| Staples 2022-23 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 878 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Thu., 8/25 | V Boys Golf | Danbury | Away - Richter Park Golf Course [Directions] | 3:00 p.m. | SHS 160 vs Danbury 171 | |
| Thu., 8/25 | JV Boys Golf | Danbury | Away - Richter Park Golf Course [Directions] | Canceled | Cancelled | |
| Thu., 8/25 | JV Boys Golf | New Canaan | Home - Longshore Golf Course [Directions] | 3:15 p.m. | ||
| Mon., 8/29 | V Boys Golf | Brien McMahon | Away - Oak Hills Golf Course [Directions] | 3:15 p.m. | SHS 173 vs McMahan 200 | |
| Mon., 8/29 | V Field Hockey | Greenwich Academy | Away - Greenwich Academy | 11:30 a.m. | ||
| Mon., 8/29 | JV Field Hockey | Greenwich Academy | Away - Greenwich Academy | 1:00 p.m. | ||
| Mon., 8/29 | JV Girls Soccer | Greens Farms Academy | Away - Greens Farms Academy-Greens Farms Academy - Turf Blue | 10:00 a.m. | ||
| Tue., 8/30 | V Boys Golf | Fairfield Prep | Away - CC of Fairfield [Directions] | 3:00 p.m. | SHHS 180 vs Fairfield Prep 144 | |
| Tue., 8/30 | JV Boys Golf | Fairfield Prep | Home - Longshore Golf Course [Directions] | 3:15 p.m. | ||
| Wed., 8/31 | V Boys Golf | Wilton | Home - Longshore Golf Course [Directions] | 3:00 p.m. | SHS 156 vs Wilton 159 | |
| Wed., 8/31 | JV Boys Golf | Wilton | Home - Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 8/31 | V Girls Soccer | Greenwich Academy | Away - Greenwich Academy-Stadium | 4:45 p.m. | ||
| Wed., 8/31 | JV Girls Soccer | Greenwich Academy | Away - Greenwich Academy-Tammaro Field | 4:45 p.m. | ||
| Sat., 9/3 | V Field Hockey | Sacred Heart of Greenwich | Away - Sacred Heart of Greenwich | 9:15 p.m. | ||
| Wed., 9/7 | V Boys Golf | Norwalk | Home - Longshore Golf Course [Directions] | 3:00 p.m. | SHS 163 vs Norwalk 184 | |
| Thu., 9/8 | FR Football | Conard | Home - Staples HS-Staples Stadium [Directions] | 6:00 p.m. | ||
| Thu., 9/8 | V Boys Soccer | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 4:00 p.m. | W 2-0 | |
| Thu., 9/8 | JV Boys Soccer | Ridgefield | Away - Ridgefield HS-RHS Lower Grass Field [Directions] | 4:00 p.m. | ||
| Thu., 9/8 | FR Boys Soccer | Ridgefield | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Thu., 9/8 | V Field Hockey | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | W 10-0 | |
| Thu., 9/8 | JV Field Hockey | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | Postponed | ||
| Fri., 9/9 | V Football | Conard | Home - Staples HS-Staples Stadium [Directions] | 7:00 p.m. | W 41-13 | |
| Fri., 9/9 | V Girls Soccer | Ridgefield | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | T 0-0 | |
| Fri., 9/9 | JV Girls Soccer | Ridgefield | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Fri., 9/9 | FR Girls Soccer | Ridgefield | Away - Ridgefield HS-Upper Grass Field [Directions] | 4:00 p.m. | ||
| Fri., 9/9 | V Girls Swimming and Diving | Westhill/Stamford | Away - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Fri., 9/9 | V Girls Volleyball | Weston | Away - Weston HS-Gym (New) [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 9/9 | JV Girls Volleyball | Weston | Away - Weston HS-Gym (New) [Directions] | 4:30 p.m. | ||
| Fri., 9/9 | FR Girls Volleyball | Weston | Away - Weston HS-Gym (Old) [Directions] | 4:30 p.m. | ||
| Sat., 9/10 | JV Football | Conard | Home - Staples HS-Staples Stadium [Directions] | 11:00 a.m. | ||
| Sat., 9/10 | V Boys Soccer | New Canaan | Home - Staples HS-Loeffler Field - Staples HS [Directions] | 10:00 a.m. | L 0-1 | |
| Sat., 9/10 | JV Boys Soccer | New Canaan | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Sat., 9/10 | FR Boys Soccer | New Canaan | Away - Saxe MS-Field 1 [Directions] | 10:00 a.m. | ||
| Mon., 9/12 | V Boys Golf | Stamford | Home - Longshore Golf Course [Directions] | Postponed | SHS 153 vs Stamford 171 | |
| Pending changes awaiting acceptance by one or more parties involved: Date to 10/3, Time to 3:15 p.m. | ||||||
| Mon., 9/12 | V Field Hockey | New Canaan | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | W 4-1 | |
| Mon., 9/12 | JV Field Hockey | New Canaan | Home - Staples HS-Ginny Parker Field [Directions] | 5:15 p.m. | ||
| Mon., 9/12 | FR Field Hockey | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Mon., 9/12 | V Girls Soccer | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 6:30 p.m. | W 4-0 | |
| Mon., 9/12 | JV Girls Soccer | New Canaan | Away - Saxe MS-Field 1 [Directions] | 4:30 p.m. | ||
| Mon., 9/12 | FR Girls Soccer | New Canaan | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Mon., 9/12 | V Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 6:00 p.m. | L 2-3 | |
| Mon., 9/12 | JV Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:30 p.m. | ||
| Mon., 9/12 | FR Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Small Gym [Directions] | 4:30 p.m. | ||
| Tue., 9/13 | V Boys Cross Country | Ridgefield, Fairfield Warde, New Canaan | Away - Ridgefield HS-Upper Grass Field [Directions] | 4:00 p.m. | ||
| Tue., 9/13 | V Boys Soccer | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 5:00 p.m. | L 0-1 | |
| Tue., 9/13 | JV Boys Soccer | Greenwich | Away - Cos Cob Park, Benvenuto Field-Benvenuto Field [Directions] | 4:45 p.m. | ||
| Tue., 9/13 | FR Boys Soccer | Greenwich | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Tue., 9/13 | V Girls Cross Country | Ridgefield, Fairfield Warde, New Canaan | Away - Ridgefield HS-Upper Grass Field [Directions] | 4:00 p.m. | ||
| Wed., 9/14 | FR Football | Trumbull | Home - Staples HS-Staples Stadium [Directions] | 6:30 p.m. | ||
| Wed., 9/14 | V Boys Golf | Fairfield Warde | Home - Longshore Golf Course [Directions] | 3:15 p.m. | SHS 150 vs Warde 143 | |
| Wed., 9/14 | JV Boys Golf | Fairfield Warde | Home - Longshore Golf Course [Directions] | 3:15 p.m. | ||
| Wed., 9/14 | V Girls Soccer | Greenwich | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 9/14 | JV Girls Soccer | Greenwich | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Thu., 9/15 | V Boys Golf | New Canaan, St. Joseph | Away - CCNC [Directions] | 3:00 p.m. | SHS 169 vs New Canaan 169 | |
| Thu., 9/15 | JV Boys Golf | New Canaan | Home - Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 9/15 | V Boys Water Polo | Greenwich | Home - Staples HS-Pool [Directions] | 4:30 p.m. | ||
| Thu., 9/15 | V Girls Diving | Fairfield Ludlowe | Home - Staples HS-Staples High School Pool [Directions] | 7:15 p.m. | ||
| Thu., 9/15 | V Field Hockey | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 6:30 p.m. | W 7-1 | |
| Thu., 9/15 | JV Field Hockey | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 5:00 p.m. | ||
| Thu., 9/15 | FR Field Hockey | Norwalk | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Fri., 9/16 | V Boys Soccer | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 3:45 p.m. | T 0-0 | |
| Fri., 9/16 | JV Boys Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 3:45 p.m. | ||
| Fri., 9/16 | FR Boys Soccer | Danbury | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Fri., 9/16 | V Girls Swimming and Diving | Fairfield Warde | Home - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Sat., 9/17 | V Football | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 1:30 p.m. | L 21-42 | |
| Sat., 9/17 | V Sideline Cheerleading | @ ST Joseph | Away - St. Joseph HS | 7:00 p.m. | ||
| Sat., 9/17 | V Field Hockey | Wilton | Away - Wilton HS-Fuijitani Field -Turf [Directions] | 3:30 p.m. | L 1-4 | |
| Sat., 9/17 | JV Field Hockey | Wilton | Away - Wilton HS-Fuijitani Field -Turf [Directions] | 2:00 p.m. | ||
| Sat., 9/17 | FR Field Hockey | Wilton | Home - Staples HS-Ginny Parker Field [Directions] | 10:00 a.m. | ||
| Sat., 9/17 | V Girls Soccer | Danbury | Home - Staples HS-Wakeman Field B (turf) [Directions] | 10:00 a.m. | T 1-1 | |
| Sat., 9/17 | JV Girls Soccer | Danbury | Home - Staples HS-Loeffler Field - Staples HS [Directions] | 10:00 a.m. | ||
| Sat., 9/17 | FR Girls Soccer | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 12:30 p.m. | ||
| Mon., 9/19 | V Boys Soccer | Westhill | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | W 4-3 | |
| Mon., 9/19 | JV Boys Soccer | Westhill | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Mon., 9/19 | FR Boys Soccer | Westhill | Away - Rippowan MS-Rippowam Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 9/19 | V Girls Diving | Darien, Brien McMahon, Norwalk | Away - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Mon., 9/19 | V Girls Volleyball | Wilton | Home - Staples HS-Staples Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Mon., 9/19 | JV Girls Volleyball | Wilton | Home - Staples HS-Staples Gym [Directions] | 4:30 p.m. | ||
| Tue., 9/20 | V Boys Cross Country | Wilton, Brien McMahon, Fairfield Ludlowe | Away - Allen's Meadow-XC Course [Directions] | 4:00 p.m. | ||
| Tue., 9/20 | V Boys Golf | Darien | Home - Longshore Golf Course [Directions] | 3:00 p.m. | SHS 148 Darien 156 | |
| Tue., 9/20 | JV Boys Golf | Darien | Home - Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 9/20 | V Girls Cross Country | Wilton, Brien McMahon, Fairfield Ludlowe | Away - Allen's Meadow-XC Course [Directions] | 4:00 p.m. | ||
| Tue., 9/20 | V Girls Soccer | Westhill | Away - Westhill HS-Westhill Front Turf Field [Directions] | 4:30 p.m. | W 6-0 | |
| Tue., 9/20 | JV Girls Soccer | Westhill | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Tue., 9/20 | FR Girls Volleyball | Wilton | Home - Staples HS-Field House [Directions] | 4:30 p.m. | ||
| Wed., 9/21 | V Boys Golf | St. Joseph | Away - Tashua Knolls Golf Course [Directions] | 3:00 p.m. | SHS 160 vs St Joe's 154 | |
| Wed., 9/21 | JV Boys Golf | St. Joseph | Away - Tashua Knolls Golf Course-Tashua Glen [Directions] | 3:15 p.m. | ||
| Thu., 9/22 | V Boys Golf | Westhill | Away - EG Brennan Golf Course-E Gaynor Brennan Golf Course [Directions] | 3:15 p.m. | SHS 156 vs Westhill 172 | |
| Thu., 9/22 | V Boys Soccer | Wilton | Away - Wilton HS-Lilly Field [Directions] | 5:30 p.m. | L 1-2 | |
| Thu., 9/22 | JV Boys Soccer | Wilton | Away - Allen's Meadow-2A [Directions] | Postponed | ||
| Thu., 9/22 | FR Boys Soccer | Wilton | Home - Staples HS-Wakeman Field E (grass) [Directions] | Postponed | ||
| Thu., 9/22 | V Field Hockey | Ridgefield | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | W 2-1 | |
| Thu., 9/22 | JV Field Hockey | Ridgefield | Home - Staples HS-Ginny Parker Field [Directions] | 5:15 p.m. | ||
| Thu., 9/22 | V Girls Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:45 p.m. | W 3-0 | |
| Thu., 9/22 | JV Girls Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:30 p.m. | ||
| Thu., 9/22 | FR Girls Volleyball | Ridgefield | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Fri., 9/23 | V Football | Newington | Away - Newington HS-Alumni Field [Directions] | 6:30 p.m. | W 37-14 | |
| Fri., 9/23 | V Boys Water Polo | Horace Mann (NY) | Away - Horace Mann School | 4:30 p.m. | ||
| Fri., 9/23 | V Sideline Cheerleading | @ Newington | Away - Newington HS | 6:30 p.m. | ||
| Fri., 9/23 | FR Field Hockey | Ridgefield | Away - Ridgefield HS-Tiger Hollow Turf Field II [Directions] | 4:00 p.m. | ||
| Fri., 9/23 | V Girls Soccer | Wilton | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | W 4-1 | |
| Fri., 9/23 | JV Girls Soccer | Wilton | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Fri., 9/23 | FR Girls Soccer | Wilton | Away - Allen's Meadow-3A [Directions] | 4:00 p.m. | ||
| Fri., 9/23 | V Girls Swimming and Diving | Ridgefield | Home - Staples HS-Staples High School Pool [Directions] | 5:30 p.m. | ||
| Sat., 9/24 | JV Football | Newington | Home - Staples HS-Staples Stadium [Directions] | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to 12:00 p.m. | ||||||
| Sat., 9/24 | FR Football | Newington | Home - Staples HS-Staples Stadium [Directions] | Postponed | ||
| Sat., 9/24 | V Boys Soccer | Glastonbury | Away - Farmington Sports Arena [Directions] | 3:00 p.m. | L 0-4 | |
| Sat., 9/24 | V Field Hockey | Garrison Forest (MD) | Away - Garrison Forest School | 3:00 p.m. | L 0-2 | |
