| Stamford 2022-23 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 670 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Thu., 8/25 | V Boys Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 2:50 p.m. | Ludlowe 153, Stamford 202 | |
| Mon., 8/29 | V Boys Golf | Darien | Home - Stamford High-Sterling Farms Golf Course [Directions] | 3:00 p.m. | Darien 164, Stamford 205 | |
| Tue., 8/30 | V Boys Golf | Fairfield Warde | Home - Stamford High-Sterling Farms Golf Course [Directions] | 2:30 p.m. | Warde 150, Stamford 201 | |
| Thu., 9/1 | V Boys Golf | Ridgefield | Away - Silver Spring Golf Course [Directions] | 3:15 p.m. | Ridgefield 161, Stamford 198 | |
| Thu., 9/8 | FR Football | Wilbur Cross | Home - Stamford HS-Boyle Stadium [Directions] | 5:00 p.m. | W 14-12 | |
| Thu., 9/8 | V Boys Soccer | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 4:00 p.m. | L 2-1 | |
| Thu., 9/8 | JV Boys Soccer | St. Joseph | Away - St. Joseph HS-Lower Grass Field [Directions] | 4:00 p.m. | ||
| Thu., 9/8 | V Field Hockey | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 6:00 p.m. | W 3-0 | |
| Thu., 9/8 | JV Field Hockey | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:30 p.m. | ||
| Fri., 9/9 | V Girls Soccer | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 4:00 p.m. | L 8-1 | |
| Fri., 9/9 | JV Girls Soccer | St. Joseph | Away - St. Joseph HS-Lower Grass Field [Directions] | 4:00 p.m. | ||
| Fri., 9/9 | V Girls Swimming and Diving | Staples | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Fri., 9/9 | V Girls Volleyball | Shelton | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | W 3-2 | |
| Sat., 9/10 | V Football | Wilbur Cross | Away - Bowen Field-Football Field [Directions] | 1:00 p.m. | W 41-12 | |
| Sat., 9/10 | FR Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 9:30 a.m. | ||
| Sat., 9/10 | V Competitive Cheerleading | Wilber Cross | Away - Not Listed | 1:00 p.m. | ||
| Sat., 9/10 | V Girls Volleyball | Foran | Home - Stamford HS-Kuczo Gymnasium [Directions] | 12:30 p.m. | W 3-1 | |
| Mon., 9/12 | V Boys Golf | Staples | Away - Longshore Golf Course [Directions] | Postponed | Staples 153, Stamford 171 | |
| Pending changes awaiting acceptance by one or more parties involved: Date to 10/3, Time to 3:15 p.m. | ||||||
| Mon., 9/12 | V Field Hockey | Brien McMahon | Home - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | W 4-3 | |
| Mon., 9/12 | JV Field Hockey | Brien McMahon | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Mon., 9/12 | V Girls Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 4:30 p.m. | L 3-0 | |
| Mon., 9/12 | JV Girls Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 6:00 p.m. | ||
| Tue., 9/13 | V Boys Golf | New Canaan | Home - Stamford High-Sterling Farms Golf Course [Directions] | 2:30 p.m. | New Canaan 166, Stamford 204 | |
| Tue., 9/13 | V Boys Soccer | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 6:00 p.m. | L 3-0 | |
| Tue., 9/13 | JV Boys Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 6:00 p.m. | ||
| Tue., 9/13 | FR Boys Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 4:00 p.m. | ||
| Wed., 9/14 | V Boys Cross Country | St. Joseph, Fairfield Ludlowe | Away - St. Joseph HS-Trail [Directions] | 4:00 p.m. | ||
| Wed., 9/14 | V Girls Cross Country | St. Joseph, Fairfield Ludlowe | Away - St. Joseph HS-Trail [Directions] | 4:00 p.m. | ||
| Wed., 9/14 | V Field Hockey | New Canaan | Home - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | L 8-0 | |
| Wed., 9/14 | JV Field Hockey | New Canaan | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Wed., 9/14 | V Girls Soccer | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 4:00 p.m. | L 2-0 | |
| Wed., 9/14 | JV Girls Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 4:00 p.m. | ||
| Wed., 9/14 | V Girls Swimming and Diving | Danbury | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Wed., 9/14 | V Girls Volleyball | Harding | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | W 3-0 | |
| Wed., 9/14 | JV Girls Volleyball | Harding | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 9/15 | V Boys Golf | Danbury | Away - Richter Park Golf Course [Directions] | 3:00 p.m. | Danbury 157, Stamford 203 | |
| Thu., 9/15 | V Boys Soccer | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 7:00 p.m. | L 2-1 | |
| Thu., 9/15 | JV Boys Soccer | Fairfield Warde | Away - Fairfield Warde HS-Fairfield Warde Grass Utility Field [Directions] | 4:00 p.m. | ||
| Fri., 9/16 | V Football | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 7:00 p.m. | L 27-54 | |
| Fri., 9/16 | FR Football | Somers (NY) | Away - Not Listed | 4:15 p.m. | W 14-7 | |
| Fri., 9/16 | FR Boys Soccer | Fairfield Warde | Home - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | ||
| Fri., 9/16 | V Competitive Cheerleading | At Danbury HS | Away - Not Listed-Danbury HS | 7:00 p.m. | ||
| Fri., 9/16 | V Girls Swimming and Diving | New Canaan | Away - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Fri., 9/16 | V Girls Volleyball | Weston | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | W 3-0 | |
| Fri., 9/16 | JV Girls Volleyball | Weston | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Sat., 9/17 | V Boys Cross Country | Wilton XC invitational | Away - Not Listed-Allen Meadow Park, Wilton HS | 9:30 a.m. | ||
| Sat., 9/17 | JV Football | Danbury | Home - Stamford HS-Boyle Stadium [Directions] | 10:00 a.m. | W 40-0 | |
| Sat., 9/17 | V Girls Cross Country | Wilton XC invitational | Away - Not Listed-Allen Meadow Park, Wilton HS | 9:30 a.m. | ||
| Sat., 9/17 | V Field Hockey | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 11:00 a.m. | W 4-0 | |
| Sat., 9/17 | JV Field Hockey | Westhill | Away - Westhill HS-Front Turf [Directions] | 12:30 p.m. | ||
| Sat., 9/17 | V Girls Soccer | Fairfield Warde | Home - Stamford HS-SHS Upper Soccer Field [Directions] | 11:00 a.m. | L 5-1 | |
| Sat., 9/17 | JV Girls Soccer | Fairfield Warde | Home - Stamford HS-SHS Upper Soccer Field [Directions] | 1:00 p.m. | ||
| Mon., 9/19 | V Boys Golf | Greenwich | Home - Stamford High-Sterling Farms Golf Course [Directions] | 3:00 p.m. | Greenwich 154, Stamford 180 | |
| Mon., 9/19 | V Boys Soccer | Wilton | Home - Stamford HS-SHS Upper Soccer Field [Directions] | 4:30 p.m. | W 2-0 | |
| Mon., 9/19 | JV Boys Soccer | Wilton | Home - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | ||
| Mon., 9/19 | FR Boys Soccer | Wilton | Away - Allen's Meadow-3A [Directions] | 4:30 p.m. | ||
| Tue., 9/20 | V Boys Cross Country | Fairfield Warde, Greenwich, Norwalk | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | ||
| Tue., 9/20 | V Boys Golf | Wilton | Home - Stamford High-Sterling Farms Golf Course [Directions] | 2:30 p.m. | Wilton 164, Stamford 184 | |
| Tue., 9/20 | V Girls Cross Country | Fairfield Warde, Greenwich, Norwalk | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | ||
| Tue., 9/20 | V Field Hockey | Wilton | Away - Wilton HS-Fuijitani Field -Turf [Directions] | 6:30 p.m. | L 0-7 | |
| Tue., 9/20 | JV Field Hockey | Wilton | Away - Wilton HS-Fuijitani Field -Turf [Directions] | 5:00 p.m. | ||
| Tue., 9/20 | V Girls Soccer | Wilton | Away - Wilton HS-Lilly Field [Directions] | 5:30 p.m. | L 3-0 | |
| Tue., 9/20 | JV Girls Soccer | Wilton | Away - Wilton HS-Allen Meadow [Directions] | 4:00 p.m. | ||
| Wed., 9/21 | V Boys Golf | Trumbull | Home - Stamford High-Sterling Farms Golf Course [Directions] | 3:00 p.m. | Trumbull 162, Stamford 195 | |
| Thu., 9/22 | FR Football | Manchester | Home - Stamford HS-Boyle Stadium [Directions] | 5:00 p.m. | L 30-8 | |
| Thu., 9/22 | V Boys Soccer | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 7:00 p.m. | L 1-0 | |
| Thu., 9/22 | JV Boys Soccer | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 4:00 p.m. | ||
| Thu., 9/22 | FR Boys Soccer | New Canaan | Home - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | ||
| Thu., 9/22 | V Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 5:30 p.m. | L 3-0 | |
| Thu., 9/22 | JV Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:00 p.m. | ||
| Thu., 9/22 | FR Girls Volleyball | St. Joseph | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | ||
| Fri., 9/23 | V Field Hockey | Norwalk | Home - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | L 3-1 | |
| Fri., 9/23 | JV Field Hockey | Norwalk | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Fri., 9/23 | V Girls Soccer | New Canaan | Home - Stamford HS-SHS Upper Soccer Field [Directions] | 4:00 p.m. | T 1-1 | |
| Fri., 9/23 | JV Girls Soccer | New Canaan | Home - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | ||
| Sat., 9/24 | V Football | Manchester | Home - Stamford HS-Boyle Stadium [Directions] | 1:00 p.m. | W 27-21 (OT) | |
| Sat., 9/24 | V Boys Soccer | Harding | Home - Stamford HS-SHS Upper Soccer Field [Directions] | 10:00 a.m. | W 6-1 | |
| Sat., 9/24 | V Girls Volleyball | Bassick | Home - Stamford HS-Kuczo Gymnasium [Directions] | 10:00 a.m. | W 3-0 | |
| Sat., 9/24 | JV Girls Volleyball | Bassick | Home - Stamford HS-Kuczo Gymnasium [Directions] | 11:30 a.m. | ||
| Mon., 9/26 | JV Football | Bullard/Kolbe | Away - Bullard Havens Tech-Football Field [Directions] | 4:00 p.m. | W 47-0 | |
| Wed., 9/28 | V Boys Cross Country | New Canaan, Westhill, Wilton | Away - Waveny Park [Directions] | 4:30 p.m. | ||
