| Greenwich 2015-16 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 1206 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| TBA | JV Baseball | Trinity Catholic | Home - Julian Curtiss School [Directions] | TBA | ||
| TBA | JV Baseball | Brien McMahon | Home - Julian Curtiss School [Directions] | TBA | ||
| TBA | FR Boys Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 3:45 p.m. | 2:30PM | |
| TBA | FR Boys Basketball | Brunswick School | Home - GHS Gymnasium [Directions] | TBA | ||
| TBA | JV Boys Ice Hockey | Westhill/Stamford | Home - Dorothy Hamill Ice Rink [Directions] | TBA | ||
| TBA | JV Boys Ice Hockey | Rye Country Day (NY) | Home - Dorothy Hamill Ice Rink [Directions] | TBA | ||
| TBA | JV Boys Ice Hockey | New Canaan | Home - Dorothy Hamill Ice Rink [Directions] | TBA | ||
| TBA | JV Boys Ice Hockey | Darien | Away - Stamford Twin Rinks [Directions] | TBA | ||
| TBA | V Boys Indoor Track | MEET | Away - Staples HS | 10:00 a.m. | ||
| TBA | V Boys Indoor Track | SCC Coaches Invitational | Away - New Haven Athletic Center | 10:00 a.m. | ||
| TBA | V Boys Lacrosse | Smithtown East (NY) | Home - Cardinal Stadium [Directions] | Cancelled | ||
| TBA | JV Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde Grass Utility Field [Directions] | 4:30 p.m. | ||
| TBA | JV Boys Lacrosse | Smithtown East (NY) | Home - GHS Field 7 [Directions] | Cancelled | ||
| TBA | V Boys Outdoor Track | TBA | Away - TBA | TBA | ||
| TBA | V Boys Outdoor Track | Tba | Away | TBA | ||
| TBA | V Boys Outdoor Track | Tba | Away | TBA | ||
| TBA | V Boys Outdoor Track | TBA | Away - TBA | TBA | ||
| TBA | V Boys Outdoor Track | TBA | Away - TBA | TBA | ||
| TBA | V Boys Outdoor Track | TBA | Away - TBA | TBA | ||
| TBA | JV Boys Tennis | Darien | Home - Central MS [Directions] | 4:30 p.m. | Freshman | |
| TBA | JV Boys Tennis | Wilton | Home - Central MS [Directions] | 4:30 p.m. | Freshman | |
| TBA | JV Boys Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | TBA | ||
| TBA | JV Wrestling | Danbury Tournament | Away - Danbury HS | 9:00 a.m. | ||
| TBA | FR Girls Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | TBA | ||
| TBA | FR Girls Basketball | Fairfield Ludlowe | Home - GHS Gymnasium [Directions] | TBA | ||
| TBA | V Girls Golf | Greenwich Academy (Scrim.) | Away - Stanwich Country Club | Cancelled | ||
| TBA | V Girls Gymnastics | New England Championships | Away - TBA | TBA | ||
| TBA | V Girls Indoor Track | SCC Coaches Invitational | Away - New Haven Athletic Center | 10:00 a.m. | ||
| TBA | V Girls Indoor Track | MEET | Away - Staples HS | 10:00 p.m. | 8:15AM | 2 Buses |
| TBA | JV Girls Lacrosse | Greenwich Academy (Scrim.) | Home - GHS Field 3 [Directions] | TBA | ||
| TBA | V Girls Outdoor Track | TBA | Away - TBA | TBA | ||
| TBA | JV Girls Soccer | Fairfield Ludlowe | Home - GHS Field 3 [Directions] | TBA | ||
| TBA | JV Girls Soccer | Wilton | Away - Allen's Field [Directions] | TBA | 2:30pm | |
| TBA | FR Girls Soccer | New Canaan | Home - GHS Field 3 [Directions] | TBA | ||
| TBA | JV Softball | TBA | Away | 3:30 p.m. | ||
| TBA | JV Softball | Fairfield Warde | Home - Julian Curtiss School [Directions] | 4:00 p.m. | ||
| TBA | JV Softball | Bridgeport Central | Home - Julian Curtiss School [Directions] | TBA | ||
| TBA | JV Softball | Staples | Home - Julian Curtiss School [Directions] | TBA | ||
| TBA | JV Softball | Staples | Away - Staples HS - Softball Field [Directions] | TBA | ||
| TBA | JV Softball | Brookfield | Home - Julian Curtiss School [Directions] | TBA | ||
| TBA | FR Softball | Norwalk | Home - GHS Softball Field [Directions] | 4:00 p.m. | ||
| TBA | JV Girls Tennis | Darien | Home - Binney Park [Directions] | 4:00 p.m. | JVB | |
| TBA | JV Girls Tennis | New Canaan | Home - Binney Park [Directions] | 4:00 p.m. | JVA | |
| TBA | JV Girls Tennis | Wilton | Away - Middlebrook School [Directions] | TBA | JVB | |
| Sat., 8/22 | V Boys Water Polo | USNA Scrimmage | Away - United States Naval Academy | 10:00 a.m. | 7:00am | |
| Sat., 8/29 | V Boys Water Polo | NYAC Scrimmage | Away - Pelham Manor | 8:30 a.m. | 7:00am | |
| Sat., 8/29 | JV Boys Water Polo | Suffield Academy | Home - GHS Pool [Directions] | 3:00 p.m. | ||
| Tue., 9/1 | V Boys Soccer | Brunswick School (Scrim.) | Home - Cardinal Stadium [Directions] | 4:30 p.m. | ||
| Tue., 9/1 | V Field Hockey | Lauralton Hall (Scrim.) | Home - GHS Field 4 [Directions] | 3:30 p.m. | ||
| Thu., 9/3 | V Boys Soccer | Notre Dame-West Haven (Scrim.) | Home - Cardinal Stadium [Directions] | 4:30 p.m. | ||
| Thu., 9/3 | JV Boys Soccer | Notre Dame-West Haven (Scrim.) | Home - GHS Field 3 [Directions] | 4:30 p.m. | ||
| Thu., 9/3 | JV Boys Soccer | Notre Dame-West Haven (Scrim.) | Home - GHS Field 3 [Directions] | 4:30 p.m. | ||
| Thu., 9/3 | V Field Hockey | Greenwich Academy (Scrim.) | Away - Greenwich Academy | 3:00 p.m. | ||
| Thu., 9/3 | V Girls Soccer | Darien (Scrim.) | Away - DHS Turf #2 [Directions] | 4:30 p.m. | 3:00pm | |
| Thu., 9/3 | JV Girls Soccer | Darien (Scrim.) | Away - Middlesex Upper Field [Directions] | 4:30 p.m. | share bus with varsity | |
| Thu., 9/3 | V Girls Volleyball | Greenwich Academy (Scrim.) | Home - GHS Gymnasium [Directions] | 3:00 p.m. | ||
| Thu., 9/3 | JV Girls Volleyball | Greenwich Academy (Scrim.) | Home - GHS Gymnasium [Directions] | 3:00 p.m. | ||
| Sat., 9/5 | JV Football | Stepinac (NY) (Scrim.) | Away - Stepinac HS | 9:30 a.m. | 8:00am | |
| Sat., 9/5 | FR Football | Stepinac (NY) (Scrim.) | Away - Stepinac HS | 12:30 p.m. | 10:30am | 2 busses |
| Sat., 9/5 | V Girls Volleyball | Scrimmage | Away - Stamford HS | 9:00 a.m. | ||
| Mon., 9/7 | School Holidays and Closings | Labor Day | ||||
| Wed., 9/9 | V Field Hockey | Wilton (Scrim.) | Away - Fujitani Field - Turf [Directions] | 4:00 p.m. | ||
| Wed., 9/9 | V Girls Soccer | Greenwich Academy (Scrim.) | Home - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Wed., 9/9 | JV Girls Soccer | Greenwich Academy (Scrim.) | Home - Cardinal Stadium [Directions] | 5:00 p.m. | ||
| Wed., 9/9 | JV Girls Soccer | Greenwich Academy (Scrim.) | Home - Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Thu., 9/10 | FR Football | Fairfield Warde (Scrim.) | Home - Cardinal Stadium [Directions] | 4:30 p.m. | ||
| Thu., 9/10 | V Girls Volleyball | King and Low-Heywood Thomas (Scrim.) | Away - KLHT School | 3:15 p.m. | 2:30 p.m. | |
| Fri., 9/11 | V Boys Soccer | St. Joseph | Home - Cardinal Stadium [Directions] | T 2-2 | ||
| Fri., 9/11 | JV Boys Soccer | St. Joseph | Home - GHS Field 3 [Directions] | 5:00 p.m. | ||
| Sat., 9/12 | SO Football | New Canaan | Home - Cardinal Stadium [Directions] | 10:00 a.m. | ||
| Sat., 9/12 | V Boys Water Polo | Battle of the Beltway | Away - United States Naval Academy | 9:00 a.m. | Yes | Saturday-Sunday |
| Sat., 9/12 | JV Boys Water Polo | Battle of the Beltway | Away - United States Naval Academy | 9:00 a.m. | Saturday-Sunday / share bus with varsity | |
| Sat., 9/12 | V Field Hockey | Fairfield Ludlowe | Away - Taft Field [Directions] | W 1-0 | 1:00pm | |
| Sat., 9/12 | JV Field Hockey | Fairfield Ludlowe | Away - Taft Field [Directions] | 4:30 p.m. | share bus with varsity | |
| Sat., 9/12 | FR Field Hockey | Fairfield Ludlowe | Home - GHS Field 3 [Directions] | 10:00 a.m. | ||
| Sat., 9/12 | V Girls Soccer | St. Joseph | Away - St. Joseph HS [Directions] | L 0-8 | 2:00pm | |
| Sat., 9/12 | JV Girls Soccer | St. Joseph | Away - St. Catherines, Trumbull, CT [Directions] | 4:00 p.m. | share bus with varsity | |
| Sat., 9/12 | V Girls Volleyball | Scrimmage | Home - GHS Gymnasium [Directions] | 9:00 a.m. | ||
| Mon., 9/14 | School Holidays and Closings | Rosh Hashana | ||||
| Tue., 9/15 | V Boys Cross Country | Ridgefield, Fairfield Warde, Norwalk | Away - RHS Upper Grass Field [Directions] | 4:00 p.m. | 2:15 | |
| Tue., 9/15 | V Boys Soccer | Westhill | Away - Westhill Front Turf Field [Directions] | W 4-0 | 2:30pm | |
| Tue., 9/15 | JV Boys Soccer | Westhill | Away - Westhill Front Turf Field [Directions] | 5:45 p.m. | 4:00pm | |
| Tue., 9/15 | FR Boys Soccer | Westhill | Home - GHS Field 7 [Directions] | 4:00 p.m. | ||
| Tue., 9/15 | V Girls Cross Country | Ridgefield, Fairfield Warde, Norwalk | Away - RHS Upper Grass Field [Directions] | 4:00 p.m. | 2:15 | |
| Tue., 9/15 | V Field Hockey | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | W 5-1 | 2:15pm | |
| Tue., 9/15 | JV Field Hockey | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 5:30 p.m. | share bus with varsity | |
| Tue., 9/15 | FR Field Hockey | Danbury | Home - GHS Field 3 [Directions] | 4:00 p.m. | ||
| Tue., 9/15 | V Girls Volleyball | Fairfield Ludlowe | Home - GHS Gymnasium [Directions] | W 3-0 | ||
| Tue., 9/15 | JV Girls Volleyball | Fairfield Ludlowe | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 9/16 | V Boys Water Polo | West Point | Away - United States Military Academy | 4:00 p.m. | 2:30pm | |
| Wed., 9/16 | JV Boys Water Polo | West Point | Away - United States Military Academy | 4:00 p.m. | share bus with varsity | |
| Wed., 9/16 | FR Field Hockey | Darien | Away - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | 2:30pm | |
| Wed., 9/16 | V Girls Soccer | Westhill | Home - Cardinal Stadium [Directions] | W 5-0 | ||
| Wed., 9/16 | JV Girls Soccer | Westhill | Home - GHS Field 3 [Directions] | 4:00 p.m. | ||
| Wed., 9/16 | V Girls Swimming and Diving | Trumbull | Home - GHS Pool [Directions] | 3:30 p.m. | ||
| Wed., 9/16 | JV Girls Swimming and Diving | Darien | Home - GHS Pool [Directions] | 6:00 p.m. | ||
| Thu., 9/17 | FR Football | Westhill | Away - Rippowam Turf Field [Directions] | 4:00 p.m. | 2:30pm | 2 busses |
| Thu., 9/17 | V Boys Soccer | Wilton | Home - Cardinal Stadium [Directions] | W 3-2 | ||
| Thu., 9/17 | JV Boys Soccer | Wilton | Home - GHS Field 3 [Directions] | 4:30 p.m. | ||
| Thu., 9/17 | FR Boys Soccer | Wilton | Away - Allen's Field [Directions] | 4:15 p.m. | 2:30pm | |
| Fri., 9/18 | V Football | Trinity Catholic | Away - Trinity Catholic Alumni Field | W 42-38 | 1:30pm | 2 busses |
| Fri., 9/18 | V Field Hockey | Darien | Home - Cardinal Stadium [Directions] | L 0-4 | ||
| Fri., 9/18 | JV Field Hockey | Darien | Home - Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Fri., 9/18 | V Girls Soccer | Wilton | Away - Lilly Field - Turf [Directions] | W 2-0 | 5:00pm | |
| Fri., 9/18 | FR Girls Soccer | Wilton | Home - GHS Field 3 [Directions] | 4:30 p.m. | ||
| Fri., 9/18 | V Girls Swimming and Diving | St. Joseph | Home - GHS Pool [Directions] | 3:30 p.m. | ||
| Sat., 9/19 | V Boys Cross Country | Wilton Invitational | Away - Wilton HS | 9:00 a.m. | ||
| Sat., 9/19 | SO Football | Brien McMahon | Away - Brien McMahon HS [Directions] | 10:00 a.m. | ||
| Sat., 9/19 | V Boys Soccer | Ridgefield | Home - Cardinal Stadium [Directions] | W 4-2 | ||
| Sat., 9/19 | JV Boys Soccer | Ridgefield | Home - GHS Field 3 [Directions] | 11:00 a.m. | ||
| Sat., 9/19 | FR Boys Soccer | Ridgefield | Away - RHS Lower Grass Field [Directions] | 4:00 p.m. | 2:30pm | |
| Sat., 9/19 | V Boys Water Polo | Dartmouth Tournament | Away - Dartmouth University | 9:00 a.m. | Yes | |
| Sat., 9/19 | JV Boys Water Polo | Dartmouth University | Away - Dartmouth University | 10:00 a.m. | share bus with varsity | |
| Sat., 9/19 | V Girls Cross Country | Wilton Invitational | Away - Wilton HS | 9:00 a.m. | ||
| Sat., 9/19 | V Girls Swimming and Diving | Glastonbury | Home - GHS Pool [Directions] | 11:00 a.m. | ||
| Mon., 9/21 | V Field Hockey | Norwalk | Away - Testa Field, NHS [Directions] | L 0-2 | 5:00pm | |
| Mon., 9/21 | JV Field Hockey | Norwalk | Away - Nathan Hale M.S. Lower [Directions] | 5:45 p.m. | 4:00pm | |
| Mon., 9/21 | FR Field Hockey | Norwalk | Home - GHS Field 3 [Directions] | 4:00 p.m. | ||
| Mon., 9/21 | V Girls Volleyball | St. Joseph | Home - GHS Gymnasium [Directions] | W 3-1 | ||
| Mon., 9/21 | JV Girls Volleyball | St. Joseph | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 9/21 | FR Girls Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | 2:30pm | |
| Tue., 9/22 | V Boys Cross Country | Trumbull, Staples, Bridgeport Central | Away - XC Course [Directions] | 3:00 p.m. | 1:15 | |
| Tue., 9/22 | V Boys Soccer | Staples | Away - Loeffler Field - Staples HS [Directions] | T 1-1 | 1:15pm | |
| Tue., 9/22 | JV Boys Soccer | Staples | Away - Wakeman Field E (grass) [Directions] | 3:00 p.m. | 1:45pm | |
| Tue., 9/22 | V Girls Cross Country | Trumbull, Staples, Bridgeport Central | Away - XC Course [Directions] | 3:00 p.m. | 1:15 | |
| Tue., 9/22 | FR Girls Soccer | Ridgefield | Home - GHS Field 3 [Directions] | 3:30 p.m. | 2:30pm | |
| Wed., 9/23 | School Holidays and Closings | Yom Kippur | ||||
| Thu., 9/24 | FR Football | Darien | Away - Royle School Field [Directions] | 4:00 p.m. | 2:30pm | 2 busses |
| Thu., 9/24 | V Boys Water Polo | Brunswick School | Away - Brunswick School | 2:15 P.M. | ||
| Thu., 9/24 | JV Boys Water Polo | Brunswick School | Away - Brunswick School | 4:00 p.m. | ||
| Thu., 9/24 | V Field Hockey | Wilton | Home - Cardinal Stadium [Directions] | L 1-2 | ||
| Thu., 9/24 | JV Field Hockey | Wilton | Home - Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Thu., 9/24 | FR Field Hockey | Wilton | Away - Wilton HS - Grass Field [Directions] | 4:00 p.m. | 2:30pm | |
| Thu., 9/24 | FR Girls Soccer | Staples | Away - Wakeman Field E (grass) [Directions] | 4:00 p.m. | 2:30pm | |
| Thu., 9/24 | V Girls Swimming and Diving | Staples | Home - GHS Pool [Directions] | 3:30 p.m. | ||
| Thu., 9/24 | V Girls Volleyball | Westhill | Away - Westhill - Main Gymnasium [Directions] | W 3-0 | 2:30pm | |
| Thu., 9/24 | JV Girls Volleyball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | share bus with varsity | |
| Fri., 9/25 | V Boys Water Polo | TBA | Away - TBA | 6:00 p.m. | Yes | Friday-Saturday |
| Fri., 9/25 | JV Boys Water Polo | Beast of the East | Away - Reading Schools | 6:00 p.m. | Friday-Saturday /share bus with varsity | |
| Fri., 9/25 | V Girls Soccer | Staples | Home - Cardinal Stadium [Directions] | T 1-1 | ||
| Fri., 9/25 | JV Girls Soccer | Staples | Home - GHS Field 3 [Directions] | 4:00 p.m. | ||
| Fri., 9/25 | JV Girls Swimming and Diving | Staples | Home - GHS Pool [Directions] | 5:30 p.m. | ||
| Sat., 9/26 | V Football | Darien | Home - Cardinal Stadium [Directions] | L 28-51 | ||
| Sat., 9/26 | FR Boys Soccer | Staples | Home - GHS Field 3 [Directions] | 10:00 a.m. | ||
| Mon., 9/28 | JV Football | Darien | Away - Royle School Field [Directions] | 4:00 p.m. | 2:30pm | |
| Mon., 9/28 | V Boys Soccer | Trumbull | Home - Cardinal Stadium [Directions] | W 2-1 | ||
| Mon., 9/28 | JV Boys Soccer | Trumbull | Home - GHS Field 3 [Directions] | 5:00 p.m. | ||
| Mon., 9/28 | FR Boys Soccer | Trumbull | Away - The Pit [Directions] | 4:00 p.m. | 2:30pm | |
| Mon., 9/28 | V Field Hockey | Ridgefield | Away - Tiger Hollow Stadium [Directions] | W 3-2 | 2:15pm | |
| Mon., 9/28 | JV Field Hockey | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 5:30 p.m. | share bus with varsity | |