| Sun., 9/25 | V Field Hockey | Conestoga (PA) | Away - Conestoga HS | 1:00 p.m. | L 3-5 | |
| Tue., 9/27 | V Boys Golf | Trumbull | Home - Longshore Golf Course [Directions] | 3:00 p.m. | SHS 145 vs Trumbull 160 | |
| Tue., 9/27 | JV Boys Golf | Trumbull | Home - Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 9/27 | V Boys Water Polo | Greenwich | Away - Greenwich HS-Pool [Directions] | 4:30 p.m. | ||
| Tue., 9/27 | V Field Hockey | Darien | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | L 0-3 | |
| Tue., 9/27 | JV Field Hockey | Darien | Home - Staples HS-Ginny Parker Field [Directions] | 5:15 p.m. | ||
| Tue., 9/27 | FR Field Hockey | Darien | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Tue., 9/27 | JV Girls Soccer | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 9/27 | FR Girls Soccer | Darien | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Tue., 9/27 | V Girls Volleyball | New Canaan | Home - Staples HS-Staples Gym [Directions] | 6:00 p.m. | W 3-2 | |
| Tue., 9/27 | JV Girls Volleyball | New Canaan | Home - Staples HS-Staples Gym [Directions] | 4:30 p.m. | ||
| Tue., 9/27 | FR Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:30 p.m. | ||
| Wed., 9/28 | V Boys Cross Country | Danbury, Greenwich, St. Joseph | Away - Tarrywile Park [Directions] | 4:00 p.m. | ||
| Wed., 9/28 | V Boys Soccer | Darien | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | L 0-1 | |
| Wed., 9/28 | FR Boys Soccer | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 9/28 | V Girls Cross Country | Danbury, Greenwich, St. Joseph | Away - Tarrywile Park [Directions] | 4:00 p.m. | ||
| Wed., 9/28 | FR Field Hockey | Darien | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Wed., 9/28 | V Girls Soccer | Darien | Away - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | T 0-0 | |
| Wed., 9/28 | V Girls Swimming and Diving | Darien | Home - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Thu., 9/29 | FR Football | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 4:30 p.m. | ||
| Thu., 9/29 | V Boys Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 2:50 p.m. | SHS 159 vs Ludlowe 161 | |
| Thu., 9/29 | JV Boys Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 2:50 p.m. | ||
| Thu., 9/29 | JV Boys Soccer | Darien | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Thu., 9/29 | V Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | L 0-3 | |
| Thu., 9/29 | JV Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:00 p.m. | ||
| Thu., 9/29 | FR Girls Volleyball | Greenwich | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/30 | V Football | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 7:00 p.m. | W 36-29 | |
| Fri., 9/30 | V Boys Soccer | Fairfield Warde | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | W 3-2 | |
| Fri., 9/30 | JV Boys Soccer | Fairfield Warde | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Fri., 9/30 | V Sideline Cheerleading | @ Trumbull | Away - trumbull high school | 7:00 p.m. | ||
| Fri., 9/30 | FR Field Hockey | Fairfield Warde | Home - Staples HS-Ginny Parker Field [Directions] | Canceled | Cancelled | |
| Sat., 10/1 | JV Football | Trumbull | Home - Staples HS-Staples Stadium [Directions] | 2:00 p.m. | ||
| Sat., 10/1 | V Boys Water Polo | Staples vs Premier | Away - Chelsea Piers - | 12:00 p.m. | ||
| Sat., 10/1 | V Field Hockey | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | W 9-0 | |
| Sat., 10/1 | JV Field Hockey | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | Postponed | ||
| Sat., 10/1 | V Girls Soccer | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 1:00 p.m. | W 5-4 | |
| Sat., 10/1 | JV Girls Soccer | Fairfield Warde | Away - Fairfield Warde HS-Fairfield Warde Grass Utility Field [Directions] | 1:00 p.m. | ||
| Sat., 10/1 | FR Girls Soccer | Fairfield Warde | Home - Staples HS-Wakeman Field E (grass) [Directions] | 10:00 a.m. | ||
| Sat., 10/1 | V Girls Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 2:00 p.m. | W 3-0 | |
| Sat., 10/1 | JV Girls Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 3:30 p.m. | ||
| Sat., 10/1 | FR Girls Volleyball | Danbury | Home - Staples HS-Staples Gym [Directions] | 11:00 a.m. | ||
| Mon., 10/3 | V Boys Cross Country | Norwalk, Westhill | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Mon., 10/3 | FR Boys Soccer | Fairfield Warde | Away - Tunxis [Directions] | 4:00 p.m. | ||
| Mon., 10/3 | V Boys Water Polo | Staples vs Greenwich Country Day | Home - Staples HS-Staples High School Pool [Directions] | 5:00 p.m. | ||
| Mon., 10/3 | V Girls Cross Country | Norwalk, Westhill | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Mon., 10/3 | V Field Hockey | Brien McMahon | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | W 10-0 | |
| Mon., 10/3 | JV Field Hockey | Brien McMahon | Home - Staples HS-Ginny Parker Field [Directions] | 5:15 p.m. | ||
| Mon., 10/3 | V Girls Swimming and Diving | Fairfield Ludlowe | Away - Fairfield University-Pool [Directions] | 4:00 p.m. | ||
| Mon., 10/3 | V Girls Volleyball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:45 p.m. | L 2-3 | |
| Mon., 10/3 | JV Girls Volleyball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Mon., 10/3 | FR Girls Volleyball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Tue., 10/4 | V Boys Golf | Ridgefield | Away - Silver Spring Golf Course [Directions] | 3:00 p.m. | SHS 173 vs Ridgefield 179 | |
| Tue., 10/4 | JV Boys Golf | Ridgefield | Away - Silver Spring Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 10/6 | V Boys Golf | Trumbull | Home - Longshore Golf Course [Directions] | TBA | match was played 9/27 | |
| Thu., 10/6 | V Boys Golf | Chappa Tournament | Home - Longshore Golf Course [Directions] | TBA | ||
| Thu., 10/6 | V Boys Soccer | Trumbull | Away - Trumbull HS-Cork Field [Directions] | 5:30 p.m. | L 1-4 | |
| Thu., 10/6 | JV Boys Soccer | Trumbull | Away - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Thu., 10/6 | FR Boys Soccer | Trumbull | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Thu., 10/6 | V Field Hockey | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 4:00 p.m. | W 8-1 | |
| Thu., 10/6 | JV Field Hockey | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 5:30 p.m. | ||
| Thu., 10/6 | V Girls Volleyball | Westhill | Home - Staples HS-Staples Gym [Directions] | 6:00 p.m. | L 2-3 | |
| Thu., 10/6 | JV Girls Volleyball | Westhill | Home - Staples HS-Staples Gym [Directions] | 4:30 p.m. | ||
| Thu., 10/6 | FR Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/7 | V Boys Water Polo | Cardinals Tournament | Away - Greenwich HS | TBA | ||
| Fri., 10/7 | FR Field Hockey | Danbury | Home - Staples HS-Ginny Parker Field [Directions] | Canceled | Cancelled | |
| Fri., 10/7 | V Girls Soccer | Trumbull | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | W 1-0 | |
| Fri., 10/7 | JV Girls Soccer | Trumbull | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Fri., 10/7 | FR Girls Soccer | Trumbull | Away - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Sat., 10/8 | JV Football | Stepinac | Away - Stepinac HS | 10:00 a.m. | ||
| Sat., 10/8 | V Boys Water Polo | Hamden Hall | Home - Staples HS-Staples High School Pool [Directions] | 1:00 p.m. | ||
| Sat., 10/8 | V Boys Water Polo | Cardinals Tournament | Away - Greenwich HS | TBA | ||
| Sat., 10/8 | V Girls Swimming and Diving | Norwalk/McMahon | Home - Staples HS-Staples High School Pool [Directions] | 10:00 a.m. | ||
| Mon., 10/10 | V Boys Golf | Greenwich | Home - Longshore Golf Course [Directions] | 3:15 p.m. | shs 157 vs Greenwich 141 | |
| Mon., 10/10 | JV Boys Golf | Greenwich | Home - Longshore Golf Course [Directions] | 3:15 p.m. | ||
| Mon., 10/10 | V Boys Soccer | Stamford | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | W 2-0 | |
| Mon., 10/10 | JV Boys Soccer | Stamford | Home - Staples HS-Wakeman Field E (grass) [Directions] | Postponed | ||
| Mon., 10/10 | FR Boys Soccer | Stamford | Away - Stamford HS-SHS Upper Soccer Field [Directions] | Postponed | ||
| Mon., 10/10 | V Girls Volleyball | Darien | Home - Staples HS-Staples Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Mon., 10/10 | JV Girls Volleyball | Darien | Home - Staples HS-Staples Gym [Directions] | 4:30 p.m. | ||
| Mon., 10/10 | FR Girls Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/11 | V Boys Cross Country | Darien, Stamford, Trumbull | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 10/11 | V Girls Cross Country | Darien, Stamford, Trumbull | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 10/11 | V Field Hockey | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | L 2-3 | |
| Tue., 10/11 | JV Field Hockey | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 5:00 p.m. | ||
| Tue., 10/11 | V Girls Soccer | Stamford | Away - Stamford HS-SHS Upper Soccer Field [Directions] | 4:00 p.m. | W 4-1 | |
| Tue., 10/11 | JV Girls Soccer | Stamford | Away - Rippowam MS-Upper Soccer/Footballl Field [Directions] | 4:00 p.m. | ||
| Tue., 10/11 | FR Girls Soccer | Greenwich | Away - Greenwich HS-Cos Cob Park, Benvenuto Field [Directions] | 4:00 p.m. | ||
| Wed., 10/12 | V Boys Soccer | Bridgeport Central | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | W 4-0 | |
| Wed., 10/12 | JV Boys Soccer | Bridgeport Central | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Wed., 10/12 | V Girls Volleyball | Fairfield Warde | Home - Staples HS-Staples Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Wed., 10/12 | JV Girls Volleyball | Fairfield Warde | Home - Staples HS-Staples Gym [Directions] | 4:30 p.m. | ||
| Wed., 10/12 | FR Girls Volleyball | Fairfield Warde | Home - Staples HS-Field House [Directions] | 4:30 p.m. | ||
| Thu., 10/13 | FR Football | Wilton | Away - Wilton HS-Fuijitani Field -Turf [Directions] | 6:00 p.m. | ||
| Thu., 10/13 | V Field Hockey | Fairfield Ludlowe | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | W 6-0 | |
| Thu., 10/13 | JV Field Hockey | Fairfield Ludlowe | Home - Staples HS-Ginny Parker Field [Directions] | 5:15 p.m. | ||
| Thu., 10/13 | FR Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Front Field [Directions] | 4:00 p.m. | ||
| Thu., 10/13 | V Girls Soccer | Bridgeport Central | Away - Bridgeport Central-Kennedy Stadium Turf [Directions] | 4:00 p.m. | W 7-0 | |
| Thu., 10/13 | V Girls Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | L 2-3 | |
| Thu., 10/13 | JV Girls Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 4:30 p.m. | ||
| Fri., 10/14 | V Football | Danbury | Home - Staples HS-Staples Stadium [Directions] | 7:00 p.m. | W 42-21 | |
| Fri., 10/14 | V Boys Soccer | St. Joseph | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | W 6-0 | |
| Fri., 10/14 | JV Boys Soccer | St. Joseph | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Fri., 10/14 | FR Girls Volleyball | Trumbull | Home - Staples HS-Staples Gym [Directions] | 4:30 p.m. | ||
| Sat., 10/15 | JV Football | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 2:00 p.m. | ||
| Sat., 10/15 | JV Field Hockey | Branford | Away - Branford HS-Athletic Turf Field [Directions] | 11:00 a.m. | ||
| Mon., 10/17 | V Boys Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 6:30 p.m. | L 3-0 | |
| Mon., 10/17 | JV Boys Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 4:15 p.m. | ||
| Mon., 10/17 | V Boys Water Polo | Staples vs G- Aquatics | Home - Staples HS-Staples High School Pool [Directions] | 6:00 p.m. | ||
| Mon., 10/17 | V Field Hockey | Stamford | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | W 9-0 | |
| Mon., 10/17 | JV Field Hockey | Stamford | Home - Staples HS-Ginny Parker Field [Directions] | 5:15 p.m. | ||
| Mon., 10/17 | V Girls Swimming and Diving | Greenwich | Away - Greenwich HS-Pool [Directions] | 4:30 p.m. | ||
| Mon., 10/17 | V Girls Volleyball | Stamford | Home - Staples HS-Staples Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Mon., 10/17 | JV Girls Volleyball | Stamford | Home - Staples HS-Staples Gym [Directions] | 4:30 p.m. | ||
