Photo Credit: FRIED ELLIOTT / friedbits.com
| YEAR | BOAT | SKIPPER | CREW | FLEET | ENTRIES | LOCATION | RESULTS |
|---|---|---|---|---|---|---|---|
| 2026 | #5618 | Jack Jennings | Phil Trinter | ChiH | 16 | Tampa, FL, USA | Results |
| 2025 | #8464 | Jack Jennings | Pedro Trouche | ChiH | 21 | Pass Christian, MS, USA | Results |
| 2024 | #8550 | Paul Cayard | Danny Cayard | WSFB | 25 | Newport Harbor, CA, USA | Results |
| 2023 | #8537 | George Szabo | Guy Avellon | SDB | 30 | Vancouver, BC CAN | Results |
| 2022 | #8218 | Jack Jennings | Pedro Trouche | ChiH | 33 | Annapolis YC, MD, USA | Results |
| 2021 | #8218 | Erik Lidecis | Greg Smith | NH | 30 | Newport Harbor YC, CA, USA | Results |
| 2020 | NOT HELD | ||||||
| 2019 | #8509 | Augie Diaz | Henry Boening | BisB | 33 | Toms River, NJ, USA | Results |
| 2018 | #8423 | Eric Doyle | Payson Infelise | SDB | 37 | Marina del Rey, CA, USA | Results |
| 2017 | #8509 | Augie Diaz | Bruno Prada | BisB | 46 | Marblehead, MA, USA | Results |
| 2016 | #8177 | Eivind Melleby | oshua. Revkin | ISOL | 27 | Chicago, IL, USA | Results |
| 2015 | #8448 | Carl Buchan | Jamie Buchan | PS | 33 | Seattle, WA, USA | Results |
| 2014 | #8444 | Torben Grael | Guilherme Almeida | Gua | 41 | Oxford, MD, USA | Results |
| 2013 | #8203 | Brian Ledbetter | Gregg Morton | PS | 42 | Newport Harbor, CA, USA | Results |
| 2012 | #8395 | J.A. MacCausland | Guy Avellon | CR | 33 | Hamilton, Ontario, Canada | Results |
| 2011 | #8434 | George Szabo, III | Mark Strube | SDB | 28 | Tampa, Florida, USA | Results |
| 2010 | #8434 | George Szabo, III | Frithjof Kleen | SDB | 42 | Marina del Rey, CA, USA | Results |
| 2009 | #8241 | Andy Horton | Steve Erickson | NB | 47 | Westport, CT, USA | Results |
| 2008 | #8195 | J.A. MacCausland | Kevin Murphy | CR | 30 | Traverse, Michigan, USA | Results |
| 2007 | #8156 | Andy Horton | Brad Nichol | NB | 49 | Vancouver, BC, Canada | Results |
| 2006 | #8187 | Hamish Pepper | Carl Williams | NZL | 78 | Miami, Florida, USA | Results |
| 2005 | #7995 | George Szabo, III | Eric Monroe | SDB | 41 | Marina del Rey, California, USA | Results |
| 2004 | #8184 | J.A. MacCausland | Brian Fatih | CR | 44 | Boston, Massachusetts, USA | Results |
| 2003 | #8159 | Paul Cayard | Phil Trinter | WSFB | 40 | San Franciso, California, USA | Results |
| 2002 | #8067 | Mark Reynolds | Magnus Liljedahl | SDB | 52 | Lake Sunapee, New Hampshire, USA | Results |
| 2001 | #7995 | George Szabo, III | George Iverson | SDB | 61 | Milford, Connecticut, USA | Results |
| 2000 | #7939 | Gavin Brady | Jamie Gale | NZL | 33 | Cleveland, Ohio, USA | Results |
| 1999 | #7934 | Eric Doyle | Tom Olson | SDB | 36 | Winthrop, MA, USA | Results |
| 1998 | #7829 | Mark Reynolds | Rick Peters | SDB | 49 | Lake George, New York, USA | Results |
| 1997 | #7711 | Joe Londrigan | Mark Strube | SDB | 24 | Marina del Rey, California, USA | Results |
| 1996 | #7872 | Ross Macdonald | Dag Nyhof | EB | 34 | Wilmette, Illinois, USA | Results |
| 1995 | #7454 | Ross Macdonald | Pat Dion | EB | 57 | Galesville, MD, USA | Results |
| 1994 | #7773 | Paul Cayard | George Iverson | WSFB | 46 | Marblehead, MA, USA | Results |
| 1993 | #7469 | Ross Macdonald | Eric Jespersen | EB | 43 | San Diego, California, USA | Results |
| 1992 | #7288 | Joe Londrigan | Phil Trinter | LS | 34 | Grosse Pointe Shores, Michigan, USA | Results |
| 1991 | #7288 | Joe Londrigan | Mark Busch | WH | 40 | Chicago, Illinois, USA | Results |
| 1990 | #7200 | Gastao Brun | Andre Lekazyki | RdJ | 48 | Winthrop, MA, USA | Results |
| 1989 | #7288 | Mark Reynolds | Hal Haenel | SDB | 44 | English Bay, Vancouver, Canada | Results |
