| Stamford 2023-24 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 792 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| Wed., 8/23 | V Football | Joint Practice at Westhill High School | Away - Not Listed-Westhill HS | 3:30 p.m. | 2:45 AM | |
| Tue., 8/29 | V Football | Joint practice/scrimmage at Bunnell | Away - Not Listed-Bunnell HS | 4:00 p.m. | 3:15 PM (2 buses - Pick up at Holcomb Ave lot) | |
| Tue., 8/29 | V Boys Golf | Fairfield Warde | Away - Smith Richardson Golf Course [Directions] | 3:00 p.m. | 1:30 PM | |
| Tue., 8/29 | V Boys Soccer | New Canaan (Scrim.) | Away - Saxe MS-Field 1 [Directions] | W 3-0 | 3:15 PM | |
| Tue., 8/29 | JV Boys Soccer | New Canaan (Scrim.) | Away - Saxe MS-Field 2 [Directions] | 4:30 p.m. | 3:15 PM | |
| Tue., 8/29 | V Field Hockey | Immaculate (Scrim.) | Away - Immaculate HS-Mustang Valley [Directions] | 4:00 p.m. | 2:00 PM | |
| Wed., 8/30 | V Boys Golf | Fairfield Ludlowe | Home - Stamford High-Sterling Farms Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 8/30 | V Girls Soccer | New Milford (Scrim.) | Home - Stamford HS-SHS Upper Soccer Field [Directions] | 6:00 p.m. | ||
| Thu., 8/31 | V Boys Soccer | Wilton (Scrim.) | Home - Stamford HS-SHS Upper Soccer Field [Directions] | W 2-1 | ||
| Thu., 8/31 | V Girls Volleyball | New Rochelle (NY) (Scrim.) | Home - Stamford HS-Kuczo Gymnasium [Directions] | 3:00 p.m. | ||
| Fri., 9/1 | V Football | Brien McMahon (Scrim.) | Away - Brien McMahon HS-Casagrande Field [Directions] | 5:30 p.m. | 3:15 PM (2 buses - pick up at Holcomb lot) | |
| Fri., 9/1 | FR Football | Brien McMahon (Scrim.) | Home - Stamford HS-Boyle Stadium [Directions] | 5:00 p.m. | ||
| Sat., 9/2 | V Field Hockey | Norwalk Play Day | Away - Not Listed-Norwalk HS | TBA | 8:30 AM | |
| Sat., 9/2 | V Girls Volleyball | Joel Barlow (Scrim.) | Home - Stamford HS-Kuczo Gymnasium [Directions] | 9:30 a.m. | ||
| Tue., 9/5 | V Boys Golf | Norwalk | Away - Oak Hills Golf Course [Directions] | 3:00 p.m. | 1:45 PM | |
| Tue., 9/5 | V Boys Soccer | Bethel (Scrim.) | Away - Bethel HS-MS Turf Soccer Field [Directions] | T 1-1 | 3:30 PM | |
| Tue., 9/5 | JV Boys Soccer | Bethel (Scrim.) | Away - Bethel HS-Rockwell Field [Directions] | 5:30 p.m. | 3:30 PM | |
| Tue., 9/5 | V Girls Volleyball | Westhill (Scrim.) | Home - Stamford HS-Kuczo Gymnasium [Directions] | 3:30 p.m. | ||
| Wed., 9/6 | V Field Hockey | Shelton (Scrim.) | Away - Shelton HS-Finn Stadium [Directions] | 5:30 p.m. | 2:45 PM | |
| Wed., 9/6 | JV Field Hockey | Shelton (Scrim.) | Away - Shelton HS-Finn Stadium [Directions] | 7:00 p.m. | 2:45 PM | |
| Wed., 9/6 | V Girls Volleyball | Greenwich (Scrim.) | Away - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | 3:00 PM | |
| Fri., 9/8 | V Football | Norwich Free Academy | Home - Stamford HS-Boyle Stadium [Directions] | W 42-27 | ||
| Fri., 9/8 | V Girls Swimming and Diving | Fairfield Ludlowe | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Fri., 9/8 | V Girls Volleyball | Norwalk | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 3-0 | ||
| Sat., 9/9 | V Boys Cross Country | Wilton Invitational | Away - Not Listed-Wilton HS | 9:00 a.m. | 8:00 AM | |
| Sat., 9/9 | JV Football | Brien McMahon | Home - Stamford HS-Boyle Stadium [Directions] | L 42-0 | ||
| Sat., 9/9 | FR Football | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | L 37-19 | 10:45 AM | |
| Sat., 9/9 | V Boys Soccer | East Hartford | Home - Farmington Sports Arena-Field 3 [Directions] | T 1-1 | 12:30 PM | |
| Sat., 9/9 | V Girls Cross Country | Wilton Invitational | Away - Not Listed-White Oak, PA | 9:00 a.m. | 8:00 AM | |
| Sat., 9/9 | V Girls Soccer | Harding | Away - Warren Harding HS-Lewis Field [Directions] | W 8-0 | 8:45 AM | |
| Sat., 9/9 | V Girls Volleyball | Brien McMahon | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 2-3 | ||
| Mon., 9/11 | V Boys Golf | St. Joseph | Home - Stamford High-Sterling Farms Golf Course [Directions] | 3:00 p.m. | ||
| Mon., 9/11 | V Field Hockey | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | L 0-3 | 3:30 PM | |
| Mon., 9/11 | JV Field Hockey | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 5:30 p.m. | 3:30 PM | |
| Mon., 9/11 | JV Girls Soccer | Brien McMahon | Home - Rippowam MS-Upper Soccer/Footballl Field [Directions] | Postponed | 2:45 PM | |
| Tue., 9/12 | V Boys Golf | Wilton | Away - Rolling Hills Country Club [Directions] | 3:30 p.m. | 1:45 PM | |
| Tue., 9/12 | V Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | W 3-2 | 2:30 PM | |
| Tue., 9/12 | JV Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 5:45 p.m. | 4:00 PM | |
| Tue., 9/12 | FR Boys Soccer | Brien McMahon | Home - Rippowam MS-Upper Soccer/Footballl Field [Directions] | 4:00 p.m. | 2:45 PM | |
| Tue., 9/12 | V Girls Soccer | Brien McMahon | Home - Stamford HS-SHS Upper Soccer Field [Directions] | L 1-2 | ||
| Wed., 9/13 | V Boys Cross Country | Westhill, Fairfield Warde, Norwalk | Away - Scofield Magnet MS-Cross Country Course [Directions] | 4:00 p.m. | 3:00 PM | |
| Wed., 9/13 | V Boys Soccer | Bridgeport Central | Away - Bridgeport Central-Kennedy Stadium Turf [Directions] | W 5-2 | 3:30 PM | |
| Wed., 9/13 | JV Boys Soccer | Bridgeport Central | Away - Bridgeport Central HS-Kennedy Stadium [Directions] | 4:30 p.m. | 2:30 PM | |
| Wed., 9/13 | V Girls Cross Country | Westhill, Fairfield Warde, Norwalk | Away - Scofield Magnet MS-Cross Country Course [Directions] | 4:00 p.m. | 3:00 PM | |
| Wed., 9/13 | V Girls Soccer | Bridgeport Central | Home - Stamford HS-SHS Upper Soccer Field [Directions] | W 8-0 | 3:00 PM | |
| Wed., 9/13 | V Girls Swimming and Diving | Trumbull | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Thu., 9/14 | V Football | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | L 14-28 | 4:00 PM (2 buses - Holcomb Ave lot) | |
| Thu., 9/14 | V Competitive Cheerleading | at Greenwich HS | Away - Not Listed | 6:00 p.m. | 5:00 PM | |
| Thu., 9/14 | V Field Hockey | Fairfield Warde | Home - Stamford HS-Boyle Stadium [Directions] | W 1-0 | ||
| Thu., 9/14 | JV Field Hockey | Fairfield Warde | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Mon., 9/18 | V Girls Soccer | Darien | Away - Darien HS-[CIAC] Willow Brook Park [Directions] | L 0-4 | 2:45 PM | |
| Mon., 9/18 | JV Girls Soccer | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | 2:45 PM | |
| Mon., 9/18 | V Girls Volleyball | Harding | Away - Warren Harding HS-Gym [Directions] | W 3-0 | 2:15 PM | |
| Mon., 9/18 | JV Girls Volleyball | Harding | Away - Warren Harding HS-Gym [Directions] | 4:30 p.m. | 2:15 PM | |
| Tue., 9/19 | V Boys Cross Country | Trumbull, Bridgeport Central, Ridgefield | Away - Trumbull HS-Cross Country Course [Directions] | 4:00 p.m. | 2:15 PM | |
| Tue., 9/19 | V Boys Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | 3:30 p.m. | 1:45 PM | |
| Tue., 9/19 | V Boys Soccer | Darien | Away - Darien HS-[CIAC] Willow Brook Park [Directions] | W 2-1 | 2:45 PM | |
| Tue., 9/19 | JV Boys Soccer | Darien | Home - Trinity Catholic-Alumni Field [Directions] | 4:30 p.m. | 3:30 PM | |
| Tue., 9/19 | FR Boys Soccer | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | 2:45 PM | |
| Tue., 9/19 | V Girls Cross Country | Trumbull, Bridgeport Central, Ridgefield | Away - Trumbull HS-Cross Country Course [Directions] | 4:00 p.m. | 2:15 PM | |
| Tue., 9/19 | V Field Hockey | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | L 1-3 | 2:30 PM | |
| Tue., 9/19 | JV Field Hockey | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 6:30 p.m. | 2:30 PM | |
| Wed., 9/20 | V Girls Soccer | Staples | Away - Staples HS-Wakeman Field B (turf) [Directions] | L 1-5 | 2:30 PM | |
| Wed., 9/20 | JV Girls Soccer | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | 4:30 p.m. | 2:30 PM | |
| Wed., 9/20 | V Girls Swimming and Diving | Wilton | Away - Wilton YMCA [Directions] | 3:40 p.m. | ||
| Wed., 9/20 | V Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | L 0-3 | 3:00 PM | |
| Wed., 9/20 | JV Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | 3:00 PM | |
| Thu., 9/21 | FR Football | Simsbury | Home - Stamford HS-Boyle Stadium [Directions] | W 27-2 | ||
| Thu., 9/21 | V Boys Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | 1:45 PM | |
| Thu., 9/21 | V Boys Soccer | Staples | Away - Staples HS-Wakeman Field B (turf) [Directions] | T 1-1 | 2:30 PM | |
| Thu., 9/21 | JV Boys Soccer | Staples | Home - Trinity Catholic-Alumni Field [Directions] | 4:30 p.m. | 3:30 PM | |
| Thu., 9/21 | FR Boys Soccer | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | 4:30 p.m. | 2:30 PM | |
| Fri., 9/22 | V Football | Simsbury | Away - Holden Field-Turf [Directions] | W 27-7 | 1:30 PM, Dismiss 1:00 PM (Coach bus from Holcomb Ave) | |
| Fri., 9/22 | V Girls Soccer | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | L 0-4 | ||
| Fri., 9/22 | JV Girls Soccer | Ridgefield | Away - Ridgefield HS-Upper Grass Field [Directions] | 4:00 p.m. | 2:30 PM | |
| Fri., 9/22 | V Girls Volleyball | St. Joseph | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 0-3 | ||
| Fri., 9/22 | JV Girls Volleyball | St. Joseph | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 9/22 | FR Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:30 p.m. | 3:20 PM | |
| Sat., 9/23 | JV Football | Simsbury | Home - Stamford HS-Boyle Stadium [Directions] | 10:00 a.m. | ||
| Sat., 9/23 | V Boys Soccer | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | T 0-0 | 9:00 AM | |
| Sat., 9/23 | JV Boys Soccer | Ridgefield | Away - Ridgefield HS-Tiger Hollow Turf Field II [Directions] | 11:00 a.m. | 9:00 AM | |
| Sat., 9/23 | FR Boys Soccer | Ridgefield | Home - Rippowam MS-Upper Soccer/Footballl Field [Directions] | 10:00 a.m. | ||
| Sat., 9/23 | V Field Hockey | Joel Barlow | Away - Joel Barlow HS-Field I (Stadium) [Directions] | L 1-2 | 10:00 AM | |
| Sat., 9/23 | JV Field Hockey | Joel Barlow | Away - Joel Barlow HS-Field I (Stadium) [Directions] | 1:30 p.m. | 10:00 AM | |
| Tue., 9/26 | V Boys Golf | Staples | Home - Stamford High-Sterling Farms Golf Course [Directions] | 2:30 p.m. | ||
| Tue., 9/26 | V Boys Soccer | New Canaan | Home - West Beach Field [Directions] | W 3-0 | 2:30 PM | |
| Tue., 9/26 | JV Boys Soccer | New Canaan | Home - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | 3:30 PM | |
| Wed., 9/27 | V Boys Cross Country | Danbury, Darien, Fairfield Ludlowe | Away - Tarrywile Park [Directions] | 4:00 p.m. | 2:15 PM | |
| Wed., 9/27 | V Boys Golf | Brien McMahon | Home - Stamford High-Sterling Farms Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 9/27 | V Girls Cross Country | Danbury, Darien, Fairfield Ludlowe | Away - Tarrywile Park [Directions] | 4:00 p.m. | 2:15 PM | |
| Wed., 9/27 | V Field Hockey | Westhill | Home - Stamford HS-Boyle Stadium [Directions] | W 1-0 | ||
| Wed., 9/27 | JV Field Hockey | Westhill | Home - Stamford HS-Boyle Stadium [Directions] | 5:00 p.m. | ||
| Wed., 9/27 | V Girls Soccer | Danbury | Home - West Beach Field [Directions] | W 2-1 | 2:45 PM | |
| Wed., 9/27 | JV Girls Soccer | Danbury | Home - Rippowam MS-Upper Soccer/Footballl Field [Directions] | 4:15 p.m. | 3:15 PM | |
| Wed., 9/27 | V Girls Swimming and Diving | Norwalk/McMahon | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Wed., 9/27 | V Girls Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | L 2-3 | 2:30 PM | |
| Wed., 9/27 | JV Girls Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 5:30 p.m. | 2:30 PM | |
| Thu., 9/28 | FR Football | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | L 27-7 | 3:15 PM | |
| Thu., 9/28 | V Boys Golf | Westhill | Away - Woodway Country Club [Directions] | 1:00 p.m. | 12:00 PM | |
| Thu., 9/28 | V Boys Soccer | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | L 2-1 | 4:30 PM | |
