| Staples 2019-20 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 236 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Sat., 8/31 | V Football | TBA | Away - TBA | Canceled | Cancelled | |
| Sat., 8/31 | FR Football | Notre Dame-West Haven (Scrim.) | Away - Notre Dame HS [Directions] | 12:30 p.m. | ||
| Tue., 9/3 | V Boys Soccer | Fairfield Prep (Scrim.) | Away - Fairfield University-Rafferty Stadium [Directions] | 4:00 p.m. | ||
| Tue., 9/3 | V Girls Soccer | Greenwich Academy (Scrim.) | Away - Greenwich Academy | 4:00 p.m. | ||
| Tue., 9/3 | JV Girls Soccer | Hamden (Scrim.) | Home - Staples HS-Loeffler Field - Staples HS [Directions] | 4:00 p.m. | ||
| Tue., 9/3 | FR Girls Soccer | Hamden (Scrim.) | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Tue., 9/3 | FR Girls Soccer | TBA | Home - Staples HS-Wakeman Field E (grass) [Directions] | Canceled | Cancelled | |
| Thu., 9/5 | V Boys Soccer | Joel Barlow (Scrim.) | Away - Joel Barlow HS-Field J (Competition Field) [Directions] | 4:30 p.m. | ||
| Thu., 9/5 | FR Girls Soccer | King and Low-Heywood Thomas (Scrim.) | Away - King School-King Turf | 4:15 p.m. | ||
| Fri., 9/6 | V Boys Cross Country | Blue and White Time Trials | Home - Staples HS-Staples Stadium [Directions] | 2:45 p.m. | ||
| Fri., 9/6 | V Football | Practice | Home - Saugatuck Elementary School-PJ Romano Field [Directions] | 3:30-6 p.m. | ||
| Fri., 9/6 | FR Football | Trumbull (Scrim.) | Away - Trumbull HS-New Turf Field [Directions] | 6:00 p.m. | ||
| Fri., 9/6 | V Girls Cross Country | Blue and White Time Trials | Home - Staples HS-Staples Stadium [Directions] | 2:45 p.m. | ||
| Sat., 9/7 | JV Football | Darien | Away - Darien HS-DHS Stadium Field [Directions] | 10:30 a.m. | ||
| Sat., 9/7 | V Boys Soccer | Wethersfield, Kingswood-Oxford, Tolland (Scrim.) | Away - Wethersfield HS-Cottone Field [Directions] | 9:00 a.m. | ||
| Mon., 9/9 | V Girls Volleyball | Stratford (Scrim.) | Home - Staples HS-Staples Gym [Directions] | 3:30 p.m. | ||
| Tue., 9/10 | V Boys Cross Country | New Canaan, St. Joseph, Westhill | Away - Waveny Park [Directions] | 4:00 p.m. | ||
| Tue., 9/10 | V Football | Practice | Home - Saugatuck Elementary School-PJ Romano Field [Directions] | 3:30-6 p.m. | ||
| Tue., 9/10 | V Boys Soccer | Glastonbury | Away - Glastonbury HS-CFC Park, Bethany, CT [Directions] | 4:30 p.m. | ||
| Tue., 9/10 | V Boys Soccer | Glastonbury (Scrim.) | Away - Glastonbury HS-CFC Park, Bethany, CT [Directions] | 4:30 p.m. | ||
| Tue., 9/10 | V Girls Cross Country | New Canaan, St. Joseph, Westhill | Away - Waveny Park [Directions] | 4:00 p.m. | ||
| Tue., 9/10 | V Girls Soccer | Weston (Scrim.) | Away - Weston HS-WHS Lower Turf Field [Directions] | 7:00 p.m. | ||
| Tue., 9/10 | JV Girls Soccer | Weston (Scrim.) | Away - Weston HS-WHS Lower Turf Field [Directions] | 5:30 p.m. | ||
| Wed., 9/11 | V Football | Practice | Home - Saugatuck Elementary School-PJ Romano Field [Directions] | 3:30-6 p.m. | ||
| Wed., 9/11 | JV Boys Soccer | Weston (Scrim.) | Away - Weston HS-WHS Stadium Field [Directions] | 6:30 p.m. | ||
| Wed., 9/11 | V Girls Soccer | Bethel (Scrim.) | Away - Bethel HS-Rourke Field [Directions] | 4:00 p.m. | ||
| Thu., 9/12 | V Football | Practice | Home - Saugatuck Elementary School-PJ Romano Field [Directions] | 3:30-6 p.m. | ||
| Thu., 9/12 | FR Football | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 4:30 p.m. | ||
| Fri., 9/13 | V Football | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 7:00 p.m. | L 13-14 | |
| Fri., 9/13 | V Boys Soccer | Bridgeport Central | Away - Bridgeport Central HS-Kennedy Stadium [Directions] | 4:00 p.m. | W 4-1 | |
