| Greenwich 2022-23 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 1002 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| Sat., 8/27 | V Football | Daniel Hand, Hamden (Scrim.) | Away - Madison Surf Club-Turf Field [Directions] | 3:30 p.m. | 1:00 PM, Dismiss 11:35 AM; 2 Buses | |
| Pending change awaiting acceptance by one or more parties involved: Facility to Daniel Hand HS-Turf Field | ||||||
| Mon., 8/29 | V Girls Soccer | Greenwich Academy (Scrim.) | Away - Greenwich Academy-Stadium | 4:30 p.m. | 1:30 PM (Varsity & JV will share a bus) | |
| Mon., 8/29 | JV Girls Soccer | Greenwich Academy (Scrim.) | Away - Greenwich Academy-2nd Field | 4:30 p.m. | ||
| Tue., 8/30 | V Boys Golf | Brien McMahon | Home - Griffith E Harris Golf Course [Directions] | Greenwich 150 McMahon 182 | ||
| Tue., 8/30 | V Boys Soccer | Scarsdale (NY) (Scrim.) | Home - Greenwich HS-Cardinal Stadium [Directions] | 4:30 p.m. | ||
| Wed., 8/31 | V Boys Golf | Danbury | Away - Richter Park Golf Course [Directions] | Greenwich 156 Danbury 171 | 1:00 PM; 1 Van (Varsity & JV will share a bus) | |
| Wed., 8/31 | JV Boys Golf | Danbury | Away - Richter Park Golf Course [Directions] | Cancelled | ||
| Wed., 8/31 | V Girls Soccer | Sacred Heart of Greenwich (Scrim.) | Away - Sacred Heart-Gym 1 | 4:00 p.m. | 2:30 PM; 1 Bus (JV and Varsity share a bus) | |
| Wed., 8/31 | JV Girls Soccer | Sacred Heart of Greenwich (Scrim.) | Away - Sacred Heart-Gym 1 | 4:00 p.m. | 2:30 PM; 1 Bus (JV and Varsity share a bus) | |
| Thu., 9/1 | JV Boys Golf | Fairfield Prep | Away - Patterson Club [Directions] | 3:00 p.m. | 1:30 PM; 1 Bus | |
| Thu., 9/1 | V Field Hockey | Rye (NY) (Scrim.) | Away - Rye HS-Turf | 4:30 p.m. | 3:30 PM; 1 Bus (Sharing a bus) | |
| Thu., 9/1 | JV Field Hockey | Rye (NY) (Scrim.) | Away - Rye HS-Turf | 5:30 p.m. | 3:30 PM; 1 Bus (Sharing a bus) | |
| Thu., 9/1 | V Girls Volleyball | Stamford (Scrim.) | Home - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | ||
| Fri., 9/2 | JV Girls Soccer | King and Low-Heywood Thomas (Scrim.) | Away - King School-Stadium | 4:45 p.m. | 3:15 PM, Dismiss 2:45 PM; 1 Bus | |
| Sat., 9/3 | V Football | Somers (NY) (Scrim.) | Home - Greenwich HS-Cardinal Stadium [Directions] | 12:00 p.m. | ||
| Sat., 9/3 | FR Football | Somers (NY) (Scrim.) | Away - Somers HS-N:Turf 1 | 9:00 a.m. | 7:30 AM; 1 Bus (Please book the 84-passenger bus) | |
| Sat., 9/3 | V Boys Soccer | Notre Dame-West Haven (Scrim.) | Home - Greenwich HS-Field 7 [Directions] | 11:00 a.m. | ||
| Sat., 9/3 | JV Boys Soccer | Notre Dame-West Haven (Scrim.) | Home - Cos Cob Park, Benvenuto Field-Benvenuto Field [Directions] | 11:00 a.m. | 7:00 AM; 1 Bus | |
| Sat., 9/3 | V Field Hockey | Glastonbury, Granby Memorial, Longmeadow (MA) (Scrim.) | Away - Glastonbury HS-Turf Field [Directions] | 9:00 a.m. | 7:00 AM; 1 Bus | |
| Sat., 9/3 | V Girls Volleyball | 2022 Nectar Volley Classic High School Preseason Tournament (Northeast Athletic Center) | Away - Northeast Athletic Center | 9:00 a.m. | 8:00 AM, Dismiss TBA; 1 Bus | |
| Tue., 9/6 | V Boys Soccer | Brunswick School (Scrim.) | Home - Greenwich HS-Cardinal Stadium [Directions] | Rainout | ||
| Tue., 9/6 | V Field Hockey | Greenwich Academy (Scrim.) | Away - Greenwich Academy-Turf field | 4:00 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus (Varsity & JV will share a bus) | |
| Tue., 9/6 | JV Field Hockey | Greenwich Academy (Scrim.) | Away - Greenwich Academy-Turf field | Rainout | 3:00 PM, Dismiss 2:45 PM (Varsity & JV will share a bus) | |
| Wed., 9/7 | V Boys Golf | Westhill | Away - EG Brennan Golf Course-E Gaynor Brennan Golf Course [Directions] | Greenwich 160 Westhill 170 | 2:15 PM, Dismiss 2:00 PM; 1 Van | |
| Wed., 9/7 | JV Boys Golf | Darien | Away - Woodway Country Club [Directions] | 3:15 p.m. | 2:30 PM, Dismiss 2:15 PM; 1 Bus | |
| Wed., 9/7 | V Girls Soccer | St. Lukes (Scrim.) | Home - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Thu., 9/8 | FR Football | Newtown | Away - Treadwell Park-Field 1 [Directions] | 5:00 p.m. | 2:45 PM, Dismiss 2:30 PM; 1 Bus | |
| Thu., 9/8 | V Boys Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | Greenwich 147 Trumbull 172 | 1:30 PM, Dismiss 1:15 PM (Varsity & JV sharing bus) | |
| Thu., 9/8 | JV Boys Golf | Trumbull | Away - Tashua Knolls Golf Course-Tashua Glen [Directions] | 3:00 p.m. | 1:30 PM, Dismiss 1:15 PM; 1 Bus (Varsity & JV sharing bus) | |
| Thu., 9/8 | V Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | W 4-1 | 3:00 PM, Dismiss 2:45 PM; 1 Bus (Varsity & JV will share a bus) | |
| Thu., 9/8 | JV Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 4:00 p.m. | 3:00 PM, Dismiss 2:45 PM (Varsity & JV will share a bus) | |
| Thu., 9/8 | FR Boys Soccer | Brien McMahon | Home - Cos Cob Park, Benvenuto Field-Benvenuto Field [Directions] | 4:00 p.m. | 3:00 PM, Dismiss 2:45 AM; 1 Bus | |
| Thu., 9/8 | V Field Hockey | Norwalk | Away - Norwalk HS-Testa Field [Directions] | W 5-0 | 3:00 PM, Dismiss 2:45 PM (Varsity & JV will share a bus) | |
| Thu., 9/8 | JV Field Hockey | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 5:00 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus (Varsity & JV will share a bus) | |
| Thu., 9/8 | FR Field Hockey | Norwalk | Home - Greenwich HS-Field 4 [Directions] | 4:30 p.m. | ||
| Thu., 9/8 | V Girls Swimming and Diving | Trumbull | Home - Greenwich HS-Pool [Directions] | GHS: 97 - THS: 80 (1-0) | ||
| Fri., 9/9 | V Football | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | W 34-14 | 3:30 PM, Dismiss 2:45 PM; 2 Buses (84 Passenger bus requested) | |
| Fri., 9/9 | V Girls Soccer | Brien McMahon | Home - Greenwich HS-Cardinal Stadium [Directions] | W 2-0 | ||
| Fri., 9/9 | JV Girls Soccer | Brien McMahon | Home - Greenwich HS-Cos Cob Park, Benvenuto Field [Directions] | 4:45 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Sat., 9/10 | JV Football | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 11:00 a.m. | 9:00 AM; 1 Bus | |
| Sat., 9/10 | JV Football | Newtown | Home - Greenwich HS-Field 7 [Directions] | 9:00 a.m. | ||
| Sat., 9/10 | V Boys Soccer | Fairfield Ludlowe | Home - Greenwich HS-Cardinal Stadium [Directions] | W 3-2 | ||
| Sat., 9/10 | JV Boys Soccer | Fairfield Ludlowe | Home - Greenwich HS-Cardinal Stadium [Directions] | 12:00 p.m. | ||
| Sat., 9/10 | FR Boys Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 10:00 a.m. | 8:15 AM; 1 Bus | |
| Sat., 9/10 | V Girls Volleyball | Daniel Hand | Away - Daniel Hand HS-DHHS Gym [Directions] | W 3-0 | 8:00 AM (request the 84 passenger and all 3 levels will travel together) | |
| Sat., 9/10 | JV Girls Volleyball | Daniel Hand | Away - Daniel Hand HS-DHHS Gym [Directions] | W 2-0 | 8:00 AM (request the 84 passenger and all 3 levels will travel together) | |
| Sat., 9/10 | FR Girls Volleyball | Daniel Hand | Away - Daniel Hand HS-DHHS Gym [Directions] | 10:00 a.m. | 8:00 AM; 1 Bus (request he 84 passenger bus and all 3 levels will travel together) | |
| Mon., 9/12 | V Field Hockey | Wilton | Home - Greenwich HS-Cardinal Stadium [Directions] | L 1-5 | ||
| Mon., 9/12 | JV Field Hockey | Wilton | Home - Greenwich HS-Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Mon., 9/12 | FR Field Hockey | Wilton | Away - Wilton HS-Fujitani Field - Turf [Directions] | 6:30 p.m. | 4:45 PM; 1 Bus | |
| Mon., 9/12 | V Girls Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | L 0-3 | 5:00 PM; 1 Bus | |
| Mon., 9/12 | JV Girls Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 4:00 p.m. | 2:45 PM, Dismiss 2:30 PM; 1 Bus | |
| Mon., 9/12 | FR Girls Soccer | Fairfield Ludlowe | Home - Greenwich HS-Cos Cob Park, Benvenuto Field [Directions] | 4:00 p.m. | 3:00 PM; 1 Bus | |
| Tue., 9/13 | V Boys Cross Country | Trumbull, Brien McMahon, Westhill | Away - Trumbull HS-Cross Country Course [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM; 1 Bus | |
| Tue., 9/13 | V Boys Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | Greenwich 158 Ludlowe 169 | 1:45 PM, Dismiss 1:30 PM; 1 Van | |
| Tue., 9/13 | JV Boys Golf | New Canaan | Away - CCNC [Directions] | 3:00 p.m. | 2:15 PM, Dismiss 2:00 PM; 1 Bus | |
| Tue., 9/13 | V Boys Soccer | Staples | Home - Greenwich HS-Cardinal Stadium [Directions] | W 1-0 | ||
| Tue., 9/13 | JV Boys Soccer | Staples | Home - Cos Cob Park, Benvenuto Field-Benvenuto Field [Directions] | 4:45 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Tue., 9/13 | FR Boys Soccer | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | 2:45 PM, Dismiss 2:30 PM; 1 Bus | |
| Tue., 9/13 | V Girls Cross Country | Trumbull, Brien McMahon, Westhill | Away - Trumbull HS-Cross Country Course [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM; 1 Bus | |
| Tue., 9/13 | V Girls Swimming and Diving | Norwalk/McMahon | Away - Norwalk HS-Pat Spinola Natatorium [Directions] | GHS: 103 - NHS: 81 (2-0) | 2:45 PM, Dismiss 2:30 PM; 1 Bus | |
| Wed., 9/14 | V Boys Golf | St. Joseph | Away - Tashua Knolls Golf Course [Directions] | Greenwich 158 St. Joe's 162 | 1:30 PM, Dismiss 1:15 PM; 1 Bus (Varsity & JV will share a bus) | |
| Wed., 9/14 | JV Boys Golf | Fairfield Prep | Home - Innis Arden GC [Directions] | 3:30 p.m. | ||
| Wed., 9/14 | V Girls Soccer | Staples | Away - Staples HS-Wakeman Field B (turf) [Directions] | L 0-3 | 2:30 PM, Dismiss 2:15 PM (Varsity & JV will share a bus Drop varsity off first then JV) | |
| Wed., 9/14 | JV Girls Soccer | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM; 1 Bus (Varsity & JV will share a bus Drop Varsity off First then JV) | |
| Thu., 9/15 | FR Football | Ridgefield | Home - Greenwich HS-Cardinal Stadium [Directions] | 4:30 p.m. | ||
| Thu., 9/15 | V Boys Golf | Norwalk | Home - Griffith E Harris Golf Course [Directions] | Greenwich 158 Norwalk | ||
| Thu., 9/15 | V Boys Water Polo | Staples | Away - Staples HS-Pool [Directions] | 4:30 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Thu., 9/15 | V Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | W 3-1 | 2:30 PM, Dismiss 2:15 PM (JV and Varsity travel together) | |
| Thu., 9/15 | JV Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | Postponed | 2:30 PM; 1 Bus (JV and Varsity travel together) | |
| Thu., 9/15 | FR Girls Volleyball | St. Joseph | Home - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | ||
| Fri., 9/16 | V Football | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | W 49-42 | 3:00 PM; 2 Buses | |
| Fri., 9/16 | V Boys Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | T 1-1 | 5:00 PM; 1 Bus | |
| Fri., 9/16 | JV Boys Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 4:15 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Fri., 9/16 | FR Boys Soccer | Norwalk | Home - Greenwich HS-Cos Cob Park, Benvenuto Field [Directions] | 4:00 p.m. | 3:00 PM, Dismiss 2:45 AM; 1 Bus | |
| Fri., 9/16 | V Girls Swimming and Diving | Fairfield Ludlowe | Away - Fairfield University-Pool [Directions] | GHS: 99 - FL: 79 (3-0) | 2:30 PM, Dismiss 2:15 PM; 1 Bus | |
| Sat., 9/17 | JV Football | Ridgefield | Home - Greenwich HS-Field 7 [Directions] | 11:00 a.m. | ||
| Sat., 9/17 | V Field Hockey | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | OT-L 3-4 | 10:00 AM; 1 Bus (Varsity & JV will share a bus) | |
| Sat., 9/17 | JV Field Hockey | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 1:30 p.m. | 10:00 AM (Varsity & JV will share a bus) | |
| Sat., 9/17 | V Girls Soccer | Norwalk | Home - Greenwich HS-Cardinal Stadium [Directions] | W 4-0 | ||
| Sat., 9/17 | JV Girls Soccer | Norwalk | Home - Greenwich HS-Cardinal Stadium [Directions] | 9:00 a.m. | ||
| Mon., 9/19 | JV Football | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Mon., 9/19 | V Boys Golf | Stamford | Away - Stamford High-Sterling Farms Golf Course [Directions] | Greenwich 154 Stamford 180 | 1:30 PM; 1 Van | |
| Mon., 9/19 | V Boys Soccer | Fairfield Warde | Home - Greenwich HS-Cardinal Stadium [Directions] | L 0-1 | ||
| Mon., 9/19 | JV Boys Soccer | Fairfield Warde | Home - Cos Cob Park, Benvenuto Field-Benvenuto Field [Directions] | 4:45 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Mon., 9/19 | FR Boys Soccer | Fairfield Warde | Away - Tunxis [Directions] | 4:00 p.m. | 2:45 PM, Dismiss 2:30 PM; 1 Bus | |
| Mon., 9/19 | V Field Hockey | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | W 8-0 | 3:00 PM, Dismiss 2:45 PM; 1 Bus (Varsity & JV will share a bus) | |
| Mon., 9/19 | JV Field Hockey | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 5:00 p.m. | 3:00 PM, Dismiss 2:45 PM (Varsity & JV will share a bus) | |
| Tue., 9/20 | V Boys Cross Country | Fairfield Warde, Norwalk, Stamford | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM; 1 Bus | |
| Tue., 9/20 | V Boys Golf | Fairfield Warde | Home - Griffith E Harris Golf Course [Directions] | Greenwich 154 Warde 159 | ||
| Tue., 9/20 | V Girls Cross Country | Fairfield Warde, Norwalk, Stamford | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM; 1 Bus | |
| Tue., 9/20 | V Girls Soccer | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | L 0-2 | 5:00 PM; 1 Bus | |
| Tue., 9/20 | JV Girls Soccer | Fairfield Warde | Away - Fairfield Warde HS-Fairfield Warde Grass Utility Field [Directions] | 4:00 p.m. | 2:45 PM, Dismiss 2:30 PM; 1 Bus | |
| Tue., 9/20 | FR Girls Soccer | Fairfield Warde | Home - Greenwich HS-Cos Cob Park, Benvenuto Field [Directions] | 4:00 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Tue., 9/20 | V Girls Volleyball | Trumbull | Home - Greenwich HS-Gymnasium [Directions] | W 3-1 | ||
| Tue., 9/20 | JV Girls Volleyball | Trumbull | Home - Greenwich HS-Gymnasium [Directions] | L 2-0 | ||
| Wed., 9/21 | V Boys Golf | Wilton | Home - Griffith E Harris Golf Course [Directions] | Greenwich 151 Wilton 162 | ||
| Wed., 9/21 | JV Boys Golf | New Canaan | Away - CCNC [Directions] | 3:00 p.m. | 2:15 PM, Dismiss 2:00 PM; 1 Bus | |
| Wed., 9/21 | V Field Hockey | Fairfield Warde | Home - Greenwich HS-Cardinal Stadium [Directions] | W 9-0 | ||
| Wed., 9/21 | JV Field Hockey | Fairfield Warde | Home - Greenwich HS-Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Wed., 9/21 | FR Field Hockey | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | Cancelled | 3:00 PM; 1 Bus | |
| Thu., 9/22 | FR Football | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:30 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Thu., 9/22 | V Boys Soccer | Trumbull | Away - Trumbull HS-Cork Field [Directions] | L 0-2 | 3:00 PM, Dismiss 2:45 PM; 1 Bus () | |
| Thu., 9/22 | JV Boys Soccer | Trumbull | Away - Trumbull HS-The Pit [Directions] | 4:00 p.m. | 2:30 PM; 1 Bus () | |
| Thu., 9/22 | FR Boys Soccer | Trumbull | Home - Greenwich HS-Cos Cob Park, Benvenuto Field [Directions] | 4:00 p.m. | 3:00 PM, Dismiss 2:45 AM; 1 Bus | |
| Thu., 9/22 | V Girls Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | W 3-0 | 3:00 PM, Dismiss 2:45 PM; 1 Bus (JV and Varsity travel together) | |
| Thu., 9/22 | JV Girls Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | W 2-0 | 3:00 PM, Dismiss 2:45 PM (JV and Varsity travel together) | |
| Thu., 9/22 | FR Girls Volleyball | Brien McMahon | Home - Greenwich HS-Gymnasium [Directions] | Postponed | ||
| Fri., 9/23 | V Girls Soccer | Trumbull | Home - Greenwich HS-Cardinal Stadium [Directions] | W 2-1 | ||
