5 times the Undertaker did not win clean

Psycho Sid, WrestleMania 13.

This ranks as one of Taker’s worst feuds of all time

WrestleMania 13’s main event saw The Dead Man go head to head with the deranged Psycho Sid for the WWE Championship. This was his first ever bout for the title at WrestleMania.

Not too much to complain about in this match, the presence and actions of Shawn Michaels and Bret Hart made it even better. One of the best moments was when Psycho Sid countered The Undertaker’s Tombstone Piledriver into one of his own and proceeded to pin him only to see him kick out.

A chair shot to the back of Psycho Sid by Bret Hart didn’t stop him. But he kept interfering and eventually, The Deadman was able to perform the Tombstone Piledriver on him and pin him, giving him his second WWE title reign.