2018 at South Boston Stanly Kostka -  #439 South Boston

2017 at Gull Lake Mike Blackwood - #452 Gull Lake

2016 at Newport Stanley Kostka - #439 South Boston

2015 at Cohasset Wiley Wakeman - #399 Wahconda Cohasset

2014 at South Boston Mark DeShong - #461 South Boston

2013 at Falmouth Wiley Wakeman- #399 Cohasset

2012 at Gull Lake Tick Ticknor - #452 The Band Gull Lake

2011 at Cohasset Wiley Wakeman - #399 Wahconda Cohasset YC

2010 at Eastern Point Ben Richardson Eastern Point YC

2009 at Hingham Dave Johnson Jr./Butch Milan - #459 Lightning Boston Harbor YC

2008 at South Boston Bill Donald/Russell Robinson - #443 South Boston

2007 at Falmouth Bill Yetman/ Jim Summers - #453 - Zephyr Falmouth

2006 at Gull Lake Ryan Staszko - #452 Breakin' Wind Cohasset

2005 at Cohasset Ryan Staszko - #452 Breakin' Wind Cohasset

2004 at Hingham Jeff Putney, Tim Putney - #451 Screamin' Tuna Milwaikee

2003 at Milwaukee Dave Johnson Jr - #454 TOPATGull Lake

2002 at Falmouth Dave Johnson Jr - #453 MARTINI II Gull Lake

2001 at South Boston Charley Henry - #444 FOUR Cohasset

2000 at Gull Lake Mike Blackwood - #397 FIREWOOD Milwaukee