| Wilton 2019-20 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 239 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| Fri., 8/30 | V Football | New London (Scrim.) | Away - New London HS- Pat Cannamela Field [Directions] | 6:30 p.m. | ||
| Wed., 9/4 | V Girls Volleyball | Jonathan Law (Scrim.) | Home - Wilton Court 2 [Directions] | 4:30 p.m. | ||
| Wed., 9/4 | JV Girls Volleyball | TBA | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Thu., 9/5 | FR Football | Norwalk (Scrim.) | Away - Norwalk HS-Testa Field [Directions] | 6:15 p.m. | ||
| Thu., 9/5 | V Boys Soccer | Branford (Scrim.) | Home - Wilton HS-Allens Grass Field [Directions] | 4:15 p.m. | ||
| Thu., 9/5 | V Girls Soccer | Glastonbury (Scrim.) | Home - Wilton HS-Lilly Field [Directions] | 5:00 p.m. | ||
| Fri., 9/6 | V Boys Soccer | Foran, Litchfield, Masuk, TBA, Northwestern, Old Saybrook, Stamford | Away - Foran HS -Foran High School - Turf Field | TBA | ||
| Sat., 9/7 | V Football | Danbury (Scrim.) | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 11:00 a.m. | ||
| Sat., 9/7 | V Girls Soccer | TBA | Home - Allen's Meadow-2B [Directions] | 9:00 a.m. | ||
| Sat., 9/7 | V Girls Soccer | Bethel (Scrim.) | Home - Allen's Meadow-2A [Directions] | 9:00 a.m. | ||
| Sat., 9/7 | V Girls Volleyball | Naugatuck (Scrim.) | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:00 a.m. | ||
| Sat., 9/7 | V Girls Volleyball | St. Joseph (Scrim.) | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:00 a.m. | ||
| Sat., 9/7 | V Girls Volleyball | Wilton Jamboree | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:00 a.m. | ||
| Sat., 9/7 | V Girls Volleyball | New Milford (Scrim.) | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 9:00 a.m. | ||
| Mon., 9/9 | V Boys Cross Country | Ridgefield, Fairfield Warde, Stamford | Away - Ridgefield HS-Upper Grass Field [Directions] | 4:00 p.m. | Wilton 24 - F. Warde 35 Ridgefield 28 - Wilton 29 Wilton 10 - Stamford 40 | |
| Mon., 9/9 | V Girls Cross Country | Ridgefield, Fairfield Warde, Stamford | Away - Ridgefield HS-Upper Grass Field [Directions] | 4:00 p.m. | Ridgefield 18 Wilton 43 Wilton 22 Warde 35 Wilton 15 Stamford | |
| Tue., 9/10 | V Boys Soccer | TBA | Home - Wilton HS-Fuijitani Field -Turf [Directions] | Canceled | Cancelled | |
| Tue., 9/10 | JV Boys Soccer | TBA | Home - Wilton HS-Lilly Field [Directions] | Canceled | Cancelled | |
| Tue., 9/10 | V Girls Soccer | Brookfield (Scrim.) | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | ||
| Tue., 9/10 | JV Girls Soccer | Brookfield | Home - Allen's Meadow-2A [Directions] | 4:00 p.m. | ||
| Tue., 9/10 | V Girls Volleyball | Weston (Scrim.) | Home - Wilton HS [Directions] | 4:15 p.m. | ||
| Tue., 9/10 | JV Girls Volleyball | Weston (Scrim.) | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:15 p.m. | ||
| Tue., 9/10 | FR Girls Volleyball | Weston (Scrim.) | Home - Wilton Court 2 [Directions] | 4:15 p.m. | ||
| Wed., 9/11 | V Boys Soccer | Fairfield Prep (Scrim.) | Away - Fairfield University-Rafferty Stadium [Directions] | 4:30 p.m. | ||
| Thu., 9/12 | V Girls Volleyball | New Milford | Away - New Milford HS-Main Gym - NMHS [Directions] | 6:00 p.m. | L 0-3 | |
| Thu., 9/12 | JV Girls Volleyball | New Milford | Away - New Milford HS-Main Gym - NMHS [Directions] | 4:45 p.m. | ||
| Thu., 9/12 | FR Girls Volleyball | Kennedy Catholic-Somers (NY) | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | W 3-2 | |
