Sep 12, 2019 @ 22:35:17 EDT
| # | Team 1 | Record | Record | Team 2 | |||
|---|---|---|---|---|---|---|---|
| Round 1 | |||||||
| 1 |  | Annapolis High School Panthers | 2-4-6 | vs | 1-3-5 | Archbishop Spalding Cavalier |  |
| 2 |  | Severna Park Varsity | 3-4-6 | vs | 1-2-5 | Severn School Varsity |  |
| 3 |  | Key School Varsity | 1-2-3 | vs | 4-5-6 | Broadneck High School Bruins |  |
| 4 |  | South River High School Varsity | 3-4-5 | vs | 1-2-6 | Walt Whitman High School Varsity |  |
| 5 |  | Indian Creek School Eagles | 4-5-6 | vs | 1-2-3 | Annapolis High School Panthers | |
| 6 | | Severn School Varsity | 1-2-3 | vs | 4-5-6 | St. Mary's Ryken Varsity |  |
| 7 | | Archbishop Spalding Cavalier | 1-2-4 | vs | 3-5-6 | Key School Varsity | |
| 8 | | Walt Whitman High School Varsity | 1-2-6 | vs | 3-4-5 | Severna Park Varsity | |
| 9 | | Broadneck High School Bruins | 1-2-3 | vs | 4-5-6 | Indian Creek School Eagles | |
| 10 | | St. Mary's Ryken Varsity | 1-4-6 | vs | 2-3-5 | South River High School Varsity | |
| 11 | | Key School Varsity | 1-2-4 | vs | 3-5-6 | Annapolis High School Panthers | |
| 12 | | Severn School Varsity | 1-2-5 | vs | 3-4-6 | Walt Whitman High School Varsity | |
| 13 | | Archbishop Spalding Cavalier | 1-2-6 | vs | 3-4-5 | Indian Creek School Eagles | |
| 14 | | St. Mary's Ryken Varsity | 4-5-6 | vs | 1-2-3 | Severna Park Varsity | |
