| Staples 2021-22 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 1214 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Fri., 7/30 | Miscellaneous Events | Cheerleading | Home - Staples HS-Staples Stadium [Directions] | 7:00 p.m. | ||
| Wed., 8/25 | V Football | Fairfield Prep, Wilton (Scrim.) | Away - Fairfield University-Rafferty Stadium [Directions] | 4:30 p.m. | ||
| Wed., 8/25 | FR Football | Wilton, Fairfield Prep (Scrim.) | Away - Wilton HS-Fuijitani Field -Turf [Directions] | 3:30 p.m. | ||
| Sat., 8/28 | V Football | Practice | Home - Shelton HS-Upper Field [Directions] | 10:30 a.m.-12:30 p.m. | ||
| Mon., 8/30 | V Boys Golf | Brien McMahon | Home - Longshore Golf Course [Directions] | 3:00 p.m. | SHS-146 McMahon-197 | |
| Mon., 8/30 | JV Field Hockey | Greenwich Academy (Scrim.) | Home - Staples HS-Ginny Parker Field [Directions] | 5:00 p.m. | ||
| Mon., 8/30 | V Girls Soccer | Greenwich Academy (Scrim.) | Away - Greenwich Academy | 4:00 p.m. | ||
| Tue., 8/31 | V Boys Soccer | Joel Barlow (Scrim.) | Away - Joel Barlow HS-Field J (Competition Field) [Directions] | 4:15 p.m. | ||
| Tue., 8/31 | V Girls Soccer | Greens Farms Academy (Scrim.) | Away - Greens Farms Academy-Greens Farms Academy - Turf Blue | 4:00 p.m. | ||
| Wed., 9/1 | V Boys Golf | Wilton | Away - Rolling Hills Country Club [Directions] | 3:15 p.m. | SHS-166 Wilton-164 | |
| Wed., 9/1 | JV Boys Golf | Wilton | Away - Rolling Hills Country Club [Directions] | 3:15 p.m. | ||
| Wed., 9/1 | JV Girls Soccer | Rye Country Day (NY) (Scrim.) | Away - Rye Country Day School | Canceled | Cancelled | |
| Thu., 9/2 | V Football | Brien McMahon (Scrim.) | Home - Staples HS-Staples Stadium [Directions] | 4:30 p.m. | ||
| Thu., 9/2 | V Boys Golf | Westhill | Home - Longshore Golf Course [Directions] | 3:00 p.m. | SHS-148 Westhill-178 | |
| Thu., 9/2 | V Boys Soccer | Fairfield Prep (Scrim.) | Away - Fairfield University-Rafferty Stadium [Directions] | 4:15 p.m. | ||
| Thu., 9/2 | V Field Hockey | Greens Farms Academy (Scrim.) | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Thu., 9/2 | V Girls Soccer | Berlin (Scrim.) | Away - Sage Park Berlin-Scalise Field [Directions] | 6:00 p.m. | ||
| Thu., 9/2 | V Girls Volleyball | New Fairfield (Scrim.) | Away - New Fairfield HS-High School Gym [Directions] | 4:30 p.m. | ||
| Thu., 9/2 | JV Girls Volleyball | New Fairfield (Scrim.) | Away - New Fairfield MS-Gym [Directions] | 4:30 p.m. | ||
| Fri., 9/3 | FR Football | Shelton (Scrim.) | Away - Shelton HS-Finn Stadium [Directions] | 4:00 p.m. | ||
| Sat., 9/4 | V Boys Soccer | Wethersfield, Kingswood-Oxford, Tolland (Scrim.) | Away - Wethersfield HS-Cottone Field [Directions] | 10:00 a.m. | ||
| Sun., 9/5 | V Girls Soccer | Pomperaug (Scrim.) | Away - Treadwell Park-Newtown Treadwell Park [Directions] | 10:20 a.m. | ||
| Sun., 9/5 | V Girls Soccer | Newtown | Away - Treadwell Park-Newtown Treadwell Park [Directions] | 11:45 a.m. | ||
| Sun., 9/5 | V Girls Soccer | Naugatuck (Scrim.) | Away - Treadwell Park-Treadwell Town Park--Tilson Field [Directions] | 9:00 a.m. | ||
| Sun., 9/5 | V Girls Soccer | Danbury (Scrim.) | Home - Treadwell Park-Newtown Treadwell Park [Directions] | 12:20 p.m. | ||
| Tue., 9/7 | Miscellaneous Events | Rosh Hashanah | Home - Staples HS-Staples Stadium [Directions] | 12:00 p.m. | ||
| Wed., 9/8 | V Boys Golf | Fairfield Warde | Away - Smith Richardson Golf Course [Directions] | 3:30 p.m. | SHS-164 Warde-165 | |
| Wed., 9/8 | JV Boys Golf | Fairfield Warde | Away - Smith Richardson Golf Course [Directions] | 3:30 p.m. | ||
| Thu., 9/9 | FR Football | Trumbull | Home - Saugatuck Elementary School-PJ Romano Field [Directions] | 4:00 p.m. | ||
| Thu., 9/9 | V Boys Golf | Norwalk | Away - Oak Hills Golf Course [Directions] | 3:30 p.m. | SHS-160 Norwalk-195 | |
| Thu., 9/9 | V Field Hockey | Norwalk | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | W 9-0 | |
| Thu., 9/9 | V Girls Soccer | Ridgefield | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | T 2-2 | |
| Thu., 9/9 | JV Girls Soccer | Ridgefield | Away - Ridgefield HS-RHS Lower Grass Field [Directions] | 4:30 p.m. | ||
| Thu., 9/9 | V Girls Volleyball | Weston | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | L 2-3 | |
| Thu., 9/9 | JV Girls Volleyball | Weston | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Thu., 9/9 | FR Girls Volleyball | Weston | Home - Staples HS-Field House [Directions] | 4:00 p.m. | ||
| Fri., 9/10 | V Football | Trumbull | Home - Staples HS-Staples Stadium [Directions] | 7:00 p.m. | W 27-20 | |
| Fri., 9/10 | V Boys Soccer | Ridgefield | Home - Staples HS-Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 5-0 | |
| Fri., 9/10 | FR Girls Volleyball | Darien | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/10 | Miscellaneous Events | Cheerleading | Home - Staples HS-Staples Stadium [Directions] | 7:00 p.m. | ||
| Sat., 9/11 | JV Football | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 10:30 a.m. | ||
| Sat., 9/11 | JV Boys Soccer | Ridgefield | Home - Staples HS-Wakeman Field E (grass) [Directions] | 10:00 a.m. | W 2-0 | |
| Sat., 9/11 | FR Boys Soccer | Darien | Home - Staples HS-Wakeman Field B (turf) [Directions] | 12:00 p.m. | W 6-0 | |
| Sat., 9/11 | V Field Hockey | Branford | Away - Branford HS-Athletic Turf Field [Directions] | 5:00 p.m. | W 5-1 | |
| Sat., 9/11 | JV Field Hockey | Branford | Away - Branford HS-Athletic Turf Field [Directions] | 3:30 p.m. | ||
| Sat., 9/11 | FR Field Hockey | Darien | Home - Staples HS-Ginny Parker Field [Directions] | 10:00 a.m. | ||
| Sat., 9/11 | FR Girls Soccer | Masuk | Home - Staples HS-Loeffler Field - Staples HS [Directions] | Postponed | ||
| Sat., 9/11 | Miscellaneous Events | ACT Date | Home - Staples HS-Staples Stadium [Directions] | 9:00 a.m. | ||
| Mon., 9/13 | V Boys Golf | Stamford | Away - Stamford High-Sterling Farms Golf Course [Directions] | 3:00 p.m. | SHS-146 Stamford-186 | |
| Mon., 9/13 | V Girls Soccer | New Canaan | Home - Staples HS-Loeffler Field - Staples HS [Directions] | 4:00 p.m. | T 1-1 | |
| Mon., 9/13 | JV Girls Soccer | New Canaan | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Mon., 9/13 | V Girls Volleyball | Fairfield Warde | Home - Staples HS-Staples Gym [Directions] | 7:00 p.m. | W 3-1 | |
| Mon., 9/13 | JV Girls Volleyball | Fairfield Warde | Home - Staples HS-Staples Gym [Directions] | 5:00 p.m. | ||
| Mon., 9/13 | FR Girls Volleyball | Trumbull | Home - Staples HS-Staples Gym [Directions] | 3:30 p.m. | ||
| Tue., 9/14 | V Boys Cross Country | Danbury, Darien, Norwalk | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 9/14 | V Boys Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:30 p.m. | SHS-161 Trumbull-181 | |
| Tue., 9/14 | JV Boys Golf | Ridgefield | Home - Longshore Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 9/14 | JV Boys Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | Canceled | Cancelled | |
| Tue., 9/14 | V Boys Soccer | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 6:30 p.m. | W 2-1 | |
| Tue., 9/14 | JV Boys Soccer | New Canaan | Away - Conner Field, New Cannan [Directions] | 4:00 p.m. | W 1-0 | |
| Tue., 9/14 | V Boys Water Polo | Greenwich | Home - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Tue., 9/14 | JV Boys Water Polo | Greenwich | Home - Staples HS-Staples High School Pool [Directions] | 5:00 p.m. | ||
| Tue., 9/14 | V Girls Cross Country | Danbury, Darien, Norwalk | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 9/14 | V Field Hockey | Wilton | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | T 2-2 | |
| Tue., 9/14 | JV Field Hockey | Wilton | Home - Staples HS-Ginny Parker Field [Directions] | 5:15 p.m. | ||
| Tue., 9/14 | V Girls Swimming and Diving | Ridgefield | Away - Barlow Mountain Pool [Directions] | 4:00 p.m. | ||
| Wed., 9/15 | FR Football | St. Joseph | Home - Saugatuck Elementary School-PJ Romano Field [Directions] | 3:00 p.m. | ||
| Wed., 9/15 | FR Boys Soccer | Trumbull | Away - Trumbull HS-The Pit [Directions] | 3:00 p.m. | T 1-1 | |
| Wed., 9/15 | FR Girls Soccer | New Canaan | Home - Staples HS-Wakeman Field E (grass) [Directions] | 3:00 p.m. | ||
| Thu., 9/16 | Miscellaneous Events | Yom Kippur | Home - Staples HS-Staples Stadium [Directions] | 12:00 p.m. | ||
| Fri., 9/17 | V Football | St. Joseph | Home - Staples HS-Staples Stadium [Directions] | 7:00 p.m. | L 14-35 | |
| Fri., 9/17 | V Girls Soccer | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:30 p.m. | W 1-0 | |
| Fri., 9/17 | JV Girls Soccer | Greenwich | Away - Cos Cob Park-Binney Park [Directions] | 4:45 p.m. | ||
| Fri., 9/17 | Miscellaneous Events | Cheerleading | Home - Staples HS-Staples Stadium [Directions] | 7:00 p.m. | ||
| Sat., 9/18 | V Boys Cross Country | Wilton | Away - Allen's Meadow-XC Course [Directions] | 9:00 a.m. | ||
| Sat., 9/18 | JV Football | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 10:00 a.m. | ||
| Sat., 9/18 | V Boys Soccer | Greenwich | Home - Staples HS-Loeffler Field - Staples HS [Directions] | 11:30 a.m. | T 0-0 | |
| Sat., 9/18 | JV Boys Soccer | Greenwich | Home - Staples HS-Wakeman Field B (turf) [Directions] | 11:00 a.m. | W 4-3 | |
| Sat., 9/18 | FR Boys Soccer | Masuk | Home - Staples HS-Wakeman Field B (turf) [Directions] | 9:00 a.m. | W 9-0 | |
| Sat., 9/18 | V Girls Cross Country | Wilton | Away - Staples HS-Staples Stadium [Directions] | 9:00 a.m. | ||
| Sat., 9/18 | FR Field Hockey | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 11:00 a.m. | ||
| Sat., 9/18 | FR Girls Soccer | Newtown | Away - Newtown HS-NHS Practice Fields [Directions] | 10:00 a.m. | ||
| Sat., 9/18 | FR Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 10:00 a.m. | ||
| Mon., 9/20 | V Boys Golf | Darien | Away - Wee Burn CC [Directions] | 3:15 p.m. | SHS-165 darien-160 | |
| Mon., 9/20 | JV Boys Golf | Darien | Home - Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Mon., 9/20 | V Field Hockey | Away - Ridgefield HS-Tiger Hollow Turf Field II | 5:00 p.m. | W 3-1 | ||
| Mon., 9/20 | JV Field Hockey | Ridgefield | Home - Staples HS-Ginny Parker Field [Directions] | 5:15 p.m. | ||
| Mon., 9/20 | FR Field Hockey | Trumbull | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Mon., 9/20 | V Girls Volleyball | Fairfield Ludlowe | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Mon., 9/20 | JV Girls Volleyball | Fairfield Ludlowe | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Mon., 9/20 | FR Girls Volleyball | Fairfield Ludlowe | Home - Staples HS-Field House [Directions] | 4:00 p.m. | ||
| Tue., 9/21 | V Boys Cross Country | Wilton, New Canaan, Stamford | Away - Allen's Meadow-XC Course [Directions] | 4:00 p.m. | ||
| Tue., 9/21 | V Boys Golf | St. Joseph | Home - Longshore Golf Course [Directions] | 3:15 p.m. | SHS-141 ST.JOES 160 | |
| Tue., 9/21 | JV Boys Golf | St. Joseph | Home - Longshore Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 9/21 | FR Boys Soccer | Brien McMahon | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | W 5-2 | |
| Tue., 9/21 | V Girls Cross Country | Wilton, New Canaan, Stamford | Away - Allen's Meadow-XC Course [Directions] | 4:00 p.m. | ||
| Tue., 9/21 | V Girls Diving | Darien | Away - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Tue., 9/21 | V Girls Soccer | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 4:00 p.m. | L 0-2 | |
| Tue., 9/21 | JV Girls Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 4:00 p.m. | ||
| Wed., 9/22 | V Boys Soccer | Danbury | Home - Staples HS-Loeffler Field - Staples HS [Directions] | 4:00 p.m. | T 0-0 | |
| Wed., 9/22 | JV Boys Soccer | Danbury | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | L 3-1 | |
| Wed., 9/22 | V Field Hockey | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | L 1-2 | |
| Wed., 9/22 | JV Field Hockey | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Wed., 9/22 | FR Field Hockey | Ridgefield | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Wed., 9/22 | FR Girls Soccer | Fairfield Ludlowe | Away - Sullivan Field Fairfield-Sullivan Field [Directions] | 3:45 p.m. | ||
| Wed., 9/22 | FR Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:00 p.m. | ||
| Thu., 9/23 | FR Football | Cheshire | Home - Staples HS-Staples Stadium [Directions] | 6:00 p.m. | ||
| Thu., 9/23 | V Boys Golf | Ridgefield | Home - Longshore Golf Course [Directions] | 3:00 p.m. | SHS-147 RIDGEFIELD-164 | |
| Thu., 9/23 | JV Boys Golf | Ridgefield | Home - Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 9/23 | V Girls Soccer | Westhill | Home - Staples HS-Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 7-0 | |
| Thu., 9/23 | JV Girls Soccer | Westhill | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Thu., 9/23 | V Girls Swimming and Diving | Darien | Away - Darien YMCA [Directions] | 3:00 p.m. | ||
| Fri., 9/24 | V Football | Cheshire | Away - Cheshire High Main Game field [Directions] | 7:00 p.m. | L 14-42 | |
| Fri., 9/24 | V Boys Soccer | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | W 1-0 | |
| Fri., 9/24 | V Boys Water Polo | Suffield Academy | Away - Suffield Academy | 4:00 p.m. | ||
| Fri., 9/24 | JV Boys Water Polo | Suffield Academy | Away - Suffield Academy | 5:00 p.m. | ||
| Fri., 9/24 | V Field Hockey | Fairfield Warde | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | W 10-0 | |
| Fri., 9/24 | JV Field Hockey | Fairfield Warde | Home - Staples HS-Ginny Parker Field [Directions] | 5:15 p.m. | ||
| Fri., 9/24 | Miscellaneous Events | Cheerleading | Home - Cheshire HS [Directions] | 7:00 p.m. | ||
| Sat., 9/25 | V Boys Cross Country | Bowdoin Park Classic | Away - Bowdoin Park | 10:00 a.m. | ||
| Sat., 9/25 | JV Football | Cheshire | Home - Staples HS-Staples Stadium [Directions] | 10:00 a.m. | ||
| Sat., 9/25 | JV Boys Soccer | Westhill | Away - Westhill HS-Westhill Front Turf Field [Directions] | 2:00 p.m. | W 6-2 | |
| Sat., 9/25 | FR Boys Soccer | Ridgefield | Home - Staples HS-Wakeman Field B (turf) [Directions] | 12:00 p.m. | W 5-0 | |
| Sat., 9/25 | V Boys Water Polo | Loomis Chaffee School | Home - Staples HS-Staples High School Pool [Directions] | 2:30 p.m. | ||
| Sat., 9/25 | V Girls Cross Country | Bowdoin Park Classic | Away - Bowdoin Park | 10:00 a.m. | ||
| Sat., 9/25 | FR Field Hockey | Westhill | Home - Staples HS-Ginny Parker Field [Directions] | 9:00 a.m. | ||
| Sat., 9/25 | FR Girls Soccer | Trumbull | Home - Staples HS-Wakeman Field B (turf) [Directions] | 10:00 a.m. | ||
| Sat., 9/25 | JV Girls Swimming and Diving | Greenwich | Away - Greenwich HS-Pool [Directions] | 8:30 a.m. | ||
| Sat., 9/25 | FR Girls Volleyball | Westhill | Home - Staples HS-Staples Gym [Directions] | 10:00 a.m. | ||
| Mon., 9/27 | V Boys Golf | Danbury | Home - Longshore Golf Course [Directions] | 3:00 p.m. | SHS-146 Danbury-178 | |
| Mon., 9/27 | JV Boys Golf | Danbury | Home - Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Mon., 9/27 | V Boys Water Polo | Horace Mann (NY) | Home - Staples HS-Staples High School Pool [Directions] | Canceled | Cancelled | |
| Mon., 9/27 | JV Boys Water Polo | Horace Mann (NY) | Home - Staples HS-Staples High School Pool [Directions] | Canceled | Cancelled | |
| Mon., 9/27 | V Girls Soccer | Wilton | Away - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | T 0-0 | |
| Mon., 9/27 | FR Girls Soccer | Greenwich | Home - Staples HS-Wakeman Field E (grass) [Directions] | Postponed | ||
| Mon., 9/27 | V Girls Swimming and Diving | Norwalk/McMahon | Away - Norwalk HS-Pat Spinola Natatorium [Directions] | 4:30 p.m. | ||
| Mon., 9/27 | V Girls Volleyball | Joel Barlow | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Mon., 9/27 | JV Girls Volleyball | Joel Barlow | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Tue., 9/28 | V Boys Soccer | Wilton | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:15 p.m. | T 0-0 | |
| Tue., 9/28 | JV Boys Soccer | Wilton | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:15 p.m. | W 5-0 | |
| Tue., 9/28 | V Boys Water Polo | Greenwich | Away - Greenwich HS-Pool [Directions] | 4:00 p.m. | ||
| Tue., 9/28 | JV Boys Water Polo | Greenwich | Away - Greenwich HS-Pool [Directions] | 5:00 p.m. | ||
| Tue., 9/28 | V Girls Diving | Fairfield Ludlowe | Home - Staples HS-Staples High School Pool [Directions] | 6:30 p.m. | ||
| Tue., 9/28 | V Field Hockey | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 6:00 p.m. | W 6-0 | |
| Tue., 9/28 | JV Field Hockey | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 7:15 p.m. | ||
| Tue., 9/28 | JV Girls Soccer | Wilton | Away - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | ||
| Tue., 9/28 | V Girls Volleyball | Ridgefield | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | L 0-3 | |
