| Round Two |
|---|
| 11 |  | St. Johns Prep Varsity | 3-4-5 | vs | 1-2-6 | Hingham High School Habormen |  |
| 12 |  | Lincoln Sudbury Reginal High School Warriors | 2-4-5 | vs | 1-3-6 | Winchester High School Sachems |  |
| 13 |  | Duxbury High School Dragons | 1-2-3 | vs | 4-5-6 | St. Johns Prep Varsity | |
| 14 | | Hingham High School Habormen | 1-3-6 | vs | 2-4-5 | Lincoln Sudbury Reginal High School Warriors | |
| 15 | | Winchester High School Sachems | 1-2-4 | vs | 3-5-6 | St. Johns Prep Varsity | |
| 16 | | Duxbury High School Dragons | 1-2-5 | vs | 3-4-6 | Hingham High School Habormen | |
| 17 | | Lincoln Sudbury Reginal High School Warriors | 1-4-5 | vs | 2-3-6 | St. Johns Prep Varsity | |
| 18 | | Winchester High School Sachems | 4-5-6 | vs | 1-2-3 | Duxbury High School Dragons | |
| 19 | | Winchester High School Sachems | 3-4-5 | vs | 1-2-6 | Hingham High School Habormen | |
| 20 | | Lincoln Sudbury Reginal High School Warriors | 3-4-5 | vs | 1-2-6 | Duxbury High School Dragons | |