| Thu., 9/28 | JV Boys Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 6:30 p.m. | 4:30 PM | |
| Thu., 9/28 | FR Boys Soccer | Danbury | Home - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | 3:15 PM | |
| Thu., 9/28 | V Girls Volleyball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | W 3-0 | 2:30 PM | |
| Thu., 9/28 | JV Girls Volleyball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | 4:00 p.m. | 2:30 PM | |
| Thu., 9/28 | FR Girls Volleyball | Brien McMahon | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 9/29 | JV Field Hockey | Ridgefield | Home - Stamford HS-Boyle Stadium [Directions] | Postponed | ||
| Fri., 9/29 | JV Girls Soccer | New Canaan | Away - New Canaan HS-WTT #2 [Directions] | Postponed | 3:00 PM | |
| Fri., 9/29 | V Girls Swimming and Diving | Greenwich | Away - Greenwich HS-Pool [Directions] | 4:00 p.m. | ||
| Sat., 9/30 | V Football | St. Joseph | Home - Stamford HS-Boyle Stadium [Directions] | L 16-17 | ||
| Sat., 9/30 | FR Boys Soccer | New Canaan | Away - Saxe MS-Field 1 [Directions] | Postponed | 9:00 AM | |
| Sat., 9/30 | V Field Hockey | Ridgefield | Home - Stamford HS-Boyle Stadium [Directions] | L 0-4 | ||
| Sat., 9/30 | V Girls Volleyball | Weston | Away - Weston HS-Gym (New) [Directions] | W 3-1 | 9:15 AM | |
| Sat., 9/30 | JV Girls Volleyball | Weston | Away - Weston HS-Gym (New) [Directions] | 12:00 p.m. | 9:15 AM | |
| Sat., 9/30 | FR Girls Volleyball | Weston | Away - Weston HS-Gym (Old) [Directions] | 10:30 a.m. | 9:15 AM | |
| Mon., 10/2 | JV Football | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | L 21-8 | 2:30 PM | |
| Tue., 10/3 | V Boys Cross Country | New Canaan, Greenwich, St. Joseph | Away - Waveny Park [Directions] | 4:00 p.m. | 2:30 PM | |
| Tue., 10/3 | V Boys Golf | New Canaan | Away - CCNC [Directions] | 3:15 p.m. | 2:15 PM | |
| Tue., 10/3 | FR Boys Soccer | Westhill | Away - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | 3:30 PM | |
| Tue., 10/3 | V Girls Cross Country | New Canaan, Greenwich, St. Joseph | Away - Waveny Park [Directions] | 4:00 p.m. | 2:30 PM | |
| Tue., 10/3 | V Field Hockey | Danbury | Home - Stamford HS-Boyle Stadium [Directions] | W 1-0 | ||
| Tue., 10/3 | JV Field Hockey | Danbury | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Tue., 10/3 | V Girls Soccer | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | W 3-1 | 2:45 AM | |
| Tue., 10/3 | JV Girls Soccer | Westhill | Away - Rippowan MS-Rippowam Turf Field [Directions] | 4:00 p.m. | 2:45 PM | |
| Tue., 10/3 | V Girls Volleyball | Darien | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 0-3 | ||
| Tue., 10/3 | JV Girls Volleyball | Darien | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 10/3 | FR Girls Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | 2:45 PM | |
| Wed., 10/4 | V Boys Soccer | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | L 4-1 | 2:45 PM | |
| Wed., 10/4 | JV Boys Soccer | Westhill | Home - West Beach Field [Directions] | 4:00 p.m. | 2:45 PM | |
| Thu., 10/5 | V Boys Golf | The Chappa @ Longshore | Away - Not Listed-Longshore Golf Course | 3:15 p.m. | 8:30 AM (Return Approx 2:30) | |
| Thu., 10/5 | V Field Hockey | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | L 0-4 | 3:15 PM | |
| Thu., 10/5 | JV Field Hockey | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 6:00 p.m. | 3:15 PM | |
| Thu., 10/5 | V Girls Soccer | Trumbull | Away - Trumbull HS-Cork Field [Directions] | T 0-0 | 3:15 PM | |
| Thu., 10/5 | JV Girls Soccer | Trumbull | Away - Trumbull HS-JV Grass Field [Directions] | 4:30 p.m. | 2:30 PM | |
| Thu., 10/5 | V Girls Swimming and Diving | Staples | Away - Staples HS-Staples High School Pool [Directions] | 4:30 p.m. | ||
| Thu., 10/5 | V Girls Volleyball | Staples | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 0-3 | ||
| Thu., 10/5 | JV Girls Volleyball | Staples | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 10/5 | FR Girls Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:30 p.m. | 2:30 PM | |
| Fri., 10/6 | V Boys Soccer | Trumbull | Away - Trumbull HS-Cork Field [Directions] | L 2-1 | 2:30 PM | |
| Fri., 10/6 | JV Boys Soccer | Trumbull | Away - Trumbull HS-JV Grass Field [Directions] | 4:30 p.m. | 2:30 PM | |
| Fri., 10/6 | FR Boys Soccer | Trumbull | Home - Rippowam MS-Upper Soccer/Footballl Field [Directions] | 4:00 p.m. | 2:45 PM | |
| Fri., 10/6 | V Girls Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | L 0-3 | 2:30 PM | |
| Fri., 10/6 | JV Girls Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:00 p.m. | 2:30 PM | |
| Sat., 10/7 | V Boys Cross Country | Wickham Invitational | Away - Not Listed-Wickham Park | Cancelled | 9:00 AM | |
| Sat., 10/7 | V Girls Cross Country | Wickham Invitational | Away - Not Listed-Wickham Park | Cancelled | 9:00 AM | |
| Sat., 10/7 | V Girls Soccer | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | L 0-3 | 11:30 AM | |
| Sat., 10/7 | FR Girls Volleyball | Ridgefield | Home - Stamford HS-Kuczo Gymnasium [Directions] | 10:00 a.m. | ||
| Mon., 10/9 | V Field Hockey | Wilton | Home - Stamford HS-Boyle Stadium [Directions] | L 0-4 | ||
| Mon., 10/9 | JV Field Hockey | Wilton | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Mon., 10/9 | V Girls Soccer | Greenwich | Away - Greenwich HS-Field 3 [Directions] | L 0-1 | 3:15 PM | |
| Mon., 10/9 | JV Girls Soccer | Greenwich | Away - Greenwich HS-Cos Cob Park, Benvenuto Field [Directions] | 4:30 p.m. | 3:15 PM | |
| Mon., 10/9 | V Girls Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | W 3-1 | 10:00 AM | |
| Mon., 10/9 | JV Girls Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 1:30 p.m. | 10:00 AM | |
| Mon., 10/9 | FR Girls Volleyball | Danbury | Away - Danbury HS-New Gym [Directions] | 12:00 p.m. | 10:00 AM | |
| Tue., 10/10 | V Boys Golf | Danbury, St. Joseph | Home - Stamford High-Sterling Farms Golf Course [Directions] | 2:30 p.m. | ||
| Tue., 10/10 | V Boys Soccer | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | T 0-0 | 3:15 PM (Varsity to GHS and Freshman to Cos Cob Park) | |
| Tue., 10/10 | JV Boys Soccer | Greenwich | Home - Trinity Catholic-Alumni Field [Directions] | 4:30 p.m. | 3:30 PM | |
| Tue., 10/10 | FR Boys Soccer | Greenwich | Away - Greenwich HS-Cos Cob Park, Benvenuto Field [Directions] | 4:30 p.m. | 3:15 PM (Varsity to GHS and Freshman to Cos Cob Park) | |
| Wed., 10/11 | V Boys Cross Country | Wilton, Brien McMahon, Staples | Away - Allen's Meadow-XC Course [Directions] | 4:00 p.m. | 2:30 PM | |
| Wed., 10/11 | V Boys Golf | Ridgefield | Home - Stamford High-Sterling Farms Golf Course [Directions] | 3:00 p.m. | ||
| Wed., 10/11 | V Girls Cross Country | Wilton, Brien McMahon, Staples | Away - Allen's Meadow-XC Course [Directions] | 4:00 p.m. | 2:30 PM | |
| Wed., 10/11 | V Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | L 0-4 | 5:00 PM | |
| Wed., 10/11 | JV Field Hockey | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 5:00 p.m. | 3:15 PM | |
| Wed., 10/11 | V Girls Swimming and Diving | St. Joseph | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Wed., 10/11 | V Girls Volleyball | New Canaan | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 3-0 | ||
| Wed., 10/11 | JV Girls Volleyball | New Canaan | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 10/11 | FR Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | 2:45 PM | |
| Thu., 10/12 | FR Football | Fairfield Ludlowe | Home - Stamford HS-Boyle Stadium [Directions] | L 34-16 | ||
| Thu., 10/12 | V Boys Golf | Darien | Away - Wee Burn CC [Directions] | 3:15 p.m. | 1:45 PM | |
| Thu., 10/12 | V Girls Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | L 5-0 | 4:30 PM | |
| Thu., 10/12 | JV Girls Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | 4:00 p.m. | 2:15 PM | |
| Fri., 10/13 | V Boys Soccer | Fairfield Ludlowe | Home - West Beach Field [Directions] | L 2-1 | 2:45 PM | |
| Fri., 10/13 | FR Boys Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | 4:30 p.m. | 2:30 PM | |
| Fri., 10/13 | V Field Hockey | Darien | Home - Stamford HS-Boyle Stadium [Directions] | L 0-6 | ||
| Fri., 10/13 | JV Field Hockey | Darien | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Fri., 10/13 | V Girls Volleyball | Westhill | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 0-3 | ||
| Fri., 10/13 | JV Girls Volleyball | Westhill | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 10/13 | FR Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:00 p.m. | 2:45 PM | |
| Sat., 10/14 | V Football | Bridgeport Central | Away - Bridgeport Central-Kennedy Stadium Turf [Directions] | W 58-6 | 8:45 AM (2 buses) | |
| Sat., 10/14 | JV Boys Soccer | Fairfield Ludlowe | Home - TBA [Directions] | Postponed | ||
| Sat., 10/14 | V Competitive Cheerleading | At Bridgeport Central | Away - Not Listed-Bridgeport central | 11:00 a.m. | 9:30 AM | |
| Mon., 10/16 | V Girls Soccer | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | L 1-2 | 4:30 PM | |
| Mon., 10/16 | JV Girls Soccer | Fairfield Warde | Away - Fairfield Warde HS-Grass Utility Field [Directions] | 4:30 p.m. | 2:30 PM | |
| Mon., 10/16 | V Girls Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | L 0-3 | 2:30 PM | |
| Mon., 10/16 | JV Girls Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 4:30 p.m. | 2:30 PM | |
| Mon., 10/16 | FR Girls Volleyball | Trumbull | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 10/17 | V Boys Soccer | Fairfield Warde | Home - West Beach Field [Directions] | W 4-0 | 2:45 PM | |
| Tue., 10/17 | JV Boys Soccer | Fairfield Warde | Home - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | 3:30 PM | |
| Tue., 10/17 | FR Boys Soccer | Fairfield Warde | Away - Fairfield Warde HS-Ward HS Grass #1 [Directions] | 4:30 p.m. | 2:30 PM | |
| Tue., 10/17 | V Field Hockey | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | OT-L 0-1 | 4:30 PM | |
| Tue., 10/17 | JV Field Hockey | Greenwich | Away - Greenwich HS-Field 3 [Directions] | 4:00 p.m. | 2:45 AM | |
| Tue., 10/17 | V Girls Swimming and Diving | Fairfield Warde | Away - Fairfield University-Pool [Directions] | 4:00 p.m. | ||
| Wed., 10/18 | V Boys Cross Country | FCIAC Championship | Away - Waveny Park | 2:15 p.m. | 12:30 PM | |
| Pending change awaiting acceptance by one or more parties involved: Facility to Not Listed-Waveny Park | ||||||
| Wed., 10/18 | FR Football | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | L 28-26 | 2:45 PM | |
| Wed., 10/18 | V Girls Cross Country | FCIAC Championship | Away - Waveny Park | 2:15 p.m. | 12:30 PM | |
| Pending change awaiting acceptance by one or more parties involved: Facility to Not Listed-Waveny Park | ||||||
| Wed., 10/18 | V Girls Soccer | Norwalk | Home - West Beach Field [Directions] | W 3-0 | 2:30 PM | |
| Wed., 10/18 | JV Girls Soccer | Norwalk | Home - Rippowam MS-Upper Soccer/Footballl Field [Directions] | Cancelled | 2:45 PM | |
| Wed., 10/18 | V Girls Volleyball | Greenwich | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 0-3 | ||
| Wed., 10/18 | JV Girls Volleyball | Greenwich | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 10/18 | FR Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | 3:00 PM | |
| Thu., 10/19 | V Boys Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | W 3-0 | 5:00 PM | |
| Thu., 10/19 | JV Boys Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 5:00 p.m. | 3:15 PM | |
| Thu., 10/19 | FR Boys Soccer | Norwalk | Home - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | 3:30 PM | |
| Thu., 10/19 | V Field Hockey | Staples | Home - Stamford HS-Boyle Stadium [Directions] | L 0-4 | ||
