| Stamford 2013-14 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 727 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time/Result | Bus Time | Note |
| TBA | FR Baseball | Greenwich | Home - Stamford High School [Directions] | 4:00 p.m. | ||
| TBA | SO Football | Staples | Home - Stamford High School [Directions] | TBA | ||
| TBA | V Boys Golf | Westhill, Trinity Catholic | Away - Woodway [Directions] | 1:00 p.m. | ||
| TBA | FR Boys Lacrosse | Westhill | Home - Stamford High Soccer Field [Directions] | 10:30 a.m. | ||
| TBA | FR Boys Soccer | Danbury | Away - Danbury High School Grass Field [Directions] | TBA | 2:15 pm | |
| TBA | JV Softball | New Rochelle (NY) | Away - New Rochelle High School | TBA | 10 :00 am | |
| Tue., 8/27 | V Field Hockey | Brien McMahon (Scrim.) | Home - Stamford High School [Directions] | 4:00 p.m. | ||
| Tue., 8/27 | JV Field Hockey | Brien McMahon (Scrim.) | Home - Stamford High School [Directions] | 4:00 p.m. | ||
| Thu., 8/29 | V Girls Volleyball | King and Low-Heywood Thomas (Scrim.) | Away - King Low Heywood Thomas | 4:00 p.m. | 2:15 pm | |
| Sat., 8/31 | V Football | New Rochelle (NY) (Scrim.) | Away - New Rochelle High School | 10:00 a.m. | 8:00am | |
| Sat., 8/31 | V Boys Soccer | King and Low-Heywood Thomas (Scrim.) | Home - Stamford High School [Directions] | 9:00 a.m. | ||
| Sat., 8/31 | V Girls Volleyball | Joel Barlow (Scrim.) | Home - Stamford High School [Directions] | 10:00 a.m. | ||
| Wed., 9/4 | V Football | Bethel (Scrim.) | Home - Stamford High School [Directions] | 4:30 p.m. | ||
| Wed., 9/4 | FR Football | Bethel (Scrim.) | Away - Bethel High School [Directions] | 4:00 p.m. | 2:15 pm | |
| Wed., 9/4 | FR Football | Bethel (Scrim.) | Away - Bethel High School [Directions] | 4:00 p.m. | 2:15 pm | |
| Tue., 9/10 | V Boys Cross Country | Ridgefield, Bassick, Greenwich | Away - RHS Upper Grass Field [Directions] | Ridgefield 23-Stamford 32 Greenwich23- Stamford 36 Stamford17-Bassick 44 | 2:15 pm | |
| Tue., 9/10 | SO Football | New Canaan | Home - Stamford High School [Directions] | 4:30 p.m. | ||
| Tue., 9/10 | V Boys Soccer | Trinity Catholic | Away - Trinity Catholic Soccer Field | W 4-0 | 2:30 PM | |
| Tue., 9/10 | V Girls Cross Country | Ridgefield, Bassick, Greenwich | Away - RHS Upper Grass Field [Directions] | 4:00 p.m. | ||
| Tue., 9/10 | V Girls Volleyball | Weston | Home - Stamford High School [Directions] | W 3-0 | ||
| Tue., 9/10 | JV Girls Volleyball | Weston | Home - Stamford High School [Directions] | W 2-0 | ||
| Wed., 9/11 | FR Football | Fairfield Prep (Scrim.) | Away - Alumni Field, Fairfield University [Directions] | 3:45 p.m. | 2:00PM | |
| Wed., 9/11 | V Field Hockey | Darien | Home - Stamford High School [Directions] | L 0-9 | ||
| Wed., 9/11 | JV Field Hockey | Darien | Home - Stamford High School [Directions] | 5:30 p.m. | ||
| Wed., 9/11 | V Girls Soccer | Danbury | Away - Danbury High School Stadium [Directions] | L 0-3 | 2:15PM | |
| Wed., 9/11 | JV Girls Soccer | Danbury | Away - Danbury High School Grass Field [Directions] | 4:00 p.m. | 1:45 PM | |
| Thu., 9/12 | V Boys Soccer | Darien | Away - DHS Turf #2 [Directions] | W 1-0 | 2:30PM | |
| Thu., 9/12 | JV Boys Soccer | Darien | Away - Middlesex Upper Field [Directions] | 4:00 p.m. | 2:30PM | |
| Thu., 9/12 | FR Boys Soccer | Darien | Home - Stamford High Soccer Field [Directions] | 4:00 p.m. | ||
| Thu., 9/12 | V Competitive Cheerleading | Fairfield Prep | Home - Stamford High School [Directions] | 7:00 p.m. | ||
| Thu., 9/12 | V Girls Volleyball | Brien McMahon | Away - Brien McMahon HS [Directions] | W 3-0 | 2:30PM | |
| Thu., 9/12 | JV Girls Volleyball | Brien McMahon | Away - Brien McMahon HS [Directions] | W 2-0 | 2:15PM | |
| Fri., 9/13 | V Football | Fairfield Prep | Home - Stamford High School [Directions] | L 0-28 | ||
| Fri., 9/13 | JV Football | Fairfield Prep | Home - Stamford High School [Directions] | 3:15 p.m. | ||
| Fri., 9/13 | V Field Hockey | Westhill | Away - Westhill Front Turf Field [Directions] | L 2-4 | 2:15 pm | |
| Fri., 9/13 | V Girls Soccer | Trumbull | Away - McDougall Stadium [Directions] | L 0-6 | 1:30PM | |
| Fri., 9/13 | JV Girls Soccer | Trumbull | Away - JV Grass Soccer Field [Directions] | 3:00 p.m. | 1:45 PM | |
| Mon., 9/16 | V Boys Soccer | Bridgeport Central | Home - Stamford High Soccer Field [Directions] | T 1-1 | ||
| Mon., 9/16 | JV Boys Soccer | Bridgeport Central | Home - Rippowam Field [Directions] | 4:00 p.m. | ||
| Mon., 9/16 | FR Boys Soccer | Bridgeport Central | Away - Kennedy Stadium [Directions] | 4:00 p.m. | 2:15 pm | |
| Mon., 9/16 | V Field Hockey | Fairfield Warde | Home - Stamford High School [Directions] | L 0-2 | ||
| Mon., 9/16 | JV Field Hockey | Fairfield Warde | Home - Stamford High School [Directions] | 5:30 p.m. | ||
| Mon., 9/16 | V Girls Volleyball | Danbury | Home - Stamford High School [Directions] | W 3-0 | ||
| Mon., 9/16 | JV Girls Volleyball | Danbury | Home - Stamford High School [Directions] | W 2-1 | ||
| Mon., 9/16 | FR Girls Volleyball | Danbury | Away - Danbury High School - MAIN gym [Directions] | 4:00 p.m. | 2:15 pm | |
| Tue., 9/17 | V Boys Cross Country | St. Joseph, Westhill, Norwalk | Away [Directions] | 4:00 p.m. | 2:15 pm | |
| Tue., 9/17 | SO Football | Greenwich | Home - Stamford High School [Directions] | 4:30 p.m. | ||
| Tue., 9/17 | V Girls Cross Country | St. Joseph, Westhill, Norwalk | Away [Directions] | 4:00 p.m. | ||
| Tue., 9/17 | V Girls Soccer | Staples | Home - Stamford High Soccer Field [Directions] | L 0-2 | ||
| Tue., 9/17 | JV Girls Soccer | Staples | Home - Rippowam Field [Directions] | 4:00 p.m. | ||
| Tue., 9/17 | V Girls Swimming and Diving | Norwalk/McMahon | Away - Norwalk High Pool [Directions] | 3:15 p.m. | 1:45 | Early Release @ 1:30 |
| Wed., 9/18 | V Boys Soccer | Bassick | Away [Directions] | W 3- 0 | 2:15 pm | |
| Wed., 9/18 | JV Boys Soccer | Bassick | Away [Directions] | 4:00 p.m. | 2:15PM | |
| Wed., 9/18 | V Girls Swimming and Diving | Danbury | Home - Westhill Pool [Directions] | 3:15 p.m. | ||
| Wed., 9/18 | V Girls Volleyball | Bridgeport Central | Home - Stamford High School [Directions] | W 3-0 | ||
| Wed., 9/18 | JV Girls Volleyball | Bridgeport Central | Home - Stamford High School [Directions] | W 2-0 | ||
| Thu., 9/19 | FR Football | Harding | Away - Harding-Hedges Field-Bridgeport [Directions] | 4:00 p.m. | 2:15 pm | |
| Thu., 9/19 | V Field Hockey | Norwalk | Home - Stamford High School [Directions] | T 1-1 | ||
| Thu., 9/19 | JV Field Hockey | Norwalk | Home - Stamford High School [Directions] | 5:30 p.m. | ||
| Thu., 9/19 | V Girls Soccer | Ridgefield | Away - Tiger Hollow Stadium [Directions] | L 0-7 | 3:30PM | |
| Thu., 9/19 | JV Girls Soccer | Ridgefield | Away - RHS Lower Grass Field [Directions] | 4:00 p.m. | 2:15 PM | |
| Fri., 9/20 | V Football | Harding | Home - Stamford High School [Directions] | L 3-14 | ||
| Fri., 9/20 | V Boys Soccer | Harding | Away - Harding-Hedges Field-Bridgeport [Directions] | W 2-1 | 2:15 pm | |
| Fri., 9/20 | V Competitive Cheerleading | Harding | Home - Stamford High School [Directions] | 6:00 p.m. | ||
| Fri., 9/20 | V Girls Volleyball | Bassick | Home - Stamford High School [Directions] | W 3-0 | ||
| Fri., 9/20 | JV Girls Volleyball | Bassick | Home - Stamford High School [Directions] | W 2-0 | ||
| Sat., 9/21 | V Girls Soccer | St. Joseph | Away - St. Joseph High School [Directions] | L 0-8 | 10:15 am | |
| Sat., 9/21 | JV Girls Soccer | St. Joseph | Away - St. Joseph High School [Directions] | 12:00 p.m. | 2 :15PM | |
| Mon., 9/23 | JV Football | Harding | Home - Stamford High School [Directions] | 4:00 p.m. | ||
| Mon., 9/23 | V Boys Soccer | Norwalk | Home - Stamford High Soccer Field [Directions] | W 3 -1 | ||
| Mon., 9/23 | JV Boys Soccer | Norwalk | Home - Rippowam Field [Directions] | 4:00 p.m. | ||
| Mon., 9/23 | FR Boys Soccer | Norwalk | Away - Nathan Hale Middle School [Directions] | 4:00 p.m. | 2:25 pm | |
| Mon., 9/23 | V Girls Volleyball | Darien | Away [Directions] | L 3-1 | 2:30 PM | |
| Mon., 9/23 | JV Girls Volleyball | Darien | Away [Directions] | L 2-0 | 2:30PM | |
| Mon., 9/23 | FR Girls Volleyball | Darien | Home [Directions] | 4:00 p.m. | ||
| Tue., 9/24 | V Boys Cross Country | Trumbull, Wilton, Danbury, Harding | Away - XC Course [Directions] | 4:00 p.m. | 2:15 pm | |
| Tue., 9/24 | SO Football | Trumbull | Home - Stamford High School [Directions] | 4:00 p.m. | ||
| Tue., 9/24 | SO Football | New Canaan | Away - Dunning Field [Directions] | Cancelled | 3:15 pm | |
| Tue., 9/24 | V Girls Cross Country | Trumbull, Wilton, Danbury, Harding | Away - XC Course [Directions] | 4:00 p.m. | ||
| Tue., 9/24 | V Girls Soccer | Fairfield Warde | Home - Stamford High Soccer Field [Directions] | L 0-3 | ||
| Tue., 9/24 | JV Girls Soccer | Fairfield Warde | Home - Rippowam Field [Directions] | 4:00 p.m. | ||
| Wed., 9/25 | V Boys Soccer | Fairfield Warde | Home - Stamford High Soccer Field [Directions] | W 1-0 | ||
| Wed., 9/25 | JV Boys Soccer | Fairfield Warde | Home - Rippowam Field [Directions] | 4:00 p.m. | ||
| Wed., 9/25 | FR Boys Soccer | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | 2:25 pm | |
| Wed., 9/25 | V Field Hockey | Ridgefield | Home - Stamford High School [Directions] | L 0-2 | ||
| Wed., 9/25 | JV Field Hockey | Ridgefield | Home - Stamford High School [Directions] | 4:00 p.m. | ||
| Wed., 9/25 | V Girls Swimming and Diving | New Canaan | Away - New Canaan YMCA [Directions] | 3:00 p.m. | 1:45 | Early Release @ 1:46 |
| Wed., 9/25 | V Girls Volleyball | Wilton | Home - Stamford High School [Directions] | W 3-0 | ||