| Mon., 10/17 | FR Girls Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | ||
| Tue., 10/18 | V Girls Soccer | Norwalk | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | W 8-1 | |
| Tue., 10/18 | JV Girls Soccer | Norwalk | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Wed., 10/19 | V Boys Water Polo | Choate Rosemary Hall | Home - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Wed., 10/19 | V Girls Volleyball | Bridgeport Central | Home - Staples HS-Staples Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Wed., 10/19 | JV Girls Volleyball | Bridgeport Central | Home - Staples HS-Staples Gym [Directions] | 4:30 p.m. | ||
| Thu., 10/20 | FR Football | Ridgefield | Away - Ridgefield HS-Tiger Hollow Turf Field II [Directions] | 6:30 p.m. | ||
| Thu., 10/20 | V Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 7:00 p.m. | L 3-1 | |
| Thu., 10/20 | JV Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 5:00 p.m. | ||
| Thu., 10/20 | FR Boys Soccer | Brien McMahon | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Thu., 10/20 | V Field Hockey | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 4:00 p.m. | W 10-0 | |
| Thu., 10/20 | JV Field Hockey | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 5:30 p.m. | ||
| Thu., 10/20 | JV Girls Soccer | St. Joseph | Away - St. Joseph HS-Lower Grass Field [Directions] | Postponed | ||
| Thu., 10/20 | V Girls Volleyball | St. Joseph | Home - Staples HS-Staples Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Thu., 10/20 | JV Girls Volleyball | St. Joseph | Home - Staples HS-Staples Gym [Directions] | 4:30 p.m. | ||
| Thu., 10/20 | FR Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/21 | V Girls Soccer | Brien McMahon | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 10/21 | JV Girls Soccer | Brien McMahon | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Sat., 10/22 | V Football | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 1:00 p.m. | W 42-7 | |
| Sat., 10/22 | V Sideline Cheerleading | @Stamford | Away - Stamford High | 1:00 p.m. | ||
| Sat., 10/22 | V Girls Soccer | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 10:00 a.m. | L 1-2 | |
| Sat., 10/22 | FR Girls Soccer | Fairfield Ludlowe | Home - Staples HS-Loeffler Field - Staples HS [Directions] | 11:00 a.m. | ||
| Sat., 10/22 | V Girls Swimming and Diving | Danbury | Home - Staples HS-Staples High School Pool [Directions] | 10:00 a.m. | ||
| Mon., 10/24 | V Boys Soccer | Fairfield Ludlowe | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | W 1-0 | |
| Mon., 10/24 | JV Boys Soccer | Fairfield Ludlowe | Home - Staples HS-Loeffler Field - Staples HS [Directions] | 4:00 p.m. | ||
| Mon., 10/24 | V Girls Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:30 p.m. | W 3-0 | |
| Mon., 10/24 | JV Girls Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 6:00 p.m. | ||
| Mon., 10/24 | FR Girls Volleyball | Norwalk | Home - Staples HS-Staples Gym [Directions] | 4:30 p.m. | ||
| Tue., 10/25 | FR Boys Soccer | Fairfield Ludlowe | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Tue., 10/25 | V Field Hockey | Trumbull | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | W 9-0 | |
| Tue., 10/25 | JV Field Hockey | Trumbull | Home - Staples HS-Ginny Parker Field [Directions] | 5:15 p.m. | ||
| Tue., 10/25 | FR Field Hockey | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 6:30 p.m. | ||
| Tue., 10/25 | V Girls Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 7:00 p.m. | T 2-2 | |
| Tue., 10/25 | FR Girls Volleyball | Brien McMahon | Home - Staples HS-Staples Gym [Directions] | 4:30 p.m. | ||
| Wed., 10/26 | V Girls Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 5:45 p.m. | W 3-2 | |
| Wed., 10/26 | JV Girls Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 10/27 | FR Football | St. Joseph | Home - Staples HS-Staples Stadium [Directions] | 6:00 p.m. | ||
| Thu., 10/27 | V Girls Swimming and Diving | Trumbull | Home - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Fri., 10/28 | V Football | Norwalk | Home - Staples HS-Staples Stadium [Directions] | 7:00 p.m. | W 56-7 | |
| Fri., 10/28 | FR Boys Soccer | Norwalk | Home - Staples HS-Wakeman Field E (grass) [Directions] | Canceled | Cancelled | |
| Fri., 10/28 | JV Girls Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | 3:30 p.m. | ||
| Fri., 10/28 | V Girls Volleyball | Fairfield Ludlowe | Home - Staples HS-Staples Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Fri., 10/28 | FR Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:30 p.m. | ||
| Sat., 10/29 | JV Football | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 10:00 a.m. | ||
| Sat., 10/29 | V Boys Water Polo | Suffield Academy | Home - Staples HS-Staples High School Pool [Directions] | 3:30 p.m. | ||
| Tue., 11/1 | V Boys Water Polo | Staples vs Premier | Home - Staples HS-Staples High School Pool [Directions] | 6:00 p.m. | ||
| Tue., 11/1 | V Girls Swimming and Diving | FCIAC Trials | Away - Greenwich HS | 5:00 p.m. | ||
| Wed., 11/2 | V Boys Water Polo | Staples Water Polo Boys vs Greenwich Country Day | Away - Greenwich YMCA-YMCA Pool | 3:00 p.m. | ||
| Wed., 11/2 | V Girls Diving | FCIAC Diving Finals | Away - Westhill HS | 5:00 p.m. | ||
| Thu., 11/3 | FR Football | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Fri., 11/4 | V Football | Westhill | Home - Staples HS-Staples Stadium [Directions] | 7:00 p.m. | W 49-0 | |
| Fri., 11/4 | V Boys Water Polo | Loomis Chaffee School | Home - Staples HS-Staples High School Pool [Directions] | 4:30 p.m. | ||
| Fri., 11/4 | V Girls Swimming and Diving | FCIAC Finals | Away - Greenwich HS | 6:30 p.m. | ||
| Sat., 11/5 | JV Football | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 11:30 a.m. | ||
| Sat., 11/5 | V Boys Water Polo | Hamden Hall | Away - Hamden Hall Beckerman Cen - Skiff St | 3:00 p.m. | ||
| Tue., 11/8 | V Girls Volleyball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:00 p.m. | ||
| Thu., 11/10 | FR Football | Greenwich | Home - Staples HS-Staples Stadium [Directions] | 6:00 p.m. | ||
| Sat., 11/12 | V Football | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 6:00 p.m. | W 14-11 | |
| Sat., 11/12 | V Sideline Cheerleading | @ Ridgefield | Away - Ridgefield HS | 6:00 p.m. | ||
| Sat., 11/12 | V Girls Soccer | Wilton | Home - Staples HS-Wakeman Field B (turf) [Directions] | 2:00 p.m. | ||
| Mon., 11/14 | JV Football | Ridgefield | Home - Staples HS-Staples Stadium [Directions] | 6:30 p.m. | ||
| Wed., 11/16 | FR Football | Fairfield Warde | Home - Staples HS-Staples Stadium [Directions] | 6:30 p.m. | ||
| Sat., 11/19 | JV Football | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 11:00 a.m. | ||
| Thu., 11/24 | V Football | Greenwich | Home - Staples HS-Staples Stadium [Directions] | 10:00 a.m. | W 39-38 | |
| Fri., 12/2 | V Boys Squash | Rye (NY) | Home - Intensity Fitness [Directions] | 7:30 p.m. | ||
| Sun., 12/4 | V Boys Squash | Boys Varsity and JV Squash vs Squash Haven Varsity and Jv | Away - Yale University | 10:00 a.m. | ||
| Sun., 12/4 | V Girls Squash | Girls V/JV Squash vs Squash Haven V/JV | Away - Yale University | 10:00 a.m. | ||
| Tue., 12/6 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Terry Conners - Stamford-Ice Rink [Directions] | 7:30 p.m. | W 2-1 (OT) | |
| Wed., 12/7 | V Boys Squash | Bronxville (NY) | Away - Chelsea Piers - -Gym | 7:30 p.m. | ||
| Sat., 12/10 | V Girls Ice Hockey | Mercy/NW Catholic/East Hampton | Away - Cromwell-Upper Rink [Directions] | 5:20 p.m. | L 3-0 | |
| Tue., 12/13 | V Girls Basketball | New Fairfield | Home - Staples HS-Staples Gym [Directions] | 5:15 p.m. | L 52-45 | |
| Tue., 12/13 | JV Girls Basketball | New Fairfield | Home - Staples HS-Staples Gym [Directions] | 3:45 p.m. | ||
| Wed., 12/14 | V Boys Ice Hockey | Wilton | Home - Milford Ice Pavillion-Ice Rink [Directions] | 6:00 p.m. | W 4-3(OT) | |
| Wed., 12/14 | V Wrestling | Ridgefield | Home - Staples HS-Staples Gym [Directions] | 7:00 p.m. | ||
| Wed., 12/14 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Terry Conners - Stamford-Ice Rink [Directions] | 8:00 p.m. | W 9-0 | |
| Sat., 12/17 | V Boys Ice Hockey | Enfield/East Granby/Stafford | Home - Milford Ice Pavillion-Ice Rink [Directions] | 6:00 p.m. | L 3-6 | |
| Sat., 12/17 | V Boys Indoor Track | Bridgeport Central, Fairfield Ludlowe, St. Joseph | Home - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Sat., 12/17 | V Boys Indoor Track | Greenwich, Stamford, Trumbull, Westhill | Home - Staples HS-Field House [Directions] | 1:30 p.m. | ||
| Sat., 12/17 | JV Boys Squash | Boys JV Squash vs Capitol Squash | Away - Chelsea Piers - -Gym | 1:00 p.m. | ||
| Sat., 12/17 | V Girls Ice Hockey | Avon | Away - Newington-Blue Rink [Directions] | 4:35 p.m. | L 5-0 | |
| Sat., 12/17 | V Girls Indoor Track | Bridgeport Central, Fairfield Ludlowe, St. Joseph | Home - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Sat., 12/17 | V Girls Indoor Track | Greenwich, Stamford, Trumbull, Westhill | Home - Staples HS-Field House [Directions] | 1:30 p.m. | ||
| Mon., 12/19 | V Boys Swimming and Diving | Danbury | Home - Staples HS-Staples High School Pool [Directions] | Postponed | ||
| Mon., 12/19 | FR Girls Basketball | New Fairfield | Away - New Fairfield MS-Gym [Directions] | 5:00 p.m. | ||
| Tue., 12/20 | V Boys Squash | Rye (NY) | Away - Chelsea Piers - -Gym | 7:30 p.m. | ||
| Tue., 12/20 | JV Girls Squash | Rye (NY) | Home - Intensity Fitness [Directions] | 7:30 p.m. | ||
| Tue., 12/20 | Miscellaneous Events | Boys and Girls Ski - preseason tryouts | Home - Mt. Southingon Ski Area [Directions] | TBA | ||
| Wed., 12/21 | V Boys Ice Hockey | Bethel/Brookfield/Danbury/Immaculate | Home - Milford Ice Pavillion-Ice Rink [Directions] | 6:00 p.m. | W 7-4 | |
| Wed., 12/21 | V Wrestling | Westhill | Home - Staples HS-Staples Gym [Directions] | 7:00 p.m. | ||
| Thu., 12/22 | V Boys Basketball | Stratford | Away - Stratford HS-Gym [Directions] | 5:30 p.m. | W 66-30 | |
| Thu., 12/22 | JV Boys Basketball | Stratford | Away - Stratford HS-Gym [Directions] | Postponed | ||
| Thu., 12/22 | V Girls Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 7:00 p.m. | L 28-60 | |
| Thu., 12/22 | JV Girls Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 5:15 p.m. | ||
| Thu., 12/22 | FR Girls Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:00 p.m. | ||
| Thu., 12/22 | JV Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice-Stadium [Directions] | 3:30 p.m. | ||
| Mon., 12/26 | JV Wrestling | Trumbull, Brien McMahon, Bristol Eastern, Fairfield Ludlowe, Fairfield Warde, Greenwich, TBA, New Milford, Newtown | Away - Trumbull HS-THS Main Gym | 9:00 a.m. | ||
| Tue., 12/27 | V Boys Basketball | Pomperaug | Home - Staples HS-Staples Gym [Directions] | 5:00 p.m. | W 61-38 | |
| Tue., 12/27 | V Girls Basketball | Fairfield Warde | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 12:00 p.m. | L 34-43 | |
| Wed., 12/28 | V Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena-Patriot Rink [Directions] | 7:30 p.m. | W 6-3 | |
| Wed., 12/28 | V Girls Basketball | St. Paul Catholic | Home - Fairfield Ludlowe HS-Main Gym [Directions] | 12:00 p.m. | L 27-59 | |
| Wed., 12/28 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Terry Conners - Stamford-Ice Rink [Directions] | 2:15 p.m. | W 4-3 | |
| Thu., 12/29 | V Boys Basketball | Berlin | Home - Staples HS-Staples Gym [Directions] | 5:00 p.m. | W 75-50 | |
| Thu., 12/29 | V Girls Ice Hockey | Hamden Coop | Away - Hamden-Lou Astorino Ice Rink [Directions] | 12:00 p.m. | W 3-1 | |
| Fri., 12/30 | V Wrestling | Darien, Danbury, Stamford | Away - Darien HS-DHS South Gym [Directions] | 10:00 a.m. | ||
| Sat., 12/31 | V Boys Ice Hockey | South Windsor | Home - Milford Ice Pavillion-Ice Rink [Directions] | 11:00 a.m. | L 1-3 | |
| Tue., 1/3 | V Boys Basketball | Newtown | Away - Newtown HS-Gym [Directions] | 7:00 p.m. | W 48-47 | |