| Fri., 9/13 | JV Boys Soccer | Bridgeport Central | Away - Bridgeport Central HS-Veterans Park [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 9/13 | V Girls Volleyball | Weston | Away - Weston HS-Gym (New) [Directions] | 5:00 p.m. | W 3-2 | |
| Fri., 9/13 | JV Girls Volleyball | Weston | Away - Weston HS-Gym (New) [Directions] | 3:45 p.m. | ||
| Sat., 9/14 | V Boys Cross Country | Stratton Brook Invitational | Away - Stratton Brook State Park | 9:00 a.m. | ||
| Sat., 9/14 | JV Football | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 3:30 p.m. | ||
| Sat., 9/14 | V Girls Cross Country | Stratton Brook Invitational | Away - Stratton Brook State Park | 9:00 a.m. | ||
| Sat., 9/14 | V Girls Soccer | Bridgeport Central | Home - Staples HS-Loeffler Field - Staples HS [Directions] | 2:00 p.m. | W 5-0 | |
| Mon., 9/16 | V Boys Cross Country | Danbury, Stamford, Trinity Catholic | Home - Tarrywile Park [Directions] | 4:00 p.m. | ||
| Mon., 9/16 | V Boys Soccer | Danbury | Away - Mill Ridge Int. School-Turf Field [Directions] | 4:00 p.m. | L 1-0 | |
| Mon., 9/16 | JV Boys Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 3:45 p.m. | L 302 | |
| Mon., 9/16 | FR Boys Soccer | Danbury | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | L 1-0 | |
| Mon., 9/16 | V Girls Cross Country | Danbury, Stamford, Trinity Catholic | Home - Tarrywile Park [Directions] | 4:00 p.m. | ||
| Tue., 9/17 | V Football | Practice | Home - Saugatuck Elementary School-PJ Romano Field [Directions] | 3:30-5:30 p.m. | ||
| Tue., 9/17 | V Girls Soccer | Danbury | Home - Staples HS-Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 7-0 | |
| Tue., 9/17 | JV Girls Soccer | Danbury | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Tue., 9/17 | FR Girls Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 4:00 p.m. | ||
| Wed., 9/18 | V Football | Practice | Home - Saugatuck Elementary School-PJ Romano Field [Directions] | 3:30-5:30 p.m. | ||
| Wed., 9/18 | V Boys Soccer | Trinity Catholic | Home - Staples HS-Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 6-0 | |
| Wed., 9/18 | V Girls Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 4:00 p.m. | W 3-2 | |
| Wed., 9/18 | JV Girls Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 5:30 p.m. | ||
| Wed., 9/18 | FR Girls Volleyball | Danbury | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Thu., 9/19 | FR Football | Danbury | Home - Saugatuck Elementary School-PJ Romano Field [Directions] | 4:00 p.m. | ||
| Thu., 9/19 | V Girls Soccer | Trinity Catholic | Away - Trinity Catholic-Gaglio Field | 4:00 p.m. | W 8-0 | |
| Fri., 9/20 | V Football | Practice | Home - Saugatuck Elementary School-PJ Romano Field [Directions] | 4:05-5:05 p.m. | ||
| Fri., 9/20 | V Boys Soccer | Norwalk | Home - Staples HS-Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 1-0 | |
| Fri., 9/20 | JV Boys Soccer | Norwalk | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | T 1-1 | |
| Fri., 9/20 | FR Boys Soccer | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 4:00 p.m. | W 2-1 | |
| Fri., 9/20 | V Girls Volleyball | Trinity Catholic | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 9/20 | JV Girls Volleyball | Trinity Catholic | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Sat., 9/21 | V Football | New Britain | Home - Norwalk HS-Testa Field, NHS [Directions] | 7:00 p.m. | W 14-8 | |
| Sat., 9/21 | V Girls Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 12:30 p.m. | W 9-2 | |
| Mon., 9/23 | FR Girls Soccer | New Canaan | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Tue., 9/24 | V Boys Cross Country | Darien, Fairfield Warde, Norwalk | Home - Fairfield Warde HS-Stadium [Directions] | 4:00 p.m. | ||
| Tue., 9/24 | V Football | Practice | Home - Saugatuck Elementary School-PJ Romano Field [Directions] | 3:20-6:05 p.m. | ||