| Tue., 9/28 | JV Girls Volleyball | Ridgefield | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Tue., 9/28 | FR Girls Volleyball | Ridgefield | Home - Staples HS-Field House [Directions] | 4:00 p.m. | ||
| Wed., 9/29 | V Boys Cross Country | Brien McMahon, Fairfield Ludlowe, Greenwich | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Wed., 9/29 | FR Boys Soccer | Norwalk | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | W 2-1 | |
| Wed., 9/29 | V Girls Cross Country | Brien McMahon, Fairfield Ludlowe, Greenwich | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Wed., 9/29 | V Girls Swimming and Diving | Fairfield Ludlowe | Home - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Thu., 9/30 | FR Football | Wilbur Cross | Away - Wilbur Cross HS-Wilbur Cross Athletic Complex [Directions] | 4:00 p.m. | ||
| Thu., 9/30 | V Boys Golf | New Canaan | Home - Longshore Golf Course [Directions] | 3:00 p.m. | SHS-147 New Canaan-142 | |
| Thu., 9/30 | JV Boys Golf | New Canaan | Home - Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 9/30 | JV Field Hockey | Norwalk | Home - Staples HS-Ginny Parker Field [Directions] | 5:15 p.m. | ||
| Thu., 9/30 | FR Field Hockey | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 3:30 p.m. | ||
| Thu., 9/30 | V Girls Soccer | Darien | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | W 2-1 | |
| Thu., 9/30 | JV Girls Soccer | Darien | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Thu., 9/30 | V Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Thu., 9/30 | JV Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 9/30 | FR Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | ||
| Fri., 10/1 | V Football | Wilbur Cross | Home - Staples HS-Staples Stadium [Directions] | 7:00 p.m. | W 57-12 | |
| Fri., 10/1 | V Boys Soccer | Darien | Away - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | L 2-1 | |
| Fri., 10/1 | JV Boys Soccer | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | W 6-1 | |
| Fri., 10/1 | V Field Hockey | Danbury | Home - Staples HS-Ginny Parker Field [Directions] | 2:30 p.m. | W 9-0 | |
| Fri., 10/1 | JV Field Hockey | Danbury | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Fri., 10/1 | V Girls Volleyball | Greenwich | Home - Staples HS-Staples Gym [Directions] | 4:30 p.m. | L 0-3 | |
| Fri., 10/1 | JV Girls Volleyball | Greenwich | Home - Staples HS-Staples Gym [Directions] | 5:15 p.m. | ||
| Fri., 10/1 | Miscellaneous Events | Cheerleading | Home - Staples HS-Staples Stadium [Directions] | 7:00 p.m. | ||
| Sat., 10/2 | JV Football | Wilbur Cross | Away - Wilbur Cross HS-Wilbur Cross Athletic Complex [Directions] | Canceled | Cancelled | |
| Sat., 10/2 | FR Boys Soccer | Stamford | Away - Stamford HS-SHS Upper Soccer Field [Directions] | 9:00 a.m. | W 1-0 | |
| Sat., 10/2 | V Boys Water Polo | Hydras | Home - Staples HS-Staples High School Pool [Directions] | 12:00 p.m. | ||
| Sat., 10/2 | JV Boys Water Polo | Hydras | Home - Staples HS-Staples High School Pool [Directions] | 1:00 p.m. | ||
| Sat., 10/2 | FR Girls Soccer | Weston | Away - Weston HS-WHS Lower Turf Field [Directions] | 10:00 a.m. | ||
| Sat., 10/2 | Miscellaneous Events | SAT Date | Home - Staples HS-Staples Stadium [Directions] | 9:00 a.m. | ||
| Mon., 10/4 | V Boys Golf | Fairfield Ludlowe | Home - Longshore Golf Course [Directions] | 3:00 p.m. | SHS-152 Ludlowe-159 | |
| Mon., 10/4 | JV Boys Golf | Fairfield Ludlowe | Home - Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Mon., 10/4 | V Girls Soccer | Fairfield Warde | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | L 0-3 | |
| Tue., 10/5 | V Boys Cross Country | St. Joseph, TBA, Trumbull, Westhill | Away - St. Joseph HS-Trail [Directions] | 4:00 p.m. | ||
| Tue., 10/5 | V Boys Soccer | Fairfield Warde | Away - Fairfield Warde HS-Varsity Grass Soccer Field [Directions] | 4:00 p.m. | W 2-1 | |
| Tue., 10/5 | JV Boys Soccer | Fairfield Warde | Away - Tunxis [Directions] | 4:00 p.m. | W 3-0 | |
| Tue., 10/5 | V Girls Cross Country | St. Joseph, TBA, Trumbull, Westhill | Away - St. Joseph HS-Trail [Directions] | 4:00 p.m. | ||
| Tue., 10/5 | V Field Hockey | Greenwich | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | W 3-2 | |
| Tue., 10/5 | JV Field Hockey | Greenwich | Home - Staples HS-Ginny Parker Field [Directions] | 5:15 p.m. | ||
| Tue., 10/5 | JV Girls Soccer | Fairfield Warde | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Tue., 10/5 | V Girls Swimming and Diving | Westhill/Stamford | Home - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Tue., 10/5 | V Girls Volleyball | Danbury | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Tue., 10/5 | JV Girls Volleyball | Danbury | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Wed., 10/6 | V Boys Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | 3:30 p.m. | SHS-165 Greenwich-158 | |
| Wed., 10/6 | FR Boys Soccer | Greenwich | Away - Central MS [Directions] | 4:45 p.m. | L 4-0 | |
| Wed., 10/6 | FR Field Hockey | Wilton | Home - Staples HS-Ginny Parker Field [Directions] | 5:15 p.m. | ||
| Wed., 10/6 | V Girls Soccer | Trumbull | Away - Trumbull HS-Cork Field [Directions] | 6:00 p.m. | W 1-0 | |
| Wed., 10/6 | JV Girls Soccer | Trumbull | Away - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Wed., 10/6 | FR Girls Soccer | Danbury | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Wed., 10/6 | FR Girls Volleyball | St. Joseph | Home - Staples HS-Field House [Directions] | 4:00 p.m. | ||
| Thu., 10/7 | V Boys Soccer | Trumbull | Home - Staples HS-Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 6-2 | |
| Thu., 10/7 | JV Boys Soccer | Trumbull | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | W 3-1 | |
| Thu., 10/7 | V Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Thu., 10/7 | JV Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/8 | JV Football | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | Postponed | ||
| Fri., 10/8 | V Boys Water Polo | Greenwich | Away - Greenwich HS-Pool [Directions] | 4:00 p.m. | ||
| Fri., 10/8 | V Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 5:00 p.m. | W 8-0 | |
| Fri., 10/8 | JV Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 6:30 p.m. | ||
| Fri., 10/8 | V Girls Soccer | Stamford | Home - Staples HS-Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 4-0 | |
| Fri., 10/8 | JV Girls Soccer | Stamford | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Fri., 10/8 | V Girls Swimming and Diving | Greenwich | Home - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Sat., 10/9 | V Boys Cross Country | Wickham Park Invitational | Away - Wickham Park | 9:00 a.m. | ||
| Sat., 10/9 | FR Boys Soccer | New Canaan | Home - Staples HS-Wakeman Field B (turf) [Directions] | 1:00 p.m. | W 5-1 | |
| Sat., 10/9 | V Boys Water Polo | Cardinal Tournament | Away - Greenwich HS | 11:20 a.m. | ||
| Sat., 10/9 | V Girls Cross Country | Wickham Park Invitational | Away - Wickham Park | 9:00 a.m. | ||
| Sat., 10/9 | FR Field Hockey | Danbury | Home - Staples HS-Ginny Parker Field [Directions] | Canceled | Cancelled | |
| Sat., 10/9 | FR Girls Soccer | Ridgefield | Home - Staples HS-Wakeman Field B (turf) [Directions] | 10:00 a.m. | ||
| Sat., 10/9 | V Girls Volleyball | Wilton | Home - Staples HS-Staples Gym [Directions] | 10:00 a.m. | L 0-3 | |
| Sat., 10/9 | JV Girls Volleyball | Wilton | Home - Staples HS-Staples Gym [Directions] | 11:30 a.m. | ||
| Sat., 10/9 | FR Girls Volleyball | Stamford | Home - Staples HS-Staples Gym [Directions] | 1:00 p.m. | ||
| Mon., 10/11 | V Boys Golf | Hollihan Tournament | Away - CCNC | 11:00 a.m. | ||
| Mon., 10/11 | V Boys Soccer | Stamford | Away - Stamford HS-SHS Upper Soccer Field [Directions] | 4:00 p.m. | W 4-1 | |
| Mon., 10/11 | JV Boys Soccer | Stamford | Away - Rippowam MS-Upper Soccer/Footballl Field [Directions] | 4:00 p.m. | W 1-0 | |
| Mon., 10/11 | V Field Hockey | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | W 6-1 | |
| Mon., 10/11 | JV Field Hockey | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Mon., 10/11 | V Girls Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | L 0-3 | |
| Mon., 10/11 | JV Girls Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 10/12 | V Boys Cross Country | Ridgefield, Fairfield Warde | Away - Ridgefield HS-Upper Grass Field [Directions] | 4:00 p.m. | ||
| Tue., 10/12 | V Girls Cross Country | Ridgefield, Fairfield Warde | Away - Ridgefield HS-Upper Grass Field [Directions] | 4:00 p.m. | ||
| Tue., 10/12 | V Girls Soccer | Bridgeport Central | Home - Staples HS-Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 6-0 | |
| Wed., 10/13 | V Boys Soccer | Bridgeport Central | Away - Bridgeport Central HS-Kennedy Stadium Turf [Directions] | 4:00 p.m. | W 7-0 | |
| Wed., 10/13 | JV Boys Soccer | Bridgeport Central | Away - Bridgeport Central HS-Seaside Park [Directions] | 4:00 p.m. | W 4-0 | |
| Wed., 10/13 | FR Boys Soccer | Fairfield Ludlowe | Away - Sullivan Field Fairfield-Sullivan Field [Directions] | 4:00 p.m. | W 5-0 | |
| Wed., 10/13 | V Field Hockey | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 7:00 p.m. | W 7-0 | |
| Wed., 10/13 | JV Field Hockey | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 5:30 p.m. | ||
| Wed., 10/13 | FR Field Hockey | Fairfield Ludlowe | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Wed., 10/13 | FR Girls Soccer | Greenwich | Away - Greenwich HS-Field 3 [Directions] | 4:00 p.m. | ||
| Wed., 10/13 | V Girls Swimming and Diving | Danbury | Away - WCSU O'Neill Center - Blue Gym-O'Neill Center [Directions] | 7:00 p.m. | ||
| Wed., 10/13 | V Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Wed., 10/13 | JV Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/13 | FR Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/14 | FR Football | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 4:00 p.m. | ||
| Thu., 10/14 | V Boys Golf | FCIAC Championship | Away - Silver Spring Golf Course | 12:00 p.m. | ||
| Thu., 10/14 | V Girls Soccer | St. Joseph | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | T 0-0 | |
| Thu., 10/14 | JV Girls Soccer | St. Joseph | Home - Staples HS-Wakeman Field E (grass) [Directions] | Canceled | Cancelled | |
| Thu., 10/14 | V Girls Swimming and Diving | Fairfield Warde | Away - Fairfield University-Pool [Directions] | 4:00 p.m. | ||
| Fri., 10/15 | JV Football | Danbury | Home - Staples HS-Staples Stadium [Directions] | 6:00 p.m. | ||
| Fri., 10/15 | V Boys Soccer | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 4:00 p.m. | W 7-0 | |
| Fri., 10/15 | V Girls Volleyball | Trumbull | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | L 2-3 | |
| Fri., 10/15 | JV Girls Volleyball | Trumbull | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Sat., 10/16 | V Football | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 2:00 p.m. | W 25-24 | |
| Sat., 10/16 | FR Boys Soccer | Wilton | Away - Allen's Meadow-3A [Directions] | 10:00 a.m. | T 2-2 | |
| Sat., 10/16 | FR Field Hockey | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 10:00 a.m. | ||
| Sat., 10/16 | FR Girls Soccer | Darien | Home - Staples HS-Wakeman Field B (turf) [Directions] | 10:00 a.m. | ||
| Sat., 10/16 | Miscellaneous Events | Cheerleading | Home - Danbury HS-Stadium Turf Field [Directions] | 2:00 p.m. | ||
| Mon., 10/18 | V Boys Golf | CIAC Fall Division I Boys Golf Championship | Away - Chippanee GC | 8:30 a.m. | ||
| Mon., 10/18 | V Boys Water Polo | Horace Mann (NY) | Away - Horace Mann School | 4:00 p.m. | ||
| Mon., 10/18 | JV Boys Water Polo | Horace Mann (NY) | Away - Horace Mann School | 5:00 p.m. | ||
| Mon., 10/18 | V Girls Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 6:00 p.m. | W 5-0 | |
| Mon., 10/18 | V Girls Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 10/18 | JV Girls Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 10/19 | V Boys Soccer | Norwalk | Home - Staples HS-Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 1-0 | |
| Tue., 10/19 | JV Boys Soccer | Norwalk | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | L 2-1 | |
| Tue., 10/19 | FR Field Hockey | Trumbull | Away - Trumbull HS-Cork Field [Directions] | 5:30 p.m. | ||
| Tue., 10/19 | FR Girls Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 10/20 | FR Boys Soccer | Fairfield Warde | Away - Tunxis [Directions] | 4:00 p.m. | W 4-0 | |
| Wed., 10/20 | V Boys Water Polo | Choate Rosemary Hall | Home - Staples HS-Staples High School Pool [Directions] | 5:45 p.m. | ||
| Wed., 10/20 | JV Boys Water Polo | Choate Rosemary Hall | Home - Staples HS-Staples High School Pool [Directions] | 6:45 p.m. | ||
| Wed., 10/20 | V Field Hockey | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | W 9-0 | ||
| Wed., 10/20 | JV Field Hockey | Westhill | Home - Staples HS-Ginny Parker Field [Directions] | Canceled | Cancelled | |
| Wed., 10/20 | JV Girls Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 6:15 p.m. | ||
| Wed., 10/20 | FR Girls Soccer | Wilton | Away - Allen's Meadow-3A [Directions] | 4:15 p.m. | ||
| Wed., 10/20 | V Girls Volleyball | Bridgeport Central | Away - Bridgeport Central HS-Barry McLeod Court [Directions] | 5:30 p.m. | W 3-0 | |
| Wed., 10/20 | JV Girls Volleyball | Bridgeport Central | Away - Bridgeport Central HS-Barry McLeod Court [Directions] | 4:00 p.m. | ||
| Thu., 10/21 | FR Football | Stamford | Home - Staples HS-Staples Stadium [Directions] | 6:00 p.m. | ||
| Thu., 10/21 | V Girls Soccer | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 6:15 p.m. | W 1-0 | |
| Thu., 10/21 | JV Girls Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 4:00 p.m. | ||
| Thu., 10/21 | V Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 5:30 p.m. | L 2-3 | |
| Thu., 10/21 | JV Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/22 | V Football | Stamford | Home - Staples HS-Staples Stadium [Directions] | 7:00 p.m. | W 54-0 | |
| Fri., 10/22 | V Boys Soccer | Brien McMahon | Home - Staples HS-Loeffler Field - Staples HS [Directions] | 4:00 p.m. | T 1-1 | |
| Fri., 10/22 | JV Boys Soccer | Brien McMahon | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | W 3-1 | |
| Fri., 10/22 | Miscellaneous Events | Cheerleading | Home - Staples HS-Staples Stadium [Directions] | 7:00 p.m. | ||
| Fri., 10/22 | Miscellaneous Events | Homecoming | Home - Staples HS-Staples Stadium [Directions] | TBA | ||
| Sat., 10/23 | JV Football | Norwalk | Home - Staples HS-Staples Stadium [Directions] | 10:30 a.m. | ||
| Sat., 10/23 | FR Boys Soccer | Greenwich | Away - Greenwich HS-Field 7 [Directions] | 9:00 a.m. | W 1-0 | |
| Sat., 10/23 | FR Field Hockey | Darien | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 2:00 p.m. | ||
| Sat., 10/23 | FR Girls Soccer | Westhill | Home - Staples HS-Wakeman Field B (turf) [Directions] | 10:00 a.m. | ||
| Sat., 10/23 | Miscellaneous Events | ACT Date | Home - Staples HS-Staples Stadium [Directions] | 9:00 a.m. | ||
| Mon., 10/25 | V Boys Water Polo | Greenwich Country Day School | Away - Greenwich YMCA | 4:00 p.m. | ||
| Mon., 10/25 | V Girls Soccer | Fairfield Ludlowe | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | W 1-0 | |
| Mon., 10/25 | JV Girls Soccer | Fairfield Ludlowe | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Tue., 10/26 | V Boys Cross Country | Wilton JV Tournament | Away - Allen's Meadow | Canceled | Cancelled | |
| Tue., 10/26 | V Girls Cross Country | Wilton JV Tournament | Away - Staples HS-Staples Stadium | Canceled | Cancelled | |
| Tue., 10/26 | FR Girls Volleyball | Wilton | Home - Staples HS-Field House [Directions] | Postponed | ||
| Wed., 10/27 | V Boys Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 7:00 p.m. | W 3-0 | |
| Wed., 10/27 | JV Boys Soccer | Fairfield Ludlowe | Away - Tomlinson MS-Turf Field [Directions] | 3:30 p.m. | W 1-0 | |
| Wed., 10/27 | FR Boys Soccer | Trumbull | Home - Staples HS-Wakeman Field E (grass) [Directions] | Postponed | ||
| Pending changes awaiting acceptance by one or more parties involved: Date to 10/29, Time to 3:45 p.m. | ||||||
| Wed., 10/27 | V Field Hockey | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | W 8-0 | ||
| Wed., 10/27 | JV Field Hockey | St. Joseph | Home - Staples HS-Ginny Parker Field [Directions] | 5:15 p.m. | ||
| Wed., 10/27 | FR Field Hockey | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:30 p.m. | ||
| Wed., 10/27 | V Girls Swimming and Diving | Trumbull | Home - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Thu., 10/28 | V Boys Cross Country | Danbury Freshman Invitational | Away - Danbury HS | 4:00 p.m. | ||
| Thu., 10/28 | FR Football | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | 6:00 p.m. | ||
