| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SAT 8/31 | 9:00 AM | Varsity | Scrimmage | Normal | Away | Bristol Central | | | | Page Park Bristol CT - Cross Country | |
| Bristol Eastern | | |
| TUE 9/10 | 4:30 PM | Varsity | League | Normal | Away | Holy Cross | | | | Holy Cross - Holy Cross | 3:30 PM |
| Watertown | | |
| Woodland | | |
| TUE 9/17 | 4:00 PM | Varsity | League | Normal | Away | Wolcott | | | | Wolcott High School - Front of Wolcott High School | 3:30 PM |
| Torrington | | |
| Kennedy | | |
| TUE 9/24 | 4:30 PM | Varsity | League | Normal | Away | WCA | | | | Bucks Hill (MONTOE) Park - XC Course | 3:30 PM |
| Crosby | | |
| TUE 10/1 | 3:45 PM | Varsity | League | Normal | Home | Derby | | | | St. Paul Catholic HS - SP Track | |
| Wilby | | |
| TUE 10/8 | 4:00 PM | Varsity | League | Normal | Away | Naugatuck | | | | Oxford High School - OHS Wolverine Field (Turf) | |
| Oxford | | |
| Seymour | | |
| THU 10/10 | 3:45 PM | Varsity | League | Normal | Away | Bristol Eastern | | | | Page Park Bristol CT - Cross Country | |
| Bristol Central | | |