| Year | Location | Helmsperson | Yacht | Country |
| 2025 | Miami, FL | Tony Parker | Bangor Packet | USA |
| 2024 | Tampa, FL | Paul Abdullah | Team Tarheel | USA |
| 2023 | Indian Harbour Beach, FL | John Mollicone | Sparcraft | USA |
| 2022 | Tampa, FL | Paul Foerster | Grand Slam 2 | USA |
| 2021 | Miami, FL | John Mollicone | Jesus Lizard | USA |
| 2020 | Indian Harbour Beach, FL | Tony Parker | Bangor Packet | USA |
| 2019 | Tampa, FL | Rossi Milev | Clear Air | CAN |
| 2018 | Miami, FL | Will Welles | Bogus | USA |
| 2017 | Indian Harbour Beach, FL | Mike Ingham | Tarheel | USA |
| 2016 | Tampa, FL | Rossi Milev | Angel of Harlem | CAN |
| 2015 | Tampa, FL | Will Welles | Cougar | USA |
| 2014 | Miami, FL | John Mollicone | Helly Hansen | USA |
| 2013 | Tampa, FL | John Mollicone | Helly Hansen | USA |
| 2012 | Tampa, FL | Peter Bream | Team Tarheel | USA |
| 2011 | Tampa, FL | Peter Bream | Team Tarheel | USA |
| 2010 | Tampa, FL | Charles Enright | Orange Blossom | USA |
| 2009 | Tampa, FL | Tim Healy | Pop Rocks | USA |
| 2008 | Tampa, FL | Chris Zaleski | Twins | USA |
| 2007 | Tampa, FL | Robby Brown | Preparation J | USA |
| 2006 | Tampa, FL | Anthony Kotoun | Bamba Charger | US Virgin Islands |
| 2005 | Tampa, FL | Max Skelley | Flying Squirrel | USA |
| 2004 | Tampa, FL | Geoff Moore | No It’s Not | USA |
| 2003 | Tampa, FL | Tim Healy | Hull #5277 | USA |
| 2002 | Key Biscayne, FL | Tim Healy | Hull #5277 | USA |
| 2001 | Tampa, FL | Tim Healy | Blind Squirrel | USA |
| 2000 | Tampa, FL | Geoff Moore | Pipedream | USA |
| 1999 | Key West, FL | Tim Healy | Mookie | USA |
| 1998 | Miami, FL | Terry Hutchinson | Evita | USA |
| 1997 | Key West, FL | Chris Larson | Writing Instrument | USA |
| 1996 | Miami, FL | Terry Hutchinson | USA | |
| 1995 | New Orleans, LA | Vince Brun | Bogus | USA |
| 1994 | New Orleans, LA | Terry Hutchinson | Northern Exposure | USA |
| 1993 | Miami, FL | Ken Read | Mookie | USA |
| 1992 | Miami, FL | Jay Lutz | Dashboard Mary | USA |
| 1991 | Miami, FL | Jim Brady | Fine 4WD | USA |
| 1990 | New Orleans, LA | Paul Foerster | Grand Slam | USA |
| 1989 | Miami, FL | Jim Brady | Slap and Tickle | USA |
| 1988 | Miami, FL | Ed Baird | Monster Fish | USA |
| 1987 | Miami, FL | John Kostecki | Pee Wee | USA |
| 1986 | Miami, FL | John Kostecki | Terminator | USA |
| 1985 | Miami, FL | Morgan Reeser | Sea Sharp | USA |
| 1984 | Miami, FL | David Curtis | HJ | USA |
| 1983 | Miami, FL | Ed Baird | Impulse | USA |
| 1982 | Miami, FL | Charlie Scott | Viva 40 | USA |
| 1981 | Key West, FL | Augie Diaz | I’ll Go | USA |
| 1980 | Key West, FL | John Jennings | Black Star | USA |
| 1979 | Key West, FL | Mark Ploch/Jim Brady | Tchau | USA |
| 1978 | Key West, FL | Mark Ploch | Tchau | USA |