| Thu., 10/28 | V Girls Cross Country | Danbury Freshman Invitational | Away - Danbury HS | 4:00 p.m. | ||
| Thu., 10/28 | V Field Hockey | Away - New Canaan HS-Dunning Stadium | 3:30 p.m. | L 2-1 | ||
| Thu., 10/28 | JV Field Hockey | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 5:00 p.m. | ||
| Thu., 10/28 | V Girls Soccer | New Canaan | Home - Staples HS-Wakeman Field B (turf) [Directions] | 3:00 p.m. | W 3-1 | |
| Thu., 10/28 | V Girls Volleyball | Brien McMahon | Home - Staples HS-Staples Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Thu., 10/28 | JV Girls Volleyball | Brien McMahon | Home - Staples HS-Staples Gym [Directions] | 4:30 p.m. | ||
| Thu., 10/28 | FR Girls Volleyball | Danbury | Home - Staples HS-Field House [Directions] | 5:15 p.m. | ||
| Fri., 10/29 | V Football | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 7:00 p.m. | W 20-13 | |
| Fri., 10/29 | V Boys Soccer | Fairfield Warde | Home - Staples HS-Wakeman Field B (turf) [Directions] | 3:00 p.m. | L 2-0 | |
| Fri., 10/29 | V Boys Water Polo | Choate Rosemary Hall | Away - Choate School | 4:00 p.m. | ||
| Fri., 10/29 | JV Boys Water Polo | Choate Rosemary Hall | Away - Choate Rosemary Hall | 5:00 p.m. | ||
| Fri., 10/29 | V Girls Swimming and Diving | FCIAC JV Championship | Away - Greenwich HS | 6:30 p.m. | ||
| Fri., 10/29 | V Girls Volleyball | Norwalk | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 10/29 | JV Girls Volleyball | Norwalk | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Fri., 10/29 | Miscellaneous Events | Cheerleading | Home - Norwalk HS-Testa Field, NHS [Directions] | 7:00 p.m. | ||
| Sat., 10/30 | JV Football | Daniel Hand | Away - Daniel Hand HS-Turf Field [Directions] | 10:00 a.m. | ||
| Sat., 10/30 | JV Football | Norwalk | Home - Staples HS-Staples Stadium [Directions] | Canceled | Cancelled | |
| Sat., 10/30 | V Boys Water Polo | Suffield Academy | Home - Staples HS-Staples High School Pool [Directions] | 2:30 p.m. | ||
| Sat., 10/30 | JV Boys Water Polo | Suffield Academy | Home - Staples HS-Staples High School Pool [Directions] | 3:30 p.m. | ||
| Sat., 10/30 | V Field Hockey | Wilton | Home - Staples HS-Ginny Parker Field [Directions] | 10:00 a.m. | W 5-4 | |
| Sat., 10/30 | FR Girls Soccer | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 11:00 a.m. | ||
| Sat., 10/30 | V Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 10:00 a.m. | L 2-3 | |
| Sat., 10/30 | JV Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 11:30 a.m. | ||
| Sat., 10/30 | FR Girls Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 10:30 a.m. | ||
| Mon., 11/1 | V Boys Cross Country | CIAC Boys Cross Country Class LL Championship | Away - Wickham Park | 1:00 p.m. | ||
| Mon., 11/1 | V Boys Water Polo | Greenwich Country Day | Home - Staples HS-Staples High School Pool [Directions] | 6:30 p.m. | ||
| Mon., 11/1 | V Girls Cross Country | CIAC Girls Cross Country Class LL Championship | Away - Wickham Park | 1:30 p.m. | ||
| Mon., 11/1 | V Girls Soccer | St. Joseph | Away - Wilton HS-Lilly Field - Turf [Directions] | 5:00 p.m. | ||
| Tue., 11/2 | V Field Hockey | Darien | Away - Brien McMahon HS-Casagrande Field [Directions] | 7:30 p.m. | ||
| Wed., 11/3 | V Girls Swimming and Diving | FCIAC Girls Swim Trials | Away - Greenwich HS | 5:00 p.m. | ||
| Thu., 11/4 | FR Football | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 3:00 p.m. | ||
| Thu., 11/4 | V Girls Soccer | Wilton | Home - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 7:00 p.m. | ||
| Thu., 11/4 | V Girls Swimming and Diving | FCIAC Girls Diving Finals | Away - Fairfield County Interscholastic Athletic Conferen-Westhill HS | 5:00 p.m. | ||
| Fri., 11/5 | V Boys Cross Country | CIAC Boys Cross Country Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Fri., 11/5 | V Boys Water Polo | Loomis Chaffee School | Away - Loomis Chaffee School | 4:30 p.m. | ||
| Fri., 11/5 | JV Boys Water Polo | Loomis Chaffee School | Away - Loomis Chaffee School | 5:30 p.m. | ||
| Fri., 11/5 | V Girls Cross Country | CIAC Girls Cross Country Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Sat., 11/6 | V Football | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 2:00 p.m. | W 42-7 | |
| Sat., 11/6 | V Boys Water Polo | Chelsea Piers | Away - Chelsea Piers Pool | 2:00 p.m. | ||
| Sat., 11/6 | JV Boys Water Polo | Chelsea Piers | Away - Chelsea Piers Pool | 3:00 p.m. | ||
| Sat., 11/6 | V Girls Swimming and Diving | FCIAC Girls Swim Finals | Away - Fairfield County Interscholastic Athletic Conferen-Greenwich HS | 4:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Greenwich HS | ||||||
| Sat., 11/6 | Miscellaneous Events | Cheerleading | Home - Westhill HS-J. Walter Kennedy Stadium [Directions] | 2:00 p.m. | ||
| Mon., 11/8 | V Girls Soccer | Norwich Free Academy | Home - Staples HS-Wakeman Field B (turf) [Directions] | 2:00 p.m. | ||
| Tue., 11/9 | V Boys Soccer | Manchester | Home - Staples HS-Wakeman Field B (turf) [Directions] | 2:00 p.m. | W 4-0 | |
| Wed., 11/10 | V Field Hockey | Wilton | Home - Staples HS-Ginny Parker Field [Directions] | 2:00 p.m. | ||
| Wed., 11/10 | V Girls Soccer | Darien | Home - Staples HS-Wakeman Field B (turf) [Directions] | 2:00 p.m. | ||
| Thu., 11/11 | FR Football | Ridgefield | Home - Staples HS-Staples Stadium [Directions] | 6:00 p.m. | ||
| Thu., 11/11 | V Boys Soccer | Conard | Home - Staples HS-Wakeman Field B (turf) [Directions] | 2:00 p.m. | W 1-0 | |
| Thu., 11/11 | V Girls Swimming and Diving | CIAC Class LL Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Fri., 11/12 | V Football | Ridgefield | Home - Staples HS-Staples Stadium [Directions] | 7:00 p.m. | W 26-10 | |
| Fri., 11/12 | V Girls Soccer | Farmington | Home - Staples HS-Wakeman Field B (turf) [Directions] | 2:00 p.m. | ||
| Fri., 11/12 | Miscellaneous Events | Cheerleading | Home - Staples HS-Staples Stadium [Directions] | 7:00 p.m. | ||
| Sat., 11/13 | JV Football | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 10:30 a.m. | ||
| Sat., 11/13 | V Boys Soccer | Fairfield Prep | Away - Fairfield University-Rafferty Stadium [Directions] | 1:00 p.m. | W 1-0 | |
| Sat., 11/13 | V Girls Swimming and Diving | CIAC Class LL Qualifying Meet | Away - East Hartford | 11:30 a.m. | ||
| Tue., 11/16 | V Girls Soccer | Fairfield Warde | Home - Trumbull HS-McDougall Stadium [Directions] | 6:30 p.m. | ||
| Wed., 11/17 | V Boys Soccer | Farmington | Home - Municipal Stadium (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 7:00 p.m. | L 1-0 | |
| Wed., 11/17 | V Girls Swimming and Diving | CIAC Class LL Swimming Championships | Away - SCSU | 6:00 p.m. | ||
| Thu., 11/18 | FR Football | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 3:30 p.m. | ||
| Thu., 11/18 | V Girls Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 11/20 | V Girls Soccer | Wilton | Home - Dillon Stadium [Directions] | 4:00 p.m. | ||
| Sun., 11/21 | V Girls Swimming and Diving | CIAC State Open Swimming Championships | Away - Cornerstone Pool | 2:00 p.m. | ||
| Mon., 11/22 | JV Football | Greenwich | Home - Staples HS-Staples Stadium [Directions] | 6:00 p.m. | ||
| Thu., 11/25 | V Football | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 10:00 a.m. | L 28-34 (OT) | |
| Thu., 11/25 | Miscellaneous Events | Cheerleading | Home - Greenwich HS [Directions] | 10:00 a.m. | ||
| Mon., 11/29 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:50-4:50 p.m. | ||
| Tue., 11/30 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:50-4:50 p.m. | ||
| Wed., 12/1 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:50-4:50 p.m. | ||
| Thu., 12/2 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:50-4:50 p.m. | ||
| Fri., 12/3 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:50-4:50 p.m. | ||
| Sat., 12/4 | V Boys Ice Hockey | North Haven (Scrim.) | Home - Milford Ice Pavillion-Ice Rink [Directions] | 7:15 p.m. | ||
| Sat., 12/4 | V Girls Ice Hockey | Rinks at Shelton Jambo | Away - Not Listed-Rinks At Shelton | 5:15 p.m. | ||
| Mon., 12/6 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:50-4:50 p.m. | ||
| Mon., 12/6 | V Girls Basketball | Stamford (Scrim.) | Away - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 12/7 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:50-4:50 p.m. | ||
| Wed., 12/8 | V Boys Basketball | Jonathan Law (Scrim.) | Away - Jonathan Law HS-James L. Richetelli Memorial Gymnasium [Directions] | 6:30 p.m. | ||
| Wed., 12/8 | V Boys Ice Hockey | Milford Coop (Scrim.) | Away - Milford Ice Pavillion-Ice Rink [Directions] | 6:00 p.m. | ||
| Wed., 12/8 | V Girls Basketball | Fairfield Warde (Scrim.) | Away - Fairfield Warde HS-Large Gym [Directions] | 6:00 p.m. | ||
| Wed., 12/8 | V Girls Ice Hockey | Avon | Home - Terry Conners - Stamford-Ice Rink [Directions] | 5:30 p.m. | W 3-2 | |
| Thu., 12/9 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:50-4:50 p.m. | ||
| Fri., 12/10 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:50-4:50 p.m. | ||
| Fri., 12/10 | V Boys Indoor Track | Practice | Home - Staples HS-Field House [Directions] | 3-8 p.m. | ||
| Fri., 12/10 | V Girls Basketball | Ridgefield (Scrim.) | Home - Staples HS-Staples Gym [Directions] | 5:15 p.m. | ||
| Sat., 12/11 | V Boys Basketball | Notre Dame-Fairfield (Scrim.) | Away - Notre Dame - Fairfield -Sister Marion Reilly Auditorium [Directions] | 11:00 a.m. | ||
| Sat., 12/11 | V Boys Indoor Track | Practice | Home - Staples HS-Field House [Directions] | 9 a.m.-2 p.m. | ||
| Sat., 12/11 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice-New [Directions] | 4:15 p.m. | W 10-3 | |
| Mon., 12/13 | V Boys Basketball | Foran (Scrim.) | Home - Staples HS-Staples Gym [Directions] | 5:00 p.m. | ||
| Mon., 12/13 | FR Boys Basketball | Fairfield Prep (Scrim.) | Away - Fairfield University-Brissette Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 12/13 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:50-4:50 p.m. | ||
| Mon., 12/13 | V Wrestling | Wrestling off | Home - Staples HS-Field House [Directions] | 4:00 p.m. | ||
| Tue., 12/14 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:50-4:50 p.m. | ||
| Wed., 12/15 | V Boys Basketball | Notre Dame-Fairfield (Scrim.) | Home - Staples HS-Staples Gym [Directions] | 3:15 p.m. | ||
| Wed., 12/15 | V Boys Ice Hockey | Amity | Home - Milford Ice Pavillion-Ice Rink [Directions] | 6:15 p.m. | L 1-5 | |
| Wed., 12/15 | V Wrestling | Wilton | Away - Wilton HS-Nicholas Zeoli Fieldhouse [Directions] | 7:00 p.m. | ||
| Wed., 12/15 | V Girls Ice Hockey | Daniel Hand Coop | Home - Terry Conners - Stamford-Ice Rink [Directions] | 7:50 p.m. | W 6-0 | |
| Thu., 12/16 | V Boys Alpine Skiing | Practice | Home - Mt. Southingon Ski Area [Directions] | 4-6 p.m. | ||
| Thu., 12/16 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:50-4:50 p.m. | ||
| Thu., 12/16 | V Boys Swimming and Diving | St. Joseph, Trumbull | Home - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Thu., 12/16 | V Girls Alpine Skiing | Practice | Home - Mt. Southingon Ski Area [Directions] | 4-6 p.m. | ||
| Thu., 12/16 | V Girls Basketball | Norwalk | Home - Staples HS-Staples Gym [Directions] | 7:00 p.m. | W 46-27 | |
| Thu., 12/16 | JV Girls Basketball | Norwalk | Home - Staples HS-Staples Gym [Directions] | 5:15 p.m. | ||
| Fri., 12/17 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:50-4:50 p.m. | ||
| Fri., 12/17 | JV Boys Squash | Fairfield HS A | Home - Intensity Fitness [Directions] | 7:30 p.m. | ||
| Fri., 12/17 | FR Girls Basketball | Norwich Free Academy | Away - Norwich Free Academy-Alumni Gym [Directions] | Postponed | ||
| Fri., 12/17 | V Girls Indoor Track | 20th Annual Hillhouse Invitational | Away - Floyd Little Athletic Center | 4:30 p.m. | ||
| Sat., 12/18 | V Boys Ice Hockey | East Haven Coop | Home - Milford Ice Pavillion-Ice Rink [Directions] | 7:30 p.m. | L 2-9 | |
| Sat., 12/18 | V Boys Indoor Track | FCIAC, Fairfield Ludlowe, Ridgefield, St. Joseph | Away - Staples HS-Field House | 10:00 a.m. | ||
| Sat., 12/18 | V Boys Indoor Track | Greenwich, Stamford, Trumbull, Westhill | Home - Staples HS-Field House [Directions] | 12:30 p.m. | ||
| Sat., 12/18 | V Wrestling | Lancer invitational | Away - Waterford HS - official -Francis X. Sweeney Field House | 10:00 a.m. | ||
| Sat., 12/18 | V Girls Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | 6:40 p.m. | L 1-8 | |
| Sat., 12/18 | V Girls Indoor Track | FCIAC, Fairfield Ludlowe, Ridgefield, St. Joseph | Away - Staples HS-Field House | 10:00 a.m. | ||
| Sat., 12/18 | V Girls Indoor Track | Greenwich, Stamford, Trumbull, Westhill | Home - Staples HS-Field House [Directions] | 12:30 p.m. | ||
| Sat., 12/18 | V Girls Indoor Track | Energice Coaches HOF Invitational | Away - Armory Track | TBA | ||
| Mon., 12/20 | V Boys Alpine Skiing | Practice | Home - Mt. Southingon Ski Area [Directions] | Canceled | Cancelled | |
| Mon., 12/20 | V Girls Alpine Skiing | Practice | Home - Mt. Southingon Ski Area [Directions] | Canceled | Cancelled | |
| Mon., 12/20 | V Girls Basketball | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | 7:00 p.m. | L 36-48 | |
| Mon., 12/20 | Miscellaneous Events | Nationals | Home - TBA [Directions] | 12:00 p.m. | ||
| Tue., 12/21 | V Boys Basketball | Joel Barlow | Home - Staples HS-Staples Gym [Directions] | 7:00 p.m. | W 68-44 | |
| Tue., 12/21 | JV Boys Basketball | Joel Barlow | Home - Staples HS-Staples Gym [Directions] | 5:15 p.m. | ||
| Tue., 12/21 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:50-4:50 p.m. | ||
| Tue., 12/21 | FR Girls Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:45 p.m. | ||
| Wed., 12/22 | V Boys Ice Hockey | JBWA | Home - Milford Ice Pavillion-Ice Rink [Directions] | 5:25 p.m. | L 2-3 | |
| Wed., 12/22 | V Girls Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 6:00 p.m. | W 50-28 | |
| Wed., 12/22 | JV Girls Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:15 p.m. | ||
| Wed., 12/22 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Terry Conners - Stamford-Ice Rink [Directions] | 7:50 p.m. | W 8-1 | |
| Thu., 12/23 | V Wrestling | Greenwich, New Canaan, St. Joseph | Away - Greenwich HS-Gymnasium [Directions] | Postponed | ||
| Sun., 12/26 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:45-5 p.m. | ||
| Mon., 12/27 | V Boys Basketball | Immaculate | Away - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | L 50-63 | |
| Mon., 12/27 | V Boys Ice Hockey | Enfield/East Granby/Stafford | Away - Enfield Twin Rinks-Rink 2 [Directions] | 1:00 p.m. | W 3-1 | |
| Mon., 12/27 | JV Wrestling | Trumbull, Brien McMahon, Bristol Eastern, Fairfield Ludlowe, Fairfield Warde, TBA, New Milford, Norwalk | Away - Trumbull HS-Aux Gym | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to TBA | ||||||
| Mon., 12/27 | V Girls Basketball | Fairfield Ludlowe | Away - Fairfield Warde HS-Large Gym [Directions] | 2:00 p.m. | L 39-56 | |
| Mon., 12/27 | V Girls Ice Hockey | West Haven/SHA | Away - West Haven HS-Bennett Rink [Directions] | 12:00 p.m. | W 3-0 | |
| Tue., 12/28 | FR Boys Basketball | West Haven (Scrim.) | Home - Staples HS-Staples Gym [Directions] | Postponed | ||
| Tue., 12/28 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 10-11:15 a.m. | ||
| Tue., 12/28 | JV Boys Ice Hockey | Masuk | Home - Milford Ice Pavillion-Ice Rink [Directions] | Postponed | ||
| Wed., 12/29 | V Boys Basketball | Pomperaug | Away - Pomperaug HS-Main Gym [Directions] | 4:00 p.m. | W 75-50 | |
| Wed., 12/29 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 10-11:15 a.m. | ||
| Wed., 12/29 | V Boys Indoor Track | Coach/Bob Saulsbury Invitational | Away - Floyd Little Athletic Center | Canceled | Cancelled | |
| Wed., 12/29 | V Wrestling | Danbury, Bristol Eastern, Brookfield, Coventry (RI), Enfield, Abbott Tech, TBA, TBA, TBA, TBA, New Canaan, New Fairfield, New Milford, Norwalk, Wilton | Away - Danbury HS-Main Gym | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to 9:15 a.m. | ||||||
| Wed., 12/29 | V Girls Ice Hockey | Mercy/NW Catholic/East Hampton | Home - Terry Conners - Stamford-Ice Rink [Directions] | 7:40 p.m. | W 7-2 | |
| Thu., 12/30 | JV Boys Ice Hockey | Guilford | Away - Blake Field - New Haven-Walker Rink [Directions] | Postponed | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 1:45 p.m. | ||||||
| Thu., 12/30 | V Boys Indoor Track | Joe Sinicrope Invitational | Away - Floyd Little Athletic Center | 12:30 p.m. | ||
| Fri., 12/31 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 10-11:15 a.m. | ||
| Mon., 1/3 | V Boys Alpine Skiing | Practice | Home - Mt. Southingon Ski Area [Directions] | Canceled | Cancelled | |