| Fri., 9/13 | V Football | Fitch | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 7:00 p.m. | W 31-14 | |
| Fri., 9/13 | V Boys Soccer | St. Joseph | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | W 6-1 | |
| Fri., 9/13 | JV Boys Soccer | St. Joseph | Home - Allen's Meadow-2A [Directions] | 4:00 p.m. | W 7-0 | |
| Fri., 9/13 | V Girls Soccer | St. Joseph | Away - St. Joseph HS-Lower Turf [Directions] | 4:00 p.m. | T 0-0 | |
| Fri., 9/13 | JV Girls Soccer | St. Joseph | Away - St. Joseph HS-Lower Grass Field [Directions] | 4:00 p.m. | W 3-1 | |
| Sat., 9/14 | V Boys Cross Country | Greenwich | Home - Wilton HS-Allen Meadow [Directions] | 10:00 a.m. | ||
| Sat., 9/14 | V Boys Cross Country | Seymour | Home - Wilton HS-Allen Meadow [Directions] | 8:00 a.m. | ||
| Sat., 9/14 | V Boys Cross Country | New Canaan | Home - Wilton HS-Allen Meadow [Directions] | 9:00 a.m. | NC 25 - Wilton 30 Trumbull 18 - Wilton 39 Danbury 18 - Wilton 41 | |
| Sat., 9/14 | V Boys Cross Country | New Fairfield | Home - Wilton HS-Allen Meadow [Directions] | 9:00 a.m. | ||
| Sat., 9/14 | V Boys Cross Country | Pomperaug | Home - Wilton HS-Allen Meadow [Directions] | 9:00 a.m. | ||
| Sat., 9/14 | V Boys Cross Country | Trumbull | Home - Wilton HS-Allen Meadow [Directions] | 9:00 a.m. | ||
| Sat., 9/14 | V Boys Cross Country | Amity | Home - Wilton HS-Allen Meadow [Directions] | 9:00 a.m. | ||
| Sat., 9/14 | V Boys Cross Country | Darien | Home - Wilton HS-Allen Meadow [Directions] | 9:30 a.m. | ||
| Sat., 9/14 | V Boys Cross Country | Glastonbury | Home - Allen's Meadow [Directions] | TBA | ||
| Sat., 9/14 | V Boys Cross Country | Glastonbury | Home - Allen's Meadow [Directions] | TBA | ||
| Sat., 9/14 | V Boys Cross Country | Glastonbury | Home - Allen's Meadow [Directions] | TBA | ||
| Sat., 9/14 | JV Boys Cross Country | Amity | Home - Wilton HS [Directions] | 9:00 a.m. | ||
| Sat., 9/14 | JV Football | Fitch | Away - Fitch HS-Dorr Field (Football Field on Campus) [Directions] | 1:00 p.m. | ||
| Sat., 9/14 | FR Football | Fitch | Away - Fitch HS-Dorr Field (Football Field on Campus) [Directions] | 1:00 p.m. | ||
| Sat., 9/14 | V Girls Cross Country | Greenwich | Home - Wilton HS-Allen Meadow [Directions] | 10:00 a.m. | ||
| Sat., 9/14 | V Girls Cross Country | Glastonbury | Home - Allen's Meadow [Directions] | 11:00 a.m. | ||
| Sat., 9/14 | V Girls Cross Country | New Canaan | Home - Wilton HS-Allen Meadow [Directions] | 9:00 a.m. | NC 20 - Wilton 38 Trumbull 20 - Wilton 37 Wilton 26 - Danbury 28 Tie Breaker | |
| Sat., 9/14 | V Girls Cross Country | Darien | Home - Wilton HS-Allen Meadow [Directions] | 9:00 a.m. | ||
| Sat., 9/14 | V Girls Cross Country | Amity | Home - Wilton HS-Allen Meadow [Directions] | 9:00 a.m. | ||
| Sat., 9/14 | V Girls Cross Country | Trumbull | Home - Wilton HS-Allen Meadow [Directions] | 9:00 a.m. | ||
| Sat., 9/14 | V Girls Cross Country | Weston | Home - Wilton HS-Allen Meadow [Directions] | 9:00 a.m. | ||
| Sat., 9/14 | V Girls Cross Country | Pomperaug | Home - Wilton HS-Allen Meadow [Directions] | 9:00 a.m. | ||
| Sat., 9/14 | V Girls Cross Country | Bethel | Home - Wilton HS-Allen Meadow [Directions] | 9:30 a.m. | ||
| Sat., 9/14 | V Girls Cross Country | Seymour | Home - Wilton HS-Allen Meadow [Directions] | 2:30 p.m. | ||
