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 as either skipper or crew. In 2017, the Trophy was awarded to the top female High Point scorers. From 2018 on, the Trophy will be awarded to the female fleet members who race on the greatest number of High Point Fleet Race days for the season as skipper or crew.
| Fleet | Year | Sailor |
| A | 2017 | |
| 2016 | Gale Pinckney | |
| 2015 | Gale Pinckney | |
| 2014 | Gale Pinckney | |
| 2013 | Diane Menninger | |
| B | 2017 | |
| 2016 | Mary Whitney | |
| 2015 | Mariah Geissman | |
| 2014 | Mariah Geissman | |
| 2013 | Jessica Newman | |
| C | 2017 | |
| 2016 | Debbie Springer | |
| 2015 | Kyrsten Munster | |
| 2014 | Kathy Reed |