| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SAT 9/21 | 10:30 AM | Freshman | League | Normal | Home | Shelton | | | | Cheshire High School - Soccer Grass Field | |
| FRI 9/27 | 3:45 PM | Freshman | League | Normal | Home | Amity | | | | Cheshire High School - Soccer Grass Field | |
| MON 10/7 | 4:00 PM | Freshman | League | Normal | Home | Daniel Hand | | | | Cheshire High School - Soccer Grass Field | |