North Division

2001: DeForest (4-0-2)
2002: DeForest (6-0-0)
2003: DeForest (5-1-0)
2004: Waunakee (6-0-0)
2005: Sauk Prairie and Waunakee (4-1-0)
2006: Sauk Prairie (6-0-0)
2007: Waunakee (6-0-0)
2008: Waunakee (6-0-0)
2009: Waunakee (5-0-1)
2010: Baraboo, Mount Horeb and Waunakee (5-1-0)
2011: Mount Horeb (3-0-2)
2012: Mount Horeb and Waunakee (4-1-0)
2013: Mount Horeb (5-0-0)
2014: Sauk Prairie (4-1-0) and Mount Horeb (3-0-2)
2015: Mount Horeb and Sauk Prairie (4-0-1)
2016: Mount Horeb and Sauk Prairie (4-0-1)
2017: Mount Horeb (7-0-0)
2018: Waunakee (6-0-1)
2019: Sauk Prairie (6-0-1)
2020: No conference competition due to COVID-19 pandemic

South Division

2001: Madison Edgewood (5-0-0)
2002: Madison Edgewood (5-0-0)
2003: Oregon (3-1-1)
2004: Oregon (4-1-0)
2005: Stoughton (5-1-0)
2006: Madison Edgewood (5-1-0)
2007: Monona Grove (5-1-0)
2008: Madison Edgewood (5-1-0)
2009: Oregon (6-0-0)
2010: Oregon (6-0-0)
2011: Oregon (6-0-0)
2012: Oregon (6-0-0)
2013: Fort Atkinson and Oregon (5-0-1)
2014: Oregon (6-0-0)
2015: Oregon (5-0-1)
2016: Oregon (6-0-0)
2017: Monona Grove (6-0-1)
2018: Oregon (6-0-1)
2019: Oregon (7-0-0)
2020: No conference competition due to COVID-19 pandemic