| Trumbull 2018-19 Athletic Events Schedule | ||||||
|---|---|---|---|---|---|---|
| 242 Events Listed || Go Back || | ||||||
| Date | Sport | Opponent | H/A-Facility | Time | Result | Note |
| TBA | JV Football | Ridgefield | Away - Tiger Hollow Stadium [Directions] | TBA | ||
| TBA | JV Boys Soccer | New Canaan | Home - The Pit [Directions] | TBA | ||
| TBA | FR Boys Soccer | New Canaan | Away - Saxe MS Field [Directions] | TBA | Early Release 2:15 | |
| TBA | JV Girls Soccer | New Canaan | Away - Saxe MS Field [Directions] | TBA | Early Release @ 2:00 | |
| TBA | FR Girls Soccer | Wilton | Home - JV Grass Field [Directions] | 4:30 p.m. | ||
| Mon., 8/27 | V Football | Bunnell (Scrim.) | Away - Bunnell Turf Field [Directions] | 6:00 p.m. | ||
| Tue., 8/28 | V Boys Soccer | Amity (Scrim.) | Away - Amity HS - Field # 3 [Directions] | 4:00 p.m. | ||
| Tue., 8/28 | JV Girls Soccer | Amity (Scrim.) | Home - The Pit [Directions] | 4:00 p.m. | ||
| Tue., 8/28 | FR Girls Soccer | Amity (Scrim.) | Home - JV Grass Field [Directions] | 4:00 p.m. | ||
| Wed., 8/29 | V Field Hockey | Greens Farms Academy Play Day | Away | 5:00 p.m. | ||
| Thu., 8/30 | V Football | Masuk (Scrim.) | Home - McDougall Stadium [Directions] | 5:30 p.m. | ||
| Thu., 8/30 | FR Football | Staples (Scrim.) | Away - Staples Stadium [Directions] | 6:00 p.m. | ||
| Thu., 8/30 | V Boys Soccer | Shelton (Scrim.) | Home - New Turf Field [Directions] | 6:00 p.m. | ||
| Thu., 8/30 | JV Boys Soccer | Shelton (Scrim.) | Home - The Pit [Directions] | 4:00 p.m. | ||
| Sat., 9/1 | V Boys Soccer | Kearny High School, New Jersey | Away | 11:00 a.m. | ||
| Sat., 9/1 | V Girls Soccer | Staples (Scrim.) | Away [Directions] | 8:00 a.m. | ||
| Sat., 9/1 | JV Girls Soccer | Staples (Scrim.) | Away [Directions] | 8:00 a.m. | ||
| Sat., 9/1 | FR Girls Soccer | Staples (Scrim.) | Away [Directions] | 8:00 a.m. | ||
| Tue., 9/4 | V Boys Soccer | Notre Dame-West Haven (Scrim.) | Home - New Turf Field [Directions] | 6:00 p.m. | ||
| Tue., 9/4 | JV Boys Soccer | Notre Dame-West Haven (Scrim.) | Home - The Pit [Directions] | Cancelled | Cancelled | |
| Tue., 9/4 | V Girls Soccer | Amity (Scrim.) | Away [Directions] | 6:00 p.m. | ||
| Tue., 9/4 | V Girls Soccer | Amity (Scrim.) | Away - Amity HS - Field # 3 [Directions] | 6:00 p.m. | ||
| Fri., 9/7 | V Girls Cross Country | Darien & Christian Heritage @ the Rail Trail | Home [Directions] | 3:30 p.m. | ||
| Fri., 9/7 | V Field Hockey | Wilton | Away - Fujitani Field - Turf [Directions] | 4:30 p.m. | L 2-7 | |
| Fri., 9/7 | JV Field Hockey | Wilton | Away [Directions] | 6:00 p.m. | ||
| Fri., 9/7 | V Girls Soccer | Stamford | Home - New Turf Field [Directions] | 5:30 p.m. | W 6-0 | |
| Fri., 9/7 | JV Girls Soccer | Stamford | Home - The Pit [Directions] | 4:00 p.m. | ||
| Fri., 9/7 | V Girls Swimming and Diving | Fairfield Warde | Home - Hillcrest MS [Directions] | 4:00 p.m. | ||
| Sat., 9/8 | V Football | Greenwich | Away - Cardinal Stadium [Directions] | 4:00 p.m. | L 7-42 | |
| Sat., 9/8 | V Boys Soccer | Stamford | Away - Stamford High Soccer Field [Directions] | 4:00 p.m. | W 4-1 | |