| Mon., 1/3 | V Boys Basketball | Stratford | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | W 66-63 | |
| Mon., 1/3 | JV Boys Basketball | Stratford | Home - Staples HS-Staples Gym [Directions] | Canceled | Cancelled | |
| Mon., 1/3 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:50-4:50 p.m. | ||
| Mon., 1/3 | V Boys Squash | Greenwich A | Away - Chelsea Piers - | 7:30 p.m. | ||
| Mon., 1/3 | V Girls Alpine Skiing | Practice | Home - Mt. Southingon Ski Area [Directions] | Canceled | Cancelled | |
| Tue., 1/4 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:50-4:50 p.m. | ||
| Tue., 1/4 | V Girls Basketball | Darien | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | W 30-28 | |
| Tue., 1/4 | JV Girls Basketball | Darien | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/4 | V Girls Gymnastics | Westhill, Norwalk, Stamford | Away - Westhill HS-New Gym [Directions] | 6:00 p.m. | 125.00 | |
| Thu., 1/6 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:50-4:50 p.m. | ||
| Thu., 1/6 | V Wrestling | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Aux Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/7 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | Canceled | Cancelled | |
| Fri., 1/7 | V Girls Gymnastics | Greenwich | Home - Westport YMCA [Directions] | 6:30 p.m. | ||
| Fri., 1/7 | V Girls Indoor Track | U.S. Air Force Hispanic Games | Away - Armory Track | Canceled | Cancelled | |
| Sat., 1/8 | V Boys Basketball | Ridgefield | Home - Staples HS-Staples Gym [Directions] | 5:00 p.m. | L 61-72 | |
| Sat., 1/8 | JV Boys Basketball | Ridgefield | Home - Staples HS-Staples Gym [Directions] | 3:15 p.m. | ||
| Sat., 1/8 | FR Boys Basketball | Ridgefield | Home - Staples HS-Staples Gym [Directions] | 2:00 p.m. | ||
| Sat., 1/8 | V Boys Ice Hockey | Newtown/New Fairfield | Home - Milford Ice Pavillion-Ice Rink [Directions] | 7:30 p.m. | W 6-1 | |
| Sat., 1/8 | V Boys Indoor Track | FCIAC Qualifier #2 | Home - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/8 | V Boys Indoor Track | Elm City Coaches Invitational | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Sat., 1/8 | V Boys Indoor Track | Air Force Hispanic Games | Away - Armory Track | 10:00 a.m. | ||
| Sat., 1/8 | V Boys Indoor Track | FCIAC, Danbury, Greenwich, St. Joseph | Away - Staples HS-Field House | 10:00 a.m. | ||
| Sat., 1/8 | V Wrestling | Simsbury, Bunnell, Norwalk, Westhill | Away - Simsbury HS-Gym 2 [Directions] | 8:15 a.m. | ||
| Sat., 1/8 | V Wrestling | Warde Invitational | Away - Fairfield Warde HS-Large Gym | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to 9:00 a.m. | ||||||
| Sat., 1/8 | JV Wrestling | JV Duals | Away - Trumbull HS-Aux Gym | Postponed | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 8:30 a.m. | ||||||
| Sat., 1/8 | V Girls Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 7:00 p.m. | L 16-45 | |
| Sat., 1/8 | JV Girls Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:30 p.m. | ||
| Sat., 1/8 | FR Girls Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 1/8 | V Girls Indoor Track | FCIAC, Danbury, Greenwich, St. Joseph | Away - Staples HS-Field House | 10:00 a.m. | ||
| Sat., 1/8 | V Girls Indoor Track | Freedom Games @ Ocean Breeze Athletic Complex 625 Father Capodanno Blvd Staten Island, NY 10305 | Away - Not Listed | 9:30 a.m. | ||
| Mon., 1/10 | V Boys Alpine Skiing | Practice | Home - Mt. Southingon Ski Area [Directions] | 4-6 p.m. | ||
| Mon., 1/10 | V Boys Basketball | Wright Tech | Home - Staples HS-Staples Gym [Directions] | 7:00 p.m. | W 73-24 | |
| Mon., 1/10 | JV Boys Basketball | Wright Tech | Home - Staples HS-Staples Gym [Directions] | 5:15 p.m. | ||
| Mon., 1/10 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:50-4:50 p.m. | ||
| Mon., 1/10 | JV Boys Squash | Bronxville JV | Away - Chelsea Piers - | 7:30 p.m. | ||
| Mon., 1/10 | V Girls Alpine Skiing | Practice | Home - Mt. Southingon Ski Area [Directions] | 4-6 p.m. | ||
| Mon., 1/10 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 3:30 p.m. | W 7-1 | |
| Tue., 1/11 | V Boys Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 7:00 p.m. | W 54-47 | |
| Tue., 1/11 | JV Boys Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/11 | FR Boys Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/11 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:50-4:50 p.m. | ||
| Tue., 1/11 | V Girls Basketball | New Canaan | Home - Staples HS-Staples Gym [Directions] | 7:00 p.m. | W 36-31 | |
| Tue., 1/11 | JV Girls Basketball | New Canaan | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/11 | FR Girls Basketball | New Canaan | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/12 | V Boys Ice Hockey | Trumbull | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | 8:00 p.m. | L 3-6 | |
| Wed., 1/12 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Home - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Wed., 1/12 | V Wrestling | Norwalk | Home - Staples HS-Staples Gym [Directions] | 7:00 p.m. | ||
| Thu., 1/13 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:50-4:50 p.m. | ||
| Thu., 1/13 | V Girls Gymnastics | Greenwich, Norwalk | Away - Greenwich YWCA [Directions] | 6:30 p.m. | 132.85 | |
| Fri., 1/14 | V Boys Basketball | Greenwich | Home - Staples HS-Staples Gym [Directions] | 7:00 p.m. | W 74-60 | |
| Fri., 1/14 | JV Boys Basketball | Greenwich | Home - Staples HS-Staples Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/14 | FR Boys Basketball | Greenwich | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/14 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:50-4:50 p.m. | ||
| Fri., 1/14 | V Boys Indoor Track | Steve Borbet Invitational | Away - Armory Track | 5:00 p.m. | ||
| Fri., 1/14 | V Boys Swimming and Diving | Ridgefield | Away - Barlow Mountain Pool [Directions] | 4:00 p.m. | ||
| Fri., 1/14 | V Girls Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 7:00 p.m. | L 45-48 | |
| Fri., 1/14 | JV Girls Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/14 | FR Girls Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/14 | V Girls Gymnastics | Fairfield Warde, Norwalk | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:00 p.m. | ||
| Fri., 1/14 | V Girls Gymnastics | Fairfield Ludlowe, Norwalk | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:00 p.m. | 131.60 | |
| Fri., 1/14 | V Girls Indoor Track | Steve Borbet Invitational | Away - Armory Track | 4:45 p.m. | ||
| Sat., 1/15 | V Boys Ice Hockey | Brien McMahon/Norwalk | Away - Sono Ice House-Main Rink [Directions] | 3:30 p.m. | W 4-2 | |
| Sat., 1/15 | V Boys Indoor Track | FCIAC, Darien, St. Joseph, Stamford | Away - Staples HS-Field House | 10:00 a.m. | ||
| Sat., 1/15 | V Wrestling | Brookfield, East Lyme/Norwich Tech, Fairfield Prep, Fairfield Ludlowe, Foran, TBA, Newtown, Shelton | Home - Staples HS-Staples Gym [Directions] | 8:45 a.m. | ||
| Sat., 1/15 | V Girls Ice Hockey | Greenwich | Home - Terry Conners - Stamford-Ice Rink [Directions] | 6:20 p.m. | W 5-1 | |
| Sat., 1/15 | V Girls Indoor Track | FCIAC, Darien, St. Joseph, Stamford | Away - Staples HS-Field House | 10:00 a.m. | ||
| Mon., 1/17 | V Boys Basketball | Danbury | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | W 72-62 | |
| Mon., 1/17 | JV Boys Basketball | Danbury | Home - Staples HS-Staples Gym [Directions] | 2:15 p.m. | ||
| Mon., 1/17 | FR Boys Basketball | Danbury | Home - Staples HS-Staples Gym [Directions] | 1:00 p.m. | ||
| Mon., 1/17 | V Boys Ice Hockey | Westhill/Stamford | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4:00 p.m. | L 2-5 | |
| Mon., 1/17 | V Girls Ice Hockey | Masuk Coop | Home - Terry Conners - Stamford-Ice Rink [Directions] | 1:00 p.m. | W 8-0 | |
| Tue., 1/18 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:50-4:50 p.m. | ||
| Tue., 1/18 | JV Wrestling | Fairfield Warde, Fairfield Ludlowe | Away - Fairfield Warde HS-Small Gym [Directions] | Canceled | Cancelled | |
| Tue., 1/18 | V Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 6:00 p.m. | L 32-43 | |
| Tue., 1/18 | JV Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 4:30 p.m. | ||
| Wed., 1/19 | V Boys Ice Hockey | New Milford | Home - Milford Ice Pavillion-Ice Rink [Directions] | 7:35 p.m. | W 2-1 | |
| Wed., 1/19 | V Boys Swimming and Diving | Darien | Home - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Wed., 1/19 | V Wrestling | Greenwich, Westhill | Home - Staples HS-Staples Gym [Directions] | 7:00 p.m. | ||
| Wed., 1/19 | V Girls Basketball | Kolbe Cathedral | Home - Staples HS-Staples Gym [Directions] | 4:30 p.m. | W 50-44 | |
| Wed., 1/19 | FR Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 5:00 p.m. | ||
| Wed., 1/19 | V Girls Ice Hockey | Darien | Home - Terry Conners - Stamford-Ice Rink [Directions] | 8:00 p.m. | T 0-0(OT) | |
| Thu., 1/20 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | Canceled | Cancelled | |
| Fri., 1/21 | V Boys Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 6:30 p.m. | L 61-66 | |
| Fri., 1/21 | JV Boys Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 5:00 p.m. | ||
| Fri., 1/21 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:50-4:50 p.m. | ||
| Fri., 1/21 | V Boys Indoor Track | New Balance Games | Away - Armory Track | TBA | ||
| Fri., 1/21 | V Boys Squash | Greens Farms Academy | Away - Greens Farms Academy | 5:00 p.m. | ||
| Fri., 1/21 | JV Boys Squash | Greens Farms Academy | Away - Greens Farms Academy | 5:00 p.m. | ||
| Fri., 1/21 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Away - Fairfield University-Pool [Directions] | 6:30 p.m. | ||
| Fri., 1/21 | V Girls Basketball | Westhill | Home - Staples HS-Staples Gym [Directions] | 6:00 p.m. | W 42-24 | |
| Fri., 1/21 | JV Girls Basketball | Westhill | Home - Staples HS-Staples Gym [Directions] | 4:30 p.m. | ||
| Fri., 1/21 | V Girls Indoor Track | New Balance Games | Away - Armory Track | TBA | ||
| Sat., 1/22 | FR Boys Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 1/22 | V Boys Ice Hockey | North Branford | Away - Northford Ice Pavilion-Red [Directions] | 7:30 p.m. | L 4-5 | |
| Sat., 1/22 | V Boys Indoor Track | FCIAC, New Canaan, Norwalk, Stamford | Away - Staples HS-Field House | 10:00 a.m. | ||
| Sat., 1/22 | V Boys Indoor Track | New Balance Games | Away - Armory Track | TBA | ||
| Sat., 1/22 | V Wrestling | Snitkin Duals | Away - Norwich Free Academy-Alumni Gym | 10:00 a.m. | ||
| Sat., 1/22 | JV Wrestling | Danbury, Bristol Central, Bunnell, Fairfield Warde, TBA, TBA, TBA, New Fairfield, Norwalk, Simsbury, Trumbull | Away - Danbury HS-Main Gym | 9:30 a.m. | ||
| Sat., 1/22 | V Competitive Cheerleading | FLHS Cheer Event | Away - Fairfield Ludlowe HS | TBA | ||
| Sat., 1/22 | V Girls Indoor Track | FCIAC, New Canaan, Norwalk, Stamford | Away - Staples HS-Field House | 10:00 a.m. | ||
| Sat., 1/22 | V Girls Indoor Track | New Balance Games | Away - Armory Track | TBA | ||
| Mon., 1/24 | V Boys Alpine Skiing | Practice | Home - Mt. Southingon Ski Area [Directions] | 4-6 p.m. | ||
| Mon., 1/24 | V Boys Basketball | Wilton | Home - Staples HS-Staples Gym [Directions] | 7:00 p.m. | L 47-50 | |
| Mon., 1/24 | JV Boys Basketball | Wilton | Home - Staples HS-Staples Gym [Directions] | 5:15 p.m. | ||
| Mon., 1/24 | FR Boys Basketball | Wilton | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Mon., 1/24 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:50-4:50 p.m. | ||
| Mon., 1/24 | V Boys Squash | Rye High School | Home - Intensity Fitness [Directions] | 7:30 p.m. | ||
| Mon., 1/24 | V Girls Alpine Skiing | Practice | Home - Mt. Southingon Ski Area [Directions] | 4-6 p.m. | ||
| Mon., 1/24 | V Girls Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 7:00 p.m. | W 41-29 | |
| Mon., 1/24 | JV Girls Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:30 p.m. | ||
| Mon., 1/24 | FR Girls Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Tue., 1/25 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:50-4:50 p.m. | ||
| Wed., 1/26 | V Boys Ice Hockey | Watertown-Pomperaug | Home - Milford Ice Pavillion-Ice Rink [Directions] | 5:25 p.m. | L 4-5 | |
| Wed., 1/26 | V Boys Swimming and Diving | St. Joseph | Home - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Wed., 1/26 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Home - Terry Conners - Stamford-Ice Rink [Directions] | 7:50 p.m. | W 9-2 | |
| Thu., 1/27 | V Boys Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 7:00 p.m. | W 58-38 | |
| Thu., 1/27 | JV Boys Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:15 p.m. | ||
| Thu., 1/27 | FR Boys Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 1/27 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:50-4:50 p.m. | ||
| Thu., 1/27 | JV Boys Squash | Briarcliff V | Away - Chelsea Piers - | 7:30 p.m. | ||
| Thu., 1/27 | V Girls Basketball | Fairfield Ludlowe | Home - Staples HS-Staples Gym [Directions] | 7:00 p.m. | L 44-29 | |
| Thu., 1/27 | JV Girls Basketball | Fairfield Ludlowe | Home - Staples HS-Staples Gym [Directions] | 5:15 p.m. | ||
| Thu., 1/27 | FR Girls Basketball | Fairfield Ludlowe | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/28 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:50-4:50 p.m. | ||
| Fri., 1/28 | FR Girls Basketball | Norwich Free Academy | Home - Staples HS-Staples Gym [Directions] | Canceled | Cancelled | |
| Fri., 1/28 | V Girls Gymnastics | Darien | Home - Westport YMCA [Directions] | 6:30 p.m. | 128.2 | |
| Sat., 1/29 | V Wrestling | SOUTHINGTON CHALLENGE | Away - Southington HS-Gym West | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to 7:00 a.m. | ||||||
| Sat., 1/29 | V Wrestling | Norwalk, Brien McMahon, Darien, Fairfield Ludlowe, Fairfield Warde, Greens Farms Academy, Greenwich, TBA, TBA, TBA, Notre Dame-Fairfield, Ridgefield, St. Joseph, Trumbull, Weston | Away - Norwalk HS-Tom Scarso Gymnasium | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to 9:00 a.m. | ||||||
| Sun., 1/30 | JV Boys Ice Hockey | Guilford | Home - Milford Ice Pavillion-Ice Rink [Directions] | Postponed | ||
| Mon., 1/31 | V Boys Alpine Skiing | Practice | Home - Mt. Southingon Ski Area [Directions] | 4-6 p.m. | ||
| Mon., 1/31 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:50-4:50 p.m. | ||
| Mon., 1/31 | JV Boys Squash | Darien JV | Away - Ox Ridge Club | 8:00 p.m. | ||
| Mon., 1/31 | V Girls Alpine Skiing | Practice | Home - Mt. Southingon Ski Area [Directions] | 4-6 p.m. | ||
| Tue., 2/1 | V Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 7:00 p.m. | W 63-62 | |
| Tue., 2/1 | JV Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/1 | FR Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 3:45 p.m. | ||
| Tue., 2/1 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:50-4:50 p.m. | ||
| Tue., 2/1 | V Girls Basketball | Fairfield Warde | Home - Staples HS-Staples Gym [Directions] | 7:00 p.m. | L 38-46 | |
| Tue., 2/1 | JV Girls Basketball | Fairfield Warde | Home - Staples HS-Staples Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/1 | FR Girls Basketball | Fairfield Warde | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/1 | V Girls Gymnastics | Norwalk, Wilton | Home - Westport YMCA [Directions] | 6:30 p.m. | 134.45 | |
| Wed., 2/2 | V Boys Ice Hockey | Masuk | Home - Milford Ice Pavillion-Ice Rink [Directions] | 7:35 p.m. | W 6-1 | |
| Wed., 2/2 | V Boys Swimming and Diving | Greenwich | Away - Greenwich HS-Pool [Directions] | 4:30 p.m. | ||
| Wed., 2/2 | V Wrestling | Trumbull | Home - Staples HS-Staples Gym [Directions] | 7:00 p.m. | ||
| Wed., 2/2 | V Girls Ice Hockey | East Catholic Coop | Home - Terry Conners - Stamford-Ice Rink [Directions] | 5:30 p.m. | W 4-0 | |
| Thu., 2/3 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:50-4:50 p.m. | ||
| Thu., 2/3 | V Boys Indoor Track | FCIAC Indoor Track Championships | Away - Floyd Little Athletic Center-Field House | 4:30 p.m. | ||
| Thu., 2/3 | JV Boys Squash | Rye Varsity | Away - Life Time Westchester | 8:00 p.m. | ||
| Thu., 2/3 | V Girls Gymnastics | New Canaan | Home - Westport YMCA [Directions] | 6:30 p.m. | 128.65 | |
| Thu., 2/3 | V Girls Indoor Track | FCIAC Indoor Track Championships | Away - Floyd Little Athletic Center-Field House | 4:30 p.m. | ||
| Fri., 2/4 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | Canceled | Cancelled | |
| Fri., 2/4 | JV Girls Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | Canceled | Cancelled | |
| Sat., 2/5 | V Boys Basketball | Trumbull | Home - Staples HS-Staples Gym [Directions] | 1:00 p.m. | W 71-63 | |
| Sat., 2/5 | JV Boys Basketball | Trumbull | Home - Staples HS-Staples Gym [Directions] | 11:15 a.m. | ||