| Wed., 9/25 | JV Girls Volleyball | Wilton | Home - Stamford High School [Directions] | W 2-0 | ||
| Wed., 9/25 | FR Girls Volleyball | Wilton | Away - Wilton Field House [Directions] | 4:00 p.m. | 2:15 pm | |
| Thu., 9/26 | FR Football | Trumbull | Home - Stamford High School [Directions] | 4:00 p.m. | ||
| Thu., 9/26 | V Girls Soccer | Fairfield Ludlowe | Home - Stamford High Soccer Field [Directions] | L 1-4 | ||
| Thu., 9/26 | JV Girls Soccer | Fairfield Ludlowe | Home - Rippowam Field [Directions] | 4:00 p.m. | ||
| Fri., 9/27 | V Football | Trumbull | Away - McDougall Stadium [Directions] | L 6-42 | 4:30pm | |
| Fri., 9/27 | V Boys Soccer | Ridgefield | Away - Tiger Hollow Stadium [Directions] | L 2-0 | 4:30 pm | |
| Fri., 9/27 | JV Boys Soccer | Ridgefield | Away - RHS Lower Grass Field [Directions] | 5:00 p.m. | 2:15PM | |
| Fri., 9/27 | FR Boys Soccer | Ridgefield | Home - Stamford High Soccer Field [Directions] | 4:00 p.m. | ||
| Fri., 9/27 | V Competitive Cheerleading | Trumbull | Away - Jerry McDougal Stadium Trumbull [Directions] | 7:00 p.m. | 5:15pm | |
| Fri., 9/27 | V Field Hockey | Brien McMahon | Home - Stamford High School [Directions] | W 3-0 | ||
| Fri., 9/27 | JV Field Hockey | Brien McMahon | Home - Stamford High School [Directions] | 5:30 p.m. | ||
| Fri., 9/27 | V Girls Swimming and Diving | St. Joseph | Home - Westhill Pool [Directions] | 3:15 p.m. | ||
| Fri., 9/27 | V Girls Volleyball | Trumbull | Home - Stamford High School [Directions] | W 3-0 | ||
| Fri., 9/27 | JV Girls Volleyball | Trumbull | Home - Stamford High School [Directions] | L 2-0 | ||
| Fri., 9/27 | FR Girls Volleyball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | 2:15 pm | |
| Mon., 9/30 | JV Football | Trumbull | Away - McDougall Stadium [Directions] | 4:00 p.m. | 2:15 PM | |
| Mon., 9/30 | V Girls Soccer | Norwalk | Home - Stamford High Soccer Field [Directions] | W 2-0 | 2:30PM | |
| Mon., 9/30 | JV Girls Soccer | Norwalk | Home - Rippowam Field [Directions] | 4:00 p.m. | ||
| Mon., 9/30 | V Girls Volleyball | Trinity Catholic | Away - Walsh Court | W 3-0 | 2:30 PM | |
| Mon., 9/30 | JV Girls Volleyball | Trinity Catholic | Away - Walsh Court | W 2-0 | 2:30PM | |
| Tue., 10/1 | V Boys Cross Country | New Canaan, Fairfield Warde, Darien, Trinity Catholic | Away - Waveny Park [Directions] | 4:00 p.m. | 2:30 pm | |
| Tue., 10/1 | V Boys Soccer | St. Joseph | Away - St. Joseph High School [Directions] | W 1-0 | 2:15pm | |
| Tue., 10/1 | JV Boys Soccer | St. Joseph | Away - St. Joseph High School [Directions] | 5:45 p.m. | 2:15PM | |
| Tue., 10/1 | V Girls Cross Country | New Canaan, Fairfield Warde, Darien, Trinity Catholic | Away - Waveny Park [Directions] | 4:00 p.m. | ||
| Tue., 10/1 | V Field Hockey | Staples | Away - Staples Stadium [Directions] | L 4-3 | 2:15PM | |
| Tue., 10/1 | JV Field Hockey | Staples | Away - Ginny Parker Field - Staples [Directions] | 4:45 p.m. | ||
| Wed., 10/2 | SO Football | Darien | Home - Stamford High School [Directions] | 4:30 p.m. | ||
| Wed., 10/2 | V Field Hockey | Greenwich | Away - Cardinal Stadium [Directions] | L 3-1 | 2:15PM | |
| Wed., 10/2 | JV Field Hockey | Greenwich | Away - Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Wed., 10/2 | V Girls Soccer | Darien | Away - DHS Turf #2 [Directions] | L 0-2 | 2:30PM | |
| Wed., 10/2 | JV Girls Soccer | Darien | Away - Middlesex Upper Field [Directions] | 4:00 p.m. | 2:30 PM | |
| Thu., 10/3 | FR Football | Staples | Away - Staples Stadium [Directions] | 6:00 p.m. | 4:00 pm | |
| Thu., 10/3 | V Boys Soccer | Trumbull | Home - Stamford High Soccer Field [Directions] | L 2-1 | ||
| Thu., 10/3 | JV Boys Soccer | Trumbull | Home - Rippowam Field [Directions] | 4:00 p.m. | ||
| Thu., 10/3 | FR Boys Soccer | Trumbull | Away - JV Grass Soccer Field [Directions] | 4:00 p.m. | 2:15 pm | |
| Thu., 10/3 | V Girls Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | L 1-3 | 2:30 PM | |
| Thu., 10/3 | JV Girls Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | L 2-1 | 2:15PM | |
| Thu., 10/3 | FR Girls Volleyball | Fairfield Ludlowe | Home [Directions] | 4:00 p.m. | ||
| Fri., 10/4 | V Football | Staples | Home - Stamford High School [Directions] | L 14-41 | ||
| Fri., 10/4 | V Competitive Cheerleading | Staples | Home - Stamford High School [Directions] | 7:00 p.m. | ||
| Fri., 10/4 | V Girls Soccer | Bridgeport Central | Home - Stamford High Soccer Field [Directions] | W 6-0 | ||
| Fri., 10/4 | V Girls Swimming and Diving | Trumbull | Away - Hillcrest Middle School [Directions] | 4:00 p.m. | 2:00 | Early Release @ 1:46 |
| Sat., 10/5 | JV Football | Staples | Home - Stamford High School [Directions] | 10:00 a.m. | ||
| Sat., 10/5 | V Girls Volleyball | Wolcott | Away - John H. Morris Gymnasium, Wolcott High School [Directions] | W 3-1 | 2:15 pm | |
| Sat., 10/5 | JV Girls Volleyball | Wolcott | Away - John H. Morris Gymnasium, Wolcott High School [Directions] | W 2-1 | 2:15 pm | |
| Mon., 10/7 | V Boys Soccer | Danbury | Home - Stamford High Soccer Field [Directions] | T 1-1 | ||
| Mon., 10/7 | JV Boys Soccer | Danbury | Home - Rippowam Field [Directions] | 4:00 p.m. | ||
| Mon., 10/7 | V Field Hockey | New Canaan | Home - Stamford High School [Directions] | L 0-4 | ||
| Mon., 10/7 | JV Field Hockey | New Canaan | Home - Stamford High School [Directions] | 5:30 p.m. | ||
| Mon., 10/7 | V Girls Volleyball | St. Joseph | Away - St. Joseph High School [Directions] | L 3-1 | 2:30 PM | |
| Mon., 10/7 | JV Girls Volleyball | St. Joseph | Away - St. Joseph High School [Directions] | W 2-0 | 2:15PM | |
| Tue., 10/8 | V Boys Cross Country | Staples, Fairfield Ludlowe, Brien McMahon, Bridgeport Central | Away - Staples Stadium [Directions] | 4:00 p.m. | 2:30 pm | |
| Tue., 10/8 | V Girls Cross Country | Staples, Fairfield Ludlowe, Brien McMahon, Bridgeport Central | Away - Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 10/8 | V Girls Soccer | Greenwich | Away - Cardinal Stadium [Directions] | L 0-1 | 2:15PM | |
| Tue., 10/8 | JV Girls Soccer | Greenwich | Away - GHS Field 3 [Directions] | 4:00 p.m. | 2:30PM | |
| Wed., 10/9 | V Girls Swimming and Diving | Staples | Home - Westhill Pool [Directions] | 3:15 p.m. | ||
| Wed., 10/9 | V Girls Volleyball | Ridgefield | Home - Stamford High School [Directions] | L 3-2 | ||
| Wed., 10/9 | JV Girls Volleyball | Ridgefield | Home - Stamford High School [Directions] | L 2-0 | ||
| Wed., 10/9 | FR Girls Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | 2:15 pm | |
| Thu., 10/10 | FR Football | Ridgefield | Away - Tiger Hollow Turf Field II [Directions] | 4:30 p.m. | 2:15 pm | |
| Thu., 10/10 | V Field Hockey | Wilton | Away - Fujitani Field - Turf [Directions] | L 0-5 | 2:15PM | |
| Thu., 10/10 | JV Field Hockey | Wilton | Away - Fujitani Field - Turf [Directions] | 5:30 p.m. | ||
| Thu., 10/10 | V Girls Soccer | Westhill | Home - Stamford High School [Directions] | L 0-4 | ||
| Thu., 10/10 | JV Girls Soccer | Westhill | Home - Rippowam Field [Directions] | 4:00 p.m. | ||
| Fri., 10/11 | V Football | Ridgefield | Home - Stamford High School [Directions] | L 22-48 | ||
| Fri., 10/11 | V Boys Soccer | Westhill | Home - Stamford High Soccer Field [Directions] | T 0-0 | ||
| Fri., 10/11 | JV Boys Soccer | Westhill | Home - Rippowam Field [Directions] | 4:00 p.m. | ||
| Fri., 10/11 | V Competitive Cheerleading | Ridgefield | Home - Stamford High School [Directions] | 6:00 p.m. | ||
| Fri., 10/11 | V Girls Swimming and Diving | Ridgefield | Away - Pool at Barlow Mountain School [Directions] | 4:00 p.m. | 2:15 | |
| Fri., 10/11 | V Girls Volleyball | New Canaan | Home - Stamford High School [Directions] | W 3-0 | ||
| Fri., 10/11 | JV Girls Volleyball | New Canaan | Home - Stamford High School [Directions] | W 2-0 | ||
| Fri., 10/11 | FR Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | 2:30 pm | |
| Sat., 10/12 | FR Boys Soccer | Westhill | Away - Westhill Front Turf Field [Directions] | 1:00 p.m. | 11:45AM | |
| Sat., 10/12 | V Field Hockey | New Canaan | Away - Dunning Stadium [Directions] | L 1-2 | 8:30 am | |
| Mon., 10/14 | JV Football | Ridgefield | Home - Stamford High School [Directions] | 10:00 a.m. | ||
| Tue., 10/15 | V Boys Soccer | Fairfield Ludlowe | Away - Taft Field [Directions] | L 0-3 | 4:00pm | |
| Tue., 10/15 | JV Boys Soccer | Fairfield Ludlowe | Away - Sturges Park [Directions] | 4:00 p.m. | 2:15PM | |
| Tue., 10/15 | FR Boys Soccer | Fairfield Ludlowe | Home - Stamford High Soccer Field [Directions] | 4:00 p.m. | ||
| Tue., 10/15 | V Field Hockey | Fairfield Ludlowe | Away - Taft Field [Directions] | L 2-4 | 2:15PM | |
| Tue., 10/15 | JV Field Hockey | Fairfield Ludlowe | Away - FLHS Front Field [Directions] | 4:00 p.m. | ||
| Tue., 10/15 | V Girls Volleyball | Norwalk | Away - Norwalk High Gym [Directions] | W 3-0 | 2:30 Pm | |
| Tue., 10/15 | JV Girls Volleyball | Norwalk | Away - Norwalk High Gym [Directions] | W 2-0 | 2:15PM | |
| Wed., 10/16 | SO Football | Westhill | Home - Stamford High School [Directions] | 4:30 p.m. | ||
| Wed., 10/16 | V Field Hockey | Nonnewaug | Away - Nonnewaug High School Field [Directions] | L 1-2 | 2:00PM | |
| Wed., 10/16 | JV Field Hockey | Nonnewaug | Away - Nonnewaug High School Field [Directions] | 5:00 p.m. | 2:00pm | |
| Wed., 10/16 | V Girls Soccer | Brien McMahon | Home - Stamford High Soccer Field [Directions] | W 1-0 | ||
| Wed., 10/16 | JV Girls Soccer | Brien McMahon | Home - Rippowam Field [Directions] | 4:00 p.m. | ||
| Wed., 10/16 | V Girls Swimming and Diving | Wilton | Home - Westhill Pool [Directions] | 3:15 p.m. | ||
| Wed., 10/16 | V Girls Volleyball | Harding | Away - Harding-Miska Gymnasium [Directions] | W 3-0 | 2:30 PM | |