| Sat., 9/14 | V Girls Cross Country | New Fairfield | Home - Wilton HS-Allen Meadow [Directions] | TBA | ||
| Sat., 9/14 | V Girls Volleyball | Immaculate | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 10:00 a.m. | L 0-3 | |
| Sat., 9/14 | JV Girls Volleyball | Immaculate | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 11:30 a.m. | ||
| Mon., 9/16 | V Boys Soccer | Norwalk | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | W 3-1 | |
| Mon., 9/16 | JV Boys Soccer | Norwalk | Home - Allen's Meadow-2A [Directions] | 4:00 p.m. | L 1-3 | |
| Mon., 9/16 | FR Boys Soccer | Norwalk | Away - Nathan Hale MS-Callahan Complex at Nathan Hale Upper [Directions] | 4:30 p.m. | ||
| Mon., 9/16 | V Girls Volleyball | St. Joseph | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:30 p.m. | L 0-3 | |
| Mon., 9/16 | JV Girls Volleyball | St. Joseph | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Mon., 9/16 | FR Girls Volleyball | St. Joseph | Away - St. Joseph HS-Gym [Directions] | 4:30 p.m. | L 0-3 | |
| Tue., 9/17 | V Boys Cross Country | Darien, Fairfield Ludlowe, Westhill | Home - Wilton HS-Allen Meadow [Directions] | 4:00 p.m. | ||
| Tue., 9/17 | V Girls Cross Country | Darien, Fairfield Ludlowe, Westhill | Home - Wilton HS-Allen Meadow [Directions] | 4:00 p.m. | ||
| Tue., 9/17 | V Girls Soccer | Norwalk | Away - Norwalk HS-Testa Field [Directions] | 7:00 p.m. | W 5-0 | |
| Wed., 9/18 | V Boys Soccer | Westhill | Away - Westhill HS-Front Turf [Directions] | 4:30 p.m. | W 4-1 | |
| Wed., 9/18 | JV Boys Soccer | Westhill | Away - Rippowan MS-Rippowam Turf Field [Directions] | 4:30 p.m. | L 0-4 | |
| Wed., 9/18 | FR Boys Soccer | Westhill | Home - Allen's Meadow-3A [Directions] | 4:00 p.m. | ||
| Wed., 9/18 | V Girls Volleyball | Norwalk | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:30 p.m. | L 1-3 | |
| Wed., 9/18 | JV Girls Volleyball | Norwalk | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Wed., 9/18 | FR Girls Volleyball | Norwalk | Away - Norwalk HS-Tom Scarso Gymnasium [Directions] | 4:00 p.m. | W 3-2 | |
| Thu., 9/19 | FR Football | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | Canceled | Cancelled | |
| Thu., 9/19 | V Girls Soccer | Westhill | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | W 3-0 | |
| Thu., 9/19 | JV Girls Soccer | Westhill | Home - Allen's Meadow-2B [Directions] | 4:00 p.m. | W 7-0 | |
| Thu., 9/19 | FR Girls Soccer | Westhill | Away - Westhill HS-TBA [Directions] | 5:00 p.m. | W 3-1 | |
| Fri., 9/20 | V Football | Brien McMahon | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 7:00 p.m. | W 37-0 | |
| Fri., 9/20 | V Boys Soccer | Darien | Away - Darien HS-DHS Center Oval Turf Field [Directions] | 4:00 p.m. | T 2-2 | |
| Fri., 9/20 | JV Boys Soccer | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | L 0-2 | |
| Fri., 9/20 | FR Boys Soccer | Darien | Home - Allen's Meadow-3A [Directions] | 4:00 p.m. | ||
| Fri., 9/20 | V Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Fri., 9/20 | JV Girls Volleyball | Westhill | Away - Westhill HS-Main Gym [Directions] | 4:30 p.m. | ||
| Fri., 9/20 | FR Girls Volleyball | Westhill | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | L 0-3 | |
| Sat., 9/21 | JV Football | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 10:30 a.m. | ||
| Sat., 9/21 | V Girls Soccer | Darien | Home - Wilton HS-Lilly Field [Directions] | 2:00 p.m. | W 1-0 | |