| Sat., 9/8 | JV Boys Soccer | Stamford | Away - Stamford High Soccer Field [Directions] | 2:00 p.m. | W 1-0 | |
| Sat., 9/8 | FR Boys Soccer | Stamford | Home - New Turf Field [Directions] | 12:00 p.m. | ||
| Sat., 9/8 | V Field Hockey | Westhill | Home - McDougall Stadium [Directions] | 2:30 p.m. | W 2-0 | |
| Sat., 9/8 | JV Field Hockey | Westhill | Home - McDougall Stadium [Directions] | 1:00 p.m. | ||
| Sat., 9/8 | FR Field Hockey | Westhill | Away - Westhill Football Field [Directions] | 12:00 p.m. | ||
| Tue., 9/11 | V Boys Cross Country | St. Joseph, Wilton, Danbury | Away [Directions] | 4:00 p.m. | ||
| Tue., 9/11 | JV Football | Greenwich | Home - McDougall Stadium [Directions] | 6:30 p.m. | ||
| Tue., 9/11 | V Girls Cross Country | St. Joseph, Wilton, Danbury | Away [Directions] | 4:00 p.m. | ||
| Tue., 9/11 | V Girls Soccer | Darien | Home - New Turf Field [Directions] | 5:30 p.m. | W 3-2 | |
| Tue., 9/11 | JV Girls Soccer | Darien | Home - The Pit [Directions] | 4:00 p.m. | ||
| Tue., 9/11 | FR Girls Soccer | Darien | Away - DHS Upper Oval Turf Field [Directions] | 4:00 p.m. | Early Release @ 2:15 | |
| Wed., 9/12 | V Boys Soccer | Darien | Away - DHS Center Oval Turf Field [Directions] | 4:00 p.m. | T 1-1 | Early Release 2:15 |
| Wed., 9/12 | JV Boys Soccer | Darien | Away - DHS Upper Oval Turf Field [Directions] | 4:30 p.m. | W 5-1 | |
| Wed., 9/12 | FR Boys Soccer | Darien | Home - JV Grass Field [Directions] | 4:00 p.m. | ||
| Wed., 9/12 | V Field Hockey | Fairfield Ludlowe | Away - Taft Field [Directions] | 4:00 p.m. | L 0-3 | |
| Wed., 9/12 | JV Field Hockey | Fairfield Ludlowe | Away - Taft Field [Directions] | 5:30 p.m. | ||
| Wed., 9/12 | FR Field Hockey | Fairfield Ludlowe | Home - New Turf Field [Directions] | 5:30 p.m. | ||
| Thu., 9/13 | FR Football | Fairfield Ludlowe | Away - Barlow Field [Directions] | 5:30 p.m. | ||
| Thu., 9/13 | V Girls Soccer | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 4:00 p.m. | L 0-2 | Early Release 1:45 |
| Thu., 9/13 | JV Girls Soccer | Ridgefield | Away - Lower Grass Field [Directions] | 4:00 p.m. | Early Release 1:45 | |
| Thu., 9/13 | FR Girls Soccer | Ridgefield | Home - Field 9 [Directions] | 3:15 p.m. | ||
| Fri., 9/14 | V Football | Fairfield Ludlowe | Home - McDougall Stadium [Directions] | 7:00 p.m. | W 47-6 | |
| Fri., 9/14 | V Boys Soccer | Ridgefield | Home - New Turf Field [Directions] | 4:00 p.m. | W 6-2 | |
| Fri., 9/14 | JV Boys Soccer | Ridgefield | Home - The Pit [Directions] | 4:00 p.m. | W 3-2 | |
| Fri., 9/14 | FR Boys Soccer | Ridgefield | Away - Lower Grass Field [Directions] | 4:00 p.m. | Early Release @ 2:15 | |
| Sat., 9/15 | V Boys Cross Country | Wilton Invitational | Away | 9:30 a.m. | ||
| Sat., 9/15 | JV Football | Fairfield Ludlowe | Away - Taft Field [Directions] | 12:30 p.m. | ||
| Sat., 9/15 | V Girls Cross Country | Wilton Invitational | Away | 9:00 a.m. | ||
| Sat., 9/15 | V Field Hockey | Norwalk | Away - Testa Field, NHS [Directions] | 10:00 a.m. | L 0-7 | |
| Sat., 9/15 | JV Field Hockey | Norwalk | Away - Testa Field, NHS [Directions] | 11:30 a.m. | ||
| Sat., 9/15 | FR Field Hockey | Norwalk | Home - New Turf Field [Directions] | 10:00 a.m. | ||
