
| Year | Award Winner | Winner's Fleet | Host Fleet | Details |
|---|---|---|---|---|
| 2025 | Adrian Van Der Wal | Newport, RI | Edgartown, MA Edgartown | 2025 Results |
| 2024 | John Burnham Reed Baer | Newport, RI | Larchmont, NY Larchmont Yacht Club | 2024 Results |
| 2023 | Graham Quinn Karl Anderson | Marion, MA | Marion, MA Beverly Yacht Club | 2023 Results |
| 2022 | Andy Green | Newport, RI | Newport, RI Ida Lewis Yacht Club | 2022 Results |
| 2021 | Robin Monk | Newport, RI | Oxford, MD Tred Avon Yacht Club | 2021 Results |
| 2020 | Cancelled due to COVID-19 | Oxford, MD Tred Avon Yacht CLub | ||
| 2019 | Tom Hirsch Tim Dawson | Newport, RI | Chicago, IL Chicago Yacht Club | 2019 Results |
| 2018 | Ted Slee | Newport, RI | Edgartown, MA Edgartown Yacht Club | 2018 Results |
| 2017 | Regatta abandoned due to Hurricane Jose | Mystic, CT Mason's Island Yacht Club | ||
| 2016 | John Burnham Reed Baer | Newport, RI | Monterey, CA Monterey Peninsula Yacht Club | 2016 Results |
| 2015 | Betsy Alison Ted Slee | Newport, RI | Newport, RI Ida Lewis Yacht Club | 2015 Results |
| 2014 | Com Crocker Kurt Weisenfluh | Larchmont, NY | W. Long Island Sound, NY Larchmont Yacht Club | 2014 Results |
| 2013 | Tim Dawson Tom Hirsch | Newport, RI | Oxford, MD Tred Avon Yacht Club | 2013 Results |
| 2012 | Tim Dawson | Newport, RI | Marion, MA Beverly Yacht Club | 2012 Results |
| 2011 | John Burnham Reed Baer | Newport, RI | Oyster Bay, NY Seawanhaka Corinthian YC | 2011 Results |
| 2010 | Robin Monk | Newport, RI | Mystic, CT Mason's Island Yacht Club | 2010 Results |
| 2009 | H.L. DeVore | Larchmont, NY | Chicago, IL Chicago Yacht Club | 2009 Results |
| 2008 | William Berry | Marion, MA | Oxford, MD Tred Avon Yacht Club | 2008 Results |
| 2007 | Peter Denton Will Welles | Newport, RI | Newport, RI Ida Lewis Yacht Club | 2007 Results |
| 2006 | William Berry | Marion, MA | Buzzards Bay/Marion, MA Beverly Yacht Club | 2006 Results |
| 2005 | Jonathan Pope | Marion, MA | W. Long Island Sound, NY Larchmont Yacht Club | 2005 Results |
| 2004 | Jonathan Pope | Marion, MA | Edgartown, MA Edgartown Yacht Club | 2004 Results |
| 2003 | Robin Monk | Newport, RI | Chicago, IL Chicago Yacht Club | 2003 Results |
| 2002 | Reed Baer John Burnham | Newport, RI | Oyster Bay, NY Seawanhaka Corinthian YC | 2002 Results |
| 2001 | Jerome Jordon Anthony Kotoun | Newport, RI | Newport, RI Ida Lewis Yacht Club | 2001 Results |
| 2000 | Joe Schulz-Heik Thierry de La Villehuchet | W. Long Island Sound, NY | W. Long Island Sound, NY Larchmont Yacht Club | 2000 Results |
| 1999 | Joe Schulz-Heik Thierry de La Villehuchet | W. Long Island Sound, NY | Buzzards Bay/Marion, MA Beverly Yacht Club | 1999 Results |
| 1998 | Joe Schulz-Heik Thierry de La Villehuchet | W. Long Island Sound, NY | Chicago, IL Chicago Yacht Club | |
