| Staples 2018-19 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 1227 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| TBA | V Baseball | Masuk | Away - John Giampaolo Baseball Field @ Masuk HS [Directions] | 4:00 p.m. | W 14-4 (5) | |
| TBA | JV Baseball | Hall | Away - Hall HS JV Baseball Field [Directions] | 4:00 p.m. | ||
| TBA | JV Boys Golf | New Canaan | Away - Country Club of New Canaan [Directions] | Cancelled | Cancelled | |
| TBA | JV Boys Golf | Ridgefield | Away - Silver Spring GC [Directions] | TBA | ED 1:50 | |
| TBA | JV Boys Ice Hockey | St. Joseph | Home - Milford Ice Pavilion [Directions] | TBA | ED 1:45 | |
| TBA | V Boys Outdoor Track | St. Joseph | Away [Directions] | Cancelled | Cancelled | |
| TBA | V Boys Soccer | Fairfield Prep (Scrim.) | Home - Wakeman Field B (turf) [Directions] | TBA | ||
| TBA | JV Boys Soccer | Danbury | Home - Wakeman Field E (grass) [Directions] | TBA | ||
| TBA | JV Boys Tennis | Darien | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| TBA | JV Girls Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 4:00 p.m. | ||
| TBA | JV Girls Basketball | Norwalk | Home - Staples H.S. Gym [Directions] | TBA | ||
| TBA | FR Girls Basketball | Greenwich | Home - Staples H.S. Gym [Directions] | TBA | ||
| TBA | JV Field Hockey | Greenwich Academy | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | ||
| TBA | JV Field Hockey | Wilton | Home - Ginny Parker Field - Staples [Directions] | Cancelled | Cancelled | |
| TBA | FR Girls Lacrosse | Darien | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | ||
| TBA | FR Girls Lacrosse | Fairfield Warde | Away - Fairfield Warde Grass Utility Field [Directions] | TBA | ||
| TBA | V Girls Soccer | Weston (Scrim.) | Home - Loeffler Field - Staples HS [Directions] | TBA | ||
| TBA | JV Girls Soccer | Greenwich | Home - Wakeman Field E (grass) [Directions] | 4:30 p.m. | ||
| TBA | JV Girls Soccer | Weston (Scrim.) | Home - Wakeman Field E (grass) [Directions] | TBA | ||
| TBA | FR Girls Soccer | Greenwich | Away - Cos Cob Park Benvenuto Field [Directions] | TBA | ||
| TBA | V Softball | CIAC Tourney 2nd Round | Away - Higher Seed | TBA | ||
| TBA | JV Softball | New Canaan | Away - Waveny Park - Orchard Field [Directions] | Cancelled | Cancelled | |
| TBA | JV Softball | Bridgeport Central | Away - Ripken Field [Directions] | 4:00 p.m. | ||
| TBA | V Girls Tennis | CIAC Tourney Qualifying Round | Away - Highest Seed | TBA | ||
| TBA | JV Girls Tennis | Darien | Away - Weed Beach [Directions] | 4:00 p.m. | ||
| TBA | JV Girls Tennis | Ridgefield | Away - Yanity Tennis Courts [Directions] | TBA | ||
| Wed., 8/22 | V Football | Fairfield Prep (Scrim.) | Away - Rafferty Stadium, Fairfield University [Directions] | 5:45 p.m. | ||
| Wed., 8/22 | FR Football | Notre Dame-West Haven (Scrim.) | Home [Directions] | 11:00 a.m. | ||
| Wed., 8/29 | V Football | Stepinac (NY) (Scrim.) | Away | 5:00 p.m. | ||
| Thu., 8/30 | FR Football | Trumbull (Scrim.) | Home - Staples Stadium [Directions] | 6:00 p.m. | ||
| Thu., 8/30 | V Boys Soccer | Joel Barlow (Scrim.) | Away - Field J (competition field) [Directions] | 4:00 p.m. | ||
| Thu., 8/30 | V Field Hockey | Greenwich Academy (Scrim.) | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | ||
| Thu., 8/30 | JV Field Hockey | Greenwich Academy (Scrim.) | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | ||
| Thu., 8/30 | V Girls Soccer | Greenwich Academy (Scrim.) | Away | 4:00 p.m. | ||
| Thu., 8/30 | JV Girls Soccer | Greenwich Academy (Scrim.) | Away | 4:00 p.m. | ||
| Thu., 8/30 | V Girls Volleyball | Fairfield Warde (Scrim.) | Away [Directions] | 3:30 p.m. | ||
| Sat., 9/1 | V Boys Soccer | Wethersfield Jamboree | Away | 10:00 a.m. | ||
| Sat., 9/1 | V Field Hockey | Sacred Heart Academy (Scrim.) | Away [Directions] | 9:00 a.m. | ||
| Sat., 9/1 | V Girls Soccer | Staples Girls Soccer Jamboree | Home - Wakeman Field B (turf) [Directions] | 8:00 a.m. | ||
| Sat., 9/1 | JV Girls Soccer | Staples Girls Soccer Jamboree | Home - Wakeman Field B (turf) [Directions] | 8:00 a.m. | ||
| Sat., 9/1 | FR Girls Soccer | New Canaan & Trumbull | Home - Loeffler Field - Staples HS [Directions] | 9:00 a.m. | ||
| Mon., 9/3 | V Boys Soccer | Martin Luther King, NYC | Away - Riverside Park (107th Street, Manhattan | 1:30 p.m. | ||
| Wed., 9/5 | V Girls Soccer | Shelton (Scrim.) | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | ||
| Wed., 9/5 | JV Girls Soccer | Shelton (Scrim.) | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Wed., 9/5 | V Girls Volleyball | Staples jamboree | Home - Staples Field House [Directions] | 4:00 p.m. | ||
| Thu., 9/6 | FR Football | Norwalk | Home - Staples Stadium [Directions] | 6:15 p.m. | ||
| Thu., 9/6 | JV Boys Soccer | Wilton | Away - Allen's Meadow [Directions] | 4:00 p.m. | W 2-1 | |
| Fri., 9/7 | V Boys Cross Country | Blue vs White Time Trial | Home [Directions] | 2:45 p.m. | ||
| Fri., 9/7 | V Football | Bridgeport Central | Away - Kennedy Stadium [Directions] | 7:00 p.m. | W 35-6 | |
| Fri., 9/7 | V Competitive Cheerleading | Bridgeport Central | Away [Directions] | 7:00 p.m. | ||
| Fri., 9/7 | V Girls Cross Country | Blue and White Time Trials | Home - Staples Stadium [Directions] | 2:45 p.m. | ||
| Fri., 9/7 | V Field Hockey | Darien | Away - DHS Stadium Field [Directions] | 3:30 p.m. | W 2-1 | |
| Fri., 9/7 | FR Field Hockey | Darien | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | ||
| Fri., 9/7 | V Girls Soccer | Fairfield Warde | Away - Fairfield Warde Grass Soccer Field [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 9/7 | JV Girls Soccer | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | ||
| Fri., 9/7 | FR Girls Soccer | Fairfield Warde | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Sat., 9/8 | JV Football | Bridgeport Central | Away - Kennedy Stadium [Directions] | 10:00 a.m. | ||
| Sat., 9/8 | V Boys Soccer | Fairfield Warde | Home - Loeffler Field - Staples HS [Directions] | 3:00 p.m. | W 3-1 | |
| Tue., 9/11 | V Boys Cross Country | New Canaan, Brien McMahon, Trinity Catholic | Away - Waveny Park [Directions] | 4:00 p.m. | ED 1:30 | |
| Tue., 9/11 | V Girls Cross Country | New Canaan, Brien McMahon, Trinity Catholic | Away - Waveny Park [Directions] | 4:00 p.m. | ED 1:30 | |
| Tue., 9/11 | V Girls Soccer | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 6:00 p.m. | W 3-1 | |
| Tue., 9/11 | JV Girls Soccer | Danbury | Away - Danbury HS Grass Soccer Field [Directions] | 6:00 p.m. | ||
| Tue., 9/11 | FR Girls Soccer | Danbury | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Tue., 9/11 | V Girls Volleyball | Weston | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Tue., 9/11 | JV Girls Volleyball | Weston | Home - Staples H.S. Gym [Directions] | 5:00 p.m. | ||
| Tue., 9/11 | FR Girls Volleyball | Weston | Home - Staples Field House [Directions] | Cancelled | Cancelled | |
| Wed., 9/12 | V Boys Soccer | Danbury | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | T 1-1 | |
| Wed., 9/12 | FR Boys Soccer | Danbury | Away - Danbury HS Grass Soccer Field [Directions] | 4:00 p.m. | W 7-0 | |
| Wed., 9/12 | V Field Hockey | Fairfield Warde | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | W 8-1 | |
| Wed., 9/12 | JV Field Hockey | Fairfield Warde | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | ||
| Wed., 9/12 | V Girls Volleyball | Fairfield Ludlowe | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | L 2-3 | |
| Wed., 9/12 | JV Girls Volleyball | Fairfield Ludlowe | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Wed., 9/12 | FR Girls Volleyball | Fairfield Ludlowe | Home - Staples Field House [Directions] | 4:00 p.m. | ||
| Thu., 9/13 | FR Football | Wilton | Away [Directions] | 6:00 p.m. | ||
| Thu., 9/13 | V Field Hockey | Brien McMahon | Away - Brien McMahon HS [Directions] | 7:00 p.m. | W 5-0 | |
| Thu., 9/13 | JV Field Hockey | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:30 p.m. | ||
| Thu., 9/13 | V Girls Soccer | Trinity Catholic | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | W 2-0 | |
| Fri., 9/14 | V Football | Wilton | Home - Staples Stadium [Directions] | 7:00 p.m. | W 37-12 | |
| Fri., 9/14 | V Boys Soccer | Trinity Catholic | Away | 4:00 p.m. | W 4-0 | |
| Fri., 9/14 | V Competitive Cheerleading | Wilton | Home - Staples Stadium [Directions] | 7:00 p.m. | ||
| Fri., 9/14 | V Girls Volleyball | Fairfield Warde | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 9/14 | JV Girls Volleyball | Fairfield Warde | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/14 | FR Girls Volleyball | Fairfield Warde | Home - Staples Field House [Directions] | 4:00 p.m. | ||
| Sat., 9/15 | V Boys Cross Country | Stratton Brook Invitational | Away | 9:00 a.m. | ||
| Sat., 9/15 | V Boys Water Polo | CP-AC, Canterbury (4:00pm) | Away - Chelsea Piers | 2:00 p.m. | JV at 3pm | |
| Sat., 9/15 | V Girls Cross Country | Stratton Brook Invitational | Away - Stratton Brook State Park. Simsbury, CT | 9:00 a.m. | ||
| Sat., 9/15 | FR Girls Soccer | Wilton | Away [Directions] | 4:00 p.m. | ||
| Mon., 9/17 | V Boys Cross Country | Fairfield Warde, Trumbull, Stamford | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Mon., 9/17 | V Boys Soccer | Wilton | Away - Lilly Field - Turf [Directions] | 6:00 p.m. | W 2-1 | |
| Mon., 9/17 | JV Boys Soccer | Wilton | Away - Lilly Field - Turf [Directions] | 4:00 p.m. | W 2-1 | |
| Mon., 9/17 | FR Boys Soccer | Wilton | Home - Wakeman Field E (grass) [Directions] | 4:30 p.m. | W 1-0 | |
| Mon., 9/17 | V Girls Cross Country | Fairfield Warde, Trumbull, Stamford | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Mon., 9/17 | V Field Hockey | Danbury | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | W 11-0 | |
| Mon., 9/17 | JV Field Hockey | Danbury | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | ||
| Mon., 9/17 | FR Field Hockey | Danbury | Away - Danbury HS Grass Field Hockey Field [Directions] | 4:00 p.m. | ED 1:50 | |
| Mon., 9/17 | V Girls Swimming and Diving | New Canaan | Home - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Mon., 9/17 | V Girls Volleyball | Danbury | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 9/17 | JV Girls Volleyball | Danbury | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Mon., 9/17 | FR Girls Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 4:00 p.m. | ED 2:00 | |
| Thu., 9/20 | JV Boys Soccer | Fairfield Warde | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | W 3-2 | |
| Thu., 9/20 | FR Boys Soccer | Fairfield Warde | Away - Fairfield Woods MS [Directions] | 4:00 p.m. | W 4-0 | |
| Thu., 9/20 | V Boys Water Polo | Suffield Academy | Away | 4:00 p.m. | ED 1:30, JV at 5pm | |
| Thu., 9/20 | V Girls Soccer | Trumbull | Away - New Turf Field [Directions] | 5:30 p.m. | W 3-0 | |
| Thu., 9/20 | JV Girls Soccer | Trumbull | Away - The Pit [Directions] | 4:00 p.m. | ||
| Thu., 9/20 | FR Girls Soccer | Trumbull | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Thu., 9/20 | V Girls Swimming and Diving | Trumbull | Home - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Thu., 9/20 | V Girls Volleyball | Trinity Catholic | Away - Walsh Court | 5:30 p.m. | W 3-1 | |
| Thu., 9/20 | JV Girls Volleyball | Trinity Catholic | Away | 4:00 p.m. | ||
| Fri., 9/21 | V Football | Brien McMahon | Home - Staples Stadium [Directions] | 7:00 p.m. | W 38-14 | Homecoming |
| Fri., 9/21 | V Boys Soccer | Trumbull | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | L 1-0 | |
| Fri., 9/21 | JV Boys Soccer | Trumbull | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | W 4-1 | |
| Fri., 9/21 | FR Boys Soccer | Trumbull | Away - JV Grass Field [Directions] | 4:00 p.m. | W 1-0 | |
| Fri., 9/21 | V Competitive Cheerleading | Brien McMahon | Home - Staples Stadium [Directions] | 7:00 p.m. | ||
| Fri., 9/21 | V Field Hockey | Greenwich | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | W 2-1 | |
| Fri., 9/21 | JV Field Hockey | Greenwich | Home - Ginny Parker Field - Staples [Directions] | 5:15 p.m. | ||
| Fri., 9/21 | FR Field Hockey | Greenwich | Away - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | ||
| Sat., 9/22 | V Boys Cross Country | Bowdoin Park Classic | Away | 10:00 a.m. | Bowdoin Park, Wappinger Falls, NY | |
| Sat., 9/22 | FR Football | Brien McMahon | Away - Brien McMahon HS [Directions] | 10:00 a.m. | ||
| Sat., 9/22 | V Girls Cross Country | Bowdoin Park Classic | Away - Bowdoin Park Wappinger Falls, NY | 10:00 a.m. | ||
| Sat., 9/22 | V Girls Soccer | Bridgeport Central | Away - Kennedy Stadium [Directions] | 4:00 p.m. | W 6-0 | |
| Sat., 9/22 | FR Girls Soccer | Weston | Home - Wakeman Field B (turf) [Directions] | 10:00 a.m. | ||
| Mon., 9/24 | V Boys Soccer | Bridgeport Central | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 2-0 | |
| Mon., 9/24 | JV Boys Soccer | Bridgeport Central | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | W 7-1 | |
| Mon., 9/24 | V Field Hockey | Fairfield Ludlowe | Away - Taft Field [Directions] | 4:00 p.m. | W 9-0 | |
| Mon., 9/24 | JV Field Hockey | Fairfield Ludlowe | Away - Taft Field [Directions] | 5:30 p.m. | ||
| Mon., 9/24 | FR Field Hockey | Fairfield Ludlowe | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | ||
| Mon., 9/24 | V Girls Volleyball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 5:30 p.m. | W 3-0 | |
| Mon., 9/24 | JV Girls Volleyball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Mon., 9/24 | FR Girls Volleyball | Wilton | Home - Staples H.S. Gym [Directions] | 4:30 p.m. | ||
| Wed., 9/26 | V Boys Soccer | Greenwich | Away - Cardinal Stadium [Directions] | 5:00 p.m. | L 2-0 | |
| Wed., 9/26 | JV Boys Soccer | Greenwich | Away - GHS Field 3 [Directions] | 5:00 p.m. | L 3-1 | |
| Wed., 9/26 | V Boys Water Polo | Loomis Chaffee and Canterbury | Away - Loomis Chaffee | 3:45 p.m. | ED 1:15 | |
| Wed., 9/26 | V Girls Soccer | Greenwich | Home - Wakeman Field B (turf) [Directions] | 4:30 p.m. | W 3-0 | |
| Wed., 9/26 | V Girls Swimming and Diving | Danbury | Away - O'Neil Center @ Western Connecticut State University [Directions] | 4:30 p.m. | ||
| Thu., 9/27 | V Boys Cross Country | Wilton, Westhill, Fairfield Ludlowe | Away - Allen's Field [Directions] | 4:00 p.m. | ED 1:30 | |
| Thu., 9/27 | FR Football | Ridgefield | Home - Staples Stadium [Directions] | 6:15 p.m. | ||
| Thu., 9/27 | V Girls Cross Country | Wilton, Westhill, Fairfield Ludlowe | Away - Allen's Field [Directions] | 4:00 p.m. | ED 1:30 | |
| Thu., 9/27 | V Girls Soccer | Norwalk | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | W 6-0 | |
| Thu., 9/27 | JV Girls Soccer | Norwalk | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Thu., 9/27 | V Girls Volleyball | Trumbull | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | L 1-3 | |
| Thu., 9/27 | JV Girls Volleyball | Trumbull | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Thu., 9/27 | FR Girls Volleyball | Trumbull | Home - Staples Field House [Directions] | 4:00 p.m. | ||
| Fri., 9/28 | V Football | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 7:00 p.m. | W 35-17 | |
| Fri., 9/28 | FR Boys Soccer | Norwalk | Home - Wakeman Field B (turf) [Directions] | 4:45 p.m. | T 1-1 | |
| Fri., 9/28 | V Competitive Cheerleading | Ridgefield | Away [Directions] | 7:00 p.m. | ||
| Fri., 9/28 | V Field Hockey | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | W 7-0 | |
| Fri., 9/28 | JV Field Hockey | Stamford | Away - Stamford HS [Directions] | 5:30 p.m. | ||
| Fri., 9/28 | V Girls Swimming and Diving | Norwalk/McMahon | Away - Pat Spinola Natatorium [Directions] | 3:30 p.m. | ED 1:55 | |
| Fri., 9/28 | V Girls Volleyball | Bridgeport Central | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | W 3-1 | |
| Fri., 9/28 | JV Girls Volleyball | Bridgeport Central | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Sat., 9/29 | V Boys Soccer | Norwalk | Away - Testa Field, NHS [Directions] | 6:00 p.m. | T 1-1 | |
