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 |
|---|---|---|---|
| 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 |
List of winners from 1915 to 1953.
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