| Flight 1 (Round 1) |
| 1 |  | Walt Whitman High School Varsity | 1 | 2 | 3 | vs | 4 | 5 | 6 | Great Mills High School Hornets |  |
| 2 | | Unregistered-MASSA Pirates 2 | 7 | 8 | 9 | vs | 10 | 11 | 12 | Severn School Admirals |  |
| 3 |  | Leonardtown High School Raiders | 13 | 14 | 15 | vs | 16 | 17 | 18 | Unregistered-MASSA Pirates 1 | |
| Flight 2 |
| 4 |  | Bethesda - Chevy Chase HS Battlin' Baron | 1 | 2 | 3 | vs | 4 | 5 | 6 | Bishop O'Connell High School Knights |  |
| 5 | | Walt Whitman High School Varsity | 7 | 8 | 9 | vs | 10 | 11 | 12 | Unregistered-MASSA Pirates 2 | |
| 6 | | Unregistered-MASSA Pirates 1 | 13 | 14 | 15 | vs | 16 | 17 | 18 | Great Mills High School Hornets | |
| Flight 3 |
| 7 | | Bishop O'Connell High School Knights | 1 | 2 | 3 | vs | 4 | 5 | 6 | Severn School Admirals | |
| 8 | | Bethesda - Chevy Chase HS Battlin' Baron | 7 | 8 | 9 | vs | 10 | 11 | 12 | Leonardtown High School Raiders | |
| 9 | | Unregistered-MASSA Pirates 2 | 13 | 14 | 15 | vs | 16 | 17 | 18 | Unregistered-MASSA Pirates 1 | |
| Flight 4 |
| 10 | | Walt Whitman High School Varsity | 1 | 2 | 3 | vs | 4 | 5 | 6 | Bishop O'Connell High School Knights | |
| 11 | | Leonardtown High School Raiders | 7 | 8 | 9 | vs | 10 | 11 | 12 | Great Mills High School Hornets | |
| 12 | | Bethesda - Chevy Chase HS Battlin' Baron | 13 | 14 | 15 | vs | 16 | 17 | 18 | Severn School Admirals | |
| Flight 5 |
| 13 | | Bishop O'Connell High School Knights | 1 | 2 | 3 | vs | 4 | 5 | 6 | Unregistered-MASSA Pirates 1 | |
| 14 | | Unregistered-MASSA Pirates 2 | 7 | 8 | 9 | vs | 10 | 11 | 12 | Leonardtown High School Raiders | |
| 15 | | Severn School Admirals | 13 | 14 | 15 | vs | 16 | 17 | 18 | Walt Whitman High School Varsity | |
| Flight 6 |
| 16 | | Bethesda - Chevy Chase HS Battlin' Baron | 1 | 2 | 3 | vs | 4 | 5 | 6 | Great Mills High School Hornets | |
| 17 | | Leonardtown High School Raiders | 7 | 8 | 9 | vs | 10 | 11 | 12 | Bishop O'Connell High School Knights | |
| 18 | | Unregistered-MASSA Pirates 1 | 13 | 14 | 15 | vs | 16 | 17 | 18 | Severn School Admirals | |
| Flight 7 |
| 19 | | Great Mills High School Hornets | 1 | 2 | 3 | vs | 4 | 5 | 6 | Unregistered-MASSA Pirates 2 | |
| 20 | | Walt Whitman High School Varsity | 7 | 8 | 9 | vs | 10 | 11 | 12 | Bethesda - Chevy Chase HS Battlin' Baron | |
| 21 | | Severn School Admirals | 13 | 14 | 15 | vs | 16 | 17 | 18 | Leonardtown High School Raiders | |
| Flight 8 |
| 22 | | Bishop O'Connell High School Knights | 1 | 2 | 3 | vs | 4 | 5 | 6 | Great Mills High School Hornets | |
| 23 | | Unregistered-MASSA Pirates 1 | 7 | 8 | 9 | vs | 10 | 11 | 12 | Walt Whitman High School Varsity | |
| 24 | | Bethesda - Chevy Chase HS Battlin' Baron | 13 | 14 | 15 | vs | 16 | 17 | 18 | Unregistered-MASSA Pirates 2 | |
| Flight 9 |
| 25 | | Great Mills High School Hornets | 1 | 2 | 3 | vs | 4 | 5 | 6 | Severn School Admirals | |
| 26 | | Walt Whitman High School Varsity | 7 | 8 | 9 | vs | 10 | 11 | 12 | Leonardtown High School Raiders | |
| 27 | | Unregistered-MASSA Pirates 2 | 13 | 14 | 15 | vs | 16 | 17 | 18 | Bishop O'Connell High School Knights | |
| Flight 10 |
| 28 | | Bethesda - Chevy Chase HS Battlin' Baron | 1 | 2 | 3 | vs | 4 | 5 | 6 | Unregistered-MASSA Pirates 1 | |