| Sat., 9/15 | V Girls Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | 10:00 a.m. | W 2-1 | |
| Sat., 9/15 | JV Girls Soccer | Brien McMahon | Away - Pride Field (BMHS) [Directions] | 9:00 a.m. | ||
| Mon., 9/17 | V Boys Cross Country | Staples, Fairfield Warde, Stamford | Away - Staples Stadium [Directions] | 4:00 p.m. | Early Release @ 2:15 | |
| Mon., 9/17 | V Boys Soccer | Brien McMahon | Home - New Turf Field [Directions] | 5:30 p.m. | W 2-1 | |
| Mon., 9/17 | JV Boys Soccer | Brien McMahon | Home - The Pit [Directions] | 4:00 p.m. | W 3-2 | |
| Mon., 9/17 | V Girls Cross Country | Staples, Fairfield Warde, Stamford | Away - Staples Stadium [Directions] | 4:00 p.m. | Early Release @ 2:15 | |
| Mon., 9/17 | V Field Hockey | Greenwich | Home - McDougall Stadium [Directions] | 7:00 p.m. | L 1-4 | |
| Mon., 9/17 | JV Field Hockey | Greenwich | Home - McDougall Stadium [Directions] | 5:30 p.m. | ||
| Mon., 9/17 | FR Field Hockey | Greenwich | Away - Cos Cob Park Benvenuto Field [Directions] | 5:15 p.m. | ||
| Mon., 9/17 | FR Girls Soccer | Amity | Away - Center Field - Woodbridge [Directions] | 4:00 p.m. | Early Release @ 2:!5 | |
| Mon., 9/17 | V Girls Swimming and Diving | Darien | Away - Darien YMCA [Directions] | 3:00 p.m. | Early Release @ 1:30 | |
| Thu., 9/20 | FR Football | New Canaan | Away - Dunning Stadium [Directions] | 5:00 p.m. | ||
| Thu., 9/20 | V Field Hockey | Danbury | Home - McDougall Stadium [Directions] | 6:30 p.m. | W 1-0(OT) | |
| Thu., 9/20 | JV Field Hockey | Danbury | Home - McDougall Stadium [Directions] | 5:00 p.m. | ||
| Thu., 9/20 | FR Field Hockey | Danbury | Away - Danbury HS Grass Field Hockey Field [Directions] | 5:30 p.m. | ||
| Thu., 9/20 | V Girls Soccer | Staples | Home - New Turf Field [Directions] | 5:30 p.m. | L 0-3 | |
| Thu., 9/20 | JV Girls Soccer | Staples | Home - The Pit [Directions] | 4:00 p.m. | ||
| Thu., 9/20 | FR Girls Soccer | Staples | Away - Wakeman Field B (turf) [Directions] | 4:00 p.m. | ||
| Thu., 9/20 | V Girls Swimming and Diving | Staples | Away - Staples HS Pool [Directions] | 4:00 p.m. | ||
| Fri., 9/21 | V Football | New Canaan | Home - McDougall Stadium [Directions] | 7:00 p.m. | L 7-48 | |
| Fri., 9/21 | V Boys Soccer | Staples | Away - Loeffler Field - Staples HS [Directions] | 4:00 p.m. | W 1-0 | Early Release 2:15 |
| Fri., 9/21 | JV Boys Soccer | Staples | Away - Wakeman Field E (grass) [Directions] | 4:00 p.m. | L 4-1 | Early Release @ 2:15 |
| Fri., 9/21 | FR Boys Soccer | Staples | Home - JV Grass Field [Directions] | 4:00 p.m. | ||
| Sat., 9/22 | V Boys Cross Country | Bowdoin Park Invitational | Away | TBA | ||
| Sat., 9/22 | V Girls Cross Country | Bowdoin Park Invitational | Away | TBA | ||
| Sat., 9/22 | V Field Hockey | Joel Barlow | Home - McDougall Stadium [Directions] | 5:00 p.m. | T 0-0 | |
| Sat., 9/22 | JV Field Hockey | Joel Barlow | Home - McDougall Stadium [Directions] | 6:30 p.m. | ||
| Sat., 9/22 | V Girls Soccer | Fairfield Ludlowe | Home - New Turf Field [Directions] | 11:00 a.m. | W 1-0 | |
| Sat., 9/22 | JV Girls Soccer | Fairfield Ludlowe | Home - New Turf Field [Directions] | 9:00 a.m. | ||
