||
| Mon., 5/8 | JV Girls Tennis | Darien | Home - Binney Park [Directions] | 4:00 p.m. | junior varsity | |
| Mon., 5/8 | V Girls Water Polo | Hopkins School | Home - GHS Pool [Directions] | 4:15 p.m. | ||
| Tue., 5/9 | V Boys Golf | Norwalk, Brien McMahon | Home - Griffith E Harris Golf Course [Directions] | Greenwich 156 Norwalk 222 Brien McMahon 218 | ||
| Tue., 5/9 | V Boys Lacrosse | Brien McMahon | Home - Cardinal Stadium [Directions] | W 17-7 | ||
| Tue., 5/9 | JV Boys Lacrosse | Brien McMahon | Home - GHS Field 7 [Directions] | 4:00 p.m. | ||
| Tue., 5/9 | FR Boys Lacrosse | Greenwich Country Day | Away | 3:30 p.m. | ||
| Tue., 5/9 | V Boys Tennis | Danbury | Home - GHS Tennis Courts [Directions] | W 7-0 | ||
| Tue., 5/9 | JV Boys Tennis | Greenwich Country Day | Home - Central MS [Directions] | 4:00 p.m. | junior varsity | |
| Tue., 5/9 | FR Girls Lacrosse | Staples | Away - Ginny Parker Field - Staples [Directions] | 5:15 p.m. | 2:30 | |
| Tue., 5/9 | FR Softball | Newtown | Home - GHS Softball Field [Directions] | 4:00 p.m. | ||
| Tue., 5/9 | V Girls Tennis | Danbury | Away - WCSU Tennis Courts, Westside Campus [Directions] | W 7-0 | 2:00 | early dismissal |
| Tue., 5/9 | JV Girls Tennis | Trumbull | Away - Unity Park [Directions] | 4:00 p.m. | freshman | |
| Tue., 5/9 | JV Girls Tennis | Trumbull | Away - Unity Park [Directions] | 4:00 p.m. | freshman | |
| Wed., 5/10 | V Baseball | Trinity Catholic | Away - Trinity Catholic's Lione Field | W 10-1 | 3:00 | |
| Wed., 5/10 | JV Baseball | Trinity Catholic | Away - Barrett Field @ Belltown Park | 4:30 p.m. | share with varsity | |
| Wed., 5/10 | FR Baseball | Trinity Catholic | Home - GHS Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/10 | JV Boys Rugby | Darien | Away - Darien HS [Directions] | 4:30 p.m. | ||
| Wed., 5/10 | V Boys Sailing | REGATTA | Home - Grass Island [Directions] | 2:45 p.m. | ||
| Wed., 5/10 | V Boys Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | L 0-3 | 2:30 | |
| Wed., 5/10 | JV Boys Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 6:00 p.m. | share with varsity | |
| Wed., 5/10 | V Girls Sailing | REGATTA | Home - Grass Island [Directions] | 2:45 p.m. | ||
| Wed., 5/10 | V Softball | Trinity Catholic | Home - GHS Softball Field [Directions] | W 4-3 | ||
| Wed., 5/10 | JV Softball | Trinity Catholic | Home - Julian Curtiss School [Directions] | 4:00 p.m. | ||
| Wed., 5/10 | JV Girls Tennis | Fairfield Ludlowe | Away - Tomlinson MS [Directions] | 4:00 p.m. | 2:30 | junior varsity |
| Thu., 5/11 | V Boys Golf | Danbury | Home - Griffith E Harris Golf Course [Directions] | Greenwich 154 Danbury 202 | ||
| Thu., 5/11 | JV Boys Golf | Brunswick School | Away | 3:30 p.m. | ||
| Thu., 5/11 | V Boys Lacrosse | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | W 17-7 | 2:30 | |
| Thu., 5/11 | JV Boys Lacrosse | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 6:00 p.m. | 4:30 | |
| Thu., 5/11 | V Boys Tennis | Fairfield Warde | Home - GHS Tennis Courts [Directions] | W 7-0 | ||
| Thu., 5/11 | JV Boys Tennis | Darien | Away - Cherry Lawn Park [Directions] | 4:00 p.m. | 2:30 | junior varsity |
