| Stamford 2021-22 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 795 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Wed., 8/25 | V Football | Hamden, Guilford (Scrim.) | Away - Hamden HS-HHS Turf Field #1 [Directions] | Canceled | Cancelled | |
| Pending change awaiting acceptance by one or more parties involved: Time to 4:00 p.m. | ||||||
| Tue., 8/31 | V Boys Golf | Fairfield Warde | Away - Smith Richardson Golf Course [Directions] | 3:30 p.m. | Fairfield Warde 150, Stamford 195 | |
| Thu., 9/2 | V Boys Soccer | Joel Barlow (Scrim.) | Home - Stamford HS-SHS Upper Soccer Field [Directions] | Postponed | ||
| Thu., 9/2 | V Girls Soccer | Hamden (Scrim.) | Away - Hamden HS-HHS Turf Field #2 [Directions] | 4:30 p.m. | ||
| Fri., 9/3 | V Football | Wilby (Scrim.) | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Sat., 9/4 | V Field Hockey | Norwalk Play Day - Norwalk HS | Away - Not Listed-Norwalk HS | 11:00 a.m. | Cancelled | |
| Sat., 9/4 | V Girls Soccer | Amity | Home - Shelton HS-Upper Field [Directions] | 8:00 a.m. | ||
| Sat., 9/4 | JV Girls Soccer | Shelton Jamboree at Shelton HS | Away - Not Listed-Shelton HS | 8:00 a.m. | ||
| Sat., 9/4 | V Girls Volleyball | Joel Barlow (Scrim.) | Home - Stamford HS-Kuczo Gymnasium [Directions] | 9:30 a.m. | ||
| Thu., 9/9 | FR Football | New Canaan | Away - New Canaan HS-WTT #1 [Directions] | 5:30 p.m. | ||
| Thu., 9/9 | V Field Hockey | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | L 0-9 | |
| Thu., 9/9 | JV Field Hockey | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 5:30 p.m. | ||
| Thu., 9/9 | V Girls Soccer | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 4:00 p.m. | L 0-5 | |
| Thu., 9/9 | JV Girls Soccer | St. Joseph | Away - St. Joseph HS-Lower Grass Field [Directions] | Postponed | ||
| Fri., 9/10 | V Boys Soccer | St. Joseph | Home - Stamford HS-SHS Upper Soccer Field [Directions] | 4:00 p.m. | W 4-3 | |
| Fri., 9/10 | V Girls Volleyball | Foran | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | W 3-0 | |
| Sat., 9/11 | FR Boys Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 11:00 a.m. | ||
| Sat., 9/11 | V Field Hockey | Shelton | Home - Stamford HS-Boyle Stadium [Directions] | 11:00 a.m. | W 4-0 | |
| Sat., 9/11 | JV Field Hockey | Shelton | Home - Stamford HS-Boyle Stadium [Directions] | 12:30 p.m. | ||
| Sat., 9/11 | V Girls Soccer | Bethel | Home - Stamford HS-SHS Upper Soccer Field [Directions] | 10:00 a.m. | L 1-3 | |
| Sat., 9/11 | JV Girls Soccer | Bethel | Home - Stamford HS-SHS Upper Soccer Field [Directions] | 12:00 p.m. | ||
| Sat., 9/11 | FR Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Small Gym [Directions] | 10:30 a.m. | ||
| Mon., 9/13 | V Boys Golf | Staples | Home - Stamford High-Sterling Farms Golf Course [Directions] | 3:00 p.m. | Staples 146, Stamford 186 | |
| Mon., 9/13 | V Girls Soccer | Brien McMahon | Home - Stamford HS-SHS Upper Soccer Field [Directions] | 4:00 p.m. | L 2-1 | |
| Mon., 9/13 | JV Girls Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 6:00 p.m. | ||
| Mon., 9/13 | FR Girls Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 9/14 | V Boys Cross Country | Westhill, Greenwich, Ridgefield | Away - Scofield Magnet MS-Cross Country Course [Directions] | 4:00 p.m. | ||
| Tue., 9/14 | V Boys Golf | New Canaan, Fairfield Warde | Away - CCNC [Directions] | 3:15 p.m. | New Canaan 145, Stamford 203 | |
| Tue., 9/14 | V Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 7:00 p.m. | T 0-0 | |
| Tue., 9/14 | JV Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 7:00 p.m. | ||
| Tue., 9/14 | V Girls Cross Country | Westhill, Greenwich, Ridgefield | Away - Scofield Magnet MS-Cross Country Course [Directions] | 4:00 p.m. | ||
| Tue., 9/14 | V Field Hockey | Westhill | Home - Stamford HS-Boyle Stadium [Directions] | 7:00 p.m. | W 3-1 | |
| Tue., 9/14 | JV Field Hockey | Westhill | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Tue., 9/14 | V Girls Volleyball | Lauralton Hall | Away - Lauralton Hall-Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Tue., 9/14 | JV Girls Volleyball | Lauralton Hall | Away - Lauralton Hall-Gym [Directions] | 4:00 p.m. | ||
| Wed., 9/15 | FR Football | Danbury | Home - Stamford HS-Boyle Stadium [Directions] | 3:00 p.m. | ||
| Wed., 9/15 | FR Boys Soccer | Westhill | Home - Stamford HS-SHS Upper Soccer Field [Directions] | 4:30 p.m. | ||
| Fri., 9/17 | V Football | Danbury | Home - Stamford HS-Boyle Stadium [Directions] | 7:00 p.m. | L 13-35 | |
| Fri., 9/17 | V Girls Soccer | Danbury | Home - Stamford HS-SHS Upper Soccer Field [Directions] | 4:00 p.m. | L 3-2 | |
| Fri., 9/17 | V Girls Volleyball | Weston | Away - Weston HS-Gym (New) [Directions] | 6:30 p.m. | L 0-3 | |
| Fri., 9/17 | JV Girls Volleyball | Weston | Away - Weston HS-Gym (New) [Directions] | 5:00 p.m. | ||
| Fri., 9/17 | FR Girls Volleyball | Weston | Away - Weston HS-Gym (Old) [Directions] | 5:00 p.m. | ||
| Sat., 9/18 | V Boys Soccer | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 11:00 a.m. | L 3-0 | |
| Sat., 9/18 | JV Boys Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 11:00 a.m. | ||
| Sat., 9/18 | FR Boys Soccer | New Canaan | Away - Saxe MS-Field 1 [Directions] | 10:00 a.m. | ||
| Sat., 9/18 | V Field Hockey | Wilton | Home - Stamford HS-Boyle Stadium [Directions] | 10:00 a.m. | L 1-5 | |
| Sat., 9/18 | JV Field Hockey | Wilton | Home - Stamford HS-Boyle Stadium [Directions] | 11:30 a.m. | ||
| Sat., 9/18 | JV Girls Soccer | Danbury | Home - Stamford HS-SHS Upper Soccer Field [Directions] | 10:00 a.m. | ||
| Sat., 9/18 | FR Girls Volleyball | Fairfield Ludlowe | Home - Stamford HS-Kuczo Gymnasium [Directions] | 10:00 a.m. | ||
| Mon., 9/20 | JV Football | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 9/20 | V Boys Golf | Danbury | Home - Stamford High-Sterling Farms Golf Course [Directions] | 3:00 p.m. | Danbury 188, Stamford 195 | |
| Mon., 9/20 | V Boys Golf | Ridgefield | Home - Stamford High-Sterling Farms Golf Course [Directions] | 3:00 p.m. | Ridgefield 149, Stamford 195 | |
| Mon., 9/20 | V Boys Soccer | Harding | Away - Warren Harding HS-Lewis Field [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 9/21 | V Boys Cross Country | Wilton, New Canaan, Staples | Away - Allen's Meadow-XC Course [Directions] | 4:00 p.m. | ||
| Tue., 9/21 | V Boys Golf | Wilton | Away - Rolling Hills Country Club [Directions] | 3:15 p.m. | Wilton 163, Stamford 198 | |
| Tue., 9/21 | FR Boys Soccer | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 5:00 p.m. | ||
| Tue., 9/21 | V Girls Cross Country | Wilton, New Canaan, Staples | Away - Allen's Meadow-XC Course [Directions] | 4:00 p.m. | ||
| Tue., 9/21 | V Field Hockey | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 7:30 p.m. | L 1-2 | |
| Tue., 9/21 | JV Field Hockey | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 6:00 p.m. | ||
| Tue., 9/21 | V Girls Soccer | Fairfield Warde | Away - Fairfield Warde HS-Varsity Grass Soccer Field [Directions] | 4:00 p.m. | L 6-0 | |
| Tue., 9/21 | JV Girls Soccer | Fairfield Warde | Away - Tunxis [Directions] | 4:00 p.m. | ||
| Tue., 9/21 | V Girls Volleyball | Shelton | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | W 3-1 | |
| Wed., 9/22 | V Boys Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:30 p.m. | Trumbull 175, Stamford 206 | |
| Wed., 9/22 | V Boys Soccer | Fairfield Warde | Home - Stamford HS-SHS Upper Soccer Field [Directions] | 4:00 p.m. | L 2-0 | |
| Wed., 9/22 | V Girls Swimming and Diving | Wilton | Away - Wilton YMCA [Directions] | 3:40 p.m. | ||
| Wed., 9/22 | FR Girls Volleyball | Danbury | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:15 p.m. | ||
| Thu., 9/23 | V Boys Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | 3:30 p.m. | Greenwich 159, Stamford 198 | |
| Thu., 9/23 | V Field Hockey | Danbury | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | W 1-0 | |
| Thu., 9/23 | JV Field Hockey | Danbury | Home - Stamford HS-Boyle Stadium [Directions] | 7:00 p.m. | ||
| Thu., 9/23 | V Girls Soccer | Wilton | Home - Stamford HS-SHS Upper Soccer Field [Directions] | 4:30 p.m. | L 5-0 | |
| Thu., 9/23 | V Girls Volleyball | Harding | Away - Warren Harding HS-Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Thu., 9/23 | JV Girls Volleyball | Harding | Away - Warren Harding HS-Gym [Directions] | 5:30 p.m. | ||
| Fri., 9/24 | V Football | Amity | Away - Amity Regional HS-William Johnson Stadium Field [Directions] | 7:00 p.m. | L 18-36 | |
| Fri., 9/24 | V Boys Soccer | Wilton | Away - Wilton HS-Lilly Field [Directions] | 5:00 p.m. | L 2-0 | |
| Fri., 9/24 | JV Boys Soccer | Wilton | Away - Allen's Meadow-2A [Directions] | 4:30 p.m. | ||
| Fri., 9/24 | V Competitive Cheerleading | Road Game - Amity Regional HS | Away - Not Listed-TBA | 7:00 p.m. | ||
| Fri., 9/24 | V Girls Swimming and Diving | Trumbull | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Sat., 9/25 | JV Boys Soccer | Fairfield Warde | Away - Fairfield Warde HS-Varsity Grass Soccer Field [Directions] | 10:00 a.m. | ||
| Sat., 9/25 | FR Boys Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | 10:00 a.m. | ||
| Sat., 9/25 | JV Girls Soccer | Wilton | Home - Stamford HS-SHS Upper Soccer Field [Directions] | 10:00 a.m. | ||
| Sat., 9/25 | FR Girls Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 11:00 a.m. | ||
| Mon., 9/27 | JV Football | Amity | Home - Stamford HS-Boyle Stadium [Directions] | 5:00 p.m. | ||
| Mon., 9/27 | V Boys Golf | Darien | Away - Wee Burn CC [Directions] | 3:15 p.m. | Darien 159, Stamford 200 | |
| Mon., 9/27 | V Girls Soccer | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 7:00 p.m. | L 2-0 | |
| Mon., 9/27 | JV Girls Soccer | New Canaan | Away - Conner Field, New Cannan [Directions] | 4:00 p.m. | ||
| Tue., 9/28 | V Boys Cross Country | Fairfield Warde, Norwalk, St. Joseph | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | ||
| Tue., 9/28 | V Boys Golf | Fairfield Ludlowe | Home - Stamford High-Sterling Farms Golf Course [Directions] | 3:00 p.m. | Ludlowe 153, Stamford 182 | |
| Tue., 9/28 | V Boys Soccer | New Canaan | Home - Stamford HS-SHS Upper Soccer Field [Directions] | 4:00 p.m. | W 4-0 | |
| Tue., 9/28 | V Girls Cross Country | Fairfield Warde, Norwalk, St. Joseph | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | ||
| Tue., 9/28 | V Field Hockey | Ridgefield | Away - Ridgefield HS-Tiger Hollow Turf Field II [Directions] | 7:00 p.m. | L 2-8 | |
