| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 8/29 | 5:00 PM | Varsity | Scrimmage | Normal | Away | Danbury | | | | Danbury High School - Stadium Turf Field | 3:15 PM - 1 Bus |
| THU 8/31 | 5:00 PM | Varsity | Scrimmage | Normal | Home | Ridgefield | | | | Joel Barlow High School - Field I (Stadium) | |
| MON 9/4 | 4:30 PM | Varsity | Scrimmage | Normal | Home | Trumbull | | | | Joel Barlow High School - Field J (Competition Field) | |
| TUE 9/12 | 6:00 PM | Varsity | League | Normal | Away | Newtown | Loss | 1-4 | | Newtown High School - Blue and Gold Stadium | |
| THU 9/14 | 4:00 PM | Varsity | League | Normal | Away | New Fairfield | Tied | 0-0 | | New Fairfield High School - Marty Morgan Field | 2:15 PM - 1 Bus |
| TUE 9/19 | 5:00 PM | Varsity | League | Normal | Home | Kolbe Cathedral | Win | 8-0 | | Joel Barlow High School - Field J (Competition Field) | |
| THU 9/21 | 5:00 PM | Varsity | League | Normal | Home | Immaculate | Win | 6-0 | | Joel Barlow High School - Field J (Competition Field) | |
| TUE 9/26 | 6:00 PM | Varsity | League | Normal | Away | Brookfield | Loss | 0-4 | | Brookfield High School - BHS Back Turf | |
| THU 9/28 | 6:00 PM | Varsity | League | Normal | Home | Stratford | Win | 1-0 | | Joel Barlow High School - Field I (Stadium) | |
| TUE 10/3 | 7:00 PM | Varsity | League | Normal | Away | Notre Dame-Fairfield | Loss | 0-4 | | Notre Dame - Fairfield - Park Ave Field | 5:30 PM - 1 Bus |
| THU 10/5 | 7:00 PM | Varsity | League | Normal | Home | New Milford | Win | 5-1 | | Joel Barlow High School - Field I (Stadium) | |
| TUE 10/10 | 7:00 PM | Varsity | League | Normal | Away | Masuk | Tied | 0-0 | | Masuk High School - Benedict Stadium Field @ Masuk HS | |
| THU 10/12 | 6:00 PM | Varsity | League | Normal | Home | Bethel | Loss | 0-5 | | Joel Barlow High School - Field I (Stadium) | |
| TUE 10/17 | 7:00 PM | Varsity | League | Normal | Home | Bunnell | Win | 5-0 | | Joel Barlow High School - Field I (Stadium) | |
| THU 10/19 | 6:00 PM | Varsity | League | Normal | Away | Weston | Loss | 0-4 | | Weston High School - WHS Stadium Field | |
| MON 10/23 | 6:00 PM | Varsity | League | Normal | Home | Pomperaug | Win | 1-0 | | Joel Barlow High School - Field J (Competition Field) | |
| SAT 10/28 | 1:00 PM | Varsity | Postseason | Normal | Away | Notre Dame-Fairfield | | | | Notre Dame - Fairfield - Park Ave Field | 11:30 AM - 1 Bus |
| WED 11/1 | Canceled | Varsity | Scrimmage | Canceled | Away | Brien McMahon | | | | Brien McMahon High School - Casagrande Field | |
| THU 11/2 | 4:00 PM | Varsity | Scrimmage | Normal | Away | New Fairfield | | | | New Fairfield High School - Marty Morgan Field | 2:15 PM - 1 Bus |
| MON 11/6 | 2:00 PM | Varsity | Postseason | Normal | Away | East Catholic | Loss | 0-3 | | East Catholic High School - Lower Field | 11:00 AM - 1 Bus |