| Tue, Sep 7 | Time trial | Larz Anderson Park | Brookline, MA | | | |
| Tue, Sep 14 | Brookline & Wellesley v. Milton | Houghton's Pond | Milton, MA | | | |
| Sat, Sep 18 | Hartford Riverfront Invitational | Riverside Park | Hartford, CT | | | |
| Tue, Sep 21 | Brookline v. Braintree | Braintree HS | Braintree, MA | | | |
| Sat, Sep 25 | Manchester Invitational | Derryfield Park | Manchester, NH | | | |
| Tue, Sep 28 | Brookline vs. Norwood vs. Walpole | Walpole HS | Walpole, MA | | | |
| Sat, Oct 2 | Bay State Cross-Country Invitational | Wrentham Development Center | Wrentham, MA | 9:30 AM | | |
| Tue, Oct 5 | @ Framingham & Natick v. Brookline | Framingham HS | Framingham, MA | | | |
| Tue, Oct 12 | Brookline v. Needham | Cutler Park | Needham, MA | | | |
| Sat, Oct 16 | Bob McIntyre Frosh-Soph Meet | Barnstable County Fairgrounds | Falmouth, MA | | | |
| Sat, Oct 16 | Brown Invitational | Goddard Memorial State Park | Warwick, RI | | | |
| Sat, Oct 16 | Catholic Memorial Invitational | Franklin Park | Boston, MA | 9:30 AM | | |
| Tue, Oct 19 | Weymouth vs. Brookline vs. Dedham | Wompatuck State park | Weymouth, MA | | | |
| Tue, Oct 26 | Brookline v. Newton North | Larz Anderson Park | Brookline, MA | 3:45 PM | | |
| Sat, Oct 30 | Bay State Conference Meet | Norwood HS XC | Norwood, MA | 9:00 AM | | |
| 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 | | | |