| Wed., 9/28 | V Boys Golf | Brien McMahon | Away - Oak Hills Golf Course [Directions] | 3:15 p.m. | McMahon 175, Stamford 186 | |
| Wed., 9/28 | V Boys Soccer | Ridgefield | Home - Stamford HS-SHS Upper Soccer Field [Directions] | 4:30 p.m. | L 2-1 | |
| Wed., 9/28 | JV Boys Soccer | Ridgefield | Home - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | ||
| Wed., 9/28 | FR Boys Soccer | Ridgefield | Away - Ridgefield HS-RHS Lower Grass Field [Directions] | 4:00 p.m. | ||
| Wed., 9/28 | V Girls Cross Country | New Canaan, Westhill, Wilton | Away - Waveny Park [Directions] | 4:30 p.m. | ||
| Wed., 9/28 | V Field Hockey | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 4:00 p.m. | W 2-1 | |
| Wed., 9/28 | JV Field Hockey | Danbury | Away - Danbury HS-Grass Field Hockey Field [Directions] | 5:30 p.m. | ||
| Wed., 9/28 | V Girls Soccer | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 4:00 p.m. | L 3-0 | |
| Wed., 9/28 | JV Girls Soccer | Ridgefield | Away - Ridgefield HS-Upper Grass Field [Directions] | 4:00 p.m. | ||
| Wed., 9/28 | V Girls Swimming and Diving | Wilton | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Wed., 9/28 | V Girls Volleyball | Brien McMahon | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | L 3-2 | |
| Wed., 9/28 | JV Girls Volleyball | Brien McMahon | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 9/28 | FR Girls Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:30 p.m. | ||
| Thu., 9/29 | FR Football | Brien McMahon | Home - Stamford HS-Boyle Stadium [Directions] | 5:00 p.m. | ||
| Thu., 9/29 | V Boys Golf | Westhill | Home - Stamford High-Sterling Farms Golf Course [Directions] | 3:00 p.m. | ||
| Thu., 9/29 | V Girls Volleyball | Danbury | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | W 3-0 | |
| Thu., 9/29 | JV Girls Volleyball | Danbury | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 9/29 | FR Girls Volleyball | Danbury | Away - Danbury HS-New gym [Directions] | 4:30 p.m. | ||
| Fri., 9/30 | V Boys Soccer | Trumbull | Home - Stamford HS-SHS Upper Soccer Field [Directions] | 4:00 p.m. | L 3-2 | |
| Fri., 9/30 | JV Boys Soccer | Trumbull | Home - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | ||
| Fri., 9/30 | FR Boys Soccer | Trumbull | Away - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Fri., 9/30 | V Field Hockey | Shelton | Away - Shelton HS-Finn Stadium [Directions] | 7:00 p.m. | W 2-0 | |
| Fri., 9/30 | JV Field Hockey | Shelton | Away - Shelton HS-Finn Stadium [Directions] | 5:30 p.m. | ||
| Fri., 9/30 | V Girls Swimming and Diving | Trumbull | Away - Bridgeport Univ Pool-Pool [Directions] | 4:00 p.m. | ||
| Sat., 10/1 | V Football | Ridgefield | Home - Stamford HS-Boyle Stadium [Directions] | 1:00 p.m. | L 29-41 | |
| Sat., 10/1 | V Girls Soccer | Trumbull | Away - Trumbull HS-Cork Field [Directions] | 3:00 p.m. | L 6-1 | |
| Sat., 10/1 | JV Girls Soccer | Trumbull | Away - Trumbull HS-The Pit [Directions] | 5:00 p.m. | ||
| Sat., 10/1 | V Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:00 p.m. | L 3-1 | |
| Sat., 10/1 | JV Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 2:30 p.m. | ||
| Sat., 10/1 | FR Girls Volleyball | Fairfield Warde | Home - Stamford HS-Kuczo Gymnasium [Directions] | 10:00 a.m. | ||
| Mon., 10/3 | V Boys Cross Country | Ridgefield, Brien McMahon, Danbury | Away - Ridgefield HS-Upper Grass Field [Directions] | 4:00 p.m. | ||
| Mon., 10/3 | JV Football | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 5:30 p.m. | L 19-6 | |
| Mon., 10/3 | V Girls Cross Country | Ridgefield, Brien McMahon, Danbury | Away - Ridgefield HS-Upper Grass Field [Directions] | 4:00 p.m. | ||
| Mon., 10/3 | V Field Hockey | Ridgefield | Home - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | L 6-1 | |
| Mon., 10/3 | JV Field Hockey | Ridgefield | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Mon., 10/3 | V Girls Swimming and Diving | Norwalk/McMahon | Away - Norwalk HS-Pat Spinola Natatorium [Directions] | 4:00 p.m. | ||
| Tue., 10/4 | FR Girls Volleyball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:15 p.m. | ||
| Thu., 10/6 | V Boys Golf | Chappa Invitational - Long Shore | Away - Not Listed-Longshore Golf Course | 9:30 a.m. | ||
| Thu., 10/6 | V Boys Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 7:00 p.m. | L 1-0 | |
| Thu., 10/6 | JV Boys Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 5:00 p.m. | ||
| Thu., 10/6 | FR Boys Soccer | Fairfield Ludlowe | Home - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | ||
| Thu., 10/6 | V Girls Swimming and Diving | Greenwich | Away - Greenwich HS-Pool [Directions] | 5:30 p.m. | ||
| Thu., 10/6 | V Girls Volleyball | Wilton | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | L 3-0 | |
| Thu., 10/6 | JV Girls Volleyball | Wilton | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 10/7 | V Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 6:30 p.m. | L 0-2 | |
| Fri., 10/7 | JV Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 5:00 p.m. | ||
| Fri., 10/7 | V Girls Soccer | Fairfield Ludlowe | Home - Stamford HS-SHS Upper Soccer Field [Directions] | 4:00 p.m. | L 0-3 | |
| Fri., 10/7 | JV Girls Soccer | Fairfield Ludlowe | Home - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | ||
| Sat., 10/8 | V Boys Soccer | Brien McMahon | Home - Stamford HS-SHS Upper Soccer Field [Directions] | 1:00 p.m. | W 1-0 | |
| Sat., 10/8 | JV Boys Soccer | Brien McMahon | Home - Stamford HS-SHS Upper Soccer Field [Directions] | 11:00 a.m. | ||
| Sat., 10/8 | V Competitive Cheerleading | Light the Night - Leukemia Walk - Calf Pasture Beach - Norwalk | Away - Not Listed | 5:00 p.m. | ||
| Sat., 10/8 | V Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 12:00 p.m. | L 3-0 | |
| Sat., 10/8 | JV Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 2:00 p.m. | ||
| Mon., 10/10 | V Boys Soccer | Staples | Away - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | L 2-0 | |
| Mon., 10/10 | JV Boys Soccer | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | Postponed | ||
| Mon., 10/10 | FR Boys Soccer | Staples | Home - Stamford HS-SHS Upper Soccer Field [Directions] | Postponed | ||
| Mon., 10/10 | V Girls Volleyball | Ridgefield | Home - Stamford HS-Kuczo Gymnasium [Directions] | 11:00 a.m. | L 3-2 | |
| Mon., 10/10 | JV Girls Volleyball | Ridgefield | Home - Stamford HS-Kuczo Gymnasium [Directions] | 12:30 p.m. | ||
| Mon., 10/10 | FR Girls Volleyball | Ridgefield | Home - Stamford HS-Kuczo Gymnasium [Directions] | 12:30 p.m. | ||
| Tue., 10/11 | V Boys Cross Country | Staples, Darien, Trumbull | Away - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 10/11 | V Boys Golf | Norwalk | Home - Stamford High-Sterling Farms Golf Course [Directions] | 2:30 p.m. | Norwalk 187, Stamford 188 | |
| Tue., 10/11 | V Girls Cross Country | Staples, Darien, Trumbull | Away - Staples HS-Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 10/11 | V Field Hockey | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 7:00 p.m. | L 0-7 | |
| Tue., 10/11 | JV Field Hockey | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 5:00 p.m. | ||
| Tue., 10/11 | V Girls Soccer | Staples | Home - Stamford HS-SHS Upper Soccer Field [Directions] | 4:00 p.m. | L 1-4 | |
| Tue., 10/11 | JV Girls Soccer | Staples | Home - Rippowam MS-Upper Soccer/Footballl Field [Directions] | 4:00 p.m. | ||
| Wed., 10/12 | FR Football | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 7:15 p.m. | L 6-0 | |
| Wed., 10/12 | V Boys Golf | Westhill | Away - EG Brennan Golf Course-E Gaynor Brennan Golf Course [Directions] | 3:15 p.m. | Westhill 155, Stamford 169 | |
| Wed., 10/12 | V Boys Soccer | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | L 4-1 | |
| Wed., 10/12 | FR Boys Soccer | Westhill | Home - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | ||
| Wed., 10/12 | V Girls Volleyball | Trumbull | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | L 3-0 | |
| Wed., 10/12 | JV Girls Volleyball | Trumbull | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 10/12 | FR Girls Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | Postponed | ||
| Thu., 10/13 | V Girls Soccer | Westhill | Home - Stamford HS-SHS Upper Soccer Field [Directions] | 4:00 p.m. | W 1-0 | |
| Thu., 10/13 | JV Girls Soccer | Westhill | Home - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | ||
| Fri., 10/14 | V Football | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 7:00 p.m. | L 14-42 | |
| Fri., 10/14 | V Boys Soccer | Norwalk | Home - Stamford HS-SHS Upper Soccer Field [Directions] | 4:00 p.m. | L 5-1 | |
| Fri., 10/14 | JV Boys Soccer | Norwalk | Home - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | ||
| Fri., 10/14 | FR Boys Soccer | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 4:00 p.m. | ||
| Fri., 10/14 | V Competitive Cheerleading | At Trumbull HS | Away - Not Listed-Trumbull | 7:00 p.m. | ||
| Fri., 10/14 | V Field Hockey | Greenwich | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | L 7-0 | |
| Fri., 10/14 | JV Field Hockey | Greenwich | Home - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | ||
| Fri., 10/14 | V Girls Swimming and Diving | Ridgefield | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Fri., 10/14 | V Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:30 p.m. | L 3-0 | |
| Fri., 10/14 | JV Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 6:00 p.m. | ||