| Sat., 9/21 | JV Girls Soccer | Darien | Home - Wilton HS-Allen Meadow [Directions] | 2:00 p.m. | W 2-0 | |
| Sat., 9/21 | FR Girls Soccer | Darien | Away - Darien HS-DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | ||
| Mon., 9/23 | JV Girls Soccer | New Canaan | Away - Saxe MS-Field 1 [Directions] | 4:00 p.m. | W 2-0 | |
| Mon., 9/23 | FR Girls Soccer | Darien | Home - Wilton HS-Allen Meadow [Directions] | 4:00 p.m. | ||
| Tue., 9/24 | V Boys Cross Country | New Canaan, Danbury, Trumbull | Away - Waveny Park [Directions] | 4:00 p.m. | ||
| Tue., 9/24 | V Girls Cross Country | New Canaan, Danbury, Trumbull | Away - Waveny Park [Directions] | 4:00 p.m. | ||
| Tue., 9/24 | V Girls Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 4:30 p.m. | L 0-3 | |
| Tue., 9/24 | JV Girls Volleyball | Darien | Away - Darien HS-DHS Main Gym [Directions] | 6:00 p.m. | ||
| Tue., 9/24 | FR Girls Volleyball | Darien | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | L 2-3 | |
| Wed., 9/25 | FR Girls Soccer | New Canaan | Away - Saxe MS-Field #2 [Directions] | 6:05 p.m. | ||
| Thu., 9/26 | FR Football | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 4:00 p.m. | ||
| Thu., 9/26 | FR Girls Volleyball | Kennedy Catholic-Somers (NY) | Away - Kennedy Catholic HS-Gym | 4:00 p.m. | W 3-2 | |
| Fri., 9/27 | V Football | St. Joseph | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 7:00 p.m. | L 14-56 | |
| Fri., 9/27 | V Boys Soccer | New Canaan | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | W 2-0 | |
| Fri., 9/27 | JV Boys Soccer | New Canaan | Home - Allen's Meadow-2A [Directions] | 4:00 p.m. | L 3-1 | |
| Fri., 9/27 | FR Boys Soccer | New Canaan | Away - Saxe MS-Field 1 [Directions] | 4:00 p.m. | ||
| Fri., 9/27 | V Girls Soccer | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 6:30 p.m. | L 0-2 | |
| Fri., 9/27 | FR Girls Soccer | New Canaan | Home - Allen's Meadow-3B [Directions] | 4:00 p.m. | L 5-1 | |
| Sat., 9/28 | JV Football | St. Joseph | Away - St. Joseph HS-Upper Turf [Directions] | 10:30 a.m. | ||
| Tue., 10/1 | V Boys Cross Country | Norwalk, St. Joseph, Trinity Catholic | Home - Wilton HS-Allen Meadow [Directions] | 4:00 p.m. | ||
| Tue., 10/1 | V Boys Soccer | Fairfield Warde | Away - Fairfield Warde HS-Varsity Grass Soccer Field [Directions] | 4:30 p.m. | T 3-3 | |
| Tue., 10/1 | JV Boys Soccer | Fairfield Warde | Away - Tunxis [Directions] | 4:00 p.m. | T 1-1 | |
| Tue., 10/1 | FR Boys Soccer | Fairfield Warde | Home - Wilton HS-Allen Meadow [Directions] | 4:00 p.m. | ||
| Tue., 10/1 | V Girls Cross Country | Norwalk, St. Joseph, Trinity Catholic | Home - Wilton HS-Allen Meadow [Directions] | 4:00 p.m. | ||
| Tue., 10/1 | V Girls Cross Country | Guilford | Home - Wilton HS [Directions] | 4:00 p.m. | ||
| Tue., 10/1 | V Girls Volleyball | New Canaan | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:30 p.m. | L 1-3 | |
| Tue., 10/1 | JV Girls Volleyball | New Canaan | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Tue., 10/1 | FR Girls Volleyball | New Canaan | Away - New Canaan HS-Main Gym [Directions] | 4:00 p.m. | L 1-3 | |
| Wed., 10/2 | V Girls Soccer | Fairfield Warde | Home - Wilton HS-Lilly Field [Directions] | 6:30 p.m. | W 3-0 | |
| Wed., 10/2 | JV Girls Soccer | Fairfield Warde | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | W 1-0 | |
