| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 8/27 | 4:00 PM | Varsity | Scrimmage | Normal | Away | New Milford | | | | New Milford High School - Joe Wiser Stadium - NMHS | 2:45 PM - 1 Bus |
| THU 8/29 | 7:00 PM | Varsity | Scrimmage | Normal | Away | Shelton | | | | Shelton High School - Finn Stadium | 6:00 PM - 1 Bus |
| SAT 8/31 | 9:00 AM | Varsity | League | Normal | Away | Shepaug Valley | | | | New Fairfield High School - Marty Morgan Field | 7:00 AM - 1 Bus |
| New Milford | | |
| Newtown | | |
| Masuk | | |
| New Fairfield | | |
| Amity | | |
| Brookfield | | |
| Lakeview | | |
| TUE 9/3 | 5:30 PM | Varsity | League | Normal | Home | New Canaan | Win | 1-0 | | Trumbull High School - McDougall Stadium | |
| SAT 9/7 | 10:00 AM | Varsity | League | Normal | Away | St. Joseph | Win | 3-2 | | St. Joseph High School - Lower Turf | |
| TUE 9/10 | 4:00 PM | Varsity | League | Normal | Away | Staples | Loss | 0-9 | | Staples High School - Ginny Parker Field | 2:30 PM - 1 Bus |
| THU 9/12 | 3:30 PM | Varsity | League | Normal | Away | Stamford | Win | 4-0 | | Stamford High School - Boyle Stadium | 1:45 PM - 1 Bus |
| TUE 9/17 | 4:30 PM | Varsity | Non-League | Normal | Home | Newtown | Loss | 2-5 | | Trumbull High School - McDougall Stadium | |
| THU 9/19 | 5:30 PM | Varsity | League | Normal | Home | Ridgefield | | | | Trumbull High School - McDougall Stadium | |
| MON 9/23 | 5:30 PM | Varsity | League | Normal | Home | Fairfield Ludlowe | | | | Trumbull High School - McDougall Stadium | |
| WED 9/25 | 6:00 PM | Varsity | League | Normal | Away | Fairfield Warde | | | | Fairfield Warde High School - Tetreau/Davis Field | 4:30 PM - 1 Bus |
| SAT 9/28 | 10:00 AM | Varsity | League | Normal | Home | Norwalk | | | | Trumbull High School - McDougall Stadium | |
| TUE 10/1 | 4:45 PM | Varsity | Non-League | Normal | Away | Masuk | | | | Masuk High School - Benedict Stadium Field @ Masuk HS | 3:30 PM - 1 Bus |
| FRI 10/4 | 5:30 PM | Varsity | League | Normal | Home | Wilton | | | | Trumbull High School - McDougall Stadium | |
| MON 10/7 | 6:30 PM | Varsity | League | Normal | Home | Brien McMahon | | | | Trumbull High School - McDougall Stadium | |
| THU 10/10 | 4:00 PM | Varsity | League | Normal | Away | Westhill | | | | Westhill High School - J. Walter Kennedy Stadium | 2:00 PM - 1 Bus |
| MON 10/14 | 4:00 PM | Varsity | League | Normal | Away | Greenwich | | | | Greenwich High School - Cardinal Stadium | 2:00 PM - 1 Bus |
| WED 10/16 | 4:00 PM | Varsity | League | Normal | Away | Danbury | | | | Danbury High School - Stadium Turf Field | 2:15 PM - 1 Bus |
| TUE 10/22 | 5:30 PM | Varsity | League | Normal | Home | Darien | | | | Trumbull High School - McDougall Stadium | |