| Fri., 10/14 | FR Girls Volleyball | Fairfield Ludlowe | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | ||
| Sat., 10/15 | JV Football | Trumbull | Home - Stamford HS-Boyle Stadium [Directions] | 10:00 a.m. | L 18-12 | |
| Sat., 10/15 | V Girls Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 4:00 p.m. | W 4-2 | |
| Sat., 10/15 | JV Girls Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | Postponed | ||
| Sat., 10/15 | FR Girls Volleyball | New Canaan | Home - Stamford HS-Kuczo Gymnasium [Directions] | 10:00 a.m. | ||
| Mon., 10/17 | V Boys Golf | Holohan | Away - Not Listed-Wee Burn CC | 11:15 a.m. | ||
| Mon., 10/17 | V Boys Soccer | Darien | Away - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | L 4-0 | |
| Mon., 10/17 | JV Boys Soccer | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 10/17 | FR Boys Soccer | Darien | Home - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | ||
| Mon., 10/17 | V Field Hockey | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 4:00 p.m. | L 0-9 | |
| Mon., 10/17 | JV Field Hockey | Staples | Away - Staples HS-Ginny Parker Field [Directions] | 5:15 p.m. | ||
| Mon., 10/17 | V Girls Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 6:00 p.m. | L 3-0 | |
| Mon., 10/17 | JV Girls Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:30 p.m. | ||
| Mon., 10/17 | FR Girls Volleyball | Staples | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | ||
| Tue., 10/18 | V Boys Golf | St. Joseph | Away - Tashua Knolls Golf Course [Directions] | 3:00 p.m. | St. Joe's 164, Stamford 193 | |
| Tue., 10/18 | V Girls Soccer | Darien | Home - Stamford HS-SHS Upper Soccer Field [Directions] | 4:00 p.m. | L 2-0 | |
| Tue., 10/18 | JV Girls Soccer | Darien | Home - Rippowam MS-Upper Soccer/Footballl Field [Directions] | 4:00 p.m. | ||
| Wed., 10/19 | V Field Hockey | Immaculate | Home - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | L 2-3 | |
| Wed., 10/19 | JV Field Hockey | Immaculate | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Wed., 10/19 | V Girls Swimming and Diving | St. Joseph | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Wed., 10/19 | V Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 6:00 p.m. | L 3-0 | |
| Wed., 10/19 | JV Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:30 p.m. | ||
| Thu., 10/20 | FR Football | Danbury | Home - Stamford HS-Boyle Stadium [Directions] | 5:00 p.m. | L 26-6 | |
| Thu., 10/20 | V Boys Soccer | Bridgeport Central | Home - Stamford HS-SHS Upper Soccer Field [Directions] | 4:30 p.m. | W 6-1 | |
| Thu., 10/20 | JV Boys Soccer | Bridgeport Central | Home - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | ||
| Fri., 10/21 | V Field Hockey | Trumbull | Home - Stamford HS-Boyle Stadium [Directions] | 4:30 p.m. | W 1-0 | |
| Fri., 10/21 | JV Field Hockey | Trumbull | Home - Stamford HS-Boyle Stadium [Directions] | 6:00 p.m. | ||
| Fri., 10/21 | V Girls Soccer | Bridgeport Central | Away - Bridgeport Central-Kennedy Stadium Turf [Directions] | 5:00 p.m. | W 2-0 | |
| Fri., 10/21 | V Girls Volleyball | Norwalk | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | W 3-0 | |
| Fri., 10/21 | JV Girls Volleyball | Norwalk | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 10/21 | FR Girls Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:30 p.m. | ||
| Sat., 10/22 | V Football | Staples | Home - Stamford HS-Boyle Stadium [Directions] | 1:00 p.m. | L 7-42 | |
| Sat., 10/22 | JV Boys Soccer | Westhill | Away - Westhill HS-Front Turf [Directions] | 12:00 p.m. | ||
| Sat., 10/22 | V Girls Soccer | Bethel | Away - Bethel HS-MS Turf Soccer Field [Directions] | 10:00 a.m. | L 3-1 | |
| Sat., 10/22 | JV Girls Soccer | Bethel | Away - Bethel HS-DeSantis Field at Bethel High [Directions] | 10:00 a.m. | ||
| Sat., 10/22 | FR Girls Volleyball | Westhill | Home - Stamford HS-Kuczo Gymnasium [Directions] | 10:00 a.m. | ||
| Mon., 10/24 | V Boys Soccer | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | L 4-0 | |
| Mon., 10/24 | JV Boys Soccer | Greenwich | Away - Cos Cob Park, Benvenuto Field-Benvenuto Field [Directions] | 4:15 p.m. | ||
| Mon., 10/24 | FR Boys Soccer | Greenwich | Home - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | ||
| Mon., 10/24 | JV Field Hockey | Greenwich | Away - Greenwich HS-Field 4 [Directions] | 4:00 p.m. | ||
| Mon., 10/24 | V Girls Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | L 0-3 | |
| Mon., 10/24 | JV Girls Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 10/24 | FR Girls Volleyball | Darien | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | ||
| Tue., 10/25 | V Field Hockey | St. Joseph | Home - Stamford HS-Boyle Stadium [Directions] | 6:00 p.m. | W 3-0 | |
| Tue., 10/25 | JV Field Hockey | St. Joseph | Home - Stamford HS-Boyle Stadium [Directions] | 4:30 p.m. | ||
| Tue., 10/25 | V Girls Soccer | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | L 7-1 | |
| Wed., 10/26 | FR Football | Norwalk | Home - Stamford HS-Boyle Stadium [Directions] | 5:00 p.m. | L 15-6 | |
| Wed., 10/26 | JV Girls Soccer | Greenwich | Home - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | ||
| Thu., 10/27 | V Girls Volleyball | Bridgeport Central | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | W 3-0 | |
| Thu., 10/27 | JV Girls Volleyball | Bridgeport Central | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | ||
| Fri., 10/28 | V Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | L 0-3 | |
| Fri., 10/28 | JV Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | ||
| Fri., 10/28 | FR Girls Volleyball | Greenwich | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | ||
| Sat., 10/29 | V Football | Brien McMahon | Home - Stamford HS-Boyle Stadium [Directions] | 1:00 p.m. | W 27-13 | |
| Mon., 10/31 | JV Football | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 3:00 p.m. | L 28-6 | |
| Thu., 11/3 | FR Football | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 5:00 p.m. | L 14-8 | |
| Sat., 11/5 | V Football | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 1:30 p.m. | L 13-17 | |
| Sat., 11/5 | V Competitive Cheerleading | @ St. Joes | Away - Not Listed-St. Joes | 1:30 p.m. | ||
| Mon., 11/7 | JV Football | St. Joseph | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | L 21-14 | |
| Thu., 11/10 | FR Football | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 2:30 p.m. | L 12-8 | |
| Sat., 11/12 | V Football | Greenwich | Home - Stamford HS-Boyle Stadium [Directions] | 1:00 p.m. | L 10-49 | |
| Sat., 11/19 | JV Football | Westhill | Home - Stamford HS-Boyle Stadium [Directions] | 1:00 p.m. | W 34-22 | |
| Thu., 11/24 | V Football | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 10:00 a.m. | W 33-6 | |
| Thu., 11/24 | V Competitive Cheerleading | Thanksgiving at Westhill | Away - Not Listed-Westhill HS | 10:00 a.m. | ||
| Tue., 12/6 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Terry Conners - Stamford-Ice Rink [Directions] | 7:30 p.m. | W 2-1 (OT) | |
| Sat., 12/10 | V Girls Ice Hockey | Mercy/NW Catholic/East Hampton | Away - Cromwell-Upper Rink [Directions] | 5:20 p.m. | L 3-0 | |
| Wed., 12/14 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland of Ice-Stadium [Directions] | 8:00 p.m. | L 2-5 | |
| Wed., 12/14 | V Girls Basketball | Scarsdale (NY) | Away - Scarsdale Senior HS | 5:00 p.m. | L 41-35 | |
| Wed., 12/14 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Terry Conners - Stamford-Ice Rink [Directions] | 8:00 p.m. | W 9-0 | |
| Fri., 12/16 | V Boys Swimming and Diving | Greenwich | Away - Greenwich HS-Pool [Directions] | 4:15 p.m. | ||
| Sat., 12/17 | V Boys Ice Hockey | Amity | Away - West Haven HS-Bennett Rink [Directions] | 8:00 p.m. | W 5-4 | |
| Sat., 12/17 | V Boys Indoor Track | Staples, Greenwich, Trumbull, Westhill | Away - Staples HS-Field House [Directions] | 1:30 p.m. | ||
| Sat., 12/17 | V Wrestling | Ludlowe Invitational | Away - Fairfield Ludlowe HS-Main Gym | 9:00 a.m. | ||
| Sat., 12/17 | V Girls Basketball | Pomperaug | Home - Stamford HS-Kuczo Gymnasium [Directions] | 2:00 p.m. | L 28-36 | |
| Sat., 12/17 | JV Girls Basketball | Pomperaug | Home - Stamford HS-Kuczo Gymnasium [Directions] | 12:30 p.m. | ||
| Sat., 12/17 | FR Girls Basketball | Greenwich | Home - Stamford HS-Kuczo Gymnasium [Directions] | 11:00 a.m. | ||
| Sat., 12/17 | V Girls Ice Hockey | Avon | Away - Newington-Blue Rink [Directions] | 4:35 p.m. | L 5-0 | |
| Sat., 12/17 | V Girls Indoor Track | Staples, Greenwich, Trumbull, Westhill | Away - Staples HS-Field House [Directions] | 1:30 p.m. | ||
| Tue., 12/20 | V Girls Basketball | Granby Memorial | Away - Granby Memorial HS-K.L. King Gymnasium [Directions] | 6:15 p.m. | L 44-43 | |
| Tue., 12/20 | JV Girls Basketball | Granby Memorial | Away - Granby Memorial HS-K.L. King Gymnasium [Directions] | 5:00 p.m. | ||
| Wed., 12/21 | V Boys Basketball | North Haven | Home - Stamford HS-Kuczo Gymnasium [Directions] | 6:30 p.m. | W 65-40 | |
| Wed., 12/21 | JV Boys Basketball | North Haven | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:00 p.m. | ||
| Wed., 12/21 | V Wrestling | New Canaan | Home - Stamford HS-SHS Aux Gym [Directions] | 5:30 p.m. | ||
| Thu., 12/22 | V Girls Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 6:15 p.m. | W 64-58 | |
| Thu., 12/22 | JV Girls Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:30 p.m. | ||
| Thu., 12/22 | JV Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice-Stadium [Directions] | 3:30 p.m. | ||