| Thu., 5/11 | JV Boys Tennis | Fairfield Warde | Home - Central MS [Directions] | 4:30 p.m. | freshman | |
| Thu., 5/11 | V Girls Golf | Staples | Away - Longshore [Directions] | GHS 177 SHS 191 | ||
| Thu., 5/11 | V Girls Lacrosse | Staples | Home - Cardinal Stadium [Directions] | W 15-10 | ||
| Thu., 5/11 | JV Girls Lacrosse | Staples | Home - Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Thu., 5/11 | V Softball | Danbury | Away - Danbury HS Varsity Softball Field [Directions] | L 1-5 | 2:00 | early dismissal |
| Thu., 5/11 | JV Softball | Danbury | Home - Julian Curtiss School [Directions] | 4:00 p.m. | share with varsity | early dismissal |
| Thu., 5/11 | FR Softball | Norwalk | Home - GHS Softball Field [Directions] | 4:00 p.m. | ||
| Thu., 5/11 | V Girls Tennis | Fairfield Warde | Away - FWHS Blake Courts [Directions] | W 6-1 | 2:00 | early dismissal |
| Thu., 5/11 | JV Girls Tennis | Darien | Home - Binney Park [Directions] | 4:00 p.m. | junior varsity | |
| Thu., 5/11 | JV Girls Tennis | Fairfield Warde | Away - Fairfield Woods MS Courts [Directions] | 4:00 p.m. | share with varsity | freshman |
| Fri., 5/12 | V Baseball | Danbury | Home - GHS Baseball Field [Directions] | W 3-2 | ||
| Fri., 5/12 | JV Baseball | Danbury | Home - Julian Curtiss School [Directions] | 4:00 p.m. | ||
| Fri., 5/12 | V Boys Outdoor Track | Glenn Loucks Games | Away - White Plain HS | 4:00 p.m. | ||
| Fri., 5/12 | V Boys Rugby | Ridgefield | Away - Ridgefield HS [Directions] | 4:00 p.m. | 2:30 | |
| Fri., 5/12 | V Boys Rugby | Ridgefield | Away - Ridgefield HS [Directions] | 5:30 p.m. | 2:30 | Varsity B |
| Fri., 5/12 | V Boys Sailing | Mallory Trophy | Away - Massachusetts Institute of Technology | 9:00 a.m. | ||
| Fri., 5/12 | V Boys Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | L 0-3 | 2:00 | early dismissal |
| Fri., 5/12 | JV Boys Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | share with varsity | early dismissal |
| Fri., 5/12 | V Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS [Directions] | W 19-10 | 2:30 | |
| Fri., 5/12 | JV Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:30 p.m. | share with varsity | |
| Fri., 5/12 | V Girls Sailing | Mallory Trophy | Away - Massachusetts Institute of Technology | 9:00 a.m. | ||
| Sat., 5/13 | V Boys Lacrosse | Darien | Home - Cardinal Stadium [Directions] | L 8-12 | ||
| Sat., 5/13 | JV Boys Lacrosse | Darien | Home - GHS Field 7 [Directions] | 1:00 p.m. | ||
| Sat., 5/13 | V Boys Sailing | Mallory Trophy | Away - Massachusetts Institute of Technology | 9:00 a.m. | ||
| Sat., 5/13 | FR Girls Lacrosse | Ridgefield | Home - GHS Field 3 [Directions] | 10:00 a.m. | ||
| Sat., 5/13 | V Girls Sailing | Mallory Trophy | Away - Massachusetts Institute of Technology | 9:00 a.m. | ||
| Sat., 5/13 | V Girls Water Polo | Cardinal Invitational | Home - GHS Pool [Directions] | 9:00 a.m. | ||
| Sun., 5/14 | V Boys Sailing | Mallory Trophy | Away - Massachusetts Institute of Technology | 9:00 a.m. | ||
| Sun., 5/14 | V Girls Sailing | Mallory Trophy | Away - Massachusetts Institute of Technology | 9:00 a.m. | ||
| Mon., 5/15 | V Baseball | Fairfield Warde | Home - GHS Baseball Field [Directions] | W 15-5 | ||
