| Wed, Sep 11
| | Landmark School | UMass Mt. Ida Turf F | 1-0 | Story | W |
| Landmark School | UMass Mt. Ida Turf F | Story | |
| Fri, Sep 13
| | Lexington Christian Academ | Lexington Christian | 0-2 | Story | L |
| Lexington Christian Academ | Lexington Christian | Story | |
| Thu, Sep 19
| | Boston Trinity Academy | Boston Trinity Acade | 0-3 | Story | L |
| Boston Trinity Academy | Boston Trinity Acade | Story | |
| Fri, Sep 20
| | Boston University Academy | Boston University A | 1-1 | Story | T |
| Boston University Academy | Boston University A | Story | |
| Tue, Sep 24
| | Cambridge School of Weston | UMass Mt. Ida Turf F | 3-0 | | W |
| Cambridge School of Weston | UMass Mt. Ida Turf F | | |
| Thu, Sep 26
| | Covenant Christian Academy | Covenant Christian A | 0-5 | | L |
| Covenant Christian Academy | Covenant Christian A | | |
| Tue, Oct 08
| 4:00 p.m. | Gann Academy | Gann Academy | | | |
| Gann Academy | Gann Academy | | |
| Tue, Oct 15
| 4:00 p.m. | Boston Trinity Academy | UMass Mt. Ida Turf | | | |
| Boston Trinity Academy | UMass Mt. Ida Turf | | |
| Fri, Oct 18
| 4:00 p.m. | Chapel Hill-Chauncy Hall S | Chapel Hill-Chauncy | | | |
| Chapel Hill-Chauncy Hall S | Chapel Hill-Chauncy | | |
| Tue, Oct 22
| 4:00 p.m. | Waring School | Waring School | | | |
| Waring School | Waring School | | |
| Thu, Oct 24
| 4:00 p.m. | The Newman School | The Newman School | | | |
| The Newman School | The Newman School | | |
| Sat, Oct 26
| 11:00 a.m. | Bradford Christian Academy | Orr Field | | | |
| Bradford Christian Academy | Orr Field | | |
