| 1999 |
Scott & Angela Anhalt |
Manitowoc |
| 2000 |
David (Patty) Endres |
Lodi |
| 2001 |
Randy Roecker & Ruth Roecker |
Loganville |
| 2002 |
Kevin & Christine Griswold |
Ixonia |
| 2003 |
Dean & Lynn Strauss |
Sheboygan Falls |
| 2004 |
Doug & Christina Rebout |
Janesville |
| 2005 |
Peter & Christina Winch |
Fennimore |
| 2006 |
Kevin & Erika Klahn |
Brooklyn |
| 2009 |
Kat Becker & Tony Schultz |
Athens |
| 2010 |
Heather & Jay Jauquet |
Pulaski |
| 2011 |
Patty & Gary Edelburg |
Scandinavia |
| 2012 - The Country Today |
Laura Daniels & Jarred Searls |
Cobb |
| 2013 - The Country Today |
Dave & Stacy Jauquet |
Luxemburg |
| 2014 - The Country Today |
Jim & Shelly Grosenick |
Watertown |
| 2015 - The Country Today |
Marieke Penterman |
Thorp |
| 2016 - The Country Today |
Daniel & Sarah Diederich |
Hobart |
| 2017 - The Country Today |
Sam & Jenn Zimmerman |
Ringle |
| 2018 - The Country Today |
Justin & Darci Daniels |
Hixton |
| 2019 - The Country Today |
Tony Mellenthin |
Eau Galle |
| 2020 - The Country Today |
Katy Schultz |
Fox Lake |
| 2021 - Agri-View |
Shane & Jennifer Sauer |
Waterloo |
| 2022 - Agri-View |
Dylan & Bryanna Handel |
Barneveld |
