Little Miss & Master Highland Past Winners
1958        Marilyn Anita Moon and Mark Swecker
1959        Donna Hooke and Brent Obaugh
1960        Betty Sue Hiner and Bobby Ralston
1961        Ellen Swecker and Jerry Hoover
1962        Julie Mullenax and Allen Thompson
1963        Debra Moon and Gene Dever
1964        Marilyn Reynolds and Eddie Hooke
1965        Tonya Kay Marshall and Michael Herold
1966        Corissa White and Kirk Billingsley
1967        Stephanie Dawn Beverage and Alan Dale Puffenbarger
1968        Dawn Smith and Craig Smith (brother and sister)
1969        Mary Ann Corbett and Kenneth Herold
1970        Lisa Crayne Swecker and Kirk Propst
1971        Connie Sue Hill and Darrin King
1972        Terri Jack and Anthony Frye
1973        Michelle Smith and Jim Armstrong
1974        Kitty Will and Michael McCray
1975        Adria Rhea and J.M. Simmons
1976        Letitia Rexrode and Roby Halterman
1977        Amy Jo Wimer and Steven Simmons
1978        Jennifer Letcher Warner and Mark Orebaugh
1979        Christy Lightner and Jason Rexrode
1980        Tammy Powers and John Colaw
1981        Marcella Townsend and John Hull
1982        Kimberly Lowry and Aaron Blagg
1983        Sarah Catherine Ashe and Danny Hull
1984        Amy Jo Hammer and Curtis Lockridge
1985        Jessica Elaine Simmons and William Alan Hooke
1986        Brittany Whitelaw and Jimmy Hagan
1987        Jessica Simmons and Joshua Curry
1988        Michele Simmons and Donnie Wayne Halterman
1989        Tarah Waybright  and Thomas Stevenson
1990        Meagan Gibson and Ben Ralston
1991        Meagan Rexrode and Brandon Smith
1992        Courtney Marshall and Jacob Colaw
1993        Stefanie Hull and Justin Siron
1994        Laura Moyers and Cody Ralston
1995        Hannah Hull and John Laramie Botkin
1996        Brittany Young and Charles Moyers
1997        Lori Beverage and Aaron King
1998        Cynthia Hull and Logan Stuber
1999        Emily Botkin and James Hancock
2000        Savannah Arnott and Michael Humphries
2001        Tabitha Hiner and Ethan Botkin
2002        Emily Kimble and Michael Lambert
2003        Brooke Harper and Noah Arnott
2004        Mary Kaytlin Lambert and Avery Smith
2005        Katelyn Hise and Lucas Wimer
2006        Hannah Newlen and Will Thomas
2007        Jadalyn Hull and Alexander Smith
2008        Rhea Bendel and Caleb Hiner
2009        Carly Thomas and Dakota Ritchie
2010        Erin Kay Brendel and Colton Williams
2011        Margaret Drummond Harmon and John William Wagner
2012        Kylie Arbogast and Tristan Carpenter
2013        Chloe Lightner and Zachary Armstrong
2014        Kristina Neil and Joseph Will
2015        MaKynley Smith and Braiden Moats