| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 8/30 | 4:30 PM | Varsity | Scrimmage | Normal | Away | Avon | | | | Cromwell High School - cross country course | |
| Cromwell | | |
| Granby Memorial | | |
| Hale Ray | | |
| TUE 9/17 | 3:45 PM | Varsity | League | Normal | Away | Bristol Eastern | | | | Page Park Bristol CT - Cross Country | |
| Maloney | | |
| TUE 9/24 | 3:45 PM | Varsity | League | Normal | Away | Bristol Central | | | | Lewis Mills High School - Cross Country Course | |
| Lewis Mills | | |
| TUE 10/1 | 12:01 AM | Varsity | League | Normal | Home | Platt | | | | Pistol Creek - Pistol Creek | |
| Middletown | | |
| TUE 10/8 | 3:45 PM | Varsity | League | Normal | Home | Plainville | | | | Pistol Creek - Pistol Creek | |
| TUE 10/15 | 3:30 PM | Varsity | League | Normal | Away | RHAM | | | | Wickham Park - Wickham Park | |
| Rocky Hill | | |
| Simsbury | | |
| Southington | | |
| South Windsor | | |
| Tolland | | |
| Wethersfield | | |
| Windsor | | |
| Hall | | |
| Central Connecticut Conference (CCC) | | |
| Platt | | |
| Plainville | | |
| New Britain | | |
| Newington | | |
| Northwest Catholic | | |
| Middletown | | |
| Maloney | | |
| Manchester | | |
| Bristol Eastern | | |
| Conard | | |
| Lewis Mills | | |
| Bristol Central | | |
| Avon | | |
| Bloomfield | | |
| East Catholic | | |
| East Hartford | | |
| Enfield | | |
| E.O. Smith | | |
| Farmington | | |
| Glastonbury | | |