| 1988 | #7302 | Ed Adams | Rick Hennig | NB | 61 | Ithica, NY, USA | Results |
| 1987 | #7265 | J.A. MacCausland | Alan Romefelt | CR | 50 | Milford, CT, USA | Results |
| 1986 | #7109, The Usual | Vince Brun | Hugo Schreiner | SDB | 49 | Cleveland, OH, USA | Results |
| 1985 | #6921, Bananas | Vince Brun | Robert Kenney | SDB | 40 | San Diego, California, USA | Results |
| 1984 | #6854, Spirit | J.A. MacCausland | Jay Brown | CR | 43 | Westport, CT, USA | Results |
| 1983 | #6854, Spirit | J.A. MacCausland | Jay Brown | CR | 37 | Cleveland, OH, USA | Results |
| 1982 | #6550, Theophilus | John Driscoll | Hugo Schreiner | SDB | 34 | Wilmette Harbor, IL, USA | Results |
| 1981 | #6432, War Hawk | Andy Menkart | Kevin Murphy | BH | 27 | Galveston Bay, TX, USA | Results |
| 1980 | #6498, Bucephalus | Alexander Hagen | Vincent Hoesch | Glu | 46 | Milford, CT, USA | Results |
| 1979 | #5761, Spirit III | Peter Wright | Todd Cozzens | SLM | 38 | Puget Sound, Seattle, WA | Results |
| 1977 | #5443, Menace | Dennis Conner | Ron Anderson | SDB | 48 | San Diego, CA, USA | Results |
| 1976 | #5681, Virgo III | Peter Wright | William Wright | SLM | 51 | Boston, MA, USA | Results |
| 1975 | #5607, Dingo | Ding Schoonmaker | Jerry Ford | BisB | 38 | Mobile Bay, AL, USA | Results |
| 1974 | #5681, Virgo | Peter Wright | William Wright | SLM | 38 | Cleveland, OH, USA | Results |
| 1973 | #5776, Big TR | Thompson Adams | Bill Richards | WH | 37 | Chesapeake Bay, MD, USA | Results |
| 1972 | #5669, Strings 'n Things | Charles Morgan | John Winters | TaB | 36 | Toronto, Canada | Results |
| 1971 | #5635, Neguinho | Joerg Bruder | Claud Biekarch | Gua | 50 | Biscayne Bay, FL, USA | Results |
| 1970 | #5455, Gem X | Durward Knowles | David Dickey | N | 52 | Rockport, MA, USA | Results |
| 1969 | #5350, Hannah | Barton Beek | Charles Beek | LB | 23 | Chicago, IL, USA | Results |
| 1968 | #5150, Good Grief | Tom Blackaller | Gary Mull | WSFB | 35 | San Francisco, CA, USA | Results |
| 1967 | #4861, Ariel | Alan Holt | Richard Gates | Shil | 48 | Toronto, Canada | Results |
| 1966 | #4862, Swingin' Star | Don Trask | William Kreysler | Ric | 41 | Cleveland, OH, USA | Results |
| 1965 | #4969, Scandale | John Albrechtson | George Yule | Vin | 45 | Oxford, MD, USA | Results |
| 1964 | #4541, Blitzkrieg | Buddy Friedrichs | Craig Nelson | NCG | 12 | Galveston Bay, TX, USA | Results |
| 1963 | #4615, Star of the Sea | Joseph Duplin | Rodney Long | BH | 62 | Rye, New York, USA | Results |
| 1962 | #4078, Boron | Bill Buchan | Jay Winberg | PS | 22 | Puget Sound, Washington, USA | Results |
| 1961 | #4241, Glider | Richard Stearns | Lynn Williams | WH | 44 | Toronto, Canada | Results |
| 1960 | #4241, Glider | Richard Stearns | Lynn Williams | WH | 40 | Milford, CT, USA | Results |
| 1959 | #4143, Turmoil | Gary Comer | William Hackel | JP | 37 | Chicago, IL, USA | Results |
| 1958 | #4025, Shaughnessy | E.W. Etchells | Mary Etchells | CLIS | 46 | Choptank River, Maryland, USA | Results |
| 1957 | #3877, North Star III | Lowell North | James Hill | SDB | 25 | Newport Harbor, CA, USA | Results |
| 1956 | #3679, Circus | Howie Lippincott | Nelson Macan | ER | 49 | Vermillion, OH, USA | Results |
| 1955 | #3076, Kurush IV | J. de Cardenas | de Cardenas, Jr | Mar | 54 | Rye, NY, USA | Results |
| 1954 | #2985, Sea Skate | Jack Van Dyke | Gerrit D. Foster | Mil | 37 | Rockport, MA, USA | Results |
| 1953 | #3188, Flower | Bob Lippincott | William Norris | WJ | 30 | Milwaukee, WI, USA | Results |
| 1952 | #2700, Flame | Stan Oglivy | William Lynn | WLIS | 31 | Toronto, Canada | Results |
| 1939 | #1162, Whitecap II | Walter Sumner | Jack Watson | SDB | 14 | San Francisco, CA, USA | Results |