| Stamford 2018-19 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 780 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| TBA | JV Baseball | Wilton | Away - JV Baseball Field [Directions] | 4:00 p.m. | 1st 2:15pm | |
| TBA | JV Baseball | Wright Tech | Away - Cubetta Field [Directions] | TBA | 1st 2:30pm | |
| TBA | JV Baseball | Brookfield | Home - SHS Baseball Field [Directions] | TBA | ||
| TBA | JV Baseball | St. Joseph | Away - Unity Park, Trumbull [Directions] | TBA | Myers 2pm | |
| TBA | FR Baseball | St. Joseph | Home - SHS Baseball Field [Directions] | TBA | ||
| TBA | FR Baseball | Wilton | Home - SHS Baseball Field [Directions] | TBA | ||
| TBA | FR Boys Basketball | Trinity Catholic | Away - Walsh Court | Cancelled | Myers 3pm | |
| TBA | FR Football | Fairfield Warde | Away - Tomlinson MS [Directions] | TBA | 2:30 (Bob) | |
| TBA | FR Boys Lacrosse | Brien McMahon | Home - Boyle Stadium, SHS [Directions] | TBA | ||
| TBA | FR Boys Soccer | Danbury | Away - Danbury HS Grass Soccer Field [Directions] | TBA | ||
| TBA | V Boys Swimming and Diving | Glastonbury | Away - Glastonbury HS Pool [Directions] | TBA | ||
| TBA | JV Softball | New Canaan | Home - SHS Softball Field [Directions] | 2:00 p.m. | Parent | |
| TBA | JV Softball | Bridgeport Central | Away - Ripken Field [Directions] | 4:00 p.m. | 1st 2:15pm | |
| TBA | JV Softball | Shelton | Away - Shelton HS Softball Field [Directions] | TBA | Myers 2pm | |
| Sat., 8/25 | V Football | Norwalk (Scrim.) | Home - Stamford HS [Directions] | 10:00 a.m. | ||
| Tue., 8/28 | V Boys Soccer | King and Low-Heywood Thomas (Scrim.) | Away - King LowHeywood Thomas | 4:00 p.m. | 2:30 pm | |
| Wed., 8/29 | V Boys Soccer | Greenwich (Scrim.) | Away - Greenwich HS [Directions] | 4:00 p.m. | 2:30 pm | |
| Fri., 8/31 | V Football | Bethel (Scrim.) | Away - DeSantis Field at Bethel HS [Directions] | 5:30 p.m. | 2:45 | |
| Fri., 8/31 | JV Football | Bethel (Scrim.) | Away - DeSantis Field at Bethel HS [Directions] | 5:30 p.m. | 2:45 | |
| Fri., 8/31 | FR Football | Bethel (Scrim.) | Away - Berry School Field [Directions] | 5:30 p.m. | 2:45 | |
| Fri., 8/31 | V Boys Soccer | Foran (Scrim.) | Away - Foran HIgh School [Directions] | 4:00 p.m. | 1:30 | |
| Fri., 8/31 | V Field Hockey | King and Low-Heywood Thomas (Scrim.) | Home - Boyle Stadium, SHS [Directions] | 4:00 p.m. | ||
| Fri., 8/31 | V Girls Soccer | Trinity Catholic (Scrim.) | Away | 4:30 p.m. | 2:15 | |
| Sat., 9/1 | V Boys Soccer | Ansonia (Scrim.) | Away - Amity HS [Directions] | 9:00 a.m. | 7:15 | |
| Sat., 9/1 | V Field Hockey | Norwalk (Scrim.) | Away [Directions] | 12:00 p.m. | 10:30 | |
| Sat., 9/1 | JV Field Hockey | Norwalk (Scrim.) | Away [Directions] | 12:00 p.m. | 10:30 | |
| Sat., 9/1 | V Girls Soccer | Shelton (Scrim.) | Away - Shelton HS [Directions] | 8:30 a.m. | 6:30am | |
| Sat., 9/1 | V Girls Volleyball | Greenwich (Scrim.) | Home - Stamford HS [Directions] | 9:00 a.m. | 9A-1P | |
| Wed., 9/5 | V Girls Volleyball | Staples (Scrim.) | Away [Directions] | 3:30 p.m. | 2:30 (Dave) | 3:30- 7:30 |
| Fri., 9/7 | V Football | Fairfield Warde | Home - Stamford HS [Directions] | L 24-28 | ||
| Fri., 9/7 | V Field Hockey | Pomperaug | Away - Sports Complex & Track [Directions] | L 0-3 | 2:45 (Dave) | |
| Fri., 9/7 | JV Field Hockey | Pomperaug | Away - Sports Complex & Track [Directions] | 5:00 p.m. | 2:45 (Dave) | |
| Fri., 9/7 | V Girls Soccer | Trumbull | Away - New Turf Field [Directions] | L 0-6 | 2:30 (Bob) | |
| Fri., 9/7 | JV Girls Soccer | Trumbull | Away - The Pit [Directions] | 4:00 p.m. | ||
| Fri., 9/7 | V Girls Volleyball | Shelton | Home - Stamford HS [Directions] | W 3-2 | 4 pm Foran vs Trinity 6 pm Stamford vs Shelton | |
| Sat., 9/8 | JV Football | Fairfield Warde | Away - Tomlinson MS [Directions] | 10:30 a.m. | 8:30am (Bob) | |
| Sat., 9/8 | V Boys Soccer | Trumbull | Home - Stamford High Soccer Field [Directions] | L 1-4 | ||
| Sat., 9/8 | JV Boys Soccer | Trumbull | Home - Stamford High Soccer Field [Directions] | L 0-1 | ||
| Sat., 9/8 | FR Boys Soccer | Trumbull | Away - New Turf Field [Directions] | T 2-2 | 10:30am (1st Student) | |
| Sat., 9/8 | V Girls Volleyball | Foran | Home - Stamford HS [Directions] | W 3-0 | 4pm Shelton vs Trinity 6pm Stamford vs Foran | |
| Tue., 9/11 | V Boys Cross Country | Ridgefield, Westhill, Darien | Away - Upper Grass Field [Directions] | 4:00 p.m. | ||
| Tue., 9/11 | V Girls Cross Country | Ridgefield, Westhill, Darien | Away - Upper Grass Field [Directions] | 4:00 p.m. | ||
| Tue., 9/11 | V Girls Soccer | Ridgefield | Home - Stamford High Soccer Field [Directions] | L 0-6 | ||
| Tue., 9/11 | JV Girls Soccer | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 5:30 p.m. | 4:00pm 1st Student | |
| Wed., 9/12 | V Boys Soccer | Ridgefield | Away - Tiger Hollow Stadium [Directions] | L 2-3 | 2:15 pm | |
| Wed., 9/12 | JV Boys Soccer | Ridgefield | Away - Lower Grass Field [Directions] | L 0-1 | ||
| Wed., 9/12 | FR Boys Soccer | Ridgefield | Home [Directions] | L 0-4 | ||
| Wed., 9/12 | V Field Hockey | Immaculate | Home - Stamford HS [Directions] | L 1-6 | ||
| Wed., 9/12 | JV Field Hockey | Immaculate | Home - Stamford HS [Directions] | 4:30 p.m. | ||
| Wed., 9/12 | V Girls Volleyball | Weston | Away - WHS Gymnasium [Directions] | W 3-1 | ||
| Wed., 9/12 | JV Girls Volleyball | Weston | Away - WHS Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 9/13 | FR Football | Ridgefield | Home [Directions] | 4:00 p.m. | ||
| Thu., 9/13 | V Girls Soccer | Fairfield Ludlowe | Away - Taft Field [Directions] | L 3-1 | ||
| Thu., 9/13 | JV Girls Soccer | Fairfield Ludlowe | Away - Sturges Park [Directions] | 4:00 p.m. | ||
| Fri., 9/14 | V Football | Ridgefield | Away - Tiger Hollow Stadium [Directions] | L 12-42 | ||
| Fri., 9/14 | V Boys Soccer | Fairfield Ludlowe | Home - Stamford High Soccer Field [Directions] | L 2-1 | ||
| Fri., 9/14 | JV Boys Soccer | Fairfield Ludlowe | Home - Rippowam Field [Directions] | L 1-4 | ||
| Fri., 9/14 | FR Boys Soccer | Fairfield Ludlowe | Away - Roger Ludlowe MS [Directions] | W 3-1 | ||
| Fri., 9/14 | V Field Hockey | Ridgefield | Away - Tiger Hollow Stadium [Directions] | L 1-3 | ||
| Fri., 9/14 | V Girls Swimming and Diving | Danbury | Away - O'Neil Center @ Western Connecticut State University [Directions] | Westhill 93 Danbury 73 | ||
| Fri., 9/14 | V Girls Volleyball | Trumbull | Home - Stamford HS [Directions] | L 1-3 | ||
| Fri., 9/14 | JV Girls Volleyball | Trumbull | Home - Stamford HS [Directions] | 5:00 p.m. | ||
| Fri., 9/14 | FR Girls Volleyball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 9/15 | JV Football | Ridgefield | Home [Directions] | 10:30 a.m. | ||
| Sat., 9/15 | JV Field Hockey | Ridgefield | Away - Tiger Hollow Turf Field II [Directions] | 4:00 p.m. | ||
| Mon., 9/17 | V Boys Cross Country | Staples, Fairfield Warde, Trumbull | Away - Staples Stadium [Directions] | 4:00 p.m. | ||
| Mon., 9/17 | V Girls Cross Country | Staples, Fairfield Warde, Trumbull | Away - Staples Stadium [Directions] | 4:00 p.m. | ||
| Mon., 9/17 | V Field Hockey | Fairfield Ludlowe | Home - Stamford HS [Directions] | L 0-4 | ||
| Mon., 9/17 | JV Field Hockey | Fairfield Ludlowe | Home - Stamford HS [Directions] | 5:30 p.m. | ||
| Mon., 9/17 | V Girls Swimming and Diving | Fairfield Warde | Home - Westhill Pool [Directions] | 3:30 p.m. | ||
| Mon., 9/17 | V Girls Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | L 3-2 | ||
| Mon., 9/17 | JV Girls Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 9/17 | FR Girls Volleyball | Ridgefield | Home [Directions] | 4:00 p.m. | ||
| Thu., 9/20 | FR Football | Newtown | Away - Blue and Gold Stadium [Directions] | 4:00 p.m. | ||
| Thu., 9/20 | V Field Hockey | Darien | Home - Stamford HS [Directions] | L 1-11 | ||
| Thu., 9/20 | JV Field Hockey | Darien | Home - Stamford HS [Directions] | 5:30 p.m. | ||
| Thu., 9/20 | V Girls Soccer | New Canaan | Home - Stamford High Soccer Field [Directions] | L 6-0 | ||
| Thu., 9/20 | JV Girls Soccer | New Canaan | Home - Rippowam Field [Directions] | 4:00 p.m. | ||
| Thu., 9/20 | FR Girls Volleyball | Fairfield Ludlowe | Away - FLHS Aux Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/21 | V Boys Soccer | New Canaan | Away - Conner Field [Directions] | W 3-2 | 2:15 pm | |
| Fri., 9/21 | JV Boys Soccer | New Canaan | Away - Saxe MS Field [Directions] | W 2-0 | ||
| Fri., 9/21 | FR Boys Soccer | New Canaan | Home [Directions] | T 1-1 | ||
| Fri., 9/21 | V Girls Volleyball | Fairfield Ludlowe | Home - Stamford HS [Directions] | L 2-3 | ||
| Fri., 9/21 | JV Girls Volleyball | Fairfield Ludlowe | Home - Stamford HS [Directions] | 5:30 p.m. | ||
| Sat., 9/22 | V Football | Trinity Catholic | Away - Gaglio Field | W 19-7 | ||
| Sat., 9/22 | JV Football | Trinity Catholic | Home [Directions] | Cancelled | ||
| Sat., 9/22 | V Girls Soccer | Brien McMahon | Home - Stamford High Soccer Field [Directions] | L 0-4 | ||
| Sat., 9/22 | JV Girls Soccer | Brien McMahon | Home - Rippowam Field [Directions] | 10:00 a.m. | ||
| Mon., 9/24 | V Boys Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | T 1-1 | 4:30 pm | |
| Mon., 9/24 | JV Boys Soccer | Brien McMahon | Away - Pride Field (BMHS) [Directions] | L 2-3 | ||
| Mon., 9/24 | FR Boys Soccer | Brien McMahon | Home [Directions] | W 1-0 | ||
| Mon., 9/24 | V Field Hockey | Greenwich | Away - Cardinal Stadium [Directions] | L 0-4 | ||
| Mon., 9/24 | JV Field Hockey | Greenwich | Away - Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Mon., 9/24 | V Girls Volleyball | Bassick | Home - Stamford HS [Directions] | W 3-0 | ||
| Mon., 9/24 | JV Girls Volleyball | Bassick | Home - Stamford HS [Directions] | 5:30 p.m. | ||
| Wed., 9/26 | FR Football | Darien | Home [Directions] | 4:00 p.m. | ||
| Wed., 9/26 | V Boys Soccer | Darien | Home - Stamford High Soccer Field [Directions] | W 4-3 | ||
| Wed., 9/26 | JV Boys Soccer | Darien | Home - Rippowam Field [Directions] | L 0-2 | ||
| Wed., 9/26 | FR Boys Soccer | Darien | Away - DHS Upper Oval Turf Field [Directions] | L 4-0 | ||
| Wed., 9/26 | V Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | W 3-1 | ||
| Wed., 9/26 | JV Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 9/26 | FR Girls Volleyball | New Canaan | Home [Directions] | 4:00 p.m. | ||
| Thu., 9/27 | V Boys Cross Country | Danbury, New Canaan, Norwalk | Away - Tarrywile Park [Directions] | 4:00 p.m. | ||
| Thu., 9/27 | V Girls Cross Country | Danbury, New Canaan, Norwalk | Away - Tarrywile Park [Directions] | 4:00 p.m. | ||