| Fri., 9/23 | JV Girls Soccer | Trumbull | Home - Cos Cob Park, Benvenuto Field-Benvenuto Field [Directions] | 4:45 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Fri., 9/23 | FR Girls Soccer | Trumbull | Away - Trumbull HS-The Pit [Directions] | 4:00 p.m. | 2:15 PM, Dismiss 2:00 PM; 1 Bus | |
| Fri., 9/23 | V Girls Swimming and Diving | Danbury | Home - Greenwich HS-Pool [Directions] | GHS: 95 - DHS: 50 (4-0) | ||
| Sat., 9/24 | V Boys Cross Country | Bowdoin Park Classic Wappingers Falls, NY | Away - Not Listed | 9:00 a.m. | 7:00 AM; 1 Bus | |
| Sat., 9/24 | V Football | Southington | Home - Greenwich HS-Cardinal Stadium [Directions] | L 28-29 | ||
| Sat., 9/24 | V Boys Soccer | Hall | Away - Farmington Sports Arena-Field 7 [Directions] | L 0-5 | 4:00 PM; 1 Bus | |
| Sat., 9/24 | V Girls Cross Country | Bowdoin Park Classic Wappingers Falls, NY | Away - Not Listed | 9:00 a.m. | 7:00 AM; 1 Bus | |
| Sat., 9/24 | V Girls Swimming and Diving | Amity, Glastonbury | Away - High Plains Community Cn [Directions] | GHS: 109 - Amity: 77 / GHS: 83 - Glastonbury: 103 (5-1) | 1:30 PM, Dismiss 1:15 PM; 1 Bus | |
| Tue., 9/27 | V Boys Golf | Ridgefield | Home - Griffith E Harris Golf Course [Directions] | Greenwich 150 Ridgefield 165 | ||
| Tue., 9/27 | JV Boys Golf | Wilton | Away - Rolling Hills Country Club [Directions] | Postponed | 2:00 PM; 1 Bus | |
| Tue., 9/27 | V Boys Water Polo | Staples | Home - Greenwich HS-Pool [Directions] | 4:30 p.m. | ||
| Tue., 9/27 | V Field Hockey | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | W 8-0 | 2:15 PM, Dismiss 2:00 PM; 1 Bus (Varsity & JV will share a bus) | |
| Tue., 9/27 | JV Field Hockey | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 5:30 p.m. | 2:15 PM, Dismiss 2:00 PM (Varsity & JV will share a bus) | |
| Tue., 9/27 | FR Field Hockey | Ridgefield | Home - Greenwich HS-Field 4 [Directions] | 5:30 p.m. | ||
| Tue., 9/27 | V Girls Soccer | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | L 1-0 | 5:30 PM; 1 Bus | |
| Tue., 9/27 | JV Girls Soccer | New Canaan | Away - Saxe MS-Field 1 [Directions] | 4:30 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Tue., 9/27 | FR Girls Soccer | New Canaan | Home - Greenwich HS-Cos Cob Park, Benvenuto Field [Directions] | 4:00 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Tue., 9/27 | V Girls Volleyball | Fairfield Ludlowe | Home - Greenwich HS-Gymnasium [Directions] | W 3-2 | ||
| Tue., 9/27 | JV Girls Volleyball | Fairfield Ludlowe | Home - Greenwich HS-Gymnasium [Directions] | W 2-0 | ||
| Tue., 9/27 | FR Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:30 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Wed., 9/28 | V Boys Cross Country | Danbury, St. Joseph, Staples | Away - Tarrywile Park [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 12:15 AM; 1 Bus | |
| Wed., 9/28 | JV Football | Southington | Away - Southington HS-3 TURF FIELD [Directions] | Postponed | 3:00 PM; 1 Bus | |
| Wed., 9/28 | V Boys Golf | New Canaan | Home - Griffith E Harris Golf Course [Directions] | Greenwich 145 NC 155 | ||
| Wed., 9/28 | V Boys Soccer | New Canaan | Home - Greenwich HS-Cardinal Stadium [Directions] | W 3-1 | ||
| Wed., 9/28 | JV Boys Soccer | New Canaan | Home - Central MS [Directions] | 4:45 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Wed., 9/28 | FR Boys Soccer | New Canaan | Away - Saxe MS-Field 1 [Directions] | 4:30 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Wed., 9/28 | V Girls Cross Country | Danbury, St. Joseph, Staples | Away - Tarrywile Park [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM; 1 Bus | |
| Thu., 9/29 | FR Football | Wilton | Home - Greenwich HS-Field 7 [Directions] | 4:30 p.m. | ||
| Thu., 9/29 | V Boys Golf | Darien | Home - Burning Tree Country Club [Directions] | Greenwich 157 Darien 161 | ||
| Thu., 9/29 | JV Boys Golf | Fairfield Prep | Home - Griffith E Harris Golf Course [Directions] | 3:15 p.m. | ||
| Thu., 9/29 | JV Boys Golf | Ridgefield | Away - Ridgefield Golf Course [Directions] | Cancelled | 1:45 PM; 1 Bus | |
| Thu., 9/29 | V Field Hockey | New Canaan | Home - Greenwich HS-Cardinal Stadium [Directions] | L 2-3 | ||
| Thu., 9/29 | JV Field Hockey | New Canaan | Home - Greenwich HS-Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Thu., 9/29 | V Girls Volleyball | Staples | Home - Greenwich HS-Gymnasium [Directions] | W 3-0 | ||
| Thu., 9/29 | JV Girls Volleyball | Staples | Home - Greenwich HS-Gymnasium [Directions] | L 2-1 | ||
| Thu., 9/29 | FR Girls Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:00 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Fri., 9/30 | V Boys Soccer | Darien | Home - Greenwich HS-Cardinal Stadium [Directions] | W 3-2 | ||
| Fri., 9/30 | JV Boys Soccer | Darien | Home - Cos Cob Park, Benvenuto Field-Benvenuto Field [Directions] | 4:45 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Fri., 9/30 | FR Boys Soccer | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Fri., 9/30 | V Girls Soccer | Darien | Away - Darien HS-DHS Stadium Field [Directions] | T 2-2 | 5:00 PM; 1 Bus | |
| Fri., 9/30 | JV Girls Soccer | Darien | Away - Darien HS-DHS Center Oval - Turf [Directions] | 4:00 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Sat., 10/1 | V Football | Westhill | Home - Greenwich HS-Cardinal Stadium [Directions] | W 62-14 | ||
| Sat., 10/1 | V Girls Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | W 3-0 | 9:00 AM; 1 Bus (JV and Varsity travel together) | |
| Sat., 10/1 | JV Girls Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | W 2-1 | 9:00 AM (JV and Varsity travel together) | |
| Sat., 10/1 | FR Girls Volleyball | Norwalk | Home - Greenwich HS-Gymnasium [Directions] | 10:30 a.m. | ||
| Mon., 10/3 | V Boys Cross Country | Darien, Fairfield Ludlowe, New Canaan | Home - Greenwich Point [Directions] | 4:00 p.m. | 2:45 PM, Dismiss 2:30 PM; 1 Bus | |
| Mon., 10/3 | JV Football | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | 2:45 PM, Dismiss 2:30 PM; 1 Bus | |
| Mon., 10/3 | V Girls Cross Country | Darien, Fairfield Ludlowe, New Canaan | Home - Greenwich Point [Directions] | 4:00 p.m. | 2:45 PM, Dismiss 2:30 PM; 1 Bus | |
| Mon., 10/3 | V Field Hockey | Westhill | Home - Greenwich HS-Cardinal Stadium [Directions] | W 8-0 | ||
| Mon., 10/3 | JV Field Hockey | Westhill | Home - Greenwich HS-Cardinal Stadium [Directions] | 5:00 p.m. | ||
| Mon., 10/3 | FR Girls Soccer | Darien | Home - Greenwich HS-Cos Cob Park, Benvenuto Field [Directions] | 4:00 p.m. | ||
| Mon., 10/3 | V Girls Swimming and Diving | Cheshire, Ridgefield | Away - Cheshire Community Pool [Directions] | GHS: 84 - Chesire: 102 / GHS: 65 - Ridgefield: 121 (5-3) | ||
| Mon., 10/3 | V Girls Volleyball | Brien McMahon | Home - Greenwich HS-Gymnasium [Directions] | W 3-0 | ||
| Mon., 10/3 | JV Girls Volleyball | Brien McMahon | Home - Greenwich HS-Gymnasium [Directions] | W 2-1 | ||
| Tue., 10/4 | V Boys Golf | Fairfield Prep | Home - Round Hill Country Club [Directions] | Greenwich 160 Fairfield Prep 162 | ||
| Thu., 10/6 | FR Football | Fairfield Ludlowe | Home - Greenwich HS-Field 7 [Directions] | 4:30 p.m. | ||
| Thu., 10/6 | FM Football | Wilton | Away - Wilton HS-Fuijitani Field -Turf [Directions] | 4:30 p.m. | 2:45 PM, Dismiss 2:30 PM | |
| Thu., 10/6 | V Boys Soccer | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | L 2-3 | 5:00 PM; 1 Bus | |
| Thu., 10/6 | JV Boys Soccer | Ridgefield | Away - Ridgefield HS-RHS Lower Grass Field [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM; 1 Bus () | |
| Thu., 10/6 | FR Boys Soccer | Ridgefield | Home - Greenwich HS-Cos Cob Park, Benvenuto Field [Directions] | Postponed | 4:00 PM; 1 Bus | |
| Thu., 10/6 | V Girls Swimming and Diving | Westhill/Stamford | Home - Greenwich HS-Pool [Directions] | GHS: 104 - Westhill/Stamford: 82 (6-3) | ||
| Thu., 10/6 | V Girls Volleyball | Fairfield Warde | Home - Greenwich HS-Gymnasium [Directions] | W 3-1 | ||
| Thu., 10/6 | JV Girls Volleyball | Fairfield Warde | Home - Greenwich HS-Gymnasium [Directions] | W 2-0 | ||
| Thu., 10/6 | FR Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:30 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Fri., 10/7 | V Girls Soccer | Ridgefield | Home - Greenwich HS-Cardinal Stadium [Directions] | W 1-0 | ||
| Fri., 10/7 | JV Girls Soccer | Ridgefield | Home - Cos Cob Park, Benvenuto Field-Benvenuto Field [Directions] | Postponed | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Fri., 10/7 | FR Girls Soccer | Ridgefield | Away - Ridgefield HS-RHS Lower Grass Field [Directions] | Postponed | 2:45 PM; 1 Bus | |
| Sat., 10/8 | V Field Hockey | Trumbull | Home - Greenwich HS-Cardinal Stadium [Directions] | W 4-1 | ||
| Sat., 10/8 | JV Field Hockey | Trumbull | Home - Greenwich HS-Cardinal Stadium [Directions] | 9:00 a.m. | ||
| Sat., 10/8 | FR Field Hockey | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 10:00 a.m. | 3:00 PM; 1 Bus | |
| Sat., 10/8 | V Girls Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | L 3-0 | 8:30 AM (JV and Varsity travel together) | |
| Sat., 10/8 | JV Girls Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | L 2-0 | 8:30 AM; 1 Bus (JV and Varsity travel together) | |
| Sat., 10/8 | FR Girls Volleyball | Trumbull | Home - Greenwich HS-Gymnasium [Directions] | 10:30 a.m. | ||
| Mon., 10/10 | V Boys Golf | Staples | Away - Longshore Golf Course [Directions] | Greenwich 141 Staples 157 | 1:45 PM, Dismiss 1:30 PM; 1 Van | |
| Mon., 10/10 | JV Boys Golf | Staples | Away - Longshore Golf Course [Directions] | 3:15 p.m. | 1:45 PM, Dismiss 1:30 PM; 1 Bus | |
| Mon., 10/10 | V Boys Soccer | Bridgeport Central | Away - Bridgeport Central-Kennedy Stadium Turf [Directions] | W 8-0 | 2:30 PM, Dismiss 2:15 PM | |
| Mon., 10/10 | JV Boys Soccer | Bridgeport Central | Away - Bridgeport Central HS-Seaside Park [Directions] | 4:30 p.m. | 2:30 PM, Dismiss 2:15 PM; 1 Bus (Varsity & JV will share a bus Drop Varsity off first the JV) | |
| Mon., 10/10 | V Girls Soccer | Bridgeport Central | Home - Greenwich HS-Cardinal Stadium [Directions] | W 5-0 | ||
| Mon., 10/10 | JV Girls Soccer | Bridgeport Central | Home - Cos Cob Park, Benvenuto Field-Benvenuto Field [Directions] | Cancelled | 3:00 PM; 1 Bus | |
| Mon., 10/10 | V Girls Volleyball | New Canaan | Home - Greenwich HS-Gymnasium [Directions] | L 3-2 | ||
| Mon., 10/10 | JV Girls Volleyball | New Canaan | Home - Greenwich HS-Gymnasium [Directions] | W 2-0 | ||
| Mon., 10/10 | FR Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:30 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Tue., 10/11 | V Boys Cross Country | Ridgefield, Wilton | Home - Greenwich Point [Directions] | 4:00 p.m. | 2:45 PM, Dismiss 2:30 PM; 1 Bus | |
| Tue., 10/11 | JV Football | Wilton | Away - Wilton HS-Fuijitani Field -Turf [Directions] | 4:00 p.m. | ||
| Tue., 10/11 | V Girls Cross Country | Ridgefield, Wilton | Home - Greenwich Point [Directions] | 4:00 p.m. | 2:45 PM, Dismiss 2:30 PM; 1 Bus | |
| Tue., 10/11 | V Field Hockey | Staples | Home - Greenwich HS-Cardinal Stadium [Directions] | W 3-2 | ||
| Tue., 10/11 | JV Field Hockey | Staples | Home - Greenwich HS-Cardinal Stadium [Directions] | 5:00 p.m. | ||
| Tue., 10/11 | FR Girls Soccer | Staples | Home - Greenwich HS-Cos Cob Park, Benvenuto Field [Directions] | 4:00 p.m. | ||
| Wed., 10/12 | V Boys Soccer | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | T 1-1 | 4:00 PM, Dismiss TBA; 1 Bus () | |
| Wed., 10/12 | JV Boys Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 6:00 p.m. | 4:00 PM; 1 Bus () | |
| Wed., 10/12 | V Girls Soccer | Danbury | Home - Greenwich HS-Cardinal Stadium [Directions] | T 0-0 | ||
| Wed., 10/12 | JV Girls Soccer | Danbury | Home - Greenwich HS-Cardinal Stadium [Directions] | 4:30 p.m. | ||
| Wed., 10/12 | V Girls Swimming and Diving | Darien | Home - Greenwich HS-Pool [Directions] | GHS: 78 - Darien: 106 (6-4) (FCIAC Record: 5-2) | ||
| Wed., 10/12 | V Girls Volleyball | Darien | Home - Greenwich HS-Gymnasium [Directions] | L 3-0 | ||
| Wed., 10/12 | JV Girls Volleyball | Darien | Home - Greenwich HS-Gymnasium [Directions] | L 2-1 | ||
| Wed., 10/12 | FR Girls Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM; 1 Bus | |
| Thu., 10/13 | FR Football | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 4:00 p.m. | 2:15 PM, Dismiss 2:00 PM; 1 Bus | |
| Thu., 10/13 | FR Boys Soccer | Danbury | Home - Greenwich HS-Cos Cob Park, Benvenuto Field [Directions] | 4:15 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Thu., 10/13 | JV Field Hockey | Greenwich Country Day | Away - Greenwich Country Day-Stadium | 4:00 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Thu., 10/13 | FR Girls Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 4:00 p.m. | 2:45 PM, Dismiss 2:30 PM; 1 Bus | |
| Fri., 10/14 | V Football | St. Joseph | Home - Greenwich HS-Cardinal Stadium [Directions] | W 36-26 | ||
| Fri., 10/14 | V Boys Soccer | Westhill | Home - Greenwich HS-Field 7 [Directions] | L 0-1 | ||
| Fri., 10/14 | JV Boys Soccer | Westhill | Home - Cos Cob Park, Benvenuto Field-Benvenuto Field [Directions] | 4:45 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Fri., 10/14 | FR Boys Soccer | Westhill | Away - Westhill HS-Front Turf [Directions] | 4:15 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Fri., 10/14 | V Field Hockey | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | W 7-0 | 3:00 PM, Dismiss 2:45 PM; 1 Bus (Varsity & JV will share a bus) | |
| Fri., 10/14 | JV Field Hockey | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | 3:00 PM, Dismiss 2:45 PM (Varsity & JV will share a bus) | |
| Fri., 10/14 | V Girls Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | W 3-0 | 2:30 PM, Dismiss 2:15 PM (JV and Varsity travel together) | |
| Fri., 10/14 | JV Girls Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | W 2-0 | 2:30 PM, Dismiss 2:15 PM; 1 Bus (JV and Varsity travel together) | |
| Fri., 10/14 | FR Girls Volleyball | Ridgefield | Home - Greenwich HS-Gymnasium [Directions] | 5:15 p.m. | ||
| Sat., 10/15 | JV Football | St. Joseph | Home - Greenwich HS-Field 7 [Directions] | Cancelled | ||
| Sat., 10/15 | V Field Hockey | Hall | Home - Greenwich HS-Cardinal Stadium [Directions] | W 10-1 | ||
| Sat., 10/15 | V Girls Soccer | Westhill | Away - Westhill HS-Westhill Front Turf Field [Directions] | W 4-1 | 9:00 AM (Varsity & JV will share a bus) | |
| Sat., 10/15 | JV Girls Soccer | Westhill | Away - Westhill HS-Westhill Front Turf Field [Directions] | 10:00 a.m. | 9:00 AM; 1 Bus (Varsity & JV will share a bus) | |
| Mon., 10/17 | JV Boys Golf | Fairfield Prep | Home - Round Hill Country Club [Directions] | 4:00 p.m. | ||
| Mon., 10/17 | V Boys Soccer | Wilton | Away - Wilton HS-Lilly Field [Directions] | W 3-2 | 3:30 PM; 1 Bus () | |
| Mon., 10/17 | JV Boys Soccer | Wilton | Away - Allen's Meadow-2A [Directions] | 4:30 p.m. | 2:45 PM, Dismiss 2:30 PM; 1 Bus () | |
| Mon., 10/17 | FR Boys Soccer | Wilton | Home - Greenwich HS-Cos Cob Park, Benvenuto Field [Directions] | 4:45 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Mon., 10/17 | V Girls Swimming and Diving | Staples | Home - Greenwich HS-Pool [Directions] | GHS: 100 - Staples: 73 (7-4, 6-2 in the FCIAC) | ||
| Mon., 10/17 | V Girls Volleyball | Bridgeport Central | Away - Bridgeport Central HS-The Barry McLeod Court [Directions] | W 3-0 | 2:45 PM, Dismiss 2:30 PM (JV and Varsity travel together) | |
| Mon., 10/17 | JV Girls Volleyball | Bridgeport Central | Away - Bridgeport Central HS-The Barry McLeod Court [Directions] | W 2-0 | 2:45 PM, Dismiss 2:30 PM; 1 Bus (JV and Varsity travel together) | |
