| Christchurch School | JV | A | 1 | Unreported Sailor '19 * | | Unreported Sailor 2 '19 * | |
| Hampton Roads Academy | JV | A | 4 | Jared Cronin '17 | | Alex Kitay '19 | |
| Kecoughtan High School | JV | A | 5 | Rachael Kilgore '14 | | Rachel Kilgore '14 | |
| Maury High School | JV | A | 6 | Unreported Sailor '19 * | | Unreported Sailor 2 '19 * | |
| Nansemond-Suffolk Academy | JV | A | 7 | Unreported Sailor '19 * | | Unreported Sailor 2 '19 * | |
| Poquoson High School | JV | A | 8 | Unreported Sailor '19 * | | Unreported Sailor 2 '19 * | |
| Smithfield High School | Smithfield | A | 3 | Unreported Sailor '19 * | | Unreported Sailor 2 '19 * | |
| York High School | JV | A | 2 | Ben Clarke '16 | | Ben Clarke '16 | |