| Tue., 9/24 | V Boys Soccer | Trumbull | Away - Trumbull HS-New Turf Field [Directions] | 5:30 p.m. | T 2-2 | |
| Tue., 9/24 | JV Boys Soccer | Trumbull | Away - Trumbull HS-The Pit [Directions] | 4:00 p.m. | W 2-0 | |
| Tue., 9/24 | FR Boys Soccer | Trumbull | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | W 4-2 | |
| Tue., 9/24 | V Girls Cross Country | Darien, Fairfield Warde, Norwalk | Home - Fairfield Warde HS-Stadium [Directions] | 4:00 p.m. | ||
| Tue., 9/24 | JV Girls Soccer | Greenwich | Home - Staples HS-Loeffler Field - Staples HS [Directions] | 4:30 p.m. | ||
| Tue., 9/24 | V Girls Volleyball | Norwalk | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | W 3-1 | |
| Tue., 9/24 | JV Girls Volleyball | Norwalk | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Tue., 9/24 | FR Girls Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 9/25 | V Football | Practice | Home - Saugatuck Elementary School-PJ Romano Field [Directions] | 3:20-6:05 p.m. | ||
| Wed., 9/25 | V Girls Soccer | Trumbull | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | W 6-3 | |
| Wed., 9/25 | JV Girls Soccer | Trumbull | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Wed., 9/25 | FR Girls Soccer | Trumbull | Away - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | ||
| Thu., 9/26 | V Football | Practice | Home - Saugatuck Elementary School-PJ Romano Field [Directions] | 3:20-6:05 p.m. | ||
| Thu., 9/26 | FR Football | Ridgefield | Away - Ridgefield HS-Tiger Hollow Turf Field II [Directions] | 4:00 p.m. | ||
| Thu., 9/26 | V Boys Soccer | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 6:30 p.m. | L 1-0 | |
| Thu., 9/26 | FR Boys Soccer | Fairfield Warde | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | W 2-0 | |
| Thu., 9/26 | V Girls Volleyball | Trumbull | Away - Trumbull HS-Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Thu., 9/26 | JV Girls Volleyball | Trumbull | Away - Trumbull HS-Gym [Directions] | 4:00 p.m. | ||
| Thu., 9/26 | FR Girls Volleyball | Trumbull | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Fri., 9/27 | V Football | Practice | Home - Saugatuck Elementary School-PJ Romano Field [Directions] | 3:20-5:05 p.m. | ||
| Fri., 9/27 | JV Boys Soccer | Fairfield Warde | Away - Fairfield Warde HS-Fairfield Warde Grass Utility Field [Directions] | 4:00 p.m. | W 3-1 | |
| Fri., 9/27 | V Girls Soccer | Fairfield Warde | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | W 2-0 | |
| Fri., 9/27 | JV Girls Soccer | Fairfield Warde | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Fri., 9/27 | FR Girls Soccer | Fairfield Warde | Away - Tunxis [Directions] | 4:00 p.m. | ||
| Sat., 9/28 | V Boys Cross Country | Bowdoin Park Classic | Away - Bowdoin Park | 10:00 a.m. | ||
| Sat., 9/28 | V Football | Ridgefield | Home - Norwalk HS-Testa Field, NHS [Directions] | 6:00 p.m. | L 0-7 | |
| Sat., 9/28 | V Girls Cross Country | Bowdoin Park Classic | Away - Stratton Brook State Park | 10:00 a.m. | ||
| Sat., 9/28 | V Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:00 p.m. | L 1-3 | |
| Sat., 9/28 | JV Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 5:30 p.m. | ||
| Tue., 10/1 | V Boys Cross Country | Fairfield Ludlowe, Ridgefield, Trumbull | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | ||
| Tue., 10/1 | V Football | Practice | Home - Saugatuck Elementary School-PJ Romano Field [Directions] | 3:15-6 p.m. | ||
| Tue., 10/1 | V Boys Soccer | Greenwich | Home - Staples HS-Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 1-0 | |
| Tue., 10/1 | JV Boys Soccer | Greenwich | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | T 1-1 | |
| Tue., 10/1 | FR Boys Soccer | Greenwich | Away - Cos Cob Park-Benvenuto Field [Directions] | 4:30 p.m. | W 2-1 | |
