Sep 6, 2023 @ 12:41:14 EDT
| # | Team 1 | Record | Record | Team 2 | |||
|---|---|---|---|---|---|---|---|
| Round 1 | |||||||
| 1 |  | Greenwich Academy Varsity | 3-4-6 | vs | 1-2-5 | Brunswick School Bruins |  |
| 2 |  | Greenwich High School Cardinals | 1-2-3 | vs | 4-5-6 | Darien High School Varsity |  |
| 3 |  | Greens Farms Academy Dragons | 1-2-6 | vs | 3-4-5 | Staples High School Varsity |  |
| 4 | | Greenwich High School Cardinals | 1-2-6 | vs | 3-4-5 | Greenwich Academy Varsity | |
| 5 | | Staples High School Varsity | 2-5-6 DNF | vs | 1-3-4 | Brunswick School Bruins | |
| 6 | | Darien High School Varsity | 3-4-5 | vs | 1-2-6 | Greens Farms Academy Dragons | |
| 7 | | Staples High School Varsity | 3-5-6 | vs | 1-2-4 | Greenwich High School Cardinals | |
| 8 | | Darien High School Varsity | 4-5-6 | vs | 1-2-3 | Greenwich Academy Varsity | |
| 9 | | Greens Farms Academy Dragons | 3-4-5 | vs | 1-2-6 | Brunswick School Bruins | |
| 10 | | Darien High School Varsity | 2-4-6 | vs | 1-3-5 | Staples High School Varsity | |
| 11 | | Brunswick School Bruins | 2-3-4 RAF | vs | 1-5-6 | Greenwich High School Cardinals | |
| 12 | | Greenwich Academy Varsity | 1-3-5 | vs | 2-4-6 | Greens Farms Academy Dragons | |