| 1998-2000 | ||| | 2001 | ||| | 2002 | ||| | 2003 ||| | 2004 ||| | 2005 ||| 2006 | ||| 2007 ||| | 2008 |
| June 3rd Winner: Stan Hoogland Calumet, IA Queen: Cassie Houtsma Sheldon, IA Picture | ![]() |
| June 18th Winner: Denny Logan Primghar, IA Queens: Cherokee, IA Picture | ![]() |
| June 24th Winner: Adam Nissin Aurelia, IA Queens: Sa11y Einck, Primghar, IA Picture | ![]() |
| July 8th Winner: Steve Miller Boyden, IA Queens: Kim Fu11er, Paullina Katie Riordan, Primghar Picture | ![]() |
| July 22 Winner: Jesse Logan Town, IA Queen: Ash1ee Vermu1m Sioux Center, IA Picture | ![]() |
| July 26th Winner: Ben Sanderson Dickens, IA Fair King & Queen: Andrew Dau, Primghar Linsay Woolston, Sutherland Picture | ![]() |
| August 5th Winner: Brandon Wilcox Everly, IA Queen: Traci Sohn King: Andrew Dau Primghar, IA Jaycee Scholarship Recipients Picture | ![]() |
| August 19th Winner: Chris Einck Primghar, IA Queens: Jordan Frerichs Kayla DeJong Orange City, IA Picture | ![]() Photo courtesy O'Brien County Bell |
| 1998-2000 | ||| | 2001 | ||| | 2002 | ||| | 2003 ||| | 2004 ||| | 2005 ||| 2006 | ||| 2007 |
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