| Tue, Sep 14 | Needham vs. Natick vs. Norwood | Cutler Park | Needham, MA | 3:45 PM | | |
| Tue, Sep 21 | Needham vs. Framingham | Framingham HS | Framingham, MA | | | |
| Sat, Sep 25 | Amherst Invitational | Hampshire College XC course | Amherst, MA | | | |
| Tue, Sep 28 | Needham vs. Braintree vs. Dedham | Braintree HS | Braintree, MA | | | |
| Sat, Oct 2 | Bay State Cross-Country Invitational | Wrentham Development Center | Wrentham, MA | 9:30 AM | | |
| Tue, Oct 5 | Needham vs. Weymouth vs. Milton | Cutler Park | Needham, MA | | | |
| Tue, Oct 12 | Brookline v. Needham | Cutler Park | Needham, MA | | | |
| Sat, Oct 16 | Brown Invitational | Goddard Memorial State Park | Warwick, RI | | | |
| Tue, Oct 19 | Needham vs. Walpole vs. Newton North | Walpole HS | Walpole, MA | | | |
| Tue, Oct 26 | Needham vs. Wellesley | Cutler Park | Needham, MA | | | |
| Sat, Oct 30 | Bay State Conference Meet | Norwood HS XC | Norwood, MA | 9:00 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 | | |
