| Staples 2020-21 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 736 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Sat., 9/26 | V Boys Soccer | Norwalk (Scrim.) | Away - Norwalk HS-Testa Field [Directions] | 3:00 p.m. | ||
| Tue., 9/29 | V Boys Soccer | Brien McMahon (Scrim.) | Away - Brien McMahon HS-Pride Field [Directions] | 5:30 p.m. | ||
| Tue., 9/29 | V Girls Soccer | Norwalk (Scrim.) | Away - Norwalk HS-Testa Field [Directions] | 4:00 p.m. | ||
| Tue., 9/29 | V Girls Volleyball | Brien McMahon (Scrim.) | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 10/1 | V Field Hockey | Danbury | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | W 10-0 | |
| Thu., 10/1 | V Girls Soccer | Danbury | Home - Staples HS-Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 2-0 | |
| Thu., 10/1 | V Girls Swimming and Diving | Ridgefield | Away - Barlow Mountain Pool [Directions] | 4:30 p.m. | ||
| Thu., 10/1 | V Girls Volleyball | Danbury | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 10/2 | V Boys Cross Country | Danbury | Away - Tarrywile Park [Directions] | 4:30 p.m. | ||
| Fri., 10/2 | V Football | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 5:00 p.m. | ||
| Fri., 10/2 | FR Football | Danbury | Away - Danbury HS-Grass football field [Directions] | 5:00 p.m. | ||
| Fri., 10/2 | V Boys Soccer | Danbury | Home - Staples HS-Loeffler Field - Staples HS [Directions] | 4:00 p.m. | L 2-1 | |
| Fri., 10/2 | V Girls Cross Country | Danbury | Away - Tarrywile Park [Directions] | 4:30 p.m. | ||
| Sat., 10/3 | JV Boys Soccer | Danbury | Home - Staples HS-Loeffler Field - Staples HS [Directions] | 12:00 p.m. | L 4-0 | |
| Sat., 10/3 | FR Boys Soccer | Danbury | Home - Staples HS-Loeffler Field - Staples HS [Directions] | 2:00 p.m. | T 1-1 | |
| Sat., 10/3 | JV Boys Water Polo | CT Premier | Away - Chelsea Piers Pool | 12:00 p.m. | ||
| Sat., 10/3 | JV Field Hockey | Danbury | Home - Staples HS-Ginny Parker Field [Directions] | 9:00 a.m. | ||
| Sat., 10/3 | FR Field Hockey | Danbury | Home - Staples HS-Ginny Parker Field [Directions] | 10:30 a.m. | ||
| Sat., 10/3 | JV Girls Soccer | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 1:00 p.m. | ||
| Sat., 10/3 | FR Girls Soccer | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 11:00 a.m. | ||
| Sat., 10/3 | JV Girls Volleyball | Danbury | Home - Staples HS-Staples Gym [Directions] | 10:00 a.m. | ||
| Sat., 10/3 | FR Girls Volleyball | Danbury | Home - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Mon., 10/5 | V Boys Soccer | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 4:30 p.m. | T 1-1 | |
| Tue., 10/6 | V Boys Cross Country | Ridgefield | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 10/6 | V Girls Cross Country | Ridgefield | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 10/6 | V Girls Soccer | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 4:30 p.m. | W 2-0 | |
| Tue., 10/6 | V Girls Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 4:30 p.m. | W 3-2 | |
| Wed., 10/7 | V Boys Soccer | Wilton | Away - Wilton HS-Lilly Field [Directions] | 4:30 p.m. | L 4-0 | |
| Wed., 10/7 | JV Boys Water Polo | CT Premier | Home - Staples HS-Staples High School Pool [Directions] | 5:30 p.m. | ||
| Wed., 10/7 | V Field Hockey | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 4:00 p.m. | W 13-0 | |
| Wed., 10/7 | V Girls Swimming and Diving | Norwalk/McMahon | Away - Norwalk HS-Pat Spinola Natatorium [Directions] | 5:00 p.m. | ||
| Wed., 10/7 | V Girls Swimming and Diving | Fairfield Ludlowe, Norwalk/McMahon | Away - Westport YMCA [Directions] | TBA | Fairfield Ludlowe is virtual | |
| Pending change awaiting acceptance by one or more parties involved: Time to 8:00 p.m. | ||||||
| Thu., 10/8 | V Boys Water Polo | Greenwich | Away - Greenwich HS-Pool [Directions] | 3:45 p.m. | ||
| Thu., 10/8 | JV Boys Water Polo | Greenwich | Away - Greenwich HS-Pool [Directions] | 5:00 p.m. | ||
| Thu., 10/8 | V Girls Soccer | Wilton | Away - Wilton HS-Lilly Field [Directions] | 4:30 p.m. | W 3-0 | |
| Thu., 10/8 | V Girls Volleyball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | L 3-1 | |
| Fri., 10/9 | V Football | Wilton | Away - Wilton HS-Fujitani Field - Turf [Directions] | 7:00 p.m. | ||
| Fri., 10/9 | V Field Hockey | Wilton | Home - Staples HS-Ginny Parker Field [Directions] | 4:30 p.m. | W 7-0 | |
| Sat., 10/10 | JV Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 9:30 a.m. | W 4-1 | |
| Sat., 10/10 | FR Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 8:00 a.m. | W 2-0 | |
| Sat., 10/10 | JV Field Hockey | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 11:00 a.m. | ||
| Sat., 10/10 | FR Field Hockey | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 12:30 p.m. | ||
| Sat., 10/10 | JV Girls Soccer | Brien McMahon | Home - Staples HS-Loeffler Field - Staples HS [Directions] | 1:00 p.m. | ||
| Sat., 10/10 | JV Girls Volleyball | Wilton | Home - Staples HS-Staples Gym [Directions] | 10:00 a.m. | ||
| Sat., 10/10 | FR Girls Volleyball | Wilton | Home - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Mon., 10/12 | JV Football | Wilton | Away - Wilton HS-Fuijitani Field -Turf [Directions] | 3:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 3:30 p.m. | ||||||
| Mon., 10/12 | FR Football | Wilton | Away - Wilton HS-Fuijitani Field -Turf [Directions] | 3:00 p.m. | ||
| Mon., 10/12 | V Boys Soccer | Wilton | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:30 p.m. | T 1-1 | |
| Tue., 10/13 | V Girls Soccer | Wilton | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:30 p.m. | W 4-0 | |
| Tue., 10/13 | V Girls Volleyball | Wilton | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 10/14 | V Boys Cross Country | Wilton | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Wed., 10/14 | V Boys Soccer | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 4:30 p.m. | W 3-2 | |
| Wed., 10/14 | JV Boys Water Polo | CT Premier | Home - Staples HS-Staples High School Pool [Directions] | 5:30 p.m. | ||
| Wed., 10/14 | V Girls Cross Country | Wilton | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Wed., 10/14 | V Field Hockey | Wilton | Away - Wilton HS-Fuijitani Field -Turf [Directions] | 4:30 p.m. | W 1-0 | |
| Thu., 10/15 | V Boys Water Polo | Greenwich | Home - Staples HS-Staples High School Pool [Directions] | 5:30 p.m. | ||
| Thu., 10/15 | JV Boys Water Polo | Greenwich | Home - Staples HS-Staples High School Pool [Directions] | 6:30 p.m. | ||
| Thu., 10/15 | V Girls Soccer | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 5:30 p.m. | T 0-0 | |
| Thu., 10/15 | V Girls Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:30 p.m. | W 3-1 | |
| Fri., 10/16 | JV Football | Ridgefield | Home - Staples HS-Staples Stadium [Directions] | Canceled | Cancelled | |
| Fri., 10/16 | FR Football | Ridgefield | Home - Staples HS-Staples Stadium [Directions] | Canceled | Cancelled | |
| Fri., 10/16 | V Boys Water Polo | Brunswick School | Away - Greenwich HS | 8:45 p.m. | ||
| Fri., 10/16 | V Girls Swimming and Diving | Wilton | Home - Staples HS-Staples High School Pool [Directions] | 4:30 p.m. | ||
| Sat., 10/17 | JV Boys Soccer | Ridgefield | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | L 1-0 | |
| Sat., 10/17 | V Boys Water Polo | G-Aquatics | Away - Greenwich HS | 12:30 p.m. | After game at Greenwich HS, take team to Greenwich YMCA | |
| Sat., 10/17 | V Boys Water Polo | Greenwich Girls B | Away - Greenwich YMCA | 2:45 p.m. | ||
| Sat., 10/17 | JV Field Hockey | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 12:30 p.m. | ||
| Sat., 10/17 | FR Field Hockey | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 11:00 a.m. | ||
| Sat., 10/17 | JV Girls Soccer | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 2:00 p.m. | ||
| Sat., 10/17 | FR Girls Soccer | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 9:00 a.m. | ||
| Mon., 10/19 | V Football | Ridgefield | Home - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Mon., 10/19 | V Boys Soccer | Ridgefield | Home - Staples HS-Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 10/19 | V Field Hockey | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 5:30 p.m. | W 1-0 | |
| Tue., 10/20 | V Boys Cross Country | Norwalk | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 10/20 | V Girls Cross Country | Norwalk | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 10/20 | V Girls Volleyball | Ridgefield | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | L 0-3 | |
| Wed., 10/21 | V Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 4:30 p.m. | ||
| Wed., 10/21 | FR Boys Soccer | Ridgefield | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:15 p.m. | W 6-1 | You can warm up on the adjacent grass field. Girls will be off the turf for a 4:15 start. |
| Wed., 10/21 | JV Boys Water Polo | CT Premier | Home - Staples HS-Staples High School Pool [Directions] | 5:30 p.m. | ||
| Wed., 10/21 | V Field Hockey | Ridgefield | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | W 2-1 | |
| Wed., 10/21 | JV Girls Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 6:00 p.m. | ||
| Wed., 10/21 | FR Girls Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:00 p.m. | ||
| Thu., 10/22 | V Girls Soccer | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 6:30 p.m. | Cancelled | |
| Thu., 10/22 | V Girls Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | Canceled | Cancelled | |
| Fri., 10/23 | V Football | Brien McMahon | Home - Staples HS-Staples Stadium [Directions] | Canceled | Cancelled | |
| Fri., 10/23 | V Field Hockey | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 4:30 p.m. | Cancelled | |
| Fri., 10/23 | V Girls Swimming and Diving | Danbury | Home - Staples HS-Staples High School Pool [Directions] | 4:30 p.m. | ||
| Fri., 10/23 | JV Girls Volleyball | Brien McMahon | Home - Staples HS-Staples Gym [Directions] | Canceled | Cancelled | |
| Fri., 10/23 | FR Girls Volleyball | Brien McMahon | Home - Staples HS-Field House [Directions] | Canceled | Cancelled | |
| Sat., 10/24 | V Boys Cross Country | Wilton | Away - Allen's Meadow-XC Course [Directions] | 11:30 a.m. | ||
