| Flight 1 (Round 1) |
| 1 |  | Staples High School Varsity | 7 | 8 | 9 | vs | 10 | 11 | 12 | Weston High School Trojans |  |
| 2 |  | Darien High School Blue Wave | 4 | 5 | 6 | vs | 25 | 26 | 27 | Greenwich Country Day School Tigers |  |
| 3 |  | Greenwich High School Cardinals | 1 | 2 | 3 | vs | 28 | 29 | 30 | Sacred Heart Greenwich Varsity |  |
| Flight 2 |
| 4 | | Darien High School Blue Wave | 4 | 5 | 6 | vs | 7 | 8 | 9 | Staples High School Varsity | |
| 5 | | Sacred Heart Greenwich Varsity | 28 | 29 | 30 | vs | 10 | 11 | 12 | Weston High School Trojans | |
| 6 | | Greenwich Country Day School Tigers | 25 | 26 | 27 | vs | 1 | 2 | 3 | Greenwich High School Cardinals | |
| Flight 3 |
| 7 | | Sacred Heart Greenwich Varsity | 28 | 29 | 30 | vs | 4 | 5 | 6 | Darien High School Blue Wave | |
| 8 | | Greenwich Country Day School Tigers | 25 | 26 | 27 | vs | 7 | 8 | 9 | Staples High School Varsity | |
| 9 | | Greenwich High School Cardinals | 1 | 2 | 3 | vs | 10 | 11 | 12 | Weston High School Trojans | |
| Flight 4 |
| 10 | | Greenwich Country Day School Tigers | 25 | 26 | 27 | vs | 28 | 29 | 30 | Sacred Heart Greenwich Varsity | |
| 11 | | Weston High School Trojans | 10 | 11 | 12 | vs | 4 | 5 | 6 | Darien High School Blue Wave | |
| 12 | | Staples High School Varsity | 7 | 8 | 9 | vs | 1 | 2 | 3 | Greenwich High School Cardinals | |
| Flight 5 |
| 13 | | Weston High School Trojans | 10 | 11 | 12 | vs | 25 | 26 | 27 | Greenwich Country Day School Tigers | |
| 14 | | Staples High School Varsity | 7 | 8 | 9 | vs | 28 | 29 | 30 | Sacred Heart Greenwich Varsity | |
| 15 | | Greenwich High School Cardinals | 1 | 2 | 3 | vs | 4 | 5 | 6 | Darien High School Blue Wave | |
