The Undertaker's 23 WrestleMania Matches - From Worst To Best

10. Ric Flair (WrestleMania X8)

By the time March 2002 rolled around, Undertaker had developed into a loathsome heel. Enraged that Ric Flair had cost him a match against The Rock at No Way Out in February, he issued a challenge for a match at WrestleMania X8. Flair, in an ownership role, declined, so The American Badass took it upon himself to change the legend's mind. He brutally assaulted his son, David, and bloodied him. From there, he targeted the great Arn Anderson, doing the same to the former Four Horsemen enforcer. After watching those so close to him be singled out and forced to pay for his transgressions, Flair accepted the match against his tormentor. But their match would not be a Flair classic. There was no catch-as-catch-can wrestling and little in the way of traditional in-ring psychology. Instead, it was a brawl. It was a No Disqualification match, which set the stage for the brutality and violence that 60,000-plus fans in Toronto would witness firsthand. The contest fit the tone of the feud, the intensity and aggression increasing with every passing moment. Flair was busted open, his white hair painted red by the blood that spilled out of his forehead. Even The Undertaker sprung a leak and shed some red stuff. In the end, though, no amount of tenacity from Flair or interference from Anderson (with a SICK spinebuster) could overcome the wrath of the Deadman. A Tombstone ended Flair's chase of vengeance and netted The Undertaker WrestleMania win number 10.