| Flight 1 (Round 1) |
| 1 |  | Cape Elizabeth High School Capers | 1 | 2 | 3 | vs | 4 | 5 | 6 | Brookline High Warriors |  |
| 2 |  | Unregistered-NESSA Southern ME | 7 | 8 | 9 | vs | 10 | 11 | 12 | Portland High School Bulldogs |  |
| 3 |  | Falmouth High School (ME) Yachtsmen | 13 | 14 | 15 | vs | 16 | 17 | 18 | Yarmouth High School Clippers |  |
| Flight 2 |
| 4 |  | Unregistered-NESSA Southern ME | 1 | 2 | 3 | vs | 4 | 5 | 6 | Cape Elizabeth High School Capers |  |
| 5 |  | Yarmouth High School Clippers | 7 | 8 | 9 | vs | 10 | 11 | 12 | Brookline High Warriors |  |
| 6 |  | Portland High School Bulldogs | 13 | 14 | 15 | vs | 16 | 17 | 18 | Falmouth High School (ME) Yachtsmen |  |
| Flight 3 |
| 7 |  | Yarmouth High School Clippers | 1 | 2 | 3 | vs | 4 | 5 | 6 | Unregistered-NESSA Southern ME |  |
| 8 |  | Portland High School Bulldogs | 7 | 8 | 9 | vs | 10 | 11 | 12 | Cape Elizabeth High School Capers |  |
| 9 |  | Falmouth High School (ME) Yachtsmen | 13 | 14 | 15 | vs | 16 | 17 | 18 | Brookline High Warriors |  |
| Flight 4 |
| 10 |  | Portland High School Bulldogs | 1 | 2 | 3 | vs | 4 | 5 | 6 | Yarmouth High School Clippers |  |
| 11 |  | Brookline High Warriors | 7 | 8 | 9 | vs | 10 | 11 | 12 | Unregistered-NESSA Southern ME |  |
| 12 |  | Cape Elizabeth High School Capers | 13 | 14 | 15 | vs | 16 | 17 | 18 | Falmouth High School (ME) Yachtsmen |  |