Photo Credit: FRIED ELLIOTT / friedbits.com
| YEAR | BOAT | SKIPPER | CREW | FLEET | ENTRIES | LOCATION | RESULTS |
|---|---|---|---|---|---|---|---|
| 2025 | 8602 | M. Kusznierewicz | Bruno Prada | ISOL | 65 | Miami | Results |
| 2024 | 8559 | M. Kusznierewicz | Bruno Prada | ISOL | 66 | Miami | Results |
| 2023 | 8548 | M. Kusznierewicz | Bruno Prada | ISOL | 73 | Miami | Results |
| 2022 | 8548 | M. Kusznierewicz | Bruno Prada | ISOL | 57 | Miami | Results |
| 2021 | 8548 | M. Kusznierewicz | Bruno Prada | ISOL | 25 | Miami | Results |
| 2020 | 8548 | M. Kusznierewicz | Bruno Prada | ISOL | 66 | Miami | Results |
| 2019 | 8423 | Eric Doyle | Payson Infelise | NH | 64 | Miami | Results |
| 2018 | 8533 | Diego Negri | Sergio Lambertenghi | VE | 73 | Miami | Results |
| 2017 | 8481 | Mark Mendelblatt | Magnus Liljedahl | TaB | 69 | Miami | Results |
| 2016 | 8340 | Robert Stanjek | Frithjof Kleen | BF | 68 | Miami | Results |
| 2015 | 8474 | Lars Grael | Samuel Goncalves | Par | 57 | Miami | Results |
| 2014 | 8474 | Lars Grael | Samuel Goncalves | Par | 55 | Miami | Results |
| 2013 | 8177 | Mark Mendelblatt | Brian Fatih | TaB | 57 | Miami | Results |
| 2012 | 8237 | Xavier Rohart | Pierre Alexis Ponsot | Ni | 62 | Miami | Results |
| 2011 | 8270 | Guillame Florent | Pascal Rambeau | VF | 90 | Miami | Results |
| 2010 | 8362 | Rick Merriman | Phil Trinter | LH | 84 | Miami | Results |
| 2009 | 8272 | Peter Bromby | Magnus Liljedahl | Isol | 64 | Miami | Results |
| 2008 | 8309 | Afonso Domingos | Bernardo Santos | POR | 114 | Miami | Results |
| 2007 | 8187 | Hamish Pepper | David Giles | Isol | 75 | Miami | Results |
| 2006 | 8230 | John Dane | Austin Sperry | MoB | 92 | Miami | Results |
| 2005 | 8147 | Mark Mendelblatt | Mark Strube | TaB | 69 | Miami | Results |
| 2004 | 8145 | Afonso Domingos | Bernardo Santos | POR | 92 | Miami | Results |
| 2003 | 7899 | Peter Bromby | Martin Siese | BER | 112 | Miami | Results |
| 2002 | 8067 | Mark Reynolds | Magnus Liljedahl | SDB | 32 | Miami | Results |
| 2001 | 7988 | Peter Bromby | Martin Siese | BER | 76 | Miami | Results |
| 2000 | 7838 | Ross MacDonald | Kai Bjorn | EB | 94 | Miami | Results |
| 1999 | 7838 | Ross MadConald | Kai Bjorn | EB | 94 | Miami | |
| 1998 | 7828 | Mark Reynolds | Magnus Liljedahl | SDB | 66 | Miami | Results |
| 1997 | 7828 | Mark Reynolds | Magnus Liljedahl | SDB | 63 | Miami | |
| 1996 | 7836 | Vince Brun | Magnus Liljedahl | SDB | 79 | Miami | |
| 1995 | 7737 | Ross MacDonald | Kai Bjorn | EB | 97 | Miami | |
| 1994 | 7737 | Ross MacDonald | Bruce MacDonald | EB | 65 | Miami | |
| 1993 | 7602 | Peter Wright | Greg Cook | SLM | 53 | Miami | |
| 1992 | 7460 | Mark Reynolds | Hal Haenel | SDB | 65 | Miami | |
| 1991 | 7302 | Ed Adams | George Iverson | NB | 66 | Miami | |
| 1990 | 7460 | Mark Reynolds | Hal Haenel | SDB | 68 | Miami | |
| 1989 | 7288 | Mark Reynolds | Hal Haenel | SDB | 53 | Miami | |
| 1988 | 7101 | Ed Adams | Tom Olsen | NB | 52 | Miami | |
| 1987 | 7209 | Vince Brun | Hugo Schreiner | SDB | 68 | Miami | |
| 1986 | 7209 | Vince Brun | Hugo Schreiner | SDB | 63 | Miami | |
| 1985 | 6921 | Vince Brun | Bob Billingham | SDB | 64 | Miami | |
