The May 27, 1989 edition of Wrestling Challenge is a Professional wrestling television show of the World Wrestling Federation. It was taped on April 25, 1989 at the Veterans Memorial Auditorium in Des Moines, Iowa.
- Numbers in parentheses indicate the length of the match.
- (c) refers to the champion(s) heading into the match.
- Jake Roberts defeated Tom Burton (3:42)
- Big John Studd defeated Al Burke (1:55)
- The Twin Towers (Akeem & The Big Boss Man) (w/ Slick) defeated JT Thomas & Red Tyler (3:31)
- The Red Rooster defeated Tom Stock (3:53)
- Mr. Perfect defeated Frank DeFalco (3:08)
- Hillbilly Jim defeated Jeff Curtis (2:37)