| Round 1 |
|---|
| 1 |  | Portland High School Bulldogs | 3-4-6 | vs | 1-2-5 | BB&N - Buckingham Browne and Nichols Knights |  |
| 2 |  | Marthas Vineyard RHS Vineyarders | 3-4-6 | vs | 1-2-5 | Barnstable HS Raiders |  |
| 3 |  | Islesboro Central School Eagles | 2-5-6 | vs | 1-3-4 | Boothbay RHS SeaHawks Gold |  |
| 4 |  | Camden Hills RHS Chills | 1-2-3 | vs | 4-5-6 | Yarmouth High School Clippers |  |
| 5 | | Portland High School Bulldogs | 3-4-5 | vs | 1-2-6 | The Prout School Crusaders |  |
| 6 | | Islesboro Central School Eagles | 3-4-5 | vs | 1-2-6 | BB&N - Buckingham Browne and Nichols Knights | |
| 7 | | Camden Hills RHS Chills | 2-4-6 | vs | 1-3-5 | Barnstable HS Raiders | |
| 8 | | Boothbay RHS SeaHawks Gold | 2-4-6 | vs | 1-3-5 | Yarmouth High School Clippers | |
| 9 | | Marthas Vineyard RHS Vineyarders | 1-3-6 | vs | 2-4-5 | Portland High School Bulldogs | |
| 10 | | Islesboro Central School Eagles | 1-2-3 | vs | 4-5-6 | The Prout School Crusaders | |
| 11 | | Boothbay RHS SeaHawks Gold | 4-5-6 | vs | 1-2-3 | BB&N - Buckingham Browne and Nichols Knights | |
| 12 | | Yarmouth High School Clippers | 3-5-6 | vs | 1-2-4 | Barnstable HS Raiders | |
| 13 | | Islesboro Central School Eagles | 2-4-6 | vs | 1-3-5 | Marthas Vineyard RHS Vineyarders | |
| 14 | | Camden Hills RHS Chills | 1-2-3 | vs | 4-5-6 | Portland High School Bulldogs | |
| 15 | | Boothbay RHS SeaHawks Gold | 1-2-3 | vs | 4-5-6 | The Prout School Crusaders | |
| 16 | | BB&N - Buckingham Browne and Nichols Knights | 1-2-3 | vs | 4-5-6 | Yarmouth High School Clippers | |
| 17 | | Camden Hills RHS Chills | 1-2-6 | vs | 3-4-5 | Islesboro Central School Eagles | |
| 18 | | Boothbay RHS SeaHawks Gold | 1-2-6 | vs | 3-4-5 | Marthas Vineyard RHS Vineyarders | |
| 19 | | Barnstable HS Raiders | 1-2-6 | vs | 3-4-5 | Portland High School Bulldogs | |
| 20 | | BB&N - Buckingham Browne and Nichols Knights | 1-2-5 | vs | 3-4-6 | The Prout School Crusaders | |
| 21 | | Boothbay RHS SeaHawks Gold | 1-4-5 | vs | 2-3-6 | Camden Hills RHS Chills | |
| 22 | | Barnstable HS Raiders | 1-3-5 | vs | 2-4-6 | Islesboro Central School Eagles | |
| 23 | | BB&N - Buckingham Browne and Nichols Knights | 1-2-5 | vs | 3-4-6 | Marthas Vineyard RHS Vineyarders | |
| 24 | | Yarmouth High School Clippers | 2-3-6 | vs | 1-4-5 | The Prout School Crusaders | |
| 25 | | Barnstable HS Raiders | | vs | | Boothbay RHS SeaHawks Gold | |
| 26 | | BB&N - Buckingham Browne and Nichols Knights | | vs | | Camden Hills RHS Chills | |
| 27 | | The Prout School Crusaders | | vs | | Marthas Vineyard RHS Vineyarders | |
| 28 | | Portland High School Bulldogs | | vs | | Yarmouth High School Clippers | |
| 29 | | BB&N - Buckingham Browne and Nichols Knights | | vs | | Barnstable HS Raiders | |
| 30 | | The Prout School Crusaders | | vs | | Camden Hills RHS Chills | |
| 31 | | Portland High School Bulldogs | | vs | | Islesboro Central School Eagles | |
| 32 | | Marthas Vineyard RHS Vineyarders | | vs | | Yarmouth High School Clippers | |
| 33 | | The Prout School Crusaders | | vs | | Barnstable HS Raiders | |
| 34 | | Portland High School Bulldogs | | vs | | Boothbay RHS SeaHawks Gold | |
| 35 | | Marthas Vineyard RHS Vineyarders | | vs | | Camden Hills RHS Chills | |
| 36 | | Islesboro Central School Eagles | | vs | | Yarmouth High School Clippers | |