| Sat., 9/29 | V Girls Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | 1:00 p.m. | T 1-1 | |
| Sat., 9/29 | JV Girls Soccer | Brien McMahon | Away - Pride Field (BMHS) [Directions] | 12:00 p.m. | ||
| Mon., 10/1 | V Boys Soccer | Brien McMahon | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 10/1 | JV Boys Soccer | Brien McMahon | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | W 4-2 | |
| Mon., 10/1 | FR Boys Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | 6:00 p.m. | W 3-0 | |
| Mon., 10/1 | V Girls Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | 4:30 p.m. | L 0-3 | |
| Mon., 10/1 | JV Girls Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | 5:30 p.m. | ||
| Mon., 10/1 | FR Girls Volleyball | Greenwich | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/2 | V Boys Cross Country | Greenwich, Danbury, Ridgefield | Away - Greenwich Point [Directions] | 4:00 p.m. | ED 1:15 | |
| Tue., 10/2 | V Girls Cross Country | Greenwich, Danbury, Ridgefield | Away - Greenwich Point [Directions] | 4:00 p.m. | ED 1:15 | |
| Tue., 10/2 | V Girls Soccer | Westhill | Away - Westhill Front Turf Field [Directions] | 4:00 p.m. | W 4-1 | |
| Tue., 10/2 | JV Girls Soccer | Westhill | Away - Rippowam MS - Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 10/3 | JV Field Hockey | Darien | Away - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | ||
| Wed., 10/3 | V Girls Swimming and Diving | Westhill/Stamford | Home - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Wed., 10/3 | V Girls Volleyball | Norwalk | Away - Scarso Gymnasium [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 10/3 | JV Girls Volleyball | Norwalk | Away - Scarso Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 10/4 | FR Football | Darien | Home - Staples Stadium [Directions] | 6:15 p.m. | ||
| Thu., 10/4 | V Boys Soccer | Westhill | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 1-0 | |
| Thu., 10/4 | JV Boys Soccer | Westhill | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | T 0-0 | |
| Thu., 10/4 | V Field Hockey | St. Joseph | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | W 10-0 | |
| Thu., 10/4 | JV Field Hockey | St. Joseph | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | ||
| Thu., 10/4 | V Girls Soccer | Wilton | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | T 0-0 | |
| Fri., 10/5 | V Girls Soccer | Stamford | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 5-0 | |
| Fri., 10/5 | JV Girls Soccer | Stamford | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Fri., 10/5 | V Girls Swimming and Diving | Greenwich | Home - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Fri., 10/5 | V Girls Volleyball | Brien McMahon | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | W 3-2 | |
| Fri., 10/5 | JV Girls Volleyball | Brien McMahon | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Sat., 10/6 | V Boys Cross Country | Wickham Park Invitational | Away | 9:40 a.m. | ||
| Sat., 10/6 | V Football | Practice | Home - Fan bus [Directions] | 1:00pm | Fan bus | |
| Sat., 10/6 | V Football | Darien | Away - DHS Stadium Field [Directions] | 2:00 p.m. | L 0-24 | |
| Sat., 10/6 | FR Boys Soccer | Westhill | Away - J. Walter Kennedy Stadium [Directions] | 2:00 p.m. | W 1-0 | |
| Sat., 10/6 | V Boys Water Polo | CP-AC | Home - Staples HS Pool [Directions] | 2:00 p.m. | JV at 3pm | |
| Sat., 10/6 | V Competitive Cheerleading | Darien | Away [Directions] | 2:00 p.m. | ||
| Sat., 10/6 | V Girls Cross Country | Wickham Park Invitational | Away - Wickham Park | 9:40 a.m. | ||
| Sat., 10/6 | V Field Hockey | Branford | Away - Branford HS-Turf Field [Directions] | 6:00 p.m. | W 5-0 | |
| Sat., 10/6 | JV Field Hockey | Branford | Away - Branford HS-Turf Field [Directions] | 4:30 p.m. | ||
| Sat., 10/6 | V Girls Swimming and Diving | St. Joseph | Away [Directions] | 4:00 p.m. | ||
| Mon., 10/8 | V Boys Soccer | Stamford | Away - Stamford High Soccer Field [Directions] | 4:00 p.m. | T 1-1 | |
| Mon., 10/8 | JV Boys Soccer | Stamford | Away - Rippowam Field [Directions] | 4:00 p.m. | T 1-1 | |
| Mon., 10/8 | FR Boys Soccer | Stamford | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | W 3-1 | |
| Mon., 10/8 | V Field Hockey | Westhill | Home - Staples Stadium [Directions] | 6:15 p.m. | W 7-0 | |
| Mon., 10/8 | JV Field Hockey | Westhill | Home - Ginny Parker Field - Staples [Directions] | 4:30 p.m. | ||
| Mon., 10/8 | FR Field Hockey | Westhill | Away - Westhill Football Field [Directions] | 4:00 p.m. | ||
| Tue., 10/9 | V Boys Cross Country | St. Joseph, Norwalk, Darien | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 10/9 | V Girls Cross Country | St. Joseph, Norwalk, Darien | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 10/9 | V Girls Soccer | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 4:00 p.m. | T 0-0 | ED 1:45 |
| Tue., 10/9 | JV Girls Soccer | Ridgefield | Away - Lower Grass Field [Directions] | 4:00 p.m. | ||
| Tue., 10/9 | FR Girls Soccer | Ridgefield | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Tue., 10/9 | V Girls Volleyball | Joel Barlow | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | L 3-0 | |
| Tue., 10/9 | JV Girls Volleyball | Joel Barlow | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Wed., 10/10 | V Boys Soccer | Ridgefield | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 4-1 | |
| Wed., 10/10 | JV Boys Soccer | Ridgefield | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | W 3-1 | |
| Wed., 10/10 | FR Boys Soccer | Ridgefield | Away - Lower Grass Field [Directions] | 4:00 p.m. | W 5-1 | |
| Wed., 10/10 | V Boys Water Polo | Hopkins School | Home - Staples HS Pool [Directions] | 4:30 p.m. | JV 5:30pm | |
| Wed., 10/10 | V Field Hockey | New Canaan | Away - Dunning Stadium [Directions] | 4:00 p.m. | W 4-0 | |
| Wed., 10/10 | JV Field Hockey | New Canaan | Away - Dunning Stadium [Directions] | 5:30 p.m. | ||
| Wed., 10/10 | FR Field Hockey | New Canaan | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | ||
| Wed., 10/10 | V Girls Volleyball | Westhill | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | L 1-3 | |
| Wed., 10/10 | JV Girls Volleyball | Westhill | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Thu., 10/11 | V Girls Swimming and Diving | Wilton | Away - Wilton YMCA [Directions] | 3:40 p.m. | ED 1:45 | |
| Thu., 10/11 | FR Girls Volleyball | Westhill | Away - Westhill - New Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 10/12 | JV Boys Soccer | Darien | Away - DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | L 2-1 | |
| Fri., 10/12 | V Boys Water Polo | Cardinals Tournament | Away | 8:20 p.m. | ||
| Fri., 10/12 | V Field Hockey | Wilton | Home - Ginny Parker Field - Staples [Directions] | 4:30 p.m. | W 4-1 | |
| Fri., 10/12 | FR Field Hockey | Wilton | Away [Directions] | 4:00 p.m. | ||
| Fri., 10/12 | V Girls Soccer | Darien | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | W 3-1 | |
| Fri., 10/12 | JV Girls Soccer | Darien | Away - DHS Center Oval Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 10/12 | V Girls Volleyball | Stamford | Away - Stamford HS [Directions] | 4:00 p.m. | L 2-3 | |
| Fri., 10/12 | JV Girls Volleyball | Stamford | Away - Stamford HS [Directions] | 5:30 p.m. | ||
| Fri., 10/12 | FR Girls Volleyball | Stamford | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/13 | V Boys Soccer | Darien | Home - Loeffler Field - Staples HS [Directions] | 2:00 p.m. | T 0-0 | |
| Sat., 10/13 | V Boys Water Polo | Cardinals Tournament | Away | 10:00 a.m. | ||
| Sat., 10/13 | V Girls Soccer | Fairfield Ludlowe | Home - Loeffler Field - Staples HS [Directions] | 10:00 a.m. | W 3-0 | |
| Sat., 10/13 | Miscellaneous Events | Adult Rugby | Home - Staples Stadium [Directions] | 2:00 p.m. | ||
| Mon., 10/15 | V Boys Soccer | Fairfield Ludlowe | Away - Taft Field [Directions] | 7:00 p.m. | W 2-0 | |
| Mon., 10/15 | V Field Hockey | Trumbull | Away - McDougall Stadium [Directions] | 7:30 p.m. | W 9-0 | |
| Mon., 10/15 | JV Field Hockey | Trumbull | Away - McDougall Stadium [Directions] | 6:00 p.m. | ||
| Mon., 10/15 | FR Field Hockey | Trumbull | Home - Ginny Parker Field - Staples [Directions] | 4:15 p.m. | ||
| Mon., 10/15 | JV Girls Soccer | Wilton | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Mon., 10/15 | V Girls Swimming and Diving | Ridgefield | Away - Pool at Barlow Mountain School [Directions] | 4:00 p.m. | ED 1:45 | |
| Mon., 10/15 | V Girls Volleyball | Ridgefield | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Mon., 10/15 | JV Girls Volleyball | Ridgefield | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Mon., 10/15 | FR Girls Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/16 | FR Boys Soccer | Fairfield Ludlowe | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | W 3-0 | |
| Tue., 10/16 | FR Girls Soccer | Darien | Away - DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Wed., 10/17 | V Boys Water Polo | Choate, Suffield | Home - Staples HS Pool [Directions] | 5:00 p.m. | JV at 6pm vs Choate | |
| Wed., 10/17 | V Field Hockey | Norwalk | Home - Ginny Parker Field - Staples [Directions] | 3:45 p.m. | W 2-1 | |
| Wed., 10/17 | JV Field Hockey | Norwalk | Home - Ginny Parker Field - Staples [Directions] | 5:00 p.m. | ||
| Wed., 10/17 | FR Field Hockey | Norwalk | Away - Callahan Complex at Nathan Hale Lower [Directions] | 4:30 p.m. | ||
| Wed., 10/17 | V Girls Volleyball | Darien | Away - DHS Main Gym [Directions] | 4:00 p.m. | W 3-2 | |
| Wed., 10/17 | JV Girls Volleyball | Darien | Away - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 10/17 | FR Girls Volleyball | Darien | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/18 | V Boys Cross Country | FCIAC Championships | Away - Waveny Park | 2:00 p.m. | ED 11:00 | |
| Thu., 10/18 | FR Football | Norwalk | Away - Callahan Complex at Nathan Hale Lower [Directions] | 4:00 p.m. | ||
| Thu., 10/18 | V Girls Cross Country | FCIAC Championships | Away - Waveny Park | 2:00 p.m. | ED 11:00 | |
| Thu., 10/18 | JV Girls Soccer | Fairfield Ludlowe | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Fri., 10/19 | V Football | Norwalk | Home - Staples Stadium [Directions] | 7:00 p.m. | W 40-20 | |
| Fri., 10/19 | JV Boys Soccer | Fairfield Ludlowe | Away - Roger Ludlowe MS [Directions] | 4:00 p.m. | T 3-3 | |
| Fri., 10/19 | FR Boys Soccer | New Canaan | Away - Saxe MS Field [Directions] | 4:00 p.m. | W 4-2 | |
| Fri., 10/19 | V Competitive Cheerleading | Norwalk | Home - Staples Stadium [Directions] | 7:00 p.m. | ||
| Fri., 10/19 | V Girls Soccer | New Canaan | Away - Dunning Stadium [Directions] | 4:00 p.m. | W 2-1 | |
| Fri., 10/19 | JV Girls Soccer | New Canaan | Away - Saxe MS Field [Directions] | 4:00 p.m. | ||
| Fri., 10/19 | FR Girls Soccer | New Canaan | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Fri., 10/19 | V Girls Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 6:00 p.m. | L 1-3 | |
| Fri., 10/19 | JV Girls Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 4:30 p.m. | ||
| Fri., 10/19 | FR Girls Volleyball | Fairfield Ludlowe | Away - FLHS Aux Gym [Directions] | 4:30 p.m. | ||
| Sat., 10/20 | V Boys Soccer | New Canaan | Home - Loeffler Field - Staples HS [Directions] | 2:00 p.m. | W 1-0 | |
| Sat., 10/20 | JV Boys Soccer | New Canaan | Home - Wakeman Field B (turf) [Directions] | 2:00 p.m. | W 5-1 | |
| Sat., 10/20 | V Field Hockey | Joel Barlow | Home - Ginny Parker Field - Staples [Directions] | 12:00 p.m. | W 8-0 | |
| Sat., 10/20 | JV Field Hockey | Joel Barlow | Home - Ginny Parker Field - Staples [Directions] | 1:30 p.m. | ||
| Mon., 10/22 | V Field Hockey | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 5:15 p.m. | W 1-0 | |
| Mon., 10/22 | JV Field Hockey | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 4:00 p.m. | ||
| Mon., 10/22 | FR Field Hockey | Ridgefield | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | ||
| Mon., 10/22 | V Girls Soccer | St. Joseph | Home - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 1-0 | |
| Mon., 10/22 | JV Girls Soccer | St. Joseph | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Tue., 10/23 | V Boys Cross Country | Wilton JV Invitational | Away | 4:00 p.m. | ED 1:30 | |
| Tue., 10/23 | V Boys Soccer | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | W 4-1 | |
| Tue., 10/23 | JV Boys Soccer | St. Joseph | Away - St. Catherines, Trumbull, CT [Directions] | Cancelled | Cancelled | |
| Tue., 10/23 | FR Boys Soccer | Greenwich | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | L 3-1 | |
| Tue., 10/23 | V Girls Cross Country | Wilton JV Invitational | Away | 4:00 p.m. | ED 1:30 | |
| Tue., 10/23 | FR Girls Soccer | Fairfield Ludlowe | Away - South Pine Creek Field [Directions] | 3:30 p.m. | ||
| Tue., 10/23 | V Girls Swimming and Diving | Fairfield Ludlowe | Home - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Wed., 10/24 | V Boys Water Polo | Horace Mann (NY) | Away | 4:00 p.m. | ED 1:30 JV @ 5:00 | |
| Wed., 10/24 | V Girls Volleyball | New Canaan | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | W 3-0 | |
| Wed., 10/24 | JV Girls Volleyball | New Canaan | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Wed., 10/24 | FR Girls Volleyball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 10/25 | V Boys Cross Country | Danbury Freshmen Invitational | Away | 4:00 p.m. | ED 1:15 | |
| Thu., 10/25 | FR Football | Fairfield Warde | Home - Staples Stadium [Directions] | 6:00 p.m. | ||
| Thu., 10/25 | JV Boys Soccer | Norwalk | Away - Callahan Complex at Nathan Hale Lower [Directions] | 4:00 p.m. | W 2-0 | |
| Thu., 10/25 | FR Boys Soccer | Darien | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | W 7-3 | |
| Thu., 10/25 | V Boys Water Polo | Hopkins School | Away | 4:15 p.m. | ED 2:00, JV @ 5:15 | |
| Thu., 10/25 | V Girls Cross Country | Danbury Freshmen Invitational | Away | 4:00 p.m. | ED 1:15 | |
| Thu., 10/25 | V Girls Soccer | Darien | Home - Loeffler Field - Staples HS [Directions] | 3:00 p.m. | ED 1:30 | |
| Thu., 10/25 | FR Girls Soccer | Weston | Away - WHS Turf Field [Directions] | 5:15 p.m. | ||
| Fri., 10/26 | V Boys Cross Country | CIAC Class LL Championship | Away - Wickham Park - East Hartford [Directions] | 10:20 a.m. | ||
| Fri., 10/26 | V Football | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 7:30 p.m. | W 28-6 | |
| Fri., 10/26 | V Boys Soccer | Greenwich | Home - Loeffler Field - Staples HS [Directions] | 3:00 p.m. | W 1-0 | ED 1:30 |
| Fri., 10/26 | V Competitive Cheerleading | Fairfield Warde | Away [Directions] | 7:30 p.m. | ||
| Fri., 10/26 | V Girls Cross Country | CIAC Class LL Championship | Away - Wickham Park - East Hartford [Directions] | 10:50 a.m. | ||
| Fri., 10/26 | V Field Hockey | Fairfield Warde | Home - Ginny Parker Field - Staples [Directions] | TBA | W 6-0 | |
| Fri., 10/26 | V Girls Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | 5:30 p.m. | L 3-2 | |
| Fri., 10/26 | JV Girls Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | ||
| Fri., 10/26 | FR Girls Volleyball | St. Joseph | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/27 | JV Girls Swimming and Diving | JV FCIAC Finals | Away - Greenwich HS | 2:00 p.m. | ||
| Sat., 10/27 | Miscellaneous Events | Adult Rugby | Home - Staples Stadium [Directions] | 2:00 p.m. | ||
| Mon., 10/29 | V Boys Soccer | Trumbull | Away - Fairfield Ludlowe HS [Directions] | 7:00 p.m. | L 1-0 | |
| Mon., 10/29 | V Field Hockey | Norwalk | Away - Brien McMahon HS [Directions] | 6:00 p.m. | W 3-1 | |
| Mon., 10/29 | V Girls Swimming and Diving | FCIAC Diving Final | Away - Westhill HS | 5:00 p.m. | ||
| Tue., 10/30 | V Girls Swimming and Diving | FCIAC Swimming Trials | Away - Greenwich | 5:30 p.m. | ||