| Tue., 1/3 | JV Boys Basketball | Newtown | Away - Newtown HS-Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/3 | FR Boys Basketball | Newtown | Away - Newtown HS-Gym [Directions] | 4:30 p.m. | ||
| Tue., 1/3 | V Girls Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 7:00 p.m. | W 37-27 | |
| Tue., 1/3 | JV Girls Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/3 | FR Girls Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/4 | V Boys Ice Hockey | New Milford | Away - Canterbury School-O'Neill Arena [Directions] | 7:00 p.m. | L 3-4(OT) | |
| Wed., 1/4 | V Boys Swimming and Diving | Westhill/Stamford | Away - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Wed., 1/4 | V Girls Ice Hockey | New Canaan | Home - Terry Conners - Stamford-Ice Rink [Directions] | 7:30 p.m. | W 3-2 | |
| Thu., 1/5 | V Girls Gymnastics | Greenwich, Norwalk | Away - Greenwich YWCA [Directions] | 6:30 p.m. | 126.75 | |
| Fri., 1/6 | V Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 7:00 p.m. | W 61-54 | |
| Fri., 1/6 | JV Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/6 | FR Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/6 | V Boys Squash | SHS Boys Varsity Squash vs Scarsdale | Home - Intensity Fitness [Directions] | 7:30 p.m. | ||
| Fri., 1/6 | V Girls Basketball | Ridgefield | Home - Staples HS-Staples Gym [Directions] | 6:00 p.m. | L 26-44 | |
| Fri., 1/6 | JV Girls Basketball | Ridgefield | Home - Staples HS-Staples Gym [Directions] | 4:30 p.m. | ||
| Sat., 1/7 | V Boys Indoor Track | Bridgeport Central, Greenwich, St. Joseph | Home - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/7 | V Wrestling | Warde Invitational | Away - Fairfield Warde HS-Large Gym | 9:00 a.m. | ||
| Sat., 1/7 | V Girls Indoor Track | Bridgeport Central, Greenwich, St. Joseph | Home - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Mon., 1/9 | V Girls Basketball | Windsor | Home - Staples HS-Staples Gym [Directions] | 5:00 p.m. | W 50-47 | |
| Mon., 1/9 | JV Girls Basketball | Windsor | Home - Staples HS-Staples Gym [Directions] | Canceled | Cancelled | |
| Mon., 1/9 | V Girls Squash | Girls Varsity Squash vs Squash City Girls Varsity | Home - Intensity Fitness [Directions] | 7:30 p.m. | ||
| Tue., 1/10 | V Boys Basketball | New Canaan | Home - Staples HS-Staples Gym [Directions] | 7:00 p.m. | W 68-67(OT) | |
| Tue., 1/10 | JV Boys Basketball | New Canaan | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/10 | FR Boys Basketball | New Canaan | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/10 | V Girls Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 7:00 p.m. | L 37-45 | |
| Tue., 1/10 | JV Girls Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/10 | FR Girls Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/11 | V Boys Ice Hockey | Trumbull | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | 8:00 p.m. | L 1-6 | |
| Wed., 1/11 | JV Boys Squash | Boys JV Squash vs City Squash Macs | Away - Chelsea Piers - -Gym | 7:30 p.m. | ||
| Wed., 1/11 | V Boys Swimming and Diving | Trumbull | Away - Univ of Bridgeport Pool [Directions] | 4:00 p.m. | ||
| Wed., 1/11 | V Wrestling | Greenwich | Home - Staples HS-Staples Gym [Directions] | 7:00 p.m. | ||
| Wed., 1/11 | V Co-ed Alpine Skiing | Race night # 1 | Home - Mt. Southingon Ski Area [Directions] | 4:00 p.m. | ||
| Wed., 1/11 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Terry Conners - Stamford-Ice Rink [Directions] | 8:00 p.m. | W 3-1 | |
| Thu., 1/12 | FR Girls Basketball | Darien | Home - Staples HS-Staples Gym [Directions] | 6:00 p.m. | ||
| Thu., 1/12 | V Girls Gymnastics | St. Joseph, Trumbull | Home - Staples HS-Westport YMCA [Directions] | 7:00 p.m. | 127.85 | |
| Fri., 1/13 | V Boys Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 7:00 p.m. | W 56-38 | |
| Fri., 1/13 | JV Boys Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/13 | FR Boys Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/13 | V Boys Swimming and Diving | Greenwich | Home - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Fri., 1/13 | V Girls Basketball | Greenwich | Home - Staples HS-Staples Gym [Directions] | 7:00 p.m. | L 48-17 | |
| Fri., 1/13 | JV Girls Basketball | Greenwich | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/13 | FR Girls Basketball | Greenwich | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/13 | V Girls Ice Hockey | Greenwich | Away - Greenwich - Dorothy Hamill-Rink [Directions] | 5:15 p.m. | L 3-1 | |
| Sat., 1/14 | V Boys Ice Hockey | Brien McMahon/Norwalk | Away - Sono Ice House-Main Rink [Directions] | 6:40 p.m. | W 3-1 | |
| Sat., 1/14 | V Boys Indoor Track | Darien, St. Joseph, Stamford | Home - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/14 | V Boys Indoor Track | Bridgeport Central, Danbury, Fairfield Ludlowe, Greenwich | Home - Staples HS-Field House [Directions] | 1:30 p.m. | ||
| Sat., 1/14 | V Wrestling | John Chacho Dual Meet | Home - Staples HS-Staples Gym [Directions] | 8:45 a.m. | ||
| Sat., 1/14 | JV Wrestling | Trumbull, Bristol Eastern, Fairfield Warde, Greenwich, TBA, Norwalk, Simsbury, Southington, Xavier | Away - Trumbull HS-THS Main Gym | 9:00 a.m. | ||
| Sat., 1/14 | V Girls Indoor Track | Darien, St. Joseph, Stamford | Home - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/14 | V Girls Indoor Track | Danbury, Fairfield Ludlowe, Greenwich | Home - Staples HS-Field House [Directions] | 1:30 p.m. | ||
| Mon., 1/16 | V Boys Ice Hockey | Fox Lane (NY) | Home - Milford Ice Pavillion-Ice Rink [Directions] | 2:45 p.m. | W 8-2 | |
| Tue., 1/17 | V Boys Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 7:00 p.m. | L 54-63 | |
| Tue., 1/17 | JV Boys Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/17 | FR Boys Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/17 | V Girls Basketball | Danbury | Home - Staples HS-Staples Gym [Directions] | 7:00 p.m. | L 45-53 | |
| Tue., 1/17 | JV Girls Basketball | Danbury | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/17 | FR Girls Basketball | Danbury | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/18 | V Boys Ice Hockey | Newington Coop | Away - Newington-Blue Rink [Directions] | 4:00 p.m. | L 1-4 | |
| Wed., 1/18 | V Wrestling | Fairfield Warde | Away - Fairfield Warde HS-Small Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/18 | V Girls Ice Hockey | Darien | Away - Darien Ice House-Ice Rink [Directions] | 4:00 p.m. | L 3-2 | |
| Thu., 1/19 | V Girls Gymnastics | Norwalk, Stamford, Westhill | Home - Staples HS-Westport YMCA [Directions] | 7:00 p.m. | 130.75 | |
| Fri., 1/20 | V Boys Basketball | Stamford | Home - Staples HS-Staples Gym [Directions] | 7:00 p.m. | L 60-63 | |
| Fri., 1/20 | JV Boys Basketball | Stamford | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/20 | FR Boys Basketball | Stamford | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/20 | V Girls Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 7:00 p.m. | L 36-40 | |
| Fri., 1/20 | JV Girls Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/20 | FR Girls Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/20 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 4:00 p.m. | T 2-2 | |
| Sat., 1/21 | V Boys Ice Hockey | Masuk | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 8:45 p.m. | L 2-6 | |
| Sat., 1/21 | V Boys Indoor Track | Darien, Norwalk, Stamford | Home - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/21 | V Boys Indoor Track | Fairfield Warde, Ridgefield, Trumbull, Westhill | Home - Staples HS-Field House [Directions] | 1:30 p.m. | ||
| Sat., 1/21 | V Girls Gymnastics | Darien, Norwalk | Away - Darien YMCA [Directions] | 2:30 p.m. | 130.25 | |
| Sat., 1/21 | V Girls Indoor Track | Darien, Norwalk, Stamford | Home - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/21 | V Girls Indoor Track | Fairfield Warde, Ridgefield, Trumbull, Westhill | Home - Staples HS-Field House [Directions] | 1:30 a.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 1:30 p.m. | ||||||
| Sat., 1/21 | JV Girls Squash | Girls JV Squash vs Capitol Squash | Home - Intensity Fitness [Directions] | 1:30 p.m. | ||
| Mon., 1/23 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Home - Terry Conners - Stamford-Ice Rink [Directions] | 5:10 p.m. | W 3-2 | |
| Tue., 1/24 | V Boys Basketball | Westhill | Home - Staples HS-Staples Gym [Directions] | 7:00 p.m. | W 60-41 | |
| Tue., 1/24 | JV Boys Basketball | Westhill | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/24 | FR Boys Basketball | Westhill | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/24 | V Girls Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 6:00 p.m. | W 56 - 32 | |
| Tue., 1/24 | JV Girls Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:30 p.m. | ||
| Tue., 1/24 | JV Girls Squash | Rye (NY) | Home - Intensity Fitness [Directions] | 7:30 a.m. | ||
| Wed., 1/25 | V Boys Ice Hockey | Wilton | Home - Milford Ice Pavillion-Ice Rink [Directions] | 6:00 p.m. | L 2-3 | |
| Wed., 1/25 | V Wrestling | Trumbull | Away - Trumbull HS-Aux Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/25 | V Co-ed Alpine Skiing | race night # 2 | Home - Mt. Southingon Ski Area [Directions] | Postponed | ||
| Wed., 1/25 | V Girls Gymnastics | Fairfield Ludlowe, Norwalk | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:30 p.m. | 132.95 | |
| Wed., 1/25 | V Girls Gymnastics | Fairfield Warde, Norwalk | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:30 p.m. | ||
| Wed., 1/25 | V Girls Ice Hockey | Greenwich | Home - Terry Conners - Stamford-Ice Rink [Directions] | 5:30 p.m. | W 2-1 | |
| Thu., 1/26 | V Boys Basketball | Wright Tech | Away - J M Wright Tech School-Thomas R. Good Gymnasium [Directions] | 7:00 p.m. | W 72-31 | |
| Thu., 1/26 | JV Boys Basketball | Wright Tech | Away - J M Wright Tech School-Thomas R. Good Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 1/26 | V Girls Basketball | Harding | Home - Staples HS-Staples Gym [Directions] | 7:00 p.m. | W 62-18 | |
| Thu., 1/26 | JV Girls Basketball | Harding | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Thu., 1/26 | FR Girls Basketball | Harding | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/27 | V Boys Basketball | Fairfield Ludlowe | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | W 60-34 | |
| Fri., 1/27 | JV Boys Basketball | Fairfield Ludlowe | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/27 | FR Boys Basketball | Fairfield Ludlowe | Home - Staples HS-Staples Gym [Directions] | 7:00 p.m. | ||
| Fri., 1/27 | JV Boys Squash | Boys Junior Varsity and JV Squash vs New Canaan | Away - Chelsea Piers - -Gym | 7:30 p.m. | ||
| Fri., 1/27 | V Boys Swimming and Diving | Ridgefield | Home - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Fri., 1/27 | V Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:30 p.m. | L 16 - 52 | |
| Fri., 1/27 | JV Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 1/28 | V Wrestling | TFC Kevin Miller Tourney | Away - East Hartford HS | 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 Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | 8:40 p.m. | L 6-0 | |
| Mon., 1/30 | V Boys Ice Hockey | Brien McMahon/Norwalk | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:45 p.m. | L 0-3 | |
| Mon., 1/30 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Away - Norwalk HS-Pat Spinola Natatorium [Directions] | 4:00 p.m. | ||
| Mon., 1/30 | V Girls Squash | Rye (NY) | Away - Chelsea Piers - -Gym | 7:30 p.m. | ||
| Tue., 1/31 | V Boys Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 7:00 p.m. | L 68-69 | |
| Tue., 1/31 | JV Boys Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:15 p.m. | ||
| Tue., 1/31 | FR Boys Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Tue., 1/31 | V Boys Diving | Darien | Away - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Tue., 1/31 | V Boys Squash | Boys Squash Varsity vs Greenwich | Home - Intensity Fitness [Directions] | 7:30 p.m. | ||
| Tue., 1/31 | JV Wrestling | Fairfield Warde, Fairfield Ludlowe | Away - Fairfield Warde HS-Small Gym [Directions] | 5:00 p.m. | ||
