| Staples 2018-19 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 240 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| 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 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 | 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 | ||
| 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. | ||
| 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. | ||
| 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 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. | ||
| 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. | ||
| 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 | |
| Sat., 9/15 | V Boys Cross Country | Stratton Brook Invitational | Away | 9:00 a.m. | ||
| 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. | ||
| 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 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. | ||
| 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 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. | ||
| 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 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. | ||
| 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 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 | |
| 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 | |
| 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. | ||
| 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. | ||
| 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 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. | ||
| 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 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. | ||
| Thu., 10/11 | V Girls Swimming and Diving | Wilton | Away - Wilton YMCA [Directions] | 3:40 p.m. | ED 1:45 | |
| 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 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. | ||
| Sat., 10/13 | V Boys Soccer | Darien | Home - Loeffler Field - Staples HS [Directions] | 2:00 p.m. | T 0-0 | |
| Sat., 10/13 | V Girls Soccer | Fairfield Ludlowe | Home - Loeffler Field - Staples HS [Directions] | 10:00 a.m. | W 3-0 | |
| 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 | |
| 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 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. | ||
| 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 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. | ||
| 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. | ||
| 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 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 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 | |
| Sat., 10/27 | JV Girls Swimming and Diving | JV FCIAC Finals | Away - Greenwich HS | 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. | ||
| 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 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 | |
| Sat., 11/3 | V Boys Soccer | Masuk (Scrim.) | Home - Wakeman Field B (turf) [Directions] | 3:00 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 | |
| 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 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 | |