| Tue., 9/28 | JV Field Hockey | Ridgefield | Away - Ridgefield HS-Tiger Hollow Turf Field II [Directions] | 5:30 p.m. | ||
| Tue., 9/28 | V Girls Volleyball | St. Joseph | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | L 0-3 | |
| Tue., 9/28 | JV Girls Volleyball | St. Joseph | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 9/29 | V Boys Golf | Brien McMahon | Home - Stamford High-Sterling Farms Golf Course [Directions] | 3:00 p.m. | Stamford 176, McMahon 178 | |
| Wed., 9/29 | FR Boys Soccer | Trumbull | Away - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | ||
| Wed., 9/29 | V Girls Swimming and Diving | Norwalk/McMahon | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Thu., 9/30 | FR Football | Harding | Away - Warren Harding HS-Lewis Field [Directions] | Canceled | Cancelled | |
| Thu., 9/30 | JV Boys Soccer | Ridgefield | Away - Ridgefield HS-Upper Grass Field [Directions] | 4:30 p.m. | ||
| Thu., 9/30 | V Girls Soccer | Ridgefield | Home - Stamford HS-SHS Upper Soccer Field [Directions] | 4:00 p.m. | L 1-0 | |
| Thu., 9/30 | JV Girls Soccer | Ridgefield | Away - Ridgefield HS-RHS Lower Grass Field [Directions] | 4:30 p.m. | ||
| Thu., 9/30 | V Girls Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:00 p.m. | L 1-3 | |
| Thu., 9/30 | JV Girls Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 5:15 p.m. | ||
| Thu., 9/30 | FR Girls Volleyball | Darien | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | ||
| Fri., 10/1 | V Football | Harding | Away - Warren Harding HS-Lewis Field [Directions] | 7:00 p.m. | L 26-36 | |
| Fri., 10/1 | V Competitive Cheerleading | Road Game - Harding High School | Away - Not Listed | 7:00 p.m. | ||
| Fri., 10/1 | V Field Hockey | Fairfield Ludlowe | Home - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | L 0-4 | |
| Fri., 10/1 | JV Field Hockey | Fairfield Ludlowe | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Fri., 10/1 | V Girls Swimming and Diving | Greenwich | Away - Greenwich HS-Pool [Directions] | 4:30 p.m. | ||
| Sat., 10/2 | V Boys Soccer | Ridgefield | Away - Ridgefield HS-Tiger Hollow Turf Field II [Directions] | 6:30 p.m. | L 5-2 | |
| Sat., 10/2 | JV Boys Soccer | New Canaan | Home - Stamford HS-SHS Upper Soccer Field [Directions] | 11:00 a.m. | ||
| Sat., 10/2 | FR Boys Soccer | Staples | Home - Stamford HS-SHS Upper Soccer Field [Directions] | 9:00 a.m. | ||
| Sat., 10/2 | V Girls Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 3:30 p.m. | W 3-2 | |
| Sat., 10/2 | JV Girls Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 2:00 p.m. | ||
| Sat., 10/2 | FR Girls Volleyball | St. Joseph | Home - Stamford HS-Kuczo Gymnasium [Directions] | 10:00 a.m. | ||
| Mon., 10/4 | JV Football | Harding | Home - Stamford HS-Boyle Stadium [Directions] | Canceled | Cancelled | |
| Mon., 10/4 | V Girls Soccer | Trumbull | Home - Stamford HS-SHS Upper Soccer Field [Directions] | 4:00 p.m. | L 2-1 | |
| Mon., 10/4 | JV Girls Soccer | Trumbull | Home - Rippowam MS-Upper Soccer/Footballl Field [Directions] | 4:00 p.m. | ||
| Tue., 10/5 | V Boys Cross Country | Danbury, Brien McMahon | Away - Tarrywile Park [Directions] | 4:00 p.m. | ||
| Tue., 10/5 | V Boys Golf | St. Joseph | Home - Stamford High-Sterling Farms Golf Course [Directions] | 3:00 p.m. | St. Joseph 152, Stamford 191 | |
| Tue., 10/5 | V Boys Soccer | Trumbull | Away - Trumbull HS-Cork Field [Directions] | 5:30 p.m. | L 0-4 | |
| Tue., 10/5 | JV Boys Soccer | Trumbull | Away - Trumbull HS-The Pit [Directions] | 4:00 p.m. | ||
| Tue., 10/5 | FR Boys Soccer | Fairfield Warde | Home - Rippowam MS-Upper Soccer/Footballl Field [Directions] | 4:00 p.m. | ||
| Tue., 10/5 | V Girls Cross Country | Danbury, Brien McMahon | Away - Tarrywile Park [Directions] | 4:00 p.m. | ||
| Tue., 10/5 | V Field Hockey | Darien | Home - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | L 0-8 | |
| Tue., 10/5 | JV Field Hockey | Darien | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Tue., 10/5 | V Girls Swimming and Diving | Staples | Away - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Tue., 10/5 | V Girls Volleyball | Fairfield Warde | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | L 2-3 | |
| Tue., 10/5 | JV Girls Volleyball | Fairfield Warde | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 10/6 | V Boys Golf | Westhill | Home - EG Brennan Golf Course-E Gaynor Brennan Golf Course [Directions] | 2:30 p.m. | Westhill 168, Stamford 182 | |
| Wed., 10/6 | V Girls Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 7:00 p.m. | L 1-0 | |
| Wed., 10/6 | JV Girls Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 4:00 p.m. | ||
| Wed., 10/6 | FR Girls Volleyball | Norwalk | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:00 p.m. | ||
| Thu., 10/7 | FR Football | Ridgefield | Away - Ridgefield HS-Tiger Hollow Turf Field II [Directions] | 7:00 p.m. | ||
| Thu., 10/7 | V Boys Golf | Chappa Invitational - Long Shore | Away - Not Listed-Longshore Golf Course | TBA | ||
| Thu., 10/7 | V Boys Soccer | Fairfield Ludlowe | Home - Stamford HS-SHS Upper Soccer Field [Directions] | 4:00 p.m. | W 3-1 | |
| Thu., 10/7 | JV Boys Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | 4:00 p.m. | ||
| Thu., 10/7 | V Girls Volleyball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:30 p.m. | L 0-3 | |
| Thu., 10/7 | JV Girls Volleyball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:15 p.m. | ||
| Fri., 10/8 | V Football | Ridgefield | Away - Ridgefield HS-Tiger Hollow Turf Field II [Directions] | 7:00 p.m. | L 6-42 | |
| Fri., 10/8 | V Competitive Cheerleading | Road Game - Ridgefield High School | Away - Not Listed-TBA | 7:00 p.m. | ||
| Fri., 10/8 | V Field Hockey | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:30 p.m. | L 0-8 | |
| Fri., 10/8 | JV Field Hockey | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Fri., 10/8 | V Girls Soccer | Staples | Away - Staples HS-Loeffler Field - Staples HS [Directions] | 4:00 p.m. | L 4-0 | |
| Fri., 10/8 | JV Girls Soccer | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Fri., 10/8 | V Girls Swimming and Diving | Ridgefield | Away - Barlow Mountain Pool [Directions] | 4:00 p.m. | ||
| Sat., 10/9 | FR Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 9:00 a.m. | ||
| Sat., 10/9 | V Girls Volleyball | New Canaan | Home - Stamford HS-Kuczo Gymnasium [Directions] | 11:30 a.m. | L 1-3 | |
| Sat., 10/9 | JV Girls Volleyball | New Canaan | Home - Stamford HS-Kuczo Gymnasium [Directions] | 10:00 a.m. | ||
| Sat., 10/9 | FR Girls Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 1:00 p.m. | ||
| Mon., 10/11 | V Boys Golf | Holohan Event | Away - Not Listed | 3:15 p.m. | ||
| Mon., 10/11 | V Boys Soccer | Staples | Home - Stamford HS-SHS Upper Soccer Field [Directions] | 4:00 p.m. | L 1-4 | |
| Mon., 10/11 | JV Boys Soccer | Staples | Home - Rippowam MS-Upper Soccer/Footballl Field [Directions] | 4:00 p.m. | ||
| Mon., 10/11 | V Field Hockey | Staples | Home - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | L 1-6 | |
| Mon., 10/11 | JV Field Hockey | Staples | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Mon., 10/11 | V Girls Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Mon., 10/11 | JV Girls Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/12 | V Boys Cross Country | Fairfield Ludlowe, Darien, Trumbull | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | ||
| Tue., 10/12 | V Boys Golf | Norwalk | Away - Oak Hills Golf Course [Directions] | 3:30 p.m. | Stamford 195, Norwalk 196 | |
| Tue., 10/12 | V Girls Cross Country | Fairfield Ludlowe, Darien, Trumbull | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | ||
| Tue., 10/12 | V Girls Soccer | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | W 4-0 | |
| Tue., 10/12 | JV Girls Soccer | Westhill | Away - Rippowan MS-Rippowam Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 10/12 | FR Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 10/13 | V Boys Soccer | Westhill | Home - Stamford HS-SHS Upper Soccer Field [Directions] | 4:00 p.m. | T 1-1 | |
| Wed., 10/13 | JV Boys Soccer | Westhill | Home - Rippowam MS-Upper Soccer/Footballl Field [Directions] | 4:00 p.m. | ||
| Wed., 10/13 | V Girls Swimming and Diving | St. Joseph | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Wed., 10/13 | V Girls Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Wed., 10/13 | JV Girls Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/14 | FR Football | Trumbull | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Thu., 10/14 | V Field Hockey | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 4:00 p.m. | L 1-2 | |
| Thu., 10/14 | JV Field Hockey | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 5:30 p.m. | ||
| Thu., 10/14 | V Girls Soccer | Norwalk | Home - Stamford HS-SHS Upper Soccer Field [Directions] | 4:00 p.m. | W 1-0 | |
| Thu., 10/14 | JV Girls Soccer | Norwalk | Home - Rippowam MS-Upper Soccer/Footballl Field [Directions] | 4:00 p.m. | ||
| Fri., 10/15 | V Field Hockey | Weston | Home - Stamford HS-Boyle Stadium [Directions] | 5:45 p.m. | W 2-0 | |
| Fri., 10/15 | JV Field Hockey | Weston | Home - Stamford HS-Boyle Stadium [Directions] | 4:15 p.m. | ||
| Fri., 10/15 | V Girls Swimming and Diving | New Canaan | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Fri., 10/15 | V Girls Volleyball | Fairfield Ludlowe | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | L 0-3 | |
| Fri., 10/15 | JV Girls Volleyball | Fairfield Ludlowe | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Sat., 10/16 | V Football | Trumbull | Home - Stamford HS-Boyle Stadium [Directions] | 12:00 p.m. | L 0-48 | |
| Sat., 10/16 | V Boys Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 5:30 p.m. | L 0-7 | |
| Sat., 10/16 | JV Boys Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 3:00 p.m. | ||
| Sat., 10/16 | FR Boys Soccer | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 11:00 a.m. | ||
| Sat., 10/16 | FR Girls Volleyball | Ridgefield | Home - Stamford HS-Kuczo Gymnasium [Directions] | 10:00 a.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 Field Hockey | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 7:30 p.m. | L 2-4 | |
| Mon., 10/18 | JV Field Hockey | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | ||
| Mon., 10/18 | V Girls Soccer | Darien | Away - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | L 2-0 | |
| Mon., 10/18 | JV Girls Soccer | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 10/18 | V Girls Volleyball | Staples | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | L 0-3 | |
