| Round 1 |
|---|
| 1 |  | Maury High School Varsity | 4-5-6 | vs | 1-2-3 | Norfolk Academy Bulldogs |  |
| 2 |  | Interscholastic Sailing Association Varsity | 3-5-6 | vs | 1-2-4 | Norfolk Collegiate School Varsity |  |
| 3 |  | Christchurch School Seahorses | 1-2-3 | vs | 4-5-6 | St. Christopher's School Varsity |  |
| 4 | | Interscholastic Sailing Association Varsity | 1-2-4 | vs | 3-5-6 | Maury High School Varsity | |
| 5 | | St. Christopher's School Varsity | 4-5-6 | vs | 1-2-3 | Norfolk Academy Bulldogs | |
| 6 | | Norfolk Collegiate School Varsity | 1-5-6 | vs | 2-3-4 DSQ | Christchurch School Seahorses | |
| 7 | | St. Christopher's School Varsity | 3-4-5 | vs | 1-2-6 DNF | Interscholastic Sailing Association Varsity | |
| 8 | | Norfolk Collegiate School Varsity | 2-3-4 | vs | 1-5-6 | Maury High School Varsity | |
| 9 | | Christchurch School Seahorses | 3-5-6 | vs | 1-2-4 | Norfolk Academy Bulldogs | |
| 10 | | Norfolk Collegiate School Varsity | 1-2-3 | vs | 4-5-6 | St. Christopher's School Varsity | |
| 11 | | Norfolk Academy Bulldogs | 1-2-4 | vs | 3-5-6 | Interscholastic Sailing Association Varsity | |
| 12 | | Maury High School Varsity | 4-5-6 | vs | 1-2-3 | Christchurch School Seahorses | |
| 13 | | Norfolk Academy Bulldogs | 1-3-5 DSQ | vs | 2-4-6 | Norfolk Collegiate School Varsity | |
| 14 | | Maury High School Varsity | 1-4-5 | vs | 2-3-6 | St. Christopher's School Varsity | |
| 15 | | Christchurch School Seahorses | 1-2-4 | vs | 3-5-6 | Interscholastic Sailing Association Varsity | |
| Round 2 |
|---|
| 16 | | Maury High School Varsity | 3-5-6 | vs | 1-2-4 | Norfolk Academy Bulldogs | |
| 17 | | Interscholastic Sailing Association Varsity | 4-5-6 | vs | 1-2-3 | Norfolk Collegiate School Varsity | |
| 18 | | Christchurch School Seahorses | 1-2-3 | vs | 4-5-6 | St. Christopher's School Varsity | |
| 19 | | Interscholastic Sailing Association Varsity | 1-2-4 | vs | 3-5-6 | Maury High School Varsity | |
| 20 | | St. Christopher's School Varsity | 4-5-6 | vs | 1-2-3 | Norfolk Academy Bulldogs | |
| 21 | | Norfolk Collegiate School Varsity | 1-3-4 | vs | 2-5-6 | Christchurch School Seahorses | |
| 22 | | St. Christopher's School Varsity | 4-5-6 | vs | 1-2-3 | Interscholastic Sailing Association Varsity | |
| 23 | | Norfolk Collegiate School Varsity | 1-2-4 | vs | 3-5-6 | Maury High School Varsity | |
| 24 | | Christchurch School Seahorses | 2-3-4 | vs | 1-5-6 | Norfolk Academy Bulldogs | |
| 25 | | Norfolk Collegiate School Varsity | 1-2-3 | vs | 4-5-6 | St. Christopher's School Varsity | |
| 26 | | Norfolk Academy Bulldogs | 1-2-5 | vs | 3-4-6 | Interscholastic Sailing Association Varsity | |
| 27 | | Maury High School Varsity | 4-5-6 | vs | 1-2-3 | Christchurch School Seahorses | |
| 28 | | Norfolk Academy Bulldogs | 3-4-5 | vs | 1-2-6 | Norfolk Collegiate School Varsity | |
| 29 | | Maury High School Varsity | 1-5-6 | vs | 2-3-4 | St. Christopher's School Varsity | |
| 30 | | Christchurch School Seahorses | 1-2-3 | vs | 4-5-6 DNF,DNF,DNF | Interscholastic Sailing Association Varsity | |
| Tiebreaker Round (3) |
|---|
| 31 | | Maury High School Varsity | | vs | | Norfolk Academy Bulldogs | |
| 32 | | Interscholastic Sailing Association Varsity | 1-5-6 | vs | 2-3-4 | Norfolk Collegiate School Varsity | |
| 33 | | Christchurch School Seahorses | | vs | | St. Christopher's School Varsity | |
| 34 | | Interscholastic Sailing Association Varsity | | vs | | Maury High School Varsity | |
| 35 | | St. Christopher's School Varsity | | vs | | Norfolk Academy Bulldogs | |
| 36 | | Norfolk Collegiate School Varsity | 3-4-5 | vs | 1-2-6 | Christchurch School Seahorses | |
| 37 | | St. Christopher's School Varsity | | vs | | Interscholastic Sailing Association Varsity | |
| 38 | | Norfolk Collegiate School Varsity | | vs | | Maury High School Varsity | |
| 39 | | Christchurch School Seahorses | 1-2-5 | vs | 3-4-6 | Norfolk Academy Bulldogs | |
| 40 | | Norfolk Collegiate School Varsity | | vs | | St. Christopher's School Varsity | |
| 41 | | Norfolk Academy Bulldogs | | vs | | Interscholastic Sailing Association Varsity | |
| 42 | | Maury High School Varsity | | vs | | Christchurch School Seahorses | |
| 43 | | Norfolk Academy Bulldogs | 2-5-6 | vs | 1-3-4 | Norfolk Collegiate School Varsity | |
| 44 | | Maury High School Varsity | | vs | | St. Christopher's School Varsity | |
| 45 | | Christchurch School Seahorses | | vs | | Interscholastic Sailing Association Varsity | |