| Sat., 10/24 | JV Boys Soccer | Wilton | Home - Staples HS-Loeffler Field - Staples HS [Directions] | 3:00 p.m. | W 1-0 | |
| Sat., 10/24 | FR Boys Soccer | Wilton | Home - Staples HS-Loeffler Field - Staples HS [Directions] | 1:00 p.m. | L 2-0 | |
| Sat., 10/24 | V Girls Cross Country | Wilton | Away - Allen's Meadow-XC Course [Directions] | 11:15 a.m. | ||
| Sat., 10/24 | JV Field Hockey | Wilton | Home - Staples HS-Ginny Parker Field [Directions] | 3:00 p.m. | ||
| Sat., 10/24 | FR Field Hockey | Wilton | Home - Staples HS-Ginny Parker Field [Directions] | 1:30 p.m. | ||
| Sat., 10/24 | FR Girls Soccer | Wilton | Away - Wilton HS-Lilly Field [Directions] | 11:00 a.m. | ||
| Mon., 10/26 | V Boys Soccer | Brien McMahon | Home - Staples HS-Loeffler Field - Staples HS [Directions] | 4:30 p.m. | Cancelled | |
| Tue., 10/27 | V Boys Cross Country | Brien McMahon | Home - Staples HS-Staples Stadium [Directions] | Canceled | Cancelled | |
| Tue., 10/27 | V Girls Cross Country | Brien McMahon | Home - Staples HS-Staples Stadium [Directions] | Canceled | Cancelled | |
| Tue., 10/27 | V Girls Soccer | Brien McMahon | Home - Staples HS-Loeffler Field - Staples HS [Directions] | 4:30 p.m. | Cancelled | |
| Tue., 10/27 | V Girls Volleyball | Brien McMahon | Home - Staples HS-Staples Gym [Directions] | Canceled | Cancelled | |
| Tue., 10/27 | JV Girls Volleyball | Away - Staples HS-Staples Gym | 5:00 p.m. | |||
| Wed., 10/28 | V Boys Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 7:00 p.m. | W 2-1 | |
| Wed., 10/28 | V Field Hockey | Brien McMahon | Home - Staples HS-Ginny Parker Field [Directions] | 4:30 p.m. | Cancelled | |
| Wed., 10/28 | V Girls Swimming and Diving | Norwalk/McMahon | Home - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Thu., 10/29 | FR Football | Ridgefield | Away - Ridgefield HS-Tiger Hollow Turf Field II [Directions] | Postponed | ||
| Thu., 10/29 | V Girls Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 7:00 p.m. | W 5-0 | |
| Thu., 10/29 | V Girls Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:30 p.m. | W 3-1 | |
| Fri., 10/30 | V Football | Norwalk | Home - Staples HS-Staples Stadium [Directions] | 7:00 p.m. | ||
| Fri., 10/30 | V Field Hockey | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 7:00 p.m. | W 6-1 | |
| Fri., 10/30 | JV Girls Volleyball | Norwalk | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/30 | FR Girls Volleyball | Norwalk | Home - Staples HS-Field House [Directions] | 4:00 p.m. | ||
| Sat., 10/31 | JV Boys Soccer | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | Canceled | Cancelled | |
| Sat., 10/31 | FR Boys Soccer | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 11:00 a.m. | L 3-1 | |
| Sat., 10/31 | JV Field Hockey | Brien McMahon | Home - Staples HS-Ginny Parker Field [Directions] | Canceled | Cancelled | |
| Sat., 10/31 | JV Girls Soccer | Norwalk | Home - Staples HS-Loeffler Field - Staples HS [Directions] | Postponed | ||
| Mon., 11/2 | V Boys Soccer | Norwalk | Home - Staples HS-Loeffler Field - Staples HS [Directions] | 3:00 p.m. | ||
| Tue., 11/3 | FR Football | Norwalk | Home - Staples HS-Staples Stadium [Directions] | Postponed | ||
| Tue., 11/3 | V Field Hockey | Norwalk | Home - Staples HS-Ginny Parker Field [Directions] | 3:00 p.m. | W 6-1 | |
| Tue., 11/3 | V Girls Soccer | Norwalk | Home - Staples HS-Loeffler Field - Staples HS [Directions] | 3:00 p.m. | W 4-0 | |
| Tue., 11/3 | V Girls Volleyball | Norwalk | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | W 3-1 | |
| Wed., 11/4 | V Boys Cross Country | FCIAC Central Division Championship | Away - Waveny Park | TBA | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 3:00 p.m. | ||||||
| Wed., 11/4 | V Boys Cross Country | Brien McMahon, TBA | Away - Brien McMahon HS-Casagrande Field [Directions] | TBA | ||
| Wed., 11/4 | V Boys Soccer | Brien McMahon | Home - Staples HS-Loeffler Field - Staples HS [Directions] | 3:00 p.m. | L 0-1 | |
| Wed., 11/4 | JV Boys Water Polo | CT Premier | Home - Staples HS-Staples High School Pool [Directions] | 5:30 p.m. | ||
| Wed., 11/4 | V Girls Cross Country | FCIAC Central Division Championship | Away - Waveny Park | TBA | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 3:30 p.m. | ||||||
| Wed., 11/4 | JV Girls Soccer | Wilton | Away - Wilton HS-Allen Meadow [Directions] | 3:15 p.m. | ||
| Thu., 11/5 | FR Football | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | 4:00 p.m. | ||
| Thu., 11/5 | V Girls Soccer | Ridgefield | Home - Staples HS-Wakeman Field B (turf) [Directions] | 3:00 p.m. | T 2-2 | |
| Fri., 11/6 | V Girls Swimming and Diving | Blue & White Meet | Home - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Sat., 11/7 | JV Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 10:30 a.m. | ||
| Sat., 11/7 | JV Boys Soccer | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | Canceled | L 3-1 | |
| Sat., 11/7 | FR Boys Soccer | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 9:00 a.m. | L 5-0 | |
| Sat., 11/7 | V Boys Water Polo | Greenwich Girls A | Away - Greenwich YMCA | 2:45 p.m. | ||
| Sat., 11/7 | JV Boys Water Polo | Greenwich | Away - Greenwich HS-Pool [Directions] | 12:00 p.m. | After game at Greenwich HS, take team to Greenwich YMCA | |
| Sat., 11/7 | V Field Hockey | Brien McMahon | Home - Staples HS-Ginny Parker Field [Directions] | 3:00 p.m. | W 8-0 | |
| Sat., 11/7 | JV Field Hockey | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 11:00 a.m. | ||
| Sat., 11/7 | JV Girls Soccer | Danbury | Home - Staples HS-Loeffler Field - Staples HS [Directions] | 3:00 p.m. | ||
| Sat., 11/7 | FR Girls Soccer | Danbury | Home - Staples HS-Loeffler Field - Staples HS [Directions] | 1:00 p.m. | ||
| Sat., 11/7 | V Girls Volleyball | Danbury | Home - Staples HS-Staples Gym [Directions] | 2:30 p.m. | W 3-1 | |
| Sat., 11/7 | JV Girls Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 11:00 a.m. | ||
| Sat., 11/7 | FR Girls Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 1:00 p.m. | ||
| Mon., 11/9 | FR Football | Ridgefield | Away - Ridgefield HS-Tiger Hollow Turf Field II [Directions] | 4:00 p.m. | ||
| Mon., 11/9 | FR Field Hockey | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 4:30 p.m. | ||
| Tue., 11/10 | V Field Hockey | Ridgefield | Home - Staples HS-Ginny Parker Field [Directions] | 2:00 p.m. | ||
| Tue., 11/10 | V Girls Soccer | Danbury | Home - Staples HS-Wakeman Field B (turf) [Directions] | 2:00 p.m. | ||
| Tue., 11/10 | V Girls Volleyball | Ridgefield | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Wed., 11/11 | JV Boys Water Polo | CT Premier | Home - Staples HS-Staples High School Pool [Directions] | 5:30 p.m. | ||
| Thu., 11/12 | V Girls Soccer | Ridgefield | Home - Staples HS-Wakeman Field B (turf) [Directions] | Postponed | ||
| Sat., 11/14 | V Girls Swimming and Diving | Norwalk/McMahon, Danbury, TBA, Ridgefield | Away - Norwalk HS-Pat Spinola Natatorium [Directions] | 10:45 a.m. | ||
| Wed., 1/20 | V Boys Alpine Skiing | Practice | Home - Mt. Southingon Ski Area [Directions] | 4-6 p.m. | ||
| Wed., 1/20 | V Girls Alpine Skiing | Practice | Home - Mt. Southingon Ski Area [Directions] | 4-6 p.m. | Bus ride with boys | |
| Mon., 1/25 | V Boys Alpine Skiing | Practice | Home - Mt. Southingon Ski Area [Directions] | 4-6 p.m. | ||
| Mon., 1/25 | V Girls Alpine Skiing | Practice | Home - Mt. Southingon Ski Area [Directions] | 4-6 p.m. | Bus ride with boys | |
| Mon., 2/1 | V Boys Alpine Skiing | Practice | Home - Mt. Southingon Ski Area [Directions] | Canceled | Cancelled | |
| Mon., 2/1 | V Girls Alpine Skiing | Practice | Home - Mt. Southingon Ski Area [Directions] | Canceled | Cancelled | Bus ride with boys |
| Thu., 2/4 | V Boys Basketball | Ridgefield (Scrim.) | Away - Ridgefield HS-Main Gym [Directions] | 5:00 p.m. | ||
| Fri., 2/5 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3-4:15 p.m. | ||
| Fri., 2/5 | V Girls Basketball | Fairfield Warde (Scrim.) | Home - Staples HS-Staples Gym [Directions] | 5:00 p.m. | ||
| Sat., 2/6 | V Boys Ice Hockey | Brookfield (Scrim.) | Home - Milford Ice Pavillion-Ice Rink [Directions] | 8:10 p.m. | ||
| Mon., 2/8 | V Boys Alpine Skiing | Practice | Home - Mt. Southingon Ski Area [Directions] | 4-6 p.m. | ||
| Mon., 2/8 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3-4:15 p.m. | ||
| Mon., 2/8 | V Girls Alpine Skiing | Practice | Home - Mt. Southingon Ski Area [Directions] | 4-6 p.m. | Bus ride with boys | |
| Tue., 2/9 | V Boys Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:00 p.m. | W 49-35 | |
| Tue., 2/9 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3-4:15 p.m. | ||
| Tue., 2/9 | V Girls Basketball | Greenwich | Home - Staples HS-Staples Gym [Directions] | 5:00 p.m. | W 61-40 | |
| Wed., 2/10 | V Boys Ice Hockey | Trumbull | Home - Milford Ice Pavillion-Ice Rink [Directions] | 6:30 p.m. | L 3-8 | |
| Wed., 2/10 | V Boys Swimming and Diving | Trumbull | Home - Staples HS-Staples High School Pool [Directions] | 4:30 p.m. | ||
| Wed., 2/10 | V Girls Gymnastics | Fairfield Ludlowe, Norwalk | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:30 p.m. | ||
| Wed., 2/10 | V Girls Gymnastics | Fairfield Warde, Norwalk | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:30 p.m. | ||
| Thu., 2/11 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3-4:15 p.m. | ||
| Thu., 2/11 | V Boys Squash | Darien | Away - Ox Ridge Club [Directions] | 7:30 p.m. | ||
| Thu., 2/11 | V Girls Gymnastics | Fairfield Ludlowe, Fairfield Warde | Home - Westport YMCA [Directions] | 7:00 p.m. | 128.75 | |
| Fri., 2/12 | V Boys Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 4:30 p.m. | W 65-44 | |
| Fri., 2/12 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3-4:15 p.m. | ||
| Fri., 2/12 | V Boys Squash | Darien | Home - Intensity Fitness [Directions] | 6:30 p.m. | ||
| Fri., 2/12 | V Boys Swimming and Diving | St. Joseph | Away - Hillcrest MS-Pool [Directions] | 3:00 p.m. | ||
| Fri., 2/12 | V Boys Swimming and Diving | Trumbull | Away - Hillcrest MS-Pool [Directions] | 3:30 p.m. | ||
| Fri., 2/12 | V Girls Basketball | Danbury | Home - Staples HS-Staples Gym [Directions] | 5:00 p.m. | W 48-47 | |
