US Midwinter Championships
| Year | Winner | Host | Results |
| 2025 | Eduardo Cordero | Bay Waveland YC, MS | BWYC 2025 |
| 2024 | David Hernadez (GUA) | Davis Island Yacht Club | DIYC 2024 |
| 2023 | Jean Paul de Trazegnies | Pensacola Yacht Club | PYC 2023 |
| 2022 | Diego Silvestre | Clearwater Yacht Club | CYC 2022 |
| 2021 | Jose Hermandez (Guatemala) | Davis Island Yacht Club | DIYC 2021 |
| 2020 | not sailed | Bay Waveland Yacht Club | |
| 2019 | Conner Blouin | Davis Island Yacht Club | DIYC 2019 |
| 2018 | Alonso Collantes de Riglos (Peru) | St. Andrews Bay YC | StABYC 2018 |
| 2017 | Eugene Schmitt | Charlotte Harbor Community Sailing Center | CHCSC 2017 |
| 2016 | Eugene Schmitt | Martin County US Sailing Center | USSCMC 2016 |
| 2015 | Jonathan Martinetti | Melbourne, FL | MYC 2015 |
| 2014 | Jonathan Martinetti | Pensacola YC | PYC 2014 |
| 2013 | David Mendelblatt | Sarasota Sailing Squadron | SSC 2013 |
| 2012 | Jeff Olson | Edison Sailing Center | |
| 2011 | Fernando Monllor | Fort Walton YC | |
| 2010 | Eduardo Cordero | Sarasota Sailing Squadron | |
| 2009 | Eduardo Cordero | Clearwater YC | |
| 2008 | Hank Saurage | St. Andrews Bay YC | |
| 2007 | David Mendelblatt | Edison Sailing Center | |
| 2006 | David Mendelblatt | Melbourne Yacht Club | |
| 2005 | David Mendelblatt | Sarasota Sailing Squadron | |
| 2004 | David Mendelblatt | Pensacola, FL | |
| 2003 | Juan Ignacio Maegli (Guatemala) | Gulfport, FL | |
| 2002 | Todd Edwards | Tampa, FL | |
| 2001 | David Loring | Clearwater, FL | |
| 2000 | Zane Yoder | Fort Walton Beach, FL | |
| 1999 | Todd Edwards | Sarasota, FL | |
| 1998 | Chip Clifton | Tampa, FL | |
| 1997 | Eduardo Cordero | Miami, FL | |
| 1996 | Eduardo Cordero | Sarasota, FL | |
| 1995 | Jeff Linton | Tampa, FL | |
| 1994 | Eduardo Cordero | Satellite Beach, FL | |
| 1993 | Robert Findlay | Sarasota, FL | |
| 1992 | Alan Beckwith | Tampa, FL | |
| 1991 | Scott Kyle | Satellite Beach, FL | |
| 1990 | Robert Findlay | Bay St. Louis, MS | |
| 1989 | Lawrence Maher | Houston, TX | |
| 1988 | Robert Findlay | Miami, FL | |
| 1987 | Robert Findlay | Tampa, FL | |
| 1986 | Nancy Haberland | Mount Dora, FL | |
| 1985 | Robert Findlay | New Orleans, LA | |
| 1984 | Robert Findlay | Sarasota, FL | |
| 1983 | Don Brennan | Mobile, AL | |
| 1982 | Donald F. Bergman | New Orleans, FL | |
| 1981 | Mike Catalano | Orlando, FL | |
| 1980 | Mike Catalano | Mt. Dora, FL | |
| 1979 | Nat Philbrick | Orlando, FL | |
| 1978 | Mike Catalano | Tampa, FL | |
| 1977 | Mike Catalano | Lake Conway, FL | |
| 1976 | Mike Catalano | ||
| 1975 | |||
| 1974 | |||
| 1973 | |||
| 1972 | |||
| 1971 | |||
| 1970 | |||
| 1969 | Doug Brown | Miami, FL | |
| 1968 | |||
| 1967 | |||
| 1966 | |||
| 1965 |