| Thu., 10/19 | JV Field Hockey | Staples | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Fri., 10/20 | V Football | Staples | Away - Staples HS-Staples Stadium [Directions] | L 10-21 | 4:15 PM (2 buses) | |
| Fri., 10/20 | V Competitive Cheerleading | At Staples | Away - Not Listed-Staples HS | 7:00 p.m. | 5:00 PM | |
| Fri., 10/20 | V Girls Soccer | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | L 0-5 | 2:15 PM | |
| Fri., 10/20 | JV Girls Soccer | St. Joseph | Away - St. Joseph HS-Lower Grass Field [Directions] | Postponed | 2:15 PM | |
| Fri., 10/20 | V Girls Volleyball | Fairfield Ludlowe | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 2-3 | ||
| Fri., 10/20 | JV Girls Volleyball | Fairfield Ludlowe | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 10/20 | FR Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:30 p.m. | 2:30 PM | |
| Sat., 10/21 | V Boys Soccer | St. Joseph | Home - Westhill HS-Westhill Front Turf Field [Directions] | W 4-0 | ||
| Sat., 10/21 | V Field Hockey | New Fairfield | Home - Stamford HS-Boyle Stadium [Directions] | T 1-1 | ||
| Sat., 10/21 | JV Field Hockey | New Fairfield | Home - Stamford HS-Boyle Stadium [Directions] | 12:30 p.m. | ||
| Mon., 10/23 | V Girls Soccer | Wilton | Home - West Beach Field [Directions] | W 2-1 | 2:45 PM | |
| Mon., 10/23 | JV Girls Soccer | Wilton | Home - Rippowam MS-Upper Soccer/Footballl Field [Directions] | 4:30 p.m. | 3:30 PM | |
| Mon., 10/23 | V Girls Swimming and Diving | Danbury | Away - WCSU O'Neill Center Pool [Directions] | 3:45 p.m. | ||
| Mon., 10/23 | V Girls Volleyball | Fairfield Warde | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 0-3 | Senior Knight | |
| Mon., 10/23 | JV Girls Volleyball | Fairfield Warde | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 10/23 | FR Girls Volleyball | Fairfield Warde | Home - Stamford HS-SHS Aux Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/24 | V Boys Golf | CIAC Division I Fall Championship | Away - Stanley GC | 8:30 a.m. | ||
| Tue., 10/24 | V Boys Soccer | Wilton | Away - Wilton HS-Lilly Field [Directions] | W 5-0 | 4:30 PM | |
| Tue., 10/24 | JV Boys Soccer | Wilton | Away - Allen's Meadow-Field 2 [Directions] | 4:30 p.m. | 2:30 PM | |
| Tue., 10/24 | FR Boys Soccer | Wilton | Home - Trinity Catholic-Gaglio Field [Directions] | 4:30 p.m. | 3:30 PM | |
| Tue., 10/24 | V Field Hockey | Norwalk | Away - Norwalk HS-Testa Field [Directions] | L 0-2 | 5:45 PM | |
| Tue., 10/24 | JV Field Hockey | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 5:30 p.m. | 4:15 PM | |
| Wed., 10/25 | V Girls Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | W 3-0 | 2:30 PM | |
| Wed., 10/25 | JV Girls Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 5:30 p.m. | 2:30 PM | |
| Wed., 10/25 | FR Girls Volleyball | Norwalk | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 10/26 | FR Football | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | L 21-12 | 3:00 PM | |
| Thu., 10/26 | V Field Hockey | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | W 3-0 | 2:15 PM | |
| Thu., 10/26 | JV Field Hockey | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 6:00 p.m. | 2:15 PM | |
| Fri., 10/27 | V Boys Soccer | Fairfield Ludlowe | Home - West Beach Field [Directions] | W 1-1 (4-2 PKs) | ||
| Fri., 10/27 | V Girls Volleyball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | W 3-2 | 2:30 PM | |
| Fri., 10/27 | JV Girls Volleyball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:30 p.m. | 2:30 PM | |
| Fri., 10/27 | FR Girls Volleyball | Wilton | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | ||
| Sat., 10/28 | V Football | Trumbull | Home - Stamford HS-Boyle Stadium [Directions] | W 34-14 | PINK OUT | |
| Sat., 10/28 | JV Girls Swimming and Diving | Greenwich, Danbury, Darien, Fairfield Ludlowe, New Canaan, Norwalk/McMahon, Ridgefield, St. Joseph, Staples, Trumbull, Wilton | Away - Greenwich HS-Pool | 9:30 a.m. | ||
| Sat., 10/28 | JV Girls Volleyball | Fairfield Warde, Brien McMahon, Darien, Fairfield Ludlowe, Greenwich Country Day, Greenwich, Shelton, Trumbull, Weston | Away - Fairfield Warde HS-Large Gym | 9:00 a.m. | 7:30 AM | |
| Mon., 10/30 | JV Football | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | L 35-12 | 3:30 PM | |
| Mon., 10/30 | V Boys Soccer | Staples | Away - Fairfield Ludlowe HS-Taft Field [Directions] | W 2-1 | 2:45 PM | |
| Tue., 10/31 | V Boys Cross Country | CIAC Class LL Championship | Away - Wickham Park | 3:15 p.m. | TBA (Shared Coach Bus with WHS) | |
| Tue., 10/31 | V Girls Cross Country | CIAC Class LL Championship | Away - Wickham Park | 2:30 p.m. | ||
| Wed., 11/1 | V Girls Swimming and Diving | Greenwich, Danbury, Darien, Fairfield Ludlowe, Fairfield Warde, New Canaan, Norwalk/McMahon, Ridgefield, St. Joseph, Staples, Trumbull, Wilton | Away - Greenwich HS-Pool | 5:30 p.m. | ||
| Thu., 11/2 | FR Football | Fairfield Warde | Home - Stamford HS-Boyle Stadium [Directions] | W 13-12 | ||
| Thu., 11/2 | V Boys Soccer | Trumbull | Away - Norwalk HS-Testa Field [Directions] | L 3-2 (ET) | ||
| Fri., 11/3 | V Football | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | W 37-7 | 4:15 PM | |
| Fri., 11/3 | V Competitive Cheerleading | At Ridgefield | Away - Not Listed-Ridgefield HS | 7:00 p.m. | 5:15 PM | |
| Sat., 11/4 | V Girls Swimming and Diving | Greenwich, Danbury, Darien, Fairfield Ludlowe, Fairfield Warde, New Canaan, Norwalk/McMahon, Ridgefield, St. Joseph, Staples, Trumbull, Wilton | Away - Greenwich HS-Pool | 3:30 p.m. | ||
| Mon., 11/6 | V Boys Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Mon., 11/6 | JV Football | Ridgefield | Home - Stamford HS-Boyle Stadium [Directions] | Cancelled | ||
| Mon., 11/6 | V Girls Cross Country | CIAC State Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Mon., 11/6 | V Girls Soccer | Cheshire | Away - Cheshire High Main Game field [Directions] | 6:00 p.m. | 2:45 PM | |
| Tue., 11/7 | V Boys Soccer | New Milford | Home - Trinity Catholic-Gaglio Field [Directions] | W 4-0 | Cannot enter the field until 4:30. Game is on main stadium field | |
| Tue., 11/7 | V Girls Volleyball | Cheshire | Away - Cheshire HS-Gym West [Directions] | 6:00 p.m. | 2:45 PM | |
| Thu., 11/9 | FR Football | Westhill | Home - Stamford HS-Boyle Stadium [Directions] | W 47-8 | ||
| Thu., 11/9 | V Boys Soccer | Naugatuck | Away - Naugatuck HS-Veterans Field [Directions] | W 4-1 | 3:30 PM | |
| Thu., 11/9 | V Girls Swimming and Diving | CIAC Class LL Diving Championship | Away - Sheehan | 5:30 p.m. | ||
| Sat., 11/11 | V Football | Danbury | Home - Stamford HS-Boyle Stadium [Directions] | W 44-7 | ||
| Sat., 11/11 | V Boys Soccer | Westhill | Home - On The Road-Darien HS Stadium [Directions] | W 2-0 | Game will be played at Darien HS Stadium | |
| Sat., 11/11 | V Girls Swimming and Diving | CIAC Class LL Qualifying Meet | Away - Cornerstone Pool | 4:30 p.m. | ||
| Mon., 11/13 | JV Football | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | L 40-0 | 3:00 PM | |
| Tue., 11/14 | V Girls Swimming and Diving | CIAC Class LL Finals | Away - Wesleyan | 6:00 p.m. | ||
| Wed., 11/15 | V Boys Soccer | Greenwich | Away - Norwalk HS - Ray Barry Field-Stadium [Directions] | W 3-0 | 3:45 PM | |
| Thu., 11/16 | V Girls Swimming and Diving | CIAC State Open Diving | Away - Middletown | 5:30 p.m. | ||
| Sat., 11/18 | JV Football | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | L 16-2 | 9:30 AM | |
| Sat., 11/18 | V Boys Soccer | Hall | Away - Trinity Health Stadium-Dillon Stadium [Directions] | L 1-0 | 3:00 PM | |
| Sun., 11/19 | V Girls Swimming and Diving | CIAC State Open Swimming | Away - Yale | 1:00 p.m. | ||
| Thu., 11/23 | V Football | Westhill | Home - Stamford HS-Boyle Stadium [Directions] | W 35-6 | ||
| Tue., 11/28 | V Football | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | L 21-47 | ||
| Tue., 11/28 | V Football | CIAC Quarterfinals | Away - Higher Seed | 6:30 p.m. | ||
| Tue., 11/28 | V Girls Ice Hockey | Greenwich (Scrim.) | Away - Greenwich - Dorothy Hamill-Rink [Directions] | 5:15 p.m. | ||
| Sat., 12/2 | V Girls Basketball | Danbury (Scrim.) | Away - Danbury HS-Main Gym [Directions] | 1:00 p.m. | 11:30 AM | |
| Sat., 12/2 | V Girls Ice Hockey | Rinks of Shelton Jambo | Away - Not Listed-Rinks At Shelton | 4:30 p.m. | 2:05 PM (2:05 at WHS - 2:30 at SHS -> pick up Staples at Exit 18.) | |
| Sun., 12/3 | V Football | CIAC Semifinals | Away - Higher Seed | 12:30 p.m. | ||
| Tue., 12/5 | V Boys Basketball | Wilbur Cross (Scrim.) | Away - Wilbur Cross HS-Gym [Directions] | 5:30 p.m. | 3:00 PM | |
| Wed., 12/6 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 7-0 | 7:50 Start | |
| Thu., 12/7 | V Boys Ice Hockey | Masuk (Scrim.) | Home - Terry Conners - Stamford-Ice Rink [Directions] | 7:20 p.m. | ||
| Fri., 12/8 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | W 3-0 | 1:45 PM (1:40 at SHS- 1:55 at WHS Staples on separate bus from Staples HS) | |
| Sat., 12/9 | V Boys Basketball | Windsor Basketball Jamboree | Away - Not Listed-Windsor HS | 2:00 p.m. | 12:30 PM | |
| Sat., 12/9 | V Football | CIAC Championship Games | Away - Site TBA | TBA | ||
| Mon., 12/11 | V Girls Ice Hockey | Simsbury | Away - Simsbury Farms Ice Rink-Ice Rink [Directions] | W 5-0 | 12:30 PM (Coach Bus to pick up at SHS - 12:30 -> exit 18 Staples) | |
| Wed., 12/13 | V Wrestling | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Aux Gym [Directions] | 5:30 p.m. | 3:30 PM | |
| Wed., 12/13 | V Girls Ice Hockey | Amity/Cheshire/North Haven | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 3-0 | ||
| Fri., 12/15 | V Girls Basketball | New Milford | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 41-40 | ||
| Fri., 12/15 | JV Girls Basketball | New Milford | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | ||
| Sat., 12/16 | V Boys Basketball | Amistad | Away - Amistad HS-Gym [Directions] | W 82-44 | 10:00 AM | |
| Sat., 12/16 | JV Boys Basketball | Amistad | Away - Amistad HS-Gym [Directions] | 12:00 p.m. | 10:00 AM | |
| Sat., 12/16 | V Boys Ice Hockey | Amity | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 2-1 | ||
| Sat., 12/16 | V Boys Indoor Track | Staples, Greenwich, Trumbull, Westhill | Away - Staples HS-Field House [Directions] | 1:00 p.m. | 11:30 AM | |
| Sat., 12/16 | V Wrestling | Ludlowe Invitational | Away - Fairfield Ludlowe HS-Main Gym | 9:00 a.m. | 7:00 AM | |
| Sat., 12/16 | V Girls Indoor Track | Staples, Greenwich, Trumbull, Westhill | Away - Staples HS-Field House [Directions] | 1:00 p.m. | 11:30 AM | |
| Mon., 12/18 | V Girls Basketball | Immaculate | Away - Immaculate HS-Immaculate Gym [Directions] | L 60-53 | 4:30 PM | |
| Mon., 12/18 | JV Girls Basketball | Immaculate | Away - Immaculate HS-Immaculate Gym [Directions] | 5:30 p.m. | 2:15 PM | |
| Mon., 12/18 | FR Girls Basketball | Immaculate | Away - Immaculate HS-Immaculate Gym [Directions] | 4:00 p.m. | 2:15 PM | |
| Mon., 12/18 | V Girls Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | L 3-0 | 5:40 PM (1 bus pick up at SHS (SHS/WHS) Staples transportation from Staples) | |
| Tue., 12/19 | V Boys Basketball | Kolbe Cathedral | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 53-68 | ||
| Tue., 12/19 | JV Boys Basketball | Kolbe Cathedral | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:00 p.m. | ||
| Tue., 12/19 | V Boys Swimming and Diving | Darien | Away - Darien YMCA [Directions] | 3:00 p.m. | ||
| Wed., 12/20 | V Boys Ice Hockey | Daniel Hand | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 4-1 | ||
| Wed., 12/20 | V Wrestling | St. Joseph | Home - Stamford HS-SHS Aux Gym [Directions] | 6:00 p.m. | ||
| Wed., 12/20 | V Girls Ice Hockey | Greenwich | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 4-1 | ||
| Thu., 12/21 | V Girls Basketball | Scarsdale (NY) | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 41-34 | ||
