| Round 1 |
|---|
| 1 |  | Fairfield Prep Jesuits | 1-2-6 DNF | vs | 3-4-5 DNS | Fairfield Ludlowe High School Falcons |  |
| 2 |  | Staples High School The Wreckers | 2-4-5 | vs | 1-3-6 | Greens Farms Academy Dragons |  |
| 3 |  | Weston High School Trojans | 3-4-6 | vs | 1-2-5 | Greenwich Country Day School Tigers |  |
| 4 | | Staples High School The Wreckers | 1-2-6 | vs | 3-4-5 | Fairfield Prep Jesuits | |
| 5 | | Greenwich Country Day School Tigers | 3-4-6 | vs | 1-2-5 | Fairfield Ludlowe High School Falcons | |
| 6 | | Greens Farms Academy Dragons | 1-2-6 DNF | vs | 3-4-5 | Weston High School Trojans | |
| 7 | | Greenwich Country Day School Tigers | 3-5-6 | vs | 1-2-4 | Staples High School The Wreckers | |
| 8 | | Greens Farms Academy Dragons | 1-3-6 | vs | 2-4-5 | Fairfield Prep Jesuits | |
| 9 | | Weston High School Trojans | 2-5-6 | vs | 1-3-4 | Fairfield Ludlowe High School Falcons | |
| 10 | | Greens Farms Academy Dragons | 1-2-3 | vs | 4-5-6 | Greenwich Country Day School Tigers | |
| 11 | | Fairfield Ludlowe High School Falcons | 2-5-6 | vs | 1-3-4 | Staples High School The Wreckers | |
| 12 | | Fairfield Prep Jesuits | 2-3-4 | vs | 1-5-6 | Weston High School Trojans | |
| 13 | | Fairfield Ludlowe High School Falcons | 3-4-6 | vs | 1-2-5 | Greens Farms Academy Dragons | |
| 14 | | Fairfield Prep Jesuits | 1-3-5 | vs | 2-4-6 | Greenwich Country Day School Tigers | |
| 15 | | Weston High School Trojans | 4-5-6 | vs | 1-2-3 | Staples High School The Wreckers | |