| Thu., 9/27 | V Girls Soccer | Greenwich | Home - Stamford High Soccer Field [Directions] | L 2-1 | ||
| Thu., 9/27 | JV Girls Soccer | Greenwich | Home - Rippowam Field [Directions] | 4:00 p.m. | ||
| Thu., 9/27 | V Girls Swimming and Diving | Trumbull | Home - Westhill Pool [Directions] | 3:30 p.m. | ||
| Fri., 9/28 | V Boys Soccer | Greenwich | Away - Cardinal Stadium [Directions] | T 1-1 [Detailed Results] | 3:15 pm | |
| Fri., 9/28 | JV Boys Soccer | Greenwich | Away - Cos Cob Park Benvenuto Field [Directions] | L 0-5 | ||
| Fri., 9/28 | FR Boys Soccer | Greenwich | Home [Directions] | L 6-1 | ||
| Fri., 9/28 | V Field Hockey | Staples | Home - Stamford HS [Directions] | L 0-7 | ||
| Fri., 9/28 | JV Field Hockey | Staples | Home - Stamford HS [Directions] | 5:30 p.m. | ||
| Fri., 9/28 | V Girls Swimming and Diving | Fairfield Ludlowe | Home - Westhill Pool [Directions] | 3:30 p.m. | ||
| Fri., 9/28 | V Girls Volleyball | Brien McMahon | Away - Brien McMahon HS [Directions] | W 3-0 | ||
| Fri., 9/28 | JV Girls Volleyball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | ||
| Sat., 9/29 | V Football | Darien | Away - DHS Stadium Field [Directions] | L 7-42 | ||
| Sat., 9/29 | V Girls Soccer | St. Joseph | Home - Stamford High Soccer Field [Directions] | L 5-0 | ||
| Sat., 9/29 | JV Girls Soccer | St. Joseph | Home - Rippowam Field [Directions] | 3:30 p.m. | ||
| Mon., 10/1 | JV Football | Darien | Home [Directions] | 4:00 p.m. | ||
| Mon., 10/1 | V Boys Soccer | St. Joseph | Away - St. Joseph HS [Directions] | W 2-0 | 2:15 pm | |
| Mon., 10/1 | JV Boys Soccer | St. Joseph | Away - St. Catherines, Trumbull, CT [Directions] | W 9-0 | ||
| Mon., 10/1 | V Girls Volleyball | Darien | Home - Stamford HS [Directions] | L 3-1 | ||
| Mon., 10/1 | JV Girls Volleyball | Darien | Home - Stamford HS [Directions] | 5:30 p.m. | ||
| Mon., 10/1 | FR Girls Volleyball | Darien | Away - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/2 | V Boys Cross Country | St. Joseph, Brien McMahon, Fairfield Ludlowe | Away [Directions] | 4:00 p.m. | ||
| Tue., 10/2 | V Girls Cross Country | St. Joseph, Brien McMahon, Fairfield Ludlowe | Away [Directions] | 4:00 p.m. | ||
| Tue., 10/2 | V Field Hockey | St. Joseph | Away - St. Joseph HS [Directions] | W 2-1 | ||
| Tue., 10/2 | JV Field Hockey | St. Joseph | Away - St. Joseph HS [Directions] | 5:30 p.m. | ||
| Tue., 10/2 | V Girls Soccer | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | L 4-2 | ||
| Tue., 10/2 | JV Girls Soccer | Danbury | Away - Danbury HS Grass Soccer Field [Directions] | 4:00 p.m. | ||
| Wed., 10/3 | V Girls Soccer | Darien | Away - DHS Center Oval Turf Field [Directions] | L 1-4 | ||
| Wed., 10/3 | JV Girls Soccer | Darien | Away - DHS Upper Oval Turf Field [Directions] | 4:30 p.m. | ||
| Wed., 10/3 | V Girls Swimming and Diving | Staples | Away - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Wed., 10/3 | V Girls Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | L 3-0 | ||
| Wed., 10/3 | JV Girls Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 10/3 | FR Girls Volleyball | Greenwich | Home [Directions] | 4:00 p.m. | ||
| Thu., 10/4 | V Boys Soccer | Danbury | Home - Stamford High Soccer Field [Directions] | L 1-0 | ||
| Thu., 10/4 | JV Boys Soccer | Danbury | Home - Rippowam Field [Directions] | L 0-1 | ||
| Fri., 10/5 | V Football | Brien McMahon | Home - Stamford HS [Directions] | L 12-27 | ||
| Fri., 10/5 | FR Football | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | ||
| Fri., 10/5 | V Field Hockey | Trumbull | Away - McDougall Stadium [Directions] | T 0-0 | ||
| Fri., 10/5 | JV Field Hockey | Trumbull | Away - McDougall Stadium [Directions] | 4:30 p.m. | ||
| Fri., 10/5 | V Girls Soccer | Staples | Away - Loeffler Field - Staples HS [Directions] | L 5-0 | ||
| Fri., 10/5 | JV Girls Soccer | Staples | Away - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Fri., 10/5 | V Girls Swimming and Diving | Ridgefield | Away - Pool at Barlow Mountain School [Directions] | 4:00 p.m. | ||
| Fri., 10/5 | V Girls Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | L 3-0 | ||
| Fri., 10/5 | JV Girls Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | ||
| Fri., 10/5 | FR Girls Volleyball | St. Joseph | Home [Directions] | 4:00 p.m. | ||
| Sat., 10/6 | JV Football | Brien McMahon | Away - Brien McMahon HS [Directions] | TBA | ||
| Sat., 10/6 | V Field Hockey | Danbury | Home - Stamford HS [Directions] | W 3-2 | ||
| Sat., 10/6 | JV Field Hockey | Danbury | Home - Stamford HS [Directions] | Cancelled | ||
| Mon., 10/8 | V Boys Soccer | Staples | Home - Stamford High Soccer Field [Directions] | T 1-1 | ||
| Mon., 10/8 | JV Boys Soccer | Staples | Home - Rippowam Field [Directions] | T 1-1 | ||
| Mon., 10/8 | FR Boys Soccer | Staples | Away - Wakeman Field E (grass) [Directions] | L 3-1 | 2:15 Bob | |
| Mon., 10/8 | V Field Hockey | Fairfield Warde | Home - Stamford HS [Directions] | OT-L 1-2 | ||
| Mon., 10/8 | JV Field Hockey | Fairfield Warde | Home - Stamford HS [Directions] | 5:30 p.m. | ||
| Tue., 10/9 | V Boys Cross Country | Greenwich, Wilton, Trinity Catholic | Away - Greenwich Point [Directions] | 4:00 p.m. | Bob 2:15 | |
| Tue., 10/9 | V Girls Cross Country | Greenwich, Wilton, Trinity Catholic | Away - Greenwich Point [Directions] | 4:00 p.m. | 2:15 Bob | |
| Tue., 10/9 | V Girls Soccer | Norwalk | Home - Stamford High Soccer Field [Directions] | W 4-0 | ||
| Tue., 10/9 | JV Girls Soccer | Norwalk | Home - Rippowam Field [Directions] | 4:00 p.m. | ||
| Wed., 10/10 | V Boys Soccer | Norwalk | Away - Testa Field, NHS [Directions] | W 1-0 | 5:30 1st Student | |
| Wed., 10/10 | JV Boys Soccer | Norwalk | Away - Callahan Complex at Nathan Hale Lower [Directions] | L 0-2 | 4:00 1st student | |
| Wed., 10/10 | FR Boys Soccer | Norwalk | Home [Directions] | W 4-0 | ||
| Wed., 10/10 | V Girls Volleyball | Danbury | Home - Stamford HS [Directions] | W 3-0 | ||
| Wed., 10/10 | JV Girls Volleyball | Danbury | Home - Stamford HS [Directions] | 5:30 p.m. | ||
| Wed., 10/10 | FR Girls Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 4:00 p.m. | 2:15 Bob | |
| Thu., 10/11 | V Girls Swimming and Diving | Darien | Away - Darien YMCA [Directions] | 3:00 p.m. | ||
| Fri., 10/12 | V Boys Soccer | Fairfield Warde | Home - Stamford High Soccer Field [Directions] | L 3-5 | ||
| Fri., 10/12 | JV Boys Soccer | Fairfield Warde | Home - Rippowam Field [Directions] | W 6-2 | ||
| Fri., 10/12 | FR Boys Soccer | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | 2:15 Bob | |
| Fri., 10/12 | V Field Hockey | Westhill | Home - Stamford HS [Directions] | W 3-0 | ||
| Fri., 10/12 | JV Field Hockey | Westhill | Home - Stamford HS [Directions] | 5:30 p.m. | ||
| Fri., 10/12 | V Girls Soccer | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | L 4-0 | 4:00 1st Student | |
| Fri., 10/12 | JV Girls Soccer | Westhill | Away - Westhill Front Turf Field [Directions] | 4:30 p.m. | 3:00 1st student | |
| Fri., 10/12 | V Girls Volleyball | Staples | Home - Stamford HS [Directions] | W 3-2 | ||
| Fri., 10/12 | JV Girls Volleyball | Staples | Home - Stamford HS [Directions] | 5:30 p.m. | ||
| Fri., 10/12 | FR Girls Volleyball | Staples | Away - Staples H.S. Gym [Directions] | 4:00 p.m. | 2:15 1st Student | |
| Sat., 10/13 | V Girls Soccer | Westhill | Away - J. Walter Kennedy Stadium [Directions] | L 3-0 | ||
| Mon., 10/15 | V Boys Soccer | Westhill | Home - Stamford High Soccer Field [Directions] | L 3-1 | ||
| Mon., 10/15 | JV Boys Soccer | Westhill | Home - Rippowam Field [Directions] | T 1-1 | ||
| Mon., 10/15 | FR Boys Soccer | Westhill | Away - J. Walter Kennedy Stadium [Directions] | 4:15 p.m. | 2:45 1st Student | |
| Mon., 10/15 | V Girls Volleyball | Norwalk | Away - Scarso Gymnasium [Directions] | W 3-0 | 2:30 Bob | |
| Mon., 10/15 | JV Girls Volleyball | Norwalk | Away - Scarso Gymnasium [Directions] | 5:30 p.m. | 2:30 Bob | |
| Tue., 10/16 | V Field Hockey | New Canaan | Away - Dunning Stadium [Directions] | L 0-3 | 2:30 1st Student | |
| Tue., 10/16 | JV Field Hockey | New Canaan | Away - Dunning Stadium [Directions] | 5:30 p.m. | 2:30 1st Student | |
| Tue., 10/16 | V Girls Soccer | Bridgeport Central | Away - Kennedy Stadium [Directions] | W 5-3 | 2:15 Bob | |
| Wed., 10/17 | V Girls Swimming and Diving | Norwalk/McMahon | Home - Westhill Pool [Directions] | 4:00 p.m. | ||
| Wed., 10/17 | V Girls Volleyball | Fairfield Warde | Home - Stamford HS [Directions] | W 3-1 | ||
| Wed., 10/17 | JV Girls Volleyball | Fairfield Warde | Home - Stamford HS [Directions] | 5:30 p.m. | ||
| Wed., 10/17 | FR Girls Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | 2:15 Bob | |
| Thu., 10/18 | V Boys Cross Country | FCIAC Championships | Away - Waveny | 2:00 p.m. | 12:30 pm | |
| Thu., 10/18 | FR Football | St. Joseph | Home [Directions] | 4:00 p.m. | ||
| Thu., 10/18 | V Boys Soccer | Bridgeport Central | Home - Stamford High Soccer Field [Directions] | W 6-2 | ||
| Thu., 10/18 | JV Boys Soccer | Bridgeport Central | Home - Rippowam Field [Directions] | T 1-1 | ||
| Thu., 10/18 | V Girls Cross Country | FCIAC Championsips | Away - Waveny | 2:00 p.m. | 12:30 pm | |
| Thu., 10/18 | JV Girls Soccer | Fairfield Warde | Away - Tomlinson MS [Directions] | 4:00 p.m. | 2:15 Bob | |
| Fri., 10/19 | V Field Hockey | Wilton | Home - Stamford HS [Directions] | L 0-2 | ||
| Fri., 10/19 | JV Field Hockey | Wilton | Home - Stamford HS [Directions] | 5:30 p.m. | ||
| Fri., 10/19 | V Girls Soccer | Wilton | Home - Stamford High Soccer Field [Directions] | L 4-1 | ||
| Fri., 10/19 | JV Girls Soccer | Wilton | Home - Rippowam Field [Directions] | 4:30 p.m. | ||
| Fri., 10/19 | V Girls Volleyball | Westhill | Home - Stamford HS [Directions] | L 3-1 | ||
| Fri., 10/19 | JV Girls Volleyball | Westhill | Home - Stamford High Aux Gym [Directions] | 5:30 p.m. | ||
| Fri., 10/19 | FR Girls Volleyball | Westhill | Away - Westhill - New Gymnasium [Directions] | 4:00 p.m. | 2:45 1st Student | |
| Sat., 10/20 | V Football | St. Joseph | Away - St. Joseph HS [Directions] | L 0-42 | 11:00 am 1st student | |
| Sat., 10/20 | V Boys Soccer | Wilton | Away - Lilly Field - Turf [Directions] | L L 8-0 | 9:15 am 1st Student | |
| Sat., 10/20 | JV Boys Soccer | Wilton | Away [Directions] | W 3-2 | 9:15 am 1st Student | |
| Sat., 10/20 | V Girls Swimming and Diving | Greenwich | Away - GHS Pool [Directions] | 12:00 p.m. | ||
