A Fleet
Class A – Merriman Trophy
| 2019 | Escape Velocity 2 | Ben Chigier | |
| 2018 | Heat Wave | Gary Weisberg | |
| 2017 | Heat Wave | Gary Weisberg | |
| 2016 | Heat Wave | Gary Weisberg | |
| 2015 | Heat Wave | Gary Weisberg | |
| 2014 | Scherherazade | Betsy McCombs | Eastern Yacht Club |
| 2013 | Katabatic | Gordon Hall | Eastern Yacht Club |
| 2012 | Katabatic | Gordon Hall | Eastern Yacht Club |
| 2011 | Indra | Tom Linkas | Boston Yacht Club |
| 2010 | Katabatic | Gordon Hall | Eastern Yacht Club |
| 2009 | Katabatic | Gordon Hall | Eastern Yacht Club |
| 2008 | Katabatic | Gordon Hall | Eastern Yacht Club |
| 2007 | Katabatic | Gordon Hall | Eastern Yacht Club |
| 2006 | Scherherazade | Hugh & Betsy Chandler | Eastern Yacht Club |
| 2005 | Indra | Tom Linkas | Boston Yacht Club |
| 2004 | Scherherazade | Hugh & Betsy Chandler | Eastern Yacht Club |
| 2003 | Katabatic | Gordon Hall | Eastern Yacht Club |
| 2002 | Katabatic | Gordon Hall | Eastern Yacht Club |
| 2001 | Katabatic | Gordon Hall | Eastern Yacht Club |
| 2000 | Katabatic | Gordon Hall | Eastern Yacht Club |
| 1999 | Shamrock Sensation | Ralph DiMattia | |
| 1998 | Scherherazade | Hugh & Betsy Chandler | Eastern Yacht Club |
| 1997 | Scherherazade | Hugh & Betsy Chandler | Eastern Yacht Club |
| 1996 | Claddagh | Leo Fallon | Boston Yacht Club |
| 1995 | Claddagh | Leo Fallon | Boston Yacht Club |
| 1994 | Claddagh | Leo Fallon | Boston Yacht Club |
| 1993 | Scherherazade | Hugh & Betsy Chandler | Eastern Yacht Club |
| 1992 | Coalition | Brian & Kathy Tedeschi | |
| 1991 | Wired | Steve & Helga Garland | |
| 1990 | Scherherazade | Hugh & Betsy Chandler | Eastern Yacht Club |
| 1989 | Scherherazade | Hugh & Betsy Chandler | Eastern Yacht Club |
| 1988 | Coalition | Brian Tedeschi | |
| 1987 | Spirit | Lou Pocharski | |
| 1986 | Scherherazade | Hugh & Betsy Chandler | Eastern Yacht Club |
| 1985 | Coalition | Brian Tedeschi | |
| 1984 | Scherherazade | Hugh & Betsy Chandler | Eastern Yacht Club |
| 1983 | DeJaVu | James Heart | |
| 1982 | Chief | Robert Maloney | |
| 1981 | Pique Dame | John Wells | |
| 1980 | Sparkler III | Jeffrey Freeman | |
| 1979 | Not Award | ||
| 1978 | Sabra | Peter Rosenberg | |
| 1977 | Swan | Donald Ross | |
| 1976 | Spirit | Louis Pocharski | |
| 1975 | Not Awarded | ||
| 1974 | Quicksliver | William K. Henze | |
| 1973 | Breeze | Crosby HItchcock | |
| 1972 | Dandelion | Frederick W. Pillsbury | |
| 1971 | Camelot | James E. Griffith | |
| 1970 | Scoot | Ralph A. Dyer | |
| 1969 | Robon Too | Lee Van Gemert | |
| 1968 | Chipper | Harold S. Lewis |