| Thu., 12/21 | JV Girls Basketball | Scarsdale (NY) | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | ||
| Fri., 12/22 | V Boys Basketball | Pomperaug | Away - Pomperaug HS-Main Gym [Directions] | W 48-39 | 3:00 PM | |
| Fri., 12/22 | JV Boys Basketball | Pomperaug | Away - Pomperaug HS-Main Gym [Directions] | 5:15 p.m. | 3:00 PM | |
| Fri., 12/22 | FR Boys Basketball | Pomperaug | Away - Pomperaug HS-Main Gym [Directions] | Cancelled | 2:00 PM | |
| Sat., 12/23 | V Boys Ice Hockey | Hamden | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 7-2 | ||
| Sat., 12/23 | V Wrestling | Wilton, New Canaan, North Haven | Away - Wilton HS-Nicholas Zeoli Fieldhouse [Directions] | 9:00 a.m. | 7:00 AM | |
| Sat., 12/23 | V Girls Basketball | Norwalk | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 52-41 | ||
| Sat., 12/23 | JV Girls Basketball | Norwalk | Home - Stamford HS-Kuczo Gymnasium [Directions] | 11:00 a.m. | ||
| Sat., 12/23 | V Girls Ice Hockey | East Catholic Coop | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 3-1 | ||
| Wed., 12/27 | V Boys Basketball | Weston | Away - New Fairfield HS-High School Gym [Directions] | W 74-53 | ||
| Wed., 12/27 | JV Boys Basketball | Weston | Away - New Fairfield HS-High School Gym [Directions] | 3:00 p.m. | 1:00 PM, Dismiss TBA | |
| Wed., 12/27 | V Girls Basketball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | W 56-51 | 10:00 AM | |
| Wed., 12/27 | JV Girls Basketball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 11:30 a.m. | 7:45 AM | |
| Wed., 12/27 | FR Girls Basketball | Amity | Away - Amity Regional HS-Paul D. Mengold Gymnasium [Directions] | 10:00 a.m. | 7:45 AM | |
| Thu., 12/28 | V Boys Ice Hockey | John Bapst (ME) | Home - East Haven HS-Patsy DiLungo Rink [Directions] | W 7-1 | ||
| Fri., 12/29 | V Boys Basketball | New Fairfield | Away - New Fairfield HS-High School Gym [Directions] | W 58-55 | 3:30 PM, Dismiss TBA | |
| Fri., 12/29 | JV Wrestling | Trumbull, Brien McMahon, Darien, Fairfield Warde, Greenwich, Masuk, TBA, New Canaan, New Fairfield, New Milford, Newtown, Ridgefield, Simsbury, Staples, Xavier | Away - Trumbull HS-THS Main Gym | 9:00 a.m. | 7:00 AM | |
| Sat., 12/30 | V Boys Ice Hockey | Staples | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 3-0 | ||
| Sat., 12/30 | V Girls Basketball | Southington | Away - Southington HS-Gym West [Directions] | L 45-36 | 9:15 AM | |
| Sat., 12/30 | JV Girls Basketball | Southington | Away - Southington HS-Gym West [Directions] | 11:30 a.m. | 9:15 AM | |
| Wed., 1/3 | V Boys Swimming and Diving | Trumbull | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Wed., 1/3 | V Wrestling | Danbury | Away - Danbury HS-New gym [Directions] | 4:30 p.m. | 2:30 PM | |
| Wed., 1/3 | V Girls Basketball | Wilton | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 52-32 | ||
| Wed., 1/3 | JV Girls Basketball | Wilton | Home - Stamford HS-Kuczo Gymnasium [Directions] | Cancelled | ||
| Pending change awaiting acceptance by one or more parties involved: Time to 4:00 p.m. | ||||||
| Wed., 1/3 | JV Girls Basketball | Wilton | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 1/3 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 5-2 | ||
| Fri., 1/5 | V Boys Basketball | St. Joseph | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 55-50 | ||
| Fri., 1/5 | JV Boys Basketball | St. Joseph | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/5 | FR Boys Basketball | St. Joseph | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/5 | V Boys Ice Hockey | JBWA | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 2-1 | ||
| Fri., 1/5 | V Girls Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | L 48-35 | 4:45 PM | |
| Fri., 1/5 | JV Girls Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 5:30 p.m. | 2:15 PM | |
| Fri., 1/5 | FR Girls Basketball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:00 p.m. | 2:15 PM | |
| Sat., 1/6 | V Boys Ice Hockey | Brien McMahon/Norwalk | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 7-3 | ||
| Sat., 1/6 | V Boys Indoor Track | Elm City Coaches Invitational | Away - Not Listed-Floyd Little Athletic Center | 9:00 a.m. | TBA | |
| Sat., 1/6 | V Boys Indoor Track | Staples, Brien McMahon, Greenwich, Westhill | Away - Staples HS-Field House [Directions] | 1:00 p.m. | 11:30 AM | |
| Sat., 1/6 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Away - Fairfield University-Pool [Directions] | 2:00 p.m. | ||
| Sat., 1/6 | V Wrestling | Warde Wrestling Invitational | Away - Fairfield Warde HS-Large Gym | TBA | 7:00 AM | |
| Pending change awaiting acceptance by one or more parties involved: Time to 9:00 a.m. | ||||||
| Sat., 1/6 | V Girls Indoor Track | Elm City Coaches Invitational | Away - Not Listed-Floyd Little Athletic Center | 9:00 a.m. | TBA | |
| Sat., 1/6 | V Girls Indoor Track | Staples, Brien McMahon, Greenwich, Westhill | Away - Staples HS-Field House [Directions] | 1:00 p.m. | 11:30 AM | |
| Tue., 1/9 | V Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | W 65-47 | 3:15 PM | |
| Tue., 1/9 | JV Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | Cancelled | 4:00 PM | |
| Tue., 1/9 | FR Boys Basketball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:00 p.m. | 2:30 PM | |
| Tue., 1/9 | V Girls Basketball | Brien McMahon | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 64-37 | ||
| Tue., 1/9 | JV Girls Basketball | Brien McMahon | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 1/10 | V Wrestling | Westhill | Home - Stamford HS-Kuczo Gymnasium [Directions] | 6:00 p.m. | ||
| Wed., 1/10 | V Girls Gymnastics | Wilton, Westhill | Away - Wilton HS-Aux Gym [Directions] | 113.85 | 12:00 PM (PIck up at WHS 2:30 - SHS 2:45 - Wilton HS. Return to SHS) | |
| Wed., 1/10 | V Girls Ice Hockey | Hamden Coop | Home - Terry Conners - Stamford-Ice Rink [Directions] | L 2-1 | ||
| Thu., 1/11 | V Girls Ice Hockey | Trumbull/St. Joseph | Away - Shelton - Sports Center of CT-Upper Rink [Directions] | W 3-1 | 6:00 PM (6:00 at Stamford HS-> pick up Staples at Exit 18.) | |
| Fri., 1/12 | V Boys Basketball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | W 63-46 | 3:45 PM | |
| Fri., 1/12 | JV Boys Basketball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | 5:30 p.m. | 3:45 PM | |
| Fri., 1/12 | FR Boys Basketball | Bridgeport Central | Away - Bridgeport Central-Barry McLeod Court [Directions] | 4:00 p.m. | 2:15 PM | |
| Fri., 1/12 | V Girls Basketball | Bridgeport Central | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 56-37 | ||
| Fri., 1/12 | JV Girls Basketball | Bridgeport Central | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/12 | FR Girls Basketball | Bridgeport Central | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Sat., 1/13 | V Boys Ice Hockey | Wilton | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | W 2-1 | ||
| Sat., 1/13 | V Boys Indoor Track | Staples, Bridgeport Central, Danbury, Darien, Greenwich, St. Joseph, Westhill | Away - Staples HS-Field House | 10:00 a.m. | 9:00 AM | |
| Sat., 1/13 | V Boys Indoor Track | Yale Invitational - Yale University | Away - Not Listed-Yale University | TBA | 8:15 AM | |
| Sat., 1/13 | V Girls Indoor Track | Staples, Bridgeport Central, Danbury, Darien, Greenwich, St. Joseph, Westhill | Away - Staples HS-Field House | 10:00 a.m. | 9:00 AM | |
| Sat., 1/13 | V Girls Indoor Track | Yale Invitational - Yale University | Away - Not Listed-Yale University | TBA | 8:15 AM | Yale Invitational - Yale University |
| Mon., 1/15 | V Boys Ice Hockey | East Haven Coop | Away - East Haven HS-Patsy DiLungo Rink [Directions] | W Forfeit | ||
| Wed., 1/17 | V Boys Basketball | Darien | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 63-59 | ||
| Wed., 1/17 | JV Boys Basketball | Darien | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 1/17 | FR Boys Basketball | Darien | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 1/17 | V Boys Ice Hockey | Darien | Home - Terry Conners - Stamford-Ice Rink [Directions] | L 4-2 | ||
| Wed., 1/17 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Away - Norwalk HS-Pat Spinola Natatorium [Directions] | 4:00 p.m. | ||
| Wed., 1/17 | V Girls Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | W 60-30 | 4:30 PM | |
| Wed., 1/17 | JV Girls Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 5:30 p.m. | 2:30 PM | |
| Wed., 1/17 | FR Girls Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | 2:30 PM | |
| Wed., 1/17 | V Girls Gymnastics | Westhill, New Canaan | Away - Westhill HS-New Gym [Directions] | 90.2 | TBA ((Parent drop off and pick up at WHS)) | |
| Wed., 1/17 | V Girls Ice Hockey | Darien | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 2-1 | ||
| Thu., 1/18 | V Wrestling | Norwalk | Home - Stamford HS-Kuczo Gymnasium [Directions] | 6:00 p.m. | ||
| Fri., 1/19 | V Boys Basketball | Staples | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 60-57 | ||
| Fri., 1/19 | JV Boys Basketball | Staples | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/19 | FR Boys Basketball | Staples | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/19 | V Girls Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | W 49-42 | 4:00 PM | |
| Fri., 1/19 | JV Girls Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 5:30 p.m. | 2:15 PM | |
| Fri., 1/19 | FR Girls Basketball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:00 p.m. | 2:15 PM | |
| Sat., 1/20 | V Boys Indoor Track | HOF Invitational @ The Armory | Away - Not Listed-Armory Athletic Center, NYC, New York | 10:00 a.m. | 8:00 AM | |
| Sat., 1/20 | V Boys Indoor Track | Wilton, Bridgeport Central, Brien McMahon, Danbury, Greenwich, New Canaan, St. Joseph | Away - Wilton HS-Nicholas Zeoli Field House | 9:30 a.m. | 8:00 AM | |
| Sat., 1/20 | JV Wrestling | Danbury, Enfield, Fairfield Ludlowe, Fairfield Warde, New Canaan, New Fairfield, Newtown, Norwalk, Ridgefield, Simsbury, Southington, Trumbull, Weston | Away - Danbury HS-Main Gym | 9:30 a.m. | 7:30 AM | |
| Sat., 1/20 | V Competitive Cheerleading | Night Hawk Cheer Classic | Away - Not Listed-North Haven HS | TBA | 3:00 PM | |
| Sat., 1/20 | V Girls Gymnastics | Darien, New Canaan, Westhill | Away - Darien YMCA [Directions] | 93.15 | 1:15 PM | |
| Sat., 1/20 | V Girls Ice Hockey | Mercy/NW Catholic/East Hampton | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 3-1 | 7:50 Start time | |
| Sat., 1/20 | V Girls Indoor Track | HOF INvitational @ The Armory NYC | Away - Not Listed-Armory Athletic Center, NYC, New York | 10:00 a.m. | 8:00 AM | |
| Sat., 1/20 | V Girls Indoor Track | Wilton, Bridgeport Central, Brien McMahon, Danbury, Greenwich, New Canaan, St. Joseph | Away - Wilton HS-Nicholas Zeoli Field House | 9:30 a.m. | 8:00 AM | |
| Mon., 1/22 | V Boys Swimming and Diving | Wilton | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Tue., 1/23 | V Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | L 61-42 | 3:30 PM | |
| Tue., 1/23 | JV Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:30 p.m. | 3:30 PM | |
| Tue., 1/23 | FR Boys Basketball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:00 p.m. | 2:15 PM | |
| Tue., 1/23 | V Girls Basketball | Ridgefield | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 42-33 | ||
| Tue., 1/23 | JV Girls Basketball | Ridgefield | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/23 | FR Girls Basketball | Ridgefield | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 1/24 | V Boys Ice Hockey | St. Joseph | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 4-2 | ||
| Wed., 1/24 | V Wrestling | Greenwich | Home - Stamford HS-Kuczo Gymnasium [Directions] | 7:00 p.m. | ||