| Sat., 9/22 | FR Girls Soccer | Fairfield Ludlowe | Away - South Pine Creek Field [Directions] | 10:00 a.m. | ||
| Mon., 9/24 | JV Football | New Canaan | Away - Dunning Stadium [Directions] | 4:30 p.m. | ||
| Mon., 9/24 | V Boys Soccer | Fairfield Ludlowe | Away - Taft Field [Directions] | 7:00 p.m. | W 3-2 | |
| Mon., 9/24 | JV Boys Soccer | Fairfield Ludlowe | Away - Roger Ludlowe MS [Directions] | 4:00 p.m. | W 4-1 | |
| Mon., 9/24 | FR Boys Soccer | Fairfield Ludlowe | Home - JV Grass Field [Directions] | 4:00 p.m. | ||
| Mon., 9/24 | V Field Hockey | Newtown | Home - McDougall Stadium [Directions] | 6:30 p.m. | OT-L 1-2(OT) | |
| Mon., 9/24 | JV Field Hockey | Newtown | Home - McDougall Stadium [Directions] | 5:00 p.m. | ||
| Mon., 9/24 | FR Girls Soccer | New Canaan | Home - The Pit [Directions] | 4:00 p.m. | ||
| Thu., 9/27 | V Boys Cross Country | Brien McMahon, Darien, Greenwich | Home - Greenwich Point [Directions] | 4:00 p.m. | ||
| Thu., 9/27 | FR Football | Xavier | Away - Larry McHugh Field (Xavier H.S.) [Directions] | 5:00 p.m. | ||
| Thu., 9/27 | V Boys Soccer | New Canaan | Home - McDougall Stadium [Directions] | 6:00 p.m. | W 2-0 | |
| Thu., 9/27 | V Girls Cross Country | Brien McMahon, Darien, Greenwich | Home - Greenwich Point [Directions] | 4:00 p.m. | ||
| Thu., 9/27 | V Girls Swimming and Diving | Westhill/Stamford | Away - Westhill Pool [Directions] | 3:30 p.m. | Early Release @ 1:30 | |
| Fri., 9/28 | V Football | Trinity Catholic | Away - Gaglio Field | 6:00 p.m. | W 38-7 | |
| Fri., 9/28 | V Field Hockey | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | W 3-0 | |
| Fri., 9/28 | JV Field Hockey | St. Joseph | Away - St. Joseph HS [Directions] | 5:30 p.m. | ||
| Sat., 9/29 | V Girls Soccer | Westhill | Home - McDougall Stadium [Directions] | 6:00 p.m. | W 2-1 | |
| Sat., 9/29 | JV Girls Soccer | Westhill | Home - McDougall Stadium [Directions] | 3:45 p.m. | ||
| Mon., 10/1 | V Boys Soccer | Westhill | Away - Westhill Front Turf Field [Directions] | 4:00 p.m. | T 0-0 | Early Release 2:00 |
| Mon., 10/1 | JV Boys Soccer | Westhill | Away - Rippowam MS - Turf Field [Directions] | 4:00 p.m. | T 0-0 | Early Release @ 2:00 |
| Mon., 10/1 | FR Boys Soccer | Westhill | Home - JV Grass Field [Directions] | 4:00 p.m. | ||
| Mon., 10/1 | V Field Hockey | Darien | Away - DHS Stadium Field [Directions] | 5:45 p.m. | L 0-6 | Early Release @ 2:15 |
| Mon., 10/1 | JV Field Hockey | Darien | Away - DHS Stadium Field [Directions] | 4:00 p.m. | Early Release @ 2:15 | |
| Mon., 10/1 | FR Field Hockey | Darien | Away - DHS Baseball Varsity Field [Directions] | 4:30 p.m. | ||
| Mon., 10/1 | V Girls Soccer | Greenwich | Away - Cardinal Stadium [Directions] | 4:30 p.m. | W 3-2 | Early Release @ 2:15 |
| Mon., 10/1 | JV Girls Soccer | Greenwich | Away - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | Early Release @ 2:15 | |
| Tue., 10/2 | V Boys Cross Country | Westhill, Norwalk, Trinity Catholic | Home [Directions] | 4:00 p.m. | ||
| Tue., 10/2 | V Girls Cross Country | Westhill, Norwalk, Trinity Catholic | Home [Directions] | 4:00 p.m. | ||
| Wed., 10/3 | V Girls Swimming and Diving | Greenwich | Home - Hillcrest MS [Directions] | 4:00 p.m. | ||
