1990 - Central
1991 - Logan
1992 - Logan, Tomah
1993 - Central, Logan
1994 - Central
1995 - Central
1996 - Central, Holmen
1997 - Logan, Holmen
1998 - Holmen
1999 - Aquinas
2000 - Logan
2001 - Aquinas
2002 - Logan
2003 - Logan
2004 - Holmen
2005 - Holmen
2006 - Logan, Sparta
2007 - Logan
2008 - Logan
2009 - Logan
2010 - Logan
2011 - Logan, Sparta
Coaches of the Year (began being awarded in the fall of 2001)
2002 - Tom Campbell, Logan
2003 - Tom Campbell, Logan
2004 - Duane Vike, Holmen
2005 - Duane Vike, Holmen, Joe Gaspard, Aquinas
2006 - Tom Campbell, Logan
2007 - Tom Campbell, Logan
2008 - Duane Vike, Holmen
2009 - Duane Vike, Holmen
2010 - Matt Watson, Aquinas
2011 - Greg Dull, Sparta