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The Undertaker (Sportskeeda)

The Undertaker (Sportskeeda)

When you think of WrestleMania, one name comes to mind: The Undertaker. Since his first WrestleMania match against Jimmy Snuka in 1991, “The Deadman” has made the biggest show of the year his playground. The Undertaker won 21 matches at the event (dubbed “The Streak”) before losing to Brock Lesnar at WrestleMania 30. While not all of them were classics (especially during his first few years), there are a lot of matches to remember.

The Undertaker is set to face Roman Reigns this Sunday at WrestleMania 33. There are rumors that this could be his final WrestleMania, and the last match of his career. Although many won’t be happy if Roman out of all people was to beat him, they may end up surprised at how good the match can be.

Looking back, we have been spoiled with great Undertaker matches over the past few years at WrestleMania. Here are my top five WrestleMania matches that have included The Undertaker:

5) WrestleMania 21 – v. Randy Orton

This is the one that started it all. While The Undertaker was already undefeated, “The Streak” was never really brought into any discussion. Around this time, The Undertaker was just starting to get momentum after going back to his roots as an undead wrestler (its pro wrestling folks). Randy Orton’s “Legend Killer” phase might be one of the best gimmicks of all time. When you mixed those two together you just knew it would be an interesting combination. The emotion and the twists involved made it one entertaining contest.

One of the highlights of the contest was Orton hitting an RKO when he reversed a chokeslam attempt. From there, it became one of the most entertaining matches in WrestleMania history regarding The Undertaker. This also created an epic feud between the two. Orton and Taker battled throughout the summer and had a great end to their rivalry via a Hell in a Cell match to end 2005.

This match helped elevate Randy Orton and it started a trend for epic Undertaker matches. Now that is a win for everyone.


4) WrestleMania XXVIII – v. Triple H

This is the third match between the two at WrestleMania, and it was by far the best. They faced off at WrestleMania X-Seven in 2001 which was pretty good, and in 2011 at WrestleMania XXVII. After the latter match, Undertaker’s health was clearly not the same as it once was. That did not stop him from going to war with Triple H in a match dubbed as an “End of an Era.” Using the man Undertaker retired and Triple H’s friend, Shawn Michaels, as the guest referee only added to the match. Having Jim Ross on commentary definitely made this feel special. Did I mention it was inside Hell in a Cell?

In a back and forth affair (with bald Taker debuting), both put it all on the line. It was a match that felt like an Attitude Era bout, with enough emotion and hard hitting shots as you can imagine. Like the millions watching, I was convinced Undertaker lost when Michaels superkicked Undertaker into a pedigree. When he kicked out, the reaction on HBK’s face was priceless.

It was everything you wanted in a match and more. While these two were old, they still tore the house down at Sun Life Stadium. There was a lot of things happening during those few hours, but during that match everything just stopped. It was a moment worth remembering.

3) WrestleMania XXIV – v. Edge

Late 2007 was an interesting time for WWE. Undertaker just became World Champion (we will get to that soon), and Edge took the Money in the Bank briefcase from Mr. Kennedy. One star was on Raw, while the other was on SmackDown. One SmackDown taping later, and everything changed.

After a brutal steel cage match against Batista, Undertaker was attacked by Mark Henry. Edge cashed in the briefcase and won the World Title a few moments after. While Taker healed from an injury, Edge became the top guy fans always dreamed he would be. When he got injured, the World Title was up for grabs. A few months went by and Undertaker and Batista renewed their rivalry. They faced off in a Hell in a Cell match at Survivor Series for the World Title. Before the end of the match Edge, disguised as a camera man, attacked Undertaker and hit him with several chair shots. The roller coaster of a feud had just begun between these two.

Edge and Undertaker had matches after WrestleMania, but this match at the biggest event of the year was as important as anything else they did. Being in the main event of WrestleMania, it solidified Edge as a legend and continued Undertaker’s streak of fantastic matches. The aftermath was great: the birth of evil Vickie Guerrero, brutal matches, and fantastic storytelling. While injuries derailed the careers of these two, they created magic from 2007-2008 and there is no denying that.


2) WrestleMania 23 – v. Batista

I’ll admit there is some bias on this choice. I started watching wrestling in late 2006, and the match between these two was at the first WrestleMania I ever saw. Undertaker finally won the Royal Rumble in 2007 and was set to face Batista. Over on SmackDown, you could tell how much the two were ready to rip each other’s heads off. Big Dave wasn’t known for amazing matches, but he proved everyone wrong with his bout against The Undertaker.

The two big men shocked the entire world when they put on a clinic. While nobody could recreate the Shawn Michaels / John Cena bout later in the night, this match tried its best. You genuinely thought Batista wouldn’t lose the World Title after reclaiming it after an injury forced him to relinquish it in 2006. In a great match, Undertaker won his first World Title since 2002, and his first at WrestleMania since WrestleMania 13.

What followed were a few epic matches that continued to surprise viewers. Watch it again, I promise you won’t be disappointed.


1) WrestleMania XXV – v. Shawn Michaels

Oh boy, where do I begin? Back in the 90’s, The Undertaker and Shawn Michaels had a feud that was just violent. They were involved in Hell in a Cell and Casket matches, the latter of the two almost ended HBK’s career. After a few years away, Michaels came back and continued to be “The Showstopper”. It wasn’t until 2007 that we would see Undertaker v. Shawn Michaels. They were the last two in the Royal Rumble match and produced a great, short match. The Undertaker won, giving us a taste of what could have been.

In 2009, it could be argued that these two were on the best runs of their career. After some small storylines that sidetracked the two, fans finally got the WrestleMania match they were waiting for: The Undertaker v. Shawn Michaels.

HBK helped elevate the feud by creating a dark v. light gimmick. With his religious beliefs forming after his comeback, Michaels used that to create a line between himself and the dark Undertaker. As you can see above, his entrance where he “entered from the heavens” was not too shabby. The match itself was out of this world. Back and forth these two went, with each blow causing fans to go crazy. The match reached its epic point when Michaels kicked out of the tombstone, resulting in one of the greatest reactions of all time from The Undertaker.

In the end, Undertaker beat HBK, resulting in fans wanting more. They had a rematch a year later, and HBK had to retire after losing. While that was a great match, there was nothing quite like the first one. There was something special about it that fans will remember.


If this is The Undertaker’s final match, will he give it his all against Roman Reigns? Will some of his old magic in these matches return. Who will survive? Tune into WrestleMania this Sunday to find out.

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Baseball Editor, Misc. Sports Editor. Covers all things combat sports (MMA, Pro Wrestling and Boxing). When he's not writing, Daniel hosts a podcast, The Main Event.
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