| Round 1 | 
|---|
| 1 |   | Lincoln Academy Eagles | 2-3-4 | vs | 1-5-6 | Moses Brown School Quakers |   | 
| 2 |   | Marthas Vineyard RHS Vineyarders | 2-4-5 | vs | 1-3-6 | Greens Farms Academy Dragons |   | 
| 3 |   | Dartmouth High School Sailing | 3-4-5 | vs | 1-2-6 | Darien High School Blue Wave |   | 
| 4 |   | Sharon High School Eagles | 1-2-3 | vs | 4-5-6 | East Greenwich High School Avengers |   | 
| 5 |   | Lincoln Academy Eagles | 3-5-6 | vs | 1-2-4 | Marthas Vineyard RHS Vineyarders |   | 
| 6 |   | Darien High School Blue Wave | 4-5-6 | vs | 1-2-3 | Moses Brown School Quakers |   | 
| 7 |   | East Greenwich High School Avengers | 2-3-5 | vs | 1-4-6 | Greens Farms Academy Dragons |   | 
| 8 |   | Sharon High School Eagles | 3-4-5 | vs | 1-2-6 | Dartmouth High School Sailing |   | 
| 9 |   | Marthas Vineyard RHS Vineyarders | 1-2-3 | vs | 4-5-6 | Darien High School Blue Wave |   | 
| 10 |   | Lincoln Academy Eagles | 2-5-6 | vs | 1-3-4 | East Greenwich High School Avengers |   | 
| 11 |   | Dartmouth High School Sailing | 1-3-6 | vs | 2-4-5 | Moses Brown School Quakers |   | 
| 12 |   | Sharon High School Eagles | 2-5-6 | vs | 1-3-4 | Greens Farms Academy Dragons |   | 
| 13 |   | East Greenwich High School Avengers | 2-5-6 | vs | 1-3-4 | Darien High School Blue Wave |   | 
| 14 |   | Marthas Vineyard RHS Vineyarders | 1-2-4 | vs | 3-5-6 | Dartmouth High School Sailing |   | 
| 15 |   | Greens Farms Academy Dragons | 1-3-4 | vs | 2-5-6 | Lincoln Academy Eagles |   | 
| 16 |   | Sharon High School Eagles | 1-2-3 | vs | 4-5-6 | Moses Brown School Quakers |   | 
| 17 |   | Dartmouth High School Sailing | 3-5-6 | vs | 1-2-4 | East Greenwich High School Avengers |   | 
| 18 |   | Darien High School Blue Wave | 2-4-6 | vs | 1-3-5 | Greens Farms Academy Dragons |   | 
| 19 |   | Moses Brown School Quakers | 3-5-6 | vs | 1-2-4 | Marthas Vineyard RHS Vineyarders |   | 
| 20 |   | Lincoln Academy Eagles | 3-5-6 | vs | 1-2-4 | Sharon High School Eagles |   | 
| 21 |   | Greens Farms Academy Dragons | 1-3-5 | vs | 2-4-6 | Dartmouth High School Sailing |   | 
| 22 |   | East Greenwich High School Avengers | 1-2-3 | vs | 4-5-6 | Moses Brown School Quakers |   | 
| 23 |   | Darien High School Blue Wave | 1-4-5 | vs | 2-3-6 | Lincoln Academy Eagles |   | 
| 24 |   | Sharon High School Eagles | 2-3-5 | vs | 1-4-6 | Marthas Vineyard RHS Vineyarders |   | 
| 25 |   | Moses Brown School Quakers | 4-5-6 | vs | 1-2-3 | Greens Farms Academy Dragons |   | 
| 26 |   | Lincoln Academy Eagles | 3-4-6 | vs | 1-2-5 | Dartmouth High School Sailing |   | 
| 27 |   | Marthas Vineyard RHS Vineyarders | 3-4-6 | vs | 1-2-5 | East Greenwich High School Avengers |   | 
| 28 |   | Sharon High School Eagles | 3-5-6 | vs | 1-2-4 | Darien High School Blue Wave |   | 
