Oct 2, 2023 @ 16:58:36 EDT
| # | Team 1 | Sails | Sails | Team 2 | |||||||
|---|---|---|---|---|---|---|---|---|---|---|---|
| Flight 1 (Round 1) | |||||||||||
| 1 |  | Rye High School Garnets | 1 | 2 | 3 | vs | 4 | 5 | 6 | St. John the Baptist Cougars |  |
| 2 |  | Mamaroneck High School Tigers | 7 | 8 | 9 | vs | 10 | 11 | 12 | The Stony Brook School Bears |  |
| Flight 2 | |||||||||||
| 3 | | The Stony Brook School Bears | 1 | 2 | 3 | vs | 4 | 5 | 6 | Rye High School Garnets | |
| 4 | | St. John the Baptist Cougars | 7 | 8 | 9 | vs | 10 | 11 | 12 | Mamaroneck High School Tigers | |
| Flight 3 | |||||||||||
| 5 | | The Stony Brook School Bears | 1 | 2 | 3 | vs | 4 | 5 | 6 | St. John the Baptist Cougars | |
| 6 | | Rye High School Garnets | 7 | 8 | 9 | vs | 10 | 11 | 12 | Mamaroneck High School Tigers | |