| Mon., 5/15 | JV Baseball | Fairfield Warde | Home - Julian Curtiss School [Directions] | 4:00 p.m. | ||
| Mon., 5/15 | FR Baseball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 4:00 p.m. | 2:30 | |
| Mon., 5/15 | V Boys Volleyball | Trumbull | Home - GHS Gymnasium [Directions] | L 2-3 | ||
| Mon., 5/15 | JV Boys Volleyball | Trumbull | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 5/15 | V Girls Lacrosse | Convent of Sacred Heart (Scrim.) | Away - Covent of Sacred Heart | 3:30 p.m. | 2:30 | |
| Mon., 5/15 | FR Girls Lacrosse | Greenwich Country Day | Away | 3:30 p.m. | ||
| Mon., 5/15 | V Girls Outdoor Track | Staples | Home - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Mon., 5/15 | V Softball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | L 0-3 | 2:00 | early dismissal |
| Mon., 5/15 | JV Girls Tennis | New Canaan | Home - Binney Park [Directions] | 4:00 p.m. | freshman | |
| Tue., 5/16 | V Baseball | Southington | Away - Baseball Varsity Field [Directions] | W 8-3 | 10:30 | |
| Tue., 5/16 | JV Baseball | Southington | Away - Baseball JV Field [Directions] | Cancelled | share with varsity | |
| Tue., 5/16 | V Boys Golf | St. Joseph | Away [Directions] | Greenwich 147 St. Joe's 173 | ||
| Tue., 5/16 | JV Boys Golf | Darien | Away - CC of Darien [Directions] | 3:15 p.m. | ||
| Tue., 5/16 | V Boys Lacrosse | Trumbull | Home - Cardinal Stadium [Directions] | W 13-7 | ||
| Tue., 5/16 | JV Boys Lacrosse | Trumbull | Home - GHS Field 7 [Directions] | 4:00 p.m. | ||
| Tue., 5/16 | FR Boys Lacrosse | Darien | Away - DHS Turf #2 [Directions] | 4:00 p.m. | 3:00 | |
| Tue., 5/16 | V Boys Outdoor Track | Staples | Away - Staples Stadium [Directions] | 4:00 p.m. | 2:00 | |
| Tue., 5/16 | V Girls Golf | Danbury | Away - Richter Park Golf Course [Directions] | GHS 172 DHS 208 | ||
| Tue., 5/16 | FR Girls Lacrosse | Norwalk | Home - GHS Field 3 [Directions] | 5:30 p.m. | ||
| Tue., 5/16 | FR Softball | Darien | Home - GHS Softball Field [Directions] | Cancelled | ||
| Wed., 5/17 | V Boys Golf | New Canaan | Away - Country Club of New Canaan [Directions] | Greenwich 152 New Canaan 158 | ||
| Wed., 5/17 | JV Boys Golf | New Canaan | Away - Country Club of New Canaan [Directions] | 3:30 p.m. | ||
| Wed., 5/17 | JV Boys Lacrosse | Fairfield Warde | Home - GHS Field 7 [Directions] | 4:00 p.m. | ||
| Wed., 5/17 | JV Boys Tennis | Wilton | Away - Wilton HS [Directions] | 4:30 p.m. | 2:30 | freshman |
| Wed., 5/17 | V Boys Volleyball | Staples | Away - Staples H.S. Gym [Directions] | L 0-3 | 2:00 | early dismissal |
| Wed., 5/17 | JV Boys Volleyball | Staples | Away - Staples H.S. Gym [Directions] | 5:30 p.m. | share with varsity | early dismissal |
| Wed., 5/17 | V Girls Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | GHS 176 THS 183 | ||
| Wed., 5/17 | Unified Sports Track | Tournament | Away | 3:00 p.m. | ||
| Thu., 5/18 | V Baseball | Westhill | Away - Westhill Baseball Field [Directions] | L 5-8 | 2:30 | |
| Thu., 5/18 | FR Baseball | Danbury | Away - Westerner Baseball Field, Rogers Park [Directions] | 3:45 p.m. | 2:30 | |
| Thu., 5/18 | V Boys Golf | Ridgefield | Home - Griffith E Harris Golf Course [Directions] | Greenwich 156 Ridgefield 173 | ||
