| Round 1 |
|---|
| 1 |  | Portsmouth Abbey School Ravens | 3-4-6 | vs | 1-2-5 | Tabor Academy Seawolves |  |
| 2 |  | Brunswick School Bruins | 1-2-6 | vs | 3-4-5 | Marthas Vineyard RHS Islanders |  |
| 3 |  | The Hotchkiss School Bearcats | 3-4-5 | vs | 1-2-6 | St. George's School Dragons |  |
| 4 |  | Cape Cod Academy Seahawks | 1-2-6 | vs | 3-4-5 | Duxbury High School Dragons |  |
| 5 | | Portsmouth Abbey School Ravens | 1-2-5 | vs | 3-4-6 | Brunswick School Bruins | |
| 6 | | St. George's School Dragons | 1-2-3 | vs | 4-5-6 | Tabor Academy Seawolves | |
| 7 | | Duxbury High School Dragons | 3-5-6 | vs | 1-2-4 | Marthas Vineyard RHS Islanders | |
| 8 | | Cape Cod Academy Seahawks | 1-2-5 | vs | 3-4-6 | The Hotchkiss School Bearcats | |
| 9 | | Brunswick School Bruins | 3-5-6 | vs | 1-2-4 | St. George's School Dragons | |
| 10 | | Portsmouth Abbey School Ravens | 1-2-6 | vs | 3-4-5 | Duxbury High School Dragons | |
| 11 | | The Hotchkiss School Bearcats | 3-4-6 | vs | 1-2-5 | Tabor Academy Seawolves | |
| 12 | | Cape Cod Academy Seahawks | 1-3-4 | vs | 2-5-6 | Marthas Vineyard RHS Islanders | |
| 13 | | Duxbury High School Dragons | 4-5-6 | vs | 1-2-3 | St. George's School Dragons | |
| 14 | | Brunswick School Bruins | 1-2-5 | vs | 3-4-6 | The Hotchkiss School Bearcats | |
| 15 | | Marthas Vineyard RHS Islanders | 1-4-6 | vs | 2-3-5 | Portsmouth Abbey School Ravens | |
| 16 | | Cape Cod Academy Seahawks | 1-3-4 | vs | 2-5-6 | Tabor Academy Seawolves | |
| 17 | | The Hotchkiss School Bearcats | 1-2-5 | vs | 3-4-6 | Duxbury High School Dragons | |
| 18 | | St. George's School Dragons | 3-4-5 | vs | 1-2-6 | Marthas Vineyard RHS Islanders | |
| 19 | | Tabor Academy Seawolves | 2-3-4 | vs | 1-5-6 | Brunswick School Bruins | |
| 20 | | Portsmouth Abbey School Ravens | 1-4-6 | vs | 2-3-5 | Cape Cod Academy Seahawks | |
| 21 | | Marthas Vineyard RHS Islanders | 2-5-6 | vs | 1-3-4 | The Hotchkiss School Bearcats | |
| 22 | | Duxbury High School Dragons | 3-4-5 | vs | 1-2-6 | Tabor Academy Seawolves | |
| 23 | | St. George's School Dragons | 2-3-5 | vs | 1-4-6 | Portsmouth Abbey School Ravens | |
| 24 | | Cape Cod Academy Seahawks | 4-5-6 | vs | 1-2-3 | Brunswick School Bruins | |
| 25 | | Tabor Academy Seawolves | 1-3-5 | vs | 2-4-6 | Marthas Vineyard RHS Islanders | |
| 26 | | Portsmouth Abbey School Ravens | 3-5-6 | vs | 1-2-4 | The Hotchkiss School Bearcats | |
| 27 | | Brunswick School Bruins | 1-2-5 | vs | 3-4-6 | Duxbury High School Dragons | |
| 28 | | Cape Cod Academy Seahawks | 3-4-6 | vs | 1-2-5 | St. George's School Dragons | |
| Round 2 |
|---|
| 29 | | Tabor Academy Seawolves | 3-4-5 | vs | 1-2-6 | Portsmouth Abbey School Ravens | |
| 30 | | Marthas Vineyard RHS Islanders | 1-2-5 | vs | 3-4-6 | Brunswick School Bruins | |
| 31 | | St. George's School Dragons | 1-3-4 | vs | 2-5-6 | The Hotchkiss School Bearcats | |
| 32 | | Duxbury High School Dragons | 3-4-6 | vs | 1-2-5 | Cape Cod Academy Seahawks | |
| 33 | | Brunswick School Bruins | 2-4-6 | vs | 1-3-5 | Portsmouth Abbey School Ravens | |
| 34 | | Tabor Academy Seawolves | 3-4-6 | vs | 1-2-5 | St. George's School Dragons | |
| 35 | | Marthas Vineyard RHS Islanders | 1-4-5 | vs | 2-3-6 | Duxbury High School Dragons | |
| 36 | | The Hotchkiss School Bearcats | 3-4-5 | vs | 1-2-6 | Cape Cod Academy Seahawks | |
| 37 | | St. George's School Dragons | 1-2-6 | vs | 3-4-5 | Brunswick School Bruins | |
| 38 | | Duxbury High School Dragons | 2-4-6 | vs | 1-3-5 | Portsmouth Abbey School Ravens | |
| 39 | | Tabor Academy Seawolves | 4-5-6 | vs | 1-2-3 | The Hotchkiss School Bearcats | |
| 40 | | Marthas Vineyard RHS Islanders | 1-4-5 | vs | 2-3-6 | Cape Cod Academy Seahawks | |
| 41 | | St. George's School Dragons | 1-2-6 | vs | 3-4-5 | Duxbury High School Dragons | |
| 42 | | The Hotchkiss School Bearcats | 1-4-5 | vs | 2-3-6 | Brunswick School Bruins | |
| 43 | | Portsmouth Abbey School Ravens | 1-5-6 | vs | 2-3-4 | Marthas Vineyard RHS Islanders | |
| 44 | | Tabor Academy Seawolves | 1-2-4 | vs | 3-5-6 | Cape Cod Academy Seahawks | |
| 45 | | Duxbury High School Dragons | 3-4-6 | vs | 1-2-5 | The Hotchkiss School Bearcats | |
| 46 | | Marthas Vineyard RHS Islanders | 3-4-5 | vs | 1-2-6 | St. George's School Dragons | |
| 47 | | Brunswick School Bruins | 1-2-4 | vs | 3-5-6 | Tabor Academy Seawolves | |
| 48 | | Cape Cod Academy Seahawks | 2-3-6 | vs | 1-4-5 | Portsmouth Abbey School Ravens | |
| 49 | | The Hotchkiss School Bearcats | 1-2-5 | vs | 3-4-6 | Marthas Vineyard RHS Islanders | |
| 50 | | Tabor Academy Seawolves | 1-2-5 | vs | 3-4-6 | Duxbury High School Dragons | |
| 51 | | Portsmouth Abbey School Ravens | 1-2-6 | vs | 3-4-5 | St. George's School Dragons | |
| 52 | | Brunswick School Bruins | 1-2-6 | vs | 3-4-5 | Cape Cod Academy Seahawks | |
| 53 | | Marthas Vineyard RHS Islanders | 1-2-4 | vs | 3-5-6 | Tabor Academy Seawolves | |
| 54 | | The Hotchkiss School Bearcats | 3-4-5 | vs | 1-2-6 | Portsmouth Abbey School Ravens | |
| 55 | | Duxbury High School Dragons | 4-5-6 | vs | 1-2-3 | Brunswick School Bruins | |
| 56 | | St. George's School Dragons | 4-5-6 | vs | 1-2-3 | Cape Cod Academy Seahawks | |