| Mon., 10/18 | JV Girls Volleyball | Staples | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 10/19 | V Boys Soccer | Darien | Home - Stamford HS-SHS Upper Soccer Field [Directions] | 4:00 p.m. | L 4-1 | |
| Tue., 10/19 | JV Boys Soccer | Darien | Home - Rippowam MS-Upper Soccer/Footballl Field [Directions] | 4:00 p.m. | ||
| Wed., 10/20 | V Boys Cross Country | FCIACs | Away - Not Listed-Waveny Park | 1:15 p.m. | ||
| Wed., 10/20 | FR Boys Soccer | Greenwich | Away - Central MS [Directions] | 4:30 p.m. | ||
| Wed., 10/20 | V Girls Cross Country | FCIACs | Away - Not Listed-Waveny Park | 1:15 p.m. | ||
| Wed., 10/20 | V Field Hockey | Fairfield Warde | Home - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | W 2-0 | |
| Wed., 10/20 | JV Field Hockey | Fairfield Warde | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Wed., 10/20 | V Girls Swimming and Diving | Danbury | Away - WCSU O'Neill Center - Blue Gym-O'Neill Center [Directions] | 7:00 p.m. | ||
| Wed., 10/20 | V Girls Volleyball | Westhill | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | L 1-3 | |
| Wed., 10/20 | JV Girls Volleyball | Westhill | Home - Stamford HS-Kuczo Gymnasium [Directions] | 6:00 p.m. | ||
| Wed., 10/20 | FR Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 3:30 p.m. | ||
| Thu., 10/21 | FR Football | Staples | Away - Staples HS-Staples Stadium [Directions] | 6:00 p.m. | ||
| Thu., 10/21 | V Girls Soccer | Bridgeport Central | Home - Stamford HS-SHS Upper Soccer Field [Directions] | 4:30 p.m. | W 4-0 | |
| Fri., 10/22 | V Football | Staples | Away - Staples HS-Staples Stadium [Directions] | 7:00 p.m. | L 0-54 | |
| Fri., 10/22 | V Boys Soccer | Bridgeport Central | Away - Bridgeport Central HS-Kennedy Stadium Turf [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 10/22 | JV Boys Soccer | Bridgeport Central | Away - Bridgeport Central HS-Seaside Park [Directions] | 4:00 p.m. | ||
| Fri., 10/22 | V Competitive Cheerleading | Road Game - Staples High School | Away - Not Listed-TBA | 7:00 p.m. | ||
| Fri., 10/22 | V Girls Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 10/22 | JV Girls Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:30 p.m. | ||
| Sat., 10/23 | FR Boys Soccer | New Canaan | Home - Stamford HS-SHS Upper Soccer Field [Directions] | 9:00 a.m. | ||
| Sat., 10/23 | FR Girls Volleyball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 10:00 a.m. | ||
| Mon., 10/25 | V Girls Soccer | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | L 0-3 | |
| Mon., 10/25 | JV Girls Soccer | Greenwich | Away - Cos Cob Park-Binney Park [Directions] | 4:30 p.m. | ||
| Wed., 10/27 | V Boys Soccer | Greenwich | Home - Stamford HS-SHS Upper Soccer Field [Directions] | 4:00 p.m. | L 3-1 | |
| Wed., 10/27 | JV Boys Soccer | Greenwich | Home - Rippowam MS-Upper Soccer/Footballl Field [Directions] | 4:00 p.m. | ||
| Wed., 10/27 | V Field Hockey | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 7:30 p.m. | T 1-1 | |
| Wed., 10/27 | JV Field Hockey | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 6:00 p.m. | ||
| Thu., 10/28 | FR Football | Fairfield Ludlowe | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Thu., 10/28 | FR Boys Soccer | Darien | Home - Stamford HS-SHS Upper Soccer Field [Directions] | 4:00 p.m. | ||
| Thu., 10/28 | V Girls Volleyball | Bridgeport Central | Away - Bridgeport Central HS-Barry McLeod Court [Directions] | 5:30 p.m. | W 3-0 | |
| Thu., 10/28 | JV Girls Volleyball | Bridgeport Central | Away - Bridgeport Central HS-Barry McLeod Court [Directions] | 4:00 p.m. | ||
| Thu., 10/28 | FR Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | ||
| Fri., 10/29 | FR Boys Soccer | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 3:30 p.m. | ||
| Fri., 10/29 | V Girls Volleyball | Darien | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | L 0-3 | |
| Fri., 10/29 | JV Girls Volleyball | Darien | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Sat., 10/30 | V Football | Fairfield Ludlowe | Home - Stamford HS-Boyle Stadium [Directions] | 12:00 p.m. | L 8-43 | |
| Sat., 10/30 | V Girls Volleyball | Greenwich | Home - Stamford HS-Kuczo Gymnasium [Directions] | 12:30 p.m. | L 0-3 | |
| Sat., 10/30 | JV Girls Volleyball | Greenwich | Home - Stamford HS-Kuczo Gymnasium [Directions] | 11:00 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 Girls Cross Country | CIAC Girls Cross Country Class LL Championship | Away - Wickham Park | 1:30 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 | St. Joseph | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 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 Girls Cross Country | CIAC Girls Cross Country Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Sat., 11/6 | V Football | St. Joseph | Home - Stamford HS-Boyle Stadium [Directions] | 12:00 p.m. | L 0-35 | |
| 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 | ||||||
| Thu., 11/11 | V Girls Swimming and Diving | CIAC Class LL Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Fri., 11/12 | FR Football | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 3:30 p.m. | ||
| Sat., 11/13 | V Football | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 1:00 p.m. | L 12-64 | |
| Sat., 11/13 | V Competitive Cheerleading | Road Game - Greenwich HS | Away - Not Listed-TBA | 3:00 p.m. | ||
| Sat., 11/13 | V Girls Swimming and Diving | CIAC Class LL Qualifying Meet | Away - East Hartford | 11:30 a.m. | ||
| Wed., 11/17 | V Girls Swimming and Diving | CIAC Class LL Swimming Championships | Away - SCSU | 6:00 p.m. | ||
| Thu., 11/18 | V Girls Swimming and Diving | CIAC State Open Diving Championships | Away - Middletown | 5:30 p.m. | ||
| Sat., 11/20 | FR Football | Westhill | Home - Stamford HS-Boyle Stadium [Directions] | 10:00 a.m. | ||
| Sun., 11/21 | V Girls Swimming and Diving | CIAC State Open Swimming Championships | Away - Cornerstone Pool | 2:00 p.m. | ||
| Thu., 11/25 | V Football | Westhill | Home - Stamford HS-Boyle Stadium [Directions] | 10:00 a.m. | W 14-7 | |
| Sat., 12/4 | V Girls Basketball | Fairfield Warde (Scrim.) | Home - Danbury HS-New Gym [Directions] | 12:00 p.m. | ||
| Sat., 12/4 | V Girls Basketball | Brookfield (Scrim.) | Home - Danbury HS-Main Gym [Directions] | 12:30 p.m. | ||
| Sat., 12/4 | V Girls Basketball | Bridgeport Central (Scrim.) | Home - Danbury HS-New Gym [Directions] | 1:30 p.m. | ||
| Sat., 12/4 | V Girls Basketball | New Fairfield | Home - Danbury HS-New Gym [Directions] | 2:00 p.m. | ||
| Sat., 12/4 | V Girls Basketball | Bethel (Scrim.) | Home - Danbury HS-G gym (freshman academy gym) [Directions] | 3:00 p.m. | ||
| Sat., 12/4 | V Girls Basketball | Capital Prep Harbor (Scrim.) | Home - Danbury HS-Main Gym [Directions] | 3:30 p.m. | ||
| Sat., 12/4 | V Girls Basketball | New Canaan (Scrim.) | Away - Danbury HS-G gym (freshman academy gym) [Directions] | 4:30 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 Girls Basketball | Staples (Scrim.) | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 12/8 | V Boys Ice Hockey | Immaculate (Scrim.) | Home - Terry Conners - Stamford-Ice Rink [Directions] | 2:30 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 | JV Football | Westhill | Home - Stamford HS-Boyle Stadium [Directions] | 3:00 p.m. | ||
| Thu., 12/9 | JV Football | Westhill | Home - Stamford HS-Boyle Stadium [Directions] | Canceled | Cancelled | |
| Sat., 12/11 | V Boys Basketball | Bristol Central (Scrim.) | Away - Bristol Central HS-Charles C. Marsh Gymnasium [Directions] | 10:00 a.m. | ||
| Sat., 12/11 | V Girls Basketball | Shelton (Scrim.) | Away - Shelton HS-Murray Gymnasium [Directions] | 10:00 a.m. | ||
| Sat., 12/11 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice-New [Directions] | 4:15 p.m. | W 10-3 | |
| Tue., 12/14 | V Boys Basketball | Bassick (Scrim.) | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | ||
| Tue., 12/14 | V Girls Basketball | Sacred Heart Academy | Away - Sacred Heart Academy-Gym [Directions] | 7:00 p.m. | L 83-48 | |
| Tue., 12/14 | JV Girls Basketball | Sacred Heart Academy | Away - Sacred Heart Academy-Gym [Directions] | 5:15 p.m. | ||
| Wed., 12/15 | V Wrestling | Trumbull | Away - Trumbull HS-Aux Gym [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 Girls Basketball | West Haven | Away - West Haven HS-Gym [Directions] | 6:00 p.m. | L 49-63 | |
| Thu., 12/16 | JV Girls Basketball | West Haven | Away - West Haven HS-Gym [Directions] | 4:15 p.m. | ||
| Sat., 12/18 | V Boys Basketball | North Haven | Away - North Haven HS-Fred Kelly Gymnasium [Directions] | 3:00 p.m. | W 50-38 | |
| Sat., 12/18 | JV Boys Basketball | North Haven | Away - North Haven HS-Fred Kelly Gymnasium [Directions] | 1:15 p.m. | ||
| Sat., 12/18 | V Boys Ice Hockey | Amity | Home - Terry Conners - Stamford-Ice Rink [Directions] | 8:00 p.m. | W 6-1 | |
| Sat., 12/18 | V Boys Indoor Track | Staples, Greenwich, Trumbull, Westhill | Away - Staples HS-Field House [Directions] | 12:30 p.m. | ||
| Sat., 12/18 | V Wrestling | Ludlowe Invitational | Away - Fairfield Ludlowe HS-Main Gym | 9:00 a.m. | ||
| Sat., 12/18 | V Girls Basketball | Pomperaug | Away - Pomperaug HS-Main Gym [Directions] | 1:15 p.m. | W 60-51 | |
| Sat., 12/18 | JV Girls Basketball | Pomperaug | Away - Pomperaug HS-Main Gym [Directions] | 11:30 a.m. | ||
| Sat., 12/18 | FR Girls Basketball | Pomperaug | Away - Pomperaug HS-Main Gym [Directions] | 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 | Staples, Greenwich, Trumbull, Westhill | Away - Staples HS-Field House [Directions] | 12:30 p.m. | ||
| Tue., 12/21 | V Boys Basketball | Kolbe Cathedral | Home - Stamford HS-Kuczo Gymnasium [Directions] | 6:00 p.m. | L 46-61 | |
| Tue., 12/21 | JV Boys Basketball | Kolbe Cathedral | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | ||
| Wed., 12/22 | V Girls Basketball | Bridgeport Central | Home - Stamford HS-Kuczo Gymnasium [Directions] | 6:00 p.m. | W 75-15 | |
| Wed., 12/22 | JV Girls Basketball | Bridgeport Central | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | ||
| Wed., 12/22 | FR Girls Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [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 | Fairfield Warde, Brien McMahon, Norwalk | Away - Fairfield Warde HS-Small Gym [Directions] | 2:00 p.m. | ||
| Mon., 12/27 | V Wrestling | Trumbull JV Tourney | Away - Not Listed-Trumbull | Canceled | Cancelled | |
| 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 | V Boys Basketball | Bridgeport Central | Home - Westhill HS-Main Gym [Directions] | 4:00 p.m. | W 55-36 | |