| Tue., 10/1 | V Girls Cross Country | Fairfield Ludlowe, Ridgefield, Trumbull | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 4:00 p.m. | ||
| Tue., 10/1 | V Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Tue., 10/1 | JV Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/1 | FR Girls Volleyball | Fairfield Warde | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/2 | V Football | Practice | Home - Saugatuck Elementary School-PJ Romano Field [Directions] | 3:15-6 p.m. | ||
| Wed., 10/2 | V Girls Soccer | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:30 p.m. | W 7-0 | |
| Wed., 10/2 | FR Girls Soccer | Greenwich | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Thu., 10/3 | V Football | Practice | Home - Saugatuck Elementary School-PJ Romano Field [Directions] | 3:15-6 p.m. | ||
| Thu., 10/3 | FR Football | Brien McMahon | Home - Brien McMahon HS-Casagrande Field [Directions] | 4:30 p.m. | ||
| Thu., 10/3 | V Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 7:00 p.m. | W 2-1 | |
| Thu., 10/3 | JV Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 5:00 p.m. | W 7-3 | |
| Thu., 10/3 | FR Boys Soccer | Brien McMahon | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | T 2-2 | |
| Thu., 10/3 | V Girls Volleyball | Greenwich | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | L 0-3 | |
| Thu., 10/3 | FR Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | ||
| Fri., 10/4 | V Football | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 7:00 p.m. | W 35-7 | |
| Fri., 10/4 | V Girls Soccer | Brien McMahon | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | W 5-0 | |
| Fri., 10/4 | JV Girls Soccer | Brien McMahon | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Sat., 10/5 | V Boys Soccer | Fairfield Ludlowe | Home - Staples HS-Loeffler Field - Staples HS [Directions] | 2:00 p.m. | T 0-0 | |
| Sat., 10/5 | JV Boys Soccer | Fairfield Ludlowe | Home - Staples HS-Wakeman Field B (turf) [Directions] | 2:00 p.m. | W 5-0 | |
| Sat., 10/5 | FR Boys Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 10:00 a.m. | W 2-0 | |
| Sat., 10/5 | V Girls Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 4:00 p.m. | W 3-2 | |
| Sat., 10/5 | JV Girls Volleyball | Brien McMahon | Away - Brien McMahon HS-Kehoe - King Gymnasium [Directions] | 2:30 p.m. | ||
| Mon., 10/7 | V Boys Cross Country | Greenwich, Brien McMahon, Wilton | Away - Greenwich Point [Directions] | 4:00 p.m. | ||
| Mon., 10/7 | V Girls Cross Country | Greenwich, Brien McMahon, Wilton | Away - Greenwich Point [Directions] | 4:00 p.m. | ||
| Mon., 10/7 | V Girls Soccer | Fairfield Ludlowe | Away - Tomlinson MS-Turf Field [Directions] | 4:30 p.m. | W 1-0 | |
| Mon., 10/7 | JV Girls Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 4:00 p.m. | ||
| Mon., 10/7 | FR Girls Soccer | Fairfield Ludlowe | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Mon., 10/7 | V Girls Volleyball | Fairfield Ludlowe | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | L 0-3 | |
| Mon., 10/7 | JV Girls Volleyball | Fairfield Ludlowe | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Mon., 10/7 | FR Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/10 | FR Girls Soccer | Darien | Away - Darien HS-MMS (Middlesex) Lower Field at 30 Edgerton Street [Directions] | 4:15 p.m. | ||
| Thu., 10/10 | V Girls Volleyball | Bridgeport Central | Away - Bridgeport Central HS-Gym [Directions] | 5:30 p.m. | W 3-0 | |
| Thu., 10/10 | JV Girls Volleyball | Bridgeport Central | Away - Bridgeport Central HS-Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/12 | V Boys Soccer | Stamford | Home - Staples HS-Loeffler Field - Staples HS [Directions] | 12:00 p.m. | L 2-0 | |
| Sat., 10/12 | JV Boys Soccer | Stamford | Home - Staples HS-Wakeman Field B (turf) [Directions] | 12:00 p.m. | W 6-1 | |
