Presented in 1989 by Commodore Harrison Hubard, Jr., and long time Junior Activities Chairman, Kenzie Sinnickson Hubard, as a perpetual trophy to be awarded annually to the outstanding woman sailor of Fishing Bay Yacht Club. The criteria shall include dedication, participation, and performance and sportsmanship in sailing. The award shall be determined by the Commodore, Trophy Chairman, Offshore Division Commander and One-Design Division Commander.
| 1989 | Catherine Rogers | |
| 1990 | Lydia J. Strickland | |
| 1991 | Kathy Whittle | |
| 1992 | Holly B. Richard | |
| 1993 | Elizabeth L. Peabody | |
| 1994 | Caroline Collins | |
| 1995 | Kelly O'Toole | |
| 1996 | Mary Carter | |
| 1997 | Kenney Cobb | |
| 1998 | Debra L. Cycotte | |
| 1999 | Janelle Monnier | |
| 2000 | Lori Moyer | |
| 2001 | Lucy Kupersmith | |
| 2002 | Anna Cobb | |
| 2003 | Sharon Bauer | |
| 2004 | Kelly O’Toole | |
| 2005 | Sharon Bauer | |
| 2006 | Madelaine Alderman | |
| 2007 | Madeleine Alderman | |
| 2008 | Carolyn J. Schott | |
| 2009 | Amy L. Miller | |
| 2010 | Cyane B. Crump | |
| 2011 | Barbara Guenther | |
| 2012 | Caroline B. Garrett | |
| 2013 | Rebecca L. Wash | |
| 2014 | Ann Lisa Braun | |
| 2015 | Lisa Fleck | |
| 2016 | Julie Ann Wash | |
| 2017 | Julia Kimbrough | |
| 2018 | Karen Soule | |
| 2019 | Anne-Kinsey Wash | |
| 2020 | Louise Moore | |
| 2021 | Katie Yudkin | |
| 2022 | Holly Sears | |
| 2023 | Elizabeth Staas |