| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| FRI 9/6 | 4:00 PM | Varsity | League | Normal | Away | | | | | Veterans Memorial Park - Veterans Park XC Course | |
| TUE 9/10 | 5:00 PM | Varsity | League | Normal | Away | Enfield | Loss | 48-50 | | Mansfield Hollow State Park - Boys Course | |
| E.O. Smith | Loss | 48-15 |
| FRI 9/13 | 3:30 PM | Varsity | Non-League | Normal | Away | Hartford Public | | | | Nevers Road Park - Nevers Road Park XC Trail | |
| Ellis Tech | | |
| Lyman Memorial | | |
| Northwest Catholic | | |
| Norwich Tech | | |
| Portland | | |
| Enfield | | |
| Bristol Eastern | | |
| East Hartford | | |
| East Windsor | | |
| Bristol Central | | |
| South Windsor | | |
| Windham Tech | | |
| Windsor | | |
| University | | |
| THU 9/19 | 3:45 PM | Varsity | League | Normal | Away | | | | | Coginchaug High School | |
| TUE 9/24 | 3:30 PM | Varsity | League | Normal | Home | Tolland | | | | Wickham Park - Wickham Park | |
| SAT 9/28 | 9:30 AM | Varsity | League | Normal | Away | | | | | Wickham Park | |
| TUE 10/8 | 3:45 PM | Varsity | League | Normal | Away | South Windsor | | | | Nevers Road Park - Nevers Road Park XC Trail | |
| TUE 10/15 | 3:00 AM | Varsity | Postseason | Normal | Away | Tolland | | | | Wickham Park - Wickham Park | |
| Windsor | | |
| Hall | | |
| Central Connecticut Conference (CCC) | | |
| Wethersfield | | |
| Bristol Central | | |
| Bristol Eastern | | |
| Avon | | |
| Berlin | | |
| Bloomfield | | |
| Conard | | |
| East Hartford | | |
| E.O. Smith | | |
| Enfield | | |
| RHAM | | |
| Rocky Hill | | |
| Simsbury | | |
| Southington | | |
| South Windsor | | |
| Platt | | |
| Plainville | | |
| Maloney | | |
| Manchester | | |
| Middletown | | |
| New Britain | | |
| Newington | | |
| Northwest Catholic | | |
| Lewis Mills | | |
| Farmington | | |
| Glastonbury | | |