| Thu., 5/18 | FR Boys Lacrosse | Wilton | Home - GHS Field 7 [Directions] | 4:30 p.m. | ||
| Thu., 5/18 | V Boys Tennis | FCIAC Tournament | Home - GHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/18 | JV Boys Tennis | Staples | Away - Town Farms Tennis Courts [Directions] | 4:00 p.m. | 2:30 | junior varsity |
| Thu., 5/18 | V Girls Golf | Trumbull | Home - Innis Arden Golf Course [Directions] | GHS 204 THS 205 played from green tees | ||
| Thu., 5/18 | V Girls Lacrosse | FCIAC Tournament | Home - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Thu., 5/18 | FR Girls Lacrosse | Wilton | Away - Allen's Field [Directions] | 5:00 p.m. | 3:30 | |
| Thu., 5/18 | FR Softball | Danbury | Home - GHS Softball Field [Directions] | 4:00 p.m. | ||
| Thu., 5/18 | JV Girls Tennis | Fairfield Warde | Away - Fairfield Woods MS Courts [Directions] | 4:00 p.m. | 2:30 | freshman |
| Fri., 5/19 | V Boys Sailing | FCSL Silver Cup | Home - Grass Island [Directions] | 3:00 p.m. | ||
| Fri., 5/19 | V Boys Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | L 0-3 | 2:30 | early dismissal |
| Fri., 5/19 | JV Boys Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | share with varsity | early dismissal |
| Fri., 5/19 | V Girls Sailing | FCSL Silver Cup | Home - Grass Island [Directions] | 3:00 p.m. | ||
| Sat., 5/20 | V Boys Lacrosse | FCIAC Tournament | Home - Cardinal Stadium [Directions] | 11:00 a.m. | ||
| Sat., 5/20 | V Boys Sailing | NESSA | Away - Bowdoin College | 9:00 a.m. | ||
| Sat., 5/20 | V Boys Sailing | FCSL Gold Cup | Home - Grass Island [Directions] | 9:00 a.m. | ||
| Sat., 5/20 | V Girls Sailing | NESSA | Away - Bowdoin College | 9:00 a.m. | ||
| Sat., 5/20 | V Girls Sailing | FSCL Gold Cup | Home - Grass Island [Directions] | 9:00 a.m. | ||
| Mon., 5/22 | V Boys Golf | Ike SQR | Away - Burning Tree Country Club | 3:00 p.m. | ||
| Mon., 5/22 | JV Boys Rugby | Fordham Prep (NY) | Away - Fordham University | 4:00 p.m. | 2:45 p.m. | |
| Mon., 5/22 | FR Boys Rugby | Fordham Prep (NY) | Away - Fordham University | 4:00 p.m. | 2:30 | |
| Mon., 5/22 | V Boys Volleyball | Kolbe Cathedral | Home - GHS Gymnasium [Directions] | W 3-0 | ||
| Mon., 5/22 | JV Boys Volleyball | Kolbe Cathedral | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 5/22 | V Girls Golf | Amity | Home - Stanwich CC [Directions] | Cancelled | ||
| Tue., 5/23 | V Boys Golf | Staples | Home - Stanwich Country Club [Directions] | Greenwich 161 Staples 170 | ||
| Tue., 5/23 | JV Boys Golf | Staples | Away - Longshore [Directions] | 3:15 p.m. | ||
| Tue., 5/23 | V Boys Lacrosse | FCIAC Tournament | Away - Brien McMahon HS | 5:00 p.m. | ||
| Tue., 5/23 | V Boys Outdoor Track | FCIAC Championships | Away - Ridgefield HS | 2:00 p.m. | ||
| Tue., 5/23 | V Boys Tennis | FCIAC Tournament | Home - GHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/23 | V Girls Golf | Ridgefield | Home - Griffith E Harris Golf Course [Directions] | GHS 182 RHS 193 | ||
| Tue., 5/23 | V Girls Lacrosse | Scrimmage | Home - GHS Field 3 [Directions] | 3:00 p.m. | ||
| Wed., 5/24 | V Baseball | Scrimmage | Away - New Canaan Baseball Field | 3:30 p.m. | ||
