WCWO Cagefest 1999 took place in Connersville, Indiana. The event took place on May 1, 1999.
Results[]
- Numbers in parentheses indicate the length of the match.
- (c) refers to the champion(s) heading into the match.
- "The Spyder" Nate Webb defeated "Dangerous Bull" Don Basher
- Indiana Kidd, Jr defeated Gunner Lee
- Gay Guy Lombardo defeated "Pretty Boy" Shawn Cook
- "The Caneman" Johnnie Walker defeated Austin James
- Indiana Kidd, Jr defeated The Convict in a Cage Match
- Rob Ramer defeated "Bad Boy" Billy Bart
- Randy "Big R" Klemme defeated "Dangerous Bull" Don Basher to win the WCWO Heavyweight Championship