| Year | Skipper | Yacht Club | Chairman |
| 2023 | Chris Poole | Seawanhaka Corinthian Yacht Club | Bob Piercy |
| 2022 | Ian Williams | Royal Yachting Association | Lisa Meier |
| 2021 | Taylor Canfield | Chicago Yacht Club | Chris Macy |
| 2019 | Ian Williams | Royal Lymington Yacht Club, Great Britain | Arleen Tolle |
| 2018 | Taylor Canfield | Chicago Yacht Club | Eric Dickinson |
| 2017 | Ian Williams | Royal Lymington Yacht Club, Great Britain | Joe Seibert |
| 2016 | Taylor Canfield | St. Thomas Yacht Club | Camille Daniels |
| 2015 | Taylor Canfield | St. Thomas Yacht Club | Bill Durant |
| 2014 | Taylor Canfield | St. Thomas Yacht Club | David Westerfield |
| 2013 | Simone Ferrarese | Circolo Della Vela | David Murray |
| 2012 | Ian Williams | Royal Lymington Yacht Club, Great Britain | Mary Voigt |
| 2011 | Ian Williams | Exe Sailing Club, Great Britain | John Satariano |
| 2010 | Francesco Bruni | Yacht Club, Costa Smeralda, Italy | Mustafa Altuner |
| 2009 | Johnie Berntsson | Royal Gothenburg Yacht Club, Sweden | David Stotler |
| 2008 | Gavin Brady | Edgartown Yacht Club | Merle Asper |
| 2007 | Mathieu Richard | APCC Voile Sportive, France | John Busch |
| 2006 | Gavin Brady | Royal Hong Kong Yacht Club, Hong Kong | Randy Smith |
| 2005 | Dean Barker | Royal New Zealand Yacht Squadron, New Zealand | Kate Banks |
| 2004 | Ed Baird | St. Petersburg Yacht Club | Charles Legeman |
| 2003 | Ken Read | New York Yacht Club | Donald Warner |
| 2002 | Peter Holmberg | Golden Gate Yacht Club | Dean Sutherland |
| 2001 | Peter Holmberg | St. Thomas Yacht Club, US Virgin Islands | Shannon Gallagher |
| 2000 | Dean Barker | Royal New Zealand Yacht Squadron, New Zealand | Camille Daniels |
| 1999 | Peter Holmberg | St. Thomas Yacht Club, US Virgin Islands | Bill Green, III |
| 1998 | Peter Holmberg | St. Thomas Yacht Club, US Virgin Islands | Mike Trainotti |
| 1997 | Gavin Brady | Royal New Zealand Yacht Squadron | Mike Van Dyke |
| 1996 | Gavin Brady | Royal New Zealand Yacht Squadron | Dave Millett |
| 1995 | Harold Cudmore | Royal Cork Yacht Club, Ireland | Bud Tretter |
| 1994 | Chris Law | Tamesis Club, Great Britain | Bob Kirstine |
| 1993 | Rod Davis | Royal Akarana Yacht Club, New Zealand | Drew Satariano |
| 1992 | Terry Hutchinson | Grand Traverse Yacht Club, Michigan | Hal Lane |
| 1991 | Chris Dickson | Nippon Ocean Racing Club, Japan | Ken Larson |
| 1990 | Chris Dickson | Tutukaka Yacht Club, New Zealand | Dick Seward |
| 1989 | Rod Davis | Royal New Zealand Yacht Squadron | Bill Uniack |
| 1988 | Peter Gilmour | Royal Freshwater Sailing Club, Australia | Tom Dessel |
| 1987 | Edward Owen | Holyhead Yacht Club, Wales | Howard Thompson |
| 1986 | Harold Cudmore | Royal Cork Yacht Club, Ireland | Brian Donaldson |
| 1985 | Rod Davis | Newport Harbor Yacht Club | Harlan Moore |
| 1984 | Dave Perry | Yale Corinthian Yacht Club | Lou Comyns |
| 1983 | Dave Perry | Yale Corinthian Yacht Club | Bruce Brown |
| 1982 | Scott Perry | Naval Academy Sailing Squadron | David Berg |
| 1981 | Rod Davis | Long Beach Yacht Club | Stan Miller |
| 1980 | Dennis Durgan | Newport Harbor Yacht Club | Dave Crandall |
| 1979 | Dennis Durgan | Newport Harbor Yacht Club | Nort Nelson |
| 1978 | Dick Deaver | Los Angeles Yacht Club | Paul Frazier |
| 1977 | Ted Turner | Atlanta Yacht Club | Peter Kent |
| 1976 | Dick Deaver | Los Angeles Yacht Club | Bill Steuber |
| 1975 | Dennis Conner | San Diego Yacht Club | Tom Shadden |
| 1974 | Bill Ficker | New York Yacht Club | Norm Scott |
| 1973 | Dennis Conner | San Diego Yacht Club | Paul W. Smith |
| 1972 | Argyle Campbell | Balboa Yacht Club | Barney Flam |
| 1971 | Tommy Pickard | Long Beach Yacht Club | Robert Graham |
| 1970 | Argyle Campbell | Balboa Yacht Club | Robert Leslie |
| 1969 | Henry Sprague | Navy Yacht Club | William Effinger |
| 1968 | Skip Allan | Los Angeles Yacht Club | Downie D. Muir, III |
| 1967 | Scott Allan | Newport Harbor Yacht Club | Robert Basham |
| 1966 | Gerry Driscoll | San Diego Yacht Club | Don Leedom |
| 1965 | Gerry Driscoll | San Diego Yacht Club | William Dalessi,Don Leedom, Clark Sweet |
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