| Wed., 1/24 | V Girls Ice Hockey | New Canaan | Home - Terry Conners - Stamford-Ice Rink [Directions] | L 2-0 | ||
| Thu., 1/25 | V Girls Gymnastics | Norwalk | Away - Westport YMCA [Directions] | 93.15 | ||
| Thu., 1/25 | V Girls Gymnastics | Staples, Westhill | Away - Staples HS-Westport YMCA [Directions] | 7:00 p.m. | 5:15 PM (one bus- pick up and drop off at SHS) | |
| Fri., 1/26 | V Boys Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | L 53-49 | 3:45 PM | |
| Fri., 1/26 | JV Boys Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 5:30 p.m. | 3:45 PM | |
| Fri., 1/26 | FR Boys Basketball | Danbury | Away - Danbury HS-Main Gym [Directions] | 4:00 p.m. | 2:15 PM | |
| Fri., 1/26 | V Boys Ice Hockey | New Canaan | Away - Darien Ice House-Ice Rink [Directions] | L 1-7 | ||
| Fri., 1/26 | V Boys Swimming and Diving | Danbury | Away - WCSU O'Neill Center Pool [Directions] | 5:30 p.m. | ||
| Fri., 1/26 | V Girls Basketball | Danbury | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 46-29 | ||
| Fri., 1/26 | JV Girls Basketball | Danbury | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 1/26 | FR Girls Basketball | Danbury | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 1/26 | V Girls Gymnastics | Fairfield Warde | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 82.4 | ||
| Fri., 1/26 | V Girls Gymnastics | Fairfield Ludlowe, Westhill | Away - Gymnastics and Cheerleading Academy at Connecticut-Gym 1 [Directions] | 6:00 p.m. | 4:15 PM (one bus from SHS) | |
| Sat., 1/27 | V Boys Cross Country | FCIAC West Divisional | Away - Not Listed-Staples HS | 10:00 a.m. | 8:30 AM | |
| Sat., 1/27 | V Wrestling | Brookfield Invitational | Away - Brookfield HS-BHS Small & Big Gym | 9:30 a.m. | 6:30 AM | |
| Sat., 1/27 | JV Wrestling | Norwalk, Brien McMahon, Darien, Fairfield Prep, Fairfield Ludlowe, Fairfield Warde, Greenwich, New Canaan, New Milford, St. Joseph, Staples, Trumbull, Westhill, Weston, Wilton | Away - Norwalk HS-Tom Scarso Gymnasium | 8:00 a.m. | 6:45 AM | |
| Sat., 1/27 | V Girls Ice Hockey | Greenwich | Away - Greenwich - Dorothy Hamill-Rink [Directions] | W 7-2 | ||
| Sat., 1/27 | V Girls Indoor Track | FCIAC West Divisional | Away - Not Listed-Staples HS | 10:00 a.m. | 8:30 AM | |
| Sun., 1/28 | V Wrestling | Queen of the Mats | Away - Not Listed-Foran HS | TBA | 6:45 AM | |
| Mon., 1/29 | V Girls Gymnastics | Westhill, St. Joseph, Trumbull | Away - Westhill HS-New Gym [Directions] | 115.8 | TBA (Parent drop off and pick up at WHS) | |
| Tue., 1/30 | V Boys Basketball | New Canaan | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 51-39 | ||
| Tue., 1/30 | JV Boys Basketball | New Canaan | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Tue., 1/30 | FR Boys Basketball | New Canaan | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/30 | V Girls Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | W 48-33 | 4:30 PM | |
| Tue., 1/30 | JV Girls Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | 2:30 PM | |
| Tue., 1/30 | FR Girls Basketball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | 2:30 PM | |
| Tue., 1/30 | V Girls Ice Hockey | West Haven/SHA | Away - West Haven HS-Bennett Rink [Directions] | W 3-1 | 3:00 PM (3:00 at Stamford HS-> pick up Staples at Exit 18.) | |
| Wed., 1/31 | V Boys Ice Hockey | Trumbull | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 7-0 | ||
| Wed., 1/31 | V Boys Swimming and Diving | New Canaan | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Wed., 1/31 | V Wrestling | Trumbull | Away - Trumbull HS-Aux Gym [Directions] | 6:00 p.m. | 3:45 PM | |
| Wed., 1/31 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - Ridgefield - Winter Garden-Ice Rink [Directions] | W 7-3 | 2:15 PM (2:15 from Stamford HS Staples transportation from Staples HS) | |
| Thu., 2/1 | V Boys Indoor Track | FCIAC Championships | Away - Not Listed-Floyd Little Athletic Center | 4:00 p.m. | 1:30 AM | |
| Thu., 2/1 | V Girls Gymnastics | Greenwich, Westhill | Away - Greenwich YWCA [Directions] | 78.8 | 5:15 PM | |
| Thu., 2/1 | V Girls Indoor Track | FCIAC Championships | Away - Not Listed-Floyd Little Athletic Center | 4:00 p.m. | 1:30 PM | |
| Thu., 2/1 | Unified Sports Basketball | Vs Brien McMahon | Home - Stamford HS-SHS Aux Gym [Directions] | 3:00 p.m. | ||
| Fri., 2/2 | JV Boys Basketball | Westhill | Home - Stamford HS-Kuczo Gymnasium [Directions] | 7:00 p.m. | ||
| Fri., 2/2 | FR Boys Basketball | Westhill | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 2/2 | V Boys Swimming and Diving | Greenwich | Away - Greenwich HS-Pool [Directions] | 4:15 p.m. | ||
| Fri., 2/2 | JV Girls Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 5:30 p.m. | 2:40 PM | |
| Fri., 2/2 | FR Girls Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:00 p.m. | 2:45 PM | |
| Sat., 2/3 | V Boys Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | W 56-44 | 12:30 PM | |
| Sat., 2/3 | V Boys Ice Hockey | Brien McMahon/Norwalk | Away - Sono Ice House-Main Rink [Directions] | W 12-4 | ||
| Sat., 2/3 | JV Wrestling | Ludlowe JV Tournament | Away - Fairfield Ludlowe HS-Main Gym | TBA | 7:15 AM | |
| Pending change awaiting acceptance by one or more parties involved: Time to 9:30 a.m. | ||||||
| Sat., 2/3 | V Girls Basketball | Westhill | Away - Westhill HS-Main Gym [Directions] | W 44-10 | 10:45 AM | |
| Sat., 2/3 | V Competitive Cheerleading | FCIAC Cheer Championship | Away - Trumbull HS-THS Main Gym | 10:00 a.m. | 8:00 AM | |
| Sat., 2/3 | V Girls Ice Hockey | Masuk Coop | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 2-0 | ||
| Sat., 2/3 | Unified Sports Basketball | Westhill | Away - Westhill HS-New Gym [Directions] | Cancelled | TBA (Parent drop off and pick up) | |
| Tue., 2/6 | V Boys Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | W 62-59 | 3:45 PM | |
| Tue., 2/6 | JV Boys Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 5:30 p.m. | 3:45 PM | |
| Tue., 2/6 | FR Boys Basketball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | 4:00 p.m. | 2:15 PM | |
| Tue., 2/6 | V Boys Ice Hockey | West Haven Coop | Away - West Haven HS-Bennett Rink [Directions] | W 2-1 | ||
| Tue., 2/6 | V Girls Basketball | Trumbull | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 33-31 | ||
| Tue., 2/6 | JV Girls Basketball | Trumbull | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 2/7 | V Boys Swimming and Diving | Staples | Away - Staples HS-Staples High School Pool [Directions] | 4:00 p.m. | ||
| Wed., 2/7 | V Wrestling | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 6:00 p.m. | 4:15 PM | |
| Wed., 2/7 | V Girls Ice Hockey | Darien | Away - Darien Ice House-Ice Rink [Directions] | L 3-1 | 5:00 PM (Pick up at Stamford HS) | |
| Thu., 2/8 | V Boys Indoor Track | CIAC Class LL Championships | Away - Not Listed-Floyd Little Athletic Center | 4:30 p.m. | 1:45 PM | |
| Thu., 2/8 | V Boys Indoor Track | CIAC LL Divisional Championship | Away - Floyd Little Athletic Center | 4:30 p.m. | ||
| Thu., 2/8 | V Girls Indoor Track | CIAC LL Divisional Championship | Away - Floyd Little Athletic Center | 4:30 p.m. | ||
| Thu., 2/8 | V Girls Indoor Track | CIAC Class LL Championships | Away - Not Listed-Floyd Little Athletic Center | 4:30 p.m. | 1:45 PM | |
| Thu., 2/8 | Unified Sports Basketball | Norwalk | Home - Stamford HS-SHS Aux Gym [Directions] | 3:00 p.m. | ||
| Fri., 2/9 | V Boys Basketball | Greenwich | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 39-45 | ||
| Fri., 2/9 | JV Boys Basketball | Greenwich | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Fri., 2/9 | FR Boys Basketball | Greenwich | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 2/9 | V Boys Swimming and Diving | Ridgefield | Home - Westhill HS-Westhill Pool [Directions] | 3:30 p.m. | ||
| Fri., 2/9 | V Wrestling | New Canaan, Bridgeport Central, Brien McMahon, Danbury, Darien, FCIAC, Fairfield Ludlowe, Fairfield Warde, Greenwich, Norwalk, Ridgefield, St. Joseph, Staples, Trumbull, Westhill, Wilton | Away - New Canaan HS-Main Gym | 4:30 p.m. | 2:45 PM | |
| Fri., 2/9 | V Girls Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | W 51-39 | 4:30 PM | |
| Fri., 2/9 | JV Girls Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | 2:30 PM | |
| Fri., 2/9 | FR Girls Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:00 p.m. | 2:30 PM | |
| Sat., 2/10 | V Boys Ice Hockey | South Windsor | Away - South Windsor Arena-Ice Rink [Directions] | T 2-2 | ||
| Sat., 2/10 | V Wrestling | FCIACS | Away - Not Listed-New Canaan | 10:00 a.m. | 8:30 AM | |
| Sat., 2/10 | V Competitive Cheerleading | Hatter Fest Cheer Competition | Away - Not Listed-Danbury HS | TBA | 8:00 AM | |
| Sat., 2/10 | V Girls Gymnastics | FCIACS | Away - Not Listed-GCA Gymnastics | 2:00 p.m. | 12:00 PM | |
| Sat., 2/10 | V Girls Ice Hockey | Southington Coop | Home - Terry Conners - Stamford-Ice Rink [Directions] | L 6-2 | 6:10 start Vs. Avon | |
| Mon., 2/12 | V Boys Basketball | Fairfield Ludlowe | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 67-45 | ||
| Mon., 2/12 | JV Boys Basketball | Fairfield Ludlowe | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 2/12 | FR Boys Basketball | Fairfield Ludlowe | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Mon., 2/12 | V Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | W 41-34 | 4:30 PM | |
| Mon., 2/12 | JV Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:30 p.m. | 2:15 PM | |
| Mon., 2/12 | FR Girls Basketball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:00 p.m. | 2:15 PM | |
| Wed., 2/14 | V Boys Basketball | Fairfield Warde | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 68-54 | ||
| Wed., 2/14 | JV Boys Basketball | Fairfield Warde | Home - Stamford HS-Kuczo Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 2/14 | FR Boys Basketball | Fairfield Warde | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 2/14 | V Boys Ice Hockey | Wilton | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 4-1 | ||
| Wed., 2/14 | V Girls Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | L 37-28 | 4:30 PM | |
| Wed., 2/14 | JV Girls Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 5:30 p.m. | 2:15 PM | |
| Wed., 2/14 | FR Girls Basketball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 4:00 p.m. | 2:15 PM | |
| Fri., 2/16 | V Wrestling | CIAC LL Divisional Championship | Away - Trumbull | TBA | 11:15 AM (Friday Bus is 11:15am - Sat bus is 8:30am) | |
| Sat., 2/17 | V Boys Ice Hockey | Trumbull | Away - Total Mortgage Arena - Harbor Yard-Ice Rink [Directions] | W 3-1 | ||
| Sat., 2/17 | V Girls Basketball | New Canaan | Home - Staples HS-Staples Gym [Directions] | 12:45 p.m. | 10:15 AM | |
| Sat., 2/17 | V Girls Indoor Track | CIAC State Open Championship | Away - Floyd Little Athletic Center | 12:00 p.m. | ||
| Mon., 2/19 | V Boys Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | W 62-52 | 3:15 PM | |
| Mon., 2/19 | JV Boys Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:30 p.m. | 3:15 PM | |
| Mon., 2/19 | FR Boys Basketball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 3:00 p.m. | 1:45 PM | |
| Mon., 2/19 | V Boys Ice Hockey | Staples | Away - Milford Ice Pavillion-Ice Rink [Directions] | W 4-0 | ||
| Wed., 2/21 | V Boys Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | L 56-54 | 3:45 PM | |
| Wed., 2/21 | JV Boys Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:15 p.m. | 3:45 PM | |
| Wed., 2/21 | FR Boys Basketball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | 2:15 PM | |
| Wed., 2/21 | V Girls Ice Hockey | Darien | Away - Darien Ice House-Ice Rink [Directions] | L 2-1 | 6:20 PM | |
| Thu., 2/22 | Unified Sports Basketball | Westhill | Home - Stamford HS-SHS Aux Gym [Directions] | 3:00 p.m. | ||
