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

League Title

Mike Anthony	93/05/22	Chicago, IL
Defeats Kevin Quinn in a tournament final to become the first Windy City Wrestling League champion.
Mike Samson	94/02/05	Chicago, IL
Mike Anthony [2]	94/04/23	Joliet, IL
Danny Dominion	95/02/18	Chicago, IL
Turbo	95/05/20	Hammond, IN
Steve Boz [2]	96/12/14	Hammond, IN
Promotion renamed Windy City Pro Wrestling in 97.
Ripper Manson	98/11/28	Chicago, IL
Greg Valentine	99/05/22	Cicero, IL
Vic Capri	99/10/09	Tinley Park, IL
Vacant on when Capri goes "on sabbatical" from The Outfit.
Jayson Reign	00/01/29	Chicago, IL
Awarded.
Christopher Daniels [2]	00/05/20	Hammond, IN
Jayson Reign [2]	00/05/28	Crete, IL
Terry Allen	00/07/01	Sandwich, IL
Baltazaar	02/02/24	Merrionette Park, IL
Terry Allen [2]	02/03/16	Chicago, IL
Baltazaar [2]	02/05/18	Cicero, IL
Robbie Dawber	03/05/17	Cicero, IL
Ivan Manson	03/08/16	Grayslake, IL
Steve Boz [2]	03/11/15	Chicago, IL
Terry Allen [3]	03/12/13	Chicago, IL
Steve Boz [3]	04/05/15	Cicero, IL
Acid Jaz	05
Abaddon	06/06/24	Midlothian, IL
Wins a 4-way match against Jaz, Marshé Rockett, and Justin Adams.
Curse	06/06/24	Midlothian, IL
Sean Mulligan	08/03/08	Chicago, IL
Austin Roberts [2]	08/05/17	Cicero, IL
Defeats Mulligan and Acid Jaz to unify the Bare Knuckles, Heavyweight, and League Titles into WCPW Unified World Heavyweight Title.
Mike Anthony [3]	10/05/09	Chicago, 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.
DTA	10/09/18	Chicago, IL
Defeats Mike Anthony; promotion closes on 10/12/16.