| Wed., 5/24 | V Boys Golf | Fairfield Prep | Home - Griffith E Harris Golf Course [Directions] | Greenwich 154 Prep 154 | ||
| Wed., 5/24 | JV Boys Golf | Fairfield Prep | Home - Griffith E Harris Golf Course [Directions] | 3:15 p.m. | ||
| Wed., 5/24 | V Boys Rugby | State Semi-Final | Home - Cardinal Stadium [Directions] | 6:00 p.m. | ||
| Wed., 5/24 | JV Girls Golf | Ekstrom Tournament | Away - South Pine Creek Golf Course | 3:00 p.m. | ||
| Wed., 5/24 | V Girls Outdoor Track | FCIAC Championships | Away - Danbury HS | 2:00 p.m. | ||
| Thu., 5/25 | V Boys Golf | CHAPPA | Away - Longshore Golf Course | TBA | ||
| Fri., 5/26 | V Boys Lacrosse | Scrimmage | Home - GHS Field 7 [Directions] | 5:00 p.m. | ||
| Fri., 5/26 | JV Boys Rugby | Tournament | Home - Cardinal Stadium [Directions] | 4:30 p.m. | ||
| Sat., 5/27 | V Boys Rugby | State Championship | Away - Fairfield Ludlowe HS | 2:00 p.m. | ||
| Sat., 5/27 | FR Boys Rugby | Tournament | Away - Fairfield University | 9:00 a.m. | 8:00 a.m. | |
| Sat., 5/27 | V Boys Tennis | CIAC Class LL State Tournament | Away - Yale University | 9:00 a.m. | ||
| Sat., 5/27 | V Girls Tennis | CIAC Class LL Tournament | Home - GHS Tennis Courts [Directions] | 12:00 p.m. | ||
| Tue., 5/30 | V Baseball | CIAC Class LL Tournament | Away - TBA | 3:00 p.m. | ||
| Tue., 5/30 | V Boys Golf | Holohan Tournament | Away - Country Club of Darien | 12:00 p.m. | ||
| Tue., 5/30 | V Boys Tennis | CIAC Class LL State Tournament | Away - Yale University | 1:00 p.m. | ||
| Tue., 5/30 | V Girls Golf | Fairfield Warde | Home - Fairchild Wheeler Golf Course [Directions] | GHS 177 FWHS 167 | ||
| Tue., 5/30 | V Girls Lacrosse | CIAC Class L State Tournament | Home - Cardinal Stadium [Directions] | 5:00 p.m. | ||
| Wed., 5/31 | V Boys Lacrosse | CIAC Class L State Tournament | Away - Cardinal Stadium | 4:30 p.m. | ||
| Wed., 5/31 | V Boys Outdoor Track | CIAC Class LL State Championships | Away - Manchester HS [Directions] | 3:00 p.m. | ||
| Wed., 5/31 | V Boys Tennis | CIAC Class LL State Tournament | Away - Yale University | 3:00 p.m. | ||
| Wed., 5/31 | V Girls Outdoor Track | Class LL State Championships | Away - Manchester HS | 3:00 p.m. | 12:00 | |
| Wed., 5/31 | V Girls Tennis | CIAC Class LL Tournament | Away - Staples HS | 1:00 p.m. | ||
| Thu., 6/1 | V Boys Golf | FCIAC Tournament | Away - Fairchild Wheeler Golf Course | 12:00 p.m. | ||
| Thu., 6/1 | V Boys Tennis | CIAC Class LL State Tournament | Away - Conard HS | 3:00 p.m. | ||
| Thu., 6/1 | V Girls Golf | FCIAC Tournament | Away - Fairchild Wheeler Golf Course | 9:00 a.m. | ||
| Thu., 6/1 | V Girls Lacrosse | CIAC Class L State Tournament | Home - Cardinal Stadium [Directions] | 5:00 p.m. | ||
| Sat., 6/3 | V Boys Lacrosse | CIAC Class L State Tournament | Away - Darien HS | 3:00 p.m. | ||
| Mon., 6/5 | V Boys Outdoor Track | CIAC State Open Championships | Away - Willowbrook Park | 1:30 p.m. | ||
| Mon., 6/5 | V Girls Outdoor Track | State Open Championships | Away - Willowbrook Park | 1:30 p.m. | ||
| Tue., 6/6 | V Boys Golf | CIAC State Tournament | Away - Fairview Farms Golf Club | 7:30 a.m. | ||
| Tue., 6/6 | V Girls Golf | CIAC State Tournament | Away - Tashua Knolls Golf Course | 8:00 a.m. | ||