| Year | Photo | Best Overall Winner |
| 2000 | Rachel Hindle | |
| 2001 | Rachel Hindle | |
| 2002 | Kristen Laing | |
| 2003 | No Coloring Contest | |
| 2004 | No Photo Available | Rachel Hindle |
| 2005 | Rachel Hindle | |
| 2006 | Grace Farley | |
| 2007 | Victoria Adkins | |
| 2008 |  | Stephanie Briggs |
| 2009 |  | Calla Janke |
| 2010 |  | Sarah M. Green |
| 2011 |  | Ceceila Rucker |
| 2012 | No Photo Available | Rachel Potter |
| 2013 |  | Rebekah Brase |
| 2014 |  | Katharine Brase |
| 2015 |  | Alexander Brase |
| 2016 |  | Amberlee Pick |
| 2017 |  | Katharina Brase |
| 2018 |  | Dietrich Brass |
| 2019 |  | Katharina Brass |
