Phyllis Rawlins Drayton Trophy
From 2013-2016, The Phyllis Rawlins Drayton Trophy was awarded to the top women finishers in A, B and C divisions at the Harbor 20 Championships each year (either
skipper or crew).
Beginning with 2017, the Trophy will be awarded to the top female High Point scorer.
| Fleet | Year | Sailor |
| A | 2016 | Gale Pinckney |
| 2015 | Gale Pinckney | |
| 2014 | Gale Pinckney | |
| 2013 | Diane Menninger | |
| B | 2016 | Mary Whitney |
| 2015 | Mariah Geissman | |
| 2014 | Mariah Geissman | |
| 2013 | Jessica Newman | |
| C | 2016 | Debbie Springer |
| 2015 | Kyrsten Munster | |
| 2014 | Kathy Reed |