| Tue., 10/30 | V Girls Volleyball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 11/1 | V Boys Cross Country | CIAC Open Championship | Away - Wickham Park - East Hartford [Directions] | 2:00 p.m. | ED 10:00am | |
| Thu., 11/1 | FR Football | St. Joseph | Away - St. Joseph HS [Directions] | 3:30 p.m. | ||
| Thu., 11/1 | V Boys Water Polo | Choate Rosemary Hall | Away | 5:00 p.m. | JV at 6pm | |
| Thu., 11/1 | V Girls Cross Country | CIAC Open Championship | Away - Wickham Park - East Hartford [Directions] | 2:45 p.m. | ED 10:00 | |
| Thu., 11/1 | V Field Hockey | Darien | Away - Brien McMahon HS [Directions] | 7:00 p.m. | ||
| Thu., 11/1 | V Girls Swimming and Diving | FCIAC Swimming Finals | Away - Greenwich HS | 6:30 p.m. | ||
| Fri., 11/2 | V Football | St. Joseph | Home - Staples Stadium [Directions] | 7:00 p.m. | L 14-17 | |
| Fri., 11/2 | V Boys Water Polo | Loomis Chaffee School | Home - Staples HS Pool [Directions] | 5:30 p.m. | ||
| Fri., 11/2 | V Boys Water Polo | JV Tournament | Away - Greenwich HS | 7:00 p.m. | ||
| Fri., 11/2 | V Competitive Cheerleading | St. Joseph | Home - Staples Stadium [Directions] | 7:00 p.m. | ||
| Sat., 11/3 | V Boys Soccer | Masuk (Scrim.) | Home - Wakeman Field B (turf) [Directions] | 3:00 p.m. | ||
| Sat., 11/3 | V Boys Water Polo | JV Tournament | Away - Greenwich HS | 11:00 a.m. | ||
| Sat., 11/3 | Miscellaneous Events | Westport Field Hockey Jamboree | Home - Staples Stadium [Directions] | 11:00 a.m. | ||
| Sat., 11/3 | Miscellaneous Events | Adult Rugby | Home - Staples Stadium [Directions] | 2:00 p.m. | ||
| Mon., 11/5 | JV Football | St. Joseph | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Mon., 11/5 | V Girls Soccer | Fairfield Warde | Home - Wakeman Field B (turf) [Directions] | 2:00 p.m. | ED 12:30 | |
| Mon., 11/5 | V Girls Volleyball | South Windsor | Away - South Windsor HS [Directions] | 5:00 p.m. | ED 2:00 | |
| Tue., 11/6 | V Boys Soccer | Darien | Home - Wakeman Field B (turf) [Directions] | 2:00 p.m. | W 2-1 | |
| Wed., 11/7 | V Field Hockey | Glastonbury | Home - Ginny Parker Field - Staples [Directions] | 2:00 p.m. | ED 12:30 | |
| Wed., 11/7 | V Girls Soccer | New Canaan | Home - Wakeman Field B (turf) [Directions] | 2:00 p.m. | ED 12:30 | |
| Wed., 11/7 | V Girls Swimming and Diving | CIAC Class LL Diving Trials/Finals | Away - Middletown HS [Directions] | 5:30 p.m. | ||
| Thu., 11/8 | FR Football | Stamford | Away [Directions] | 4:00 p.m. | ||
| Thu., 11/8 | V Boys Soccer | Cheshire | Away - Cheshire High Main Game field [Directions] | 5:00 p.m. | L 3-1 | |
| Fri., 11/9 | V Football | Stamford | Home - Staples Stadium [Directions] | 7:00 p.m. | W 37-0 | |
| Fri., 11/9 | V Competitive Cheerleading | Stamford | Home - Staples Stadium [Directions] | 7:00 p.m. | ||
| Fri., 11/9 | V Field Hockey | Norwalk | Home - Ginny Parker Field - Staples [Directions] | 2:00 p.m. | ||
| Fri., 11/9 | V Girls Soccer | Trumbull | Home - Wakeman Field B (turf) [Directions] | 2:00 p.m. | ED 12:30 | |
| Sat., 11/10 | V Boys Cross Country | New England Championship | Away - Derryfield Park (Manchester, NH) [Directions] | 11:00 a.m. | ||
| Sat., 11/10 | JV Football | Stamford | Home - Staples Stadium [Directions] | 10:00 a.m. | ||
| Sat., 11/10 | V Girls Cross Country | New England Championship | Away - Derryfield Park (Manchester, NH) [Directions] | 11:00 a.m. | ||
| Sat., 11/10 | V Girls Swimming and Diving | CIAC Class LL Qualifying | Away - East Hartford [Directions] | 11:30 a.m. | ||
| Mon., 11/12 | V Girls Soccer | Glastonbury | Away - Naugatuck H.S. [Directions] | 6:30 p.m. | ||
| Tue., 11/13 | V Field Hockey | Darien | Away - Brien McMahon HS [Directions] | 6:00 p.m. | ||
| Wed., 11/14 | FR Football | Greenwich | Home - Staples Stadium [Directions] | 5:00 p.m. | ||
| Wed., 11/14 | V Girls Swimming and Diving | CIAC Class LL Finals | Away - SCSU [Directions] | 6:00 p.m. | ||
| Fri., 11/16 | V Girls Swimming and Diving | CIAC Open Diving | Away - Middletown HS [Directions] | 5:30 p.m. | ||
| Sat., 11/17 | V Girls Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 12:00 p.m. | ||
| Sun., 11/18 | V Field Hockey | Cheshire | Away - Wethersfield HS [Directions] | 12:30 p.m. | ||
| Sun., 11/18 | V Girls Soccer | Ridgefield | Away - West Haven HS [Directions] | 3:00 p.m. | ||
| Thu., 11/22 | V Football | Greenwich | Away - Cardinal Stadium [Directions] | 10:00 a.m. | L 0-29 | |
| Thu., 11/22 | V Competitive Cheerleading | Greenwich | Away [Directions] | 10:00 a.m. | ||
| Mon., 11/26 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10pm-5:10pm | ||
| Tue., 11/27 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10pm-5:10pm | ||
| Wed., 11/28 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10pm-5:10pm | ||
| Thu., 11/29 | V Boys Ice Hockey | Immaculate (Scrim.) | Home - Milford Ice Pavilion [Directions] | 8:30 p.m. | ||
| Fri., 11/30 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10pm-5:10pm | ||
| Fri., 11/30 | Unified Sports Soccer | Youth Leadership Summit | Away | 7:00 a.m. | ||
| Sat., 12/1 | V Boys Ice Hockey | North Haven (Scrim.) | Home - Milford Ice Pavilion [Directions] | 3:00 p.m. | ||
| Sat., 12/1 | V Girls Ice Hockey | HS Girls Hockey Jamboree | Away - The Rinks at Shelton | 5:45 p.m. | ||
| Mon., 12/3 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10pm-5:10pm | ||
| Mon., 12/3 | ALL Co-ed Squash | Practice | Home - Intensity [Directions] | 2:20pm | ||
| Tue., 12/4 | V Boys Basketball | Foran (Scrim.) | Away - Edna L. Fraser Gymnasium [Directions] | 6:00 p.m. | ||
| Tue., 12/4 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10pm-5:10pm | ||
| Tue., 12/4 | ALL Co-ed Squash | Practice | Home - Intensity [Directions] | 2:20pm | ||
| Wed., 12/5 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10pm-5:10pm | ||
| Wed., 12/5 | ALL Co-ed Squash | Practice | Home - Intensity [Directions] | 2:20pm | ||
| Wed., 12/5 | V Girls Basketball | Kolbe Cathedral (Scrim.) | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Wed., 12/5 | V Girls Ice Hockey | Notre Dame-Fairfield | Away - The Rinks at Shelton - Upper [Directions] | 4:15 p.m. | L 2-8 | |
| Thu., 12/6 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10pm-5:10pm | ||
| Thu., 12/6 | ALL Co-ed Squash | Practice | Home - Intensity [Directions] | 2:20pm | ||
| Fri., 12/7 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10pm-5:10pm | ||
| Fri., 12/7 | V Girls Indoor Track | Blue and White Time Trials | Home - Staples Field House [Directions] | TBA | ||
| Sat., 12/8 | V Boys Ice Hockey | Shelton Jamboree | Away | 7:15 p.m. | ||
| Sat., 12/8 | V Girls Indoor Track | Hillhouse Developmental Meet | Away - Floyd Little Athletic Complex | TBA | ||
| Sat., 12/8 | V Girls Indoor Track | Blue and White Time Trials | Home - Staples Field House [Directions] | TBA | ||
| Mon., 12/10 | V Boys Basketball | Jonathan Law (Scrim.) | Away - Jonathan Law HS-Richetelli Gymnasium [Directions] | 7:00 p.m. | ||
| Mon., 12/10 | JV Boys Ice Hockey | Eastern CT Eagles | Home - Milford Ice Pavilion [Directions] | 4:10 p.m. | ED 1:45 | |
| Mon., 12/10 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 3:00pm - 4:00pm | ED 1:45 | |
| Mon., 12/10 | ALL Co-ed Squash | Practice | Home - Intensity [Directions] | 2:20pm | ||
| Mon., 12/10 | V Girls Basketball | Bethel | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | W 67-61 | |
| Mon., 12/10 | JV Girls Basketball | Bethel | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Tue., 12/11 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10pm-5:10pm | ||
| Tue., 12/11 | ALL Co-ed Squash | Practice | Home - Intensity [Directions] | 2:20pm | ||
| Wed., 12/12 | V Boys Basketball | Stratford (Scrim.) | Home - Staples H.S. Gym [Directions] | 3:30 p.m. | ||
| Wed., 12/12 | V Boys Ice Hockey | Newtown/New Fairfield | Home - Milford Ice Pavilion [Directions] | 6:00 p.m. | W 4-2 | |
| Wed., 12/12 | V Wrestling | Fairfield Ludlowe | Away - FLHS Aux Gym [Directions] | 6:00 p.m. | ||
| Wed., 12/12 | ALL Co-ed Squash | Practice | Home - Intensity [Directions] | 2:20pm | ||
| Wed., 12/12 | V Girls Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 7:00 p.m. | W 40-38 | |
| Wed., 12/12 | JV Girls Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 5:15 p.m. | ||
| Wed., 12/12 | FR Girls Basketball | New Canaan | Away - NCHS Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 12/12 | V Girls Ice Hockey | Trumbull/St. Joseph | Home - Terry Conners Ice Rink [Directions] | 7:50 p.m. | W 5-4 | |
| Thu., 12/13 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10pm-5:10pm | ||
| Thu., 12/13 | ALL Co-ed Squash | Practice | Home - Intensity [Directions] | 2:20pm | ||
| Fri., 12/14 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10pm-5:10pm | ||
| Fri., 12/14 | V Co-ed Squash | Yale | Away | 4:00 p.m.p.m. | ||
| Fri., 12/14 | V Girls Basketball | St. Joseph | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | W 48-44 | |
| Fri., 12/14 | JV Girls Basketball | St. Joseph | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Fri., 12/14 | FR Girls Basketball | St. Joseph | Home - Staples H.S. Gym [Directions] | 4:15 p.m. | ||
| Sat., 12/15 | V Boys Basketball | Weston | Away - WHS Gymnasium [Directions] | 6:00 p.m. | W 71-49 | |
| Sat., 12/15 | JV Boys Basketball | Weston | Away - WHS Gymnasium [Directions] | 4:15 p.m. | ||
| Sat., 12/15 | FR Boys Basketball | Weston | Away - WHS Gymnasium [Directions] | 2:30 p.m. | ||
| Sat., 12/15 | V Boys Ice Hockey | Enfield/East Granby/Stafford | Away - Enfield Twin Rinks [Directions] | 4:00 p.m. | L 2-3 | |
| Sat., 12/15 | V Boys Indoor Track | St. Joe's, FLHS, Ridgefield, Trumbull, Greenwich, Stamford, Westhill | Home - Staples Field House [Directions] | 10:00 a.m. | ||
| Sat., 12/15 | V Wrestling | Ludlowe Invitational | Away | 8:30 a.m. | ||
| Sat., 12/15 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Away - Wonderland of Ice [Directions] | 6:00 p.m. | L 3-9 | |
| Sat., 12/15 | V Girls Indoor Track | St. Joe's, FLHS, Ridgefield, Trumbull, Greenwich, Stamford, Westhill | Home - Staples Field House [Directions] | 10:00 a.m. | ||
| Mon., 12/17 | V Boys Basketball | Joel Barlow | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | W 52-47 | |
| Mon., 12/17 | JV Boys Basketball | Joel Barlow | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Mon., 12/17 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10pm-5:10pm | ||
| Mon., 12/17 | ALL Co-ed Squash | Practice | Home - Intensity [Directions] | 2:20pm | ||
| Tue., 12/18 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10pm-5:10pm | ||
| Tue., 12/18 | V Wrestling | New Canaan | Away - NCHS Gymnasium [Directions] | 6:00 p.m. | ||
| Tue., 12/18 | ALL Co-ed Squash | Practice | Home - Intensity [Directions] | 2:20pm | ||
| Wed., 12/19 | V Boys Basketball | Fairfield Warde | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | L 47-49 | |
| Wed., 12/19 | JV Boys Basketball | Fairfield Warde | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Wed., 12/19 | FR Boys Basketball | Fairfield Warde | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Wed., 12/19 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 3:00pm-4:00pm | ED 1:45 | |
| Wed., 12/19 | V Boys Swimming and Diving | Trumbull | Away - Hillcrest MS [Directions] | 4:00 p.m. | ||
| Wed., 12/19 | V Co-ed Alpine Skiing | Practice | Home - Mt Southington [Directions] | 4:00pm | ||
| Wed., 12/19 | ALL Co-ed Squash | Practice | Home - Intensity [Directions] | 2:20pm | ||
| Wed., 12/19 | V Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 7:00 p.m. | W 59-43 | |
| Wed., 12/19 | JV Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 5:15 p.m. | ||
| Wed., 12/19 | FR Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 4:00 p.m. | ||
| Wed., 12/19 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Away - Winter Garden Ice Arena [Directions] | 3:30 p.m. | L 1-6 | |
| Thu., 12/20 | JV Boys Ice Hockey | Notre Dame-West Haven | Home - Milford Ice Pavilion [Directions] | 4:10 p.m. | ED 1:45 | |
| Thu., 12/20 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 3:00-4:00 | ED 1:45 | |
| Thu., 12/20 | ALL Co-ed Squash | Practice | Home - Intensity [Directions] | 2:20pm | ||
| Fri., 12/21 | V Boys Basketball | Danbury | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | L 48-62 | |
| Fri., 12/21 | JV Boys Basketball | Danbury | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Fri., 12/21 | FR Boys Basketball | Danbury | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Fri., 12/21 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10pm-5:10pm | ||
| Fri., 12/21 | V Boys Swimming and Diving | Ridgefield | Away - Pool at Barlow Mountain School [Directions] | 4:00 p.m. | ED 1:45 | |
| Fri., 12/21 | V Girls Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 7:00 p.m. | L 37-43 | |
| Fri., 12/21 | JV Girls Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 5:15 p.m. | ||
| Fri., 12/21 | FR Girls Basketball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 4:00 p.m. | ||
| Fri., 12/21 | V Girls Gymnastics | Greenwich | Away - Greenwich YWCA [Directions] | 5:00 p.m. | 128.65 | |
| Sat., 12/22 | V Boys Ice Hockey | East Haven Coop | Home - Milford Ice Pavilion [Directions] | 3:00 p.m. | L 0-3 | |
| Sat., 12/22 | V Wrestling | Wilton, Brien McMahon | Away - Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Wed., 12/26 | JV Boys Ice Hockey | Eastern CT Eagles | Away - Connecticut College [Directions] | 6:00 p.m. | Start and End at MIP | |
| Wed., 12/26 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 9:30-11:00 | ||
| Thu., 12/27 | V Boys Basketball | Westhill | Home - Staples H.S. Gym [Directions] | 5:00 p.m. | W 70-51 | |
| Thu., 12/27 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 2:00-3:45pm | ||
| Thu., 12/27 | V Boys Indoor Track | Jack Long Invitational | Away - Hillhouse | 12:00 p.m. | ||
| Thu., 12/27 | V Girls Basketball | Fairfield Warde | Away - Fairfield Warde Large Gym [Directions] | 2:00 p.m. | W 49-42 | |
| Fri., 12/28 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:45pm-6:00pm | ||
| Fri., 12/28 | V Girls Basketball | Fairfield Ludlowe | Away [Directions] | TBA | L 36-48 | |
| Sat., 12/29 | V Boys Basketball | Newtown | Home - Staples H.S. Gym [Directions] | TBA | L 44-54 | |
| Sat., 12/29 | V Boys Ice Hockey | Amity | Away - Bennett Rink - West Haven [Directions] | 1:00 p.m. | L 2-3(OT) | Start and End at MIP |
| Sat., 12/29 | V Boys Indoor Track | Hillhouse Winter Relays | Away - Hillhouse | 10:00 a.m. | ||
| Sat., 12/29 | V Wrestling | Danbury Holiday Tournament | Away | 8:30 a.m. | ||
| Sat., 12/29 | V Girls Indoor Track | Holiday Classic | Away | 8:30 a.m. | ||
| Mon., 12/31 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 3:00/4:45 | ||
| Tue., 1/1 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 3:30-5:00 | ||
| Wed., 1/2 | V Boys Ice Hockey | Lyman Hall | Away - Northford Ice Pavilion [Directions] | 8:30 p.m. | L 1-4 | |
| Wed., 1/2 | V Wrestling | Greenwich | Home - Staples H.S. Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/2 | ALL Co-ed Squash | Practice | Home - Intensity [Directions] | 2:20pm | ||
| Thu., 1/3 | V Boys Basketball | Trinity Catholic | Away - Walsh Court | 7:00 p.m. | L 56-62 | |
| Thu., 1/3 | JV Boys Basketball | Trinity Catholic | Away - Walsh Court | 5:15 p.m. | ||
| Thu., 1/3 | FR Boys Basketball | Trinity Catholic | Away | 4:00 p.m. | ||
| Thu., 1/3 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10pm-5:10pm | ||
| Thu., 1/3 | ALL Co-ed Squash | Practice | Home - Intensity [Directions] | 2:20pm | ||
| Thu., 1/3 | V Girls Basketball | Trinity Catholic | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | L 49-68 | |
| Thu., 1/3 | JV Girls Basketball | Trinity Catholic | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/4 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10pm-5:10pm | ||
| Fri., 1/4 | V Boys Indoor Track | Hispanic Games | Away - Armory NYC | Cancelled | Cancelled | |
