| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/28 | 3:30 p.m. | Varsity | League | Normal | Away | Tournament Game - Opponent Not Known | | | | Cromwell High School-cross country course | |
| TUE 10/5 | 3:30 p.m. | Varsity | League | Normal | Away | Tournament Game - Opponent Not Known | | | | Totoket Valley Park - North Branford-Totoket Park - North Branford | |
| THU 10/14 | 2:30 p.m. | Varsity | League | Normal | Away | Tournament Game - Opponent Not Known | | | | East Hampton High School-Cross Country Course | |
| TUE 10/26 | 3:45 p.m. | Varsity | League | Normal | Away | Tournament Game - Opponent Not Known | | | | Old Saybrook High School-Old Saybrook Campus | |