| Thu., 10/4 | V Boys Soccer | Greenwich | Home - New Turf Field [Directions] | 5:30 p.m. | L 0-1 | |
| Thu., 10/4 | FR Boys Soccer | Greenwich | Away - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | ||
| Fri., 10/5 | V Football | Norwalk | Away - Testa Field, NHS [Directions] | 7:00 p.m. | L 17-21 | |
| Fri., 10/5 | FR Football | Norwalk | Home - New Turf Field [Directions] | 4:30 p.m. | ||
| Fri., 10/5 | JV Boys Soccer | Greenwich | Home - The Pit [Directions] | 4:30 p.m. | T 2-2 | |
| Fri., 10/5 | V Field Hockey | Stamford | Home - McDougall Stadium [Directions] | 6:00 p.m. | T 0-0 | |
| Fri., 10/5 | JV Field Hockey | Stamford | Home - McDougall Stadium [Directions] | 4:30 p.m. | ||
| Fri., 10/5 | V Girls Soccer | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | L 901 | |
| Fri., 10/5 | JV Girls Soccer | St. Joseph | Away - St. Joseph HS [Directions] | 4:00 p.m. | ||
| Fri., 10/5 | FR Girls Soccer | Greenwich | Home - JV Grass Field [Directions] | 4:30 p.m. | ||
| Sat., 10/6 | V Boys Cross Country | Wickham Invitational | Away | 10:00 a.m. | ||
| Sat., 10/6 | JV Football | Norwalk | Home - New Turf Field [Directions] | 2:00 p.m. | ||
| Sat., 10/6 | V Girls Cross Country | Wickham Invitational | Away | TBA | ||
| Mon., 10/8 | V Boys Soccer | St. Joseph | Home - McDougall Stadium [Directions] | 6:00 p.m. | W 4-1 | |
| Mon., 10/8 | JV Boys Soccer | St. Joseph | Home - McDougall Stadium [Directions] | 4:00 p.m. | W 9-0 | |
| Mon., 10/8 | FR Girls Soccer | Weston | Away - WHS Turf Field [Directions] | 4:00 p.m. | ||
| Tue., 10/9 | V Boys Cross Country | Ridgefield, New Canaan, Fairfield Ludlowe | Away - Upper Grass Field [Directions] | 4:00 p.m. | Early Release @ 1:45 | |
| Tue., 10/9 | V Girls Cross Country | Ridgefield, New Canaan, Fairfield Ludlowe | Away - Upper Grass Field [Directions] | 4:00 p.m. | Early Release @ 1:45 | |
| Tue., 10/9 | V Girls Soccer | Fairfield Warde | Home - New Turf Field [Directions] | 5:30 p.m. | W 4-1 | |
| Tue., 10/9 | JV Girls Soccer | Fairfield Warde | Home - The Pit [Directions] | 4:00 p.m. | ||
| Tue., 10/9 | FR Girls Soccer | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | ||
| Wed., 10/10 | V Boys Soccer | Fairfield Warde | Away - Fairfield Warde Grass Soccer Field [Directions] | 4:00 p.m. | T 3-3 | |
| Wed., 10/10 | JV Boys Soccer | Fairfield Warde | Away - Tunxis Hill Park [Directions] | 4:00 p.m. | T 2-2 | |
| Wed., 10/10 | FR Boys Soccer | Fairfield Warde | Home - The Pit [Directions] | 4:00 p.m. | ||
| Wed., 10/10 | V Girls Swimming and Diving | Norwalk/McMahon | Home - Hillcrest MS [Directions] | 4:00 p.m. | ||
| Thu., 10/11 | V Field Hockey | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 6:00 p.m. | L 0-2 | |
| Thu., 10/11 | JV Field Hockey | Ridgefield | Away - Tiger Hollow Stadium [Directions] | 4:30 p.m. | ||
| Fri., 10/12 | V Boys Soccer | Wilton | Home - New Turf Field [Directions] | 5:30 p.m. | W 3-0 | |
| Fri., 10/12 | FR Boys Soccer | Wilton | Away [Directions] | 4:00 p.m. | Early Release 2:15 | |
| Fri., 10/12 | V Field Hockey | Fairfield Warde | Home - McDougall Stadium [Directions] | 7:00 p.m. | L 1-4 | |