| Fri., 1/4 | V Boys Swimming and Diving | Darien | Home - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Fri., 1/4 | V Girls Indoor Track | Hispanic Games | Away | 4:00 p.m. | ||
| Sat., 1/5 | V Boys Ice Hockey | New Milford | Home - Milford Ice Pavilion [Directions] | 3:00 p.m. | W 4-0 | |
| Sat., 1/5 | V Boys Indoor Track | Greenwich, Danbury, St Joe's, McMahon, Trumbull, Westhill | Home - Staples Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/5 | V Boys Indoor Track | Hispanic Games | Away - Armory NYC | 8:30 a.m. | ||
| Sat., 1/5 | V Wrestling | Warde Invitational | Away | 8:30 a.m. | ||
| Sat., 1/5 | V Girls Gymnastics | Pomperaug | Away [Directions] | TBA | 121.5 | |
| Sat., 1/5 | V Girls Ice Hockey | East Catholic Coop | Away - Newington Arena [Directions] | 8:50 p.m. | L 3-7 | |
| Sat., 1/5 | V Girls Indoor Track | Greenwich, Danbury, St Joe's, McMahon, Trumbull, Westhill | Home - Staples Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/5 | V Girls Indoor Track | Hispanic Games | Away | 8:30 a.m. | ||
| Mon., 1/7 | V Boys Basketball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 7:00 p.m. | W 55-50 | |
| Mon., 1/7 | JV Boys Basketball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 5:15 p.m. | ||
| Mon., 1/7 | FR Boys Basketball | Wilton | Away - Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Mon., 1/7 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10pm-5:10pm | ||
| Mon., 1/7 | V Co-ed Alpine Skiing | Practice | Home - Mt Southington [Directions] | 4:00pm | ||
| Mon., 1/7 | ALL Co-ed Squash | Practice | Home - Intensity [Directions] | 2:20pm | ||
| Mon., 1/7 | V Girls Basketball | Wilton | Home - Staples H.S. Gym [Directions] | 6:00 p.m. | W 47-26 | |
| Mon., 1/7 | JV Girls Basketball | Wilton | Home - Staples H.S. Gym [Directions] | 4:30 p.m. | ||
| Tue., 1/8 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10pm-5:10pm | ||
| Tue., 1/8 | V Co-ed Squash | St. Lukes | Away | 4:00 p.m. | ||
| Tue., 1/8 | ALL Co-ed Squash | Practice | Home - Intensity [Directions] | 2:20pm | ||
| Tue., 1/8 | V Girls Gymnastics | Westhill, New Canaan | Away - Westhill - New Gymnasium [Directions] | 6:15 p.m. | 119.4 | |
| Wed., 1/9 | V Boys Ice Hockey | Ridgefield | Away - Winter Garden Ice Arena [Directions] | 8:30 p.m. | L 0-9 | |
| Wed., 1/9 | V Wrestling | Danbury | Home - Staples H.S. Gym [Directions] | 6:00 p.m. | Danbury will wrestle Ridgefield | |
| Wed., 1/9 | ALL Co-ed Squash | Practice | Home - Intensity [Directions] | 2:20pm | ||
| Wed., 1/9 | V Girls Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | 8:15 p.m. | L 0-8 | |
| Thu., 1/10 | V Boys Basketball | Trumbull | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | L 45-63 | |
| Thu., 1/10 | JV Boys Basketball | Trumbull | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Thu., 1/10 | FR Boys Basketball | Trumbull | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Thu., 1/10 | JV Boys Ice Hockey | Notre Dame-West Haven | Away - Bennett Rink [Directions] | 4:00 p.m. | ED 1:45 | |
| Thu., 1/10 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 3:00pm-4:00pm | ||
| Thu., 1/10 | V Co-ed Alpine Skiing | Race #1 | Away - Mt Southington | 4:00 p.m. | ED 1:30 | |
| Thu., 1/10 | ALL Co-ed Squash | Practice | Home - Intensity [Directions] | 2:20pm | ||
| Thu., 1/10 | V Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | 7:00 p.m. | L 25-36 | |
| Thu., 1/10 | JV Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | 5:15 p.m. | ||
| Thu., 1/10 | FR Girls Basketball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/11 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10pm-5:10pm | ||
| Fri., 1/11 | V Boys Indoor Track | Yale Invitational | Away | 1:00 p.m. | ||
| Fri., 1/11 | V Girls Indoor Track | Yale Track and Field Classic | Away | 1:00 p.m. | ||
| Sat., 1/12 | V Boys Ice Hockey | Wilton | Away - Winter Garden Rink-Ridgefield [Directions] | 8:50 p.m. | L 4-5(OT) | |
| Sat., 1/12 | V Boys Indoor Track | Ridgefield, Norwalk, Westhill, Trumbull, Warde, New Canaan, Stamford | Home - Staples Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/12 | V Boys Indoor Track | Yale Invitational | Away | 9:00 a.m. | ||
| Sat., 1/12 | V Wrestling | John Chacho Duals, Fairfield Prep, Stamford, Mahopac | Home - Staples H.S. Gym [Directions] | 8:45 a.m. | ||
| Sat., 1/12 | V Girls Gymnastics | Trumbull | Away - Next Dimension Gymnastics [Directions] | 6:30 p.m. | 121.8 | |
| Sat., 1/12 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Home - Terry Conners Ice Rink [Directions] | 5:30 p.m. | W 8-7 | |
| Sat., 1/12 | V Girls Indoor Track | Ridgefield, Norwalk, Westhill, Trumbull, Warde, New Canaan, Stamford | Home - Staples Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/12 | V Girls Indoor Track | Yale Track and Field Classic | Away | 8:00 a.m. | ||
| Mon., 1/14 | V Boys Basketball | Bridgeport Central | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | W 78-60 | |
| Mon., 1/14 | JV Boys Basketball | Bridgeport Central | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Mon., 1/14 | FR Boys Basketball | Bridgeport Central | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Mon., 1/14 | V Boys Ice Hockey | Fairfield Warde/Ludlowe | Away - Wonderland Of Ice [Directions] | 8:00 p.m. | L 2-7 | |
| Mon., 1/14 | V Girls Basketball | Bridgeport Central | Away - Central H.S. Gym [Directions] | 4:00 p.m. | W 70-13 | |
| Tue., 1/15 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10pm-5:10pm | ||
| Tue., 1/15 | V Co-ed Alpine Skiing | Practice | Home - Mt Southington [Directions] | 4:00pm | ||
| Tue., 1/15 | V Girls Gymnastics | Wilton | Away - Wilton HS Aux. Gym [Directions] | 4:00 p.m. | 121.15 | |
| Wed., 1/16 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10pm-5:10pm | ||
| Wed., 1/16 | V Wrestling | Westhill | Home - Staples H.S. Gym [Directions] | 6:00 p.m. | ||
| Wed., 1/16 | V Girls Ice Hockey | New Canaan | Home - Terry Conners Ice Rink [Directions] | 5:40 p.m. | L 0-7 | |
| Thu., 1/17 | V Boys Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 5:30 p.m. | L 49-61 | |
| Thu., 1/17 | JV Boys Basketball | Greenwich | Away - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Thu., 1/17 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10pm | ed 1:45 | |
| Thu., 1/17 | V Boys Swimming and Diving | New Canaan | Home - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Thu., 1/17 | V Co-ed Alpine Skiing | Race #2 | Away - Mt Southington | 4:00 p.m. | ED 1:30 | |
| Thu., 1/17 | V Girls Basketball | Greenwich | Home - Staples H.S. Gym [Directions] | 5:00 p.m. | W 48-34 | |
| Thu., 1/17 | JV Girls Basketball | Greenwich | Home - Staples H.S. Gym [Directions] | 3:30 p.m. | ||
| Fri., 1/18 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10pm-5:10pm | ||
| Fri., 1/18 | V Girls Ice Hockey | Trumbull/St. Joseph | Away [Directions] | 5:30 p.m. | L 4-5 | |
| Fri., 1/18 | V Girls Indoor Track | East Coast Classic | Away | Cancelled | Cancelled | Providence Career & Tech Center |
| Sat., 1/19 | FR Boys Basketball | Greenwich | Away - Central MS [Directions] | 9:00 a.m. | ||
| Sat., 1/19 | V Boys Indoor Track | Stamford, St Joe's, Darien, Greenwich, Danbury, McMahon | Home - Staples Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/19 | V Boys Indoor Track | SCC Coaches Invitational | Away - Hillhouse | 9:00 a.m. | ||
| Sat., 1/19 | V Wrestling | New Milford Invitational | Away | 8:00 a.m. | ||
| Sat., 1/19 | JV Wrestling | JV Patton Tournament | Away - Danbury HS | 9:00 a.m. | ||
| Sat., 1/19 | V Competitive Cheerleading | Seymour HS | Away | TBA | ||
| Sat., 1/19 | V Girls Indoor Track | Stamford, St Joe's, Darien, Greenwich, Danbury, McMahon | Home - Staples Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/19 | V Girls Indoor Track | SCC Invitational | Away | 2:00 p.m. | ||
| Mon., 1/21 | V Boys Ice Hockey | Darien | Home - Milford Ice Pavilion [Directions] | 6:00 p.m. | L 0-8 | |
| Mon., 1/21 | JV Wrestling | 23rd ANNUAL GRISWOLD JV WRESTLING TOURNAMENT | Away - Griswold HS | 8:45 a.m. | ||
| Mon., 1/21 | V Girls Ice Hockey | Avon | Home - Terry Conners Ice Rink [Directions] | 2:00 p.m. | L 3-4 | |
| Tue., 1/22 | V Boys Basketball | Norwalk | Away - Scarso Gymnasium [Directions] | 7:00 p.m. | W 68-62(2OT) | |
| Tue., 1/22 | JV Boys Basketball | Norwalk | Away - Scarso Gymnasium [Directions] | 5:15 p.m. | ||
| Tue., 1/22 | FR Boys Basketball | Norwalk | Away - Scarso Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/22 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10pm-5:10pm | ||
| Tue., 1/22 | V Co-ed Alpine Skiing | Practice | Home - Mt Southington [Directions] | 4:00pm | ||
| Tue., 1/22 | ALL Co-ed Squash | Practice | Home - Intensity [Directions] | 2:20pm | ||
| Tue., 1/22 | V Girls Basketball | Norwalk | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | L 53-63 | |
| Wed., 1/23 | V Boys Ice Hockey | Trinity Catholic | Away - Terry Conners Ice Rink | 6:00 p.m. | W 2-1(OT) | |
| Wed., 1/23 | V Boys Swimming and Diving | Norwalk/Brien McMahon | Home - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Wed., 1/23 | V Wrestling | Stamford | Away - Stamford High Aux Gym [Directions] | 4:00 p.m. | ||
| Wed., 1/23 | ALL Co-ed Squash | Practice | Home - Intensity [Directions] | 2:20pm | ||
| Wed., 1/23 | V Girls Ice Hockey | Fairfield Ludlowe/Warde | Home - Terry Conners Ice Rink [Directions] | 8:00 p.m. | L 1-8 | |
| Thu., 1/24 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10pm-5:10pm | ||
| Thu., 1/24 | V Boys Swimming and Diving | Wilton | Away [Directions] | 3:40 p.m. | ED 1:45 | |
| Thu., 1/24 | JV Wrestling | Fairfield Warde | Away [Directions] | 3:30 p.m. | ||
| Thu., 1/24 | V Co-ed Alpine Skiing | Race #3 | Away | 4:00 p.m. | ED 1:30 | |
| Thu., 1/24 | ALL Co-ed Squash | Practice | Home - Intensity [Directions] | 2:20pm | ||
| Fri., 1/25 | V Boys Basketball | Brien McMahon | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | W 55-50 | |
| Fri., 1/25 | JV Boys Basketball | Brien McMahon | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Fri., 1/25 | FR Boys Basketball | Brien McMahon | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Fri., 1/25 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10pm-5:10pm | ||
| Fri., 1/25 | V Wrestling | Town Crown | Away - Greens Farms Academy | 6:00 p.m. | ||
| Fri., 1/25 | V Girls Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:30 p.m. | W 68-43 | |
| Fri., 1/25 | JV Girls Basketball | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | ||
| Sat., 1/26 | V Boys Ice Hockey | St. Joseph | Home - Milford Ice Pavilion [Directions] | 8:00 p.m. | W 2-1 | |
| Sat., 1/26 | V Boys Indoor Track | FCIAC Western Division Championships | Home - Staples Field House [Directions] | 10:00 a.m. | ||
| Sat., 1/26 | JV Wrestling | Godleskl Invitational | Away - Norwalk HS | 9:00 a.m. | ||
| Sat., 1/26 | V Competitive Cheerleading | St Joseph Tournament | Away | 10:00 a.m. | ||
| Sat., 1/26 | V Girls Ice Hockey | Ridgefield/Danbury/Immaculate | Home - Terry Conners Ice Rink [Directions] | 2:15 p.m. | L 1-6 | |
| Sat., 1/26 | V Girls Indoor Track | FCIAC Western Division Championships | Home - Staples Field House [Directions] | 10:00 a.m. | ||
| Mon., 1/28 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10pm-5:10pm | ||
| Mon., 1/28 | V Co-ed Alpine Skiing | Practice | Home - Mt Southington [Directions] | 4:00pm | ||
| Mon., 1/28 | V Co-ed Squash | Hopkins School | Away | 4:00 p.m. | ||
| Mon., 1/28 | ALL Co-ed Squash | Practice | Home - Intensity [Directions] | 2:20pm | ||
| Mon., 1/28 | V Girls Ice Hockey | Darien | Away - Darien Ice Rink [Directions] | 7:40 p.m. | L 1-8 | |
| Tue., 1/29 | V Boys Basketball | Westhill | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | W 64-44 | |
| Tue., 1/29 | JV Boys Basketball | Westhill | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Tue., 1/29 | FR Boys Basketball | Westhill | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Tue., 1/29 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10pm-5:10pm | ||
| Tue., 1/29 | ALL Co-ed Squash | Practice | Home - Intensity [Directions] | 2:20pm | ||
| Tue., 1/29 | V Girls Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | W 44-42 | |
| Tue., 1/29 | JV Girls Basketball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | ||
| Tue., 1/29 | V Girls Ice Hockey | Darien | Home - Terry Conners Ice Rink [Directions] | 7:40 p.m. | L 1-8 | |
| Wed., 1/30 | ALL Co-ed Squash | Practice | Home - Intensity [Directions] | 2:20pm | ||
| Thu., 1/31 | V Boys Basketball | Stamford | Away - Kuzco Gymnasium at Stamford HS [Directions] | 7:00 p.m. | L 47-75 | |
| Thu., 1/31 | JV Boys Basketball | Stamford | Away - Kuzco Gymnasium at Stamford HS [Directions] | 5:15 p.m. | ||
| Thu., 1/31 | FR Boys Basketball | Stamford | Away - Kuzco Gymnasium at Stamford HS [Directions] | 4:00 p.m. | ||
| Thu., 1/31 | V Boys Indoor Track | FCIAC Championship | Away - Floyd Little AC | 4:30 p.m. | ||
| Thu., 1/31 | V Boys Swimming and Diving | Greenwich | Away - GHS Pool [Directions] | 4:30 p.m. | ||
| Thu., 1/31 | V Wrestling | Trumbull | Home - Staples Field House [Directions] | 5:00 p.m. | ||
| Thu., 1/31 | ALL Co-ed Squash | Practice | Home - Intensity [Directions] | 2:20pm | ||
| Thu., 1/31 | V Girls Basketball | Stamford | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | L 50-54 | |
| Thu., 1/31 | JV Girls Basketball | Stamford | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Thu., 1/31 | FR Girls Basketball | Stamford | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Thu., 1/31 | V Girls Gymnastics | Fairfield Warde, Fairfield Ludlowe | Away [Directions] | 6:30 p.m. | 124.05 | |
| Thu., 1/31 | V Girls Ice Hockey | Hall/Conard | Home - Terry Conners Ice Rink [Directions] | 7:40 p.m. | L 0-4 | |
| Thu., 1/31 | V Girls Indoor Track | FCIAC Championship | Away - Floyd Little AC | 5:30 p.m. | ||
| Fri., 2/1 | V Girls Squash | Nationals | Away | 4:00 p.m. | ||
| Sat., 2/2 | V Boys Indoor Track | FCIAC JV Tournament | Home [Directions] | 10:00 a.m. | ||
| Sat., 2/2 | JV Wrestling | Souther CT JV Wrestling Championships | Away | 9:30 a.m. | ||
| Sat., 2/2 | V Competitive Cheerleading | FCIAC Championship | Away | 9:00 a.m. | ||
| Sat., 2/2 | V Girls Gymnastics | Darien | Away [Directions] | 2:30 p.m. | 124.40 | |
| Mon., 2/4 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10pm-5:10pm | ||
| Mon., 2/4 | ALL Co-ed Squash | Practice | Home - Intensity [Directions] | 2:20pm | ||
| Mon., 2/4 | V Girls Ice Hockey | Branford | Home - Terry Conners Ice Rink [Directions] | 6:00 p.m. | L 3-4 | |
| Tue., 2/5 | V Boys Basketball | Ridgefield | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | L 57-60 | |
| Tue., 2/5 | JV Boys Basketball | Ridgefield | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/5 | FR Boys Basketball | Ridgefield | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Tue., 2/5 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10pm-5:10pm | ||
| Tue., 2/5 | V Wrestling | Ridgefield | Away - RHS Aux Gym [Directions] | 6:30 p.m. | ||
| Tue., 2/5 | V Co-ed Alpine Skiing | Race #4 | Away - Mt Southington | 4:00 p.m. | ED 1:30 | |
| Tue., 2/5 | ALL Co-ed Squash | Practice | Home - Intensity [Directions] | 2:20pm | ||
| Tue., 2/5 | V Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 7:00 p.m. | W 59-45 | |
| Tue., 2/5 | JV Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 5:15 p.m. | ||
| Tue., 2/5 | FR Girls Basketball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Wed., 2/6 | V Boys Ice Hockey | Masuk | Away - The Rinks at Shelton [Directions] | 4:15 p.m. | W 3-1 | ED 1:45 |
| Wed., 2/6 | V Boys Swimming and Diving | Westhill/Stamford | Home - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Wed., 2/6 | ALL Co-ed Squash | Practice | Home - Intensity [Directions] | 2:20pm | ||
| Wed., 2/6 | V Girls Gymnastics | Greenwich | Away - Greenwich YWCA [Directions] | 6:00 p.m. | 121.25 | |
