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| Windy City Wrestling | ( | 1992 | - | 1997 | ) |
| Windy City Pro Wrestling | ( | 1997 | - | 2001 | ) |
| Little Tokyo | 92/05/10 | St. Joseph, MO |
| Defeats Cowboy Catrell to become the first champion. | ||
| Cowboy Catrell | 92/05/16 | Chicago, IL |
| Little Tokyo [2] | 92 | |
| Chris Cruz | 92/10/24 | Mt. Vernon, IL |
| Karate Kid | 93/01/17 | Springfield, IL |
| Little Tokyo [3] | 96/02/10 | St. Joseph, MO |
| Bobby Dean | 96/08/17 | Springfield, IL |
| Lone Eagle | 97/09/15 | Nashville, TN |
| Vacant on 99/08/03. | ||
| Puppet the Psycho Dwarf | 99/08/17 | Seidella, MO |
| Stripped in 99/08. | ||
| Lone Eagle [2] | 99/08 | |
| Awarded; title retired in 01. | ||
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