| Wed., 10/16 | JV Girls Volleyball | Harding | Away - Harding-Miska Gymnasium [Directions] | W 2-0 | 2:15PM | |
| Thu., 10/17 | FR Football | Brien McMahon | Home - Stamford High School [Directions] | 4:00 p.m. | ||
| Thu., 10/17 | V Boys Soccer | New Canaan | Home - Stamford High Soccer Field [Directions] | W 3-1 | ||
| Thu., 10/17 | JV Boys Soccer | New Canaan | Home - Rippowam Field [Directions] | 4:00 p.m. | ||
| Thu., 10/17 | FR Boys Soccer | New Canaan | Away - Saxe Middle School Field [Directions] | 4:00 p.m. | 2:30 pm | |
| Fri., 10/18 | V Football | Brien McMahon | Away - Brien McMahon HS [Directions] | L 6-39 | 4:00pm | |
| Fri., 10/18 | V Competitive Cheerleading | Brien McMahon | Away - Brien McMahon Jack Casagrande Field [Directions] | 7:00 p.m. | 5:30 PM | |
| Fri., 10/18 | V Field Hockey | Danbury | Away - Danbury High School Stadium [Directions] | W 1-0 | 2:15PM | |
| Fri., 10/18 | JV Field Hockey | Danbury | Away - Danbury High School Stadium [Directions] | 5:30 p.m. | ||
| Fri., 10/18 | V Girls Soccer | Trinity Catholic | Home - Stamford High School [Directions] | W 6-0 | ||
| Fri., 10/18 | V Girls Volleyball | Greenwich | Home - Stamford High School [Directions] | L 3-2 | ||
| Fri., 10/18 | JV Girls Volleyball | Greenwich | Home - Stamford High School [Directions] | L 2-1 | ||
| Fri., 10/18 | FR Girls Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | 4:00 p.m. | 2:30 pm | |
| Sat., 10/19 | JV Football | Brien McMahon | Away - Brien McMahon HS [Directions] | 10:00 a.m. | 8:15 AM | |
| Mon., 10/21 | V Boys Soccer | Greenwich | Away - Cardinal Stadium [Directions] | L 1-0 | 3:15pm | |
| Mon., 10/21 | JV Boys Soccer | Greenwich | Away - Cardinal Stadium [Directions] | 4:30 p.m. | 2:30PM | |
| Mon., 10/21 | FR Boys Soccer | Greenwich | Home - Stamford High Soccer Field [Directions] | 4:00 p.m. | ||
| Mon., 10/21 | V Field Hockey | Westhill | Home - Stamford High School [Directions] | L 0-3 | ||
| Mon., 10/21 | JV Field Hockey | Westhill | Home - Stamford High School [Directions] | 4:30 p.m. | ||
| Mon., 10/21 | V Girls Volleyball | Staples | Home - Stamford High School [Directions] | L 0-3 | ||
| Mon., 10/21 | JV Girls Volleyball | Staples | Home - Stamford High School [Directions] | L 0-2 | ||
| Mon., 10/21 | FR Girls Volleyball | Staples | Away - Staples H.S. Gym [Directions] | 4:00 p.m. | 2:30 pm | |
| Tue., 10/22 | V Girls Soccer | New Canaan | Away - Dunning Stadium [Directions] | L 0-5 | 5:15PM | |
| Tue., 10/22 | JV Girls Soccer | New Canaan | Away - Saxe Middle School Field [Directions] | 4:00 p.m. | 2:30 PM | |
| Tue., 10/22 | V Girls Swimming and Diving | Watertown | Away - Frank M. Reinhold Pool @ Watertown High School [Directions] | 5:00 p.m. | 2:30 | |
| Wed., 10/23 | V Boys Soccer | Brien McMahon | Home - Stamford High Soccer Field [Directions] | W 7-0 | ||
| Wed., 10/23 | JV Boys Soccer | Brien McMahon | Home - Rippowam Field [Directions] | 4:00 p.m. | ||
| Wed., 10/23 | V Girls Swimming and Diving | Greenwich | Away - GHS Pool [Directions] | 3:30 p.m. | 2:00 | |
| Wed., 10/23 | V Girls Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | W 3-1 | 2:30PM | |
| Wed., 10/23 | JV Girls Volleyball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | W 2-0 | 2:15PM | |
| Wed., 10/23 | FR Girls Volleyball | Fairfield Warde | Home [Directions] | 4:00 p.m. | ||
| Thu., 10/24 | FR Football | Bassick | Away [Directions] | Cancelled | 2:15 pm | |
| Thu., 10/24 | V Field Hockey | Trumbull | Away - McDougall Stadium [Directions] | W 5-1 | 3:30PM | |
| Thu., 10/24 | JV Field Hockey | Trumbull | Away - McDougall Stadium [Directions] | 5:30 p.m. | ||
| Thu., 10/24 | V Girls Soccer | Wilton | Away - Lilly Field - Turf [Directions] | L 0-7 | 4:00PM | |
| Thu., 10/24 | JV Girls Soccer | Wilton | Away - Allen's Field #1 [Directions] | 4:00 p.m. | 2:15 PM | |
| Fri., 10/25 | V Football | Bassick | Home - Stamford High School [Directions] | W 19-14 | ||
| Fri., 10/25 | V Competitive Cheerleading | Bassick | Home - Stamford High School [Directions] | 6:00 p.m. | ||
| Fri., 10/25 | V Girls Volleyball | Westhill | Away - Westhill - Main Gymnasium [Directions] | W 3-0 | 2:30PM | |
| Fri., 10/25 | JV Girls Volleyball | Westhill | Away - Westhill - Main Gymnasium [Directions] | L 2-1 | 2:30PM | |
| Fri., 10/25 | FR Girls Volleyball | Westhill | Home [Directions] | 4:00 p.m. | ||
| Sat., 10/26 | JV Football | Bassick | Home - Stamford High School [Directions] | 10:00 a.m. | ||
| Mon., 10/28 | V Girls Swimming and Diving | FCIAC Trials @ Greenwich H.S. | Away | 4:00 p.m. | 2:00 | |
| Tue., 10/29 | V Girls Swimming and Diving | FCIAC Diving Meet @ Westhill | Home [Directions] | 4:30 p.m. | ||
| Wed., 10/30 | V Girls Swimming and Diving | FCIAC Finals @ Greenwich H.S. | Away | 4:00 p.m. | 2:00 | |
| Thu., 10/31 | FR Football | Trinity Catholic | Home - Boyle Stadium [Directions] | 4:00 p.m. | 2:30 pm | |
| Fri., 11/1 | V Football | Trinity Catholic | Home - Stamford High School [Directions] | W 21-15 | ||
| Fri., 11/1 | V Competitive Cheerleading | Trinity Catholic | Home - Stamford High School [Directions] | 6:00 p.m. | ||
| Mon., 11/4 | JV Football | Trinity Catholic | Home - Stamford High School [Directions] | 4:00 p.m. | ||
| Wed., 11/6 | SO Football | Trinity Catholic | Home - Stamford High School [Directions] | 4:00 p.m. | ||
| Wed., 11/6 | V Girls Swimming and Diving | State LL Diving Championships @ Bulkelly H.S. | Away | 5:30 p.m. | ||
| Thu., 11/7 | FR Football | Norwalk | Home - Stamford High School [Directions] | 4:00 p.m. | ||
| Fri., 11/8 | V Football | Norwalk | Away - Testa Field, NHS [Directions] | L 6-20 | 3:45pm | |
| Fri., 11/8 | V Competitive Cheerleading | Norwalk | Away - Norwalk High School [Directions] | 6:00 p.m. | 4:45 pm | |
| Sat., 11/9 | JV Football | Norwalk | Away - Testa Field, NHS [Directions] | 2:00 p.m. | 12:00 pm | |
| Sat., 11/9 | V Girls Swimming and Diving | LL State Meet at East Hartford H.S. | Away | 6:00 p.m. | ||
| Tue., 11/12 | V Girls Swimming and Diving | State LL Swim Championships @ SCSU | Away | 6:00 p.m. | 3:00 | |
| Thu., 11/14 | FR Football | Fairfield Ludlowe | Home - Stamford High School [Directions] | 4:00 p.m. | ||
| Fri., 11/15 | V Football | Fairfield Ludlowe | Away - Taft Field [Directions] | L 40-42 | 3:00pm | |
| Fri., 11/15 | V Competitive Cheerleading | Fairfield Ludlowe | Away [Directions] | 6:00 p.m. | 4:45 pm | |
| Fri., 11/15 | V Girls Swimming and Diving | State open Diving Championships @ Middletown | Away | 5:30 p.m. | ||
| Sat., 11/16 | V Girls Swimming and Diving | State open Swim Championship @ Yale | Away | 12:00 p.m. | 8:30 | |
| Mon., 11/18 | JV Football | Westhill | Away - Westhill Football Field [Directions] | 3:00 p.m. | 2:30 PM | |
| Thu., 11/21 | FR Football | Westhill | Home - Stamford High School [Directions] | 4:00 p.m. | ||
| Thu., 11/28 | V Football | Westhill | Away - Westhill Football Field [Directions] | L 0-40 | 8:00am | |
| Thu., 11/28 | V Competitive Cheerleading | Westhill | Away - J Walter Kennedy Stadium [Directions] | 10:00 a.m. | 8:45 pm | |
| Fri., 11/29 | V Girls Basketball | Oswego (NY) (Scrim.) | Home - Stamford High School [Directions] | 11:00 a.m. | ||
| Mon., 12/2 | V Girls Basketball | Scarsdale (NY) (Scrim.) | Away - Scarsdale High School | 4:00 p.m. | 2:30 pm | |
| Wed., 12/4 | V Boys Ice Hockey | North Haven (Scrim.) | Home - Terry Conners Ice Rink [Directions] | 8:00 p.m. | ||
| Wed., 12/4 | V Boys Ice Hockey | North Haven (Scrim.) | Home - Terry Conners Ice Rink [Directions] | 8:00 p.m. | ||
| Wed., 12/4 | V Girls Basketball | Newtown (Scrim.) | Away - Newtown High School Gymnasium [Directions] | 6:00 p.m. | 3:45 pm | |
| Sat., 12/7 | V Boys Basketball | Notre Dame-West Haven (Scrim.) | Home - Stamford High School [Directions] | 11:00 a.m. | ||
| Sat., 12/7 | V Girls Ice Hockey | Tournament Game - Opponent Not Known (Scrim.) | Home - Shelton Ice Rink [Directions] | 5:30 p.m. | 3; 00 pm | |
| Tue., 12/10 | V Boys Basketball | Notre Dame-Fairfield (Scrim.) | Home - Stamford High School [Directions] | 4:45 p.m. | ||
| Wed., 12/11 | V Girls Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | W 48-34 | 2:30 pm | |
| Wed., 12/11 | JV Girls Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 4:00 p.m. | 2:20 pm | |
| Wed., 12/11 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home [Directions] | 8:40 p.m. | ||
| Fri., 12/13 | V Boys Basketball | Crosby (Scrim.) | Home - Stamford High School [Directions] | 3:30 p.m. | ||
| Fri., 12/13 | V Girls Basketball | Darien | Away - DHS Main Gym [Directions] | W 67-57 | 2 :30pm | |
| Fri., 12/13 | JV Girls Basketball | Darien | Away - DHS Main Gym [Directions] | 5:15 p.m. | 2:30 pm | |
| Fri., 12/13 | FR Girls Basketball | Darien | Away - DHS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 12/14 | V Wrestling | Wilton (Scrim.) | Away - wilton Field House [Directions] | 9:00 a.m. | 8:00 am | |
| Sat., 12/14 | V Girls Ice Hockey | Darien | Away - Darien Ice Darien Ice Rink [Directions] | Cancelled | ||
| Sat., 12/14 | V Girls Indoor Track | New Haven Invitational | Away | 9:00 a.m. | 7:00 am | |
| Mon., 12/16 | V Boys Ice Hockey | King and Low-Heywood Thomas (Scrim.) | Away | 4:30 p.m. | ||
| Wed., 12/18 | V Boys Basketball | Norwalk | Home - Stamford High School [Directions] | W 62-51 | ||
| Wed., 12/18 | JV Boys Basketball | Norwalk | Home - Stamford High School [Directions] | 5:15 p.m. | ||
| Wed., 12/18 | FR Boys Basketball | Norwalk | Home - Stamford High School [Directions] | 4:00 p.m. | ||
| Wed., 12/18 | V Boys Ice Hockey | Watertown-Pomperaug | Away - Taft-Mays Rink [Directions] | W 3-2 | 4:00 pm | |
| Wed., 12/18 | V Boys Swimming and Diving | Darien | Away [Directions] | 3:00 p.m. | 1:30 | |