| Mon., 10/22 | JV Football | St. Joseph | Home [Directions] | 4:00 p.m. | ||
| Mon., 10/22 | V Field Hockey | Norwalk | Away - Testa Field, NHS [Directions] | L 0-9 | 4:00 1st student | |
| Mon., 10/22 | JV Field Hockey | Norwalk | Away - Testa Field, NHS [Directions] | 5:30 p.m. | 4:00 1st Student | |
| Mon., 10/22 | V Girls Soccer | Trinity Catholic | Home - Stamford High Soccer Field [Directions] | W 4-1 | ||
| Mon., 10/22 | V Girls Swimming and Diving | St. Joseph | Home - Westhill Pool [Directions] | 4:00 p.m. | ||
| Mon., 10/22 | V Girls Volleyball | Bridgeport Central | Home - Stamford HS [Directions] | W 3-0 | ||
| Mon., 10/22 | JV Girls Volleyball | Bridgeport Central | Home - Kuzco Gymnasium at Stamford HS [Directions] | 4:00 p.m. | ||
| Tue., 10/23 | V Boys Soccer | Trinity Catholic | Away | W 6-3 | 2:30 1st student | |
| Tue., 10/23 | V Field Hockey | Brien McMahon | Away - Brien McMahon HS [Directions] | L 1-3 | 4:00 1st student | |
| Tue., 10/23 | JV Field Hockey | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:30 p.m. | 4:00 1st Student | |
| Wed., 10/24 | V Girls Volleyball | Wilton | Away - Nicholas Zeoli Field House [Directions] | W 3-0 | 2:15 1st student | |
| Wed., 10/24 | JV Girls Volleyball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 4:00 p.m. | 2:15 1st student | |
| Wed., 10/24 | FR Girls Volleyball | Wilton | Home [Directions] | 4:30 p.m. | ||
| Thu., 10/25 | FR Football | Wilton | Away [Directions] | 6:00 p.m. | 3:45 1st student | |
| Thu., 10/25 | FR Boys Soccer | Wilton | Away - Lilly Field - Turf [Directions] | 4:00 p.m.. | ||
| Fri., 10/26 | V Football | Wilton | Home - Stamford HS [Directions] | L 0-27 | ||
| Fri., 10/26 | V Boys Indoor Track | State Championships | Home - Wickham Park - East Hartford [Directions] | 9:00 a.m. | 7:00am | |
| Fri., 10/26 | V Girls Volleyball | Trinity Catholic | Away - Walsh Court | W 3-0 | 3:15 1st student | |
| Fri., 10/26 | JV Girls Volleyball | Trinity Catholic | Away | 4:00 p.m. | 3:15 1st student | |
| Mon., 10/29 | JV Football | Wilton | Away - Fujitani Field - Turf [Directions] | 6:00 p.m. | 8:30 am 1st student | |
| Mon., 10/29 | V Girls Swimming and Diving | FCIAC Diving Championship | Home - Westhill Pool [Directions] | 4:30 p.m. | ||
| Tue., 10/30 | V Girls Swimming and Diving | FCIAC Trials | Away - Greenwich HS | TBA | ||
| Wed., 10/31 | V Boys Soccer | Westhill (Scrim.) | Away - Westhill HS [Directions] | 3:00 p.m. | 2:00 | |
| Thu., 11/1 | FR Football | Bridgeport Central | Away - Kennedy Stadium [Directions] | 5:00 p.m. | ||
| Thu., 11/1 | V Girls Swimming and Diving | FCIAC Finals | Away - Greenwich HS | TBA | ||
| Fri., 11/2 | V Girls Volleyball | Greenwich (Scrim.) | Away - Greenwich HS [Directions] | 4:00 p.m. | 3:00 | |
| Sat., 11/3 | V Football | Bridgeport Central | Home - Stamford HS [Directions] | W 7-0 | ||
| Mon., 11/5 | JV Football | Bridgeport Central | Away - Kennedy Stadium [Directions] | 5:00 p.m. | ||
| Mon., 11/5 | V Girls Volleyball | Hamden | Home - Kuzco Gymnasium at Stamford HS [Directions] | 4:00 p.m. | Bring Canned good/non perishable food | |
| Tue., 11/6 | V Boys Soccer | Fairfield Prep | Away - Rafferty Stadium, Fairfield University [Directions] | L 5-1 | 2:00 - Bob | |
| Wed., 11/7 | V Girls Swimming and Diving | CIAC Class LL Diving Championships | Away - Middletown HS. | 5:30 p.m. | ||
| Thu., 11/8 | FR Football | Staples | Home [Directions] | 4:00 p.m. | ||
| Fri., 11/9 | V Football | Staples | Away - Staples Stadium [Directions] | L 0-37 | ||
| Sat., 11/10 | JV Football | Staples | Away - Staples Stadium [Directions] | 10:00 a.m. | 8:00 | |
| Sat., 11/10 | V Girls Swimming and Diving | CIAC Class LL Trials | Away - East Hartford HS | 11:30 a.m. | ||
| Wed., 11/14 | V Girls Swimming and Diving | CIAC Class LL Finals | Away - Southern Connecticut State Univ. | 6:00 p.m. | ||
| Thu., 11/15 | V Girls Swimming and Diving | CIAC Open Diving Championships | Away - Middletown HS | 5:30 p.m. | ||
| Sat., 11/17 | JV Football | Westhill | Away - J. Walter Kennedy Stadium [Directions] | 12:00 p.m. | ||
| Sat., 11/17 | FR Football | Westhill | Away - J. Walter Kennedy Stadium [Directions] | 10:00 a.m. | ||
| Sat., 11/17 | V Girls Swimming and Diving | CIAC Open Championships | Away - Yale University | 12:00 p.m. | ||
| Wed., 11/21 | V Football | Westhill | Home - Stamford HS [Directions] | W 19-0 | ||
| Sat., 12/1 | V Girls Basketball | Lady Hatters Jamboree | Away - Danbury HS | 12:00 p.m. | ||
| Sat., 12/1 | V Girls Ice Hockey | HS Girls Hockey Jamboree | Away - The Rinks at Shelton | 5:45 p.m. | ||
| Wed., 12/5 | V Girls Ice Hockey | Notre Dame-Fairfield | Away - The Rinks at Shelton - Upper [Directions] | L 2-8 | ||
| Thu., 12/6 | V Boys Basketball | Stratford (Scrim.) | Home - Kuzco Gymnasium at Stamford HS [Directions] | 3:00 p.m. | 4 quarters Varsity - 2 quarters JV | |
| Thu., 12/6 | V Girls Basketball | Immaculate (Scrim.) | Away - Immaculate HS [Directions] | 4:30 p.m. | 2:45pm Myers | |
| Mon., 12/10 | V Boys Basketball | Joel Barlow (Scrim.) | Away - JBHS Lower Gym [Directions] | 5:30 p.m. | Myers - 3:45 | |
| Wed., 12/12 | V Boys Ice Hockey | North Branford | Away - Northford Ice Pavilion [Directions] | L 7-8 | ||
| Wed., 12/12 | V Girls Basketball | Wilton | Home - Kuzco Gymnasium at Stamford HS [Directions] | W 48-33 | ||
| Wed., 12/12 | JV Girls Basketball | Wilton | Home - Kuzco Gymnasium at Stamford HS [Directions] | 5:15 p.m. | ||
| Wed., 12/12 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Terry Conners Ice Rink [Directions] | W 5-4 | ||
| Thu., 12/13 | V Boys Basketball | Masuk | Home - Kuzco Gymnasium at Stamford HS [Directions] | W 101-72 | ||
| Thu., 12/13 | JV Boys Basketball | Masuk | Home - Kuzco Gymnasium at Stamford HS [Directions] | 5:15 p.m. | ||
| Fri., 12/14 | V Girls Basketball | Trinity Catholic | Home - Kuzco Gymnasium at Stamford HS [Directions] | L 46-43 | ||
| Fri., 12/14 | JV Girls Basketball | Trinity Catholic | Home - Kuzco Gymnasium at Stamford HS [Directions] | 4:00 p.m. | ||
| Sat., 12/15 | V Boys Ice Hockey | Brien McMahon/Norwalk | Home - SoNo Ice House [Directions] | W 4-1 | ||
| Sat., 12/15 | V Boys Indoor Track | Staples, St. Joseph, Trumbull, Westhill | Away - Staples Field House [Directions] | 10:00 a.m. | 8:15am 1st student | |
| Sat., 12/15 | V Wrestling | Ludlowe Invitational | Away | 8:00 a.m. | 7:00pm Myers | |
| Sat., 12/15 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice [Directions] | L 3-9 | 1st -4pm SHS - Exit 18 | |
| Sat., 12/15 | V Girls Indoor Track | Staples | Away - Staples Field House [Directions] | 10:00 a.m. | 8:15am 1st student | |
| Wed., 12/19 | V Boys Basketball | Trumbull | Home - Kuzco Gymnasium at Stamford HS [Directions] | L 70-84 | ||
| Wed., 12/19 | JV Boys Basketball | Trumbull | Home - Kuzco Gymnasium at Stamford HS [Directions] | 5:15 p.m. | ||
| Wed., 12/19 | FR Boys Basketball | Trumbull | Home - Kuzco Gymnasium at Stamford HS [Directions] | 4:00 p.m. | ||
| Wed., 12/19 | V Boys Ice Hockey | West Haven Coop | Away - Bennett Rink [Directions] | L 2-5 | ||
| Wed., 12/19 | V Boys Swimming and Diving | Danbury | Home - Westhill Pool [Directions] | 5:15 p.m. | ||
| Wed., 12/19 | V Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | L 66-28 | Ron 4:00pm | |
| Wed., 12/19 | JV Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | 5:15 p.m. | 1st 2:15pm | |
| Wed., 12/19 | FR Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | 1st 2:15pm | |
| Wed., 12/19 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Winter Garden Ice Arena [Directions] | L 1-6 | Myers -1:45pm WHS -2pm SHS | |
| Thu., 12/20 | V Wrestling | Brien McMahon | Away - Brien McMahon HS [Directions] | 6:00 p.m. | 1st student 4:00pm | |
| Fri., 12/21 | V Boys Basketball | Ridgefield | Away - RHS Main Gym [Directions] | L 46-71 | 4:00pm 1st student | |
| Fri., 12/21 | JV Boys Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 5:15 p.m. | Myers 2:15 | |
| Fri., 12/21 | FR Boys Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | 2:15pm Myers | |
| Fri., 12/21 | V Girls Basketball | Ridgefield | Home - Kuzco Gymnasium at Stamford HS [Directions] | L 33-40 | ||
| Fri., 12/21 | JV Girls Basketball | Ridgefield | Home - Kuzco Gymnasium at Stamford HS [Directions] | 5:15 p.m. | ||
| Fri., 12/21 | FR Girls Basketball | Ridgefield | Home - Kuzco Gymnasium at Stamford HS [Directions] | 4:00 p.m. | ||
| Sat., 12/22 | V Boys Ice Hockey | North Haven | Home - Terry Conners Ice Rink [Directions] | W 5-1 | ||
| Sat., 12/22 | V Boys Indoor Track | Hillhouse Qualifier | Away - Floyd Little athletic center | 10:00 a.m. | Myers 7:45 am | |
| Sat., 12/22 | V Wrestling | Ridgefield, Darien, Norwalk, John Jay (NY) | Away - RHS Main and Aux Gyms [Directions] | 10:00 a.m. | 1st student 1:30pm | Time Change- 7:30 Bus - 8:30 Weigh in |
| Sat., 12/22 | V Girls Indoor Track | Hillhouse Qualifier | Away - Floyd Little athletic center | 10:00 a.m. | Myers 7:45 | |
| Thu., 12/27 | V Boys Basketball | RHAM | Away - West Haven HS [Directions] | W 84-41 | Myers 2:30 | |
| Thu., 12/27 | V Girls Basketball | Westhill | Home - Kuzco Gymnasium at Stamford HS [Directions] | W 46-36 | Kobly Vs Scarsdale 4pm Stamford vs WHS 6PM | |
| Fri., 12/28 | JV Boys Basketball | Greenwich | Home - Kuzco Gymnasium at Stamford HS [Directions] | 4:00 p.m. | ||
| Sat., 12/29 | V Boys Basketball | Notre Dame-West Haven | Away - Notre Dame HS [Directions] | L 60-75 | Myers 11am | |
| Sat., 12/29 | V Boys Ice Hockey | East Haven Coop | Home - Terry Conners Ice Rink [Directions] | L 4-7 | ||
| Sat., 12/29 | V Girls Basketball | Kolbe Cathedral | Home - Kuzco Gymnasium at Stamford HS [Directions] | L 37-53 | WHS - Scarsdale -4PM & SHS-Kolbe 6PM | |
| Wed., 1/2 | V Girls Basketball | Norwich Free Academy | Home - Kuzco Gymnasium at Stamford HS [Directions] | W 44-32 | ||
| Wed., 1/2 | JV Girls Basketball | Norwich Free Academy | Home - Kuzco Gymnasium at Stamford HS [Directions] | 5:15 p.m. | ||
| Thu., 1/3 | V Boys Basketball | Fairfield Ludlowe | Home - Kuzco Gymnasium at Stamford HS [Directions] | W 52-49 | ||
| Thu., 1/3 | JV Boys Basketball | Fairfield Ludlowe | Home - Kuzco Gymnasium at Stamford HS [Directions] | 5:15 p.m. | ||
| Thu., 1/3 | FR Boys Basketball | Fairfield Ludlowe | Home - Kuzco Gymnasium at Stamford HS [Directions] | 4:00 p.m. | ||
| Thu., 1/3 | V Wrestling | Greenwich | Home - Stamford High Aux Gym [Directions] | 6:30 p.m. | ||
| Thu., 1/3 | V Girls Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | L 50-39 | myers 4:15pm | |