| Tue., 12/27 | V Boys Basketball | Bridgeport Central | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | W 47-46 | |
| Wed., 12/28 | V Boys Ice Hockey | Shepaug Valley Ice Hockey | Home - Terry Conners - Stamford-Ice Rink [Directions] | 4:10 p.m. | W 9-3 | |
| Wed., 12/28 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Terry Conners - Stamford-Ice Rink [Directions] | 2:15 p.m. | W 4-3 | |
| Thu., 12/29 | V Boys Basketball | Bethel | Away - Westhill HS-Main Gym [Directions] | 6:00 p.m. | W 59-34 | |
| Thu., 12/29 | V Boys Ice Hockey | JBWA | Away - Danbury Ice Arena-LIberty Rink [Directions] | 6:00 p.m. | W 7-2 | |
| Thu., 12/29 | V Girls Ice Hockey | Hamden Coop | Away - Hamden-Lou Astorino Ice Rink [Directions] | 12:00 p.m. | W 3-1 | |
| Fri., 12/30 | V Wrestling | Darien, Danbury, Staples | Away - Darien HS-DHS South Gym [Directions] | 10:00 a.m. | ||
| Fri., 12/30 | V Girls Basketball | Southington | Home - Stamford HS-Kuczo Gymnasium [Directions] | 12:30 p.m. | L 60-35 | |
| Fri., 12/30 | JV Girls Basketball | Southington | Home - Stamford HS-Kuczo Gymnasium [Directions] | 11:00 a.m. | ||
| Tue., 1/3 | V Girls Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 7:00 p.m. | L 49-36 | |
| Tue., 1/3 | JV Girls Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/3 | FR Girls Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | Canceled | Cancelled | |
| Wed., 1/4 | V Boys Ice Hockey | Brien McMahon/Norwalk | Home - Terry Conners - Stamford-Ice Rink [Directions] | 5:40 p.m. | W 9-2 | |
| Wed., 1/4 | V Boys Swimming and Diving | Staples | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Wed., 1/4 | V Wrestling | Wilton | Away - Wilton HS-Nicholas Zeoli Fieldhouse [Directions] | 6:00 p.m. | ||
| Wed., 1/4 | V Girls Ice Hockey | New Canaan | Home - Terry Conners - Stamford-Ice Rink [Directions] | 7:30 p.m. | W 3-2 | |
| Thu., 1/5 | V Girls Gymnastics | Westhill, Darien, New Canaan | Away - Westhill HS-New Gym [Directions] | 6:00 p.m. | 93.88 | |
| Fri., 1/6 | V Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 7:00 p.m. | W 61-54 | |
| Fri., 1/6 | JV Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/6 | FR Boys Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/6 | V Boys Swimming and Diving | Ridgefield | Away - Barlow Mountain Pool [Directions] | 4:00 p.m. | ||
| Fri., 1/6 | V Girls Basketball | St. Joseph | Home - Stamford HS-Kuczo Gymnasium [Directions] | 7:00 p.m. | L 49-35 | |
| Fri., 1/6 | JV Girls Basketball | St. Joseph | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/6 | FR Girls Basketball | St. Joseph | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 1/7 | V Boys Ice Hockey | Watertown-Pomperaug | Home - Terry Conners - Stamford-Ice Rink [Directions] | 8:10 p.m. | W 4-3 | |
| Sat., 1/7 | V Boys Indoor Track | The Bethel 8 Invitational | Home - Stamford HS-Boyle Stadium [Directions] | 3:00 p.m. | ||
| Sat., 1/7 | V Wrestling | Warde Invitational | Away - Fairfield Warde HS-Large Gym | 9:00 a.m. | ||
| Sat., 1/7 | V Girls Indoor Track | The Bethel 8 Invitational | Home - Stamford HS-Boyle Stadium [Directions] | 3:00 p.m. | ||
| Mon., 1/9 | V Girls Gymnastics | Westhill, Greenwich | Away - Westhill HS-New Gym [Directions] | 6:00 p.m. | 108.2 | |
| Tue., 1/10 | V Boys Basketball | Brien McMahon | Home - Stamford HS-Kuczo Gymnasium [Directions] | 7:00 p.m. | L 65-60 | |
| Tue., 1/10 | JV Boys Basketball | Brien McMahon | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/10 | FR Boys Basketball | Brien McMahon | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/10 | V Girls Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 5:30 p.m. | W 51-28 | |
| Tue., 1/10 | JV Girls Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 1/11 | V Boys Ice Hockey | Wilton | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:30 p.m. | W 7-1 | |
| Wed., 1/11 | V Wrestling | Fairfield Warde | Home - Stamford HS-SHS Aux Gym [Directions] | 5:30 p.m. | ||
| Wed., 1/11 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Terry Conners - Stamford-Ice Rink [Directions] | 8:00 p.m. | W 3-1 | |
| Thu., 1/12 | V Boys Basketball | Danbury | Home - Stamford HS-Kuczo Gymnasium [Directions] | 7:00 p.m. | L 52-71 | |
| Thu., 1/12 | JV Boys Basketball | Danbury | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 1/12 | FR Boys Basketball | Danbury | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 1/12 | V Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 7:00 p.m. | L 52-43 | |
| Thu., 1/12 | JV Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 5:30 p.m. | ||
| Thu., 1/12 | FR Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/13 | V Boys Swimming and Diving | Darien | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Fri., 1/13 | V Girls Ice Hockey | Greenwich | Away - Greenwich - Dorothy Hamill-Rink [Directions] | 5:15 p.m. | L 3-1 | |
| Sat., 1/14 | V Boys Basketball | Westhill | Home - Stamford HS-Kuczo Gymnasium [Directions] | 3:00 p.m. | W 70-38 | |
| Sat., 1/14 | V Boys Ice Hockey | Darien | Away - Darien Ice House-Ice Rink [Directions] | 7:10 p.m. | L 1-6 | |
| Sat., 1/14 | V Boys Indoor Track | Staples, Darien, St. Joseph | Away - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/14 | V Girls Basketball | Westhill | Home - Stamford HS-Kuczo Gymnasium [Directions] | 12:00 p.m. | W 51-36 | |
| Sat., 1/14 | V Girls Indoor Track | Staples, Darien, St. Joseph | Away - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/14 | Unified Sports Basketball | Westhill | Home - Stamford HS-SHS Aux Gym [Directions] | 1:45 p.m. | ||
| Mon., 1/16 | V Boys Ice Hockey | East Haven Coop | Home - Terry Conners - Stamford-Ice Rink [Directions] | 1:45 p.m. | W 4-2 | |
| Tue., 1/17 | V Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 7:00 p.m. | L 69-71 | |
| Tue., 1/17 | JV Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/17 | FR Boys Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/17 | V Girls Basketball | Fairfield Warde | Home - Stamford HS-Kuczo Gymnasium [Directions] | 7:00 p.m. | L 45-53 | |
| Tue., 1/17 | JV Girls Basketball | Fairfield Warde | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/17 | FR Girls Basketball | Fairfield Warde | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 1/18 | V Boys Swimming and Diving | Trumbull | Away - Univ of Bridgeport Pool [Directions] | 4:00 p.m. | ||
| Wed., 1/18 | V Wrestling | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 1/18 | V Girls Ice Hockey | Darien | Away - Darien Ice House-Ice Rink [Directions] | 4:00 p.m. | L 3-2 | |
| Thu., 1/19 | V Boys Ice Hockey | St. Joseph | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | 7:30 p.m. | W 5-2 | |
| Thu., 1/19 | V Girls Gymnastics | Staples, Norwalk, Westhill | Away - Staples HS-Westport YMCA [Directions] | 7:00 p.m. | 103.65 | |
| Fri., 1/20 | V Boys Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 7:00 p.m. | W 63-60 | |
| Fri., 1/20 | JV Boys Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Fri., 1/20 | FR Boys Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/20 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Fri., 1/20 | V Girls Basketball | Staples | Home - Stamford HS-Kuczo Gymnasium [Directions] | 7:00 p.m. | W 40-36 | |
| Fri., 1/20 | JV Girls Basketball | Staples | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/20 | FR Girls Basketball | Staples | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/20 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 4:00 p.m. | T 2-2 | |
| Sat., 1/21 | V Boys Indoor Track | Staples, Darien, Norwalk | Away - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/21 | V Boys Indoor Track | U.S. Army Officials Hall of Fame Invitational | Away - Not Listed-Armory Athletic Center, NYC, New York | 8:00 a.m. | ||
| Sat., 1/21 | V Competitive Cheerleading | Nighthawk Cheer Classic @ North Haven HS | Away - Not Listed-North Haven HS | TBA | ||
| Sat., 1/21 | V Girls Gymnastics | Trumbull, Westhill | Away - Next Dimension Gymnastics-Next Dimension [Directions] | 5:30 p.m. | 55.95 | |
| Sat., 1/21 | V Girls Gymnastics | St. Joseph, Westhill | Away - St. Joseph HS-Next Dimensions [Directions] | 5:30 p.m. | 55.95 | |
| Sat., 1/21 | V Girls Indoor Track | Staples, Darien, Norwalk | Away - Staples HS-Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/21 | V Girls Indoor Track | U.S. Army Officials Hall of Fame Invitational | Away - Not Listed-Armory Athletic Center, NYC, New York | 8:00 a.m. | U.S. Army Officials Hall of Fame Invitational | |
| Mon., 1/23 | V Girls Gymnastics | Westhill, Wilton | Away - Westhill HS-New Gym [Directions] | 6:00 p.m. | 113.05 | |
| Mon., 1/23 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Home - Terry Conners - Stamford-Ice Rink [Directions] | 5:10 p.m. | W 3-2 | |
| Tue., 1/24 | V Boys Basketball | Wilton | Home - Stamford HS-Kuczo Gymnasium [Directions] | 7:00 p.m. | L 48-51 | |
| Tue., 1/24 | JV Boys Basketball | Wilton | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/24 | FR Boys Basketball | Wilton | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/24 | V Girls Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 6:00 p.m. | W 50-39 | |
| Tue., 1/24 | JV Girls Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | ||
| Wed., 1/25 | V Boys Ice Hockey | New Canaan | Home - Terry Conners - Stamford-Ice Rink [Directions] | 7:30 p.m. | L 6-3 | |
