Sep 6, 2023 @ 12:41:13 EDT
| # | Team 1 | Sails | Sails | Team 2 | |||||||
|---|---|---|---|---|---|---|---|---|---|---|---|
| Flight 1 (Round 1) | |||||||||||
| 1 |  | Greenwich Academy Varsity | 19 | 20 | 21 | vs | 16 | 17 | 18 | Brunswick School Bruins |  |
| 2 |  | Greenwich High School Cardinals | 1 | 2 | 3 | vs | 7 | 8 | 9 | Darien High School Varsity |  |
| 3 |  | Greens Farms Academy Dragons | 4 | 5 | 6 | vs | 10 | 11 | 12 | Staples High School Varsity |  |
| Flight 2 | |||||||||||
| 4 | | Greenwich High School Cardinals | 1 | 2 | 3 | vs | 19 | 20 | 21 | Greenwich Academy Varsity | |
| 5 | | Staples High School Varsity | 10 | 11 | 12 | vs | 16 | 17 | 18 | Brunswick School Bruins | |
| 6 | | Darien High School Varsity | 7 | 8 | 9 | vs | 4 | 5 | 6 | Greens Farms Academy Dragons | |
| Flight 3 | |||||||||||
| 7 | | Staples High School Varsity | 10 | 11 | 12 | vs | 1 | 2 | 3 | Greenwich High School Cardinals | |
| 8 | | Darien High School Varsity | 7 | 8 | 9 | vs | 19 | 20 | 21 | Greenwich Academy Varsity | |
| 9 | | Greens Farms Academy Dragons | 4 | 5 | 6 | vs | 16 | 17 | 18 | Brunswick School Bruins | |
| Flight 4 | |||||||||||
| 10 | | Darien High School Varsity | 7 | 8 | 9 | vs | 10 | 11 | 12 | Staples High School Varsity | |
| 11 | | Brunswick School Bruins | 16 | 17 | 18 | vs | 1 | 2 | 3 | Greenwich High School Cardinals | |
| 12 | | Greenwich Academy Varsity | 19 | 20 | 21 | vs | 4 | 5 | 6 | Greens Farms Academy Dragons | |