| Wed., 12/18 | V Girls Basketball | Norwalk | Away - Norwalk High Gym [Directions] | W 38-37 | 2:30 pm | |
| Wed., 12/18 | JV Girls Basketball | Norwalk | Away - Norwalk High Gym [Directions] | Cancelled | 2 :15 pm | |
| Fri., 12/20 | V Boys Basketball | Harding | Away - Harding-Miska Gymnasium [Directions] | L 76-80 | 4:30 pm | |
| Fri., 12/20 | JV Boys Basketball | Harding | Away - Harding-Miska Gymnasium [Directions] | 5:15 p.m. | ||
| Fri., 12/20 | FR Boys Basketball | Harding | Away - Harding-Miska Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 12/20 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Home - Westhill Pool [Directions] | 3:30 p.m. | ||
| Fri., 12/20 | V Girls Basketball | Harding | Home - Stamford High School [Directions] | W 64-39 | ||
| Fri., 12/20 | JV Girls Basketball | Harding | Home - Stamford High School [Directions] | 4:00 p.m. | ||
| Fri., 12/20 | V Girls Ice Hockey | West Haven/SHA | Home - Terry Conners Ice Rink [Directions] | 8:30 p.m. | ||
| Fri., 12/20 | V Girls Indoor Track | New Haven Varsity Invitational | Away - Floyd Little Athletic Center | 4:00 p.m. | 2:15 pm | |
| Sat., 12/21 | V Boys Ice Hockey | Branford | Home - Terry Conners Ice Rink [Directions] | L 2-6 | ||
| Sat., 12/21 | V Boys Ice Hockey | EnricoFermi | Away - Enfield Twin Rinks | L 5-4 | 1:00 | |
| Sat., 12/21 | V Boys Indoor Track | Staples, Darien, Greenwich, Fairfield Warde | Away - Staples Field House [Directions] | 10:00 a.m. | 8:30 am | |
| Sat., 12/21 | V Girls Indoor Track | Staples, Darien, Greenwich, Fairfield Warde | Away - Staples Field House [Directions] | 10:00 a.m. | 8:30 am | |
| Sat., 12/21 | V Girls Indoor Track | Staples, Darien, Greenwich, Fairfield Warde | Away - Staples Field House [Directions] | 10:00 a.m. | 8:30 am | |
| Mon., 12/23 | V Boys Ice Hockey | East Haven Coop | Away - DiLungo Rink [Directions] | L 1-9 | 3:45 pm | |
| Thu., 12/26 | V Boys Ice Hockey | Stamford | Home - Terry Connors [Directions] | W 6-3 | ||
| Thu., 12/26 | V Boys Ice Hockey | Westhill/Stamford | Away - Terry Connors [Directions] | L 3-6 | ||
| Thu., 12/26 | V Girls Basketball | Foran | Home - Westhill High School [Directions] | W 47-42 | 2:45 pm | |
| Fri., 12/27 | V Boys Basketball | Joel Barlow | Home - Weston High School [Directions] | W 77-55 | 4:00 pm | |
| Fri., 12/27 | V Wrestling | Danbury | Away - Danbury High School - NEW gym [Directions] | 2:00 p.m. | 7:00am | |
| Fri., 12/27 | JV Girls Basketball | Staples | Away - Staples H.S. Gym [Directions] | 10:00 a.m. | 8:30 AM | |
| Sat., 12/28 | V Boys Basketball | Weston | Away - WHS Gymnasium [Directions] | L 36-44 | TBA | |
| Sat., 12/28 | V Boys Ice Hockey | Newtown/New Fairfield | Away - Danbury Ice Arena [Directions] | W 4-0 | 3:45 | |
| Sat., 12/28 | V Boys Ice Hockey | Suffield/Granby/Windsor Locks Wildcats | Away - Enfield Twin Rinks [Directions] | L 2-9 | 2:15 pm | |
| Sat., 12/28 | V Wrestling | Danbury, New Milford, Amity, Westhill | Away - Danbury high [Directions] | 9:15 a.m. | 6:45 am | |
| Sat., 12/28 | V Girls Basketball | Jonathan Law | Home - Westhill High School [Directions] | W 59-37 | 2:45 pm | |
| Mon., 12/30 | V Boys Ice Hockey | New Milford | Home - Terry Connors [Directions] | L 3-7 | ||
| Mon., 12/30 | V Girls Ice Hockey | Notre Dame-Fairfield | Away - Wonderland of Ice [Directions] | 9:30 a.m. | 7:30 am | |
| Sat., 1/4 | V Boys Basketball | Bassick | Away - Bassick Gymnasium [Directions] | W 75-53 | 4:00PM | |
| Sat., 1/4 | JV Boys Basketball | Bassick | Away - Bassick Gymnasium [Directions] | 3:00 p.m. | 2:30 pm | |
| Sat., 1/4 | FR Boys Basketball | Bassick | Away - Bassick Gymnasium [Directions] | Cancelled | 2:30 pm | |
| Sat., 1/4 | V Boys Ice Hockey | Guilford | Home - Terry Conners Ice Rink [Directions] | W 4-2 | ||
| Sat., 1/4 | V Boys Ice Hockey | Suffield/Granby/Windsor Locks Wildcats | Away - Enfield Twin Rinks [Directions] | L 0-6 | 3:00 | |
| Sat., 1/4 | V Boys Indoor Track | Wilton, Darien, Ridgefield, Norwalk | Away - Wilton Field House [Directions] | 9:30 a.m. | 8:00am | |
| Sat., 1/4 | V Wrestling | Fairfield Warde | Away [Directions] | 9:30 a.m. | ||
| Sat., 1/4 | V Girls Basketball | Bassick | Home - Stamford High School [Directions] | W 59 to 19 | ||
| Sat., 1/4 | JV Girls Basketball | Bassick | Home - Stamford High School [Directions] | 3:00 p.m. | ||
| Sat., 1/4 | V Girls Ice Hockey | Greenwich | Home [Directions] | 8:40 p.m. | ||
| Sat., 1/4 | V Girls Indoor Track | Wilton, Darien, Ridgefield, Norwalk | Away - Wilton Field House [Directions] | 9:30 a.m. | 8:00 am | |
| Sat., 1/4 | V Girls Indoor Track | Wilton, Darien, Ridgefield, Norwalk | Away - Wilton Field House [Directions] | 9:30 a.m. | 8:00 am | |
| Tue., 1/7 | V Boys Basketball | St. Joseph | Away - St. Joseph High School [Directions] | W 57-53 | 4:00 PM | |
| Tue., 1/7 | JV Boys Basketball | St. Joseph | Away - St. Joseph High School [Directions] | 5:15 p.m. | 2:30 pm | |
| Tue., 1/7 | FR Boys Basketball | St. Joseph | Away - St. Joseph High School [Directions] | 4:00 p.m. | 2:30 pm | |
| Tue., 1/7 | V Boys Ice Hockey | Greenwich | Home - Terry Conners Ice Rink [Directions] | L 0-5 | ||
| Tue., 1/7 | V Girls Basketball | St. Joseph | Home - Stamford High School [Directions] | W 59-40 | ||
| Tue., 1/7 | JV Girls Basketball | St. Joseph | Home - Stamford High School [Directions] | 5:15 p.m. | ||
| Tue., 1/7 | FR Girls Basketball | St. Joseph | Home - Stamford High School [Directions] | 4:00 p.m. | ||
| Wed., 1/8 | V Boys Ice Hockey | East Haven Coop | Away - DiLungo Rink [Directions] | L 1-7 | 3:30 | |
| Wed., 1/8 | V Boys Swimming and Diving | Ridgefield | Away - Pool at Barlow Mountain School [Directions] | 4:00 p.m. | 2:15 | |
| Wed., 1/8 | V Wrestling | Trumbull | Home [Directions] | 6:00 p.m. | ||
| Wed., 1/8 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - Norwalk Ice House [Directions] | 5:45 p.m. | ||
| Fri., 1/10 | V Boys Basketball | Ridgefield | Home - Stamford High School [Directions] | W 53-49 | ||
| Fri., 1/10 | JV Boys Basketball | Ridgefield | Home - Stamford High School [Directions] | 5:15 p.m. | ||
| Fri., 1/10 | FR Boys Basketball | Ridgefield | Home - Stamford High School [Directions] | 4:00 p.m. | ||
| Fri., 1/10 | V Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | L 40-57 | ||
| Fri., 1/10 | JV Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 5:15 p.m. | 2:15 pm | |
| Fri., 1/10 | FR Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 1/11 | V Boys Ice Hockey | Staples | Home - Terry Conners Ice Rink [Directions] | L 2-6 | ||
| Sat., 1/11 | V Boys Ice Hockey | St. Joseph | Home - Terry Connors [Directions] | L 2-11 | ||
| Sat., 1/11 | V Boys Indoor Track | Wilton, Danbury, Brien McMahon, Westhill | Away - Wilton Field House [Directions] | 9:30 a.m. | 8:00 am | |
| Sat., 1/11 | V Girls Ice Hockey | New Canaan | Away - Darien Rink [Directions] | 7:40 p.m. | ||
| Sat., 1/11 | V Girls Indoor Track | Wilton, Danbury, Brien McMahon, Westhill | Away - Wilton Field House [Directions] | 9:30 a.m. | 8:00 am | |
| Sat., 1/11 | V Girls Indoor Track | Wilton, Danbury, Brien McMahon, Westhill | Away - Wilton Field House [Directions] | 9:30 a.m. | 8:00am | |
| Mon., 1/13 | V Girls Ice Hockey | Darien | Home - Terry Conners Ice Rink [Directions] | 3:30 p.m. | ||
| Tue., 1/14 | V Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | W 54-47 | 5:00 pm | |
| Tue., 1/14 | JV Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:15 p.m. | 2:15pm | |
| Tue., 1/14 | FR Boys Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | 2:30 pm | |
| Tue., 1/14 | V Girls Basketball | Brien McMahon | Home - Stamford High School [Directions] | W 58-22 | ||
| Tue., 1/14 | JV Girls Basketball | Brien McMahon | Home - Stamford High School [Directions] | 4:00 p.m. | ||
| Tue., 1/14 | V Girls Ice Hockey | Trumbull/St. Joseph | Home [Directions] | 8:20 p.m. | ||
| Wed., 1/15 | V Boys Ice Hockey | Trinity Catholic | Away - Terry Conners Ice Rink | L 2-6 | N/A | |
| Wed., 1/15 | V Boys Ice Hockey | Trumbull | Home - Terry Conners Ice Rink [Directions] | L 1-3 | ||
| Wed., 1/15 | V Wrestling | Bridgeport Central | Away - Central Cafe [Directions] | 4:00 p.m. | 3:15 pm | |
| Fri., 1/17 | V Boys Basketball | Danbury | Home - Stamford High School [Directions] | L 44-49 | ||
| Fri., 1/17 | JV Boys Basketball | Danbury | Home - Stamford High School [Directions] | 5:15 p.m. | ||
| Fri., 1/17 | FR Boys Basketball | Danbury | Home - Stamford High School [Directions] | 4:00 p.m. | ||
| Fri., 1/17 | V Boys Swimming and Diving | Staples | Home - Westhill Pool [Directions] | 3:30 p.m. | ||
| Fri., 1/17 | V Girls Basketball | Danbury | Away - Danbury High School - MAIN gym [Directions] | L 27-40 | 4:15 pm | |
| Fri., 1/17 | JV Girls Basketball | Danbury | Away - Danbury High School - MAIN gym [Directions] | 5:15 p.m. | 2 :15 pm | |
| Fri., 1/17 | FR Girls Basketball | Danbury | Away - Danbury High School - MAIN gym [Directions] | 4:00 p.m. | ||
| Sat., 1/18 | V Boys Ice Hockey | Darien | Away - Darien Ice Rink [Directions] | L 2-6 | N/A | |
| Sat., 1/18 | V Boys Ice Hockey | Norwalk | Home - Terry Conners Ice Rink [Directions] | W 5-2 | ||
| Sat., 1/18 | V Boys Indoor Track | Staples, Danbury, Ridgefield, St. Joseph | Away - Staples Field House [Directions] | 10:00 a.m. | 8:30 am | |
| Sat., 1/18 | V Wrestling | Hall | Away - William Hall High School [Directions] | 9:00 a.m. | 6:15 am | |
| Sat., 1/18 | V Wrestling | Staples, New Canaan, Hall, Thomaston | Away [Directions] | 9:00 a.m. | 7:30 am | |
| Sat., 1/18 | V Girls Ice Hockey | Fairfield Warde | Away - Wonderland of Ice [Directions] | 1:00 p.m. | 11:00 am | |
