| Flight 1 (Gold Cup Round Robin) |
| 1 |  | Fairfield Ludlowe High School Falcons | 4 | 5 | 6 | vs | 13 | 14 | 15 | Brunswick School Bruins |  |
| 2 |  | Darien High School Blue Wave | 7 | 8 | 9 | vs | 22 | 23 | 24 | Greens Farms Academy Dragons |  |
| 3 |  | Greenwich Academy Varsity | 19 | 20 | 21 | vs | 1 | 2 | 3 | Greenwich High School Cardinals |  |
| Flight 2 |
| 4 | | Darien High School Blue Wave | 7 | 8 | 9 | vs | 4 | 5 | 6 | Fairfield Ludlowe High School Falcons | |
| 5 | | Greenwich Academy Varsity | 19 | 20 | 21 | vs | 13 | 14 | 15 | Brunswick School Bruins | |
| 6 | | Greenwich High School Cardinals | 1 | 2 | 3 | vs | 22 | 23 | 24 | Greens Farms Academy Dragons | |
| Flight 3 |
| 7 | | Greenwich Academy Varsity | 19 | 20 | 21 | vs | 7 | 8 | 9 | Darien High School Blue Wave | |
| 8 | | Greens Farms Academy Dragons | 22 | 23 | 24 | vs | 4 | 5 | 6 | Fairfield Ludlowe High School Falcons | |
| 9 | | Brunswick School Bruins | 13 | 14 | 15 | vs | 1 | 2 | 3 | Greenwich High School Cardinals | |
| Flight 4 |
| 10 | | Greens Farms Academy Dragons | 22 | 23 | 24 | vs | 19 | 20 | 21 | Greenwich Academy Varsity | |
| 11 | | Brunswick School Bruins | 13 | 14 | 15 | vs | 7 | 8 | 9 | Darien High School Blue Wave | |
| 12 | | Greenwich High School Cardinals | 1 | 2 | 3 | vs | 4 | 5 | 6 | Fairfield Ludlowe High School Falcons | |
| Flight 5 |
| 13 | | Brunswick School Bruins | 13 | 14 | 15 | vs | 22 | 23 | 24 | Greens Farms Academy Dragons | |
| 14 | | Fairfield Ludlowe High School Falcons | 4 | 5 | 6 | vs | 19 | 20 | 21 | Greenwich Academy Varsity | |
| 15 | | Greenwich High School Cardinals | 1 | 2 | 3 | vs | 7 | 8 | 9 | Darien High School Blue Wave | |
