| 2005 – Blackhawk Valley OT | Kathryn Strause | Rock Island | |
| 2006 – Miss John A Logan OT | Campbell Hunt | Marion | |
| 2007 Miss Greater Woodfield OT | Merriebeth Cox | Roselle | Talent and Evening Gown Preliminary Awards at MAOTeen; Miss Indiana 2012 |
| 2008 – Miss Metropolis OT | Emily Travis | Metropolis | |
| 2009 – Miss Dupage County OT | Andrea Novak | Arlington Heights | Troy University MAOTeen Scholarship |
| 2010 – Miss Blackhawk Valley OT | Kaitlyn Wehr | Moline | |
| 2011 – Miss Southern Illinois OT | Summer Robbins | Hillsboro | Preliminary Evening Gown Award at MAOTeen |
| 2012 – Miss Central Illinois OT | Grace Khachaturian | Champaign | |
| 2013 – Miss Northern Suburbs OT | Isabelle Hanson | Glen Ellyn | Dr. Glenn Harman Instrumental Scholarship Award at MAOTeen |
| 2014 – Miss Windy City OT | Grace Etzkorn | Lisle | |
| 2015 – Miss Windy City OT | Peyton Tucker | Moline | |
| 2016 – Miss Southern Illinois OT | Christine Bryant | Marion | |
