| Flight 1 (Round 1) |
| 1 |  | Staples High School Wreckers | Fl1 | Fl2 | Fl3 | vs | Fl4 | Fl5 | Fl6 | Fairfield Ludlowe High School Falcons |  |
| 2 |  | Greenwich Country Day School Tigers | St1 | St2 | St3 | vs | St4 | St5 | St6 | Darien High School Blue Wave |  |
| Flight 2 |
| 3 |  | Fairfield Prep Jesuits | Fl1 | Fl2 | Fl3 | vs | Fl4 | Fl5 | Fl6 | Weston High School Trojans |  |
| 4 |  | Greenwich Country Day School Tigers | St1 | St2 | St3 | vs | St4 | St5 | St6 | Staples High School Wreckers |  |
| Flight 3 |
| 5 |  | Fairfield Prep Jesuits | Fl1 | Fl2 | Fl3 | vs | Fl4 | Fl5 | Fl6 | Fairfield Ludlowe High School Falcons |  |
| 6 |  | Darien High School Blue Wave | St1 | St2 | St3 | vs | St4 | St5 | St6 | Weston High School Trojans |  |
| Flight 4 |
| 7 |  | Fairfield Prep Jesuits | Fl1 | Fl2 | Fl3 | vs | Fl4 | Fl5 | Fl6 | Greenwich Country Day School Tigers |  |
| 8 |  | Darien High School Blue Wave | St1 | St2 | St3 | vs | St4 | St5 | St6 | Staples High School Wreckers |  |
| Flight 5 |
| 9 |  | Fairfield Ludlowe High School Falcons | Fl1 | Fl2 | Fl3 | vs | Fl4 | Fl5 | Fl6 | Weston High School Trojans |  |
| 10 |  | Darien High School Blue Wave | St1 | St2 | St3 | vs | St4 | St5 | St6 | Fairfield Prep Jesuits |  |
| Flight 6 |
| 11 |  | Fairfield Ludlowe High School Falcons | Fl1 | Fl2 | Fl3 | vs | Fl4 | Fl5 | Fl6 | Greenwich Country Day School Tigers |  |
| 12 |  | Staples High School Wreckers | St1 | St2 | St3 | vs | St4 | St5 | St6 | Weston High School Trojans |  |
| Flight 7 |
| 13 |  | Fairfield Ludlowe High School Falcons | Fl1 | Fl2 | Fl3 | vs | Fl4 | Fl5 | Fl6 | Darien High School Blue Wave |  |
| 14 |  | Staples High School Wreckers | St1 | St2 | St3 | vs | St4 | St5 | St6 | Fairfield Prep Jesuits |  |
| Flight 8 |
| 15 |  | Greenwich Country Day School Tigers | Fl1 | Fl2 | Fl3 | vs | Fl4 | Fl5 | Fl6 | Weston High School Trojans |  |