| Sat., 10/12 | FR Boys Soccer | Stamford | Away - Stamford HS-SHS Upper Soccer Field [Directions] | 9:00 a.m. | W 2-0 | |
| Sat., 10/12 | V Girls Volleyball | Girls Volleyball Fall Brawl | Away - RHAM HS-RHAM MS | TBA | ||
| Mon., 10/14 | JV Football | Ridgefield | Away - Ridgefield HS-Tiger Hollow Turf Field II [Directions] | 4:00 p.m. | ||
| Mon., 10/14 | V Girls Soccer | Stamford | Away - Stamford HS-SHS Upper Soccer Field [Directions] | 4:00 p.m. | W 8-0 | |
| Mon., 10/14 | JV Girls Soccer | Stamford | Away - Rippowam MS-Upper Soccer/Footballl Field [Directions] | 4:00 p.m. | ||
| Tue., 10/15 | V Boys Cross Country | FCIAC Championship | Away - Waveny Park | 2:00 p.m. | ||
| Tue., 10/15 | V Boys Soccer | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 4:00 p.m. | T 0-0 | |
| Tue., 10/15 | JV Boys Soccer | Ridgefield | Away - Ridgefield HS-RHS Lower Grass Field [Directions] | 4:00 p.m. | W 2-1 | |
| Tue., 10/15 | V Girls Cross Country | FCIAC Championship | Away - Waveny Park | 2:00 p.m. | ||
| Tue., 10/15 | FR Girls Soccer | Ridgefield | Away - Ridgefield HS-Upper Grass Field [Directions] | 4:00 p.m. | ||
| Tue., 10/15 | V Girls Volleyball | Stamford | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | W 3-2 | |
| Tue., 10/15 | JV Girls Volleyball | Stamford | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/15 | FR Girls Volleyball | Stamford | Away - Stamford HS-Kuzco Gymnasium [Directions] | 4:00 p.m. | ||
| Wed., 10/16 | V Girls Soccer | Ridgefield | Home - Staples HS-Wakeman Field B (turf) [Directions] | 3:30 p.m. | T 0-0 | |
| Thu., 10/17 | FR Football | Darien | Home - Staples HS-Staples Stadium [Directions] | 6:00 p.m. | ||
| Thu., 10/17 | V Boys Soccer | Darien | Away - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | L 3-1 | |
| Thu., 10/17 | JV Boys Soccer | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | W 4-1 | |
| Thu., 10/17 | FR Boys Soccer | Darien | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | W 5-1 | |
| Thu., 10/17 | V Girls Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 5:30 p.m. | W 3-1 | |
| Thu., 10/17 | JV Girls Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/17 | FR Girls Volleyball | Ridgefield | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/18 | V Football | North Haven | Away - North Haven MS-Vanacore Field [Directions] | 7:00 p.m. | L 20-53 | |
| Fri., 10/18 | V Girls Soccer | Darien | Away - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 10/18 | JV Girls Soccer | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 10/18 | FR Girls Soccer | Darien | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Sat., 10/19 | JV Football | North Haven | Home - Staples HS-Staples Stadium [Directions] | 2:00 p.m. | ||
| Sat., 10/19 | V Boys Soccer | St. Joseph | Home - Staples HS-Loeffler Field - Staples HS [Directions] | 2:00 p.m. | W 1-0 | |
| Sat., 10/19 | JV Boys Soccer | St. Joseph | Home - Staples HS-Wakeman Field E (grass) [Directions] | 2:00 p.m. | W 6-0 | |
| Mon., 10/21 | V Girls Soccer | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 3:30 p.m. | T 1-1 | |
| Mon., 10/21 | V Girls Volleyball | Darien | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | W 3-2 | |
| Mon., 10/21 | JV Girls Volleyball | Darien | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Mon., 10/21 | FR Girls Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/22 | V Boys Cross Country | Wilton JV Invitational | Away - Allen's Meadow | 4:00 p.m. | ||
| Tue., 10/22 | V Boys Soccer | Westhill | Away - Westhill HS-Front Turf [Directions] | 4:00 p.m. | W 2-0 | |
| Tue., 10/22 | JV Boys Soccer | Westhill | Away - Rippowan MS-Rippowam Turf Field [Directions] | 4:00 p.m. | W 2-0 | |
