Norm Cressy, longtime Rhodes 19 sailor and many times National’s bridesmaid, donated the Cressy Trophy to be presented annually to the 2nd place National’s skipper.
| Year | Winner |
|---|---|
| 2023 | James (Rocky) Sanchez |
| 2022 | Kim Pandapas |
| 2021 | Joe Fava |
| 2020 | Not Held / COVID |
| 2019 | Dave Nelson |
| 2018 | Benz Faget |
| 2017 | Ben Richardson |
| 2016 | Bob Bernstein |
| 2015 | Nat Taylor |
| 2014 | Dave Nelson |
| 2013 | Benz Faget |
| 2012 | Frank McNamara |
| 2011 | Jim Raisides/Charlie Pendleton |
| 2010 | Kim/Christina Pandapas |
| 2009 | Peter Sladovich |
| 2008 | Peter Sladovich |
| 2007 | Paul Adam |
| 2006 | Gretchen Curtis |
| 2005 | Event not held due to Hurricane Katrina |
| 2004 | Zane Yoder |
| 2003 | Jerry Blouin |
| 2002 | Shan McAdoo |
| 2001 | Kim G Pandapas |
| 2000 | Bill and Renee Heffernan |
| 1999 | Alan Grogono |
| 1998 | Bob Jensen |
| 1997 | Justin Scott |
| 1996 | Justin Scott |