| Tue., 1/31 | V Girls Basketball | Wilton | Home - Staples HS-Staples Gym [Directions] | 6:00 p.m. | W 56 - 20 | |
| Tue., 1/31 | JV Girls Basketball | Wilton | Home - Staples HS-Staples Gym [Directions] | 4:30 p.m. | ||
| Wed., 2/1 | JV Boys Squash | Darien | Away - Chelsea Piers - -Gym [Directions] | 7:30 p.m. | ||
| Wed., 2/1 | V Boys Swimming and Diving | Darien | Away - Darien YMCA [Directions] | 3:30 p.m. | ||
| Wed., 2/1 | V Wrestling | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 6:30 p.m. | ||
| Wed., 2/1 | V Co-ed Alpine Skiing | Race night #3 | Home - Mt. Southingon Ski Area [Directions] | 4:00 p.m. | ||
| Wed., 2/1 | V Co-ed Fencing | Fairfield Warde | Away - Holy Family Church [Directions] | 7:00 p.m. | ||
| Wed., 2/1 | V Girls Ice Hockey | Masuk Coop | Home - Terry Conners - Stamford-Ice Rink [Directions] | 8:00 p.m. | W 3-0 | |
| Thu., 2/2 | JV Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 6:00 p.m. | ||
| Thu., 2/2 | FR Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:30 p.m. | ||
| Thu., 2/2 | V Boys Indoor Track | FCIAC CHAMPIONSHIPS - BOYS INDOOR TRACK AND FIELD | Away - Floyd Little Athletic Center | 5:00 p.m. | ||
| Thu., 2/2 | V Girls Basketball | Brien McMahon | Home - Staples HS-Staples Gym [Directions] | 7:00 p.m. | W 61 - 40 | |
| Thu., 2/2 | JV Girls Basketball | Brien McMahon | Home - Staples HS-Staples Gym [Directions] | 5:15 p.m. | ||
| Thu., 2/2 | V Girls Gymnastics | Norwalk, Wilton | Home - Staples HS-Westport YMCA [Directions] | 7:00 p.m. | 138.25 | |
| Fri., 2/3 | V Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:00 p.m. | L 51-62 | |
| Fri., 2/3 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Home - Staples HS-Staples High School Pool [Directions] | 3:30 p.m. | ||
| Fri., 2/3 | FR Girls Basketball | Darien | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Sat., 2/4 | V Boys Ice Hockey | Westhill/Stamford | Home - Milford Ice Pavillion-Ice Rink [Directions] | 8:00 p.m. | L 0-7 | |
| Sat., 2/4 | FR Girls Basketball | Fairfield Ludlowe | Home - Staples HS-Staples Gym [Directions] | 9:00 a.m. | ||
| Sat., 2/4 | V Girls Ice Hockey | Daniel Hand Coop | Home - Terry Conners - Stamford-Ice Rink [Directions] | 8:00 p.m. | L 4-3 | |
| Tue., 2/7 | V Boys Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 7:00 p.m. | W 50-45 | |
| Tue., 2/7 | JV Boys Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/7 | FR Boys Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/7 | V Girls Basketball | Trumbull | Home - Staples HS-Staples Gym [Directions] | 7:00 p.m. | L 38-58 | |
| Tue., 2/7 | JV Girls Basketball | Trumbull | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/7 | FR Girls Basketball | Trumbull | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/8 | V Boys Ice Hockey | Westhill/Stamford | Away - Terry Conners - Stamford-Ice Rink [Directions] | 7:30 p.m. | L 2-5 | |
| Wed., 2/8 | V Wrestling | Brien McMahon | Home - Staples HS-Staples Gym [Directions] | 7:00 p.m. | ||
| Wed., 2/8 | V Co-ed Fencing | Fairfield Warde | Away - Holy Family Church [Directions] | 7:00 p.m. | ||
| Wed., 2/8 | V Girls Ice Hockey | Darien | Home - Terry Conners - Stamford-Ice Rink [Directions] | 5:30 p.m. | L 1-0 | |
| Thu., 2/9 | V Girls Gymnastics | Greenwich, New Canaan, Norwalk | Home - Staples HS-Westport YMCA [Directions] | 7:00 p.m. | 133.65 | |
| Fri., 2/10 | V Boys Basketball | Bridgeport Central | Home - Staples HS-Staples Gym [Directions] | 7:00 p.m. | W 67-51 | |
| Fri., 2/10 | JV Boys Basketball | Bridgeport Central | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/10 | FR Boys Basketball | Bridgeport Central | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Fri., 2/10 | V Wrestling | New Canaan, Bridgeport Central, Brien McMahon, Danbury, Darien, FCIAC, Fairfield Ludlowe, Fairfield Warde, Greenwich, Norwalk, Ridgefield, St. Joseph, Stamford, Trumbull, Westhill, Wilton | Away - New Canaan HS-Main Gym | 4:00 p.m. | ||
| Fri., 2/10 | V Girls Basketball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | 7:00 p.m. | W 57-35 | |
| Fri., 2/10 | JV Girls Basketball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | 5:30 p.m. | ||
| Fri., 2/10 | FR Girls Basketball | Bridgeport Central | Away - Bridgeport Central HS-The Barry McLeod Court [Directions] | 4:00 p.m. | ||
| Sat., 2/11 | V Boys Ice Hockey | Trumbull | Home - Milford Ice Pavillion-Ice Rink [Directions] | 6:00 p.m. | L 3-4 | |
| Sat., 2/11 | V Boys Rugby | College Showcase | Home - Staples HS-Staples Stadium [Directions] | 12:00 p.m. | ||
| Sat., 2/11 | V Girls Ice Hockey | Simsbury | Home - Terry Conners - Stamford-Ice Rink [Directions] | 5:00 p.m. | L 2-1 | |
| Mon., 2/13 | V Boys Basketball | Fairfield Warde | Home - Staples HS-Staples Gym [Directions] | 7:00 p.m. | L 44-51 | |
| Mon., 2/13 | JV Boys Basketball | Fairfield Warde | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/13 | FR Boys Basketball | Fairfield Warde | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Mon., 2/13 | V Boys Swimming and Diving | Wilton | Home - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Mon., 2/13 | V Girls Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 7:00 p.m. | L 18-44 | |
| Mon., 2/13 | JV Girls Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/13 | FR Girls Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/14 | V Boys Squash | Darien | Away - Chelsea Piers - -Gym [Directions] | 7:30 p.m. | ||
| Tue., 2/14 | FR Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 3:30 p.m. | ||
| Wed., 2/15 | V Boys Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 7:00 p.m. | W 69-58 | |
| Wed., 2/15 | JV Boys Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 2/15 | FR Boys Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 2/15 | V Boys Swimming and Diving | New Canaan | Away - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Wed., 2/15 | V Girls Basketball | Norwalk | Home - Staples HS-Staples Gym [Directions] | 6:00 p.m. | W 47-33 | |
| Wed., 2/15 | JV Girls Basketball | Norwalk | Home - Staples HS-Staples Gym [Directions] | 4:15 p.m. | ||
| Wed., 2/15 | JV Girls Squash | Darien | Home - Intensity Fitness [Directions] | 7:30 p.m. | ||
| Thu., 2/16 | V Girls Gymnastics | Darien, Norwalk | Home - Staples HS-Westport YMCA [Directions] | 7:00 p.m. | 131.7 | |
| Fri., 2/17 | V Boys Ice Hockey | Wilton | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 4:00 p.m. | W 5-0 | |
| Fri., 2/17 | V Girls Ice Hockey | East Catholic Coop | Away - Newington-Blue Rink [Directions] | 8:30 p.m. | L 3-0 | |
| Sat., 2/18 | V Girls Ice Hockey | Mercy/NW Catholic/East Hampton | Home - Terry Conners - Stamford-Ice Rink [Directions] | 8:00 p.m. | L 1-0 | |
| Mon., 2/20 | V Boys Basketball | St. Joseph | Home - Staples HS-Staples Gym [Directions] | 7:00 p.m. | W 72-35 | |
| Mon., 2/20 | JV Boys Basketball | St. Joseph | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/20 | FR Boys Basketball | St. Joseph | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Mon., 2/20 | V Boys Ice Hockey | SCW Knights | Away - Cromwell-Upper Rink [Directions] | 5:00 p.m. | L 2-4 | |
| Wed., 2/22 | V Boys Basketball | Darien | Home - Staples HS-Staples Gym [Directions] | 7:00 p.m. | W 55-39 | |
| Wed., 2/22 | JV Boys Basketball | Darien | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/22 | FR Boys Basketball | Darien | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/22 | V Boys Ice Hockey | JBWA | Home - Milford Ice Pavillion-Ice Rink [Directions] | 6:00 p.m. | L 3-4 (OT) | |
| Fri., 2/24 | V Boys Ice Hockey | Milford Coop | Away - Milford Ice Pavillion-Ice Rink [Directions] | 8:15 p.m. | W 7-3 | |
| Tue., 2/28 | V Boys Swimming and Diving | FCIAC Swim Trial Boys | Away - Greenwich HS-Pool | 5:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 3/1 | ||||||
| Fri., 3/3 | V Boys Swimming and Diving | Greenwich, Danbury, Darien, Farfield Ludlowe/Warde, Fairfield Warde, TBA, New Canaan, Norwalk/Brien McMahon, Ridgefield, St. Joseph, Trumbull, Westhill/Stamford, Wilton | Away - Greenwich HS-Pool | 6:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 5:30 p.m. | ||||||
| Sat., 3/11 | V Boys Rugby | Staples Rugby, Boys Varsity vs Georgetown Prep | Home - Staples HS-Staples Stadium [Directions] | 1:00 p.m. | ||
| Thu., 3/16 | V Boys Rugby | Staples Rugby, Boys Varsity vs Woodlands Rugby Club | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Sat., 3/25 | V Boys Rugby | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 2:00 p.m. | ||
| Sat., 3/25 | JV Boys Rugby | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 3:30 p.m. | ||
| Sat., 3/25 | FM Boys Rugby | Greenwich | Away - Greenwich HS-Field 7 [Directions] | 12:00 p.m. | ||
| Mon., 3/27 | V Girls Water Polo | Greenwich | Away - Greenwich HS-Pool [Directions] | 4:30 p.m. | ||
| Wed., 3/29 | V Co-ed Sailing | Regatta @ BS/GA/GHS | Away - Indian Harbor Yacht Club | 3:00 p.m. | ||
| Sat., 4/1 | V Boys Lacrosse | Iona Prep (NY) | Home - Staples HS-Staples Stadium [Directions] | 5:00 p.m. | W 10-5 | |
| Sat., 4/1 | JV Boys Lacrosse | Iona Prep (NY) | Away - Iona Preparatory School-Stadium | 5:00 p.m. | ||
| Sat., 4/1 | V Boys Rugby | Staples Ruby, Boys Varsity vs Aspetuck Rugby Football Club | Home - Staples HS-Staples Stadium [Directions] | 12:00 p.m. | ||
| Sat., 4/1 | JV Boys Rugby | Staples Rugby, Boys JV ( D2) vs Aspetuck Rugby Football Club | Home - Staples HS-Staples Stadium [Directions] | 2:00 p.m. | ||
| Sat., 4/1 | V Boys Volleyball | Boys Volleyball Jamboree at Connecticut Sports Center | Away - . | 7:30 a.m. | ||
| Sat., 4/1 | V Girls Water Polo | Choate Rosemary Hall | Away - Choate School | 1:00 p.m. | ||
| Mon., 4/3 | FR Boys Lacrosse | Notre Dame-West Haven | Away - Notre Dame HS-Veteran's Stadium [Directions] | 3:45 p.m. | ||
| Mon., 4/3 | V Boys Volleyball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | 6:00 p.m. | L 0-3 | |
| Mon., 4/3 | JV Boys Volleyball | Shelton | Away - Shelton HS-Murray Gymnasium [Directions] | 4:30 p.m. | ||
| Mon., 4/3 | JV Girls Lacrosse | Greenwich Academy | Away - Greenwich Academy-2nd Field | 4:30 p.m. | ||
| Mon., 4/3 | FR Girls Lacrosse | Greenwich Academy | Away - Greenwich Academy-2nd Field | 4:00 p.m. | ||
| Mon., 4/3 | V Softball | North Haven | Away - North Haven Athletic Complex-Varsity Softball Field [Directions] | 3:45 p.m. | L 11-6 | |
| Tue., 4/4 | V Baseball | Greenwich | Away - Greenwich HS-Baseball Field [Directions] | 4:30 p.m. | W 8-0 | |
| Tue., 4/4 | JV Baseball | Greenwich | Away - Julian Curtiss School [Directions] | 4:30 p.m. | ||
| Tue., 4/4 | FR Baseball | Darien | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Tue., 4/4 | JV Boys Lacrosse | Massapequa (NY) | Away - Massapequa HS | 5:00 p.m. | ||
| Tue., 4/4 | FR Boys Lacrosse | Wilton | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:30 p.m. | ||
| Tue., 4/4 | V Boys Outdoor Track | Danbury | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/4 | V Boys Tennis | Avon | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | L 2-5 [Detailed Results] | |
| Tue., 4/4 | V Boys Volleyball | Joel Barlow | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | L 1-3 | |
| Tue., 4/4 | JV Boys Volleyball | Joel Barlow | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Tue., 4/4 | V Co-ed Sailing | Regatta @ GHS/GCDS | Away - Pettipaug Yacht Club | 4:00 p.m. | ||
| Tue., 4/4 | V Girls Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 4/4 | V Girls Outdoor Track | Danbury | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Wed., 4/5 | V Baseball | Fairfield Prep | Away - Fairfield University-Alumni Diamond [Directions] | 4:00 p.m. | L 8-7 | |
| Wed., 4/5 | V Co-ed Sailing | Regetta @ Inidan Harbor Yacht club | Away - Indian Harbor Yacht Club | 3:00 p.m. | ||
| Wed., 4/5 | JV Girls Lacrosse | St. Joseph | Home - Staples HS-Ginny Parker Field [Directions] | 5:00 p.m. | ||
| Wed., 4/5 | FR Girls Lacrosse | Wilton | Away - Allen's Meadow-Lacrosse Field #5 [Directions] | 4:00 p.m. | ||
