| Flight 1 (Round 2) |
| 1 |  | Duxbury High School Dragons | 10 | 11 | 12 | vs | 13 | 14 | 15 | Manchester/Essex RHS Hornets |  |
| 2 |  | Dartmouth High School Sailing | 7 | 8 | 9 | vs | 16 | 17 | 18 | Marthas Vineyard RHS Vineyarders |  |
| 3 |  | Boston College High School Eagles | 4 | 5 | 6 | vs | 19 | 20 | 21 | Milton Academy Mustangs |  |
| 4 |  | Wellesley High School Varsity | 1 | 2 | 3 | vs | 22 | 23 | 24 | Sharon High School Varsity |  |
| Flight 2 |
| 5 | | Dartmouth High School Sailing | 7 | 8 | 9 | vs | 10 | 11 | 12 | Duxbury High School Dragons | |
| 6 | | Boston College High School Eagles | 4 | 5 | 6 | vs | 13 | 14 | 15 | Manchester/Essex RHS Hornets | |
| 7 | | Sharon High School Varsity | 22 | 23 | 24 | vs | 16 | 17 | 18 | Marthas Vineyard RHS Vineyarders | |
| 8 | | Milton Academy Mustangs | 19 | 20 | 21 | vs | 1 | 2 | 3 | Wellesley High School Varsity | |
| Flight 3 |
| 9 | | Boston College High School Eagles | 4 | 5 | 6 | vs | 7 | 8 | 9 | Dartmouth High School Sailing | |
| 10 | | Sharon High School Varsity | 22 | 23 | 24 | vs | 10 | 11 | 12 | Duxbury High School Dragons | |
| 11 | | Milton Academy Mustangs | 19 | 20 | 21 | vs | 13 | 14 | 15 | Manchester/Essex RHS Hornets | |
| 12 | | Wellesley High School Varsity | 1 | 2 | 3 | vs | 16 | 17 | 18 | Marthas Vineyard RHS Vineyarders | |
| Flight 4 |
| 13 | | Sharon High School Varsity | 22 | 23 | 24 | vs | 4 | 5 | 6 | Boston College High School Eagles | |
| 14 | | Milton Academy Mustangs | 19 | 20 | 21 | vs | 7 | 8 | 9 | Dartmouth High School Sailing | |
| 15 | | Marthas Vineyard RHS Vineyarders | 16 | 17 | 18 | vs | 10 | 11 | 12 | Duxbury High School Dragons | |
| 16 | | Manchester/Essex RHS Hornets | 13 | 14 | 15 | vs | 1 | 2 | 3 | Wellesley High School Varsity | |
| Flight 5 |
| 17 | | Milton Academy Mustangs | 19 | 20 | 21 | vs | 22 | 23 | 24 | Sharon High School Varsity | |
| 18 | | Marthas Vineyard RHS Vineyarders | 16 | 17 | 18 | vs | 4 | 5 | 6 | Boston College High School Eagles | |
| 19 | | Manchester/Essex RHS Hornets | 13 | 14 | 15 | vs | 7 | 8 | 9 | Dartmouth High School Sailing | |
| 20 | | Wellesley High School Varsity | 1 | 2 | 3 | vs | 10 | 11 | 12 | Duxbury High School Dragons | |
| Flight 6 |
| 21 | | Marthas Vineyard RHS Vineyarders | 16 | 17 | 18 | vs | 19 | 20 | 21 | Milton Academy Mustangs | |
| 22 | | Manchester/Essex RHS Hornets | 13 | 14 | 15 | vs | 22 | 23 | 24 | Sharon High School Varsity | |
| 23 | | Duxbury High School Dragons | 10 | 11 | 12 | vs | 4 | 5 | 6 | Boston College High School Eagles | |
| 24 | | Dartmouth High School Sailing | 7 | 8 | 9 | vs | 1 | 2 | 3 | Wellesley High School Varsity | |
| Flight 7 |
| 25 | | Manchester/Essex RHS Hornets | 13 | 14 | 15 | vs | 16 | 17 | 18 | Marthas Vineyard RHS Vineyarders | |
| 26 | | Duxbury High School Dragons | 10 | 11 | 12 | vs | 19 | 20 | 21 | Milton Academy Mustangs | |
| 27 | | Dartmouth High School Sailing | 7 | 8 | 9 | vs | 22 | 23 | 24 | Sharon High School Varsity | |
| 28 | | Wellesley High School Varsity | 1 | 2 | 3 | vs | 4 | 5 | 6 | Boston College High School Eagles | |
