| Round 1 |
|---|
| 1 |  | St. Mary's High School (MD) Saints | 4-5-6 | vs | 1-2-3 | Severn School Admirals |  |
| 2 |  | Key School Zags | 4-5-6 | vs | 1-2-3 | Archbishop Spalding Cavaliers |  |
| 3 |  | Great Mills High School Hornets | 1-5-6 | vs | 2-3-4 | Broadneck High School Bruins |  |
| 4 |  | Leonardtown High School Raiders | 2-3-6 | vs | 1-4-5 | Gilman School Greyhounds |  |
| 5 | | St. Mary's High School (MD) Saints | 2-5-6 | vs | 1-3-4 | Severna Park Falcons |  |
| 6 | | Great Mills High School Hornets | 4-5-6 | vs | 1-2-3 | Severn School Admirals | |
| 7 | | Leonardtown High School Raiders | 3-4-5 | vs | 1-2-6 | Archbishop Spalding Cavaliers | |
| 8 | | Broadneck High School Bruins | 1-2-3 | vs | 4-5-6 | Gilman School Greyhounds | |
| 9 | | Key School Zags | 2-4-5 | vs | 1-3-6 | St. Mary's High School (MD) Saints | |
| 10 | | Great Mills High School Hornets | 1-2-4 | vs | 3-5-6 | Severna Park Falcons | |
| 11 | | Broadneck High School Bruins | 4-5-6 | vs | 1-2-3 | Severn School Admirals | |
| 12 | | Archbishop Spalding Cavaliers | 1-2-4 | vs | 3-5-6 | Gilman School Greyhounds | |
| 13 | | Great Mills High School Hornets | 1-3-5 | vs | 2-4-6 | Key School Zags | |
| 14 | | Leonardtown High School Raiders | 3-4-6 | vs | 1-2-5 | St. Mary's High School (MD) Saints | |
| 15 | | Broadneck High School Bruins | 1-2-3 | vs | 4-5-6 | Severna Park Falcons | |
| 16 | | Severn School Admirals | 1-2-3 | vs | 4-5-6 | Gilman School Greyhounds | |
| 17 | | Leonardtown High School Raiders | 1-2-4 | vs | 3-5-6 | Great Mills High School Hornets | |
| 18 | | Broadneck High School Bruins | 1-3-6 | vs | 2-4-5 | Key School Zags | |
| 19 | | Archbishop Spalding Cavaliers | 1-2-5 | vs | 3-4-6 | St. Mary's High School (MD) Saints | |
| 20 | | Severn School Admirals | 1-2-3 | vs | 4-5-6 | Severna Park Falcons | |
| 21 | | Broadneck High School Bruins | 1-4-5 | vs | 2-3-6 | Leonardtown High School Raiders | |
| 22 | | Archbishop Spalding Cavaliers | 1-2-3 | vs | 4-5-6 | Great Mills High School Hornets | |
| 23 | | Severn School Admirals | 1-2-3 | vs | 4-5-6 | Key School Zags | |
| 24 | | Severna Park Falcons | 3-5-6 | vs | 1-2-4 | Gilman School Greyhounds | |
| 25 | | Archbishop Spalding Cavaliers | 1-2-6 | vs | 3-4-5 | Broadneck High School Bruins | |
| 26 | | Severn School Admirals | 1-2-3 | vs | 4-5-6 | Leonardtown High School Raiders | |
| 27 | | Severna Park Falcons | 3-4-6 | vs | 1-2-5 | Key School Zags | |
| 28 | | St. Mary's High School (MD) Saints | 1-3-5 | vs | 2-4-6 | Gilman School Greyhounds | |
| 29 | | Severn School Admirals | 2-3-4 | vs | 1-5-6 DNF | Archbishop Spalding Cavaliers | |
| 30 | | Severna Park Falcons | 4-5-6 | vs | 1-2-3 | Leonardtown High School Raiders | |
| 31 | | St. Mary's High School (MD) Saints | 3-5-6 | vs | 1-2-4 | Great Mills High School Hornets | |
| 32 | | Key School Zags | 3-4-6 | vs | 1-2-5 | Gilman School Greyhounds | |
| 33 | | Severna Park Falcons | 3-4-6 | vs | 1-2-5 | Archbishop Spalding Cavaliers | |
| 34 | | St. Mary's High School (MD) Saints | 2-4-5 | vs | 1-3-6 | Broadneck High School Bruins | |
| 35 | | Key School Zags | 1-4-6 | vs | 2-3-5 | Leonardtown High School Raiders | |
| 36 | | Great Mills High School Hornets | 1-2-5 | vs | 3-4-6 | Gilman School Greyhounds | |