| Thu., 10/3 | FR Football | Fairfield Warde | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 6:05 p.m. | ||
| Thu., 10/3 | V Boys Soccer | Trinity Catholic | Away - Trinity Catholic-Gaglio Field | 4:45 p.m. | W 6-0 | |
| Thu., 10/3 | V Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Large Gym [Directions] | 5:30 p.m. | L 3-1 | |
| Thu., 10/3 | JV Girls Volleyball | Fairfield Warde | Away - Fairfield Warde HS-Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/3 | FR Girls Volleyball | Fairfield Warde | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | L 2-3 | |
| Fri., 10/4 | V Football | Fairfield Warde | Away - Fairfield Warde HS-Tetreau/Davis Field [Directions] | 7:00 p.m. | W 42-6 | |
| Fri., 10/4 | V Girls Soccer | Trinity Catholic | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | W 6-0 | |
| Fri., 10/4 | FR Girls Soccer | Weston | Away - Weston HS-WHS Lower Turf Field [Directions] | 4:00 p.m. | ||
| Fri., 10/4 | V Girls Volleyball | Trinity Catholic | Away - Trinity Catholic-Gym | 4:30 p.m. | L 1-3 | |
| Fri., 10/4 | JV Girls Volleyball | Trinity Catholic | Away - Trinity Catholic-Gym | 6:00 p.m. | ||
| Sat., 10/5 | JV Football | Fairfield Warde | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 4:00 p.m. | ||
| Sat., 10/5 | V Boys Soccer | Danbury | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | W 3-0 | |
| Sat., 10/5 | JV Boys Soccer | Danbury | Home - Allen's Meadow-2A [Directions] | 4:00 p.m. | ||
| Sat., 10/5 | FR Boys Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 2:00 p.m. | ||
| Mon., 10/7 | V Boys Cross Country | Greenwich, Brien McMahon, Staples | Away - Greenwich Point [Directions] | 4:00 p.m. | ||
| Mon., 10/7 | V Girls Cross Country | Greenwich, Brien McMahon, Staples | Away - Greenwich Point [Directions] | 4:00 p.m. | ||
| Mon., 10/7 | V Girls Soccer | Danbury | Away - Mill Ridge Int. School-Turf Field [Directions] | 4:00 p.m. | W 3-0 | |
| Mon., 10/7 | JV Girls Soccer | Danbury | Away - Danbury HS-Grass Soccer Field [Directions] | 4:30 p.m. | W 3-1 | |
| Mon., 10/7 | FR Girls Soccer | Danbury | Home - Allen's Meadow-3B [Directions] | 4:00 p.m. | ||
| Mon., 10/7 | V Girls Volleyball | Danbury | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:30 p.m. | L 1-3 | |
| Mon., 10/7 | JV Girls Volleyball | Danbury | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Mon., 10/7 | FR Girls Volleyball | Danbury | Away - Danbury HS-Main Gym [Directions] | 4:00 p.m. | ||
| Thu., 10/10 | V Boys Soccer | Brien McMahon | Home - Wilton HS-Lilly Field [Directions] | 6:30 p.m. | T 4-4 | |
| Thu., 10/10 | JV Boys Soccer | Brien McMahon | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | ||
| Thu., 10/10 | FR Boys Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 5:00 p.m. | ||
| Fri., 10/11 | V Girls Soccer | Brien McMahon | Away - Brien McMahon HS-Casagrande Field [Directions] | 6:30 p.m. | W 5-1 | |
| Fri., 10/11 | JV Girls Soccer | Brien McMahon | Away - Brien McMahon HS-Pride Field [Directions] | 5:00 p.m. | W 5-0 | |
| Fri., 10/11 | V Girls Volleyball | Brien McMahon | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:30 p.m. | L 0-3 | |
| Fri., 10/11 | JV Girls Volleyball | Brien McMahon | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Sat., 10/12 | V Boys Soccer | Bridgeport Central | Home - Wilton HS-Lilly Field [Directions] | 10:30 a.m. | W 4-0 | |