| Tue., 10/18 | V Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | W 6-0 | 2:30 PM, Dismiss 2:15 PM; 1 Bus (Varsity & JV will share a bus) | |
| Tue., 10/18 | JV Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 5:30 p.m. | 2:30 PM, Dismiss 2:15 PM (Varsity & JV will share a bus) | |
| Tue., 10/18 | FR Field Hockey | Fairfield Ludlowe | Home - Greenwich HS-Field 4 [Directions] | 4:30 p.m. | ||
| Tue., 10/18 | V Girls Soccer | Wilton | Home - Greenwich HS-Cardinal Stadium [Directions] | T 0-0 | ||
| Tue., 10/18 | JV Girls Soccer | Wilton | Home - Cos Cob Park, Benvenuto Field-Benvenuto Field [Directions] | 4:30 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Tue., 10/18 | FR Girls Soccer | Wilton | Away - Allen's Meadow-3A [Directions] | 4:00 p.m. | 2:45 PM, Dismiss 2:30 PM; 1 Bus | |
| Wed., 10/19 | V Boys Cross Country | FCIAC Championship | Away - Waveny Park | 2:15 p.m. | 1:15 PM, Dismiss 1:00 PM; 1 Bus | |
| Wed., 10/19 | V Girls Cross Country | FCIAC Championship | Away - Waveny Park | 2:15 p.m. | 1:15 PM, Dismiss 1:00 PM; 1 Bus | |
| Wed., 10/19 | V Field Hockey | Darien | Home - Greenwich HS-Cardinal Stadium [Directions] | L 1-2 | ||
| Wed., 10/19 | JV Field Hockey | Darien | Home - Greenwich HS-Cardinal Stadium [Directions] | 5:00 p.m. | ||
| Wed., 10/19 | FR Field Hockey | Darien | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:30 p.m. | 3:00 PM; 1 Bus | |
| Wed., 10/19 | V Girls Volleyball | Danbury | Away - Danbury HS-New Gym [Directions] | W 3-0 | 2:45 PM, Dismiss 2:30 PM; 1 Bus (JV and Varsity travel together) | |
| Wed., 10/19 | JV Girls Volleyball | Danbury | Away - Danbury HS-New Gym [Directions] | W 2-0 | 2:45 PM, Dismiss 2:30 PM (JV and Varsity travel together) | |
| Wed., 10/19 | FR Girls Volleyball | Danbury | Home - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | ||
| Thu., 10/20 | V Football | Trumbull | Home - Greenwich HS-Cardinal Stadium [Directions] | W 37-24 | ||
| Thu., 10/20 | FR Football | New Canaan | Home - Greenwich HS-Field 7 [Directions] | 4:15 p.m. | ||
| Thu., 10/20 | V Girls Swimming and Diving | Fairfield Warde | Away - Fairfield University-Pool [Directions] | GHS: 102 - F. Warde: 74 (8-4) (7-2 in FCIAC) | 1:45 PM, Dismiss 1:30 PM | |
| Fri., 10/21 | JV Football | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 5:30 p.m. | ||
| Fri., 10/21 | V Boys Soccer | St. Joseph | Home - Greenwich HS-Cardinal Stadium [Directions] | W 8-0 | ||
| Fri., 10/21 | JV Boys Soccer | St. Joseph | Home - Greenwich HS-Cardinal Stadium [Directions] | Cancelled | ||
| Fri., 10/21 | V Girls Soccer | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | T 0-0 | 2:15 PM, Dismiss 2:00 PM (Varsity & JV will share a bus) | |
| Fri., 10/21 | JV Girls Soccer | St. Joseph | Away - St. Joseph HS-Lower Grass Field [Directions] | 4:00 p.m. | 2:15 PM, Dismiss 2:00 PM; 1 Bus (Varsity & JV will share a bus) | |
| Fri., 10/21 | V Girls Volleyball | Westhill | Home - Greenwich HS-Gymnasium [Directions] | W 3-1 | ||
| Fri., 10/21 | JV Girls Volleyball | Westhill | Home - Greenwich HS-Gymnasium [Directions] | W 2-0 | ||
| Sat., 10/22 | V Field Hockey | Newtown | Home - Greenwich HS-Cardinal Stadium [Directions] | W 7-0 | ||
| Sat., 10/22 | JV Field Hockey | Newtown | Home - Greenwich HS-Cardinal Stadium [Directions] | 10:30 a.m. | ||
| Mon., 10/24 | JV Football | JV Football against Iona Prep at Iona Prep | Away - Not Listed | 4:30 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Mon., 10/24 | V Boys Soccer | Stamford | Home - Greenwich HS-Cardinal Stadium [Directions] | W 4-0 | ||
| Mon., 10/24 | JV Boys Soccer | Stamford | Home - Cos Cob Park, Benvenuto Field-Benvenuto Field [Directions] | 4:15 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Mon., 10/24 | FR Boys Soccer | Stamford | Away - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Mon., 10/24 | V Field Hockey | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | W 9-0 | 2:30 PM, Dismiss 2:15 PM; 1 Bus (Varsity & JV will share a bus) | |
| Mon., 10/24 | JV Field Hockey | Stamford | Home - Greenwich HS-Field 4 [Directions] | 4:00 p.m. | ||
| Mon., 10/24 | JV Field Hockey | Danbury | Away - Danbury HS-Grass Field Hockey Field [Directions] | 5:30 p.m. | 2:30 PM, Dismiss 2:15 PM (Varsity & JV will share a bus) | |
| Mon., 10/24 | FR Field Hockey | Danbury | Home - Greenwich HS-Field 4 [Directions] | Cancelled | ||
| Mon., 10/24 | V Girls Volleyball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | L 3-2 | 3:00 PM, Dismiss 2:45 PM (JV and Varsity travel together) | |
| Mon., 10/24 | JV Girls Volleyball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | W 2-1 | 3:00 PM, Dismiss 2:45 PM; 1 Bus (JV and Varsity travel together) | |
| Mon., 10/24 | FR Girls Volleyball | Wilton | Home - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | ||
| Tue., 10/25 | V Girls Soccer | Stamford | Home - Greenwich HS-Cardinal Stadium [Directions] | W 7-1 | ||
| Wed., 10/26 | FR Field Hockey | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 4:30 p.m. | 3:30 PM; 1 Bus | |
| Wed., 10/26 | JV Girls Soccer | Stamford | Away - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | 2:45 PM, Dismiss 2:30 PM; 1 Bus (Varsity & JV will share a bus Drop off Varsity first then JV) | |
| Wed., 10/26 | V Girls Volleyball | St. Joseph | Home - Greenwich HS-Gymnasium [Directions] | W 3-1 | ||
| Wed., 10/26 | JV Girls Volleyball | St. Joseph | Home - Greenwich HS-Gymnasium [Directions] | W 2-1 | ||
| Wed., 10/26 | FR Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:30 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Thu., 10/27 | FR Football | Darien | Home - Greenwich HS-Field 7 [Directions] | 4:30 p.m. | ||
| Thu., 10/27 | V Boys Soccer | Danbury | Home - Greenwich HS-Cardinal Stadium [Directions] | 3:30 p.m. | ||
| Thu., 10/27 | V Girls Volleyball | Masuk | Home - Greenwich HS-Gymnasium [Directions] | W 3-0 | ||
| Thu., 10/27 | JV Girls Volleyball | Masuk | Home - Greenwich HS-Gymnasium [Directions] | W 2-0 | ||
| Fri., 10/28 | V Field Hockey | Staples | Away - Staples HS-Ginny Parker Field [Directions] | L 0-2 | 1:00 PM, Dismiss 12:45 PM; 1 Bus | |
| Fri., 10/28 | V Girls Soccer | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 3:30 p.m. | ||
| Fri., 10/28 | V Girls Volleyball | Stamford | Home - Greenwich HS-Gymnasium [Directions] | W 3-0 | ||
| Fri., 10/28 | JV Girls Volleyball | Stamford | Home - Greenwich HS-Gymnasium [Directions] | W 2-0 | ||
| Fri., 10/28 | FR Girls Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Sat., 10/29 | V Boys Cross Country | CIAC Class LL Championship | Away - Wickham Park | 10:45 a.m. | ||
| Sat., 10/29 | V Football | Darien | Away - Darien HS-DHS Stadium Field [Directions] | W 28-20 | 12:00 PM; 2 Buses (84 passenger busses needed) | |
| Sat., 10/29 | V Girls Cross Country | CIAC Class LL Championship | Away - Wickham Park | 10:10 a.m. | ||
| Sat., 10/29 | JV Girls Swimming and Diving | Brien McMahon, Danbury, Darien, Fairfield Ludlowe, Fairfield Warde, New Canaan, Norwalk/McMahon, Ridgefield, St. Joseph, Stamford, Staples, Trumbull, Westhill/Stamford, Wilton | Home - Greenwich HS-Pool [Directions] | 10:15 a.m. | ||
| Sat., 10/29 | JV Girls Volleyball | Fairfield Warde, Fairfield Ludlowe, TBA, Newtown, Stamford, Trumbull, Westhill | Away - Fairfield Warde HS-Large Gym | 9:00 a.m. | 8:00 AM, Dismiss 2:45 PM; 1 Bus | |
| Sat., 10/29 | FR Girls Volleyball | Westhill | Away - Westhill HS-New Gym [Directions] | 10:30 a.m. | 3:00 PM; 1 Bus | |
| Mon., 10/31 | JV Football | Darien | Home - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Tue., 11/1 | V Boys Golf | CIAC Division I Championship | Away - Stanley GC | 9:00 a.m. | ||
| Tue., 11/1 | V Boys Soccer | Trumbull | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 7:00 p.m. | 5:00 PM; 1 Bus | |
| Tue., 11/1 | V Girls Soccer | Staples | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 7:00 p.m. | 5:00 PM; 1 Bus | |
| Tue., 11/1 | V Girls Swimming and Diving | Danbury, Darien, Fairfield Ludlowe, Fairfield Warde, New Canaan, Norwalk/McMahon, Ridgefield, St. Joseph, Staples, Trumbull, Westhill/Stamford, Wilton | Home - Greenwich HS-Pool [Directions] | 5:15 p.m. | ||
| Tue., 11/1 | V Girls Volleyball | Fairfield Ludlowe | Home - Greenwich HS-Gymnasium [Directions] | W 3-2 | ||
| Wed., 11/2 | V Girls Swimming and Diving | FCIAC Diving Championship | Away - Westhill HS-Westhill Pool | 5:00 p.m. | ||
| Thu., 11/3 | FR Football | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Thu., 11/3 | V Girls Volleyball | Darien | Away - Fairfield Ludlowe HS-Main Gym [Directions] | L 3-1 | 2:45 PM, Dismiss 2:30 PM; 1 Bus | |
| Fri., 11/4 | V Boys Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Fri., 11/4 | V Girls Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Fri., 11/4 | V Girls Swimming and Diving | Danbury, Darien, Fairfield Ludlowe, Fairfield Warde, New Canaan, Norwalk/McMahon, Ridgefield, St. Joseph, Staples, Trumbull, Westhill/Stamford, Wilton | Home - Greenwich HS-Pool [Directions] | FCIAC Finals - Top 3 Teams: 1. Ridgefield 2. Darien 3. Greenwich | ||
| Sat., 11/5 | V Football | Danbury | Home - Greenwich HS-Cardinal Stadium [Directions] | W 59-6 | ||
| Mon., 11/7 | JV Football | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | Cancelled | 3:00 PM; 1 Bus | |
| Mon., 11/7 | V Boys Soccer | Farmington | Home - Greenwich HS-Cardinal Stadium [Directions] | 2:00 p.m. | ||
| Mon., 11/7 | V Girls Volleyball | South Windsor | Home - Greenwich HS-Gymnasium [Directions] | W 3-1 | ||
| Tue., 11/8 | V Girls Soccer | Shelton | Home - Greenwich HS-Cardinal Stadium [Directions] | 2:00 p.m. | ||
| Wed., 11/9 | V Boys Soccer | Trumbull | Away - Trumbull HS-Cork Field [Directions] | 2:00 p.m. | ||
| Wed., 11/9 | V Field Hockey | Conard | Home - Greenwich HS-Cardinal Stadium [Directions] | W 7-0 | ||
| Thu., 11/10 | FR Football | Staples | Away - Staples HS-Staples Stadium [Directions] | 6:00 p.m. | 4:00 PM; 1 Bus | |
| Thu., 11/10 | V Girls Soccer | Staples | Away - Staples HS-Wakeman Field B (turf) [Directions] | 2:00 p.m. | ||
| Thu., 11/10 | V Girls Swimming and Diving | CIAC Class LL Diving Championships | Away - Sheehan | 5:30 p.m. | ||
| Thu., 11/10 | V Girls Volleyball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | W 3-0 | 4:00 PM; 1 Bus | |
| Fri., 11/11 | V Boys Soccer | Newington | Away - Newington HS-Fields in front of the VA Hospital next to NHS [Directions] | 2:00 p.m. | 11:00 AM, Dismiss 10:45 AM; 1 Bus | |
| Fri., 11/11 | V Field Hockey | Darien | Away - Darien HS-DHS Stadium Field [Directions] | L 2-4 | 12:45 PM, Dismiss 12:30 PM; 1 Bus | |
| Sat., 11/12 | V Football | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | W 49-10 | 11:00 AM; 2 Buses (84 passenger busses) | |
| Sat., 11/12 | V Girls Swimming and Diving | CIAC Class LL Trials | Away - Cornerstone Pool | 11:15 a.m. | 8:00 AM; 1 Bus | |
| Mon., 11/14 | JV Football | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 5:00 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Mon., 11/14 | V Girls Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | L 3-0 | 11:30 AM; 1 Bus | |
| Tue., 11/15 | V Boys Soccer | Fairfield Prep | Away - Fairfield Warde HS-Stadium [Directions] | 6:30 p.m. | 4:00 PM; 1 Bus | |
| Wed., 11/16 | V Girls Swimming and Diving | CIAC Class LL Final | Away - Cornerstone Pool | Class LL Runner-Up Champions (2nd Place Team) | ||
| Thu., 11/17 | V Girls Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 11/19 | JV Football | Staples | Home - Greenwich HS-Cardinal Stadium [Directions] | 11:00 a.m. | ||
| Sat., 11/19 | V Boys Soccer | Hall | Away - Trinity Health Stadium-Dillon Stadium [Directions] | 6:30 p.m. | 3:30 PM; 1 Bus | |
| Sun., 11/20 | V Girls Swimming and Diving | CIAC State Open Swimming Championship | Away - Yale | State Opens - 6th Place Team | ||
| Thu., 11/24 | V Football | Staples | Away - Staples HS-Staples Stadium [Directions] | L 38-39 | 8:00 AM; 2 Buses (84 passesanger busses) | |
| Tue., 11/29 | V Football | Hamden | Home - Greenwich HS-Cardinal Stadium [Directions] | 6:30 p.m. | ||
| Wed., 11/30 | V Girls Ice Hockey | Stamford/Westhill/Staples (Scrim.) | Home - Greenwich - Dorothy Hamill-Rink [Directions] | 5:15 p.m. | ||
| Sat., 12/3 | V Girls Basketball | Joel Barlow (Scrim.) | Away - Joel Barlow HS-Lower Gym [Directions] | 11:00 a.m. | ||
| Sat., 12/3 | JV Girls Basketball | Joel Barlow (Scrim.) | Away - Joel Barlow HS-Lower Gym [Directions] | 11:00 a.m. | ||
| Sat., 12/3 | V Girls Ice Hockey | New Canaan (Scrim.) | Away - Darien Ice House-Ice Rink [Directions] | 6:40 p.m. | ||
| Sun., 12/4 | V Football | Cheshire | Home - New Canaan HS-Dunning Stadium [Directions] | 12:30 p.m. | ||
| Sun., 12/4 | V Football | Glastonbury | Home - Greenwich HS-Cardinal Stadium [Directions] | 12:30 p.m. | ||
| Wed., 12/7 | V Boys Ice Hockey | North Haven (Scrim.) | Away - Northford-Red [Directions] | 8:30 p.m. | ||
| Wed., 12/7 | V Girls Ice Hockey | Guilford Coop | Away - East Haven HS-Veterans Rink [Directions] | L 2-1 | 2:30 PM, Dismiss 2:15 PM; 1 Bus | |
| Fri., 12/9 | V Boys Basketball | Wright Tech (Scrim.) | Away - J M Wright Tech School-Thomas R. Good Gymnasium [Directions] | 6:00 p.m. | 3:00 PM, Dismiss 2:45 PM | |
| Fri., 12/9 | JV Boys Basketball | Wright Tech (Scrim.) | Away - J M Wright Tech School-Thomas R. Good Gymnasium [Directions] | 4:30 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus (Share bus) | |
| Fri., 12/9 | V Girls Ice Hockey | Darien | Away - Darien Ice House-Ice Rink [Directions] | L 0-4 | 7:00 PM; 1 Bus | |
| Sat., 12/10 | V Football | Fairfield Prep | Home - Rentschler Field [Directions] | 5:30 p.m. | 1:00 PM; 2 Buses | |
| Sat., 12/10 | JV Boys Ice Hockey | Fairfield Prep (Scrim.) | Away - Wonderland of Ice-Stadium [Directions] | Postponed | 4:15 PM | |
| Pending change awaiting acceptance by one or more parties involved: Time to 5:45 p.m. | ||||||
| Mon., 12/12 | V Girls Basketball | Wright Tech | Home - Greenwich HS-Gymnasium [Directions] | W 51-8 | ||
| Tue., 12/13 | V Boys Ice Hockey | Fairfield Prep | Home - Greenwich - Dorothy Hamill-Rink [Directions] | L 5-3 | ||
| Wed., 12/14 | V Wrestling | Darien | Home - Greenwich HS-Gymnasium [Directions] | Darien 30 Greenwich 45 | ||
| Fri., 12/16 | JV Boys Ice Hockey | Rye (NY) | Away - Rye HS-Rye Playland Ice | 8:00 p.m. | 6:30 PM; 1 Bus | |
| Fri., 12/16 | V Boys Swimming and Diving | Westhill/Stamford | Home - Greenwich HS-Pool [Directions] | 4:15 p.m. | ||
| Fri., 12/16 | V Girls Basketball | Bethel | Away - Bethel HS-BHS gym [Directions] | L 30-43 | 2:30 PM, Dismiss 2:15 PM; 1 Bus | |
| Fri., 12/16 | JV Girls Basketball | Bethel | Away - Bethel HS-BHS gym [Directions] | 4:15 p.m. | 2:30 PM, Dismiss 2:15 PM; 1 Bus | |
| Fri., 12/16 | V Girls Ice Hockey | New Canaan | Home - Greenwich - Dorothy Hamill-Rink [Directions] | L 2-7 | ||
| Sat., 12/17 | V Boys Ice Hockey | Xavier | Away - Cromwell-Upper Rink [Directions] | L 1-3 | ||
| Sat., 12/17 | JV Boys Ice Hockey | Notre Dame-West Haven | Home - Greenwich - Dorothy Hamill-Rink [Directions] | 4:30 p.m. | ||
| Sat., 12/17 | V Boys Indoor Track | Staples, Stamford, Trumbull, Westhill | Away - Staples HS-Field House [Directions] | 1:30 p.m. | ||
| Sat., 12/17 | V Wrestling | Guilford Invitational | Away - Guilford HS-Main gym at GHS | 9:00 a.m. | ||