| Fri., 10/12 | JV Field Hockey | Fairfield Warde | Home - McDougall Stadium [Directions] | 5:30 p.m. | ||
| Fri., 10/12 | FR Field Hockey | Ridgefield | Home - New Turf Field [Directions] | 7:15 p.m. | ||
| Fri., 10/12 | V Girls Soccer | Wilton | Away - Lilly Field - Turf [Directions] | 4:00 p.m. | L 0-2 | Early Release @ 1:45 |
| Fri., 10/12 | JV Girls Soccer | Wilton | Away - Allen's Field [Directions] | 4:00 p.m. | Early Release @ 1:45 | |
| Sat., 10/13 | FR Field Hockey | Amity | Home - New Turf Field [Directions] | 10:00 a.m. | ||
| Sat., 10/13 | V Girls Soccer | Norwalk | Away - Testa Field, NHS [Directions] | 1:00 p.m. | W 3-0 | |
| Sat., 10/13 | JV Girls Soccer | Norwalk | Away - Testa Field, NHS [Directions] | 11:00 a.m. | ||
| Mon., 10/15 | V Boys Soccer | Norwalk | Home - New Turf Field [Directions] | 6:00 p.m. | T 1-1 | |
| Mon., 10/15 | JV Boys Soccer | Norwalk | Home - New Turf Field [Directions] | 3:45 p.m. | W 1-0 | |
| Mon., 10/15 | FR Boys Soccer | Norwalk | Away - Callahan Complex at Nathan Hale Upper [Directions] | 4:30 p.m. | ||
| Mon., 10/15 | V Field Hockey | Staples | Home - McDougall Stadium [Directions] | 7:30 p.m. | L 0-9 | |
| Mon., 10/15 | JV Field Hockey | Staples | Home - McDougall Stadium [Directions] | 6:00 p.m. | ||
| Mon., 10/15 | FR Field Hockey | Staples | Away - Ginny Parker Field - Staples [Directions] | 4:15 p.m. | ||
| Mon., 10/15 | V Girls Soccer | New Canaan | Away - Dunning Stadium [Directions] | 4:00 p.m. | L 0-6 | Early Release @ 200 |
| Mon., 10/15 | V Girls Swimming and Diving | Fairfield Ludlowe | Away - Fairfield University Rec Plex Pool [Directions] | 4:00 p.m. | ||
| Tue., 10/16 | JV Boys Soccer | Wilton | Home - New Turf Field [Directions] | 5:00 p.m. | W 2-1 | |
| Tue., 10/16 | FR Boys Soccer | Brien McMahon | Away - Brien McMahon HS [Directions] | 4:00 p.m. | ||
| Tue., 10/16 | V Girls Soccer | Trinity Catholic | Away | 4:00 p.m. | W 6-0 | Early Release @ 2:00 |
| Tue., 10/16 | FR Girls Soccer | Amity | Home - Field 14 [Directions] | 4:00 p.m. | ||
| Wed., 10/17 | V Field Hockey | Brien McMahon | Away - Brien McMahon HS [Directions] | 7:00 p.m. | L 0-2 | |
| Wed., 10/17 | JV Field Hockey | Brien McMahon | Away - Brien McMahon HS [Directions] | 5:30 p.m. | ||
| Thu., 10/18 | V Boys Cross Country | FCIAC Championship @ Waveny Park New Canaan | Away | 2:30 p.m. | ||
| Thu., 10/18 | FR Football | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 4:00 p.m. | Early Release @ 2:00 | |
| Thu., 10/18 | V Boys Soccer | Trinity Catholic | Home - McDougall Stadium [Directions] | 6:00 p.m. | W 5-0 | |
| Thu., 10/18 | V Girls Cross Country | FCIAC's @ Waveny Park New Canaan | Away | 2:30 p.m. | ||
| Thu., 10/18 | FR Field Hockey | Amity | Away - Amity HS [Directions] | 4:45 p.m. | ||
| Thu., 10/18 | V Girls Soccer | Bridgeport Central | Home - New Turf Field [Directions] | 5:30 p.m. | W 6-0 | |
| Fri., 10/19 | V Football | Danbury | Home - McDougall Stadium [Directions] | 7:00 p.m. | W 37-26 | |
| Fri., 10/19 | FR Field Hockey | Wilton | Home - New Turf Field [Directions] | 5:30 p.m. | ||
| Sat., 10/20 | JV Football | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 2:00 p.m. | ||
