| Round 1 |
|---|
| 1 |  | Dartmouth High School Sailing | 4-5-6 | vs | 1-2-3 | Greenwich Academy Varsity |  |
| 2 |  | Wellesley High School Varsity | 2-5-6 | vs | 1-3-4 | Milton Academy Mustangs |  |
| 3 |  | Lincoln Academy Eagles | 1-3-4 | vs | 2-5-6 | Marthas Vineyard RHS Vineyarders |  |
| 4 | | Dartmouth High School Sailing | 3-4-5 | vs | 1-2-6 | Fairfield Ludlowe High School Falcons |  |
| 5 | | Lincoln Academy Eagles | 3-4-5 | vs | 1-2-6 | Greenwich Academy Varsity | |
| 6 | | Milton Academy Mustangs | 1-2-3 | vs | 4-5-6 | Marthas Vineyard RHS Vineyarders | |
| 7 | | Wellesley High School Varsity | 2-3-4 | vs | 1-5-6 | Dartmouth High School Sailing | |
| 8 | | Lincoln Academy Eagles | 3-4-5 | vs | 1-2-6 | Fairfield Ludlowe High School Falcons | |
| 9 | | Greenwich Academy Varsity | 1-3-6 | vs | 2-4-5 | Marthas Vineyard RHS Vineyarders | |
| 10 | | Lincoln Academy Eagles | 3-4-5 | vs | 1-2-6 | Wellesley High School Varsity | |
| 11 | | Milton Academy Mustangs | 1-2-5 | vs | 3-4-6 | Dartmouth High School Sailing | |
| 12 | | Greenwich Academy Varsity | 1-2-6 | vs | 3-4-5 | Fairfield Ludlowe High School Falcons | |
| 13 | | Milton Academy Mustangs | 1-2-4 | vs | 3-5-6 | Lincoln Academy Eagles | |
| 14 | | Greenwich Academy Varsity | 3-4-5 | vs | 1-2-6 | Wellesley High School Varsity | |
| 15 | | Fairfield Ludlowe High School Falcons | 1-2-4 | vs | 3-5-6 | Marthas Vineyard RHS Vineyarders | |
| 16 | | Greenwich Academy Varsity | 3-4-6 | vs | 1-2-5 | Milton Academy Mustangs | |
| 17 | | Fairfield Ludlowe High School Falcons | 1-2-4 | vs | 3-5-6 | Wellesley High School Varsity | |
| 18 | | Dartmouth High School Sailing | 1-4-6 | vs | 2-3-5 | Marthas Vineyard RHS Vineyarders | |
| 19 | | Fairfield Ludlowe High School Falcons | 1-5-6 | vs | 2-3-4 | Milton Academy Mustangs | |
| 20 | | Dartmouth High School Sailing | 1-5-6 | vs | 2-3-4 | Lincoln Academy Eagles | |
| 21 | | Wellesley High School Varsity | 1-2-4 | vs | 3-5-6 | Marthas Vineyard RHS Vineyarders | |
| Round 2 |
|---|
| 22 | | Dartmouth High School Sailing | 3-5-6 | vs | 1-2-4 | Greenwich Academy Varsity | |
| 23 | | Wellesley High School Varsity | 1-5-6 | vs | 2-3-4 | Milton Academy Mustangs | |
| 24 | | Lincoln Academy Eagles | 1-2-5 | vs | 3-4-6 | Marthas Vineyard RHS Vineyarders | |
| 25 | | Dartmouth High School Sailing | 1-5-6 | vs | 2-3-4 | Fairfield Ludlowe High School Falcons | |
| 26 | | Lincoln Academy Eagles | 4-5-6 | vs | 1-2-3 | Greenwich Academy Varsity | |
| 27 | | Milton Academy Mustangs | 1-2-6 | vs | 3-4-5 | Marthas Vineyard RHS Vineyarders | |
| 28 | | Wellesley High School Varsity | 1-3-4 | vs | 2-5-6 | Dartmouth High School Sailing | |
| 29 | | Lincoln Academy Eagles | 2-3-6 | vs | 1-4-5 | Fairfield Ludlowe High School Falcons | |
| 30 | | Greenwich Academy Varsity | 1-2-3 | vs | 4-5-6 | Marthas Vineyard RHS Vineyarders | |
| 31 | | Lincoln Academy Eagles | 2-3-5 | vs | 1-4-6 | Wellesley High School Varsity | |
| 32 | | Milton Academy Mustangs | 1-2-6 | vs | 3-4-5 | Dartmouth High School Sailing | |
| 33 | | Greenwich Academy Varsity | 2-4-6 | vs | 1-3-5 | Fairfield Ludlowe High School Falcons | |
| 34 | | Milton Academy Mustangs | 1-2-5 | vs | 3-4-6 | Lincoln Academy Eagles | |
| 35 | | Greenwich Academy Varsity | 1-3-4 | vs | 2-5-6 | Wellesley High School Varsity | |
| 36 | | Fairfield Ludlowe High School Falcons | 1-2-3 | vs | 4-5-6 | Marthas Vineyard RHS Vineyarders | |
| 37 | | Greenwich Academy Varsity | 2-4-5 | vs | 1-3-6 | Milton Academy Mustangs | |
| 38 | | Fairfield Ludlowe High School Falcons | 2-3-5 | vs | 1-4-6 | Wellesley High School Varsity | |
| 39 | | Dartmouth High School Sailing | 1-5-6 | vs | 2-3-4 | Marthas Vineyard RHS Vineyarders | |
| 40 | | Fairfield Ludlowe High School Falcons | 1-4-5 | vs | 2-3-6 | Milton Academy Mustangs | |
| 41 | | Dartmouth High School Sailing | 3-4-5 | vs | 1-2-6 | Lincoln Academy Eagles | |
| 42 | | Wellesley High School Varsity | 2-4-6 | vs | 1-3-5 | Marthas Vineyard RHS Vineyarders | |
