| 1998-2000 | ||| | 2001 | ||| | 2002 | ||| | 2003 ||| | 2004 | ||| | 2005 ||| | 2006 ||| | 2007 ||| | 2008 ||| 2009 |
| May 30th Winner: Chris Einck Primghar, IA Queen: Whitney Smythe HerTown, IA | ![]() | ![]() Photo: O'Brien County Bell. |
| June 6th Winner: Brandon Cronin Orange City, IA Queen: Rylee Smith HerTown, IA | ![]() | ![]() Photo: O'Brien County Bell. |
| June 20th Winner: Joe Hunt Granville, IA Queen: Tiana Tesch HerTown, IA | ![]() | ![]() Photo: O'Brien County Bell. |
| July 11th Winner: Stan Hoogland Granville, IA Queen: Autumn Wahl HerTown, IA | ![]() | ![]() Photo: O'Brien County Bell. |
| July 18th Winner: Taylor Hofmeyer Granville, IA Queen: Katie Hunt HerTown, IA | ![]() | ![]() Photo: O'Brien County Bell. |
| July 22nd Justin Hunt Cedar Falls, IA Fair Queen: Jill Jurgenson Fair King Andrew Koehlmoos Primghar | ![]() | Photo: Primghar Jaycees' Facebook |
| August 8th Winner: Lance Hulstein Rock Valley, IA Queen: Melinda Wulf HerTown, IA | ![]() | ![]() Photo: O'Brien County Bell. |
| August 15th Winner: Brandon Wilcox Everly, IA Primghar Jaycee Scholarship to: Megan McCauley; Ashli Sohn; Matt Cole Primghar, IA | ![]() | ![]() Photo: O'Brien County Bell. |
| 1998-2000 | ||| | 2001 | ||| | 2002 | ||| | 2003 ||| | 2004 ||| | 2005 ||| | 2006 ||| | 2007 ||| | 2008 ||| 2009 |
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