| Sat., 12/17 | FR Girls Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 11:00 a.m. | ||
| Sat., 12/17 | V Girls Indoor Track | Staples, Stamford, Trumbull, Westhill | Away - Staples HS-Field House [Directions] | 1:30 p.m. | ||
| Wed., 12/21 | V Boys Ice Hockey | North Haven | Home - Greenwich - Dorothy Hamill-Rink [Directions] | L 1-3 | ||
| Wed., 12/21 | V Wrestling | Trumbull | Away - Trumbull HS-Aux Gym [Directions] | Greenwich 6 Trumbull 66 | 3:30 PM; 1 Bus | |
| Wed., 12/21 | V Co-ed Fencing | Guilford | Away - Guilford HS-Aux gym at GHS [Directions] | 6:00 p.m. | 4:00 PM; 1 Bus | |
| Wed., 12/21 | FR Girls Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:30 p.m. | 3:05 PM, Dismiss 2:45 PM; 1 Bus | |
| Mon., 12/26 | V Wrestling | New Canaan, Norwalk, Trumbull | Away - New Canaan HS-Main Gym [Directions] | 9:15 a.m. | ||
| Mon., 12/26 | JV Wrestling | Trumbull, Brien McMahon, Bristol Eastern, Fairfield Ludlowe, Fairfield Warde, TBA, New Milford, Newtown, Staples | Away - Trumbull HS-THS Main Gym | 9:00 a.m. | ||
| Tue., 12/27 | V Boys Basketball | Bunnell | Away - Bunnell HS-David Johnson Gymnasium [Directions] | L 44-47 | ||
| Tue., 12/27 | V Girls Ice Hockey | Hall/Conard | Home - Greenwich - Dorothy Hamill-Rink [Directions] | L 1-2 | ||
| Thu., 12/29 | V Boys Basketball | Masuk | Home - Bunnell HS-David Johnson Gymnasium [Directions] | W 52-37 | ||
| Thu., 12/29 | V Boys Ice Hockey | Darien | Home - Greenwich Skating Club [Directions] | L 0-1 | ||
| Thu., 12/29 | JV Boys Ice Hockey | Darien | Home - Greenwich Skating Club-Ice Rink [Directions] | 10:00 a.m. | ||
| Thu., 12/29 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Greenwich Skating Club-Ice Rink [Directions] | W 6-4 | ||
| Fri., 12/30 | V Wrestling | Trumbull, Amity, Berlin, Foran, Manchester, Masuk, Minnechaug (MA), TBA, Pomperaug, Stratford | Away - Trumbull HS-Aux Gym | Masuk 36 Greenwich 39 Greenwich 18 Amity 63 Greenwich 24 Berlin 60 Greenwich 17 Foran 66 Greenwich 24 Stratford 58 | 7:00 AM; 1 Bus | |
| Pending change awaiting acceptance by one or more parties involved: Time to 9:00 a.m. | ||||||
| Fri., 12/30 | V Girls Basketball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | L 39-48 | ||
| Fri., 12/30 | JV Girls Basketball | Brookfield | Away - Brookfield HS-BHS Big Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/3 | V Boys Ice Hockey | New Canaan | Home - Greenwich - Dorothy Hamill-Rink [Directions] | L 2-6 | ||
| Tue., 1/3 | V Girls Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | L 42-43 | 3:45 PM (JV & V share the bus) | |
| Tue., 1/3 | JV Girls Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | 3:45 PM; 1 Bus (JV & V share the bus) | |
| Tue., 1/3 | FR Girls Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Wed., 1/4 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Away - Fairfield University-Pool [Directions] | 7:30 p.m. | 5:15 PM; 1 Bus | |
| Wed., 1/4 | V Wrestling | Westhill | Away - Westhill HS-Main Gym [Directions] | Greenwich 54 Westhill 27 | 4:15 PM; 1 Bus | |
| Thu., 1/5 | V Girls Gymnastics | Norwalk, Staples | Home - Greenwich YWCA [Directions] | 117.55 [Detailed Results] | ||
| Thu., 1/5 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Greenwich - Dorothy Hamill-Rink [Directions] | W 3-1 | ||
| Fri., 1/6 | V Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | W 58-44 | 3:45 PM (JV & V share the bus) | |
| Fri., 1/6 | JV Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 5:30 p.m. | 3:45 PM; 1 Bus (JV & V share the bus) | |
| Fri., 1/6 | FR Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:00 p.m. | 2:45 PM, Dismiss 2:30 PM; 1 Bus | |
| Fri., 1/6 | V Girls Basketball | Brien McMahon | Home - Greenwich HS-Gymnasium [Directions] | W 54-34 | ||
| Fri., 1/6 | JV Girls Basketball | Brien McMahon | Home - Greenwich HS-Gymnasium [Directions] | 5:00 p.m. | ||
| Fri., 1/6 | FR Girls Basketball | Darien | Home - Greenwich HS-Gymnasium [Directions] | 3:45 p.m. | ||
| Sat., 1/7 | V Boys Basketball | Newtown | Away - Newtown HS-Gym [Directions] | W 51-45 | 9:45 AM (JV & V share the bus) | |
| Sat., 1/7 | JV Boys Basketball | Newtown | Away - Newtown HS-Gym [Directions] | 12:00 p.m. | 9:45 AM; 1 Bus (JV & V share the bus) | |
| Sat., 1/7 | V Boys Ice Hockey | Hamden | Home - Greenwich - Dorothy Hamill-Rink [Directions] | W 6-3 | ||
| Sat., 1/7 | V Boys Indoor Track | Staples, Bridgeport Central, St. Joseph | Away - Staples HS-Field House [Directions] | 10:00 a.m. | 8:30 AM; 1 Bus | |
| Sat., 1/7 | V Girls Basketball | Amistad | Home - Greenwich HS-Gymnasium [Directions] | W 58-35 | ||
| Sat., 1/7 | JV Girls Basketball | Amistad | Home - Greenwich HS-Gymnasium [Directions] | 12:00 p.m. | ||
| Sat., 1/7 | FR Girls Basketball | Greenwich Academy | Home - Greenwich HS-Gymnasium [Directions] | 10:30 a.m. | ||
| Sat., 1/7 | V Girls Indoor Track | Staples, Bridgeport Central, St. Joseph | Away - Staples HS-Field House [Directions] | 10:00 a.m. | 8:45 AM; 1 Bus | |
| Mon., 1/9 | V Boys Ice Hockey | St. Joseph | Home - Greenwich - Dorothy Hamill-Rink [Directions] | W 4-1 | ||
| Mon., 1/9 | V Girls Gymnastics | Westhill, Stamford | Away - Westhill HS-New Gym [Directions] | 114.25 | ||
| Tue., 1/10 | V Boys Basketball | Fairfield Ludlowe | Home - Greenwich HS-Gymnasium [Directions] | W 47-43 | ||
| Tue., 1/10 | JV Boys Basketball | Fairfield Ludlowe | Home - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/10 | FR Boys Basketball | Fairfield Ludlowe | Home - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/10 | V Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | L 39-49 | ||
| Tue., 1/10 | JV Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/10 | FR Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/10 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Greenwich - Dorothy Hamill-Rink [Directions] | W 7-4 | ||
| Wed., 1/11 | V Boys Swimming and Diving | Darien | Home - Greenwich HS-Pool [Directions] | 4:15 p.m. | ||
| Wed., 1/11 | V Wrestling | Staples | Away - Staples HS-Staples Gym [Directions] | Greenwich 24 Staples 56 | ||
| Wed., 1/11 | V Co-ed Fencing | Fairfield Warde | Away - Holy Family Church [Directions] | 6:30 p.m. | ||
| Thu., 1/12 | V Girls Gymnastics | Wilton | Home - Greenwich YWCA [Directions] | Greenwich 128.85 Wilton 139.7 | ||
| Fri., 1/13 | V Boys Basketball | Staples | Home - Greenwich HS-Gymnasium [Directions] | L 38-56 | ||
| Fri., 1/13 | JV Boys Basketball | Staples | Home - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/13 | FR Boys Basketball | Staples | Home - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/13 | V Boys Swimming and Diving | Staples | Away - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Fri., 1/13 | V Girls Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | W 42-17 | ||
| Fri., 1/13 | JV Girls Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/13 | FR Girls Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/13 | V Girls Ice Hockey | Stamford/Westhill/Staples | Home - Greenwich - Dorothy Hamill-Rink [Directions] | W 3-1 | ||
| Fri., 1/13 | JV Girls Ice Hockey | New Canaan | Away - New Canaan Winter Club-Rink [Directions] | 5:40 p.m. | ||
| Sat., 1/14 | V Boys Ice Hockey | Ridgefield | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | L 0-3 | ||
| Sat., 1/14 | JV Boys Ice Hockey | Ridgefield | Away - Danbury Ice Arena-TBA [Directions] | 2:30 p.m. | ||
| Sat., 1/14 | V Boys Indoor Track | Staples, Bridgeport Central, Danbury, Fairfield Ludlowe | Away - Staples HS-Field House [Directions] | 1:30 p.m. | ||
| Sat., 1/14 | V Wrestling | Greater Hartford Open | Away - Hall HS-Robinson Gym | 9:00 a.m. | ||
| Sat., 1/14 | JV Wrestling | Trumbull, Bristol Eastern, Fairfield Warde, TBA, Norwalk, Simsbury, Southington, Staples, Xavier | Away - Trumbull HS-THS Main Gym | 9:00 a.m. | ||
| Sat., 1/14 | JV Co-ed Fencing | North Haven, Cheshire, Daniel Hand, Daniel Hand, Fairfield Warde, Old Lyme, Morgan, North Branford | Away - North Haven HS-Fred Kelly Gymnasium | 8:00 a.m. | ||
| Sat., 1/14 | V Girls Indoor Track | Staples, Danbury, Fairfield Ludlowe | Away - Staples HS-Field House [Directions] | 1:30 p.m. | ||
| Mon., 1/16 | V Girls Gymnastics | St. Joseph | Away - St. Joseph HS-Next Dimensions [Directions] | Greenwich 121.0 St. Joe 123.5 Trumbull 124.35 | ||
| Mon., 1/16 | V Girls Gymnastics | Trumbull | Away - Next Dimension Gymnastics-Next Dimension [Directions] | 12:45 p.m. | ||
| Mon., 1/16 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | L 5-2 | ||
| Tue., 1/17 | V Boys Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | W 88-82 | ||
| Tue., 1/17 | JV Boys Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/17 | FR Boys Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/17 | V Bowling | Fairfield Warde | Away - Nutmeg Bowling Alley [Directions] | 3:00 p.m. | ||
| Tue., 1/17 | V Girls Basketball | Norwalk | Home - Greenwich HS-Gymnasium [Directions] | W 59-44 | ||
| Tue., 1/17 | JV Girls Basketball | Norwalk | Home - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 1/18 | V Boys Ice Hockey | Daniel Hand | Away - Northford-Red [Directions] | W 3-2(OT) | ||
| Wed., 1/18 | JV Boys Ice Hockey | New Canaan | Home - Greenwich - Dorothy Hamill-Rink [Directions] | 7:00 p.m. | ||
| Wed., 1/18 | V Wrestling | Stamford | Home - Greenwich HS-Gymnasium [Directions] | Greenwich 34 Stamford 36 | ||
| Thu., 1/19 | V Girls Gymnastics | New Canaan | Home - Greenwich YWCA [Directions] | Greenwich 129.55 New Canaan 108.25 | ||
| Fri., 1/20 | V Boys Basketball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | L 49-55 | ||
| Fri., 1/20 | JV Boys Basketball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | 5:15 p.m. | ||
| Fri., 1/20 | FR Boys Basketball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | 4:00 p.m. | ||
| Fri., 1/20 | V Boys Swimming and Diving | Ridgefield | Home - Greenwich HS-Pool [Directions] | 4:15 p.m. | ||
| Fri., 1/20 | V Girls Basketball | Bridgeport Central | Home - Greenwich HS-Gymnasium [Directions] | W 56-28 | ||
| Fri., 1/20 | JV Girls Basketball | Bridgeport Central | Home - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/20 | FR Girls Basketball | Bridgeport Central | Home - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 1/21 | V Boys Basketball | Hamden | Away - Hamden HS-HHS Gym [Directions] | W 73-72 | ||
| Sat., 1/21 | JV Boys Basketball | Hamden | Away - Hamden HS-HHS Gym [Directions] | 12:00 p.m. | ||
| Sat., 1/21 | FR Boys Basketball | Hamden | Away - Hamden HS-HHS Gym [Directions] | 10:30 a.m. | ||
| Sat., 1/21 | V Boys Ice Hockey | Trumbull | Home - Greenwich - Dorothy Hamill-Rink [Directions] | W 1-0 | ||
| Sat., 1/21 | V Boys Indoor Track | Wilton, Bridgeport Central, Danbury, Fairfield Ludlowe | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 12:00 p.m. | ||
| Sat., 1/21 | V Boys Indoor Track | Bridgeport Central, Danbury, Fairfield Ludlowe | Home - Wilton HS-Wilton Field House [Directions] | 12:00 p.m. | ||
| Sat., 1/21 | V Boys Swimming and Diving | Fairfield Prep | Away - Fairfield University-Pool [Directions] | 3:00 p.m. | ||
| Sat., 1/21 | JV Wrestling | Patton JV Tournament | Away - Danbury HS-Main Gym | 9:30 a.m. | ||
| Sat., 1/21 | V Girls Basketball | Newtown | Home - Greenwich HS-Gymnasium [Directions] | L 32-47 | ||
| Sat., 1/21 | JV Girls Basketball | Newtown | Home - Greenwich HS-Gymnasium [Directions] | 11:15 a.m. | ||
| Sat., 1/21 | FR Girls Basketball | Newtown | Home - Greenwich HS-Gymnasium [Directions] | 10:00 a.m. | ||
| Sat., 1/21 | V Girls Indoor Track | Wilton, Bridgeport Central, Danbury, Fairfield Ludlowe | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 12:00 p.m. | ||
| Sat., 1/21 | V Girls Indoor Track | Bridgeport Central, Danbury, Fairfield Ludlowe | Home - Wilton HS-Wilton Field House [Directions] | 12:00 p.m. | ||
| Sun., 1/22 | JV Boys Ice Hockey | Notre Dame-West Haven | Away - West Haven HS-Bennett Rink [Directions] | 7:45 p.m. | ||
| Mon., 1/23 | V Girls Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | L 6-0 | ||
| Tue., 1/24 | V Boys Basketball | Fairfield Warde | Home - Greenwich HS-Gymnasium [Directions] | L 47-51 | ||
| Tue., 1/24 | JV Boys Basketball | Fairfield Warde | Home - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/24 | FR Boys Basketball | Fairfield Warde | Home - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/24 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Home - Greenwich - Dorothy Hamill-Rink [Directions] | W 3-0 | ||
| Tue., 1/24 | V Girls Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | L 46-49 | ||
| Tue., 1/24 | JV Girls Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/24 | FR Girls Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/25 | V Boys Swimming and Diving | Danbury | Away - WCSU O'Neill Center Pool [Directions] | Cancelled | ||
| Wed., 1/25 | V Wrestling | Norwalk | Home - Greenwich HS-Gymnasium [Directions] | Greenwich 30 Norwalk 47 | ||
| Wed., 1/25 | V Girls Ice Hockey | Stamford/Westhill/Staples | Away - Terry Conners - Stamford-Ice Rink [Directions] | L 2-1 | ||
| Fri., 1/27 | V Boys Basketball | Stamford | Home - Greenwich HS-Gymnasium [Directions] | W 50-49 | ||
| Fri., 1/27 | JV Boys Basketball | Stamford | Home - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/27 | FR Boys Basketball | Stamford | Home - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/27 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Home - Greenwich HS-Pool [Directions] | 4:15 p.m. | ||
| Fri., 1/27 | V Co-ed Fencing | Guilford | Home - Central MS-Gym 1 [Directions] | 6:00 p.m. | ||
| Fri., 1/27 | V Girls Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | W 44-35 | ||
| Fri., 1/27 | JV Girls Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/27 | FR Girls Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 1/28 | V Boys Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | L 4-0 | ||
| Sat., 1/28 | V Wrestling | Ridgefield, Amity, Arlington (NY), Bethel, Brewster (NY), Bristol Central, Coventry (RI), Fairfield Prep, Fairfield Warde, Hope (RI), Middlebury Union (VT), TBA, New Milford, Washingtonville (NY) | Away - Ridgefield HS-Main Gym | 9:30 a.m. | ||
| Sat., 1/28 | JV Wrestling | Neil Godleski Wrestling Tournament | Away - Norwalk HS-Tom Scarso Gymnasium | 9:00 a.m. | ||
| Sat., 1/28 | V Girls Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | W 60-30 | ||
| Sat., 1/28 | JV Girls Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 11:00 a.m. | 12:45 PM, Dismiss 12:30 PM; 1 Bus | |
| Sat., 1/28 | V Girls Ice Hockey | Darien | Home - Greenwich - Dorothy Hamill-Rink [Directions] | L 6-0 | ||
| Mon., 1/30 | V Boys Ice Hockey | Ridgefield | Home - Greenwich - Dorothy Hamill-Rink [Directions] | L 1-2 | ||
| Mon., 1/30 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | L 5-3 | ||
| Tue., 1/31 | V Boys Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | L 45-62 | ||
| Tue., 1/31 | JV Boys Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/31 | FR Boys Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/31 | V Girls Basketball | Trumbull | Home - Greenwich HS-Gymnasium [Directions] | L 37-40 | ||
| Tue., 1/31 | JV Girls Basketball | Trumbull | Home - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/31 | FR Girls Basketball | Trumbull | Home - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/31 | V Girls Ice Hockey | West Haven/SHA | Away - West Haven HS-Bennett Rink [Directions] | W 4-2 | ||
