Sep 12, 2019 @ 22:35:17 EDT
| # | Team 1 | Sails | Sails | Team 2 | |||||||
|---|---|---|---|---|---|---|---|---|---|---|---|
| Flight 1 (Round 1) | |||||||||||
| 1 |  | Annapolis High School Panthers | 1 | 2 | 3 | vs | 4 | 5 | 6 | Archbishop Spalding Cavalier |  |
| 2 |  | Severna Park Varsity | 7 | 8 | 9 | vs | 10 | 11 | 12 | Severn School Varsity |  |
| 3 |  | Key School Varsity | 13 | 14 | 15 | vs | 16 | 17 | 18 | Broadneck High School Bruins |  |
| 4 |  | South River High School Varsity | AYC 13 | AYC 14 | AYC 15 | vs | AYC 16 | AYC 17 | AYC 18 | Walt Whitman High School Varsity |  |
| Flight 2 | |||||||||||
| 5 |  | Indian Creek School Eagles | 1 | 2 | 3 | vs | 4 | 5 | 6 | Annapolis High School Panthers | |
| 6 | | Severn School Varsity | 7 | 8 | 9 | vs | 10 | 11 | 12 | St. Mary's Ryken Varsity |  |
| 7 | | Archbishop Spalding Cavalier | 13 | 14 | 15 | vs | 16 | 17 | 18 | Key School Varsity | |
| 8 | | Walt Whitman High School Varsity | AYC 13 | AYC 14 | AYC 15 | vs | AYC 16 | AYC 17 | AYC 18 | Severna Park Varsity | |
| Flight 3 | |||||||||||
| 9 | | Broadneck High School Bruins | 1 | 2 | 3 | vs | 4 | 5 | 6 | Indian Creek School Eagles | |
| 10 | | St. Mary's Ryken Varsity | 7 | 8 | 9 | vs | 10 | 11 | 12 | South River High School Varsity | |
| 11 | | Key School Varsity | 13 | 14 | 15 | vs | 16 | 17 | 18 | Annapolis High School Panthers | |
| 12 | | Severn School Varsity | AYC 13 | AYC 14 | AYC 15 | vs | AYC 16 | AYC 17 | AYC 18 | Walt Whitman High School Varsity | |
| Flight 4 | |||||||||||
| 13 | | Archbishop Spalding Cavalier | 1 | 2 | 3 | vs | 4 | 5 | 6 | Indian Creek School Eagles | |
| 14 | | St. Mary's Ryken Varsity | 7 | 8 | 9 | vs | 10 | 11 | 12 | Severna Park Varsity | |