| Wed., 4/5 | V Girls Water Polo | Sacred Heart of Greenwich | Home - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Thu., 4/6 | V Baseball | Bridgeport Central | Home - Staples HS-Baseball Diamond [Directions] | 4:30 p.m. | W 10-0 | |
| Thu., 4/6 | FR Baseball | Fairfield Ludlowe | Home - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | ||
| Thu., 4/6 | FR Boys Lacrosse | Fairfield Ludlowe | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Thu., 4/6 | V Boys Volleyball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 6:00 p.m. | L 3-2 | |
| Thu., 4/6 | JV Boys Volleyball | Masuk | Away - Masuk HS-David Strong Gymnasium @ Masuk HS [Directions] | 4:30 p.m. | ||
| Thu., 4/6 | V Girls Lacrosse | East Lyme | Away - East Lyme HS-Dick North Turf Field [Directions] | 5:00 p.m. | L 9-6 | |
| Thu., 4/6 | JV Girls Lacrosse | East Lyme | Away - East Lyme HS-Dick North Turf Field [Directions] | 3:45 p.m. | ||
| Thu., 4/6 | FR Girls Lacrosse | Westhill | Away - Westhill HS-Westhill Front Turf Field [Directions] | Canceled | Cancelled | |
| Thu., 4/6 | V Softball | East Hartford | Away - McAuliffe Park-Varsity Field [Directions] | 4:00 p.m. | W 13-2 | |
| Sat., 4/8 | V Boys Lacrosse | Rye (NY) | Away - Rye HS-Turf | 3:30 p.m. | W 10-6 | |
| Sat., 4/8 | JV Boys Lacrosse | Rye (NY) | Away - Rye HS-Turf | 1:00 p.m. | ||
| Mon., 4/10 | V Baseball | Fairfield Warde | Home - Staples HS-Baseball Diamond [Directions] | 4:00 p.m. | W 5-4 | |
| Mon., 4/10 | JV Baseball | Fairfield Warde | Home - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | ||
| Mon., 4/10 | FR Baseball | Fairfield Warde | Away - Fairfield Warde HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Mon., 4/10 | FR Boys Lacrosse | Stamford | Away - Stamford HS-Upper Lacrosse Field [Directions] | 5:00 p.m. | ||
| Mon., 4/10 | V Boys Tennis | Ridgefield | Away - Ridgefield HS-RHS Tennis Courts [Directions] | 12:00 p.m. | W 5-2 [Detailed Results] | |
| Mon., 4/10 | V Softball | Stamford | Away - Stamford HS-SHS Softball Diamond [Directions] | 4:00 p.m. | L 7-3 | |
| Mon., 4/10 | V Girls Tennis | Ridgefield | Home - Staples HS-Staples Tennis Courts [Directions] | 12:00 p.m. | W 7-0 [Detailed Results] | |
| Mon., 4/10 | JV Girls Tennis | Ridgefield | Home - Staples HS-Town Farms Tennis Courts [Directions] | 12:00 p.m. | ||
| Tue., 4/11 | V Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | W 16-3 | |
| Tue., 4/11 | JV Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 5:30 p.m. | ||
| Tue., 4/11 | FR Boys Lacrosse | Chaminade (NY) | Away - Chaminade-OTT FIELD | 11:00 a.m. | ||
| Tue., 4/11 | V Boys Tennis | New Canaan | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | W 4-3 [Detailed Results] | |
| Tue., 4/11 | JV Boys Tennis | New Canaan | Home - Staples HS-Town Farms Tennis Courts [Directions] | Postponed | ||
| Tue., 4/11 | V Girls Lacrosse | Fairfield Warde | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | W 19-5 | |
| Tue., 4/11 | JV Girls Lacrosse | Fairfield Warde | Home - Staples HS-Ginny Parker Field [Directions] | 5:30 p.m. | ||
| Tue., 4/11 | V Girls Tennis | New Canaan | Away - New Canaan HS-NCHS Tennis Courts [Directions] | 12:00 p.m. | L 7-0 [Detailed Results] | |
| Wed., 4/12 | JV Boys Lacrosse | St. Anthonys (NY) | Home - Staples HS-Staples Stadium [Directions] | 12:00 p.m. | ||
| Wed., 4/12 | FR Boys Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 12:00 p.m. | ||
| Wed., 4/12 | V Softball | Norwalk | Home - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | L 10-9 | |
| Wed., 4/12 | JV Softball | Norwalk | Home - Staples HS-Staples Softball Field [Directions] | Postponed | ||
| Thu., 4/13 | V Boys Lacrosse | Massapequa (NY) | Home - Staples HS-Staples Stadium [Directions] | 5:00 p.m. | W 17-5 | |
| Thu., 4/13 | JV Boys Lacrosse | Cheshire | Away - Cheshire HS-Grass Fields [Directions] | 1:00 p.m. | ||
| Thu., 4/13 | V Boys Tennis | Greenwich | Away - Greenwich HS-Tennis Courts [Directions] | 4:30 p.m. | L 0-7 [Detailed Results] | |
| Thu., 4/13 | JV Boys Tennis | Greenwich | Away - Central MS [Directions] | Postponed | ||
| Thu., 4/13 | V Girls Lacrosse | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 10:00 a.m. | L 17-3 | |
| Thu., 4/13 | JV Girls Lacrosse | Darien | Away - Darien HS-DHS Center Oval - Turf [Directions] | 11:30 a.m. | ||
| Thu., 4/13 | V Girls Tennis | Greenwich | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | L 6-1 [Detailed Results] | |
| Fri., 4/14 | V Baseball | Ridgefield | Home - Staples HS-Baseball Diamond [Directions] | 4:00 p.m. | W 9-1 | |
| Fri., 4/14 | JV Baseball | Ridgefield | Home - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | ||
| Fri., 4/14 | FR Baseball | Ridgefield | Away - Governor Field [Directions] | 4:00 p.m. | ||
| Fri., 4/14 | FR Boys Lacrosse | Trumbull | Home - Staples HS-Staples Stadium [Directions] | 3:00 p.m. | ||
| Fri., 4/14 | V Boys Volleyball | Danbury | Home - Staples HS-Staples Gym [Directions] | 12:00 p.m. | W 3-0 | |
| Fri., 4/14 | JV Boys Volleyball | Danbury | Home - Staples HS-Staples Gym [Directions] | 1:30 p.m. | ||
| Fri., 4/14 | V Softball | Ridgefield | Away - Ridgefield HS-Varsity Softball Field [Directions] | 4:00 p.m. | L 5-0 | |
| Fri., 4/14 | JV Softball | Ridgefield | Away - Ridgefield HS-JV Softball Field [Directions] | Postponed | ||
| Sat., 4/15 | V Boys Lacrosse | Darien | Home - Staples HS-Staples Stadium [Directions] | 5:00 p.m. | W 13-11 | |
| Sat., 4/15 | JV Boys Lacrosse | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 2:00 p.m. | ||
| Sat., 4/15 | FR Boys Lacrosse | Bergen Catholic (NJ) | Home - Staples HS-Wakeman Field B (turf) [Directions] | 11:00 a.m. | ||
| Sat., 4/15 | V Boys Rugby | Staples Ruby, Boys Varsity vs St. Andrew's College from South Africa | Home - Staples HS-Staples Stadium [Directions] | 12:00 p.m. | ||
| Sat., 4/15 | JV Boys Rugby | Staples Ruby, Boys JV ( D2) vs St. Andrew's College from South Africa | Home - Staples HS-Staples Stadium [Directions] | 2:00 p.m. | ||
| Sat., 4/15 | V Girls Lacrosse | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 12:45 p.m. | W 6-4 | |
| Sat., 4/15 | JV Girls Lacrosse | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 11:00 a.m. | ||
| Mon., 4/17 | V Baseball | New Canaan | Away - Mead Park-Baseball Field [Directions] | 4:00 p.m. | W 1-0 | |
| Mon., 4/17 | JV Baseball | New Canaan | Away - Waveny Park-Coppo Field [Directions] | 4:00 p.m. | ||
| Mon., 4/17 | FR Baseball | New Canaan | Home - Staples HS-Baseball Diamond [Directions] | 4:30 p.m. | ||
| Mon., 4/17 | JV Boys Lacrosse | St. Joseph | Home - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Mon., 4/17 | FR Boys Lacrosse | Greenwich | Home - Staples HS-Wakeman Field B (turf) [Directions] | 5:00 p.m. | ||
| Mon., 4/17 | V Boys Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:00 p.m. | L 0-3 | |
| Mon., 4/17 | JV Boys Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 4/17 | V Softball | New Canaan | Home - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | L 10-9 | |
| Tue., 4/18 | V Boys Lacrosse | Bergen Catholic (NJ) | Away - Bergen Catholic HS-Stadium2 | 4:30 p.m. | W 10-8 | |
| Tue., 4/18 | V Boys Outdoor Track | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/18 | V Boys Tennis | Westhill | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | L 3-4 [Detailed Results] | |
| Tue., 4/18 | JV Boys Tennis | Darien | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/18 | V Girls Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 4:45 p.m. | L 14-11 | |
| Tue., 4/18 | JV Girls Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 6:00 p.m. | ||
| Tue., 4/18 | FR Girls Lacrosse | Wilton | Home - Staples HS-Ginny Parker Field [Directions] | Postponed | ||
| Tue., 4/18 | V Girls Outdoor Track | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/18 | JV Softball | New Canaan | Home - Staples HS-Staples Softball Field [Directions] | Canceled | Cancelled | |
| Tue., 4/18 | V Girls Tennis | Westhill | Away - Westhill HS-Westhill Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Tue., 4/18 | JV Girls Tennis | Darien | Away - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/19 | V Baseball | Greenwich | Home - Staples HS-Baseball Diamond [Directions] | 4:30 p.m. | W 4-2 | |
| Wed., 4/19 | JV Baseball | Greenwich | Home - Staples HS-Wakeman Field [Directions] | 4:30 p.m. | ||
| Wed., 4/19 | FR Baseball | Greenwich | Away - Greenwich HS-Baseball Field [Directions] | 4:30 p.m. | ||
| Wed., 4/19 | FR Boys Lacrosse | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 4/19 | V Boys Rugby | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 6:30 p.m. | ||
| Wed., 4/19 | JV Boys Rugby | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | Canceled | Cancelled | |
| Wed., 4/19 | V Boys Tennis | Danbury | Away - Danbury HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Wed., 4/19 | JV Boys Tennis | New Canaan | Away - New Canaan HS-NCHS Tennis Courts [Directions] | 5:30 p.m. | ||
| Wed., 4/19 | V Boys Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:30 p.m. | L 3-1 | |
| Wed., 4/19 | JV Boys Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 6:00 p.m. | ||
| Wed., 4/19 | V Girls Golf | St. Joseph | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 4/19 | JV Girls Golf | St. Joseph | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 4/19 | FR Girls Lacrosse | Darien | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Wed., 4/19 | V Softball | Greenwich | Away - Greenwich HS-Softball Field [Directions] | 4:30 p.m. | W 12-4 | |
| Wed., 4/19 | JV Softball | Greenwich | Away - Julian Curtiss School [Directions] | Postponed | ||
| Wed., 4/19 | V Girls Tennis | Danbury | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Wed., 4/19 | JV Girls Tennis | Fairfield Warde | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 4/20 | V Boys Lacrosse | Wilton | Away - Wilton HS-Veterans Memorial Stadium [Directions] | 7:00 p.m. | L 6-4 | |
| Thu., 4/20 | JV Boys Lacrosse | Wilton | Away - Wilton HS-Fuijitani Field -Turf [Directions] | 4:30 p.m. | ||
| Thu., 4/20 | V Boys Tennis | Wilton | Away - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | L 2-5 [Detailed Results] | |
| Thu., 4/20 | JV Boys Tennis | Wilton | Away - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 4/20 | V Girls Golf | Ridgefield | Away - Ridgefield Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 4/20 | JV Girls Golf | Ridgefield | Away - Ridgefield Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 4/20 | V Girls Lacrosse | Wilton | Away - Wilton HS-Lilly Field [Directions] | 6:00 p.m. | L 18-1 | |
| Thu., 4/20 | JV Girls Lacrosse | Wilton | Away - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | ||
| Thu., 4/20 | V Girls Rugby | Darien | Home - Staples HS-Staples Stadium [Directions] | 5:00 p.m. | ||
| Thu., 4/20 | V Girls Tennis | Wilton | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | W 5-2 [Detailed Results] | |
| Thu., 4/20 | JV Girls Tennis | Wilton | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 4/21 | V Baseball | Danbury | Home - Staples HS-Baseball Diamond [Directions] | 4:30 p.m. | W 10-0 | |
| Fri., 4/21 | JV Baseball | Danbury | Home - Staples HS-Wakeman Field [Directions] | 4:30 p.m. | ||
| Fri., 4/21 | FR Baseball | Danbury | Away - Danbury HS-V Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 4/21 | V Boys Volleyball | Westhill | Home - Staples HS-Staples Gym [Directions] | 4:15 p.m. | L 3-0 | |
| Fri., 4/21 | JV Boys Volleyball | Westhill | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Fri., 4/21 | V Softball | Danbury | Away - Danbury HS-V Softball field [Directions] | 4:00 p.m. | L 9-6 | |
| Sat., 4/22 | V Boys Lacrosse | Bishop Guertin (NH) | Away - Providence College - Chapey Field | 3:00 p.m. | W 11-10 | |
| Sat., 4/22 | JV Boys Lacrosse | Chaminade (NY) | Home - Staples HS-Wakeman Field B (turf) [Directions] | 10:00 a.m. | ||
| Sat., 4/22 | FR Boys Lacrosse | Chaminade (NY) | Home - Staples HS-Staples Stadium [Directions] | 12:30 p.m. | ||
