Photo Credit: FRIED ELLIOTT / friedbits.com
| YEAR | BOAT | SKIPPER | CREW | FLEET | ENTRIES | LOCATION | RESULTS |
|---|---|---|---|---|---|---|---|
| 2025 | #8537 | George Szabo | Guy Avellon | SDB | 33 | Gibson Island, MD, USA | Results |
| 2024 | #8474 | Tomas Hornos | Mauricio Bueno | BH | 33 | Miami, FL, USA | Results |
| 2023 | #8509 | Augie Diaz | Bruno Prada | BisB | 21 | Cleveland, OH | Results |
| 2022 | #8466 | Paul Cayard | Brad NIchol | WSFB | 33 | Sunapee, NH, USA | Results |
| 2021 | #8466 | Paul Cayard | Luke Lawrence | WSFB | 20 | Miami, FL, USA | Results |
| 2020 | Not Held | ||||||
| 2019 | #8448 | Carl Buchan | Jamie Buchan | PS | 26 | San Diego, CA, USA | Results |
| 2018 | #8474 | Lars Grael | Samuel Goncalves | Par | 37 | Miami, FL, USA | Results |
| 2017 | #8000 | Arthur Anosov | David Caesar | GL | 31 | Cleveland, OH, USA | Results |
| 2016 | Not Held | ||||||
| 2015 | #8203 | Brian Ledbetter | Joshua Revkin | PS | 38 | Miami, FL, USA | Results |
| 2014 | #8241 | Lars Grael | Brad Nichol | Par | 30 | Sunapee, NH, USA | Results |
| 2013 | #8465 | Augie Diaz | Arnis Baltins | BisB | 21 | Nassau, Bahamas | Results |
| 2012 | #8177 | Tomas Hornos | Kip Gardner | BH | 30 | Annapolis, MD, USA | Results |
| 2011 | #8170 | Tom Londrigan Jr. | LS | ||||
| 2010 | #8401 | Richard Clarke | Tyler Bjorn | VI | 29 | Nassau, Bahamas | Results |
| 2009 | #8259 | Paul Cayard | WSFB | ||||
| 2008 | #8362 | Rick Merriman | LH | ||||
| 2007 | #8256 | F. Loof | BK | ||||
| 2006 | #8230 | John Dane III | Austin Sperry | MoB | 42 | Annapolis, MD, USA | Results |
| 2005 | #8159 | Paul Cayard | WSFB | ||||
| 2004 | #8061 | Lovell | NOG | ||||
| 2003 | #8077 | Shiebler | WSFB | ||||
| 2002 | #8088 | Paul Cayard | SDB | ||||
| 2001 | Gigibee | Vince Brun | SDB | ||||
| 2000 | #7737 | Eric Doyle | SDB | ||||
| 1999 | #7910 | Pickel | Brm | ||||
| 1998 | #7862 | John MacCausland | CR | ||||
| 1997 | #7829 | Mark Reynolds | SDB | ||||
| 1996 | #7775 | Paul Cayard | SDB | ||||
| 1995 | #7737 | Ross Macdonald | EB | ||||
| 1994 | #7732 | Vince Brun | SDB | ||||
| 1993 | #7640 | John Kostecki | WSFB | ||||
| 1992 | #7460 | Mark Reynolds | SDB | ||||
| 1991 | #7460 | Mark Reynolds | SDB | ||||
| 1990 | #7338 | Johansson | Vin | ||||
| 1989 | #7209 | Vince Brun | SDB | ||||
| 1988 | #7288 | Mark Reynolds | SDB | ||||
| 1987 | Anna | Vince Brun | SDB | ||||
| 1986 | Bardolino Class. | Vince Brun | SDB | ||||
| 1985 | Trigger Happy | Paul Cayard | WSFB | ||||
| 1984 | Paul Cayard | WSFB | |||||
| 1983 | Virgo IV | Wright | SLM | ||||
| 1982 | Menkart | BH | |||||
| 1981 | Faster Horses | Tom Blackaller | WSFB | ||||
| 1980 | Frolic | Buchan | PS | ||||
| 1979 | Not Held | ||||||
| 1978 | Chewbacca | Tom Blackaller | WSFB | ||||
| 1977 | Chewbacca | Tom Blackaller | WSFB | ||||
| 1976 | Not Held | ||||||
| 1975 | Gem | Knowles | N | ||||
| 1974 | Mustard Seed | Morgan | TaB | ||||
| 1973 | Frolic | Buchan | PS | ||||
| 1972 | Menace | Dennis Conner | SDB | ||||
| 1971 | Gilder | Stearns | WH | ||||
| 1970 | North Star | Lowell North | SDB | ||||
| 1969 | Dingo | Ding Schoonmaker | BisB | ||||
| 1968 | Good Grief | Tom Blackaller WSFB) | |||||
| 1967 | Dingo | Ding Schoonmaker | BisB | ||||
| 1966 | Gilder | Stearns | WH | ||||
| 1965 | Gilder | Stearns | WH | ||||
| 1964 | Gilder | Stearns | WH | ||||
| 1963 | Gilder | Stearns | WH | ||||
| 1962 | Gilder | Stearns | WH | ||||
| 1961 | Shandon | Skip Etchells | CLIS | ||||
| 1960 | Gilder | Stearns | WH | ||||
| 1959 | Shaughnessy | Skip Etchells | CLIS | ||||
| 1958 | Shannon | Skip Etchells | CLIS | ||||
| 1957 | La Flor | R. Lippincott | WJ | ||||
| 1956 | Flower | R. Lippincott | WJ | ||||
| 1955 | Gem III | Knowles | N | ||||
| 1954 | Vega IV | Lyon | BB | ||||
| 1953 | Gem | Knowles | N | ||||
| 1952 | Kathleen | Williams | SLM | ||||
| 1951 | Sea Robin | R. Lippincott | WJ | ||||
| 1950 | Glider | Stearns | WH | ||||
| 1949 | Wahini | O'Gorman | WLIS | ||||
| 1948 | Cajin | Knowles | N | ||||
| 1947 | Whip | Ogilvy | WLIS | ||||
| 1946 | Not Held | ||||||
| 1945 | Not Held | ||||||
| 1944 | Not Held | ||||||
| 1943 | Not Held | ||||||
| 1942 | Not Held | ||||||
| 1941 | Gale | Nye | SLM | ||||
| 1940 | Shucks | White | WLIS | ||||
| 1939 | Scout | Jahncke | NOG | ||||
| 1938 | Gale | Nye | SLM | ||||
| 1937 | Pioneer | Smith | OtL | ||||
| 1936 | Shucks | White | WLIS | ||||
| 1935 | Ace | Iselin | WLIS | ||||
| 1934 | Ace | Iselin | WLIS |