
| Year | Award Winner | Winner's Fleet | Host Fleet | Details |
|---|---|---|---|---|
| 2025 | Fleet #9 | Newport, RI | Edgartown, MA Edgartown | 2025 Results |
| 2024 | Fleet #9 | Newport, RI | Larchmont, NY Larchmont Yacht Club | 2024 Results |
| 2023 | Fleet #9 | Newport, RI | Marion, MA Beverly Yacht Club | 2023 Results |
| 2022 | Fleet #9 | Newport, RI | Newport, RI Ida Lewis Yacht Club | 2022 Results |
| 2021 | Fleet #9 | Newport, RI | Oxford, MD Tred Avon Yacht Club | 2021 Results |
| 2020 | Cancelled due to COVID-19 | Oxford, MD Tred Avon Yacht CLub | ||
| 2019 | Fleet #10 | Marion, MA | Chicago, IL Chicago Yacht Club | 2019 Results |
| 2018 | Fleet #10 | Marion, MA | Edgartown, MA Edgartown Yacht Club | 2018 Results |
| 2017 | Regatta abandoned | Mystic, CT Mason's Island Yacht Club | ||
| 2016 | Fleet # 9 | Newport, RI | Monterey, CA Monterey Peninsula Yacht Club | 2016 Results |
| 2015 | Fleet # 9 | Newport, RI | Newport, RI Ida Lewis Yacht Club | 2015 Results |
| 2014 | Fleet # 9 | Newport, RI | W. Long Island Sound, NY Larchmont Yacht Club | 2014 Results |
| 2013 | Fleet # 9 | Newport, RI | Oxford, MD Tred Avon Yacht Club | 2013 Results |
| 2012 | Fleet # 9 | Newport, RI | Marion, MA Beverly Yacht Club | 2012 Results |
| 2011 | Fleet # 9 | Newport, RI | Oyster Bay, NY Seawanhaka Corinthian YC | 2011 Results |
| 2010 | Fleet # 9 | Newport, RI | Mystic, CT Mason's Island Yacht Club | 2010 Results |
| 2009 | Fleet # 3 | Chicago, IL | Chicago, IL Chicago Yacht Club | 2009 Results |
| 2008 | Fleet # 9 | Newport, RI | Oxford, MD Tred Avon Yacht Club | 2008 Results |