The Undertaker’s 10 Biggest Regrets In His WWE Career

8. Not Working A WrestleMania With Stone Cold Steve Austin

When Stone Cold Steve Austin talks about his own regrets, he often brings up the fact that he never went one on one with The Undertaker at WrestleMania. After the Deadman lost to Brock Lesnar last year, Austin spoke of his regret at not having a streak match, during an interview with The Sun.

It is very likely that The Undertaker felt the same way. The two texans are cut from the same cloth, they’re both old school. They also had epic in-ring chemistry during their feuds in the late nineties. Unfortunately, fate never put them up against each other at WrestleMania.

Had both been fit for action at WrestleMania 2000, then there’s a chance they would’ve clashed at that event. As it happened, both sat that Mania out due to injury.

Taker will regret missing the chance to work with Austin on the grandest stage of them all. It would have been huge business and delivered critically in the ring. It is definitely one of those “what if” moments from WWE history.