The Winkie Award was conceived by Fred M. Meyer and Marc Lewis to honor individuals who have contributed significantly to OzCon International, the International Wizard of Oz Club, and Oz in general over the years. Unlike the L. Frank Baum Memorial Award, which is managed by past recipients of that award, the Winkie Award is selected by ballot vote by those attending OzCon International each year.

1992 Peter E. Hanff
1993 C. Warren Hollister
1994 Langley Brookes Brandt
1995 Virginia Fowler
1996 Patrick Maund
1997 Eric Gjovaag
1998 Robin Olderman
1999 Eric Shanower
2000 Katie Fleming
2001 Lynn Beltz
2002 Lee Speth
2003 Fred M. Meyer
2004 Karyl Carlson
2005 Margaret Koontz
2006 Stan Sieler
2007 Paul Bienvenue
2008 David Maxine
2009 Bill Thompson
2010 Bob Baum
2011 Edith Hollister
2012 Laura Gjovaag
2013 Anna Wyatt
2014 Susan Johnson
2015 Ryan Bunch
2016 Gina Wickwar
2017 John Fricke
2018 Susan Hall

2019 John L. Bell

2020 Colin Ayres

2021 Marc Lewis

2022 Herm Bieber

2023 Freddy Fogarty