E Fleet
Class E – Vice President's Bowl
| 2019 | Not Awarded | ||
| 2018 | Not Awarded | ||
| 2017 | Not Awarded | ||
| 2016 | Not Awarded | ||
| 2015 | Not Awarded | ||
| 2014 | Not Awarded | ||
| 2013 | Not Awarded | ||
| 2012 | Not Awarded | ||
| 2011 | Not Awarded | ||
| 2010 | Mysterious Ways | Steve Kavanaugh | Savin Hill Yacht Club |
| 2009 | Mysterious Ways | Steve Kavanaugh | Savin Hill Yacht Club |
| 2008 | Pterodactyl | Paul Smith | Swampscott Yacht Club |
| 2007 | Pterodactyl | Paul Smith | Swampscott Yacht Club |
| 2006 | Evelyn | Luke Buxton | Palmer's Cove Yacht Club |
| 2005 | Barra | Jim & Jan Maxwell | Jubilee Yacht Club |
| 2004 | Shenanigan | Bob Maxwell | Jubilee Yacht Club |
| 2003 | Barra | Jim & Jan Maxwell | Jubilee Yacht Club |
| 2002 | Not Awarded | ||
| 2001 | Pterodactyl | Paul Smith | Swampscott Yacht Club |
| 2000 | Barra | Jim & Jan Maxwell | Jubilee Yacht Club |
| 1999 | Barra | Jim & Jan Maxwell | Jubilee Yacht Club |