| Sat., 2/13 | JV Boys Basketball | Greenwich | Home - Staples HS-Staples Gym [Directions] | 9:00 a.m. | ||
| Sat., 2/13 | FR Boys Basketball | Greenwich | Home - Staples HS-Staples Gym [Directions] | 10:30 a.m. | ||
| Sat., 2/13 | JV Girls Basketball | Stamford | Away - Stamford HS-Kuzco Gymnasium [Directions] | 11:00 a.m. | ||
| Sat., 2/13 | V Girls Gymnastics | Trumbull | Away - Next Dimension Gymnastics-Next Dimension [Directions] | 2:00 p.m. | 127.75 | |
| Sat., 2/13 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Terry Conners - Stamford-Ice Rink [Directions] | 6:00 p.m. | L 1-7 | |
| Sat., 2/13 | V Girls Ice Hockey | St. Joseph | Home - Terry Conners - Stamford-Ice Rink [Directions] | 6:20 p.m. | L 1-7 | |
| Sun., 2/14 | JV Boys Ice Hockey | Xavier | Away - Champions Skating Rink - Cromwell-Lower Rink [Directions] | 12:00 p.m. | ||
| Mon., 2/15 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3-4:15 p.m. | ||
| Mon., 2/15 | V Girls Gymnastics | Greenwich, Norwalk | Away - Greenwich YWCA [Directions] | 2:45 p.m. | ||
| Mon., 2/15 | V Girls Ice Hockey | New Canaan | Home - Terry Conners - Stamford-Ice Rink [Directions] | 3:00 p.m. | L 0-8 | |
| Tue., 2/16 | V Boys Alpine Skiing | Practice | Home - Mt. Southingon Ski Area [Directions] | 4-6 p.m. | ||
| Tue., 2/16 | V Boys Basketball | Westhill | Home - Staples HS-Staples Gym [Directions] | 2:30 p.m. | W 60-53 | |
| Tue., 2/16 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3-4:15 p.m. | ||
| Tue., 2/16 | V Girls Alpine Skiing | Practice | Home - Mt. Southingon Ski Area [Directions] | 4-6 p.m. | Bus ride with boys | |
| Tue., 2/16 | V Girls Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 3:00 p.m. | W 53-31 | |
| Tue., 2/16 | V Girls Squash | Darien | Away - Ox Ridge Club [Directions] | 7:30 p.m. | ||
| Wed., 2/17 | JV Boys Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 2/17 | V Boys Ice Hockey | Milford Coop | Home - Milford Ice Pavillion-Ice Rink [Directions] | 6:30 p.m. | W 6-1 | |
| Wed., 2/17 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Away - Norwalk HS-Pat Spinola Natatorium [Directions] | 5:00 p.m. | ||
| Wed., 2/17 | JV Girls Basketball | Brien McMahon | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/17 | V Girls Gymnastics | Wilton | Away - Wilton HS-Aux Gym [Directions] | 3:45 p.m. | 129.35 | |
| Pending change awaiting acceptance by one or more parties involved: Time to 6:00 p.m. | ||||||
| Wed., 2/17 | V Girls Ice Hockey | Greenwich | Away - Greenwich - Dorothy Hamill-Rink [Directions] | 5:15 p.m. | L 3-6 | |
| Fri., 2/19 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | Canceled | Cancelled | |
| Sat., 2/20 | V Boys Basketball | Brien McMahon | Home - Staples HS-Staples Gym [Directions] | 12:30 p.m. | W 62-44 | |
| Sat., 2/20 | JV Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 9:00 a.m. | ||
| Sat., 2/20 | FR Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 9:00 a.m. | ||
| Sat., 2/20 | V Boys Ice Hockey | Brien McMahon/Norwalk | Away - Sono Ice House-Main Rink [Directions] | 8:10 p.m. | L 3-4(OT) | |
| Sat., 2/20 | JV Boys Ice Hockey | Milford Coop | Home - Milford Ice Pavillion-Ice Rink [Directions] | Canceled | Cancelled | |
| Sat., 2/20 | V Boys Swimming and Diving | New Canaan | Away - New Canaan YMCA-Pool [Directions] | 4:00 p.m. | ||
| Sat., 2/20 | V Girls Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 11:30 a.m. | W 48-21 | |
| Sat., 2/20 | JV Girls Basketball | Fairfield Warde | Home - Staples HS-Staples Gym [Directions] | 10:00 a.m. | ||
| Sat., 2/20 | V Girls Gymnastics | Greenwich | Home - Westport YMCA [Directions] | 5:00 p.m. | 128.6 | |
| Sat., 2/20 | V Girls Ice Hockey | Darien | Away - Darien Ice House-Ice Rink [Directions] | 4:20 p.m. | L 0-8 | |
| Sun., 2/21 | V Girls Squash | Darien | Away - Ox Ridge Club [Directions] | 7:30 p.m. | ||
| Mon., 2/22 | V Boys Alpine Skiing | Practice | Home - Mt. Southingon Ski Area [Directions] | 4-6 p.m. | ||
| Mon., 2/22 | V Boys Ice Hockey | New Milford | Home - Milford Ice Pavillion-Ice Rink [Directions] | 6:00 p.m. | ||
| Mon., 2/22 | V Girls Alpine Skiing | Practice | Home - Mt. Southingon Ski Area [Directions] | 4-6 p.m. | Bus ride with boys | |
| Tue., 2/23 | V Boys Basketball | Fairfield Ludlowe | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | W 58-48 | |
| Tue., 2/23 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3-4:15 p.m. | ||
| Tue., 2/23 | V Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:00 p.m. | W 61-57 | |
| Tue., 2/23 | V Girls Squash | Darien | Away - Ox Ridge Club [Directions] | 7:30 p.m. | ||
| Wed., 2/24 | JV Boys Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/24 | FR Boys Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/24 | V Boys Ice Hockey | Wilton | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:30 p.m. | W 5-2 | |
| Wed., 2/24 | JV Boys Ice Hockey | Trumbull | Home - Milford Ice Pavillion-Ice Rink [Directions] | Canceled | Cancelled | |
| Wed., 2/24 | V Boys Swimming and Diving | Ridgefield | Home - Staples HS-Staples High School Pool [Directions] | 3:30 p.m. | ||
| Wed., 2/24 | JV Girls Basketball | Fairfield Ludlowe | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/24 | V Girls Ice Hockey | St. Joseph | Away - Sports Center of Connecticut-Upper [Directions] | 4:00 p.m. | L 5-11 | |
| Wed., 2/24 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 4:00 p.m. | L 5-11 | |
| Thu., 2/25 | V Boys Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 5:00 p.m. | W 63-56 | |
| Thu., 2/25 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3-4:15 p.m. | ||
| Thu., 2/25 | V Boys Squash | Darien | Away - Ox Ridge Club [Directions] | 7:30 p.m. | ||
| Thu., 2/25 | V Girls Basketball | Trumbull | Home - Staples HS-Staples Gym [Directions] | 5:00 p.m. | W 44-38 | |
| Fri., 2/26 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3-4:15 p.m. | ||
| Fri., 2/26 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Home - Staples HS-Staples High School Pool [Directions] | 3:30 p.m. | ||
| Fri., 2/26 | V Girls Gymnastics | Norwalk | Home - Westport YMCA [Directions] | 7:00 p.m. | ||
| Sat., 2/27 | V Boys Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 1:00 p.m. | W 67-44 | |
| Sat., 2/27 | JV Boys Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 10:30 a.m. | ||
| Sat., 2/27 | FR Boys Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 9:00 a.m. | ||
| Sat., 2/27 | V Boys Ice Hockey | Masuk | Home - Milford Ice Pavillion-Ice Rink [Directions] | 6:50 p.m. | W 6-0 | |
| Sat., 2/27 | V Girls Basketball | Norwalk | Home - Staples HS-Staples Gym [Directions] | 2:00 p.m. | Cancelled | |
| Sat., 2/27 | V Girls Basketball | Wilton | Home - Staples HS-Staples Gym [Directions] | 2:00 p.m. | Cancelled | |
| Sat., 2/27 | JV Girls Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 11:30 a.m. | ||
| Sat., 2/27 | JV Girls Basketball | Wilton | Home - Staples HS-Staples Gym [Directions] | Canceled | Cancelled | |
| Sat., 2/27 | V Girls Gymnastics | Darien | Away - Darien YMCA [Directions] | 2:30 p.m. | 126.1 | |
| Sat., 2/27 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Terry Conners - Stamford-Ice Rink [Directions] | 4:40 p.m. | L 4-5 | |
| Mon., 3/1 | V Boys Ice Hockey | Westhill/Stamford | Away - Terry Conners - Stamford-Ice Rink [Directions] | 7:40 p.m. | W 5-3 | |
| Mon., 3/1 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Terry Conners - Stamford-Ice Rink [Directions] | 5:30 p.m. | W 4-3 | |
| Tue., 3/2 | V Boys Basketball | New Canaan | Home - Staples HS-Staples Gym [Directions] | 5:00 p.m. | L 50-59 | |
| Tue., 3/2 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3-4:15 p.m. | ||
| Tue., 3/2 | V Girls Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 5:00 p.m. | W 33-30 | |
| Tue., 3/2 | V Girls Gymnastics | Stamford, Westhill | Home - Westport YMCA [Directions] | 3:00 p.m. | ||
| Pending changes awaiting acceptance by one or more parties involved: Date to 3/11, Time to 7:00 p.m. | ||||||
| Wed., 3/3 | JV Boys Basketball | Trumbull | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Wed., 3/3 | V Boys Ice Hockey | Milford Coop | Away - Milford Ice Pavillion-Ice Rink [Directions] | 6:30 p.m. | W 2-1(OT) | |
| Wed., 3/3 | JV Girls Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 3:30 p.m. | ||
| Wed., 3/3 | FR Girls Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | Canceled | Cancelled | |
| Wed., 3/3 | V Girls Gymnastics | New Canaan | Away - Chelsea Piers - -Gym [Directions] | 7:30 p.m. | ||
| Wed., 3/3 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:30 p.m. | L 8-9 | |
| Thu., 3/4 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3-4:15 p.m. | ||
| Thu., 3/4 | V Girls Gymnastics | Westhill, Norwalk | Away - Chelsea Piers - Stamford-Virtual Meet [Directions] | 7:30 p.m. | 134.55 | |
| Thu., 3/4 | V Girls Gymnastics | Stamford, Norwalk | Away - Chelsea Piers-Virtual Meet [Directions] | 7:30 p.m. | ||
| Fri., 3/5 | V Boys Basketball | Stamford | Home - Staples HS-Staples Gym [Directions] | 5:00 p.m. | W 70-46 | |
| Fri., 3/5 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3-4:15 p.m. | ||
| Fri., 3/5 | V Girls Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 5:00 p.m. | W 53-23 | |
| Sat., 3/6 | JV Boys Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 11:15 a.m. | ||
| Sat., 3/6 | FR Boys Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 9:30 a.m. | ||
| Sat., 3/6 | V Boys Ice Hockey | Trumbull | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | 8:30 p.m. | L 1-6 | |
| Sat., 3/6 | JV Boys Ice Hockey | Fairfield Warde/Ludlowe | Home - Milford Ice Pavillion-Ice Rink [Directions] | Canceled | Cancelled | |
| Sat., 3/6 | JV Girls Basketball | Brien McMahon | Home - Staples HS-Staples Gym [Directions] | 9:00 a.m. | ||
| Sat., 3/6 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Terry Conners - Stamford-Ice Rink [Directions] | 2:30 p.m. | W 7-4 | |
| Sat., 3/6 | V Girls Indoor Track | Virtual meet | Home - Staples HS-Field House [Directions] | 9:00 a.m. | ||
| Sun., 3/7 | V Girls Squash | Darien | Away - Ox Ridge Club [Directions] | 7:30 p.m. | ||