| Wed., 2/1 | V Boys Ice Hockey | Notre Dame-West Haven | Away - West Haven HS-Bennett Rink [Directions] | L 2-6 | ||
| Wed., 2/1 | V Wrestling | Brien McMahon | Home - Greenwich HS-Gymnasium [Directions] | Greenwich 49 Brien McMahon 30 | ||
| Thu., 2/2 | V Boys Indoor Track | FCIAC Championships | Away - Floyd Little Athletic Center-Field House | 5:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Not Listed-Floyd Little Athletic Center | ||||||
| Thu., 2/2 | V Boys Swimming and Diving | Danbury, Trumbull | Home - Greenwich HS-Pool [Directions] | 4:15 p.m. | ||
| Thu., 2/2 | V Girls Gymnastics | Fairfield Ludlowe, Fairfield Warde | Home - Greenwich YWCA [Directions] | Greenwich 123.05 Ludlowe 129.8 Warde 131.85 | ||
| Thu., 2/2 | JV Girls Ice Hockey | Stamford/Westhill/Staples (Scrim.) | Home - Greenwich - Dorothy Hamill-Rink [Directions] | 8:00 p.m. | ||
| Thu., 2/2 | V Girls Indoor Track | FCIAC, Bridgeport Central, Brien McMahon, Danbury, Darien, Fairfield Ludlowe, Fairfield Warde, New Canaan, Norwalk, Ridgefield, St. Joseph, Stamford, Staples, Trumbull, Westhill, Wilton | Away - Floyd Little Athletic Center-Field House | 5:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Not Listed-Floyd Little Athletic Center | ||||||
| Fri., 2/3 | V Boys Basketball | St. Joseph | Home - Greenwich HS-Gymnasium [Directions] | W 62-57 | ||
| Fri., 2/3 | JV Boys Basketball | St. Joseph | Home - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 2/3 | FR Boys Basketball | St. Joseph | Home - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 2/3 | V Co-ed Fencing | Hopkins School | Home - Central MS-Gym 1 [Directions] | 6:00 p.m. | ||
| Fri., 2/3 | V Girls Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | L 27-40 | ||
| Fri., 2/3 | JV Girls Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/3 | FR Girls Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:00 p.m. | ||
| Sat., 2/4 | V Boys Ice Hockey | LaSalle Academy (RI) | Away - La Salle Academy-Thayer/Warburton Ice Arena | T 1-1 | TBA | |
| Sat., 2/4 | V Wrestling | Fairfield Ludlowe, Cheshire, New Milford, Norwalk, Shelton | Away - Fairfield Ludlowe HS-Main Gym | Greenwich 36 Fairfield Ludlowe 48 Greenwich 57 Shelton 24 Greenwich 60 Cheshire 17 | ||
| Sat., 2/4 | V Competitive Cheerleading | FCIAC Cheer Championship | Away - Trumbull HS-THS Main Gym | 11:00 a.m. | ||
| Sat., 2/4 | V Girls Gymnastics | Darien | Away - Darien YMCA [Directions] | Greenwich 120.05 Darien 131.25 | ||
| Sat., 2/4 | V Girls Ice Hockey | East Catholic Coop | Away - Newington-Red Rink [Directions] | L 0-7 | ||
| Sun., 2/5 | V Boys Ice Hockey | Bishop Hendricken (RI) | Away - Bishop Hendricken HS-Baseball Field | L 1-5 | TBA | |
| Tue., 2/7 | V Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | L 30-47 | ||
| Tue., 2/7 | JV Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/7 | FR Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/7 | V Wrestling | Danbury | Away - Danbury HS-New gym [Directions] | 5:00 p.m. | ||
| Tue., 2/7 | V Girls Basketball | Ridgefield | Home - Greenwich HS-Gymnasium [Directions] | W 44-35 | ||
| Tue., 2/7 | JV Girls Basketball | Ridgefield | Home - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 2/7 | FR Girls Basketball | Ridgefield | Home - Greenwich HS-Gymnasium [Directions] | Cancelled | ||
| Tue., 2/7 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Away - Hamden-Lou Astorino Ice Rink [Directions] | T 3-3 | ||
| Wed., 2/8 | V Boys Ice Hockey | Darien | Away - Darien Ice House-Ice Rink [Directions] | L 1-5 | ||
| Wed., 2/8 | JV Boys Ice Hockey | Rye (NY) | Home - Greenwich - Dorothy Hamill-Rink [Directions] | 6:45 p.m. | ||
| Wed., 2/8 | V Boys Swimming and Diving | Wilton | Home - Greenwich HS-Pool [Directions] | 4:15 p.m. | ||
| Wed., 2/8 | JV Wrestling | Fairfield Warde, St. Joseph | Away - Fairfield Warde HS-Small Gym [Directions] | 5:30 p.m. | ||
| Thu., 2/9 | V Boys Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | L 39-52 | ||
| Thu., 2/9 | JV Boys Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 2/9 | FR Boys Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 2/9 | V Co-ed Fencing | North Haven | Away - North Haven HS-Auxiliary Gymnasium [Directions] | Cancelled | ||
| Thu., 2/9 | V Girls Basketball | Danbury | Home - Greenwich HS-Gymnasium [Directions] | L 39-43 | ||
| Thu., 2/9 | JV Girls Basketball | Danbury | Home - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 2/9 | FR Girls Basketball | Danbury | Home - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 2/9 | V Girls Gymnastics | Staples, New Canaan, Norwalk | Away - Staples HS-Westport YMCA [Directions] | Greenwich 125.1 Staples 133.65 | ||
| Fri., 2/10 | JV Boys Ice Hockey | Darien | Away - Stamford Twin Rinks-West [Directions] | 8:30 p.m. | ||
| Fri., 2/10 | V Boys Swimming and Diving | New Canaan | Away - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Fri., 2/10 | V Wrestling | New Canaan, Bridgeport Central, Brien McMahon, Danbury, Darien, FCIAC, Fairfield Ludlowe, Fairfield Warde, Norwalk, Ridgefield, St. Joseph, Stamford, Staples, Trumbull, Westhill, Wilton | Away - New Canaan HS-Main Gym | 4:00 p.m. | ||
| Sat., 2/11 | V Boys Basketball | East Hartford | Home - Greenwich HS-Gymnasium [Directions] | W 52-42 | ||
| Sat., 2/11 | JV Boys Basketball | East Hartford | Home - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 2/11 | FR Boys Basketball | East Hartford | Home - Greenwich HS-Gymnasium [Directions] | 2:30 p.m. | ||
| Sat., 2/11 | V Boys Ice Hockey | St. Joseph | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | L 0-5 | ||
| Sat., 2/11 | V Boys Indoor Track | CIAC Class LL Championships | Away - Floyd Little Athletic Center | 4:00 p.m. | ||
| Sat., 2/11 | V Girls Gymnastics | FCIAC Championship | Home - Greenwich YWCA [Directions] | 5:00 p.m. | ||
| Sat., 2/11 | V Girls Ice Hockey | Hamden Coop | Home - Greenwich - Dorothy Hamill-Rink [Directions] | W 3-2 | ||
| Sat., 2/11 | V Girls Indoor Track | CIAC Class LL Championships | Away - Floyd Little Athletic Center | 4:00 p.m. | ||
| Mon., 2/13 | V Boys Basketball | Darien | Home - Greenwich HS-Gymnasium [Directions] | L 55-64 | ||
| Mon., 2/13 | JV Boys Basketball | Darien | Home - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 2/13 | FR Boys Basketball | Darien | Home - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 2/13 | V Girls Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | W 48-20 | ||
| Mon., 2/13 | JV Girls Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/13 | FR Girls Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | Cancelled | 12:00 PM | |
| Mon., 2/13 | V Girls Ice Hockey | Simsbury | Away - Simsbury Farms Ice Rink-Ice Rink [Directions] | L 1-2 | ||
| Wed., 2/15 | V Boys Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | L 52-62 | ||
| Wed., 2/15 | JV Boys Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:15 p.m. | ||
| Wed., 2/15 | FR Boys Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Wed., 2/15 | V Boys Ice Hockey | Northwest Catholic | Home - Greenwich - Dorothy Hamill-Rink [Directions] | W 6-3 | ||
| Wed., 2/15 | V Girls Basketball | Wilton | Home - Greenwich HS-Gymnasium [Directions] | L 49-52 | ||
| Wed., 2/15 | JV Girls Basketball | Wilton | Home - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 2/17 | V Wrestling | CIAC LL Championship | Away - Trumbull | 4:00 p.m. | ||
| Sat., 2/18 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland of Ice-Stadium [Directions] | L 0-2 | 6:00 PM; 1 Bus | |
| Sat., 2/18 | V Boys Indoor Track | CIAC State Open Championships | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/18 | V Wrestling | CIAC LL Championship | Away - Trumbull | 10:30 a.m. | ||
| Sat., 2/18 | V Girls Basketball | Fairfield Ludlowe | Away - Staples HS-Staples Gym [Directions] | L 36-62 | 5:00 PM; 1 Bus | |
| Sat., 2/18 | V Girls Ice Hockey | Avon | Home - Greenwich - Dorothy Hamill-Rink [Directions] | L 2-5 | ||
| Sat., 2/18 | V Girls Indoor Track | CIAC State Open Championships | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Mon., 2/20 | V Boys Basketball | Westhill | Home - Greenwich HS-Gymnasium [Directions] | W 61-34 | ||
| Mon., 2/20 | JV Boys Basketball | Westhill | Home - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 2/20 | FR Boys Basketball | Westhill | Home - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 2/22 | V Boys Basketball | New Canaan | Home - Greenwich HS-Gymnasium [Directions] | L 52-64 | ||
| Wed., 2/22 | JV Boys Basketball | New Canaan | Home - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 2/22 | FR Boys Basketball | New Canaan | Home - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 2/22 | V Girls Ice Hockey | Darien | Away - Darien Ice House-Ice Rink [Directions] | 6:00 p.m. | 4:00 PM; 1 Bus | |
| Fri., 2/24 | V Wrestling | CIAC State Open | Away - Floyd Little Athletic Center | 12:45 p.m. | ||
| Sat., 2/25 | V Boys Ice Hockey | Ridgefield | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | W 3-1 | 6:30 PM; 1 Bus | |
| Sat., 2/25 | V Wrestling | CIAC State Open | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Sat., 2/25 | V Competitive Cheerleading | Competition @ Wolcott HS | Home - TBA [Directions] | 11:00 p.m. | 9:45 AM, Dismiss TBA; 1 Bus | |
| Sat., 2/25 | Winter Dance Team | Competition @ Hamden HS | Home - TBA [Directions] | 9:30 p.m. | 8:15 AM; 1 Bus | |
| Sat., 2/25 | V Girls Gymnastics | CIAC Divisional Championships | Away - Jonathan Law | TBA | 7:00 AM; 1 Bus | |
| Mon., 2/27 | V Co-ed Alpine Skiing | CIAC Championship @ Mt. Southington | Home - Mt Southington [Directions] | 2:00 p.m. | 11:45 AM, Dismiss 11:30 AM; 1 Bus | |
| Tue., 2/28 | V Boys Swimming and Diving | FCIAC Swim Trial Boys | Home - Greenwich HS-Pool [Directions] | 5:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 3/1 | ||||||
| Wed., 3/1 | V Boys Ice Hockey | Darien | Away - Darien Ice House-Ice Rink [Directions] | 5:00 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Wed., 3/1 | JV Boys Ice Hockey | New Canaan | Away - Blake Field - New Haven-Walker Rink [Directions] | 6:30 p.m. | ||
| Wed., 3/1 | JV Boys Ice Hockey | St. Joseph | Away - Blake Field - New Haven-Walker Rink [Directions] | Cancelled | ||
| Wed., 3/1 | V Girls Basketball | East Hartford | Away - East Hartford [Directions] | L 39-54 | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Thu., 3/2 | JV Boys Ice Hockey | St. Joseph | Away - Blake Field - New Haven-Walker Rink [Directions] | 6:45 p.m. | ||
| Thu., 3/2 | V Boys Swimming and Diving | Diving Championship @ Westhill HS | Home - TBA [Directions] | 5:30 p.m. | ||
| Thu., 3/2 | Unified Sports Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 3:15 p.m. | ||
| Fri., 3/3 | V Boys Swimming and Diving | Danbury, Darien, Farfield Ludlowe/Warde, Fairfield Warde, TBA, New Canaan, Norwalk/Brien McMahon, Ridgefield, St. Joseph, Staples, Trumbull, Westhill/Stamford, Wilton | Home - Greenwich HS-Pool [Directions] | 6:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 5:30 p.m. | ||||||
| Sat., 3/4 | V Girls Gymnastics | CIAC State Open | Away - New Milford | 4:00 p.m. | ||
| Tue., 3/7 | V Boys Basketball | Kennedy | Away - John F. Kennedy HS-Jack Taglia Gymnasium [Directions] | 6:30 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Wed., 3/8 | V Boys Ice Hockey | Northwest Catholic | Away - Simsbury - ISCC-NHL [Directions] | 7:15 p.m. | 4:00 PM; 1 Bus | |
| Thu., 3/9 | V Boys Swimming and Diving | CIAC Class LL Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/11 | V Boys Ice Hockey | Simsbury | Away - Wesleyan University-Snyder Rink [Directions] | 12:00 p.m. | 9:30 AM; 1 Bus | |
| Sat., 3/11 | V Boys Swimming and Diving | CIAC Class LL Trials | Away - Cornerstone Pool | 4:30 p.m. | 1:45 PM; 1 Bus | |
| Tue., 3/14 | V Boys Rugby | Woodlands | Home - Greenwich HS-Cardinal Stadium [Directions] | 4:30 p.m. | ||
| Tue., 3/14 | JV Boys Rugby | Woodlands | Home - Greenwich HS-Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Thu., 3/16 | V Boys Ice Hockey | Fairfield Prep | Away - Quinnipiac University-TD Bank Sports Center [Directions] | 5:30 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Thu., 3/16 | V Boys Swimming and Diving | CIAC Class LL Finals | Away - Cornerstone Pool | 1:30 p.m. | ||
| Fri., 3/17 | V Boys Swimming and Diving | CIAC Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/18 | V Boys Swimming and Diving | CIAC State Open Championship | Away - Yale | 1:00 p.m. | ||
| Tue., 3/21 | V Boys Lacrosse | TBA | Home - Greenwich HS-Cardinal Stadium [Directions] | 5:00 p.m. | ||
| Thu., 3/23 | V Baseball | Fairfield Warde (Scrim.) | Home - Julian Curtiss School [Directions] | 4:30 p.m. | ||
| Fri., 3/24 | V Baseball | Stamford (Scrim.) | Away - Stamford HS-SHS Baseball Diamond [Directions] | 4:00 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Sat., 3/25 | V Boys Lacrosse | 4 Team Jamboree | Home - Greenwich HS-Field 7 [Directions] | 2:00 p.m. | ||
| Sat., 3/25 | V Boys Lacrosse | 4 Team Jamboree | Home - Greenwich HS-Field 4 [Directions] | 2:00 p.m. | ||
| Sat., 3/25 | V Boys Rugby | Staples | Home - Greenwich HS-Cardinal Stadium [Directions] | 2:00 p.m. | ||
| Sat., 3/25 | JV Boys Rugby | Staples | Home - Greenwich HS-Cardinal Stadium [Directions] | 3:30 p.m. | ||
| Sat., 3/25 | FM Boys Rugby | Staples | Home - Greenwich HS-Field 7 [Directions] | 12:00 p.m. | ||
| Sat., 3/25 | V Girls Lacrosse | Play Day - Girls Lax | Away - Staples HS-Ginny Parker Field | 9:00 a.m. | ||
| Sat., 3/25 | V Girls Rugby | Morris | Home - Greenwich HS-Cardinal Stadium [Directions] | 11:00 a.m. | Morris | |
| Sun., 3/26 | V Baseball | Norwalk (Scrim.) | Home - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 11:00 a.m. | ||
| Sun., 3/26 | V Baseball | New Canaan (Scrim.) | Home - Norwalk HS-Callahan Complex at Nathan Hale Upper [Directions] | 1:30 p.m. | ||
| Mon., 3/27 | V Boys Volleyball | Westhill (Scrim.) | Away - Westhill HS-Main Gym [Directions] | 4:00 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Mon., 3/27 | V Softball | Brien McMahon (Scrim.) | Away - Brien McMahon HS-Softball Diamond [Directions] | 4:30 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Mon., 3/27 | V Girls Water Polo | Staples | Home - Greenwich HS-Pool [Directions] | 4:30 p.m. | ||
| Tue., 3/28 | JV Girls Tennis | Sacred Heart of Greenwich (Scrim.) | Away - Sacred Heart | 4:30 p.m. | 3:30 PM; 1 Bus | JV A |
| Wed., 3/29 | V Baseball | Darien (Scrim.) | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 3/29 | JV Baseball | Darien (Scrim.) | Away - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Wed., 3/29 | V Boys Lacrosse | Fairfield Prep (Scrim.) | Away - Fairfield University-Rafferty Stadium [Directions] | 5:00 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Wed., 3/29 | V Boys Tennis | Brunswick School (Scrim.) | Away - Brunswick School | 4:00 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Wed., 3/29 | V Boys Volleyball | Iona Prep (NY) | Away - Iona Preparatory School-Gym | 4:00 p.m. | ||
| Wed., 3/29 | JV Boys Volleyball | Iona Prep (NY) | Away - Iona Preparatory School-Gym | 5:30 p.m. | ||
| Wed., 3/29 | V Co-ed Sailing | Darien | Home - Grass Island [Directions] | 3:00 p.m. | ||
| Thu., 3/30 | V Baseball | Greenwich Country Day (Scrim.) | Home - Greenwich HS-Baseball Field [Directions] | 4:15 p.m. | ||
| Thu., 3/30 | JV Girls Rugby | Rye (NY) | Home - Greenwich HS-Field 6 [Directions] | 4:30 p.m. | ||
