Ranking The Undertaker's 5 greatest WrestleMania matches

The Undertaker has had multiple classics at WrestleMania.
The Undertaker has had multiple classics at WrestleMania.

On the final part of the 'Last Ride' documentary series that was released yesterday, The Undertaker said that he has no desire to get back into the ring anymore. And this time, it feels real. The Cowboy may have finally ridden away.

The Undertaker has left behind an unbelievable WWE career, spanning close to 3 decades of consistent character development and commitment to the game. The Deadman has sacrificed a lot for Vince McMahon and the company, carving his legacy as possibly the greatest WWE Superstar of all time.

One of the most legendary things associated with The Undertaker was his historic record at WrestleMania. For the majority of his career, he had a streak of victories at the Show of Shows. 'Taker won 21 straight matches in a row at WrestleMania, before finally losing to Brock Lesnar in 2014.

Some of the greatest matches and moments of The Undertaker's illustrious career came at 'Mania, particularly in the latter years of his streak. He was responsible for some all-time classics against a variety of opponents, creating magic on multiple occasions. But which match was the best of the bunch?

Here are The Undertaker's 5 greatest WrestleMania matches ranked. But first, a few honorable mentions.

  • The Undertaker vs Triple H (WrestleMania 27)
  • The Undertaker vs CM Punk (WrestleMania 29)
  • The Undertaker vs AJ Styles (WrestleMania 36)

#5 The Undertaker vs Batista (WrestleMania 23)

The first of many.
The first of many.

After The Undertaker won the 2007 Royal Rumble Match, he had the choice to face either John Cena, Batista, and Bobby Lashley at WrestleMania. WWE made a big deal of it, hyping up the Deadman's decision for a week. He eventually chose Batista, who was the World Heavyweight Champion.

The Undertaker was set for another WrestleMania showdown against a big man but this time, the big man stepped up to his level. While the placement of their match on the card was unfortunate, Batista and Undertaker vowed to tear the house down.

They did exactly that, stealing the show with an extremely physical slugfest. Both Superstars brought it on the night, crafting a compelling contest that felt like it could go either way. This was possibly Batista's greatest ever match, while setting Undertaker off on a path of consecutive WrestleMania classics.

An intense and nail-biting finish saw the Deadman finally come away victorious, winning the World Heavyweight Championship from the Animal. Despite happening in the middle of the show, The Undertaker and Batista stole WrestleMania 23.

#4 The Undertaker vs Shawn Michaels (WrestleMania 26)

Possibly the best build to a 'Streak' match.
Possibly the best build to a 'Streak' match.

One of the most iconic moments of The Undertaker's career came in 2010 when he gave Shawn Michaels a retirement to remember. The story of this match was excellent, featuring desperation, urgency, and some shocking twists. Ultimately, the match was signed when HBK decided to put his career on the line.

This would have been as good as, if not better than the previous year, but Undertaker suffered a pretty painful leg injury early on into the match. And while it took away some of the smoothness of it, the two of them were still able to tell an incredible story and put on a captivating contest.

The emotions were running high here, with Michaels fighting with everything he had left. However, The Undertaker was simply too strong. He did look beaten at one moment though, after a Moonsault through the announce table and a Sweet Chin Music in the ring made for one of the most convincing 2-counts in the history of the Streak.

In the end, the Deadman put down a defiant Shawn Michaels with the most frightening Tombstone Piledriver you will ever see. Despite its limitations, the main event of WrestleMania 26 was still an excellent match. This felt like the biggest match of Undertaker's WrestleMania streak, and rightly so.

#3 The Undertaker vs Edge (WrestleMania 24)

Edge gained a lot from this match.
Edge gained a lot from this match.

One year after winning the World Heavyweight Championship from Batista, The Undertaker returned to the Grandest Stage in the hunt for the Big Gold Belt once again, this time in the main event. He was up against Edge, who had manipulated his way to the top of SmackDown.

He was a slimy heel, who seemed to have the Deadman's number at every turn. That showed during the match, with Edge having a counter for pretty much all of Undertaker's moves. This was an incredible see-saw battle, with 'Taker unable to gain any extended momentum.

The Rated-R Superstar looked very good here, thanks to his wits and in-ring awareness. He had The Undertaker's number but just couldn't put him away. The final stretch saw some shenanigans involving the Edgeheads and Charles Robinson, who famously ran the entire length of the ramp to count a pinfall.

After a couple of Spears, Edge was caught in a triangle chokehold. The Undertaker debuted a new submission move, eventually calling it the Hell's Gate. And after really working for it, he finally got the victory over the dastardly villain. It was an immense match that did so much for Edge, probably even more so than Undertaker himself.

#2 The Undertaker vs Triple H (WrestleMania 28)

The height of storytelling in WWE.
The height of storytelling in WWE.

As the culmination of a 4-year long story arc between The Undertaker, Shawn Michaels, and Triple H, this needed to be a blockbuster of a match. It hit all the right notes in terms of in-ring action, storytelling, and pure emotion.

Billed as the 'End of an Era', Undertaker and Triple H faced off in a brutal Hell in a Cell Match with HBK as the special guest referee. The intrigue surrounding that made for the most compelling of scenarios. Was Michaels going to be a fair referee? Would he gift his best friend the one accomplishment he could not earn?

Both Undertaker and Triple H had periods of dominance with the Heartbreak Kid caught in the middle of it all. He was visibly torn and emotional, even contributing to the greatest 2-count in WWE history. Everybody was convinced that the streak had died when he hit the Deadman with Sweet Chin Music before Triple H delivered the Pedigree.

In the end, though, The Undertaker stood tall as he always did. But the most emotional scenes were after the match, as all three legends made their way up the ramp together. They shared a hug on the stage, putting a bow to the "era" that seemingly ended.

They may have had more matches against each other after this, but Undertaker vs Triple H at WrestleMania 28 was a special occasion.

#1 The Undertaker vs Shawn Michaels (WrestleMania 25)

A pro wrestling masterpiece.
A pro wrestling masterpiece.

Here it is. The greatest match that The Undertaker has ever had at WrestleMania, as well as his entire career. It might be the greatest match in WrestleMania history. Heck, it might even be the greatest wrestling match ever, no disrespect to Randy Orton and Edge.

The match between Undertaker and Shawn Michaels at WrestleMania 25 was as perfect a match could get. This was a dream encounter, especially with HBK's new lease on life, teased for years at the Royal Rumble. The story was perfect, with Michaels descending from the heavens and Undertaker rising from the depths of hell.

The atmosphere was electric and both performers brought it. The two had an exceptional battle of wills, enduring many roadblocks along the way. The biggest one was a terribly scary bump that the Deadman took, diving from over the top rope onto a poor cameraman. A slightly lesser man would have called it a day right there.

However, The Undertaker fought on and constructed an epic masterpiece with Shawn Michaels. We saw a barrage of near-falls from both sides, including a very convincing one following a Sweet Chin Music. The match finally ended after Undertaker countered a Moonsault into a Tombstone Piledriver, collapsing to the mat upon the 3-count.

This match was pro wrestling storytelling at it's absolute best and words cannot do it justice. It is well worth a watch whether it is your first time watching it, or 50th time. The Undertaker vs Shawn Michaels will stand the test of time as possibly the greatest match in WWE history.

And if the Cowboy actually did ride into the sunset, we can only thank the most legendary character in wrestling history. Thank you 'Taker, there will never be another Superstar like you.

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Edited by Kaushik Das
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