| Round 2 | 
|---|
| 29 |   | Lincoln Academy Eagles | 1-5-6 | vs | 2-3-4 | Moses Brown School Quakers |   | 
| 30 |   | Marthas Vineyard RHS Vineyarders | 1-3-4 | vs | 2-5-6 | Greens Farms Academy Dragons |   | 
| 31 |   | Dartmouth High School Sailing | 1-2-5 | vs | 3-4-6 | Darien High School Blue Wave |   | 
| 32 |   | Sharon High School Eagles | 1-2-4 | vs | 3-5-6 | East Greenwich High School Avengers |   | 
| 33 |   | Lincoln Academy Eagles | 4-5-6 | vs | 1-2-3 | Marthas Vineyard RHS Vineyarders |   | 
| 34 |   | Darien High School Blue Wave | 1-4-5 | vs | 2-3-6 | Moses Brown School Quakers |   | 
| 35 |   | East Greenwich High School Avengers | 2-3-4 | vs | 1-5-6 | Greens Farms Academy Dragons |   | 
| 36 |   | Sharon High School Eagles | 1-2-3 | vs | 4-5-6 | Dartmouth High School Sailing |   | 
| 37 |   | Marthas Vineyard RHS Vineyarders | 2-3-4 | vs | 1-5-6 | Darien High School Blue Wave |   | 
| 38 |   | Lincoln Academy Eagles | 3-4-6 | vs | 1-2-5 | East Greenwich High School Avengers |   | 
| 39 |   | Dartmouth High School Sailing | 1-3-6 | vs | 2-4-5 | Moses Brown School Quakers |   | 
| 40 |   | Sharon High School Eagles | 1-3-4 | vs | 2-5-6 | Greens Farms Academy Dragons |   | 
| 41 |   | East Greenwich High School Avengers | 1-2-5 | vs | 3-4-6 | Darien High School Blue Wave |   | 
| 42 |   | Marthas Vineyard RHS Vineyarders | 2-4-5 | vs | 1-3-6 | Dartmouth High School Sailing |   | 
| 43 |   | Greens Farms Academy Dragons | 1-5-6 | vs | 2-3-4 | Lincoln Academy Eagles |   | 
| 44 |   | Sharon High School Eagles | 1-2-3 | vs | 4-5-6 | Moses Brown School Quakers |   | 
| 45 |   | Dartmouth High School Sailing | 1-4-6 | vs | 2-3-5 | East Greenwich High School Avengers |   | 
| 46 |   | Darien High School Blue Wave | 1-3-5 | vs | 2-4-6 | Greens Farms Academy Dragons |   | 
| 47 |   | Moses Brown School Quakers | 2-3-4 | vs | 1-5-6 | Marthas Vineyard RHS Vineyarders |   | 
| 48 |   | Lincoln Academy Eagles | 4-5-6 | vs | 1-2-3 | Sharon High School Eagles |   | 
| 49 |   | Greens Farms Academy Dragons | 3-4-6 | vs | 1-2-5 | Dartmouth High School Sailing |   | 
| 50 |   | East Greenwich High School Avengers | 1-2-6 | vs | 3-4-5 | Moses Brown School Quakers |   | 
| 51 |   | Darien High School Blue Wave | 1-2-6 | vs | 3-4-5 | Lincoln Academy Eagles |   | 
| 52 |   | Sharon High School Eagles | 2-3-6 | vs | 1-4-5 | Marthas Vineyard RHS Vineyarders |   | 
| 53 |   | Moses Brown School Quakers | 3-4-5 | vs | 1-2-6 | Greens Farms Academy Dragons |   | 
| 54 |   | Lincoln Academy Eagles | 1-3-6 | vs | 2-4-5 | Dartmouth High School Sailing |   | 
| 55 |   | Marthas Vineyard RHS Vineyarders | 1-5-6 | vs | 2-3-4 | East Greenwich High School Avengers |   | 
| 56 |   | Sharon High School Eagles | 1-3-5 | vs | 2-4-6 | Darien High School Blue Wave |   |