| Wed., 1/25 | V Boys Swimming and Diving | New Canaan | Away - New Canaan YMCA-Pool [Directions] | 3:30 p.m. | ||
| Wed., 1/25 | V Wrestling | St. Joseph | Home - Stamford HS-SHS Aux Gym [Directions] | 4:30 p.m. | ||
| Wed., 1/25 | V Girls Ice Hockey | Greenwich | Home - Terry Conners - Stamford-Ice Rink [Directions] | 5:30 p.m. | W 2-1 | |
| Fri., 1/27 | V Boys Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 7:00 p.m. | L 49-50 | |
| Fri., 1/27 | JV Boys Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/27 | FR Boys Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/27 | V Girls Basketball | Greenwich | Home - Stamford HS-Kuczo Gymnasium [Directions] | 7:00 p.m. | L 44-35 | |
| Fri., 1/27 | JV Girls Basketball | Greenwich | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/27 | FR Girls Basketball | Greenwich | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 1/28 | V Boys Ice Hockey | Trumbull | Home - Terry Conners - Stamford-Ice Rink [Directions] | 7:50 p.m. | W 4-0 | |
| Sat., 1/28 | JV Wrestling | Neil Godleski Wrestling Tournament | Away - Norwalk HS-Tom Scarso Gymnasium | 9:00 a.m. | ||
| Sat., 1/28 | V Girls Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | 8:40 p.m. | L 6-0 | |
| Sun., 1/29 | V Wrestling | Queen of the Mat at Foran HS | Away - Not Listed-Foran HS | 1:00 p.m. | ||
| Mon., 1/30 | V Boys Swimming and Diving | Wilton | Away - Wilton YMCA [Directions] | 3:40 p.m. | ||
| Tue., 1/31 | V Boys Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 7:00 p.m. | W 36-25 | |
| Tue., 1/31 | JV Boys Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 1/31 | FR Boys Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/31 | V Girls Basketball | New Canaan | Home - Stamford HS-Kuczo Gymnasium [Directions] | 7:00 p.m. | W 34-27 | |
| Tue., 1/31 | JV Girls Basketball | New Canaan | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/31 | FR Girls Basketball | New Canaan | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 2/1 | V Boys Ice Hockey | Brien McMahon/Norwalk | Away - Sono Ice House-Main Rink [Directions] | 8:50 p.m. | W 4-2 | |
| Wed., 2/1 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Wed., 2/1 | V Wrestling | Fairfield Ludlowe | Home - Stamford HS-SHS Aux Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/1 | V Girls Gymnastics | Fairfield Ludlowe, Westhill | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:30 p.m. | 118.9 | |
| Wed., 2/1 | V Girls Ice Hockey | Masuk Coop | Home - Terry Conners - Stamford-Ice Rink [Directions] | 8:00 p.m. | W 3-0 | |
| Thu., 2/2 | V Boys Basketball | Bridgeport Central | Home - Stamford HS-Kuczo Gymnasium [Directions] | 7:00 p.m. | W 55-49 | |
| Thu., 2/2 | JV Boys Basketball | Bridgeport Central | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 2/2 | FR Boys Basketball | Bridgeport Central | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 2/3 | V Girls Basketball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | 7:00 p.m. | W 62-33 | |
| Fri., 2/3 | JV Girls Basketball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | 5:30 p.m. | ||
| Fri., 2/3 | FR Girls Basketball | Bridgeport Central | Away - Bridgeport Central HS-The Barry McLeod Court [Directions] | 4:00 p.m. | ||
| Sat., 2/4 | V Boys Basketball | Kolbe Cathedral | Away - Cardinal Sheehan Center Bridgeport [Directions] | 4:45 p.m. | L 50-60 | |
| Sat., 2/4 | JV Boys Basketball | Kolbe Cathedral | Away - Cardinal Sheehan Center Bridgeport [Directions] | 3:00 p.m. | ||
| Sat., 2/4 | V Boys Ice Hockey | Staples | Away - Milford Ice Pavillion-Ice Rink [Directions] | 8:00 p.m. | W 7-0 | |
| Sat., 2/4 | V Wrestling | Westhill | Home - Stamford HS-Kuczo Gymnasium [Directions] | 12:00 p.m. | ||
| Sat., 2/4 | V Girls Ice Hockey | Daniel Hand Coop | Home - Terry Conners - Stamford-Ice Rink [Directions] | 8:00 p.m. | L 4-3 | |
| Mon., 2/6 | V Boys Ice Hockey | Bethel/Brookfield/Danbury/Immaculate | Away - Danbury Ice Arena-Patriot Rink [Directions] | 8:00 p.m. | W 8-1 | |
| Tue., 2/7 | V Boys Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 7:00 p.m. | W 54-44 | |
| Tue., 2/7 | JV Boys Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 2/7 | FR Boys Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/7 | V Wrestling | Ridgefield | Away - Ridgefield HS-Aux Gym [Directions] | 6:00 p.m. | ||
| Tue., 2/7 | V Girls Basketball | Fairfield Ludlowe | Home - Stamford HS-Kuczo Gymnasium [Directions] | 7:00 p.m. | L 50-42 | |
| Tue., 2/7 | JV Girls Basketball | Fairfield Ludlowe | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 2/7 | FR Girls Basketball | Fairfield Ludlowe | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 2/8 | V Boys Ice Hockey | Staples | Home - Terry Conners - Stamford-Ice Rink [Directions] | 7:30 p.m. | W 5-2 | |
| Wed., 2/8 | V Girls Ice Hockey | Darien | Home - Terry Conners - Stamford-Ice Rink [Directions] | 5:30 p.m. | L 1-0 | |
| Thu., 2/9 | V Boys Basketball | Fitch | Away - Fitch HS-Big Gym [Directions] | 7:00 p.m. | L 46-44 | |
| Thu., 2/9 | JV Boys Basketball | Fitch | Away - Fitch HS-Big Gym [Directions] | 5:30 p.m. | ||
| Thu., 2/9 | Unified Sports Basketball | Westhill | Away - Westhill HS-New Gym [Directions] | 3:00 p.m. | ||
| Fri., 2/10 | JV Boys Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 2/10 | FR Boys Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 2/10 | V Boys Swimming and Diving | Danbury | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Fri., 2/10 | V Wrestling | New Canaan, Bridgeport Central, Brien McMahon, Danbury, Darien, FCIAC, Fairfield Ludlowe, Fairfield Warde, Greenwich, Norwalk, Ridgefield, St. Joseph, Staples, Trumbull, Westhill, Wilton | Away - New Canaan HS-Main Gym | 4:00 p.m. | ||
| Fri., 2/10 | JV Girls Basketball | Westhill | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Sat., 2/11 | V Boys Ice Hockey | Wilton | Home - Terry Conners - Stamford-Ice Rink [Directions] | 7:00 p.m. | W 7-0 | |
| Sat., 2/11 | V Girls Basketball | Pomperaug | Away - Pomperaug HS-Main Gym [Directions] | 2:00 p.m. | L 26-53 | |
| Sat., 2/11 | JV Girls Basketball | Pomperaug | Away - Pomperaug HS-Main Gym [Directions] | 12:30 p.m. | ||
| Sat., 2/11 | FR Girls Basketball | Pomperaug | Away - Pomperaug HS-Main Gym [Directions] | 11:00 a.m. | ||
| Sat., 2/11 | V Competitive Cheerleading | Watertown Cheer Open | Away - Not Listed-Watertown | TBA | ||
| Sat., 2/11 | V Girls Gymnastics | FCIACs | Away - Not Listed-GCA Gymnastics | 10:00 a.m. | ||
| Sat., 2/11 | V Girls Ice Hockey | Simsbury | Home - Terry Conners - Stamford-Ice Rink [Directions] | 5:00 p.m. | L 2-1 | |
| Mon., 2/13 | V Boys Basketball | Trumbull | Home - Stamford HS-Kuczo Gymnasium [Directions] | 7:00 p.m. | W 75-72 3OT | |
| Mon., 2/13 | JV Boys Basketball | Trumbull | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 2/13 | FR Boys Basketball | Trumbull | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 2/13 | V Girls Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 7:00 p.m. | L 24-40 | |
| Mon., 2/13 | JV Girls Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | ||
| Mon., 2/13 | FR Girls Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/15 | V Boys Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 7:00 p.m. | W 46-45 | |
| Wed., 2/15 | JV Boys Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/15 | FR Boys Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/15 | V Boys Ice Hockey | Trumbull | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | 8:00 p.m. | W 5-4 | |
| Wed., 2/15 | V Girls Basketball | Darien | Home - Stamford HS-Kuczo Gymnasium [Directions] | 7:00 p.m. | W 48-45 | Senior Knight |
| Wed., 2/15 | JV Girls Basketball | Darien | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 2/15 | FR Girls Basketball | Darien | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 2/17 | V Girls Ice Hockey | East Catholic Coop | Away - Newington-Blue Rink [Directions] | 8:30 p.m. | L 3-0 | |
| Sat., 2/18 | V Boys Ice Hockey | Hall | Home - Terry Conners - Stamford-Ice Rink [Directions] | 6:20 p.m. | W 4-1 | |
| Sat., 2/18 | V Girls Ice Hockey | Mercy/NW Catholic/East Hampton | Home - Terry Conners - Stamford-Ice Rink [Directions] | 8:00 p.m. | L 1-0 | |
| Mon., 2/20 | V Boys Basketball | Norwalk | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | W 72-47 | |
| Mon., 2/20 | JV Boys Basketball | Norwalk | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 2/20 | FR Boys Basketball | Norwalk | Home - Stamford HS-Kuczo Gymnasium [Directions] | 2:30 p.m. | ||
| Mon., 2/20 | V Boys Ice Hockey | North Haven | Away - Northford-Red [Directions] | 1:00 p.m. | L 2-1 | |
| Wed., 2/22 | V Boys Basketball | Ridgefield | Home - Stamford HS-Kuczo Gymnasium [Directions] | 7:00 p.m. | L 42-53 | |
| Wed., 2/22 | JV Boys Basketball | Ridgefield | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 2/22 | FR Boys Basketball | Ridgefield | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 2/23 | Unified Sports Basketball | Vs, Brien McMahon | Home - Stamford HS-Kuczo Gymnasium [Directions] | 3:00 p.m. | ||
| Sat., 2/25 | V Competitive Cheerleading | Oxford Spirit Spectacular | Away - Not Listed-Oxford | 9:30 a.m. | ||
| Tue., 2/28 | V Boys Swimming and Diving | FCIAC Swim Trial Boys | Away - Greenwich HS-Pool | 5:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Date to 3/1 | ||||||
| Thu., 3/2 | Unified Sports Basketball | Greenwich | Home - Stamford HS-Kuczo Gymnasium [Directions] | 3:15 p.m. | ||