| Mon., 9/28 | V Girls Volleyball | Wilton | Home - GHS Gymnasium [Directions] | W 3-0 | ||
| Mon., 9/28 | JV Girls Volleyball | Wilton | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 9/28 | FR Girls Volleyball | Wilton | Away - Nicholas Zeioli Field House [Directions] | 4:00 p.m. | 2:30pm | |
| Tue., 9/29 | V Boys Cross Country | St. Joseph, Westhill, Brien McMahon | Away - St. Joseph HS [Directions] | 4:00 p.m. | 2:15 | |
| Tue., 9/29 | V Boys Water Polo | Greenwich Aquatics | Home - GHS Pool [Directions] | 7:30 p.m. | ||
| Tue., 9/29 | JV Boys Water Polo | Greenwich Aquatics | Away - Greenwich YMCA | 7:30 p.m. | ||
| Tue., 9/29 | V Girls Cross Country | St. Joseph, Westhill, Brien McMahon | Away [Directions] | 4:00 p.m. | 2:15 | |
| Tue., 9/29 | FR Field Hockey | Ridgefield | Away - RHS Upper Grass Field [Directions] | 4:00 p.m. | ||
| Tue., 9/29 | V Girls Soccer | Trumbull | Away - McDougall Stadium [Directions] | W 3-0 | 5:00pm | |
| Tue., 9/29 | JV Girls Soccer | Trumbull | Away - Varsity Grass Field [Directions] | 4:00 p.m. | 2:30pm | |
| Tue., 9/29 | FR Girls Soccer | Trumbull | Home - GHS Field 3 [Directions] | 4:00 p.m. | ||
| Tue., 9/29 | V Girls Swimming and Diving | New Canaan | Away - New Canaan YMCA [Directions] | 3:00 p.m. | 1:00 | |
| Tue., 9/29 | JV Girls Swimming and Diving | Darien | Home - GHS Pool [Directions] | 3:30 p.m. | ||
| Wed., 9/30 | V Boys Soccer | Norwalk | Home - Cardinal Stadium [Directions] | W 1-0 | ||
| Wed., 9/30 | JV Boys Soccer | Norwalk | Home - GHS Field 3 [Directions] | 4:45 p.m. | ||
| Wed., 9/30 | FR Boys Soccer | Norwalk | Away - Testa Field, NHS [Directions] | 5:30 p.m. | 4:15 | |
| Wed., 9/30 | V Girls Volleyball | Ridgefield | Home - GHS Gymnasium [Directions] | W 3-2 | ||
| Wed., 9/30 | JV Girls Volleyball | Ridgefield | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 9/30 | FR Girls Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | 2:30pm | |
| Thu., 10/1 | FR Football | Bridgeport Central | Home - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Thu., 10/1 | FR Field Hockey | Greenwich Country Day | Home - GHS Field 3 [Directions] | 3:30 p.m. | ||
| Thu., 10/1 | V Girls Soccer | Norwalk | Away - Nathan Hale M.S. Lower [Directions] | W 1-0 | 4:30pm | |
| Thu., 10/1 | JV Girls Soccer | Norwalk | Away - Nathan Hale M.S. Upper [Directions] | 4:30 p.m. | 2:30pm | |
| Thu., 10/1 | FR Girls Soccer | Wilton | Away - Allen's Field [Directions] | 4:00 p.m. | ||
| Fri., 10/2 | V Football | Bridgeport Central | Away - Kennedy Stadium [Directions] | W 42-0 | 3:30pm | 2 busses |
| Fri., 10/2 | V Boys Soccer | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | L 0-2 | 2:15pm | |
| Fri., 10/2 | JV Boys Soccer | Fairfield Warde | Home - Cardinal Stadium [Directions] | 4:00 p.m. | 2:30pm | |
| Fri., 10/2 | FR Boys Soccer | Fairfield Warde | Home - GHS Field 3 [Directions] | 4:00 p.m. | ||
| Fri., 10/2 | JV Boys Water Polo | Novice Tournament | Home - GHS Pool [Directions] | 6:00 p.m. | Friday-Saturday | |
| Fri., 10/2 | V Girls Soccer | Ridgefield | Away - Tiger Hollow Stadium [Directions] | T 0-0 | 4:00pm | |
| Fri., 10/2 | JV Girls Soccer | Ridgefield | Away - Scotts Ridge MS Turf [Directions] | 3:30 p.m. | 2:30pm | |
| Fri., 10/2 | V Girls Volleyball | Staples | Away - Staples H.S. Gym [Directions] | L 2-3 | 2:00pm | |
| Fri., 10/2 | JV Girls Volleyball | Staples | Away - Staples H.S. Gym [Directions] | 5:30 p.m. | share bus with varsity | |
| Fri., 10/2 | FR Girls Volleyball | Staples | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 10/3 | School Holidays and Closings | SAT Testing | ||||
| Mon., 10/5 | V Field Hockey | Brien McMahon | Away - Brien McMahon HS [Directions] | W 7-0 | 4:45pm | |
| Mon., 10/5 | JV Field Hockey | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:30 p.m. | 4:00pm | |
| Mon., 10/5 | V Girls Soccer | Fairfield Warde | Home - Cardinal Stadium [Directions] | L 1-3 | ||
| Mon., 10/5 | JV Girls Soccer | Fairfield Warde | Home - GHS Field 3 [Directions] | 4:00 p.m. | ||
| Mon., 10/5 | FR Girls Soccer | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | 2:30pm | |
| Mon., 10/5 | V Girls Swimming and Diving | Darien | Home - GHS Pool [Directions] | 3:30 p.m. | ||
| Tue., 10/6 | V Boys Cross Country | Danbury, Darien, New Canaan, Trinity Catholic | Home - Greenwich Point [Directions] | 4:00 p.m. | ||
| Tue., 10/6 | SO Football | Trumbull | Away - McDougall Stadium [Directions] | 5:00 p.m. | ||
| Tue., 10/6 | V Boys Soccer | Stamford | Away - Stamford High Soccer Field [Directions] | W 3-0 | 2:30pm | |
| Tue., 10/6 | JV Boys Soccer | Stamford | Away - Rippowam Field [Directions] | 4:00 p.m. | 2:30pm | |
| Tue., 10/6 | FR Boys Soccer | Stamford | Home - GHS Field 3 [Directions] | 4:00 p.m. | ||
| Tue., 10/6 | V Girls Cross Country | Danbury, Darien, New Canaan, Trinity Catholic | Home - Greenwich Point [Directions] | 4:00 p.m. | ||
| Wed., 10/7 | V Field Hockey | Fairfield Warde | Home - Cardinal Stadium [Directions] | W 3-1 | ||
| Wed., 10/7 | JV Field Hockey | Fairfield Warde | Home - Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Wed., 10/7 | V Girls Volleyball | Trumbull | Home - GHS Gymnasium [Directions] | W 3-0 | ||
| Wed., 10/7 | JV Girls Volleyball | Trumbull | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 10/7 | FR Girls Volleyball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | 2:30pm | |
| Thu., 10/8 | V Boys Soccer | Bridgeport Central | Away - Kennedy Stadium [Directions] | T 2-2 | 3:45pm | |
| Thu., 10/8 | JV Boys Soccer | Bridgeport Central | Away - Kennedy Stadium [Directions] | 4:00 p.m. | 2:30pm | |
| Thu., 10/8 | V Girls Soccer | Stamford | Home - Cardinal Stadium [Directions] | W 3-0 | ||
| Thu., 10/8 | JV Girls Soccer | Stamford | Home - GHS Field 3 [Directions] | 4:00 p.m. | ||
| Fri., 10/9 | V Boys Water Polo | CPCT | Away - Chelsea Piers | 7:00 p.m. | ||
| Fri., 10/9 | V Field Hockey | St. Joseph | Away - St. Joseph HS [Directions] | W 9-0 | 2:15pm | |
| Fri., 10/9 | JV Field Hockey | St. Joseph | Away - St. Catherines, Trumbull, CT [Directions] | 4:00 p.m. | share bus with varsity | |
| Fri., 10/9 | V Girls Soccer | Bridgeport Central | Home - Cardinal Stadium [Directions] | W 3-0 | ||
| Fri., 10/9 | V Girls Swimming and Diving | Ridgefield | Away - Pool at Barlow Mountain School [Directions] | 4:00 p.m. | 1:45pm | |
| Fri., 10/9 | V Girls Volleyball | Norwalk | Home - GHS Gymnasium [Directions] | W 3-0 | ||
| Fri., 10/9 | JV Girls Volleyball | Norwalk | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Sat., 10/10 | V Boys Cross Country | Wickham Invitational | Away - Wickham Park | 10:00 a.m. | ||
| Sat., 10/10 | V Girls Cross Country | Wickham Invitational | Away - Wickham Park | 10:00 a.m. | ||
| Mon., 10/12 | V Boys Soccer | Trinity Catholic | Home - Cardinal Stadium [Directions] | W 2-1 | ||
| Mon., 10/12 | FR Boys Soccer | Danbury | Home - GHS Field 3 [Directions] | 4:00 p.m. | ||
| Mon., 10/12 | V Field Hockey | Pomperaug | Away - Taft Field [Directions] | L 1-2 | 2:00pm | |
| Mon., 10/12 | V Girls Swimming and Diving | Wilton | Home - GHS Pool [Directions] | 3:30 p.m. | ||
| Mon., 10/12 | JV Girls Swimming and Diving | Darien | Home - GHS Pool [Directions] | 6:00 p.m. | ||
| Tue., 10/13 | V Boys Cross Country | Wilton, Fairfield Ludlowe, Stamford | Home - Greenwich Point [Directions] | 4:00 p.m. | ||
| Tue., 10/13 | V Girls Cross Country | Wilton, Fairfield Ludlowe, Stamford | Home - Greenwich Point [Directions] | 4:00 p.m. | ||
| Tue., 10/13 | V Girls Soccer | Trinity Catholic | Away - Trinity Catholic Soccer Field | W 8-2 | 2:30pm | |
| Tue., 10/13 | V Girls Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | W 3-0 | 2:30pm | |
| Tue., 10/13 | JV Girls Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | share bus with varsity | |
| Tue., 10/13 | FR Girls Volleyball | Fairfield Warde | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 10/14 | V Boys Soccer | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | T 2-2 | 3:45 | |
| Wed., 10/14 | JV Boys Soccer | Danbury | Away - Danbury HS Grass Soccer Field [Directions] | 6:00 p.m. | 3:45 | |
| Wed., 10/14 | V Boys Water Polo | West Point | Away - United States Military Academy | 4:00 p.m. | 2:30pm | |
| Wed., 10/14 | JV Boys Water Polo | West Point | Away - United States Military Academy | 4:00 p.m. | share bus with varsity | |
| Wed., 10/14 | V Field Hockey | New Canaan | Home - Cardinal Stadium [Directions] | W 1-0 | ||
| Wed., 10/14 | JV Field Hockey | New Canaan | Home - Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Wed., 10/14 | FR Field Hockey | New Canaan | Away - NCHS Water Tower Turf Field [Directions] | 3:30 p.m. | 2:30pm | |
| Thu., 10/15 | V Girls Soccer | Danbury | Home - Cardinal Stadium [Directions] | W 3-0 | ||
| Thu., 10/15 | JV Girls Soccer | Danbury | Home - GHS Field 3 [Directions] | 4:00 p.m. | ||
| Thu., 10/15 | V Girls Swimming and Diving | Danbury | Away - O'Neil Center @ Western Connecticut State University [Directions] | 4:00 p.m. | 2:00pm | |
| Thu., 10/15 | JV Girls Swimming and Diving | Staples, Trumbull | Home - GHS Pool [Directions] | 5:30 p.m. | ||
| Thu., 10/15 | V Girls Volleyball | Stamford | Away - Stamford HS [Directions] | W 3-0 | 2:30pm | |
| Thu., 10/15 | JV Girls Volleyball | Stamford | Away - Stamford HS [Directions] | 5:30 p.m. | share bus with varsity | |
| Thu., 10/15 | FR Girls Volleyball | Stamford | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 10/16 | V Football | Trumbull | Away - McDougall Stadium [Directions] | L 23-28 | 4:00pm | 2 busses |
| Fri., 10/16 | V Boys Soccer | Fairfield Ludlowe | Away - Taft Field [Directions] | L 0-1 | 3:45 | |
| Fri., 10/16 | JV Boys Soccer | Fairfield Ludlowe | Away - Roger Ludlowe MS [Directions] | 4:00 p.m. | 2:30pm | |
| Fri., 10/16 | FR Boys Soccer | Fairfield Ludlowe | Home - GHS Field 3 [Directions] | 4:00 p.m. | ||
| Fri., 10/16 | V Boys Water Polo | Brunswick School | Away - Brunswick School | 6:00 p.m. | 4:30pm | |
| Fri., 10/16 | JV Boys Water Polo | Brunswick School | Away - Brunswick School | 5:00 p.m. | share bus with varsity | |
| Fri., 10/16 | V Field Hockey | Trumbull | Home - Cardinal Stadium [Directions] | W 1-0 | ||
| Fri., 10/16 | JV Field Hockey | Trumbull | Home - Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Fri., 10/16 | FR Field Hockey | Trumbull | Away - Indian Ledge Turf [Directions] | 4:00 p.m. | 2:30pm | |
| Fri., 10/16 | V Girls Volleyball | Bridgeport Central | Away - Central H.S. Gym [Directions] | W 3-0 | 2:30pm | |
| Fri., 10/16 | JV Girls Volleyball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 4:00 p.m. | share bus with varsity | |
| Sat., 10/17 | FR Football | Trumbull | Home - GHS Field 7 [Directions] | 10:00 a.m. | ||
| Sat., 10/17 | V Boys Water Polo | Cardinal Tournament | Home - GHS Pool [Directions] | 9:00 a.m. | Saturday-Sunday | |
| Sat., 10/17 | JV Boys Water Polo | Cardinal Tournament | Home - GHS Pool [Directions] | 9:00 a.m. | Saturday-Sunday | |
| Sat., 10/17 | V Girls Soccer | Fairfield Ludlowe | Home - Cardinal Stadium [Directions] | W 2-0 | ||
| Sat., 10/17 | FR Girls Soccer | Fairfield Ludlowe | Away - Sturges Park [Directions] | 12:00 p.m. | 10:30am | |
| Mon., 10/19 | JV Football | Trumbull | Away - McDougall Stadium [Directions] | 4:00 p.m. | 2:30pm | |
| Mon., 10/19 | V Boys Soccer | Brien McMahon | Home - Cardinal Stadium [Directions] | T 1-1 | ||
| Mon., 10/19 | JV Boys Soccer | Brien McMahon | Home - GHS Field 3 [Directions] | 4:15 p.m. | ||
| Mon., 10/19 | FR Field Hockey | Westhill | Away [Directions] | Cancelled | 2:30pm | |
| Mon., 10/19 | V Girls Swimming and Diving | Westhill/Stamford | Home - GHS Pool [Directions] | 3:30 p.m. | ||
| Mon., 10/19 | V Girls Volleyball | Trinity Catholic | Home - GHS Gymnasium [Directions] | W 3-0 | ||
| Mon., 10/19 | JV Girls Volleyball | Trinity Catholic | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 10/20 | V Boys Water Polo | Greenwich Aquatics | Away - Greenwich YMCA | 7:30 p.m. | ||
| Tue., 10/20 | JV Boys Water Polo | Greenwich Aquatics | Away - Greenwich YMCA | 7:30 p.m. | ||
| Tue., 10/20 | V Field Hockey | Westhill | Home - Cardinal Stadium [Directions] | W 7-0 | ||
| Tue., 10/20 | JV Field Hockey | Westhill | Home - Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Tue., 10/20 | V Girls Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | W 3-0 | 5:00pm | |
| Tue., 10/20 | JV Girls Soccer | Brien McMahon | Away - Brien McMahon [Directions] | 5:15 p.m. | 3:30pm | |
| Wed., 10/21 | V Boys Cross Country | FCIAC Championships | Away - Waveny Park | 2:15 p.m. | ||
| Wed., 10/21 | V Boys Soccer | Darien | Away - DHS Turf #2 [Directions] | L 0-3 | 2:30pm | |
| Wed., 10/21 | FR Boys Soccer | Darien | Home - GHS Field 3 [Directions] | 4:00 p.m. | ||
| Wed., 10/21 | V Girls Cross Country | FCIAC Championships | Away - Waveny Park | 2:15 p.m. | ||
| Wed., 10/21 | V Girls Swimming and Diving | Norwalk/McMahon | Away - Norwalk High Pool [Directions] | 6:00 p.m. | 4:00pm | |
| Wed., 10/21 | JV Girls Swimming and Diving | Ridgefield | Home - GHS Pool [Directions] | 3:30 p.m. | ||
| Wed., 10/21 | V Girls Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | W 3-1 | 2:15pm | |
| Wed., 10/21 | JV Girls Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 5:30 p.m. | share bus with varsity | |
| Wed., 10/21 | FR Girls Volleyball | Danbury | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 10/21 | School Holidays and Closings | Early Release | ||||
| Thu., 10/22 | SO Football | Darien | Away - DHS Baseball JV Field [Directions] | 4:00 p.m. | ||
| Thu., 10/22 | FR Football | New Canaan | Away - Dunning Stadium [Directions] | 5:00 p.m. | 3:00pm | 2 busses |
| Thu., 10/22 | JV Boys Soccer | Darien | Away - DHS Turf #2 [Directions] | 4:15 p.m. | 2:30pm | |
| Thu., 10/22 | V Field Hockey | Stamford | Away - Stamford HS [Directions] | W 2-0 | 2:30pm | |
| Thu., 10/22 | JV Field Hockey | Stamford | Away - Stamford HS [Directions] | 5:30 p.m. | share bus with varsity | |
| Thu., 10/22 | FR Girls Soccer | Darien | Away - DHS Field #1 -Turf [Directions] | 4:15 p.m. | 2:30pm | |
| Fri., 10/23 | V Girls Soccer | Darien | Home - Cardinal Stadium [Directions] | L 1-0 | ||
| Fri., 10/23 | JV Girls Soccer | Darien | Home - GHS Field 3 [Directions] | 4:00 p.m. | ||
| Fri., 10/23 | FR Girls Volleyball | Fairfield Ludlowe | Home - GHS Gymnasium [Directions] | Cancelled | ||
| Sat., 10/24 | V Football | New Canaan | Home - Cardinal Stadium [Directions] | L 14-24 | ||
| Sat., 10/24 | V Boys Water Polo | Annapolis Classic | Away - United States Naval Academy | 9:00 a.m. | Yes | Saturday-Sunday |
| Sat., 10/24 | JV Boys Water Polo | Annapolis Classic | Away - United States Naval Academy | 9:00 a.m. | Saturday-Sunday/share bus with varsity | |
| Sat., 10/24 | V Field Hockey | Cheshire | Home - GHS Field 3 [Directions] | OT-L 0-1 | ||
| Sat., 10/24 | School Holidays and Closings | Homecoming | ||||
| Sat., 10/24 | School Holidays and Closings | ACT Testing | ||||
