1987 Kimberly Valentine, Boone Co Fair
1988 Tracey Ann Conley, Ewing-Fleming Co Fair
1989 Stephanie Michelle Taylor, Adair Co Fair
1990 Kristi Allen Rice, Clark Co Fair
1991 LeAnn Chaney, Bluegrass Fair
1992 Mitzi Jones, Temple Hill-Barren Co Fair
1993 Tanisha Harris, Hardin Co Fair
1994 Lori West, Clinton Co Fair
1995 Jolene Youngster, Allen Co Fair
1996 Crystal M Travis, Cumberland Co Fair
1997 Keri Lynn Bazzell, Murray-Calloway Co Fair
1998 Mary Catherine Correll, Clinton Co Fair
1999 Jo Tara Pritchard, Buechel Bash (Jefferson Co)
2000 Lori Brooke Mitchell, Adair Co Fair
2001 Jessica Kay Carmicle, Adair Co Fair
2002 Emily Renee Sloan, Woodford Co Fair
2003 Karmen Cordell, McCreary Co Fair
2004 Tara Elizabeth Conner, Russell Co Fair
2005 Brittany Michelle Denney, Clinton Co Fair
2006 Krista Keith Ennis, Clinton Co Fair
2007 Kassidy Rae Dees, Adair Co Fair
2008 Maria Montgomery, Boyle Co Fair
2009 Kelli Elizabeth Rush, Southern Kentucky Fair
2010 Megan Ann Kasama, Southern Kentucky Fair
2011 Corinna Shanice Hughes, Allen Co Fair
2012 Ashley Renee Young, Cumberland Co Fair
2013 Jenna Brooke Walters, Hardin Co Fair
2014 Kyle Nicole Hornback, Nelson Co Fair
2015 Bria Hays, Hardin Co Fair
2016 Lacey Nicole Graham, Larue Co Fair
2017 Molly Matney (resigned) Taylor Co. Fair
2017 Bethany Nicole Roberts, Marion Co. Fair
2018 Alexys Koeninger, Nicholas Co. Fair
2019 Veronica Chisholm, Nelson Co. Fair
2020 Anna Law, Ohio Co. Fair
2021 Anna Law, Ohio Co. Fair *continued reign due to covid
2022 Sydney Poor, Lincoln Co. Fair