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Windy City Wrestling ( 1993 - 1997 )
Windy City Pro Wrestling ( 1997 - 2010 )
League Title

Mike Anthony1993/05/22Chicago, IL
Defeats Kevin Quinn in a tournament final to become the first Windy City Wrestling League champion.
Mike Samson1994/02/05Chicago, IL
Mike Anthony [2]1994/04/23Joliet, IL
Danny Dominion1995/02/18Chicago, IL
Turbo1995/05/20Hammond, IN
Steve Boz [2]1996/12/14Hammond, IN
Promotion renamed Windy City Pro Wrestling in 97.
Ripper Manson1998/11/28Chicago, IL
Greg Valentine1999/05/22Cicero, IL
Vic Capri1999/10/09Tinley Park, IL
Vacant on when Capri goes "on sabbatical" from The Outfit.
Jayson Reign2000/01/29Chicago, IL
Christopher Daniels [2]2000/05/20Hammond, IN
Jayson Reign [2]2000/05/28Crete, IL
Terry Allen2000/07/01Sandwich, IL
Baltazaar2002/02/24Merrionette Park, IL
Terry Allen [2]2002/03/16Chicago, IL
Baltazaar [2]2002/05/18Cicero, IL
Robbie Dawber2003/05/17Cicero, IL
Ivan Manson2003/08/16Grayslake, IL
Steve Boz [2]2003/11/15Chicago, IL
Terry Allen [3]2003/12/13Chicago, IL
Steve Boz [3]2004/05/15Cicero, IL
Acid Jaz 2005
Abaddon2006/06/24Midlothian, IL
Wins a 4-way match against Jaz, Marshé Rockett, and Justin Adams.
Curse 2006/06/24 Midlothian, IL
Sean Mulligan2008/03/08Chicago, IL
Austin Roberts [2]2008/05/17Cicero, IL
Defeats Mulligan and Acid Jaz to unify the Bare Knuckles, Heavyweight, and League Titles into WCPW Unified World Heavyweight Title.

Mike Anthony [3]2010/05/09Chicago, IL
Wins a tournament for the reinstated title; vacant on 10/09/18 when all the champions in the organization are stripped of their titles.
DTA2010/09/18Chicago, IL
Defeats Mike Anthony; promotion closes on 10/12/16.