| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/10 | 4:00 p.m. | Varsity | League | Normal | Away | Sheehan | | | | Sheehan High School-Sheehan HS Cross Country Course | |
| SAT 9/14 | 9:00 a.m. | Varsity | League | Normal | Away | Wilton | | | | Wilton High School-Allen Meadow | |
| TUE 9/17 | 4:00 p.m. | Varsity | League | Normal | Away | LymanHall | | | | Wharton Brook State Park | |
| TUE 9/24 | 3:45 p.m. | Varsity | League | Normal | Home | WilburCross | | | | Fitzgerald Field | |
| SAT 9/28 | 9:00 a.m. | Varsity | League | Normal | Away | Tournament Game - Opponent Not Known | | | | Warwick Vets High School | |
| MON 10/7 | 3:45 p.m. | Varsity | League | Normal | Away | Shelton | | | | Shelton High School-Shelton High - Track | |