| Round 1 |
|---|
| 1 |  | Boston College High School Eagles | 4-5-6 | vs | 1-2-3 | The Hotchkiss School Bearcats |  |
| 2 |  | Tabor Academy Seawolves | 1-2-3 | vs | 4-5-6 | Portsmouth Abbey School Ravens |  |
| 3 |  | Greenwich High School Cardinals | 3-4-6 | vs | 1-2-5 | St. George's School Dragons |  |
| 4 |  | Milton Academy Mustangs | 1-2-3 | vs | 4-5-6 | Falmouth High School Yachtsmen |  |
| 5 | | Boston College High School Eagles | 4-5-6 | vs | 1-2-3 | Tabor Academy Seawolves | |
| 6 | | St. George's School Dragons | 1-2-6 | vs | 3-4-5 | The Hotchkiss School Bearcats | |
| 7 | | Falmouth High School Yachtsmen | 1-2-5 | vs | 3-4-6 | Portsmouth Abbey School Ravens | |
| 8 | | Milton Academy Mustangs | 1-2-3 | vs | 4-5-6 | Greenwich High School Cardinals | |
| 9 | | Tabor Academy Seawolves | 1-5-6 | vs | 2-3-4 | St. George's School Dragons | |
| 10 | | Boston College High School Eagles | 4-5-6 | vs | 1-2-3 | Falmouth High School Yachtsmen | |
| 11 | | Greenwich High School Cardinals | 1-5-6 | vs | 2-3-4 | The Hotchkiss School Bearcats | |
| 12 | | Milton Academy Mustangs | 1-2-4 | vs | 3-5-6 | Portsmouth Abbey School Ravens | |
| 13 | | Falmouth High School Yachtsmen | 3-4-6 | vs | 1-2-5 | St. George's School Dragons | |
| 14 | | Tabor Academy Seawolves | 1-2-3 | vs | 4-5-6 | Greenwich High School Cardinals | |
| 15 | | Portsmouth Abbey School Ravens | 3-4-6 | vs | 1-2-5 | Boston College High School Eagles | |
| 16 | | Milton Academy Mustangs | 1-2-4 DSQ | vs | 3-5-6 | The Hotchkiss School Bearcats | |
| 17 | | Greenwich High School Cardinals | 1-2-3 | vs | 4-5-6 | Falmouth High School Yachtsmen | |
| 18 | | St. George's School Dragons | 1-3-5 | vs | 2-4-6 | Portsmouth Abbey School Ravens | |
| 19 | | The Hotchkiss School Bearcats | 1-2-4 | vs | 3-5-6 | Tabor Academy Seawolves | |
| 20 | | Boston College High School Eagles | 4-5-6 | vs | 1-2-3 | Milton Academy Mustangs | |
| 21 | | Portsmouth Abbey School Ravens | 3-5-6 | vs | 1-2-4 | Greenwich High School Cardinals | |
| 22 | | Falmouth High School Yachtsmen | 4-5-6 | vs | 1-2-3 | The Hotchkiss School Bearcats | |
| 23 | | St. George's School Dragons | 1-2-3 | vs | 4-5-6 | Boston College High School Eagles | |
| 24 | | Milton Academy Mustangs | 1-2-3 | vs | 4-5-6 | Tabor Academy Seawolves | |
| 25 | | The Hotchkiss School Bearcats | 2-3-4 | vs | 1-5-6 | Portsmouth Abbey School Ravens | |
| 26 | | Boston College High School Eagles | 3-5-6 | vs | 1-2-4 | Greenwich High School Cardinals | |
| 27 | | Tabor Academy Seawolves | 1-2-4 | vs | 3-5-6 | Falmouth High School Yachtsmen | |
| 28 | | Milton Academy Mustangs | 2-3-6 | vs | 1-4-5 | St. George's School Dragons | |
| Round 2 |
|---|
| 29 | | The Hotchkiss School Bearcats | 1-2-3 | vs | 4-5-6 | Boston College High School Eagles | |
| 30 | | Portsmouth Abbey School Ravens | 2-3-6 | vs | 1-4-5 | Tabor Academy Seawolves | |
| 31 | | St. George's School Dragons | 1-2-3 | vs | 4-5-6 | Greenwich High School Cardinals | |
| 32 | | Falmouth High School Yachtsmen | 2-5-6 | vs | 1-3-4 | Milton Academy Mustangs | |
| 33 | | Tabor Academy Seawolves | 1-2-3 | vs | 4-5-6 | Boston College High School Eagles | |
| 34 | | The Hotchkiss School Bearcats | 3-4-6 | vs | 1-2-5 | St. George's School Dragons | |
| 35 | | Portsmouth Abbey School Ravens | 3-5-6 | vs | 1-2-4 | Falmouth High School Yachtsmen | |
| 36 | | Greenwich High School Cardinals | 3-4-6 DSQ | vs | 1-2-5 | Milton Academy Mustangs | |
| 37 | | St. George's School Dragons | 1-2-6 | vs | 3-4-5 | Tabor Academy Seawolves | |
| 38 | | Falmouth High School Yachtsmen | 1-2-5 | vs | 3-4-6 | Boston College High School Eagles | |
| 39 | | The Hotchkiss School Bearcats | 1-2-4 | vs | 3-5-6 | Greenwich High School Cardinals | |
| 40 | | Portsmouth Abbey School Ravens | 4-5-6 | vs | 1-2-3 | Milton Academy Mustangs | |
| 41 | | St. George's School Dragons | 1-2-4 | vs | 3-5-6 | Falmouth High School Yachtsmen | |
| 42 | | Greenwich High School Cardinals | 2-3-6 | vs | 1-4-5 | Tabor Academy Seawolves | |
| 43 | | Boston College High School Eagles | 2-5-6 | vs | 1-3-4 | Portsmouth Abbey School Ravens | |
| 44 | | The Hotchkiss School Bearcats | 1-5-6 | vs | 2-3-4 | Milton Academy Mustangs | |
| 45 | | Falmouth High School Yachtsmen | 3-5-6 | vs | 1-2-4 | Greenwich High School Cardinals | |
| 46 | | Portsmouth Abbey School Ravens | 4-5-6 | vs | 1-2-3 | St. George's School Dragons | |
| 47 | | Tabor Academy Seawolves | 1-2-5 | vs | 3-4-6 | The Hotchkiss School Bearcats | |
| 48 | | Milton Academy Mustangs | 1-2-3 | vs | 4-5-6 | Boston College High School Eagles | |
| 49 | | Greenwich High School Cardinals | 2-3-4 | vs | 1-5-6 | Portsmouth Abbey School Ravens | |
| 50 | | The Hotchkiss School Bearcats | 1-2-4 | vs | 3-5-6 | Falmouth High School Yachtsmen | |
| 51 | | Boston College High School Eagles | 3-5-6 | vs | 1-2-4 | St. George's School Dragons | |
| 52 | | Tabor Academy Seawolves | 1-3-5 | vs | 2-4-6 | Milton Academy Mustangs | |
| 53 | | Portsmouth Abbey School Ravens | 3-5-6 | vs | 1-2-4 | The Hotchkiss School Bearcats | |
| 54 | | Greenwich High School Cardinals | 1-2-3 | vs | 4-5-6 | Boston College High School Eagles | |
| 55 | | Falmouth High School Yachtsmen | 3-5-6 | vs | 1-2-4 | Tabor Academy Seawolves | |
| 56 | | St. George's School Dragons | 3-5-6 | vs | 1-2-4 | Milton Academy Mustangs | |