| Mon., 10/26 | JV Football | New Canaan | Away - Dunning Stadium [Directions] | 4:00 p.m. | 2:30pm | |
| Mon., 10/26 | FR Boys Soccer | New Canaan | Away - Saxe MS Field [Directions] | 4:00 p.m. | 2:30pm | |
| Mon., 10/26 | V Field Hockey | Staples | Home - Cardinal Stadium [Directions] | L 0-2 | ||
| Mon., 10/26 | JV Field Hockey | Staples | Home - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Mon., 10/26 | FR Field Hockey | Staples | Away - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | 2:30pm | |
| Mon., 10/26 | FR Girls Soccer | Ridgefield | Away - Scotts Ridge MS Turf [Directions] | 4:30 p.m. | ||
| Mon., 10/26 | V Girls Volleyball | Brien McMahon | Home - GHS Gymnasium [Directions] | L 3-2 | ||
| Mon., 10/26 | JV Girls Volleyball | Brien McMahon | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 10/27 | V Boys Soccer | New Canaan | Home - Cardinal Stadium [Directions] | W 3-1 | ||
| Tue., 10/27 | JV Boys Soccer | New Canaan | Home - GHS Field 3 [Directions] | 4:00 p.m. | ||
| Tue., 10/27 | V Girls Soccer | New Canaan | Away - Dunning Stadium [Directions] | W 2-0 | ||
| Tue., 10/27 | JV Girls Soccer | New Canaan | Away - Saxe MS Field [Directions] | 4:00 p.m. | 2:30pm | |
| Tue., 10/27 | V Girls Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | L 1-3 | 2:30pm | |
| Tue., 10/27 | JV Girls Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 4:15 p.m. | share bus with varsity | |
| Wed., 10/28 | V Girls Volleyball | Darien | Away - DHS Main Gym [Directions] | L 0-3 | 2:30pm | |
| Wed., 10/28 | JV Girls Volleyball | Darien | Away - DHS Main Gym [Directions] | 5:30 p.m. | share bus with varsity | |
| Wed., 10/28 | FR Girls Volleyball | Darien | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 10/29 | FR Football | Fairfield Ludlowe | Home - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Thu., 10/29 | V Boys Soccer | FCIAC Tournament | Away - Wilton HS | 6:00 p.m. | ||
| Thu., 10/29 | FR Girls Soccer | Danbury | Away - Danbury HS Grass Soccer Field [Directions] | 4:30 p.m. | 2:30pm | |
| Thu., 10/29 | Unified Sports Soccer | Tournament | Away - Ludlowe HS | 3:00 p.m. | 1:45 pm | |
| Fri., 10/30 | V Football | Fairfield Ludlowe | Away - Taft Field [Directions] | W 35-14 | 4:00pm | 2 busses |
| Fri., 10/30 | V Boys Water Polo | State Championship | Away - Connecticut College | 6:00 p.m. | Yes | Friday |
| Fri., 10/30 | V Girls Soccer | FCIAC Tournament | Home - Cardinal Stadium [Directions] | 3:30 p.m. | ||
| Fri., 10/30 | V Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | W 3-0 | ||
| Fri., 10/30 | JV Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 10/30 | FR Girls Volleyball | New Canaan | Home - Greenwich [Directions] | 4:00 p.m. | ||
| Sat., 10/31 | V Boys Cross Country | CIAC Class LL Championship | Away - Wickham Park | 10:55 a.m. | ||
| Sat., 10/31 | SO Football | Darien | Home - Cardinal Stadium [Directions] | 9:00 a.m. | ||
| Sat., 10/31 | V Boys Water Polo | State Championship | Away - Connecticut College | 10:00 a.m. | Yes | |
| Sat., 10/31 | V Girls Cross Country | CIAC Class LL Championships | Away - Wickham Park | 10:20 a.m. | ||
| Sat., 10/31 | V Field Hockey | FCIAC Tournament | Away - New Canaan | 10:00 a.m. | ||
| Sat., 10/31 | JV Girls Swimming and Diving | JV FCIAC Championships | Home - GHS Pool [Directions] | 12:00 p.m. | ||
| Sat., 10/31 | JV Girls Volleyball | Invitational Tournament | Away - Fairfield Warde HS | 9:00 a.m. | ||
| Mon., 11/2 | JV Football | Fairfield Ludlowe | Home - Cardinal Stadium [Directions] | 3:30 p.m. | 3:00pm | |
| Mon., 11/2 | V Boys Soccer | FCIAC Tournament | Away - Fairfield Ludlowe | 5:00 p.m. | ||
| Mon., 11/2 | V Girls Soccer | FCIAC Tournament | Away - Wilton HS | 7:00 p.m. | ||
| Tue., 11/3 | V Girls Volleyball | FCIAC Tournament | Away - Brien McMahon HS | 5:00 p.m. | ||
| Tue., 11/3 | School Holidays and Closings | Election Day | ||||
| Thu., 11/5 | FR Football | Norwalk | Away - Nathan Hale M.S. Lower [Directions] | 4:00 p.m. | 2:30pm | 2 busses |
| Thu., 11/5 | V Girls Volleyball | FCIAC Tournament | Away - Fairfield Ludlowe HS | 7:00 p.m. | ||
| Fri., 11/6 | V Boys Cross Country | CIAC Class Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Fri., 11/6 | V Football | Norwalk | Home - Cardinal Stadium [Directions] | W 32-28 | ||
| Fri., 11/6 | V Girls Cross Country | CIAC State Open Championships | Away - Wickham Park | 2:00 p.m. | ||
| Sat., 11/7 | JV Football | Norwalk | Home - Cardinal Stadium [Directions] | 9:00 a.m. | ||
| Sat., 11/7 | School Holidays and Closings | SAT Testing | ||||
| Mon., 11/9 | V Girls Soccer | Class LL State Tournament | Home - Cardinal Stadium [Directions] | 2:00 p.m. | ||
| Mon., 11/9 | V Girls Volleyball | Class LL State Tournament | Home - GHS Gymnasium [Directions] | 5:00 p.m. | ||
| Tue., 11/10 | V Boys Soccer | Class LL State Tournament | Away - Fairfield Ludlowe HS | 5:00 p.m. | ||
| Wed., 11/11 | V Field Hockey | Class L State Tournament | Away - Simsbury HS | 5:00 p.m. | ||
| Wed., 11/11 | V Girls Soccer | Class LL State Tournament | Home - Cardinal Stadium [Directions] | 2:00 p.m. | ||
| Wed., 11/11 | V Girls Swimming and Diving | Class LL Diving Championships | Away - Bulkeley HS | 4:30 p.m. | ||
| Thu., 11/12 | SO Football | New Canaan | Away - Dunning Stadium [Directions] | 5:00 p.m. | ||
| Thu., 11/12 | FR Football | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 5:00 p.m. | 3:00pm | 2 busses |
| Thu., 11/12 | V Boys Soccer | Class LL State Tournament | Away - Fairfield Prep | 4:00 p.m. | ||
| Thu., 11/12 | V Girls Volleyball | Class LL State Tournament | Away - Brien McMahon HS | 6:00 p.m. | ||
| Thu., 11/12 | V Girls Volleyball | Class LL State Tournament | Away - Brien McMahon HS | 6:00 p.m. | ||
| Fri., 11/13 | V Field Hockey | Class L State Tournament | Away - Glastonbury HS | 2:00 p.m. | ||
| Fri., 11/13 | V Girls Soccer | Class LL State Tournament | Away - Glastonbury HS | 2:00 p.m. | ||
| Sat., 11/14 | V Football | Ridgefield | Home - Cardinal Stadium [Directions] | L 7-37 | ||
| Sat., 11/14 | V Girls Swimming and Diving | Class LL State Swimming Trials | Away - East Hartford HS | 11:30 a.m. | ||
| Sat., 11/14 | V Girls Volleyball | Class LL State Tournament | Away - Amity HS | 5:00 p.m. | ||
| Mon., 11/16 | JV Football | Staples | Away - Staples Stadium [Directions] | 5:00 p.m. | 3:00pm | |
| Tue., 11/17 | V Girls Swimming and Diving | Class LL State Championship | Away - Southern Connecticut State University | 6:00 p.m. | ||
| Thu., 11/19 | FR Football | Staples | Home - Cardinal Stadium [Directions] | 3:15 p.m. | ||
| Thu., 11/19 | V Girls Swimming and Diving | State Open Diving Championships | Away - Middletown HS | 5:30 p.m. | ||
| Thu., 11/19 | V Girls Volleyball | Class LL State Tournament | Away - Trumbull HS | 6:00 p.m. | ||
| Sat., 11/21 | V Girls Swimming and Diving | State Open Championships | Away - Yale University | 12:00 p.m. | ||
| Sat., 11/21 | V Girls Volleyball | Class LL State Championship | Away - Berlin HS | 7:00 p.m. | ||
| Thu., 11/26 | V Football | Staples | Away - Staples Stadium [Directions] | L 26-28 | 7:30pm | 2 busses |
| Thu., 11/26 | School Holidays and Closings | Thanksgiving Day | ||||
| Tue., 12/1 | V Bowling | Match | Away - Nutmeg Lanes | 3:00 p.m. | ||
| Sat., 12/5 | V Girls Basketball | Hillhouse (Scrim.) | Home - GHS Gymnasium [Directions] | 12:00 p.m. | ||
| Sat., 12/5 | V Girls Ice Hockey | Scrimmage | Away - Shelton Rinks | 4:00 p.m. | ||
| Sat., 12/5 | School Holidays and Closings | SAT Testing | ||||
| Tue., 12/8 | V Bowling | Match | Away - Nutmeg Lanes | 3:00 p.m. | ||
| Tue., 12/8 | V Girls Basketball | Kennedy (Scrim.) | Away - Kennedy HS [Directions] | 4:00 p.m. | ||
| Tue., 12/8 | JV Girls Basketball | Kennedy (Scrim.) | Away - Kennedy HS [Directions] | 4:00 p.m. | ||
| Thu., 12/10 | V Boys Fencing | Brunswick School | Away - Greenwich Academy | L 12-15 | ||
| Thu., 12/10 | V Girls Basketball | Shelton (Scrim.) | Away - Shelton HS Gym [Directions] | 6:00 p.m. | 3:00PM | Share with JV |
| Thu., 12/10 | V Girls Fencing | Greenwich Academy | Away - Greenwich Academy | L 11-16 | ||
| Fri., 12/11 | V Boys Ice Hockey | Hingham (MA) (Scrim.) | Away - Pilgram Area Rink | 7:00 p.m. | ||
| Fri., 12/11 | V Girls Ice Hockey | Rye Country Day (NY) | Away - RCDS | L L | ||
| Sat., 12/12 | V Boys Basketball | Hoops for Food | Away - Windsor HS | 4:00 p.m. | 12:00PM | |
| Sat., 12/12 | V Boys Fencing | Greens Farms Academy | Away - Greens Farms Academy | 2:00 p.m. | ||
| Sat., 12/12 | V Boys Ice Hockey | Northwest Catholic (Scrim.) | Away - International Skating Center of Connecticut [Directions] | 6:00 p.m. | ||
| Sat., 12/12 | V Wrestling | Westhill (Scrim.) | Away - Westhill HS [Directions] | 10:00 a.m. | ||
| Sat., 12/12 | V Girls Fencing | Greens Farms Academy | Away - Greens Farms Academy | 2:00 p.m. | ||
| Sat., 12/12 | School Holidays and Closings | ACT Testing | ||||
| Tue., 12/15 | V Wrestling | Brewster (NY) | Away - Brewster HS | 39-38 W | ||
| Tue., 12/15 | V Bowling | Match | Away - Nutmeg Lanes | 3:00 p.m. | ||
| Tue., 12/15 | V Girls Ice Hockey | Darien | Home - Dorothy Hamill Ice Rink [Directions] | L 1-6 | ||
| Wed., 12/16 | V Boys Ice Hockey | New Canaan (Scrim.) | Home - Dorothy Hamill Ice Rink [Directions] | 5:15 p.m. | ||
| Thu., 12/17 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Dorothy Hamill Ice Rink [Directions] | W 3-2 | ||
| Fri., 12/18 | FR Girls Basketball | Stamford | Away - Stamford High Aux Gym [Directions] | 4:00 p.m. | ||
| Fri., 12/18 | V Girls Ice Hockey | Northwest Catholic | Away - Kingswood Oxford Rink [Directions] | W 4-3 | ||
| Sat., 12/19 | V Boys Ice Hockey | Milford Coop (Scrim.) | Away - Milford Ice Pavilion [Directions] | 2:15 p.m. | ||
| Sat., 12/19 | V Boys Indoor Track | MEET | Away - Staples HS | 10:00 a.m. | ||
| Sat., 12/19 | V Boys Indoor Track | New Haven Invitational | Away - New Haven Athletic Center | 10:00 a.m. | ||
| Sat., 12/19 | V Wrestling | Shelton Invitational | Away - Shelton HS | 10:00 a.m. | ||
| Sat., 12/19 | JV Wrestling | Trumbull Tournament | Away - Trumbull HS | 9:00 a.m. | ||
| Sat., 12/19 | V Girls Ice Hockey | Hamden Coop | Away - Lou Astorino Ice Rink [Directions] | L 0-8 | ||
| Sat., 12/19 | V Girls Indoor Track | MEET | Away - Staples HS | 10:00 a.m. | 8:15AM | 2 Buses |
| Sat., 12/19 | V Girls Indoor Track | New Haven Invitational | Away - New Haven Athletic Center | 10:00 a.m. | 7:30AM | |
| Sun., 12/20 | JV Girls Ice Hockey | New Canaan | Away - Darien Ice Rink [Directions] | 8:50 p.m. | ||
| Mon., 12/21 | V Boys Basketball | Notre Dame-West Haven | Away - Notre Dame HS [Directions] | L 62-63 | 3:30PM | Share with JV |
| Mon., 12/21 | JV Boys Basketball | Notre Dame-West Haven | Away - Notre Dame HS [Directions] | 5:15 p.m. | ||
| Mon., 12/21 | FR Boys Basketball | Notre Dame-West Haven | Away - Notre Dame HS [Directions] | 4:00 p.m. | 2:30PM | |
| Mon., 12/21 | V Boys Ice Hockey | Xavier | Away - Freeman Athletic Center, Wesleyan University [Directions] | W 4-2 | ||
| Mon., 12/21 | V Girls Basketball | Darien | Home - GHS Gymnasium [Directions] | W 63-50 | ||
| Mon., 12/21 | JV Girls Basketball | Darien | Home - GHS Gymnasium [Directions] | 5:15 p.m. | ||
| Mon., 12/21 | V Girls Ice Hockey | New Canaan | Away - Darien Ice Rink [Directions] | L 0-3 | ||
| Wed., 12/23 | V Boys Ice Hockey | West Haven Coop | Home - Dorothy Hamill Ice Rink [Directions] | W 12-0 | ||
| Wed., 12/23 | V Wrestling | Trumbull | Away - Auxiliary gym [Directions] | 49-24 L | ||
| Wed., 12/23 | V Girls Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | W 58-31 | 3:15PM | Share with JV |
| Wed., 12/23 | JV Girls Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 3:15 p.m. | 3:15PM | Share with V |
| Wed., 12/23 | FR Girls Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 2:00 p.m. | 2:30PM | |
| Fri., 12/25 | School Holidays and Closings | Christmas Day | ||||
| Mon., 12/28 | JV Boys Ice Hockey | New Canaan | Away - Darien Ice Rink [Directions] | 4:30 p.m. | ||
| Mon., 12/28 | V Wrestling | Holiday Tournament | Away - Danbury HS | 9:15 a.m. | ||
| Mon., 12/28 | V Girls Basketball | University | Away - Woodstock Academy [Directions] | W 95-31 | ||
| Tue., 12/29 | V Boys Basketball | Cheney Tech | Away - Woodstock Academy [Directions] | W 80-40 | ||
| Tue., 12/29 | V Girls Basketball | Woodstock Academy | Away - Alumni Fieldhouse [Directions] | W 71-43 | ||
| Wed., 12/30 | V Boys Basketball | Woodstock Academy | Away - Alumni Fieldhouse [Directions] | W 54-41 | ||
| Wed., 12/30 | V Wrestling | Darien, Staples, Fairfield Warde | Home - GHS Gymnasium [Directions] | Warde 40-27 L Darien 66-9 W Staples 62-11 W | ||
| Wed., 12/30 | V Girls Gymnastics | Staples | Home - Greenwich YWCA [Directions] | 144.35 | ||
| Fri., 1/1 | School Holidays and Closings | New Years Day | ||||
| Sat., 1/2 | V Boys Ice Hockey | New Canaan | Away - Darien Ice Rink [Directions] | W 3-1 | ||
| Sat., 1/2 | JV Wrestling | Norwalk Tournament | Away - Norwalk HS | 9:00 a.m. | ||
| Sat., 1/2 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice [Directions] | W 4-1 | ||
| Tue., 1/5 | V Boys Basketball | St. Joseph | Home - GHS Gymnasium [Directions] | W 75-66(OT) | ||
| Tue., 1/5 | JV Boys Basketball | St. Joseph | Home - GHS Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/5 | FR Boys Basketball | St. Joseph | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/5 | V Bowling | Match | Away - Nutmeg Lanes | 3:00 p.m. | ||
| Tue., 1/5 | V Girls Basketball | St. Joseph | Away - St. Joseph HS [Directions] | W 57-51 | 3:00PM | Share with JV |
| Tue., 1/5 | JV Girls Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 5:15 p.m. | 3:00PM | Share with V |
| Tue., 1/5 | FR Girls Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | 2:30PM | |
| Tue., 1/5 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Dorothy Hamill Ice Rink [Directions] | W 5-2 | ||
| Wed., 1/6 | V Boys Ice Hockey | Rye Country Day (NY) | Away | W 5-0 | ||
| Wed., 1/6 | V Boys Swimming and Diving | Trumbull | Home - GHS Pool [Directions] | Greenwich 124 Trumbull 38 | ||
| Thu., 1/7 | V Girls Gymnastics | Fairfield Warde | Home - Greenwich YWCA [Directions] | 142.0 | ||
| Fri., 1/8 | V Boys Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | L 54-57 | 4:30PM | Share with JV |
| Fri., 1/8 | JV Boys Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/8 | FR Boys Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | 2:30PM | |
| Fri., 1/8 | V Boys Indoor Track | Alpha Owl Invitational | Away - Southern Connecticut State University | 5:00 p.m. | ||
| Fri., 1/8 | V Boys Swimming and Diving | Ridgefield | Home - GHS Pool [Directions] | Greenwich 113 Ridgefield 72 | ||
| Fri., 1/8 | JV Wrestling | Shoreline Tournament | Away - New Rochelle HS | 4:00 p.m. | ||
| Fri., 1/8 | V Girls Basketball | Westhill | Home - GHS Gymnasium [Directions] | W 73-40 | ||
