| Year | # | Event | Venue | Winner |
|---|---|---|---|---|
| 2019 | 51 | Charles Galloway Trophy | Gulfport YC | O’Mara, Martha Ellis |
| 2018 | 50 | Charles Galloway Trophy | Gulfport YC | O’Mara, Martha Ellis |
| 2017 | 49 | Charles Galloway Trophy | Gulfport YC | Saurage, Hank |
| 2016 | 48 | Charles Galloway Trophy | Gulfport YC | Saurage, Hank |
| 2015 | 47 | Charles Galloway Trophy | Gulfport YC | Saurage, Hank |
| 2014 | 46 | Charles Galloway Trophy | Gulfport YC | Saurage, Hank |
| 2013 | 45 | Charles Galloway Trophy | Gullport YC | Edwards, Todd |
| 2012 | 44 | Charles Galloway Trophy | Gulfport YC | Whitehurst, Thomas |
| 2011 | 43 | Charles Galloway Trophy | Gulfport YC | Saurage, Hank |
| 2010 | 42 | Charles Galloway Trophy | Gulfport YC | Saurage, Hank |
| 2009 | 41 | Charles Galloway Trophy | Gulfport YC | Edwards, Todd |
| 2008 | 40 | Charles Galloway Trophy | Gulfport YC | Whitehurst, Thomas |
| 2007 | 39 | Charles Galloway Trophy | Gulfport YC | Kleinschrodt, Karl |
| 2006 | 38 | Charles Galloway Trophy | Gulfport YC | Whitehurst, Thomas |
| 2005 | 37 | Charles Galloway Trophy | Gulfport YC | Edwards, Clinton |
| 2004 | 36 | Charles Galloway Trophy | Gulfport YC | Whitehurst, Thomas |
| 2003 | 35 | Charles Galloway Trophy | Gulfport YC | Whitehurst, Thomas |
| 2002 | 34 | Charles Galloway Trophy | Gulfport YC | Stieffel, Bishop |
| 2001 | 33 | Charles Galloway Trophy | Gulfport YC | Saurage, Hank |
| 2000 | 32 | Charles Galloway Trophy | Gulfport YC | Yoder, Zane |
| 1999 | 31 | Charles Galloway Trophy | Gulfport YC | Edwards, Todd |
| 1998 | 30 | Charles Galloway Trophy | Gulfport YC | Edwards, Clinton |
| 1997 | 29 | Charles Galloway Trophy | Gulfport YC | Edwards, Clinton |
| 1996 | 28 | Charles Galloway Trophy | Gulfport YC | Beatty, Ash |
| 1995 | 27 | Charles Galloway Trophy | Gulfport YC | Ollinger, Ellis |
| 1994 | 26 | Charles Galloway Trophy | Gulfport YC | Kelly, Leslie |
| 1993 | 25 | Charles Galloway Trophy | Gulfport YC | Edwards, Todd |
| 1992 | 24 | Charles Galloway Trophy | Gulfport YC | Mitchel, Kam |
| 1991 | 23 | Charles Galloway Trophy | Gulfport YC | Edwards, Todd |
| 1990 | 22 | Charles Galloway Trophy | Gulfport YC | Saurage, Hank |
| 1989 | 21 | Charles Galloway Trophy | Gulfport YC | Saurage, Hank |
| 1988 | 20 | Charles Galloway Trophy | Gulfport YC | Doyle, Michael |
| 1987 | 19 | Charles Galloway Trophy | Gulfport YC | Edwards, Clinton |
| 1986 | 18 | Charles Galloway Trophy | Gulfport YC | Evans, Todd |
| 1985 | 17 | Charles Galloway Trophy | Gulfport YC | Hopkins,Sam |
| 1984 | 16 | Charles Galloway Trophy | Gulfport YC | Bell, Jeff |
| 1983 | 15 | Charles Galloway Trophy | Gulfport YC | Weatherly, Shannon |
| 1982 | 14 | Charles Galloway Trophy | Gulfport YC | Weatherly, Shannon |
| 1981 | 13 | Charles Galloway Trophy | Gulfport YC | Dane-Weatherly, Leslie |
| 1980 | 12 | Charles Galloway Trophy | Gulfport YC | Hopkins,Sam |
| 1979 | 11 | Charles Galloway Trophy | Gulfport YC | Hopkins,Sam |
| 1978 | 10 | Charles Galloway Trophy | Gulfport YC | Hopkins,Sam |
| 1977 | 9 | Charles Galloway Trophy | Gulfport YC | McGinnis, Kelly |
| 1976 | 8 | Charles Galloway Trophy | Gulfport YC | McGinnis, Kelly |
| 1975 | 7 | Charles Galloway Trophy | Gulfport YC | Heausler, Buzzy |
| 1974 | 6 | Charles Galloway Trophy | Gulfport YC | Heausler, Buzzy |
| 1973 | 5 | Charles Galloway Trophy | Gulfport YC | McDonald, Bill |
| 1972 | 4 | Charles Galloway Trophy | Gulfport YC | Perry, Mike |
| 1971 | 3 | Charles Galloway Trophy | Gulfport YC | Stieffel, Woody |
| 1970 | 2 | Charles Galloway Trophy | Gulfport YC | Quave, Gerald |
| 1969 | 1 | Charles Galloway Trophy | Gulfport YC | Grimes, Willis |