| Tue., 10/22 | FR Boys Soccer | Westhill | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | W 3-2 | |
| Tue., 10/22 | V Girls Cross Country | Wilton JV Invitational | Away - Allen's Meadow | 4:00 p.m. | ||
| Tue., 10/22 | JV Girls Soccer | St. Joseph | Away - St. Joseph HS-Lower Grass Field [Directions] | 3:30 p.m. | ||
| Wed., 10/23 | V Girls Soccer | Westhill | Home - Staples HS-Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 7-0 | |
| Wed., 10/23 | JV Girls Soccer | Westhill | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | ||
| Wed., 10/23 | FR Girls Soccer | Westhill | Away - Westhill HS-Westhill Front Turf Field [Directions] | Canceled | Cancelled | |
| Wed., 10/23 | V Girls Volleyball | St. Joseph | Home - Staples HS-Staples Gym [Directions] | 7:00 p.m. | W 3-1 | |
| Wed., 10/23 | JV Girls Volleyball | St. Joseph | Home - Staples HS-Staples Gym [Directions] | 5:00 p.m. | ||
| Wed., 10/23 | FR Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/24 | V Boys Cross Country | Hatter Freshmen Invitational | Away - Danbury HS | 4:00 p.m. | ||
| Thu., 10/24 | FR Football | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 7:00 p.m. | ||
| Thu., 10/24 | V Boys Soccer | New Canaan | Away - New Canaan HS-WTT #1 [Directions] | 4:00 p.m. | W 3-1 | |
| Thu., 10/24 | JV Boys Soccer | New Canaan | Away - Saxe MS-Field 1 [Directions] | 4:00 p.m. | W 3-1 | |
| Thu., 10/24 | FR Boys Soccer | New Canaan | Home - Staples HS-Wakeman Field E (grass) [Directions] | 4:00 p.m. | W 2-0 | |
| Thu., 10/24 | V Girls Cross Country | Hatter Freshmen Invitational | Away - Danbury HS | 4:00 p.m. | ||
| Fri., 10/25 | V Football | New Canaan | Home - Staples HS-Staples Stadium [Directions] | 7:00 p.m. | L 21-41 | |
| Fri., 10/25 | V Girls Soccer | New Canaan | Home - Staples HS-Wakeman Field B (turf) [Directions] | 3:30 p.m. | W 1-0 | |
| Fri., 10/25 | JV Girls Soccer | New Canaan | Home - Staples HS-Wakeman Field E (grass) [Directions] | 3:30 p.m. | ||
| Fri., 10/25 | FR Girls Soccer | New Canaan | Away - Saxe MS-Field 1 [Directions] | 4:00 p.m. | ||
| Fri., 10/25 | V Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 5:30 p.m. | L 0-3 | |
| Fri., 10/25 | JV Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:00 p.m. | ||
| Fri., 10/25 | FR Girls Volleyball | Westhill | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/26 | V Boys Cross Country | CIAC Boys Class LL Divisional Championship | Away - Wickham Park | 3:45 p.m. | ||
| Sat., 10/26 | V Girls Cross Country | CIAC Girls Class LL Divisional Championship | Away - Wickham Park | 3:10 p.m. | ||
| Mon., 10/28 | JV Football | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 4:00 p.m. | ||
| Mon., 10/28 | V Boys Soccer | Wilton | Home - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | T 1-1 | |
| Tue., 10/29 | V Girls Soccer | Wilton | Away - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | W 3-0 | |
| Tue., 10/29 | JV Girls Soccer | Wilton | Away - Allen's Meadow-2B [Directions] | 4:00 p.m. | ||
| Tue., 10/29 | FR Girls Soccer | Wilton | Home - Staples HS-Loeffler Field - Staples HS [Directions] | 4:00 p.m. | ||
| Tue., 10/29 | V Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 5:30 p.m. | L 1-3 | |
| Tue., 10/29 | JV Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/29 | FR Girls Volleyball | New Canaan | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | ||
| Wed., 10/30 | FR Boys Soccer | Ridgefield | Home - Staples HS-Loeffler Field - Staples HS [Directions] | Canceled | Cancelled | |
| Wed., 10/30 | JV Girls Soccer | Ridgefield | Home - Staples HS-Wakeman Field E (grass) [Directions] | Canceled | Cancelled | |
| Thu., 10/31 | FR Football | Wilton | Home - Staples HS-Staples Stadium [Directions] | 5:00 p.m. | ||
