| Year | Pennant Winners | ` | Playoff winners | |
| 2008 | Colorado Bob's | Colorado Bob's | ||
| 2007 | Reinhold Electric | Colonial Morturaries | ||
| 2006 | Kutis Funeral Homes | Kutis Funeral Homes | ||
| 2005 | John L. Zeigenhein & Sons | John L. Ziegenhein & Sons | ||
| 2004 | Wintergreen Development | Markwort Sporting Goods | ||
| 2003 | AMG | Reinhold Electric | ||
| 2002 | Reinhold Flooring | Kriegshauser Mortuary | ||
| 2001 | Reinhold Flooring | NGG | ||
| 2000 | NGG | Reinhold Flooring | ||
| 1999 | Reinhold Electric | Reinhold Construction | ||
| 1998 | Jay-Em Trucking | Kutis Funeral Homes | ||
| 1997 | Young's Red Birds | NGG | ||
| 1996 | Reinhold Electric | NGG | ||
| 1995 | Kriegshauser Mortuary | Kutis Funeral Homes | ||
| 1994 | Jay-Em Trucking | Jay-Em Trucking | ||
| 1993 | Reinhold Construction | Kutis Funeral Homes | ||
| 1992 | Wagner Floor Co. | Reinhold Electric | ||
| 1991 | John L. Zeigenhein & Sons | Ill-MO Supply | ||
| 1990 | Reinhold Electric | Reinhold Electric | ||
| 1989 | Ross Construction | Ross Construction | ||
| 1988 | Ross Construction | Reinhold Electric | ||
| 1987 | Wagner Follr Co. | Kutis Funeral Homes | ||
| 1986 | ILL_MO Supply | Wagner Flooring | ||
| 1985 | Kriegshauser Mortuary | Kreigshauser Mortuaries | ||
| 1984 | Kutis Funeral Homes | John L. Ziegeenhein & Sons | ||
| 1983 | Lamplighter Liquor | Ill-MO Supply | ||
| 1982 | John L. Zeigenhein & Sons | Schmidt's | ||
| 1981 | ILL_MO Supply | Kreigshauser Mortuaries | ||
| 1980 | Lamplighter Liquor | Martin Office Machines | ||
| 1979 | Martin Office Machines | Crawford Trucking | ||
| 1978 | Alpha Fence | Kutis Funeral Homes | ||
| 1977 | Ezra Pizza | Ezra Pizza | ||
| 1976 | Kutis Funeral Homes | Wacker-Helderle | ||
| 1975 | Irv Martin | Irv. Martin | ||
| 1974 | Midtown Optical | ? | ||
| 1973 | Ellenwood Café | ? | ||
| 1972 | Plaza Drug | ? |