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NAME FORMAT CHANGE IN PROCESS: Names of the wrestlers from countries where the family names come before the given names will be listed as such (Japan, Korea, etc.). The family names will be in bold letters.

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Windy City Wrestling Heavyweight Title ( 1988 ~ 1997 )
Windy City Pro Wrestling Heavyweight Title ( 1997 ~ 2008 )
Windy City Pro Wrestling World Heavyweight Title ( 2008 ~ 2010 )
[over 240lbs]

Steve Regal1988-04-13Chicago, IL
First champion.
Frank Melson1989-12-23Harvard, IL
Hurricane Smith1990-04-28Dixon, IL
Frank Melson [2]1990-12-22Harvard, IL
Ron Powers1991-05-18Chicago, IL
K.C. Knight1992-07-12Stone Park, IL
Mike Samson1994-05-07Hammond, IN
Mike Anthony1996-12-14Hammond, IN
The Polish Crippler1999-07-10Chicago, IL
Killer Khalsa Singh1999-10-06Schaumburg, IL
Stripped in 99-11.
Polish Crippler [2]1999-12-11
Wins tournament.
Willie Richardson2000-05-20Hammond, IN
Steve Boz2001-05-26Hammond, IN
Willie Richardson [2]2001-08-16Fairbury, IL
Steve Boz [2]2001-12-01Chicago, IL
Ripper Manson2002-05-18Cicero, IL
Retires as champion on 05-05-14.
Vito Fontaine2005
Baltazar2006-06-24Midlothian, IL
Vacant in 07-06 when Baltazar leaves the promotion.
Austin Roberts2007-10-26Chicago, IL
Defeats Sean Mulligan in a tournament final; defeats Mulligan and Acid Jaz to unity Bare Knuckles and League titles into WCPW Unified World Heavyweight Title on 08-05-17.
Sean Mulligan2009-05-09Calumet City, IL
Psycho2009-07-10Bridgeview, IL
Wins "Pot of Gold" battle royal for all of the promotion's titles, except the lighweight title.
Sean Mulligan [2]2009-08-15Chicago, IL
All the titles held by Psycho are returned to the previous champions.
Mike Anthony [2]2009-08-15Chicago, IL
Sean Mulligan [3]2009-10-24Chicago, IL
Bailey Mannix2010-02-20Chicago, IL
Vacant on 10-09-18 when all the champions in the organization are stripped of their titles.
Sean Mulligan [4] 2010-09-18 Chicago, IL
Defeats Justin Reno; promotion closes on 10-12-16.
DTA 2011-10-01 Burbank, IL
Cashes in "Money In The Bank" after Mulligan defends the title earlier on the same card.