| Year | Award Winner | Winner's Fleet | Host Fleet | Details |
|---|---|---|---|---|
| 2025 | John Burnham | Newport, RI | Edgartown, MA Edgartown | 2025 Results |
| 2024 | John Burnham | Newport, RI | Larchmont, NY Larchmont Yacht Club | 2024 Results |
| 2023 | John Burnham | Newport, RI | Marion, MA Beverly Yacht Club | 2023 Results |
| 2022 | Mike Toppa | Newport, RI | Newport, RI Ida Lewis Yacht Club | 2022 Results |
| 2021 | Bill Berry | Marion, MA | Oxford, MD Tred Avon Yacht Club | 2021 Results |
| 2020 | Cancelled due to COVID-19 | Oxford, MD Tred Avon Yacht CLub | ||
| 2019 | William Berry | Marion, MA | Chicago, IL Chicago Yacht Club | 2019 Results |
| 2018 | William Berry | Marion, MA | Edgartown, MA Edgartown Yacht Club | 2018 Results |
| 2017 | Regatta abandoned due to Hurricane Jose | Mystic, CT Mason's Island Yacht Club | ||
| 2016 | William Berry | Marion, MA | Monterey, CA Monterey Peninsula Yacht Club | 2016 Results |
| 2015 | Walter Bundy | Newport, RI | Newport, RI Ida Lewis Yacht Club | 2015 Results |
| 2014 | Mike Carr | Larchmont, NY | W. Long Island Sound, NY Larchmont Yacht Club | 2014 Results |
| 2013 | Skip McGuire | Larchmont, NY | Oxford, MD Tred Avon Yacht Club | 2013 Results |
| 2012 | Charlie Shoemaker | Newport, RI | Marion, MA Beverly Yacht Club | 2012 Results |
| 2011 | Alan Burnett | Mason's Island, CT | Oyster Bay, NY Seawanhaka Corinthian YC | 2011 Results |
| 2010 | Paul Sollitto | Newport, RI | Mystic, CT Mason's Island Yacht Club | 2010 Results |
| 2009 | Peter Bailey | Oxford, MD | Chicago, IL Chicago Yacht Club | 2009 Results |
| 2008 | Charlie Shoemaker | Newport, RI | Oxford, MD Tred Avon Yacht Club | 2008 Results |
| 2007 | Peter Denton | Newport, RI | Newport, RI Ida Lewis Yacht Club | 2007 Results |
| 2006 | Chris Withers | Newport, RI | Buzzards Bay/Marion, MA Beverly Yacht Club | 2006 Results |
| 2005 | W. Long Island Sound, NY Larchmont Yacht Club | 2005 Results | ||
| 2004 | Edgartown, MA Edgartown Yacht Club | 2004 Results | ||
| 2003 | Chicago, IL Chicago Yacht Club | 2003 Results | ||
| 2002 | Oyster Bay, NY Seawanhaka Corinthian YC | 2002 Results | ||
| 2001 | Newport, RI Ida Lewis Yacht Club | 2001 Results | ||
| 2000 | W. Long Island Sound, NY Larchmont Yacht Club | 2000 Results | ||
| 1999 | Chris Withers | Newport, RI | Buzzards Bay/Marion, MA Beverly Yacht Club | 1999 Results |
| 1998 | Chicago, IL Chicago Yacht Club | |||
| 1997 | Narragansett Bay, RI ? | 1997 Results | ||
| 1996 | Marblehead, MA | |||
| 1994 | Marthas Vineyard, MA Edgartown Yacht Club | 1994 Results | ||
| 1993 | Dallas, TX Rush Creek Yacht Club | 1993 Results | ||
| 1992 | Buzzards Bay/Marion, MA Beverly Yacht Club | 1992 Results | ||
| 1991 | Victor Onet | None | Narragansett Bay, RI ? | 1991 Results |
| 1990 | Manhasset Bay, NY ? | 1990 Results | ||
| 1989 | Chicago, IL Chicago Yacht Club | 1989 Results | ||
| 1988 | Seawanhaka, NY Seawanhaka Corithian Yacht Club | 1988 Results | ||
| 1987 | Marthas Vineyard, MA Edgartown Yacht Club | 1987 Results | ||
| 1986 | Buzzards Bay/Marion, MA Beverly Yacht Club | 1986 Results | ||
| 1985 | Northern Mass. Bay, MA | |||
| 1984 | Monterey Bay, CA | |||
| 1983 | W. Long Island Sound, NY ? | 1983 Results | ||
| 1982 | Narragansett Bay, RI ? | 1982 Results | ||
| 1981 | Dallas, TX ? | 1981 Results |