| 1984 | 6464 | Mark Reynolds | Chris Gould | SDB | 68 | Miami | |
| 1983 | 6910 | Andy Menkart | James Kavle | WS | 75 | Miami | |
| 1982 | 6680 | Vince Brun | Randy MacLaren | SDB | 70 | Miami | |
| 1981 | 6680 | Vince Brun | Todd Cozzens | SDB | 66 | Miami | |
| 1980 | 6560 | Bill Buchan | Douglas Knight | PS | 47 | Miami | |
| 1979 | 6042 | Bill Buchan | Douglas Knight | PS | 54 | Miami | |
| 1978 | 5681 | Peter Wright | Todd Cozzens | SLM | 82 | Miami | |
| 1977 | 5607 | Ding Schoonmaker | Chris Rogers | BisB | 58 | Miami | |
| 1976 | 5607 | Ding Schoonmaker | Jerry Ford | BisB | 63 | Miami | |
| 1975 | 5681 | Peter Wright | William Wright | SLM | 43 | Miami | Results |
| 1974 | 5607 | Ding Schoonmaker | Jerry Ford | BisB | 30 | Miami | |
| 1973 | 5660 | Bill Buchan | Craig Thomas | PS | 57 | Miami | |
| 1972 | 5524 | Read Ruggles | David Dickey | BisB | 45 | Miami | |
| 1971 | 5407 | Ding Schoonmaker | Joerg Bruder | BisB | 49 | Miami | |
| 1970 | 5407 | Ding Schoonmaker | Joerg Bruder | BisB | 39 | Miami | |
| 1969 | 4621 | Frank Zagarino | Gould Ryder | BisB | 38 | Miami | |
| 1968 | 5271 | Richard Stearns | Lynn Williams | WH | 32 | Miami | |
| 1967 | 5271 | Richard Stearns | Lynn Williams | WH | 26 | Miami | |
| 1966 | 5012 | Joe Duplin | Rodney Long | BH | 30 | Miami | |
| 1965 | 4459 | Read Ruggles | David Dickey | BisB | 24 | Miami | |
| 1964 | 4207 | Ding Schoonmaker | Asa Colson | BisB | 22 | Miami | |
| 1963 | 4589 | Howard Lippincott | Herb Hild | ES | 31 | Miami | Results |
| 1962 | 4305 | Basil Kelly | David Kelley | CoH | 20 | Miami | |
| 1959 | 3076 | Alvaro de Cardenas | Jorge de Cardenas | Mar | 22 | Havana | |
| 1955 | 3076 | Jorge de Cardenas | Alvaro de Cadenas | Mar | 15 | Havana | |
| 1954 | 2934 | Alberto Reyes | Jose de la Campa | FdeH | 28 | Havana | |
| 1953 | 3167 | Ding Schoonmaker | Donald Pritchard | N | 25 | Havana | |
| 1952 | 3081 | Robert Lippincott | Bob Levine | WJ | 22 | Havana | |
| 1951 | 2967 | Durward Knowles | Ding Schoonmaker | N | 26 | Havana | |
| 1950 | 2125 | Skip Etchells | Mary Etchells | WLIS | 15 | Havana | |
| 1949 | 1961 | Woodie Pirie | F.S. Dixon | WH | 12 | Havana | |
| 1948 | 1961 | Woodie Pirie | Sam Pirie | WH | 11 | Havana | |
| 1942 | 1902 | Alfred de Marigny | - | N | 6 | Havana | |
| 1941 | 1563 | Harry Nye | - | SLM | 13 | Havana | |
| 1940 | 1563 | Harry Nye | - | SLM | 14 | Havana | |
| 1939 | 1310 | Paul Smart | - | CLIS | 17 | Havana | |
| 1938 | 1563 | Harry Nye | - | SLM | 14 | Havana | |
| 1937 | 1367 | Paul Shields | Corny Shields | PGB | 19 | Havana | |
| 1936 | 202 | Adrian Iselin II | Elwood White | WLIS | 14 | Havana | |
| 1935 | 202 | Adrian Iselin II | Sr. Carricabura | WLIS | 13 | Havana | |
| 1934 | - | not sailed | - | - | |||
| 1933 | 202 | Adrian Iselin II | Elwood White | WLIS | 18 | Havana | |
| 1932 | 700 | David Atwater | Charles Lawton | NB | 16 | Havana | |
| 1931 | 388 | Carlos de Cardenas | - | BdeH | - | Havana | |
| 1930 | 499 | W.F. Teves | - | WLIS | 24 | Havana | |
| 1929 | 333 | Fred Bedford | Brigs Cunningham | CLIS | 9 | Havana | |
| 1928 | 510 | R. Robinson | D. Robinson | PGB | 9 | Havana | |
| 1927 | 202 | Adrian Iselin II | Ed Willis | WLIS | 13 | Havana | Results |