| Sat., 1/18 | V Girls Indoor Track | Staples, Danbury, Ridgefield, St. Joseph | Away - Staples Field House [Directions] | 10:00 a.m. | 8:30 am | |
| Sat., 1/18 | V Girls Indoor Track | Staples, Danbury, Ridgefield, St. Joseph | Away - Staples Field House [Directions] | 10:00 a.m. | 8:30 am | |
| Mon., 1/20 | V Boys Ice Hockey | Ridgefield | Away - Winter Garden Ice Arena [Directions] | L 3-4 | Yes | |
| Mon., 1/20 | V Girls Ice Hockey | West Haven/SHA | Away - West Haven High School [Directions] | 10:00 a.m. | 8 :00 am | |
| Thu., 1/23 | V Boys Basketball | Wilton | Home - Stamford High School [Directions] | W 67-47 | ||
| Thu., 1/23 | JV Boys Basketball | Wilton | Home - Stamford High School [Directions] | 5:15 p.m. | ||
| Thu., 1/23 | FR Boys Basketball | Wilton | Home - Stamford High School [Directions] | 4:00 p.m. | ||
| Thu., 1/23 | V Wrestling | Ridgefield | Away - RHS Main Gym [Directions] | 6:00 p.m. | ||
| Fri., 1/24 | V Boys Basketball | Trinity Catholic | Away - Walsh Court | L 52-66 | 5:00 pm | |
| Fri., 1/24 | JV Boys Basketball | Trinity Catholic | Away - Walsh Court | 5:15 p.m. | 2:45 pm | |
| Fri., 1/24 | FR Boys Basketball | Trinity Catholic | Away - Walsh Court | 4:00 p.m. | 2:30 pm | |
| Fri., 1/24 | V Boys Indoor Track | Brien McMahon, Fairfield Warde, Ridgefield, Norwalk | Away - Wilton Field House [Directions] | 5:00 p.m. | 3:00 pm | |
| Fri., 1/24 | V Boys Swimming and Diving | Trumbull | Home - Westhill Pool [Directions] | 3:30 p.m. | ||
| Fri., 1/24 | V Girls Basketball | Trinity Catholic | Home - Stamford High School [Directions] | W 69-29 | ||
| Fri., 1/24 | JV Girls Basketball | Trinity Catholic | Home - Stamford High School [Directions] | 4:00 p.m. | ||
| Sat., 1/25 | V Boys Ice Hockey | Wilton | Home - Terry Connors [Directions] | L 2-8 | ||
| Sat., 1/25 | V Boys Ice Hockey | New Canaan | Away - Darien Ice Rink [Directions] | L 0-5 | ||
| Sat., 1/25 | V Boys Swimming and Diving | Glastonbury | Away - GHS Pool [Directions] | 3:00 p.m. | 12:00 | |
| Sat., 1/25 | V Wrestling | Ridgefield, Greenwich, Bethel, Wilton | Away [Directions] | 9:30 a.m. | 7:15 am | |
| Sat., 1/25 | V Girls Ice Hockey | Darien | Home - Terry Conners Ice Rink [Directions] | 1:30 p.m. | ||
| Sat., 1/25 | V Girls Indoor Track | Brien McMahon, Fairfield Warde, Ridgefield, Norwalk | Away - Wilton Field House [Directions] | 2:00 p.m. | 12:30 pm | |
| Mon., 1/27 | V Boys Swimming and Diving | Wilton | Home - Westhill Pool [Directions] | 3:30 p.m. | ||
| Mon., 1/27 | V Wrestling | New Canaan | Away - NCHS Gymnasium [Directions] | 7:00 p.m. | 5:30 pm | |
| Mon., 1/27 | V Girls Basketball | Wilton | Away - Wilton Field House [Directions] | W 55-50 | 2:30 pm | |
| Mon., 1/27 | JV Girls Basketball | Wilton | Away - Wilton Field House [Directions] | 5:15 p.m. | 2:15 pm | |
| Mon., 1/27 | FR Girls Basketball | Wilton | Away - Wilton Field House [Directions] | 4:00 p.m. | ||
| Tue., 1/28 | V Boys Basketball | Fairfield Warde | Home - Stamford High School [Directions] | W 56-39 | ||
| Tue., 1/28 | JV Boys Basketball | Fairfield Warde | Home - Stamford High School [Directions] | 5:15 p.m. | ||
| Tue., 1/28 | FR Boys Basketball | Fairfield Warde | Home - Stamford High School [Directions] | 4:00 p.m. | ||
| Tue., 1/28 | V Boys Ice Hockey | New Canaan | Home - Terry Connors [Directions] | L 1-6 | ||
| Tue., 1/28 | V Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | W 37-28 | 2:30 pm | |
| Tue., 1/28 | JV Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 5:15 p.m. | 2:20 pm | |
| Tue., 1/28 | FR Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 3:45 p.m. | ||
| Wed., 1/29 | V Boys Ice Hockey | Ridgefield | Home - Terry Conners Ice Rink [Directions] | L 1-7 | ||
| Wed., 1/29 | V Boys Swimming and Diving | New Canaan | Away - New Canaan YMCA [Directions] | 3:00 p.m. | 1:30 | |
| Wed., 1/29 | V Wrestling | Staples | Away - Staples H.S. Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/29 | V Girls Ice Hockey | Daniel Hand Coop | Home - Terry Conners Ice Rink [Directions] | 4:50 p.m. | ||
| Thu., 1/30 | V Boys Indoor Track | FCIAC Championships | Away - Floyd Little Athletic Center | 4:30 p.m. | 2:15 pm | |
| Thu., 1/30 | V Girls Ice Hockey | Masuk Coop | Away - Shelton High School [Directions] | 5:30 p.m. | 3:15 pm | |
| Thu., 1/30 | V Girls Indoor Track | FCIAC Championships | Away - Floyd Little Athletic Center | 4:30 p.m. | 2:30 pm | |
| Thu., 1/30 | V Girls Indoor Track | FCIAC Championships | Away - Floyd Little Athletic Center | 4:30 p.m. | Yes | |
| Fri., 1/31 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Home - Westhill Pool [Directions] | 3:15 p.m. | ||
| Sat., 2/1 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland Of Ice [Directions] | L 2-3 (OT) | 5:45 | |
| Sat., 2/1 | V Boys Ice Hockey | Wilton | Home - Terry Conners Ice Rink [Directions] | L 4-5 | ||
| Sat., 2/1 | V Wrestling | Doc Meyers Brawl | Away - Hartford | TBA | tba | |
| Tue., 2/4 | V Boys Basketball | Staples | Home - Stamford High School [Directions] | W 77-60 | ||
| Tue., 2/4 | JV Boys Basketball | Staples | Home - Stamford High School [Directions] | 5:15 p.m. | ||
| Tue., 2/4 | FR Boys Basketball | Staples | Home - Stamford High School [Directions] | 4:00 p.m. | ||
| Tue., 2/4 | V Girls Basketball | Staples | Away - Staples H.S. Gym [Directions] | W 41-28 | 2:30 pm | |
| Tue., 2/4 | JV Girls Basketball | Staples | Away - Staples H.S. Gym [Directions] | 5:15 p.m. | 2:15 pm | |
| Tue., 2/4 | FR Girls Basketball | Staples | Away - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/4 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Terry Conners Ice Rink [Directions] | 8:20 p.m. | ||
| Thu., 2/6 | V Boys Swimming and Diving | Greenwich | Away - GHS Pool [Directions] | 3:45 p.m. | 2:00 | |
| Thu., 2/6 | V Wrestling | Wilton | Home - Stamford High Aux Gym [Directions] | 6:00 p.m. | ||
| Thu., 2/6 | V Girls Ice Hockey | New Canaan | Home [Directions] | 8:40 p.m. | ||
| Fri., 2/7 | V Boys Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | W 47-42 | 4 :15 pm | |
| Fri., 2/7 | JV Boys Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 5:15 p.m. | 2:30 pm | |
| Fri., 2/7 | FR Boys Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 4:00 p.m. | 2:30 pm | |
| Fri., 2/7 | V Wrestling | Westhill, Brien McMahon, Fairfield Ludlowe | Away - FLHS Aux Gym [Directions] | 4:00 p.m. | ||
| Fri., 2/7 | V Girls Basketball | Fairfield Ludlowe | Home - Stamford High School [Directions] | W 60-47 | ||
| Fri., 2/7 | JV Girls Basketball | Fairfield Ludlowe | Home - Stamford High School [Directions] | 5:15 p.m. | ||
| Fri., 2/7 | FR Girls Basketball | Fairfield Ludlowe | Home - Stamford High School [Directions] | 4:00 p.m. | ||
| Sat., 2/8 | V Boys Ice Hockey | Masuk | Home - Terry Conners Ice Rink [Directions] | L 3-4 | ||
| Sat., 2/8 | V Boys Ice Hockey | Staples | Away - Milford Ice Pavilion [Directions] | W 2-1 | 5:30 | |
| Sat., 2/8 | V Boys Indoor Track | CIAC Championships | Away - Floyd Little Athletic Center | TBA | TBA | |
| Sat., 2/8 | V Girls Indoor Track | CIAC Championships | Away - Floyd Little Athletic Center | TBA | ||
| Sat., 2/8 | V Girls Indoor Track | CIAC Championships | Away - Floyd Little Athletic Center | TBA | ||
| Mon., 2/10 | V Girls Ice Hockey | Trumbull/St. Joseph | Away [Directions] | 8:30 p.m. | 6 :00 pm | |
| Tue., 2/11 | V Wrestling | Greenwich | Away - GHS Gymnasium [Directions] | 5:00 p.m. | 4:00 pm | |
| Wed., 2/12 | V Boys Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | W 62-49 | 4:45 PM | |
| Wed., 2/12 | JV Boys Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 5:15 p.m. | 2:30 pm | |
| Wed., 2/12 | FR Boys Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | 2:30 pm | |
| Wed., 2/12 | V Boys Ice Hockey | Trinity Catholic | Away - Terry Conners Ice Rink | L 1-5 | ||
| Wed., 2/12 | V Boys Ice Hockey | Trumbull | Away - Shelton Rinks [Directions] | W 2-1 | 3:45 | |
| Wed., 2/12 | V Girls Basketball | Westhill | Home - Stamford High School [Directions] | L 33-42 | ||
| Wed., 2/12 | JV Girls Basketball | Westhill | Home - Stamford High School [Directions] | 4:00 p.m. | ||
| Wed., 2/12 | V Girls Ice Hockey | Notre Dame-Fairfield | Home - Terry Conners Ice Rink [Directions] | 3:40 p.m. | ||
| Fri., 2/14 | V Wrestling | FCIAC Tourney | Away | 4:30 p.m. | 2:30 pm | |
| Sat., 2/15 | V Boys Basketball | Trumbull | Home - Stamford High School [Directions] | W 72-44 | ||
| Sat., 2/15 | JV Boys Basketball | Trumbull | Home - Stamford High School [Directions] | 12:00 p.m. | ||
| Sat., 2/15 | FR Boys Basketball | Trumbull | Home - Stamford High School [Directions] | 10:00 a.m. | ||
| Sat., 2/15 | V Boys Ice Hockey | Darien | Away - Darien Ice Rink [Directions] | L 1-5 | ||
| Sat., 2/15 | V Wrestling | FCIAC Tournament | Away - New Canaan High | 10:00 a.m. | ||
| Sat., 2/15 | V Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | L 55-65 | 2:30 pm | |
| Sat., 2/15 | JV Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | 12:00 p.m. | 2:25 pm | |
| Sat., 2/15 | FR Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | 10:00 a.m. | ||
| Sat., 2/15 | V Girls Ice Hockey | Fairfield Warde | Home - Terry Conners Ice Rink [Directions] | 3:10 p.m. | ||
| Mon., 2/17 | V Boys Basketball | Greenwich | Away - GHS Gymnasium [Directions] | L 63-66 | 4:30 pm | |
| Mon., 2/17 | JV Boys Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 3:30 p.m. | 2:30 pm | |
| Mon., 2/17 | FR Boys Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 2:00 p.m. | 2:30 pm | |
| Mon., 2/17 | V Boys Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | L 0-5 | 2:00 | |
| Mon., 2/17 | V Girls Basketball | Greenwich | Home - Stamford High School [Directions] | W 58-51 | ||
