| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| MON 8/28 | 4:00 PM | Varsity | Scrimmage | Normal | Home | West Haven | | | | Penders Field - Penders Field - Stratford | |
| THU 8/31 | 6:00 PM | Varsity | Scrimmage | Normal | Away | Jonathan Law | | | | Jonathan Law High School - Lawmen Stadium | 4:45 PM - 1 Bus |
| FRI 9/8 | 6:00 PM | Varsity | Non-League | Normal | Away | Seymour | Loss | 1-2 | | Seymour High School - Seymour High School Turf Field | 4:15 PM - 1 Bus |
| TUE 9/12 | 7:00 PM | Varsity | League | Normal | Home | Brookfield | Loss | 0-5 | | Penders Field - Penders Field - Stratford | |
| THU 9/14 | 5:30 PM | Varsity | League | Normal | Away | Bethel | Loss | 0-7 | | Bethel High School - Middle School Turf Soccer Field | 2:15 PM - 1 Bus |
| TUE 9/19 | 5:00 PM | Varsity | League | Normal | Away | Notre Dame-Fairfield | Loss | 1-7 | | Notre Dame - Fairfield - Park Ave Field | 4:00 PM - 1 Bus |
| THU 9/21 | 7:00 PM | Varsity | League | Normal | Home | New Milford | Loss | 0-4 | | Penders Field - Penders Field - Stratford | |
| SAT 9/23 | 11:00 AM | Varsity | Non-League | Normal | Home | Amistad | Win | 2-1 | | Penders Field - Penders Field - Stratford | |
| TUE 9/26 | 6:00 PM | Varsity | League | Normal | Away | Masuk | Loss | 0-5 | | Masuk High School - Benedict Stadium Field @ Masuk HS | 2:30 PM - 1 Bus |
| THU 9/28 | 7:00 PM | Varsity | League | Normal | Home | Joel Barlow | Loss | 0-4 | | Penders Field - Penders Field - Stratford | |
| TUE 10/3 | 5:00 PM | Varsity | League | Normal | Home | Bunnell | Loss | 0-9 | | Penders Field - Penders Field - Stratford | |
| THU 10/5 | 7:00 PM | Varsity | League | Normal | Home | Weston | Loss | 0-3 | | Penders Field - Penders Field - Stratford | |
| TUE 10/10 | 7:00 PM | Varsity | League | Normal | Home | Pomperaug | Loss | 0-6 | | Penders Field - Penders Field - Stratford | |
| THU 10/12 | 6:30 PM | Varsity | League | Normal | Away | Newtown | Loss | 0-5 | | Newtown High School - Blue and Gold Stadium | 2:15 PM - 1 Bus |
| SAT 10/14 | 3:00 PM | Varsity | League | Normal | Away | Bunnell | Loss | 3-7 | | Bunnell HS - Mastroni Field | |
| TUE 10/17 | 7:00 PM | Varsity | League | Normal | Home | New Fairfield | Loss | 1-7 | | Penders Field - Penders Field - Stratford | |
| THU 10/19 | 4:45 PM | Varsity | League | Normal | Away | Kolbe Cathedral | Loss | 1-3 | | Veterans Memorial Park CT - Veterans Memorial Park CT | 4:00 PM - 1 Bus |
| MON 10/23 | 7:00 PM | Varsity | League | Normal | Home | Immaculate | Loss | 0-3 | | Penders Field - Penders Field - Stratford | |