| Fri., 3/3 | V Boys Swimming and Diving | Greenwich, Danbury, Darien, Farfield Ludlowe/Warde, Fairfield Warde, TBA, New Canaan, Norwalk/Brien McMahon, Ridgefield, St. Joseph, Staples, Trumbull, Wilton | Away - Greenwich HS-Pool | 6:30 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 5:30 p.m. | ||||||
| Sat., 3/4 | V Competitive Cheerleading | State Open Championships | Away - Not Listed-Floyd Little Athletic Center | 9:00 p.m. | ||
| Sat., 3/18 | V Competitive Cheerleading | New England Regionals | Home - Not Listed [Directions] | TBA | ||
| Sat., 4/1 | FR Boys Lacrosse | Conard | Home - Stamford HS-Upper Lacrosse Field [Directions] | 12:00 p.m. | ||
| Sat., 4/1 | V Girls Lacrosse | Rockville | Home - Stamford HS-Boyle Stadium [Directions] | 12:00 p.m. | W 15-5 | |
| Sun., 4/2 | V Baseball | Cheshire | Home - Stamford HS-SHS Baseball Diamond [Directions] | 2:00 p.m. | L 0-1 | |
| Mon., 4/3 | V Baseball | New Milford | Away - New Milford HS-Baseball Varsity Field - NMHS [Directions] | 4:15 p.m. | W 6-3 | |
| Mon., 4/3 | JV Baseball | New Milford | Away - New Milford HS-Baseball Sub Varsity Field - NMHS [Directions] | 4:15 p.m. | L 5-13 | |
| Mon., 4/3 | FR Baseball | Greenwich | Home - Stamford HS-SHS Baseball Diamond [Directions] | 4:30 p.m. | ||
| Mon., 4/3 | V Girls Lacrosse | Weston | Home - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | L 5-17 | |
| Mon., 4/3 | JV Girls Lacrosse | Weston | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Mon., 4/3 | V Softball | New Fairfield | Home - Stamford HS-SHS Softball Diamond [Directions] | 4:00 p.m. | W 13-3 | |
| Tue., 4/4 | V Boys Lacrosse | Danbury | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | W 21-2 | |
| Tue., 4/4 | JV Boys Lacrosse | Danbury | Home - Stamford HS-Boyle Stadium [Directions] | 4:15 p.m. | ||
| Tue., 4/4 | FR Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Fairfield Warde Grass Utility Field [Directions] | 4:30 p.m. | ||
| Tue., 4/4 | V Softball | Lauralton Hall | Away - Lauralton Hall-Softball Varsity Diamond [Directions] | 4:00 p.m. | L 8-4 | |
| Wed., 4/5 | V Baseball | Weston | Home - Stamford HS-SHS Baseball Diamond [Directions] | 4:00 p.m. | L 13-11 | |
| Wed., 4/5 | JV Baseball | Weston | Home - Belltown Park-Barrett Field, Belltown Park [Directions] | 4:00 p.m. | W 10-3 | |
| Wed., 4/5 | V Boys Volleyball | Daniel Hand | Away - Daniel Hand HS-DHHS Gym [Directions] | 4:00 p.m. | L 0-3 | |
| Thu., 4/6 | V Boys Lacrosse | Brien McMahon | Home - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | L 13-6 | |
| Thu., 4/6 | JV Boys Lacrosse | Brien McMahon | Home - Stamford HS-Upper Lacrosse Field [Directions] | 4:00 p.m. | ||
| Thu., 4/6 | FR Boys Lacrosse | Greenwich | Away - Cos Cob Park, Benvenuto Field-Benvenuto Field [Directions] | Postponed | ||
| Thu., 4/6 | V Boys Volleyball | Kolbe Cathedral | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | W 3-1 | |
| Thu., 4/6 | JV Boys Volleyball | Kolbe Cathedral | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | L 0-2 | |
| Thu., 4/6 | V Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 4:00 p.m. | W 10-8 | |
| Thu., 4/6 | JV Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 5:15 p.m. | ||
| Sat., 4/8 | V Baseball | Greenwich | Home - Stamford HS-SHS Baseball Diamond [Directions] | 12:00 p.m. | W 4-1 | |
| Sat., 4/8 | JV Baseball | Greenwich | Home - Belltown Park-Barrett Field, Belltown Park [Directions] | 10:00 a.m. | L 7-14 | |
| Sat., 4/8 | V Boys Lacrosse | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 11:00 a.m. | W 15-5 | |
| Sat., 4/8 | JV Boys Lacrosse | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 12:30 p.m. | ||
| Sat., 4/8 | V Girls Lacrosse | Danbury | Home - Stamford HS-Boyle Stadium [Directions] | 12:00 p.m. | W 14-5 | |
| Sat., 4/8 | JV Girls Lacrosse | Danbury | Home - Stamford HS-Boyle Stadium [Directions] | 1:30 p.m. | ||
| Sat., 4/8 | V Softball | Amity | Away - Amity Regional HS-Amity HS - Softball Field [Directions] | 11:00 a.m. | L 8-0 | |
| Sat., 4/8 | JV Softball | Amity | Away - Amity Regional HS-CENTER FIELD [Directions] | Canceled | Cancelled | |
| Mon., 4/10 | V Baseball | Norwalk | Home - Stamford HS-SHS Baseball Diamond [Directions] | 4:00 p.m. | W 10-9 | |
| Mon., 4/10 | JV Baseball | Norwalk | Home - Belltown Park-Barrett Field, Belltown Park [Directions] | 4:00 p.m. | L 3-4 | |
| Mon., 4/10 | FR Boys Lacrosse | Staples | Home - Stamford HS-Upper Lacrosse Field [Directions] | 5:00 p.m. | Vs Staples #2 | |
| Mon., 4/10 | V Boys Tennis | St. Joseph | Away - St. Joseph HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Mon., 4/10 | V Softball | Staples | Home - Stamford HS-SHS Softball Diamond [Directions] | 4:00 p.m. | W 7-3 | |
| Mon., 4/10 | V Girls Tennis | St. Joseph | Home - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | L 3 [Detailed Results] | |
| Tue., 4/11 | V Boys Lacrosse | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:30 p.m. | L 19-7 | |
| Tue., 4/11 | JV Boys Lacrosse | Greenwich | Away - Greenwich HS-Field 4 [Directions] | 4:30 p.m. | ||
| Tue., 4/11 | V Boys Outdoor Track | Westhill | Away - Westhill HS-Upper Grass Field [Directions] | 3:00 p.m. | ||
| Tue., 4/11 | V Boys Tennis | Brien McMahon | Home - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | W 6-1 [Detailed Results] | |
| Tue., 4/11 | V Boys Volleyball | HMTCA | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | W 3-0 | |
| Tue., 4/11 | V Girls Lacrosse | Greenwich | Home - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | L 1-16 | |
| Tue., 4/11 | JV Girls Lacrosse | Greenwich | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Tue., 4/11 | V Girls Outdoor Track | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 3:00 p.m. | Jump and Field Events Only | |
| Tue., 4/11 | V Girls Tennis | Brien McMahon | Away - Brien McMahon HS-Tennis Courts [Directions] | 4:15 p.m. | L 3 [Detailed Results] | |
| Wed., 4/12 | FR Boys Lacrosse | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:00 p.m. | ||
| Wed., 4/12 | V Boys Outdoor Track | Westhill | Home - Stamford HS-Boyle Stadium [Directions] | 3:30 p.m. | Running events only | |
| Wed., 4/12 | V Girls Outdoor Track | Westhill | Home - Stamford HS-Boyle Stadium [Directions] | 3:30 p.m. | Running events only | |
| Wed., 4/12 | V Softball | Fairfield Warde | Home - Stamford HS-SHS Softball Diamond [Directions] | 4:00 p.m. | W 7-6 | |
| Thu., 4/13 | V Boys Tennis | Danbury | Home - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | W 5-2 [Detailed Results] | |
| Thu., 4/13 | V Boys Volleyball | Bridgeport Central | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | L 2-3 | |
| Thu., 4/13 | JV Boys Volleyball | Bridgeport Central | Home - Stamford HS-Kuczo Gymnasium [Directions] | 6:00 p.m. | L 0-2 | |
| Thu., 4/13 | V Girls Tennis | Danbury | Away - Danbury HS-DHS Tennis Courts [Directions] | 4:00 p.m. | W 7 [Detailed Results] | |
| Fri., 4/14 | V Baseball | St. Joseph | Home - Stamford HS-SHS Baseball Diamond [Directions] | 4:00 p.m. | L 11-1 | |
| Fri., 4/14 | JV Baseball | St. Joseph | Home - Belltown Park-Barrett Field, Belltown Park [Directions] | 4:00 p.m. | W 9-5 | |
| Fri., 4/14 | FR Baseball | St. Joseph | Away - St. Joseph HS-Baseball Diamond [Directions] | 4:30 p.m. | ||
| Fri., 4/14 | FR Boys Lacrosse | Wilton | Away - Allen's Meadow-Lacrosse Field #1 [Directions] | 4:30 p.m. | ||
| Fri., 4/14 | V Girls Lacrosse | Lauralton Hall | Away - Lauralton Hall-Turf Field [Directions] | 3:45 p.m. | W 12-6 | |
| Fri., 4/14 | JV Girls Lacrosse | Lauralton Hall | Away - Lauralton Hall-Turf Field [Directions] | Canceled | Cancelled | |
| Fri., 4/14 | V Softball | St. Joseph | Away - St. Joseph HS-Softball Diamond [Directions] | 4:30 p.m. | L 21-2 | |
| Sat., 4/15 | V Boys Lacrosse | Jonathan Law | Away - Jonathan Law HS-Lawmen Stadium [Directions] | 12:00 p.m. | W 14-3 | |
| Sat., 4/15 | JV Boys Lacrosse | Jonathan Law | Away - Jonathan Law HS-Lawmen Stadium [Directions] | 1:30 p.m. | ||
| Sat., 4/15 | JV Softball | St. Joseph | Away - St. Joseph HS-Softball Diamond [Directions] | 10:30 a.m. | ||
| Mon., 4/17 | V Baseball | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 4:15 p.m. | W 7-0 | |
| Mon., 4/17 | JV Baseball | Brien McMahon | Away - City Hall Field [Directions] | 4:30 p.m. | W 8-1 | |
| Mon., 4/17 | FR Boys Lacrosse | Trumbull | Away - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | ||
| Mon., 4/17 | V Boys Tennis | Fairfield Warde | Away - Fairfield Warde HS-Blake Courts [Directions] | 4:30 p.m. | L 1-6 [Detailed Results] | |
| Mon., 4/17 | JV Boys Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:00 p.m. | L 2-1 | |
| Mon., 4/17 | V Softball | Brien McMahon | Home - Stamford HS-SHS Softball Diamond [Directions] | 4:00 p.m. | W 7-1 | |
| Tue., 4/18 | V Boys Lacrosse | St. Joseph | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | L 16-3 | |
| Tue., 4/18 | JV Boys Lacrosse | St. Joseph | Home - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/18 | V Boys Outdoor Track | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 4:00 p.m. | ||
| Tue., 4/18 | V Girls Lacrosse | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 4:00 p.m. | L 8-9 | |
| Tue., 4/18 | JV Girls Lacrosse | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 5:30 p.m. | ||
| Tue., 4/18 | V Girls Outdoor Track | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 4:00 p.m. | ||