| Wed., 2/6 | V Girls Ice Hockey | Greenwich | Home - Terry Conners Ice Rink [Directions] | 7:40 p.m. | L 0-5 | |
| Thu., 2/7 | V Boys Ice Hockey | Greenwich | Away - Dorothy Hamill Ice Rink [Directions] | 8:00 p.m. | L 0-6 | |
| Thu., 2/7 | V Co-ed Alpine Skiing | Race #5 | Away | 4:00 p.m. | ED 1:30 | |
| Thu., 2/7 | ALL Co-ed Squash | Practice | Home - Intensity [Directions] | 2:20pm | ||
| Fri., 2/8 | V Boys Basketball | Darien | Away - DHS Main Gym [Directions] | 7:00 p.m. | L 51-56 | |
| Fri., 2/8 | JV Boys Basketball | Darien | Away - DHS Main Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/8 | FR Boys Basketball | Darien | Away - DHS Main Gym [Directions] | 3:45 p.m. | ||
| Fri., 2/8 | V Wrestling | FCIAC Tournament | Away - New Canaan HS | 4:30 p.m. | ED 1:45 | |
| Fri., 2/8 | V Girls Basketball | Darien | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | W 50-38 | Senior Night |
| Fri., 2/8 | JV Girls Basketball | Darien | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Fri., 2/8 | FR Girls Basketball | Darien | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Fri., 2/8 | V Girls Ice Hockey | Wilton/Norwalk/McMahon | Away - So No Icehouse - Norwalk [Directions] | 8:50 p.m. | L 6-8 | |
| Sat., 2/9 | V Boys Indoor Track | CIAC Class LL Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:30 p.m. | ||
| Sat., 2/9 | V Wrestling | FCIAC Tournament | Away - New Canaan HS | TBA | ||
| Sat., 2/9 | V Competitive Cheerleading | Fairfield Warde | Away [Directions] | 9:00 a.m. | ||
| Sat., 2/9 | V Girls Gymnastics | FCIAC Championship | Away - Westhill | 10:00 a.m. | 122.65 | |
| Sat., 2/9 | V Girls Indoor Track | CIAC Class LL Championships | Away - Floyd Little Athletic Center-New Haven [Directions] | 4:30 p.m. | ||
| Sun., 2/10 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 10:00am-11:15am | ||
| Mon., 2/11 | V Boys Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 7:00 p.m. | L 26-57 | |
| Mon., 2/11 | JV Boys Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 5:15 p.m. | ||
| Mon., 2/11 | FR Boys Basketball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 2/11 | V Boys Ice Hockey | Westhill/Stamford | Home - Milford Ice Pavilion [Directions] | 6:30 p.m. | L 0-5 | |
| Mon., 2/11 | V Boys Swimming and Diving | Danbury | Away - O'Neil Center @ Western Connecticut State University [Directions] | 4:30 p.m. | ||
| Mon., 2/11 | V Co-ed Alpine Skiing | Practice | Home - Mt Southington [Directions] | 4:00pm | ||
| Mon., 2/11 | ALL Co-ed Squash | Practice | Home - Intensity [Directions] | 2:20pm | ||
| Mon., 2/11 | V Girls Basketball | Fairfield Ludlowe | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | W 48-42 | |
| Mon., 2/11 | JV Girls Basketball | Fairfield Ludlowe | Home - Staples H.S. Gym [Directions] | 5:15 p.m. | ||
| Mon., 2/11 | FR Girls Basketball | Fairfield Ludlowe | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Mon., 2/11 | V Girls Gymnastics | New Milford | Away - New Milford HS [Directions] | 5:00 p.m. | 128.2 | |
| Mon., 2/11 | V Girls Ice Hockey | New Canaan | Away - Darien Ice Rink [Directions] | 7:10 p.m. | L 0-7 | |
| Tue., 2/12 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10pm-5:10pm | ||
| Tue., 2/12 | ALL Co-ed Squash | Practice | Home - Intensity [Directions] | 2:20pm | ||
| Wed., 2/13 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10pm-5:10pm | ||
| Wed., 2/13 | V Boys Swimming and Diving | Fairfield Ludlowe/Fairfield Wardee | Home - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Wed., 2/13 | V Co-ed Alpine Skiing | Race | Away - Mt Southington | 4:00 p.m. | ||
| Wed., 2/13 | ALL Co-ed Squash | Practice | Home - Intensity [Directions] | 2:20pm | ||
| Wed., 2/13 | V Girls Basketball | Bassick | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | L 51-54 | |
| Wed., 2/13 | JV Girls Basketball | Bassick | Home - Staples H.S. Gym [Directions] | Cancelled | Cancelled | |
| Wed., 2/13 | V Girls Gymnastics | JV Gymnastics | Away - Westhill HS | 5:30 p.m. | ||
| Thu., 2/14 | JV Boys Ice Hockey | Cheshire | Home - Milford Ice Pavilion [Directions] | 4:10 p.m. | ||
| Thu., 2/14 | ALL Co-ed Squash | Practice | Home - Intensity [Directions] | 2:20pm | ||
| Fri., 2/15 | V Wrestling | CIAC Class LL State Championship | Away - Trumbull HS | 5:00 p.m. | ||
| Fri., 2/15 | V Girls Ice Hockey | Northwest Catholic | Home - Terry Conners Ice Rink [Directions] | 7:30 p.m. | W 8-6 | |
| Sat., 2/16 | V Boys Ice Hockey | New Canaan | Home - Milford Ice Pavilion [Directions] | 8:00 p.m. | L 1-3 | |
| Sat., 2/16 | V Boys Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | ||
| Sat., 2/16 | V Wrestling | CIAC Class LL State Championship | Away - Trumbull HS | TBA | ||
| Sat., 2/16 | V Girls Basketball | Danbury | Away - Fairfield Ludlowe HS [Directions] | 5:00 p.m. | ||
| Sat., 2/16 | V Girls Indoor Track | CIAC Open Championship | Away - Floyd Little Athletic Center-New Haven [Directions] | 12:00 p.m. | ||
| Mon., 2/18 | V Boys Basketball | New Canaan | Home - Staples H.S. Gym [Directions] | 5:00 p.m. | L 55-62 | |
| Mon., 2/18 | JV Boys Basketball | New Canaan | Home - Staples H.S. Gym [Directions] | 3:15 p.m. | ||
| Mon., 2/18 | FR Boys Basketball | New Canaan | Home - Staples H.S. Gym [Directions] | 2:00 p.m. | ||
| Mon., 2/18 | V Boys Ice Hockey | North Branford | Home - Milford Ice Pavilion [Directions] | 6:00 p.m. | L 2-5 | |
| Mon., 2/18 | JV Wrestling | JV State's | Away - Simsbury HS | 10:00 a.m. | ||
| Tue., 2/19 | JV Boys Ice Hockey | Cheshire | Away - Wesleyan University Ice Rink [Directions] | 2:30 p.m. | ||
| Tue., 2/19 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10pm-5:10pm | ||
| Thu., 2/21 | V Boys Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 7:00 p.m. | W 69-66 | |
| Thu., 2/21 | JV Boys Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 5:15 p.m. | ||
| Thu., 2/21 | FR Boys Basketball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | ||
| Thu., 2/21 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10pm-5:10pm | ||
| Fri., 2/22 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10pm-5:10pm | ||
| Fri., 2/22 | V Wrestling | CIAC Class Open State Championship | Away - Hillhouse HS | 5:00 p.m. | ||
| Sat., 2/23 | V Boys Ice Hockey | Trumbull | Home - Milford Ice Pavilion [Directions] | 5:30 p.m. | W 2-1 | |
| Sat., 2/23 | V Wrestling | CIAC Class Open State Championship | Away - Hillhouse HS | TBA | ||
| Sat., 2/23 | V Competitive Cheerleading | Mercy High School Competition | Away | 9:00 a.m. | ||
| Sat., 2/23 | V Girls Gymnastics | State Championship | Away | 1:00 p.m. | ||
| Mon., 2/25 | V Boys Ice Hockey | Brien McMahon/Norwalk | Home - Milford Ice Pavilion [Directions] | 8:10 p.m. | W 4-2 | |
| Tue., 2/26 | V Boys Basketball | Brien McMahon (Scrim.) | Away [Directions] | 3:30 p.m. | ||
| Tue., 2/26 | V Boys Ice Hockey | Milford Coop | Away - Milford Ice Pavilion [Directions] | 6:00 p.m. | L 2-3 | |
| Tue., 2/26 | V Boys Swimming and Diving | FCIAC Boys Swimming Trials | Away - Greenwich HS | 5:30 p.m. | ||
| Tue., 2/26 | V Co-ed Alpine Skiing | Final Race | Away - Mt Southington | 4:00 p.m. | ||
| Tue., 2/26 | V Girls Basketball | Hall | Home - Staples H.S. Gym [Directions] | 7:00 p.m. | ||
| Wed., 2/27 | V Boys Swimming and Diving | FCIAC Boys Diving Trials | Away - Westhill HS | 5:00 p.m. | ||
| Thu., 2/28 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10pm-5:10pm | ||
| Thu., 2/28 | V Boys Swimming and Diving | FCIAC Boys Swimming Championship | Away - Greenwich HS | 6:30 p.m. | ||
| Fri., 3/1 | ALL Boys Ice Hockey | Practice | Home - Milford Ice Pavilion [Directions] | 4:10pm-5:10pm | ||
| Fri., 3/1 | V Wrestling | New England Championship | Away | TBA | ||
| Fri., 3/1 | V Girls Basketball | Norwalk | Away - Scarso Gymnasium [Directions] | 6:00 p.m. | ||
| Sat., 3/2 | V Boys Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | TBA | ||
| Sat., 3/2 | V Wrestling | New England Championship | Away | TBA | ||
| Sat., 3/2 | V Competitive Cheerleading | States | Away - Floyd Little Athletic Complex | TBA | ||
| Sat., 3/2 | V Girls Indoor Track | New England Championships | Away - Reggie Lewis Center - Boston, MA | TBA | ||
| Tue., 3/5 | V Boys Basketball | Hall | Away - Hall HS - Gym A [Directions] | 6:45 p.m. | ||
| Tue., 3/5 | V Boys Ice Hockey | Tri-Town | Away - Enfield Twin Rinks [Directions] | 2:40 p.m. | ED 10:45 | |
| Tue., 3/5 | V Co-ed Alpine Skiing | State race | Away - Mt Southington | TBA | ED 12:15 | |
| Thu., 3/7 | V Boys Swimming and Diving | CIAC Class LL Diving Trials/Finals | Away - Middletown HS [Directions] | 5:30 p.m. | ||
| Fri., 3/8 | V Boys Indoor Track | New Balance Indoor Nationals | Away - Armory NYC | TBA | ||
| Sat., 3/9 | V Boys Indoor Track | New Balance Indoor Nationals | Away - Armory NYC | TBA | ||
| Sat., 3/9 | V Boys Rugby | St. Anthonys (NY) (Scrim.) | Home - Staples Stadium [Directions] | 12:00 p.m. | ||
| Sat., 3/9 | V Boys Swimming and Diving | CIAC Class LL Qualifying | Away - East Hartford HS [Directions] | 6:00 p.m. | ||
| Sun., 3/10 | V Boys Indoor Track | New Balance Indoor Nationals | Away - Armory NYC | TBA | ||
| Mon., 3/11 | V Boys Swimming and Diving | CIAC Class LL Finals | Away - SCSU [Directions] | 1:30 p.m. | ||
| Tue., 3/12 | V Boys Swimming and Diving | CIAC Open Diving | Away - Bulkeley [Directions] | 5:30 p.m. | ||
| Thu., 3/14 | V Boys Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 7:00 p.m. | ||
| Fri., 3/15 | V Boys Rugby | Fairfield Warde | Away [Directions] | 6:00 p.m. | ||
| Sat., 3/16 | JV Boys Rugby | Fairfield Warde | Away - Tomlinson MS [Directions] | 10:00 a.m. | ||
| Sat., 3/16 | V Competitive Cheerleading | Regionals | Away - Worcester State Univ | TBA | ||
| Mon., 3/18 | ALL Boys Golf | Practice | Home - Golf performance Center [Directions] | 2:30 | ||
| Tue., 3/19 | ALL Boys Golf | Practice | Home - Fairchild Wheeler [Directions] | 2:30 | ||
| Wed., 3/20 | ALL Boys Golf | Practice | Home - Tashua Knolls [Directions] | 2:45 | ||
| Wed., 3/20 | V Co-ed Sailing | Meeting | Home - Pequot Yacht Club [Directions] | |||
| Thu., 3/21 | ALL Boys Golf | Practice | Home - Fairchild Wheeler [Directions] | 2:45 | ||
| Thu., 3/21 | V Boys Lacrosse | Iona Prep (NY) (Scrim.) | Away | 4:30 p.m. | ||
| Fri., 3/22 | ALL Boys Golf | Practice | Home - Fairchild Wheeler [Directions] | 2:45 | ||
| Fri., 3/22 | V Boys Rugby | Aspetuck | Away | 7:00 p.m. | 120 Meadow St., Shelton Ct. | |
| Fri., 3/22 | JV Boys Rugby | Aspetuck | Away | 8:30 p.m. | ||
| Fri., 3/22 | V Girls Water Polo | Greenwich | Away [Directions] | 4:30 p.m. | ||
| Sat., 3/23 | V Boys Lacrosse | Weston, Cheshire | Away - Weston | 10:00 a.m. | ||
| Sat., 3/23 | FR Boys Rugby | Aspetuck | Home - PJ Romano Field - Saugatuck Elem School [Directions] | 11:00 a.m. | ||
| Sat., 3/23 | V Girls Lacrosse | Staples Girls Lacrosse Play Day | Home - Ginny Parker Field - Staples [Directions] | 8:00 a.m. | 2-3 fields in use | |
| Sun., 3/24 | V Baseball | Oxford (Scrim.) | Home - Staples Baseball Field [Directions] | 12:30 p.m. | ||
| Sun., 3/24 | V Softball | Brien McMahon (Scrim.) | Home - Wakeman Field [Directions] | 3:00 p.m. | ||
| Mon., 3/25 | V Baseball | Trumbull (Scrim.) | Away - Varsity Baseball Field [Directions] | 3:30 p.m. | ||
| Mon., 3/25 | JV Baseball | Trumbull (Scrim.) | Home - Staples HS Baseball Field [Directions] | 3:30 p.m. | ||
| Mon., 3/25 | ALL Boys Golf | Practice | Home - Fairchild Wheeler [Directions] | 2:45 | ||
| Mon., 3/25 | V Boys Volleyball | Southington (Scrim.) | Away - West Gym [Directions] | 5:00 p.m. | ||
| Mon., 3/25 | V Co-ed Sailing | Sailor's Clinic | Away - Greenwich Academy | TBA | ||
| Tue., 3/26 | V Baseball | Fairfield Warde (Scrim.) | Away - Fairfield Warde H.S. [Directions] | 3:30 p.m. | ||
| Tue., 3/26 | ALL Boys Golf | Practice | Home - Fairchild Wheeler [Directions] | 2:45 | ||
| Tue., 3/26 | V Boys Lacrosse | New Canaan (Scrim.) | Away - Dunning Stadium [Directions] | 4:00 p.m. | ||
| Wed., 3/27 | V Baseball | Amity (Scrim.) | Away - John Janenda Baseball Field @ Amity HS [Directions] | 3:30 p.m. | ||
| Wed., 3/27 | ALL Boys Golf | Practice | Home - Fairchild Wheeler [Directions] | 2:45 | ||
| Wed., 3/27 | V Co-ed Sailing | Darien | Away - Rowayton Yacht Club [Directions] | TBA | ||
| Wed., 3/27 | V Girls Water Polo | Sacred Heart Academy | Home - Staples HS Pool [Directions] | 4:30 p.m. | ||
| Thu., 3/28 | V Baseball | Fairfield Prep (Scrim.) | Home - Staples HS Baseball Field [Directions] | 3:30 p.m. | ||
| Thu., 3/28 | ALL Boys Golf | Practice | Home - Fairchild Wheeler [Directions] | 2:45 | ||
| Thu., 3/28 | V Girls Lacrosse | Weston (Scrim.) | Home - Ginny Parker Field - Staples [Directions] | 5:00 p.m. | ||
| Thu., 3/28 | JV Girls Lacrosse | Weston (Scrim.) | Home - Ginny Parker Field - Staples [Directions] | 3:45 p.m. | ||
| Thu., 3/28 | V Softball | Westhill (Scrim.) | Home - Wakeman Field [Directions] | 4:00 p.m. | ||
| Fri., 3/29 | ALL Boys Golf | Practice | Home - Fairchild Wheeler [Directions] | 2:45 | ||
| Fri., 3/29 | JV Boys Rugby | Southington | Away [Directions] | 5:00 p.m. | ||
| Fri., 3/29 | V Boys Tennis | Brunswick School (Scrim.) | Home - Staples HS-Tennis Courts [Directions] | 3:30 p.m. | ||
| Fri., 3/29 | V Wrestling | Nationals | Away - Virginia Beach, VA | TBA | ||
| Sat., 3/30 | V Boys Lacrosse | Germantown Academy (PA) | Home - Staples Stadium [Directions] | 11:00 a.m. | W 7-6(OT) | |
| Sat., 3/30 | FR Boys Lacrosse | Fairfield Prep (Scrim.) | Away - Tomlinson MS, Fairfield, CT [Directions] | 11:15 a.m. | ||
| Sat., 3/30 | FR Boys Lacrosse | Fairfield Ludlowe (Scrim.) | Away - Tomlinson MS [Directions] | 9:30 a.m. | ||
| Sat., 3/30 | V Boys Rugby | Bishop Hendricken | Home - Staples Stadium [Directions] | 1:00 p.m. | ||
| Sat., 3/30 | JV Boys Rugby | Bishop Hendricken | Home - Staples Stadium [Directions] | 2:30 p.m. | SOPHOMORE GAME | |
| Sat., 3/30 | V Wrestling | Nationals | Away | TBA | ||
| Sat., 3/30 | V Girls Lacrosse | Rye (NY) | Away | 12:45 p.m. | W 15-14 | |
| Sat., 3/30 | JV Girls Lacrosse | Rye (NY) (Scrim.) | Away | 11:00 a.m. | ||
| Sat., 3/30 | V Softball | Ridgefield | Home - Wakeman Field [Directions] | 12:00 p.m. | W 10-9 | |
| Sun., 3/31 | V Wrestling | Nationals | Away | TBA | ||
| Mon., 4/1 | V Baseball | Hall | Away - Hall HS Varsity Baseball Field [Directions] | 4:00 p.m. | W 15-1 (6) | |
| Mon., 4/1 | V Boys Lacrosse | Brien McMahon | Away - Brien McMahon HS [Directions] | 7:00 p.m. | W 13-3 | |
| Mon., 4/1 | JV Boys Lacrosse | Brien McMahon | Away [Directions] | Cancelled | Cancelled | |
| Mon., 4/1 | V Boys Tennis | Fairfield Warde | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Mon., 4/1 | JV Boys Tennis | Fairfield Warde | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 4/1 | V Boys Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 5:30 p.m. | W 3-1 | |
| Mon., 4/1 | JV Boys Volleyball | Ridgefield | Away - RHS Main Gym [Directions] | 4:00 p.m. | ||
| Mon., 4/1 | V Softball | Masuk | Away - Masuk HS Softball Field [Directions] | 4:15 p.m. | L 0-14 | |
| Mon., 4/1 | V Girls Tennis | Fairfield Warde | Away - FWHS Blake Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 4/2 | FR Boys Lacrosse | Trumbull | Home - Wakeman Field E (grass) [Directions] | 4:00 p.m. | W 15-4 | |
| Tue., 4/2 | JV Boys Rugby | Ridgefield | Home - Staples Stadium [Directions] | 5:30 p.m. | ||
| Tue., 4/2 | V Boys Tennis | Danbury | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 4/2 | V Girls Lacrosse | Greenwich | Away - Cardinal Stadium [Directions] | 4:30 p.m. | W 16-10 | |
| Tue., 4/2 | JV Girls Lacrosse | Greenwich | Away - Cardinal Stadium [Directions] | 5:30 p.m. | ||
| Tue., 4/2 | FR Girls Lacrosse | Trumbull | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | ||
| Tue., 4/2 | V Girls Tennis | Danbury | Away - WCSU Tennis Courts, Westside Campus [Directions] | 4:00 p.m. | W 7-0 | ED 1:45 |