| Mon., 3/8 | V Boys Basketball | Fairfield Warde | Home - Staples HS-Staples Gym [Directions] | 5:00 p.m. | W 56-44 | |
| Mon., 3/8 | V Boys Ice Hockey | Wilton | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:30 p.m. | L 0-2 | |
| Mon., 3/8 | V Girls Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 5:00 p.m. | W 49-38 | |
| Mon., 3/8 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 3:30 p.m. | W 8-5 | |
| Tue., 3/9 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3-4:15 p.m. | ||
| Wed., 3/10 | JV Boys Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 3:30 p.m. | ||
| Wed., 3/10 | FR Boys Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:00 p.m. | ||
| Wed., 3/10 | V Boys Ice Hockey | Westhill/Stamford | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4:50 p.m. | L 1-4 | |
| Wed., 3/10 | V Boys Swimming and Diving | Danbury | Home - Staples HS-Staples High School Pool [Directions] | 4:30 p.m. | ||
| Wed., 3/10 | V Girls Basketball | St. Joseph | Home - Staples HS-Staples Gym [Directions] | 5:15 p.m. | L 35-43 | |
| Wed., 3/10 | JV Girls Basketball | Westhill | Home - Staples HS-Staples Gym [Directions] | Canceled | Cancelled | |
| Wed., 3/10 | V Girls Ice Hockey | Greenwich | Home - Terry Conners - Stamford-Ice Rink [Directions] | 7:00 p.m. | L 3-7 | |
| Thu., 3/11 | V Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 5:15 p.m. | W 67-58 | |
| Thu., 3/11 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3-4:15 p.m. | ||
| Fri., 3/12 | JV Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland of Ice-Stadium [Directions] | 4:30 p.m. | ||
| Fri., 3/12 | V Boys Squash | Darien | Home - Intensity Fitness [Directions] | 6:30 p.m. | ||
| Fri., 3/12 | V Girls Basketball | Bassick | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | W 54-32 | |
| Sat., 3/13 | V Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:00 p.m. | L 53-70 | |
| Sat., 3/13 | FR Boys Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 9:30 a.m. | ||
| Sat., 3/13 | V Boys Ice Hockey | Brien McMahon/Norwalk | Home - Milford Ice Pavillion-Ice Rink [Directions] | 5:25 p.m. | W 3-2 | |
| Sat., 3/13 | V Girls Basketball | Ridgefield | Home - Staples HS-Staples Gym [Directions] | 3:30 p.m. | L 37-40 | |
| Sat., 3/13 | JV Girls Basketball | Greenwich | Home - Staples HS-Staples Gym [Directions] | 12:00 p.m. | ||
| Sat., 3/13 | FR Girls Basketball | Danbury | Home - Staples HS-Staples Gym [Directions] | Canceled | Cancelled | |
| Sat., 3/13 | FR Girls Basketball | Brien McMahon | Home - Staples HS-Staples Gym [Directions] | 9:45 a.m. | ||
| Sat., 3/13 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice-New [Directions] | 6:30 p.m. | W 4-3 | |
| Sat., 3/13 | V Girls Indoor Track | Danbury | Home - Staples HS-Field House [Directions] | 11:00 a.m. | ||
| Sun., 3/14 | JV Boys Ice Hockey | Notre Dame-West Haven | Away - West Haven HS-Bennett Rink [Directions] | 8:40 p.m. | ||
| Mon., 3/15 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3-4:15 p.m. | ||
| Mon., 3/15 | JV Girls Basketball | Westhill | Home - Staples HS-Staples Gym [Directions] | 6:15 p.m. | ||
| Mon., 3/15 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 3:15 p.m. | L 2-6 | |
| Tue., 3/16 | V Boys Basketball | Bassick | Home - Staples HS-Staples Gym [Directions] | 5:00 p.m. | L 53-56 | |
| Tue., 3/16 | JV Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena-Patriot Rink [Directions] | 5:20 p.m. | ||
| Wed., 3/17 | FR Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 3:15 p.m. | ||
| Wed., 3/17 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | Canceled | Cancelled | |
| Wed., 3/17 | V Boys Ice Hockey | New Milford | Home - Milford Ice Pavillion-Ice Rink [Directions] | Canceled | Cancelled | |
| Wed., 3/17 | V Girls Basketball | Norwalk | Home - Staples HS-Staples Gym [Directions] | 5:00 p.m. | W 46-39 | |
| Thu., 3/18 | JV Boys Basketball | St. Joseph | Home - Staples HS-Staples Gym [Directions] | Canceled | Cancelled | |
| Thu., 3/18 | V Boys Diving | FCIAC Championship | Away - Norwalk HS-Pool | 4:30 p.m. | ||
| Thu., 3/18 | JV Boys Ice Hockey | Trumbull | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | 4:00 p.m. | ||
| Thu., 3/18 | JV Girls Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 3:30 p.m. | ||
| Thu., 3/18 | V Girls Gymnastics | Norwalk | Home - Westport YMCA [Directions] | 7:00 p.m. | 128.75 | |
| Fri., 3/19 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3-4:15 p.m. | ||
| Fri., 3/19 | V Boys Swimming and Diving | Trumbull, St. Joseph | Away - Hillcrest MS-Pool [Directions] | 3:30 p.m. | ||
| Fri., 3/19 | V Boys Swimming and Diving | TBA | Away - TBA | 4:00 p.m. | ||
| Sat., 3/20 | V Girls Basketball | Danbury | Home - Staples HS-Staples Gym [Directions] | 12:00 p.m. | L 30-47 | |
| Sat., 3/20 | V Girls Indoor Track | New Canaan | Home - Staples HS-Field House [Directions] | 11:00 a.m. | ||
| Mon., 3/22 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3-4:15 p.m. | ||
| Tue., 3/23 | V Girls Gymnastics | Wilton | Away - Wilton HS-Aux Gym [Directions] | 3:45 p.m. | ||
| Thu., 3/25 | V Boys Ice Hockey | Brien McMahon/Norwalk | Home - Milford Ice Pavillion-Ice Rink [Directions] | 5:30 p.m. | ||
| Thu., 3/25 | V Wrestling | Practice | Home - Danbury HS-All Gyms [Directions] | 3-5 p.m. | ||
| Fri., 3/26 | V Girls Gymnastics | FCIAC Championship | Away - Gymnastics and Cheerleading Academy at Connecticut | 5:00 p.m. | 131.05 | |
| Mon., 3/29 | V Boys Golf | Practice | Home - Fairchild Wheeler Golf Course [Directions] | 3-4:30 p.m. | ||
| Tue., 3/30 | V Boys Golf | Practice | Home - Fairchild Wheeler Golf Course [Directions] | 3-4:30 p.m. | ||
| Wed., 3/31 | V Boys Golf | Practice | Home - Fairchild Wheeler Golf Course [Directions] | 3-4:30 p.m. | ||
| Wed., 3/31 | V Co-ed Sailing | GFA, Fairfield Prep | Away - Pequot Yacht Club | 3:00 p.m. | ||
| Wed., 3/31 | V Girls Water Polo | Greenwich YMCA | Home - Greenwich YMCA [Directions] | 7:00 p.m. | ||
| Thu., 4/1 | V Boys Golf | Practice | Home - Fairchild Wheeler Golf Course [Directions] | 3-4:30 p.m. | ||
| Sat., 4/3 | V Baseball | Amity (Scrim.) | Away - Amity Regional HS-John Janenda Field [Directions] | 10:30 a.m. | ||
| Sat., 4/3 | V Baseball | Amity (Scrim.) | Away - Amity Regional HS-John Janenda Field [Directions] | 1:00 p.m. | ||
| Sat., 4/3 | V Boys Lacrosse | Newtown (Scrim.) | Away - Newtown HS-Blue and Gold Stadium [Directions] | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to 2:00 p.m. | ||||||
| Sat., 4/3 | V Boys Rugby | Rugby Trial vs Aspetuck Trial | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Sat., 4/3 | JV Boys Rugby | Rugby Trial vs Aspetuck Trial | Home - Staples HS-Staples Stadium [Directions] | 3:00 p.m. | ||
| Sat., 4/3 | FM Boys Rugby | Rugby Trial vs Aspetuck Trial | Home - Staples HS-Staples Stadium [Directions] | 2:00 p.m. | ||
| Sat., 4/3 | V Girls Rugby | Rugby Trial vs Aspetuck Trial | Home - Staples HS-Staples Stadium [Directions] | 1:00 p.m. | ||
| Mon., 4/5 | V Boys Golf | Practice | Home - Fairchild Wheeler Golf Course [Directions] | 3-4:30 p.m. | ||
| Tue., 4/6 | V Baseball | Fairfield Warde (Scrim.) | Home - Staples HS-Baseball Diamond [Directions] | 3:30 p.m. | ||
| Tue., 4/6 | V Boys Lacrosse | Notre Dame-West Haven (Scrim.) | Home - Staples HS-Staples Stadium [Directions] | 5:00 p.m. | ||
| Wed., 4/7 | V Baseball | Weston (Scrim.) | Home - Staples HS-Baseball Diamond [Directions] | 3:30 p.m. | ||
| Wed., 4/7 | V Co-ed Sailing | GA, Fairfield Prep | Away - Indian Harbor Yacht Club | 3:00 p.m. | ||
| Sat., 4/10 | V Baseball | Darien | Home - Staples HS-Baseball Diamond [Directions] | 1:00 p.m. | W 6-0 | |
| Sat., 4/10 | JV Baseball | Darien | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 9:30 a.m. | ||
| Sat., 4/10 | FR Baseball | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 12:30 p.m. | W 13-0 | |
| Sat., 4/10 | V Boys Lacrosse | New Canaan | Home - Staples HS-Staples Stadium [Directions] | 3:00 p.m. | W 7-3 | |
| Sat., 4/10 | JV Boys Lacrosse | New Canaan | Home - Staples HS-Staples Stadium [Directions] | 12:30 p.m. | W 9-6 | |
| Sat., 4/10 | V Boys Tennis | Ridgefield | Away - Ridgefield HS-RHS Tennis Courts [Directions] | 12:00 p.m. | W 7-0 [Detailed Results] | |
| Sat., 4/10 | V Boys Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 11:00 a.m. | L 0-3 | |
| Sat., 4/10 | JV Boys Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 1:00 p.m. | ||
| Sat., 4/10 | V Co-ed Sailing | Supers Satruday SHS vs GHS, FFLD, DHS, Prep | Away - Indian Harbor Yacht Club | 5:00 a.m. | ||
| Sat., 4/10 | V Softball | Greenwich | Away - Greenwich HS-Softball Field [Directions] | 11:00 a.m. | W 7-0 | |
| Sat., 4/10 | V Girls Tennis | Ridgefield | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Sun., 4/11 | V Boys Rugby | Fairfield Rugby Club | Home - Staples HS-Staples Stadium [Directions] | Postponed | ||
| Sun., 4/11 | JV Boys Rugby | Fairfield Rugby Club | Home - Staples HS-Staples Stadium [Directions] | Postponed | ||
| Sun., 4/11 | FM Boys Rugby | Fairfield Rugby Club | Home - Staples HS-Staples Stadium [Directions] | 2:00 p.m. | ||
| Sun., 4/11 | V Girls Rugby | Fairfield Rugby Club | Home - Staples HS-Staples Stadium [Directions] | 1:00 p.m. | ||
| Mon., 4/12 | V Baseball | Harding | Away - Warren Harding HS-Baseball Field [Directions] | 3:30 p.m. | W 17-0 | |
| Mon., 4/12 | JV Baseball | Darien | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 10:00 a.m. | ||
| Mon., 4/12 | V Softball | Harding | Home - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | W 10-0 | |
| Tue., 4/13 | V Boys Tennis | Greenwich | Away - Greenwich HS-Tennis Courts [Directions] | 1:00 p.m. | W 5-2 [Detailed Results] | |
| Tue., 4/13 | V Girls Lacrosse | Ridgefield | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | W 11-10 | |
| Tue., 4/13 | V Girls Tennis | Greenwich | Home - Staples HS-Staples Tennis Courts [Directions] | 12:00 p.m. | W 7-0 | |
| Wed., 4/14 | V Baseball | St. Joseph | Home - Staples HS-Baseball Diamond [Directions] | 3:00 p.m. | W 7-2 | |
| Wed., 4/14 | JV Baseball | St. Joseph | Away - St. Joseph HS-Baseball Diamond [Directions] | 3:00 p.m. | ||
