| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| TUE 9/10 | 4:30 PM | Varsity | League | Normal | Away | Griswold | | | | Griswold High School - Hopeville State Park | 2:10 PM - P/U Flanders - Shared w/Girls |
| Stonington | | |
| TUE 9/17 | 4:30 PM | Varsity | League | Normal | Home | Stonington | | | | Rocky Neck State Park - Rocky Neck State Park | |
| Woodstock Academy | | |
| TUE 9/24 | 4:00 PM | Varsity | League | Normal | Away | Fitch | | | | Haley Farm State Park - Haley Farm State Park | 2:10 PM - P/U Flanders - Share W/Girls Xcountry |
| TUE 10/1 | 4:30 PM | Varsity | League | Normal | Home | New London | | | | East Lyme High School | |
| NFA | | |
| Putnam | | |
| Tourtellotte | | |
| TUE 10/8 | 4:00 PM | Varsity | League | Normal | Away | Ledyard | | | | Ledyard High School - Ledyard High School Track | 2:00 PM - Share w/Girls Xcountry |
| THU 10/17 | 1:30 PM | Varsity | Postseason | Normal | Away | Lyman Memorial | | | | Norwich Golf Course - Norwich Golf Course | 10:30 AM - Shared w/Girls Xcountry |
| Montville | | |
| Killingly | | |
| Ledyard | | |
| Griswold | | |
| Bacon Academy | | |
| Fitch | | |
| Putnam | | |
| St. Bernard | | |
| Stonington | | |
| Plainfield | | |
| New London | | |
| NFA | | |
| Waterford | | |
| Wheeler | | |
| Windham | | |
| Woodstock Academy | | |
| Tourtellotte | | |