| Thu., 3/30 | V Softball | Darien (Scrim.) | Away - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | ||
| Thu., 3/30 | V Girls Tennis | Sacred Heart of Greenwich (Scrim.) | Away - Sacred Heart of Greenwich | W 7-0 | 3:00 PM, Dismiss 2:45 PM; 1 Bus (Share bus with JV) | |
| Thu., 3/30 | JV Girls Tennis | Greenwich Academy (Scrim.) | Away - Greenwich Academy | 3:45 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus (Share with Varsity) | JV A |
| Thu., 3/30 | JV Girls Tennis | King and Low-Heywood Thomas (Scrim.) | Home - Binney Park [Directions] | 4:15 p.m. | JV B | |
| Fri., 3/31 | V Boys Rugby | Rye (NY) | Away - Rye HS-Field | TBA | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Fri., 3/31 | V Boys Tennis | Horace Greeley (NY) (Scrim.) | Home - Greenwich HS-Tennis Courts [Directions] | 4:30 p.m. | ||
| Fri., 3/31 | V Girls Tennis | Greenwich Academy (Scrim.) | Away - Greenwich Academy | W 4-3 | 3:00 PM, Dismiss 2:45 PM | |
| Sat., 4/1 | V Boys Lacrosse | Pleasantville (NY) | Away - Pleasantville HS-Main | L 6-12 | 10:15 AM; 1 Bus | |
| Sat., 4/1 | JV Boys Lacrosse | Pleasantville (NY) | Away - Pleasantville HS-Main | 10:00 a.m. | 8:00 AM; 1 Bus | |
| Mon., 4/3 | V Baseball | Notre Dame-West Haven | Away - West Haven HS-Whitey Piurek Field [Directions] | L 0-8 | 1:45 PM, Dismiss 1:30 PM; 1 Bus | |
| Mon., 4/3 | FR Baseball | Stamford | Away - Stamford HS-SHS Baseball Diamond [Directions] | 4:30 p.m. | ||
| Mon., 4/3 | JV Boys Tennis | Darien | Away - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | JV A |
| Mon., 4/3 | V Boys Volleyball | New Canaan | Home - Greenwich HS-Gymnasium [Directions] | L 0-3 | ||
| Mon., 4/3 | JV Boys Volleyball | New Canaan | Home - Greenwich HS-Gymnasium [Directions] | L 0-2 | ||
| Mon., 4/3 | V Girls Lacrosse | Norwalk | Home - Greenwich HS-Cardinal Stadium [Directions] | W 20-4 | ||
| Mon., 4/3 | JV Girls Lacrosse | Norwalk | Home - Greenwich HS-Cardinal Stadium [Directions] | 5:45 p.m. | ||
| Mon., 4/3 | V Softball | Stratford | Away - DeLuca Field-Deluca Field [Directions] | L 7-10 | 2:30 PM, Dismiss 2:15 PM (V & JV shared bus) | |
| Mon., 4/3 | JV Softball | Stratford | Away - Birdseye Rec Complex-Birdseye 2 [Directions] | 4:15 p.m. | 2:30 PM, Dismiss 2:15 PM; 1 Bus (V & JV shared bus) | |
| Mon., 4/3 | JV Girls Tennis | Darien | Home - Binney Park [Directions] | 4:30 p.m. | JV A | |
| Mon., 4/3 | V Girls Water Polo | Greenwich Academy | Home - Greenwich HS-Pool [Directions] | 4:15 p.m. | ||
| Tue., 4/4 | V Baseball | Staples | Home - Greenwich HS-Baseball Field [Directions] | L 0-8 | ||
| Tue., 4/4 | JV Baseball | Staples | Home - Julian Curtiss School [Directions] | 4:30 p.m. | ||
| Tue., 4/4 | V Boys Lacrosse | Bronxville (NY) | Away - Bronxville HS-Field | W 8-7 3OT | 2:45 PM, Dismiss 2:30 PM; 1 Bus | |
| Tue., 4/4 | JV Boys Lacrosse | Bronxville (NY) | Home - Greenwich HS-Field 4 [Directions] | 4:30 p.m. | ||
| Tue., 4/4 | FR Boys Lacrosse | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Tue., 4/4 | V Boys Outdoor Track | Trumbull | Home - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/4 | JV Boys Tennis | Fairfield Ludlowe | Home - Central MS [Directions] | 4:30 p.m. | JV B | |
| Tue., 4/4 | V Co-ed Sailing | Darien | Home - Grass Island [Directions] | 3:00 p.m. | ||
| Tue., 4/4 | V Girls Lacrosse | Glastonbury | Away - Glastonbury HS-Field 1 [Directions] | W 16-2 | 2:00 PM, Dismiss 1:45 PM; 1 Bus (V & JV shared bus) | |
| Tue., 4/4 | JV Girls Lacrosse | Glastonbury | Away - Glastonbury HS-Field 1 [Directions] | 6:15 p.m. | 2:00 PM, Dismiss 1:45 PM; 1 Bus (V & JV shared bus) | |
| Tue., 4/4 | V Girls Outdoor Track | Trumbull | Home - Greenwich HS-Cardinal Stadium [Directions] | W 88-57 | ||
| Tue., 4/4 | V Softball | Westhill | Home - Greenwich HS-Softball Field [Directions] | L 7-2 | ||
| Tue., 4/4 | V Girls Tennis | Rye Country Day (NY) (Scrim.) | Away - Rye Country Day School | W 7-0 | 3:00 PM, Dismiss 2:45 PM; 1 Bus | Played at SUNY Purchase Courts are the upper courts, parking lot East #6. |
| Tue., 4/4 | JV Girls Tennis | Fairfield Ludlowe | Away - Tomlinson MS-Tennis Courts [Directions] | 4:00 p.m. | 2:45 PM, Dismiss 2:30 PM; 1 Bus | JV A |
| Thu., 4/6 | FR Boys Lacrosse | Stamford | Home - Cos Cob Park, Benvenuto Field-Benvenuto Field [Directions] | Postponed | 3:30 PM; 1 Bus (Drop off only) | |
| Thu., 4/6 | V Boys Rugby | BC High | Home - Greenwich HS-Cardinal Stadium [Directions] | Cancelled | ||
| Thu., 4/6 | JV Boys Rugby | BC High | Home - Greenwich HS-Cardinal Stadium [Directions] | Cancelled | ||
| Sat., 4/8 | V Baseball | Stamford | Away - Stamford HS-SHS Baseball Diamond [Directions] | L 1-4 | 10:15 AM; 1 Bus | |
| Sat., 4/8 | JV Baseball | Stamford | Away - Belltown Park-Barrett Field, Belltown Park [Directions] | 10:00 a.m. | 10:15 AM; 1 Bus | |
| Sat., 4/8 | V Boys Lacrosse | Weston | Home - Greenwich HS-Cardinal Stadium [Directions] | W 12-8 | ||
| Sat., 4/8 | JV Boys Lacrosse | Weston | Home - Greenwich HS-Cardinal Stadium [Directions] | 10:00 a.m. | ||
| Sat., 4/8 | V Softball | New Fairfield | Away - New Fairfield HS-Softball Field [Directions] | L 5-6 | 8:45 AM; 1 Bus | |
| Sat., 4/8 | V Girls Tennis | Weston | Home - Greenwich HS-Tennis Courts [Directions] | W 7-0 [Detailed Results] | ||
| Mon., 4/10 | FR Boys Lacrosse | Wilton | Home - Greenwich HS-Field 7 [Directions] | 11:00 a.m. | ||
| Mon., 4/10 | V Boys Tennis | Brien McMahon | Away - Brien McMahon HS-Tennis Courts [Directions] | W 7-0 [Detailed Results] | ||
| Mon., 4/10 | V Girls Tennis | Brien McMahon | Home - Greenwich HS-Tennis Courts [Directions] | W 7-0 [Detailed Results] | ||
| Tue., 4/11 | V Baseball | Fairfield Ludlowe | Home - Greenwich HS-Baseball Field [Directions] | L 3-19 F5 | ||
| Tue., 4/11 | JV Baseball | Fairfield Ludlowe | Home - Julian Curtiss School [Directions] | 4:00 p.m. | ||
| Tue., 4/11 | V Boys Lacrosse | Stamford | Home - Greenwich HS-Cardinal Stadium [Directions] | W 19-7 | ||
| Tue., 4/11 | JV Boys Lacrosse | Stamford | Home - Greenwich HS-Field 4 [Directions] | 4:30 p.m. | ||
| Tue., 4/11 | V Boys Tennis | Fairfield Ludlowe | Home - Greenwich HS-Tennis Courts [Directions] | W 7-0 [Detailed Results] | ||
| Tue., 4/11 | V Girls Lacrosse | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | W 16-1 | ||
| Tue., 4/11 | JV Girls Lacrosse | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Tue., 4/11 | V Softball | Brien McMahon | Home - Greenwich HS-Softball Field [Directions] | L 0-2 | ||
| Tue., 4/11 | V Girls Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Tennis Courts [Directions] | W 5-2 [Detailed Results] | ||
| Wed., 4/12 | FR Boys Lacrosse | Darien | Home - Greenwich HS-Field 7 [Directions] | 11:00 a.m. | ||
| Wed., 4/12 | V Softball | Westhill | Away - Westhill HS-Varsity Softball Field [Directions] | L 1-8 | ||
| Thu., 4/13 | V Boys Tennis | Staples | Home - Greenwich HS-Tennis Courts [Directions] | W 7-0 [Detailed Results] | ||
| Thu., 4/13 | JV Boys Tennis | Staples | Home - Central MS [Directions] | Postponed | JV A | |
| Thu., 4/13 | V Boys Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | L 1-3 | ||
| Thu., 4/13 | JV Boys Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | L 0-2 | ||
| Thu., 4/13 | V Girls Lacrosse | Simsbury | Home - Greenwich HS-Cardinal Stadium [Directions] | W 12-4 | ||
| Thu., 4/13 | V Girls Tennis | Staples | Away - Staples HS-Staples Tennis Courts [Directions] | W 6-1 [Detailed Results] | 2:00 PM; 1 Bus | |
| Fri., 4/14 | V Baseball | Brien McMahon | Home - Greenwich HS-Baseball Field [Directions] | W 6-2 | ||
| Fri., 4/14 | JV Baseball | Brien McMahon | Home - Julian Curtiss School [Directions] | 4:30 p.m. | ||
| Fri., 4/14 | FR Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Fairfield Warde Grass Utility Field [Directions] | 11:00 a.m. | 2:30 PM, Dismiss 2:15 PM; 1 Bus | |
| Fri., 4/14 | V Boys Rugby | Fairfield Prep | Home - Greenwich HS-Cardinal Stadium [Directions] | 4:30 p.m. | ||
| Fri., 4/14 | JV Boys Rugby | Fairfield Prep | Home - Greenwich HS-Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Fri., 4/14 | FM Boys Rugby | Fairfield Prep | Home - Greenwich HS-Field 7 [Directions] | 4:30 p.m. | ||
| Fri., 4/14 | V Softball | Brien McMahon | Away - Brien McMahon HS-Softball Diamond [Directions] | L 1-10 | ||
| Sat., 4/15 | V Boys Lacrosse | Wilton | Home - Greenwich HS-Cardinal Stadium [Directions] | L 9-3 | ||
| Sat., 4/15 | JV Boys Lacrosse | Wilton | Home - Greenwich HS-Field 4 [Directions] | 2:00 p.m. | ||
| Sat., 4/15 | JV Softball | Brien McMahon | Away - Brien McMahon HS-Softball Diamond [Directions] | Cancelled | 9:55 AM | |
| Mon., 4/17 | V Baseball | Fairfield Ludlowe | Away - Kiwanis Field-Baseball Diamond [Directions] | L 1-2 | 2:45 PM, Dismiss 2:30 PM; 1 Bus | |
| Mon., 4/17 | JV Baseball | Fairfield Ludlowe | Away - Owen Fish Park-Owen Fish [Directions] | 4:30 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Mon., 4/17 | FR Baseball | Fairfield Ludlowe | Home - Greenwich HS-Baseball Field [Directions] | 4:30 p.m. | ||
| Mon., 4/17 | FR Boys Lacrosse | Staples | Away - Staples HS-Wakeman Field B (turf) [Directions] | 5:00 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Mon., 4/17 | V Boys Outdoor Track | Westhill | Home - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Mon., 4/17 | V Boys Volleyball | Fairfield Warde | Home - Greenwich HS-Gymnasium [Directions] | L 1-3 | ||
| Mon., 4/17 | JV Boys Volleyball | Fairfield Warde | Home - Greenwich HS-Gymnasium [Directions] | W 2-0 | ||
| Mon., 4/17 | V Girls Golf | New Canaan | Home - Griffith E Harris Golf Course [Directions] | 3:30 p.m. | ||
| Mon., 4/17 | JV Girls Golf | New Canaan | Home - Griffith E Harris Golf Course [Directions] | 4:00 p.m. | ||
| Mon., 4/17 | FR Girls Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | 5:00 p.m. | 3:45 PM; 1 Bus | |
| Mon., 4/17 | V Girls Outdoor Track | Westhill | Home - Greenwich HS-Cardinal Stadium [Directions] | W 115-29 | ||
| Mon., 4/17 | V Softball | Fairfield Ludlowe | Home - Greenwich HS-Softball Field [Directions] | L 1-17 | ||
| Mon., 4/17 | JV Softball | Fairfield Ludlowe | Home - Julian Curtiss School [Directions] | 4:30 p.m. | ||
| Tue., 4/18 | V Boys Tennis | Fairfield Warde | Home - Greenwich HS-Tennis Courts [Directions] | W 6-1 [Detailed Results] | ||
| Tue., 4/18 | JV Boys Tennis | Fairfield Warde | Home - Central MS [Directions] | 4:30 p.m. | JV A | |
| Tue., 4/18 | V Girls Lacrosse | Wilton | Home - Greenwich HS-Cardinal Stadium [Directions] | L 3-13 | ||
| Tue., 4/18 | JV Girls Lacrosse | Wilton | Home - Greenwich HS-Cardinal Stadium [Directions] | 6:00 p.m. | ||
| Tue., 4/18 | V Girls Tennis | Fairfield Warde | Away - Fairfield Warde HS-Blake Courts [Directions] | W 6-1 [Detailed Results] | 2:30 PM, Dismiss 2:15 PM; 1 Bus (Varsity and JV share bus) | |
| Tue., 4/18 | JV Girls Tennis | Fairfield Warde | Away - Fairfield Warde HS-Knapps Courts [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM (Varsity and JV share bus) | JV B |
| Wed., 4/19 | V Baseball | Staples | Away - Staples HS-Baseball Diamond [Directions] | L 2-4 | 2:45 PM, Dismiss 2:30 PM; 1 Bus | |
| Wed., 4/19 | JV Baseball | Staples | Away - Staples HS-Wakeman Field [Directions] | 4:30 p.m. | 3:00 PM, Dismiss 2:45 PM | |
| Wed., 4/19 | FR Baseball | Staples | Home - Greenwich HS-Baseball Field [Directions] | 4:30 p.m. | ||
| Wed., 4/19 | FR Boys Lacrosse | Fairfield Prep | Away - Fairfield University - Barlow Field-Barlow Field Fairfield University [Directions] | 5:00 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Wed., 4/19 | V Boys Tennis | Norwalk | Away - Norwalk HS-Tennis Courts [Directions] | W 7-0 [Detailed Results] | 2:45 PM, Dismiss 2:30 PM; 1 Bus | |
| Wed., 4/19 | JV Boys Tennis | Horace Greeley (NY) | Home - Central MS [Directions] | 4:00 p.m. | JV B | |
| Wed., 4/19 | JV Boys Tennis | Horace Greeley (NY) | Away - Horace Greeley HS | 4:00 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | JV A |
| Wed., 4/19 | V Boys Volleyball | Bridgeport Central | Away - Bridgeport Central HS-The Barry McLeod Court [Directions] | W 3-2 | 3:00 PM, Dismiss 2:45 PM | |
| Wed., 4/19 | JV Boys Volleyball | Bridgeport Central | Away - Bridgeport Central HS-The Barry McLeod Court [Directions] | W 2-0 | 3:00 PM, Dismiss 2:45 PM; 1 Bus (Varsity and JV share bus) | |
| Wed., 4/19 | V Co-ed Sailing | Darien, Fairfield Ludlowe | Home - Grass Island [Directions] | 3:00 p.m. | ||
| Wed., 4/19 | V Softball | Staples | Home - Greenwich HS-Softball Field [Directions] | L 4-12 | ||
| Wed., 4/19 | JV Softball | Staples | Home - Julian Curtiss School [Directions] | Postponed | ||
| Wed., 4/19 | V Girls Tennis | Norwalk | Home - Greenwich HS-Tennis Courts [Directions] | W 7-0 [Detailed Results] | ||
| Wed., 4/19 | JV Girls Tennis | New Canaan | Home - Binney Park [Directions] | 4:30 p.m. | JV A | |
| Thu., 4/20 | V Boys Lacrosse | New Canaan | Home - Greenwich HS-Cardinal Stadium [Directions] | L 14-6 | ||
| Thu., 4/20 | JV Boys Lacrosse | New Canaan | Home - Greenwich HS-Field 4 [Directions] | 5:00 p.m. | ||
| Thu., 4/20 | V Boys Tennis | Trumbull | Away - Trumbull HS-Tennis Courts [Directions] | W 4-3 [Detailed Results] | 2:30 PM, Dismiss 2:15 PM; 1 Bus (Varsity and JV share bus) | |
| Thu., 4/20 | JV Boys Tennis | Trumbull | Away - Tashua Knolls Golf Course-Tennis Courts [Directions] | 4:30 p.m. | 2:30 PM, Dismiss 2:15 PM (Varsity and JV share bus) | JV B |
| Thu., 4/20 | V Girls Golf | Wilton | Away - Silvermine Golf Club [Directions] | 3:30 p.m. | ||
| Thu., 4/20 | V Girls Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | L 6-14 | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Thu., 4/20 | JV Girls Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 6:00 p.m. | 4:15 PM; 1 Bus | |
| Thu., 4/20 | V Girls Tennis | Trumbull | Home - Greenwich HS-Tennis Courts [Directions] | W 7-0 [Detailed Results] | ||
| Thu., 4/20 | JV Girls Tennis | Trumbull | Home - Binney Park [Directions] | 4:30 p.m. | JV B | |
| Fri., 4/21 | V Baseball | Norwalk | Home - Greenwich HS-Baseball Field [Directions] | L 0-4 | ||
| Fri., 4/21 | JV Baseball | Norwalk | Home - Julian Curtiss School [Directions] | 4:30 p.m. | ||
| Fri., 4/21 | FR Baseball | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 4:00 p.m. | 2:45 PM, Dismiss 2:30 PM; 1 Bus | |
| Fri., 4/21 | FR Boys Lacrosse | New Canaan | Home - Cos Cob Park, Benvenuto Field-Benvenuto Field [Directions] | 4:30 p.m. | 2:55 PM, Dismiss 2:35 PM; 1 Bus (drop off only) | |
| Fri., 4/21 | V Boys Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | W 3-1 | 2:45 PM, Dismiss 2:30 PM; 1 Bus (Varsity and JV share bus) | |
| Fri., 4/21 | JV Boys Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | W 2-0 | 2:45 PM, Dismiss 2:30 PM (Varsity and JV share bus) | |
| Fri., 4/21 | V Softball | Norwalk | Away - Norwalk HS-Ray Barry Field [Directions] | L 0-12 | 2:45 PM, Dismiss 2:30 PM; 1 Bus (Varsity and JV share bus) | |
| Fri., 4/21 | JV Softball | Norwalk | Away - Naramake School Field [Directions] | Postponed | 2:45 PM (Varsity and JV share bus) | |
| Sat., 4/22 | V Boys Lacrosse | Mamaroneck (NY) | Home - Greenwich HS-Cardinal Stadium [Directions] | L 10-9 | played at Cardinal Stadium | |
| Sat., 4/22 | JV Boys Lacrosse | Mamaroneck (NY) | Home - Greenwich HS-Field 7 [Directions] | 12:00 p.m. | ||