| Wed., 4/14 | FR Boys Lacrosse | Ridgefield | Away - Ridgefield HS-RHS Lower Grass Field [Directions] | 4:00 p.m. | W 10-1 | |
| Wed., 4/14 | V Boys Tennis | New Canaan | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | W 6-1 [Detailed Results] | |
| Wed., 4/14 | V Softball | St. Joseph | Away - St. Joseph HS-Softball Diamond [Directions] | 4:00 p.m. | L 0-7 | |
| Wed., 4/14 | V Girls Tennis | New Canaan | Away - New Canaan HS-NCHS Tennis Courts [Directions] | 3:15 p.m. | W 5-2 | |
| Wed., 4/14 | V Girls Water Polo | Sacred Heart of Greenwich | Home - Staples HS-Staples High School Pool [Directions] | 4:30 p.m. | ||
| Thu., 4/15 | V Boys Lacrosse | Stamford | Away - Stamford HS-Upper Lacrosse Field [Directions] | 4:00 p.m. | W 25-0 | |
| Thu., 4/15 | JV Boys Lacrosse | Stamford | Away - Stamford HS-Upper Lacrosse Field [Directions] | 5:30 p.m. | W 14-0 | |
| Thu., 4/15 | V Girls Lacrosse | Stamford | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | W 16-5 | |
| Fri., 4/16 | JV Baseball | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 4:30 p.m. | ||
| Fri., 4/16 | FR Boys Lacrosse | Fairfield Ludlowe | Home - Staples HS-Staples Stadium [Directions] | Postponed | ||
| Fri., 4/16 | JV Softball | Brien McMahon | Home - Staples HS-Wakeman Field [Directions] | Postponed | ||
| Sat., 4/17 | V Baseball | Brien McMahon | Home - Staples HS-Baseball Diamond [Directions] | 3:00 p.m. | W 5-4 | |
| Sat., 4/17 | FR Baseball | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 11:00 a.m. | W 10-5 | |
| Sat., 4/17 | FR Baseball | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 9:00 a.m. | L 3-7 | |
| Sat., 4/17 | V Co-ed Sailing | Supers Saturday SHS vs BS, GA, GFA, GHS, FFLD, DHS, Prep | Away - Indian Harbor Yacht Club | 5:00 a.m. | ||
| Mon., 4/19 | V Baseball | Wilton | Away - Wilton HS-Varsity Baseball Field [Directions] | 4:00 p.m. | W 6-0 | |
| Mon., 4/19 | JV Baseball | Wilton | Home - Staples HS-Baseball Diamond [Directions] | 4:30 p.m. | ||
| Mon., 4/19 | V Boys Golf | Stamford | Away - Stamford High-Sterling Farms Golf Course [Directions] | 3:00 p.m. | Staples 180 Stamford 261 | |
| Mon., 4/19 | FR Boys Lacrosse | Wilton | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:30 p.m. | L 6-8 | |
| Mon., 4/19 | V Boys Tennis | Westhill | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | W 6-1 [Detailed Results] | |
| Mon., 4/19 | V Boys Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:30 p.m. | W 3-2 | |
| Mon., 4/19 | JV Boys Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 4/19 | V Softball | Wilton | Home - Staples HS-Wakeman Field [Directions] | 4:30 p.m. | W 3-0 | |
| Tue., 4/20 | V Boys Outdoor Track | St. Joseph | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/20 | V Boys Tennis | Wilton | Away - Wilton HS-Wilton Varsity Tennis Courts [Directions] | 4:30 p.m. | W 6-1 [Detailed Results] | |
| Tue., 4/20 | JV Boys Tennis | Wilton | Away - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/20 | V Girls Outdoor Track | St. Joseph | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/20 | JV Softball | Wilton | Away - Wilton HS-JV Softball Field [Directions] | 4:00 p.m. | ||
| Tue., 4/20 | V Girls Tennis | Wilton | Home - Staples HS-Staples Tennis Courts [Directions] | 4:30 p.m. | W 6-1 | |
| Tue., 4/20 | JV Girls Tennis | Wilton | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:30 p.m. | ||
| Wed., 4/21 | JV Boys Tennis | Fairfield Ludlowe | Home - Staples HS-Town Farms Tennis Courts [Directions] | Postponed | ||
| Wed., 4/21 | JV Boys Volleyball | Fairfield Ludlowe | Home - Staples HS-Staples Gym [Directions] | Canceled | Cancelled | |
| Wed., 4/21 | V Co-ed Sailing | BS, GA, GFA | Away - Indian Harbor Yacht Club | 3:00 p.m. | ||
| Wed., 4/21 | V Girls Golf | Fairfield Warde | Home - Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 4/21 | JV Softball | Danbury | Home - Staples HS-Wakeman Field [Directions] | Postponed | ||
| Wed., 4/21 | V Girls Water Polo | CT Premier | Home - Staples HS-Staples High School Pool [Directions] | 4:30 p.m. | ||
| Thu., 4/22 | JV Baseball | Danbury | Away - Danbury HS-V Baseball Field [Directions] | 4:00 p.m. | ||
| Thu., 4/22 | V Boys Golf | Westhill | Away - EG Brennan Golf Course-E Gaynor Brennan Golf Course [Directions] | 3:20 p.m. | Staples 167 Westhill 182 | |
| Thu., 4/22 | V Boys Lacrosse | Greenwich | Home - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | W 9-6 | |
| Thu., 4/22 | JV Boys Lacrosse | Greenwich | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:30 p.m. | W 13-0 | |
| Thu., 4/22 | V Boys Tennis | Darien | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | W 4-3 [Detailed Results] | |
| Thu., 4/22 | JV Boys Tennis | Darien | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 4/22 | V Boys Volleyball | Fairfield Ludlowe | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Thu., 4/22 | V Girls Golf | Darien | Home - Longshore Golf Course [Directions] | 3:00 p.m. | W 200 - 214 | |
| Thu., 4/22 | JV Girls Golf | Darien | Home - Longshore Golf Course [Directions] | 3:30 p.m. | ||
| Thu., 4/22 | V Girls Lacrosse | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:30 p.m. | L 10-11 | |
| Thu., 4/22 | V Girls Rugby | Notre Dame-Fairfield | Home - Staples HS-Wakeman A [Directions] | 5:00 p.m. | ||
| Thu., 4/22 | V Softball | Brien McMahon | Away - Brien McMahon HS-Softball Diamond [Directions] | 4:30 p.m. | W 14-2 | |
| Thu., 4/22 | V Girls Tennis | Darien | Away - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | L 3-4 | |
| Thu., 4/22 | JV Girls Tennis | Darien | Away - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 4/23 | V Baseball | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 4:30 p.m. | L 5-3 | |
| Fri., 4/23 | JV Baseball | Norwalk | Home - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | ||
| Fri., 4/23 | JV Boys Lacrosse | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 4:00 p.m. | W 16-3 | |
| Fri., 4/23 | FR Boys Lacrosse | Greenwich | Away - Greenwich HS-Cos Cob Park, Benvenuto Field [Directions] | 4:30 p.m. | W 14-0 | |
| Fri., 4/23 | V Boys Rugby | Simsbury | Home - Staples HS-Staples Stadium [Directions] | 6:00 p.m. | ||
| Fri., 4/23 | JV Boys Rugby | Simsbury | Home - Staples HS-Staples Stadium [Directions] | 7:15 p.m. | ||
| Fri., 4/23 | V Boys Tennis | Danbury | Away - Danbury HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 6-1 [Detailed Results] | |
| Fri., 4/23 | V Softball | Norwalk | Home - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | W 16-4 | |
| Fri., 4/23 | V Girls Tennis | Danbury | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Sat., 4/24 | V Baseball | Danbury | Home - Staples HS-Baseball Diamond [Directions] | 12:00 p.m. | W 9-1 | |
| Sat., 4/24 | FR Baseball | Greenwich | Away - Greenwich HS-Baseball Field [Directions] | 10:00 a.m. | W 9-5 | |
| Sat., 4/24 | FR Baseball | Greenwich | Away - Greenwich HS-Baseball Field [Directions] | 12:00 p.m. | L 5-14 | |
| Sat., 4/24 | V Boys Lacrosse | Brien McMahon | Home - Staples HS-Staples Stadium [Directions] | 7:00 p.m. | W 17-4 | |
| Sat., 4/24 | JV Boys Lacrosse | Brien McMahon | Home - Staples HS-Wakeman Field B (turf) [Directions] | 5:30 p.m. | W 16-0 | |
| Sat., 4/24 | FM Boys Rugby | Southington | Home - Staples HS-Staples Stadium [Directions] | 1:00 p.m. | ||
| Sat., 4/24 | FM Boys Rugby | Simsbury | Home - Staples HS-Staples Stadium [Directions] | Canceled | Cancelled | |
| Sat., 4/24 | V Boys Volleyball | Stamford | Home - Staples HS-Staples Gym [Directions] | 10:30 a.m. | W 3-0 | |
| Sat., 4/24 | JV Boys Volleyball | Stamford | Home - Staples HS-Staples Gym [Directions] | 12:00 p.m. | ||
| Sat., 4/24 | V Girls Lacrosse | St. Joseph | Home - Staples HS-Ginny Parker Field [Directions] | 2:00 p.m. | W 14-4 | |
| Sat., 4/24 | V Softball | Danbury | Away - Danbury HS-V Softball field [Directions] | 11:00 a.m. | W 5-3 | |
| Sat., 4/24 | JV Softball | Norwalk | Away - Norwalk HS-Ray Barry Field [Directions] | 10:00 a.m. | ||
| Mon., 4/26 | V Baseball | Stamford | Away - Stamford HS-SHS Baseball Diamond [Directions] | 4:00 p.m. | W 7-5 | |
| Mon., 4/26 | JV Baseball | Stamford | Home - Staples HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Mon., 4/26 | V Boys Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | Staple 169 Trumbull 199 | |
| Mon., 4/26 | FR Boys Lacrosse | New Canaan | Home - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | L 7-8 | |
| Mon., 4/26 | V Boys Tennis | Fairfield Warde | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | W 6-1 [Detailed Results] | |
| Mon., 4/26 | JV Boys Tennis | Fairfield Warde | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 4/26 | V Girls Golf | Greenwich | Home - Longshore Golf Course [Directions] | 3:00 p.m. | W 190 - 210 | |
| Mon., 4/26 | JV Girls Golf | Greenwich | Home - Longshore Golf Course [Directions] | 3:30 p.m. | ||
| Mon., 4/26 | V Softball | Stamford | Home - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | W 2-1 | |
| Mon., 4/26 | V Girls Tennis | Fairfield Warde | Away - Fairfield Warde [Directions] | 4:30 p.m. | W 7-0 | |
| Mon., 4/26 | JV Girls Tennis | Fairfield Warde | Away - Fairfield Woods-Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/27 | JV | Cheshire | Away - Cheshire HS-Grass Fields [Directions] | 4:00 p.m. | W 7-4 | |
| Tue., 4/27 | V Boys Lacrosse | Cheshire | Away - Cheshire HS-Cheshire High School Main Game field [Directions] | 6:00 p.m. | W 12-9 | |
| Tue., 4/27 | JV Boys Lacrosse | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | Postponed | ||
| Tue., 4/27 | V Boys Outdoor Track | Trumbull | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/27 | V Boys Tennis | Trumbull | Away - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Tue., 4/27 | V Boys Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | W 3-1 | |
| Tue., 4/27 | JV Boys Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 4/27 | V Girls Golf | St. Joseph | Home - Longshore Golf Course [Directions] | 3:00 p.m. | W 197 - 217 | |
| Tue., 4/27 | V Girls Lacrosse | Danbury | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | W 23-4 | |