| Tue., 4/2 | JV Girls Tennis | Fairfield Warde | Away - Fairfield Woods MS [Directions] | 4:00 p.m. | ||
| Wed., 4/3 | V Boys Lacrosse | Stamford | Home - Staples Stadium [Directions] | 5:30 p.m. | W 17-1 | |
| Wed., 4/3 | JV Boys Lacrosse | Stamford | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | W 12-1 | |
| Wed., 4/3 | JV Boys Rugby | Harvey | Home - PJ Romano Field - Saugatuck Elem School [Directions] | Cancelled | Cancelled | SOPHOMORE GAME |
| Wed., 4/3 | V Boys Volleyball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 4:00 p.m. | W 3-1 | |
| Wed., 4/3 | JV Boys Volleyball | Westhill | Away - Westhill - Main Gymnasium [Directions] | 5:30 p.m. | ||
| Wed., 4/3 | V Co-ed Sailing | Stamford Yacht CLub | Away | TBA | ||
| Wed., 4/3 | V Girls Water Polo | Sacred Heart | Home - Staples HS Pool [Directions] | Cancelled | Cancelled | |
| Thu., 4/4 | V Baseball | New Milford | Home - Staples HS Baseball Field [Directions] | 4:00 p.m. | W 11-1 (5) | |
| Thu., 4/4 | FR Baseball | Masuk | Away - Wolfe Park [Directions] | 3:45 p.m. | W 12-0 | |
| Thu., 4/4 | V Boys Tennis | Trinity Catholic | Away | 4:00 p.m. | W 7-0 | |
| Thu., 4/4 | V Girls Tennis | Trinity Catholic | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Fri., 4/5 | V Boys Lacrosse | Glastonbury | Home - Staples Stadium [Directions] | 7:00 p.m. | L 6-8 | |
| Fri., 4/5 | JV Boys Lacrosse | Glastonbury | Home - Wakeman Field B (turf) [Directions] | 4:30 p.m. | W 12-5 | |
| Fri., 4/5 | FR Boys Lacrosse | Greenwich | Home - Wakeman Field E (grass) [Directions] | 4:30 p.m. | W 8-7 | |
| Fri., 4/5 | V Boys Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 4/5 | JV Boys Volleyball | Greenwich | Away - GHS Gymnasium [Directions] | 4:00 p.m. | ||
| Fri., 4/5 | FR Girls Lacrosse | Greenwich | Away - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | Ride with B Vball, separate returns | |
| Sat., 4/6 | V Baseball | Xavier | Away - Pat Kidney Field, Farm Hill Rd, Middletown [Directions] | 1:00 p.m. | L 2-3 | |
| Sat., 4/6 | FR Baseball | Xavier | Away - Xavier H.S. Magner Field [Directions] | 1:00 p.m. | L 9-7 | |
| Sat., 4/6 | V Boys Rugby | Armoskeag | Home - Staples Stadium [Directions] | 12:30 p.m. | ||
| Sat., 4/6 | JV Boys Rugby | Armoskeag | Home - Staples Stadium [Directions] | 2:30 p.m. | SOPHOMORE GAME | |
| Sat., 4/6 | FR Boys Rugby | Fordham Prep (NY) | Home - Staples Stadium [Directions] | Cancelled | Cancelled | |
| Sat., 4/6 | V Girls Lacrosse | Fairfield Warde | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | W 15-7 | |
| Sat., 4/6 | JV Girls Lacrosse | Fairfield Warde | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | ||
| Sat., 4/6 | V Girls Water Polo | Choate Rosemary Hall, Sacred Heart | Away | 1:00 p.m. | ||
| Sun., 4/7 | JV Baseball | Xavier | Away - Xavier H.S. [Directions] | 3:00 p.m. | ||
| Mon., 4/8 | FR Baseball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 4:00 p.m. | L 9-6 | |
| Mon., 4/8 | JV Boys Golf | Darien | Home - Longshore [Directions] | 3:00 p.m. | ||
| Mon., 4/8 | JV Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde Grass Utility Field [Directions] | 4:00 p.m. | W 13-2 | |
| Mon., 4/8 | JV Boys Rugby | Midstate | Away - 522 high hill road, meriden CT | 5:00 p.m. | ||
| Mon., 4/8 | V Boys Tennis | Wilton | Away - Wilton Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Mon., 4/8 | JV Boys Tennis | Wilton | Away - Middlebrook School [Directions] | 4:00 p.m. | ||
| Mon., 4/8 | V Boys Volleyball | Stamford | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 4/8 | JV Boys Volleyball | Stamford | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Mon., 4/8 | V Girls Outdoor Track | Ridgefield, Trumbull | Away - Tiger Hollow Stadium [Directions] | 4:00 p.m. | 2 buses, ED 1:45 | |
| Mon., 4/8 | V Girls Tennis | Wilton | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Tue., 4/9 | JV Boys Golf | Fairfield Ludlowe | Home - Longshore [Directions] | 3:30 p.m. | ||
| Tue., 4/9 | V Boys Lacrosse | Fairfield Warde | Away - Tetreau/Davis Field [Directions] | 6:00 p.m. | W 13-5 | |
| Tue., 4/9 | FR Boys Lacrosse | Ridgefield | Home - Wakeman Field E (grass) [Directions] | Cancelled | Cancelled | |
| Tue., 4/9 | V Boys Outdoor Track | Trumbull, Ridgefield | Away - McDougall Stadium [Directions] | 4:00 p.m. | 2 buses | |
| Tue., 4/9 | V Co-ed Sailing | Noroton Yacht Club & Stamford yacht Club | Away | TBA | ||
| Tue., 4/9 | V Girls Lacrosse | Danbury | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | W 20-3 | |
| Tue., 4/9 | JV Girls Lacrosse | Danbury | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | ||
| Tue., 4/9 | FR Girls Lacrosse | Ridgefield | Away - Scotts Ridge MS Turf [Directions] | 4:00 p.m. | ||
| Tue., 4/9 | V Softball | Fairfield Warde | Away - Fairfield Warde H.S. [Directions] | 3:30 p.m. | L 4-13 | |
| Tue., 4/9 | JV Softball | Fairfield Warde | Away - Melville Park [Directions] | 3:30 p.m. | ||
| Wed., 4/10 | V Baseball | Danbury | Home - Staples HS Baseball Field [Directions] | 4:00 p.m. | W 6-4 | |
| Wed., 4/10 | JV Baseball | Danbury | Home - Wakeman Field [Directions] | 4:00 p.m. | ||
| Wed., 4/10 | FR Baseball | Danbury | Away - Danbury HS Varsity Baseball Field [Directions] | 4:00 p.m. | W 7-6 | |
| Wed., 4/10 | V Boys Tennis | Trumbull | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Wed., 4/10 | V Boys Volleyball | Fairfield Warde | Home - Staples H.S. Gym [Directions] | 4:30 p.m. | W 3-0 | |
| Wed., 4/10 | JV Boys Volleyball | Fairfield Warde | Home - Staples H.S. Gym [Directions] | 6:00 p.m. | ||
| Wed., 4/10 | V Co-ed Sailing | Regatta | Away - Grass Island | TBA | ||
| Wed., 4/10 | V Softball | Danbury | Away - Danbury HS Varsity Softball Field [Directions] | 4:00 p.m. | W 15-4 | ED 1:45 |
| Wed., 4/10 | JV Softball | Danbury | Away - Danbury HS Junior Varsity Softball Field [Directions] | 4:00 p.m. | ||
| Wed., 4/10 | V Girls Tennis | Trumbull | Away - THS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Wed., 4/10 | JV Girls Tennis | New Canaan | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/10 | V Girls Water Polo | Sacred Heart Academy | Home - Staples HS Pool [Directions] | 4:30 p.m. | ||
| Thu., 4/11 | V Baseball | Fairfield Warde | Home - Staples HS Baseball Field [Directions] | 4:00 p.m. | W 14-8 | |
| Thu., 4/11 | JV Baseball | Fairfield Warde | Home - Wakeman Field [Directions] | 4:00 p.m. | ||
| Thu., 4/11 | V Boys Golf | Fairfield Warde | Home - Longshore [Directions] | 3:00 p.m. | SHS 159 Warde 167 | |
| Thu., 4/11 | V Boys Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 6:30 p.m. | W 16-4 | |
| Thu., 4/11 | JV Boys Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 4:30 p.m. | W 12-0 | |
| Thu., 4/11 | JV Boys Rugby | Xavier | Home - Staples Stadium [Directions] | 5:30 p.m. | ||
| Thu., 4/11 | V Boys Tennis | Bridgeport Central | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Thu., 4/11 | V Girls Lacrosse | Daniel Hand | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | W 14-1 | |
| Thu., 4/11 | JV Girls Lacrosse | Daniel Hand | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | ||
| Thu., 4/11 | V Girls Tennis | Bridgeport Central | Away [Directions] | 4:00 p.m. | W 7-0 | |
| Fri., 4/12 | V Baseball | Trinity Catholic | Away - Trinity Catholic's Lione Field | 4:15 p.m. | W 13-0 (5) | |
| Fri., 4/12 | V Boys Golf | Trinity Catholic | Away | 3:15 p.m. | SHS 158 trinity 239 | ED 1:45 |
| Fri., 4/12 | FR Boys Lacrosse | Darien | Away - DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | L 1-11 | |
| Fri., 4/12 | JV Boys Rugby | West Hartford | Home - Staples Stadium [Directions] | 5:30 p.m. | ||
| Fri., 4/12 | V Boys Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 4/12 | JV Boys Volleyball | Fairfield Ludlowe | Away - FLHS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 4/12 | V Softball | Trinity Catholic | Home - Wakeman Field [Directions] | 4:00 p.m. | W 15-0 [Detailed Results] | |
| Fri., 4/12 | JV Softball | Trinity Catholic | Home - Staples HS - Softball Field [Directions] | Cancelled | Cancelled | |
| Fri., 4/12 | V Girls Water Polo | Loomis Chaffee School | Away | 4:30 p.m. | ||
| Sat., 4/13 | V Boys Lacrosse | Rye (NY) | Home - Staples Stadium [Directions] | 3:00 p.m. | W 12-2 | Hall of Fame Day |
| Sat., 4/13 | JV Boys Rugby | Xavier | Home - Staples Stadium [Directions] | 12:30 p.m. | SOPHOMORE GAME | |
| Sat., 4/13 | V Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS [Directions] | 1:00 p.m. | W 16-4 | |
| Sat., 4/13 | JV Girls Lacrosse | Brien McMahon | Away - Brien McMahon HS [Directions] | 3:00 p.m. | ||
| Sat., 4/13 | V Girls Outdoor Track | Bullis Bulldog Invitational | Away | TBA | ||
| Mon., 4/15 | FR Boys Lacrosse | Brien McMahon | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | W 11-1 | |
| Mon., 4/15 | JV Softball | Wilton | Home - Staples HS - Softball Field [Directions] | Cancelled | Cancelled | |
| Tue., 4/16 | V Baseball | Wilton | Away - WHS Varsity Baseball Field [Directions] | 4:00 p.m. | W 16-2 (5) | |
| Tue., 4/16 | JV Baseball | Wilton | Away - Allen's Meadow - Fr. Baseball Field [Directions] | 4:00 p.m. | ||
| Tue., 4/16 | FR Baseball | Wilton | Home - Staples HS Baseball Field [Directions] | 4:00 p.m. | W 13-9 | |
| Tue., 4/16 | ALL Boys Golf | Practice | Home - Fairchild Wheeler [Directions] | 2:00 | ||
| Tue., 4/16 | V Boys Lacrosse | Greenwich | Away - Cardinal Stadium [Directions] | 1:00 p.m. | W 10-7 | |
| Tue., 4/16 | JV Boys Lacrosse | Greenwich | Away - GHS Field 7 [Directions] | 1:00 p.m. | W 3-2 | |
| Tue., 4/16 | V Boys Tennis | Norwalk | Away - Norwalk HS [Directions] | 10:00 a.m. | W 6-1 | |
| Tue., 4/16 | V Girls Lacrosse | Westhill | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | W 17-7 | |
| Tue., 4/16 | JV Girls Lacrosse | Westhill | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | ||
| Tue., 4/16 | V Softball | Wilton | Home - Wakeman Field [Directions] | 4:00 p.m. | W 20-8 | |
| Tue., 4/16 | V Girls Tennis | Norwalk | Home - Staples HS-Tennis Courts [Directions] | 10:00 a.m. | W 7-0 | |
| Wed., 4/17 | V Baseball | Trumbull | Home - Staples HS Baseball Field [Directions] | 12:00 p.m. | W 1-0 | |
| Wed., 4/17 | JV Baseball | Trumbull | Home - Wakeman Field [Directions] | 12:00 p.m. | ||
| Wed., 4/17 | FR Baseball | Trumbull | Away - JV Baseball Field [Directions] | 2:00 p.m. | L 3-1 | |
| Wed., 4/17 | FR Boys Lacrosse | Wilton | Away - Allen's Field [Directions] | 4:00 p.m. | W 13-6 | |
| Wed., 4/17 | V Softball | Trumbull | Away - Varsity Softball Field [Directions] | 4:15 p.m. | L 0-8 | 83 pax bus |
| Wed., 4/17 | JV Softball | Trumbull | Away - JV Softball Field [Directions] | 4:00 p.m. | ||
| Thu., 4/18 | V Boys Lacrosse | Trumbull | Away - McDougall Stadium [Directions] | 6:00 p.m. | W 12-3 | |
| Thu., 4/18 | JV Boys Lacrosse | Trumbull | Away - McDougall Stadium [Directions] | 4:00 p.m. | W 14-4 | |
| Thu., 4/18 | V Boys Volleyball | Oxford | Away - OHS-Main Gym [Directions] | 5:15 p.m. | W 3-0 | |
| Thu., 4/18 | JV Boys Volleyball | Oxford | Away - OHS-Main Gym [Directions] | 4:30 p.m. | ||
| Thu., 4/18 | V Girls Lacrosse | Cheshire | Home - Ginny Parker Field - Staples [Directions] | 4:30 p.m. | L 15-16 | |
| Thu., 4/18 | JV Girls Lacrosse | Cheshire | Home - Ginny Parker Field - Staples [Directions] | 6:00 p.m. | ||
| Thu., 4/18 | V Softball | Bridgeport Central | Away - Ripken Turf Field [Directions] | 4:00 p.m. | W 14-2 | 83 pax bus |
| Sat., 4/20 | V Boys Outdoor Track | Hillhouse Invitational | Away - Hillhouse HS | 10:00 a.m. | ||
| Mon., 4/22 | V Boys Golf | Westhill | Home - Longshore [Directions] | 3:00 p.m. | SHS 154 WESTHILL 178 | |
| Mon., 4/22 | FR Boys Lacrosse | New Canaan | Away - NCHS Water Tower Turf Field [Directions] | 4:00 p.m. | L 9-8 | |
| Mon., 4/22 | JV Boys Rugby | Fordham Prep (NY) | Away | TBA | ED 2:00 SOPHOMORE | |
| Mon., 4/22 | FR Boys Rugby | Fairfield Warde | Home - Staples Stadium [Directions] | 4:30 p.m. | ||
| Mon., 4/22 | V Boys Volleyball | Ridgefield | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 4/22 | JV Boys Volleyball | Ridgefield | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Mon., 4/22 | V Girls Golf | Darien | Away - Wee Burn CC [Directions] | 3:00 p.m. | S 197 D 210 | ED 1:45 |
| Mon., 4/22 | JV Girls Golf | Darien | Away - Wee Burn CC [Directions] | 3:00 p.m. | ED 2:00 | |
| Mon., 4/22 | FR Girls Lacrosse | New Canaan | Home - Ginny Parker Field - Staples [Directions] | 5:00 p.m. | ||
| Tue., 4/23 | V Baseball | Greenwich | Away - Julian Curtiss School [Directions] | 4:30 p.m. | W 7-5 | |
| Tue., 4/23 | JV Baseball | Greenwich | Away - Havemeyer Field [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | FR Baseball | Greenwich | Home - Staples HS Baseball Field [Directions] | 4:00 p.m. | L 8-7 | |
| Tue., 4/23 | V Boys Lacrosse | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 6:30 p.m. | L 4-5 | |
| Tue., 4/23 | JV Boys Lacrosse | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 4:30 p.m. | W 6-3 | |
| Tue., 4/23 | V Boys Outdoor Track | Stamford, Bridgeport Central | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | V Boys Tennis | Westhill | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 4/23 | JV Boys Tennis | Greenwich | Away - Central MS [Directions] | 4:30 p.m. | ||
| Tue., 4/23 | V Girls Golf | Fairfield Warde | Home - Longshore [Directions] | 3:00 p.m. | S 188, FW 193 | |
| Tue., 4/23 | JV Girls Golf | Fairfield Warde | Home - Longshore [Directions] | 3:15 p.m. | ||
| Tue., 4/23 | V Girls Outdoor Track | Stamford, Bridgeport Central | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | V Softball | Greenwich | Home - Wakeman Field [Directions] | 4:00 p.m. | W 12-11 | |
| Tue., 4/23 | JV Softball | Greenwich | Home - Staples HS - Softball Field [Directions] | 4:00 p.m. | ||
| Tue., 4/23 | V Girls Tennis | Westhill | Away [Directions] | 4:00 p.m. | W 6-1 | |
| Tue., 4/23 | JV Girls Tennis | Greenwich | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | V Baseball | Norwalk | Away - Callahan Complex at Nathan Hale Upper [Directions] | 4:00 p.m. | W 13-1 | |
| Wed., 4/24 | JV Baseball | Norwalk | Away - City Hall Field [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | FR Baseball | Norwalk | Home - Staples HS Baseball Field [Directions] | 4:00 p.m. | W 19-3 | |
| Wed., 4/24 | V Boys Golf | Stamford | Away - EG Brennan [Directions] | 3:00 p.m. | SHS 169 Stamford 200 | ED 1:45 small bus |
| Wed., 4/24 | FR Boys Lacrosse | Greenwich | Away - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | W 5-4 | |
| Wed., 4/24 | V Boys Tennis | Greenwich | Away - GHS Tennis Courts [Directions] | 4:30 p.m. | L 3-4 | |
| Wed., 4/24 | V Boys Volleyball | Westhill | Home - Staples H.S. Gym [Directions] | 4:30 p.m. | W 3-1 | |
| Wed., 4/24 | JV Boys Volleyball | Westhill | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Wed., 4/24 | V Co-ed Sailing | Regatta | Away - Indian Harbor | TBA | ||
| Wed., 4/24 | V Softball | Norwalk | Home - Wakeman Field [Directions] | 4:00 p.m. | L 3-16 | |
| Wed., 4/24 | JV Softball | Norwalk | Home - Staples HS - Softball Field [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | V Girls Tennis | Greenwich | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Wed., 4/24 | JV Girls Tennis | Wilton | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 4/24 | V Girls Water Polo | Suffield, Loomis Chaffee | Home - Staples HS Pool [Directions] | 3:30 p.m. | ||
| Thu., 4/25 | JV Baseball | Brien McMahon | Home - Wakeman Field [Directions] | 4:00 p.m. | ||
| Thu., 4/25 | V Boys Golf | Norwalk | Away - Oak Hills G.C. [Directions] | 3:15 p.m. | SHS 157 NORWALK 203 | |
| Thu., 4/25 | V Boys Lacrosse | Cold Spring Harbor (NY) | Home - Staples Stadium [Directions] | 5:30 p.m. | W 7-6 | |
| Thu., 4/25 | JV Boys Lacrosse | Rye (NY) | Home - Wakeman Field B (turf) [Directions] | 4:30 p.m. | W 4-2 | |