| Sat., 4/22 | V Boys Rugby | GHS Rugby all day | Home - Greenwich HS-Cardinal Stadium [Directions] | 11:00 a.m. | ||
| Sat., 4/22 | V Girls Rugby | Simsbury | Away - Holden Field-Simsbury 2 [Directions] | 11:00 a.m. | 8:00 AM; 1 Bus | |
| Sat., 4/22 | V Softball | Weston | Home - Greenwich HS-Softball Field [Directions] | W 12-5 | ||
| Mon., 4/24 | V Baseball | Fairfield Warde | Away - Fairfield Warde HS-Baseball Diamond [Directions] | L 1-10 | 2:45 PM, Dismiss 2:30 PM; 1 Bus | |
| Mon., 4/24 | JV Baseball | Fairfield Warde | Away - Tunxis [Directions] | 4:30 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Mon., 4/24 | FR Baseball | Fairfield Warde | Home - Greenwich HS-Baseball Field [Directions] | 4:30 p.m. | ||
| Mon., 4/24 | FR Boys Lacrosse | Fairfield Ludlowe | Home - Cos Cob Park, Benvenuto Field-Benvenuto Field [Directions] | 4:30 p.m. | 2:55 PM, Dismiss 2:35 PM; 1 Bus (Drop off only Shared with Softball) | |
| Mon., 4/24 | V Boys Tennis | New Canaan | Home - Greenwich HS-Tennis Courts [Directions] | W 6-1 [Detailed Results] | ||
| Mon., 4/24 | JV Boys Tennis | New Canaan | Home - Central MS [Directions] | 4:30 p.m. | JV A | |
| Mon., 4/24 | V Boys Volleyball | Fairfield Ludlowe | Home - Greenwich HS-Gymnasium [Directions] | L 1-3 | ||
| Mon., 4/24 | JV Boys Volleyball | Brien McMahon | Home - Greenwich HS-Gymnasium [Directions] | L 1-2 | ||
| Mon., 4/24 | FR Girls Lacrosse | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 5:00 p.m. | 3:45 PM; 1 Bus | |
| Mon., 4/24 | V Softball | Fairfield Warde | Home - Greenwich HS-Softball Field [Directions] | L 3-13 | ||
| Mon., 4/24 | JV Softball | Fairfield Warde | Home - Julian Curtiss School [Directions] | Postponed | 2:55 PM (Drop off only, shared with freshmen lax) | |
| Mon., 4/24 | V Girls Tennis | New Canaan | Away - New Canaan HS-NCHS Tennis Courts [Directions] | W 4-3 [Detailed Results] | 2:45 PM, Dismiss 2:30 PM; 1 Bus | |
| Tue., 4/25 | V Boys Lacrosse | Fairfield Ludlowe | Home - Greenwich HS-Cardinal Stadium [Directions] | W 12-4 | ||
| Tue., 4/25 | JV Boys Lacrosse | Fairfield Ludlowe | Home - Greenwich HS-Field 4 [Directions] | 5:00 p.m. | ||
| Tue., 4/25 | V Boys Outdoor Track | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM; 2 Buses | |
| Tue., 4/25 | V Boys Tennis | Darien | Home - Greenwich HS-Tennis Courts [Directions] | W 4-3 [Detailed Results] | ||
| Tue., 4/25 | JV Boys Tennis | Darien | Home - Central MS [Directions] | 4:30 p.m. | JV B | |
| Tue., 4/25 | JV Boys Tennis | Horace Greeley (NY) | Away - Horace Greeley HS | 4:30 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | JV A |
| Tue., 4/25 | V Girls Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | W 12-7 | 2:30 PM, Dismiss 2:15 PM; 1 Bus | |
| Tue., 4/25 | JV Girls Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 5:30 p.m. | 3:45 PM; 1 Bus | |
| Tue., 4/25 | V Girls Outdoor Track | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | W 85-60 | 2:30 PM, Dismiss 2:15 PM; 2 Buses | |
| Tue., 4/25 | V Girls Tennis | Darien | Away - Darien HS-DHS Tennis Courts [Directions] | W 5-2 [Detailed Results] | 2:45 PM, Dismiss 2:30 PM (Varsity and JV share bus) | |
| Tue., 4/25 | JV Girls Tennis | Rye Country Day (NY) | Away - Rye Country Day School | 4:00 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | JV B |
| Tue., 4/25 | JV Girls Tennis | Darien | Away - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | 2:45 PM, Dismiss 2:30 PM; 1 Bus (Varsity and JV share bus) | JV A |
| Wed., 4/26 | FR Boys Lacrosse | Stamford | Away - Stamford HS-Upper Lacrosse Field [Directions] | 5:00 p.m. | 3:30 PM; 1 Bus | |
| Wed., 4/26 | JV Boys Tennis | Brunswick School | Away - Brunswick School | 4:00 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | JV A |
| Wed., 4/26 | V Boys Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | L 0-3 | 2:30 PM, Dismiss 2:15 PM (Varsity and JV share bus) | |
| Wed., 4/26 | JV Boys Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | L 0-2 | 2:30 PM, Dismiss 2:15 PM; 1 Bus (Varsity and JV share bus) | |
| Wed., 4/26 | V Co-ed Sailing | Darien | Home - Grass Island [Directions] | 3:00 p.m. | ||
| Wed., 4/26 | V Girls Golf | St. Joseph | Home - Griffith E Harris Golf Course [Directions] | 3:30 p.m. | ||
| Wed., 4/26 | FR Girls Lacrosse | Fairfield Ludlowe | Home - Cos Cob Park, Benvenuto Field-Benvenuto Field [Directions] | 5:30 p.m. | ||
| Wed., 4/26 | V Softball | Trumbull | Away - Trumbull HS-Varsity Softball Diamond [Directions] | L 0-15 | 2:30 PM, Dismiss 2:15 PM; 1 Bus (Varsity and JV share bus) | |
| Wed., 4/26 | JV Softball | Trumbull | Away - Trumbull HS-JV Softball Diamond [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM; 1 Bus (Varsity and JV share bus) | |
| Wed., 4/26 | JV Girls Tennis | Staples | Away - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | 2:45 PM, Dismiss 2:30 PM; 1 Bus | JV A |
| Thu., 4/27 | V Baseball | Trumbull | Home - Greenwich HS-Baseball Field [Directions] | L 1-11 F5 | ||
| Thu., 4/27 | JV Baseball | Trumbull | Home - Julian Curtiss School [Directions] | 4:30 p.m. | ||
| Thu., 4/27 | V Boys Lacrosse | Notre Dame-West Haven | Away - Notre Dame HS-Veteran's Stadium [Directions] | W 14-10 | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Thu., 4/27 | V Girls Golf | Fairfield Warde | Away - Smith Richardson Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 4/27 | V Girls Rugby | Darien | Home - Greenwich HS-Cardinal Stadium [Directions] | Cancelled | ||
| Thu., 4/27 | V Girls Rugby | Trumbull | Home - Greenwich HS-Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Fri., 4/28 | V Baseball | New Canaan | Away - Mead Park-Baseball Field [Directions] | W 7-5 | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Fri., 4/28 | JV Baseball | New Canaan | Away - Waveny Park-Coppo Field [Directions] | 4:30 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Fri., 4/28 | FR Baseball | New Canaan | Home - Greenwich HS-Baseball Field [Directions] | 4:30 p.m. | ||
| Fri., 4/28 | FR Boys Lacrosse | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Fri., 4/28 | JV Boys Rugby | Rye (NY) | Away - Rye HS-Field | Cancelled | ||
| Fri., 4/28 | V Boys Tennis | Ridgefield | Away - Ridgefield HS-RHS Tennis Courts [Directions] | W 5-2 [Detailed Results] | 2:30 PM, Dismiss 2:15 PM (Varsity and JV share bus) | |
| Fri., 4/28 | JV Boys Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM; 1 Bus (Varsity and JV share bus) | JV B |
| Fri., 4/28 | V Boys Volleyball | Danbury | Home - Greenwich HS-Gymnasium [Directions] | W 3-1 | ||
| Fri., 4/28 | JV Boys Volleyball | Danbury | Home - Greenwich HS-Gymnasium [Directions] | L 1-2 | ||
| Fri., 4/28 | V Softball | New Canaan | Home - Greenwich HS-Softball Field [Directions] | L 4-15 | ||
| Fri., 4/28 | V Girls Tennis | Ridgefield | Home - Greenwich HS-Tennis Courts [Directions] | W 7-0 [Detailed Results] | ||
| Fri., 4/28 | JV Girls Tennis | Ridgefield | Home - Binney Park [Directions] | 4:30 p.m. | JV B | |
| Fri., 4/28 | V Girls Water Polo | Greenwich Academy | Home - Greenwich HS-Pool [Directions] | 4:15 p.m. | ||
| Sat., 4/29 | V Boys Lacrosse | Staples | Away - Staples HS-Staples Stadium [Directions] | L 15-3 | 11:00 AM; 1 Bus | |
| Sat., 4/29 | JV Boys Lacrosse | Staples | Away - Staples HS-Wakeman Field B (turf) [Directions] | 11:00 a.m. | 1:00 PM; 1 Bus | |
| Sat., 4/29 | V Girls Lacrosse | Staples | Home - Greenwich HS-Cardinal Stadium [Directions] | W 13-8 | ||
| Sat., 4/29 | JV Girls Lacrosse | Staples | Home - Greenwich HS-Cardinal Stadium [Directions] | 11:30 a.m. | ||
| Sat., 4/29 | JV Softball | New Canaan | Home - Greenwich HS-Softball Field [Directions] | Postponed | ||
| Sat., 4/29 | V Girls Water Polo | @ Northampton vs Andover & Williston | Away - . | TBA | 3:00 PM, Dismiss 2:45 PM | |
| Mon., 5/1 | V Baseball | Darien | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | W 4-3 | ||
| Mon., 5/1 | JV Baseball | Darien | Away - Darien HS-DHS Baseball - JV Field [Directions] | 4:30 p.m. | ||
| Mon., 5/1 | FR Baseball | Darien | Home - Julian Curtiss School [Directions] | 4:30 p.m. | ||
| Mon., 5/1 | FR Boys Lacrosse | Wilton | Away - Allen's Meadow-Lacrosse Field #1 [Directions] | 4:30 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Mon., 5/1 | V Boys Outdoor Track | Danbury | Away - Danbury HS-Stadium Track [Directions] | 4:00 p.m. | ||
| Mon., 5/1 | V Boys Tennis | Bridgeport Central | Away - Bridgeport Central HS-Central High School Tennis Courts [Directions] | W 7-0 [Detailed Results] | ||
| Mon., 5/1 | V Boys Volleyball | Westhill | Home - Greenwich HS-Gymnasium [Directions] | L 1-3 | ||
| Mon., 5/1 | JV Boys Volleyball | Westhill | Home - Greenwich HS-Gymnasium [Directions] | W 2-1 | ||
| Mon., 5/1 | FR Girls Lacrosse | Darien | Home - Cos Cob Park, Benvenuto Field-Benvenuto Field [Directions] | Cancelled | ||
| Mon., 5/1 | V Girls Outdoor Track | Danbury | Away - Danbury HS-Stadium Track [Directions] | W 82-63 | ||
| Mon., 5/1 | V Softball | Darien | Home - Bruce Park Field [Directions] | W 6-3 | ||
| Mon., 5/1 | V Girls Tennis | Bridgeport Central | Home - Greenwich HS-Tennis Courts [Directions] | W 7-0 [Detailed Results] | ||
| Mon., 5/1 | JV Girls Tennis | St. Joseph | Home - Binney Park [Directions] | 4:30 p.m. | JV B | |
| Tue., 5/2 | FR Baseball | Trumbull | Away - Trumbull HS-JV Baseball Field [Directions] | Postponed | 2:30 PM; 1 Bus | |
| Tue., 5/2 | JV Boys Lacrosse | Greenwich Country Day | Away - Greenwich Country Day School-Stanwich Rd. Back Turf | 4:15 p.m. | ||
| Tue., 5/2 | JV Girls Golf | Darien | Away - Country Club of Darien [Directions] | 3:00 p.m. | ||
| Wed., 5/3 | V Baseball | Ridgefield | Home - Julian Curtiss School [Directions] | W 1-0 | ||
| Wed., 5/3 | FR Baseball | Ridgefield | Away - Governor Field [Directions] | 4:00 p.m. | ||
| Wed., 5/3 | FR Boys Lacrosse | Fairfield Warde | Home - Cos Cob Park, Benvenuto Field-Benvenuto Field [Directions] | 4:30 p.m. | 3:30 PM; 1 Bus (Drop off only) | |
| Wed., 5/3 | V Boys Tennis | Danbury | Away - Danbury HS-DHS Tennis Courts [Directions] | W 7-0 [Detailed Results] | ||
| Wed., 5/3 | JV Boys Tennis | Staples | Away - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | 12:00 PM | JV A |
| Wed., 5/3 | V Boys Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | W 3-0 | ||
| Wed., 5/3 | JV Boys Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | L 0-2 | ||
| Wed., 5/3 | V Girls Golf | Darien | Away - Woodway Country Club [Directions] | 3:00 p.m. | ||
| Wed., 5/3 | V Girls Rugby | Darien, Fairfield Ludlowe | Away - Darien HS-Royle Field @ 133 Mansfield Ave, Darien, CT 06820 [Directions] | Cancelled | 12:00 PM | |
| Pending change awaiting acceptance by one or more parties involved: Time to 4:30 p.m. | ||||||
| Wed., 5/3 | JV Softball | Ridgefield | Away - Ridgefield HS-Varsity Softball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/3 | V Girls Tennis | Danbury | Home - Greenwich HS-Tennis Courts [Directions] | W 7-0 [Detailed Results] | ||
| Wed., 5/3 | JV Girls Tennis | Staples | Home - Binney Park [Directions] | 4:30 p.m. | JV A | |
| Wed., 5/3 | V Girls Water Polo | Sacred Heart of Greenwich | Home - Greenwich HS-Pool [Directions] | 4:15 p.m. | ||
| Thu., 5/4 | JV Baseball | Ridgefield | Home - Julian Curtiss School [Directions] | 4:30 p.m. | ||
| Thu., 5/4 | V Boys Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | L 15-10 | 2:30 PM, Dismiss 2:15 PM; 1 Bus | |
| Thu., 5/4 | JV Boys Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 4:30 p.m. | 2:30 PM, Dismiss 2:15 PM; 1 Bus | |
| Thu., 5/4 | V Boys Rugby | Trumbull | Home - Greenwich HS-Field 7 [Directions] | 4:30 p.m. | ||
| Thu., 5/4 | V Boys Tennis | Westhill | Home - Greenwich HS-Tennis Courts [Directions] | W 7-0 [Detailed Results] | ||
| Thu., 5/4 | JV Boys Tennis | Staples | Home - Central MS [Directions] | 4:30 p.m. | JV B | |
| Thu., 5/4 | V Girls Golf | Danbury | Away - Richter Park Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 5/4 | V Girls Lacrosse | Ridgefield | Home - Greenwich HS-Cardinal Stadium [Directions] | W 11-4 | ||
| Thu., 5/4 | JV Girls Lacrosse | Ridgefield | Home - Greenwich HS-Cardinal Stadium [Directions] | 5:00 p.m. | ||
| Thu., 5/4 | V Girls Tennis | Westhill | Away - Westhill HS-Westhill Tennis Courts [Directions] | W 7-0 [Detailed Results] | ||
| Thu., 5/4 | JV Girls Tennis | Staples | Away - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | 12:00 PM | JV A |
| Fri., 5/5 | V Baseball | Bridgeport Central | Home - Greenwich HS-Baseball Field [Directions] | W 11-1 F5 | ||
| Fri., 5/5 | FR Boys Lacrosse | Westhill | Home - Cos Cob Park, Benvenuto Field-Benvenuto Field [Directions] | 4:30 p.m. | 3:30 PM; 1 Bus (drop off only) | |
| Fri., 5/5 | JV Boys Tennis | New Canaan | Home - Central MS [Directions] | 4:15 p.m. | JV B | |
| Fri., 5/5 | V Boys Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | L 1-3 | ||
| Fri., 5/5 | JV Boys Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | W 2-0 | ||
| Fri., 5/5 | FR Girls Lacrosse | Wilton | Away - Wilton HS-Allen Meadow [Directions] | 4:30 p.m. | ||
| Fri., 5/5 | V Softball | Bridgeport Central | Away - Bridgeport Central-Varsity Softball Field [Directions] | W 18-0 | ||
| Fri., 5/5 | JV Girls Tennis | Greenwich Academy | Away - Greenwich Academy - Everett Field | 3:30 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus | JV B |
| Sat., 5/6 | V Boys Lacrosse | Fordham Prep (NY) | Away - Murphy Field | L 14-12 | 3:00 PM; 1 Bus | |
| Sat., 5/6 | JV Boys Lacrosse | Fordham Prep (NY) | Home - Greenwich HS-Field 7 [Directions] | 2:00 p.m. | ||
| Sat., 5/6 | JV Boys Rugby | Trumbull | Home - Greenwich HS-Field 7 [Directions] | 10:00 a.m. | ||
| Sat., 5/6 | V Girls Lacrosse | Fox Lane (NY) | Away - Fox Lane HS | W 10-9 | 1:00 PM; 1 Bus | |
| Sat., 5/6 | JV Girls Lacrosse | Fox Lane (NY) | Away - Fox Lane HS | 11:30 a.m. | 9:15 AM; 1 Bus | |
| Sat., 5/6 | V Girls Rugby | Morris Rugby (Morristown NJ) | Away - . | 12:00 p.m. | 9:45 AM; 1 Bus | Morris Rugby (Morristown NJ) |
| Sat., 5/6 | V Softball | Ridgefield | Away - Ridgefield HS-Varsity Softball Field [Directions] | L 12-0 | ||
| Sat., 5/6 | JV Softball | Bridgeport Central | Home - Greenwich HS-Softball Field [Directions] | 10:00 a.m. | ||
| Sun., 5/7 | V Girls Water Polo | Cardinal Tournament | Home - Greenwich HS-Pool [Directions] | 11:00 a.m. | ||
| Mon., 5/8 | V Baseball | Danbury | Home - Greenwich HS-Baseball Field [Directions] | L 0-4 | ||
| Mon., 5/8 | JV Baseball | Danbury | Home - Julian Curtiss School [Directions] | 4:30 p.m. | ||
| Mon., 5/8 | FR Baseball | Danbury | Away - Danbury HS-V Baseball Field [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM; 1 Bus | |
| Mon., 5/8 | V Boys Lacrosse | Norwalk | Away - Norwalk HS-Testa Field [Directions] | W 18-2 | 4:30 PM; 1 Bus | |
| Mon., 5/8 | JV Boys Lacrosse | Norwalk | Away - Norwalk HS-Testa Field [Directions] | Cancelled | 3:00 PM; 1 Bus | |
| Mon., 5/8 | FR Boys Lacrosse | Trumbull | Away - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM; 1 Bus | |
| Mon., 5/8 | V Boys Tennis | Wilton | Away - Wilton HS-Tennis Courts [Directions] | W 6-1 [Detailed Results] | 2:45 PM, Dismiss 2:30 PM; 1 Bus | |
| Mon., 5/8 | V Boys Volleyball | Darien | Home - Greenwich HS-Gymnasium [Directions] | L 0-3 | ||
| Mon., 5/8 | JV Boys Volleyball | Darien | Home - Greenwich HS-Gymnasium [Directions] | W 2-0 | ||
| Mon., 5/8 | V Girls Lacrosse | Bronxville (NY) | Away - Bronxville HS | L 3-7 | 3:00 PM, Dismiss 2:45 PM | |