| Tue., 4/27 | V Girls Outdoor Track | Trumbull | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/27 | JV Softball | Stamford | Away - Stamford HS-SHS Softball Diamond [Directions] | 4:00 p.m. | ||
| Tue., 4/27 | V Girls Tennis | Trumbull | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 4/27 | JV Girls Tennis | Trumbull | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/28 | V Baseball | Ridgefield | Home - Staples HS-Baseball Diamond [Directions] | 4:00 p.m. | L 6-3 | |
| Wed., 4/28 | JV Baseball | Ridgefield | Away - Governor Field [Directions] | 4:00 p.m. | ||
| Wed., 4/28 | V Boys Golf | Fairfield Warde | Home - Longshore Golf Course [Directions] | 3:00 p.m. | Staple 149 Warde 157 | |
| Wed., 4/28 | JV Boys Golf | Fairfield Warde | Home - Longshore Golf Course [Directions] | 3:15 p.m. | ||
| Wed., 4/28 | FR Boys Lacrosse | Trumbull | Away - Trumbull HS-The Pit [Directions] | 4:00 p.m. | W 13-1 | |
| Wed., 4/28 | JV Boys Tennis | New Canaan | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/28 | V Boys Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 4/28 | JV Boys Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 4/28 | V Co-ed Sailing | Darien | Home - Pequot Yacht Club [Directions] | 3:45 p.m. | ||
| Wed., 4/28 | V Girls Lacrosse | Wilton | Home - Staples HS-Ginny Parker Field [Directions] | 4:30 p.m. | L 8-10 | |
| Wed., 4/28 | V Softball | Ridgefield | Away - Ridgefield HS-Varsity Field [Directions] | 3:30 p.m. | W 7-0 | |
| Wed., 4/28 | JV Softball | Ridgefield | Away - Ridgefield HS-Varsity Field [Directions] | 5:30 p.m. | ||
| Wed., 4/28 | V Girls Water Polo | CT Premier | Home - Staples HS-Staples High School Pool [Directions] | 4:30 p.m. | ||
| Thu., 4/29 | JV Boys Golf | Ridgefield | Home - Longshore Golf Course [Directions] | Postponed | ||
| Thu., 4/29 | V Boys Lacrosse | Darien | Home - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | L 7-10 | |
| Thu., 4/29 | JV Boys Lacrosse | Darien | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:30 p.m. | W 6-5 | |
| Fri., 4/30 | V Baseball | Trumbull | Away - Trumbull HS-Varsity Baseball Field [Directions] | 4:00 p.m. | W 15-5 | |
| Fri., 4/30 | JV Baseball | Trumbull | Home - Staples HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Fri., 4/30 | FR Boys Lacrosse | Stamford | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | W 14-1 | |
| Fri., 4/30 | V Boys Outdoor Track | Westhill | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Fri., 4/30 | V Boys Rugby | Fairfield Prep | Away - Fairfield University-Grauert Field [Directions] | 4:00 p.m. | ||
| Fri., 4/30 | JV Boys Rugby | Fairfield Prep | Away - Fairfield University-Grauert Field [Directions] | 5:15 p.m. | ||
| Fri., 4/30 | V Boys Tennis | Stamford | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Fri., 4/30 | JV Boys Tennis | Weston | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 4/30 | V Boys Volleyball | St. Joseph | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 4/30 | JV Boys Volleyball | St. Joseph | Home - Staples HS-Staples Gym [Directions] | Canceled | Cancelled | |
| Fri., 4/30 | V Girls Lacrosse | Darien | Away - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | L 8-16 | |
| Fri., 4/30 | V Girls Outdoor Track | Westhill | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Fri., 4/30 | V Softball | Trumbull | Home - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | W 3-2 | |
| Sat., 5/1 | FR Baseball | Darien | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 12:00 p.m. | W 10-9 | |
| Sat., 5/1 | V Boys Lacrosse | Wilton | Away - Wilton HS-Veterans Memorial Stadium [Directions] | 7:00 p.m. | L 10-13 | |
| Sat., 5/1 | JV Boys Lacrosse | Wilton | Away - Wilton HS-Veterans Memorial Stadium [Directions] | 4:30 p.m. | W 12-8 | |
| Sat., 5/1 | FM Boys Rugby | Fairfield Prep | Away - Fairfield University-Grauert Field [Directions] | 10:30 a.m. | ||
| Mon., 5/3 | V Baseball | Bridgeport Central | Home - Staples HS-Baseball Diamond [Directions] | 3:45 p.m. | W 13-0 (5) | |
| Mon., 5/3 | FR Boys Lacrosse | Fairfield Prep | Home - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | W 6-4 | |
| Mon., 5/3 | V Boys Tennis | Bridgeport Central | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Mon., 5/3 | V Girls Golf | Fairfield Warde, Wilton | Home - Longshore Golf Course [Directions] | 3:00 p.m. | W 194 - 211 | |
| Mon., 5/3 | V Girls Tennis | Bridgeport Central | Away - Bridgeport Central HS-Central High School Tennis Courts [Directions] | 5:00 p.m. | W 7-0 | |
| Tue., 5/4 | FR Baseball | Wilton | Home - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | W 9-8 | |
| Tue., 5/4 | V Boys Lacrosse | Glastonbury | Away - Glastonbury HS-Field 1 [Directions] | 6:00 p.m. | W 16-5 | |
| Tue., 5/4 | JV Boys Lacrosse | Glastonbury | Away - Glastonbury HS-Field 11 [Directions] | 4:30 p.m. | W 11-2 | |
| Tue., 5/4 | V Boys Outdoor Track | Ridgefield | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/4 | V Boys Tennis | St. Joseph | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Tue., 5/4 | JV Boys Tennis | Greenwich | Away - Central MS [Directions] | 4:30 p.m. | ||
| Tue., 5/4 | V Boys Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Tue., 5/4 | JV Boys Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 5/4 | JV Girls Golf | Fairfield Ludlowe | Away - Carl Dickman Par 3 [Directions] | 3:15 p.m. | ||
| Tue., 5/4 | JV Girls Golf | Fairfield Warde | Away - Carl Dickman Par 3-Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 5/4 | V Girls Lacrosse | Daniel Hand | Away - Madison Surf Club-Strong Field [Directions] | 5:30 p.m. | W 19-12 | |
| Tue., 5/4 | V Girls Outdoor Track | Ridgefield | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/4 | V Girls Tennis | St. Joseph | Away - St. Joseph HS-Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Tue., 5/4 | JV Girls Tennis | Greenwich | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/5 | V Boys Golf | St. Joseph | Home - Longshore Golf Course [Directions] | 3:00 p.m. | Staple 151 St Joe's 158 | |
| Wed., 5/5 | JV Boys Golf | St. Joseph | Home - Longshore Golf Course [Directions] | 3:15 p.m. | ||
| Wed., 5/5 | FR Boys Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 4:00 p.m. | W 15-0 | |
| Wed., 5/5 | V Girls Water Polo | Sacred Heart of Greenwich | Home - Staples HS-Staples High School Pool [Directions] | 4:30 p.m. | ||
| Thu., 5/6 | JV Baseball | Greenwich | Home - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | ||
| Thu., 5/6 | V Boys Golf | Danbury | Away - Richter Park Golf Course [Directions] | 3:00 p.m. | SHS 168 Danbury 185 | |
| Thu., 5/6 | V Boys Lacrosse | Fairfield Prep | Away - Fairfield University-Rafferty Stadium [Directions] | 7:00 p.m. | L 9-13 | |
| Thu., 5/6 | JV Boys Lacrosse | Fairfield Prep | Away - Fairfield University-Barlow Field [Directions] | 4:00 p.m. | W 6-4 | |
| Thu., 5/6 | V Boys Tennis | Norwalk | Away - Norwalk HS-Tennis Courts [Directions] | 4:30 p.m. | W 7-0 [Detailed Results] | |
| Thu., 5/6 | JV Boys Tennis | Fairfield Warde | Away - Fairfield Warde HS-Knapps Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/6 | V Boys Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Gym [Directions] | 4:30 p.m. | W 3-0 | |
| Thu., 5/6 | JV Boys Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Gym [Directions] | 6:00 p.m. | ||
| Thu., 5/6 | V Girls Golf | New Canaan | Away - New Canaan HS-CCNC [Directions] | 4:00 p.m. | L 205 - 189 | |
| Thu., 5/6 | JV Girls Golf | New Canaan | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 5/6 | V Girls Lacrosse | Guilford | Home - Staples HS-Ginny Parker Field [Directions] | 4:30 p.m. | W 12-10 | |
| Thu., 5/6 | V Girls Rugby | Greenwich | Home - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Thu., 5/6 | V Softball | Greenwich | Home - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | W 18-5 | |
| Thu., 5/6 | JV Softball | Greenwich | Away - Greenwich HS-Softball Field [Directions] | 4:30 p.m. | ||
| Thu., 5/6 | V Girls Tennis | Norwalk | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Thu., 5/6 | JV Girls Tennis | Fairfield Warde | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 5/7 | V Baseball | Fairfield Ludlowe | Home - Staples HS-Baseball Diamond [Directions] | 4:00 p.m. | W 3-1 | |
| Fri., 5/7 | JV Baseball | Fairfield Ludlowe | Away - Owen Fish Park-Owen Fish [Directions] | 4:00 p.m. | ||
| Fri., 5/7 | FR Boys Lacrosse | Darien | Home - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | L 1-8 | |
| Fri., 5/7 | V Boys Rugby | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 5:00 p.m. | ||
| Fri., 5/7 | JV Boys Rugby | Greenwich | Away - Greenwich HS-Field 7 [Directions] | 5:30 p.m. | ||
| Fri., 5/7 | FR Boys Rugby | Greenwich | Away - Greenwich HS-Field 7 [Directions] | 4:30 p.m. | ||
| Fri., 5/7 | V Softball | Fairfield Ludlowe | Away - Sturges Park (Ludlowe HS)-Softball Diamond [Directions] | 4:00 p.m. | L 2-10 | |
| Fri., 5/7 | JV Softball | Fairfield Ludlowe | Home - Staples HS-Wakeman Field [Directions] | Canceled | Cancelled | |
| Fri., 5/7 | V Girls Tennis | Stamford | Away - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Fri., 5/7 | V Girls Water Polo | Greenwich | Away - Greenwich HS-Pool [Directions] | 5:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 4:00 p.m. | ||||||
| Sat., 5/8 | V Baseball | Greenwich | Away - Greenwich HS-Baseball Field [Directions] | 3:00 p.m. | L 7-6 11inn | |
| Sat., 5/8 | FR Baseball | Stamford | Home - Staples HS-Baseball Diamond [Directions] | 10:00 a.m. | W 11-1 | |
| Sat., 5/8 | FR Baseball | Stamford | Home - Staples HS-Baseball Diamond [Directions] | 12:00 p.m. | W 18-3 | |
| Sat., 5/8 | V Boys Lacrosse | Trumbull | Home - Staples HS-Staples Stadium [Directions] | 3:00 p.m. | W 19-8 | |
| Sat., 5/8 | JV Boys Lacrosse | Trumbull | Home - Staples HS-Staples Stadium [Directions] | 12:30 p.m. | W 12-2 | |
| Sat., 5/8 | V Boys Outdoor Track | CT Classic | Away - Danbury HS-Stadium Track | 3:00 p.m. | ||
| Sat., 5/8 | V Boys Volleyball | Darien | Home - Staples HS-Staples Gym [Directions] | 10:00 a.m. | L 0-3 | |
| Sat., 5/8 | JV Boys Volleyball | Darien | Home - Staples HS-Staples Gym [Directions] | 11:30 a.m. | ||
