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The May 27, 1990 edition of Wrestling Challenge is a Professional wrestling television show of the World Wrestling Federation. It was taped on April 24, 1990 at the Freeman Coliseum in San Antonio, Texas.
- Numbers in parentheses indicate the length of the match.
- (c) refers to the champion(s) heading into the match.
- Rhythm and Blues (Greg Valentine & The Honky Tonk Man) defeat Jim Powers & Rudy Boyd
- The Rockers (Marty Jannetty & Shawn Michaels) defeat The Bolsheviks (Boris Zhukov & Nikolai Volkoff)
- Hercules defeats Bob Bradley
- Haku (w/ Bobby Heenan) defeats Omar Atlas
- Jim Duggan defeats Pez Whatley
- Bad News Brown defeats Jim Gorman
- Dino Bravo (w/ Jimmy Hart) defeats Louie Spicolli
- Brutus Beefcake defeats Kenny Johnson
- Dark match: Dustin Rhodes defeats Black Bart
- Dark match: Jim Brunzell defeats The Black Knight
- Dark match: Hulk Hogan defeats Earthquake by DQ
- Dark match: Hillbilly Jim defeats Pez Whatley (3:51)
- Dark match: Power and Glory (Hercules & Paul Roma) defeat Buddy Rose & Kenny Johnson (7:22)
- Dark match: Shawn Michaels vs. Ted DiBiase ended in a Double DQ (14:42)
- Dark match: Mr. Perfect defeats Jim Brunzell (5:03)
- Dark match: Greg Valentine defeats Mark Youn
- Dark match: Tito Santana defeats Buddy Rose
- Dark match: Rhythm and Blues (Greg Valentine & Honky Tonk Man) defeat The Bushwhackers (Butch & Luke) by DQ
- Dark match: The Big Bossman defeats Ted DiBiase
- Dark match: The Ultimate Warrior (c) defeats Rick Rude to retain the WWF Intercontinental Championship