| Sat., 10/12 | JV Boys Soccer | Bridgeport Central | Home - Allen's Meadow-2A [Directions] | 10:00 a.m. | ||
| Mon., 10/14 | V Girls Soccer | Bridgeport Central | Away - Bridgeport Central HS-Kennedy Stadium [Directions] | 4:00 p.m. | W 4-0 | |
| Tue., 10/15 | FR Boys Soccer | Greenwich | Home - Allen's Meadow-3A [Directions] | 4:00 p.m. | ||
| Tue., 10/15 | FR Girls Soccer | Greenwich | Away - Cos Cob Park-Benvenuto Field [Directions] | 4:30 p.m. | ||
| Tue., 10/15 | V Girls Volleyball | Bridgeport Central | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:30 p.m. | W 3-0 | |
| Tue., 10/15 | JV Girls Volleyball | Bridgeport Central | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Thu., 10/17 | FR Football | Ridgefield | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 6:00 p.m. | ||
| Thu., 10/17 | V Boys Soccer | Trumbull | Home - Wilton HS-Lilly Field [Directions] | 6:30 p.m. | W 2-0 | |
| Thu., 10/17 | JV Boys Soccer | Trumbull | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | ||
| Thu., 10/17 | FR Boys Soccer | Trumbull | Away - Trumbull HS-JV Grass Field [Directions] | 4:00 p.m. | ||
| Thu., 10/17 | V Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 4:30 p.m. | L 2-3 | |
| Thu., 10/17 | JV Girls Volleyball | Greenwich | Away - Greenwich HS-Gymnasium [Directions] | 5:30 p.m. | ||
| Thu., 10/17 | FR Girls Volleyball | Greenwich | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Fri., 10/18 | V Football | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 5:30 p.m. | L 0-21 | |
| Fri., 10/18 | V Girls Soccer | Trumbull | Away - Trumbull HS-New Turf Field [Directions] | 3:30 p.m. | W 4-2 | |
| Fri., 10/18 | JV Girls Soccer | Trumbull | Away - Trumbull HS-The Pit [Directions] | 3:30 p.m. | T 1-1 | |
| Fri., 10/18 | FR Girls Soccer | Trumbull | Home - Allen's Meadow-3B [Directions] | 4:00 p.m. | ||
| Sat., 10/19 | JV Football | Ridgefield | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 2:30 p.m. | ||
| Sat., 10/19 | V Boys Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Taft Field [Directions] | 10:00 a.m. | T 1-1 | |
| Sat., 10/19 | JV Boys Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-RLMS [Directions] | 10:00 a.m. | ||
| Sat., 10/19 | FR Boys Soccer | Fairfield Ludlowe | Home - Allen's Meadow-3A [Directions] | 4:00 p.m. | ||
| Mon., 10/21 | FR Boys Soccer | Ridgefield | Away - Ridgefield HS-Upper Grass Field [Directions] | 4:00 p.m. | ||
| Mon., 10/21 | V Girls Soccer | Fairfield Ludlowe | Home - Wilton HS-Lilly Field [Directions] | 6:30 p.m. | T 2-2 | |
| Mon., 10/21 | JV Girls Soccer | Fairfield Ludlowe | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | L 0-1 | |
| Mon., 10/21 | FR Girls Soccer | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Sturges Park [Directions] | 4:00 p.m. | ||
| Mon., 10/21 | V Girls Volleyball | Trumbull | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:30 p.m. | L 0-3 | |
| Mon., 10/21 | JV Girls Volleyball | Trumbull | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Mon., 10/21 | FR Girls Volleyball | Trumbull | Away - Trumbull HS-Gym [Directions] | 4:00 p.m. | ||
| Tue., 10/22 | V Boys Cross Country | New Canaan | Home - Allen's Meadow [Directions] | 4:00 p.m. | ||
| Tue., 10/22 | V Boys Cross Country | Pomperaug | Home - Wilton HS-Allen Meadow [Directions] | 4:00 p.m. | ||
| Tue., 10/22 | V Boys Soccer | Ridgefield | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | T 1-1 | |