| Mon., 2/17 | JV Girls Basketball | Greenwich | Home - Stamford High School [Directions] | 3:30 p.m. | ||
| Mon., 2/17 | FR Girls Basketball | Greenwich | Home - Stamford High School [Directions] | 2:00 p.m. | ||
| Tue., 2/18 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away [Directions] | 2:20 p.m. | 12:00 pm | |
| Wed., 2/19 | V Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | W 65-36 | 4:45 pm | |
| Wed., 2/19 | JV Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 5:15 p.m. | 2:30 pm | |
| Wed., 2/19 | FR Boys Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | 2:30 pm | |
| Wed., 2/19 | V Boys Ice Hockey | Branford | Away - NORTHFORD ICE PAVILION [Directions] | L 2-8 | 1:00 | |
| Wed., 2/19 | V Boys Ice Hockey | St. Joseph | Away - Shelton Rinks [Directions] | L 5-6 | ||
| Wed., 2/19 | V Girls Basketball | New Canaan | Home - Stamford High School [Directions] | W 65-36 | ||
| Wed., 2/19 | JV Girls Basketball | New Canaan | Home - Stamford High School [Directions] | 5:15 p.m. | ||
| Wed., 2/19 | FR Girls Basketball | New Canaan | Home - Stamford High School [Directions] | 4:00 p.m. | ||
| Fri., 2/21 | V Boys Ice Hockey | Westhill/Stamford | Away - Terry Connors [Directions] | L 3-4 | ||
| Fri., 2/21 | V Boys Ice Hockey | Stamford | Home - Terry Connors [Directions] | W 4-3 | ||
| Fri., 2/21 | V Boys Swimming and Diving | Danbury | Home - Westhill High School [Directions] | 3:30 p.m. | 1:45 | |
| Sun., 2/23 | V Boys Ice Hockey | Norwalk | Home - Terry Connors [Directions] | W 8-2 | ||
| Mon., 2/24 | V Boys Basketball | Bridgeport Central | Home - Stamford High School [Directions] | L 53-74 | ||
| Mon., 2/24 | JV Boys Basketball | Bridgeport Central | Home - Stamford High School [Directions] | 5:15 p.m. | ||
| Mon., 2/24 | FR Boys Basketball | Bridgeport Central | Home - Stamford High School [Directions] | 4:00 p.m. | ||
| Mon., 2/24 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland Of Ice [Directions] | L 1-7 | 4:45 pm | |
| Tue., 2/25 | V Boys Swimming and Diving | FCIAC Trials @ Greenwich | Away | 4:30 p.m. | 2:00 | |
| Wed., 2/26 | V Boys Basketball | Darien | Home - Stamford High School [Directions] | W 61-49 | ||
| Wed., 2/26 | JV Boys Basketball | Darien | Home - Stamford High School [Directions] | 5:15 p.m. | ||
| Wed., 2/26 | FR Boys Basketball | Darien | Home - Stamford High School [Directions] | 4:00 p.m. | ||
| Wed., 2/26 | V Boys Ice Hockey | New Milford | Home - Terry Conners Ice Rink [Directions] | L 1-7 | ||
| Wed., 2/26 | V Boys Ice Hockey | Masuk | Away - The Rinks at Shelton [Directions] | W 4-3 | 5:30 | |
| Wed., 2/26 | V Boys Swimming and Diving | FCIAC Diving | Home [Directions] | 4:30 p.m. | ||
| Wed., 2/26 | V Girls Ice Hockey | Greenwich | Away [Directions] | 6:45 p.m. | 4:30 pm | |
| Thu., 2/27 | V Boys Swimming and Diving | FCIAC Championship @ Greenwich | Away | 6:00 p.m. | 4:00 | |
| Sat., 3/1 | V Boys Indoor Track | New England Championships | Away - Reggie Lewis Athletic Center | TBA | ||
| Sat., 3/1 | V Girls Indoor Track | New England Championships | Away - Reggie Lewis Athletic Center | TBA | ||
| Sat., 3/1 | V Girls Indoor Track | New England Championships | Away - Reggie Lewis Athletic Center | TBA | ||
| Mon., 3/10 | V Boys Ice Hockey | New Fairfield | Away [Directions] | 7:40 p.m. | 5:00 | |
| Wed., 3/12 | V Boys Swimming and Diving | State LL Diving Meet @ Hampden H.S. | Away | 4:30 p.m. | 1:30 | |
| Wed., 3/19 | V Boys Swimming and Diving | LL State Tournament @ Wesleyan University | Away | 3:00 p.m. | 12:00 | |
| Wed., 3/26 | V Softball | Fairfield Ludlowe (Scrim.) | Home - Stamford High School [Directions] | 4:00 p.m. | ||
| Fri., 3/28 | V Softball | Newtown (Scrim.) | Home - Stamford High School [Directions] | 4:00 p.m. | ||
| Sat., 3/29 | V Baseball | Kolbe Cathedral (Scrim.) | Home - Stamford High School [Directions] | 12:00 a.m. | ||
| Sat., 3/29 | V Girls Lacrosse | Norwalk (Scrim.) | Away - Norwalk High School [Directions] | 3:00 p.m. | 2:00 pm | |
| Sat., 3/29 | V Softball | Darien (Scrim.) | Away - Darien High School [Directions] | 4:00 p.m. | 2:30 pm | |
| Sun., 3/30 | V Boys Lacrosse | Bridgeport Central (Scrim.) | Away - Bridgeport Central [Directions] | 8:00 a.m. | 6:45 am | |
| Sun., 3/30 | V Girls Lacrosse | Crunch time Clinic | Away - Western CT State University | 9:00 a.m. | 7:15 am | |
| Sun., 3/30 | V Softball | St. Joseph (Scrim.) | Home - Cummings Park [Directions] | 10:00 a.m. | ||
| Sun., 3/30 | V Softball | Newtown (Scrim.) | Home - Cummings Park [Directions] | 9:00 a.m. | ||
| Wed., 4/2 | V Baseball | New Canaan (Scrim.) | Home - Stamford High School [Directions] | 4:00 p.m. | ||
| Wed., 4/2 | V Softball | Foran (Scrim.) | Home - Stamford High School [Directions] | 4:00 p.m. | 2:15 pm | |
| Thu., 4/3 | V Boys Lacrosse | King and Low-Heywood Thomas (Scrim.) | Home - Stamford High Soccer Field [Directions] | 4:00 p.m. | ||
| Thu., 4/3 | V Girls Tennis | Danbury (Scrim.) | Home - Stamford High School [Directions] | 4:00 p.m. | ||
| Fri., 4/4 | V Baseball | New Canaan (Scrim.) | Away - Mead Park [Directions] | 3:30 p.m. | 2:30 pm | |
| Fri., 4/4 | V Softball | Newtown (Scrim.) | Away - Newtown High School Softball Field [Directions] | 4:00 p.m. | 2:15 pm | |
| Fri., 4/4 | V Girls Tennis | Brien McMahon (Scrim.) | Away - Brien McMahon [Directions] | 4:00 p.m. | 2:30 pm | |
| Sat., 4/5 | V Boys Lacrosse | Notre Dame-Fairfield (Scrim.) | Home - Stamford High Soccer Field [Directions] | 9:00 a.m. | Jamboree Westhill,Stratford | |
| Sat., 4/5 | V Girls Lacrosse | Weston (Scrim.) | Away - WHS Turf Field [Directions] | 1:00 p.m. | 10:30 am | |
| Sat., 4/5 | JV Girls Lacrosse | Weston (Scrim.) | Away - WHS Turf Field [Directions] | 11:00 a.m. | ||
| Sat., 4/5 | V Softball | Shelton (Scrim.) | Away - Shelton High School [Directions] | 9:00 a.m. | 7:30 am | |
| Wed., 4/9 | V Boys Golf | St. Joseph | Away - Tashua Knolls, Trumbull [Directions] | St. Joes 186 Stamford 200 | 1:55 pm | |
| Wed., 4/9 | V Boys Lacrosse | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | L 9-3 | 5:00 pm | |
| Wed., 4/9 | JV Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde Grass Utility Field [Directions] | L 8-1 | ||
| Wed., 4/9 | V Boys Tennis | Trinity Catholic | Home [Directions] | W 7-0 | ||
| Wed., 4/9 | V Softball | Fairfield Ludlowe | Away - Sturges Park [Directions] | W 4-0 | 2:30 pm | |
| Wed., 4/9 | JV Softball | Fairfield Ludlowe | Away [Directions] | 4:00 p.m. | 2:30 PM | |
| Wed., 4/9 | V Girls Tennis | Trinity Catholic | Away - Scalzi Park | W 6-1 | 2:30 PM | |
| Thu., 4/10 | V Baseball | Trinity Catholic | Home - Stamford High School [Directions] | W 9-1 | ||
| Thu., 4/10 | V Boys Outdoor Track | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 4:00 p.m. | 2:15 PM | |
| Thu., 4/10 | V Boys Tennis | New Canaan | Home [Directions] | L 0-7 | ||
| Thu., 4/10 | V Girls Outdoor Track | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 4:00 p.m. | 2:15 PM | |
| Thu., 4/10 | V Girls Tennis | New Canaan | Away [Directions] | L 0-7 | 2 :30 PM | |
| Fri., 4/11 | V Baseball | Norwalk | Home - Stamford High School [Directions] | L 2-8 | ||
| Fri., 4/11 | JV Baseball | Norwalk | Home - Belltown Field [Directions] | 4:00 p.m. | ||
| Fri., 4/11 | FR Baseball | Norwalk | Away - City Hall Field [Directions] | 4:00 p.m. | ||
| Fri., 4/11 | FR Boys Lacrosse | Danbury | Home - Stamford High Soccer Field [Directions] | L 6-2 | ||
| Fri., 4/11 | V Girls Lacrosse | Trumbull | Away - McDougall Stadium [Directions] | T 10-10 | 2:30 pm | |
| Fri., 4/11 | JV Girls Lacrosse | Trumbull | Away - McDougall Stadium [Directions] | 4:30 p.m. | 2:15 pm | |
| Fri., 4/11 | V Softball | Norwalk | Away - Ray Barry Field, NHS [Directions] | W 5-1 | 2:20 pm | |
| Fri., 4/11 | JV Softball | Norwalk | Away - Naramake School [Directions] | 4:00 p.m. | ||
| Sat., 4/12 | V Baseball | East Hampton | Away - East Hampton High School [Directions] | L 4-6 | 11:45 am | |
| Sat., 4/12 | JV Baseball | East Hampton | Away - East Hampton [Directions] | Cancelled | 9:00am | |
| Sat., 4/12 | V Boys Lacrosse | Pomperaug | Home - Stamford High Soccer Field [Directions] | W 7-6 | ||
| Sat., 4/12 | JV Boys Lacrosse | Pomperaug | Home - Stamford High Soccer Field [Directions] | L 10-5 | ||
| Sat., 4/12 | V Softball | New Rochelle (NY) | Away - New Rochelle High School | L 2-3 | 1:00 pm | |
| Mon., 4/14 | V Baseball | Harding | Away - Beardsley Park - Baseball [Directions] | W 18-2 | 2:30 pm | |
| Mon., 4/14 | JV Baseball | Harding | Away - Seaside Park [Directions] | 4:00 p.m. | 2:30 pm | |
| Mon., 4/14 | V Boys Tennis | Wilton | Away - WHS Tennis Courts [Directions] | L 0-7 | 2:20 PM | |
| Mon., 4/14 | V Softball | Harding | Home - Stamford High School [Directions] | W 13-3 | ||
| Mon., 4/14 | JV Softball | Harding | Home - Cummings Park [Directions] | 4:00 p.m. | ||
| Mon., 4/14 | V Girls Tennis | Wilton | Home [Directions] | L 0-7 | ||
| Tue., 4/15 | JV Boys Lacrosse | Westhill | Home - Stamford High Soccer Field [Directions] | Cancelled | ||
| Tue., 4/15 | FR Boys Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | L 11-1 | 2:30 pm | |
| Tue., 4/15 | V Girls Lacrosse | St. Joseph | Away - St. Joseph High School [Directions] | W 9-8 | 2:15 pm | |
| Tue., 4/15 | JV Girls Lacrosse | St. Joseph | Away - St. Joseph High School [Directions] | 3:30 p.m. | 2:15 pm | |
| Wed., 4/16 | V Boys Tennis | Danbury | Home [Directions] | W 4-3 | ||
| Wed., 4/16 | V Softball | Bassick | Home - Stamford High School [Directions] | W 12-0 | ||
| Wed., 4/16 | V Girls Tennis | Danbury | Away - Danbury High School Tennis Courts [Directions] | W 5-2 | 10:00 am | |
| Thu., 4/17 | V Baseball | St. Joseph | Away - St. Joseph High School [Directions] | L 0-14 | 10:00 am | |