| Sat., 4/22 | FM Boys Rugby | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 3:00 p.m. | ||
| Sat., 4/22 | V Girls Lacrosse | Branford | Away - Branford HS-Athletic Turf Field [Directions] | 1:30 p.m. | W 12-8 | |
| Sat., 4/22 | JV Softball | Danbury | Away - Danbury HS-V Softball field [Directions] | 11:00 a.m. | ||
| Mon., 4/24 | V Baseball | Westhill | Away - Westhill HS-Varsity Baseball Field [Directions] | 4:00 p.m. | L 5-4 | |
| Mon., 4/24 | JV Baseball | Westhill | Away - Rippowan MS-Rippowam Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/24 | FR Baseball | Westhill | Home - Staples HS-Baseball Diamond [Directions] | 4:30 p.m. | ||
| Mon., 4/24 | V Boys Lacrosse | Trumbull | Home - Staples HS-Staples Stadium [Directions] | 6:30 p.m. | W 19-2 | |
| Mon., 4/24 | FR Boys Lacrosse | Westhill | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:15 p.m. | ||
| Mon., 4/24 | V Boys Tennis | Darien | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | L 0-7 [Detailed Results] | |
| Mon., 4/24 | V Boys Volleyball | Bridgeport Central | Away - Bridgeport Central HS-The Barry McLeod Court [Directions] | 6:00 p.m. | W 3-2 | |
| Mon., 4/24 | JV Boys Volleyball | Bridgeport Central | Away - Bridgeport Central HS-The Barry McLeod Court [Directions] | 4:30 p.m. | ||
| Mon., 4/24 | V Girls Golf | New Canaan | Away - CCNC [Directions] | 3:30 p.m. | ||
| Mon., 4/24 | FR Girls Lacrosse | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | 4:30 p.m. | ||
| Mon., 4/24 | V Softball | Westhill | Home - Staples HS-Wakeman Field [Directions] | 4:15 p.m. | W 7-6 | |
| Mon., 4/24 | JV Softball | Westhill | Home - Staples HS-Staples Softball Field [Directions] | Canceled | Cancelled | |
| Mon., 4/24 | V Girls Tennis | Darien | Away - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 4-3 [Detailed Results] | |
| Mon., 4/24 | JV Girls Tennis | Darien | Away - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/25 | JV Boys Lacrosse | Trumbull | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Tue., 4/25 | V Boys Outdoor Track | Westhill | Home - Staples HS-Staples Stadium [Directions] | 4:15 p.m. | ||
| Tue., 4/25 | V Boys Tennis | Fairfield Warde | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | L 3-4 [Detailed Results] | |
| Tue., 4/25 | JV Boys Tennis | Fairfield Warde | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/25 | V Co-ed Sailing | COED SAILING - REGATTA @ HOTCHKISS | Away - The Hotchkiss Boat House | 4:00 p.m. | ||
| Tue., 4/25 | V Girls Golf | Darien | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 4/25 | JV Girls Golf | Fairfield Ludlowe | Away - Carl Dickman Par 3 [Directions] | 3:15 p.m. | ||
| Tue., 4/25 | V Girls Lacrosse | Trumbull | Away - Trumbull HS-Cork Field [Directions] | 6:00 p.m. | W 15-2 | |
| Tue., 4/25 | JV Girls Lacrosse | Trumbull | Away - Trumbull HS-Cork Field [Directions] | 4:00 p.m. | ||
| Tue., 4/25 | FR Girls Lacrosse | Fairfield Ludlowe | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Tue., 4/25 | V Girls Outdoor Track | Westhill | Home - Staples HS-Staples Stadium [Directions] | 4:15 p.m. | ||
| Tue., 4/25 | JV Softball | Wilton | Away - Wilton HS-JV Softball Field [Directions] | 4:00 p.m. | ||
| Tue., 4/25 | V Girls Tennis | Fairfield Warde | Away - Fairfield Warde HS-Blake Courts [Directions] | 4:00 p.m. | W 4-3 [Detailed Results] | |
| Tue., 4/25 | JV Girls Tennis | Fairfield Warde | Away - Fairfield Warde HS-Knapps Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/26 | V Baseball | Wilton | Home - Staples HS-Baseball Diamond [Directions] | 4:30 p.m. | W 2-0 | |
| Wed., 4/26 | JV Baseball | Wilton | Home - Staples HS-Wakeman Field [Directions] | 4:30 p.m. | ||
| Wed., 4/26 | FR Baseball | Wilton | Away - Allen's Meadow-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 4/26 | V Boys Lacrosse | St. Anthonys (NY) | Home - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | L 16-4 | |
| Wed., 4/26 | FR Boys Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | 4:00 p.m. | ||
| Wed., 4/26 | V Boys Volleyball | Norwalk | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | L 3-2 | |
| Wed., 4/26 | JV Boys Volleyball | Brien McMahon | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Wed., 4/26 | V Co-ed Sailing | CO-ED SAILING REGATTA @ GREENWICH | Away - Indian Harbor Yacht Club | 5:00 a.m. | ||
| Wed., 4/26 | FR Girls Lacrosse | Trumbull | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Wed., 4/26 | V Softball | Wilton | Away - Wilton HS-Varsity Softball Field [Directions] | 4:00 p.m. | W 3-2 | |
| Wed., 4/26 | JV Girls Tennis | Greenwich | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/26 | V Girls Water Polo | Girls Varsity Water Polo vs Hamden Country Day School | Away - . | 4:00 p.m. | ||
| Thu., 4/27 | V Girls Rugby | Darien, Fairfield Ludlowe | Home - Staples HS-Staples Stadium [Directions] | 5:00 p.m. | ||
| Fri., 4/28 | V Baseball | Darien | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | W 2-1 | |
| Fri., 4/28 | JV Baseball | Darien | Away - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | ||
| Fri., 4/28 | FR Baseball | Darien | Home - Staples HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Fri., 4/28 | FR Boys Lacrosse | New Canaan | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:15 p.m. | ||
| Fri., 4/28 | V Boys Tennis | Trumbull | Away - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | W 5-2 [Detailed Results] | |
| Fri., 4/28 | JV Boys Tennis | Trumbull | Away - Tashua Knolls Golf Course-Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 4/28 | V Boys Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:30 p.m. | L 3-0 | |
| Fri., 4/28 | JV Boys Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 4/28 | V Softball | Darien | Home - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | L 8-2 | |
| Fri., 4/28 | V Girls Tennis | Trumbull | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Fri., 4/28 | JV Girls Tennis | Fairfield Ludlowe | Away - Tomlinson MS-Tennis Courts [Directions] | Postponed | ||
| Fri., 4/28 | JV Girls Tennis | Trumbull | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Sat., 4/29 | V Boys Lacrosse | Greenwich | Home - Staples HS-Staples Stadium [Directions] | 1:00 p.m. | W 15-3 | |
| Sat., 4/29 | JV Boys Lacrosse | Greenwich | Home - Staples HS-Wakeman Field B (turf) [Directions] | 11:00 a.m. | ||
| Sat., 4/29 | V Girls Lacrosse | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 10:00 a.m. | L 13-8 | |
| Sat., 4/29 | JV Girls Lacrosse | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 11:30 a.m. | ||
| Mon., 5/1 | V Baseball | Fairfield Warde | Away - Fairfield Warde HS-Baseball Diamond [Directions] | 4:00 p.m. | L 7-0 | |
| Mon., 5/1 | FR Baseball | Fairfield Warde | Home - Staples HS-Baseball Diamond [Directions] | Postponed | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 4:00 p.m. | ||||||
| Mon., 5/1 | V Boys Tennis | Stamford | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | W 5-2 [Detailed Results] | |
| Mon., 5/1 | JV Boys Tennis | Ridgefield | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 5/1 | V Boys Volleyball | Fairfield Ludlowe | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | L 3-1 | |
| Mon., 5/1 | JV Boys Volleyball | Fairfield Ludlowe | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Mon., 5/1 | FR Girls Lacrosse | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Mon., 5/1 | V Softball | Fairfield Warde | Home - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | L 10-7 | |
| Mon., 5/1 | JV Softball | Fairfield Warde | Home - Staples HS-Staples Softball Field [Directions] | Postponed | ||
| Mon., 5/1 | V Girls Tennis | Stamford | Away - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Mon., 5/1 | JV Girls Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/2 | JV Boys Lacrosse | Bergen Catholic (NJ) | Home - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Tue., 5/2 | V Boys Outdoor Track | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 4:00 p.m. | ||
| Tue., 5/2 | V Girls Golf | Fairfield Warde | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 5/2 | V Girls Lacrosse | Fairfield Ludlowe | Home - Staples HS-Ginny Parker Field [Directions] | 5:30 p.m. | L 10-7 | |
| Tue., 5/2 | JV Girls Lacrosse | Fairfield Ludlowe | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Tue., 5/2 | V Girls Outdoor Track | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 4:00 p.m. | ||
| Wed., 5/3 | V Baseball | Trumbull | Home - Staples HS-Baseball Diamond [Directions] | 4:30 p.m. | W 4-0 | |
| Wed., 5/3 | JV Baseball | Trumbull | Home - Staples HS-Wakeman Field [Directions] | 4:30 p.m. | ||
| Wed., 5/3 | FR Baseball | Trumbull | Away - Trumbull HS-Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/3 | FR Boys Lacrosse | Trumbull | Away - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | ||
| Wed., 5/3 | V Boys Tennis | Bridgeport Central | Home - Staples HS-Staples Tennis Courts [Directions] | 4:45 p.m. | W 7-0 [Detailed Results] | |
| Wed., 5/3 | JV Boys Tennis | Greenwich | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/3 | V Boys Volleyball | Stamford | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | W 3-1 | |
| Wed., 5/3 | JV Boys Volleyball | Stamford | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Wed., 5/3 | V Girls Golf | St. Joseph | Away - Tashua Knolls Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 5/3 | V Softball | Trumbull | Away - Trumbull HS-Varsity Softball Diamond [Directions] | 4:30 p.m. | W 3-1 | |
| Wed., 5/3 | JV Softball | Trumbull | Away - Trumbull HS-JV Softball Diamond [Directions] | Canceled | Cancelled | |
| Wed., 5/3 | V Girls Tennis | Bridgeport Central | Away - Bridgeport Central HS-Central High School Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Wed., 5/3 | JV Girls Tennis | Greenwich | Away - Binney Park [Directions] | 4:30 p.m. | ||
| Thu., 5/4 | V Boys Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 6:30 p.m. | W 6-5 | |
| Thu., 5/4 | JV Boys Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | ||
| Thu., 5/4 | V Boys Rugby | Fairfield Prep | Away - Fairfield University-Grauert Field [Directions] | 4:00 p.m. | ||
| Thu., 5/4 | JV Boys Rugby | Fairfield Prep | Away - Fairfield University-Grauert Field [Directions] | 5:30 p.m. | ||
| Thu., 5/4 | V Boys Tennis | St. Joseph | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Thu., 5/4 | JV Boys Tennis | Greenwich | Away - Central MS [Directions] | 4:30 p.m. | ||
| Thu., 5/4 | V Girls Lacrosse | New Canaan | Home - Staples HS-Ginny Parker Field [Directions] | 5:30 p.m. | L 15-2 | |
| Thu., 5/4 | JV Girls Lacrosse | New Canaan | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Thu., 5/4 | V Girls Rugby | North Haven | Away - field at Morgan School [Directions] | 5:00 p.m. | ||
| Thu., 5/4 | V Girls Tennis | St. Joseph | Away - St. Joseph HS-Tennis Courts [Directions] | 4:00 p.m. | W 4-3 [Detailed Results] | |
| Thu., 5/4 | JV Girls Tennis | Greenwich | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 5/5 | V Baseball | Stamford | Away - Stamford HS-SHS Baseball Diamond [Directions] | 4:00 p.m. | W 8-0 | |
| Fri., 5/5 | JV Baseball | Stamford | Away - Belltown Park-Barrett Field, Belltown Park [Directions] | 4:00 p.m. | ||
| Fri., 5/5 | FR Baseball | Stamford | Home - Staples HS-Baseball Diamond [Directions] | Postponed | ||
| Fri., 5/5 | V Boys Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | L 3-0 | |
| Fri., 5/5 | JV Boys Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 5/5 | FR Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Fairfield Warde Grass Utility Field [Directions] | 4:00 p.m. | ||
| Fri., 5/5 | V Softball | Stamford | Home - Greens Farms Elementary School-Softball Field [Directions] | 7:00 p.m. | W 7-6 | |
| Fri., 5/5 | JV Softball | Stamford | Home - Staples HS-Staples Softball Field [Directions] | Postponed | ||
| Sat., 5/6 | V Baseball | Waterford | Away - Waterford HS-Alumni Baseball Field [Directions] | 1:00 p.m. | W 10-1 | |