| Sat., 5/8 | V Girls Outdoor Track | CT Classic | Away - Danbury HS-Stadium Track | 3:00 p.m. | ||
| Sat., 5/8 | JV Girls Tennis | St. Joseph | Away - St. Joseph HS-Tennis Courts [Directions] | Postponed | ||
| Sat., 5/8 | V Girls Water Polo | CT Premier & Hydras | Away - Chelsea Piers Pool | 1:00 p.m. | ||
| Mon., 5/10 | V Baseball | Fairfield Warde | Away - Fairfield Warde HS-Baseball Diamond [Directions] | 4:00 p.m. | L 4-3 9inn | |
| Mon., 5/10 | V Boys Golf | Brien McMahon | Home - Longshore Golf Course [Directions] | 3:00 p.m. | SHS 154 McMahon 194 | |
| Mon., 5/10 | JV Boys Golf | Fairfield Warde | Away - Smith Richardson Golf Course [Directions] | 3:30 p.m. | ||
| Mon., 5/10 | V Boys Lacrosse | Danbury | Home - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | W 17-1 | |
| Mon., 5/10 | JV Boys Lacrosse | Darien | Away - Darien HS-DHS Center Oval Turf Field [Directions] | 5:45 p.m. | W 4-3 | |
| Mon., 5/10 | FR Boys Lacrosse | Wilton | Away - Allen's Meadow-Lacrosse Field #1 [Directions] | 4:30 p.m. | ||
| Mon., 5/10 | V Boys Outdoor Track | Danbury | Away - Danbury HS-DHS Stadium [Directions] | 4:00 p.m. | ||
| Mon., 5/10 | V Boys Tennis | Brien McMahon | Away - Brien McMahon HS-Tennis Courts [Directions] | 4:30 p.m. | W 7-0 [Detailed Results] | |
| Mon., 5/10 | JV Boys Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 5/10 | V Boys Volleyball | Ridgefield | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 5/10 | JV Boys Volleyball | Ridgefield | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Mon., 5/10 | V Girls Golf | Ridgefield | Home - Longshore Golf Course [Directions] | 3:30 p.m. | W 190 - 194 | |
| Mon., 5/10 | V Girls Outdoor Track | Danbury | Away - Danbury HS-DHS Stadium [Directions] | 4:00 p.m. | ||
| Mon., 5/10 | V Girls Tennis | Brien McMahon | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Mon., 5/10 | JV Girls Tennis | Ridgefield | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/11 | JV Baseball | Fairfield Warde | Home - Staples HS-Baseball Diamond [Directions] | 3:30 p.m. | ||
| Tue., 5/11 | V Boys Golf | Ridgefield | Away - Silver Spring Golf Course [Directions] | 3:15 p.m. | SHS 172 Ridgefield 157 | |
| Tue., 5/11 | JV Boys Golf | Ridgefield | Away - Silver Spring Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 5/11 | V Boys Lacrosse | Westhill | Home - Staples HS-Staples Stadium [Directions] | 7:00 p.m. | W 20-1 | |
| Tue., 5/11 | JV Boys Lacrosse | Westhill | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:30 p.m. | W 15-0 | |
| Tue., 5/11 | V Boys Tennis | Fairfield Ludlowe | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Tue., 5/11 | JV Boys Tennis | Trumbull | Away - Unity Park [Directions] | Postponed | ||
| Tue., 5/11 | V Boys Volleyball | Norwalk | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | W 3-1 | |
| Tue., 5/11 | V Girls Golf | Danbury | Home - Longshore Golf Course [Directions] | 3:00 p.m. | W 188 - 254 | |
| Tue., 5/11 | JV Girls Golf | Danbury | Home - Longshore Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 5/11 | V Girls Lacrosse | Westhill | Away - Westhill HS-Westhill Front Turf Field [Directions] | 4:00 p.m. | W 18-6 | |
| Tue., 5/11 | V Softball | Fairfield Warde | Home - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | L 4-11 | |
| Tue., 5/11 | JV Softball | Fairfield Warde | Away - Melville Park [Directions] | Canceled | Cancelled | |
| Tue., 5/11 | V Girls Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 5/11 | JV Girls Tennis | Fairfield Ludlowe | Away - Dwight Elementary School-Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/12 | JV Boys Golf | Wilton | Home - Longshore Golf Course [Directions] | 3:15 p.m. | ||
| Wed., 5/12 | FR Boys Lacrosse | Fairfield Warde | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Wed., 5/12 | V Girls Golf | Ridgefield | Away - Ridgefield Golf Course [Directions] | 2:30 p.m. | W 200 - 213 | |
| Wed., 5/12 | JV Girls Golf | Ridgefield | Away - Ridgefield Golf Course [Directions] | 2:30 p.m. | ||
| Wed., 5/12 | V Girls Lacrosse | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 5:30 p.m. | W 15-7 | |
| Wed., 5/12 | V Girls Tennis | Westhill | Away - Westhill HS-Westhill Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Wed., 5/12 | JV Girls Tennis | Greenwich | Away - Binney Park [Directions] | 4:30 p.m. | ||
| Wed., 5/12 | V Girls Water Polo | G-Aquatics | Home - Staples HS-Staples High School Pool [Directions] | 4:30 p.m. | ||
| Thu., 5/13 | V Baseball | Westhill | Home - Staples HS-Baseball Diamond [Directions] | 4:00 p.m. | W 14-2 (5) | |
| Thu., 5/13 | V Boys Golf | Darien | Home - Longshore Golf Course [Directions] | 3:00 p.m. | SHS 150 Darien 153 | |
| Thu., 5/13 | JV Boys Golf | Darien | Home - Longshore Golf Course [Directions] | 3:15 p.m. | ||
| Thu., 5/13 | V Boys Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS [Directions] | 6:00 p.m. | W 12-9 | |
| Thu., 5/13 | JV Boys Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | W 12-1 | |
| Thu., 5/13 | V Boys Outdoor Track | Stamford | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Thu., 5/13 | JV Boys Tennis | Greenwich | Away - Central MS [Directions] | 4:30 p.m. | ||
| Thu., 5/13 | V Boys Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Thu., 5/13 | JV Boys Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 5/13 | V Girls Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | 3:30 p.m. | L 194 - 186 | |
| Thu., 5/13 | V Girls Lacrosse | Fairfield Ludlowe | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | L 11-12 | |
| Thu., 5/13 | V Girls Outdoor Track | Stamford | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Thu., 5/13 | V Softball | Westhill | Away - Westhill HS-Varsity Softball Field [Directions] | 4:00 p.m. | W 4-1 | |
| Thu., 5/13 | JV Softball | Greenwich | Home - Staples HS-Wakeman Field [Directions] | Canceled | Cancelled | |
| Thu., 5/13 | V Girls Water Polo | Greenwich | Home - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Fri., 5/14 | JV Baseball | Westhill | Away - Westhill HS-Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 5/14 | JV Boys Lacrosse | Fairfield Warde | Home - Staples HS-Wakeman Field B (turf) [Directions] | Canceled | Cancelled | |
| Fri., 5/14 | FR Boys Lacrosse | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 4:30 p.m. | ||
| Fri., 5/14 | V Boys Rugby | Darien | Away - Royle School Field [Directions] | Canceled | Cancelled | |
| Fri., 5/14 | JV Boys Rugby | Darien | Away - Darien HS-Royle Field @ 133 Mansfield Ave, Darien, CT 06820 [Directions] | 4:00 p.m. | ||
| Fri., 5/14 | V Boys Volleyball | Greenwich | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 5/14 | JV Boys Volleyball | Greenwich | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Fri., 5/14 | JV Softball | Westhill | Home - Staples HS-Wakeman Field [Directions] | Canceled | Cancelled | |
| Fri., 5/14 | V Girls Tennis | Norwalk | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 5/14 | V Girls Water Polo | Greenwich | Home - Staples HS-Staples High School Pool [Directions] | Canceled | Cancelled | |
| Sat., 5/15 | FR Baseball | Stamford | Home - Fairfield Warde HS-Baseball Diamond [Directions] | 11:00 a.m. | W 10-0 | |
| Sat., 5/15 | FR Baseball | Fairfield Warde | Away - Fairfield Warde HS-Baseball Diamond [Directions] | 9:00 a.m. | L 2-3 | |
| Sat., 5/15 | V Boys Lacrosse | Ridgefield | Home - Staples HS-Staples Stadium [Directions] | 3:00 p.m. | W 12-11 | |
| Sat., 5/15 | JV Boys Lacrosse | Ridgefield | Home - Staples HS-Staples Stadium [Directions] | 12:30 p.m. | W 12-2 | |
| Sun., 5/16 | V Boys Rugby | Notre Dame-Fairfield | Home - Staples HS-Staples Stadium [Directions] | 5:00 p.m. | ||
| Sun., 5/16 | FM Boys Rugby | Notre Dame-Fairfield | Home - Staples HS-Staples Stadium [Directions] | 6:15 p.m. | ||
| Mon., 5/17 | V Baseball | New Canaan | Home - Staples HS-Baseball Diamond [Directions] | 4:00 p.m. | W 2-1 | |
| Mon., 5/17 | JV Baseball | New Canaan | Away - Mead Park-Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/17 | FR Boys Lacrosse | Trumbull | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:15 p.m. | W 12-0 | |
| Mon., 5/17 | V Boys Outdoor Track | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Mon., 5/17 | V Boys Volleyball | Westhill | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 5/17 | JV Boys Volleyball | Westhill | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Mon., 5/17 | V Girls Outdoor Track | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Mon., 5/17 | V Softball | New Canaan | Away - Waveny Park-Orchard Field [Directions] | 6:30 p.m. | W 15-2 | |
| Tue., 5/18 | V Boys Golf | Wilton | Home - Longshore Golf Course [Directions] | 3:00 p.m. | SHS 154 Wilton 157 | |
| Tue., 5/18 | JV Boys Golf | Wilton | Away - Rolling Hills Country Club [Directions] | 3:15 p.m. | ||
| Tue., 5/18 | V Boys Tennis | Westhill | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/18 | V Boys Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Tue., 5/18 | JV Boys Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | Canceled | Cancelled | |
| Tue., 5/18 | V Girls Golf | Trumbull | Home - Longshore Golf Course [Directions] | 3:30 p.m. | W 187 - 196 | |
| Tue., 5/18 | JV Girls Golf | Fairfield Ludlowe | Away - Carl Dickman Par 3 [Directions] | 3:15 p.m. | ||
| Tue., 5/18 | JV Girls Golf | Fairfield Warde | Away - Carl Dickman Par 3-Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 5/18 | V Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 5:30 p.m. | W 11-3 | |
| Tue., 5/18 | V Girls Rugby | Fairfield Rugby Club & Mid-State | Home - Staples HS-Staples Stadium [Directions] | 5:00 p.m. | ||
| Wed., 5/19 | V Baseball | Darien | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | W 4-0 | |
| Wed., 5/19 | JV Baseball | Darien | Home - Staples HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 5/19 | FR Baseball | St. Joseph | Home - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | W 5-2 | |
| Wed., 5/19 | V Boys Golf | Norwalk | Home - Longshore Golf Course [Directions] | 3:00 p.m. | SHS 150 Norwalk 182 | |