| Sat., 2/5 | FR Boys Basketball | Trumbull | Home - Staples HS-Staples Gym [Directions] | 10:00 a.m. | ||
| Sat., 2/5 | V Boys Ice Hockey | Brookfield | Away - Danbury Ice Arena-Patriot Rink [Directions] | 12:00 p.m. | W 4-2 | |
| Sat., 2/5 | V Boys Indoor Track | FCIAC JV/LAST CHANCE INVITATIONAL | Home - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Sat., 2/5 | V Wrestling | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 5:00 p.m. | ||
| Sat., 2/5 | V Girls Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 5:00 p.m. | W 35-23 | |
| Sat., 2/5 | V Competitive Cheerleading | FCIAC Championship | Away - trumbull high school | 9:30 a.m. | ||
| Sat., 2/5 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:30 p.m. | W 10-1 | |
| Sat., 2/5 | V Girls Indoor Track | FCIAC JV/LAST CHANCE INVITATIONAL | Home - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Sun., 2/6 | JV Boys Ice Hockey | Brien McMahon/Norwalk | Home - Milford Ice Pavillion-Ice Rink [Directions] | Canceled | Cancelled | |
| Sun., 2/6 | V Boys Squash | Squash Haven | Away - New haven Lawn Club | 1:00 p.m. | ||
| Mon., 2/7 | V Boys Alpine Skiing | Practice | Home - Mt. Southingon Ski Area [Directions] | 4-6 p.m. | ||
| Mon., 2/7 | FR Boys Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 6:00 p.m. | ||
| Mon., 2/7 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:50-4:50 p.m. | ||
| Mon., 2/7 | JV Boys Ice Hockey | Newtown-New Fairfield | Away - Danbury Ice Arena | 5:00 p.m. | ||
| Mon., 2/7 | V Boys Squash | Darien | Home - Intensity Fitness [Directions] | 7:30 p.m. | ||
| Mon., 2/7 | V Boys Swimming and Diving | Westhill/Stamford | Away - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Mon., 2/7 | V Wrestling | Danbury | Home - Staples HS-Staples Gym [Directions] | 7:00 p.m. | ||
| Mon., 2/7 | V Girls Alpine Skiing | Practice | Home - Mt. Southingon Ski Area [Directions] | 4-6 p.m. | ||
| Mon., 2/7 | FR Girls Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 3:30 p.m. | ||
| Mon., 2/7 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Terry Conners - Stamford-Ice Rink [Directions] | 3:30 p.m. | W 7-1 | |
| Tue., 2/8 | V Boys Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 6:00 p.m. | W 62-32 | |
| Tue., 2/8 | JV Boys Basketball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | ||
| Tue., 2/8 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:50-4:50 p.m. | ||
| Tue., 2/8 | V Girls Basketball | Stamford | Home - Staples HS-Staples Gym [Directions] | 7:00 p.m. | L 39-27 | |
| Tue., 2/8 | JV Girls Basketball | Stamford | Home - Staples HS-Staples Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/8 | FR Girls Basketball | Stamford | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/8 | V Girls Gymnastics | Norwalk, St. Joseph, Trumbull | Home - Westport YMCA [Directions] | 6:30 p.m. | 132.6 | |
| Wed., 2/9 | V Boys Ice Hockey | Westhill/Stamford | Away - Terry Conners - Stamford-Ice Rink [Directions] | 7:30 p.m. | L 2-5 | |
| Wed., 2/9 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Terry Conners - Stamford-Ice Rink [Directions] | 5:30 p.m. | W 5-2 | |
| Thu., 2/10 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:50-4:50 p.m. | ||
| Thu., 2/10 | JV Boys Squash | Greenwich B | Away - Chelsea Piers - | 7:30 p.m. | ||
| Fri., 2/11 | V Boys Basketball | Bridgeport Central | Away - Bridgeport Central HS-Barry McLeod Court [Directions] | 7:00 p.m. | W 76-32 | |
| Fri., 2/11 | JV Boys Basketball | Bridgeport Central | Away - Bridgeport Central HS-Barry McLeod Court [Directions] | 5:30 p.m. | ||
| Fri., 2/11 | FR Boys Basketball | Bridgeport Central | Away - Bridgeport Central HS-Barry McLeod Court [Directions] | 4:00 p.m. | ||
| Fri., 2/11 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:50-4:50 p.m. | ||
| Fri., 2/11 | JV Boys Ice Hockey | Wilton Hockey Club | Away - Winter Garden Ice Arena | 4:00 p.m. | ||
| Fri., 2/11 | V Boys Indoor Track | Class LL Championship | Away - Floyd Little Athletic Center | 4:00 p.m. | ||
| Fri., 2/11 | V Wrestling | FCIAC, Danbury, Darien, Fairfield Ludlowe, Fairfield Warde, Greenwich, TBA, New Canaan, Norwalk, Ridgefield, St. Joseph, Stamford, Trumbull, Westhill, Wilton | Away - New Canaan HS-Main Gym | 4:30 p.m. | ||
| Fri., 2/11 | V Girls Basketball | Bridgeport Central | Home - Staples HS-Staples Gym [Directions] | 6:00 p.m. | W 65-18 | |
| Fri., 2/11 | JV Girls Basketball | Bridgeport Central | Home - Staples HS-Staples Gym [Directions] | 4:30 p.m. | ||
| Fri., 2/11 | FR Girls Basketball | Darien | Home - Staples HS-Staples Gym [Directions] | Postponed | ||
| Fri., 2/11 | V Girls Indoor Track | Class LL Championship | Away - Floyd Little Athletic Center | 4:00 p.m. | ||
| Sat., 2/12 | V Boys Ice Hockey | Trumbull | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4:30 p.m. | L 1-6 | |
| Sat., 2/12 | V Wrestling | FCIAC Wrestling Championships Wrestlebacks | Away - New Canaan HS-Main Gym | 10:00 a.m. | ||
| Sat., 2/12 | V Competitive Cheerleading | Cheer Your Heart Out at East Haven HS | Away - Not Listed | TBA | ||
| Sat., 2/12 | V Girls Gymnastics | FCIAC Gymnastics Championships | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 | 11:00 a.m. | 134.15 | |
| Sat., 2/12 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Terry Conners - Stamford-Ice Rink [Directions] | 6:20 p.m. | W 7-2 | |
| Mon., 2/14 | V Boys Alpine Skiing | Practice | Home - Mt. Southingon Ski Area [Directions] | 4-6 p.m. | ||
| Mon., 2/14 | V Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 7:00 p.m. | L 71-76 | |
| Mon., 2/14 | JV Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 5:15 p.m. | ||
| Mon., 2/14 | FR Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:00 p.m. | ||
| Mon., 2/14 | V Boys Ice Hockey | SCW Knights | Home - Milford Ice Pavillion-Ice Rink [Directions] | 7:30 p.m. | L 3-2 | |
| Mon., 2/14 | V Boys Swimming and Diving | New Canaan | Home - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Mon., 2/14 | V Girls Alpine Skiing | Practice | Home - Mt. Southingon Ski Area [Directions] | 4-6 p.m. | ||
| Mon., 2/14 | V Girls Basketball | St. Joseph | Home - Staples HS-Staples Gym [Directions] | 7:00 p.m. | L 45-20 | |
| Mon., 2/14 | JV Girls Basketball | St. Joseph | Home - Staples HS-Staples Gym [Directions] | 5:15 p.m. | ||
| Mon., 2/14 | FR Girls Basketball | St. Joseph | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/15 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:50-4:50 p.m. | ||
| Tue., 2/15 | V Girls Gymnastics | Wilton, Norwalk | Away - Wilton HS-Aux Gym [Directions] | 4:30 p.m. | 126.8 | |
| Wed., 2/16 | V Boys Basketball | Norwalk | Home - Staples HS-Staples Gym [Directions] | 7:00 p.m. | W 50-34 | |
| Wed., 2/16 | JV Boys Basketball | Norwalk | Home - Staples HS-Staples Gym [Directions] | 5:15 p.m. | ||
| Wed., 2/16 | FR Boys Basketball | Norwalk | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/16 | V Boys Ice Hockey | Milford Coop | Away - Milford Ice Pavillion-Ice Rink [Directions] | 6:15 p.m. | W 6-0 | |
| Wed., 2/16 | V Boys Swimming and Diving | Wilton | Away - Wilton YMCA [Directions] | 3:40 p.m. | ||
| Wed., 2/16 | V Girls Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 6:15 p.m. | W 38-32 | |
| Wed., 2/16 | JV Girls Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:30 p.m. | ||
| Wed., 2/16 | V Girls Gymnastics | Norwalk | Home - Westport YMCA [Directions] | 7:00 p.m. | 126.45 | |
| Wed., 2/16 | V Girls Ice Hockey | Guilford Coop | Away - Milford Ice Pavillion-Ice Rink [Directions] | 8:15 p.m. | W 7-0 | |
| Thu., 2/17 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:50-4:50 p.m. | ||
| Thu., 2/17 | FR Girls Basketball | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | 4:15 p.m. | ||
| Fri., 2/18 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 4-5:15 p.m. | ||
| Fri., 2/18 | V Wrestling | Class LL Championship - Day 1 | Away - Trumbull | 1:45 p.m. | ||
| Fri., 2/18 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | 5:30 p.m. | W 5-2 | |
| Sat., 2/19 | V Boys Ice Hockey | Tri-Town | Away - Enfield Twin Rinks-Rink 1 [Directions] | 6:00 p.m. | L 0-9 | |
| Sat., 2/19 | V Boys Indoor Track | State Open | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Sat., 2/19 | V Wrestling | Class LL Championship - Day 2 | Away - Trumbull | 12:00 p.m. | ||
| Sat., 2/19 | V Competitive Cheerleading | Hatterfest | Away - Danbury HS | TBA | ||
| Sat., 2/19 | V Girls Ice Hockey | Mercy/NW Catholic/East Hampton | Away - Champions Skating Rink - Cromwell-Upper Rink [Directions] | 12:00 p.m. | L 5-2 | |
| Sat., 2/19 | V Girls Indoor Track | State Open | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Mon., 2/21 | V Boys Basketball | Brien McMahon | Home - Staples HS-Staples Gym [Directions] | 7:00 p.m. | W 58-32 | |
| Mon., 2/21 | JV Boys Basketball | Brien McMahon | Home - Staples HS-Staples Gym [Directions] | 5:15 p.m. | ||
| Mon., 2/21 | FR Boys Basketball | Brien McMahon | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Mon., 2/21 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 10-11:15 a.m. | ||
| Mon., 2/21 | V Boys Ice Hockey | Brien McMahon/Norwalk | Home - Milford Ice Pavillion-Ice Rink [Directions] | 6:10 p.m. | W 4-0 | |
| Tue., 2/22 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 10-11:15 a.m. | ||
| Wed., 2/23 | V Boys Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | W 66-55 | |
| Wed., 2/23 | JV Boys Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/23 | FR Boys Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 2:30 p.m. | ||
| Wed., 2/23 | V Boys Ice Hockey | JBWA | Away - Danbury Ice Arena-Patriot Rink [Directions] | 5:00 p.m. | L 3-5 | |
| Wed., 2/23 | V Boys Swimming and Diving | Danbury | Away - WCSU O'Neill Center - Blue Gym-O'Neill Center [Directions] | 5:00 p.m. | ||
| Wed., 2/23 | V Girls Basketball | Fairfield Warde | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/23 | V Girls Basketball | Fairfield Warde | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/23 | V Girls Ice Hockey | Darien | Home - Darien Ice House-Ice Rink [Directions] | 5:50 p.m. | ||
| Thu., 2/24 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 10-11:15 a.m. | ||
| Fri., 2/25 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 10-11:15 a.m. | ||
| Sat., 2/26 | V Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 5:00 p.m. | L 52-55 | |
| Sat., 2/26 | V Wrestling | State Open - Day 1 | Away - Floyd Little Athletic Center | 12:45 p.m. | ||
| Sat., 2/26 | V Girls Gymnastics | CIAC Class L Divisional Championship | Away - Richetelli Gymnasium @Jonathan Law | 2:00 p.m. | ||
| Sat., 2/26 | V Girls Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | 2:30 p.m. | ||
| Sun., 2/27 | V Wrestling | State Open - Day 2 | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Mon., 2/28 | V Boys Alpine Skiing | Practice | Home - Mt. Southingon Ski Area [Directions] | Canceled | Cancelled | |
| Mon., 2/28 | FR Boys Basketball | Weston | Away - Weston HS-Gym (New) [Directions] | 5:30 p.m. | ||
| Mon., 2/28 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:50-4:50 p.m. | ||
| Mon., 2/28 | V Girls Alpine Skiing | Practice | Home - Mt. Southingon Ski Area [Directions] | Canceled | Cancelled | |
| Mon., 2/28 | V Girls Basketball | Hillhouse | Away - Hillhouse HS-Gym [Directions] | 6:30 p.m. | ||
| Tue., 3/1 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:50-4:50 p.m. | ||
| Tue., 3/1 | V Boys Swimming and Diving | FCIAC Boys' Swim Trials | Away - Greenwich HS | 5:30 p.m. | ||
| Wed., 3/2 | V Boys Swimming and Diving | FCIAC Diving Finals | Away - Westhill High-Westhill HS | 5:00 p.m. | ||
| Thu., 3/3 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:50-4:50 p.m. | ||
| Thu., 3/3 | V Boys Swimming and Diving | FCIAC Boys' Swim Finals | Away - Greenwich HS | 6:30 p.m. | ||
| Thu., 3/3 | V Girls Ice Hockey | East Catholic Coop | Home - Terry Conners - Stamford-Ice Rink [Directions] | 7:30 p.m. | ||
| Fri., 3/4 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 3:50-4:50 p.m. | ||
| Sat., 3/5 | V Boys Indoor Track | New England Championship | Away - Reggie Lewis Center | 10:30 a.m. | ||
| Sat., 3/5 | V Boys Rugby | Practice | Home - Fordham Prep School-Fordham Prep [Directions] | TBA | ||
| Sat., 3/5 | V Competitive Cheerleading | State Championship | Away - Floyd Little Athletic Center | TBA | ||
| Sat., 3/5 | V Girls Gymnastics | State Open | Away - New Milford | 10:00 a.m. | ||
| Sat., 3/5 | V Girls Indoor Track | New England Championship | Away - Reggie Lewis Center | 10:00 a.m. | ||
| Sun., 3/6 | V Boys Ice Hockey | Practice | Home - Milford Ice Pavillion-Ice Rink [Directions] | 2-3 p.m. | ||
| Mon., 3/7 | V Boys Basketball | Sheehan | Home - Staples HS-Staples Gym [Directions] | 6:30 p.m. | W 70-23 | |
| Mon., 3/7 | V Boys Ice Hockey | Suffield/Granby/Windsor Locks Wildcats | Away - Enfield Twin Rinks-Rink 1 [Directions] | 2:50 p.m. | W 4-3 | |
| Thu., 3/10 | V Boys Basketball | Waterford | Away - Waterford HS-Francis X. Sweeney Field House [Directions] | 6:30 p.m. | ||
| Thu., 3/10 | V Boys Ice Hockey | Newington Coop | Away - Northford Ice Pavilion-Red [Directions] | 7:00 p.m. | ||
| Fri., 3/11 | V Boys Indoor Track | Indoor National Championship | Away - Ocean Breeze Athletic Complex | TBA | ||
| Fri., 3/11 | V Girls Indoor Track | Indoor National Championship | Away - Staples HS-Field House | 10:00 a.m. | ||
| Sat., 3/12 | V Boys Indoor Track | Indoor National Championship | Away - Ocean Breeze Athletic Complex | TBA | ||
| Sat., 3/12 | V Boys Rugby | Xavier High School NYC D1 & D2 | Home - Staples HS-Staples Stadium [Directions] | 3:00 p.m. | ||
| Sat., 3/12 | V Girls Indoor Track | Indoor National Championship | Away - Staples HS-Field House | 10:00 a.m. | ||
| Sun., 3/13 | V Boys Indoor Track | Indoor National Championship | Away - Ocean Breeze Athletic Complex | TBA | ||
| Sun., 3/13 | V Boys Swimming and Diving | CIAC Class LL Qualifying Meet | Away - Cornerstone Pool | 5:30 p.m. | ||
| Sun., 3/13 | V Girls Indoor Track | Indoor National Championship | Away - Staples HS-Field House | 10:00 a.m. | ||
| Mon., 3/14 | V Boys Swimming and Diving | CIAC Class LL Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Wed., 3/16 | V Boys Swimming and Diving | CIAC Class LL Swimming Championships | Away - Cornerstone Pool | 1:30 p.m. | ||
| Thu., 3/17 | V Boys Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 3/19 | V Boys Rugby | Georgetown Prep | Away - Georgetown Preparatory School | TBA | ||
| Sat., 3/19 | V Boys Swimming and Diving | CIAC State Open Swimming Championships | Away - Cornerstone Pool | 3:15 p.m. | ||
| Wed., 3/23 | V Boys Lacrosse | Deerfield MA | Away - Farmington Sports Arena | 3:30 p.m. | ||
| Wed., 3/23 | V Co-ed Sailing | SHS vs DHS, BMHS, FL | Home - Cedar Point Yacht Club [Directions] | 3:30 p.m. | ||
| Thu., 3/24 | JV Boys Rugby | Darien | Home - Staples HS-Staples Stadium [Directions] | 5:00 p.m. | ||
| Thu., 3/24 | V Boys Volleyball | Shelton (Scrim.) | Away - Shelton HS-Murray Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 3/24 | JV Boys Volleyball | Shelton (Scrim.) | Away - Shelton HS-Murray Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 3/25 | V Baseball | Trumbull (Scrim.) | Home - Staples HS-Baseball Diamond [Directions] | 3:45 p.m. | Cancelled | |
| Fri., 3/25 | JV Baseball | Trumbull (Scrim.) | Away - Trumbull HS-Varsity Baseball Field [Directions] | Canceled | Cancelled | |
| Fri., 3/25 | V Softball | Notre Dame-Fairfield (Scrim.) | Away - Notre Dame - Fairfield -Park Ave Field [Directions] | 4:30 p.m. | ||
| Sat., 3/26 | V Baseball | Amity (Scrim.) | Away - Amity Regional HS-John Janenda Field [Directions] | 10:30 a.m. | ||
| Sat., 3/26 | V Boys Lacrosse | St. Anthonys (NY) (Scrim.) | Away - St. Anthony's HS | 10:00 a.m. | ||
| Sat., 3/26 | JV Boys Lacrosse | St. Anthonys (NY) (Scrim.) | Away - St. Anthony's HS-Stadium | 10:00 a.m. | ||
| Sat., 3/26 | V Girls Lacrosse | Bishop Guertin (NH), Fairfield Ludlowe, Greenwich Academy, Greenwich, Guilford, TBA, New Canaan, Sacred Heart of Greenwich, St. Joseph, Weston | Home - Staples HS-Staples Stadium [Directions] | 9:00 a.m. | ||
| Sat., 3/26 | V Girls Lacrosse | TBA | Home - Staples HS-Ginny Parker Field [Directions] | 9:00 a.m. | ||
| Tue., 3/29 | V Baseball | Weston (Scrim.) | Away - Weston HS-Revson #1 (Varsity) [Directions] | 4:00 p.m. | Cancelled | |
| Tue., 3/29 | V Boys Volleyball | Fairfield Ludlowe (Scrim.) | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 3:30 p.m. | ||
| Tue., 3/29 | JV Boys Volleyball | Fairfield Ludlowe (Scrim.) | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:00 p.m. | ||
| Tue., 3/29 | V Girls Lacrosse | Cheshire (Scrim.) | Away - Cheshire HS-Cheshire High School Main Game field [Directions] | 5:00 p.m. | ||
