| Round 1 |
|---|
| 1 |  | The Hotchkiss School Bearcats | 1-2-4 | vs | 3-5-6 | Yarmouth High School Clippers |  |
| 2 |  | Falmouth High School Yachtsmen | 1-3-6 | vs | 2-4-5 | Barnstable HS Raiders |  |
| 3 |  | Sturgis Charter Public School Varsity | 3-4-6 | vs | 1-2-5 | Camden Hills RHS Varsity |  |
| 4 | | Falmouth High School Yachtsmen | 1-2-6 | vs | 3-4-5 | The Hotchkiss School Bearcats | |
| 5 | | Camden Hills RHS Varsity | 1-3-6 | vs | 2-4-5 | Yarmouth High School Clippers | |
| 6 | | Barnstable HS Raiders | 1-2-3 | vs | 4-5-6 | Sturgis Charter Public School Varsity | |
| 7 | | Camden Hills RHS Varsity | 3-5-6 | vs | 1-2-4 | Falmouth High School Yachtsmen | |
| 8 | | Barnstable HS Raiders | 2-3-6 | vs | 1-4-5 | The Hotchkiss School Bearcats | |
| 9 | | Sturgis Charter Public School Varsity | 1-2-6 | vs | 3-4-5 | Yarmouth High School Clippers | |
| 10 | | Barnstable HS Raiders | 3-4-5 | vs | 1-2-6 | Camden Hills RHS Varsity | |
| 11 | | Yarmouth High School Clippers | 1-4-5 | vs | 2-3-6 | Falmouth High School Yachtsmen | |
| 12 | | The Hotchkiss School Bearcats | 2-3-5 | vs | 1-4-6 | Sturgis Charter Public School Varsity | |
| 13 | | Yarmouth High School Clippers | 3-5-6 DNF | vs | 1-2-4 | Barnstable HS Raiders | |
| 14 | | The Hotchkiss School Bearcats | 1-2-3 | vs | 4-5-6 | Camden Hills RHS Varsity | |
| 15 | | Sturgis Charter Public School Varsity | 4-5-6 | vs | 1-2-3 | Falmouth High School Yachtsmen | |
| Round 2 |
|---|
| 16 | | The Hotchkiss School Bearcats | 1-2-3 | vs | 4-5-6 | Yarmouth High School Clippers | |
| 17 | | Falmouth High School Yachtsmen | 1-4-5 | vs | 2-3-6 | Barnstable HS Raiders | |
| 18 | | Sturgis Charter Public School Varsity | 1-4-6 | vs | 2-3-5 | Camden Hills RHS Varsity | |
| 19 | | Falmouth High School Yachtsmen | 3-4-5 | vs | 1-2-6 | The Hotchkiss School Bearcats | |
| 20 | | Camden Hills RHS Varsity | 3-4-6 | vs | 1-2-5 | Yarmouth High School Clippers | |
| 21 | | Barnstable HS Raiders | 1-2-3 | vs | 4-5-6 | Sturgis Charter Public School Varsity | |
| 22 | | Camden Hills RHS Varsity | 2-5-6 | vs | 1-3-4 | Falmouth High School Yachtsmen | |
| 23 | | Barnstable HS Raiders | 2-5-6 | vs | 1-3-4 | The Hotchkiss School Bearcats | |
| 24 | | Sturgis Charter Public School Varsity | 2-3-6 | vs | 1-4-5 | Yarmouth High School Clippers | |
| 25 | | Barnstable HS Raiders | 2-4-5 | vs | 1-3-6 | Camden Hills RHS Varsity | |
| 26 | | Yarmouth High School Clippers | 2-5-6 | vs | 1-3-4 | Falmouth High School Yachtsmen | |
| 27 | | The Hotchkiss School Bearcats | 1-2-4 | vs | 3-5-6 | Sturgis Charter Public School Varsity | |
| 28 | | Yarmouth High School Clippers | 4-5-6 DNS,DNS,DNS | vs | 1-2-3 | Barnstable HS Raiders | |
| 29 | | The Hotchkiss School Bearcats | 1-2-3 | vs | 4-5-6 | Camden Hills RHS Varsity | |
| 30 | | Sturgis Charter Public School Varsity | 3-4-5 | vs | 1-2-6 | Falmouth High School Yachtsmen | |