| 1997 | Joe Schulz-Heik Thierry de La Villehuchet | W. Long Island Sound, NY | Narragansett Bay, RI ? | 1997 Results |
| 1996 | Ched Proctor John Hardy | Manhasset Bay, NY | Marblehead, MA | |
| 1995 | Ched Proctor John Hardy | Manhasset Bay, NY | W. Long Island Sound, NY Larchmont Yacht Club | |
| 1994 | Ched Proctor John Hardy | Manhasset Bay, NY | Marthas Vineyard, MA Edgartown Yacht Club | 1994 Results |
| 1993 | Ched Proctor John Hardy | Manhasset Bay, NY | Dallas, TX Rush Creek Yacht Club | 1993 Results |
| 1992 | Wayne Kennedy Nick Burke | Marblehead, MA | Buzzards Bay/Marion, MA Beverly Yacht Club | 1992 Results |
| 1991 | Ched Proctor John Hardy | Manhasset Bay, NY | Narragansett Bay, RI ? | 1991 Results |
| 1990 | Ched Proctor John Hardy | Manhasset Bay, NY | Manhasset Bay, NY ? | 1990 Results |
| 1989 | Ched Proctor John Hardy | Manhasset Bay, NY | Chicago, IL Chicago Yacht Club | 1989 Results |
| 1988 | Victor M. Onet Jr. | Seawanhaka, NY | Seawanhaka, NY Seawanhaka Corithian Yacht Club | 1988 Results |
| 1987 | Mike Deland | Marion, MA | Marthas Vineyard, MA Edgartown Yacht Club | 1987 Results |
| 1986 | Dave McClintock | Narragansett Bay, RI | Buzzards Bay/Marion, MA Beverly Yacht Club | 1986 Results |
| 1985 | Earle Stubbs | Narragansett Bay, RI | Northern Mass. Bay, MA | |
| 1984 | Mike Polkabla | Monterey Bay, CA | Monterey Bay, CA | |
| 1983 | Chris Withers | Narragansett Bay, RI | W. Long Island Sound, NY ? | 1983 Results |
| 1982 | Rick Tears | Dallas, TX | Narragansett Bay, RI ? | 1982 Results |
| 1981 | Chris Withers | Narragansett Bay, RI | Dallas, TX ? | 1981 Results |
| 1980 | Mike Deland | Marion, MA | Marthas Vineyard, MA Edgartown Yacht Club | 1980 Results |
| 1979 | Al Merll | Dallas, TX | Buzzards Bay/Marion, MA Beverly Yacht Club | 1979 Results |
| 1978 | Richard Clark | Monterey Bay, CA | W. Long Island Sound, NY | |
| 1977 | Frank Scully | Marblehead, MA | Marblehead, MA | |
| 1976 | Gordon Benjamin Bonnie Shore | Narragansett Bay, RI | Narragansett Bay, RI | |
| 1975 | Richard Clark | Monterey Bay, CA | Monterey Bay, CA | |
| 1974 | Martin Plonus | Chicago, IL | Chicago, IL | |
| 1973 | Arthur Knapp Jr. | W. Long Island Sound, NY | W. Long Island Sound, NY | |
| 1972 | Joseph OHora George Brazill | W. Long Island Sound, NY | Narragansett Bay, RI | |
| 1971 | George Brazill Joseph OHora | W. Long Island Sound, NY | W. Long Island Sound, NY | |
| 1970 | Lance McCabe | Southern California | W. Long Island Sound, NY | |
| 1969 | Patrick ONeal | W. Long Island Sound, NY | W. Long Island Sound, NY | |
| 1968 | Richard Sykes Jim Sykes | W. Long Island Sound, NY | Seawanhaka, NY | |
| 1967 | Richard Sykes Jim Sykes | W. Long Island Sound, NY | Seawanhaka, NY | |
| 1966 | David Smalley | W. Long Island Sound, NY | W. Long Island Sound, NY | |
| 1965 | Patrick ONeal | W. Long Island Sound, NY | Greenwich, CT |