| Tue., 3/29 | JV Girls Lacrosse | Cheshire (Scrim.) | Away - Cheshire HS-Bartlem Park [Directions] | Canceled | Cancelled | |
| Wed., 3/30 | V Boys Lacrosse | Trinity Pawling (NY) (Scrim.) | Home - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Wed., 3/30 | JV Boys Lacrosse | Brien McMahon (Scrim.) | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Wed., 3/30 | V Co-ed Sailing | SHS vs GHS, GFA, FL | Away - Grass Island | 3:30 p.m. | ||
| Thu., 3/31 | V Baseball | Fairfield Warde (Scrim.) | Home - Staples HS-Baseball Diamond [Directions] | 3:00 p.m. | ||
| Thu., 3/31 | FR Baseball | Fairfield Warde (Scrim.) | Home - Staples HS-Wakeman Field [Directions] | Canceled | Cancelled | |
| Thu., 3/31 | FR Baseball | Fairfield Warde (Scrim.) | Home - Staples HS-Wakeman Field [Directions] | Canceled | Cancelled | |
| Thu., 3/31 | V Boys Volleyball | Joel Barlow, Fairfield Warde, Greenwich, New Canaan, Newington, Newtown, Simsbury | Away - Joel Barlow HS-Lower Gym | 3:30 p.m. | ||
| Thu., 3/31 | V Softball | Newtown (Scrim.) | Away - Newtown HS-NHS Softball Field [Directions] | 4:30 p.m. | ||
| Thu., 3/31 | V Softball | Notre Dame-Fairfield (Scrim.) | Away - Notre Dame - Fairfield -Park Ave Field [Directions] | 4:30 p.m. | Cancelled | |
| Fri., 4/1 | V Boys Rugby | Aspetuck Club | Away - Not Listed | 4:30 p.m. | ||
| Fri., 4/1 | JV Boys Rugby | Aspetuck Club | Away - Not Listed | 6:00 p.m. | ||
| Fri., 4/1 | V Girls Lacrosse | Joel Barlow (Scrim.) | Home - Staples HS-Ginny Parker Field [Directions] | 3:45 p.m. | ||
| Fri., 4/1 | JV Girls Lacrosse | Joel Barlow (Scrim.) | Home - Staples HS-Ginny Parker Field [Directions] | 5:00 p.m. | ||
| Sat., 4/2 | V Baseball | Notre Dame-West Haven | Home - Staples HS-Baseball Diamond [Directions] | 2:00 p.m. | W 8-3 | |
| Sat., 4/2 | JV Baseball | Darien | Away - Darien HS-DHS Baseball - JV Field [Directions] | 2:00 p.m. | ||
| Sat., 4/2 | V Boys Lacrosse | Bronxville (NY) | Home - Staples HS-Staples Stadium [Directions] | 4:30 p.m. | W 17-3 | |
| Sat., 4/2 | JV Boys Lacrosse | Chaminade (NY) | Away - Chaminade-OTT FIELD | 10:00 a.m. | ||
| Sat., 4/2 | FR Boys Lacrosse | Chaminade (NY) | Away - Chaminade-OTT FIELD | 12:30 p.m. | ||
| Sat., 4/2 | V Girls Water Polo | Choate Rosemary Hall | Home - Staples HS-Staples High School Pool [Directions] | 3:00 p.m. | ||
| Sat., 4/2 | Miscellaneous Events | ACT testing | Home - Staples HS-Cafeteria [Directions] | 9:00 a.m. | ||
| Mon., 4/4 | V Boys Outdoor Track | St. Joseph | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Mon., 4/4 | V Girls Lacrosse | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | W 18-7 | |
| Mon., 4/4 | JV Girls Lacrosse | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Mon., 4/4 | FR Girls Lacrosse | Ridgefield | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Mon., 4/4 | V Girls Outdoor Track | St. Joseph | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/5 | V Baseball | Bridgeport Central | Away - Bridgeport Central HS-Baseball Diamond [Directions] | 4:00 p.m. | W 12-1 (5) | |
| Tue., 4/5 | JV Baseball | Fairfield Ludlowe | Home - Staples HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Tue., 4/5 | V Boys Lacrosse | Stamford | Home - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | W 22-0 | |
| Tue., 4/5 | JV Boys Lacrosse | Stamford | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Tue., 4/5 | V Girls Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 3:15 p.m. | 170-234W [Detailed Results] | |
| Tue., 4/5 | JV Girls Golf | Greens Farms Academy | Home - Staples HS-Longshore Golf Course [Directions] | 3:30 p.m. | ||
| Tue., 4/5 | V Girls Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 4:30 p.m. | L 11-13 | |
| Tue., 4/5 | JV Girls Lacrosse | Ridgefield | Away - Ridgefield HS-Tiger Hollow Turf Field II [Directions] | 6:00 p.m. | ||
| Wed., 4/6 | FR Boys Lacrosse | Ridgefield | Away - Scotts Ridge MS [Directions] | 4:00 p.m. | ||
| Wed., 4/6 | V Boys Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:30 p.m. | L 1-3 | |
| Wed., 4/6 | JV Boys Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 4/6 | V Co-ed Sailing | SHS vs GHS, GFA, Prep, BMHS | Away - Grass Island | 3:30 p.m. | ||
| Wed., 4/6 | V Girls Rugby | Trumbull | Home - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Wed., 4/6 | V Girls Water Polo | Sacred Heart of Greenwich | Home - Staples HS-Staples High School Pool [Directions] | 3:00 p.m. | ||
| Thu., 4/7 | JV Boys Lacrosse | Cheshire | Home - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Thu., 4/7 | V Girls Water Polo | Greenwich | Home - Staples HS-Staples High School Pool [Directions] | 3:30 p.m. | ||
| Fri., 4/8 | FR Baseball | Fairfield Ludlowe | Home - Staples HS-Wakeman Field [Directions] | Postponed | ||
| Fri., 4/8 | FR Boys Lacrosse | Fairfield Ludlowe | Home - Staples HS-Wakeman Field [Directions] | 5:30 p.m. | ||
| Fri., 4/8 | V Boys Outdoor Track | Trumbull | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Fri., 4/8 | V Boys Rugby | Trumbull | Away - Trumbull HS-Cork Field [Directions] | 7:00 p.m. | ||
| Fri., 4/8 | JV Boys Rugby | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 5:00 p.m. | ||
| Fri., 4/8 | V Girls Outdoor Track | Trumbull | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Sat., 4/9 | V Boys Lacrosse | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 12:00 p.m. | W 22-3 | |
| Sat., 4/9 | JV Boys Lacrosse | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 10:00 a.m. | ||
| Mon., 4/11 | FR Boys Lacrosse | Wilton | Home - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Mon., 4/11 | V Boys Tennis | Ridgefield | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Mon., 4/11 | JV Boys Tennis | Ridgefield | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 4/11 | FR Girls Lacrosse | Wilton | Away - Wilton HS-Allen Meadow [Directions] | 4:00 p.m. | ||
| Mon., 4/11 | V Girls Tennis | Ridgefield | Away - Ridgefield HS-RHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Mon., 4/11 | JV Girls Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | Postponed | ||
| Tue., 4/12 | V Boys Outdoor Track | Bassick, Bridgeport Central, Harding | Home - Staples HS-Staples Stadium [Directions] | 4:30 p.m. | ||
| Tue., 4/12 | V Boys Tennis | New Canaan | Away - New Canaan HS-NCHS Tennis Courts [Directions] | 4:00 p.m. | W 6-1 [Detailed Results] | |
| Tue., 4/12 | JV Girls Golf | Fairfield Warde | Away - Carl Dickman Par 3-Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 4/12 | JV Girls Golf | Fairfield Ludlowe | Away - Carl Dickman Par 3 [Directions] | 3:15 p.m. | ||
| Tue., 4/12 | V Girls Lacrosse | Fairfield Warde | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | W 16-5 | |
| Tue., 4/12 | JV Girls Lacrosse | Fairfield Warde | Home - Staples HS-Ginny Parker Field [Directions] | 5:30 p.m. | ||
| Tue., 4/12 | V Girls Outdoor Track | Bassick, Bridgeport Central, Harding | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/12 | V Girls Tennis | New Canaan | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 4/12 | V Girls Water Polo | Greenwich Aquatics | Home - Staples HS-Staples High School Pool [Directions] | 5:00 p.m. | ||
| Wed., 4/13 | FR Baseball | Fairfield Warde | Home - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | ||
| Wed., 4/13 | V Boys Volleyball | Glastonbury | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | L 1-3 | |
| Wed., 4/13 | JV Boys Volleyball | Glastonbury | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Wed., 4/13 | V Co-ed Sailing | SHS vs BS, GA, Prep | Away - Indian Harbor Yacht Club | 3:30 p.m. | ||
| Wed., 4/13 | JV Girls Tennis | Wilton | Away - Wilton Middlebrook School-JV Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 4/14 | JV Baseball | Ridgefield | Away - East Ridge MS-Baseball Field [Directions] | 4:00 p.m. | ||
| Thu., 4/14 | FR Baseball | Ridgefield | Home - Staples HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Thu., 4/14 | V Boys Lacrosse | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 3:30 p.m. | W 12-8 | |
| Thu., 4/14 | JV Boys Lacrosse | Greenwich | Away - Greenwich HS-Field 4 [Directions] | Postponed | ||
| Thu., 4/14 | V Boys Rugby | Fairfield Club | Home - Staples HS-Staples Stadium [Directions] | 5:45 p.m. | ||
| Thu., 4/14 | JV Boys Tennis | Greenwich | Home - Staples HS-Town Farms Tennis Courts [Directions] | 3:30 p.m. | ||
| Thu., 4/14 | V Boys Volleyball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Thu., 4/14 | JV Boys Volleyball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 4:00 p.m. | ||
| Thu., 4/14 | V Girls Golf | Danbury | Away - Richter Park Golf Course [Directions] | 3:00 p.m. | 191-261 W | |
| Thu., 4/14 | V Girls Lacrosse | Greenwich | Home - Staples HS-Ginny Parker Field [Directions] | 3:30 p.m. | W 10-6 | |
| Thu., 4/14 | JV Girls Lacrosse | Greenwich | Home - Staples HS-Ginny Parker Field [Directions] | 5:00 p.m. | ||
| Thu., 4/14 | V Girls Rugby | Greenwich | Away - Greenwich HS-Field 7 [Directions] | 4:30 p.m. | ||
| Thu., 4/14 | V Softball | Ridgefield | Home - Staples HS-Wakeman Field [Directions] | 3:00 p.m. | W 3-1 | |
| Thu., 4/14 | JV Softball | Ridgefield | Home - Staples HS-Staples Softball Field [Directions] | 4:30 p.m. | ||
| Thu., 4/14 | JV Girls Tennis | Greenwich | Away - Binney Park [Directions] | 4:00 p.m. | ||
| Thu., 4/14 | V Girls Water Polo | Loomis Chaffee School | Home - Staples HS-Staples High School Pool [Directions] | 5:00 p.m. | ||
| Sat., 4/16 | V Boys Lacrosse | St. Joseph | Home - Staples HS-Staples Stadium [Directions] | 10:00 a.m. | W 19-10 | |
| Sat., 4/16 | JV Boys Lacrosse | St. Joseph | Home - Staples HS-Wakeman Field B (turf) [Directions] | 11:45 a.m. | ||
| Sat., 4/16 | FR Boys Lacrosse | Greenwich | Away - Greenwich HS-Field 4 [Directions] | 10:00 a.m. | ||
| Sat., 4/16 | V Boys Volleyball | Darien | Home - Staples HS-Staples Gym [Directions] | 10:00 a.m. | L 0-3 | |
| Sat., 4/16 | JV Boys Volleyball | Darien | Home - Staples HS-Staples Gym [Directions] | 11:30 a.m. | ||
| Sat., 4/16 | V Softball | Trumbull | Away - Trumbull HS-Varsity Softball Diamond [Directions] | 12:00 p.m. | L 4-5 | |
| Sat., 4/16 | JV Softball | Trumbull | Away - Trumbull HS-JV Softball Diamond [Directions] | 10:00 a.m. | ||
| Mon., 4/18 | V Baseball | New Canaan | Home - Staples HS-Baseball Diamond [Directions] | 4:30 p.m. | W 7-3 | |
| Mon., 4/18 | JV Baseball | New Canaan | Home - Staples HS-Wakeman Field [Directions] | 4:30 p.m. | ||
| Mon., 4/18 | FR Baseball | New Canaan | Away - New Canaan HS-Coppo Field [Directions] | 4:00 p.m. | ||
| Mon., 4/18 | FR Boys Lacrosse | New Canaan | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Mon., 4/18 | V Boys Tennis | Danbury | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Mon., 4/18 | V Boys Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | L 2-3 | |
| Mon., 4/18 | JV Boys Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 4/18 | FR Girls Lacrosse | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | Canceled | Cancelled | |
| Mon., 4/18 | V Softball | New Canaan | Away - Waveny Park-Orchard Field [Directions] | 4:00 p.m. | L 4-5 | |
| Mon., 4/18 | JV Softball | New Canaan | Away - Waveny Park-Orchard Field [Directions] | 4:00 p.m. | ||
| Mon., 4/18 | V Girls Tennis | Danbury | Away - Danbury HS-DHS Tennis Courts [Directions] | 11:00 a.m. | W 7-0 | |
| Mon., 4/18 | JV Girls Tennis | Fairfield Warde | Away - Fairfield Woods-Tennis Courts [Directions] | Postponed | ||
| Tue., 4/19 | V Boys Lacrosse | St. Johns Prep (NY) | Home - Staples HS-Staples Stadium [Directions] | 1:00 p.m. | W 14-9 | |
| Tue., 4/19 | JV Boys Lacrosse | Danbury | Home - Staples HS-Wakeman Field B (turf) [Directions] | Canceled | Cancelled | |
| Tue., 4/19 | V Boys Tennis | Westhill | Away - Westhill HS-Westhill Tennis Courts [Directions] | 3:00 p.m. | W 5-2 [Detailed Results] | |
| Tue., 4/19 | V Girls Lacrosse | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 6:00 p.m. | W 17-5 | |
| Tue., 4/19 | JV Girls Lacrosse | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 4:30 p.m. | ||
| Tue., 4/19 | JV Girls Tennis | St. Joseph | Home - Staples HS-Town Farms Tennis Courts [Directions] | Postponed | ||
| Wed., 4/20 | V Baseball | Greenwich | Away - Greenwich HS-Baseball Field [Directions] | 4:30 p.m. | L 2-1 | |
| Wed., 4/20 | JV Baseball | Greenwich | Away - Julian Curtiss School [Directions] | 4:30 p.m. | ||
| Wed., 4/20 | FR Baseball | Greenwich | Home - Staples HS-Baseball Diamond [Directions] | 4:30 p.m. | ||
| Wed., 4/20 | FR Boys Lacrosse | Trumbull | Away - Trumbull HS-The Pit [Directions] | Postponed | ||
| Wed., 4/20 | V Boys Tennis | Greenwich | Home - Staples HS-Staples Tennis Courts [Directions] | 11:00 a.m. | L 3-4 [Detailed Results] | |
| Wed., 4/20 | V Boys Volleyball | Greenwich | Home - Staples HS-Staples Gym [Directions] | 11:30 a.m. | W 3-1 | |
| Wed., 4/20 | JV Boys Volleyball | Greenwich | Home - Staples HS-Staples Gym [Directions] | 10:00 a.m. | ||
| Wed., 4/20 | V Girls Lacrosse | Darien | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | L 14-8 | |
| Wed., 4/20 | JV Girls Lacrosse | Darien | Home - Staples HS-Ginny Parker Field [Directions] | 5:30 p.m. | ||
| Wed., 4/20 | V Softball | Greenwich | Home - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | W 9-1 | |
| Wed., 4/20 | JV Softball | Greenwich | Home - Staples HS-Wakeman Field [Directions] | Postponed | ||
| Wed., 4/20 | V Girls Tennis | Greenwich | Away - Greenwich HS-Tennis Courts [Directions] | 11:00 a.m. | W 5-1 | |
| Wed., 4/20 | V Girls Tennis | Westhill | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | W 4-3 | |
| Thu., 4/21 | V Boys Rugby | Practice | Home - Staples HS-Staples Stadium [Directions] | 1-4 p.m. | ||
| Thu., 4/21 | V Boys Tennis | Wilton | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | W 6-1 [Detailed Results] | |
| Thu., 4/21 | JV Boys Tennis | Wilton | Home - Staples HS-Town Farms Tennis Courts [Directions] | Postponed | ||
| Thu., 4/21 | V Girls Tennis | Wilton | Away - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | W 4-3 | |
| Fri., 4/22 | V Baseball | Danbury | Away - Danbury HS-V Baseball Field [Directions] | 1:00 p.m. | L 12-2 | |
| Fri., 4/22 | JV Baseball | Danbury | Away - Danbury HS-JV Baseball Field [Directions] | 1:00 p.m. | ||
| Fri., 4/22 | FR Baseball | Danbury | Home - Staples HS-Baseball Diamond [Directions] | 1:00 p.m. | ||
| Fri., 4/22 | FR Boys Lacrosse | Stamford | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Fri., 4/22 | V Boys Outdoor Track | CT Distance Festival | Away - William H Hall HS | 5:00 p.m. | ||
| Fri., 4/22 | V Boys Rugby | Practice | Home - Staples HS-Staples Stadium [Directions] | 10-11:30 a.m. | ||
| Fri., 4/22 | V Boys Rugby | Gonzage Classic | Away - TBA | TBA | ||
| Fri., 4/22 | V Boys Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:00 p.m. | L 2-3 | |
| Fri., 4/22 | JV Boys Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 4/22 | V Softball | Danbury | Home - Staples HS-Wakeman Field [Directions] | 2:00 p.m. | L 0-4 | |
| Fri., 4/22 | JV Softball | Danbury | Home - Staples HS-Wakeman Field [Directions] | 3:30 p.m. | ||
| Sat., 4/23 | V Baseball | Hall | Home - Staples HS-Baseball Diamond [Directions] | 1:00 p.m. | W 5-4 | |
| Sat., 4/23 | JV Baseball | Hall | Home - Staples HS-Wakeman Field [Directions] | 1:00 p.m. | ||
| Sat., 4/23 | V Boys Lacrosse | Wilton | Home - Staples HS-Staples Stadium [Directions] | 3:00 p.m. | W 8-6 | |
| Sat., 4/23 | JV Boys Lacrosse | Wilton | Home - Staples HS-Wakeman Field B (turf) [Directions] | 12:30 p.m. | ||
| Sat., 4/23 | FR Boys Lacrosse | Chaminade (NY) | Home - Staples HS-Staples Stadium [Directions] | 12:30 p.m. | ||
| Sat., 4/23 | V Boys Outdoor Track | Hill House Invitational | Away - Floyd Little Athletic Center | 10:00 a.m. | ||
| Sat., 4/23 | V Girls Lacrosse | Wilton | Away - Wilton HS-Lilly Field [Directions] | 6:00 p.m. | L 8-17 | |
| Sat., 4/23 | JV Girls Lacrosse | Wilton | Away - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | ||
| Sat., 4/23 | V Girls Outdoor Track | Hill House Invitational | Away - Floyd Little Athletic Center | 9:30 a.m. | ||
| Mon., 4/25 | V Baseball | Westhill | Home - Staples HS-Baseball Diamond [Directions] | 4:30 p.m. | L 5-0 | |
| Mon., 4/25 | JV Baseball | Westhill | Home - Staples HS-Wakeman Field [Directions] | 4:30 p.m. | ||
| Mon., 4/25 | FR Baseball | Westhill | Away - Westhill HS-Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/25 | V Boys Outdoor Track | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 4:00 p.m. | ||
