The Undertaker
Photo Credit: WWE

The Undertaker’s 5 Best WrestleMania Matches

The Undertaker will forever remain one of the most prolific performers at WWE WrestleMania. The Phenom went years without being pinned on the Grandest Stage of them All. His streak was synonymous with the event until Brock Lesnar conquered it.

The decision, in my humble opinion, has aged poorly because WWE are now attempting to minimize Lesnar’s association with them. I was never a fan of Vince McMahon’s decision to have Lesnar go over Taker in the first place.

But what’s done is done and it would just be a waste of time to lament over the infamous booking decision. On the bright side, we have this list of The Undertaker’s five best WrestleMania matches up for your reading pleasure.

Enjoy!

The Undertaker vs. AJ Styles – Boneyard Match: SmackDown, June 26, 2020
Video Credit: YouTube

The Undertaker vs. AJ Styles (Boneyard Match – WrestleMania 36)

AJ Styles arriving in WWE in 2016 turned out be a game-changer signing for WWE. The Phenomenal One got the best out of the likes of Roman Reigns and John Cena. Styles received the ultimate honor when he was picked to be Taker’s farewell opponent.

However, the pandemic forced a worldwide shutdown. WWE would come up with a creative solution to deliver the match. The pair would film a cinematic match that aired as the main event of WrestleMania 26, Night 1.

Both men did a brilliant job in the boneyard match. There was a lot of trash talk and a lot of a** kicking. Styles did a great job selling Taker’s offense. Both performers got the time they needed to deliver a cinematic spectacle.

WWE Classics -- Wrestlemania 23 4/1/07
Video Credit: YouTube

The Undertaker vs. Batista (World Heavyweight Title Match – WrestleMania 23)

Batista believes his match against The Undertaker should’ve headlined WrestleMania 23. There are a lot of fans who echo similar sentiment. The Phenom versus The Animal was the premier feud for SmackDown in 2007.

Taker had won the 2007 Royal Rumble to earn a shot at the World Heavyweight Championship. Both men would engage in a series of tag team matches with their RAW counterparts in John Cena and Shawn Michaels.

Batista showing no fear of The Deadman made for compelling storytelling. The two pair went out and delivered what many thought was the Match of the Night. They’ have a series of excellent matches following WrestleMania 23.

The Undertaker VS CM Punk @WWE Wrestlemania 29 HD Highlights
Video Credit: YouTube

The Undertaker vs. CM Punk (WrestleMania 29)

CM Punk not getting a spot in the main event of WrestleMania 29 will forever remain a huge part of the wrestling lore. The Straight Edge Superstar had reigned as WWE Championship for over 400 days. He’d drop the title to The Rock at Royal Rumble 2013.

After failing to win the rematch at Elimination Chamber 2013, Punk would win a fatal four-way to challenge for The Undertaker’s streak at WrestleMania 29. WWE would insert Paul Bearer’s death into the feud to gain traction.

This was a controversial decision but it ended up making the feud much more personal. The Deadman and the Voice of the Voiceless would steal the show with their in-ring work. Many believe this to be Taker’s last great WrestleMania match before he rode off to the sunset with the iconic cinematic match against AJ Styles.

Superstars respond to Triple H vs. The Undertaker - Hell In A Cell: WrestleMania XXVIII
Video Credit: YouTube

The Undertaker vs. Triple H (Hell in a Cell Match – WrestleMania 28)

The Undertaker is super proud of his four-year program with Shawn Michaels and Triple H. And why shouldn’t be be? The two feuds put the three men on a higher pedestal. Taker had an extremely grueling No Holds Barred Match against Hunter at WrestleMania 28.

Both men met again in a match dubbed “The End of an Era.” The Phenom also debuted a new look inside the demonic structure. While the No Holds Barred Match focused on the physicality aspect, this outing emphasized in-ring storytelling.

Shawn Michaels’ involvement as the Special Guest Referee served as the cherry on top. The Heartbreak Kid did a great job showcasing his emotions for one man who was his best friend and the other who was his greatest opponent.

Taker would extend his streak to 20-0 with his second consecutive win over Hunter (third overall) inside Hell in a Cell.

FULL MATCH - Undertaker vs. Shawn Michaels: WrestleMania XXV
Video Credit: YouTube

The Undertaker vs. Shawn Michaels (WrestleMania XXV)

When it comes to getting the crowd emotionally invested, no match (arguably) comes close to capturing the wild emotions than The Undertaker versus Shawn Michaels from WrestleMania XXV. This match saw the two veterans of the business give more than their 100% to give a spectacle for the ages.

In my years of watching (and reviewing) countless wrestling matches, this legendary outing stands out as an all-time great spectacle. It perfectly sums up what WrestleMania is suppose to be: the Showcase of Immortals. From the sheer in-ring psychology to the crowd reaction, Taker vs. Michaels is perhaps the greatest WrestleMania match of all time.

Honorable Mentions

  • The Undertaker vs. Kane (WrestleMania 14)
  • vs. Edge (WrestleMania XXIV)
  • The Undertaker vs. Randy Orton (WrestleMania 21)
  • vs. Triple H (WrestleMania 27)
  • The Undertaker vs. Shawn Michaels (WrestleMania XXVI)

Also read: 5 Best WWE Elimination Chamber Matches

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