Already a two-time WWE Champion, Undertaker walked into Kansas City, Missouri, on May 23, 1999, looking for yet another reign. His opponent that night was “Stone Cold” Steve Austin, who was riding high after defeating The Rock at WrestleMania XV.

Austin’s title reign came to a screeching halt, however, when Undertaker pinned his shoulders to the mat. The victory came with controversy, though. As Shane McMahon, who was acting as special referee, conducted a speedy three count to ensure Undertaker defeated Austin.