| Mon., 4/25 | V Boys Tennis | Darien | Away - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | L 3-4 [Detailed Results] | |
| Mon., 4/25 | JV Boys Tennis | Darien | Away - Weed Beach Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 4/25 | V Boys Volleyball | Bridgeport Central | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 4/25 | JV Boys Volleyball | Bridgeport Central | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Mon., 4/25 | V Girls Outdoor Track | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 4:00 p.m. | ||
| Mon., 4/25 | V Softball | Westhill | Away - Westhill HS-Varsity Softball Field [Directions] | 4:00 p.m. | W 8-0 | |
| Mon., 4/25 | JV Softball | Westhill | Away - Westhill HS-Varsity Softball Field [Directions] | 6:00 p.m. | ||
| Mon., 4/25 | JV Girls Tennis | Darien | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/26 | V Boys Lacrosse | Iona Prep (NY) | Away - IONA PREP-Lacrosse Field | 5:30 p.m. | L 13-14 | |
| Tue., 4/26 | JV Boys Lacrosse | Iona Prep (NY) | Home - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Tue., 4/26 | V Girls Golf | Darien | Away - Country Club of Darien [Directions] | 3:00 p.m. | 185-231 W | |
| Wed., 4/27 | V Baseball | Wilton | Away - Wilton HS-Varsity Baseball Field [Directions] | 4:30 p.m. | W 12-2 (6) | |
| Wed., 4/27 | JV Baseball | Wilton | Away - Wilton HS-JV Baseball Field [Directions] | 4:30 p.m. | ||
| Wed., 4/27 | FR Baseball | Wilton | Home - Staples HS-Baseball Diamond [Directions] | Postponed | ||
| Wed., 4/27 | FR Boys Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 4:00 p.m. | ||
| Wed., 4/27 | V Boys Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:00 p.m. | W 3-1 | |
| Wed., 4/27 | JV Boys Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 4/27 | V Girls Golf | St. Joseph | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | 186-232 W | |
| Wed., 4/27 | V Softball | Wilton | Home - Staples HS-Wakeman Field [Directions] | 4:30 p.m. | W 12-8 | |
| Wed., 4/27 | JV Softball | Wilton | Home - Staples HS-Staples Softball Field [Directions] | 5:30 p.m. | ||
| Wed., 4/27 | V Girls Tennis | Fairfield Warde | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Wed., 4/27 | JV Girls Tennis | Fairfield Warde | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/27 | V Girls Water Polo | Greenwich | Away - Greenwich HS-Pool [Directions] | 4:15 p.m. | ||
| Thu., 4/28 | V Boys Lacrosse | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | L 10-15 | |
| Thu., 4/28 | JV Boys Lacrosse | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Thu., 4/28 | V Boys Tennis | Trumbull | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Thu., 4/28 | JV Boys Tennis | Trumbull | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 4/28 | V Girls Golf | Fairfield Ludlowe | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | 183-240 W | |
| Thu., 4/28 | JV Girls Golf | Fairfield Ludlowe | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 4/28 | V Girls Lacrosse | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 4:00 p.m. | W 13-3 | |
| Thu., 4/28 | JV Girls Lacrosse | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 5:30 p.m. | ||
| Thu., 4/28 | FR Girls Lacrosse | Fairfield Ludlowe | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Thu., 4/28 | V Girls Rugby | Darien | Home - Staples HS-Staples Stadium [Directions] | Canceled | Cancelled | |
| Thu., 4/28 | V Girls Tennis | Trumbull | Away - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Thu., 4/28 | JV Girls Tennis | Trumbull | Away - Tashua Knolls Golf Course-Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 4/29 | V Baseball | Darien | Home - Staples HS-Baseball Diamond [Directions] | 4:30 p.m. | W 7-1 | |
| Fri., 4/29 | JV Baseball | Darien | Home - Staples HS-Wakeman Field [Directions] | 4:30 p.m. | ||
| Fri., 4/29 | FR Baseball | Darien | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Fri., 4/29 | FR Boys Lacrosse | Darien | Home - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Fri., 4/29 | V Boys Outdoor Track | O'Grady Relays | Away - Danbury HS | 5:00 p.m. | ||
| Fri., 4/29 | V Boys Tennis | Fairfield Warde | Away - Fairfield Warde HS-Blake Courts [Directions] | 3:00 p.m. | W 5-2 [Detailed Results] | |
| Fri., 4/29 | JV Boys Tennis | Fairfield Warde | Away - Fairfield Warde HS-Knapps Courts [Directions] | 4:00 p.m. | ||
| Fri., 4/29 | V Boys Volleyball | Ridgefield | Home - Staples HS-Staples Gym [Directions] | 4:30 p.m. | L 0-3 | |
| Fri., 4/29 | JV Boys Volleyball | Ridgefield | Home - Staples HS-Staples Gym [Directions] | 6:00 p.m. | ||
| Fri., 4/29 | FR Girls Lacrosse | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 4/29 | V Girls Outdoor Track | O'Grady Relays | Away - Danbury HS | 5:00 p.m. | ||
| Fri., 4/29 | V Softball | Darien | Away - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | W 19-9 | |
| Fri., 4/29 | JV Softball | Darien | Away - Darien HS-DHS - Softball - JV Field [Directions] | Canceled | Cancelled | |
| Sat., 4/30 | V Boys Lacrosse | Bishop Guertin (NH) | Away - Bryant University | 4:00 p.m. | W 17-8 | |
| Sat., 4/30 | V Boys Outdoor Track | O'Grady Relays | Away - Danbury HS | 9:00 a.m. | ||
| Sat., 4/30 | V Boys Rugby | Greenwich | Home - Staples HS-Staples Stadium [Directions] | 1:00 p.m. | ||
| Sat., 4/30 | JV Boys Rugby | Greenwich | Home - Staples HS-Staples Stadium [Directions] | 2:15 p.m. | ||
| Sat., 4/30 | V Girls Lacrosse | Trumbull | Home - Staples HS-Staples Stadium [Directions] | 7:00 p.m. | W 19-8 | |
| Sat., 4/30 | JV Girls Lacrosse | Trumbull | Home - Staples HS-Ginny Parker Field [Directions] | 5:00 p.m. | ||
| Sat., 4/30 | V Girls Outdoor Track | O'Grady Relays | Away - Danbury HS | 9:00 a.m. | ||
| Sat., 4/30 | V Girls Water Polo | Choate Rosemary Hall | Away - Choate School | 1:30 p.m. | ||
| Mon., 5/2 | JV Boys Lacrosse | Weston | Away - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 5/2 | FR Boys Lacrosse | Wilton | Away - Allen's Meadow-Lacrosse Field #1 [Directions] | 4:30 p.m. | ||
| Mon., 5/2 | JV Boys Tennis | Fairfield Ludlowe | Away - Tomlinson MS-Tennis Courts [Directions] | Postponed | ||
| Mon., 5/2 | V Boys Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:30 p.m. | L 2-3 | |
| Mon., 5/2 | JV Boys Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 5/2 | JV Girls Golf | New Canaan | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Mon., 5/2 | V Girls Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | L 11-12 | |
| Mon., 5/2 | JV Girls Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 5:30 p.m. | ||
| Mon., 5/2 | FR Girls Lacrosse | Wilton | Home - Staples HS-Ginny Parker Field [Directions] | 4:30 p.m. | ||
| Mon., 5/2 | JV Softball | Fairfield Warde | Away - Fairfield Warde HS-Softball Diamond [Directions] | 5:30 p.m. | ||
| Tue., 5/3 | V Baseball | Fairfield Warde | Home - Staples HS-Baseball Diamond [Directions] | 4:00 p.m. | L 13-2 | |
| Tue., 5/3 | JV Baseball | Fairfield Warde | Home - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | ||
| Tue., 5/3 | FR Baseball | Fairfield Warde | Away - Fairfield Warde HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Tue., 5/3 | V Boys Outdoor Track | Norwalk | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/3 | V Boys Tennis | Bridgeport Central | Away - Bridgeport Central HS-Central High School Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Tue., 5/3 | JV Boys Tennis | Greenwich | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/3 | JV Girls Golf | Fairfield Warde | Away - Carl Dickman Par 3-Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 5/3 | JV Girls Golf | Fairfield Ludlowe | Away - Carl Dickman Par 3 [Directions] | 3:15 p.m. | ||
| Tue., 5/3 | V Girls Outdoor Track | Norwalk | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/3 | V Girls Tennis | Bridgeport Central | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 5/3 | JV Girls Tennis | Greenwich | Away - Binney Park [Directions] | 4:30 p.m. | ||
| Tue., 5/3 | V Girls Water Polo | Greenwich Aquatics | Away - Greenwich YMCA | 6:00 p.m. | ||
| Wed., 5/4 | V Boys Lacrosse | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 4:30 p.m. | W 23-0 | |
| Wed., 5/4 | FR Boys Lacrosse | Fairfield Warde | Home - Staples HS-Wakeman Field E (grass) [Directions] | Canceled | Cancelled | |
| Wed., 5/4 | V Boys Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 5/4 | JV Boys Volleyball | Stamford | Away - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 5/4 | V Co-ed Sailing | BS/GA/GHS, Greenwich Cleanup All Schools | Away - Indian Harbor Yacht Club | 3:30 p.m. | ||
| Wed., 5/4 | V Girls Golf | Fairfield Warde | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | 173-242 W | |
| Thu., 5/5 | V Baseball | Trumbull | Away - Trumbull HS-Varsity Baseball Field [Directions] | 4:30 p.m. | L 5-1 | |
| Thu., 5/5 | JV Baseball | Trumbull | Away - Trumbull HS-JV Baseball Field [Directions] | 4:30 p.m. | ||
| Thu., 5/5 | FR Baseball | Trumbull | Home - Staples HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Thu., 5/5 | V Boys Lacrosse | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | W 20-2 | |
| Thu., 5/5 | JV Boys Lacrosse | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | ||
| Thu., 5/5 | V Boys Tennis | St. Joseph | Away - St. Joseph HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Thu., 5/5 | V Boys Volleyball | Trumbull | Home - Staples HS-Staples Gym [Directions] | 5:00 p.m. | L 0-3 | |
| Thu., 5/5 | JV Boys Volleyball | Trumbull | Home - Staples HS-Staples Gym [Directions] | 6:30 p.m. | ||
| Thu., 5/5 | V Girls Rugby | North Haven | Home - North Haven Athletic Complex-All-Purpose Field [Directions] | 5:30 p.m. | ||
| Thu., 5/5 | V Softball | Fairfield Warde | Away - Fairfield Warde HS-Softball Diamond [Directions] | 4:00 p.m. | L 1-2 | |
| Thu., 5/5 | JV Softball | Fairfield Warde | Away - Fairfield Warde HS-Softball Diamond [Directions] | 5:30 p.m. | ||
| Thu., 5/5 | V Girls Tennis | St. Joseph | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Thu., 5/5 | JV Girls Tennis | St. Joseph | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 5/6 | FR Boys Lacrosse | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | Postponed | ||
| Fri., 5/6 | V Boys Outdoor Track | Middletown Invitational - FR & Soph | Away - Middletown HS | 3:30 p.m. | ||
| Fri., 5/6 | V Boys Tennis | Weston | Away - Weston HS-WHS Tennis Courts [Directions] | Canceled | Cancelled | |
| Fri., 5/6 | V Girls Lacrosse | Westhill | Home - Staples HS-Ginny Parker Field [Directions] | 4:30 p.m. | W 17-9 | |
| Fri., 5/6 | JV Girls Lacrosse | Westhill | Home - Staples HS-Ginny Parker Field [Directions] | 6:00 p.m. | ||
| Fri., 5/6 | JV Girls Tennis | New Canaan | Home - Staples HS-Town Farms Tennis Courts [Directions] | Postponed | ||
| Sat., 5/7 | V Boys Outdoor Track | Middletown Invitational - Varsity | Away - Middletown HS | 12:00 p.m. | ||
| Sat., 5/7 | V Boys Rugby | Simsbury | Away - Holden Field-Simsbury 2 [Directions] | 1:00 p.m. | ||
| Sat., 5/7 | V Girls Lacrosse | Bishop Guertin (NH) | Home - Staples HS-Ginny Parker Field [Directions] | 12:30 p.m. | L 7-14 | |
| Sat., 5/7 | JV Girls Lacrosse | Bishop Guertin (NH) | Home - Staples HS-Ginny Parker Field [Directions] | Canceled | Cancelled | |
| Sat., 5/7 | V Girls Outdoor Track | Jake Spartan Invitational | Away - Amity Regional HS | TBA | ||
| Sat., 5/7 | Miscellaneous Events | SAT testing | Home - Staples HS-Cafeteria [Directions] | 9:00 a.m. | ||
| Mon., 5/9 | V Baseball | Bridgeport Central | Home - Staples HS-Baseball Diamond [Directions] | 4:30 p.m. | W 13-2 | |
| Mon., 5/9 | JV Baseball | Bassick | Home - Staples HS-Wakeman Field [Directions] | 4:30 p.m. | ||
| Mon., 5/9 | JV Boys Lacrosse | Darien (Scrim.) | Home - Staples HS-Wakeman Field B (turf) [Directions] | 5:30 p.m. | ||
| Mon., 5/9 | FR Boys Lacrosse | Trumbull | Home - Staples HS-Wakeman Field E (grass) [Directions] | Postponed | ||
| Mon., 5/9 | V Boys Outdoor Track | Danbury | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Mon., 5/9 | V Boys Tennis | Norwalk | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Mon., 5/9 | JV Boys Tennis | Trumbull | Away - Tashua Knolls Golf Course-Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 5/9 | V Boys Volleyball | Danbury | Home - Staples HS-Staples Gym [Directions] | 4:30 p.m. | W 3-1 | |
| Mon., 5/9 | JV Boys Volleyball | Danbury | Home - Staples HS-Staples Gym [Directions] | 6:00 p.m. | ||
| Mon., 5/9 | V Girls Golf | New Canaan | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | L 191-188 | |
| Mon., 5/9 | FR Girls Lacrosse | Trumbull | Away - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Mon., 5/9 | V Girls Outdoor Track | Danbury | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Mon., 5/9 | V Softball | Bridgeport Central | Away - Bridgeport Central HS-Varsity Softball Field [Directions] | 4:00 p.m. | W Forfeit | |
| Mon., 5/9 | V Girls Tennis | Norwalk | Away - Norwalk HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Mon., 5/9 | JV Girls Tennis | Trumbull | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/10 | V Baseball | Ridgefield | Away - Governor Field [Directions] | 4:00 p.m. | L 1-5 | |
| Tue., 5/10 | FR Baseball | Greenwich | Away - Greenwich HS-Baseball Field [Directions] | 4:30 p.m. | ||
| Tue., 5/10 | V Boys Lacrosse | Glastonbury | Home - Staples HS-Staples Stadium [Directions] | 6:00 p.m. | W 15-4 | |
| Tue., 5/10 | JV Boys Lacrosse | Glastonbury | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:30 p.m. | ||
| Tue., 5/10 | FR Boys Lacrosse | Notre Dame-West Haven | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Tue., 5/10 | V Boys Tennis | Brien McMahon | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Tue., 5/10 | JV Boys Tennis | Fairfield Ludlowe | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/10 | V Co-ed Sailing | FCSL Silver Cup | Away - Indian Harbor Yacht Club | 3:30 p.m. | ||
| Tue., 5/10 | V Girls Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | 187-199 W | |
| Tue., 5/10 | JV Girls Golf | Trumbull | Away - Tashua Knolls Golf Course-Tashua Glen [Directions] | 3:15 p.m. | ||
| Tue., 5/10 | V Girls Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 6:00 p.m. | L 3-13 | |
| Tue., 5/10 | JV Girls Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/10 | V Softball | Trumbull | Home - Staples HS-Wakeman Field [Directions] | 4:15 p.m. | L 2-6 | |
| Tue., 5/10 | JV Softball | Trumbull | Home - Staples HS-Staples Softball Field [Directions] | 6:00 p.m. | ||
| Tue., 5/10 | V Girls Tennis | Brien McMahon | Away - Brien McMahon HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 5/10 | JV Girls Tennis | Fairfield Ludlowe | Away - Tomlinson MS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/11 | V Baseball | St. Joseph | Home - Staples HS-Baseball Diamond [Directions] | 4:00 p.m. | W 2-1 | |
| Wed., 5/11 | JV Baseball | St. Joseph | Home - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | ||
| Wed., 5/11 | FR Baseball | St. Joseph | Away - St. Joseph HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 5/11 | FR Boys Lacrosse | Greenwich | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:30 p.m. | ||
| Wed., 5/11 | V Boys Tennis | Stamford | Away - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Wed., 5/11 | V Boys Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:00 p.m. | W 3-1 | |
| Wed., 5/11 | JV Boys Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 5:30 p.m. | ||
| Wed., 5/11 | V Co-ed Sailing | FCSL GOld Cup | Away - Indian Harbor Yacht Club | 3:30 p.m. | ||
| Wed., 5/11 | V Girls Golf | Ridgefield | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | 176-236 W | |
| Wed., 5/11 | JV Girls Golf | Ridgefield | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 5/11 | FR Girls Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 4:30 p.m. | ||
| Wed., 5/11 | V Girls Rugby | Greenwich | Home - Staples HS-Staples Stadium [Directions] | Postponed | ||
| Wed., 5/11 | V Softball | St. Joseph | Away - St. Joseph HS-Softball Diamond [Directions] | 4:30 p.m. | L 0-6 | |
| Wed., 5/11 | JV Softball | St. Joseph | Away - Long Hill Administration Bldg-Softball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/11 | V Girls Tennis | Darien | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | L 3-4 | |
| Wed., 5/11 | V Girls Tennis | Stamford | Home - Staples HS-Staples Tennis Courts [Directions] | 4:30 p.m. | W 7-0 | |
| Thu., 5/12 | V Baseball | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 6:00 p.m. | L 2-1 | |
| Thu., 5/12 | JV Baseball | Norwalk | Away - City Hall Field [Directions] | 4:30 p.m. | ||