| Thu., 10/31 | V Boys Soccer | Danbury | Away - Mill Ridge Int. School-Turf Field [Directions] | 3:30 p.m. | W 1-0 | |
| Thu., 10/31 | V Girls Volleyball | Joel Barlow | Away - Joel Barlow HS-Lower Gym [Directions] | 4:30 p.m. | W 3-2 | |
| Fri., 11/1 | V Boys Cross Country | CIAC Boys State Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Fri., 11/1 | V Football | Wilton | Away - Wilton HS-Veterans Memorial Stadium [Directions] | 7:00 p.m. | L 24-35 | |
| Fri., 11/1 | V Girls Cross Country | CIAC Girls State Open Championship | Away - Wickham Park | 2:00 p.m. | ||
| Fri., 11/1 | V Girls Soccer | Trumbull | Home - Staples HS-Wakeman Field B (turf) [Directions] | 3:00 p.m. | ||
| Fri., 11/1 | V Girls Volleyball | Wilton | Home - Staples HS-Staples Gym [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 11/1 | JV Girls Volleyball | Wilton | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Fri., 11/1 | FR Girls Volleyball | Wilton | Away - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Sat., 11/2 | JV Girls Volleyball | Fairfield Warde, Brookfield, Fairfield Ludlowe, Greenwich, Joel Barlow, Masuk, Newtown, Ridgefield, Stamford, Trumbull, Westhill | Away - Fairfield Warde HS-Large Gym | 9:00 a.m. | ||
| Mon., 11/4 | JV Football | Wilton | Home - Staples HS-Staples Stadium [Directions] | 6:00 p.m. | ||
| Mon., 11/4 | V Girls Soccer | New Canaan | Home - Wilton HS Varsity Field [Directions] | 5:00 p.m. | ||
| Tue., 11/5 | V Boys Soccer | Fairfield Warde | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 5:00 p.m. | ||
| Tue., 11/5 | V Boys Soccer | Trumbull | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 7:00 p.m. | L 4-1 | |
| Tue., 11/5 | V Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 6:00 p.m. | ||
| Thu., 11/7 | FR Football | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 4:00 p.m. | ||
| Thu., 11/7 | V Girls Soccer | St. Joseph | Home - Wilton HS-Lilly Field - Turf [Directions] | 5:00 p.m. | ||
| Thu., 11/7 | V Girls Soccer | St. Joseph | Home - Wilton HS-Lilly Field - Turf [Directions] | Canceled | Cancelled | |
| Fri., 11/8 | V Football | Fairfield Warde | Home - Staples HS-Staples Stadium [Directions] | 7:00 p.m. | L 7-12 | |
| Sat., 11/9 | JV Football | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 10:30 a.m. | ||
| Mon., 11/11 | V Boys Soccer | Wilbur Cross | Away - Bowen Field-Football Field [Directions] | 6:00 p.m. | W 3-0 | |
| Mon., 11/11 | V Girls Volleyball | Newtown | Home - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Wed., 11/13 | V Boys Soccer | Glastonbury | Away - Glastonbury HS-Turf Field [Directions] | 2:00 p.m. | W 3-2 | |
| Thu., 11/14 | FR Football | St. Joseph | Home - Staples HS-Staples Stadium [Directions] | 6:00 p.m. | ||
| Thu., 11/14 | V Girls Soccer | Brien McMahon | Home - Staples HS-Wakeman Field B (turf) [Directions] | 2:00 p.m. | ||
| Fri., 11/15 | V Boys Soccer | Trumbull | Away - Trumbull HS-New Turf Field [Directions] | 4:00 p.m. | L 2-1 | |
| Sat., 11/16 | V Football | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 11:00 a.m. | L 0-50 | |
| Sat., 11/16 | V Girls Soccer | Farmington | Home - Staples HS-Wakeman Field B (turf) [Directions] | 2:00 p.m. | ||
| Mon., 11/18 | JV Football | St. Joseph | Home - Staples HS-Staples Stadium [Directions] | 6:00 p.m. | ||
| Tue., 11/19 | V Girls Soccer | Glastonbury | Home - Municipal Stadium (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 6:00 p.m. | ||
| Sat., 11/23 | JV Football | Greenwich | Away - Greenwich HS-Field 7 [Directions] | 10:00 a.m. | ||
| Sat., 11/23 | FR Football | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 10:00 a.m. | ||
| Thu., 11/28 | V Football | Greenwich | Home - Staples HS-Staples Stadium [Directions] | 10:00 a.m. | L 14-38 | |