| Tue, Sep 11 | Brookline v. Walpole & Norwood | Norwood HS XC | Norwood, MA | 4:00 PM | | |
| Thu, Sep 20 | Brooklin v. Framingham & Natick | Elm Bank Park | Natick, MA | 4:00 PM | | |
| Sat, Sep 22 | Amherst Invitational | Hampshire College XC course | Amherst, MA | | | |
| Thu, Sep 27 | Brookline v. Needham | Cutler Park | Needham, MA | 4:00 PM | | |
| Sat, Sep 29 | MSTCA Frank Kelley Invitational | Wrentham Development Center | Wrentham, MA | | | |
| Tue, Oct 2 | Brookline v. Weymouth & Dedham | Wompatuck State park | Weymouth, MA | 4:00 PM | | |
| Wed, Oct 10 | Brookline v. Milton & Wellesley | Larz Anderson Park | Brookline, MA | 4:00 PM | | |
| Sat, Oct 13 | MSTCA Bob McIntyre Twilight Invitational | Barnstable County Fairgrounds | Falmouth, MA | 4:30 PM | | |
| Tue, Oct 16 | Brookline v. Braintree | Braintree HS | Braintree, MA | 4:00 PM | | |
| Tue, Oct 23 | Brookline v. Newton North | Larz Anderson Park | Brookline, MA | 4:00 PM | | |
| Sat, Oct 27 | BSC Conference Meet | Norwood HS XC | Norwood, MA | 10:00 AM | | |
| Sat, Nov 3 | MSTCA Invitational | Wrentham Development Center | Wrentham, MA | 12:15 PM | | |
| Sat, Nov 10 | MIAA EMASS Divisional | Wrentham Development Center | Wrentham, MA | | | |
| Sat, Nov 17 | MIAA All State | Northfield Mountain | Northfield, MA | | | |
| Sat, Nov 24 | Nike New York / Northeast Regional (NXN) | Bowdoin Park | Wappinger Falls, NY | | | |