| Thu., 1/3 | JV Girls Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 5:15 p.m. | 1st 2:15pm drop only | |
| Thu., 1/3 | FR Girls Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 4:00 p.m. | 1st 2:15pm | |
| Fri., 1/4 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Away - Pat Spinola Natatorium [Directions] | 3:30 p.m. | ||
| Sat., 1/5 | V Boys Ice Hockey | Lyman Hall | Away - Northford Ice Pavilion [Directions] | L 4-6 | ||
| Sat., 1/5 | V Boys Indoor Track | Wilton, Greenwich, Fairfield Ludlowe, Danbury | Away [Directions] | 10:00 a.m.` | myers 8am | |
| Sat., 1/5 | V Boys Indoor Track | 3rd James Barber Invitational | Away - Southern Connecticut State University | 12:00 p.m. | 1st 10:00am | |
| Sat., 1/5 | V Girls Ice Hockey | East Catholic Coop | Away - Newington Arena [Directions] | L 3-7 | 1st leave shs 6pm go to exit 18 | |
| Sat., 1/5 | V Girls Indoor Track | Wilton | Away - wilton [Directions] | 10:00 a.m. | 8am Myers | |
| Sat., 1/5 | V Girls Indoor Track | 3rd James Barber Invitational | Away - Southern Connecticut State University | 12:00 p.m. | 1st 10:00am | |
| Mon., 1/7 | V Boys Ice Hockey | Brien McMahon/Norwalk | Away - SoNo Ice House [Directions] | W 7-3 | ||
| Mon., 1/7 | FR Girls Basketball | Wright Tech | Away - Wright Tech [Directions] | 4:00 p.m. | 1st 3pm | |
| Wed., 1/9 | V Boys Swimming and Diving | Darien | Home - Westhill Pool [Directions] | 3:15 p.m. | ||
| Wed., 1/9 | V Wrestling | Westhill | Home - Kuzco Gymnasium at Stamford HS [Directions] | 6:30 p.m. | ||
| Wed., 1/9 | V Girls Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | L 0-8 | Staples Buses | |
| Thu., 1/10 | V Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | L 49-52 | myers 4:30pm | |
| Thu., 1/10 | JV Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 5:15 p.m. | myers 2:30pm | |
| Thu., 1/10 | FR Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | myers 2:30pm | |
| Thu., 1/10 | V Boys Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | W 8-5 | ||
| Thu., 1/10 | V Girls Basketball | New Canaan | Home - Kuzco Gymnasium at Stamford HS [Directions] | W 35-27 | ||
| Thu., 1/10 | JV Girls Basketball | New Canaan | Home - Kuzco Gymnasium at Stamford HS [Directions] | 5:15 p.m. | ||
| Thu., 1/10 | FR Girls Basketball | New Canaan | Home - Kuzco Gymnasium at Stamford HS [Directions] | 4:00 p.m. | ||
| Sat., 1/12 | V Boys Basketball | New Britain | Home - Kuzco Gymnasium at Stamford HS [Directions] | W 50-49 | ||
| Sat., 1/12 | JV Boys Basketball | New Britain | Home - Kuzco Gymnasium at Stamford HS [Directions] | 1:30 p.m. | ||
| Sat., 1/12 | V Boys Indoor Track | Staples, Ridgefield, Norwalk, Westhill | Away - Staples Field House [Directions] | 10:00 a.m. | 1st 8am | |
| Sat., 1/12 | V Wrestling | John Chacho Duals | Away - Staples HS | 7:30 a.m. | myers 6:30am | |
| Sat., 1/12 | FR Girls Basketball | Norwich Free Academy | Home - Kuzco Gymnasium at Stamford HS [Directions] | 10:00 a.m. | ||
| Sat., 1/12 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Terry Conners Ice Rink [Directions] | W 8-7 | ||
| Sat., 1/12 | V Girls Indoor Track | Staples | Away - Staples Field House [Directions] | 10:00 a.m. | 1st 8am | |
| Mon., 1/14 | V Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | L 59-61 | myers 4:15pm | |
| Mon., 1/14 | JV Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:15 p.m. | myers 2:30pm | |
| Mon., 1/14 | FR Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | myers 2:30pm | |
| Mon., 1/14 | V Girls Basketball | Brien McMahon | Home - Kuzco Gymnasium at Stamford HS [Directions] | W 38-17 | ||
| Mon., 1/14 | JV Girls Basketball | Brien McMahon | Home - Kuzco Gymnasium at Stamford HS [Directions] | 4:00 p.m. | ||
| Tue., 1/15 | V Boys Swimming and Diving | Wilton | Away [Directions] | 3:40 p.m. | ||
| Wed., 1/16 | V Boys Ice Hockey | Trinity Catholic | Home - Terry Conners Ice Rink [Directions] | W 8-3 | ||
| Wed., 1/16 | V Girls Ice Hockey | New Canaan | Home - Terry Conners Ice Rink [Directions] | L 0-7 | ||
| Thu., 1/17 | V Boys Basketball | Darien | Home - Kuzco Gymnasium at Stamford HS [Directions] | W 60-53 | ||
| Thu., 1/17 | JV Boys Basketball | Darien | Home - Kuzco Gymnasium at Stamford HS [Directions] | 5:15 p.m. | ||
| Thu., 1/17 | FR Boys Basketball | Darien | Home - Kuzco Gymnasium at Stamford HS [Directions] | 4:00 p.m. | ||
| Thu., 1/17 | V Girls Basketball | Darien | Away - DHS Main Gym [Directions] | W 52-48 | myers 4:30pm | |
| Thu., 1/17 | JV Girls Basketball | Darien | Away - DHS Main Gym [Directions] | 5:15 p.m. | myers 2:30pm | |
| Thu., 1/17 | FR Girls Basketball | Darien | Away - DHS Main Gym [Directions] | 3:45 p.m. | myers 2:30pm | |
| Fri., 1/18 | V Girls Ice Hockey | Trumbull/St. Joseph | Away [Directions] | L 4-5 | Myers 2:15pm shs -westport 4 | |
| Sat., 1/19 | V Boys Basketball | Westhill | Home - Kuzco Gymnasium at Stamford HS [Directions] | W 68-52 | ||
| Sat., 1/19 | V Boys Ice Hockey | Amity | Home - Terry Conners Ice Rink [Directions] | W 3-2 | ||
| Sat., 1/19 | V Boys Indoor Track | Staples, St. Joseph, Darien, Greenwich | Away - Staples Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/19 | V Boys Indoor Track | New Balance Games | Away - Armory - NYC | 8:30 a.m. | 1st 6:45am | |
| Sat., 1/19 | V Girls Basketball | Westhill | Home - Kuzco Gymnasium at Stamford HS [Directions] | W 49-17 | ||
| Sat., 1/19 | V Girls Indoor Track | Staples | Away [Directions] | 10:00 a.m. | Myers 8:15am | |
| Sat., 1/19 | V Girls Indoor Track | New Balance Games | Away - Armory - NYC | 8:30 a.m. | 1st 6:45 | |
| Mon., 1/21 | V Girls Ice Hockey | Avon | Home - Terry Conners Ice Rink [Directions] | L 3-4 | ||
| Tue., 1/22 | V Boys Basketball | Greenwich | Away - GHS Gymnasium [Directions] | W 66-60 | myers 4:15pm | |
| Tue., 1/22 | JV Boys Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 5:15 p.m. | myers 2:30pm | |
| Tue., 1/22 | FR Boys Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 4:00 p.m. | myers 2:30pm | |
| Tue., 1/22 | V Girls Basketball | Greenwich | Home - Kuzco Gymnasium at Stamford HS [Directions] | W 34-29 | ||
| Tue., 1/22 | JV Girls Basketball | Greenwich | Home - Kuzco Gymnasium at Stamford HS [Directions] | 5:15 p.m. | ||
| Tue., 1/22 | FR Girls Basketball | Greenwich | Home - Kuzco Gymnasium at Stamford HS [Directions] | 4:00 p.m. | ||
| Wed., 1/23 | V Boys Ice Hockey | Darien | Home - Terry Conners Ice Rink [Directions] | L 0-8 | ||
| Wed., 1/23 | V Boys Swimming and Diving | Greenwich | Away - GHS Pool [Directions] | 4:10 p.m. | ||
| Wed., 1/23 | V Wrestling | Staples | Home - Stamford High Aux Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/23 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Terry Conners Ice Rink [Directions] | L 1-8 | ||
| Fri., 1/25 | V Boys Basketball | St. Joseph | Away - St. Joseph HS [Directions] | L 74-75 OT | myers 4pm | |
| Fri., 1/25 | JV Boys Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 5:15 p.m. | 1st 2:15pm drop only | |
| Fri., 1/25 | FR Boys Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | 1st 2:15pm | |
| Fri., 1/25 | V Boys Ice Hockey | Wilton | Away - Winter Garden Rink-Ridgefield [Directions] | W 5-0 | ||
| Fri., 1/25 | V Boys Swimming and Diving | Ridgefield | Home - Westhill Pool [Directions] | 3:15 p.m. | ||
| Fri., 1/25 | V Girls Basketball | St. Joseph | Home - Kuzco Gymnasium at Stamford HS [Directions] | W 53-44 | ||
| Fri., 1/25 | JV Girls Basketball | St. Joseph | Home - Kuzco Gymnasium at Stamford HS [Directions] | 5:15 p.m. | ||
| Fri., 1/25 | FR Girls Basketball | St. Joseph | Home - Kuzco Gymnasium at Stamford HS [Directions] | 4:00 p.m. | ||
| Sat., 1/26 | V Boys Ice Hockey | Watertown-Pomperaug | Away - Taft-Mays Rink [Directions] | L 2-4 | ||
| Sat., 1/26 | V Boys Indoor Track | FCIAC Division Finals | Away - Staples Field House | 10:00 a.m. | 1st 8am | |
| Sat., 1/26 | V Wrestling | 2019 Ridgefield Challenge | Away - Ridgefield HS | 7:30 a.m. | 1st Student 6:30am | |
| Sat., 1/26 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Terry Conners Ice Rink [Directions] | L 1-6 | ||
| Sat., 1/26 | V Girls Indoor Track | FCIAC Division Championships | Away - Staples Field House | 10:00 a.m. | 1st 8am | |
| Mon., 1/28 | V Girls Ice Hockey | Darien | Away - Darien Ice Rink [Directions] | L 1-8 | 6:25pm Myers | |
| Tue., 1/29 | V Girls Ice Hockey | Darien | Home - Terry Conners Ice Rink [Directions] | L 1-8 | ||
| Thu., 1/31 | V Boys Basketball | Staples | Home - Kuzco Gymnasium at Stamford HS [Directions] | W 75-47 | ||
| Thu., 1/31 | JV Boys Basketball | Staples | Home - Kuzco Gymnasium at Stamford HS [Directions] | 5:15 p.m. | ||
| Thu., 1/31 | FR Boys Basketball | Staples | Home - Kuzco Gymnasium at Stamford HS [Directions] | 4:00 p.m. | ||
| Thu., 1/31 | V Boys Indoor Track | FCIAC Champioships | Away - Floyd Little AC | 4:30 p.m. | myers 2:45 pm | |
| Thu., 1/31 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Home - Westhill Pool [Directions] | 3:15 p.m. | ||
| Thu., 1/31 | V Wrestling | Danbury | Home - Stamford High Aux Gym [Directions] | 6:00 p.m. | ||
| Thu., 1/31 | V Girls Basketball | Staples | Away - Staples H.S. Gym [Directions] | W 54-50 | 1st 4:15pm stay | |
| Thu., 1/31 | JV Girls Basketball | Staples | Away - Staples H.S. Gym [Directions] | 5:15 p.m. | 1st 2:15 drop only | |
| Thu., 1/31 | FR Girls Basketball | Staples | Away - Staples H.S. Gym [Directions] | 4:00 p.m. | 1st 2:15pm drop only | |
| Thu., 1/31 | V Girls Ice Hockey | Hall/Conard | Home - Terry Conners Ice Rink [Directions] | L 0-4 | ||
| Thu., 1/31 | V Girls Indoor Track | FCIAC Championships | Away - Floyd Little AC | 4:30 p.m. | meyers 2:45 pm | |
| Fri., 2/1 | V Boys Swimming and Diving | New Canaan | Home - Westhill Pool [Directions] | 3:15 p.m. | ||
| Sat., 2/2 | V Boys Ice Hockey | New Canaan | Home - Terry Conners Ice Rink [Directions] | L 2-5 | ||
| Sat., 2/2 | V Wrestling | JV Chanpionships | Away - Ludlowe HS | 8:00 a.m. | 1st - 7:00 am | |
| Sat., 2/2 | V Competitive Cheerleading | FCIAC's | Away | TBA | Myers 7am | |
| Sat., 2/2 | V Girls Basketball | Ursuline (NY) | Away - Ossining HS - Ossining NY | L 44-65 | 1st - 8:30 pick up | |
| Mon., 2/4 | V Girls Ice Hockey | Branford | Home - Terry Conners Ice Rink [Directions] | L 3-4 | ||
| Tue., 2/5 | V Boys Basketball | Norwalk | Away - Scarso Gymnasium [Directions] | W 70-61 | Myers 4pm | |
| Tue., 2/5 | JV Boys Basketball | Norwalk | Away - Scarso Gymnasium [Directions] | 5:15 p.m. | Myers 2:30pm | |
