| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SAT 9/9 | 11:00 AM | Freshman | League | Normal | Home | Oxford | | | | Wilby High School - Football Field | |
| SAT 9/16 | 11:00 AM | Freshman | League | Normal | Home | Watertown | | | | Wilby High School - Football Field | |
| SAT 9/30 | 11:00 AM | Freshman | League | Normal | Away | Wolcott | | | | Wolcott High School - Turf Field | 9:30 AM - 1 Bus |
| SAT 10/7 | 11:00 AM | Freshman | Non-League | Normal | Home | Northwest United | | | | Wilby High School - Football Field | |
| WED 10/18 | 4:45 PM | Freshman | League | Normal | Home | Crosby | | | | Wilby High School - Football Field | |
| SAT 10/28 | Postponed | Freshman | League | Postponed | Home | Holy Cross | | | | Wilby High School - Football Field | |
| SAT 11/11 | 10:00 AM | Freshman | League | Normal | Away | Torrington | | | | Torrington High School - Robert Frost Sports Complex | 8:30 AM - 1 Bus |