
| Year | Award Winner | Winner's Fleet | Host Fleet | Details |
|---|---|---|---|---|
| 2025 | Adrian Van Der Wal | Newport, RI | Edgartown, MA Edgartown | 2025 Results |
| 2024 | Ward Young | Larchmont, NY | Larchmont, NY Larchmont Yacht Club | 2024 Results |
| 2023 | Jeff Hayden | Newport, RI | Marion, MA Beverly Yacht Club | 2023 Results |
| 2022 | Lindsey Turowski | Newport, RI | Newport, RI Ida Lewis Yacht Club | 2022 Results |
| 2021 | R. J. Cooper | Oxford, MD | Oxford, MD Tred Avon Yacht Club | 2021 Results |
| 2020 | Cancelled due to COVID-19 | Oxford, MD Tred Avon Yacht CLub | ||
| 2019 | Tom McManus | Fairfield, CT | Chicago, IL Chicago Yacht Club | 2019 Results |
| 2018 | Ken Deyett | Marion. MA | Edgartown, MA Edgartown Yacht Club | 2018 Results |
| 2017 | Regatta abandoned due to Hurricane Jose | Mystic, CT Mason's Island Yacht Club | ||
| 2016 | Tina Pryne | Monterey, CA | Monterey, CA Monterey Peninsula Yacht Club | 2016 Results |
| 2015 | Arianne Rettinger | Monterey, CA | Newport, RI Ida Lewis Yacht Club | 2015 Results |
| 2014 | Ashley Hobson | Monterey, CA | W. Long Island Sound, NY Larchmont Yacht Club | 2014 Results |
| 2013 | Drew Kellog | Oxford, MD | Oxford, MD Tred Avon Yacht Club | 2013 Results |
| 2012 | Not awarded | Marion, MA Beverly Yacht Club | 2012 Results | |
| 2011 | Mark Swanson | Seawanhaka, NY | Oyster Bay, NY Seawanhaka Corinthian YC | 2011 Results |
| 2010 | Kyle Martin Tom Hirsh | Newport, RI | Mystic, CT Mason's Island Yacht Club | 2010 Results |
| 2009 | Kristian Martincic | Chicago, IL | Chicago, IL Chicago Yacht Club | 2009 Results |
| 2008 | Schuyler Benson | Oxford, MD | Oxford, MD Tred Avon Yacht Club | 2008 Results |
| 2007 | Jeff Gladchun | Newport, RI | Newport, RI Ida Lewis Yacht Club | 2007 Results |