| Fri., 2/23 | V Boys Ice Hockey | Watertown-Pomperaug | Away - Taft School-Mays [Directions] | W 4-1 | ||
| Fri., 2/23 | V Wrestling | CIAC State Open & Girls Championship | Away - Floyd Little Athletic Center | TBA | 10:30 AM (Friday - 10:30 depart SHS Sat. - 7am Depart SHS) | |
| Sat., 2/24 | V Boys Basketball | Danbury | Home - Fairfield Warde HS-Large Gym [Directions] | 12:00 p.m. | 10:00 AM | |
| Sat., 2/24 | V Boys Ice Hockey | Darien | Away - Darien Ice House-Ice Rink [Directions] | 5:00 p.m. | ||
| Sat., 2/24 | V Competitive Cheerleading | Oxford Spirit Spectacular | Away - Not Listed-Oxford | TBA | 8:00 AM | |
| Mon., 2/26 | V Girls Basketball | West Haven | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 47-34 | ||
| Thu., 2/29 | V Girls Basketball | Danbury | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 54-34 | ||
| Thu., 2/29 | V Girls Ice Hockey | Mercy/NW Catholic/East Hampton | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 2-1 | ||
| Thu., 2/29 | Unified Sports Basketball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 3:30 p.m. | 2:30 PM | |
| Sat., 3/2 | V Competitive Cheerleading | CIAC State Championships | Away - Not Listed-Shelton HS | TBA | 3:30 AM | |
| Sat., 3/2 | V Girls Ice Hockey | Darien | Away - Shelton - Sports Center of CT-Lower Rink [Directions] | W 2-1 | 3:15 PM (Bus will pick up at Stamford HS 3:15 -> To Exit 18 to pick up Staples) | |
| Mon., 3/4 | V Boys Basketball | Enfield | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 71-58 | ||
| Mon., 3/4 | V Girls Basketball | Sacred Heart Academy | Away - Sacred Heart Academy-Gym [Directions] | L 49-72 | 3:30 PM | |
| Tue., 3/5 | V Boys Ice Hockey | Lyman Hall | Home - Terry Conners - Stamford-Ice Rink [Directions] | W 5-3 | ||
| Tue., 3/5 | V Boys Ice Hockey | CIAC Div II First Round | Away - Higher Seed | TBA | ||
| Wed., 3/6 | V Boys Basketball | Farmington | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 50-47 | ||
| Wed., 3/6 | V Girls Ice Hockey | New Canaan | Away - Quinnipiac University-TD Bank Sports Center [Directions] | 7:00 p.m. | 3:30 PM (Bus Departs SHS 3:30 -> Stops at Exits 18 for Staples -> Quinnipiac) | |
| Thu., 3/7 | V Boys Swimming and Diving | CIAC Class LL Diving Championship | Away - Sheehan | 5:30 p.m. | ||
| Thu., 3/7 | Unified Sports Basketball | Fairfield Ludlowe High School Tourney | Away - Not Listed-Fairfield Ludlowe HS | 3:00 p.m. | 2:30 PM | |
| Fri., 3/8 | V Boys Basketball | Manchester | Away - Manchester HS-Gym [Directions] | W 65-55 | 1:30 PM, Dismiss 1:20 PM | |
| Fri., 3/8 | V Boys Ice Hockey | Amity | Home - Wonderland of Ice-Stadium [Directions] | L 2-3 | ||
| Fri., 3/8 | V Boys Ice Hockey | CIAC Div II Quarterfinal | Away - Site TBA | TBA | ||
| Sat., 3/9 | V Boys Swimming and Diving | CIAC Class LL Qualifying Meet | Away - Cornerstone Pool | 4:30 p.m. | ||
| Tue., 3/12 | V Boys Basketball | West Haven | Home - University of Hartford [Directions] | L 32-46 | 2:30 PM | |
| Tue., 3/12 | V Boys Ice Hockey | CIAC Div II Semifinal | Away - Site TBA | TBA | ||
| Tue., 3/12 | V Boys Swimming and Diving | CIAC Class LL Finals | Away - Wesleyan | 6:00 p.m. | ||
| Thu., 3/14 | V Boys Swimming and Diving | CIAC State Open Diving | Away - Middletown | 5:30 p.m. | ||
| Thu., 3/14 | Unified Sports Basketball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 3:00 p.m. | 2:30 PM | |
| Sat., 3/16 | V Boys Swimming and Diving | CIAC State Open Swimming | Away - Yale | 1:00 p.m. | ||
| Mon., 3/18 | V Boys Ice Hockey | CIAC Div II Final | Away - Site TBA | TBA | ||
| Thu., 3/21 | V Boys Lacrosse | North Haven (Scrim.) | Away - North Haven MS-East Turf Field [Directions] | 6:00 p.m. | 3:45 PM | |
| Thu., 3/21 | V Girls Lacrosse | West Haven (Scrim.) | Home - Stamford HS-Boyle Stadium [Directions] | 4:30 p.m. | ||
| Sat., 3/23 | V Boys Lacrosse | Wooster (Scrim.) | Home - Shelton HS-Finn Stadium [Directions] | Cancelled | ||
| Sat., 3/23 | V Boys Lacrosse | Newtown (Scrim.) | Away - Shelton HS-Lower Field [Directions] | Cancelled | ||
| Sat., 3/23 | V Boys Lacrosse | Pomperaug (Scrim.) | Away - Shelton HS-Finn Stadium [Directions] | Cancelled | ||
| Sat., 3/23 | V Boys Lacrosse | Wooster (Scrim.) | Away - Shelton HS-Lower Field | Cancelled | ||
| Sat., 3/23 | V Boys Volleyball | Westhill (Scrim.) | Away - Westhill HS-Main Gym [Directions] | 10:00 a.m. | 9:00 AM | |
| Sun., 3/24 | V Girls Lacrosse | New Milford Jamboree | Away - New Milford HS-Joe Wiser Stadium - NMHS | 8:00 a.m. | TBA (11am departure time for Stamford HS) | |
| Mon., 3/25 | V Softball | Darien (Scrim.) | Away - Darien HS-DHS Softball - Varsity Field [Directions] | 4:00 p.m. | 2:45 PM | |
| Tue., 3/26 | V Baseball | Greenwich (Scrim.) | Home - Cubeta Stadium [Directions] | 5:15 p.m. | ||
| Tue., 3/26 | V Boys Lacrosse | Newtown (Scrim.) | Away - Newtown HS-Blue and Gold Stadium [Directions] | 7:00 p.m. | 4:45 PM | |
| Wed., 3/27 | V Baseball | New Canaan (Scrim.) | Away - Mead Park-Baseball Field [Directions] | 4:00 p.m. | 2:30 PM (Varsity only) | |
| Wed., 3/27 | JV Baseball | New Canaan (Scrim.) | Away - Waveny Park-Coppo Field [Directions] | 4:00 p.m. | 2:30 PM (JV Only) | |
| Wed., 3/27 | JV Boys Lacrosse | Staples (Scrim.) | Away - Staples HS-Wakeman Field B (turf) [Directions] | 4:30 p.m. | 2:30 PM | |
| Wed., 3/27 | V Boys Volleyball | Greenwich (Scrim.) | Home - Stamford HS-Kuczo Gymnasium [Directions] | 4:30 p.m. | ||
| Wed., 3/27 | V Softball | New Fairfield (Scrim.) | Away - New Fairfield HS-Softball Field [Directions] | W 10-6 | 2:30 PM | |
| Thu., 3/28 | V Boys Lacrosse | Rocky Hill (Scrim.) | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Thu., 3/28 | V Girls Lacrosse | Joel Barlow (Scrim.) | Away - Joel Barlow HS-Joel Barlow HS Stadium [Directions] | 6:00 p.m. | 3:45 PM | |
| Sat., 3/30 | V Baseball | Weston | Home - Stamford HS-Cubeta Stadium [Directions] | L 8-10 | ||
| Sat., 3/30 | V Boys Volleyball | Kolbe Cathedral | Away - Kolbe Cathedral HS-Gym [Directions] | W 3-1 | 10:00 AM | |
| Sat., 3/30 | JV Boys Volleyball | Kolbe Cathedral | Away - Kolbe Cathedral HS-Gym [Directions] | L 2-0 | 10:00 AM | |
| Sat., 3/30 | V Girls Lacrosse | Southington | Away - Southington HS-2 TURF FIELD [Directions] | 10:00 a.m. | 7:30 AM | |
| Sat., 3/30 | JV Girls Lacrosse | Southington | Away - Southington HS-8 SubVLacrosse/Soccer [Directions] | 12:00 p.m. | 7:30 AM | |
| Sat., 3/30 | V Softball | Mercy | Home - Troy Complex-Diamond 1 [Directions] | L 2-5 | ||
| Sat., 3/30 | Miscellaneous Events | B. Lax to Marist college - Marist vs. Manhattan College | Home - TBA [Directions] | 1:00 p.m. | 11:00 AM (2 buses to Marist college) | B. Lax to Marist college - Marist vs. Manhattan College |
| Mon., 4/1 | V Baseball | Hall | Away - Hall HS-Varsity Baseball Diamond [Directions] | L 4-14 | 2:30 PM ( JV & V) | |
| Mon., 4/1 | JV Baseball | Hall | Away - Hall HS-JV Baseball Diamond [Directions] | 4:30 p.m. | 2:30 PM ( JV & V) | |
| Mon., 4/1 | FR Baseball | Darien | Away - Darien HS-DHS Baseball - JV Field [Directions] | 4:00 p.m. | 3:00 PM | |
| Mon., 4/1 | V Boys Outdoor Track | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 4:00 p.m. | 2:30 PM | |
| Mon., 4/1 | V Boys Volleyball | Newtown | Home - Westhill HS-Main Gym [Directions] | W 3-1 | ||
| Mon., 4/1 | V Girls Outdoor Track | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 4:00 p.m. | 2:30 PM | |
| Mon., 4/1 | V Softball | Kolbe Cathedral | Away - Went Field-Diamond #3 [Directions] | W 15-2 | 2:30 PM | |
| Wed., 4/3 | FR Boys Lacrosse | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 4:30 p.m. | 2:30 PM | |
| Wed., 4/3 | V Boys Volleyball | Harding | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 3-0 | ||
| Thu., 4/4 | V Boys Lacrosse | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 5:00 p.m. | 3:30 PM | |
| Thu., 4/4 | JV Boys Lacrosse | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 6:30 p.m. | 4:45 PM | |
| Thu., 4/4 | FR Boys Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | Postponed | 2:30 PM | |
| Thu., 4/4 | V Girls Lacrosse | Brien McMahon | Home - Stamford HS-Boyle Stadium [Directions] | 6:00 p.m. | ||
| Thu., 4/4 | JV Girls Lacrosse | Brien McMahon | Home - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | ||
| Fri., 4/5 | Miscellaneous Events | B. Volleyball to Sacred Heart U to see SHU vs. LIU game | Home - TBA [Directions] | 5:00 p.m. | 3:15 PM | B. Volleyball to Sacred Heart U to see SHU vs. LIU game - 5pm game |
| Sat., 4/6 | V Baseball | Sheehan | Away - West Side Field [Directions] | L 10-11 | 8:45 AM | |
| Sat., 4/6 | V Boys Lacrosse | Danbury | Home - Stamford HS-Boyle Stadium [Directions] | 12:00 p.m. | ||
| Sat., 4/6 | JV Boys Lacrosse | Danbury | Home - Stamford HS-Boyle Stadium [Directions] | 10:00 a.m. | ||
| Sat., 4/6 | FR Boys Lacrosse | Newtown | Away - Newtown HS-Blue and Gold Stadium [Directions] | 2:00 p.m. | 12:00 PM | |
| Sat., 4/6 | V Girls Lacrosse | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 11:00 a.m. | 9:00 AM ( JV & V) | |
| Sat., 4/6 | JV Girls Lacrosse | Danbury | Away - Danbury HS-Stadium Turf Field [Directions] | 12:30 p.m. | 9:00 AM ( JV & V) | |
| Sat., 4/6 | V Softball | Lauralton Hall | Home - Troy Complex-Diamond 1 [Directions] | 12:00 p.m. | ||
| Mon., 4/8 | V Baseball | Wilton | Away - Wilton HS-Varsity Baseball Field [Directions] | L 0-10 | 4:00 PM | |
| Mon., 4/8 | V Boys Outdoor Track | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 5:00 p.m. | 4:00 PM | |
| Mon., 4/8 | V Boys Tennis | St. Joseph | Home - Stamford HS-SHS Tennis Courts [Directions] | W 7-0 [Detailed Results] | ||
| Mon., 4/8 | V Girls Outdoor Track | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 5:00 p.m. | 4:00 PM | |
| Mon., 4/8 | V Softball | Staples | Away - Staples HS-Wakeman Field [Directions] | 5:00 p.m. | 2:45 PM | |
| Mon., 4/8 | V Girls Tennis | St. Joseph | Away - St. Joseph HS-Tennis Courts [Directions] | 5:00 p.m. | 3:15 PM | |
| Tue., 4/9 | V Boys Lacrosse | Greenwich | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Tue., 4/9 | JV Boys Lacrosse | Greenwich | Home - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/9 | V Boys Tennis | Brien McMahon | Away - Brien McMahon HS-Tennis Courts [Directions] | L 1-6 [Detailed Results] | 2:45 PM | |
| Tue., 4/9 | V Boys Volleyball | Bunnell | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 3-0 | ||
| Tue., 4/9 | JV Boys Volleyball | Bunnell | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 2-0 | ||
| Tue., 4/9 | V Girls Lacrosse | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 5:10 p.m. | 3:30 PM ( JV & V) | |
| Tue., 4/9 | JV Girls Lacrosse | Greenwich | Away - Greenwich HS-Field 3 [Directions] | Postponed | 3:30 PM ( JV & V) | |
| Tue., 4/9 | V Girls Tennis | Brien McMahon | Home - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/10 | V Baseball | Brien McMahon | Home - Stamford HS-Cubeta Stadium [Directions] | L 0-3 | ||
| Wed., 4/10 | JV Baseball | Brien McMahon | Home - Belltown Park-Barrett Field, Belltown Park [Directions] | 4:00 p.m. | ||
| Wed., 4/10 | V Softball | Fairfield Warde | Away - Fairfield Warde HS-Softball Diamond [Directions] | 4:00 p.m. | 2:30 PM | |
| Thu., 4/11 | V Girls Tennis | Bridgeport Central | Home - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 4/12 | V Boys Volleyball | Bridgeport Central | Away - Bridgeport Central HS-The Barry McLeod Court [Directions] | W 3-2 | 2:30 PM ( JV & V) | |
| Fri., 4/12 | JV Boys Volleyball | Bridgeport Central | Away - Bridgeport Central HS-The Barry McLeod Court [Directions] | L 0-2 | 2:45 PM ( JV & V) | |
| Sat., 4/13 | V Baseball | St. Joseph | Away - St. Joseph HS-Baseball Diamond [Directions] | 12:00 p.m. | 10:00 AM (Varsity) | |
