| Year | Champion | Fleet | Host Fleet |
|---|
| 2009 | H.L. DeVore | W. Long Island Sound | Chicago, IL
(Chicago Yacht Club) |
| 2008 | William Berry | Buzzards Bay | Oxford, Maryland
(Tred Avon Yacht Club) |
| 2007 | Peter Denton
Will Welles | Newport | Newport
(Ida Lewis Yacht Club) |
| 2006 | William Berry | Buzzards Bay | Buzzards Bay/Marion
(Beverly Yacht Club) |
| 2005 | Jonathan Pope | Buzzards Bay | W. Long Island Sound
(Larchmont Yacht Club) |
| 2004 | Jonathan Pope | Buzzards Bay | Martha’s Vineyard
(Edgartown Yacht Club) |
| 2003 | Robin Monk | Newport | Chicago
(Chicago Yacht Club) |
| 2002 | Reed Baer
John Burnham | Newport | Seawanhaka
(Seawanhaka Corinthian YC) |
| 2001 | Jerome Jordon
Anthony Kotoun | Newport | Newport
(Ida Lewis Yacht Club) |
| 2000 | Joe Schulz-Heik
Thierry de La Villehuchet | W. Long Island Sound | W. Long Island Sound
(Larchmont Yacht Club) |
| 1999 | Joe Schulz-Heik
Thierry de La Villehuchet | W. Long Island Sound | Buzzards Bay/Marion
(Beverly Yacht Club) |
| 1998 | Joe Schulz-Heik
Thierry de La Villehuchet | W. Long Island Sound | Chicago |
| 1997 | Joe Schulz-Heik
Thierry de La Villehuchet | W. Long Island Sound | Narragansett Bay |
| 1996 | Ched Proctor
John Hardy | Manhasset Bay | Marblehead |
| 1995 | Ched Proctor
John Hardy | Manhasset Bay | Martha’s Vineyard |
| 1994 | Ched Proctor
John Hardy | Manhasset Bay | W. Long Island Sound |
| 1993 | Ched Proctor
John Hardy | Manhasset Bay | Dallas |
| 1992 | Wayne Kennedy
Nick Burke | Marblehead | Buzzards Bay/Marion
(Beverly Yacht Club) |
| 1991 | Ched Proctor
John Hardy | Manhasset Bay | Narragansett Bay |
| 1990 | Ched Proctor
John Hardy | Manhasset Bay | Manhasset Bay |
| 1989 | Ched Proctor
John Hardy | Manhasset Bay | Chicago |
| 1988 | Victor M. Onet, Jr. | Seawanhaka | Seawanhaka |
| 1987 | Mike Deland | Buzzards Bay | Martha’s Vineyard |
| 1986 | Dave McClintock | Narragansett Bay | Buzzards Bay/Marion
(Beverly Yacht Club) |
| 1985 | Earle Stubbs | Narragansett Bay | Northern Mass. Bay |
| 1984 | Mike Polkabla | Monterey Bay | Monterey Bay |
| 1983 | Chris Withers | Narragansett Bay | W. Long Island Sound |
| 1982 | Rick Tears | Dallas | Narragansett Bay |
| 1981 | Chris Withers | Narragansett Bay | Dallas |
| 1980 | Mike Deland | Buzzards Bay | Martha’s Vineyard |
| 1979 | Al Merll | Dallas | Buzzards Bay/Marion
(Beverly Yacht Club) |
| 1978 | Richard Clark | Monterey Bay | W. Long Island Sound |
| 1977 | Frank Scully | Marblehead | Marblehead |
| 1976 | Gordon Benjamin
Bonnie Shore | Narragansett Bay | Narragansett Bay |
| 1975 | Richard Clark | Monterey Bay | Monterey Bay |
| 1974 | Martin Plonus | Chicago | Chicago |
| 1973 | Arthur Knapp, Jr. | W. Long Island Sound | W. Long Island Sound |
| 1972 | Joseph O’Hora
George Brazill | W. Long Island Sound | Narragansett Bay |
| 1971 | George Brazill
Joseph O’Hora | W. Long Island Sound | W. Long Island Sound |
| 1970 | Lance McCabe | Southern California | W. Long Island Sound |
| 1969 | Patrick O’Neal | W. Long Island Sound | W. Long Island Sound |
| 1968 | Richard Sykes
Jim Sykes | W. Long Island Sound | Seawanhaka |
| 1967 | Richard Sykes
Jim Sykes | W. Long Island Sound | Seawanhaka |
| 1966 | David Smalley | W. Long Island Sound | W. Long Island Sound |
| 1965 | Patrick O’Neal | W. Long Island Sound | Greenwich |