| Tue., 2/5 | FR Boys Basketball | Norwalk | Away - Scarso Gymnasium [Directions] | 4:00 p.m. | Myers 2:30pm | |
| Tue., 2/5 | V Wrestling | Trumbull | Away - Auxiliary gym [Directions] | 6:00 p.m. | 1st student 3:30pm | |
| Tue., 2/5 | V Girls Basketball | Norwalk | Home - Kuzco Gymnasium at Stamford HS [Directions] | L 24-51 | ||
| Tue., 2/5 | JV Girls Basketball | Norwalk | Home - Kuzco Gymnasium at Stamford HS [Directions] | 5:15 p.m. | ||
| Tue., 2/5 | FR Girls Basketball | Wright Tech | Home - Kuzco Gymnasium at Stamford HS [Directions] | 4:00 p.m. | ||
| Tue., 2/5 | Unified Sports Basketball | Norwalk | Home - Stamford High Aux Gym [Directions] | 2:45 p.m. | ||
| Wed., 2/6 | V Boys Basketball | Danbury | Home - Kuzco Gymnasium at Stamford HS [Directions] | W 51-48 | ||
| Wed., 2/6 | JV Boys Basketball | Danbury | Home - Kuzco Gymnasium at Stamford HS [Directions] | 5:15 p.m. | ||
| Wed., 2/6 | FR Boys Basketball | Danbury | Home - Kuzco Gymnasium at Stamford HS [Directions] | 4:00 p.m. | ||
| Wed., 2/6 | V Boys Swimming and Diving | Staples | Away - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Wed., 2/6 | V Girls Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | L 30-45 | myers 4pm | |
| Wed., 2/6 | JV Girls Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 5:15 p.m. | 1st 2:15pm drop only | |
| Wed., 2/6 | FR Girls Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 4:00 p.m. | 1st 2:15pm | |
| Wed., 2/6 | V Girls Ice Hockey | Greenwich | Home - Terry Conners Ice Rink [Directions] | L 0-5 | ||
| Fri., 2/8 | V Boys Basketball | Fairfield Warde | Home - Kuzco Gymnasium at Stamford HS [Directions] | W 75-66 | ||
| Fri., 2/8 | JV Boys Basketball | Fairfield Warde | Home - Kuzco Gymnasium at Stamford HS [Directions] | 5:15 p.m. | ||
| Fri., 2/8 | FR Boys Basketball | Fairfield Warde | Home - Kuzco Gymnasium at Stamford HS [Directions] | 4:00 p.m. | ||
| Fri., 2/8 | V Wrestling | FCIAC Tournament | Away - New Canaan | 4:30 p.m. | 1st student 2:30pm | |
| Fri., 2/8 | V Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | W 38-30 | Meyers 4pm | |
| Fri., 2/8 | JV Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 5:15 p.m. | 1st student 2:30pm Drop only | |
| Fri., 2/8 | FR Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | 1st student 2:30pm Drop only | |
| Fri., 2/8 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - So No Icehouse - Norwalk [Directions] | L 6-8 | Parent drop off and pick up | |
| Sat., 2/9 | V Boys Ice Hockey | Trumbull | Away - Shelton Rinks [Directions] | L 4-5(OT) | ||
| Sat., 2/9 | V Boys Indoor Track | CIAC States | Away - Floyd Little Athletic Center, New Haven | 4:30 p.m. | ||
| Sat., 2/9 | V Wrestling | FCIAC Tournament | Away - New Canaan | 9:00 a.m.and4:pm | Myers 8am | |
| Sat., 2/9 | V Girls Indoor Track | CIAC States | Away - Floyd Little Athletic Center, New Haven | 4:30 p.m. | ||
| Mon., 2/11 | JV Boys Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 7:00 p.m. | Myers 5:30 | |
| Mon., 2/11 | FR Boys Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | Myers 3pm | |
| Mon., 2/11 | V Boys Ice Hockey | Staples | Away - Milford Ice Pavilion [Directions] | W 5-0 | ||
| Mon., 2/11 | JV Girls Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | Myers 3pm | |
| Mon., 2/11 | V Girls Ice Hockey | New Canaan | Away - Darien Ice Rink [Directions] | L 0-7 | 1st 5:15 Drop only - Parent pick up | |
| Wed., 2/13 | V Boys Basketball | Bridgeport Central | Home - Kuzco Gymnasium at Stamford HS [Directions] | W 83-62 | ||
| Wed., 2/13 | JV Boys Basketball | Bridgeport Central | Home - Kuzco Gymnasium at Stamford HS [Directions] | 5:15 p.m. | ||
| Wed., 2/13 | FR Boys Basketball | Bridgeport Central | Home - Kuzco Gymnasium at Stamford HS [Directions] | 4:00 p.m. | ||
| Wed., 2/13 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Home - Terry Conners Ice Rink [Directions] | W 5-4(OT) | ||
| Wed., 2/13 | V Girls Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | W 47-28 | Myers 2:30pm | |
| Wed., 2/13 | JV Girls Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 4:00 p.m. | Myers 2:30pm | |
| Fri., 2/15 | V Wrestling | CIAC Class LL Tournament | Away - Trumbull HS | 4:45 p.m. | Myers 1:30pm | |
| Fri., 2/15 | V Girls Ice Hockey | Northwest Catholic | Home - Terry Conners Ice Rink [Directions] | W 8-6 | ||
| Sat., 2/16 | V Boys Ice Hockey | St. Joseph | Home - Terry Conners Ice Rink [Directions] | W 9-4 | ||
| Sat., 2/16 | V Wrestling | CIAC Class LL Tournament Finals | Away - Trumbull HS | 9:00 a.m. | ||
| Sat., 2/16 | V Girls Basketball | Norwalk | Away - Ludlowe HS [Directions] | L 59-29 | Bob - 4pm | Vs. Norwalk |
| Sun., 2/17 | V Competitive Cheerleading | SCSU 1st Annual Winter Showdown | Away - Southern CT State University | 10:00 a.m. | ||
| Mon., 2/18 | V Boys Basketball | Wilton | Away - Nicholas Zeoli Field House [Directions] | L 62-81 | Myers 4pm | |
| Mon., 2/18 | JV Boys Basketball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 5:15 p.m. | 1st student 2:30pm drop off | |
| Mon., 2/18 | FR Boys Basketball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 4:00 p.m. | 1st student 2:30pm drop off | |
| Mon., 2/18 | V Boys Ice Hockey | Ridgefield | Away - Winter Garden Ice Arena [Directions] | L 1-7 | ||
| Tue., 2/19 | V Girls Basketball | FCIAC Semifinals | Home - Trumbull HS [Directions] | Cancelled | ||
| Thu., 2/21 | V Boys Basketball | Trinity Catholic | Away - Walsh Court | W 62-56 | Myers 4:30pm | |
| Thu., 2/21 | JV Boys Basketball | Trinity Catholic | Away - Walsh Court | Cancelled | Myers 3pm | |
| Thu., 2/21 | V Boys Ice Hockey | Guilford | Home - Terry Conners Ice Rink [Directions] | W 7-3 | ||
| Thu., 2/21 | V Boys Swimming and Diving | Trumbull | Away - Hillcrest MS [Directions] | 3:30 p.m. | ||
| Thu., 2/21 | Unified Sports Basketball | Greenwich | Home - Stamford High Aux Gym [Directions] | 3:15 p.m. | ||
| Fri., 2/22 | V Wrestling | State Open | Away - Floyd Little Ath. Ctr-Hillhouse HS (New Haven) | 3:00 p.m. | ||
| Sat., 2/23 | V Boys Basketball | FCIAC Quarterfinals | Away - Warde HS | TBA | ||
| Sat., 2/23 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Home - Terry Conners Ice Rink [Directions] | W 7-4 | ||
| Sat., 2/23 | V Wrestling | State Open Finals | Away - Floyd Little Ath. Ctr-Hillhouse HS (New Haven) | 9:00 a.m. | ||
| Sat., 2/23 | V Competitive Cheerleading | OHS Spirit Spectacular | Away - Oxford HS | 11:00 a.m. | Myers 7:30am | |
| Mon., 2/25 | Unified Sports Basketball | Ridgefield | Away [Directions] | 3:30 p.m. | Meyers - 2:10 | |
| Tue., 2/26 | V Boys Basketball | FCIAC Semifinals | Away - Wilton HS | Cancelled | ||
| Tue., 2/26 | V Boys Swimming and Diving | FCIAC Trials | Away - Greenwich HS | 5:30 p.m. | ||
| Tue., 2/26 | V Girls Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | W 47-44 | Bob Meyers 4:30 | |
| Wed., 2/27 | V Boys Basketball | Newtown (Scrim.) | Home - Kuzco Gymnasium at Stamford HS [Directions] | 4:30 p.m. | ||
| Wed., 2/27 | V Boys Ice Hockey | Ridgefield | Away - Winter Garden Ice Arena [Directions] | 3:30 p.m. | ||
| Wed., 2/27 | V Boys Swimming and Diving | FCIAC Diving Championship | Home - Westhill Pool [Directions] | 5:00 p.m. | ||
| Thu., 2/28 | V Boys Swimming and Diving | FCIAC Championship | Away - Greenwich HS | 6:30 p.m. | ||
| Thu., 2/28 | Unified Sports Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 3:30 p.m. | Bob 2:15 | |
| Fri., 3/1 | V Girls Basketball | Trumbull | Away - Higher Seed [Directions] | W 47-42 | Bob Meyers - 4:30 | |
| Sun., 3/3 | V Competitive Cheerleading | CIAC State Championships | Away - Floyd Little Athletic Center - New Haven | 10:00 a.m. | Myers 8am | Scheduled performance time - 10:20 |
| Tue., 3/5 | V Boys Basketball | Northwest Catholic | Home - Kuzco Gymnasium at Stamford HS [Directions] | W 48-47 | Northwest Catholic | |
| Tue., 3/5 | Unified Sports Basketball | Westhill | Away [Directions] | 2:45 p.m. | Bob-2:15 | |
| Wed., 3/6 | V Boys Basketball | Bunnell | Away - Bunnell HS [Directions] | 7:00 p.m. | Bob - 4:30 | |
| Thu., 3/7 | V Boys Swimming and Diving | CIAC Class LL Diving Championship | Away - Middletown HS | 5:30 p.m. | ||
| Thu., 3/7 | V Girls Basketball | Wilbur Cross | Away - Wilber Cross HS [Directions] | 7:00 p.m. | Bob - 4:00pm | |
| Thu., 3/7 | Unified Sports Basketball | Fairfield Ludlowe | Away [Directions] | 3:30 p.m. | 1st Student - 2:15 | |
| Sat., 3/9 | V Boys Swimming and Diving | CIAC Class LL Trials | Away - East Hartford HS | 6:00 p.m. | ||
| Sat., 3/9 | V Competitive Cheerleading | Team Of The Year | Away - North Haven HS | 3:00 p.m. | 1st Student - 11:30 | Girls performance time is 3pm |
| Mon., 3/11 | V Boys Swimming and Diving | CIAC Class LL Championship | Away - Southern CT State University | 1:30 p.m. | ||
| Mon., 3/11 | Unified Sports Basketball | Fairfield Ludlowe | Away [Directions] | 3:30 p.m. | 1st - 2:15 | Ludlowe Unified Tournament |
| Tue., 3/12 | V Boys Swimming and Diving | CIAC Open Diving Championship | Away - Bulkeley HS/Hartford | 5:30 p.m. | ||
| Thu., 3/14 | V Boys Swimming and Diving | CIAC Open Championship | Away - Yale University | 7:00 p.m. | ||
| Tue., 3/19 | V Boys Lacrosse | Shelton (Scrim.) | Away - Shelton HS Finn Stadium [Directions] | 5:00 p.m. | 3pm - bob | |
| Thu., 3/21 | V Baseball | New Canaan (Scrim.) | Away - Mead Park [Directions] | 3:30 p.m. | Bob 2:15 | |
| Sat., 3/23 | V Boys Lacrosse | North Haven (Scrim.) | Away [Directions] | 9:00 a.m. | Myers 7am | |
| Sat., 3/23 | V Boys Volleyball | Glastonbury Jamboree | Away - Glastonbury HS | 9:00 a.m. | 1st - 7 am | |
| Sat., 3/23 | V Girls Lacrosse | UPenn scrimmage and trip | Away | TBA | ||
| Sat., 3/23 | V Softball | Darien (Scrim.) | Away - Darien HS Softball Field [Directions] | TBA | Parent transportation | |
| Tue., 3/26 | V Baseball | Jonathan Law (Scrim.) | Home - SHS Baseball Field [Directions] | 3:30 p.m. | ||
| Tue., 3/26 | V Boys Lacrosse | Masuk (Scrim.) | Home - Upper Lacrosse field at SHS [Directions] | L 5-2 | ||
| Tue., 3/26 | V Softball | Newtown (Scrim.) | Home - SHS Softball Field [Directions] | 4:30 p.m. | ||
| Tue., 3/26 | JV Softball | Newtown (Scrim.) | Home - Cummings Park Field #4 [Directions] | 4:30 p.m. | 1st - 3pm | |
| Wed., 3/27 | V Co-ed Sailing | Greenwich | Away - Greenwich YC [Directions] | 3:00 p.m. | 1st - 2pm | |
| Wed., 3/27 | JV Co-ed Sailing | Greenwich | Away - Greenwich YC [Directions] | 3:00 p.m. | ||