| Fri., 1/8 | JV Girls Basketball | Westhill | Home - GHS Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/8 | FR Girls Basketball | Westhill | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/8 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Winter Garden Ice Arena [Directions] | L 3-5 | ||
| Fri., 1/8 | V Girls Indoor Track | Alpha Owl Invitational | Away - Southern Connecticut State University | 5:00 p.m. | ||
| Sat., 1/9 | V Boys Ice Hockey | St. Joseph | Home - Dorothy Hamill Ice Rink [Directions] | W 2-0 | ||
| Sat., 1/9 | V Boys Indoor Track | MEET | Away - Staples HS | 10:00 a.m. | ||
| Sat., 1/9 | V Wrestling | Shoreline Tournament | Away - New Rochelle HS | 9:30 a.m. | ||
| Sat., 1/9 | V Girls Gymnastics | Trumbull, Joel Barlow | Away - Next Dimension Gymnastics [Directions] | 142.1 | ||
| Sat., 1/9 | V Girls Indoor Track | MEET | Away - Staples HS | 10:00 a.m. | 8:15AM | 2 Buses |
| Mon., 1/11 | V Boys Ice Hockey | New Canaan | Home - Dorothy Hamill Ice Rink [Directions] | W 6-3 | ||
| Tue., 1/12 | V Boys Basketball | Wilton | Home - GHS Gymnasium [Directions] | L 51-55 | ||
| Tue., 1/12 | JV Boys Basketball | Wilton | Home - GHS Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/12 | FR Boys Basketball | Wilton | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/12 | V Bowling | Match | Away - Nutmeg Lanes | 3:00 p.m. | ||
| Tue., 1/12 | V Girls Basketball | Wilton | Away - Nicholas Zeoli Field House [Directions] | W 66-55 | 3:00PM | Share with JV |
| Tue., 1/12 | JV Girls Basketball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 5:15 p.m. | 3:00PM | Share with V |
| Tue., 1/12 | V Girls Ice Hockey | Stamford/Westhill/Staples | Home - Dorothy Hamill Ice Rink [Directions] | L 3-4(OT) | ||
| Wed., 1/13 | V Boys Fencing | North Haven | Home - GHS Gymnasium [Directions] | 6:00 p.m. | ||
| Wed., 1/13 | V Boys Ice Hockey | Notre Dame-Fairfield | Home - Dorothy Hamill Ice Rink [Directions] | W 4-1 | ||
| Wed., 1/13 | V Boys Swimming and Diving | Danbury | Home - GHS Pool [Directions] | Greenwich 111 Danbury 57 | ||
| Wed., 1/13 | V Wrestling | Westhill | Away - Westhill - New Gymnasium [Directions] | 37-36 W | ||
| Wed., 1/13 | V Girls Fencing | North Haven | Home - GHS Gymnasium [Directions] | 6:00 p.m. | ||
| Wed., 1/13 | JV Girls Ice Hockey | Stamford/Westhill/Staples | Away - Westport PAL Rink [Directions] | 6:00 p.m. | ||
| Wed., 1/13 | School Holidays and Closings | Early Release | ||||
| Thu., 1/14 | FR Boys Basketball | Brunswick School | Away - Brunswick HS | 4:00 p.m. | 3:00PM | |
| Thu., 1/14 | JV Boys Ice Hockey | Brunswick School | Away - Brunswick School | 5:00 p.m. | ||
| Thu., 1/14 | V Girls Gymnastics | Darien, New Milford | Home - Greenwich YWCA [Directions] | Darien 133.15 New Milford 127.4 | ||
| Fri., 1/15 | V Boys Basketball | Ridgefield | Home - GHS Gymnasium [Directions] | W 56-53 | ||
| Fri., 1/15 | JV Boys Basketball | Ridgefield | Home - GHS Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/15 | FR Boys Basketball | Ridgefield | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/15 | V Boys Indoor Track | Yale Indoor Classic | Away - Coxe Cage | 1:00 p.m. | ||
| Fri., 1/15 | V Boys Swimming and Diving | Staples | Away - Staples HS Pool [Directions] | Greenwich 117 Staples 69 | ||
| Fri., 1/15 | V Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | L 42-67 | 3:00PM | Share with JV |
| Fri., 1/15 | JV Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 5:15 p.m. | 3:00PM | Share with V |
| Fri., 1/15 | FR Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 3:45 p.m. | 2:30pm | |
| Fri., 1/15 | V Girls Ice Hockey | Darien | Away - Darien Ice Rink [Directions] | L 0-9 | ||
| Fri., 1/15 | V Girls Indoor Track | Yale Indoor Classic | Away - Coxe Cage | 1:00 p.m. | 10:30AM | |
| Sat., 1/16 | V Boys Ice Hockey | Trumbull | Away - Shelton Rinks [Directions] | W 5-2 | ||
| Sat., 1/16 | V Boys Indoor Track | MEET | Away - Wilton HS | 9:30 a.m. | ||
| Sat., 1/16 | V Wrestling | Staples | Away - Staples HS [Directions] | 64-16 W | ||
| Sat., 1/16 | Winter Dance Team | Dance in the Woods | Away | 4:00 p.m. | ||
| Sat., 1/16 | V Girls Indoor Track | MEET | Away - Wilton HS | 9:30 a.m. | 7:45AM | 2 Buses |
| Mon., 1/18 | V Boys Ice Hockey | Darien | Home - Dorothy Hamill Ice Rink [Directions] | L 0-3 | ||
| Mon., 1/18 | JV Boys Ice Hockey | Milford Coop | Away - Milford Ice Pavilion [Directions] | 9:30 a.m. | ||
| Mon., 1/18 | V Girls Gymnastics | Wilton | Home - Greenwich YWCA [Directions] | Greenwich 142.2 Wilton 133.3 | ||
| Mon., 1/18 | School Holidays and Closings | MLK Day | ||||
| Tue., 1/19 | V Boys Basketball | Staples | Away - Staples H.S. Gym [Directions] | W 52-51 | 4:15PM | Share with JV |
| Tue., 1/19 | JV Boys Basketball | Staples | Away - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/19 | FR Boys Basketball | Staples | Away - Staples H.S. Gym [Directions] | 4:00 p.m. | 2:30pm | |
| Tue., 1/19 | V Bowling | Match | Away - Nutmeg Lanes | 3:00 p.m. | ||
| Tue., 1/19 | V Girls Basketball | Staples | Home - GHS Gymnasium [Directions] | W 71-25 | ||
| Tue., 1/19 | JV Girls Basketball | Staples | Home - GHS Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/19 | FR Girls Basketball | Staples | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 1/20 | JV Boys Ice Hockey | Darien | Home - Dorothy Hamill Ice Rink [Directions] | 8:30 p.m. | ||
| Wed., 1/20 | V Boys Swimming and Diving | Darien | Home - GHS Pool [Directions] | Greenwich 113 Darien 73 | ||
| Wed., 1/20 | V Wrestling | Ridgefield | Away - RHS Main Gym [Directions] | 42-30 W | ||
| Wed., 1/20 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away [Directions] | W 6-1 | ||
| Fri., 1/22 | V Boys Swimming and Diving | Wilton | Away - Wilton YMCA [Directions] | Greenwich 118 Wilton 52 | ||
| Fri., 1/22 | FR Girls Basketball | Fairfield Ludlowe | Away - FLHS Aux Gym [Directions] | 5:30 p.m. | ||
| Sat., 1/23 | School Holidays and Closings | SAT Testing | ||||
| Sun., 1/24 | V Wrestling | Walkill Duals | Away | 11:00 a.m. | ||
| Tue., 1/26 | V Boys Basketball | Trumbull | Home - GHS Gymnasium [Directions] | W 69-64 | ||
| Tue., 1/26 | JV Boys Basketball | Trumbull | Home - GHS Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/26 | FR Boys Basketball | Trumbull | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/26 | V Bowling | Match | Away - Nutmeg Lanes | 3:00 p.m. | ||
| Tue., 1/26 | V Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | L 64-70 | 3:00PM | Share with JV |
| Tue., 1/26 | JV Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | 5:15 p.m. | 3:00PM | Share with V |
| Tue., 1/26 | FR Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | 2:30pm | |
| Wed., 1/27 | V Boys Ice Hockey | Westhill/Stamford | Away - Terry Connors [Directions] | W 6-3 | ||
| Wed., 1/27 | V Boys Swimming and Diving | Westhill/Stamford | Home - GHS Pool [Directions] | Greenwich 106 Westhill/Stamford 80 | ||
| Wed., 1/27 | V Wrestling | Norwalk | Away - Norwalk High Gym [Directions] | 69-9 W | ||
| Wed., 1/27 | FR Girls Basketball | Greenwich Country Day | Away - Greenwich Country Day | 4:30 p.m. | 3:45pm | |
| Wed., 1/27 | V Girls Gymnastics | New Canaan, Westhill | Away [Directions] | 138.9 | ||
| Thu., 1/28 | V Boys Alpine Skiing | RACE | Away - Mt Southington | 4:00 p.m. | ||
| Thu., 1/28 | V Boys Fencing | Fairfield Warde | Away - Fairfield Warde HS [Directions] | 6:30 p.m. | ||
| Thu., 1/28 | V Girls Alpine Skiing | RACE | Away - Mt Southington | 4:00 p.m. | ||
| Thu., 1/28 | V Girls Fencing | Fairfield Warde | Away - Fairfield Warde HS [Directions] | 6:30 p.m. | ||
| Thu., 1/28 | V Girls Ice Hockey | Northwest Catholic | Home - Dorothy Hamill Ice Rink [Directions] | W 4-3 | ||
| Fri., 1/29 | V Boys Basketball | Norwalk | Home - GHS Gymnasium [Directions] | L 59-70 | ||
| Fri., 1/29 | JV Boys Basketball | Norwalk | Home - GHS Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 1/29 | FR Boys Basketball | Norwalk | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/29 | JV Boys Ice Hockey | Pelham Memorial (NY) | Home - Dorothy Hamill Ice Rink [Directions] | 9:15 p.m. | ||
| Fri., 1/29 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Home - GHS Pool [Directions] | Greenwich 126 Brien McMahon/Norwalk 59 | ||
| Fri., 1/29 | V Girls Basketball | Norwalk | Away - Norwalk High Gym [Directions] | W 80-49 | 2:30pm | Share with JV |
| Fri., 1/29 | JV Girls Basketball | Norwalk | Away - Norwalk High Gym [Directions] | 4:00 p.m. | 2:30pm | Share with V |
| Sat., 1/30 | V Boys Fencing | Hopkins School | Away - Hopkins School | 10:00 a.m. | ||
| Sat., 1/30 | V Boys Ice Hockey | Trinity Catholic | Away - Terry Conners Ice Rink | W 9-0 | ||
| Sat., 1/30 | V Boys Indoor Track | Division Championships | Away - Staples HS | 10:00 a.m. | ||
| Sat., 1/30 | V Boys Swimming and Diving | Fairfield Prep | Home - GHS Pool [Directions] | Greenwich 122 Fairfield Prep 64 | ||
| Sat., 1/30 | V Wrestling | Ridgefield Challenge | Away - Ridgefield HS | 9:30 a.m. | ||
| Sat., 1/30 | V Competitive Cheerleading | Walcott Competition | Away - WHS | TBA | ||
| Sat., 1/30 | V Girls Fencing | Hopkins School | Away - Hopkins School | 10:00 a.m. | ||
| Sat., 1/30 | V Girls Ice Hockey | Farmington | Home - Dorothy Hamill Ice Rink [Directions] | W 5-2 | ||
| Sat., 1/30 | V Girls Indoor Track | Division Championships | Away - Staples HS | 9:30 a.m. | 8:15AM | 2 Buses |
| Mon., 2/1 | V Boys Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | W 70-64 | 4:15PM | Share with JV |
| Mon., 2/1 | JV Boys Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 5:15 p.m. | ||
| Mon., 2/1 | FR Boys Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | 2:30PM | |
| Mon., 2/1 | V Boys Ice Hockey | Hamden | Away - Lou Astorino Ice Rink [Directions] | L 1-2(OT) | ||
| Mon., 2/1 | V Girls Basketball | Fairfield Warde | Home - GHS Gymnasium [Directions] | L 47-50 | ||
| Mon., 2/1 | JV Girls Basketball | Fairfield Warde | Home - GHS Gymnasium [Directions] | 5:15 p.m. | ||
| Mon., 2/1 | FR Girls Basketball | Fairfield Warde | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 2/2 | V Boys Alpine Skiing | RACE | Away - Mt Southington | 4:00 p.m. | ||
| Tue., 2/2 | JV Boys Ice Hockey | Pelham Memorial (NY) | Away - Ice Hutch | 8:30 p.m. | ||
| Tue., 2/2 | JV Wrestling | Fairfield Warde | Away - Fairfield Warde Small Gym [Directions] | 4:30 p.m. | ||
| Tue., 2/2 | V Bowling | Match | Away - Nutmeg Lanes | 3:00 p.m. | ||
| Tue., 2/2 | V Girls Alpine Skiing | RACE | Away - Mt Southington | 4:00 p.m. | ||
| Wed., 2/3 | V Boys Basketball | Stamford | Away - Stamford HS [Directions] | L 37-48 | 4:30PM | Share with JV |
| Wed., 2/3 | JV Boys Basketball | Stamford | Away - Stamford HS [Directions] | 5:15 p.m. | ||
| Wed., 2/3 | FR Boys Basketball | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | 2:30pm | |
| Wed., 2/3 | V Boys Ice Hockey | Staples | Away - Milford Ice Pavilion [Directions] | W 5-1 | ||
| Wed., 2/3 | V Boys Swimming and Diving | New Canaan | Away - New Canaan YMCA [Directions] | 3:00 p.m. | ||
| Wed., 2/3 | V Wrestling | Stamford | Home - GHS Gymnasium [Directions] | 45-17 W | ||
| Wed., 2/3 | V Girls Basketball | Stamford | Home - GHS Gymnasium [Directions] | W 64-55 | ||
| Wed., 2/3 | JV Girls Basketball | Stamford | Home - GHS Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 2/3 | FR Girls Basketball | Stamford | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 2/3 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton Rinks [Directions] | W 7-2 | ||
| Thu., 2/4 | V Boys Alpine Skiing | RACE | Away - Mt Southington | 4:00 p.m. | ||
| Thu., 2/4 | V Boys Fencing | Brunswick School | Home - GHS Gymnasium [Directions] | 4:30 p.m. | ||
| Thu., 2/4 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Home - Dorothy Hamill Ice Rink [Directions] | W 1-0 | ||
| Thu., 2/4 | V Boys Indoor Track | FCIAC Championships | Away - New Haven Athletic Center | 4:00 p.m. | ||
| Thu., 2/4 | V Girls Alpine Skiing | RACE | Away - Mt Southington | 4:00 p.m. | ||
| Thu., 2/4 | V Girls Fencing | Brunswick School | Home - GHS Gymnasium [Directions] | 4:30 p.m. | ||
| Thu., 2/4 | V Girls Indoor Track | FCIAC Championships | Away - New Haven Athletic Center | 4:00 p.m. | 1:30PM | |
| Fri., 2/5 | JV Boys Ice Hockey | Scarsdale (NY) | Away - EJ Murray Rink | Cancelled | ||
| Fri., 2/5 | V Wrestling | Fairfield Ludlowe, Masuk | Away - FLHS Aux Gym [Directions] | Cancelled | ||
| Sat., 2/6 | JV Boys Fencing | Novice Tournament | Away - Guilford HS | 10:00 a.m. | ||
| Sat., 2/6 | JV Wrestling | JV Championships | Away - Fairfield Ludlowe HS | 9:00 a.m. | ||
| Sat., 2/6 | V Competitive Cheerleading | FCIAC Championships | Away - Wilton HS | 11:00 a.m. | ||
| Sat., 2/6 | JV Girls Fencing | Novice Tournament | Away - Guilford HS | 10:00 a.m. | ||
| Sat., 2/6 | V Girls Gymnastics | Fairfield Ludlowe | Away [Directions] | 140.9 | ||
| Sat., 2/6 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Dorothy Hamill Ice Rink [Directions] | L 2-3 | ||
| Sat., 2/6 | School Holidays and Closings | ACT Testing | ||||
| Tue., 2/9 | V Boys Basketball | Trinity Catholic | Home - GHS Gymnasium [Directions] | W 77-67 | ||
| Tue., 2/9 | JV Boys Basketball | Trinity Catholic | Home - GHS Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 2/9 | FR Boys Basketball | Trinity Catholic | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 2/9 | V Boys Ice Hockey | St. Joseph | Away - Shelton Rinks [Directions] | L 0-3 | ||
| Tue., 2/9 | V Wrestling | Danbury | Away - Danbury HS - NEW gym [Directions] | 68-3 L | ||
| Tue., 2/9 | V Girls Basketball | Trinity Catholic | Away - Walsh Court | W 73-31 | 2:30pm | Share with JV |
| Tue., 2/9 | JV Girls Basketball | Trinity Catholic | Away - Walsh Court | 4:00 p.m. | 2:30pm | Share with V |
| Tue., 2/9 | V Girls Gymnastics | Staples | Home - Greenwich YWCA [Directions] | 135.0 | ||
| Wed., 2/10 | V Boys Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | W 76-47 | 4:00PM | Share with JV |
| Wed., 2/10 | JV Boys Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 5:15 p.m. | ||
| Wed., 2/10 | FR Boys Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 4:00 p.m. | 2:30pm | |
| Wed., 2/10 | V Girls Basketball | Bridgeport Central | Home - GHS Gymnasium [Directions] | W 69-18 | ||
| Wed., 2/10 | JV Girls Basketball | Bridgeport Central | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 2/10 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away [Directions] | W 1-0 | ||
| Thu., 2/11 | V Boys Ice Hockey | Norwalk | Home - Dorothy Hamill Ice Rink [Directions] | W 6-0 | ||
| Thu., 2/11 | V Boys Indoor Track | CIAC Class LL State Championships | Away - New Haven Athletic Center | 4:00 p.m. | ||
| Thu., 2/11 | V Girls Indoor Track | CIAC Class LL State Championships | Away - New Haven Athletic Center | 4:00 p.m. | Yes | |
| Fri., 2/12 | V Boys Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | L 57-58 | 3:45PM | Share with JV |
| Fri., 2/12 | JV Boys Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 5:15 p.m. | ||
| Fri., 2/12 | FR Boys Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 4:00 p.m. | 2:30pm | |