| Tue., 4/18 | V Girls Tennis | Wilton | Away - Wilton HS-Tennis Courts [Directions] | 4:30 p.m. | L 1 [Detailed Results] | |
| Wed., 4/19 | V Baseball | Danbury | Away - Danbury HS-V Baseball Field [Directions] | 4:30 p.m. | L 2-1 | |
| Wed., 4/19 | JV Baseball | Danbury | Away - Danbury HS-JV Baseball Field [Directions] | 4:30 p.m. | L 11-13 | |
| Wed., 4/19 | FR Baseball | Danbury | Home - Stamford HS-SHS Baseball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 4/19 | V Boys Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:00 p.m. | W 3-1 | |
| Wed., 4/19 | JV Boys Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 5:30 p.m. | L 2-0 | |
| Wed., 4/19 | V Softball | Danbury | Home - Stamford HS-SHS Softball Diamond [Directions] | 4:00 p.m. | W 6-3 | |
| Wed., 4/19 | JV Softball | Danbury | Home - Cummings Park Field #4-Stamford JV Softball at Cummings Park [Directions] | 4:00 p.m. | ||
| Wed., 4/19 | V Girls Tennis | Fairfield Warde | Home - Stamford HS-SHS Tennis Courts [Directions] | 4:30 p.m. | L 2 [Detailed Results] | |
| Thu., 4/20 | V Boys Tennis | New Canaan | Away - New Canaan HS-NCHS Tennis Courts [Directions] | 4:00 p.m. | L 2-5 [Detailed Results] | |
| Thu., 4/20 | V Girls Tennis | New Canaan | Home - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | L 00 [Detailed Results] | |
| Fri., 4/21 | V Baseball | Fairfield Warde | Home - Stamford HS-SHS Baseball Diamond [Directions] | 4:00 p.m. | L 16-2 | |
| Fri., 4/21 | JV Baseball | Fairfield Warde | Home - Belltown Park-Barrett Field, Belltown Park [Directions] | 4:00 p.m. | L 1 - 13 | |
| Fri., 4/21 | FR Baseball | Fairfield Warde | Away - Fairfield Warde HS-Baseball Diamond [Directions] | 4:30 p.m. | ||
| Fri., 4/21 | FR Boys Lacrosse | Fairfield Warde | Home - Stamford HS-Upper Lacrosse Field [Directions] | 5:00 p.m. | ||
| Fri., 4/21 | V Boys Tennis | Wilton | Home - Stamford HS-SHS Tennis Courts [Directions] | 4:30 p.m. | L 1-6 [Detailed Results] | |
| Fri., 4/21 | V Boys Volleyball | Greenwich | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | L 1-3 | |
| Fri., 4/21 | JV Boys Volleyball | Greenwich | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | L 0-2 | |
| Fri., 4/21 | V Softball | Fairfield Warde | Away - Fairfield Warde HS-Softball Diamond [Directions] | 4:30 p.m. | W 9-8 | |
| Sat., 4/22 | V Boys Lacrosse | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 11:00 a.m. | L 9-5 | |
| Sat., 4/22 | JV Boys Lacrosse | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 9:00 a.m. | ||
| Sat., 4/22 | V Girls Lacrosse | Trumbull | Home - Stamford HS-Boyle Stadium [Directions] | 12:00 p.m. | W 15-5 | |
| Sat., 4/22 | JV Girls Lacrosse | Trumbull | Home - Stamford HS-Boyle Stadium [Directions] | 1:30 p.m. | ||
| Sat., 4/22 | JV Softball | Fairfield Warde | Away - Fairfield Warde HS-Softball Diamond [Directions] | 10:00 a.m. | ||
| Mon., 4/24 | V Baseball | Wilton | Away - Wilton HS-Varsity Baseball Field [Directions] | 4:30 p.m. | W 1-0 | |
| Mon., 4/24 | JV Baseball | Wilton | Away - Wilton HS-JV Baseball Field [Directions] | 4:30 p.m. | L 5 - 7 | |
| Mon., 4/24 | FR Baseball | Wilton | Home - Stamford HS-SHS Baseball Diamond [Directions] | 4:30 p.m. | ||
| Mon., 4/24 | FR Boys Lacrosse | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 4:30 p.m. | ||
| Mon., 4/24 | V Boys Outdoor Track | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | ||
| Mon., 4/24 | V Boys Tennis | Ridgefield | Home - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | W 4-3 [Detailed Results] | |
| Mon., 4/24 | V Boys Volleyball | Trumbull | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | L 0-3 | |
| Mon., 4/24 | JV Boys Volleyball | Trumbull | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | L 0-2 | |
| Mon., 4/24 | V Girls Outdoor Track | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | ||
| Mon., 4/24 | V Softball | Wilton | Home - Troy Complex-Diamond 1 [Directions] | 7:00 p.m. | L 5-4 | |
| Mon., 4/24 | V Girls Tennis | Ridgefield | Away - Ridgefield HS-RHS Tennis Courts [Directions] | 4:00 p.m. | L 2 [Detailed Results] | |
| Tue., 4/25 | V Boys Lacrosse | Bunnell-Stratford | Away - Bunnell HS-Mastroni Field [Directions] | 5:15 p.m. | W 16-12 | |
| Tue., 4/25 | JV Boys Lacrosse | Bunnell-Stratford | Away - Bunnell HS-Mastroni Field [Directions] | 7:00 p.m. | ||
| Tue., 4/25 | V Boys Tennis | Trumbull | Home - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | L 2-5 [Detailed Results] | |
| Tue., 4/25 | V Softball | New Canaan | Away - Waveny Park-Orchard Field [Directions] | 4:00 p.m. | L 3-2 | |
| Tue., 4/25 | JV Softball | New Canaan | Away - Waveny Park-Orchard Field [Directions] | 6:30 p.m. | ||
| Tue., 4/25 | V Girls Tennis | Trumbull | Away - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | W 5 [Detailed Results] | |
| Wed., 4/26 | FR Boys Lacrosse | Greenwich | Home - Stamford HS-Upper Lacrosse Field [Directions] | 5:00 p.m. | Tier #2 Greenwich | |
| Wed., 4/26 | V Boys Volleyball | Danbury | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | L 2-3 | |
| Wed., 4/26 | JV Boys Volleyball | Danbury | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | L 0-2 | |
| Thu., 4/27 | V Boys Lacrosse | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 6:30 p.m. | L 9-8 | |
| Thu., 4/27 | JV Boys Lacrosse | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 4:30 p.m. | ||
| Thu., 4/27 | V Girls Lacrosse | Norwalk | Home - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | W 9-8 | |
| Thu., 4/27 | JV Girls Lacrosse | Norwalk | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Fri., 4/28 | V Baseball | Ridgefield | Away - Governor Field [Directions] | 4:30 p.m. | L 10-0 | |
| Fri., 4/28 | JV Baseball | Ridgefield | Away - East Ridge MS-Baseball Field [Directions] | 4:30 p.m. | W 13 - 5 | |
| Fri., 4/28 | FR Baseball | Ridgefield | Home - Stamford HS-SHS Baseball Diamond [Directions] | 4:00 p.m. | ||
| Fri., 4/28 | FR Boys Lacrosse | Westhill | Home - Stamford HS-Upper Lacrosse Field [Directions] | 5:00 p.m. | ||
| Fri., 4/28 | V Boys Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:00 p.m. | L 0-3 | |
| Fri., 4/28 | JV Boys Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 5:30 p.m. | L 2-0 | |
| Fri., 4/28 | V Softball | Ridgefield | Home - Stamford HS-SHS Softball Diamond [Directions] | 4:30 p.m. | L 4-2 | |
| Fri., 4/28 | JV Softball | Ridgefield | Home - Cummings Park Field #4-Stamford JV Softball at Cummings Park [Directions] | 4:30 p.m. | ||
| Sat., 4/29 | V Boys Lacrosse | Immaculate | Away - Immaculate HS [Directions] | 1:00 p.m. | W 7-1 | |
| Sat., 4/29 | V Girls Lacrosse | Immaculate | Away - Immaculate HS-Mustang Valley [Directions] | 11:00 a.m. | W 15-2 | |
| Sat., 4/29 | JV Softball | Wilton | Home - Stamford HS-SHS Softball Diamond [Directions] | Postponed | ||
| Mon., 5/1 | V Boys Lacrosse | Brookfield | Home - Stamford HS-Boyle Stadium [Directions] | 6:00 p.m. | W 10-5 | |
| Mon., 5/1 | JV Boys Lacrosse | Brookfield | Home - Stamford HS-Upper Lacrosse Field [Directions] | Canceled | Cancelled | |
| Mon., 5/1 | FR Boys Lacrosse | Conard | Away - Conard HS-McKee Stadium [Directions] | 5:00 p.m. | ||
| Mon., 5/1 | V Boys Tennis | Staples | Away - Staples HS-Staples Tennis Courts [Directions] | 4:00 p.m. | L 2-5 [Detailed Results] | |
| Mon., 5/1 | V Boys Volleyball | New Canaan | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | L 0-3 | |
| Mon., 5/1 | JV Boys Volleyball | New Canaan | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | L 0-2 | |
| Mon., 5/1 | V Softball | Trumbull | Home - Stamford HS-SHS Softball Diamond [Directions] | 5:00 p.m. | L 2-8 | |
| Mon., 5/1 | JV Softball | Trumbull | Home - Cummings Park Field #4-Stamford JV Softball at Cummings Park [Directions] | 4:00 p.m. | ||
| Mon., 5/1 | V Girls Tennis | Staples | Home - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | L 00 [Detailed Results] | |
| Tue., 5/2 | V Boys Outdoor Track | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 4:00 p.m. | ||
| Tue., 5/2 | V Girls Lacrosse | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | W 18-7 | |
| Tue., 5/2 | JV Girls Lacrosse | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | ||
| Tue., 5/2 | V Girls Outdoor Track | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 4:00 p.m. | ||
| Wed., 5/3 | V Baseball | Fairfield Ludlowe | Home - Stamford HS-SHS Baseball Diamond [Directions] | 4:00 p.m. | L 8-0 | |
| Wed., 5/3 | JV Baseball | Fairfield Ludlowe | Home - Belltown Park-Barrett Field, Belltown Park [Directions] | 4:00 p.m. | L 2 - 6 | |
| Wed., 5/3 | FR Baseball | Fairfield Ludlowe | Away - Kiwanis Field-Baseball Diamond [Directions] | 4:30 p.m. | ||
| Wed., 5/3 | FR Boys Lacrosse | Wilton | Home - Stamford HS-Upper Lacrosse Field [Directions] | 5:00 p.m. | Wilton Team #2 | |
| Wed., 5/3 | V Boys Tennis | Westhill | Away - Westhill HS-Westhill Tennis Courts [Directions] | 4:00 p.m. | L 1-6 [Detailed Results] | |
| Wed., 5/3 | V Boys Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:00 p.m. | L 1-3 | |
| Wed., 5/3 | JV Boys Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 5:30 p.m. | L 2-0 | |
| Wed., 5/3 | V Softball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 4:30 p.m. | L 0-16 | |
| Wed., 5/3 | JV Softball | Fairfield Ludlowe | Away - Tom Hayden Field [Directions] | 4:30 p.m. | ||