| Thu., 3/28 | V Baseball | Greenwich (Scrim.) | Home - SHS Baseball Field [Directions] | 4:00 p.m. | ||
| Thu., 3/28 | JV Baseball | Greenwich (Scrim.) | Home - Belltown Field [Directions] | 4:15 p.m. | ||
| Thu., 3/28 | V Girls Lacrosse | St. Lukes (Scrim.) | Away - St.Lukes | 4:30 p.m. | 1st 3:00 | |
| Thu., 3/28 | V Softball | Lauralton Hall (Scrim.) | Away - Lauralton Hall Field [Directions] | 4:00 p.m. | Bob 2:15pm | |
| Fri., 3/29 | V Baseball | Darien (Scrim.) | Away - DHS Baseball Varsity Field [Directions] | 3:15 p.m. | Myers 2pm | |
| Fri., 3/29 | JV Baseball | Darien (Scrim.) | Away - DHS Baseball JV Field [Directions] | 3:15 p.m. | Myers 2pm | |
| Sat., 3/30 | V Boys Lacrosse | Bunnell-Stratford | Away - Bunnell Turf Field [Directions] | W 9-5 | 1st student 10:15am | |
| Sat., 3/30 | JV Boys Lacrosse | Bunnell-Stratford | Away - Bunnell Turf Field [Directions] | 2:00 p.m. | 1st student 12:15 | |
| Sat., 3/30 | V Boys Volleyball | Kolbe Cathedral | Away - Kolbe Cathedral Gym [Directions] | L 1-3 | Myers 10:30am | |
| Sat., 3/30 | JV Boys Volleyball | Kolbe Cathedral | Away - Kolbe Cathedral Gym [Directions] | W 2-0 | Meyers - 10:30 | |
| Mon., 4/1 | V Boys Tennis | Trumbull | Home - SHS Tennis Courts [Directions] | L 1-6-0 | ||
| Mon., 4/1 | V Boys Volleyball | Shelton | Home - Kuzco Gymnasium at Stamford HS [Directions] | L 0-3 | ||
| Mon., 4/1 | JV Boys Volleyball | Shelton | Home - Kuzco Gymnasium at Stamford HS [Directions] | W 2-0 | ||
| Mon., 4/1 | V Girls Lacrosse | Weston | Home - Boyle Stadium, SHS [Directions] | L 5-15 | ||
| Mon., 4/1 | JV Girls Lacrosse | Weston | Home - Boyle Stadium, SHS [Directions] | 5:30 p.m. | ||
| Mon., 4/1 | V Girls Tennis | Trumbull | Away - THS Tennis Courts [Directions] | L 3-4 | Myers 2:15pm | |
| Tue., 4/2 | V Boys Lacrosse | Wilton | Away - Fujitani Field - Turf [Directions] | L 16-2 | 1st 4:15pm | |
| Tue., 4/2 | JV Boys Lacrosse | Wilton | Away - Fujitani Field - Turf [Directions] | 4:00 p.m. | 1st 2:15pm | |
| Tue., 4/2 | V Boys Tennis | Ridgefield | Away - RHS Tennis Courts [Directions] | L 0-7 | Myers 2pm | |
| Tue., 4/2 | JV Softball | New Canaan | Away - Waveny Park - Orchard Field [Directions] | 4:00 p.m. | 1st 2:15pm | |
| Tue., 4/2 | V Girls Tennis | Ridgefield | Home - Stamford HS [Directions] | L 2-5 | ||
| Wed., 4/3 | V Baseball | Trinity Catholic | Home - SHS Baseball Field [Directions] | W 17-2 | ||
| Wed., 4/3 | JV Baseball | Greenwich | Home - Belltown Field [Directions] | Cancelled | In place of cancelled Trinity game | |
| Wed., 4/3 | FR Baseball | Wright Tech | Away - Cubetta Field [Directions] | 3:45 p.m. | 1st 2:30pm | |
| Wed., 4/3 | V Boys Lacrosse | Staples | Away - Staples Stadium [Directions] | L 17-1 | 1st 3:30pm | |
| Wed., 4/3 | JV Boys Lacrosse | Staples | Away - Wakeman Field B (turf) [Directions] | 4:00 p.m. | 1st 2:15pm | |
| Wed., 4/3 | FR Boys Lacrosse | Greenwich | Away - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | 1st 3:15pm | |
| Wed., 4/3 | V Boys Volleyball | Danbury | Home - Kuzco Gymnasium at Stamford HS [Directions] | L 0-3 | ||
| Wed., 4/3 | JV Boys Volleyball | Danbury | Home - Kuzco Gymnasium at Stamford HS [Directions] | W 2-0 | ||
| Wed., 4/3 | V Co-ed Sailing | Staples | Home - Stamford YC [Directions] | 3:00 p.m. | ||
| Wed., 4/3 | JV Co-ed Sailing | Staples | Home - Stamford YC [Directions] | 3:00 p.m. | ||
| Wed., 4/3 | V Girls Lacrosse | Trumbull | Home - Boyle Stadium, SHS [Directions] | L 7-16 | ||
| Wed., 4/3 | JV Girls Lacrosse | Trumbull | Home - Boyle Stadium, SHS [Directions] | 4:00 p.m. | ||
| Wed., 4/3 | V Softball | New Canaan | Away - Waveny Park - Orchard Field [Directions] | W 15-3 | Myers 2:15pm | |
| Thu., 4/4 | V Boys Tennis | Fairfield Ludlowe | Home [Directions] | L 0-7 | ||
| Thu., 4/4 | V Girls Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe Tennis Courts [Directions] | L 1-6 | Myers 2:15pm | |
| Fri., 4/5 | V Boys Volleyball | Trumbull | Away - THS Main Gym [Directions] | L 0-3 | 1st 2:15pm | |
| Fri., 4/5 | JV Boys Volleyball | Trumbull | Away - THS Main Gym [Directions] | W 2-1 | 1st 2:15pm | |
| Sat., 4/6 | V Softball | Danbury | Home - SHS Softball Field [Directions] | W 8-7 | Non League game | |
| Mon., 4/8 | V Baseball | Trumbull | Home - SHS Baseball Field [Directions] | L 4-5 | ||
| Mon., 4/8 | JV Baseball | Trumbull | Home - Rippowam Field [Directions] | 4:00 p.m. | ||
| Mon., 4/8 | V Boys Volleyball | Staples | Away - Staples H.S. Gym [Directions] | L 0-3 | Myers 2:15pm | |
| Mon., 4/8 | JV Boys Volleyball | Staples | Away - Staples H.S. Gym [Directions] | W 2-0 | Myers 2:15pm | |
| Mon., 4/8 | V Softball | Trumbull | Away - Varsity Softball Field [Directions] | L 0-5 | 1st 2:15pm | |
| Tue., 4/9 | V Boys Lacrosse | Stratford | Home - Boyle Stadium, SHS [Directions] | W 11-3 | ||
| Tue., 4/9 | FR Boys Lacrosse | Fairfield Ludlowe | Home - Upper Lacrosse field at SHS [Directions] | 4:00 p.m. | ||
| Tue., 4/9 | V Girls Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | L 11-12(OT) | Myers 3:15pm | |
| Tue., 4/9 | JV Girls Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 4:30 p.m. | Myers 3:15pm | |
| Wed., 4/10 | V Baseball | Ridgefield | Home - SHS Baseball Field [Directions] | L 3-6 | Myers 2pm | |
| Wed., 4/10 | JV Baseball | Ridgefield | Away - East Ridge MS [Directions] | 4:00 p.m. | Myers 2pm | |
| Wed., 4/10 | FR Baseball | Ridgefield | Home - Belltown Field [Directions] | 4:00 p.m. | ||
| Wed., 4/10 | V Boys Golf | Darien | Home - EG Brennan [Directions] | Darien 147 Stamford 205 | ||
| Wed., 4/10 | V Boys Outdoor Track | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | 1st 2:15pm (2nd bus) | |
| Wed., 4/10 | V Boys Tennis | New Canaan | Away - NCHS Tennis Courts [Directions] | L 0-7 | 1st 2:15pm | |
| Wed., 4/10 | V Boys Volleyball | Darien | Home - Kuzco Gymnasium at Stamford HS [Directions] | L 0-3 | ||
| Wed., 4/10 | JV Boys Volleyball | Darien | Home - Kuzco Gymnasium at Stamford HS [Directions] | W 2-0 | ||
| Wed., 4/10 | V Co-ed Sailing | Rye Country Day (NY) | Home - Stamford YC [Directions] | 3:00 p.m. | ||
| Wed., 4/10 | JV Co-ed Sailing | Rye Country Day (NY) | Home - Stamford YC [Directions] | 3:00 p.m. | ||
| Wed., 4/10 | V Girls Outdoor Track | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | 1st 2:15pm | |
| Wed., 4/10 | V Softball | Ridgefield | Home - SHS Softball Field [Directions] | W 9-2 | 1st 3:00 | |
| Wed., 4/10 | JV Softball | Ridgefield | Home - Cummings Park Field #4 [Directions] | 4:30 p.m. | 1ST - 3:00 | |
| Wed., 4/10 | V Girls Tennis | New Canaan | Home - Stamford HS [Directions] | L 1-6 | ||
| Thu., 4/11 | FR Baseball | Trumbull | Away - JV Baseball Field [Directions] | 4:00 p.m. | 1st 2:15pm | |
| Thu., 4/11 | V Boys Golf | Norwalk, Westhill | Away - Oak Hills G.C. [Directions] | Norwalk 215 Stamford 196 | 1st 2pm | |
| Thu., 4/11 | JV Boys Lacrosse | Trinity Catholic | Home - Upper Lacrosse field at SHS [Directions] | 4:00 p.m. | ||
| Thu., 4/11 | V Boys Tennis | Brien McMahon | Away - Brien McMahon HS [Directions] | W 5-2 | 1st 2:15pm | |
| Thu., 4/11 | V Girls Lacrosse | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | L 3-14 | Myers 2:15pm | |
| Thu., 4/11 | JV Girls Lacrosse | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 5:30 p.m. | Myers 2:15pm | |
| Thu., 4/11 | JV Softball | Trumbull | Away - JV Softball Field [Directions] | 4:00 p.m. | 1st 2:15pm | |
| Thu., 4/11 | V Girls Tennis | Brien McMahon | Home - Stamford HS [Directions] | W 6-1 | ||
| Fri., 4/12 | V Baseball | Fairfield Ludlowe | Home - SHS Baseball Field [Directions] | L 0-4 | ||
| Fri., 4/12 | JV Baseball | Fairfield Ludlowe | Home - Belltown Field [Directions] | 4:00 p.m. | ||
| Fri., 4/12 | FR Baseball | Fairfield Ludlowe | Away - Kiwanis Field [Directions] | 4:00 p.m. | 1st 2:15pm | |
| Fri., 4/12 | FR Boys Lacrosse | Westhill | Home - Upper Lacrosse field at SHS [Directions] | 5:00 p.m. | ||
| Fri., 4/12 | V Boys Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | L 0-3 | 1st 2:15pm | |
| Fri., 4/12 | JV Boys Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | W 2-0 | 1st 2:15pm | |
| Fri., 4/12 | V Girls Lacrosse | Daniel Hand | Away - Surf Club [Directions] | L 5-16 | Myers 2pm | |
| Fri., 4/12 | JV Girls Lacrosse | Daniel Hand | Away - Surf Club [Directions] | 5:30 p.m. | Myers 2pm | |
| Fri., 4/12 | V Softball | Fairfield Ludlowe | Away - Sturges Park [Directions] | L 3-2 | 1st 2:15pm | |
| Fri., 4/12 | JV Softball | Fairfield Ludlowe | Away - Tom Hayden field [Directions] | 4:00 p.m. | 1st 2:15 | |
| Mon., 4/15 | FR Boys Lacrosse | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 5:00 p.m. | 1st 3:15pm | |
| Mon., 4/15 | JV Boys Volleyball | Norwalk | Home - Kuzco Gymnasium at Stamford HS [Directions] | Cancelled | ||
| Mon., 4/15 | V Girls Lacrosse | Fairfield Ludlowe | Home - Boyle Stadium, SHS [Directions] | L 4-13 | ||
| Mon., 4/15 | JV Girls Lacrosse | Fairfield Ludlowe | Home - Boyle Stadium, SHS [Directions] | 5:30 p.m. | ||
| Tue., 4/16 | V Baseball | Harding | Home - SHS Baseball Field [Directions] | W 16-6 | ||
| Tue., 4/16 | V Boys Lacrosse | Brien McMahon | Home - Boyle Stadium, SHS [Directions] | W 5-4 | ||
| Tue., 4/16 | JV Boys Lacrosse | Brien McMahon | Home - Upper Lacrosse field at SHS [Directions] | 5:00 p.m. | ||
| Tue., 4/16 | V Boys Tennis | Greenwich | Away - GHS Tennis Courts [Directions] | L 0-7 | 1st 8:30am | |
| Tue., 4/16 | V Softball | Shelton | Away - Shelton HS Softball Field [Directions] | W 20-14 | 10am - 1st | |
| Tue., 4/16 | V Girls Tennis | Greenwich | Home - Stamford HS [Directions] | L 1-6 | ||
| Wed., 4/17 | V Baseball | New Canaan | Away - Mead Park [Directions] | W 7-1 | 1st 10:15am | |
| Wed., 4/17 | JV Baseball | New Canaan | Away - Waveny Park - Coppo Field [Directions] | 12:00 p.m. | 1st 10:15am | |
| Wed., 4/17 | FR Baseball | New Canaan | Home - SHS Baseball Field [Directions] | 12:00 p.m. | ||
| Wed., 4/17 | FR Boys Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 10:30 a.m. | 8:30 am - 1st | |
| Wed., 4/17 | V Boys Volleyball | Darien | Away - DHS Main Gym [Directions] | L 0-3 | 1st 9:15am | |
| Wed., 4/17 | JV Boys Volleyball | Darien | Away - DHS Main Gym [Directions] | L 1-2 | 1st 9:15am | |
| Wed., 4/17 | V Girls Lacrosse | New Milford | Home - Boyle Stadium, SHS [Directions] | W 11-6 | ||
| Wed., 4/17 | JV Girls Lacrosse | New Milford | Home - Boyle Stadium, SHS [Directions] | 5:30 p.m. | ||
| Wed., 4/17 | V Softball | New Canaan | Home - SHS Softball Field [Directions] | W 15-0 | ||
