| NAME | VICTORIES | TITLES |
| Phil Rapp | 8 | 2007 Futurity Open, 2002 Futurity Open, 2000 Futurity Non-Pro, 1999 Classic Non-Pro, 1998 Classic Non-Pro, 1998 Classic Open, 1994 Futurity Non-Pro, 1991 Futurity Non-Pro |
| Faron Hightower | 5 | 2005 Classic Open, 2001 Futurity Open, 2001 Classic Open, 1996 Classic Open, 1993 Classic Open |
| Tag Rice | 5 | 2008 Classic Open, 2006 Western Horseman Cup Open, 2004 Western Horseman Cup Open, 2004 Classic Open, 2003 Futurity Open |
| Pete Branch | 4 | 1995 Classic Open, 1994 Classic Open, 1992 Classic Open, 1986 Classic Open |
| Terry Riddle | 4 | 1997 Classic Open, 1989 Classic Open, 1986 Futurity Open, 1981 Futurity Open |
| Lloyd Cox | 3 | 2000 Classic Open, 2000 Futurity Open, 1999 Futurity Open |
| Kobie Wood | 3 | 1994 America's Greatest Cowboy, 1992 America's Greatest Cowboy, 1990 America's Greatest Cowboy |
| H.B. Bartlett | 3 | 2000 $50,000 Amateur 4-year-old, 2000 $50,000 Amateur 5/6-year-old, 1999 $20,000 Amateur |
| Buster Welch | 3 | 1988 Futurity Open, 1987 Futurity Open, 1983 Futurity Open |
| Tommy Manion | 3 | 1997 Classic Non-Pro, 1995 Futurity Non-Pro, 1992 Classic Non-Pro |
| Ronnie Rice | 3 | 1999 America's Greatest Cowboy, 1991 America's Greatest Cowboy, 1990 Futurity Open |
| Skip Queen | 3 | 2007 Classic Non-Pro, 2002 Classic Non-Pro, 1999 $50,000 Amateur 4-year-old |
| Elizabeth Queen | 2 | 2008 Futurity Non-Pro, 1998 Futurity Non-Pro |
| Austin Shepard | 2 | 2008 Futurity Open, 2007 Classic Open |
| Matt Gaines | 2 | 2006 Classic Open, 2003 Classic Open |
| Matt Miller | 2 | 2008 Classic Non-Pro, 2006 Futurity Non-Pro |
| Rachel Johnson | 2 | $100,000 Non-Pro Any Age, 2003 $50,000 Amateur Any Age |
| Glade Knight | 2 | 2001 $50,000 Amateur 5/6-year-old, 2001 $50,000 Amateur 4-year-old |
| Seth Wooten | 2 | 2000 $20,000 Amateur, 2000 $5,000 Non-Pro |
| Wilbert Roller | 2 | 2000 $50,000 Amateur Any Age, 1990 Amateur 4-year-old |
| Bill Freeman | 2 | 1998 Futurity Open, 1995 Futurity Open |
| Larry Reeder | 2 | 1985 Futurity Open, 1984 Futurity Open |
| Greg Welch | 2 | 1991 Classic Open, 1987 Classic Open |
| Bill Riddle | 2 | 1991 Classic Open, 1988 Futurity Open |
| Pat Earnheart | 2 | 1990 Classic Open, 1980 Futurity Open |
| Sumer Hightower | 2 | 1990 Non-Pro Shootout, 1988 Futurity Non-Pro |
| Judy Venezia | 2 | 1992 $50,000 Amateur, 1991 Amateur Any Age |
| Julie Roddy | 2 | 1991 Classic Non-Pro, 1991 Non-Pro Shootout |
| Billy Parker | 2 | 1989 Classic Non-Pro, 1989 Amateur Any Age |
| Norman Bruce | 2 | 1993 Non-Pro Shootout, 1990 Classic Non-Pro |
| Helen Groves | 2 | 1995 Classic Non-Pro, 1993 Futurity Non-Pro |
| Jason Surles | 2 | 1995 Amateur 4-year-old, 1995 $50,000 Amateur |
| Jody Galyean | 2 | 1996 Futurity Open, 1989 Futurity Open |
| Mary Ann Rapp | 2 | 2003 Futurity Non-Pro, 2003 Futurity Non-Pro |
| Billy Martin | 2 | 1997 Futurity Non-Pro, 1993 Classic Non-Pro |
| Steven Feiner | 2 | 2003 $50,000 Amateur 5/6-year-old, 1999 $50,000 Amateur 4-year-old |
| Jim Vangilder | 2 | 2005 Futurity Non-Pro, 2004 Classic Non-Pro |
| William S. Morris III | 2 | 2005 $50,000 Amateur 5/6-year-old, 1993 $50,000 Amateur |
| Paul Hansma | 2 | 2007 Western Horseman Cup Open, 1994 Futurity Open |
| Nicole Aldridge | 2 | 2007 $100,000 Amateur 5/6-year-old, 2006 $50,000 Amateur Any Age |
| Adam Koontz | 2 | 2007 $50,000 Amateur Any Age, 2002 $50,000 Amateur 4-year-old |