| Wed, Sep 8 | MV vs Mashpee | Mashpee home course | Mashpee, MA | | | |
| Sat, Sep 11 | Martha's Vineyard | Manuel Correllus State Forest | Oak Bluffs, MA | | | |
| Wed, Sep 15 | MV vs Stang | Bishop Stang | Dartmouth, MA | | | |
| Tue, Sep 21 | MV vs Barnstable | Hathaway's Pond | Barnstable, MA | | | |
| Sat, Sep 25 | Manchester Invitational | Derryfield Park | Manchester, NH | | | |
| Wed, Sep 29 | MV vs Coyle | Manuel Correllus State Forest | Oak Bluffs, MA | | | |
| Sat, Oct 2 | Bay State Cross-Country Invitational | Wrentham Development Center | Wrentham, MA | 9:30 AM | | |
| Sat, Oct 16 | Brown Invitational | Goddard Memorial State Park | Warwick, RI | | | |
| Mon, Oct 18 | MV vs Somerset | Somerset Middle School | Somerset, MA | | | |
| Wed, Oct 20 | MV vs Bishop Feehan | Manuel Correllus State Forest | Oak Bluffs, MA | | | |
| Sat, Oct 23 | EAC League Meet | Borderland State Park | North Easton, MA | | | |
| Wed, Nov 3 | MV vs Malden Catholic | Franklin Park | Boston, MA | | | |
| Sat, Nov 6 | MSTCA Invitational | Wrentham Development Center | Wrentham, MA | 9:30 AM | | |
| Sat, Nov 13 | MIAA Eastern Massachusetts Divisional Championship | Franklin Park | Boston, MA | | | |
| Sat, Nov 20 | MIAA All-State Championship | Gardner Golf Course | Gardner, MA | 11:00 AM | | |
