ISCA Master World Championship / International Master Championship Winners
| Year | Winner | Host |
| 2024 | Andy Beeckman | Davis Island Yacht Club |
| 2023 | David Loring | Pensacola Yacht Club |
| 2022 | Paul-John Patin | Clearwater Yacht Club |
| 2021 | Eugene Schmitt | Davis Island Yacht Club |
| 2019 | Alex Zimmerman | Bonaire Sailing Foundation |
| ISCA Master World Championship | ||
| 2018 | Eric Oetgen | St Andrews Bay YC |
| International Masters Championship | ||
| 2017 | Paul-Jon Patin | Charlotte Harbor Community Sailing Center |
| 2016 | Paul-Jon Patin | US Sailing Center, Martin County, FL |
| 2015 | Greg Gust | Davis Island YC |
| 2014 | Greg Gust | Pensacola YC |
| 2013 | Greg Gust | Davis Island YC |
| 2012 | Bill Brangiforte | Lake Monroe Sailing Association |
| 2011 | Malcolm Smith | Fort Walton YC |
| 2010 | Nancy Heffernan-Haberland | Melbourne YC |
| 2009 | Donald Martinborough | Davis Island YC |
| 2008 | Thomas Whitehurst | PYC |
| 2007 | Thomas Whitehurst | Charlotte Harbor Community SC |
| 2006 | Todd Edwards | Davis Island YC |
| 2005 | Malcolm Smith | The Netherlands |
| 2004 | Jou Blouin | Melbourne YC |
| 2003 | Chris Williams | Upper Keys SC |
| 2002 | Dick Tillman | US Sailing Center |
| 2001 | Clifton Charles | Charlot Harbour |
| 2000 | Jou Blouin | Sarasota Sailing Squadron |
| 1999 | Malcolm Smith | Davis Island Yacht Club |
| 1998 | Dick Tillman | Coconut Grove SC |
| 1997 | Jou Blouin | Tampa |
| 1996 | Dick Tillman | Eau Gallie YC |
| 1995 | Dick Tillman | Sarasota Sailing Squadron |
| 1994 | Joe Blouin | Davis Island YC |
| 1993 | Don Bergman | Key West |
| 1992 | ||
| 1991 | Jou Blouin | Miami YC |
| 1990 | Don Bergman | Sarasota Sailing Squadron |
| 1989 | Don Bergman | Davis Island YC |
