| Pennant vs Playoff Winners | ||||||||
| Year | Pennant Winners | Playoff Wwinners | Winning Pitcher Pennant | Winning Pitcher Play-offs | ||||
| 2017 | Busey Bank | Colorado Bob's | Dave WIlliams | Mike Beckerman | ||||
| 2016 | John L. Zeigenhein & Sons | Markwort Sporting Goods | Dave Williams | Tim Kobler | ||||
| 2015 | All American Satellite | All American Satellite | Adam Kobler | Adam Kobler | ||||
| 2014 | John L. Zeigenhein & Sons | Colorado Bob's | Dave Williams | Adam Kobler | ||||
| 2013 | Markwort Sporting Goods | John L. Zeigenhein & Sons | Adam Kobler | Dave Williams | ||||
| 2012 | All American | Colorado Bob's | Adam Kobler | Adam Kobler | ||||
| 2011 | Reinhold Flooring | Reinhold Flooring | Jeff Vilmer | Jeff Vilmer | ||||
| 2010 | All American | Reinhold Flooring | Andy Coldberg | Tim Kobler | ||||
| 2009 | John L. Zeigenhein & Sons | John L. Zeigenhein & Sons | Jeff Greaves | Jeff Greaves | ||||
| 2008 | Colorado Bob's | Colorado Bob's | Jason Vilmer | Jason Vilmer | ||||
| 2007 | Reinhold Electric | Colonial Morturaries | Jason Vilmer | Wade Baxter | ||||
| 2006 | Kutis Funeral Homes | Kutis Funeral Homes | Jeff Vilmer | Jeff Vilmer | ||||
| 2005 | John L. Zeigenhein & Sons | John L. Ziegenhein & Sons | Bob Eller | Bob Eller | ||||
| 2004 | Wintergreen Development | Markwort Sporting Goods | Denny Roedner | Bob Eller | ||||
| 2003 | AMG | Reinhold Electric | Mike Jockish | Tim Kobler | ||||
| 2002 | Reinhold Flooring | Kriegshauser Mortuary | Mike Jockish | Bob Eller | ||||
| 2001 | Reinhold Flooring | NGG | Bob Eller | Mike Jockish | ||||
| 2000 | NGG | Reinhold Flooring | Mike Wyatt | Vern Weida | ||||
| 1999 | Reinhold Electric | Reinhold Construction | Dan Braden | Dan Howard | ||||
| 1998 | Jay-Em Trucking | Kutis Funeral Homes | Mike Jockish | Jason Wolf | ||||
| 1997 | Young's Red Birds | NGG | Rick Wolf | Tim Kobler | ||||
| 1996 | Reinhold Electric | NGG | Tim Kobler | Dan Braden | ||||
| 1995 | Kriegshauser Mortuary | Kutis Funeral Homes | Brad Martin | Tim Kobler | ||||
| 1994 | Jay-Em Trucking | Jay-Em Trucking | Don Johnson | Don Johnson | ||||
| 1993 | Reinhold Construction | Kutis Funeral Homes | Jeff Greaves | Dan Braden | ||||
| 1992 | Wagner Floor Co. | Reinhold Electric | Don Johnson | Terry Meyer | ||||
| 1991 | John L. Zeigenhein & Sons | Ill-MO Supply | Don Johnson | Terry Meyer | ||||
| 1990 | Reinhold Electric | Reinhold Electric | Don Johnson | Don Johnson | ||||
| 1989 | Ross Construction | Ross Construction | Bob Moran | Bob Moran | ||||
| 1988 | Ross Construction | Reinhold Electric | Vern Weida | Steve Reinhold (14 Innings) | ||||
| 1987 | Wagner Follr Co. | Kutis Funeral Homes | Steve Reinhold | Curt Wisely (28 Innings) | ||||
| 1986 | ILL_MO Supply | Wagner Flooring | Vern Weida | Steve Reinhold | ||||
| 1985 | Kriegshauser Mortuary | Kreigshauser Mortuaries | Bob Kleen | Bob Kleen | ||||
| 1984 | Kutis Funeral Homes | John L. Ziegeenhein & Sons | Vern Weida | Tom Brinker | ||||
| 1983 | Lamplighter Liquor | Ill-MO Supply | Vern Weida | Ron Vogt | ||||
| 1982 | John L. Zeigenhein & Sons | Schmidt's | Bob Kleen | Carl Poinsett | ||||
| 1981 | ILL_MO Supply | Kreigshauser Mortuaries | Ron Vogt | Phil Scheer | ||||
| 1980 | Lamplighter Liquor | Martin Office Machines | Gene Brown | Gene Brown | ||||
| 1979 | Martin Office Machines | Crawford Trucking | ? | Ken Attchission | ||||
| 1978 | Alpha Fence | Kutis Funeral Homes | Carl Poinsett | Carl Ponisett (24 Innings) | ||||
| 1977 | Ezra Pizza | Ezra Pizza | ||||||
| 1976 | Kutis Funeral Homes | Wacker-Helderle | Doug Casanova | |||||
| 1975 | Irv Martin | Irv. Martin | ||||||
| 1974 | Midtown Optical | ? | ||||||
| 1973 | Ellenwood Café | ? | ||||||
| 1972 | Plaza Drug | ? | ||||||
| 1947 | Squeeze Box Tavern | Squeeze Box Tavern | Don Young | Don Young | ||||
| 1946 | Squeeze Box Tavern | ? | Don Young | |||||
