| Sat, Sep 25 | Amherst Invitational | Hampshire College XC course | Amherst, MA | | | |
| Sat, Oct 2 | Bay State Cross-Country Invitational | Wrentham Development Center | Wrentham, MA | 9:30 AM | | |
| Sat, Oct 16 | Catholic Memorial Invitational | Franklin Park | Boston, MA | 9:30 AM | | |
| Fri, Oct 29 | Dual County All-League Meet | Lincoln-Sudbury RHS Course | Sudbury, 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 | | |
| Sat, Nov 27 | Nike New York / Northeast Regional (NXN) | Bowdoin Park | Wappinger Falls, NY | | | |
