Previous Champions
| 2011 | Lickety Split | Jed Hoffer | Beverly YC |
| 2010 | Katy | Chad Demarest | Buzzards YC |
| 2009 | Swan Song | George Moffat | Beverly YC |
| 2008 | Moonglade | D. Warren Vose Jr. | Edgartown YC |
| 2007 | Swizzle | Ted Grayson | Quissett YC |
| 2006 | Swan Song | George Moffat | Beverly YC |
| 2005 | Nobska II | Andy&Tad Chase | Buzzards YC |
| 2004 | Moonglade | D. Warren Vose Jr. | Edgartown YC |
| 2003 | Moonglade | D. Warren Vose Jr. | Edgartown YC |
| 2002 | Wendy | Rob Hurd/M. Callahan | Tabor Acadamy |
| 2001 | George Eberstadt | Edgartown YC | |
| 2000 | Wendy | Rob Hurd/M. Callahan/E. Hurd | Tabor Acadamy |
| 1999 | Wendy | Rob Hurd/M. Callahan | Tabor Acadamy |
| 1998 | Wendy | Rob Hurd/M. Callahan | Tabor Acadamy |
| 1997 | Tagalong | C. David Burt | Quissett YC |
| 1996 | Lickety Split | Rich McNeil | Beverly YC |
| 1995 | Songsparrow | Phip Hallowell | Buzzards YC |
| 1994 | Wendy | Rob Hurd/P. Cloos | Quissett YC |
| 1993 | Wendy | Rob Hurd | Quissett YC |
| 1992 | Sea Breeze | Janet Chalmers | Quissett YC |
| 1991 | Fast Enough | Joey Hetzeck | Beverly YC |
| 1990 | Lorelei | Terry Cronburg | Buzzards YC |
| 1989 | Nobska II | Tad Chase | Buzzards YC |
| 1988 | Weemark | Bill Ware | Buzzards YC |
| 1987 | Wendy | Rob Hurd | Quissett YC |
| 1986 | What Time | Daniel M. Schley | Buzzards YC |
| 1985 | Cutlass | Douglass Cooper | Quissett YC |
| 1984 | Cutlass | Douglass Cooper | Quissett YC |
| 1983 | What Time | Daniel M. Schley | Buzzards YC |
| 1982 | What Time | Daniel M. Schley | Buzzards YC |
| 1981 | Vireo | Katharine Saltonstall | Beverly YC |
| 1980 | Tagalong | C. David Burt | Quissett YC |
| 1979 | Indefatigable | Richard Von Herzen | Quissett YC |
| 1978 | Fast Enough | Josephine Hetzeck | Beverly YC |
| 1977 | Doughdish | William G. Harding | Buzzards YC |
| 1976 | Privateer | John N. Fisher Jr. | Buzzards YC |
| 1975 | Lickety Split | Richard Parsons | Beverly YC |
| 1974 | Aloha II | Michael Vassalotti | Wild Harbor YC |
| 1973 | Dinghao | Thomas T. Crowley | Beverly YC |