| Sat., 10/20 | V Boys Soccer | Bridgeport Central | Away - Kennedy Stadium [Directions] | 11:30 a.m. | W 2-1 | |
| Sat., 10/20 | JV Boys Soccer | Bridgeport Central | Away - Veteran Park turf field [Directions] | 10:30 a.m. | W 3-0 | |
| Mon., 10/22 | FR Boys Soccer | Greenwich | Away - Cos Cob Park Benvenuto Field [Directions] | 4:30 p.m. | ||
| Mon., 10/22 | V Field Hockey | New Canaan | Away - Dunning Stadium [Directions] | 4:00 p.m. | L 0-5 | Early Release @ 2:15 |
| Mon., 10/22 | JV Field Hockey | New Canaan | Away - WTT2 [Directions] | 5:30 p.m. | Early Release at 2:15 | |
| Mon., 10/22 | FR Field Hockey | New Canaan | Home - New Turf Field [Directions] | 5:30 p.m. | ||
| Mon., 10/22 | V Girls Soccer | Danbury | Home - McDougall Stadium [Directions] | 6:00 p.m. | W 4-0 | |
| Mon., 10/22 | JV Girls Soccer | Danbury | Home - The Pit [Directions] | 4:00 p.m. | ||
| Mon., 10/22 | V Girls Swimming and Diving | Ridgefield | Home - Hillcrest MS [Directions] | 4:00 p.m. | ||
| Tue., 10/23 | V Boys Cross Country | Wilton JV Meet | Away | TBA | ||
| Tue., 10/23 | V Boys Soccer | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 6:00 p.m. | L 0-1 | |
| Tue., 10/23 | JV Boys Soccer | Danbury | Away - Danbury HS Stadium Turf Field [Directions] | 4:00 p.m. | Early Release @ 2:00 | |
| Tue., 10/23 | FR Boys Soccer | Danbury | Home - JV Grass Field [Directions] | 4:00 p.m. | ||
| Tue., 10/23 | JV Girls Soccer | Amity | Home - The Pit [Directions] | 4:15 p.m. | ||
| Tue., 10/23 | FR Girls Soccer | Danbury | Away - Danbury HS Grass Soccer Field [Directions] | 4:00 p.m. | Early Release @ 2:00 | |
| Wed., 10/24 | V Girls Swimming and Diving | Danbury | Home - Hillcrest MS [Directions] | 4:00 p.m. | ||
| Thu., 10/25 | V Boys Cross Country | Freshman Invitational Meet Tarrywile Park, Danbury | Away | TBA | ||
| Thu., 10/25 | FR Football | Darien | Home - McDougall Stadium [Directions] | 6:30 p.m. | ||
| Thu., 10/25 | V Girls Soccer | FCIAC Quarter-Finals @ Ridgefield | Away | 6:00 p.m. | ||
| Fri., 10/26 | V Football | Darien | Away - DHS Stadium Field [Directions] | 7:00 p.m. | L 13-42 | |
| Fri., 10/26 | V Boys Soccer | Norwalk | Home - New Turf Field [Directions] | 6:00 p.m. | W 1-0 (7-5 PK) | |
| Sat., 10/27 | V Boys Cross Country | CIAC Class LL Championship | Away - Wickham Park - East Hartford [Directions] | 10:20 a.m. | ||
| Sat., 10/27 | V Girls Cross Country | CIAC Class LL Championship | Away - Wickham Park - East Hartford [Directions] | 10:50 a.m. | ||
| Mon., 10/29 | JV Football | Darien | Home - McDougall Stadium [Directions] | 6:30 p.m. | ||
| Mon., 10/29 | V Boys Soccer | Staples | Away [Directions] | 7:00 p.m. | W 1-0 (3-1 PK) | |
| Mon., 10/29 | V Girls Swimming and Diving | FCIAC Dive Trials & Finals @ Westhill | Away | 5:00 p.m. | ||
| Tue., 10/30 | FR Football | Westhill | Away - Rippowam MS - Turf Field [Directions] | 3:30 p.m. | ||
| Tue., 10/30 | V Girls Swimming and Diving | FCIAC Trials @ Greenwich | Away | 5:30 p.m. | ||
| Thu., 11/1 | V Boys Soccer | Danbury | Away [Directions] | 7:00 p.m. | W 1-0 | |
| Thu., 11/1 | V Girls Soccer | Weston (Scrim.) | Home - New Turf Field [Directions] | 4:15 p.m. | ||
