| 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 Eastern | | | | Page Park Bristol CT - Cross Country | |
| St. Paul Catholic | | |
| FRI 9/13 | 3:30 PM | Varsity | Non-League | Normal | Away | University | | | | Nevers Road Park - Nevers Road Park XC Trail | |
| Windham Tech | | |
| Windsor | | |
| Portland | | |
| South Windsor | | |
| East Catholic | | |
| Enfield | | |
| Bristol Eastern | | |
| Hartford Public | | |
| Ellis Tech | | |
| East Hartford | | |
| East Windsor | | |
| Lyman Memorial | | |
| Northwest Catholic | | |
| Norwich Tech | | |
| TUE 9/17 | 3:45 PM | Varsity | League | Normal | Away | Platt | | | | Plainville Middle School - Cross Country Course | |
| Plainville | | |
| TUE 9/24 | 3:45 PM | Varsity | League | Normal | Away | Lewis Mills | | | | Lewis Mills High School - Cross Country Course | |
| Berlin | | |
| FRI 10/4 | 3:45 PM | Varsity | League | Normal | Home | Maloney | | | | Rockwell Park - Cross Country Course | |
| Middletown | | |
| THU 10/10 | 3:45 PM | Varsity | League | Normal | Away | Bristol Eastern | | | | Page Park Bristol CT - Cross Country | 12:00 PM |
| St. Paul Catholic | | |
| TUE 10/15 | 3:00 AM | Varsity | Postseason | Normal | Away | Plainville | | | | Wickham Park - Wickham Park | |
| RHAM | | |
| Rocky Hill | | |
| Simsbury | | |
| Southington | | |
| South Windsor | | |
| Windsor | | |
| Hall | | |
| Central Connecticut Conference (CCC) | | |
| Wethersfield | | |
| Tolland | | |
| Conard | | |
| East Catholic | | |
| Bloomfield | | |
| Avon | | |
| Berlin | | |
| E.O. Smith | | |
| Farmington | | |
| Glastonbury | | |
| East Hartford | | |
| Bristol Eastern | | |
| New Britain | | |
| Newington | | |
| Northwest Catholic | | |
| Manchester | | |
| Middletown | | |
| Platt | | |
| Lewis Mills | | |
| Maloney | | |
| Enfield | | |