1999 Meade Co.Blake Andrew TyreeKaitlyn Alexie Mattingly
2000 Western KY. StateSawyer StalcupJaysie Campbell
2001 Meade Co.Brady SmithRebecca Clark
2002 Larue Co.Brandon GrayKayla Nunn
2003 Franklin Co.Tucker PhelpsCarolyn Mefford
2004 Garrard Co.Jordan DeckerKylie Brockman
2005 Adair Co.Zachary GloverBailey Gibson
2006 Henderson Co.Abbot StinsonLatta Rose Stinson
2007 Union Co. FairHunter RobinsonTori French
2008 Casey Apple Fest.James Dylan BrownMcKenzie Marie Smithers
2009 Grant Co. FairKasey Marie HillEvan George Dunaway
2010 Pendleton Co. FairNate GosneyKennadi Mayer
2011 Oldham Co. FairIsaac StaffKylie Stanley
2012 Taylor Co. FairTrace HigdonHarper Johnson
2013 Clark Co. FairKayleigh CarderAshton Bain Arvin
2014 Casey Co. FairNathan AntleCamdin Ally Cooper
2015 Adair Co. FairJasper William KempGabrielle Rachelle Kemp
2016 Henderson Co. Fair Walker TrammelAmeliaGail “Millie” Jones