| Round 1 |
|---|
| 1 |  | St. Mary's High School (MD) Saints | 1-3-6 | vs | 2-4-5 | Broadneck High School Bruins |  |
| 2 |  | Archbishop Spalding Cavaliers | 2-5-6 | vs | 1-3-4 | Severn School Admirals |  |
| 3 |  | Leonardtown High School Raiders | 1-2-6 | vs | 3-4-5 | Great Mills High School Hornets |  |
| 4 |  | Key School Zags | 1-2-3 | vs | 4-5-6 | Severna Park Falcons |  |
| 5 | | St. Mary's High School (MD) Saints | 3-4-5 | vs | 1-2-6 | Archbishop Spalding Cavaliers | |
| 6 | | Great Mills High School Hornets | 1-2-5 | vs | 3-4-6 | Broadneck High School Bruins | |
| 7 | | Severna Park Falcons | 4-5-6 | vs | 1-2-3 | Severn School Admirals | |
| 8 | | Key School Zags | 1-2-5 | vs | 3-4-6 | Leonardtown High School Raiders | |
| 9 | | Archbishop Spalding Cavaliers | 1-2-6 | vs | 3-4-5 | Great Mills High School Hornets | |
| 10 | | St. Mary's High School (MD) Saints | 1-2-3 | vs | 4-5-6 | Severna Park Falcons | |
| 11 | | Leonardtown High School Raiders | 2-3-6 | vs | 1-4-5 | Broadneck High School Bruins | |
| 12 | | Key School Zags | 4-5-6 | vs | 1-2-3 | Severn School Admirals | |
| 13 | | Severna Park Falcons | 2-5-6 | vs | 1-3-4 | Great Mills High School Hornets | |
| 14 | | Archbishop Spalding Cavaliers | 1-2-6 | vs | 3-4-5 | Leonardtown High School Raiders | |
| 15 | | Severn School Admirals | 1-2-4 | vs | 3-5-6 | St. Mary's High School (MD) Saints | |
| 16 | | Key School Zags | 1-2-3 | vs | 4-5-6 | Broadneck High School Bruins | |
| 17 | | Leonardtown High School Raiders | 1-2-4 | vs | 3-5-6 | Severna Park Falcons | |
| 18 | | Great Mills High School Hornets | 1-3-5 | vs | 2-4-6 | Severn School Admirals | |
| 19 | | Broadneck High School Bruins | 1-4-5 | vs | 2-3-6 | Archbishop Spalding Cavaliers | |
| 20 | | St. Mary's High School (MD) Saints | 2-4-6 | vs | 1-3-5 | Key School Zags | |
| 21 | | Severn School Admirals | 1-2-6 | vs | 3-4-5 | Leonardtown High School Raiders | |
| 22 | | Severna Park Falcons | 3-4-6 | vs | 1-2-5 | Broadneck High School Bruins | |
| 23 | | Great Mills High School Hornets | 1-2-6 | vs | 3-4-5 | St. Mary's High School (MD) Saints | |
| 24 | | Key School Zags | 1-5-6 | vs | 2-3-4 | Archbishop Spalding Cavaliers | |
| 25 | | Broadneck High School Bruins | 4-5-6 | vs | 1-2-3 | Severn School Admirals | |
| 26 | | St. Mary's High School (MD) Saints | 3-4-5 | vs | 1-2-6 | Leonardtown High School Raiders | |
| 27 | | Archbishop Spalding Cavaliers | 1-2-5 | vs | 3-4-6 | Severna Park Falcons | |
| 28 | | Key School Zags | 1-5-6 | vs | 2-3-4 | Great Mills High School Hornets | |
| Round 2 |
|---|
| 29 | | St. Mary's High School (MD) Saints | 1-2-6 | vs | 3-4-5 | Broadneck High School Bruins | |
| 30 | | Archbishop Spalding Cavaliers | 3-4-6 | vs | 1-2-5 | Severn School Admirals | |
| 31 | | Leonardtown High School Raiders | 1-2-5 | vs | 3-4-6 | Great Mills High School Hornets | |
| 32 | | Key School Zags | 1-2-5 | vs | 3-4-6 | Severna Park Falcons | |
| 33 | | St. Mary's High School (MD) Saints | 2-3-4 | vs | 1-5-6 | Archbishop Spalding Cavaliers | |
| 34 | | Great Mills High School Hornets | 2-3-6 | vs | 1-4-5 | Broadneck High School Bruins | |
| 35 | | Severna Park Falcons | 3-4-6 | vs | 1-2-5 | Severn School Admirals | |
| 36 | | Key School Zags | 1-5-6 | vs | 2-3-4 | Leonardtown High School Raiders | |
| 37 | | Archbishop Spalding Cavaliers | 1-3-4 | vs | 2-5-6 | Great Mills High School Hornets | |
| 38 | | St. Mary's High School (MD) Saints | 1-2-4 | vs | 3-5-6 | Severna Park Falcons | |
| 39 | | Leonardtown High School Raiders | 3-5-6 | vs | 1-2-4 | Broadneck High School Bruins | |
| 40 | | Key School Zags | 4-5-6 | vs | 1-2-3 | Severn School Admirals | |
| 41 | | Severna Park Falcons | 2-5-6 | vs | 1-3-4 | Great Mills High School Hornets | |
| 42 | | Archbishop Spalding Cavaliers | 3-4-6 | vs | 1-2-5 | Leonardtown High School Raiders | |
| 43 | | Severn School Admirals | 1-4-6 | vs | 2-3-5 | St. Mary's High School (MD) Saints | |
| 44 | | Key School Zags | 3-5-6 | vs | 1-2-4 | Broadneck High School Bruins | |
| 45 | | Leonardtown High School Raiders | 1-4-5 | vs | 2-3-6 | Severna Park Falcons | |
| 46 | | Great Mills High School Hornets | 4-5-6 | vs | 1-2-3 | Severn School Admirals | |
| 47 | | Broadneck High School Bruins | 4-5-6 | vs | 1-2-3 | Archbishop Spalding Cavaliers | |
| 48 | | St. Mary's High School (MD) Saints | 1-4-6 | vs | 2-3-5 | Key School Zags | |
| 49 | | Severn School Admirals | 1-2-3 | vs | 4-5-6 | Leonardtown High School Raiders | |
| 50 | | Severna Park Falcons | 3-4-6 | vs | 1-2-5 | Broadneck High School Bruins | |
| 51 | | Great Mills High School Hornets | 4-5-6 | vs | 1-2-3 | St. Mary's High School (MD) Saints | |
| 52 | | Key School Zags | 3-4-6 | vs | 1-2-5 | Archbishop Spalding Cavaliers | |
| 53 | | Broadneck High School Bruins | 4-5-6 | vs | 1-2-3 | Severn School Admirals | |
| 54 | | St. Mary's High School (MD) Saints | 1-2-6 OCS | vs | 3-4-5 | Leonardtown High School Raiders | |
| 55 | | Archbishop Spalding Cavaliers | 1-4-6 | vs | 2-3-5 | Severna Park Falcons | |
| 56 | | Key School Zags | 2-3-4 | vs | 1-5-6 | Great Mills High School Hornets | |