| Fri., 2/12 | V Boys Ice Hockey | Notre Dame-West Haven | Away - Bennett Rink [Directions] | L 2-3 | ||
| Fri., 2/12 | V Wrestling | FCIAC Championships | Away - New Canaan HS | 4:30 p.m. | ||
| Fri., 2/12 | V Girls Basketball | Danbury | Home - GHS Gymnasium [Directions] | W 81-46 | ||
| Fri., 2/12 | JV Girls Basketball | Danbury | Home - GHS Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 2/12 | FR Girls Basketball | Danbury | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 2/13 | V Wrestling | FCIAC Championships | Away - New Canaan HS | 11:00 a.m. | ||
| Sat., 2/13 | V Girls Gymnastics | FCIAC Championships | Away - Jonathan Law HS | 143.0 | ||
| Mon., 2/15 | V Boys Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | L 55-64 | 9:00am | Share with JV |
| Mon., 2/15 | JV Boys Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 10:30 a.m. | ||
| Mon., 2/15 | V Girls Basketball | Fairfield Ludlowe | Home - GHS Gymnasium [Directions] | W 57-41 | ||
| Mon., 2/15 | JV Girls Basketball | Fairfield Ludlowe | Home - GHS Gymnasium [Directions] | 10:30 a.m. | ||
| Mon., 2/15 | V Girls Ice Hockey | New Canaan | Home - Dorothy Hamill Ice Rink [Directions] | L 0-2 | ||
| Mon., 2/15 | School Holidays and Closings | President Day | ||||
| Tue., 2/16 | V Wrestling | Brunswick School (Scrim.) | Away - Brunswick School | 4:30 p.m. | ||
| Tue., 2/16 | JV Girls Ice Hockey | New Canaan | Home - Dorothy Hamill Ice Rink [Directions] | 5:00 p.m. | ||
| Wed., 2/17 | V Boys Alpine Skiing | RACE | Away - Mt Southington | 4:00 p.m. | ||
| Wed., 2/17 | V Boys Basketball | Brien McMahon | Home - GHS Gymnasium [Directions] | L 45-47 | ||
| Wed., 2/17 | JV Boys Basketball | Brien McMahon | Home - GHS Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 2/17 | FR Boys Basketball | Brien McMahon | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 2/17 | V Boys Ice Hockey | Darien | Away - Darien Ice Rink [Directions] | W 2-1 | ||
| Wed., 2/17 | V Girls Alpine Skiing | RACE | Away - Mt Southington | 4:00 p.m. | ||
| Wed., 2/17 | V Girls Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | W 62-30 | 2:30pm | Share with JV |
| Wed., 2/17 | JV Girls Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | 2:30pm | Share with V |
| Thu., 2/18 | V Boys Fencing | Rye Country Day (NY) | Away - Rye Country Day School | 4:00 p.m. | ||
| Thu., 2/18 | V Boys Ice Hockey | Ridgefield | Home - Dorothy Hamill Ice Rink [Directions] | W 3-2 | ||
| Thu., 2/18 | V Girls Fencing | Rye Country Day (NY) | Away - Rye Country Day School | 4:00 p.m. | ||
| Fri., 2/19 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Home - GHS Pool [Directions] | Greenwich 123 Fairfield Ludlowe/Warde 62 | ||
| Fri., 2/19 | V Wrestling | Class LL State Championships | Away - Trumbull HS | 4:30 p.m. | ||
| Fri., 2/19 | V Girls Ice Hockey | Farmington | Away [Directions] | W 5-2 | ||
| Sat., 2/20 | JV Boys Ice Hockey | Fairfield | Away - Wonderland of Ice | 7:30 p.m. | ||
| Sat., 2/20 | V Boys Indoor Track | CIAC State Open Championships | Away - New Haven Athletic Center | 9:00 a.m. | ||
| Sat., 2/20 | JV Boys Swimming and Diving | MEET | Home - GHS Pool [Directions] | 1:30 p.m. | ||
| Sat., 2/20 | V Wrestling | Class LL State Championships | Away - Trumbull HS | 9:00 a.m. | ||
| Sat., 2/20 | V Girls Basketball | FCIAC Tournament | Away - Stamford HS | 4:00 p.m. | ||
| Sat., 2/20 | Winter Dance Team | Dance Jam | Away - Fairfield Warde HS | 4:00 p.m. | ||
| Sat., 2/20 | V Girls Indoor Track | CIAC State Open Championships | Away - New Haven Athletic Center | 9:00 a.m. | ||
| Mon., 2/22 | V Boys Basketball | Darien | Away - DHS Main Gym [Directions] | W 46-45 | 4:15PM | Share with JV |
| Mon., 2/22 | JV Boys Basketball | Darien | Away - DHS Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 2/22 | FR Boys Basketball | Darien | Away - DHS Main Gym [Directions] | 3:45 p.m. | 2:30PM | |
| Mon., 2/22 | V Boys Swimming and Diving | FCIAC Trials | Home - GHS Pool [Directions] | 4:30 p.m. | ||
| Mon., 2/22 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Dorothy Hamill Ice Rink [Directions] | W 8-3 | ||
| Wed., 2/24 | V Boys Basketball | New Canaan | Home - GHS Gymnasium [Directions] | W 57-44 | ||
| Wed., 2/24 | JV Boys Basketball | New Canaan | Home - GHS Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 2/24 | FR Boys Basketball | New Canaan | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 2/24 | V Boys Ice Hockey | Wilton | Away - Winter Garden Rink-Ridgefield [Directions] | W 5-0 | ||
| Wed., 2/24 | V Boys Swimming and Diving | FCIAC Diving Championships | Away - Westhill HS | 4:30 p.m. | ||
| Thu., 2/25 | V Boys Fencing | Milford | Away | 6:00 p.m. | ||
| Thu., 2/25 | JV Boys Ice Hockey | Brunswick School | Away - Brunswick HS | 5:00 p.m. | ||
| Thu., 2/25 | V Girls Fencing | Milford | Away | 6:00 p.m. | ||
| Fri., 2/26 | FR Boys Basketball | Greenwich Country Day | Away - Greenwich Country Day | 6:00 p.m. | ||
| Fri., 2/26 | V Boys Swimming and Diving | FCIAC Championships | Home [Directions] | 6:30 p.m. | ||
| Sat., 2/27 | V Boys Fencing | Hopkins School | Away - Hopkins School | 10:00 a.m. | ||
| Sat., 2/27 | V Competitive Cheerleading | New England Open Cheer and Dance Championship | Away - East Haven HS | 11:00 a.m. | ||
| Sat., 2/27 | V Girls Basketball | Avon | Home - GHS Gymnasium [Directions] | W 74-55 | ||
| Sat., 2/27 | Winter Dance Team | State Championship | Away | 11:00 a.m. | ||
| Sat., 2/27 | V Girls Fencing | Hopkins School | Away - Hopkins School | 10:00 a.m. | ||
| Sat., 2/27 | V Girls Gymnastics | Class L State Championships | Away - Pomperaug HS | 11:45 a.m. | ||
| Sun., 2/28 | V Boys Indoor Track | New England Championships | Away - Reggie Lewis Center | 1:00 p.m. | ||
| Sun., 2/28 | V Girls Indoor Track | New England Championships | Away - Reggie Lewis Center | 1:00 p.m. | ||
| Tue., 3/1 | V Boys Indoor Track | Eastern Championships | Away - New York Armory | 3:30 p.m. | ||
| Tue., 3/1 | V Bowling | Match | Away - Nutmeg Lanes | 3:00 p.m. | ||
| Tue., 3/1 | V Girls Indoor Track | Eastern Championships | Away - New York Armory | 3:30 p.m. | ||
| Wed., 3/2 | V Boys Alpine Skiing | RACE | Away - Mt Southington | 4:00 p.m. | ||
| Wed., 3/2 | V Boys Basketball | Masuk (Scrim.) | Away - David Strong Gymnasium @ Masuk HS [Directions] | 3:30 p.m. | ||
| Wed., 3/2 | V Boys Ice Hockey | FCIAC Tournament | Away - Terry Connors Ice Rink | 7:00 p.m. | ||
| Wed., 3/2 | V Girls Alpine Skiing | RACE | Away - Mt Southington | 4:00 p.m. | ||
| Thu., 3/3 | V Girls Basketball | CIAC Class LL Tournament | Away - Southington HS | 6:00 p.m. | ||
| Fri., 3/4 | V Boys Basketball | Trinity Catholic (Scrim.) | Away - Walsh Court | 3:30 p.m. | ||
| Sat., 3/5 | V Boys Ice Hockey | FCIAC Championship | Away - Terry Conners Ice Rink | 3:00 p.m. | ||
| Sat., 3/5 | V Boys Indoor Track | National Championships | Away - New York Armory | TBA | ||
| Sat., 3/5 | V Competitive Cheerleading | State Championships | Away - New Haven Athletic Center | 11:00 a.m. | ||
| Sat., 3/5 | V Girls Gymnastics | State Open Championships | Away - New Milford HS | 10:00 a.m. | ||
| Sat., 3/5 | V Girls Indoor Track | National Championships | Away - New York Armory | TBA | ||
| Sun., 3/6 | V Boys Fencing | State Individual Championship | Away - Fairfield Ludlowe HS | 9:00 a.m. | ||
| Sun., 3/6 | V Girls Fencing | State Individual Championships | Away - Fairfield Ludlowe HS | 9:00 a.m. | ||
| Mon., 3/7 | V Girls Basketball | CIAC Class LL Tournament | Away - Fairfield Warde HS | 7:00 p.m. | ||
| Tue., 3/8 | V Boys Alpine Skiing | State Championships | Away - Mt Southington | 3:00 p.m. | ||
| Tue., 3/8 | V Boys Basketball | Class LL State Tournament | Away - Stamford HS | 7:00 p.m. | ||
| Tue., 3/8 | V Girls Alpine Skiing | State Championships | Away - Mt Southington | 3:00 p.m. | ||
| Wed., 3/9 | V Boys Ice Hockey | State Tournament | Home - Dorothy Hamill Ice Rink [Directions] | 5:15 p.m. | ||
| Wed., 3/9 | V Boys Swimming and Diving | CIAC Class LL Diving Championships | Away - Hamden HS | 5:30 p.m. | ||
| Wed., 3/9 | School Holidays and Closings | Early Release | ||||
| Thu., 3/10 | V Boys Basketball | Class LL State Tournament | Away - Classical Magnet Gymnasium | 7:00 p.m. | ||
| Fri., 3/11 | V Girls Basketball | Class LL State Tournament | Away - Sheehan HS | 7:00 p.m. | ||
| Sat., 3/12 | V Boys Fencing | State Team Championship | Away - North Haven HS | 8:30 a.m. | ||
| Sat., 3/12 | V Boys Ice Hockey | State Tournament | Away - Webster Bank Arena | 2:00 p.m. | ||
| Sat., 3/12 | V Boys Swimming and Diving | CIAC Class LL Trials | Away - Hamden HS | 3:30 p.m. | ||
| Sat., 3/12 | V Girls Fencing | State Team Championship | Away - North Haven HS | 8:30 a.m. | ||
| Sat., 3/12 | School Holidays and Closings | SAT Testing | ||||
| Mon., 3/14 | Unified Sports Basketball | Tournament | Away - Fairfield Ludlowe HS | 3:00 p.m. | ||
| Wed., 3/16 | V Boys Swimming and Diving | CIAC Class LL Championships | Away - Wesleyan University | 1:30 p.m. | ||
| Thu., 3/17 | V Boys Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown HS | 5:30 p.m. | ||
| Sat., 3/19 | V Boys Rugby | Four Leaf | Away | TBA | ||
| Sat., 3/19 | JV Boys Rugby | Four Leaf | Away - Randell Island | 1:00 p.m. | ||
| Sat., 3/19 | V Boys Swimming and Diving | CIAC State Open Championships | Away - Yale University | 2:30 p.m. | ||
| Tue., 3/22 | V Boys Rugby | Ridgefield | Home - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Tue., 3/22 | JV Boys Rugby | Ridgefield | Home - Cardinal Stadium [Directions] | 5:00 p.m. | ||
| Wed., 3/23 | V Boys Sailing | REGATTA | Home - Grass Island [Directions] | 3:00 p.m. | ||
| Wed., 3/23 | V Boys Tennis | Byram Hills (NY) (Scrim.) | Home - GHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 3/23 | V Girls Sailing | REGATTA | Home - Grass Island [Directions] | 3:00 p.m. | ||
| Thu., 3/24 | V Boys Lacrosse | John Jay (NY) (Scrim.) | Away - John Jay HS | 4:00 p.m. | ||
| Thu., 3/24 | V Girls Lacrosse | Norwalk (Scrim.) | Away - Testa Field, NHS [Directions] | 4:00 p.m. | ||
| Thu., 3/24 | V Softball | Trinity Catholic (Scrim.) | Home - GHS Softball Field [Directions] | 3:45 p.m. | ||
| Fri., 3/25 | School Holidays and Closings | Good Friday | ||||
| Sat., 3/26 | V Boys Lacrosse | Scrimmage Day | Away - Darien HS | 8:00 a.m. | ||
| Sat., 3/26 | V Boys Rugby | Union | Away | TBA | ||
| Sat., 3/26 | JV Girls Lacrosse | Joel Barlow (Scrim.) | Away - Field I (Stadium) [Directions] | 1:00 p.m. | ||
| Mon., 3/28 | V Girls Lacrosse | Fairfield Ludlowe (Scrim.) | Away - Taft Field [Directions] | 3:30 p.m. | ||
| Tue., 3/29 | V Baseball | Trinity Catholic (Scrim.) | Home - GHS Baseball Field [Directions] | 3:30 p.m. | ||
| Tue., 3/29 | V Softball | Mamaroneck (NY) (Scrim.) | Away - Mamaroneck HS | 4:15 p.m. | ||
| Tue., 3/29 | JV Softball | Mamaroneck (NY) (Scrim.) | Away | 4:00 p.m. | ||
| Wed., 3/30 | V Baseball | New Canaan (Scrim.) | Away - Mead Park [Directions] | 4:00 p.m. | ||
| Wed., 3/30 | V Baseball | New Canaan (Scrim.) | Away - Mead Park [Directions] | 4:00 p.m. | ||
| Wed., 3/30 | V Boys Lacrosse | Brunswick School (Scrim.) | Home - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Wed., 3/30 | JV Boys Lacrosse | Brunswick School (Scrim.) | Home - GHS Field 7 [Directions] | 4:00 p.m. | ||
| Wed., 3/30 | FR Boys Rugby | Simsbury | Away - Simsbury [Directions] | 5:00 p.m. | ||
| Wed., 3/30 | V Boys Sailing | REGATTA | Home - Grass Island [Directions] | 3:00 p.m. | ||
| Wed., 3/30 | V Boys Tennis | Brunswick School (Scrim.) | Away - Brunswick School | 4:00 p.m. | ||
| Wed., 3/30 | V Girls Lacrosse | Loomis Chaffee School (Scrim.) | Away - Trumbull Insports Center | 3:00 p.m. | ||
| Wed., 3/30 | V Girls Sailing | REGATTA | Home - Grass Island [Directions] | 3:00 p.m. | ||
| Wed., 3/30 | V Girls Tennis | Daniel Hand (Scrim.) | Home - GHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 3/30 | V Girls Water Polo | Greenwich Aquatics | Away - Greenwich YMCA | 6:45 p.m. | ||
| Thu., 3/31 | JV Boys Rugby | Fairfield Prep | Away - Fairfield Prep [Directions] | 4:00 p.m. | ||
| Thu., 3/31 | V Boys Volleyball | New Canaan (Scrim.) | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 3/31 | V Softball | Bethel (Scrim.) | Away - Kasack Field at Johnson School [Directions] | 3:30 p.m. | ||
| Fri., 4/1 | JV Boys Lacrosse | St. Anthonys (NY) (Scrim.) | Home - GHS Field 7 [Directions] | 4:00 p.m. | ||
| Fri., 4/1 | V Boys Rugby | Fairfield | Away - Fairfield Warde HS | 7:00 p.m. | ||
| Fri., 4/1 | JV Boys Rugby | Fairfield | Away - Fairfield Warde HS | 8:00 p.m. | ||
| Sat., 4/2 | V Boys Lacrosse | St. Anthonys (NY) | Away - St Anthony School | L 6-15 | ||
| Sat., 4/2 | V Boys Sailing | REGATTA | Home [Directions] | 9:00 a.m. | ||
| Sat., 4/2 | V Girls Lacrosse | Scrimmage | Away - Greenwich Academy | 3:30 p.m. | ||
| Sat., 4/2 | V Girls Sailing | REGATTA | Home - Grass Island [Directions] | 9:00 a.m. | ||
| Tue., 4/5 | V Boys Lacrosse | Westhill | Home - Cardinal Stadium [Directions] | W 20-1 | ||
| Tue., 4/5 | JV Boys Lacrosse | Westhill | Home - GHS Field 7 [Directions] | 4:00 p.m. | ||
| Wed., 4/6 | JV Boys Rugby | French American School | Home - GHS Field 7 [Directions] | 4:30 p.m. | ||
| Wed., 4/6 | V Boys Sailing | REGATTA | Home - Grass Island [Directions] | 3:00 p.m. | ||
| Wed., 4/6 | V Boys Tennis | St. Joseph | Home - GHS Tennis Courts [Directions] | W 6-0 | ||
| Wed., 4/6 | V Girls Golf | Fairfield Warde | Away - Smith Richardson [Directions] | GHS 184 FWHS 186 | ||
| Wed., 4/6 | V Girls Lacrosse | Cheshire | Home - Cardinal Stadium [Directions] | W 10-6 | ||
| Wed., 4/6 | JV Girls Lacrosse | Cheshire | Home - Cardinal Stadium [Directions] | W 9-8 | ||
| Wed., 4/6 | FR Girls Lacrosse | New Canaan | Home - GHS Field 3 [Directions] | 4:00 p.m. | ||
| Wed., 4/6 | V Girls Sailing | REGATTA | Home - Grass Island [Directions] | 3:00 p.m. | ||
| Wed., 4/6 | V Softball | Brookfield | Home - GHS Softball Field [Directions] | L 6-10 | ||
| Wed., 4/6 | V Girls Tennis | St. Joseph | Away - St. Joseph HS [Directions] | W 6-0 | ||
| Wed., 4/6 | V Girls Water Polo | Staples | Home - GHS Pool [Directions] | 3:00 p.m. | ||
| Thu., 4/7 | FR Boys Lacrosse | Fairfield Prep | Home - GHS Field 7 [Directions] | 4:00 p.m. | ||
| Thu., 4/7 | FR Boys Rugby | Harvey School (NY) | Away - Harvey School | 4:30 p.m. | ||
| Fri., 4/8 | V Boys Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | L 0-3 | ||
| Fri., 4/8 | JV Boys Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 5:30 p.m. | ||
| Fri., 4/8 | V Girls Lacrosse | John Jay (NY) | Home - Cardinal Stadium [Directions] | W 15-8 | ||
| Fri., 4/8 | JV Girls Lacrosse | John Jay (NY) | Home - Cardinal Stadium [Directions] | W 11-4 | ||
| Fri., 4/8 | FR Girls Lacrosse | Trumbull | Away - The Pit [Directions] | 4:00 p.m. | ||
| Fri., 4/8 | V Softball | New Canaan | Home - GHS Softball Field [Directions] | L 3-15 | ||
