| Round 1 |
|---|
| 1 |  | Staples High School Varsity | 1-2-3 | vs | 4-5-6 | Weston High School Trojans |  |
| 2 |  | Darien High School Blue Wave | 1-2-4 | vs | 3-5-6 | Greenwich Country Day School Tigers |  |
| 3 |  | Greenwich High School Cardinals | 1-2-3 | vs | 4-5-6 | Sacred Heart Greenwich Varsity |  |
| 4 | | Darien High School Blue Wave | 1-2-4 | vs | 3-5-6 | Staples High School Varsity | |
| 5 | | Sacred Heart Greenwich Varsity | 3-4-5 | vs | 1-2-6 | Weston High School Trojans | |
| 6 | | Greenwich Country Day School Tigers | 3-4-6 | vs | 1-2-5 | Greenwich High School Cardinals | |
| 7 | | Sacred Heart Greenwich Varsity | 4-5-6 | vs | 1-2-3 | Darien High School Blue Wave | |
| 8 | | Greenwich Country Day School Tigers | 1-2-6 DNF | vs | 3-4-5 | Staples High School Varsity | |
| 9 | | Greenwich High School Cardinals | 1-2-3 | vs | 4-5-6 | Weston High School Trojans | |
| 10 | | Greenwich Country Day School Tigers | 1-2-3 | vs | 4-5-6 | Sacred Heart Greenwich Varsity | |
| 11 | | Weston High School Trojans | 3-5-6 | vs | 1-2-4 | Darien High School Blue Wave | |
| 12 | | Staples High School Varsity | 3-5-6 | vs | 1-2-4 | Greenwich High School Cardinals | |
| 13 | | Weston High School Trojans | 3-5-6 | vs | 1-2-4 | Greenwich Country Day School Tigers | |
| 14 | | Staples High School Varsity | 1-2-3 | vs | 4-5-6 | Sacred Heart Greenwich Varsity | |
| 15 | | Greenwich High School Cardinals | 1-3-6 | vs | 2-4-5 | Darien High School Blue Wave | |