| Sat., 4/13 | JV Baseball | St. Joseph | Away - Unity Park-Field 1 [Directions] | 11:00 a.m. | 9:00 AM (JV Only) | |
| Sat., 4/13 | FR Baseball | St. Joseph | Home - Belltown Park-Barrett Field, Belltown Park [Directions] | 1:00 p.m. | ||
| Sat., 4/13 | V Boys Lacrosse | Brookfield | Away - Brookfield HS-BHS Stadium Field [Directions] | 2:00 p.m. | 11:45 AM | |
| Sat., 4/13 | JV Boys Lacrosse | Brookfield | Away - Brookfield HS-BHS Stadium Field [Directions] | 12:00 p.m. | 9:45 AM | |
| Sat., 4/13 | FR Boys Lacrosse | New Canaan | Home - Stamford HS-Boyle Stadium [Directions] | 9:00 a.m. | ||
| Sat., 4/13 | V Girls Lacrosse | Brookfield | Home - Stamford HS-Boyle Stadium [Directions] | 11:00 a.m. | ||
| Sat., 4/13 | JV Girls Lacrosse | Brookfield | Home - Stamford HS-Boyle Stadium [Directions] | 12:30 p.m. | ||
| Sat., 4/13 | V Softball | St. Joseph | Home - Troy Complex-Diamond 1 [Directions] | 1:00 p.m. | ||
| Sat., 4/13 | JV Softball | St. Joseph | Home - Troy Complex-Diamond 2 [Directions] | 3:00 p.m. | ||
| Mon., 4/15 | V Baseball | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 4:00 p.m. | 2:30 PM (JV & V - 2 stops- Brien McMahon HS Then Roton MS (201 Highland Ave, Norwalk)) | |
| Mon., 4/15 | JV Baseball | Brien McMahon | Away - Roton MS [Directions] | 4:00 p.m. | 2:30 PM (JV & V - 2 stops- Brien McMahon HS Then Roton MS (201 Highland Ave, Norwalk)) | |
| Mon., 4/15 | FR Boys Lacrosse | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 12:00 p.m. | 10:45 AM | |
| Mon., 4/15 | V Boys Tennis | Darien | Home - Stamford HS-SHS Tennis Courts [Directions] | L 0-7 [Detailed Results] | ||
| Mon., 4/15 | V Boys Volleyball | Daniel Hand | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 3-0 | ||
| Mon., 4/15 | V Softball | Brien McMahon | Away - Brien McMahon HS-Softball Diamond [Directions] | 4:00 p.m. | 2:30 PM ( JV & V 2 Stops - Brien McMahon HS Then Brookside elementary (382 Highland Ave, Norwalk)) | |
| Mon., 4/15 | JV Softball | Brien McMahon | Away - Brookside Elementary School [Directions] | 4:30 p.m. | 2:30 PM ( JV & V 2 Stops - Brien McMahon HS Then Brookside elementary (382 Highland Ave, Norwalk)) | |
| Mon., 4/15 | V Girls Tennis | Darien | Away - Darien HS-DHS Tennis Courts [Directions] | 11:00 a.m. | 10:00 AM | |
| Tue., 4/16 | V Boys Lacrosse | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 4:30 p.m. | 2:30 PM | |
| Tue., 4/16 | JV Boys Lacrosse | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 6:00 p.m. | 4:00 PM | |
| Tue., 4/16 | V Boys Tennis | Staples | Home - Stamford HS-SHS Tennis Courts [Directions] | L 0-7 [Detailed Results] | ||
| Tue., 4/16 | V Girls Lacrosse | St. Joseph | Home - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/16 | JV Girls Lacrosse | St. Joseph | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Tue., 4/16 | V Girls Tennis | Staples | Away - Staples HS-Staples Tennis Courts [Directions] | 4:30 p.m. | 2:30 PM | |
| Wed., 4/17 | V Baseball | Bridgeport Central | Home - Cubeta Stadium [Directions] | 12:00 p.m. | ||
| Wed., 4/17 | V Boys Tennis | Bridgeport Central | Away - Bridgeport Central HS-Central High School Tennis Courts [Directions] | W 6-0 [Detailed Results] | 9:30 AM | |
| Wed., 4/17 | V Boys Volleyball | St. Joseph | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 3-1 | ||
| Wed., 4/17 | JV Boys Volleyball | St. Joseph | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 2-1 | ||
| Wed., 4/17 | V Softball | Bridgeport Central | Away - Bridgeport Central-Varsity Softball Field [Directions] | 12:00 p.m. | 10:00 AM ( JV & V) | |
| Wed., 4/17 | JV Softball | Bridgeport Central | Away - Bridgeport Central HS-Softball Diamond 2 [Directions] | 12:00 p.m. | 10:00 AM ( JV & V) | |
| Wed., 4/17 | Miscellaneous Events | G. Lax to Pace University to see Pace versus Southern CT State | Home - TBA [Directions] | 7:00 p.m. | G. Lax to Pace University to see Pace versus Southern CT State | |
| Thu., 4/18 | V Boys Lacrosse | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | 6:00 p.m. | 4:00 PM | |
| Thu., 4/18 | JV Boys Lacrosse | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | 4:00 p.m. | 2:15 PM | |
| Thu., 4/18 | V Boys Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | W 3-0 | 9:30 AM ( JV & V) | |
| Thu., 4/18 | JV Boys Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | W 2-0 | 9:30 AM ( JV & V) | |
| Thu., 4/18 | V Girls Lacrosse | Norwalk | Home - Stamford HS-Boyle Stadium [Directions] | 4:30 p.m. | ||
| Fri., 4/19 | V Baseball | Darien | Away - Darien HS-DHS Baseball - Varsity Field [Directions] | 12:00 p.m. | 10:30 AM ( JV & V) | |
| Fri., 4/19 | JV Baseball | Darien | Away - Darien HS-DHS Baseball - JV Field [Directions] | 12:00 p.m. | 10:30 AM ( JV & V) | |
| Fri., 4/19 | FR Baseball | Darien | Home - Belltown Park-Barrett Field, Belltown Park [Directions] | 12:00 p.m. | ||
| Fri., 4/19 | V Softball | Darien | Home - Troy Complex-Diamond 1 [Directions] | 1:00 p.m. | ||
| Fri., 4/19 | JV Softball | Darien | Home - Troy Complex-Diamond 1 [Directions] | 2:45 p.m. | ||
| Sat., 4/20 | V Boys Lacrosse | Trumbull | Home - Stamford HS-Boyle Stadium [Directions] | 12:00 p.m. | ||
| Sat., 4/20 | JV Boys Lacrosse | Trumbull | Home - Stamford HS-Boyle Stadium [Directions] | 10:00 a.m. | ||
| Sat., 4/20 | V Girls Lacrosse | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 12:00 p.m. | 8:00 AM ( JV & V) | |
| Sat., 4/20 | JV Girls Lacrosse | Trumbull | Away - Trumbull HS-McDougall Stadium [Directions] | 10:15 a.m. | 8:00 AM ( JV & V) | |
| Mon., 4/22 | V Baseball | Staples | Away - Staples HS-Baseball Diamond [Directions] | 4:30 p.m. | 2:30 PM ( JV & V - 2 stops - Staples Hs then Wakeman Field (on the other side of the campus)) | |
| Mon., 4/22 | JV Baseball | Staples | Away - Staples HS-Wakeman Field [Directions] | 4:30 p.m. | 2:30 PM ( JV & V - 2 stops - Staples Hs then Wakeman Field (on the other side of the campus)) | |
| Mon., 4/22 | FR Baseball | Staples | Home - Belltown Park-Barrett Field, Belltown Park [Directions] | 4:00 p.m. | ||
| Mon., 4/22 | FR Boys Lacrosse | Trumbull | Away - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | 2:30 PM | |
| Mon., 4/22 | V Boys Outdoor Track | Danbury | Away - Danbury HS-Stadium Track [Directions] | 4:30 p.m. | 2:30 PM | |
| Mon., 4/22 | V Boys Tennis | Danbury | Away - Danbury HS-DHS Tennis Courts [Directions] | L 2-5 [Detailed Results] | 2:30 PM | |
| Mon., 4/22 | V Girls Outdoor Track | Danbury | Away - Danbury HS-Stadium Track [Directions] | 4:30 p.m. | 2:30 PM | |
| Mon., 4/22 | V Softball | Staples | Home - Troy Complex-Diamond 1 [Directions] | 4:00 p.m. | ||
| Mon., 4/22 | JV Softball | Staples | Home - Troy Complex-Diamond 1 [Directions] | Cancelled | 12:00 PM | |
| Mon., 4/22 | V Girls Tennis | Danbury | Home - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | V Boys Tennis | New Canaan | Home - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | V Boys Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | L 0-3 | 2:30 PM ( JV & V) | |
| Tue., 4/23 | JV Boys Volleyball | Trumbull | Away - Trumbull HS-THS Main Gym [Directions] | L 0-2 | 2:30 PM | |
| Tue., 4/23 | V Girls Tennis | New Canaan | Away - New Canaan HS-NCHS Tennis Courts [Directions] | 4:00 p.m. | 2:45 PM | |
| Wed., 4/24 | V Baseball | Ridgefield | Away - Governor Field [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | JV Baseball | Ridgefield | Home - Belltown Park-Barrett Field, Belltown Park [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | FR Baseball | Ridgefield | Away - East Ridge MS-Baseball Field [Directions] | 4:00 p.m. | 2:30 PM (Freshman and Varsity) | |
| Wed., 4/24 | FR Boys Lacrosse | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | 4:15 PM | |
| Wed., 4/24 | V Boys Tennis | Ridgefield | Away - Ridgefield HS-RHS Tennis Courts [Directions] | 4:30 p.m. | ||
| Wed., 4/24 | V Softball | Ridgefield | Away - Ridgefield HS-Varsity Softball Field [Directions] | 4:00 p.m. | 2:30 PM ( JV & V) | |
| Wed., 4/24 | V Girls Tennis | Ridgefield | Home - Stamford HS-SHS Tennis Courts [Directions] | 4:30 p.m. | ||
| Thu., 4/25 | V Boys Lacrosse | Norwalk | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Thu., 4/25 | JV Boys Lacrosse | Norwalk | Home - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | ||
| Thu., 4/25 | V Boys Tennis | Westhill | Home - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 4/25 | V Boys Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | L 0-3 | 2:30 PM ( JV & V) | |
| Thu., 4/25 | JV Boys Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | W 2-0 | 2:30 PM ( JV & V) | |
| Thu., 4/25 | V Girls Lacrosse | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | 5:30 p.m. | 4:00 PM ( Varsity only) | |
| Thu., 4/25 | JV Girls Lacrosse | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Lower [Directions] | 4:00 p.m. | 2:30 PM ( JV only) | |
| Thu., 4/25 | V Girls Tennis | Westhill | Away - Westhill HS-Westhill Tennis Courts [Directions] | 4:00 p.m. | 3:00 PM | |
| Fri., 4/26 | V Baseball | Danbury | Home - Cubeta Stadium [Directions] | 4:00 p.m. | ||
| Fri., 4/26 | JV Baseball | Danbury | Home - Belltown Park-Barrett Field, Belltown Park [Directions] | 4:00 p.m. | ||
| Fri., 4/26 | FR Baseball | Danbury | Away - Danbury HS-V Baseball Field [Directions] | 4:30 p.m. | 2:30 PM ( JV & V) | |
| Fri., 4/26 | V Softball | Danbury | Away - Danbury HS-V Softball field [Directions] | 4:30 p.m. | 2:30 PM ( JV & V) | |
| Fri., 4/26 | JV Softball | Danbury | Away - Danbury HS-JV Softball Field [Directions] | 4:30 p.m. | 2:30 PM ( JV & V) | |
| Sat., 4/27 | V Boys Lacrosse | Bunnell-Stratford | Home - Stamford HS-Boyle Stadium [Directions] | 12:30 p.m. | ||
| Sat., 4/27 | FR Boys Lacrosse | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 10:00 a.m. | 9:00 AM | |
| Sat., 4/27 | V Boys Volleyball | Westhill | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 0-3 | ||
| Sat., 4/27 | JV Boys Volleyball | Westhill | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 2-1 | ||
| Sat., 4/27 | V Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 10:30 a.m. | 9:00 AM ( JV & V) | |
| Sat., 4/27 | JV Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 12:00 p.m. | 9:00 AM ( JV & V) | |
| Sat., 4/27 | Miscellaneous Events | Softball to see UConn softball vs Villanova | Home - TBA [Directions] | 6:00 p.m. | 3:30 PM | UConn softball vs Villanova - Storrs - 6pm |
| Mon., 4/29 | V Baseball | New Canaan | Away - Mead Park-Baseball Field [Directions] | 4:00 p.m. | 2:45 PM (Varsity Only) | |
| Mon., 4/29 | JV Baseball | New Canaan | Away - Waveny Park-Coppo Field [Directions] | 4:00 p.m. | 2:45 PM (JV Only) | |
| Mon., 4/29 | FR Baseball | New Canaan | Home - Belltown Park-Barrett Field, Belltown Park [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | V Boys Lacrosse | Immaculate | Home - Stamford HS-Boyle Stadium [Directions] | 4:30 p.m. | ||
| Mon., 4/29 | V Boys Tennis | Trumbull | Away - Trumbull HS-Tennis Courts [Directions] | 4:00 p.m. | 2:30 PM | |
| Mon., 4/29 | V Girls Lacrosse | Immaculate | Away - Immaculate HS-Mustang Valley [Directions] | 4:30 p.m. | 2:30 PM | |
| Mon., 4/29 | V Softball | New Canaan | Home - Troy Complex-Diamond 1 [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | JV Softball | New Canaan | Home - Troy Complex-Diamond 2 [Directions] | 4:00 p.m. | 12:00 PM | |
| Mon., 4/29 | V Girls Tennis | Trumbull | Home - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/30 | V Boys Tennis | Greenwich | Home - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 4/30 | V Boys Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | L 2-3 | 2:45 PM (No JV Game this day) | |
| Tue., 4/30 | V Girls Tennis | Greenwich | Away - Greenwich HS-Tennis Courts [Directions] | 4:15 p.m. | 3:00 PM | |
