| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 8/30 | 4:00 PM | Varsity | Scrimmage | Normal | Away | Avon | | | | Cromwell High School - cross country course | |
| Berlin | | |
| Cromwell | | |
| Granby Memorial | | |
| WED 9/4 | 3:45 PM | Varsity | Scrimmage | Normal | Away | Glastonbury | | | | JB Williams Park - JB Williams Park | |
| Portland | | |
| RHAM | | |
| FRI 9/6 | 4:00 PM | Varsity | Non-League | Normal | Away | | | | | . | 2:15 PM |
| TUE 9/10 | 4:00 PM | Varsity | Non-League | Normal | Away | East Hampton | | | | Camp Ingersoll - Camp Ingersoll | |
| Plainville | | |
| Portland | | |
| SAT 9/14 | 8:00 AM | Varsity | Non-League | Normal | Away | | | | | . | 7:00 AM |
| THU 9/19 | 3:45 PM | Varsity | Non-League | Normal | Away | | | | | . | 2:15 PM |
| TUE 9/24 | 3:45 PM | Varsity | League | Normal | Away | Coginchaug | | | | Camp Ingersoll - Camp Ingersoll | |
| Old Lyme | | |
| Old Saybrook | | |
| Portland | | |
| Westbrook | | |
| SAT 9/28 | 12:01 AM | Varsity | Non-League | Normal | Away | | | | | Wickham Park | 2:15 PM |
| FRI 10/4 | 4:00 PM | Varsity | Non-League | Normal | Away | | | | | TBA - TBA | 2:00 PM |
| THU 10/17 | 1:30 PM | Varsity | Postseason | Normal | Away | Coginchaug | | | | Hammonasset Park | |
| Cromwell | | |
| East Hampton | | |
| East Hampton | | |
| | |
| Haddam Killingworth | | |
| Valley Regional | | |
| Westbrook | | |
| Old Lyme | | |
| Morgan | | |
| North Branford | | |
| Old Saybrook | | |
| Old Saybrook | | |
| Portland | | |
| Portland | | |