| Tue., 10/22 | JV Boys Soccer | Ridgefield | Home - Allen's Meadow-2A [Directions] | 4:00 p.m. | ||
| Tue., 10/22 | V Girls Cross Country | Pomperaug | Home - Wilton HS-Allen Meadow [Directions] | 4:00 p.m. | ||
| Wed., 10/23 | V Girls Soccer | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 4:00 p.m. | L 1-2 | |
| Wed., 10/23 | JV Girls Soccer | Ridgefield | Away - Ridgefield HS-Tiger Hollow Stadium [Directions] | 5:30 p.m. | L 0-1 | |
| Wed., 10/23 | V Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 6:00 p.m. | L 0-3 | |
| Wed., 10/23 | JV Girls Volleyball | Fairfield Ludlowe | Away - Fairfield Ludlowe HS-Main Gym [Directions] | 4:30 p.m. | ||
| Wed., 10/23 | FR Girls Volleyball | Fairfield Ludlowe | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Thu., 10/24 | FR Football | Bunnell | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 6:00 p.m. | ||
| Thu., 10/24 | V Boys Soccer | Stamford | Away - Stamford HS-SHS Upper Soccer Field [Directions] | 4:30 p.m. | L 3-2 | |
| Thu., 10/24 | JV Boys Soccer | Stamford | Away - Rippowam MS-Upper Soccer/Footballl Field [Directions] | 4:30 p.m. | ||
| Thu., 10/24 | FR Boys Soccer | Stamford | Home - Allen's Meadow-3A [Directions] | 4:00 p.m. | ||
| Fri., 10/25 | V Football | Bunnell | Away - Bunnell HS-Bunnell Turf Field [Directions] | 7:00 p.m. | W 45-14 | |
| Fri., 10/25 | V Boys Soccer | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 4:00 p.m. | L 2-4 | |
| Fri., 10/25 | JV Boys Soccer | Greenwich | Away - Greenwich HS-Field 3 [Directions] | 4:00 p.m. | ||
| Fri., 10/25 | V Girls Soccer | Stamford | Home - Wilton HS-Lilly Field [Directions] | 6:30 p.m. | W 3-0 | |
| Fri., 10/25 | JV Girls Soccer | Stamford | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | W 2-1 | |
| Fri., 10/25 | V Girls Volleyball | Ridgefield | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 5:30 p.m. | L 0-3 | |
| Fri., 10/25 | JV Girls Volleyball | Ridgefield | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Fri., 10/25 | FR Girls Volleyball | Ridgefield | Away - Ridgefield HS-Main Gym [Directions] | 4:00 p.m. | ||
| Sat., 10/26 | V Boys Cross Country | CIAC Boys Class L Divisional Championship | Away - Wickham Park | 2:40 p.m. | ||
| Sat., 10/26 | V Girls Cross Country | CIAC Girls Class L Divisional Championship | Away - Wickham Park | 2:05 p.m. | ||
| Sat., 10/26 | V Girls Soccer | Greenwich | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | W 4-1 | |
| Sat., 10/26 | JV Girls Soccer | Greenwich | Home - Allen's Meadow-2B [Directions] | 4:00 p.m. | W 2-1 | |
| Sat., 10/26 | FR Girls Soccer | Greenwich | Away - Greenwich HS-Field 3 [Directions] | 12:00 p.m. | ||
| Sat., 10/26 | V Girls Volleyball | Masuk | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 11:30 a.m. | L 1-3 | |
| Sat., 10/26 | JV Girls Volleyball | Masuk | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 10:00 a.m. | ||
| Mon., 10/28 | V Boys Soccer | Staples | Away - Staples HS-Wakeman Field B (turf) [Directions] | 4:00 p.m. | T 1-1 | |
| Tue., 10/29 | V Girls Soccer | Staples | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | L 0-3 | |
| Tue., 10/29 | JV Girls Soccer | Staples | Home - Allen's Meadow-2B [Directions] | 4:00 p.m. | ||
| Tue., 10/29 | FR Girls Soccer | Staples | Away - Staples HS-Loeffler Field - Staples HS [Directions] | 4:00 p.m. | ||