| Mon., 5/8 | JV Girls Lacrosse | Bronxville (NY) | Away - Bronxville HS | 5:45 p.m. | 4:15 PM | |
| Mon., 5/8 | V Softball | Danbury | Away - Danbury HS-V Softball field [Directions] | W 4-1 | 2:45 PM, Dismiss 2:30 PM; 1 Bus (Varsity & JV share a bus) | |
| Mon., 5/8 | JV Softball | Danbury | Away - Danbury HS-JV Softball Field [Directions] | 4:30 p.m. | 2:45 PM, Dismiss 2:30 PM (Varsity & JV share a bus) | |
| Mon., 5/8 | V Girls Tennis | Wilton | Home - Greenwich HS-Tennis Courts [Directions] | W 6-1 [Detailed Results] | ||
| Mon., 5/8 | JV Girls Tennis | Wilton | Home - Binney Park [Directions] | 4:30 p.m. | JV A | |
| Tue., 5/9 | V Boys Outdoor Track | Stamford | Home - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/9 | V Boys Tennis | St. Joseph | Home - Greenwich HS-Tennis Courts [Directions] | W 6-1 [Detailed Results] | ||
| Tue., 5/9 | JV Boys Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | 2:45 PM, Dismiss 2:30 PM; 1 Bus | JV B |
| Tue., 5/9 | V Girls Golf | Fairfield Ludlowe | Home - Griffith E Harris Golf Course [Directions] | 3:30 p.m. | ||
| Tue., 5/9 | V Girls Outdoor Track | Stamford | Home - Greenwich HS-Cardinal Stadium [Directions] | W 106-38 | ||
| Tue., 5/9 | V Girls Tennis | St. Joseph | Away - St. Joseph HS-Tennis Courts [Directions] | W 7-0 [Detailed Results] | 2:30 PM, Dismiss 2:15 PM; 1 Bus | |
| Wed., 5/10 | V Baseball | Westhill | Away - Cubeta Stadium [Directions] | L 6-16 F5 | 5:00 PM; 1 Bus | |
| Wed., 5/10 | JV Baseball | Westhill | Away - Westhill HS-Varsity Baseball Field [Directions] | 4:00 p.m. | 2:45 PM, Dismiss 2:30 PM; 1 Bus | |
| Wed., 5/10 | FR Baseball | Westhill | Home - Greenwich HS-Baseball Field [Directions] | 4:30 p.m. | ||
| Wed., 5/10 | V Boys Lacrosse | Somers (NY) | Home - Greenwich HS-Cardinal Stadium [Directions] | L 10-5 | ||
| Wed., 5/10 | JV Boys Lacrosse | Somers (NY) | Home - Greenwich HS-Field 7 [Directions] | 5:00 p.m. | ||
| Wed., 5/10 | FR Boys Lacrosse | Staples | Home - Cos Cob Park, Benvenuto Field-Benvenuto Field [Directions] | 4:30 p.m. | 3:30 PM; 1 Bus (drop off only) | |
| Wed., 5/10 | V Boys Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | W 3-1 | 2:30 PM, Dismiss 2:15 PM; 1 Bus (Varsity & JV share a bus) | |
| Wed., 5/10 | JV Boys Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | W 2-1 | 2:30 PM, Dismiss 2:15 PM (Varsity & JV share a bus) | |
| Wed., 5/10 | V Girls Lacrosse | Daniel Hand | Home - Greenwich HS-Cardinal Stadium [Directions] | W 13-8 | ||
| Wed., 5/10 | JV Girls Lacrosse | Daniel Hand | Home - Greenwich HS-Field 4 [Directions] | 5:45 p.m. | ||
| Wed., 5/10 | JV Girls Tennis | Greenwich Academy | Home - Binney Park [Directions] | 4:30 p.m. | JV B | |
| Thu., 5/11 | V Boys Rugby | Ridgefield | Home - Greenwich HS-Cardinal Stadium [Directions] | 4:30 p.m. | ||
| Thu., 5/11 | JV Boys Rugby | Ridgefield | Home - Greenwich HS-Field 7 [Directions] | 5:15 p.m. | ||
| Thu., 5/11 | V Boys Tennis | Stamford | Home - Greenwich HS-Tennis Courts [Directions] | W 6-1 [Detailed Results] | ||
| Thu., 5/11 | JV Boys Tennis | Wilton | Home - Central MS [Directions] | 4:30 p.m. | JV A | |
| Thu., 5/11 | V Girls Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Thu., 5/11 | JV Girls Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Thu., 5/11 | V Girls Rugby | TBA, Rye (NY), Staples | Away - Darien HS-Royle Field @ 133 Mansfield Ave, Darien, CT 06820 | Cancelled | 2:45 PM; 1 Bus | |
| Thu., 5/11 | V Girls Rugby | Southington | Home - Greenwich HS-Cardinal Stadium [Directions] | 7:00 p.m. | ||
| Thu., 5/11 | JV Softball | Wilton | Away - Wilton HS-JV Softball Field [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM; 1 Bus | |
| Thu., 5/11 | V Girls Tennis | Stamford | Away - Stamford HS-SHS Tennis Courts [Directions] | W 7-0 [Detailed Results] | 2:45 PM, Dismiss 2:30 PM; 1 Bus | |
| Thu., 5/11 | JV Girls Tennis | Trumbull | Away - Tashua Knolls Golf Course-Tennis Courts [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM; 1 Bus | JV B |
| Fri., 5/12 | V Boys Volleyball | Staples | Home - Greenwich HS-Gymnasium [Directions] | W 3-0 | ||
| Fri., 5/12 | JV Boys Volleyball | Staples | Home - Greenwich HS-Gymnasium [Directions] | W 2-1 | ||
| Fri., 5/12 | V Girls Lacrosse | Greenwich Academy (Scrim.) | Home - Greenwich HS-Field 4 [Directions] | 5:00 p.m. | ||
| Fri., 5/12 | JV Girls Lacrosse | Greenwich Academy (Scrim.) | Home - Greenwich HS-Cardinal Stadium [Directions] | 6:15 p.m. | ||
| Fri., 5/12 | V Softball | Wilton | Away - Wilton HS-Varsity Softball Field [Directions] | L 2-9 | 5:00 PM; 1 Bus | |
| Sat., 5/13 | V Baseball | Wilton | Home - Greenwich HS-Baseball Field [Directions] | W 6-5 | ||
| Sat., 5/13 | JV Baseball | Wilton | Home - Julian Curtiss School [Directions] | 10:30 a.m. | ||
| Sat., 5/13 | FR Baseball | Wilton | Away - Allen's Meadow-Baseball Diamond [Directions] | 2:30 p.m. | 12:30 PM | |
| Sat., 5/13 | V Boys Lacrosse | Darien | Away - Darien HS-DHS Stadium Field [Directions] | L 2-15 | 1:00 PM; 1 Bus | |
| Sat., 5/13 | JV Boys Lacrosse | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 1:30 p.m. | 12:00 PM; 1 Bus | |
| Sat., 5/13 | V Boys Rugby | Xavier | Away - TBA | TBA | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Sat., 5/13 | JV Boys Rugby | Xavier JV | Away - . | TBA | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Sat., 5/13 | FM Boys Rugby | Xavier Frosh | Away - . | TBA | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Mon., 5/15 | V Baseball | St. Joseph | Away - St. Joseph HS-Baseball Diamond [Directions] | L 1-5 | 2:45 PM, Dismiss 2:30 PM; 1 Bus | |
| Mon., 5/15 | JV Baseball | St. Joseph | Away - Unity Park-Field 1 [Directions] | 4:00 p.m. | 2:30 PM, Dismiss 2:15 PM; 1 Bus | |
| Mon., 5/15 | FR Baseball | St. Joseph | Home - Greenwich HS-Baseball Field [Directions] | 4:30 p.m. | ||
| Mon., 5/15 | V Boys Tennis | Trumbull | Home - Greenwich HS-Tennis Courts [Directions] | W 4-0 | FCIAC 1/4 Finals | |
| Mon., 5/15 | V Boys Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | L 0-3 | 2:15 PM, Dismiss 2:00 PM (Varsity and JV will share a bus) | |
| Mon., 5/15 | JV Boys Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | W 2-0 | 2:15 PM, Dismiss 2:00 PM; 1 Bus (Varsity and JV will share a bus) | |
| Mon., 5/15 | V Girls Lacrosse | Darien | Away - Darien HS-DHS Stadium Field [Directions] | L 8-20 | 2:45 PM, Dismiss 2:30 PM; 1 Bus | |
| Mon., 5/15 | JV Girls Lacrosse | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | 4:00 PM; 1 Bus | |
| Mon., 5/15 | V Softball | St. Joseph | Home - Greenwich HS-Softball Field [Directions] | L 18-0 | ||
| Mon., 5/15 | JV Softball | St. Joseph | Home - Julian Curtiss School [Directions] | 4:30 p.m. | ||
| Mon., 5/15 | JV Girls Tennis | Ridgefield | Away - Ridgefield HS-RHS Tennis Courts [Directions] | 4:30 p.m. | 3:00 PM; 1 Bus | |
| Tue., 5/16 | V Baseball | Whitney Tech | Home - Greenwich HS-Baseball Field [Directions] | W 12-2 F5 | ||
| Tue., 5/16 | V Boys Outdoor Track | Staples | Away - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | 2:00 PM, Dismiss 1:45 PM; 2 Buses | |
| Tue., 5/16 | V Girls Golf | Staples | Home - Griffith E Harris Golf Course [Directions] | 3:30 p.m. | ||
| Tue., 5/16 | V Girls Outdoor Track | Staples | Away - Staples HS-Staples Stadium [Directions] | W 80-65 | 2:00 PM, Dismiss 1:45 PM; 2 Buses | |
| Tue., 5/16 | V Girls Tennis | Westhill | Home - Greenwich HS-Tennis Courts [Directions] | 4:00 p.m. | FCIAC 1/4 Finals | |
| Wed., 5/17 | V Baseball | Stamford | Away - Cubeta Stadium [Directions] | L 0-3 | 5:30 PM; 1 Bus | |
| Wed., 5/17 | JV Baseball | Stamford | Away - Stamford HS-SHS Baseball Diamond [Directions] | 4:00 p.m. | 2:45 PM, Dismiss 2:30 PM; 1 Bus | |
| Wed., 5/17 | FR Baseball | Stamford | Home - Greenwich HS-Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/17 | V Boys Lacrosse | St. Joseph | Home - Greenwich HS-Cardinal Stadium [Directions] | L 11-10 | ||
| Wed., 5/17 | JV Boys Lacrosse | St. Joseph | Home - Greenwich HS-Field 4 [Directions] | 4:30 p.m. | ||
| Wed., 5/17 | V Boys Rugby | Simsbury | Away - Holden Field-Simsbury 2 [Directions] | 6:00 p.m. | ||
| Wed., 5/17 | V Boys Tennis | Staples | Home - Greenwich HS-Tennis Courts [Directions] | W 4-0 | FCIAC Semi-Finals | |
| Wed., 5/17 | V Boys Volleyball | St. Joseph | Home - Greenwich HS-Gymnasium [Directions] | W 3-0 | ||
| Wed., 5/17 | JV Boys Volleyball | St. Joseph | Home - Greenwich HS-Gymnasium [Directions] | W 2-0 | ||
| Wed., 5/17 | V Girls Golf | Ridgefield | Home - Griffith E Harris Golf Course [Directions] | 3:30 p.m. | ||
| Wed., 5/17 | V Softball | Stamford | Home - Greenwich HS-Softball Field [Directions] | L 0-14 | ||
| Wed., 5/17 | JV Softball | Stamford | Home - Julian Curtiss School [Directions] | 4:30 p.m. | ||
| Thu., 5/18 | JV Baseball | Darien | Home - Julian Curtiss School [Directions] | 4:30 p.m. | ||
| Thu., 5/18 | V Girls Lacrosse | Ridgefield | Home - Greenwich HS-Cardinal Stadium [Directions] | W 13-12 | ||
| Thu., 5/18 | V Girls Tennis | Darien | Home - Greenwich HS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 5/19 | V Boys Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | L 0-3 | 2:30 PM, Dismiss 2:15 PM; 1 Bus | |
| Fri., 5/19 | V Girls Rugby | Trumbull | Away - Trumbull HS-Aux Gym [Directions] | 5:30 p.m. | 3:00 PM, Dismiss 2:45 PM; 1 Bus (1 bus for Varsity and JV) | |
| Fri., 5/19 | JV Girls Rugby | Trumbull | Away - Trumbull HS-Cork Field [Directions] | 7:30 p.m. | 3:00 PM, Dismiss 2:45 PM (1 bus for Varsity and JV) | |
| Sat., 5/20 | V Boys Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 3:00 p.m. | 1:00 PM; 1 Bus | |
| Sat., 5/20 | JV Boys Rugby | Simsbury | Home - Greenwich HS-Field 7 [Directions] | 11:30 a.m. | Froshmore Game | |
| Mon., 5/22 | FM Boys Rugby | Rye (NY) | Away - Rye HS-Field | TBA | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Mon., 5/22 | V Girls Lacrosse | Darien | Away - Greenwich HS-Cardinal Stadium [Directions] | L 2-16 | ||
| Tue., 5/23 | V Boys Outdoor Track | FCIAC Track Championship | Away - Danbury HS-Danbury HS Stadium | 2:30 p.m. | 12:30 PM, Dismiss 12:15 PM; 1 Bus | |
| Tue., 5/23 | V Boys Tennis | Darien | Home - Wilton HS-Wilton HS tennis courts [Directions] | W 4-3 | 12:30 PM, Dismiss 12:15 PM; 1 Bus | |
| Tue., 5/23 | V Girls Golf | Danbury | Home - Griffith E Harris Golf Course [Directions] | 3:30 p.m. | ||
| Tue., 5/23 | JV Girls Golf | Danbury | Home - Griffith E Harris Golf Course [Directions] | 3:30 p.m. | ||
| Tue., 5/23 | V Girls Outdoor Track | FCIAC Track Championship | Away - Danbury HS-DHS Stadium | 2:30 p.m. | 12:30 PM, Dismiss 12:15 PM; 1 Bus | |
| Wed., 5/24 | V Baseball | New Canaan (Scrim.) | Away - Mead Park-Baseball Field [Directions] | 4:30 p.m. | ||
| Wed., 5/24 | V Girls Golf | Staples | Away - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 5/24 | JV Girls Golf | Staples | Away - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 5/25 | V Boys Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | W 3-0 | 2:45 PM, Dismiss 2:30 PM; 1 Bus | |
| Sat., 5/27 | V Boys Rugby | Nationals | Away - . | TBA | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Sat., 5/27 | V Boys Tennis | East Hartford | Home - Greenwich HS-Tennis Courts [Directions] | W 7-0 | CIAC First Round | |
| Sat., 5/27 | V Girls Tennis | CIAC First Round | Home - Greenwich HS-Tennis Courts [Directions] | 1:00 p.m. | CIAC First Round | |
| Tue., 5/30 | V Boys Tennis | Westhill | Home - Greenwich HS-Tennis Courts [Directions] | W 6-1 | CIAC 1/4 Finals | |
| Tue., 5/30 | V Girls Lacrosse | Staples | Home - Greenwich HS-Cardinal Stadium [Directions] | W 13-5 | CIAC First Round | |
| Tue., 5/30 | V Girls Tennis | Glastonbury | Home - Greenwich HS-Tennis Courts [Directions] | 4:30 p.m. | CIAC 1/4 Finals | |
| Wed., 5/31 | V Boys Outdoor Track | CIAC Class LL Championships | Away - Willow Brook Park | 10:00 a.m. | 7:00 AM; 1 Bus (Shared bus with both track teams) | |
| Wed., 5/31 | V Boys Tennis | Darien | Home - Greenwich HS-Tennis Courts [Directions] | W 4-3 | CIAC Semifinals | |
| Wed., 5/31 | V Boys Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | 2:45 PM, Dismiss 2:30 PM; 1 Bus | |
| Wed., 5/31 | V Girls Outdoor Track | CIAC Class LL Championships | Away - Willow Brook Park | 10:00 a.m. | 7:00 AM (Shared bus with both track teams) | |
| Wed., 5/31 | V Girls Tennis | Wilton | Home - Greenwich HS-Tennis Courts [Directions] | 1:30 p.m. | CIAC Semifinals | |
| Thu., 6/1 | V Boys Rugby | Staples | Home - Greenwich HS-Cardinal Stadium [Directions] | 7:00 p.m. | State Semifinals | |
| Thu., 6/1 | V Boys Tennis | Staples | Home - [CIAC] Wesleyan [Directions] | W 4-0 | ||
| Thu., 6/1 | V Girls Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | W 13-8 | 2:45 PM, Dismiss 2:30 PM; 1 Bus | |
| Sat., 6/3 | FM Boys Rugby | Fairfield Ludlowe | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 3:00 p.m. | 1:00 PM; 1 Bus | |
| Mon., 6/5 | V Boys Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/5 | V Boys Tennis | CIAC Individual Invitational Opening Rounds | Away - Wesleyan | 10:00 a.m. | ||
| Mon., 6/5 | V Girls Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/5 | V Girls Tennis | CIAC Individual Invitational Opening Rounds | Away - Wesleyan | 10:00 a.m. | ||
| Tue., 6/6 | V Boys Tennis | CIAC Individual Invitational Round of 16 | Away - Wesleyan | 12:00 p.m. | ||
| Tue., 6/6 | V Boys Tennis | CIAC Individual Invitational Quarterfinals | Away - Wesleyan | 3:30 p.m. | ||
| Tue., 6/6 | V Girls Tennis | CIAC Individual Invitational Round of 16 | Away - Wesleyan | 12:00 p.m. | ||
| Tue., 6/6 | V Girls Tennis | CIAC Individual Invitational Quarterfinals | Away - Wesleyan | 3:30 p.m. | ||
| Wed., 6/7 | V Boys Tennis | CIAC Individual Invitational Semifinals | Away - Wesleyan | 3:30 p.m. | ||
| Wed., 6/7 | V Girls Golf | CIAC Division I Championship | Away - Timberlin GC | 8:30 a.m. | ||
| Wed., 6/7 | V Girls Tennis | CIAC Individual Invitational Semifinals | Away - Wesleyan | 3:30 p.m. | ||
| Thu., 6/8 | V Boys Tennis | CIAC Individual Invitational Finals | Away - Wesleyan | 3:30 p.m. | ||
| Thu., 6/8 | V Girls Tennis | CIAC Individual Invitational Finals | Away - Wesleyan | 3:30 p.m. | ||
| Fri., 6/9 | V Girls Lacrosse | Darien | Away - Darien HS-DHS Stadium Field [Directions] | L 5-15 | 4:30 PM; 1 Bus | |
| Sat., 6/10 | V Boys Rugby | State Finals | Away - . | TBA | 3:00 PM, Dismiss 2:45 PM; 1 Bus | |
| Sat., 6/10 | V Girls Golf | CIAC State Open Championship | Away - Black Hall Club | 1:00 p.m. | ||
| Mon., 6/12 | V Boys Outdoor Track | CIAC Hammer Throw Championship | Away - Willow Brook Park | 2:00 p.m. | ||
| Mon., 6/12 | V Girls Outdoor Track | CIAC Hammer Throw Championship | Away - Willow Brook Park | 4:00 p.m. | ||
| Tue., 6/13 | V Boys Outdoor Track | CIAC Decathlon Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 6/13 | V Girls Outdoor Track | CIAC Heptathlon Championship | Away - Willow Brook Park | 10:30 a.m. | ||
| Tue., 6/13 | V Girls Outdoor Track | CIAC Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/14 | V Boys Outdoor Track | CIAC Decathlon Championship | Away - Willow Brook Park | 8:30 a.m. | ||
| Wed., 6/14 | V Boys Outdoor Track | CIAC Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/14 | V Girls Outdoor Track | CIAC Heptathlon Championship | Away - Willow Brook Park | 8:30 a.m. | ||