| Fri., 4/8 | V Girls Tennis | Greenwich Academy (Scrim.) | Home - GHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Sat., 4/9 | FR Boys Rugby | Fairfield Prep | Away - Fairfield Prep [Directions] | 11:30 a.m. | ||
| Sat., 4/9 | V Boys Sailing | REGATTA | Home - Grass Island [Directions] | 9:00 a.m. | ||
| Sat., 4/9 | V Girls Sailing | REGATTA | Home - Grass Island [Directions] | 9:00 a.m. | ||
| Sat., 4/9 | School Holidays and Closings | ACT Testing | ||||
| Sun., 4/10 | V Softball | Staples | Away - Wakeman Field [Directions] | W 16-7 | ||
| Mon., 4/11 | V Baseball | St. Joseph | Home - GHS Baseball Field [Directions] | W 10-5 | ||
| Mon., 4/11 | JV Baseball | St. Joseph | Home - Julian Curtiss School [Directions] | 4:00 p.m. | ||
| Mon., 4/11 | FR Baseball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | ||
| Mon., 4/11 | FR Boys Lacrosse | Staples | Home - GHS Field 7 [Directions] | 4:00 p.m. | ||
| Mon., 4/11 | V Boys Tennis | Wilton | Away - Wilton Tennis Courts [Directions] | L 2-5 | ||
| Mon., 4/11 | V Softball | St. Joseph | Away - St. Joseph HS [Directions] | L 0-9 | ||
| Mon., 4/11 | JV Softball | St. Joseph | Away - Long Hill Admin.,Trumbull,CT [Directions] | Cancelled | ||
| Mon., 4/11 | V Girls Tennis | Wilton | Away - Wilton Tennis Courts [Directions] | L 3-4 | ||
| Tue., 4/12 | V Boys Lacrosse | Ridgefield | Away - Tiger Hollow Stadium [Directions] | L 7-10 | ||
| Tue., 4/12 | JV Boys Lacrosse | Ridgefield | Away - Tiger Hollow Turf Field II [Directions] | 3:30 p.m. | ||
| Tue., 4/12 | FR Boys Lacrosse | Wilton | Away - Allen's Field [Directions] | 4:00 p.m. | ||
| Tue., 4/12 | V Boys Volleyball | Shelton | Away - Shelton HS Gym [Directions] | L 2-3 | ||
| Tue., 4/12 | JV Boys Volleyball | Shelton | Away - Shelton HS Gym [Directions] | 4:00 p.m. | ||
| Tue., 4/12 | V Girls Lacrosse | New Canaan | Away - Dunning Stadium [Directions] | L 10-14 | ||
| Tue., 4/12 | JV Girls Lacrosse | New Canaan | Away - Dunning Stadium [Directions] | 5:30 p.m. | ||
| Wed., 4/13 | V Baseball | Westhill | Away - Westhill Baseball Field [Directions] | L 6-18 | ||
| Wed., 4/13 | JV Baseball | Westhill | Away - Rippowam MS [Directions] | 4:00 p.m. | ||
| Wed., 4/13 | FR Baseball | Westhill | Home - GHS Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 4/13 | V Boys Tennis | Ridgefield | Home - GHS Tennis Courts [Directions] | W 5-2 | ||
| Wed., 4/13 | V Boys Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | L 0-3 | ||
| Wed., 4/13 | JV Boys Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 4/13 | V Softball | Westhill | Home - GHS Softball Field [Directions] | L 1-3 | ||
| Wed., 4/13 | JV Softball | Westhill | Home - Julian Curtiss School [Directions] | 4:00 p.m. | ||
| Wed., 4/13 | V Girls Tennis | Ridgefield | Away - RHS Tennis Courts [Directions] | W 5-2 | ||
| Thu., 4/14 | V Baseball | New Milford | Away - New Milford HS [Directions] | W 6-5 | ||
| Thu., 4/14 | JV Baseball | New Milford | Away - New Milford HS [Directions] | 4:00 p.m. | ||
| Thu., 4/14 | FR Boys Lacrosse | Stamford | Away - Stamford High Soccer Field [Directions] | 5:30 p.m. | ||
| Fri., 4/15 | V Baseball | Wilton | Home - GHS Baseball Field [Directions] | W 3-1 | ||
| Fri., 4/15 | JV Baseball | Wilton | Home - Julian Curtiss School [Directions] | 2:00 p.m. | ||
| Fri., 4/15 | FR Baseball | Wilton | Away - Allen's Meadow - Fr. Baseball Field [Directions] | 2:30 p.m. | ||
| Fri., 4/15 | V Boys Lacrosse | Wilton | Home - Cardinal Stadium [Directions] | W 12-10 | ||
| Fri., 4/15 | JV Boys Lacrosse | Wilton | Home - GHS Field 7 [Directions] | 2:00 p.m. | ||
| Fri., 4/15 | V Boys Volleyball | Trumbull | Home - GHS Gymnasium [Directions] | L 0-3 | ||
| Fri., 4/15 | JV Boys Volleyball | Trumbull | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 4/15 | V Softball | Wilton | Away - WHS Varsity Softball Field [Directions] | L 1-7 | ||
| Sat., 4/16 | V Boys Rugby | Jesuit Tournament | Away - Morven Park Field | 4:00 p.m. | Friday-Saturday | |
| Sat., 4/16 | V Boys Sailing | NESSA O'Day Qualifiers | Away - Indian Harbor Yacht Club | 9:00 a.m. | ||
| Sat., 4/16 | V Girls Lacrosse | Wilton | Home - Cardinal Stadium [Directions] | W 12-11(OT) | ||
| Sat., 4/16 | JV Girls Lacrosse | Wilton | Home - Cardinal Stadium [Directions] | 10:00 a.m. | ||
| Sat., 4/16 | V Girls Sailing | NESSA O'Day Qualifiers | Away - Indian Harbor Yacht Club | 9:00 a.m. | ||
| Sat., 4/16 | V Girls Water Polo | Choate Invitational | Away - Choate Rosemary Hall | 9:00 a.m. | Saturday - Sunday | |
| Sun., 4/17 | V Boys Sailing | NESSA O'Day Championship | Away - Indian Harbor Yacht Club | 9:00 a.m. | ||
| Sun., 4/17 | V Girls Sailing | NESSA O'Day Championship | Away - Indian Harbor Yacht Club | 9:00 a.m. | ||
| Mon., 4/18 | V Baseball | Ridgefield | Home - GHS Baseball Field [Directions] | L 5-12 | ||
| Mon., 4/18 | JV Baseball | Ridgefield | Home - Julian Curtiss School [Directions] | 4:00 p.m. | ||
| Mon., 4/18 | FR Baseball | Ridgefield | Away - Governor's Park Field (aka Ciuccoli or Old HS) [Directions] | 4:00 p.m. | ||
| Mon., 4/18 | V Boys Golf | Westhill | Home - Griffith E Harris Golf Course [Directions] | Greenwich 162 Westhill 174 | ||
| Mon., 4/18 | FR Boys Lacrosse | Greenwich Country Day | Away - GCDS | 3:30 p.m. | ||
| Mon., 4/18 | V Boys Outdoor Track | Bridgeport Central | Home - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Mon., 4/18 | V Boys Tennis | Staples | Away - Staples HS-Tennis Courts [Directions] | W 4-3 | ||
| Mon., 4/18 | JV Boys Tennis | Staples | Away - Town Farms Tennis Courts [Directions] | 4:00 p.m. | Junior Varsity | |
| Mon., 4/18 | V Boys Volleyball | Staples | Away - Staples H.S. Gym [Directions] | L 0-3 | ||
| Mon., 4/18 | JV Boys Volleyball | Staples | Away - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Mon., 4/18 | V Girls Golf | Darien | Away - Wee Burn CC [Directions] | GHS 191 DHS 213 | ||
| Mon., 4/18 | V Girls Outdoor Track | Bridgeport Central | Home - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Mon., 4/18 | V Softball | Ridgefield | Away - RHS Upper Grass Field [Directions] | L 0-11 | ||
| Mon., 4/18 | JV Softball | Ridgefield | Away - RHS Upper Grass Field [Directions] | 4:00 p.m. | ||
| Mon., 4/18 | V Girls Tennis | Staples | Home - GHS Tennis Courts [Directions] | L 6-1 | ||
| Mon., 4/18 | JV Girls Tennis | New Canaan | Home - Binney Park [Directions] | 4:00 p.m. | JVB | |
| Tue., 4/19 | V Boys Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | Greenwich 167 Trumbull 166 | ||
| Tue., 4/19 | JV Boys Golf | Darien | Away - CC of Darien [Directions] | 3:15 p.m. | ||
| Tue., 4/19 | V Boys Lacrosse | Staples | Away - Staples Stadium [Directions] | L 12-13(2OT) | ||
| Tue., 4/19 | JV Boys Lacrosse | Staples | Away - Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Tue., 4/19 | JV Boys Rugby | Harvey School (NY) | Home - GHS Field 7 [Directions] | 4:00 p.m. | ||
| Tue., 4/19 | JV Boys Tennis | Darien | Away - Cherry Lawn Park [Directions] | 4:00 p.m. | Freshman | |
| Tue., 4/19 | V Girls Golf | Wilton | Away - Silver Mine CC [Directions] | GHS 168 Wilton 182 | ||
| Tue., 4/19 | V Girls Lacrosse | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | W 15-9 | ||
| Tue., 4/19 | JV Girls Lacrosse | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 6:00 p.m. | ||
| Tue., 4/19 | FR Girls Lacrosse | Wilton | Home - GHS Field 3 [Directions] | 4:00 p.m. | ||
| Tue., 4/19 | FR Softball | Norwalk | Home - GHS Softball Field [Directions] | 4:00 p.m. | ||
| Tue., 4/19 | JV Girls Tennis | Darien | Away - Weed Beach [Directions] | 4:00 p.m. | JVA | |
| Wed., 4/20 | V Baseball | Staples | Away - Staples HS Baseball Field [Directions] | W 9-6 | ||
| Wed., 4/20 | JV Baseball | Staples | Away - Wakeman Field [Directions] | 4:00 p.m. | ||
| Wed., 4/20 | FR Baseball | Staples | Home - GHS Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 4/20 | V Boys Golf | Bridgeport Central | Away - Fairchild Wheeler Golf Course [Directions] | Greenwich 155 Central 175 | ||
| Wed., 4/20 | FR Boys Lacrosse | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 4:30 p.m. | ||
| Wed., 4/20 | V Boys Sailing | REGATTA | Home - Grass Island [Directions] | 3:00 p.m. | ||
| Wed., 4/20 | V Boys Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | W 3-2 | ||
| Wed., 4/20 | JV Boys Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | ||
| Wed., 4/20 | FR Girls Lacrosse | Darien | Home - GHS Field 3 [Directions] | 5:00 p.m. | ||
| Wed., 4/20 | V Girls Sailing | REGATTA | Home - Grass Island [Directions] | 3:00 p.m. | ||
| Wed., 4/20 | V Softball | Staples | Home - GHS Softball Field [Directions] | L 6-23 | ||
| Wed., 4/20 | V Girls Tennis | Westhill | Home - GHS Tennis Courts [Directions] | W 7-0 | ||
| Wed., 4/20 | JV Girls Tennis | Greenwich Country Day | Away - GCDS | 4:15 p.m. | JVB | |
| Thu., 4/21 | JV Boys Golf | Brien McMahon | Away [Directions] | 3:15 p.m. | ||
| Thu., 4/21 | V Boys Lacrosse | New Canaan | Home - Cardinal Stadium [Directions] | L 6-8 | ||
| Thu., 4/21 | JV Boys Lacrosse | New Canaan | Home - GHS Field 7 [Directions] | 4:00 p.m. | ||
| Thu., 4/21 | V Boys Outdoor Track | New Canaan | Away - NCHS Track Field [Directions] | 4:00 p.m. | ||
| Thu., 4/21 | V Boys Tennis | Trumbull | Home - GHS Tennis Courts [Directions] | W 7-0 | ||
| Thu., 4/21 | JV Boys Tennis | Fairfield Ludlowe | Away - Dwight Elementary School Courts [Directions] | 4:00 p.m. | Freshman | |
| Thu., 4/21 | V Boys Volleyball | New Canaan | Home - GHS Gymnasium [Directions] | L 0-3 | ||
| Thu., 4/21 | JV Boys Volleyball | New Canaan | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 4/21 | V Girls Golf | Fairfield Ludlowe | Home - Griffith E Harris Golf Course [Directions] | GHS 177 FLHS 234 | ||
| Thu., 4/21 | JV Girls Golf | Darien | Home - Millbrook Country Club [Directions] | 3:00 p.m. | ||
| Thu., 4/21 | V Girls Lacrosse | St. Joseph | Home - Cardinal Stadium [Directions] | W 16-3 | ||
| Thu., 4/21 | JV Girls Lacrosse | St. Joseph | Home - GHS Field 3 [Directions] | 4:30 p.m. | ||
| Thu., 4/21 | V Girls Outdoor Track | New Canaan | Away - NCHS Track Field [Directions] | 4:00 p.m. | ||
| Thu., 4/21 | V Girls Tennis | Trumbull | Away - THS Tennis Courts [Directions] | W 6-1 | ||
| Thu., 4/21 | JV Girls Tennis | Fairfield Ludlowe | Away - Tomlinson MS Tennis Courts [Directions] | 4:00 p.m. | JVA | |
| Fri., 4/22 | FR Boys Lacrosse | St. Joseph | Home - GHS Field 7 [Directions] | 4:00 p.m. | ||
| Fri., 4/22 | V Boys Tennis | Westhill | Away - Westhill Tennis Courts [Directions] | W 6-1 | ||
| Fri., 4/22 | V Girls Lacrosse | Glastonbury | Home - Cardinal Stadium [Directions] | W 12-6 | ||
| Fri., 4/22 | JV Girls Lacrosse | Glastonbury | Home - Cardinal Stadium [Directions] | 5:00 p.m. | ||
| Fri., 4/22 | FR Girls Lacrosse | Ridgefield | Away - Scotts Ridge MS Turf [Directions] | 4:00 p.m. | ||
| Sat., 4/23 | V Baseball | Southington | Home - GHS Baseball Field [Directions] | L 1-2 | ||
| Sat., 4/23 | JV Baseball | Southington | Home - Julian Curtiss School [Directions] | 3:00 p.m. | ||
| Sat., 4/23 | V Boys Lacrosse | Fairfield Ludlowe | Home - Cardinal Stadium [Directions] | W 10-4 | ||
| Sat., 4/23 | JV Boys Lacrosse | Fairfield Ludlowe | Home - GHS Field 7 [Directions] | 2:00 p.m. | ||
| Sat., 4/23 | V Boys Rugby | Xavier (NY) | Home - Cardinal Stadium [Directions] | 7:00 p.m. | ||
| Sat., 4/23 | JV Boys Rugby | Xavier (NY) | Home - Cardinal Stadium [Directions] | 5:00 p.m. | ||
| Sat., 4/23 | FR Boys Rugby | Xavier (NY) | Home - GHS Field 7 [Directions] | 5:00 p.m. | ||
| Mon., 4/25 | V Baseball | Trumbull | Home - GHS Baseball Field [Directions] | W 4-3 | ||
| Mon., 4/25 | JV Baseball | Trumbull | Home - Julian Curtiss School [Directions] | 4:00 p.m. | ||
| Mon., 4/25 | FR Baseball | Trumbull | Away - Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/25 | V Boys Golf | Stamford | Home - Griffith E Harris Golf Course [Directions] | Greenwich 161 Stamford 216 | ||
| Mon., 4/25 | JV Boys Golf | Brunswick School | Home - Greenwich Country Club [Directions] | 3:15 p.m. | ||
| Mon., 4/25 | V Boys Tennis | Norwalk | Home - GHS Tennis Courts [Directions] | W 6-1 | ||
| Mon., 4/25 | JV Boys Tennis | Brunswick School | Home - Central MS [Directions] | 4:30 p.m. | Junior Varsity | |
| Mon., 4/25 | JV Girls Golf | Darien | Away - Wee Burn CC [Directions] | 3:00 p.m. | ||
| Mon., 4/25 | FR Girls Lacrosse | Staples | Away - Ginny Parker Field - Staples [Directions] | 5:15 p.m. | ||
| Mon., 4/25 | V Girls Outdoor Track | Danbury, Stamford | Home - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Mon., 4/25 | V Softball | Trumbull | Away - Varsity Softball Field [Directions] | L 0-13 | ||
| Mon., 4/25 | JV Softball | Trumbull | Away - JV Softball Field [Directions] | 4:15 p.m. | ||
| Mon., 4/25 | V Girls Tennis | Norwalk | Away - Norwalk HS [Directions] | W 7-0 | ||
| Tue., 4/26 | V Boys Lacrosse | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | W 12-7 | ||
| Tue., 4/26 | V Girls Golf | Danbury | Away - Richter Park Golf Course [Directions] | GHS 189 DHS 194 | ||
| Tue., 4/26 | V Girls Lacrosse | Stamford | Away - Stamford HS [Directions] | W 15-7 | ||
| Tue., 4/26 | JV Girls Lacrosse | Stamford | Away - Stamford HS [Directions] | 5:30 p.m. | ||
| Tue., 4/26 | FR Girls Lacrosse | Greenwich Country Day | Away - CGDS | 3:30 p.m. | ||
| Tue., 4/26 | School Holidays and Closings | School Closed | ||||
| Wed., 4/27 | V Baseball | Norwalk | Home - GHS Baseball Field [Directions] | L 1-2 | ||
| Wed., 4/27 | JV Baseball | Norwalk | Home - Julian Curtiss School [Directions] | 4:00 p.m. | ||
| Wed., 4/27 | FR Baseball | Norwalk | Away - Nathan Hale M.S. Upper [Directions] | 4:00 p.m. | ||
| Wed., 4/27 | V Boys Golf | Wilton | Home - Round Hill Club [Directions] | Greenwich 162 Wilton 187 | ||
| Wed., 4/27 | JV Boys Golf | Darien | Home - Griffith E Harris Golf Course [Directions] | 3:15 p.m. | ||
| Wed., 4/27 | FR Boys Lacrosse | Ridgefield | Home - GHS Field 7 [Directions] | 5:00 p.m. | ||
| Wed., 4/27 | V Boys Outdoor Track | Danbury, Stamford | Home - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Wed., 4/27 | V Boys Sailing | REGATTA | Home - Grass Island [Directions] | 3:00 p.m. | ||
| Wed., 4/27 | V Boys Tennis | Fairfield Warde | Away - FWHS Blake Courts [Directions] | W 7-0 | ||
| Wed., 4/27 | JV Boys Tennis | Fairfield Warde | Away - FWHS Knapps Courts [Directions] | 4:00 p.m. | Junior Varsity | |
| Wed., 4/27 | JV Boys Tennis | Wilton | Away [Directions] | 4:30 p.m. | Freshman | |
| Wed., 4/27 | V Boys Volleyball | Darien | Home - GHS Gymnasium [Directions] | L 0-3 | ||
| Wed., 4/27 | JV Boys Volleyball | Darien | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 4/27 | V Girls Golf | Staples | Away - Longshore [Directions] | GHS 193 SHS 187 | ||
| Wed., 4/27 | JV Girls Golf | Staples | Away [Directions] | 3:00 p.m. | ||
| Wed., 4/27 | FR Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde Grass Utility Field [Directions] | 4:00 p.m. | ||
| Wed., 4/27 | V Girls Sailing | REGATTA | Home - Grass Island [Directions] | 3:00 p.m. | ||