| Wed., 5/19 | JV Boys Golf | Fairfield Prep | Home - Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 5/19 | V Boys Lacrosse | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 4:30 p.m. | W 16-14 | |
| Wed., 5/19 | FR Boys Lacrosse | Greenwich | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Wed., 5/19 | V Girls Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 3:50 p.m. | L 209-197 | |
| Wed., 5/19 | V Softball | Darien | Home - Greens Farms Elementary School-Softball Field [Directions] | 7:00 p.m. | W 5-4 | |
| Wed., 5/19 | JV Softball | Darien | Away - Darien HS-DHS - Softball - JV Field [Directions] | Canceled | Cancelled | |
| Wed., 5/19 | V Girls Tennis | Wilton | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/20 | V Boys Golf | New Canaan | Away - CCNC [Directions] | 3:45 p.m. | SHS 170 New Canaan 148 | |
| Thu., 5/20 | JV Boys Golf | New Canaan | Home - Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 5/20 | V Boys Rugby | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 5:00 p.m. | ||
| Thu., 5/20 | JV Boys Rugby | Ridgefield | Away - Ridgefield HS-Tiger Hollow Turf Field II [Directions] | 6:30 p.m. | ||
| Thu., 5/20 | V Boys Tennis | New Canaan | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/20 | V Boys Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | L 0-3 | |
| Thu., 5/20 | JV Boys Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 5/20 | V Girls Golf | Fairfield Warde | Away - Smith Richardson Golf Course [Directions] | 3:00 p.m. | L 204 - 199 | |
| Thu., 5/20 | V Girls Rugby | Midstate | Home - Staples HS-Staples Stadium [Directions] | Canceled | Cancelled | |
| Thu., 5/20 | JV Softball | St. Joseph | Home - Staples HS-Wakeman Field [Directions] | Canceled | Cancelled | |
| Fri., 5/21 | V Baseball | Darien | Home - Staples HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Fri., 5/21 | FR Boys Lacrosse | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 5/21 | V Boys Volleyball | St. Joseph | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 5/21 | V Girls Lacrosse | New Canaan | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | L 2-15 | |
| Fri., 5/21 | V Softball | Brien McMahon | Home - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | ||
| Sat., 5/22 | FR Baseball | St. Joseph | Home - Staples HS-Baseball Diamond [Directions] | 10:00 a.m. | W 8-7 | |
| Sat., 5/22 | FR Baseball | St. Joseph | Home - Staples HS-Baseball Diamond [Directions] | 12:00 p.m. | W 8-7 | |
| Sat., 5/22 | V Boys Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 2:00 p.m. | W 12-9 | |
| Sat., 5/22 | JV Boys Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 4:30 p.m. | W 9-2 | |
| Sat., 5/22 | FM Boys Rugby | Southington | Home - Staples HS-Staples Stadium [Directions] | Canceled | Cancelled | |
| Sat., 5/22 | JV Softball | Harding | Away - Warren Harding HS-Beardsley Park #3 [Directions] | Canceled | Cancelled | |
| Sun., 5/23 | V Boys Rugby | Xavier NY | Home - Staples HS-Staples Stadium [Directions] | 1:00 p.m. | ||
| Sun., 5/23 | JV Boys Rugby | Xavier NY | Home - Staples HS-Staples Stadium [Directions] | 2:15 p.m. | ||
| Sun., 5/23 | FM Boys Rugby | Xavier NY | Home - Staples HS-Staples Stadium [Directions] | 3:30 p.m. | ||
| Mon., 5/24 | V Boys Golf | Fairfield Ludlowe | Home - Longshore Golf Course [Directions] | 3:00 p.m. | SHS 151 Ludlowe 152 | |
| Mon., 5/24 | JV Boys Golf | Fairfield Ludlowe | Home - Longshore Golf Course [Directions] | 3:15 p.m. | ||
| Mon., 5/24 | V Boys Lacrosse | Fairfield Ludlowe | Home - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | W 15-9 | |
| Mon., 5/24 | V Boys Volleyball | Ridgefield | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Mon., 5/24 | V Girls Outdoor Track | FCIAC Championship | Away - Danbury HS | 4:00 p.m. | ||
| Mon., 5/24 | V Softball | Fairfield Warde | Home - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | ||
| Mon., 5/24 | V Girls Tennis | New Canaan | Home - Staples HS-Staples Tennis Courts [Directions] | 3:30 p.m. | ||
| Tue., 5/25 | V Boys Golf | Greenwich | Home - Longshore Golf Course [Directions] | 3:00 p.m. | SHS 149 GHS 149 | |
| Tue., 5/25 | JV Boys Golf | Greenwich | Home - Longshore Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 5/25 | FR Boys Lacrosse | Fairfield Prep | Away - Fairfield University - Barlow Field-Barlow Field Fairfield University [Directions] | Postponed | ||
| Tue., 5/25 | V Boys Outdoor Track | FCIAC Championship | Away - Danbury HS | 4:00 p.m. | ||
| Tue., 5/25 | V Boys Tennis | Darien | Home - Wilton HS-Wilton HS tennis courts [Directions] | 4:00 p.m. | ||
| Tue., 5/25 | V Girls Golf | Darien | Away - Country Club of Darien [Directions] | 3:00 p.m. | W 187 - 219 | |
| Tue., 5/25 | JV Softball | Trumbull | Away - Trumbull HS-Varsity Softball Diamond [Directions] | Canceled | Cancelled | |
| Wed., 5/26 | V Baseball | St. Joseph (Scrim.) | Away - St. Joseph HS-Baseball Diamond [Directions] | 3:00 p.m. | ||
| Wed., 5/26 | JV Boys Golf | Fairfield Prep | Away - Patterson Club [Directions] | 3:05 p.m. | ||
| Wed., 5/26 | V Boys Lacrosse | Wilton | Home - Staples HS-Staples Stadium [Directions] | 5:00 p.m. | W 16-2 | |
| Wed., 5/26 | V Girls Golf | Fairfield Ludlowe | Home - Longshore Golf Course [Directions] | 3:00 p.m. | W 181 - 187 | |
| Wed., 5/26 | V Softball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 5:00 p.m. | ||
| Thu., 5/27 | FR Boys Lacrosse | Ridgefield | Home - Staples HS-Staples Stadium [Directions] | Canceled | Cancelled | |
| Thu., 5/27 | V Girls Golf | St. Joseph | Away - Tashua Knolls Golf Course [Directions] | 3:00 p.m. | W 189 - 200 | |
| Thu., 5/27 | V Girls Rugby | North Haven | Away - North Haven Athletic Complex-All-Purpose Field [Directions] | 4:30 p.m. | ||
| Thu., 5/27 | V Girls Tennis | Darien | Home - Wilton HS-Wilton HS tennis courts [Directions] | 5:00 p.m. | ||
| Fri., 5/28 | V Boys Lacrosse | Darien | Away - New Canaan HS-Dunning Stadium [Directions] | 5:00 p.m. | L 3-15 | |
| Fri., 5/28 | V Girls Lacrosse | Trumbull | Home - Staples HS-Ginny Parker Field [Directions] | 5:00 p.m. | W 15-4 | |
| Fri., 5/28 | V Girls Tennis | Shelton | Home - Staples HS-Staples Tennis Courts [Directions] | 1:00 p.m. | ||
| Sat., 5/29 | V Boys Rugby | Ridgefield | Away - Ridgefield HS-Tiger Hollow Turf Field II [Directions] | 9:00 a.m. | ||
| Sat., 5/29 | V Boys Tennis | Trumbull | Home - Staples HS-Intensity Racquet Club [Directions] | 5:00 p.m. | ||
| Tue., 6/1 | V Baseball | New Canaan | Home - Staples HS-Baseball Diamond [Directions] | 3:30 p.m. | ||
| Tue., 6/1 | V Boys Outdoor Track | CIAC Class LL Boys Outdoor Track Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 6/1 | V Boys Tennis | Greenwich | Home - Staples HS-Staples Tennis Courts [Directions] | 3:00 p.m. | ||
| Tue., 6/1 | V Girls Golf | New Canaan (Scrim.) | Home - Staples HS-Fairfield Wheeler [Directions] | TBA | ||
| Tue., 6/1 | V Girls Lacrosse | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 5:00 p.m. | L 15-8 | |
| Tue., 6/1 | V Girls Outdoor Track | CIAC Class LL Girls Outdoor Track Championship | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 6/1 | V Softball | Danbury | Home - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | ||
| Tue., 6/1 | V Girls Tennis | Darien | Away - Darien HS-DHS Tennis Courts [Directions] | 3:00 p.m. | ||
| Wed., 6/2 | V Boys Lacrosse | Ridgefield | Home - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | L 3-4 | |
| Wed., 6/2 | V Boys Tennis | Ridgefield | Home - Staples HS-Staples Tennis Courts [Directions] | 3:00 p.m. | ||
| Wed., 6/2 | V Boys Volleyball | Ridgefield | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Wed., 6/2 | V Softball | Maloney | Home - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | ||
| Wed., 6/2 | V Girls Tennis | Fairfield Ludlowe | Home - Staples HS-Staples Tennis Courts [Directions] | 1:00 p.m. | ||
| Thu., 6/3 | V Boys Golf | FCIAC Championship | Away - Fairchild Wheeler Golf Course | TBA | ||
| Thu., 6/3 | V Boys Tennis | Westhill | Away - Tennis & Fitness Ctr (Rocky Hill) [Directions] | 12:00 p.m. | ||
| Thu., 6/3 | V Girls Golf | FCIAC Championship | Away - Fairchild Wheeler Golf Course | TBA | ||
| Thu., 6/3 | V Girls Rugby | Darien | Away - Royle School Field [Directions] | 4:00 p.m. | ||
| Thu., 6/3 | V Girls Tennis | Amity | Away - Tennis & Fitness Ctr (Rocky Hill) [Directions] | 10:00 a.m. | ||
| Sat., 6/5 | V Boys Rugby | Greenwich | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Sat., 6/5 | V Softball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 3:00 p.m. | ||
| Mon., 6/7 | V Boys Golf | CIAC Boys Div. I Golf Championship | Away - Tallwood CC | 8:00 a.m. | ||
| Wed., 6/9 | V Boys Outdoor Track | CIAC Open Boys Outdoor Track Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Wed., 6/9 | V Girls Golf | CIAC Girls Div. I Golf Championship | Away - Grassy Hill | 8:30 a.m. | ||
| Wed., 6/9 | V Girls Outdoor Track | CIAC Open Girls Outdoor Track Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Sat., 6/12 | V Boys Golf | CIAC State Open Golf Championship | Away - Black Hall Club | 1:00 p.m. | ||
| Sat., 6/12 | V Boys Rugby | Practice | Home - Staples HS-Staples Stadium [Directions] | 9:30 a.m.-12:30 p.m. | ||
| Sat., 6/12 | V Girls Golf | CIAC State Open Golf Championship | Away - Black Hall Club | 1:00 p.m. | ||
| Mon., 6/14 | V Boys Outdoor Track | CIAC Boys Hammer Throw Championship | Away - Manchester | 3:30 p.m. | ||
| Mon., 6/14 | V Girls Outdoor Track | CIAC Girls Hammer Throw Championship | Away - Manchester | 3:30 p.m. | ||
| Tue., 6/15 | V Boys Outdoor Track | CIAC Boys Decathlon Championship Day 1 | Away - Manchester | 10:00 a.m. | ||
| Tue., 6/15 | V Girls Outdoor Track | CIAC Girls Heptathlon Championship Day 1 | Away - Manchester | 10:30 a.m. | ||
| Tue., 6/15 | V Girls Outdoor Track | CIAC Girls Steeplechase Championship | Away - Manchester | 3:30 p.m. | ||
| Wed., 6/16 | V Boys Outdoor Track | CIAC Boys Decathlon Championship Day 2 | Away - Manchester | 10:00 a.m. | ||
| Wed., 6/16 | V Boys Outdoor Track | CIAC Boys Steeplechase Championship | Away - Manchester | 3:30 p.m. | ||
| Wed., 6/16 | V Girls Outdoor Track | CIAC Girls Heptathlon Championship Day 2 | Away - Manchester | 10:00 a.m. | ||