The Undertaker vs Shawn Michaels and other rivalries in WWE

The Undertaker's scary persona coupled with his old school wrestling technique had fans purring after every match and wanting for more as he fought some iconic wrestlers along the way.

The Undertaker and Shawn Michaels at WrestleMania 26. (Image credits: twitter)
By Sujay Gaurav | Mar 30, 2022 | 3 Min Read follow icon Follow Us

The Undertaker had a career spanning almost 30 years so it’s only natural that he had some awesome rivalries along the way. Commentator Michael Cole referred to the Deadman as the finest striker in the game and he was right. There were not many who could land a punch like The Undertaker.

His scary persona coupled with his old school wrestling technique had fans purring after every match and wanted for more. He fought some iconic wrestlers along the way. Here we see some of his best rivals.

Shawn Michaels

The rivalry between Shawn Michaels and The Undertaker was the gift that kept on giving. The two icons of the sport were involved in unforgettable matches over the span of two decades.

They first crossed paths in 1997 and never looked back since. As personalities come and go, the two men were as different as they come. One was a supernatural force of nature who could summon the dead and the other was a cocky and brash showman who loved showing off.

The two matches that they had at WrestleMania 25 and 26 will forever live in the memory of the WWE universe. The story. The fight. The ending. They had it all. If there ever was a prime time slot for wrestling, the rivalry between Taker and Michaels would take that spot without question. These two men would be in anybody’s Mount Rushmore of wrestling.

Read more: The Rock vs Stone Cold and other Rivalries in WWE

Kane

The Undertaker had an on-screen brother whose name was Kane. Just like his personality, he was a terrifying colossus of a man. Kane debuted at Bad Blood: In Your House on October 5, 1997, when he interfered in a Hell in a Cell match against Shawn Michaels and the Undertaker. The sight of him ripping the cell door off its hinges and manhandling his brother put everyone on notice about the newest monster in town.

Their matches at WrestleMania and especially the first-ever inferno match at Unforgiven 1998 raised the bar when it came to five-star matches in the wrestling world. What is interesting is the fact that both the superstars have also fought together as a tag team known as The Brothers of Destruction and laid waste to the tag team division. The greatness of their rivalry will never be matched and it was just one of those things that can happen only once in a lifetime.

Brock Lesnar

If there was one man who had The Undertaker’s number, it was Brock Lesnar. Lesnar has the distinction of being the only superstar to break the Undertaker’s legendary undefeated WrestleMania streak. It was truly a shocking moment for the Deadman and the world.

The pair’s rivalry started all the way back in 2002 when the Phenom sent the young rookie through the entrance set. The ending of that match only served to act as a catalyst for many legendary encounters between the two. The animosity they had towards each other was evident even when Lesnar was a part of the UFC. This rivalry has produced some of the best matches in recent memory. Although The Undertaker had some classics in his long and storied career, few have pushed him the way The Beast has.