| Flight 1 (Round 2) |
| 29 |  | Fairfield Prep Jesuits | 4 | 5 | 6 | vs | 1 | 2 | 3 | St. George's School Dragons |  |
| 30 |  | Brunswick School Bruins | 10 | 11 | 12 | vs | 7 | 8 | 9 | Milton Academy Mustangs |  |
| 31 |  | Marblehead High School Fishwagons | 16 | 17 | 18 | vs | 13 | 14 | 15 | Tabor Academy Seawolves |  |
| Flight 2 |
| 32 |  | The Hotchkiss School Bearcats | 4 | 5 | 6 | vs | 1 | 2 | 3 | Greenwich High School Cardinals |  |
| 33 | | Fairfield Prep Jesuits | 10 | 11 | 12 | vs | 7 | 8 | 9 | Brunswick School Bruins | |
| 34 | | Tabor Academy Seawolves | 16 | 17 | 18 | vs | 13 | 14 | 15 | St. George's School Dragons | |
| Flight 3 |
| 35 | | Greenwich High School Cardinals | 4 | 5 | 6 | vs | 1 | 2 | 3 | Milton Academy Mustangs | |
| 36 | | The Hotchkiss School Bearcats | 10 | 11 | 12 | vs | 7 | 8 | 9 | Marblehead High School Fishwagons | |
| 37 | | Brunswick School Bruins | 16 | 17 | 18 | vs | 13 | 14 | 15 | Tabor Academy Seawolves | |
| Flight 4 |
| 38 | | Fairfield Prep Jesuits | 4 | 5 | 6 | vs | 1 | 2 | 3 | Greenwich High School Cardinals | |
| 39 | | Marblehead High School Fishwagons | 10 | 11 | 12 | vs | 7 | 8 | 9 | St. George's School Dragons | |
| 40 | | The Hotchkiss School Bearcats | 16 | 17 | 18 | vs | 13 | 14 | 15 | Milton Academy Mustangs | |
| Flight 5 |
| 41 | | Greenwich High School Cardinals | 4 | 5 | 6 | vs | 1 | 2 | 3 | Tabor Academy Seawolves | |
| 42 | | Brunswick School Bruins | 10 | 11 | 12 | vs | 7 | 8 | 9 | Marblehead High School Fishwagons | |
| 43 | | Milton Academy Mustangs | 16 | 17 | 18 | vs | 13 | 14 | 15 | Fairfield Prep Jesuits | |
| Flight 6 |
| 44 | | The Hotchkiss School Bearcats | 4 | 5 | 6 | vs | 1 | 2 | 3 | St. George's School Dragons | |
| 45 | | Marblehead High School Fishwagons | 10 | 11 | 12 | vs | 7 | 8 | 9 | Greenwich High School Cardinals | |
| 46 | | Tabor Academy Seawolves | 16 | 17 | 18 | vs | 13 | 14 | 15 | Milton Academy Mustangs | |
| Flight 7 |
| 47 | | St. George's School Dragons | 4 | 5 | 6 | vs | 1 | 2 | 3 | Brunswick School Bruins | |
| 48 | | Fairfield Prep Jesuits | 10 | 11 | 12 | vs | 7 | 8 | 9 | The Hotchkiss School Bearcats | |
| 49 | | Milton Academy Mustangs | 16 | 17 | 18 | vs | 13 | 14 | 15 | Marblehead High School Fishwagons | |
| Flight 8 |
| 50 | | Greenwich High School Cardinals | 4 | 5 | 6 | vs | 1 | 2 | 3 | St. George's School Dragons | |
| 51 | | Tabor Academy Seawolves | 10 | 11 | 12 | vs | 7 | 8 | 9 | Fairfield Prep Jesuits | |
| 52 | | The Hotchkiss School Bearcats | 16 | 17 | 18 | vs | 13 | 14 | 15 | Brunswick School Bruins | |
| Flight 9 |
| 53 | | St. George's School Dragons | 4 | 5 | 6 | vs | 1 | 2 | 3 | Milton Academy Mustangs | |
| 54 | | Fairfield Prep Jesuits | 10 | 11 | 12 | vs | 7 | 8 | 9 | Marblehead High School Fishwagons | |
| 55 | | Brunswick School Bruins | 16 | 17 | 18 | vs | 13 | 14 | 15 | Greenwich High School Cardinals | |
| Flight 10 |
| 56 | | The Hotchkiss School Bearcats | 4 | 5 | 6 | vs | 1 | 2 | 3 | Tabor Academy Seawolves | |
