| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| THU 10/1 | 5:15 p.m. | Varsity | League | Normal | Away | BrienMcMahon | | | | Brien McMahon High School-Allen Meadows | |
| MON 10/5 | 4:30 p.m. | Varsity | League | Normal | Away | Danbury | | | | Tarrywile Park | |
| TUE 10/13 | 4:30 p.m. | Varsity | League | Normal | Away | Ridgefield | | | | Ridgefield High School-Upper Grass Field | |
| TUE 10/20 | 4:00 p.m. | Varsity | League | Normal | Away | Staples | | | | Staples High School-Staples Stadium | |
| TUE 10/27 | 4:30 p.m. | Varsity | League | Normal | Away | Wilton | | | | Allen's Meadow-XC Course | |
| WED 11/4 | TBA | Varsity | League | Normal | Away | Tournament Game - Opponent Not Known | | | | Waveny Park | |