| Thu., 4/25 | V Boys Tennis | Stamford | Away [Directions] | 4:00 p.m. | W 7-0 | |
| Thu., 4/25 | V Girls Golf | Trumbull | Home - Longshore [Directions] | 3:00 p.m. | S 186, Trumbull 217 | |
| Thu., 4/25 | V Girls Lacrosse | Ridgefield | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | W 14-12 | |
| Thu., 4/25 | JV Girls Lacrosse | Ridgefield | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | ||
| Thu., 4/25 | V Girls Tennis | Stamford | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Fri., 4/26 | FR Boys Lacrosse | Darien | Home - Wakeman Field B (turf) [Directions] | 4:00 p.m. | L 7-8 OT | |
| Fri., 4/26 | V Boys Outdoor Track | Dan O'Grady Relays | Away - Bethel HS | Cancelled | Cancelled | |
| Fri., 4/26 | V Boys Volleyball | Trumbull | Away - THS Main Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 4/26 | JV Boys Volleyball | Trumbull | Away - THS Main Gym [Directions] | 5:30 p.m. | ||
| Fri., 4/26 | V Girls Outdoor Track | O'Grady Relays | Away - Danbury HS | Cancelled | Cancelled | |
| Sat., 4/27 | V Baseball | Brien McMahon | Home - Staples HS Baseball Field [Directions] | 2:00 p.m. | W 7-6 | |
| Sat., 4/27 | FR Baseball | Brien McMahon | Away - Pride Field (BMHS) [Directions] | 10:00 a.m. | W 11-1 | |
| Sat., 4/27 | V Boys Lacrosse | Wilton | Home - Staples Stadium [Directions] | 5:30 p.m. | L 6-7(2OT) | Youth Day |
| Sat., 4/27 | JV Boys Lacrosse | Wilton | Home - Staples Stadium [Directions] | 3:00 p.m. | L 4-9 | |
| Sat., 4/27 | V Boys Outdoor Track | Dan O'Grady Relays | Away | 9:00 a.m. | ||
| Sat., 4/27 | V Girls Lacrosse | Joel Barlow | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | W 17-5 | Senior Day Double Header with Boys Lacrosse |
| Sat., 4/27 | JV Girls Lacrosse | Joel Barlow | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | ||
| Sat., 4/27 | FR Girls Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 10:00 a.m. | ||
| Sat., 4/27 | V Girls Outdoor Track | O'Grady Relays | Away - Danbury HS | TBA | ||
| Sat., 4/27 | V Girls Water Polo | Suffield, Williston | Away | 3:00 p.m. | ||
| Mon., 4/29 | V Baseball | Westhill | Home - Staples HS Baseball Field [Directions] | 4:00 p.m. | L 7-2 | |
| Mon., 4/29 | JV Baseball | Westhill | Home - Wakeman Field [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | FR Baseball | Westhill | Away - Westhill Baseball Field [Directions] | 4:00 p.m. | L 8-2 | |
| Mon., 4/29 | V Boys Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 3:15 p.m. | shs 173 ludlowe 173 | |
| Mon., 4/29 | JV Boys Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 3:15 p.m. | ||
| Mon., 4/29 | JV Boys Rugby | Darien | Home - Staples Stadium [Directions] | 5:30 p.m. | ||
| Mon., 4/29 | V Boys Tennis | Ridgefield | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 4-3 | |
| Mon., 4/29 | JV Boys Tennis | Ridgefield | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | V Boys Volleyball | New Canaan | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 4/29 | JV Boys Volleyball | New Canaan | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Mon., 4/29 | V Girls Golf | Wilton | Away - Silver Mine CC [Directions] | 3:15 p.m. | S 177, W 207 | ED 1:50pm |
| Mon., 4/29 | FR Girls Lacrosse | Wilton | Home - Ginny Parker Field - Staples [Directions] | 5:00 p.m. | ||
| Mon., 4/29 | V Girls Outdoor Track | Danbury, Westhill | Home - Staples HS [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | V Softball | Westhill | Away - Westhill Softball Field [Directions] | 4:00 p.m. | W 13-6 | 83 pax bus |
| Mon., 4/29 | JV Softball | Westhill | Away - Roxbury Elementary School [Directions] | 4:00 p.m. | ||
| Mon., 4/29 | V Girls Tennis | Ridgefield | Away - RHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | ED 1:45 |
| Tue., 4/30 | V Boys Golf | Wilton | Away - Rolling Hills CC [Directions] | 3:15 p.m. | shs 165 wilton 176 | ED 2:05 |
| Tue., 4/30 | JV Boys Golf | Wilton | Away - Rolling Hills CC [Directions] | 3:15 p.m. | ||
| Tue., 4/30 | V Boys Outdoor Track | Danbury, Westhill | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 4/30 | V Boys Tennis | Darien | Away - DHS Tennis Courts [Directions] | 4:00 p.m. | W 4-3 | |
| Tue., 4/30 | JV Boys Tennis | Darien | Away - Cherry Lawn Park [Directions] | 4:00 p.m. | ||
| Tue., 4/30 | V Girls Tennis | Darien | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 4-3 | |
| Tue., 4/30 | JV Girls Tennis | Darien | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | V Baseball | Stamford | Away - SHS Baseball Field [Directions] | 4:00 p.m. | W 11-1 (5) | |
| Wed., 5/1 | JV Baseball | Stamford | Away - Belltown Field [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | FR Baseball | Stamford | Home - Staples HS Baseball Field [Directions] | 4:00 p.m. | W 5-0 | |
| Wed., 5/1 | V Boys Golf | Ridgefield | Home - Longshore [Directions] | 3:00 p.m. | shs 149 Ridgefield 156 | |
| Wed., 5/1 | JV Boys Golf | Ridgefield | Home - Longshore [Directions] | 3:00 p.m. | ||
| Wed., 5/1 | V Boys Tennis | Brien McMahon | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Wed., 5/1 | V Boys Volleyball | Darien | Away - DHS Main Gym [Directions] | 4:00 p.m. | L 3-0 | |
| Wed., 5/1 | JV Boys Volleyball | Darien | Away - DHS Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 5/1 | V Co-ed Sailing | Regatta | Away - Indian Harbor | TBA | ||
| Wed., 5/1 | V Girls Golf | Fairfield Ludlowe | Away - Smith Richardson Golf Course [Directions] | 3:30 p.m. | S 190, FL 200 | |
| Wed., 5/1 | FR Girls Lacrosse | Trumbull | Home - Ginny Parker Field - Staples [Directions] | 5:00 p.m. | ||
| Wed., 5/1 | V Girls Outdoor Track | St. Joseph | Home - Staples Stadium [Directions] | Cancelled | Cancelled | |
| Wed., 5/1 | V Softball | Stamford | Home - Wakeman Field [Directions] | 4:00 p.m. | L 2-6 | |
| Wed., 5/1 | JV Softball | Stamford | Home - Staples HS - Softball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/1 | V Girls Tennis | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | W 7-0 | |
| Thu., 5/2 | FR Baseball | Ridgefield | Away - East Ridge MS [Directions] | 4:00 p.m. | L 5-4 | |
| Thu., 5/2 | JV Boys Golf | Wilton | Home - Longshore [Directions] | 3:30 p.m. | ||
| Thu., 5/2 | JV Boys Lacrosse | Darien | Away - DHS Upper Oval Turf Field [Directions] | 4:30 p.m. | L 5-9 | |
| Thu., 5/2 | V Boys Tennis | Fairfield Ludlowe | Away - Fairfield Ludlowe Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Thu., 5/2 | JV Boys Tennis | Fairfield Ludlowe | Away - Tomlinson MS Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/2 | V Girls Golf | New Canaan | Home - Longshore [Directions] | 3:00 p.m. | S 191, NC 177 | |
| Thu., 5/2 | JV Girls Golf | Fairfield Ludlowe | Away - South Pine Creek Par 3 [Directions] | 3:15 p.m. | ||
| Thu., 5/2 | V Girls Tennis | Fairfield Ludlowe | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 6-1 | |
| Thu., 5/2 | JV Girls Tennis | Fairfield Ludlowe | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 5/3 | V Baseball | Ridgefield | Home - Staples HS Baseball Field [Directions] | 4:00 p.m. | W 2-0 | Little League Day |
| Fri., 5/3 | JV Baseball | Ridgefield | Home - Wakeman Field [Directions] | 4:00 p.m. | ||
| Fri., 5/3 | FR Boys Lacrosse | Fairfield Ludlowe | Away - Tomlinson MS [Directions] | Cancelled | Cancelled | |
| Fri., 5/3 | V Boys Outdoor Track | Middletown Invitational (FR & SO) | Away - Middletown HS | Cancelled | Cancelled | ED 12:30 |
| Fri., 5/3 | V Boys Rugby | Simsbury | Away [Directions] | 5:45 p.m. | ||
| Fri., 5/3 | JV Boys Rugby | Simsbury | Away [Directions] | 7:05 p.m. | ||
| Fri., 5/3 | V Boys Volleyball | Danbury | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 5/3 | JV Boys Volleyball | Danbury | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Fri., 5/3 | V Girls Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 6:00 p.m. | W 20-4 | |
| Fri., 5/3 | JV Girls Lacrosse | Norwalk | Away - Testa Field, NHS [Directions] | 4:30 p.m. | ||
| Fri., 5/3 | V Girls Outdoor Track | FR/SO Middletown Tournament | Away - Middletown HS | Cancelled | Cancelled | ED 12:30 |
| Sat., 5/4 | V Boys Lacrosse | Fairfield Ludlowe | Home - Staples Stadium [Directions] | 5:00 p.m. | W 12-6 | Sticks for Soldiers |
| Sat., 5/4 | JV Boys Lacrosse | Fairfield Ludlowe | Home - Staples Stadium [Directions] | Cancelled | Cancelled | |
| Sat., 5/4 | V Boys Outdoor Track | Middletown Invitational (Varsity) | Away | 1:00 p.m. | ||
| Sat., 5/4 | JV Boys Rugby | Simsbury | Away [Directions] | 11:30 a.m. | SOPHOMORE GAME | |
| Sat., 5/4 | FR Boys Rugby | Xavier | Home - Staples Stadium [Directions] | 12:30 p.m. | ||
| Sat., 5/4 | V Girls Lacrosse | Trumbull | Away - McDougall Stadium [Directions] | 5:45 p.m. | W 14-6 | |
| Sat., 5/4 | JV Girls Lacrosse | Trumbull | Away - McDougall Stadium [Directions] | 4:00 p.m. | ||
| Sat., 5/4 | V Girls Outdoor Track | Middletown Tournament | Away - Middletown HS | TBA | ||
| Sat., 5/4 | V Girls Water Polo | Hopkins, Sacred Heart | Away | 3:00 p.m. | ||
| Mon., 5/6 | V Baseball | Darien | Away - DHS Baseball Varsity Field [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 5/6 | JV Baseball | Darien | Away - DHS Baseball JV Field [Directions] | 4:00 p.m. | ||
| Mon., 5/6 | FR Baseball | Darien | Home - Staples HS Baseball Field [Directions] | 4:00 p.m. | L 4-1 | |
| Mon., 5/6 | V Boys Golf | Wildcat Invitational | Away - Norwich Golf Course | 12:30 p.m. | ||
| Mon., 5/6 | FR Boys Lacrosse | Ridgefield | Away - Tiger Hollow Turf Field II [Directions] | 4:00 p.m. | W 8-5 | |
| Mon., 5/6 | V Boys Volleyball | Stamford | Away - Kuzco Gymnasium at Stamford HS [Directions] | 4:30 p.m. | W 3-0 | |
| Mon., 5/6 | JV Boys Volleyball | Stamford | Away - Kuzco Gymnasium at Stamford HS [Directions] | 5:30 p.m. | ||
| Mon., 5/6 | V Girls Golf | St. Joseph | Home - Longshore [Directions] | 3:00 p.m. | S 179, SJHS 226 | |
| Mon., 5/6 | FR Girls Lacrosse | Ridgefield | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | ||
| Mon., 5/6 | V Girls Outdoor Track | Wilton | Home - Staples Stadium [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | V Boys Golf | Trumbull | Home - Longshore [Directions] | 3:00 p.m. | shs 155 trumbull 166 | |
| Tue., 5/7 | JV Boys Golf | Trumbull | Home - Longshore [Directions] | 3:30 p.m. | ||
| Tue., 5/7 | V Boys Lacrosse | Westhill | Away - J. Walter Kennedy Stadium [Directions] | 5:30 p.m. | W 22-1 | |
| Tue., 5/7 | JV Boys Lacrosse | Westhill | Away - J. Walter Kennedy Stadium [Directions] | 4:00 p.m. | W 11-1 | |
| Tue., 5/7 | V Boys Outdoor Track | Wilton | Home - Staples HS Track [Directions] | 4:00 p.m. | 2 buses | |
| Tue., 5/7 | V Boys Tennis | New Canaan | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Tue., 5/7 | JV Boys Tennis | New Canaan | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | V Girls Golf | Fairfield Warde | Away - Smith Richardson [Directions] | 3:00 p.m. | S 200 Warde 187 | ED 1:50 |
| Tue., 5/7 | JV Girls Golf | Fairfield Ludlowe | Away - South Pine Creek Par 3 [Directions] | 3:15 p.m. | ||
| Tue., 5/7 | V Girls Lacrosse | Wilton | Away - Lilly Field - Turf [Directions] | 6:00 p.m. | L 6-9 | |
| Tue., 5/7 | JV Girls Lacrosse | Wilton | Away - Lilly Field - Turf [Directions] | 4:00 p.m. | ||
| Tue., 5/7 | V Softball | Darien | Home - Greens Farms Elementary School [Directions] | 7:00 p.m. | W 8-7 | |
| Tue., 5/7 | V Girls Tennis | New Canaan | Away - NCHS Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Wed., 5/8 | V Baseball | Fairfield Ludlowe | Away - Kiwanis Field [Directions] | 4:00 p.m. | L 14-0 | |
| Wed., 5/8 | JV Baseball | Fairfield Ludlowe | Away - Owen Fish Park [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | FR Baseball | Fairfield Ludlowe | Home - Staples HS Baseball Field [Directions] | 4:00 p.m. | W 12-5 | |
| Wed., 5/8 | V Boys Golf | New Canaan | Home - Longshore [Directions] | 3:00 p.m. | shs 151 NC 154 | |
| Wed., 5/8 | JV Boys Golf | New Canaan | Home - Longshore [Directions] | 3:00 p.m. | ||
| Wed., 5/8 | V Boys Tennis | Weston | Away - WHS Tennis Courts [Directions] | 3:45 p.m. | W 7-0 | |
| Wed., 5/8 | JV Boys Tennis | Weston | Away - WHS Tennis Courts [Directions] | 5:00 p.m. | ||
| Wed., 5/8 | V Boys Volleyball | Greenwich | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Wed., 5/8 | JV Boys Volleyball | Greenwich | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | ||
| Wed., 5/8 | V Co-ed Sailing | Regatta | Away - Indian Harbor | TBA | ||
| Wed., 5/8 | FR Girls Lacrosse | Westhill | Away - Westhill Front Turf Field [Directions] | 5:00 p.m. | ||
| Wed., 5/8 | V Girls Outdoor Track | FR/SO FCIAC Championship | Home - Staples Stadium [Directions] | TBA | ||
| Wed., 5/8 | V Softball | Fairfield Ludlowe | Home - Wakeman Field [Directions] | 4:00 p.m. | L 3-9 | |
| Wed., 5/8 | JV Softball | Fairfield Ludlowe | Home - Staples HS - Softball Field [Directions] | 4:00 p.m. | ||
| Wed., 5/8 | V Girls Tennis | Weston | Home - Staples HS-Tennis Courts [Directions] | 3:45 p.m. | W 6-1 | |
| Wed., 5/8 | JV Girls Tennis | Weston | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Thu., 5/9 | FR Boys Lacrosse | Fairfield Warde | Away - Fairfield Warde Grass Utility Field [Directions] | 4:00 p.m. | W 11-3 | |
| Thu., 5/9 | V Boys Outdoor Track | Louckes Games | Away - White Plains HS | TBA | ||
| Thu., 5/9 | V Boys Rugby | Greenwich | Home - Staples Stadium [Directions] | 5:30 p.m. | ||
| Thu., 5/9 | JV Boys Rugby | Greenwich | Home - Staples Stadium [Directions] | 7:00 p.m. | ||
| Thu., 5/9 | V Boys Tennis | St. Joseph | Away [Directions] | 4:00 p.m. | W 6-1 | |
| Thu., 5/9 | V Boys Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | W 3-0 | |
| Thu., 5/9 | JV Boys Volleyball | St. Joseph | Away - St. Joseph HS [Directions] | 5:30 p.m. | ||
| Thu., 5/9 | V Girls Golf | Fairfield Ludlowe | Home - Longshore [Directions] | 3:00 p.m. | S 187, LUDLOWE 192 | |
| Thu., 5/9 | JV Girls Golf | Greenwich | Away - Milbrook Country Club [Directions] | 3:30 p.m. | ||
| Thu., 5/9 | V Girls Lacrosse | Stamford | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | W 18-6 | |
| Thu., 5/9 | JV Girls Lacrosse | Stamford | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | ||
| Thu., 5/9 | V Softball | Joel Barlow | Away - Field E (Softball) [Directions] | 4:00 p.m. | W 12-2 | |
| Thu., 5/9 | V Girls Tennis | St. Joseph | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Fri., 5/10 | V Baseball | Bridgeport Central | Home - Staples HS Baseball Field [Directions] | 4:00 p.m. | W 5-4 | |
| Fri., 5/10 | V Boys Lacrosse | Danbury | Home - Staples Stadium [Directions] | 7:00 p.m. | W 17-1 | Senior Night |
| Fri., 5/10 | JV Boys Lacrosse | Danbury | Home - Staples Stadium [Directions] | 5:15 p.m. | W 11-1 | |
| Fri., 5/10 | V Boys Outdoor Track | Greater Hartford Invitational | Away - East Hartford HS | 4:00 p.m. | ||
| Fri., 5/10 | V Boys Outdoor Track | Louckes Games | Away - White Plains HS | TBA | ||
| Fri., 5/10 | FR Girls Lacrosse | Fairfield Ludlowe | Home - Ginny Parker Field - Staples [Directions] | 5:30 p.m. | ||
| Fri., 5/10 | V Girls Outdoor Track | Glenn D Louckes Games | Away - Glenn D Louckes Games | TBA | ||
| Fri., 5/10 | V Girls Water Polo | Hopkins School | Home - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Sat., 5/11 | V Boys Outdoor Track | Greater Hartford Invitational | Away | 9:00 a.m. | ||
| Sat., 5/11 | V Boys Outdoor Track | Louckes Games | Away - White Plains HS | TBA | ||
| Sat., 5/11 | JV Boys Rugby | Fairfield Prep | Away [Directions] | 11:30 a.m. | SOPHOMORE GAME | |
| Sat., 5/11 | FR Boys Rugby | Fairfield Prep | Away [Directions] | 1:00 p.m. | ||
| Sat., 5/11 | V Girls Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | 7:00 p.m. | W 11-10 | |
| Sat., 5/11 | JV Girls Lacrosse | Fairfield Ludlowe | Away - Taft Field [Directions] | 5:15 p.m. | ||
| Sat., 5/11 | V Girls Outdoor Track | Greater Hartford Open | Away - East Hartford HS | TBA | ||