| Thu., 4/18 | V Baseball | Brien McMahon | Away - Pride Field (BMHS) [Directions] | W 12-5 | 1st 9am | |
| Thu., 4/18 | JV Baseball | Brien McMahon | Away - Roton Field [Directions] | 11:00 a.m. | 1st 9am | |
| Thu., 4/18 | FR Baseball | Brien McMahon | Home - SHS Baseball Field [Directions] | 12:00 p.m. | ||
| Thu., 4/18 | V Boys Lacrosse | Foran | Away - Foran HS - Turf Field [Directions] | W 14-7 | 1st 3:30pm | |
| Thu., 4/18 | JV Boys Lacrosse | Foran | Away - Foran HS - Turf Field [Directions] | 4:00 p.m. | 1st 2pm | |
| Thu., 4/18 | V Softball | Brien McMahon | Home - SHS Softball Field [Directions] | W 21-3 | ||
| Sat., 4/20 | V Boys Lacrosse | Ridgefield | Home - Upper Lacrosse field at SHS [Directions] | L 4-21 | ||
| Sat., 4/20 | JV Boys Lacrosse | Ridgefield | Home - Upper Lacrosse field at SHS [Directions] | 3:00 p.m. | ||
| Mon., 4/22 | V Boys Golf | Ridgefield | Away - Ridgefield Public GC (DHLY Ridge) [Directions] | Ridgefield 161 Stamford 197 | Myers 1:30pm | |
| Mon., 4/22 | FR Boys Lacrosse | St. Joseph | Home - Upper Lacrosse field at SHS [Directions] | 5:00 p.m. | ||
| Mon., 4/22 | V Boys Volleyball | Fairfield Ludlowe | Home - Kuzco Gymnasium at Stamford HS [Directions] | L 2-3 [Detailed Results] | ||
| Mon., 4/22 | JV Boys Volleyball | Fairfield Ludlowe | Home - Kuzco Gymnasium at Stamford HS [Directions] | W 2-0 | ||
| Tue., 4/23 | V Boys Lacrosse | Greenwich | Home - Upper Lacrosse field at SHS [Directions] | L 2-12 | ||
| Tue., 4/23 | JV Boys Lacrosse | Greenwich | Home - Upper Lacrosse field at SHS [Directions] | 5:30 p.m. | ||
| Tue., 4/23 | V Boys Outdoor Track | Staples, Bridgeport Central | Away - Staples Stadium [Directions] | 4:00 p.m. | Myers 2:15pm | |
| Tue., 4/23 | V Girls Lacrosse | Hamden | Home - Boyle Stadium, SHS [Directions] | W 13-9 | ||
| Tue., 4/23 | JV Girls Lacrosse | Hamden | Home - Boyle Stadium, SHS [Directions] | 5:30 p.m. | ||
| Tue., 4/23 | V Girls Outdoor Track | Staples, Bridgeport Central | Away - Staples Stadium [Directions] | 4:00 p.m. | 1st 2:15pm | |
| Tue., 4/23 | V Softball | Darien | Away - DHS Softball Varsity Field [Directions] | W 12-2 | 1st 2:15pm | |
| Tue., 4/23 | V Girls Tennis | Danbury | Away - Henry Abbott Tech tennis courts [Directions] | W 7-0 | 1st 2:45pm | at Abbott Tech HS |
| Wed., 4/24 | V Baseball | Greenwich | Away - GHS Baseball Field [Directions] | L 4-10 | 1st 2:15pm | |
| Wed., 4/24 | JV Baseball | Greenwich | Away - Julian Curtiss School [Directions] | 4:00 p.m. | 1st 2:15pm | |
| Wed., 4/24 | FR Baseball | Greenwich | Home - SHS Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | V Boys Golf | Staples | Home - EG Brennan [Directions] | Staples 169 Stamford 200 | ||
| Wed., 4/24 | V Boys Tennis | Danbury | Home [Directions] | W 6-1 | ||
| Wed., 4/24 | V Boys Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | L 0-3 | 1st 2:15pm | |
| Wed., 4/24 | JV Boys Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | W 2-0 | 1st 2:15pm | |
| Wed., 4/24 | V Co-ed Sailing | Greenwich Academy | Away - Indian Harbor Yacht Club, Greenwich | 3:00 p.m. | 1st 2pm | |
| Wed., 4/24 | JV Co-ed Sailing | Greenwich Academy | Away - Indian Harbor Yacht Club, Greenwich | 3:00 p.m. | ||
| Wed., 4/24 | V Softball | Greenwich | Home - SHS Softball Field [Directions] | W 11-10 | ||
| Wed., 4/24 | JV Softball | Greenwich | Home - Cummings Park Field #4 [Directions] | 4:00 p.m. | 1st 2:30pm | |
| Thu., 4/25 | V Baseball | Darien | Home - SHS Baseball Field [Directions] | L 0-7 | ||
| Thu., 4/25 | JV Baseball | Darien | Home - Belltown Field [Directions] | 4:00 p.m. | ||
| Thu., 4/25 | FR Baseball | Darien | Away - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | 1st 2:15pm | |
| Thu., 4/25 | V Boys Golf | Danbury | Away - Richter Park Golf Course [Directions] | Danbury 189 Stamford 231 | 1st 1:30pm | |
| Thu., 4/25 | FR Boys Lacrosse | Trumbull | Home - Upper Lacrosse field at SHS [Directions] | 5:00 p.m. | ||
| Thu., 4/25 | V Boys Tennis | Staples | Home [Directions] | L 0-7 | ||
| Thu., 4/25 | V Girls Lacrosse | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | W 14-13 | Myers 2:30pm | |
| Thu., 4/25 | JV Girls Lacrosse | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 6:00 p.m. | Myers 2:30pm | |
| Thu., 4/25 | V Girls Tennis | Staples | Away - Staples HS-Tennis Courts [Directions] | L 1-6 | 1st 2:15pm | |
| Fri., 4/26 | V Boys Lacrosse | Westhill | Away - J. Walter Kennedy Stadium [Directions] | W 11-3 | 1st 3:45pm | |
| Fri., 4/26 | V Boys Volleyball | Westhill | Away - Westhill - Main Gymnasium [Directions] | L 0-3 | 1st 2:45pm | |
| Fri., 4/26 | JV Boys Volleyball | Westhill | Away - Westhill - Main Gymnasium [Directions] | W 2-0 | 1st 2:45pm | |
| Sat., 4/27 | V Baseball | St. Joseph | Home - Stamford HS [Directions] | L 9-10 | Meyers 1:30 | |
| Sat., 4/27 | JV Boys Lacrosse | Westhill | Away - J. Walter Kennedy Stadium [Directions] | 11:00 a.m. | 1st 9:45am | |
| Sat., 4/27 | V Boys Tennis | Darien | Home [Directions] | L 0-7 | ||
| Sat., 4/27 | V Co-ed Sailing | CT States | Away - Sail Black Rock, Captain's Cove, 1 Bostwick Avenue, Bridgeport | 9:30 a.m. | ||
| Sat., 4/27 | JV Co-ed Sailing | CT States | Away - Sail Black Rock, Captain's Cove, 1 Bostwick Avenue, Bridgeport | 9:30 a.m. | ||
| Sat., 4/27 | V Softball | St. Joseph | Home - SHS Softball Field [Directions] | L 2-5 | ||
| Sat., 4/27 | JV Softball | St. Joseph | Home - Roxbury elementary school [Directions] | 3:30 p.m. | 1st 2:30pm | |
| Mon., 4/29 | V Baseball | Danbury | Home - SHS Baseball Field [Directions] | L 1-11 | ||
| Mon., 4/29 | JV Baseball | Danbury | Home - Belltown Field [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | FR Baseball | Danbury | Away - Danbury HS Varsity Baseball Field [Directions] | 4:00 p.m. | Myers 2pm | |
| Mon., 4/29 | FR Boys Lacrosse | Ridgefield | Away - Tiger Hollow Turf Field II [Directions] | Cancelled | Myers 2pm | |
| Mon., 4/29 | V Boys Tennis | Norwalk | Away - Norwalk HS [Directions] | W 4-3 | 1st 2:15pm | |
| Mon., 4/29 | V Boys Volleyball | St. Joseph | Home - Kuzco Gymnasium at Stamford HS [Directions] | L 0-3 | ||
| Mon., 4/29 | JV Boys Volleyball | St. Joseph | Home - Kuzco Gymnasium at Stamford HS [Directions] | W 2-0 | ||
| Mon., 4/29 | V Girls Outdoor Track | Greenwich, Ridgefield | Away - Cardinal Stadium [Directions] | 4:00 p.m. | 1st 2:15pm | |
| Mon., 4/29 | V Softball | Danbury | Away - Danbury HS Varsity Softball Field [Directions] | L 3-1 | 1st 2pm | |
| Mon., 4/29 | JV Softball | Danbury | Away - Danbury HS Junior Varsity Softball Field [Directions] | 4:00 p.m. | 1st 2pm | |
| Mon., 4/29 | V Girls Tennis | Norwalk | Home - Stamford HS [Directions] | W 7-0 | ||
| Tue., 4/30 | V Boys Golf | Westhill, Greenwich | Away - E. Gaynor Brennan Golf Course [Directions] | Greenwich 156 Stamford 194 | parent | |
| Tue., 4/30 | V Boys Outdoor Track | Ridgefield, Greenwich | Away - Tiger Hollow Stadium [Directions] | 4:00 p.m. | Myers 2:15pm | |
| Tue., 4/30 | V Boys Tennis | Fairfield Warde | Home [Directions] | L 0-7 | ||
| Tue., 4/30 | V Girls Lacrosse | Brien McMahon | Home - Boyle Stadium, SHS [Directions] | L 10-11 | ||
| Tue., 4/30 | JV Girls Lacrosse | Brien McMahon | Home - Boyle Stadium, SHS [Directions] | 5:30 p.m. | ||
| Tue., 4/30 | V Girls Tennis | Fairfield Warde | Away - FWHS Blake Courts [Directions] | L 3-4 | 1st 2:15pm | |
| Wed., 5/1 | V Baseball | Staples | Home - SHS Baseball Field [Directions] | L 1-11 | ||
| Wed., 5/1 | JV Baseball | Staples | Home - Belltown Field [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | FR Baseball | Staples | Away - Staples HS Baseball Field [Directions] | 4:00 p.m. | 1st 2:15 (w/softball) | |
| Wed., 5/1 | V Boys Lacrosse | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | L 8-7 | Bob 2:15 | |
| Wed., 5/1 | JV Boys Lacrosse | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 6:00 p.m. | 1st 4pm | |
| Wed., 5/1 | FR Boys Lacrosse | Darien | Away - DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | 1st 2:30 | |
| Wed., 5/1 | V Boys Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | L 0-3 | 1st 2:30 | |
| Wed., 5/1 | JV Boys Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | W 2-0 | 1st 2:30 | |
| Wed., 5/1 | V Co-ed Sailing | Fairfield Warde | Away - Pequot Yacht Club, Fairfield [Directions] | 3:00 p.m. | 1st 1:30 | |
| Wed., 5/1 | JV Co-ed Sailing | Fairfield Warde | Away - Pequot Yacht Club, Fairfield [Directions] | 3:00 p.m. | ||
| Wed., 5/1 | V Softball | Staples | Away - Wakeman Field [Directions] | W 6-2 | 1st 2:15 (w/ fr baseball) | |
| Wed., 5/1 | JV Softball | Staples | Away - Staples HS - Softball Field [Directions] | 4:00 p.m. | 1st 2:15 | |
| Thu., 5/2 | V Boys Golf | Westhill, Trinity Catholic | Away - Woodway Country Club [Directions] | Westhill 176 Trinity 242 Stamford 209 | Parent | |
| Thu., 5/2 | V Boys Outdoor Track | Norwalk | Away - Testa Field, NHS [Directions] | Cancelled | 1st 2:15 | |
| Thu., 5/2 | V Boys Tennis | Westhill | Home - SHS Tennis Courts [Directions] | L 0-7 | ||
| Thu., 5/2 | V Girls Lacrosse | Greenwich | Away - GHS Field 3 [Directions] | L 4-17 | Myers 2:45 | |
| Thu., 5/2 | JV Girls Lacrosse | Greenwich | Away - GHS Field 3 [Directions] | 5:30 p.m. | Myers 2:45 | |
| Thu., 5/2 | V Girls Outdoor Track | Norwalk | Away - Testa Field, NHS [Directions] | Cancelled | 1st 2:15 | |
| Thu., 5/2 | V Girls Tennis | Westhill | Away - Westhill Tennis Courts [Directions] | L 1-6 | 1st 2:30 | |
| Fri., 5/3 | V Baseball | Norwalk | Away - Callahan Complex at Nathan Hale Upper [Directions] | L 0-1 | 1st 4:00 | |
| Fri., 5/3 | JV Baseball | Norwalk | Away - City Hall Field [Directions] | 4:00 p.m. | 1st 2:30 | |
| Fri., 5/3 | FR Baseball | Norwalk | Home - SHS Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 5/3 | FR Boys Lacrosse | Westhill | Away - J. Walter Kennedy Stadium [Directions] | 3:30 p.m. | 1st 2:15 | |
| Fri., 5/3 | V Boys Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | L 0-3 | Bob 2:15 | |
| Fri., 5/3 | JV Boys Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | W 2-0 | Bob 2:15 | |
| Fri., 5/3 | V Softball | Norwalk | Home - SHS Softball Field [Directions] | W 9-1 | ||
| Fri., 5/3 | JV Softball | Norwalk | Home - Roxbuy Elementary school [Directions] | 4:00 p.m. | 1st 2:30 | |
| Fri., 5/3 | V Girls Tennis | Darien | Away - DHS Tennis Courts [Directions] | L 1-6 | 1st 2:30pm | |
| Sat., 5/4 | V Baseball | Foran | Away - Ken Walker Field [Directions] | W 8-1 | Bob 10:45 | |