| Wed., 5/1 | V Baseball | Westhill | Away - Cubeta Stadium [Directions] | 7:00 p.m. | TBA (Night Game At Cubeta - Parent Drop off / Pick up) | |
| Wed., 5/1 | JV Baseball | Westhill | Away - Westhill HS-Varsity Baseball Field [Directions] | 4:00 p.m. | 2:45 PM (JV Only) | |
| Wed., 5/1 | FR Baseball | Westhill | Home - Belltown Park-Barrett Field, Belltown Park [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | FR Boys Lacrosse | Wilton | Away - Allen's Meadow-Lacrosse Field #1 [Directions] | 4:15 p.m. | 2:30 PM | |
| Wed., 5/1 | V Girls Lacrosse | Masuk | Home - Stamford HS-Boyle Stadium [Directions] | 4:30 p.m. | ||
| Wed., 5/1 | JV Girls Lacrosse | Masuk | Home - Stamford HS-Boyle Stadium [Directions] | 6:00 p.m. | ||
| Wed., 5/1 | JV Softball | Westhill | Home - Troy Complex-Diamond 1 [Directions] | 4:00 p.m. | 12:00 PM | |
| Thu., 5/2 | V Boys Tennis | Fairfield Ludlowe | Home - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/2 | V Boys Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | L 1-3 | 2:00 PM | |
| Thu., 5/2 | JV Boys Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | W 2-0 | 2:00 PM | |
| Thu., 5/2 | V Softball | Westhill | Home - Troy Complex-Diamond 1 [Directions] | 6:30 p.m. | ||
| Thu., 5/2 | V Girls Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Tennis Courts [Directions] | 4:00 p.m. | 2:30 PM | |
| Fri., 5/3 | V Baseball | Trumbull | Home - Cubeta Stadium [Directions] | 5:00 p.m. | ||
| Fri., 5/3 | JV Baseball | Trumbull | Home - Belltown Park-Barrett Field, Belltown Park [Directions] | 5:00 p.m. | ||
| Fri., 5/3 | FR Baseball | Trumbull | Away - Trumbull HS-Varsity Baseball Field [Directions] | 5:15 p.m. | 2:30 PM | |
| Fri., 5/3 | V Boys Volleyball | Darien | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 0-3 | ||
| Fri., 5/3 | JV Boys Volleyball | Darien | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 2-1 | ||
| Fri., 5/3 | V Softball | Trumbull | Away - Trumbull HS-Varsity Softball Diamond [Directions] | 5:15 p.m. | 2:30 PM ( JV & V) | |
| Fri., 5/3 | JV Softball | Trumbull | Away - Trumbull HS-JV Softball Diamond [Directions] | 5:15 p.m. | 2:30 PM ( JV & V) | |
| Sat., 5/4 | V Boys Lacrosse | Masuk | Away - Masuk HS-Benedict Stadium Field @ Masuk HS [Directions] | 1:00 p.m. | 10:15 AM | |
| Mon., 5/6 | V Baseball | Greenwich | Away - Julian Curtiss School [Directions] | 4:30 p.m. | 2:30 PM ( V only to Julian Curtis) | |
| Mon., 5/6 | FR Baseball | Greenwich | Home - Belltown Park-Barrett Field, Belltown Park [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | FR Boys Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | 4:00 p.m. | 2:30 PM | |
| Mon., 5/6 | V Boys Tennis | Fairfield Warde | Home - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | V Boys Volleyball | Bridgeport Central | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 3-0 | ||
| Mon., 5/6 | JV Boys Volleyball | Bridgeport Central | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 2-0 | ||
| Mon., 5/6 | V Softball | Greenwich | Home - Troy Complex-Diamond 1 [Directions] | 7:00 p.m. | ||
| Mon., 5/6 | JV Softball | Greenwich | Home - Troy Complex-Diamond 1 [Directions] | 4:00 p.m. | 12:00 PM | |
| Mon., 5/6 | V Girls Tennis | Fairfield Warde | Away - Fairfield Warde HS-Blake Courts [Directions] | 4:30 p.m. | 2:30 PM | |
| Tue., 5/7 | JV Baseball | Greenwich | Away - Julian Curtiss School [Directions] | 4:30 p.m. | 3:15 PM (JV only) | |
| Tue., 5/7 | V Boys Lacrosse | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 6:30 p.m. | 5:15 PM | |
| Tue., 5/7 | JV Boys Lacrosse | Darien | Away - Darien HS-DHS Center Oval - Turf [Directions] | 4:00 p.m. | 2:45 PM | |
| Tue., 5/7 | V Boys Outdoor Track | Wilton | Away - Wilton HS-Track [Directions] | 4:30 p.m. | 2:30 PM | |
| Tue., 5/7 | V Boys Tennis | Norwalk | Away - Grassroots Tennis and Education-Grassroots Tennis Courts [Directions] | 4:00 p.m. | 2:45 PM | |
| Tue., 5/7 | V Girls Lacrosse | Darien | Home - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | JV Girls Lacrosse | Darien | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Tue., 5/7 | V Girls Outdoor Track | Wilton | Away - Wilton HS-Track [Directions] | 4:30 p.m. | 2:30 PM | |
| Tue., 5/7 | V Girls Tennis | Norwalk | Home - Stamford HS-SHS Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | V Baseball | Fairfield Ludlowe | Away - Kiwanis Field-Baseball Diamond [Directions] | 4:00 p.m. | 2:30 PM (Varsity Only) | |
| Wed., 5/8 | JV Baseball | Fairfield Ludlowe | Away - Owen Fish Park-Owen Fish [Directions] | 4:00 p.m. | 2:30 PM (JV Only) | |
| Wed., 5/8 | FR Baseball | Fairfield Ludlowe | Home - Belltown Park-Barrett Field, Belltown Park [Directions] | Postponed | ||
| Wed., 5/8 | FR Boys Lacrosse | Staples | Away - Staples HS-Wakeman Field E (grass) [Directions] | 4:30 p.m. | 2:30 PM | |
| Wed., 5/8 | V Boys Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | L 0-3 | 2:30 PM ( JV & V) | |
| Wed., 5/8 | JV Boys Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | L 0-2 | 2:30 PM ( JV & V) | |
| Wed., 5/8 | V Softball | Fairfield Ludlowe | Home - Troy Complex-Diamond 1 [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | JV Softball | Fairfield Ludlowe | Home - Troy Complex-Diamond 2 [Directions] | Postponed | ||
| Thu., 5/9 | V Boys Lacrosse | Fairfield Ludlowe | Home - Stamford HS-Boyle Stadium [Directions] | 5:30 p.m. | ||
| Thu., 5/9 | JV Boys Lacrosse | Fairfield Ludlowe | Home - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | ||
| Thu., 5/9 | V Boys Tennis | Wilton | Away - Wilton HS-Tennis Courts [Directions] | 4:30 p.m. | 2:30 PM | |
| Thu., 5/9 | V Boys Volleyball | Norwalk | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 3-0 | ||
| Thu., 5/9 | JV Boys Volleyball | Brien McMahon | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 2-1 | ||
| Thu., 5/9 | V Girls Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 6:00 p.m. | 3:45 PM (Varsity Only) | |
| Thu., 5/9 | JV Girls Lacrosse | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | 2:30 PM ( JV only) | |
| Thu., 5/9 | V Girls Tennis | Wilton | Home - Stamford HS-SHS Tennis Courts [Directions] | 4:30 p.m. | ||
| Sat., 5/11 | V Baseball | Fairfield Warde | Away - Fairfield Warde HS-Baseball Diamond [Directions] | 12:00 p.m. | 10:00 AM (Varsity Only) | |
| Sat., 5/11 | JV Baseball | Fairfield Warde | Away - Fairfield Warde HS-Baseball Diamond [Directions] | 2:00 p.m. | 12:00 PM (JV Only) | |
| Sat., 5/11 | FR Baseball | Fairfield Warde | Home - Belltown Park-Barrett Field, Belltown Park [Directions] | 12:00 p.m. | ||
| Sat., 5/11 | V Boys Lacrosse | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 5:15 p.m. | 4:00 PM | |
| Sat., 5/11 | JV Boys Lacrosse | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 3:00 p.m. | 1:45 PM | |
| Sat., 5/11 | V Girls Lacrosse | Westhill | Home - Stamford HS-Boyle Stadium [Directions] | 12:00 p.m. | ||
| Sat., 5/11 | JV Girls Lacrosse | Westhill | Home - Stamford HS-Boyle Stadium [Directions] | 10:30 a.m. | ||
| Sat., 5/11 | V Softball | Fairfield Warde | Home - Fairfield Warde HS-Softball Diamond [Directions] | 11:30 a.m. | 9:45 AM | |
| Sat., 5/11 | JV Softball | Fairfield Warde | Home - Troy Complex-Diamond 1 [Directions] | Cancelled | ||
| Mon., 5/13 | V Baseball | Norwalk | Home - Cubeta Stadium [Directions] | 7:00 p.m. | ||
| Mon., 5/13 | JV Baseball | Norwalk | Home - Belltown Park-Barrett Field, Belltown Park [Directions] | 4:00 p.m. | ||
| Mon., 5/13 | FR Baseball | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 4:00 p.m. | 2:45 PM | |
| Mon., 5/13 | FR Boys Lacrosse | Trumbull | Away - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | 2:30 PM | |
| Mon., 5/13 | V Boys Volleyball | Fairfield Ludlowe | Home - Stamford HS-Kuczo Gymnasium [Directions] | L 0-3 | ||
| Mon., 5/13 | JV Boys Volleyball | Fairfield Ludlowe | Home - Stamford HS-Kuczo Gymnasium [Directions] | W 2-1 | ||
| Mon., 5/13 | V Softball | Norwalk | Away - Brien McMahon HS-Softball Diamond [Directions] | 4:00 p.m. | 2:30 PM (Jv and Varsity) | |
| Mon., 5/13 | JV Softball | Norwalk | Away - Naramake School Field [Directions] | 4:00 p.m. | 2:30 PM (JV and varsity) | |
| Tue., 5/14 | V Baseball | Wilton | Home - Stamford HS-SHS Baseball Diamond [Directions] | 4:30 p.m. | ||
| Tue., 5/14 | JV Baseball | Wilton | Home - Belltown Park-Barrett Field, Belltown Park [Directions] | 4:30 p.m. | ||
| Tue., 5/14 | FR Baseball | Wilton | Away - Allen's Meadow-Baseball Diamond [Directions] | 4:15 p.m. | 2:30 PM | |
| Tue., 5/14 | V Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 6:00 p.m. | 3:45 PM | |
| Tue., 5/14 | JV Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | 2:30 PM | |
| Tue., 5/14 | V Boys Outdoor Track | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 2:30 p.m. | 2:45 PM (Boys and Girls Field team) | |
| Tue., 5/14 | V Girls Lacrosse | Fairfield Warde | Home - Stamford HS-Boyle Stadium [Directions] | 4:15 p.m. | ||
| Tue., 5/14 | JV Girls Lacrosse | Fairfield Warde | Home - Stamford HS-Boyle Stadium [Directions] | 5:45 p.m. | ||
| Tue., 5/14 | V Girls Outdoor Track | Westhill | Away - Westhill HS-J. Walter Kennedy Stadium [Directions] | 2:30 p.m. | 2:45 PM (Boys and Girls Field team) | |
| Tue., 5/14 | V Softball | Wilton | Away - Wilton HS-Varsity Softball Field [Directions] | 7:00 p.m. | 4:45 PM (Varsity only) | |
| Tue., 5/14 | JV Softball | Wilton | Away - Wilton HS-JV Softball Field [Directions] | Cancelled | 2:30 PM (JV Only) | |
| Wed., 5/15 | FR Boys Lacrosse | Westhill | Home - Stamford HS-Boyle Stadium [Directions] | 5:00 p.m. | ||
| Wed., 5/15 | V Boys Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | W 3-0 | 2:30 PM | |
| Wed., 5/15 | JV Boys Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | W 2-1 | 2:30 PM | |
| Thu., 5/16 | V Boys Outdoor Track | Westhill | Home - Stamford HS-Boyle Stadium [Directions] | 3:00 p.m. | ||
| Thu., 5/16 | V Girls Outdoor Track | Westhill | Home - Stamford HS-Boyle Stadium [Directions] | 3:00 p.m. | ||
| Sat., 5/18 | V Boys Lacrosse | Jonathan Law | Home - Stamford HS-Boyle Stadium [Directions] | 2:00 p.m. | ||
| Sat., 5/18 | JV Boys Lacrosse | Jonathan Law | Home - Stamford HS-Boyle Stadium [Directions] | 12:00 p.m. | ||
| Tue., 5/21 | V Boys Outdoor Track | FCIAC Championship | Away - Danbury HS-Danbury HS Stadium | 4:30 p.m. | 12:15 PM | |
| Pending change awaiting acceptance by one or more parties involved: Time to 2:30 p.m. | ||||||
| Tue., 5/21 | V Girls Outdoor Track | FCIAC Championship | Away - Danbury HS-Danbury HS Stadium | 2:00 p.m. | 12:15 PM | |
| Pending change awaiting acceptance by one or more parties involved: Time to 2:30 p.m. | ||||||
| Fri., 5/24 | V Boys Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 5:00 p.m. | 2:40 PM | |
| Tue., 5/28 | V Girls Lacrosse | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 5:00 p.m. | 3:00 PM | |
| Wed., 5/29 | V Boys Lacrosse | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 5:30 p.m. | 3:30 PM | |
| Wed., 5/29 | V Boys Outdoor Track | LL State Championships - Veterans Stadium - New Britain | Away - Not Listed | 4:00 p.m. | 12:30 PM | |
| Wed., 5/29 | V Boys Volleyball | Farmington | Away - Farmington HS [Directions] | 6:00 p.m. | 2:30 PM | |
| Wed., 5/29 | V Girls Outdoor Track | LL State Championships - Veterans Stadium - New Britain | Away - Not Listed | 4:00 p.m. | 12:30 PM | |
| Fri., 6/21 | V Boys Basketball | NCAA Showcase At Connecticut College (1pm Vs Warde - 3pm vs Fitch) | Away - Not Listed-Connecticut College - New London | 1:00 p.m. | 10:00 AM | |
| Sat., 6/22 | V Boys Basketball | NCAA Showcase At Connecticut College (9am vs Fitch) | Away - Not Listed-Connecticut College - New London | 9:00 a.m. | 6:15 AM | |