First offered by Chicago Yacht Club in 1915 to encourage competition between the club and eastern yacht clubs. The challenge was re-started in Shields in 2014.
| Year | Award Winner | Winner's Fleet | Host Fleet |
|---|---|---|---|
| 2019 | Eric Anderson | Fleet #12 Monterey, CA | Monterey, CA Monterey Pennisula |
| 2018 | Eric Anderson Todd Greene | Fleet #12 Monterey, CA | Newport, RI Ida Lewis Yacht Club |
| 2017 | John Burnham Reed Baer | Fleet #9 Newport, RI | Larchmont, NY Larchmont Yacht Club |
| 2016 | William Berry | Fleet #10, Marion, MA | Marion, MA Beverly Yacht Club |
| 2015 | William Berry | Fleet #10, Marion, MA | Monterey, CA Monterey Peninsula Yacht Club |
| 2014 | Pahktun Shah | Fleet #12, Monterey, CA | Chicago, IL Chicago Yacht Club |