1990 Torri Annett Lee, Metcalfe Co. Fair
1991 Lindsey DeShea Cavitt, Western Kentucky State Fair
1992 Nicole Marie Hankins, Oldham Co. Fair
1993 Crystal Michele Travis, Marshall Co. Fair
1994 Melissa Sharp, Perry Co. Heart of Gold Festival
1995 Julie Ann Hall, Union Co. Fair
1996 Elizabeth Rose Henshaw, Union Co. Fair
1997 Shalonda Marie Dixon, Hardin Co. Fair
1998 Bethany Michelle Denny, Franklin-Simpson Co. Fair
1999 Druanne Greenwell, Union Co. Fair
2000 Taryn Kelli Hagan, Monroe Co. Fair
2001 Margaret Ellen Correll, Legion-Logan Co. Fair
2002 Sarah Bryan Withers, Southern Kentucky Fair
2003 Jordon Elizabeth Clemons, Grayson Co. Fair
2004 Jonneatha Boggs, Morehead-Rowan Co. Fair
2005 Linsay Michelle Piersawl, Woodford Co. Fair
2006 Stephanie Hagan, Allen Co. Fair
2007 Kim Kasama, Nelson Co. Fair