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