| Tue., 12/28 | V Girls Basketball | Clarkstown North (NY) | Home - Stamford HS-Kuczo Gymnasium [Directions] | 6:00 p.m. | W 48-32 | |
| 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 | V Boys Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 6:00 p.m. | W 53-39 | |
| Thu., 12/30 | V Girls Basketball | Kolbe Cathedral | Home - Stamford HS-Kuczo Gymnasium [Directions] | 6:00 p.m. | W 57-34 | |
| Tue., 1/4 | V Girls Basketball | Ridgefield | Home - Stamford HS-Kuczo Gymnasium [Directions] | 6:00 p.m. | L 50-62 | |
| Tue., 1/4 | JV Girls Basketball | Ridgefield | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | ||
| Tue., 1/4 | V Girls Gymnastics | Westhill, Norwalk, Staples | Away - Westhill HS-New Gym [Directions] | 6:00 p.m. | 97.95 | |
| Wed., 1/5 | V Boys Ice Hockey | Brien McMahon/Norwalk | Home - Terry Conners - Stamford-Ice Rink [Directions] | 7:45 p.m. | W 4-2 | |
| Wed., 1/5 | FR Girls Basketball | Ridgefield | Home - Stamford HS-Kuczo Gymnasium [Directions] | Postponed | ||
| Thu., 1/6 | V Wrestling | Westhill | Away - Westhill HS-Main Gym [Directions] | 6:00 p.m. | ||
| Sat., 1/8 | V Boys Basketball | St. Joseph | Home - Stamford HS-Kuczo Gymnasium [Directions] | 1:00 p.m. | W 52-44 | |
| Sat., 1/8 | JV Boys Basketball | St. Joseph | Home - Stamford HS-Kuczo Gymnasium [Directions] | 10:30 a.m. | ||
| Sat., 1/8 | FR Boys Basketball | St. Joseph | Home - Stamford HS-Kuczo Gymnasium [Directions] | 9:00 a.m. | ||
| Sat., 1/8 | V Boys Ice Hockey | North Haven | Home - Terry Conners - Stamford-Ice Rink [Directions] | 8:00 p.m. | L 2-5 | |
| Sat., 1/8 | V Boys Indoor Track | FCIAC, Fairfield Ludlowe, Fairfield Warde, Norwalk | Away - Wilton HS-Wilton Field House | 11:00 a.m. | ||
| Sat., 1/8 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Away - Fairfield University-Pool [Directions] | 11:30 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 | V Girls Indoor Track | FCIAC, Fairfield Ludlowe, Fairfield Warde, Norwalk | Away - Wilton HS-Wilton Field House | 11:00 a.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 | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 6:15 p.m. | W 59-54 | |
| Tue., 1/11 | JV Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:30 p.m. | ||
| Tue., 1/11 | V Girls Basketball | Brien McMahon | Home - Stamford HS-Kuczo Gymnasium [Directions] | 6:00 p.m. | W 60-31 | |
| Tue., 1/11 | JV Girls Basketball | Brien McMahon | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | ||
| Tue., 1/11 | V Girls Gymnastics | Greenwich, Westhill | Away - Greenwich YWCA [Directions] | 6:30 p.m. | 111.55 | |
| Wed., 1/12 | FR Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:45 p.m. | ||
| Wed., 1/12 | V Boys Ice Hockey | North Branford | Away - Northford Ice Pavilion-Red [Directions] | 8:30 p.m. | W 3-2 | |
| Wed., 1/12 | V Boys Swimming and Diving | New Canaan | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Wed., 1/12 | V Wrestling | St. Joseph, Greenwich | Away - St Joseph [Directions] | 5:00 p.m. | ||
| Wed., 1/12 | FR Girls Basketball | Danbury | Home - Stamford HS-Kuczo Gymnasium [Directions] | 6:00 p.m. | ||
| Thu., 1/13 | V Boys Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 6:00 p.m. | L 61-73 | |
| Thu., 1/13 | JV Boys Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 4:30 p.m. | ||
| Thu., 1/13 | V Girls Basketball | Danbury | Home - Stamford HS-Kuczo Gymnasium [Directions] | 6:00 p.m. | L 49-66 | |
| Thu., 1/13 | JV Girls Basketball | Danbury | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | ||
| Thu., 1/13 | V Girls Gymnastics | Westhill, St. Joseph, Trumbull | Away - Westhill HS-New Gym [Directions] | 6:00 p.m. | ||
| Fri., 1/14 | FR Boys Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 5:00 p.m. | ||
| Sat., 1/15 | V Boys Ice Hockey | Darien | Home - Terry Conners - Stamford-Ice Rink [Directions] | 8:15 p.m. | L 1-5 | |
| Sat., 1/15 | V Boys Indoor Track | FCIAC, Darien, St. Joseph, Staples | Away - Staples HS-Field House | 10:00 a.m. | ||
| Sat., 1/15 | V Girls Basketball | Westhill | Home - Stamford HS-Kuczo Gymnasium [Directions] | 11:30 a.m. | W 53-34 | |
| Sat., 1/15 | JV Girls Basketball | Westhill | Home - Stamford HS-Kuczo Gymnasium [Directions] | 10:00 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, Staples | Away - Staples HS-Field House | 10:00 a.m. | ||
| Mon., 1/17 | V Boys Basketball | Fairfield Warde | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:00 p.m. | L 54-74 | |
| Mon., 1/17 | JV Boys Basketball | Fairfield Warde | Home - Stamford HS-Kuczo Gymnasium [Directions] | 3:30 p.m. | ||
| Mon., 1/17 | V Boys Ice Hockey | Staples | Away - Milford Ice Pavillion-Ice Rink [Directions] | 4:00 p.m. | W 5-2 | |
| Mon., 1/17 | V Girls Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 5:30 p.m. | W 54-26 | |
| Mon., 1/17 | JV Girls Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 3:45 p.m. | ||
| Mon., 1/17 | V Girls Gymnastics | Fairfield Ludlowe, Westhill | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 10:00 a.m. | 122.60 | |
| Mon., 1/17 | V Girls Gymnastics | Fairfield Warde, Westhill | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 10:00 a.m. | 122.60 | |
| 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 | FR Boys Basketball | Fairfield Warde | Home - Stamford HS-Kuczo Gymnasium [Directions] | 6:00 p.m. | ||
| Wed., 1/19 | V Boys Ice Hockey | Sheehan | Away - Choate Rosemary Hall-Ice Rink [Directions] | 7:30 p.m. | L 2-5 | |
| Wed., 1/19 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Wed., 1/19 | V Wrestling | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:30 p.m. | ||
| Wed., 1/19 | FR Girls Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 5:30 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) | |
| Fri., 1/21 | V Boys Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 7:00 p.m. | L 47-64 | |
| Fri., 1/21 | JV Boys Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:30 p.m. | ||
| Fri., 1/21 | V Boys Swimming and Diving | St. Joseph, Trumbull | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Sat., 1/22 | FR Boys Basketball | Wilton | Home - Stamford HS-Kuczo Gymnasium [Directions] | 11:30 a.m. | ||
| Sat., 1/22 | V Boys Ice Hockey | St. Joseph | Home - Terry Conners - Stamford-Ice Rink [Directions] | 8:00 p.m. | L 2-7 | |
| Sat., 1/22 | V Boys Indoor Track | FCIAC, New Canaan, Norwalk, Staples | Away - Staples HS-Field House | 10:00 a.m. | ||
| Sat., 1/22 | FR Girls Basketball | Wilton | Home - Stamford HS-Kuczo Gymnasium [Directions] | 10:00 a.m. | ||
| Sat., 1/22 | V Girls Indoor Track | FCIAC, New Canaan, Norwalk, Staples | Away - Staples HS-Field House | 10:00 a.m. | ||
| Mon., 1/24 | V Boys Basketball | New Canaan | Home - Stamford HS-Kuczo Gymnasium [Directions] | 6:00 p.m. | W 63-50 | |
| Mon., 1/24 | JV Boys Basketball | New Canaan | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | ||
| Mon., 1/24 | V Boys Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | 8:10 p.m. | L 2-5 | |
| Mon., 1/24 | V Boys Swimming and Diving | Wilton | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Mon., 1/24 | V Girls Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 6:15 p.m. | W 56-26 | |
| Mon., 1/24 | JV Girls Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:30 p.m. | ||
| Tue., 1/25 | FR Boys Basketball | New Canaan | Home - Stamford HS-Kuczo Gymnasium [Directions] | Postponed | ||
| Tue., 1/25 | V Girls Basketball | Wilton | Home - Stamford HS-Kuczo Gymnasium [Directions] | 6:00 p.m. | L 45-57 | |
| Tue., 1/25 | JV Girls Basketball | Wilton | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | ||
| Tue., 1/25 | FR Girls Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 6:30 p.m. | ||
| Tue., 1/25 | V Girls Gymnastics | Wilton, Westhill | Away - Wilton HS-Aux Gym [Directions] | 5:00 p.m. | 121.05 | |
| Wed., 1/26 | V Boys Ice Hockey | Daniel Hand | Home - Terry Conners - Stamford-Ice Rink [Directions] | 3:30 p.m. | W 2-1(OT) | |
| Wed., 1/26 | V Wrestling | Ridgefield | Away - Ridgefield HS-Aux Gym [Directions] | 6:30 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 | Greenwich | Home - Stamford HS-Kuczo Gymnasium [Directions] | 6:00 p.m. | L 46-50 | |
| Thu., 1/27 | JV Boys Basketball | Greenwich | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | ||
| Thu., 1/27 | V Girls Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 6:30 p.m. | L 48-47 | |
| Thu., 1/27 | JV Girls Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:15 p.m. | ||
| Thu., 1/27 | FR Girls Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/28 | V Boys Swimming and Diving | Danbury | Away - WCSU O'Neill Center - Blue Gym-O'Neill Center [Directions] | 5:00 p.m. | ||
| Sat., 1/29 | V Boys Indoor Track | FCIAC Divisional meet | Away - Not Listed-Wilton HS | Canceled | Cancelled | |
| Sat., 1/29 | V Wrestling | Norwalk JV Invite | Away - Not Listed-Norwalk HS | Canceled | Cancelled | |
| Sat., 1/29 | FR Girls Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | Postponed | ||
| Sat., 1/29 | V Girls Indoor Track | FCIAC Divisional meet | Away - Not Listed-Wilton HS | Canceled | Cancelled | |
| Mon., 1/31 | V Wrestling | Wilton | Away - Wilton HS-Nicholas Zeoli Fieldhouse [Directions] | 7:00 p.m. | ||
| Mon., 1/31 | V Girls Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 6:00 p.m. | L 22-44 | |
| Mon., 1/31 | JV Girls Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:30 p.m. | ||
| Tue., 2/1 | V Boys Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | W 56-43 | |
| Tue., 2/1 | JV Boys Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 4:30 p.m. | ||
| Tue., 2/1 | V Girls Basketball | Trumbull | Home - Stamford HS-Kuczo Gymnasium [Directions] | 6:00 p.m. | W 59-41 | |
| Tue., 2/1 | JV Girls Basketball | Trumbull | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | ||
| Wed., 2/2 | FR Boys Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | ||
| Wed., 2/2 | V Boys Ice Hockey | Brien McMahon/Norwalk | Away - Sono Ice House-Main Rink [Directions] | 8:00 p.m. | W 6-3 | |
| Wed., 2/2 | V Boys Swimming and Diving | Darien | Away - Darien YMCA [Directions] | 3:00 p.m. | ||
| Wed., 2/2 | FR Girls Basketball | Darien | Home - Stamford HS-Kuczo Gymnasium [Directions] | 6:00 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 Indoor Track | FCIAC Indoor Track Championships | Away - Floyd Little Athletic Center-Field House | 4:30 p.m. | ||
