| Year | Champion | Runner-up | MVP |
| 1969 | Maywood Agents | Forest Park All-Stars | N/A |
| 1970 | Ambro Dukes | Bruins, Chicago, IL | N/A |
| 1971 | Chiefs | Relatives | N/A |
| 1972 | The Cabin | Bobcats, Chicago, IL | N/A |
| 1973 | Strikers, Chicago, IL | Bobcats, Chicago, IL | N/A |
| 1974 | Bobcats, Chicago, IL | Bruins, Chicago, IL | N/A |
| 1975 | Sobies, Chicago, IL | Strikers, Chicago, IL | N/A |
| 1976 | Bobcats, Chicago, IL | American Rivet, Chicago, IL | N/A |
| 1977 | American Rivet, Chicago, IL | Josef’s Restaurant, Chicago, IL | N/A |
| 1978 | Bobcats, Chicago, IL | Stompers | N/A |
| 1979 | Mr. A Lucky | Railbirds | N/A |
| 1980 | Stompers | Down the Hatch | N/A |
| 1981 | Otto’s | Budweiser Whips, Chicago, IL | N/A |
| 1982 | Otto’s | Budweiser Whips, Chicago, IL | N/A |
| 1983 | Budweiser Whips, Chicago, IL | Flames | Larry Kelly, Budweiser Whips |
| 1984 | Budweiser Whips, Chicago, IL | Stompers | N/A |
| 1985 | Budweiser Whips, Chicago, IL | Magic, Villa Park, IL | N/A |
| 1986 | Bud Chicago, Chicago, IL | Coopers Sporting Goods, Meadows, IL | Willie Simpson, Bud Chicago |
| 1987 | Bud North, Mt. Prospect, IL | J-Birds, Mt. Prospect, IL | Mark Frighetto, Bud North |
| 1988 | Bud North/Auto Mart, Mt. Prospect, IL | Whips, Chicago, IL | Keith Kilkins, Whips |
| 1989 | Bud North, Mt. Prospect, IL | Whips, Chicago, IL | Keith Kilkins, Whips |
| 1990 | Pete’s Hideway Whips, Chicago, IL | March Manufacturing, Des Plains, IL | Dave Ruehl, Pete’s Hideway Whips |
| 1991 | Lettuce, Chicago, IL | Miller Taggers, Mt. Prospect, IL | Matt Biondic, Lettuce |
| 1992 | Splinters Sports, Hodgkins, IL | Lettuce, Chicago, IL | John O’Conner, Splinters |
| 1993 | Lettuce, Chicago, IL | Bud 45’s, Mt. Prospect, IL | Frank Mustari and Bob Lopez, Lettuce (Co-MVPs) |
| 1994 | Lettuce, Chicago, IL | March Manufacturing, Des Plains, IL | Bob Russ, Lettuce |
| 1995 | Thee Dollhouse Orland Park, IL | Lettuce, Chicago, IL | Frank Ferresese, Dollhouse |
| 1996 | Bud 45’s, Mt. Prospect, IL | Lettuce, Chicago, IL | Kurt Keisel, Bud 45s |
| 1997 | Lettuce, Chicago, IL | Gamblers, Cicero, IL | Matt Biondic, Lettuce |
| 1998 | Rizza Rockers, Hinsdale, IL | Puglise Softball, Riverside, IL | Greg Ziegler, Rizza Rockers |
| 1999 | Puglise Cartage, Riverside, IL | Lettuce, Chicago, IL | Keith Filkins and John Wolnik, Puglise Cartage |
| 2000 | Bucks Softball, Mt. Prospect, IL | Licorice, Mt. Prospect, IL | Dave Bischoff, Bucks Softball |
| 2001 | Miller 45’s, Mt. Prospect, IL | Cuervo Gold Crush, Chicago, IL | Rick Gancarz, Miller 45’s |
| 2002 | Licorice, Mt. Prospect, IL | Miller 45’s, Mt. Prospect, IL | Bobby Russ & Randy Russ, Licorice |
| 2003 | Miller 45’s, Mt. Prospect, IL | March Manufacturing/Flash, Des Plains, IL | Jim Matlock, Miller 45’s |
| 2004 | Miller 45’s, Mt. Prospect, IL | Paragon, Mt. Prospect, IL | Israel Sanchez, Miller 45’s |
| 2005 | Flash, Des Plains, IL | Sage, Mt. Prospect, IL | John Scimone, Flash |
| 2006 | Miller 45’s, Mt. Prospect, IL | Mudville, Mt. Prospect, IL | Israel Sanchez, Miller 45’s |
| 2007 | Miller 45’s, Mt. Prospect, IL | Windy City, Woodlake, IL | Jeff Berger & Rick Gancarz, Miller 45’s (Co-MVPs) |
| 2008 | Miller 45’s, Mt. Prospect, IL | Windy City, Woodlake, IL | Keith Filkins, Miller 45’s |
| 2009 | Miller 45’s, Mt. Prospect, IL | Jynx, Chicago, IL | Mark Holstein, Miller 45’s |
| 2010 | Flashback, Des Plains, IL | Roadrunners, Rolling Meadows, IL | Anthony Tyler, Flash |
| 2011 | Flashback, Des Plains, IL | Roadrunners, Rolling Meadows, IL | John Westermeyer, Flashback |
| 2012 | Flashback, Des Plains, IL | Windy City, Woodlake, IL | Max Sakellaris, Flashback |
| 2013 | Windy City, Woodlake, IL | OBI, Chicago, IL | Keith Duffy and Chris Geron, Windy City |
| 2014 | Chicago Dynasty, Chicago, IL | OBI, Chicago, IL | Mike Alongi, Chicago Dynasty |
| 2015 | OBI, Chicago, IL | Signature, Forest Park, IL | Brian Koronkowski, OBI |
| 2016 | Signature, Forest Park, IL | Hexx, Forest Park, IL | Sal Milazzo and Matt Richards, Signature |
| 2017 | Tito’s 45’s, Forest Park, IL | Chicago Dynasty, Chicago, IL | Alex Smith, Tito’s 45’s |
| 2018 | Tito’s 45’s, Forest Park, IL | Chicago Dynasty, Chicago, IL | Brian Blackwell Jr., Tito’s 45’s |
| 2019 | Tito’s 45’s, Forest Park, IL | Chicago Dynasty, Chicago, IL | Mark Holstein, Tito’s 45’s |
| 2020 | Cancelled due to Covid-19 | ||
| 2021 | Circus | Tito’s 45’s, Forest Park, IL | N/A |
