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