| Thu., 4/17 | JV Baseball | St. Joseph | Away - Madison Middle School, Trumbull [Directions] | 12:00 p.m. | 10:00 am | |
| Thu., 4/17 | FR Baseball | St. Joseph | Home - Stamford High School [Directions] | 12:00 p.m. | ||
| Thu., 4/17 | V Boys Lacrosse | Stratford | Away - Penders Field [Directions] | W 7-3 | 1:00 pm | |
| Thu., 4/17 | FR Boys Lacrosse | Hamden | Home - Stamford High Soccer Field [Directions] | L 12-2 | ||
| Thu., 4/17 | V Softball | St. Joseph | Home - Stamford High School [Directions] | L 2-13 | ||
| Thu., 4/17 | JV Softball | St. Joseph | Home - Cummings Park [Directions] | 4:00 p.m. | ||
| Sat., 4/19 | V Boys Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | L 6-10 | 10:45 AM | |
| Sat., 4/19 | JV Boys Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | L 11-1 | 10:45 am | |
| Sat., 4/19 | FR Boys Lacrosse | East Lyme | Home - Stamford High Soccer Field [Directions] | L 11-1 | ||
| Sat., 4/19 | V Girls Lacrosse | Greenwich | Home - Stamford High School [Directions] | L 5-10 | ||
| Sat., 4/19 | JV Girls Lacrosse | Greenwich | Home - Stamford High School [Directions] | 12:30 p.m. | ||
| Mon., 4/21 | V Baseball | Ridgefield | Home - Stamford High School [Directions] | L 4-7 | ||
| Mon., 4/21 | JV Baseball | Ridgefield | Home - Belltown Field [Directions] | 4:00 p.m. | ||
| Mon., 4/21 | FR Baseball | Ridgefield | Away - Governor's Park Field (aka Ciuccoli or Old High School) [Directions] | 4:00 p.m. | ||
| Mon., 4/21 | V Boys Golf | Greenwich | Away - Griffith E Harris Golf Course [Directions] | Greenwich 149 Stamford 203 | ||
| Mon., 4/21 | FR Boys Lacrosse | Trumbull | Home - Stamford High Soccer Field [Directions] | L 8-4 | ||
| Mon., 4/21 | V Boys Tennis | Ridgefield | Away - RHS Tennis Courts [Directions] | L 0-7 | 2:15 pm | |
| Mon., 4/21 | V Softball | Ridgefield | Away - RHS Upper Grass Field [Directions] | W 10-2 | 2:15 pm | |
| Mon., 4/21 | JV Softball | Ridgefield | Away - RHS Upper Grass Field [Directions] | 4:00 p.m. | ||
| Mon., 4/21 | V Girls Tennis | Ridgefield | Home [Directions] | L 0-7 | ||
| Tue., 4/22 | FR Baseball | Westhill | Home [Directions] | 4:00 p.m. | ||
| Tue., 4/22 | V Boys Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | Fairfield Ludlowe 163 Stamford 201 | 1:55 PM | |
| Tue., 4/22 | V Boys Lacrosse | Brien McMahon | Away - Brien McMahon HS [Directions] | L 7-13 | 3:30 pm | |
| Tue., 4/22 | JV Boys Lacrosse | Brien McMahon | Away - Brien McMahon HS [Directions] | L 6-3 | 3:30 pm | |
| Tue., 4/22 | V Boys Tennis | Staples | Home [Directions] | L 0-7 | ||
| Tue., 4/22 | V Girls Lacrosse | Fairfield Warde | Home - Stamford High School [Directions] | L 6-12 | ||
| Tue., 4/22 | JV Girls Lacrosse | Fairfield Warde | Home - Stamford High School [Directions] | 5:30 p.m. | ||
| Tue., 4/22 | V Girls Outdoor Track | New Canaan, Fairfield Warde | Away - NCHS Track Field [Directions] | 4:00 p.m. | 2:30 PM | |
| Tue., 4/22 | V Girls Tennis | Staples | Away - Staples HS-Tennis Courts [Directions] | L 0-6 | 2:15 PM | |
| Wed., 4/23 | V Baseball | Brien McMahon | Away - Brien McMahon HS [Directions] | L 4-6 | 2:30 PM | |
| Wed., 4/23 | FR Baseball | Brien McMahon | Away - Roton [Directions] | 4:00 p.m. | 2:30 pm | |
| Wed., 4/23 | V Boys Golf | Staples | Home - EG Brennan [Directions] | Staples 160 Stamford 218 | ||
| Wed., 4/23 | V Boys Outdoor Track | Fairfield Warde, New Canaan | Away - Tetreau/Davis Field [Directions] | 4:00 p.m. | 2:30 pm | |
| Wed., 4/23 | V Softball | Brien McMahon | Home - Stamford High School [Directions] | W 15-2 | ||
| Wed., 4/23 | JV Softball | Brien McMahon | Home - Cummings Park [Directions] | 4:00 p.m. | ||
| Thu., 4/24 | JV Baseball | Brien McMahon | Home - Belltown Field [Directions] | 4:00 p.m. | ||
| Thu., 4/24 | V Boys Lacrosse | Ridgefield | Away - Tiger Hollow Stadium [Directions] | L 3-20 | 4:00 pm | |
| Thu., 4/24 | JV Boys Lacrosse | Ridgefield | Away - Tiger Hollow Turf Field II [Directions] | L 15-0 | ||
| Thu., 4/24 | V Boys Tennis | Brien McMahon | Home [Directions] | L 1-6 | ||
| Thu., 4/24 | V Girls Lacrosse | Danbury | Home - Stamford High School [Directions] | L 8-10 | ||
| Thu., 4/24 | JV Girls Lacrosse | Danbury | Home - Stamford High School [Directions] | 5:30 p.m. | ||
| Thu., 4/24 | V Girls Tennis | Brien McMahon | Away - Brien McMahon HS [Directions] | L 2-5 | 2:30 PM | |
| Fri., 4/25 | V Baseball | Danbury | Home - Stamford High School [Directions] | L 2-11 | ||
| Fri., 4/25 | JV Baseball | Danbury | Home - Belltown Field [Directions] | 4:00 p.m. | ||
| Fri., 4/25 | FR Baseball | Danbury | Away - Danbury High School Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Fri., 4/25 | V Girls Outdoor Track | OGrady Relays | Away - Danbury High School | 5:00 p.m. | 2:30 pm | |
| Fri., 4/25 | V Softball | Danbury | Away - Danbury High Varsity Softball Field [Directions] | W 7-3 | 2:15 pm | |
| Fri., 4/25 | JV Softball | Danbury | Away - Danbury High School Junior Varsity Softball Field [Directions] | 4:00 p.m. | ||
| Sat., 4/26 | V Boys Lacrosse | Trinity Catholic | Home - Stamford High Soccer Field [Directions] | W 12-1 | ||
| Sat., 4/26 | V Girls Outdoor Track | O'Grady Relays | Away - Danbury High School | TBA | TBA | |
| Mon., 4/28 | V Baseball | Wilton | Home - Stamford High School [Directions] | L 0-4 | ||
| Mon., 4/28 | JV Baseball | Wilton | Home - Belltown Field [Directions] | 4:30 p.m. | ||
| Mon., 4/28 | FR Baseball | Wilton | Away - Allen's Meadow - Fr. Baseball Field [Directions] | 4:30 p.m. | ||
| Mon., 4/28 | V Boys Lacrosse | Greenwich | Away - Cardinal Stadium [Directions] | L 3-16 | 2:45 pm | |
| Mon., 4/28 | JV Boys Lacrosse | Greenwich | Away - GHS Field 7 [Directions] | L 15-1 | 2:45 pm | |
| Mon., 4/28 | V Boys Tennis | Trumbull | Away - THS Tennis Courts [Directions] | L 0-7 | 2:15 pm | |
| Mon., 4/28 | V Girls Outdoor Track | Darien, Harding | Away - DHS Track [Directions] | 4:00 p.m. | 2:30 PM | |
| Mon., 4/28 | V Softball | Wilton | Away - WHS Varsity Softball Field [Directions] | W 11-3 | 2 :15 pm | |
| Mon., 4/28 | JV Softball | Wilton | Away - JV Softball Field [Directions] | 4:00 p.m. | ||
| Mon., 4/28 | V Girls Tennis | Trumbull | Home [Directions] | L 0-7 | ||
| Tue., 4/29 | V Boys Golf | Norwalk | Home - EG Brennan [Directions] | Norwalk 158 Stamford 181 | ||
| Tue., 4/29 | V Boys Outdoor Track | Darien, Harding | Away - DHS Track [Directions] | 4:00 p.m. | 2:30 PM | |
| Tue., 4/29 | V Boys Tennis | Bridgeport Central | Away [Directions] | W 6-1 | 2:15 pm | |
| Tue., 4/29 | V Girls Lacrosse | Darien | Away - DHS Turf #2 [Directions] | L 1-20 | 2:15 pm | |
| Tue., 4/29 | JV Girls Lacrosse | Darien | Away - DHS Turf #2 [Directions] | 5:30 p.m. | 2:15pm | |
| Wed., 4/30 | JV Girls Lacrosse | West Haven | Away - Ken Strong Stadium [Directions] | 5:30 p.m. | 3:30 pm | |
| Thu., 5/1 | V Boys Lacrosse | Wilton | Home - Stamford High Soccer Field [Directions] | L 5-13 | ||
| Thu., 5/1 | JV Boys Lacrosse | Wilton | Home - Stamford High Soccer Field [Directions] | L 12-4 | ||
| Thu., 5/1 | V Boys Tennis | Darien | Home [Directions] | L 0-7 | ||
| Thu., 5/1 | V Girls Tennis | Darien | Away - DHS Tennis Courts [Directions] | L 0-7 | 2:30 PM | |
| Fri., 5/2 | V Baseball | Fairfield Warde | Home - Stamford High School [Directions] | W 6-5 | ||
| Fri., 5/2 | JV Baseball | Fairfield Warde | Home - Belltown Field [Directions] | 4:00 p.m. | ||
| Fri., 5/2 | FR Baseball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 4:00 p.m. | ||
| Fri., 5/2 | V Girls Lacrosse | Ridgefield | Away - Tiger Hollow Stadium [Directions] | L 6-12 | 2:45 pm | |
| Fri., 5/2 | JV Girls Lacrosse | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 4:30 p.m. | 2:45 pm | |
| Fri., 5/2 | V Softball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | W 4-1 | 2 :15 pm | |
| Fri., 5/2 | JV Softball | Fairfield Warde | Away - Melville Park [Directions] | 4:00 p.m. | ||
| Sat., 5/3 | V Boys Lacrosse | Masuk | Home - Stamford High Soccer Field [Directions] | W 11-4 | ||
| Sat., 5/3 | JV Boys Lacrosse | Masuk | Home - Stamford High Soccer Field [Directions] | L 9-8 | ||
| Sat., 5/3 | V Girls Lacrosse | West Haven | Away - Ken Strong Stadium [Directions] | W 8-7 | 3:30 pm | |
| Mon., 5/5 | FR Baseball | Westhill | Away - Belltown [Directions] | 4:00 p.m. | 2:30 pm | |
| Mon., 5/5 | FR Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde Grass Utility Field [Directions] | W 8-6 | 2:30 pm | |
| Mon., 5/5 | V Boys Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe Tennis Courts [Directions] | L 0-7 | 2:20 pm | |
| Mon., 5/5 | V Girls Outdoor Track | Brien McMahon, Trumbull | Away - Brien McMahon HS [Directions] | 4:00 p.m. | 2:30 PM | |
| Mon., 5/5 | V Girls Tennis | Fairfield Ludlowe | Home [Directions] | L 0-7 | ||
| Tue., 5/6 | V Baseball | Trinity Catholic | Away - Trinity Catholic's Lione Field | L 0-3 | 2:45 pm | |
| Tue., 5/6 | JV Baseball | Trinity Catholic | Home - Stamford High School [Directions] | 4:00 p.m. | 2:30 pm | |
| Tue., 5/6 | FR Baseball | Trinity Catholic | Home - Barrett Field @ Belltown Park [Directions] | 4:00 p.m. | ||
| Tue., 5/6 | V Boys Golf | New Canaan | Away - Country Club of New Canaan [Directions] | New Canaan 165 Stamford 200 | ||
| Tue., 5/6 | V Boys Lacrosse | Danbury | Home - Stamford High Soccer Field [Directions] | L 4-5 | ||
| Tue., 5/6 | JV Boys Lacrosse | Danbury | Home - Stamford High Soccer Field [Directions] | L 8-5 | ||
| Tue., 5/6 | V Boys Tennis | St. Joseph | Home [Directions] | L 2-5 | ||
| Tue., 5/6 | V Girls Lacrosse | New Canaan | Home - Stamford High School [Directions] | L 3-16 | ||
| Tue., 5/6 | JV Girls Lacrosse | New Canaan | Home - Stamford High School [Directions] | 5:30 p.m. | ||
