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) defeated Jim Powers & Rudy Boyd
- The Rockers (Marty Jannetty & Shawn Michaels) defeated The Bolsheviks (Boris Zhukov & Nikolai Volkoff)
- Hercules defeated Bob Bradley
- Haku (w/ Bobby Heenan) defeated Omar Atlas
- Jim Duggan defeated Pez Whatley
- Bad News Brown defeated Jim Gorman
- Dino Bravo (w/ Jimmy Hart) defeated Louie Spicolli
- Brutus Beefcake defeated Kenny Johnson
- Dark match: Dustin Rhodes defeated Black Bart
- Dark match: Jim Brunzell defeated The Black Knight
- Dark match: Hulk Hogan defeated Earthquake by DQ
- Dark match: Hillbilly Jim defeated Pez Whatley (3:51)
- Dark match: Power and Glory (Hercules & Paul Roma) defeated Buddy Rose & Kenny Johnson (7:22)
- Dark match: Shawn Michaels vs. Ted DiBiase ended in a Double DQ (14:42)
- Dark match: Mr. Perfect defeated Jim Brunzell (5:03)
- Dark match: Greg Valentine defeated Mark Youn
- Dark match: Tito Santana defeated Buddy Rose
- Dark match: Rhythm and Blues (Greg Valentine & Honky Tonk Man) defeated The Bushwhackers (Butch & Luke) by DQ
- Dark match: The Big Bossman defeated Ted DiBiase
- Dark match: The Ultimate Warrior (c) defeated Rick Rude to retain the WWF Intercontinental Championship
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