
| Year | Award Winner | Winner's Fleet | Host Fleet | Details |
|---|---|---|---|---|
| 2025 | Richard Robbins Ethan Robbins | Marion, MA | Edgartown, MA Edgartown | 2025 Results |
| 2024 | Michael Rajacich Jr | Oxford, MD | Larchmont, NY Larchmont Yacht Club | 2024 Results |
| 2023 | Daniel Goodwin | Marion, MA | Marion, MA Beverly Yacht Club | 2023 Results |
| 2022 | John Burnham Reid Baer | Newport, RI | Newport, RI Ida Lewis Yacht Club | 2022 Results |
| 2021 | Ethan Robbins Richard Robbins | Marion, MA | Oxford, MD Tred Avon Yacht Club | 2021 Results |
| 2020 | Cancelled due to COVID-19 | Oxford, MD Tred Avon Yacht CLub | ||
| 2019 | Kenneth Deyett | Marion, MA | Chicago, IL Chicago Yacht Club | 2019 Results |
| 2018 | Steve Mettler | Edgartown, MA | Edgartown, MA Edgartown Yacht Club | 2018 Results |
| 2017 | Regatta abandoned due to Hurricane Jose | Mystic, CT Mason's Island Yacht Club | ||
| 2016 | Pakhtun Shah | Monterey, CA | Monterey, CA Monterey Peninsula Yacht Club | 2016 Results |
| 2015 | Eric Anderson | Monterey, CA | Newport, RI Ida Lewis Yacht Club | 2015 Results |
| 2014 | Rolan Schultz | Larchmon, NY | W. Long Island Sound, NY Larchmont Yacht Club | 2014 Results |
| 2013 | John Shannahan | Oxford, MD | Oxford, MD Tred Avon Yacht Club | 2013 Results |
| 2012 | Shane Wells | Marion, MA | Marion, MA Beverly Yacht Club | 2012 Results |
| 2011 | Bill Berry | Marion, MA | Oyster Bay, NY Seawanhaka Corinthian YC | 2011 Results |
| 2010 | Richard Robbins Ethan Robbins | Marion, MA | Mystic, CT Mason's Island Yacht Club | 2010 Results |
| 2009 | Peter Bailey | Oxford, MD | Chicago, IL Chicago Yacht Club | 2009 Results |
| 2008 | Mike McCaffery Jan Slee | Newport, RI | Oxford, MD Tred Avon Yacht Club | 2008 Results |
| 2007 | Jonathan Pope | Marion, MA | Newport, RI Ida Lewis Yacht Club | 2007 Results |
| 2006 | John Burnham | Newport, RI | Buzzards Bay/Marion, MA Beverly Yacht Club | 2006 Results |
| 2005 | W. Long Island Sound, NY Larchmont Yacht Club | 2005 Results | ||
| 2004 | Charles Shoemaker | Newport, RI | Edgartown, MA Edgartown Yacht Club | 2004 Results |
| 2003 | Robert E. Radway | Chicago, IL | Chicago, IL Chicago Yacht Club | 2003 Results |
| 2002 | Roland Schulz | Larchmont, NY | 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 | Bill Berry | Marion, MA | Buzzards Bay/Marion, MA Beverly Yacht Club | 1999 Results |
| 1998 | Chicago, IL Chicago Yacht Club | |||
| 1997 | Narragansett Bay, RI ? | 1997 Results | ||
| 1996 | Chris Cardoza | Larchmont, NY | Marblehead, MA | |
| 1995 | Charles Levy | Newport, RI | W. Long Island Sound, NY Larchmont Yacht Club | |
| 1994 | Bill Berry | Marion, MA | Marthas Vineyard, MA Edgartown Yacht Club | 1994 Results |
| 1993 | Dallas, TX Rush Creek Yacht Club | 1993 Results | ||
| 1992 | Harold F. Skip McGuire | Larchmont, NY | Buzzards Bay/Marion, MA Beverly Yacht Club | 1992 Results |
| 1991 | Bruce Muir | Newport, RI | Narragansett Bay, RI ? | 1991 Results |
| 1990 | Rick Tears | Dallas, TX | Manhasset Bay, NY ? | 1990 Results |
| 1989 | Jay Higgins | Chicago, IL | Chicago, IL Chicago Yacht Club | 1989 Results |
| 1988 | Donald R. Tomlin | Larchmont, NY | Seawanhaka, NY Seawanhaka Corithian Yacht Club | 1988 Results |
| 1987 | David Crowley Bill Saltonstall | Marion, MA | Marthas Vineyard, MA Edgartown Yacht Club | 1987 Results |
| 1986 | David S. Cooke | Marblehead, MA | Buzzards Bay/Marion, MA Beverly Yacht Club | 1986 Results |
| 1985 | Brian J. Ladouceur | Marion, MA | Northern Mass. Bay, MA | |
| 1984 | James B. Moore Jr. | Manhasset Bay, NY | Monterey Bay, CA | |
| 1983 | William Rich | Larchmont, NY | W. Long Island Sound, NY ? | 1983 Results |