Odd-numbered teams rotate into next boat while even-numbered teams rotate into previous boat (swap) every 2 races, with starting sails offset for subsequent divisions.
| Team | 1A | 2A | 3A | 4A | 5A | 6A | 7A | 8A | 9A | 10A | 11A | 12A | 13A | 14A | 15A | 16A | |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Christian Brothers Colts 1 | 1 | 1 | 2 | 2 | 3 | 3 | 4 | 4 | 5 | 5 | 6 | 6 | 7 | 7 | 8 | 8 | |
| Christian Brothers Colts 2 | 2 | 2 | 1 | 1 | 18 | 18 | 17 | 17 | 16 | 16 | 15 | 15 | 14 | 14 | 13 | 13 | |
| Donovan Catholic Griffins | 3 | 3 | 4 | 4 | 5 | 5 | 6 | 6 | 7 | 7 | 8 | 8 | 9 | 9 | 10 | 10 | |
| Greenwich Cardinals | 4 | 4 | 3 | 3 | 2 | 2 | 1 | 1 | 18 | 18 | 17 | 17 | 16 | 16 | 15 | 15 | |
| Mamaroneck Tigers | 5 | 5 | 6 | 6 | 7 | 7 | 8 | 8 | 9 | 9 | 10 | 10 | 11 | 11 | 12 | 12 | |
| Portsmouth RI Patriots | 6 | 6 | 5 | 5 | 4 | 4 | 3 | 3 | 2 | 2 | 1 | 1 | 18 | 18 | 17 | 17 | |
| Ridge Red Devils | 7 | 7 | 8 | 8 | 9 | 9 | 10 | 10 | 11 | 11 | 12 | 12 | 13 | 13 | 14 | 14 | |
| Rye Country Day Wildcats 1 | 8 | 8 | 7 | 7 | 6 | 6 | 5 | 5 | 4 | 4 | 3 | 3 | 2 | 2 | 1 | 1 | |
| Rye Country Day Wildcats 2 | 9 | 9 | 10 | 10 | 11 | 11 | 12 | 12 | 13 | 13 | 14 | 14 | 15 | 15 | 16 | 16 | |
| Sacred Heart CT Tigers | 10 | 10 | 9 | 9 | 8 | 8 | 7 | 7 | 6 | 6 | 5 | 5 | 4 | 4 | 3 | 3 | |
| Seton Hall Prep Pirates | 11 | 11 | 12 | 12 | 13 | 13 | 14 | 14 | 15 | 15 | 16 | 16 | 17 | 17 | 18 | 18 | |
| Southern Regional Rams | 12 | 12 | 11 | 11 | 10 | 10 | 9 | 9 | 8 | 8 | 7 | 7 | 6 | 6 | 5 | 5 | |
| St. John the Baptist Cougars | 13 | 13 | 14 | 14 | 15 | 15 | 16 | 16 | 17 | 17 | 18 | 18 | 1 | 1 | 2 | 2 | |
| Staples Wreckers | 14 | 14 | 13 | 13 | 12 | 12 | 11 | 11 | 10 | 10 | 9 | 9 | 8 | 8 | 7 | 7 | |
| Summit Hilltoppers | 15 | 15 | 16 | 16 | 17 | 17 | 18 | 18 | 1 | 1 | 2 | 2 | 3 | 3 | 4 | 4 | |
| The Stony Brook Bears One | 16 | 16 | 15 | 15 | 14 | 14 | 13 | 13 | 12 | 12 | 11 | 11 | 10 | 10 | 9 | 9 | |
| Weston Trojans | 17 | 17 | 18 | 18 | 1 | 1 | 2 | 2 | 3 | 3 | 4 | 4 | 5 | 5 | 6 | 6 | |
| Wilton Warriors | 18 | 18 | 17 | 17 | 16 | 16 | 15 | 15 | 14 | 14 | 13 | 13 | 12 | 12 | 11 | 11 |
| Team | 1B | 2B | 3B | 4B | 5B | 6B | 7B | 8B | 9B | 10B | 11B | 12B | 13B | 14B | 15B | 16B | |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Christian Brothers Colts 1 | 10 | 10 | 11 | 11 | 12 | 12 | 13 | 13 | 14 | 14 | 15 | 15 | 16 | 16 | 17 | 17 | |
| Christian Brothers Colts 2 | 11 | 11 | 10 | 10 | 9 | 9 | 8 | 8 | 7 | 7 | 6 | 6 | 5 | 5 | 4 | 4 | |
| Donovan Catholic Griffins | 12 | 12 | 13 | 13 | 14 | 14 | 15 | 15 | 16 | 16 | 17 | 17 | 18 | 18 | 1 | 1 | |
| Greenwich Cardinals | 13 | 13 | 12 | 12 | 11 | 11 | 10 | 10 | 9 | 9 | 8 | 8 | 7 | 7 | 6 | 6 | |
| Mamaroneck Tigers | 14 | 14 | 15 | 15 | 16 | 16 | 17 | 17 | 18 | 18 | 1 | 1 | 2 | 2 | 3 | 3 | |
| Portsmouth RI Patriots | 15 | 15 | 14 | 14 | 13 | 13 | 12 | 12 | 11 | 11 | 10 | 10 | 9 | 9 | 8 | 8 | |
| Ridge Red Devils | 16 | 16 | 17 | 17 | 18 | 18 | 1 | 1 | 2 | 2 | 3 | 3 | 4 | 4 | 5 | 5 | |
| Rye Country Day Wildcats 1 | 17 | 17 | 16 | 16 | 15 | 15 | 14 | 14 | 13 | 13 | 12 | 12 | 11 | 11 | 10 | 10 | |
| Rye Country Day Wildcats 2 | 18 | 18 | 1 | 1 | 2 | 2 | 3 | 3 | 4 | 4 | 5 | 5 | 6 | 6 | 7 | 7 | |
| Sacred Heart CT Tigers | 1 | 1 | 18 | 18 | 17 | 17 | 16 | 16 | 15 | 15 | 14 | 14 | 13 | 13 | 12 | 12 | |
| Seton Hall Prep Pirates | 2 | 2 | 3 | 3 | 4 | 4 | 5 | 5 | 6 | 6 | 7 | 7 | 8 | 8 | 9 | 9 | |
| Southern Regional Rams | 3 | 3 | 2 | 2 | 1 | 1 | 18 | 18 | 17 | 17 | 16 | 16 | 15 | 15 | 14 | 14 | |
| St. John the Baptist Cougars | 4 | 4 | 5 | 5 | 6 | 6 | 7 | 7 | 8 | 8 | 9 | 9 | 10 | 10 | 11 | 11 | |
| Staples Wreckers | 5 | 5 | 4 | 4 | 3 | 3 | 2 | 2 | 1 | 1 | 18 | 18 | 17 | 17 | 16 | 16 | |
| Summit Hilltoppers | 6 | 6 | 7 | 7 | 8 | 8 | 9 | 9 | 10 | 10 | 11 | 11 | 12 | 12 | 13 | 13 | |
| The Stony Brook Bears One | 7 | 7 | 6 | 6 | 5 | 5 | 4 | 4 | 3 | 3 | 2 | 2 | 1 | 1 | 18 | 18 | |
| Weston Trojans | 8 | 8 | 9 | 9 | 10 | 10 | 11 | 11 | 12 | 12 | 13 | 13 | 14 | 14 | 15 | 15 | |
| Wilton Warriors | 9 | 9 | 8 | 8 | 7 | 7 | 6 | 6 | 5 | 5 | 4 | 4 | 3 | 3 | 2 | 2 |