| Thu., 2/3 | V Girls Indoor Track | FCIAC Indoor Track Championships | Away - Floyd Little Athletic Center-Field House | 4:30 p.m. | ||
| Sat., 2/5 | V Boys Basketball | Fairfield Ludlowe | Home - Stamford HS-Kuczo Gymnasium [Directions] | 1:00 p.m. | W 66-53 | |
| Sat., 2/5 | JV Boys Basketball | Fairfield Ludlowe | Home - Stamford HS-Kuczo Gymnasium [Directions] | 11:30 a.m. | ||
| Sat., 2/5 | FR Boys Basketball | Fairfield Ludlowe | Home - Stamford HS-Kuczo Gymnasium [Directions] | 10:00 a.m. | ||
| Sat., 2/5 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland of Ice-Stadium [Directions] | 6:30 p.m. | L 2-5 | |
| Sat., 2/5 | V Wrestling | Fairfield Ludlowe, Joel Barlow | Away - Fairfield Ludlowe HS-Aux Gym [Directions] | 4:00 p.m. | ||
| Sat., 2/5 | V Competitive Cheerleading | FCIACs | Home - Stamford HS-SHS Aux Gym [Directions] | 10:00 a.m. | ||
| Sat., 2/5 | V Girls Gymnastics | Darien, Westhill | Away - Darien YMCA [Directions] | 2:30 p.m. | 73.55 | |
| Sat., 2/5 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | 8:30 p.m. | W 10-1 | |
| Mon., 2/7 | FR Boys Basketball | Staples | Home - Stamford HS-Kuczo Gymnasium [Directions] | 6:00 p.m. | ||
| Mon., 2/7 | V Boys Ice Hockey | Trumbull | Home - Terry Conners - Stamford-Ice Rink [Directions] | 1:00 p.m. | W 5-1 | |
| Mon., 2/7 | V Boys Swimming and Diving | Staples | Home - Westhill HS-Westhill Pool [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 | Staples | Home - Stamford HS-Kuczo Gymnasium [Directions] | 6:00 p.m. | L 32-62 | |
| Tue., 2/8 | JV Boys Basketball | Staples | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | ||
| Tue., 2/8 | V Girls Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 7:00 p.m. | W 39-27 | |
| Tue., 2/8 | JV Girls Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/8 | FR Girls Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/8 | Unified Sports Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 3:30 p.m. | ||
| Wed., 2/9 | V Boys Ice Hockey | Staples | Home - Terry Conners - Stamford-Ice Rink [Directions] | 7:30 p.m. | W 5-2 | |
| Wed., 2/9 | V Wrestling | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 7:00 p.m. | ||
| Wed., 2/9 | V Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 7:00 p.m. | L 50-37 | |
| Wed., 2/9 | JV Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:15 p.m. | ||
| Wed., 2/9 | FR Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/9 | FR Girls Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | Postponed | ||
| Wed., 2/9 | V Girls Gymnastics | Trumbull, St. Joseph, Westhill | Away - Westhill HS-New Gym [Directions] | 6:00 p.m. | 118.45 | |
| 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 | Unified Sports Basketball | Westhill | Home - Stamford HS-SHS Aux Gym [Directions] | 2:45 p.m. | ||
| Fri., 2/11 | V Boys Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 5:30 p.m. | L 55-59 | |
| Fri., 2/11 | JV Boys Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 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 Boys Swimming and Diving | Ridgefield | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Fri., 2/11 | V Wrestling | FCIAC, Danbury, Darien, Fairfield Ludlowe, Fairfield Warde, Greenwich, TBA, New Canaan, Norwalk, Ridgefield, St. Joseph, Staples, Trumbull, Westhill, Wilton | Away - New Canaan HS-Main Gym | 4:30 p.m. | ||
| Fri., 2/11 | V Girls Indoor Track | Class LL Championship | Away - Floyd Little Athletic Center | 4:00 p.m. | ||
| Sat., 2/12 | FR Boys Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 2/12 | V Wrestling | FCIAC Wrestling Championships Wrestlebacks | Away - New Canaan HS-Main Gym | 10:00 a.m. | ||
| Sat., 2/12 | V Girls Gymnastics | FCIAC Gymnastics Championships | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 | 11:00 a.m. | ||
| 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 Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 6:15 p.m. | L 44-48 | |
| Mon., 2/14 | JV Boys Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:30 p.m. | ||
| Mon., 2/14 | V Girls Basketball | Norwalk | Home - Stamford HS-Kuczo Gymnasium [Directions] | 6:00 p.m. | W 38-35 | |
| Mon., 2/14 | JV Girls Basketball | Norwalk | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | ||
| Tue., 2/15 | FR Boys Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:45 p.m. | ||
| Wed., 2/16 | V Boys Basketball | Darien | Home - Stamford HS-Kuczo Gymnasium [Directions] | 6:00 p.m. | L 57-59 | |
| Wed., 2/16 | JV Boys Basketball | Darien | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | ||
| Wed., 2/16 | V Girls Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | W 49-36 | |
| Wed., 2/16 | JV Girls Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| 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 | Trumbull | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | 7:30 p.m. | W 2-1 | |
| Thu., 2/17 | FR Girls Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 2/17 | Unified Sports Basketball | Vs Greenwich HS | Away - Not Listed-Greenwich HS | Postponed | ||
| Fri., 2/18 | V Boys Basketball | Bridgeport Central | Away - Bridgeport Central HS-Barry McLeod Court [Directions] | 2:00 p.m. | W 71-27 | |
| Fri., 2/18 | JV Boys Basketball | Bridgeport Central | Away - Bridgeport Central HS-Barry McLeod Court [Directions] | 12:00 p.m. | ||
| Fri., 2/18 | FR Boys Basketball | Bridgeport Central | Away - Bridgeport Central HS-Barry McLeod Court [Directions] | 10:00 a.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 | FR Boys Basketball | Darien | Home - Stamford HS-Kuczo Gymnasium [Directions] | 10:00 a.m. | ||
| Sat., 2/19 | V Boys Ice Hockey | Branford | Home - Terry Conners - Stamford-Ice Rink [Directions] | 6:30 p.m. | W 6-5 | |
| 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 Girls Basketball | Danbury | Away - Staples HS-Staples Gym [Directions] | 2:00 p.m. | ||
| 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 | Fitch | Home - Stamford HS-Kuczo Gymnasium [Directions] | 12:30 p.m. | W 67-58 | |
| Mon., 2/21 | JV Boys Basketball | Fitch | Home - Stamford HS-Kuczo Gymnasium [Directions] | 11:00 a.m. | ||
| Tue., 2/22 | V Boys Ice Hockey | Hall | Away - Veterans Memorial Ice Rink - West Hartford-Ice Rink [Directions] | 10:00 a.m. | W 4-1 | |
| Tue., 2/22 | V Girls Basketball | St. Joseph | Away - Trumbull HS-THS Main Gym [Directions] | 6:00 p.m. | ||
| Tue., 2/22 | V Girls Basketball | Fairfield Ludlowe | Away - Trumbull HS-Gym [Directions] | 7:30 p.m. | ||
| Wed., 2/23 | V Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 7:00 p.m. | L 53-66 | |
| Wed., 2/23 | JV Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 2/23 | FR Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:15 p.m. | ||
| Wed., 2/23 | V Boys Ice Hockey | Watertown-Pomperaug | Away - Taft School-Mays [Directions] | 7:30 p.m. | L 1-2 | |
| Wed., 2/23 | V Boys Swimming and Diving | Greenwich | Away - Greenwich HS-Pool [Directions] | 4:30 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 Girls Basketball | St. Joseph | Away - Trumbull HS-Gym [Directions] | 7:00 p.m. | ||
| Thu., 2/24 | Unified Sports Basketball | Westhill | Away - Westhill HS-New Gym [Directions] | 3:00 p.m. | ||
| Fri., 2/25 | V Boys Ice Hockey | Lyman Hall | Away - Northford Ice Pavilion-Red [Directions] | 8:00 p.m. | L 0-5 | |
| Sat., 2/26 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland of Ice-Stadium [Directions] | 6:30 p.m. | ||
| Sat., 2/26 | V Wrestling | State Open - Day 1 | Away - Floyd Little Athletic Center | 12:45 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 Girls Basketball | Fairfield Warde | Home - Stamford HS-Kuczo Gymnasium [Directions] | 6:30 p.m. | ||
| Tue., 3/1 | V Boys Ice Hockey | East Haven Coop | Away - Northford Ice Pavilion-White [Directions] | 8:45 p.m. | W 5-1 | |
| 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 Swimming and Diving | FCIAC Boys' Swim Finals | Away - Greenwich HS | 6:30 p.m. | ||
| Thu., 3/3 | V Girls Basketball | Middletown | Away - Middletown HS-Main Gym [Directions] | 6:00 p.m. | ||
| Thu., 3/3 | V Girls Ice Hockey | East Catholic Coop | Home - Terry Conners - Stamford-Ice Rink [Directions] | 7:30 p.m. | ||
| Sat., 3/5 | V Girls Gymnastics | State Open | Away - New Milford | 10:00 a.m. | ||
| Mon., 3/7 | V Boys Basketball | Stratford | Away - Stratford HS-Gym [Directions] | 6:30 p.m. | W 65-62 | |
| Mon., 3/7 | V Boys Ice Hockey | Daniel Hand | Away - Northford Ice Pavilion-Red [Directions] | 8:30 p.m. | ||
| Wed., 3/9 | Unified Sports Basketball | Fairfield Ludelowe Tournament | Away - Not Listed-Fairfield Ludlowe HS | 3:30 p.m. | ||
| Thu., 3/10 | V Boys Basketball | Crosby | Away - Crosby HS-CHS - Augelli Court [Directions] | 6:30 p.m. | ||
| Thu., 3/10 | Unified Sports Basketball | Greenwich | Home - Stamford HS-SHS Aux Gym [Directions] | 3:45 p.m. | ||
| Sun., 3/13 | V Boys Swimming and Diving | CIAC Class LL Qualifying Meet | Away - Cornerstone Pool | 5:30 p.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 Swimming and Diving | CIAC State Open Swimming Championships | Away - Cornerstone Pool | 3:15 p.m. | ||
| Wed., 3/23 | V Softball | Foran (Scrim.) | Home - Stamford HS-SHS Softball Diamond [Directions] | 4:00 p.m. | ||
| Fri., 3/25 | V Baseball | Greenwich (Scrim.) | Away - Julian Curtiss School [Directions] | 4:15 p.m. | ||
| Fri., 3/25 | V Boys Lacrosse | Fairfield Warde (Scrim.) | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | ||
| Sat., 3/26 | V Baseball | New Canaan (Scrim.) | Home - Stamford HS-SHS Baseball Diamond [Directions] | 11:00 a.m. | ||
| Sat., 3/26 | V Softball | Westhill (Scrim.) | Home - Darien HS-DHS - Softball - JV Field [Directions] | 10:00 a.m. | ||
| Sat., 3/26 | V Softball | Darien (Scrim.) | Away - Darien HS-DHS Softball - Varsity Field [Directions] | 10:00 a.m. | ||
| Sat., 3/26 | V Softball | Darien (Scrim.) | Away - Darien HS-DHS Softball - Varsity Field [Directions] | 2:00 p.m. | ||
| Sat., 3/26 | V Softball | Greenwich (Scrim.) | Away - Darien HS-DHS - Softball - JV Field [Directions] | 3:30 p.m. | ||
| Mon., 3/28 | JV Softball | Shelton | Away - Shelton HS-Upper Field [Directions] | Canceled | Cancelled | |
| Tue., 3/29 | V Baseball | Wright Tech (Scrim.) | Home - Stamford HS-SHS Baseball Diamond [Directions] | 3:45 p.m. | ||
| Tue., 3/29 | V Boys Lacrosse | Jonathan Law (Scrim.) | Home - Stamford HS-Upper Lacrosse Field [Directions] | 4:00 p.m. | ||
| Tue., 3/29 | V Girls Lacrosse | Norwalk (Scrim.) | Home - Stamford HS-Boyle Stadium [Directions] | 4:30 p.m. | ||