| Wed., 5/3 | V Girls Tennis | Westhill | Home - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | L 3 [Detailed Results] | |
| Thu., 5/4 | V Baseball | Trumbull | Away - Trumbull HS-Varsity Baseball Field [Directions] | 4:00 p.m. | L 7-6 | |
| Thu., 5/4 | JV Baseball | Trumbull | Away - Trumbull HS-JV Baseball Field [Directions] | 4:00 p.m. | L 5 - 6 | |
| Thu., 5/4 | FR Baseball | Trumbull | Home - Stamford HS-SHS Baseball Diamond [Directions] | 4:00 p.m. | ||
| Thu., 5/4 | V Boys Tennis | Norwalk | Home - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 [Detailed Results] | |
| Thu., 5/4 | V Girls Lacrosse | Brien McMahon | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | W 12-7 | |
| Thu., 5/4 | JV Girls Lacrosse | Brien McMahon | Home - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | ||
| Thu., 5/4 | V Girls Tennis | Norwalk | Away - Norwalk HS-Tennis Courts [Directions] | 4:00 p.m. | W 6 [Detailed Results] | |
| Fri., 5/5 | V Baseball | Staples | Home - Stamford HS-SHS Baseball Diamond [Directions] | 4:00 p.m. | L 8-0 | |
| Fri., 5/5 | JV Baseball | Staples | Home - Belltown Park-Barrett Field, Belltown Park [Directions] | 4:00 p.m. | L 1 - 11 | |
| Fri., 5/5 | FR Baseball | Staples | Away - Staples HS-Baseball Diamond [Directions] | Postponed | ||
| Fri., 5/5 | FR Boys Lacrosse | Newtown | Home - Stamford HS-Upper Lacrosse Field [Directions] | 5:00 p.m. | ||
| Fri., 5/5 | V Boys Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Tennis Courts [Directions] | 4:00 p.m. | L 3-4 [Detailed Results] | |
| Fri., 5/5 | V Boys Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | L 0-3 | |
| Fri., 5/5 | JV Boys Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | L 2-0 | |
| Fri., 5/5 | V Softball | Staples | Away - Greens Farms Elementary School-Softball Field [Directions] | 7:00 p.m. | L 6-7 | |
| Fri., 5/5 | JV Softball | Staples | Away - Staples HS-Staples Softball Field [Directions] | Postponed | ||
| Sat., 5/6 | V Baseball | New Canaan | Home - Stamford HS-SHS Baseball Diamond [Directions] | 1:00 p.m. | W 11-6 | |
| Sat., 5/6 | JV Baseball | New Canaan | Home - Belltown Park-Barrett Field, Belltown Park [Directions] | 10:00 a.m. | L 10 - 24 | |
| Sat., 5/6 | FR Baseball | New Canaan | Away - New Canaan HS-Coppo Field [Directions] | Postponed | ||
| Sat., 5/6 | V Boys Lacrosse | Masuk | Home - Stamford HS-Boyle Stadium [Directions] | 12:00 p.m. | W 9-4 | |
| Sat., 5/6 | JV Softball | Westhill | Away - Westhill HS-Varsity Softball Field [Directions] | Canceled | Cancelled | |
| Sat., 5/6 | V Girls Tennis | Fairfield Ludlowe | Home - Stamford HS-SHS Tennis Courts [Directions] | 10:00 a.m. | L 00 [Detailed Results] | |
| Sun., 5/7 | V Softball | Westhill | Away - Westhill HS-Varsity Softball Field [Directions] | 1:00 p.m. | L 6-1 | |
| Mon., 5/8 | V Baseball | Westhill | Home - Cubeta Stadium [Directions] | 7:00 p.m. | L 7-4 | |
| Mon., 5/8 | JV Baseball | Westhill | Home - Cubeta Stadium [Directions] | 3:30 p.m. | L 3 - 7 | |
| Mon., 5/8 | FR Baseball | Westhill | Away - Westhill HS-Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/8 | FR Boys Lacrosse | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 5/8 | V Boys Tennis | Darien | Away - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | L 1-6 [Detailed Results] | |
| Mon., 5/8 | V Boys Volleyball | Bridgeport Central | Away - Bridgeport Central HS-The Barry McLeod Court [Directions] | 6:00 p.m. | L 0-3 | |
| Mon., 5/8 | JV Boys Volleyball | Bridgeport Central | Away - Bridgeport Central HS-The Barry McLeod Court [Directions] | 4:30 p.m. | L 2-0 | |
| Mon., 5/8 | V Girls Lacrosse | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | L 0-20 | |
| Mon., 5/8 | JV Girls Lacrosse | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Mon., 5/8 | V Girls Tennis | Darien | Home - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | L 00 [Detailed Results] | |
| Tue., 5/9 | V Boys Lacrosse | Darien | Home - Stamford HS-Boyle Stadium [Directions] | 5:00 p.m. | L 19-1 | |
| Tue., 5/9 | JV Boys Lacrosse | Darien | Home - Stamford HS-Upper Lacrosse Field [Directions] | 5:00 p.m. | ||
| Tue., 5/9 | V Boys Outdoor Track | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/9 | V Boys Tennis | Bridgeport Central | Home - Stamford HS-SHS Tennis Courts [Directions] | 4:30 p.m. | W 7-0 [Detailed Results] | |
| Tue., 5/9 | V Girls Outdoor Track | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/9 | V Girls Tennis | Bridgeport Central | Away - Bridgeport Central HS-Central High School Tennis Courts [Directions] | 4:30 p.m. | W 6 [Detailed Results] | |
| Wed., 5/10 | V Baseball | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 6:00 p.m. | L 9-3 | |
| Wed., 5/10 | JV Baseball | Norwalk | Away - City Hall Field [Directions] | 4:30 p.m. | L 2 - 9 | |
| Wed., 5/10 | FR Baseball | Norwalk | Home - Stamford HS-SHS Baseball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 5/10 | FR Boys Lacrosse | Trumbull | Home - Stamford HS-Upper Lacrosse Field [Directions] | 5:00 p.m. | Trumbull Team #2 | |
| Wed., 5/10 | V Boys Volleyball | Ridgefield | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | L 1-3 | |
| Wed., 5/10 | V Softball | Norwalk | Home - Troy Complex-Diamond 1 [Directions] | 7:00 p.m. | L 6-2 | |
| Wed., 5/10 | JV Softball | Norwalk | Home - Stamford HS-SHS Softball Diamond [Directions] | 4:00 p.m. | ||
| Thu., 5/11 | V Baseball | Darien | Home - Stamford HS-SHS Baseball Diamond [Directions] | 4:00 p.m. | W 6-5 | |
| Thu., 5/11 | JV Baseball | Darien | Home - Belltown Park-Barrett Field, Belltown Park [Directions] | 4:00 p.m. | L 4 - 12 | |
| Thu., 5/11 | FR Baseball | Darien | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | ||
| Thu., 5/11 | V Boys Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 6:00 p.m. | L 12-7 | |
| Thu., 5/11 | JV Boys Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | 4:00 p.m. | ||
| Thu., 5/11 | V Boys Tennis | Greenwich | Away - Greenwich HS-Tennis Courts [Directions] | 4:30 p.m. | L 1-6 [Detailed Results] | |
| Thu., 5/11 | V Boys Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:30 p.m. | L 0-3 | |
| Thu., 5/11 | V Girls Lacrosse | Fairfield Ludlowe | Home - Stamford HS-Boyle Stadium [Directions] | 5:45 p.m. | L 10-18 | Senior Knight |
| Thu., 5/11 | JV Girls Lacrosse | Fairfield Ludlowe | Home - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | ||
| Thu., 5/11 | V Softball | Darien | Away - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | W 3-1 | |
| Thu., 5/11 | V Girls Tennis | Greenwich | Home - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | L 00 [Detailed Results] | |
| Sat., 5/13 | V Boys Lacrosse | Westhill | Home - Stamford HS-Boyle Stadium [Directions] | 6:00 p.m. | L 4-8 | |
| Sat., 5/13 | JV Boys Lacrosse | Westhill | Home - Stamford HS-Boyle Stadium [Directions] | 3:30 p.m. | ||
| Sat., 5/13 | V Girls Lacrosse | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 3:00 p.m. | L 8-11 | |
| Sat., 5/13 | JV Girls Lacrosse | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 1:30 p.m. | ||
| Mon., 5/15 | V Baseball | Bridgeport Central | Away - Bridgeport Central HS-Baseball Diamond [Directions] | 4:30 p.m. | W 12-0 | |
| Mon., 5/15 | FR Boys Lacrosse | Fairfield Ludlowe | Home - Stamford HS-Upper Lacrosse Field [Directions] | 5:00 p.m. | Ludlowe Team #2 | |
| Mon., 5/15 | V Boys Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:00 p.m. | L 0-3 | |
| Mon., 5/15 | JV Boys Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:30 p.m. | L 2-1 | |
| Mon., 5/15 | V Softball | Bridgeport Central | Home - Troy Complex-Diamond 1 [Directions] | 7:00 p.m. | W 20-0 | |
| Tue., 5/16 | V Boys Lacrosse | Fairfield Warde | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | L 10-7 | |
| Tue., 5/16 | JV Boys Lacrosse | Fairfield Warde | Home - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/16 | V Boys Outdoor Track | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/16 | V Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 6:30 p.m. | W 11-5 | |
| Tue., 5/16 | JV Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:30 p.m. | ||
| Tue., 5/16 | V Girls Outdoor Track | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 4:00 p.m. | ||
| Wed., 5/17 | V Baseball | Greenwich | Home - Cubeta Stadium [Directions] | 7:00 p.m. | W 3-0 | |
| Wed., 5/17 | JV Baseball | Greenwich | Home - Stamford HS-SHS Baseball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 5/17 | FR Baseball | Greenwich | Away - Greenwich HS-Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/17 | V Boys Volleyball | Fairfield Warde | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | L 0-3 | |
| Wed., 5/17 | JV Boys Volleyball | Fairfield Warde | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | L 0-2 | |
| Wed., 5/17 | V Softball | Greenwich | Away - Greenwich HS-Softball Field [Directions] | 4:30 p.m. | W 14-0 | |
| Wed., 5/17 | JV Softball | Greenwich | Away - Julian Curtiss School [Directions] | 4:30 p.m. | ||
| Thu., 5/18 | FR Boys Lacrosse | Westhill | Home - Stamford HS-Boyle Stadium [Directions] | 5:00 p.m. | ||
| Thu., 5/18 | JV Softball | Darien | Away - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | ||
| Sat., 5/20 | V Boys Volleyball | Rockville | Away - Rockville HS-Main gymnasium [Directions] | 12:00 p.m. | L 0-3 | |
| Sat., 5/20 | JV Boys Volleyball | Rockville | Away - Rockville HS-Main gymnasium [Directions] | 11:00 a.m. | L 2-1 | |