| Flight 1 (Tiebreaker Round (3)) |
| 31 |  | Maury High School Varsity | 7 | 8 | 9 | vs | 10 | 11 | 12 | Norfolk Academy Bulldogs |  |
| 32 |  | Interscholastic Sailing Association Varsity | 4 | 5 | 6 | vs | 13 | 14 | 15 | Norfolk Collegiate School Varsity |  |
| 33 |  | Christchurch School Seahorses | 1 | 2 | 3 | vs | 16 | 17 | 18 | St. Christopher's School Varsity |  |
| Flight 2 |
| 34 |  | Interscholastic Sailing Association Varsity | 4 | 5 | 6 | vs | 7 | 8 | 9 | Maury High School Varsity |  |
| 35 |  | St. Christopher's School Varsity | 16 | 17 | 18 | vs | 10 | 11 | 12 | Norfolk Academy Bulldogs |  |
| 36 |  | Norfolk Collegiate School Varsity | 13 | 14 | 15 | vs | 1 | 2 | 3 | Christchurch School Seahorses |  |
| Flight 3 |
| 37 |  | St. Christopher's School Varsity | 16 | 17 | 18 | vs | 4 | 5 | 6 | Interscholastic Sailing Association Varsity |  |
| 38 |  | Norfolk Collegiate School Varsity | 13 | 14 | 15 | vs | 7 | 8 | 9 | Maury High School Varsity |  |
| 39 |  | Christchurch School Seahorses | 1 | 2 | 3 | vs | 10 | 11 | 12 | Norfolk Academy Bulldogs |  |
| Flight 4 |
| 40 |  | Norfolk Collegiate School Varsity | 13 | 14 | 15 | vs | 16 | 17 | 18 | St. Christopher's School Varsity |  |
| 41 |  | Norfolk Academy Bulldogs | 10 | 11 | 12 | vs | 4 | 5 | 6 | Interscholastic Sailing Association Varsity |  |
| 42 |  | Maury High School Varsity | 7 | 8 | 9 | vs | 1 | 2 | 3 | Christchurch School Seahorses |  |
| Flight 5 |
| 43 |  | Norfolk Academy Bulldogs | 10 | 11 | 12 | vs | 13 | 14 | 15 | Norfolk Collegiate School Varsity |  |
| 44 |  | Maury High School Varsity | 7 | 8 | 9 | vs | 16 | 17 | 18 | St. Christopher's School Varsity |  |
| 45 |  | Christchurch School Seahorses | 1 | 2 | 3 | vs | 4 | 5 | 6 | Interscholastic Sailing Association Varsity |  |