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| League Playoff Winners | ||||||
| Team | Year | Notes | ||||
| Markwort Sporting Goods | 2022 | |||||
| Third Wheel Brewing | 2021 | |||||
| JA Freight | 2020 | |||||
| One Eyed Willies | 2019 | |||||
| Kutis Funeral Homes | 2018 | |||||
| Colorado Bobs | 2017 | |||||
| Markwort Sporting Goods | 2016 | |||||
| All American Satellite | 2015 | |||||
| Colorado's Bobs | 2014 | |||||
| John L. Ziegenhein | 2013 | |||||
| Colorado's Bobs | 2012 | |||||
| Reinhold Flooring | 2011 | |||||
| Reinhold Flooring | 2010 | 3 days to complete | ||||
| John L. Zeigenhein & Sons | 2009 | |||||
| Colorado's Bobs | 2008 | |||||
| Colonial Morturaries | 2007 | |||||
| Kutis Funeral Homes | 2006 | 13 innings | ||||
| John L. Ziegenhein & Sons | 2005 | |||||
| Markwort Sporting Goods | 2004 | |||||
| Reinhold Electric | 2003 | |||||
| Kriegshauser Mortuary | 2002 | |||||
| NGG | 2001 | |||||
| Reinhold Flooring | 2000 | |||||
| Reinhold Construction | 1999 | |||||
| Kutis Funeral Homes | 1998 | |||||
| NGG | 1997 | |||||
| NGG | 1996 | |||||
| Kutis Funeral Homes | 1995 | |||||
| Jay-Em Trucking | 1994 | |||||
| Kutis Funeral Homes | 1993 | |||||
| Reinhold Electric | 1992 | |||||
| Ill-MO Supply | 1991 | |||||
| Reinhold Electric | 1990 | |||||
| Ross Construction | 1989 | |||||
| Reinhold Electric | 1988 | |||||
| Kutis Funeral Homes | 1987 | 28 innings, club record | ||||
| Wagner Flooring | 1986 | |||||
| Kreigshauser Mortuaries | 1985 | |||||
| John L. Ziegeenhein & Sons | 1984 | |||||
| Ill-MO Supply | 1983 | |||||
| Schmidt's | 1982 | |||||
| Kreigshauser Mortuaries | 1981 | |||||
| Martin Office Machines | 1980 | |||||
| Crawford Trucking | 1979 | 1st annual Don Young Playoffs | ||||
| Kutis Funeral Homes | 1978 | |||||
| Ezra Pizza | 1977 | |||||
| Wacker-Helderle | 1976 | |||||
| Irv. Martin | 1975 | |||||
| 1974 | ||||||
| 1973 | ||||||
| 1972 | ||||||
| 1971 | ||||||
| 1970 | ||||||