WCWO (October 23, 1999) took place in Paragon, Indiana. The event took place on October 23, 1999.
Results[]
- Numbers in parentheses indicate the length of the match.
- (c) refers to the champion(s) heading into the match.
- Indiana Kidd, Jr defeated "The Spyder" Nate Webb
- "The Caneman" Johnnie Walker defeated Itch Coma Wieder
- Big Red, The Wrestling Preacher defeated Lamar, Eddie Wolf, and Kenny Burns
- Gay Guy Lombardo (c) defeated "Pretty Boy" Shawn Cook to retain the WCWO Heavyweight Championship
- Johnny Eagle defeated The Executioner to retain the WCWO Midwest Championship
- The Homeboys defeated The Country Boys
- 16-man Over-The-Top-Rope Battle Royal: Winner: Shiloh Hunter