| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/14 | 4:00 p.m. | Varsity | League | Normal | Home | BrienMcMahon | | | | Trumbull High School-Cross Country Course | |
| TUE 9/21 | 4:00 p.m. | Varsity | League | Normal | Home | Greenwich | | | | Trumbull High School-Cross Country Course | |
| WED 9/29 | 4:30 p.m. | Varsity | League | Normal | Away | NewCanaan | | | | Waveny Park | |
| TUE 10/5 | 4:00 p.m. | Varsity | League | Normal | Away | StJoseph | | | | St. Joseph High School-Trail | |
| TUE 10/12 | 4:00 p.m. | Varsity | League | Normal | Away | FairfieldLudlowe | | | | Fairfield Ludlowe High School-Taft Field | |
| WED 10/20 | 2:15 p.m. | Varsity | League | Normal | Away | Tournament Game - Opponent Not Known | | | | Waveny Park, Coppo Field | |
| THU 10/28 | 4:00 p.m. | Varsity | League | Normal | Away | Danbury | | | | Tarrywile Park | |