| Tue., 10/29 | V Girls Volleyball | Stamford | Away - Stamford HS-Kuzco Gymnasium [Directions] | 4:30 p.m. | L 0-3 | |
| Tue., 10/29 | JV Girls Volleyball | Stamford | Away - Stamford HS-Kuzco Gymnasium [Directions] | 5:45 p.m. | ||
| Tue., 10/29 | FR Girls Volleyball | Stamford | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Thu., 10/31 | FR Football | Staples | Away - Staples HS-Staples Stadium [Directions] | 5:00 p.m. | ||
| Thu., 10/31 | V Boys Soccer | Greenwich | Away - Greenwich HS-Cardinal Stadium [Directions] | 3:00 p.m. | W 2-1 | |
| Fri., 11/1 | V Boys Cross Country | CIAC Boys State Open Championship | Away - Wickham Park | 2:45 p.m. | ||
| Fri., 11/1 | V Football | Staples | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 7:00 p.m. | W 35-24 | |
| 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 | New Canaan | Away - New Canaan HS-WTT #1 [Directions] | 4:00 p.m. | L 6-7 PK | |
| Fri., 11/1 | V Girls Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 4:00 p.m. | L 0-3 | |
| Fri., 11/1 | JV Girls Volleyball | Staples | Away - Staples HS-Staples Gym [Directions] | 5:30 p.m. | ||
| Fri., 11/1 | FR Girls Volleyball | Staples | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 4:00 p.m. | ||
| Sat., 11/2 | V Girls Volleyball | Brookfield | Home - Wilton HS-Nicholas Zeoli Field House [Directions] | 12:00 p.m. | W 3-1 | |
| Mon., 11/4 | JV Football | Staples | Away - Staples HS-Staples Stadium [Directions] | 6:00 p.m. | ||
| Thu., 11/7 | FR Football | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 4:00 p.m. | ||
| Sat., 11/9 | V Football | Stamford | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 2:00 p.m. | W 42-0 | |
| Sat., 11/9 | V Girls Soccer | Granby Memorial (Scrim.) | Home - Wilton HS-Lilly Field [Directions] | 9:00 a.m. | ||
| Mon., 11/11 | JV Football | Stamford | Away - Stamford HS-Boyle Stadium [Directions] | 4:30 p.m. | ||
| Mon., 11/11 | V Boys Soccer | Branford | Home - Wilton HS-Lilly Field [Directions] | 4:30 p.m. | W 3-0 | |
| Tue., 11/12 | V Girls Soccer | Fairfield Warde | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | W 1-0 | |
| Wed., 11/13 | V Boys Soccer | Maloney | Home - Wilton HS-Lilly Field [Directions] | 4:30 p.m. | W 3-0 | |
| Thu., 11/14 | FR Football | New Canaan | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 6:00 p.m. | ||
| Thu., 11/14 | V Girls Soccer | Newington | Away - Newington HS-Fields in front of the VA Hospital next to NHS [Directions] | 2:00 p.m. | W 1-0 | |
| Fri., 11/15 | V Football | New Canaan | Away - New Canaan HS-Dunning Stadium [Directions] | 7:00 p.m. | L 20-38 | |
| Fri., 11/15 | V Boys Soccer | Joel Barlow | Home - Wilton HS-Lilly Field [Directions] | 4:00 p.m. | W 5-1 | |
| Sat., 11/16 | JV Football | New Canaan | Home - Wilton HS-Veterans Memorial Stadium [Directions] | 10:30 a.m. | ||
| Sat., 11/16 | V Girls Soccer | Glastonbury | Away - Glastonbury HS-Turf Field [Directions] | 1:00 p.m. | L 0-1 | |
| Mon., 11/18 | V Boys Soccer | Wethersfield | Away - Municipal Stadium (Waterbury, CT)-Ray Snyder, Sr. Turf Field [Directions] | 6:00 p.m. | W 2-1 | |
| Sat., 11/23 | V Boys Soccer | Daniel Hand | Away - Dillon Stadium [Directions] | 3:00 p.m. | L 3-4 | |
| Thu., 11/28 | V Football | Trinity Catholic | Away - Trinity Catholic-Gaglio Field | 10:00 a.m. | W 63-20 | |
| Wed., 12/4 | V Football | St. Joseph | Away - Trumbull HS-McDougall Stadium [Directions] | 6:30 p.m. | ||