| Wed., 4/27 | V Softball | Norwalk | Away - Ray Barry Field, NHS [Directions] | L 8-9 | ||
| Wed., 4/27 | JV Softball | Norwalk | Away - Naramake School [Directions] | 4:00 p.m. | ||
| Wed., 4/27 | V Girls Tennis | Fairfield Warde | Home - GHS Tennis Courts [Directions] | W 6-1 | ||
| Wed., 4/27 | JV Girls Tennis | Wilton | Home - Binney Park [Directions] | 4:00 p.m. | JVB | |
| Thu., 4/28 | V Boys Golf | Brunswick Invitational | Away | Greenwich 323 (155) Bergen Catholic 300 NC 323 Brunswick 323 | ||
| Thu., 4/28 | JV Boys Golf | Ridgefield | Away [Directions] | 3:15 p.m. | ||
| Thu., 4/28 | V Boys Lacrosse | Stamford | Home - Cardinal Stadium [Directions] | W 16-0 | ||
| Thu., 4/28 | JV Boys Lacrosse | Stamford | Home - GHS Field 7 [Directions] | 4:00 p.m. | ||
| Thu., 4/28 | V Boys Tennis | Stamford | Away - Stamford HS [Directions] | W 7-0 | ||
| Thu., 4/28 | V Girls Golf | Trumbull | Home - Griffith E Harris Golf Course [Directions] | GHS 177 THS 218 | ||
| Thu., 4/28 | JV Girls Golf | Trumbull | Home - Millbrook Country Club [Directions] | 3:00 p.m. | ||
| Thu., 4/28 | V Girls Outdoor Track | Penn Relays | Away - Franklin Field | 4:00 p.m. | ||
| Thu., 4/28 | V Girls Outdoor Track | Penn Relays | Away - Franklin Field | 4:00 p.m. | ||
| Thu., 4/28 | FR Softball | Darien | Away - DHS Softball JV Field [Directions] | 4:00 p.m. | ||
| Thu., 4/28 | V Girls Tennis | Stamford | Home - GHS Tennis Courts [Directions] | W 7-0 | ||
| Thu., 4/28 | JV Girls Tennis | Staples | Home - Binney Park [Directions] | 4:00 p.m. | JVA | |
| Thu., 4/28 | V Girls Water Polo | Greenwich Aquatics | Home - GHS Pool [Directions] | 5:00 p.m. | ||
| Fri., 4/29 | V Baseball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | W 7-3 | ||
| Fri., 4/29 | JV Baseball | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | ||
| Fri., 4/29 | FR Baseball | Fairfield Warde | Home - GHS Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 4/29 | V Boys Outdoor Track | O'Grady Relays | Away - Danbury HS | 6:00 p.m. | Friday - Saturday | |
| Fri., 4/29 | V Boys Outdoor Track | O'Grady Relays | Away - Danbury HS | 6:00 p.m. | Friday - Saturday | |
| Fri., 4/29 | V Boys Outdoor Track | O'Grady Relays | Away - Danbury HS | 6:00 p.m. | Friday - Saturday | |
| Fri., 4/29 | V Girls Lacrosse | Yorktown (NY) | Home - Cardinal Stadium [Directions] | W 12-11 | ||
| Fri., 4/29 | JV Girls Lacrosse | Yorktown (NY) | Home - Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Fri., 4/29 | FR Girls Lacrosse | Trumbull | Home - GHS Field 3 [Directions] | 4:00 p.m. | ||
| Fri., 4/29 | V Girls Outdoor Track | O'Grady Relays | Away - Danbury HS | 6:00 p.m. | Friday-Saturday | |
| Fri., 4/29 | V Girls Outdoor Track | O'Grady Relays | Away - Danbury HS | 6:00 p.m. | Friday-Saturday | |
| Fri., 4/29 | V Softball | Fairfield Warde | Home - GHS Softball Field [Directions] | L 4-5 | ||
| Fri., 4/29 | V Girls Water Polo | Staples | Away - Staples HS [Directions] | 3:00 p.m. | ||
| Sat., 4/30 | V Boys Rugby | Aspetuck | Away | TBA | ||
| Sat., 4/30 | JV Boys Rugby | Aspetuck | Away | TBA | ||
| Sat., 4/30 | V Girls Water Polo | Deerfield Academy | Away - Deerfield Academy | 3:00 p.m. | ||
| Sun., 5/1 | V Boys Sailing | Hotchkiss Invitational | Away - Lake Wononscopomuc | 1:00 p.m. | ||
| Sun., 5/1 | V Girls Sailing | Hotchkiss Invitational | Away - Lake Wononscopomuc | 1:00 p.m. | ||
| Mon., 5/2 | V Baseball | Stamford | Away - Stamford HS [Directions] | W 4-3 | ||
| Mon., 5/2 | JV Baseball | Stamford | Away [Directions] | 4:00 p.m. | ||
| Mon., 5/2 | FR Baseball | Stamford | Home - GHS Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/2 | V Boys Golf | Danbury | Away - Richter Park Golf Course [Directions] | Greenwich 159 Danbury 157 | ||
| Mon., 5/2 | JV Boys Golf | Fairfield Prep | Home - Griffith E Harris Golf Course [Directions] | 3:15 p.m. | ||
| Mon., 5/2 | V Boys Tennis | Bridgeport Central | Away [Directions] | W 7-0 | ||
| Mon., 5/2 | V Boys Volleyball | Danbury | Home - GHS Gymnasium [Directions] | W 3-0 | ||
| Mon., 5/2 | JV Boys Volleyball | Danbury | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 5/2 | FR Girls Lacrosse | Fairfield Ludlowe | Away - FLHS Front Lawn [Directions] | 4:00 p.m. | ||
| Mon., 5/2 | V Girls Outdoor Track | Ridgefield, Trumbull | Home - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Mon., 5/2 | V Softball | Stamford | Home - GHS Softball Field [Directions] | L 6-19 | ||
| Mon., 5/2 | JV Softball | Stamford | Home - Julian Curtiss School [Directions] | 4:00 p.m. | ||
| Mon., 5/2 | V Girls Tennis | Bridgeport Central | Home - GHS Tennis Courts [Directions] | W 7-0 | ||
| Mon., 5/2 | JV Girls Tennis | Darien | Away - Weed Beach [Directions] | 4:00 p.m. | JVB | |
| Tue., 5/3 | V Boys Golf | Trinity Catholic | Home - Griffith E Harris Golf Course [Directions] | Greenwich 163 Trinity 198 | ||
| Tue., 5/3 | JV Boys Golf | Fairfield Ludlowe | Away [Directions] | Cancelled | ||
| Tue., 5/3 | JV Boys Rugby | Fordham Prep (NY) | Away - Fordham Prep | 4:00 p.m. | ||
| Tue., 5/3 | FR Boys Rugby | Fordham Prep (NY) | Away - Fordham Prep | 5:00 p.m. | ||
| Tue., 5/3 | V Girls Golf | Ridgefield | Away - Silver Spring Golf Course [Directions] | GHS 180 RHS 225 | ||
| Tue., 5/3 | V Girls Lacrosse | Darien | Home - Cardinal Stadium [Directions] | L 6-16 | ||
| Tue., 5/3 | JV Girls Lacrosse | Darien | Home - Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Tue., 5/3 | FR Softball | Norwalk | Away - Naramake School [Directions] | Cancelled | ||
| Wed., 5/4 | JV Baseball | Bridgeport Central | Away - Seaside Park Diamond 10 [Directions] | 4:00 p.m. | ||
| Wed., 5/4 | FR Boys Lacrosse | New Canaan | Home - GHS Field 7 [Directions] | 4:00 p.m. | ||
| Wed., 5/4 | V Boys Outdoor Track | Ridgefield, Trumbull | Home - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Wed., 5/4 | V Boys Sailing | REGATTA | Home - Grass Island [Directions] | 3:00 p.m. | ||
| Wed., 5/4 | V Boys Volleyball | Ridgefield | Home - GHS Gymnasium [Directions] | L 0-3 | ||
| Wed., 5/4 | JV Boys Volleyball | Ridgefield | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 5/4 | V Girls Golf | Danbury | Home - Griffith E Harris Golf Course [Directions] | GHS 187 DHS 191 | ||
| Wed., 5/4 | JV Girls Golf | Danbury | Home - Griffith E Harris Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 5/4 | V Girls Sailing | REGATTA | Home - Grass Island [Directions] | 3:00 p.m. | ||
| Wed., 5/4 | V Softball | Bridgeport Central | Home - Julian Curtiss School [Directions] | W 9-7 | ||
| Wed., 5/4 | V Girls Water Polo | Greenwich Academy | Away - Greenwich YMCA | 3:30 p.m. | ||
| Thu., 5/5 | V Boys Golf | Norwalk, Brien McMahon | Away - Oak Hills G.C. [Directions] | Greenwich 166 Norwalk 219 McMahon 244 | ||
| Thu., 5/5 | JV Boys Golf | Ridgefield | Home - Griffith E Harris Golf Course [Directions] | 3:30 p.m. | ||
| Thu., 5/5 | V Boys Lacrosse | Norwalk | Home - Cardinal Stadium [Directions] | W 13-5 | ||
| Thu., 5/5 | JV Boys Lacrosse | Norwalk | Home - GHS Field 7 [Directions] | 4:00 p.m. | ||
| Thu., 5/5 | FR Boys Rugby | Harvey School (NY) | Away - Harvey School | 4:00 p.m. | ||
| Thu., 5/5 | V Boys Sailing | Regatta | Home - Grass Island [Directions] | 3:00 p.m. | ||
| Thu., 5/5 | V Boys Tennis | Danbury | Away - Danbury HS Tennis Courts [Directions] | W 7-0 | ||
| Thu., 5/5 | JV Boys Tennis | Greenwich Country Day | Away - Greenwich Country Day | 4:00 p.m. | Junior Varsity | |
| Thu., 5/5 | JV Boys Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | Freshman | |
| Thu., 5/5 | V Girls Lacrosse | Trumbull | Away - McDougall Stadium [Directions] | W 17-7 | ||
| Thu., 5/5 | JV Girls Lacrosse | Trumbull | Away - McDougall Stadium [Directions] | 5:00 p.m. | ||
| Thu., 5/5 | FR Girls Lacrosse | New Canaan | Away - Dunning Stadium [Directions] | TBA | ||
| Thu., 5/5 | V Girls Sailing | Regatta | Home - Grass Island [Directions] | 3:00 p.m. | ||
| Thu., 5/5 | V Softball | Trinity Catholic | Away - Stamford HS | W 19-17 | ||
| Thu., 5/5 | FR Softball | Danbury | Home - GHS Softball Field [Directions] | 4:00 p.m. | ||
| Thu., 5/5 | V Girls Tennis | Danbury | Home - GHS Tennis Courts [Directions] | W 7-0 | ||
| Thu., 5/5 | JV Girls Tennis | Ridgefield | Home - Binney Park [Directions] | 4:00 p.m. | JVB | |
| Fri., 5/6 | V Boys Rugby | Fairfield Prep | Away - Fairfield University [Directions] | 4:00 p.m. | ||
| Fri., 5/6 | V Boys Volleyball | Trumbull | Away - THS Main Gym [Directions] | L 2-3 | ||
| Fri., 5/6 | JV Boys Volleyball | Trumbull | Away - THS Main Gym [Directions] | 3:30 p.m. | ||
| Fri., 5/6 | V Girls Lacrosse | Westhill | Home - Cardinal Stadium [Directions] | W 15-4 | ||
| Fri., 5/6 | JV Girls Lacrosse | Westhill | Home - Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Fri., 5/6 | FR Girls Lacrosse | Darien | Away - DHS Field #1 -Turf [Directions] | 3:30 p.m. | ||
| Fri., 5/6 | V Girls Outdoor Track | Irv Black Invitational | Away - Willowbrook Park | 3:30 p.m. | ||
| Fri., 5/6 | V Girls Outdoor Track | Irv Black Invitational | Away - Willowbrook Park | 3:30 p.m. | ||
| Sat., 5/7 | V Boys Lacrosse | Chaminade (NY) | Home - Cardinal Stadium [Directions] | L 8-14 | ||
| Sat., 5/7 | JV Boys Lacrosse | Chaminade (NY) | Home - GHS Field 7 [Directions] | 3:00 p.m. | ||
| Sat., 5/7 | V Boys Outdoor Track | Irv Black Invitational | Away - Willowbrook Park | 10:00 a.m. | Saturday | |
| Sat., 5/7 | JV Boys Rugby | Fairfield Prep | Home - GHS Field 7 [Directions] | 5:00 p.m. | ||
| Sat., 5/7 | V Boys Sailing | Fairfield Cup | Away - Pequot Yacht Club | 9:00 a.m. | ||
| Sat., 5/7 | V Girls Outdoor Track | Middletown Invitational | Away - Middletown HS | 1:00 p.m. | ||
| Sat., 5/7 | V Girls Outdoor Track | Middletown Invitational | Away - Middletown HS | 1:00 p.m. | ||
| Sat., 5/7 | V Girls Sailing | Fairfield Cup | Away - Pequot Yacht Club | 9:00 a.m. | ||
| Sat., 5/7 | School Holidays and Closings | SAT Testing | ||||
| Mon., 5/9 | V Baseball | Danbury | Away - Danbury HS Varsity Baseball Field [Directions] | W 13-2 | ||
| Mon., 5/9 | JV Baseball | Danbury | Away - Danbury HS Junior Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/9 | FR Baseball | Danbury | Home - GHS Baseball Field [Directions] | 4:30 p.m. | ||
| Mon., 5/9 | V Boys Golf | Fairfield Warde | Away - Smith Richardson [Directions] | Greenwich 158 Warde 172 | ||
| Mon., 5/9 | FR Boys Lacrosse | Staples | Away - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Mon., 5/9 | V Boys Tennis | Fairfield Ludlowe | Away - FLHS Tennis Courts [Directions] | W 6-1 | ||
| Mon., 5/9 | JV Boys Tennis | Fairfield Ludlowe | Away - Dwight Elementary School Courts [Directions] | 4:00 p.m. | Freshman | |
| Mon., 5/9 | V Boys Volleyball | Staples | Home - GHS Gymnasium [Directions] | L 0-3 | ||
| Mon., 5/9 | JV Boys Volleyball | Staples | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 5/9 | V Girls Lacrosse | Staples | Away - Ginny Parker Field - Staples [Directions] | W 10-9 | ||
| Mon., 5/9 | JV Girls Lacrosse | Staples | Away - Ginny Parker Field - Staples [Directions] | 5:15 p.m. | ||
| Mon., 5/9 | FR Girls Lacrosse | Staples | Home - GHS Field 3 [Directions] | 5:00 p.m. | ||
| Mon., 5/9 | V Girls Outdoor Track | Westhill | Away - Westhill Football Field [Directions] | 4:00 p.m. | ||
| Mon., 5/9 | V Softball | Danbury | Home - GHS Softball Field [Directions] | L 2-15 | ||
| Mon., 5/9 | JV Softball | Danbury | Home - Julian Curtiss School [Directions] | 4:00 p.m. | ||
| Mon., 5/9 | FR Softball | Danbury | Away - Danbury HS Varsity Softball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/9 | V Girls Tennis | Fairfield Ludlowe | Home - GHS Tennis Courts [Directions] | W 7-0 | ||
| Mon., 5/9 | JV Girls Tennis | Fairfield Ludlowe | Home - Binney Park [Directions] | 4:00 p.m. | JVA | |
| Mon., 5/9 | V Girls Water Polo | Hopkins School | Away - Hopkins School | 4:15 p.m. | ||
| Tue., 5/10 | V Baseball | Bridgeport Central | Away - Central H.S. Baseball Field [Directions] | W 8-0 | ||
| Tue., 5/10 | V Boys Golf | Fairfield Ludlowe | Home - Griffith E Harris Golf Course [Directions] | Greenwich 157 Ludlowe 181 | ||
| Tue., 5/10 | JV Boys Golf | Wilton | Away [Directions] | 3:15 p.m. | ||
| Tue., 5/10 | V Boys Lacrosse | Brien McMahon | Away - Brien McMahon HS [Directions] | W 13-3 | ||
| Tue., 5/10 | JV Boys Lacrosse | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:00 p.m. | ||
| Tue., 5/10 | V Boys Outdoor Track | Westhill | Away [Directions] | 4:00 p.m. | ||
| Tue., 5/10 | JV Boys Rugby | Stamford | Home - GHS Field 7 [Directions] | 5:00 p.m. | ||
| Tue., 5/10 | V Boys Tennis | Brien McMahon | Home - GHS Tennis Courts [Directions] | W 6-1 | ||
| Tue., 5/10 | JV Girls Golf | Fairfield | Away - South Pine Creek | 3:30 p.m. | ||
| Tue., 5/10 | FR Softball | Darien | Home - Julian Curtiss School [Directions] | 4:00 p.m. | ||
| Tue., 5/10 | V Girls Tennis | Brien McMahon | Away - Brien McMahon HS [Directions] | W 7-0 | ||
| Wed., 5/11 | V Baseball | Fairfield Ludlowe | Away - Kiwanis Field [Directions] | W 5-0 | ||
| Wed., 5/11 | JV Baseball | Fairfield Ludlowe | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | ||
| Wed., 5/11 | FR Baseball | Fairfield Ludlowe | Home - GHS Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/11 | FR Boys Lacrosse | New Canaan | Away - Saxe MS Field [Directions] | 4:00 p.m. | ||
| Wed., 5/11 | V Boys Sailing | REGATTA | Home - Grass Island [Directions] | 3:00 p.m. | ||
| Wed., 5/11 | JV Boys Tennis | Darien | Home - Central MS [Directions] | 4:30 p.m. | Freshman | |
| Wed., 5/11 | V Boys Volleyball | Fairfield Warde | Home - GHS Gymnasium [Directions] | L 2-3 | ||
| Wed., 5/11 | JV Boys Volleyball | Fairfield Warde | Home - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 5/11 | V Girls Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | GHS 170 THS 194 | ||
| Wed., 5/11 | JV Girls Golf | Trumbull | Away [Directions] | 3:15 p.m. | ||
| Wed., 5/11 | V Girls Lacrosse | Daniel Hand | Home - Cardinal Stadium [Directions] | L 8-9 | ||
| Wed., 5/11 | JV Girls Lacrosse | Daniel Hand | Home - Cardinal Stadium [Directions] | 6:00 p.m. | ||
| Wed., 5/11 | V Girls Sailing | FCSL Championship | Away - Indian Harbor Yacht Club | 3:00 p.m. | ||
| Wed., 5/11 | V Softball | Fairfield Ludlowe | Home - GHS Softball Field [Directions] | L 8-13 | ||
| Wed., 5/11 | JV Softball | Fairfield Ludlowe | Home - Julian Curtiss School [Directions] | 4:00 p.m. | ||
| Wed., 5/11 | JV Girls Tennis | Fairfield Warde | Away - Fairfield Woods MS Courts [Directions] | 4:00 p.m. | JVA | |
| Wed., 5/11 | School Holidays and Closings | Early Release | ||||
| Thu., 5/12 | V Baseball | Trinity Catholic | Home - GHS Baseball Field [Directions] | W 4-1 | ||
| Thu., 5/12 | V Boys Golf | St. Joseph | Home - Griffith E Harris Golf Course [Directions] | Greenwich 161 St. Joseph 205 | ||
| Thu., 5/12 | V Boys Lacrosse | Danbury | Home - Cardinal Stadium [Directions] | W 17-4 | ||
| Thu., 5/12 | JV Boys Lacrosse | Danbury | Home - GHS Field 7 [Directions] | 4:00 p.m. | ||