| Tue., 3/29 | V Softball | Shelton (Scrim.) | Away - Shelton HS-Softball Diamond [Directions] | 4:15 p.m. | Cancelled | |
| Wed., 3/30 | JV Baseball | Norwalk (Scrim.) | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 4:00 p.m. | ||
| Wed., 3/30 | FR Baseball | Norwalk (Scrim.) | Away - City Hall Field [Directions] | 4:00 p.m. | ||
| Wed., 3/30 | V Softball | Newtown (Scrim.) | Home - Stamford HS-SHS Softball Diamond [Directions] | 4:00 p.m. | ||
| Thu., 3/31 | V Baseball | Brien McMahon (Scrim.) | Away - Brien McMahon HS-Pride Field [Directions] | 4:00 p.m. | ||
| Thu., 3/31 | V Girls Lacrosse | St. Lukes (Scrim.) | Home - Stamford HS-Boyle Stadium [Directions] | 4:15 p.m. | ||
| Thu., 3/31 | JV Girls Lacrosse | St. Lukes (Scrim.) | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Sat., 4/2 | V Baseball | North Haven | Away - North Haven Athletic Complex-Robert E. DeMayo Field [Directions] | 2:00 p.m. | L 11-1 | |
| Sat., 4/2 | V Boys Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 11:30 a.m. | L 0-3 [Detailed Results] | |
| Sat., 4/2 | JV Boys Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 10:00 a.m. | W 2-0 | |
| Sat., 4/2 | V Girls Lacrosse | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 2:00 p.m. | L 4-18 | |
| Sat., 4/2 | JV Girls Lacrosse | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | 3:30 p.m. | ||
| Sat., 4/2 | JV Softball | Glastonbury | Away - Glastonbury HS-Field 9 [Directions] | Canceled | Cancelled | |
| Sat., 4/2 | Miscellaneous Events | B. Lax trip to Fairfield U. vs Drexel | Home - TBA [Directions] | 1:00 p.m. | ||
| Mon., 4/4 | V Baseball | New Milford | Home - Stamford HS-SHS Baseball Diamond [Directions] | 4:00 p.m. | W 9-7 | |
| Mon., 4/4 | JV Baseball | New Milford | Home - Belltown Park-Barrett Field, Belltown Park [Directions] | 4:00 p.m. | W 5-4 | |
| Mon., 4/4 | V Boys Outdoor Track | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | ||
| Mon., 4/4 | V Girls Lacrosse | Staples | Home - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | L 7-18 | |
| Mon., 4/4 | JV Girls Lacrosse | Staples | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Mon., 4/4 | V Girls Outdoor Track | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | ||
| Tue., 4/5 | V Boys Lacrosse | Staples | Away - Staples HS-Staples Stadium [Directions] | 5:30 p.m. | L 0-22 | |
| Tue., 4/5 | JV Boys Lacrosse | Staples | Away - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Tue., 4/5 | V Softball | New Fairfield | Away - New Fairfield HS-Softball Field [Directions] | 4:15 p.m. | W 13-3 | |
| Wed., 4/6 | FR Boys Lacrosse | Fairfield Ludlowe | Home - Stamford HS-Boyle Stadium [Directions] | 6:00 p.m. | ||
| Wed., 4/6 | V Boys Volleyball | Danbury | Home - Stamford HS-Kuczo Gymnasium [Directions] | 6:00 p.m. | L 0-3 [Detailed Results] | |
| Wed., 4/6 | JV Boys Volleyball | Danbury | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | W 2-1 | |
| Fri., 4/8 | V Baseball | Harding | Away - Warren Harding HS-Baseball Field [Directions] | 5:15 p.m. | W 16-0 | |
| Fri., 4/8 | JV Baseball | Darien | Away - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | W 6-4 | |
| Fri., 4/8 | V Boys Lacrosse | Brookfield | Away - Brookfield HS-BHS Stadium Field [Directions] | 6:00 p.m. | L 4-12 | |
| Fri., 4/8 | JV Boys Lacrosse | Brookfield | Away - Brookfield HS-BHS Stadium Field [Directions] | 4:00 p.m. | ||
| Fri., 4/8 | FR Boys Lacrosse | Trumbull | Home - Stamford HS-Upper Lacrosse Field [Directions] | Postponed | ||
| Fri., 4/8 | V Boys Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:30 p.m. | L 0-3 [Detailed Results] | |
| Fri., 4/8 | JV Boys Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 6:00 p.m. | L 0-2 [Detailed Results] | |
| Fri., 4/8 | V Softball | New Canaan | Away - Waveny Park-Orchard Field [Directions] | 5:00 p.m. | L 8-10 | |
| Sat., 4/9 | V Baseball | Kolbe Cathedral | Home - Stamford HS-SHS Baseball Diamond [Directions] | 12:00 p.m. | W 13-0 | |
| Sat., 4/9 | FR Baseball | Greenwich (Scrim.) | Away - Julian Curtiss School [Directions] | 2:30 p.m. | ||
| Sat., 4/9 | V Girls Lacrosse | Weston | Away - Weston HS-WHS Lower Turf Field [Directions] | 12:00 p.m. | L 6-13 | |
| Sat., 4/9 | JV Girls Lacrosse | Weston | Away - Weston HS-WHS Lower Turf Field [Directions] | 10:15 a.m. | ||
| Sat., 4/9 | V Softball | Joel Barlow | Home - Stamford HS-SHS Softball Diamond [Directions] | 12:00 p.m. | W 9-0 | |
| Mon., 4/11 | V Boys Outdoor Track | Wilton | Away - Wilton HS-Veterans Memorial Stadium [Directions] | 4:00 p.m. | ||
| Mon., 4/11 | V Boys Tennis | St. Joseph | Home - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | W 4-3 [Detailed Results] | |
| Mon., 4/11 | V Boys Volleyball | Kolbe Cathedral | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | L 0-3 [Detailed Results] | |
| Mon., 4/11 | JV Boys Volleyball | Kolbe Cathedral | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:45 p.m. | L 0-2 | |
| Mon., 4/11 | V Girls Lacrosse | Lauralton Hall | Home - Stamford HS-Boyle Stadium [Directions] | 4:30 p.m. | W 11-8 | |
| Mon., 4/11 | JV Girls Lacrosse | Lauralton Hall | Home - Stamford HS-Boyle Stadium [Directions] | Postponed | ||
| Mon., 4/11 | V Girls Outdoor Track | Wilton | Away - Wilton HS-Veterans Memorial Stadium [Directions] | 4:00 p.m. | ||
| Mon., 4/11 | V Girls Tennis | St. Joseph | Away - St. Joseph HS-Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Tue., 4/12 | V Boys Lacrosse | Wilton | Away - Wilton HS-Veterans Memorial Stadium [Directions] | 6:30 p.m. | L 0-15 | |
| Tue., 4/12 | JV Boys Lacrosse | Wilton | Away - Wilton HS-Veterans Memorial Stadium [Directions] | 4:30 p.m. | ||
| Tue., 4/12 | V Boys Tennis | Brien McMahon | Away - Brien McMahon HS-Tennis Courts [Directions] | 4:00 p.m. | L 1-6 [Detailed Results] | |
| Tue., 4/12 | V Softball | Darien | Away - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | L 4-5 | |
| Tue., 4/12 | V Girls Tennis | Brien McMahon | Home - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | W 6-0 | |
| Wed., 4/13 | V Baseball | St. Joseph | Away - St. Joseph HS-Baseball Diamond [Directions] | 4:00 p.m. | L 6-5 | |
| Wed., 4/13 | JV Baseball | St. Joseph | Away - Unity Park-Field 1 [Directions] | 4:00 p.m. | L 10-0 | |
| Wed., 4/13 | FR Baseball | St. Joseph | Home - Stamford HS-SHS Baseball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 4/13 | FR Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Fairfield Warde Grass Utility Field [Directions] | 4:00 p.m. | ||
| Wed., 4/13 | V Boys Volleyball | Rockville | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:00 p.m. | L 0-3 [Detailed Results] | |
| Wed., 4/13 | JV Boys Volleyball | Rockville | Home - Stamford HS-Kuczo Gymnasium [Directions] | 6:00 p.m. | L 0-2 [Detailed Results] | |
| Wed., 4/13 | V Softball | St. Joseph | Home - Stamford HS-SHS Softball Diamond [Directions] | 4:00 p.m. | L 0-14 | |
| Thu., 4/14 | V Boys Lacrosse | Brien McMahon | Home - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | L 0-16 | |
| Thu., 4/14 | JV Boys Lacrosse | Brien McMahon | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Sat., 4/16 | V Baseball | Weston | Away - Weston HS-Revson #1 (Varsity) [Directions] | 12:00 p.m. | L 8-7 | |
| Sat., 4/16 | V Boys Lacrosse | Bunnell-Stratford | Home - Stamford HS-Upper Lacrosse Field [Directions] | 12:00 p.m. | L 4-5 | |
| Sat., 4/16 | JV Boys Lacrosse | Bunnell-Stratford | Home - Stamford HS-Upper Lacrosse Field [Directions] | 1:30 p.m. | ||
| Sat., 4/16 | V Boys Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 11:00 a.m. | L 0-3 [Detailed Results] | |
| Sat., 4/16 | JV Boys Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 12:30 p.m. | L 0-2 | |
| Sat., 4/16 | V Girls Lacrosse | New Milford | Home - Stamford HS-Boyle Stadium [Directions] | 12:00 p.m. | W 22-7 | |
| Sat., 4/16 | JV Girls Lacrosse | New Milford | Home - Stamford HS-Boyle Stadium [Directions] | 1:30 p.m. | ||
| Sat., 4/16 | V Softball | Glastonbury | Away - Glastonbury HS-Field 10 [Directions] | 11:00 a.m. | L 1-15 | |
| Sat., 4/16 | JV Softball | St. Joseph | Home - Stamford HS-SHS Softball Diamond [Directions] | Postponed | ||
| Mon., 4/18 | V Baseball | Brien McMahon | Home - Stamford HS-SHS Baseball Diamond [Directions] | 4:00 p.m. | W 7-6 | |
| Mon., 4/18 | JV Baseball | Brien McMahon | Home - Belltown Park-Barrett Field, Belltown Park [Directions] | 4:00 p.m. | W 9-1 | |
| Mon., 4/18 | FR Boys Lacrosse | Ridgefield | Away - Ridgefield HS-RHS Lower Grass Field [Directions] | 4:00 p.m. | ||
| Mon., 4/18 | V Boys Tennis | Fairfield Warde | Home - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Mon., 4/18 | V Boys Volleyball | Fairfield Warde | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | L 0-3 [Detailed Results] | |
| Mon., 4/18 | JV Boys Volleyball | Fairfield Warde | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | L 0-2 | |
| Mon., 4/18 | V Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 5:00 p.m. | W 15-8 | |
| Mon., 4/18 | JV Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | Canceled | Cancelled | |
| Mon., 4/18 | V Softball | Brien McMahon | Away - Norwalk HS - Ray Barry Field-Softball Field [Directions] | 3:45 p.m. | L 6-7 | |
| Mon., 4/18 | JV Softball | Brien McMahon | Away - Norwalk HS - Ray Barry Field-Softball Field [Directions] | Canceled | Cancelled | |
| Mon., 4/18 | V Girls Tennis | Fairfield Warde | Away - Fairfield Warde HS-Blake Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Tue., 4/19 | V Boys Tennis | Wilton | Away - Wilton HS-Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Tue., 4/19 | V Girls Tennis | Wilton | Home - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Wed., 4/20 | V Baseball | Danbury | Home - Stamford HS-Cubeta Stadium [Directions] | 7:00 p.m. | L 2-3 | |
| Wed., 4/20 | JV Baseball | Danbury | Home - Stamford HS-SHS Baseball Diamond [Directions] | 4:00 p.m. | L 7-6 | |
| Wed., 4/20 | FR Baseball | Danbury | Away - Danbury HS-V Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 4/20 | FR Boys Lacrosse | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:15 p.m. | ||
| Wed., 4/20 | V Boys Volleyball | Norwalk | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | L 0-3 [Detailed Results] | |
| Wed., 4/20 | JV Boys Volleyball | Norwalk | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | W 2-0 | |
| Wed., 4/20 | V Girls Lacrosse | Newtown (Scrim.) | Away - Treadwell Park-Newtown Treadwell Park [Directions] | 4:30 p.m. | Cancelled | |
| Wed., 4/20 | V Softball | Danbury | Away - Danbury HS-V Softball field [Directions] | 4:00 p.m. | L 1-7 | |