| Tue., 5/6 | V Softball | Trinity Catholic | Home - Stamford High School [Directions] | W 3-0 | ||
| Tue., 5/6 | V Girls Tennis | St. Joseph | Away - St. Joseph High School [Directions] | W 5-2 | 2:15 PM | |
| Wed., 5/7 | V Baseball | Staples | Home - Stamford High School [Directions] | L 1-10 | ||
| Wed., 5/7 | JV Baseball | Staples | Home - Belltown Field [Directions] | 4:00 p.m. | ||
| Wed., 5/7 | FR Baseball | Staples | Away - Staples HS Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/7 | V Boys Outdoor Track | Trumbull, Brien McMahon | Away - McDougall Stadium [Directions] | 4:00 p.m. | 2:15 PM | |
| Wed., 5/7 | V Boys Tennis | Fairfield Warde | Home [Directions] | L 1-6 | ||
| Wed., 5/7 | V Girls Tennis | Fairfield Warde | Away - FWHS Blake Courts [Directions] | L 0-7 | 2:15 PM | |
| Thu., 5/8 | V Girls Lacrosse | Staples | Home - Stamford High School [Directions] | L 8-14 | ||
| Thu., 5/8 | JV Girls Lacrosse | Staples | Home - Stamford High School [Directions] | 5:30 p.m. | ||
| Thu., 5/8 | V Softball | Staples | Away - Wakeman Field C [Directions] | W 10-1 | 2;15 PM | |
| Thu., 5/8 | JV Softball | Staples | Away - Staples HS - Softball Field [Directions] | 4:00 p.m. | ||
| Fri., 5/9 | JV Baseball | Fairfield Ludlowe | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | 2:30 pm | |
| Fri., 5/9 | FR Baseball | Fairfield Ludlowe | Home - Stamford High School [Directions] | 4:00 p.m. | ||
| Fri., 5/9 | FR Boys Lacrosse | Staples | Away - Wakeman Field E (grass) [Directions] | L 13-0 | 2:30 pm | |
| Fri., 5/9 | JV Softball | Fairfield Ludlowe | Home - Cummings Park [Directions] | 4:00 p.m. | ||
| Sat., 5/10 | V Baseball | Fairfield Ludlowe | Away - Kiwanis Field [Directions] | L 5-6 | 2:30 pm | |
| Sat., 5/10 | V Boys Lacrosse | Norwalk | Home - Stamford High Soccer Field [Directions] | L 7-10 | ||
| Sat., 5/10 | V Softball | Fairfield Ludlowe | Home - Stamford High School [Directions] | L 5-6 | ||
| Mon., 5/12 | V Baseball | Westhill | Away - Cubeta [Directions] | L 2-3 | 2:30 pm | |
| Mon., 5/12 | JV Baseball | Westhill | Away - Westhill High School [Directions] | 4:00 p.m. | ||
| Mon., 5/12 | FR Baseball | Westhill | Away - Stamford High School [Directions] | 4:00 p.m. | 2:30 pm | |
| Mon., 5/12 | FR Boys Lacrosse | Westhill | Away - Westhill Front Turf Field [Directions] | L 10-4 | 3:15 pm | |
| Mon., 5/12 | V Boys Tennis | Norwalk | Away - Norwalk High Courts [Directions] | W 6-1 | 2:30 pm | |
| Mon., 5/12 | V Girls Outdoor Track | Fairfield Ludlowe, Norwalk | Away - Taft Field [Directions] | 4:00 p.m. | 2:15 PM | |
| Mon., 5/12 | V Softball | Westhill | Home - Cove Island Park [Directions] | W 4-3 | ||
| Mon., 5/12 | JV Softball | Westhill | Away - Cove Island Beach Sotball Field [Directions] | 4:00 p.m. | ||
| Mon., 5/12 | V Girls Tennis | Norwalk | Home [Directions] | W 5-2 | ||
| Tue., 5/13 | V Baseball | Bassick | Away - Seaside #1 [Directions] | W 22-2 | 2:30 pm | |
| Tue., 5/13 | V Boys Golf | Danbury | Home - EG Brennan [Directions] | Danbury 173 Stamford 191 | ||
| Tue., 5/13 | FR Boys Lacrosse | Hamden | Away - Hamden Middle, 2623 Dixwell Ave, Hamden [Directions] | L 8-0 | 2:15 PM | |
| Tue., 5/13 | V Boys Outdoor Track | Fairfield Ludlowe, Norwalk | Away - Taft Field [Directions] | 3:45 p.m. | 2:30 PM | |
| Tue., 5/13 | V Boys Tennis | Greenwich | Away - GHS Tennis Courts [Directions] | L 0-7 | 2:30 pm | |
| Tue., 5/13 | V Girls Lacrosse | Westhill | Away - Westhill Front Turf Field [Directions] | W 18-2 | 2:15 pm | |
| Tue., 5/13 | JV Girls Lacrosse | Westhill | Away - Westhill Front Turf Field [Directions] | 5:30 p.m. | 3:15 pm | |
| Tue., 5/13 | V Girls Tennis | Greenwich | Home [Directions] | L 0-7 | ||
| Wed., 5/14 | V Baseball | Trumbull | Home - Stamford High School [Directions] | L 3-7 | ||
| Wed., 5/14 | JV Baseball | Trumbull | Home - Belltown Field [Directions] | 4:00 p.m. | ||
| Wed., 5/14 | FR Baseball | Trumbull | Away - Varsity Baseball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/14 | V Boys Golf | Fairfield Warde | Home - EG Brennan [Directions] | Fairfield Warde 171 Stamford 185 | ||
| Wed., 5/14 | V Boys Golf | Darien, Trumbull | Home - EG Brennan [Directions] | Darien 147 Trumbull 165 Stamford 185 | ||
| Wed., 5/14 | V Softball | Trumbull | Away - Varsity Softball Field [Directions] | L 2-5 | 2:20 pm | |
| Wed., 5/14 | JV Softball | Trumbull | Away - JV Softball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/14 | V Girls Tennis | Bridgeport Central | Home [Directions] | W 7-0 | ||
| Thu., 5/15 | V Baseball | Greenwich | Away - GHS Baseball Field [Directions] | L 4-8 | 2:30 pm | |
| Thu., 5/15 | JV Baseball | Greenwich | Away - Julian Curtiss School [Directions] | 4:00 p.m. | 2:30 pm | |
| Thu., 5/15 | V Boys Golf | Brien McMahon, Wilton | Away - Oak Hills [Directions] | Brien McMahon 186 Wilton 160 Stamford 211 | ||
| Thu., 5/15 | V Boys Lacrosse | Trumbull | Away - McDougall Stadium [Directions] | L 13-17 | 2:30 pm | |
| Thu., 5/15 | JV Boys Lacrosse | Trumbull | Away - McDougall Stadium [Directions] | L 10-2 | ||
| Thu., 5/15 | V Girls Lacrosse | Wilton | Home - Stamford High School [Directions] | L 3-15 | ||
| Thu., 5/15 | JV Girls Lacrosse | Wilton | Home - Stamford High School [Directions] | 5:30 p.m. | ||
| Thu., 5/15 | V Softball | Greenwich | Home - Stamford High School [Directions] | L 3-6 | ||
| Thu., 5/15 | JV Softball | Greenwich | Home - Cummings Park [Directions] | 4:00 p.m. | ||
| Sat., 5/17 | V Boys Lacrosse | Staples | Home - Stamford High Soccer Field [Directions] | L 3-17 | ||
| Sat., 5/17 | JV Boys Lacrosse | Staples | Home - Stamford High Soccer Field [Directions] | L 8-7 | ||
| Sat., 5/17 | V Boys Outdoor Track | Westhill | Home - Stamford High School [Directions] | 11:30 a.m. | ||
| Sat., 5/17 | V Girls Outdoor Track | Westhill | Home - Stamford High School [Directions] | 11:30 a.m. | ||
| Mon., 5/19 | V Baseball | New Canaan | Away - Mead Park [Directions] | L 6-13 | 2:30 pm | |
| Mon., 5/19 | JV Baseball | New Canaan | Away - Waveny Park - Coppo Field [Directions] | 4:00 p.m. | 2:30 pm | |
| Mon., 5/19 | FR Baseball | New Canaan | Home - Stamford High School [Directions] | 4:00 p.m. | ||
| Mon., 5/19 | V Boys Golf | Ridgefield | Away - Ridgefield Public GC (DHLY Ridge) [Directions] | Ridgefield 154 Stamford 207 | ||
| Mon., 5/19 | JV Boys Lacrosse | Norwalk | Home - Stamford High Soccer Field [Directions] | W 8-2 | ||
| Mon., 5/19 | FR Boys Lacrosse | Norwalk | Home - Stamford High Soccer Field [Directions] | W 5-3 | ||
| Mon., 5/19 | FR Boys Lacrosse | Norwalk | Home - Stamford High Soccer Field [Directions] | 5:30 p.m. | ||
| Mon., 5/19 | V Boys Tennis | Westhill | Away - Westhill Tennis Courts [Directions] | L 0-7 | 2:30 pm | |
| Mon., 5/19 | V Girls Outdoor Track | Danbury, Wilton | Away - Danbury High School Stadium [Directions] | 4:00 p.m. | 2:15 PM | |
| Mon., 5/19 | V Softball | New Canaan | Home - Stamford High School [Directions] | W 4-1 | ||
| Mon., 5/19 | JV Softball | New Canaan | Home - Cummings Park [Directions] | 4:00 p.m. | ||
| Mon., 5/19 | V Girls Tennis | Westhill | Home [Directions] | L 3-4 | ||
| Tue., 5/20 | V Boys Golf | Bassick, Bridgeport Central, Harding | Away - Fairchild-Wheeler [Directions] | Harding 276 Stamford 174 | ||
| Tue., 5/20 | V Boys Lacrosse | Bethel | Home - Stamford High Soccer Field [Directions] | W 13-8 | ||
| Tue., 5/20 | JV Boys Lacrosse | Bethel | Home - Stamford High Soccer Field [Directions] | 5:30 p.m. | ||
| Tue., 5/20 | V Boys Outdoor Track | Wilton, Danbury | Away - Fujitani Field - Turf [Directions] | 4:00 p.m. | 2:15 PM | |
| Tue., 5/20 | V Girls Lacrosse | Westhill | Home - Stamford High School [Directions] | W 13-1 | ||
| Wed., 5/21 | V Baseball | Bridgeport Central | Home - Stamford High School [Directions] | W 8-4 | ||
| Wed., 5/21 | JV Baseball | Bridgeport Central | Home - Belltown Field [Directions] | 4:00 p.m. | ||
| Wed., 5/21 | V Boys Golf | Wilton | Away - Rolling Hills [Directions] | Cancelled | ||
| Wed., 5/21 | V Boys Golf | Wilton | Home - EG Brennan [Directions] | Cancelled | ||
| Wed., 5/21 | V Softball | Bridgeport Central | Away - Central H.S. Varsity Softball Field [Directions] | W 9-1 | 2:20 pm | |
| Wed., 5/21 | JV Softball | Bridgeport Central | Away - Central H.S. Junior Varsity Softball Field [Directions] | 4:00 p.m. | ||
| Thu., 5/22 | V Boys Lacrosse | Westhill | Home - Stamford High School [Directions] | W 8-2 | ||
| Thu., 5/22 | JV Boys Lacrosse | Westhill | Home - Stamford High Soccer Field [Directions] | 5:30 p.m. | ||
| Thu., 5/22 | JV Girls Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 5:15 p.m. | 2:15 pm | |
| Thu., 5/22 | V Girls Outdoor Track | Coaches vs Cancer | Away - Staples High School | 4:00 p.m. | 2:15 pm | |
| Fri., 5/23 | V Baseball | Darien | Home - Stamford High School [Directions] | L 2-4(12) | ||
| Fri., 5/23 | JV Baseball | Darien | Home - Belltown Field [Directions] | 4:00 p.m. | ||
| Fri., 5/23 | FR Baseball | Darien | Away - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Fri., 5/23 | V Girls Lacrosse | FCIAC Tournament | Away - TBA | TBA | ||
| Fri., 5/23 | V Softball | Darien | Away - DHS Softball Varsity Field [Directions] | L 3-10 | 2:30 pm | |
| Fri., 5/23 | JV Softball | Darien | Away - DHS Softball JV Field [Directions] | 4:00 p.m. | ||
| Sat., 5/24 | V Girls Lacrosse | Amity | Away - Amity High School - Field # 3 [Directions] | W 11-10 | 8:00 am | |
| Sat., 5/24 | JV Girls Lacrosse | Amity | Away - Amity High School - Field # 3 [Directions] | 11:15 a.m. | 8:00 am | |
| Tue., 5/27 | V Girls Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | L 11-13 | 3:15 pm | |