| Thu., 11/1 | V Girls Swimming and Diving | FCIAC Championships @ Greenwich | Away | 6:30 p.m. | ||
| Fri., 11/2 | V Boys Cross Country | CIAC Open Championship | Away - Wickham Park - East Hartford [Directions] | 2:00 p.m. | ||
| Fri., 11/2 | V Football | Westhill | Home - McDougall Stadium [Directions] | 5:00 p.m. | W 35-15 | |
| Fri., 11/2 | V Girls Cross Country | CIAC Open Championship | Away - Wickham Park - East Hartford [Directions] | 2:45 p.m. | ||
| Sat., 11/3 | JV Football | Westhill | Away - J. Walter Kennedy Stadium [Directions] | 12:00 p.m. | ||
| Sat., 11/3 | V Boys Soccer | CIAC Tourney Qualifying Round | Away - Site TBA | TBA | ||
| Sat., 11/3 | V Girls Soccer | CIAC Tourney Qualifying Round | Away - Site TBA | TBA | ||
| Mon., 11/5 | V Girls Soccer | Cheshire | Home - New Turf Field [Directions] | 2:00 p.m. | ||
| Tue., 11/6 | V Boys Soccer | Hamden | Home - New Turf Field [Directions] | 6:00 p.m. | W 2-1 (4-2 PK) | |
| Wed., 11/7 | V Girls Soccer | Shelton | Away - Shelton HS [Directions] | 6:30 p.m. | ||
| Wed., 11/7 | V Girls Soccer | State Tournament - Second Round vs. Shelton | Away | 6:30 p.m. | ||
| 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 | Fairfield Prep | Home - New Turf Game [Directions] | 5:00 p.m. | ||
| Thu., 11/8 | V Boys Soccer | Glastonbury | Away - GHS Turf Field [Directions] | 2:00 p.m. | L 0-2 | Early dismissal at 10:45 |
| Fri., 11/9 | V Football | Griswold/Wheeler | Away - Griswold Football Field [Directions] | 7:00 p.m. | W 14-6 | |
| Fri., 11/9 | V Girls Soccer | Staples | Away - Wakeman Field B (turf) [Directions] | 2:00 p.m. | Early Release at 11:45 | |
| Sat., 11/10 | V Boys Cross Country | New England Championship | Away - Derryfield Park (Manchester, NH) [Directions] | TBA | ||
| Sat., 11/10 | JV Football | Nonnewaug | Home - New Turf Field [Directions] | 2:30 p.m. | ||
| Sat., 11/10 | V Boys Soccer | CIAC Tourney Quarterfinals | Away - Higher Seed | TBA | ||
| Sat., 11/10 | V Girls Cross Country | New England Championship | Away - Derryfield Park (Manchester, NH) [Directions] | TBA | ||
| 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 | CIAC Tourney Semifinals (Possible Date) | Away - Site TBA | TBA | ||
| Tue., 11/13 | V Boys Soccer | CIAC Tourney Semifinals (Possible Date) | Away - Site TBA | TBA | ||
| Tue., 11/13 | V Girls Soccer | CIAC Tourney Semifinals (Possible Date) | Away - Site TBA | TBA | ||
| Wed., 11/14 | V Boys Soccer | CIAC Tourney Semifinals (Possible Date) | Away - Site TBA | TBA | ||
| 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 Boys Soccer | CIAC Tourney Final | Away - Site TBA | TBA | ||
| Sat., 11/17 | V Girls Soccer | CIAC Tourney Final | Away - Site TBA | TBA | ||
| Sat., 11/17 | V Girls Swimming and Diving | CIAC Open Swimming | Away - Yale Univ. [Directions] | 12:00 p.m. | ||
| Mon., 11/19 | JV Football | St. Joseph | Home - Trumbull HS [Directions] | 6:30 p.m. | ||
| Tue., 11/20 | FR Football | St. Joseph | Away - St. Joseph HS [Directions] | 3:00 p.m. | Early dismissal at 1:45 | |
| Thu., 11/22 | V Football | St. Joseph | Home - McDougall Stadium [Directions] | 10:00 a.m. | L 6-42 | |