| Sat., 5/4 | V Boys Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | L 2-5 | 1st 12:30 | |
| Sat., 5/4 | JV Boys Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 4:00 p.m. | 1st 2:30 | |
| Sat., 5/4 | V Boys Tennis | St. Joseph | Away [Directions] | W 4-3 | 1st 12:15pm | |
| Sat., 5/4 | JV Boys Volleyball | Norwalk (Scrim.) | Away - Scarso Gymnasium [Directions] | 10:30 a.m. | 1st 9am | |
| Sat., 5/4 | V Girls Lacrosse | Ridgefield | Home - Boyle Stadium, SHS [Directions] | L 2-14 | ||
| Sat., 5/4 | JV Girls Lacrosse | Ridgefield | Home - Boyle Stadium, SHS [Directions] | 5:30 p.m. | ||
| Sat., 5/4 | V Girls Tennis | St. Joseph | Home - Stamford HS [Directions] | L 3-4 | ||
| Mon., 5/6 | V Baseball | Fairfield Warde | Home - SHS Baseball Field [Directions] | W 4-3 | ||
| Mon., 5/6 | FR Baseball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 4:00 p.m. | 1st 2:15pm (w/ softball) | |
| Mon., 5/6 | V Boys Outdoor Track | Danbury, Trumbull | Away - Trumbull HS [Directions] | 4:00 p.m. | Myers 2:15pm | |
| Mon., 5/6 | V Boys Tennis | Bridgeport Central | Home [Directions] | W 7-0 | ||
| Mon., 5/6 | V Boys Volleyball | Staples | Home - Kuzco Gymnasium at Stamford HS [Directions] | L 0-3 | ||
| Mon., 5/6 | JV Boys Volleyball | Staples | Home - Kuzco Gymnasium at Stamford HS [Directions] | W 2-0 | ||
| Mon., 5/6 | V Girls Lacrosse | Immaculate | Home - Boyle Stadium, SHS [Directions] | W 10-5 | ||
| Mon., 5/6 | V Girls Outdoor Track | Danbury, Trumbull | Away - Trumbull HS [Directions] | 4:00 p.m. | 1st 2:15pm | |
| Mon., 5/6 | V Softball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | W 2-0 | 1st 2:15pm (w/ fr baseball) | |
| Mon., 5/6 | JV Softball | Fairfield Warde | Away - Melville Park [Directions] | 4:00 p.m. | 1st 2:15pm | |
| Mon., 5/6 | V Girls Tennis | Bridgeport Central | Away [Directions] | W 7-0 | 1st 2:15pm | |
| Tue., 5/7 | V Boys Golf | Fairfield Ludlowe | Home - EG Brennan [Directions] | Ludlowe 163 Stamford 203 | Parent | |
| Tue., 5/7 | V Boys Lacrosse | Fairfield Warde | Home - Upper Lacrosse field at SHS [Directions] | L 7-16 | ||
| Tue., 5/7 | FR Boys Lacrosse | Wilton | Away - Allen's Field [Directions] | 4:00 p.m. | 1st - 2:15 | |
| Tue., 5/7 | V Boys Tennis | Wilton | Away - Wilton Tennis Courts [Directions] | L 0-7 | Myers 2:15pm | |
| Tue., 5/7 | V Girls Tennis | Wilton | Home - Stamford HS [Directions] | L 0-7 | ||
| Wed., 5/8 | V Baseball | Westhill | Home - Cubeta Stadium [Directions] | L 0-6 | ||
| Wed., 5/8 | JV Baseball | Westhill | Home - Belltown Field [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | FR Baseball | Westhill | Away - Westhill Baseball Field [Directions] | 4:00 p.m. | 1st 2;15pm (w/ softball) | |
| Wed., 5/8 | V Boys Golf | St. Joseph | Away [Directions] | St. Joes 176 Stamford 201 | Myers 1:45pm | |
| Wed., 5/8 | FR Boys Lacrosse | Norwalk | Home - Upper Lacrosse field at SHS [Directions] | 5:00 p.m. | ||
| Wed., 5/8 | V Boys Volleyball | Trumbull | Home - Kuzco Gymnasium at Stamford HS [Directions] | L 1-3 [Detailed Results] | ||
| Wed., 5/8 | JV Boys Volleyball | Trumbull | Home - Kuzco Gymnasium at Stamford HS [Directions] | W 2-1 | ||
| Wed., 5/8 | V Co-ed Sailing | Greenwich | Away - Indian Harbor Yacht club [Directions] | 4:00 p.m. | 1st 2:30pm | |
| Wed., 5/8 | JV Co-ed Sailing | Rye (NY) | Away - American YC - 499 Stuyvesant Ave, Rye, NY 10580 | Cancelled | 1st 1:30pm | |
| Wed., 5/8 | V Softball | Westhill | Away - Westhill Softball Field [Directions] | W 6-4 | 1st 2:15pm (w/ fr baseball) | |
| Wed., 5/8 | JV Softball | Westhill | Away - Roxbury Elementary School [Directions] | 4:00 p.m. | 1st 2:15pm | |
| Thu., 5/9 | V Baseball | Bridgeport Central | Home - SHS Baseball Field [Directions] | W 12-0 | ||
| Thu., 5/9 | V Boys Golf | Fairfield Warde | Home - EG Brennan [Directions] | Warde 156 Stamford 182 | Parent | |
| Thu., 5/9 | V Boys Lacrosse | Fairfield Ludlowe | Home - Boyle Stadium, SHS [Directions] | L 4-20 | ||
| Thu., 5/9 | JV Boys Lacrosse | Fairfield Ludlowe | Home - Upper Lacrosse field at SHS [Directions] | 5:00 p.m. | ||
| Thu., 5/9 | V Boys Tennis | Trinity Catholic | Away | W 6-1 | 1st 2:45pm | At Scalzi Park |
| Thu., 5/9 | V Girls Lacrosse | Staples | Away - Ginny Parker Field - Staples [Directions] | L 6-18 | Myers 2:15pm | |
| Thu., 5/9 | JV Girls Lacrosse | Staples | Away - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | Myers 2:15pm | |
| Thu., 5/9 | V Softball | Bridgeport Central | Away - Central H.S. Varsity Softball Field [Directions] | W 19-1 | 1st 2:15pm | |
| Thu., 5/9 | V Girls Tennis | Trinity Catholic | Home - Stamford HS [Directions] | W 6-1 | ||
| Fri., 5/10 | FR Boys Lacrosse | Trumbull | Away - The Pit [Directions] | 4:00 p.m. | 1st 2:15pm | |
| Fri., 5/10 | V Boys Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | L 0-3 | Bob 3pm | |
| Fri., 5/10 | JV Boys Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | W 2-0 | Bob 3pm | |
| Sat., 5/11 | V Baseball | Brookfield | Away - BHS Baseball Field [Directions] | W 3-1 | 1st 9:45am | |
| Sat., 5/11 | V Boys Lacrosse | Trumbull | Home - Upper Lacrosse field at SHS [Directions] | L 3-17 | ||
| Sat., 5/11 | JV Boys Lacrosse | Trumbull | Home - Upper Lacrosse field at SHS [Directions] | 1:00 p.m. | ||
| Sat., 5/11 | V Softball | Norwich Free Academy | Home - SHS Softball Field [Directions] | W 6-3 | ||
| Sat., 5/11 | JV Softball | Norwich Free Academy | Home - Cummings Park Field #4 [Directions] | 2:00 p.m. | Parent transportation | |
| Mon., 5/13 | FR Boys Lacrosse | New Canaan | Home - Upper Lacrosse field at SHS [Directions] | 5:00 p.m. | ||
| Mon., 5/13 | V Boys Volleyball | Westhill | Home - Kuzco Gymnasium at Stamford HS [Directions] | L 2-3 | ||
| Mon., 5/13 | JV Boys Volleyball | Westhill | Home - Kuzco Gymnasium at Stamford HS [Directions] | W 2-0 | ||
| Tue., 5/14 | V Baseball | Wilton | Away - WHS Varsity Baseball Field [Directions] | W 7-4 | 1st 4pm | |
| Tue., 5/14 | V Boys Golf | Wilton | Away - Rolling Hills CC [Directions] | 3:15 p.m. | 1st 2pm | |
| Tue., 5/14 | FR Boys Lacrosse | Fairfield Warde | Home - Upper Lacrosse field at SHS [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | V Boys Outdoor Track | Westhill | Away - J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | 1st 2:30pm | Boys & Girls throwing/jumping events only |
| Tue., 5/14 | V Co-ed Sailing | Silver Cup | Away - Greenwich | 4:00 p.m. | 2:30 1st | |
| Tue., 5/14 | JV Co-ed Sailing | Silver Cup | Away - TBA | Cancelled | ||
| Tue., 5/14 | V Girls Lacrosse | Westhill | Home - Boyle Stadium, SHS [Directions] | W 9-8 | ||
| Tue., 5/14 | JV Girls Lacrosse | Westhill | Home - Boyle Stadium, SHS [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | V Softball | Wilton | Home - SHS Softball Field [Directions] | W 9-0 | ||
| Wed., 5/15 | V Baseball | Trinity Catholic | Away - Trinity Catholic's Lione Field | L 2-4 | 1st 2:45pm | |
| Wed., 5/15 | V Boys Golf | Westhill, Brien McMahon | Away - E. Gaynor Brennan Golf Course [Directions] | 3:15 p.m. | Parent | |
| Wed., 5/15 | V Boys Lacrosse | Notre Dame-Fairfield | Away - Park Avenue Field at Notre Dame [Directions] | W 13-0 | 1st 2:15pm | |
| Wed., 5/15 | JV Boys Lacrosse | Fairfield Warde | Home - Upper Lacrosse field at SHS [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | V Boys Volleyball | Greenwich | Home - Kuzco Gymnasium at Stamford HS [Directions] | L 0-3 | ||
| Wed., 5/15 | JV Boys Volleyball | Greenwich | Home - Kuzco Gymnasium at Stamford HS [Directions] | W 2-0 | ||
| Wed., 5/15 | V Co-ed Sailing | Gold Cup | Away - Greenwich | 4:00 p.m. | 1st 2:30 | |
| Wed., 5/15 | V Girls Outdoor Track | Westhill | Home [Directions] | 4:00 p.m. | Boys & Girls Running events only | |
| Wed., 5/15 | V Softball | Trinity Catholic | Home - SHS Softball Field [Directions] | W 20-0 | ||
| Thu., 5/16 | JV Baseball | Fairfield Warde | Home - Belltown Field [Directions] | 4:00 p.m. | ||
| Thu., 5/16 | V Boys Golf | Trumbull | Home - EG Brennan [Directions] | 3:15 p.m. | Parent | |
| Thu., 5/16 | V Boys Volleyball | Shelton | Away - Shelton HS Gym [Directions] | L 0-3 | 1st 2:30pm | |
| Thu., 5/16 | JV Boys Volleyball | Shelton | Away - Shelton HS Gym [Directions] | 4:30 p.m. | 1st 2:30pm | |
| Fri., 5/17 | V Softball | Ridgefield | Home - SHS Softball Field [Directions] | W 10-7 | ||
| Sat., 5/18 | V Boys Lacrosse | Hamden | Home - Boyle Stadium, SHS [Directions] | W 11-2 | ||
| Sat., 5/18 | JV Boys Lacrosse | Hamden | Home - Upper Lacrosse field at SHS [Directions] | 4:00 p.m. | ||
| Sat., 5/18 | V Girls Lacrosse | Lauralton Hall | Home - Boyle Stadium, SHS [Directions] | L 7-10 | ||
| Sat., 5/18 | JV Girls Lacrosse | Lauralton Hall | Home - Boyle Stadium, SHS [Directions] | 1:30 p.m. | ||
| Mon., 5/20 | V Softball | St. Joseph | Away - Sacred Heart University [Directions] | L 6-1 | 12:30 1st | |
| Tue., 5/21 | V Boys Golf | New Canaan | Away - Country Club of New Canaan [Directions] | 3:15 p.m. | Myers 2:15 | |
| Tue., 5/21 | V Boys Outdoor Track | FCIACs | Away - Southern CT State U | 12:00 p.m. | 11:15 am | |
| Tue., 5/21 | V Girls Outdoor Track | FCAICs | Away - Southern CT State U | 12:00 p.m. | 11:15am | |
| Wed., 5/22 | V Boys Lacrosse | Bethel (Scrim.) | Home - Upper Lacrosse field at SHS [Directions] | 4:00 p.m. | ||
| Thu., 5/23 | V Baseball | Brien McMahon (Scrim.) | Away - BMHS [Directions] | 4:00 p.m. | 2:15 Bob | |
| Thu., 5/23 | V Boys Golf | Call To The Tee - Chappa Invitational | Away - Longshore Golf Course | TBA | ||
| Thu., 5/23 | V Softball | Greenwich (Scrim.) | Away - Greenwich HS [Directions] | 4:00 p.m. | 2:30 1st | |
| Sat., 5/25 | V Baseball | Middletown | Away - Middletown HS [Directions] | 11:00 a.m. | 8:30 - 1st | |
| Sat., 5/25 | V Boys Lacrosse | Southington | Away - Southington HS [Directions] | 4:00 p.m. | 1pm Bob | |
| Tue., 5/28 | V Softball | State Playoffs Opening Round | Home - TBA [Directions] | Cancelled | ||
| Wed., 5/29 | V Boys Outdoor Track | State LL Championships | Away - Willowbrook Park - New Britain | 3:00 p.m. | 12:15 Bob | |
| Wed., 5/29 | V Girls Outdoor Track | State LL Championships | Away - Willowbrook Park - New Britain | 3:00 p.m. | 12:15 Bob | |
| Wed., 5/29 | V Softball | New Milford | Home - SHS Softball Field [Directions] | W 10-0 | ||
| Thu., 5/30 | V Softball | Fairfield Warde | Home - SHS Softball Field [Directions] | W 8-3 | ||
| Sat., 6/1 | V Softball | Trumbull | Away - Varsity Softball Field [Directions] | 2:00 p.m. | 11:30am - Bob | |