| Round 1 |
|---|
| 1 |  | St. John Paul II High School (MA) Varsity | 3-5-6 | vs | 1-2-4 | Marthas Vineyard RHS Vineyarders |  |
| 2 |  | Nantucket High School Nantucket Whalers | 2-4-6 | vs | 1-3-5 | Bishop Stang High Spartans |  |
| 3 |  | Sandwich High School Varsity | 4-5-6 | vs | 1-2-3 | Dartmouth High School Indians |  |
| 4 |  | Barnstable HS Raiders 1 | 1-2-3 | vs | 4-5-6 | Barnstable HS Raiders 2 | |
| 5 | | St. John Paul II High School (MA) Varsity | 3-4-5 | vs | 1-2-6 | Nantucket High School Nantucket Whalers | |
| 6 | | Dartmouth High School Indians | 1-3-5 | vs | 2-4-6 | Marthas Vineyard RHS Vineyarders | |
| 7 | | Barnstable HS Raiders 2 | 4-5-6 | vs | 1-2-3 | Bishop Stang High Spartans | |
| 8 | | Barnstable HS Raiders 1 | 1-2-4 | vs | 3-5-6 | Sandwich High School Varsity | |
| 9 | | Nantucket High School Nantucket Whalers | 1-2-4 | vs | 3-5-6 | Dartmouth High School Indians | |
| 10 | | St. John Paul II High School (MA) Varsity | 1-2-3 | vs | 4-5-6 | Barnstable HS Raiders 2 | |
| 11 | | Sandwich High School Varsity | 4-5-6 | vs | 1-2-3 | Marthas Vineyard RHS Vineyarders | |
| 12 | | Barnstable HS Raiders 1 | 4-5-6 | vs | 1-2-3 | Bishop Stang High Spartans | |
| 13 | | Barnstable HS Raiders 2 | 4-5-6 | vs | 1-2-3 | Dartmouth High School Indians | |
| 14 | | Nantucket High School Nantucket Whalers | 1-3-4 | vs | 2-5-6 | Sandwich High School Varsity | |
| 15 | | Bishop Stang High Spartans | 2-3-4 | vs | 1-5-6 | St. John Paul II High School (MA) Varsity | |
| 16 | | Barnstable HS Raiders 1 | 4-5-6 | vs | 1-2-3 | Marthas Vineyard RHS Vineyarders | |
| 17 | | Sandwich High School Varsity | 1-2-3 | vs | 4-5-6 | Barnstable HS Raiders 2 | |
| 18 | | Dartmouth High School Indians | 1-3-5 | vs | 2-4-6 | Bishop Stang High Spartans | |
| 19 | | Marthas Vineyard RHS Vineyarders | 1-2-5 | vs | 3-4-6 | Nantucket High School Nantucket Whalers | |
| 20 | | St. John Paul II High School (MA) Varsity | 1-2-5 | vs | 3-4-6 | Barnstable HS Raiders 1 | |
| 21 | | Bishop Stang High Spartans | 1-3-4 | vs | 2-5-6 | Sandwich High School Varsity | |
| 22 | | Barnstable HS Raiders 2 | 4-5-6 | vs | 1-2-3 | Marthas Vineyard RHS Vineyarders | |
| 23 | | Dartmouth High School Indians | 1-2-4 | vs | 3-5-6 | St. John Paul II High School (MA) Varsity | |
| 24 | | Barnstable HS Raiders 1 | 3-4-6 | vs | 1-2-5 | Nantucket High School Nantucket Whalers | |
| 25 | | Marthas Vineyard RHS Vineyarders | 1-2-6 | vs | 3-4-5 | Bishop Stang High Spartans | |
| 26 | | St. John Paul II High School (MA) Varsity | 2-3-4 | vs | 1-5-6 | Sandwich High School Varsity | |
| 27 | | Nantucket High School Nantucket Whalers | 1-2-6 | vs | 3-4-5 | Barnstable HS Raiders 2 | |
| 28 | | Barnstable HS Raiders 1 | 4-5-6 | vs | 1-2-3 | Dartmouth High School Indians | |