| Thu., 5/12 | V Boys Lacrosse | Bergen Catholic (NJ) | Home - Sacred Heart University-Turf Field [Directions] | 5:30 p.m. | W 17-5 | |
| Thu., 5/12 | JV Boys Lacrosse | Bergen Catholic (NJ) | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Thu., 5/12 | FR Boys Lacrosse | Bergen Catholic (NJ) | Away - Bergen Catholic HS-Stadium Turf | 4:15 p.m. | ||
| Thu., 5/12 | V Boys Outdoor Track | Loucks Games | Away - White Plains HS | TBA | ||
| Thu., 5/12 | V Boys Rugby | Fairfield Prep | Home - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Thu., 5/12 | JV Boys Rugby | Fairfield Prep | Home - Staples HS-Staples Stadium [Directions] | 6:45 p.m. | ||
| Thu., 5/12 | V Boys Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Thu., 5/12 | JV Boys Tennis | Fairfield Ludlowe | Away - Tomlinson MS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/12 | V Boys Volleyball | New Canaan | Home - Staples HS-Staples Gym [Directions] | 4:30 p.m. | L 1-3 | |
| Thu., 5/12 | JV Boys Volleyball | New Canaan | Home - Staples HS-Staples Gym [Directions] | 6:00 p.m. | ||
| Thu., 5/12 | V Girls Lacrosse | Guilford | Away - Guilford HS-Kavanaugh Turf Field and Track [Directions] | 6:00 p.m. | L 19-8 | |
| Thu., 5/12 | JV Girls Lacrosse | Guilford | Away - Guilford HS-Kavanaugh Turf Field and Track [Directions] | 4:30 p.m. | ||
| Thu., 5/12 | V Softball | Norwalk | Home - Staples HS-Wakeman Field [Directions] | 4:00 p.m. | W 7-6 | |
| Thu., 5/12 | JV Softball | Norwalk | Home - Staples HS-Staples Softball Field [Directions] | 5:30 p.m. | ||
| Thu., 5/12 | V Girls Tennis | Fairfield Ludlowe | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | W 4-3 | |
| Thu., 5/12 | JV Girls Tennis | Fairfield Ludlowe | Home - Staples HS-Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 5/13 | FR Baseball | Norwalk | Home - Staples HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Fri., 5/13 | FR Boys Lacrosse | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 5/13 | V Boys Outdoor Track | Loucks Games | Away - White Plains HS | TBA | ||
| Fri., 5/13 | FR Girls Lacrosse | Darien | Home - Staples HS-Ginny Parker Field [Directions] | 4:30 p.m. | ||
| Fri., 5/13 | V Girls Outdoor Track | Loucks Games | Away - White Plains HS | TBA | ||
| Sat., 5/14 | V Baseball | Waterford | Home - Staples HS-Baseball Diamond [Directions] | 1:00 p.m. | W 9-5 | |
| Sat., 5/14 | JV Baseball | Waterford | Home - Staples HS-Wakeman Field [Directions] | 1:00 p.m. | ||
| Sat., 5/14 | V Boys Lacrosse | New Canaan | Home - Staples HS-Staples Stadium [Directions] | 3:00 p.m. | W 11-3 | |
| Sat., 5/14 | JV Boys Lacrosse | New Canaan | Home - Staples HS-Staples Stadium [Directions] | 12:30 p.m. | ||
| Sat., 5/14 | V Boys Outdoor Track | Greater Hartford Invitational | Away - East Hartford HS | 9:00 a.m. | ||
| Sat., 5/14 | V Boys Outdoor Track | Loucks Games | Away - White Plains HS | TBA | ||
| Sat., 5/14 | V Girls Outdoor Track | Froshmore Invitational | Away - Floyd Little Athletic Center | 9:30 a.m. | ||
| Sat., 5/14 | V Girls Outdoor Track | Loucks Games | Away - White Plains HS | TBA | ||
| Sun., 5/15 | V Boys Rugby | Practice | Home - Staples HS-Staples Stadium [Directions] | 11 a.m.-1 p.m. | ||
| Mon., 5/16 | JV Softball | Brien McMahon | Home - Staples HS-Wakeman Field [Directions] | Postponed | ||
| Mon., 5/16 | JV Girls Tennis | New Canaan | Home - Staples HS-Town Farms Tennis Courts [Directions] | Canceled | Cancelled | |
| Tue., 5/17 | V Baseball | Stamford | Home - Staples HS-Baseball Diamond [Directions] | 4:30 p.m. | W 16-3 | |
| Tue., 5/17 | JV Baseball | Stamford | Home - Staples HS-Wakeman Field [Directions] | 4:30 p.m. | ||
| Tue., 5/17 | FR Baseball | Stamford | Away - Stamford HS-SHS Baseball Diamond [Directions] | 4:00 p.m. | ||
| Tue., 5/17 | V Boys Lacrosse | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 5:00 p.m. | W 15-4 | |
| Tue., 5/17 | JV Boys Lacrosse | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 6:30 p.m. | ||
| Tue., 5/17 | FR Boys Lacrosse | Newtown | Away - Treadwell Park-Newtown Treadwell Park [Directions] | 6:00 p.m. | ||
| Tue., 5/17 | V Boys Outdoor Track | Greenwich | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/17 | V Girls Golf | Fairfield Warde | Away - Smith Richardson Golf Course [Directions] | 3:00 p.m. | 181-247 W | |
| Tue., 5/17 | V Girls Lacrosse | Brien McMahon | Home - Staples HS-Ginny Parker Field [Directions] | 7:45 p.m. | W 15-3 | |
| Tue., 5/17 | FR Girls Lacrosse | New Canaan | Away - New Canaan HS-WTT #1 [Directions] | 4:00 p.m. | ||
| Tue., 5/17 | V Girls Outdoor Track | Greenwich | Home - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/17 | V Softball | Stamford | Away - Stamford HS-SHS Softball Diamond [Directions] | 4:00 p.m. | L 6-11 | |
| Tue., 5/17 | JV Softball | Stamford | Away - Stamford HS-SHS Softball Diamond [Directions] | Canceled | Cancelled | |
| Tue., 5/17 | V Girls Tennis | Greenwich | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/18 | V Baseball | Fairfield Ludlowe | Home - Staples HS-Baseball Diamond [Directions] | 4:15 p.m. | W 8-0 | |
| Wed., 5/18 | JV Baseball | Fairfield Ludlowe | Home - Staples HS-Wakeman Field [Directions] | 4:15 p.m. | ||
| Wed., 5/18 | FR Baseball | Fairfield Ludlowe | Away - Kiwanis Field-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 5/18 | V Boys Tennis | Fairfield Warde | Home - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/18 | V Boys Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Wed., 5/18 | JV Boys Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 5/18 | V Girls Golf | St. Joseph | Home - Staples HS-Longshore Golf Course [Directions] | 2:40 p.m. | 182-210 W | |
| Wed., 5/18 | JV Girls Golf | New Canaan | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 5/18 | JV Girls Lacrosse | Brien McMahon | Home - Staples HS-Ginny Parker Field [Directions] | 5:00 p.m. | ||
| Wed., 5/18 | V Softball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 4:00 p.m. | L 1-9 | |
| Wed., 5/18 | JV Softball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 5:30 p.m. | ||
| Thu., 5/19 | V Baseball | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 5:45 p.m. | W 9-6 | |
| Thu., 5/19 | FR Baseball | Darien | Away - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | ||
| Thu., 5/19 | JV Boys Lacrosse | Fairfield Ludlowe (Scrim.) | Home - Staples HS-Staples Stadium [Directions] | Canceled | Cancelled | |
| Thu., 5/19 | V Boys Volleyball | Fairfield Warde | Home - Staples HS-Staples Gym [Directions] | 4:30 p.m. | W 3-1 | |
| Thu., 5/19 | JV Boys Volleyball | Fairfield Warde | Home - Staples HS-Staples Gym [Directions] | 6:00 p.m. | ||
| Thu., 5/19 | V Girls Golf | Wilton | Away - Silvermine Golf Club [Directions] | 3:30 p.m. | 157-170 W | |
| Thu., 5/19 | V Girls Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 7:00 p.m. | ||
| Thu., 5/19 | V Girls Rugby | Darien | Away - Royle School Field [Directions] | 5:00 p.m. | ||
| Fri., 5/20 | JV Baseball | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 4:00 p.m. | ||
| Fri., 5/20 | V Boys Outdoor Track | Dream Invitational | Away - Danbury HS | 5:00 p.m. | ||
| Fri., 5/20 | V Boys Tennis | Darien | Away - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 5/23 | ||||||
| Fri., 5/20 | V Softball | Brien McMahon | Home - Wakeman Field-Field C [Directions] | 3:00 p.m. | W 10-1 | |
| Fri., 5/20 | V Girls Tennis | Westhill | Home - Staples HS-Staples Tennis Courts [Directions] | 3:00 p.m. | W 5-0 | |
| Sat., 5/21 | V Boys Lacrosse | St. Joseph | Home - Staples HS-Staples Stadium [Directions] | 11:00 a.m. | ||
| Sat., 5/21 | V Boys Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 11:00 a.m. | ||
| Sat., 5/21 | V Softball | Danbury | Away - Danbury HS-V Softball field [Directions] | 11:00 a.m. | ||
| Sun., 5/22 | V Softball | Masuk | Away - Masuk HS-Masuk High School Softball Field [Directions] | 12:30 p.m. | L 1-8 | |
| Mon., 5/23 | JV Baseball | Darien | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Mon., 5/23 | FR Baseball | Westhill | Away - Rippowan MS-Rippowam Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/23 | FR Boys Lacrosse | Ridgefield | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Mon., 5/23 | V Boys Tennis | Darien | Away - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 5/23 | V Girls Golf | Darien | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | 179-223 W | |
| Mon., 5/23 | JV Girls Golf | Darien | Away - Wee Burn CC [Directions] | Canceled | Cancelled | |
| Mon., 5/23 | V Girls Outdoor Track | FCIAC Championships | Away - Wilton HS-Fujitani Field - Turf | 3:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Facility to Danbury HS-Wilton HS-Fujitani Field - Turf | ||||||
| Tue., 5/24 | V Baseball | Greenwich | Home - Staples HS-Baseball Diamond [Directions] | 4:00 p.m. | W 15-5 | |
| Tue., 5/24 | JV Baseball | Greenwich | Away - Greenwich HS-Baseball Field [Directions] | 4:15 p.m. | ||
| Tue., 5/24 | V Boys Lacrosse | Wilton | Home - Brien McMahon HS-Casagrande Field [Directions] | 5:00 p.m. | ||
| Tue., 5/24 | V Boys Outdoor Track | FCIAC Championship | Away - Danbury HS | 1:30 p.m. | ||
| Tue., 5/24 | V Boys Outdoor Track | FCIAC Championships | Away - Danbury HS-Stadium Track | 3:30 p.m. | ||
| Tue., 5/24 | V Girls Golf | Greenwich | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | 181-186 W | |
| Tue., 5/24 | JV Girls Golf | Greenwich | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | ||
| Tue., 5/24 | JV Girls Golf | Fairfield Warde | Away - Carl Dickman Par 3-Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 5/24 | JV Girls Golf | Fairfield Ludlowe | Away - Carl Dickman Par 3 [Directions] | 3:15 p.m. | ||
| Tue., 5/24 | V Girls Lacrosse | Greenwich (Scrim.) | Away - Greenwich HS-Field 3 [Directions] | 4:00 p.m. | Cancelled | |
| Tue., 5/24 | V Girls Tennis | Darien | Away - Wilton HS-Staples Tennis Courts [Directions] | 3:00 p.m. | ||
| Wed., 5/25 | V Baseball | St. Joseph (Scrim.) | Away - St. Joseph HS-Baseball Diamond [Directions] | 3:15 p.m. | ||
| Wed., 5/25 | FR Baseball | St. Joseph | Home - Staples HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 5/25 | JV Boys Lacrosse | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 4:30 p.m. | ||
| Wed., 5/25 | V Girls Golf | Trumbull | Home - Staples HS-Longshore Golf Course [Directions] | 3:00 p.m. | 172-197 W | |
| Wed., 5/25 | JV Girls Golf | Ekstrom JV Tournament | Away - Carl Dickman Par 3 | 3:00 p.m. | ||
| Wed., 5/25 | JV Girls Golf | Trumbull | Home - Staples HS-Longshore Golf Course [Directions] | 3:15 p.m. | ||
| Wed., 5/25 | V Girls Lacrosse | St. Joseph (Scrim.) | Home - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | ||
| Thu., 5/26 | V Boys Lacrosse | FCIAC Finals | Away - Brien McMahon HS | TBA | ||
| Thu., 5/26 | V Boys Rugby | Ridgefield | Home - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Thu., 5/26 | JV Boys Rugby | Ridgefield | Home - Staples HS-Staples Stadium [Directions] | 6:45 p.m. | ||
| Thu., 5/26 | V Girls Rugby | CT HS Girls Championship | Away - trumbull high school | 4:00 p.m. | ||
| Fri., 5/27 | V Girls Lacrosse | Stratford/Bunnell | Away - Penders Field-Penders Field - Stratford [Directions] | 4:00 p.m. | W 18-3 | |
| Sat., 5/28 | JV Baseball | Hall | Home - Staples HS-Wakeman Field [Directions] | 3:15 p.m. | ||
| Tue., 5/31 | V Baseball | Fairfield Ludlowe | Home - Staples HS-Baseball Diamond [Directions] | 4:00 p.m. | ||
| Tue., 5/31 | V Boys Outdoor Track | CIAC Class LL Championship | Away - Willow Brook Park | 4:00 p.m. | ||
| Tue., 5/31 | V Boys Tennis | Ridgefield | Home - Staples HS-Staples Tennis Courts [Directions] | 3:00 p.m. | ||
| Tue., 5/31 | V Girls Golf | New Canaan | Home - Fairchild Wheeler Golf Course [Directions] | 2:30 p.m. | 184-177 L | |
| Tue., 5/31 | V Girls Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 5:00 p.m. | L 13-5 | |
| Tue., 5/31 | V Girls Outdoor Track | CIAC Class LL Championship | Away - Willow Brook Park | 4:00 p.m. | ||
| Tue., 5/31 | V Softball | Newtown | Away - Newtown HS-Lindell A. Hertberg Softball Field [Directions] | 4:00 p.m. | ||
| Tue., 5/31 | V Girls Tennis | Greenwich | Home - Staples HS-Staples Tennis Courts [Directions] | 1:00 p.m. | ||
| Tue., 5/31 | V Girls Tennis | CIAC First Round vs. Greenwich/Cheshire winner | Home - Staples HS-Staples Tennis Courts [Directions] | 1:00 p.m. | [Detailed Results] | |
| Wed., 6/1 | V Baseball | Amity | Away - Amity Regional HS-John Janenda Field [Directions] | 3:45 p.m. | ||
| Wed., 6/1 | V Boys Lacrosse | Norwich Free Academy | Home - Staples HS-Staples Stadium [Directions] | 4:30 p.m. | ||
| Wed., 6/1 | V Boys Tennis | Fairfield Prep | Away - Fairfield University-Walsh Athletic Center - Tennis Courts [Directions] | 3:00 p.m. | ||
| Wed., 6/1 | V Softball | West Haven | Away - West Haven HS-Frank Biondi Field [Directions] | 4:00 p.m. | ||
| Wed., 6/1 | V Girls Tennis | CIAC Quarterfinals vs. East Hartford | Home - Staples HS-Staples Tennis Courts [Directions] | 3:30 p.m. | ||
| Thu., 6/2 | V Girls Golf | FCIAC Championship | Home - Fairchild Wheeler Golf Course [Directions] | 12:00 p.m. | ||
| Thu., 6/2 | V Girls Tennis | Darien | Away - Solaris Racquet Club [Directions] | 2:00 p.m. | ||
| Fri., 6/3 | V Boys Tennis | Amity | Home - Staples HS-Staples Tennis Courts [Directions] | 3:00 p.m. | ||
| Sat., 6/4 | V Baseball | Trumbull | Away - Trumbull HS-Varsity Baseball Field [Directions] | 2:00 p.m. | ||
| Sat., 6/4 | V Boys Lacrosse | Fairfield Ludlowe | Home - Staples HS-Staples Stadium [Directions] | 3:00 p.m. | ||
| Sat., 6/4 | Miscellaneous Events | SAT testing | Home - Staples HS-Cafeteria [Directions] | 9:00 a.m. | ||
| Mon., 6/6 | V Boys Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/6 | V Boys Rugby | Trumbull | Home - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Mon., 6/6 | V Boys Tennis | CIAC Individual Invitational - Opening Round, Singles and Doubles | Away - Wesleyan | 10:00 a.m. | ||
| Mon., 6/6 | V Girls Golf | CIAC Division I Championship | Away - Tashua Knolls GC | 8:30 a.m. | ||
| Mon., 6/6 | V Girls Golf | State Championship | Away - Tashua Knolls Golf Course | 8:30 a.m. | ||
| Mon., 6/6 | V Girls Outdoor Track | CIAC State Open Championship | Away - Willow Brook Park | 1:30 p.m. | ||
| Mon., 6/6 | V Girls Tennis | CIAC Individual Invitational - Opening Round, Singles and Doubles | Away - Wesleyan | 10:00 a.m. | ||
| Tue., 6/7 | V Boys Tennis | CIAC Individual Invitational - Round of 16 | Away - Wesleyan | 9:00 a.m. | ||
| Tue., 6/7 | V Girls Tennis | CIAC Individual Invitational - Round of 16 | Away - Wesleyan | 9:00 a.m. | ||
| Wed., 6/8 | V Boys Lacrosse | Ridgefield | Home - Fairfield University-Rafferty Stadium [Directions] | 5:00 p.m. | ||
| Wed., 6/8 | V Boys Tennis | CIAC Individual Invitational - Quarterfinals | Away - Wesleyan | 3:00 p.m. | ||
| Wed., 6/8 | V Girls Tennis | CIAC Individual Invitational - Quarterfinals | Away - Wesleyan | 3:00 p.m. | ||
| Thu., 6/9 | V Boys Rugby | Greenwich | Home - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | ||
| Thu., 6/9 | V Boys Tennis | CIAC Individual Invitational - Semifinals | Away - Wesleyan | 3:00 p.m. | ||
| Thu., 6/9 | V Girls Tennis | CIAC Individual Invitational - Semifinals | Away - Wesleyan | 3:00 p.m. | ||
| Fri., 6/10 | V Boys Tennis | CIAC Individual Invitational - Finals | Away - Wesleyan | 3:00 p.m. | ||
| Fri., 6/10 | V Girls Tennis | CIAC Individual Invitational - Finals | Away - Wesleyan | 3:00 p.m. | ||
| Sat., 6/11 | V Girls Golf | CIAC Girls State Open | Away - Black Hall Club | 1:00 p.m. | ||
| Sat., 6/11 | Miscellaneous Events | ACT testing | Home - Staples HS-Cafeteria [Directions] | 9:00 a.m. | ||
| Sun., 6/12 | V Boys Lacrosse | Darien | Away - Sacred Heart University [Directions] | 3:00 p.m. | ||
| Mon., 6/13 | V Boys Outdoor Track | CIAC Boys Hammer Throw Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Mon., 6/13 | V Girls Outdoor Track | CIAC Girls Hammer Throw Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Tue., 6/14 | V Boys Outdoor Track | CIAC Decathlon Championship Day 1 | Away - Willow Brook Park | 10:00 a.m. | ||
| Tue., 6/14 | V Girls Outdoor Track | CIAC Heptathlon Championship Day 1 | Away - Willow Brook Park | 10:30 a.m. | ||
| Tue., 6/14 | V Girls Outdoor Track | CIAC Girls Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/15 | V Boys Outdoor Track | CIAC Decathlon Championship Day 2 | Away - Willow Brook Park | 10:00 a.m. | ||
| Wed., 6/15 | V Boys Outdoor Track | CIAC Boys Steeplechase Championship | Away - Willow Brook Park | 3:30 p.m. | ||
| Wed., 6/15 | V Girls Outdoor Track | CIAC Heptathlon Championship Day 2 | Away - Willow Brook Park | 10:00 a.m. | ||