| Sat., 5/11 | V Girls Outdoor Track | Glenn D Louckes Games | Away - White Plains NY | TBA | ||
| Sat., 5/11 | V Softball | Ridgefield | Away - Tiger Ridge Softball Field (RHS) [Directions] | 11:00 a.m. | L 3-7 | |
| Sat., 5/11 | V Softball | Brien McMahon | Home - Wakeman Field [Directions] | 3:30 p.m. | W 6-3 | 83 pax bus |
| Sat., 5/11 | JV Softball | Ridgefield | Away - RHS Upper Grass Field [Directions] | 11:00 a.m. | ||
| Mon., 5/13 | JV Boys Golf | Darien | Away - Wee Burn CC [Directions] | Cancelled | Cancelled | |
| Mon., 5/13 | V Boys Volleyball | Trumbull | Home - Staples H.S. Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Mon., 5/13 | JV Boys Volleyball | Trumbull | Home - Staples H.S. Gym [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | JV Boys Golf | Fairfield Prep | Home - Longshore [Directions] | 3:00 p.m. | ||
| Tue., 5/14 | V Boys Lacrosse | New Fairfield | Away - Rebel Turf [Directions] | 6:30 p.m. | L 1-10 | Coach bus |
| Tue., 5/14 | JV Boys Lacrosse | Greenwich | Home - Wakeman Field B (turf) [Directions] | 4:30 p.m. | W 8-3 | |
| Tue., 5/14 | JV Boys Lacrosse | Greenwich | Home - Wakeman Field B (turf) [Directions] | Cancelled | Cancelled | |
| Tue., 5/14 | JV Boys Tennis | Greenwich | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/14 | V Co-ed Sailing | Silver cup qualifier | Away - Indian Harbor | TBA | ||
| Tue., 5/14 | V Girls Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | S 188, T 206 | ED 2:00 |
| Tue., 5/14 | JV Girls Golf | Trumbull | Away - Tashua Knolls Golf Course [Directions] | 3:15 p.m. | ||
| Tue., 5/14 | V Girls Lacrosse | New Fairfield | Away - Rebel Turf [Directions] | 4:30 p.m. | W 11-10 | |
| Tue., 5/14 | JV Girls Lacrosse | New Fairfield | Away - Rebel Stadium [Directions] | 5:45 p.m. | ||
| Tue., 5/14 | V Softball | New Canaan | Away - Waveny Park - Orchard Field [Directions] | 4:00 p.m. | W 5-0 | 83 pax bus |
| Tue., 5/14 | V Girls Tennis | Fairfield Warde | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 5/14 | JV Girls Tennis | Fairfield Ludlowe | Away - Dwight Elementary School Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | V Baseball | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | W 14-1 (5) | |
| Wed., 5/15 | JV Baseball | St. Joseph | Away - Unity Park, Trumbull [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | FR Baseball | St. Joseph | Home - Staples HS Baseball Field [Directions] | 4:00 p.m. | W 12-2 | |
| Wed., 5/15 | V Boys Golf | Greenwich | Away - Burning Tree Country Club [Directions] | 3:30 p.m. | shs 171 Greenwich 150 | ED 2:00 |
| Wed., 5/15 | JV Boys Golf | Greenwich | Away [Directions] | Cancelled | Cancelled | ED 1:45 |
| Wed., 5/15 | FR Boys Lacrosse | New Canaan | Home - Staples Stadium [Directions] | 5:30 p.m. | W 10-9 (OT) | |
| Wed., 5/15 | V Boys Tennis | FCIAC Quarter finals vs Ludlowe | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | JV Boys Tennis | Trumbull | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | V Boys Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 5:30 p.m. | L 2-3 | |
| Wed., 5/15 | JV Boys Volleyball | Danbury | Away - Danbury HS - MAIN gym [Directions] | 4:00 p.m. | ||
| Wed., 5/15 | V Co-ed Sailing | Gold Cup | Away - Indian Harbor | TBA | ||
| Wed., 5/15 | V Girls Golf | Greenwich | Home - Longshore [Directions] | 3:00 p.m. | S 188, G 177 | |
| Wed., 5/15 | JV Girls Golf | Greenwich | Home - Longshore [Directions] | 3:00 p.m. | ||
| Wed., 5/15 | FR Girls Lacrosse | Fairfield Warde | Home - Ginny Parker Field - Staples [Directions] | 5:00 p.m. | ||
| Wed., 5/15 | V Softball | St. Joseph | Home - Wakeman Field [Directions] | 4:30 p.m. | L 4-7 | |
| Wed., 5/15 | JV Softball | St. Joseph | Home - Staples HS - Softball Field [Directions] | 4:30 p.m. | ||
| Wed., 5/15 | Unified Sports Soccer | Fairfield Ludlowe | Away [Directions] | 3:00 p.m. | ||
| Thu., 5/16 | V Baseball | New Canaan | Home - Staples HS Baseball Field [Directions] | 4:00 p.m. | W 6-2 | Senior Day |
| Thu., 5/16 | JV Baseball | New Canaan | Home - Wakeman Field [Directions] | 4:00 p.m. | ||
| Thu., 5/16 | FR Baseball | New Canaan | Away - Waveny Park - Coppo Field [Directions] | 4:00 p.m. | W 5-0 | |
| Thu., 5/16 | V Boys Golf | Danbury | Home - Longshore [Directions] | 3:00 p.m. | shs 151 Danbury 168 | |
| Thu., 5/16 | V Boys Outdoor Track | Greenwich | Away - Greenwich HS [Directions] | 4:00 p.m. | ||
| Thu., 5/16 | V Boys Rugby | Fairfield Prep | Home - Staples Stadium [Directions] | 6:00 p.m. | ||
| Thu., 5/16 | JV Boys Rugby | Fairfield Prep | Home - Staples Stadium [Directions] | Cancelled | Cancelled | |
| Thu., 5/16 | V Girls Golf | Danbury | Away - Richter Park Golf Course [Directions] | 3:15 p.m. | S 201 D 282 | ED 1:30 |
| Thu., 5/16 | V Girls Outdoor Track | Greenwich | Away - Cardinal Stadium [Directions] | 4:00 p.m. | ||
| Thu., 5/16 | V Softball | North Haven | Away - North Haven Athletic Complex [Directions] | 7:00 p.m. | L 0-9 | 83 pax bus |
| Thu., 5/16 | JV Softball | North Haven | Away - North Haven Athletic Complex - Brook Field [Directions] | 4:00 p.m. | ||
| Thu., 5/16 | V Girls Tennis | New Canaan | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | W 5-2 | |
| Thu., 5/16 | JV Girls Tennis | Trumbull | Home - Town Farms Tennis Courts [Directions] | 4:00 p.m. | ||
| Fri., 5/17 | JV Boys Lacrosse | New Canaan | Home - Staples Stadium [Directions] | 5:30 p.m. | W 10-2 | |
| Fri., 5/17 | FR Boys Lacrosse | Wilton | Home - PJ Romano Field - Saugatuck Elem School [Directions] | 4:00 p.m. | W 9-7 | |
| Fri., 5/17 | V Boys Outdoor Track | Hatter Freshman Invitational | Away - New Milford HS | Cancelled | Cancelled | |
| Fri., 5/17 | V Boys Outdoor Track | Dream Invitational | Away - New Milford HS | Cancelled | Cancelled | |
| Fri., 5/17 | V Girls Lacrosse | Fairfield Ludlowe | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | ||
| Sat., 5/18 | V Baseball | Brien McMahon | Home - Staples HS - Baseball Field [Directions] | 1:00 p.m. | ||
| Sat., 5/18 | V Boys Lacrosse | FCIAC Quarterfinals at Wilton | Away | 12:00 p.m. | ||
| Mon., 5/20 | V Boys Golf | St. Joseph | Away [Directions] | 3:15 p.m. | shs 157 st joe's 178 | |
| Mon., 5/20 | JV Boys Golf | Greenwich | Home - Longshore [Directions] | 3:00 p.m. | ||
| Mon., 5/20 | JV Boys Rugby | Greenwich | Home - Staples Stadium [Directions] | 5:30 p.m. | SOPHOMORE GAME | |
| Mon., 5/20 | FR Boys Rugby | Greenwich | Away [Directions] | TBA | ||
| Mon., 5/20 | V Girls Golf | Ridgefield | Away - Ridgefield Public GC (DHLY Ridge) [Directions] | 3:15 p.m. | ED 1:30 | |
| Mon., 5/20 | JV Girls Golf | New Canaan | Home - Longshore [Directions] | 3:15 p.m. | ||
| Mon., 5/20 | V Girls Lacrosse | New Canaan | Away - Norwalk HS [Directions] | 7:00 p.m. | ||
| Tue., 5/21 | V Baseball | St. Joseph | Away - Cubeta Stadium [Directions] | 5:00 p.m. | ||
| Tue., 5/21 | V Boys Golf | Darien | Away - Wee Burn CC [Directions] | 3:00 p.m. | SHS 177 DARIEN 150 | ED 1:45 |
| Tue., 5/21 | V Boys Outdoor Track | FCIAC Championship | Away - SCSU | 1:30 p.m. | ED 10:15 | |
| Tue., 5/21 | V Boys Tennis | FCIAC semi-finals vs Greenwich | Home - Staples HS-Tennis Courts [Directions] | 4:00 p.m. | ||
| Tue., 5/21 | V Girls Golf | Ridgefield | Home - Longshore [Directions] | 3:00 p.m. | S 193 R 197 | |
| Tue., 5/21 | JV Girls Golf | Trumbull | Away [Directions] | 3:15 p.m. | ||
| Tue., 5/21 | V Girls Outdoor Track | FCIAC Championship | Away - SCSU | 1:00 p.m. | ED 10:15 | |
| Tue., 5/21 | V Girls Tennis | Wilton | Away - Wilton Tennis Courts [Directions] | 4:00 p.m. | W 4-0 | |
| Wed., 5/22 | V Baseball | Fairfield Ludlowe | Away - Cubeta Stadium [Directions] | 7:00 p.m. | ||
| Wed., 5/22 | V Boys Golf | Brien McMahon | Home - Longshore [Directions] | 3:00 p.m. | shs 152 BM 186 | |
| Wed., 5/22 | JV Boys Golf | Fairfield Prep | Away - Brooklawn Country Club, Fairfield, CT [Directions] | 3:00 p.m. | ||
| Wed., 5/22 | V Boys Tennis | Darien | Away - Wilton HS [Directions] | 4:00 p.m. | ||
| Wed., 5/22 | V Boys Volleyball | FCIAC Quarterfinals vs Trumbull/Danbury winner | Away - Fairfield Ludlowe HS | 7:00 p.m. | ||
| Wed., 5/22 | JV Girls Golf | Trumbull | Away [Directions] | 3:15 p.m. | ||
| Thu., 5/23 | V Boys Golf | Chappa Tournament | Home - Longshore [Directions] | TBA | ||
| Thu., 5/23 | V Girls Golf | Darien | Home - Longshore [Directions] | 3:00 p.m. | S 180 D 205 | |
| Thu., 5/23 | V Softball | Fairfield Ludlowe (Scrim.) | Away [Directions] | 4:00 p.m. | ||
| Fri., 5/24 | V Boys Rugby | Greenwich | Away [Directions] | 5:00 p.m. | ||
| Fri., 5/24 | V Boys Tennis | CIAC Tourney Through Rnd. of 16 | Away - Hall HS [Directions] | 8:30 a.m. | ||
| Fri., 5/24 | V Boys Volleyball | Darien | Away - Fairfield Ludlowe HS [Directions] | 7:00 p.m. | ||
| Sat., 5/25 | V Boys Tennis | CIAC Tourney Through Quarterfinals | Away - Hall HS [Directions] | TBA | ||
| Sat., 5/25 | V Girls Tennis | CIAC Tourney 1st Rounds VS FLHS/Westhill winner | Home - Staples HS-Tennis Courts [Directions] | 12:30 p.m. | ||
| Tue., 5/28 | V Boys Golf | Hollohan Tournament | Away - Woodway GC | 12:00 p.m. | ||
| Tue., 5/28 | V Boys Tennis | CIAC Tourney Quarterfinals | Away - Wesleyan University [Directions] | 4:00 p.m. | ||
| Tue., 5/28 | V Girls Golf | New Canaan | Away - Fairchild Wheeler [Directions] | 2:20 p.m. | S 193 NC 170 | |
| Tue., 5/28 | JV Girls Golf | New Canaan | Home - Longshore [Directions] | Cancelled | Cancelled | |
| Tue., 5/28 | V Girls Lacrosse | States First Round vs. S. Windsor | Home - Ginny Parker Field - Staples [Directions] | 5:00 p.m. | ||
| Tue., 5/28 | V Girls Tennis | CIAC Tourney Quarterfinals | Away - Trumbull Racket Club | TBA | ||
| Wed., 5/29 | V Baseball | CIAC Tourney 1st Round vs. Norwalk | Home - Staples HS Baseball Field [Directions] | 2:00 p.m. | ||
| Wed., 5/29 | V Boys Lacrosse | CIAC Tourney 1st Round vs FWHS | Home - Staples Stadium [Directions] | 3:00 p.m. | ||
| Wed., 5/29 | V Boys Outdoor Track | CIAC Class LL Championship | Away - Willow Brook Park [Directions] | 3:00 p.m. | ||
| Wed., 5/29 | V Boys Tennis | CIAC Tourney Semifinals | Away - Wesleyan University [Directions] | 4:00 p.m. | ||
| Wed., 5/29 | V Boys Volleyball | CIAC Tourney 1st Round vs Enfield | Home - Staples H.S. Gym [Directions] | 6:00 p.m. | ||
| Wed., 5/29 | JV Girls Golf | FCIAC JV Tournament | Away - South Pine Creek Par 3 | TBA | ||
| Wed., 5/29 | V Girls Outdoor Track | CIAC Class LL Championship | Away - Willow Brook Park [Directions] | 3:00 p.m. | ||
| Wed., 5/29 | V Softball | CIAC Tourney 1st Round vs Fairfield Warde | Away - Fairfield Warde | 3:00 p.m. | ||
| Wed., 5/29 | V Girls Tennis | CIAC Tourney Semifinals vs Amity | Home - Staples HS-Tennis Courts [Directions] | 1:30 p.m. | ||
| Thu., 5/30 | V Baseball | CIAC Tourney 2nd Round vs Wilbur Cross | Home - Staples HS Baseball Field [Directions] | 3:30 p.m. | ||
| Thu., 5/30 | V Boys Golf | FCIAC Finals | Away - Fairchild Wheeler | 12:30 p.m. | ||
| Thu., 5/30 | V Boys Tennis | CIAC Tourney Finals | Away - Wesleyan University [Directions] | 4:00 p.m. | ||
| Thu., 5/30 | V Girls Golf | FCIAC Finals | Away - Fairchild Wheeler | 9:00 a.m. | ||
| Fri., 5/31 | V Boys Volleyball | Glastonbury | Home - Staples H.S. Gym [Directions] | 6:00 p.m. | W 3-0 | |
| Fri., 5/31 | V Girls Lacrosse | CIAC Quarterfinals vs Wilton | Home - Ginny Parker Field - Staples [Directions] | 4:00 p.m. | ||
| Fri., 5/31 | V Softball | CIAC Tourney Quarterfinals | Away - Higher Seed | Cancelled | Cancelled | |
| Fri., 5/31 | V Girls Tennis | CIAC Tourney Final vs Wilton | Away - New Canaan HS | 3:00 p.m. | ||
| Sat., 6/1 | V Baseball | Trumbull | Home - Staples Baseball Field [Directions] | 1:30 p.m. | ||
| Sat., 6/1 | V Boys Lacrosse | CIAC Tourney Quarterfinals vs Ridgefield | Away - Ridgefield HS | 2:00 p.m. | ||
| Sat., 6/1 | V Boys Tennis | State Open Singles Rd. of 16/Doubles Quarterfinals | Away - Wesleyan [Directions] | 12:00 p.m. | ||
| Sat., 6/1 | V Girls Tennis | State Open Qualifying, 1st and 2nd Rounds | Away - Singles @ Conard/Doubles @ Hall | 1:00 p.m. | ||
| Mon., 6/3 | V Boys Golf | CIAC Div. I Championship | Away - Timberlin GC - Kensington [Directions] | 8:00 a.m. | ||
| Mon., 6/3 | V Boys Outdoor Track | CIAC Open Championship | Away - Willow Brook Park [Directions] | 2:00 p.m. | ||
| Mon., 6/3 | V Boys Tennis | State Open Singles Quarterfinals/Doubles Semifinals | Away - Wesleyan University [Directions] | 4:00 p.m. | ||
| Mon., 6/3 | V Girls Outdoor Track | CIAC Open Championship | Away - Willow Brook Park [Directions] | 2:00 p.m. | ||
| Mon., 6/3 | V Girls Tennis | State Open Round of 16/Quarterfinals | Away - Yale University [Directions] | 12:00 p.m. | ||
| Tue., 6/4 | V Baseball | Cheshire | Away - Municipal Stadium [Directions] | 7:00 p.m. | ||
| Tue., 6/4 | V Boys Tennis | State Open Singles Semifinals | Away - Wesleyan University [Directions] | 4:00 p.m. | ||
| Tue., 6/4 | V Boys Volleyball | Southington | Away - Oxford Hs [Directions] | 5:00 p.m. | ||
| Tue., 6/4 | V Girls Golf | CIAC Girls Golf Championship | Away - Tashua Knolls CC [Directions] | 8:30 a.m. | ||
| Tue., 6/4 | V Softball | CIAC Tourney Semifinals | Away - Site TBA | Cancelled | Cancelled | |
| Tue., 6/4 | V Girls Tennis | State Open Semifinals | Away - Yale University [Directions] | 3:00 p.m. | ||
| Wed., 6/5 | V Boys Lacrosse | Darien | Away - Brien McMahon HS [Directions] | 7:15 p.m. | ||
| Wed., 6/5 | V Boys Tennis | State Open Finals | Away - Connecticut Tennis Center [Directions] | TBA | ||
| Wed., 6/5 | V Girls Tennis | State Open Finals | Away - Connecticut Tennis Center [Directions] | TBA | ||
| Thu., 6/6 | V Boys Volleyball | Darien | Away - Shelton HS [Directions] | 5:00 p.m. | ||
| Sat., 6/8 | V Baseball | Southington | Away - Palmer Field, Middletown [Directions] | 12:00 p.m. | ||
| Sat., 6/8 | V Boys Golf | CIAC Open Championship | Away - Black Hall GC | 1:00 p.m. | ||
| Sat., 6/8 | V Boys Lacrosse | CIAC Tourney Final | Away - Brien McMahon HS [Directions] | TBA | ||
| Sat., 6/8 | V Boys Outdoor Track | New England Championship | Away - Thornton Academy, Saco, ME [Directions] | TBA | ||
| Sat., 6/8 | V Girls Golf | CIAC Open Championship | Away - Black Hall GC | 1:00 p.m. | ||
| Sat., 6/8 | V Girls Outdoor Track | New England Championship | Away - Thornton Academy, Saco, ME [Directions] | TBA | ||
| Sat., 6/8 | V Softball | CIAC Tourney Final | Away - Site TBA | Cancelled | Cancelled | |
| Tue., 6/11 | V Boys Outdoor Track | CIAC Decathlon Champ. | Away - Manchester [Directions] | 11:00 a.m. | ||
| Tue., 6/11 | V Girls Outdoor Track | CIAC Heptathlon/Hammer/Steeplechase Champ. | Away - Manchester [Directions] | 11:30 a.m. | ||
| Wed., 6/12 | V Boys Outdoor Track | CIAC Decathlon/Hammer/Steeplechase Champ. | Away - Manchester [Directions] | 11:00 a.m. | ||
| Wed., 6/12 | V Girls Outdoor Track | CIAC Heptathlon Champ. | Away - Manchester [Directions] | 11:00 a.m. | ||
| Thu., 6/13 | V Boys Outdoor Track | New Balance Outdoor Nationals | Away - A & T Univ, Greensboro, NC | TBA | ||
| Thu., 6/13 | V Girls Outdoor Track | New Balance Outdoor Nationals | Away - North carolina A&T, Greensboro, NC | TBA | ||
| Fri., 6/14 | V Boys Outdoor Track | New Balance Outdoor Nationals | Away | TBA | ||
| Fri., 6/14 | V Girls Outdoor Track | New Balance Outdoor Nationals | Away | TBA | ||
| Sat., 6/15 | V Boys Outdoor Track | New Balance Outdoor Nationals | Away | TBA | ||
| Sat., 6/15 | V Girls Outdoor Track | New Balance Outdoor Nationals | Away | TBA | ||
| Sun., 6/16 | V Boys Outdoor Track | New Balance Outdoor Nationals | Away | TBA | ||
| Sun., 6/16 | V Girls Outdoor Track | New Balance Outdoor Nationals | Away | TBA | ||
| Wed., 6/19 | V Boys Golf | New England Championships | Away - Bretwood GC - Keene, NH | 8:00 a.m. | ||
| Wed., 6/19 | V Girls Golf | New England Championships | Away - Bretwood GC - Keene, NH | 8:00 a.m. | ||