| Wed., 4/20 | JV Softball | Danbury | Away - Danbury HS-JV Softball Field [Directions] | 5:30 p.m. | ||
| Thu., 4/21 | V Boys Lacrosse | New Canaan | Home - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | L 3-18 | |
| Thu., 4/21 | JV Boys Lacrosse | New Canaan | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Thu., 4/21 | V Boys Outdoor Track | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 4:00 p.m. | ||
| Thu., 4/21 | V Boys Tennis | New Canaan | Home - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | L 3-4 [Detailed Results] | |
| Thu., 4/21 | V Girls Outdoor Track | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 4:00 p.m. | ||
| Thu., 4/21 | V Girls Tennis | New Canaan | Away - New Canaan HS-NCHS Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Fri., 4/22 | V Baseball | Fairfield Warde | Away - Kiwanis Field-Baseball Diamond [Directions] | 4:00 p.m. | L 12-3 | |
| Fri., 4/22 | JV Baseball | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 4:30 p.m. | L 9-3 | |
| Fri., 4/22 | FR Baseball | Fairfield Warde | Home - Stamford HS-SHS Baseball Diamond [Directions] | 4:00 p.m. | ||
| Fri., 4/22 | FR Boys Lacrosse | Staples | Away - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Fri., 4/22 | V Boys Tennis | Danbury | Away - Danbury HS-DHS Tennis Courts [Directions] | 4:00 p.m. | L 3-4 | |
| Fri., 4/22 | V Boys Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | L 0-3 [Detailed Results] | |
| Fri., 4/22 | JV Boys Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | L 0-2 | |
| Fri., 4/22 | JV Girls Lacrosse | Westhill | Away - Westhill HS-Westhill Front Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 4/22 | V Softball | Fairfield Warde | Home - Stamford HS-SHS Softball Diamond [Directions] | 4:00 p.m. | L 4-16 | |
| Fri., 4/22 | JV Softball | Fairfield Warde | Home - Stamford HS-SHS Softball Diamond [Directions] | 5:30 p.m. | ||
| Fri., 4/22 | V Girls Tennis | Danbury | Home - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | W 7-1 | |
| Sat., 4/23 | V Boys Lacrosse | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 12:00 p.m. | L 4-14 | |
| Sat., 4/23 | JV Boys Lacrosse | Watertown | Away - Watertown High-John J Mills Complex @ Watertown HS [Directions] | 1:30 p.m. | ||
| Sat., 4/23 | V Girls Lacrosse | Rockville | Away - Rockville HS-Stadium Field [Directions] | 11:00 a.m. | W 17-6 | |
| Sat., 4/23 | JV Girls Lacrosse | Rockville | Away - Rockville HS-Stadium Field [Directions] | Canceled | Cancelled | |
| Mon., 4/25 | V Baseball | Wilton | Home - Cubeta Stadium [Directions] | 7:00 p.m. | L 8-5 | |
| Mon., 4/25 | JV Baseball | Wilton | Home - Stamford HS-SHS Baseball Diamond [Directions] | 4:00 p.m. | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 4:30 p.m. | ||||||
| Mon., 4/25 | FR Baseball | Wilton | Away - Allen's Meadow-Baseball Diamond [Directions] | Canceled | Cancelled | |
| Mon., 4/25 | FR Boys Lacrosse | Greenwich | Home - Stamford HS-Upper Lacrosse Field [Directions] | 5:00 p.m. | ||
| Mon., 4/25 | V Boys Tennis | Ridgefield | Away - Ridgefield HS-RHS Tennis Courts [Directions] | 4:00 p.m. | L 1-6 [Detailed Results] | |
| Mon., 4/25 | V Boys Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Mon., 4/25 | JV Boys Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | L 0-2 | |
| Mon., 4/25 | V Softball | Wilton | Away - Wilton HS-Varsity Softball Field [Directions] | 4:30 p.m. | W 7-2 | |
| Mon., 4/25 | JV Softball | Wilton | Away - Wilton HS-JV Softball Field [Directions] | Postponed | ||
| Mon., 4/25 | V Girls Tennis | Ridgefield | Home - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | L 1-6 | |
| Tue., 4/26 | V Boys Lacrosse | Greenwich | Home - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | L 1-18 | |
| Tue., 4/26 | JV Boys Lacrosse | Greenwich | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Tue., 4/26 | V Boys Outdoor Track | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Tue., 4/26 | V Girls Lacrosse | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:30 p.m. | L 15-4 | |
| Tue., 4/26 | JV Girls Lacrosse | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Tue., 4/26 | V Girls Outdoor Track | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | ||
| Wed., 4/27 | V Baseball | New Canaan | Away - Mead Park-Baseball Field [Directions] | 4:00 p.m. | W 8-5 | |
| Wed., 4/27 | JV Baseball | New Canaan | Away - Waveny Park-Coppo Field [Directions] | 4:00 p.m. | L 6-4 | |
| Wed., 4/27 | FR Baseball | New Canaan | Home - Stamford HS-SHS Baseball Diamond [Directions] | 4:00 p.m. | ||
| Wed., 4/27 | FR Boys Lacrosse | Fairfield Warde | Home - Stamford HS-Upper Lacrosse Field [Directions] | 5:00 p.m. | ||
| Wed., 4/27 | V Boys Tennis | Trumbull | Away - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | L 1-6 [Detailed Results] | |
| Wed., 4/27 | V Boys Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 4:00 p.m. | L 0-3 [Detailed Results] | |
| Wed., 4/27 | JV Boys Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 5:30 p.m. | W 2-1 | |
| Wed., 4/27 | V Softball | New Canaan | Home - Stamford HS-SHS Baseball Diamond [Directions] | 4:00 p.m. | W 4-2 | |
| Wed., 4/27 | JV Softball | New Canaan | Home - Stamford HS-SHS Softball Diamond [Directions] | 5:30 p.m. | ||
| Wed., 4/27 | V Girls Tennis | Trumbull | Home - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Thu., 4/28 | V Boys Lacrosse | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 4:30 p.m. | W 10-6 | |
| Thu., 4/28 | JV Boys Lacrosse | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | Canceled | Cancelled | |
| Thu., 4/28 | V Boys Tennis | Fairfield Ludlowe | Home - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | L 1-6 [Detailed Results] | |
| Thu., 4/28 | V Girls Lacrosse | Danbury | Home - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | W 18-7 | |
| Thu., 4/28 | JV Girls Lacrosse | Danbury | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Thu., 4/28 | V Girls Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Fri., 4/29 | V Baseball | Ridgefield | Home - Stamford HS-SHS Baseball Diamond [Directions] | 4:30 p.m. | L 11-6 | |
| Fri., 4/29 | JV Baseball | Ridgefield | Home - Belltown Park-Barrett Field, Belltown Park [Directions] | 4:30 p.m. | L 10-2 | |
| Fri., 4/29 | FR Baseball | Ridgefield | Away - Governor Field [Directions] | 4:30 p.m. | ||
| Fri., 4/29 | FR Boys Lacrosse | Wilton | Home - Stamford HS-Upper Lacrosse Field [Directions] | 5:00 p.m. | ||
| Fri., 4/29 | V Boys Volleyball | Westhill | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | L 0-3 [Detailed Results] | |
| Fri., 4/29 | JV Boys Volleyball | Westhill | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | L 0-2 | |
| Fri., 4/29 | V Softball | Ridgefield | Away - Ridgefield HS-Varsity Field [Directions] | 4:00 p.m. | W 11-5 | |
| Fri., 4/29 | JV Softball | Ridgefield | Away - Ridgefield HS-JV Field [Directions] | 5:30 p.m. | ||
| Sat., 4/30 | V Boys Lacrosse | Immaculate | Home - Stamford HS-Upper Lacrosse Field [Directions] | 1:30 p.m. | W 13-1 | |
| Sat., 4/30 | V Girls Lacrosse | Immaculate | Home - Stamford HS-Boyle Stadium [Directions] | 12:00 p.m. | W 20-5 | |
| Mon., 5/2 | V Boys Lacrosse | Norwalk | Home - Stamford HS-Boyle Stadium [Directions] | 7:00 p.m. | L 8-11 | |
| Mon., 5/2 | JV Boys Lacrosse | Norwalk | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Mon., 5/2 | V Boys Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | L 0-3 [Detailed Results] | |
| Mon., 5/2 | JV Boys Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 6:00 p.m. | W 2-1 [Detailed Results] | |
| Tue., 5/3 | V Baseball | Trumbull | Home - Stamford HS-SHS Baseball Diamond [Directions] | 4:30 p.m. | L 6-1 | |
| Tue., 5/3 | JV Baseball | Trumbull | Home - Belltown Park-Barrett Field, Belltown Park [Directions] | 4:30 p.m. | L 15-9 | |
| Tue., 5/3 | FR Baseball | Trumbull | Away - Trumbull HS-Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Tue., 5/3 | V Boys Lacrosse | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 4:00 p.m. | L 0-18 | |
| Tue., 5/3 | JV Boys Lacrosse | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 5:30 p.m. | ||
| Tue., 5/3 | FR Boys Lacrosse | Darien | Home - Stamford HS-Boyle Stadium [Directions] | 4:30 p.m. | ||
| Tue., 5/3 | V Boys Outdoor Track | New Canaan | Away - New Canaan HS-NCHS Track [Directions] | 4:00 p.m. | ||
| Tue., 5/3 | V Boys Tennis | Westhill | Home - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | L 1-6 [Detailed Results] | |
| Tue., 5/3 | V Girls Lacrosse | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 6:00 p.m. | W 12-11 | |
| Tue., 5/3 | JV Girls Lacrosse | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 4:30 p.m. | ||
| Tue., 5/3 | V Girls Outdoor Track | New Canaan | Away - New Canaan HS-NCHS Track [Directions] | 4:00 p.m. | ||
| Tue., 5/3 | V Softball | Trumbull | Away - Trumbull HS-Varsity Softball Diamond [Directions] | 4:15 p.m. | L 7-4 | |
| Tue., 5/3 | JV Softball | Trumbull | Away - Trumbull HS-JV Softball Diamond [Directions] | 6:15 p.m. | ||
| Tue., 5/3 | V Girls Tennis | Westhill | Away - Westhill HS-Westhill Tennis Courts [Directions] | 4:00 p.m. | L 1-6 | |
| Wed., 5/4 | FR Boys Lacrosse | Westhill | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Wed., 5/4 | V Boys Volleyball | Staples | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | L 0-3 [Detailed Results] | |
| Wed., 5/4 | JV Boys Volleyball | Staples | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | L 0-2 | |
| Wed., 5/4 | JV Softball | Fairfield Ludlowe | Home - Stamford HS-SHS Softball Diamond [Directions] | 5:30 p.m. | ||
| Thu., 5/5 | V Baseball | Fairfield Ludlowe | Away - Kiwanis Field-Baseball Diamond [Directions] | 4:30 p.m. | W 3-0 | |
| Thu., 5/5 | JV Baseball | Fairfield Ludlowe | Away - Owen Fish Park-Owen Fish [Directions] | 4:30 p.m. | L 2-1 | |
| Thu., 5/5 | FR Baseball | Fairfield Ludlowe | Home - Stamford HS-SHS Baseball Diamond [Directions] | Postponed | ||
| Thu., 5/5 | V Boys Tennis | Norwalk | Away - Norwalk HS-Tennis Courts [Directions] | 4:00 p.m. | W 4-3 | |
| Thu., 5/5 | V Boys Volleyball | Darien | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | L 0-3 [Detailed Results] | |
| Thu., 5/5 | JV Boys Volleyball | Darien | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | L 0-2 [Detailed Results] | |
| Thu., 5/5 | V Girls Lacrosse | Darien | Home - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | L 2-19 | |