| Thu., 5/12 | V Boys Outdoor Track | Loucks Games | Away - White Plains HS | 4:00 p.m. | Thursday-Friday-Saturday-Sunday | |
| Thu., 5/12 | V Boys Outdoor Track | Loucks Games | Away - White Plains HS | 4:00 p.m. | Thursday-Friday-Saturday-Sunday | |
| Thu., 5/12 | V Boys Outdoor Track | Loucks Games | Away - White Plains HS | 4:00 p.m. | Thursday-Friday-Saturday-Sunday | |
| Thu., 5/12 | JV Boys Rugby | Darien | Away - Darien HS [Directions] | 4:00 p.m. | ||
| Thu., 5/12 | V Boys Tennis | Darien | Away - DHS Tennis Courts [Directions] | W 5-2 | ||
| Thu., 5/12 | JV Boys Tennis | Darien | Away - Cherry Lawn Park [Directions] | 4:30 p.m. | Junior Varsity | |
| Thu., 5/12 | V Boys Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | L 1-3 | ||
| Thu., 5/12 | JV Boys Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 5/12 | V Girls Golf | New Canaan | Home - Millbrook Country Club [Directions] | GHS 186 NCHS 210 Red tees | ||
| Thu., 5/12 | JV Girls Golf | New Canaan | Home - Millbrook Country Club [Directions] | 3:00 p.m. | ||
| Thu., 5/12 | JV Girls Golf | New Canaan | Home - Millbrook Country Club [Directions] | Cancelled | ||
| Thu., 5/12 | V Girls Outdoor Track | Glenn Loucks Games | Away - White Plains HS | 4:00 p.m. | Thursday-Friday-Saturday-Sunday | |
| Thu., 5/12 | V Girls Outdoor Track | Glenn Loucks Games | Away - White Plains HS | 4:00 p.m. | Thursday-Friday-Saturday-Sunday | |
| Thu., 5/12 | V Softball | Brien McMahon | Away - Brien McMahon HS [Directions] | W 20-7 | ||
| Thu., 5/12 | JV Softball | Brien McMahon | Away - Brookside Elementary School [Directions] | 4:15 p.m. | ||
| Thu., 5/12 | FR Softball | Danbury | Away - Danbury HS Varsity Softball Field [Directions] | 4:00 p.m. | ||
| Thu., 5/12 | V Girls Tennis | Darien | Home - GHS Tennis Courts [Directions] | L 7-0 | ||
| Thu., 5/12 | JV Girls Tennis | Darien | Home - Binney Park [Directions] | 4:00 p.m. | JVB | |
| Fri., 5/13 | V Boys Rugby | Staples | Away - Staples HS [Directions] | 4:00 p.m. | ||
| Fri., 5/13 | JV Boys Rugby | Staples | Away - Staples HS [Directions] | 4:00 p.m. | ||
| Fri., 5/13 | V Boys Tennis | Trinity Catholic | Home - Sound Shore Indoor Tennis [Directions] | W 5-0 | ||
| Fri., 5/13 | V Girls Tennis | Trinity Catholic | Home - Sound Shore Indoor Tennis [Directions] | W 7-0 | ||
| Sat., 5/14 | V Baseball | Brien McMahon | Home - GHS Baseball Field [Directions] | W 7-1 | ||
| Sat., 5/14 | V Baseball | Westhill | Away - Cubeta Field [Directions] | L 2-5 | ||
| Sat., 5/14 | V Boys Lacrosse | Darien | Away - DHS Stadium Field [Directions] | L 12-13(OT) | ||
| Sat., 5/14 | JV Boys Lacrosse | Darien | Away - DHS Field #1 -Turf [Directions] | 10:30 a.m. | ||
| Sat., 5/14 | FR Boys Lacrosse | Darien | Home - GHS Field 7 [Directions] | 10:00 a.m. | ||
| Sat., 5/14 | FR Boys Rugby | Fairfield Prep Tournament | Away - Fairfield Prep | 10:00 a.m. | ||
| Sat., 5/14 | V Boys Sailing | NESSA MASSA Intersectional | Away - Sail Black Rock | 9:00 a.m. | ||
| Sat., 5/14 | V Girls Lacrosse | Manhassett (NY) | Home - Cardinal Stadium [Directions] | L 5-15 | ||
| Sat., 5/14 | JV Girls Lacrosse | Manhassett (NY) | Home - Cardinal Stadium [Directions] | 9:30 a.m. | ||
| Sat., 5/14 | FR Girls Lacrosse | Ridgefield | Home - GHS Field 3 [Directions] | 10:00 a.m. | ||
| Sat., 5/14 | V Girls Sailing | NESSA MESSA Intersectional | Away - Sail Black Rock | 9:00 a.m. | ||
| Sat., 5/14 | V Softball | Bacon Academy | Away - BA Softball Field [Directions] | W 8-5 | ||
| Sat., 5/14 | V Girls Water Polo | Lady Cardinal Invitational | Home - GHS Pool [Directions] | 9:00 a.m. | ||
| Sun., 5/15 | V Boys Sailing | NESSA MASSA Intersectional | Away - Sail Black Rock | 9:00 a.m. | ||
| Sun., 5/15 | V Girls Sailing | NESSA MESSA Intersectional | Away - Sail Black Rock | 9:00 a.m. | ||
| Mon., 5/16 | V Baseball | Darien | Away - DHS Baseball Varsity Field [Directions] | L 0-1 | ||
| Mon., 5/16 | JV Baseball | Darien | Away - DHS Baseball JV Field [Directions] | 4:00 p.m. | ||
| Mon., 5/16 | FR Baseball | Darien | Home - GHS Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/16 | V Boys Sailing | FCSL Silver Cup | Home - Grass Island [Directions] | 3:00 p.m. | ||
| Mon., 5/16 | V Boys Tennis | New Canaan | Home - GHS Tennis Courts [Directions] | W 6-1 | ||
| Mon., 5/16 | JV Boys Tennis | New Canaan | Home - Central MS [Directions] | 5:00 p.m. | Freshman | |
| Mon., 5/16 | V Boys Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | W 3-1 | ||
| Mon., 5/16 | V Girls Outdoor Track | Staples | Away - Staples Stadium [Directions] | 4:00 p.m. | ||
| Mon., 5/16 | V Girls Sailing | FCSL Silver Cup | Home - Grass Island [Directions] | 3:00 p.m. | ||
| Mon., 5/16 | V Softball | Darien | Home - GHS Softball Field [Directions] | L 8-10 | ||
| Mon., 5/16 | JV Softball | Darien | Home - Julian Curtiss School [Directions] | 4:00 p.m. | ||
| Mon., 5/16 | V Girls Tennis | New Canaan | Away - NCHS Tennis Courts [Directions] | L 4-3 | ||
| Mon., 5/16 | JV Girls Tennis | New Canaan | Home - Binney Park [Directions] | 4:00 p.m. | JVB | |
| Tue., 5/17 | V Boys Golf | Ridgefield | Away - Silver Spring Country Club [Directions] | Greenwich 163 Ridgefield 157 | ||
| Tue., 5/17 | V Boys Lacrosse | Trumbull | Away - McDougall Stadium [Directions] | W 16-10 | ||
| Tue., 5/17 | JV Boys Lacrosse | Trumbull | Away - McDougall Stadium [Directions] | 4:45 p.m. | ||
| Tue., 5/17 | FR Boys Lacrosse | Darien | Away - Middlesex Lower Field [Directions] | 4:00 p.m. | ||
| Tue., 5/17 | V Boys Outdoor Track | Staples | Away - Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/17 | FR Boys Rugby | Fordham Prep | Home - GHS Field 7 [Directions] | 4:30 p.m. | ||
| Tue., 5/17 | V Boys Sailing | FCSL Gold Cup | Home - Grass Island [Directions] | 3:00 p.m. | ||
| Tue., 5/17 | JV Boys Tennis | Horace Greeley (NY) | Away - Horace Greeley HS | 4:00 p.m. | ||
| Tue., 5/17 | JV Boys Tennis | Staples | Home - Central MS [Directions] | 4:30 p.m. | Junior Varsity | |
| Tue., 5/17 | V Boys Volleyball | St. Joseph | Home - GHS Gymnasium [Directions] | W 3-0 | ||
| Tue., 5/17 | JV Boys Volleyball | St. Joseph | Home - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 5/17 | V Girls Golf | Ridgefield | Home - Griffith E Harris Golf Course [Directions] | GHS 174 RHS 224 | ||
| Tue., 5/17 | V Girls Lacrosse | Ridgefield | Home - Cardinal Stadium [Directions] | L 7-8 | ||
| Tue., 5/17 | JV Girls Lacrosse | Ridgefield | Home - Cardinal Stadium [Directions] | 6:00 p.m. | ||
| Tue., 5/17 | FR Girls Lacrosse | Norwalk | Home - GHS Field 3 [Directions] | 4:00 p.m. | ||
| Tue., 5/17 | V Girls Sailing | FCSL Gold Cup | Home - Grass Island [Directions] | 3:00 p.m. | ||
| Tue., 5/17 | FR Softball | Darien | Away - DHS Softball JV Field [Directions] | 4:00 p.m. | ||
| Tue., 5/17 | JV Girls Tennis | Fairfield Warde | Home - Binney Park [Directions] | 4:00 p.m. | JVA | |
| Wed., 5/18 | V Baseball | New Canaan | Home - GHS Baseball Field [Directions] | L 1-7 | ||
| Wed., 5/18 | JV Baseball | New Canaan | Home - Julian Curtiss School [Directions] | 4:00 p.m. | ||
| Wed., 5/18 | FR Baseball | New Canaan | Away - Waveny Park - Coppo Field [Directions] | 4:00 p.m. | ||
| Wed., 5/18 | V Boys Golf | New Canaan | Home - Griffith E Harris Golf Course [Directions] | Greenwich 155 New Canaan 157 | ||
| Wed., 5/18 | JV Boys Golf | Faith Prep | Away | 3:15 p.m. | ||
| Wed., 5/18 | V Boys Outdoor Track | JV Championships | Away - Darien HS | 3:00 p.m. | ||
| Wed., 5/18 | JV Boys Tennis | Fairfield Warde | Away - FWHS Knapps Courts [Directions] | 4:00 p.m. | Junior Varsity | |
| Wed., 5/18 | V Boys Volleyball | Darien | Away - DHS Main Gym [Directions] | L 1-3 | ||
| Wed., 5/18 | JV Boys Volleyball | Darien | Away - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 5/18 | V Girls Outdoor Track | JV Championships | Away - Darien HS | 3:00 p.m. | ||
| Wed., 5/18 | V Softball | New Canaan | Away - Waveny Park - Orchard Field [Directions] | L 3-6 | ||
| Wed., 5/18 | JV Softball | New Canaan | Away - Waveny Park - Orchard Field [Directions] | 4:00 p.m. | ||
| Wed., 5/18 | V Girls Tennis | FCIAC Tournament | Home - GHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/18 | JV Girls Tennis | Staples | Away - Town Farms Tennis Courts [Directions] | 4:00 p.m. | JVA | |
| Wed., 5/18 | JV Girls Tennis | Staples | Away - Town Farms Tennis Courts [Directions] | 4:00 p.m. | JVA | |
| Thu., 5/19 | FR Boys Lacrosse | Wilton | Home - GHS Field 7 [Directions] | 4:30 p.m. | ||
| Thu., 5/19 | JV Boys Tennis | Ridgefield | Home - Central MS [Directions] | 4:30 p.m. | Junior Varsity | |
| Thu., 5/19 | V Girls Golf | Fairfield Warde | Home - Griffith E Harris Golf Course [Directions] | GHS 172 FWHS 188 | ||
| Thu., 5/19 | FR Girls Lacrosse | Wilton | Away - Allen's Field [Directions] | 4:00 p.m. | ||
| Thu., 5/19 | JV Girls Tennis | Ridgefield | Away - RHS Tennis Courts [Directions] | 4:00 p.m. | JVA | |
| Fri., 5/20 | V Baseball | FCIAC Tournament | Home - GHS Baseball Field [Directions] | 4:30 p.m. | ||
| Fri., 5/20 | V Boys Rugby | National Championships | Away | TBA | ||
| Fri., 5/20 | V Boys Tennis | FCIAC Tournament | Home - GHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 5/20 | V Girls Lacrosse | Wilton | Home - Cardinal Stadium [Directions] | W 15-12 | ||
| Fri., 5/20 | V Girls Tennis | FCIAC Tournament | Away - Darien HS | 4:00 p.m. | ||
| Sat., 5/21 | V Baseball | Xavier | Away - Palmer Field [Directions] | W 11-2 | ||
| Sat., 5/21 | JV Baseball | Xavier | Away - Xavier H.S. [Directions] | 1:30 p.m. | ||
| Sat., 5/21 | FR Baseball | Xavier | Home - Julian Curtiss School [Directions] | 11:00 a.m. | ||
| Sat., 5/21 | V Boys Lacrosse | FCIAC Tournament | Away - Staples HS | 12:00 p.m. | ||
| Sat., 5/21 | V Boys Outdoor Track | FCIAC Championships | Away - Bethel HS | 8:00 a.m. | ||
| Sat., 5/21 | V Boys Outdoor Track | FCIAC Championships | Away - Bethel HS | 8:00 a.m. | ||
| Sat., 5/21 | V Boys Outdoor Track | FCIAC Championships | Away - Bethel HS | 8:00 a.m. | ||
| Sat., 5/21 | V Boys Sailing | NESSA Championships | Away - MIT | 9:00 a.m. | ||
| Sat., 5/21 | V Girls Outdoor Track | FCIAC Championships | Away - Bethel HS | 8:00 a.m. | ||
| Sat., 5/21 | V Girls Outdoor Track | FCIAC Championships | Away - Bethel HS | 8:00 a.m. | ||
| Sat., 5/21 | V Girls Sailing | NESSA Championships | Away - MIT | 9:00 a.m. | ||
| Sun., 5/22 | V Boys Sailing | NESSA Championships | Away - MIT | 9:00 a.m. | ||
| Sun., 5/22 | V Girls Sailing | NESSA Championships | Away - MIT | 9:00 a.m. | ||
| Mon., 5/23 | JV Boys Golf | New Canaan | Home - Griffith E Harris Golf Course [Directions] | 3:15 p.m. | ||
| Mon., 5/23 | V Boys Tennis | FCIAC Tournament | Home - GHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 5/23 | JV Boys Tennis | Greenwich Country Day | Away - Greenwich Country Day | 4:00 p.m. | Junior Varsity | |
| Tue., 5/24 | V Boys Golf | Staples | Away - Longshore [Directions] | Greenwich 143 Staples 148 | ||
| Tue., 5/24 | JV Boys Golf | Staples | Away - Longshore [Directions] | 3:00 p.m. | ||
| Tue., 5/24 | V Girls Golf | Staples | Home - Griffith E Harris Golf Course [Directions] | GHS 204 SHS 181 | ||
| Wed., 5/25 | V Boys Rugby | State Semi-final | Home - Cardinal Stadium [Directions] | 4:30 p.m. | ||
| Wed., 5/25 | V Boys Tennis | FCIAC Tournament | Away - Wilton HS | 4:00 p.m. | ||
| Wed., 5/25 | JV Girls Golf | Ekstrom Tournament | Away | 3:00 p.m. | ||
| Thu., 5/26 | V Boys Golf | CHAPPA Tournament | Away - Longshore Golf Course | TBA | ||
| Thu., 5/26 | V Boys Outdoor Track | Dream Invitational | Away - Danbury HS | 7:00 p.m. | ||
| Thu., 5/26 | V Boys Outdoor Track | Dream Invitational | Away - Danbury HS | 7:00 p.m. | ||
| Thu., 5/26 | V Boys Outdoor Track | Dream Invitational | Away - Danbury HS | 7:00 p.m. | ||
| Thu., 5/26 | V Girls Golf | Weston | Home - Fairchild Wheeler Golf Course [Directions] | GHS 174 WHS 213 | ||
| Sat., 5/28 | V Boys Lacrosse | CIAC State Tournament | Home - Cardinal Stadium [Directions] | 11:00 a.m. | ||
| Sat., 5/28 | V Boys Rugby | State Championship | Away | 11:00 a.m. | ||
| Sat., 5/28 | V Boys Tennis | CIAC State Tournament | Away - Yale University | 8:30 a.m. | ||
| Mon., 5/30 | School Holidays and Closings | Memorial Day | ||||
| Tue., 5/31 | V Baseball | CIAC State Tournament | Home - GHS Baseball Field [Directions] | 3:30 p.m. | ||
| Tue., 5/31 | V Boys Golf | Holohan Tournament | Away | 12:30 p.m. | ||
| Tue., 5/31 | V Boys Tennis | CIAC State Tournament | Away - Yale University | 12:00 p.m. | ||
| Tue., 5/31 | V Girls Lacrosse | CIAC State Tournament | Home - Cardinal Stadium [Directions] | 5:00 p.m. | ||
| Tue., 5/31 | V Girls Tennis | CIAC State Tournament | Away - GHS Tennis Courts | 3:30 p.m. | ||
| Wed., 6/1 | V Boys Golf | Darien | Away - Woodway CC [Directions] | Greenwich 155 Darien 150 | ||
| Wed., 6/1 | V Boys Lacrosse | CIAC State Tournament | Away - Glastonbury HS | 4:30 p.m. | ||
| Wed., 6/1 | V Boys Outdoor Track | CIAC Class LL Championships | Away - Willowbrook Park | 2:30 p.m. | ||
| Wed., 6/1 | V Boys Tennis | CIAC State Tournament | Away - Yale University | 3:30 p.m. | ||
| Wed., 6/1 | V Girls Outdoor Track | CIAC Class LL State Championships | Away - Willowbrook Park | 2:30 p.m. | ||
| Wed., 6/1 | V Girls Tennis | CIAC State Tournament | Home - GHS Tennis Courts [Directions] | 3:00 p.m. | ||
| Thu., 6/2 | V Boys Golf | FCIAC Championships | Away | TBA | ||
| Thu., 6/2 | V Boys Tennis | CIAC State Tournament | Away - Conard HS | 4:00 p.m. | ||
| Thu., 6/2 | V Girls Lacrosse | CIAC State Tournament | Away - Ridgefield HS | 5:00 p.m. | ||
| Thu., 6/2 | V Girls Tennis | CIAC State Tournament | Away - Amity HS | 3:00 p.m. | ||
| Fri., 6/3 | V Girls Tennis | CIAC State Tournament | Away - Trumbull Tennis Center | 2:30 p.m. | ||
| Sat., 6/4 | V Boys Lacrosse | CIAC State Tournament | Away - Fairfield Prep | 2:30 p.m. | ||
| Sat., 6/4 | School Holidays and Closings | SAT Testing | ||||
| Mon., 6/6 | V Boys Golf | State Championships | Away | TBA | ||
| Mon., 6/6 | V Boys Outdoor Track | CIAC State Open Championships | Away - Willowbrook Park | 1:30 p.m. | ||
| Mon., 6/6 | V Boys Outdoor Track | CIAC State Open Championships | Away - Willowbrook Park | 1:30 p.m. | ||
| Mon., 6/6 | V Girls Outdoor Track | CIAC State Open Championships | Away - Willowbrook Park | 1:30 p.m. | ||
| Mon., 6/6 | V Girls Outdoor Track | CIAC State Open Championships | Away - Willowbrook Park | 1:30 p.m. | ||
| Tue., 6/7 | V Girls Lacrosse | CIAC State Tournament | Away - Fairfield Ludlowe HS | 5:00 p.m. | ||
| Wed., 6/8 | V Boys Lacrosse | CIAC State Tournament | Away - TBA | TBA | ||
| Sat., 6/11 | V Boys Outdoor Track | New England Championships | Away - Willowbrook Park | 11:00 a.m. | ||
| Sat., 6/11 | V Girls Outdoor Track | New England Championships | Away - Willowbrook Park | 11:00 a.m. | ||
| Sat., 6/11 | V Girls Outdoor Track | New England Championships | Away - Willowbrook Park | 11:00 a.m. | ||
| Sat., 6/11 | School Holidays and Closings | ACT Testing | ||||