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