| Thu., 5/5 | JV Girls Lacrosse | Darien | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Thu., 5/5 | V Softball | Fairfield Ludlowe | Home - Stamford HS-SHS Softball Diamond [Directions] | 4:30 p.m. | L 10-6 | |
| Thu., 5/5 | JV Softball | Fairfield Ludlowe | Home - Stamford HS-SHS Softball Diamond [Directions] | Postponed | ||
| Thu., 5/5 | V Girls Tennis | Norwalk | Home - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Fri., 5/6 | FR Boys Lacrosse | Ridgefield | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Sat., 5/7 | V Boys Lacrosse | St. Joseph | Home - Stamford HS-Boyle Stadium [Directions] | 3:00 p.m. | L 23-1 | |
| Sat., 5/7 | JV Boys Lacrosse | St. Joseph | Home - Stamford HS-Boyle Stadium [Directions] | 4:30 p.m. | ||
| Sat., 5/7 | V Girls Lacrosse | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 3:00 p.m. | L 12-13 | |
| Sat., 5/7 | JV Girls Lacrosse | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 4:30 p.m. | ||
| Mon., 5/9 | V Baseball | Westhill | Away - Cubeta Stadium [Directions] | 7:00 p.m. | L 3-1 | |
| Mon., 5/9 | JV Baseball | Westhill | Away - Westhill HS-Varsity Baseball Field [Directions] | 4:00 p.m. | L 9-1 | |
| Mon., 5/9 | FR Baseball | Westhill | Home - Stamford HS-SHS Baseball Diamond [Directions] | 4:00 p.m. | ||
| Mon., 5/9 | V Boys Lacrosse | Sheehan | Away - Sheehan HS-Sheehan HS Riccitelli Field (Turf) [Directions] | 4:30 p.m. | L 3-15 | |
| Mon., 5/9 | JV Boys Lacrosse | Sheehan | Away - Sheehan HS-Sheehan HS Riccitelli Field (Turf) [Directions] | 6:00 p.m. | ||
| Mon., 5/9 | V Boys Outdoor Track | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | ||
| Mon., 5/9 | V Boys Tennis | Darien | Home - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | L 7-0 [Detailed Results] | |
| Mon., 5/9 | V Boys Volleyball | Bridgeport Central | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | L 2-3 [Detailed Results] | |
| Mon., 5/9 | JV Boys Volleyball | Bridgeport Central | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | L 1-2 | |
| Mon., 5/9 | V Girls Outdoor Track | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | ||
| Mon., 5/9 | JV Softball | Westhill | Home - Stamford HS-SHS Softball Diamond [Directions] | 3:30 p.m. | ||
| Mon., 5/9 | V Girls Tennis | Darien | Away - Darien HS-DHS Tennis Courts [Directions] | 4:00 p.m. | L 0-7 | |
| Tue., 5/10 | V Boys Tennis | Bridgeport Central | Away - Bridgeport Central HS-Central High School Tennis Courts [Directions] | 4:30 p.m. | W 5-2 | |
| Tue., 5/10 | V Boys Volleyball | St. Joseph | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | L 0-3 | |
| Tue., 5/10 | JV Boys Volleyball | St. Joseph | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | L 1-2 | |
| Tue., 5/10 | V Girls Lacrosse | Wilton | Home - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | L 1-17 | |
| Tue., 5/10 | JV Girls Lacrosse | Wilton | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Tue., 5/10 | V Girls Tennis | Bridgeport Central | Home - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Wed., 5/11 | V Baseball | Norwalk | Home - Stamford HS-Cubeta Stadium [Directions] | 7:00 p.m. | L 10-4 | |
| Wed., 5/11 | JV Baseball | Norwalk | Home - Stamford HS-SHS Baseball Diamond [Directions] | 4:00 p.m. | L 12-2 | |
| Wed., 5/11 | FR Baseball | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 4:00 p.m. | ||
| Wed., 5/11 | V Boys Tennis | Staples | Home - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | L 7-0 | |
| Wed., 5/11 | V Boys Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:30 p.m. | L 0-3 [Detailed Results] | |
| Wed., 5/11 | JV Boys Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 7:00 p.m. | L 0-2 | |
| Wed., 5/11 | V Softball | Norwalk | Away - Norwalk HS-Ray Barry Field [Directions] | 4:30 p.m. | W 10-8 | |
| Wed., 5/11 | JV Softball | Norwalk | Away - Norwalk HS-Ray Barry Field [Directions] | 6:00 p.m. | ||
| Wed., 5/11 | V Girls Tennis | Staples | Away - Staples HS-Staples Tennis Courts [Directions] | 4:30 p.m. | L 0-7 | |
| Thu., 5/12 | V Baseball | Darien | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 4:00 p.m. | L 9-3 | |
| Thu., 5/12 | JV Baseball | Darien | Away - Darien HS-DHS Baseball - JV Field [Directions] | 3:30 p.m. | W 12-6 | |
| Thu., 5/12 | FR Baseball | Darien | Home - Stamford HS-SHS Baseball Diamond [Directions] | 4:00 p.m. | ||
| Thu., 5/12 | V Boys Lacrosse | Trumbull | Home - Stamford HS-Boyle Stadium [Directions] | 7:00 p.m. | L 1-11 | |
| Thu., 5/12 | JV Boys Lacrosse | Trumbull | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Thu., 5/12 | V Boys Tennis | Greenwich | Home - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | L 1-6 | |
| Thu., 5/12 | V Girls Lacrosse | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 6:00 p.m. | W 14-7 | |
| Thu., 5/12 | JV Girls Lacrosse | Trumbull | Away - Trumbull HS-Cork Field [Directions] | 4:00 p.m. | ||
| Thu., 5/12 | V Softball | Darien | Home - Stamford HS-SHS Softball Diamond [Directions] | 4:00 p.m. | W 5-4 | |
| Thu., 5/12 | V Girls Tennis | Greenwich | Away - Greenwich HS-Tennis Courts [Directions] | 4:30 p.m. | L 0-7 | |
| Sat., 5/14 | V Boys Lacrosse | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | L 5-6 | |
| Sat., 5/14 | JV Boys Lacrosse | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 1:45 p.m. | ||
| Sat., 5/14 | V Softball | Westhill | Home - Troy Complex [Directions] | 6:30 p.m. | W 14-2 | |
| Tue., 5/17 | V Baseball | Staples | Away - Staples HS-Baseball Diamond [Directions] | 4:30 p.m. | L 16-3 | |
| Tue., 5/17 | JV Baseball | Staples | Away - Staples HS-Wakeman Field [Directions] | 4:30 p.m. | L 8-2 | |
| Tue., 5/17 | FR Baseball | Staples | Home - Stamford HS-SHS Baseball Diamond [Directions] | 4:00 p.m. | ||
| Tue., 5/17 | JV Boys Lacrosse | Weston | Away - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 5/17 | FR Boys Lacrosse | New Canaan | Home - Stamford HS-Boyle Stadium [Directions] | Canceled | Cancelled | |
| Tue., 5/17 | V Girls Lacrosse | Westhill | Home - Stamford HS-Boyle Stadium [Directions] | 7:00 p.m. | W 12-9 | |
| Tue., 5/17 | JV Girls Lacrosse | Westhill | Home - Stamford HS-Boyle Stadium [Directions] | 5:00 p.m. | ||
| Tue., 5/17 | V Softball | Staples | Home - Stamford HS-SHS Softball Diamond [Directions] | 4:00 p.m. | W 11-6 | |
| Tue., 5/17 | V Softball | Bridgeport Central | Home - Troy Complex-Diamond 1 [Directions] | 6:45 p.m. | W 19-0 | |
| Tue., 5/17 | JV Softball | Staples | Home - Stamford HS-SHS Softball Diamond [Directions] | Canceled | Cancelled | |
| Wed., 5/18 | V Baseball | Greenwich | Away - Greenwich HS-Baseball Field [Directions] | 4:30 p.m. | L 11-1 | |
| Wed., 5/18 | JV Baseball | Greenwich | Away - Julian Curtiss School [Directions] | 4:30 p.m. | W 14-4 | |
| Wed., 5/18 | FR Baseball | Greenwich | Home - Stamford HS-SHS Baseball Diamond [Directions] | 4:30 p.m. | ||
| Wed., 5/18 | FR Boys Lacrosse | Fairfield Ludlowe | Home - Stamford HS-Boyle Stadium [Directions] | 6:30 p.m. | ||
| Wed., 5/18 | V Boys Outdoor Track | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 2:45 p.m. | Field events only | |
| Wed., 5/18 | V Boys Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Gym [Directions] | 6:30 p.m. | L 0-3 | |
| Wed., 5/18 | JV Boys Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Gym [Directions] | 4:30 p.m. | L 1-2 | |
| Wed., 5/18 | V Girls Outdoor Track | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 2:45 p.m. | Field events only | |
| Wed., 5/18 | V Softball | Greenwich | Home - Troy Complex-Diamond 1 [Directions] | 7:00 p.m. | W 7-1 | |
| Thu., 5/19 | JV Baseball | Bassick | Home - Belltown Park-Barrett Field, Belltown Park [Directions] | Canceled | Cancelled | |
| Thu., 5/19 | V Boys Outdoor Track | Westhill | Home - Stamford HS-Boyle Stadium [Directions] | 3:30 p.m. | ||
| Thu., 5/19 | V Boys Volleyball | Fairfield Ludlowe | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | L 0-3 | |
| Thu., 5/19 | JV Boys Volleyball | Fairfield Ludlowe | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 5/19 | V Girls Outdoor Track | Westhill | Home - Stamford HS-Boyle Stadium [Directions] | 3:30 p.m. | ||
| Thu., 5/19 | JV Softball | Greenwich | Home - Stamford HS-SHS Softball Diamond [Directions] | Canceled | Cancelled | |
| Sat., 5/21 | FR Baseball | Fairfield Ludlowe | Home - Stamford HS-SHS Baseball Diamond [Directions] | Canceled | Cancelled | |
| Sat., 5/21 | FR Boys Lacrosse | Trumbull | Away - Trumbull HS-The Pit [Directions] | Postponed | ||
| Sat., 5/21 | V Softball | St. Joseph | Away - St. Joseph HS-Softball Diamond [Directions] | 12:00 p.m. | ||
| Mon., 5/23 | V Baseball | Bridgeport Central | Home - Stamford HS-SHS Baseball Diamond [Directions] | 4:30 p.m. | W 13-1 | |
| 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 Boys Outdoor Track | FCIAC Championships | Away - Danbury HS-Stadium Track | 3:30 p.m. | ||
| Wed., 5/25 | V Softball | Darien (Scrim.) | Away - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | ||
| Thu., 5/26 | V Baseball | Norwalk (Scrim.) | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 4:30 p.m. | ||
| Fri., 5/27 | V Girls Lacrosse | Glastonbury | Away - Glastonbury HS-Field 1 [Directions] | 5:00 p.m. | ||
| Tue., 5/31 | V Baseball | Amity | Away - Amity Regional HS-John Janenda Field [Directions] | 3:45 p.m. | L 7-1 | |
| Tue., 5/31 | V Boys Outdoor Track | CIAC Class LL Championship | Away - Willow Brook Park | 4:00 p.m. | ||
| Tue., 5/31 | V Girls Outdoor Track | CIAC Class LL Championship | Away - Willow Brook Park | 4:00 p.m. | ||
| Tue., 5/31 | V Softball | Trumbull | Away - Trumbull HS-Varsity Softball Diamond [Directions] | 4:30 p.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 Tennis | CIAC Individual Invitational - Opening Round, Singles and Doubles | Away - Wesleyan | 10:00 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 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. | ||
| Wed., 6/8 | Miscellaneous Events | Meet the coaches Knight | Home - Stamford HS-Boyle Stadium [Directions] | 6:30 p.m. | A chance for incoming 9th graders and transfers to meet the coaches | |
| 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. | ||
| 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. | ||
| Sat., 6/25 | Baseball | Danbury | Away - Danbury HS-Baseball Diamond [Directions] | 11:00 a.m. | ||
| Sat., 6/25 | Baseball | Danbury | Away - Danbury HS-Baseball Diamond [Directions] | 1:30 p.m. | ||
| Sun., 6/26 | Baseball | Danbury | Away - Rogers Park (Westerners Field) [Directions] | 12:00 p.m. | ||