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