| Sat., 5/6 | JV Baseball | Waterford | Away - Leary Park-Baseball Diamond [Directions] | 1:00 p.m. | ||
| Sat., 5/6 | FR Baseball | Fairfield Warde | Home - Staples HS-Baseball Diamond [Directions] | 10:30 a.m. | ||
| Sat., 5/6 | V Boys Lacrosse | St. Johns Prep (MA) | Away - St. John's Preparatory School-Cronin Glatz | 3:00 p.m. | L 12-11 | |
| Sat., 5/6 | V Girls Lacrosse | Amity | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | L 15-11 | |
| Sat., 5/6 | JV Girls Lacrosse | Amity | Home - Staples HS-Staples Stadium [Directions] | 2:00 p.m. | ||
| Mon., 5/8 | V Baseball | Bridgeport Central | Away - Bridgeport Central HS-Baseball Diamond [Directions] | 4:00 p.m. | W 14-2 | |
| Mon., 5/8 | FR Baseball | Bridgeport Central | Home - Staples HS-Baseball Diamond [Directions] | Canceled | Cancelled | |
| Mon., 5/8 | FR Boys Lacrosse | Fairfield Warde | Home - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Mon., 5/8 | V Boys Tennis | Norwalk | Away - Norwalk HS-Tennis Courts [Directions] | 4:00 p.m. | W 6-1 [Detailed Results] | |
| Mon., 5/8 | JV Boys Tennis | Fairfield Warde | Away - Fairfield Warde HS-Knapps Courts [Directions] | 4:00 p.m. | ||
| Mon., 5/8 | V Boys Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 4:00 p.m. | L 3-2 | |
| Mon., 5/8 | JV Boys Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 5/8 | V Softball | Bridgeport Central | Home - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | W 17-1 | |
| Mon., 5/8 | V Girls Tennis | Norwalk | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Mon., 5/8 | JV Girls Tennis | Trumbull | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/9 | V Boys Lacrosse | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | W 23-1 | |
| Tue., 5/9 | JV Boys Lacrosse | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/9 | V Boys Outdoor Track | Darien | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/9 | V Boys Tennis | Brien McMahon | Away - Brien McMahon HS-Tennis Courts [Directions] | 4:00 p.m. | W 6-1 [Detailed Results] | |
| Tue., 5/9 | V Girls Golf | Wilton | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 5/9 | JV Girls Golf | Fairfield Ludlowe | Away - Carl Dickman Par 3 [Directions] | 3:15 p.m. | ||
| Tue., 5/9 | FR Girls Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | 3:30 p.m. | ||
| Tue., 5/9 | V Girls Outdoor Track | Darien | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/9 | JV Softball | Bridgeport Central | Home - Staples HS-Wakeman Field [Directions] | 4:30 p.m. | ||
| Tue., 5/9 | V Girls Tennis | Brien McMahon | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Tue., 5/9 | JV Girls Tennis | New Canaan | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/10 | V Baseball | St. Joseph | Away - St. Joseph HS-Baseball Diamond [Directions] | 4:00 p.m. | L 3-0 | |
| Wed., 5/10 | JV Baseball | St. Joseph | Away - Unity Park-Field 1 [Directions] | 4:00 p.m. | ||
| Wed., 5/10 | FR Baseball | St. Joseph | Home - Staples HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 5/10 | V Boys Lacrosse | Glastonbury | Away - Glastonbury HS-Field 1 [Directions] | 6:00 p.m. | W 16-5 | |
| Wed., 5/10 | JV Boys Lacrosse | Glastonbury | Away - Glastonbury HS-Field 11 [Directions] | 4:30 p.m. | ||
| Wed., 5/10 | FR Boys Lacrosse | Greenwich | Away - Cos Cob Park, Benvenuto Field-Benvenuto Field [Directions] | 4:30 p.m. | ||
| Wed., 5/10 | V Boys Rugby | Darien | Away - Royle School Field [Directions] | 4:00 p.m. | ||
| Wed., 5/10 | JV Boys Tennis | Fairfield Ludlowe | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:30 p.m. | ||
| Wed., 5/10 | V Boys Volleyball | St. Joseph | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | L 3-0 | |
| Wed., 5/10 | JV Boys Volleyball | St. Joseph | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Wed., 5/10 | V Girls Golf | Ridgefield | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 5/10 | JV Girls Golf | Ridgefield | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 5/10 | V Girls Lacrosse | Westhill | Home - Staples HS-Staples Stadium [Directions] | 6:00 p.m. | W 21-8 | |
| Wed., 5/10 | JV Girls Lacrosse | Westhill | Home - Staples HS-Ginny Parker Field [Directions] | 4:15 p.m. | ||
| Wed., 5/10 | V Softball | St. Joseph | Home - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | L 10-4 | |
| Wed., 5/10 | JV Softball | St. Joseph | Home - Staples HS-Staples Softball Field [Directions] | Canceled | Cancelled | |
| Thu., 5/11 | V Baseball | Norwalk | Home - Staples HS-Baseball Diamond [Directions] | 4:30 p.m. | W 9-0 | |
| Thu., 5/11 | JV Baseball | Norwalk | Home - Staples HS-Wakeman Field [Directions] | 4:30 p.m. | ||
| Thu., 5/11 | FR Baseball | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 4:00 p.m. | ||
| Thu., 5/11 | V Boys Rugby | Simsbury | Home - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Thu., 5/11 | V Boys Tennis | Fairfield Ludlowe | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | W 5-2 [Detailed Results] | |
| Thu., 5/11 | JV Boys Tennis | Fairfield Ludlowe | Away - Tomlinson MS-Tennis Courts [Directions] | 4:30 p.m. | ||
| Thu., 5/11 | V Girls Golf | Danbury | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 5/11 | V Girls Lacrosse | Cheshire | Home - Staples HS-Ginny Parker Field [Directions] | 5:00 p.m. | L 11-7 | |
| Thu., 5/11 | JV Girls Lacrosse | Cheshire | Home - Staples HS-Ginny Parker Field [Directions] | 6:30 p.m. | ||
| Thu., 5/11 | V Girls Rugby | TBA, Greenwich, Rye (NY) | Away - Darien HS-Royle Field @ 133 Mansfield Ave, Darien, CT 06820 | Canceled | Cancelled | |
| Thu., 5/11 | V Softball | Norwalk | Away - Norwalk HS-Ray Barry Field [Directions] | 4:00 p.m. | L 2-1 | |
| Thu., 5/11 | JV Softball | Norwalk | Away - Naramake School Field [Directions] | Postponed | ||
| Thu., 5/11 | V Girls Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Tennis Courts [Directions] | 4:00 p.m. | L 5-2 [Detailed Results] | |
| Thu., 5/11 | Miscellaneous Events | STAPLES UNIFIED TRACK MEET @ FAIRFIELD LUDLOWE | Home - Fairfield Ludlowe HS-Fairfield Ludlowe [Directions] | 3:00 p.m. | ||
| Fri., 5/12 | JV Boys Lacrosse | Notre Dame-West Haven | Home - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Fri., 5/12 | JV Boys Tennis | Darien | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 5/12 | V Boys Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | L 3-0 | |
| Fri., 5/12 | JV Boys Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 6:00 p.m. | ||
| Fri., 5/12 | V Girls Water Polo | Girls Varsity Water Polo vs Hamden Country Day School | Home - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Sat., 5/13 | JV Baseball | Fairfield Warde | Away - Fairfield Warde HS-Baseball Diamond [Directions] | 10:00 a.m. | ||
| Sat., 5/13 | V Boys Lacrosse | Ridgefield | Home - Staples HS-Staples Stadium [Directions] | 1:00 p.m. | L 6-5 | |
| Sat., 5/13 | JV Boys Lacrosse | Ridgefield | Home - Staples HS-Staples Stadium [Directions] | 10:30 a.m. | ||
| Mon., 5/15 | V Baseball | Brien McMahon | Home - Staples HS-Baseball Diamond [Directions] | 4:30 p.m. | W 3-0 | |
| Mon., 5/15 | JV Baseball | Brien McMahon | Home - Staples HS-Wakeman Field [Directions] | 4:30 p.m. | ||
| Mon., 5/15 | FR Baseball | Woodland | Away - Pent Field - Beacon Falls Recreation Complex [Directions] | 3:45 p.m. | ||
| Mon., 5/15 | V Boys Rugby | Fairfield Ludlowe | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 7:00 p.m. | ||
| Mon., 5/15 | V Boys Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:00 p.m. | L 3-0 | |
| Mon., 5/15 | V Softball | Brien McMahon | Away - Brien McMahon HS-Softball Diamond [Directions] | 6:00 p.m. | W 7-3 | |
| Tue., 5/16 | JV Boys Lacrosse | Fairfield Ludlowe | Home - Staples HS-Wakeman Field B (turf) [Directions] | 5:00 p.m. | ||
| Tue., 5/16 | FR Boys Lacrosse | Darien | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Tue., 5/16 | V Boys Outdoor Track | Greenwich | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/16 | V Girls Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | 3:30 p.m. | ||
| Tue., 5/16 | V Girls Lacrosse | Guilford | Home - Staples HS-Ginny Parker Field [Directions] | 5:30 p.m. | W 8-6 | |
| Tue., 5/16 | JV Girls Lacrosse | Guilford | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Tue., 5/16 | FR Girls Lacrosse | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 5/16 | V Girls Outdoor Track | Greenwich | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/16 | JV Softball | Brien McMahon | Away - Brien McMahon HS-Softball Diamond [Directions] | 4:30 p.m. | ||
| Wed., 5/17 | V Baseball | Fairfield Ludlowe | Away - Kiwanis Field-Baseball Diamond [Directions] | 4:00 p.m. | W 14-4 | |
| Wed., 5/17 | JV Baseball | Fairfield Ludlowe | Away - Owen Fish Park-Owen Fish [Directions] | 4:00 p.m. | ||
| Wed., 5/17 | FR Baseball | Fairfield Ludlowe | Home - Staples HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 5/17 | V Boys Volleyball | Darien | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | L 3-0 | |
| Wed., 5/17 | JV Boys Volleyball | Darien | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Wed., 5/17 | V Girls Golf | Trumbull | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 5/17 | JV Girls Golf | Trumbull | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 5/17 | V Girls Rugby | Southington | Away - Southington HS-10 FB JV PRACTICE FIELD [Directions] | 5:00 p.m. | ||
| Wed., 5/17 | V Softball | Fairfield Ludlowe | Home - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | L 9-0 | |
| Wed., 5/17 | JV Softball | Fairfield Ludlowe | Home - Staples HS-Staples Softball Field [Directions] | Canceled | Cancelled | |
| Wed., 5/17 | Miscellaneous Events | COED SAILING - REGATTA @ NOROTON YACHT CLUB | Home - Noroton Yacht Club [Directions] | 3:00 p.m. | ||
| Thu., 5/18 | JV Boys Lacrosse | Darien | Home - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Thu., 5/18 | FR Boys Lacrosse | Wilton | Away - Allen's Meadow-Lacrosse Field #1 [Directions] | 4:30 p.m. | ||
| Thu., 5/18 | V Girls Golf | Darien | Away - Wee Burn CC [Directions] | 3:00 p.m. | ||
| Fri., 5/19 | FR Baseball | Fairfield Prep | Home - Staples HS-Wakeman Field [Directions] | 3:30 p.m. | ||
| Fri., 5/19 | V Boys Rugby | Trumbull | Home - Staples HS-Staples Stadium [Directions] | 7:00 p.m. | ||
| Fri., 5/19 | JV Boys Rugby | Trumbull | Home - Staples HS-Staples Stadium [Directions] | 5:00 p.m. | ||
| Sat., 5/20 | Miscellaneous Events | Junior Prom | Home - Staples HS [Directions] | 7:00 p.m. | ||
| Mon., 5/22 | JV Girls Golf | New Canaan | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 5/23 | V Girls Golf | Fairfield Ludlowe | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 5/23 | JV Girls Golf | Fairfield Ludlowe | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 5/23 | Miscellaneous Events | 3 v 3 Fundraiser Soccer | Home - Staples HS-Staples Stadium [Directions] | 3:00 p.m. | ||
| Wed., 5/24 | JV Boys Lacrosse | New Canaan | Home - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Wed., 5/24 | V Girls Golf | Greenwich | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 5/24 | JV Girls Golf | Greenwich | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 5/24 | V Softball | Suffield | Home - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | W 8-4 | |
| Thu., 5/25 | V Boys Rugby | Ridgefield | Home - Staples HS-Staples Stadium [Directions] | 6:00 p.m. | ||
| Thu., 5/25 | Miscellaneous Events | Girls Rugby Championship Game at Morgan School | Home [Directions] | 5:00 p.m. | ||
| Tue., 5/30 | V Girls Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 5/30 | JV Girls Golf | Trumbull | Away - Tashua Knolls Golf Course-Tashua Glen [Directions] | 3:15 p.m. | ||
| Sat., 6/3 | Miscellaneous Events | Senior Prom | Home - Staples HS [Directions] | 7:00 p.m. | ||
| Sat., 6/10 | V Boys Rugby | Rugby State Championships - TBA | Home - Staples HS-Staples Stadium [Directions] | TBA | ||
| Tue., 6/13 | Miscellaneous Events | Graduation | Home - Staples HS-Staples Stadium [Directions] | 6:00 p.m. | ||