| Round 1 |
|---|
| 1 |  | Rye High School Garnets | 1-2-3 | vs | 4-5-6 | St. John the Baptist Cougars |  |
| 2 |  | Mattituck High School Tuckers | 3-4-6 | vs | 1-2-5 | The Stony Brook School Bears |  |
| 3 |  | Bay Shore High School Marauders | 3-4-5 | vs | 1-2-6 | WHB Hurricane Sailing Hurricanes |  |
| 4 | | Mattituck High School Tuckers | 4-5-6 | vs | 1-2-3 | Rye High School Garnets | |
| 5 | | WHB Hurricane Sailing Hurricanes | 1-5-6 | vs | 2-3-4 | St. John the Baptist Cougars | |
| 6 | | The Stony Brook School Bears | 1-2-3 | vs | 4-5-6 | Bay Shore High School Marauders | |
| 7 | | WHB Hurricane Sailing Hurricanes | 3-4-6 | vs | 1-2-5 | Mattituck High School Tuckers | |
| 8 | | The Stony Brook School Bears | 1-2-6 | vs | 3-4-5 | Rye High School Garnets | |
| 9 | | Bay Shore High School Marauders | 1-3-6 | vs | 2-4-5 | St. John the Baptist Cougars | |
| 10 | | The Stony Brook School Bears | 1-2-3 | vs | 4-5-6 | WHB Hurricane Sailing Hurricanes | |
| 11 | | St. John the Baptist Cougars | 2-3-5 | vs | 1-4-6 | Mattituck High School Tuckers | |
| 12 | | Rye High School Garnets | 1-2-5 | vs | 3-4-6 | Bay Shore High School Marauders | |
| 13 | | St. John the Baptist Cougars | 2-5-6 | vs | 1-3-4 | The Stony Brook School Bears | |
| 14 | | Rye High School Garnets | 1-2-3 | vs | 4-5-6 | WHB Hurricane Sailing Hurricanes | |
| 15 | | Bay Shore High School Marauders | 1-2-5 | vs | 3-4-6 | Mattituck High School Tuckers | |
| Round 2 |
|---|
| 16 | | Rye High School Garnets | 1-2-3 | vs | 4-5-6 | St. John the Baptist Cougars | |
| 17 | | Mattituck High School Tuckers | 4-5-6 | vs | 1-2-3 | The Stony Brook School Bears | |
| 18 | | Bay Shore High School Marauders | 3-4-6 | vs | 1-2-5 | WHB Hurricane Sailing Hurricanes | |
| 19 | | Mattituck High School Tuckers | 4-5-6 | vs | 1-2-3 | Rye High School Garnets | |
| 20 | | WHB Hurricane Sailing Hurricanes | 1-3-4 | vs | 2-5-6 | St. John the Baptist Cougars | |
| 21 | | The Stony Brook School Bears | 1-2-3 | vs | 4-5-6 | Bay Shore High School Marauders | |
| 22 | | WHB Hurricane Sailing Hurricanes | 1-5-6 | vs | 2-3-4 | Mattituck High School Tuckers | |
| 23 | | The Stony Brook School Bears | 3-5-6 | vs | 1-2-4 | Rye High School Garnets | |
| 24 | | Bay Shore High School Marauders | 2-3-6 | vs | 1-4-5 | St. John the Baptist Cougars | |
| 25 | | The Stony Brook School Bears | 1-2-3 | vs | 4-5-6 | WHB Hurricane Sailing Hurricanes | |
| 26 | | St. John the Baptist Cougars | 1-4-5 | vs | 2-3-6 | Mattituck High School Tuckers | |
| 27 | | Rye High School Garnets | 1-2-3 | vs | 4-5-6 | Bay Shore High School Marauders | |
| 28 | | St. John the Baptist Cougars | 4-5-6 | vs | 1-2-3 | The Stony Brook School Bears | |
| 29 | | Rye High School Garnets | 1-2-5 | vs | 3-4-6 | WHB Hurricane Sailing Hurricanes | |
| 30 | | Bay Shore High School Marauders | 1-2-3 | vs | 4-5-6 DNS,DNS,DNS | Mattituck High School Tuckers | |
