Undertaker WrestleMania History: A Legacy of The Phenom’s Streak

The history of The Undertaker at WrestleMania is deeply interwoven with the chronicles of professional wrestling. If you’re a fan, you’re likely familiar with the legendary streak of victories held by this iconic WWE superstar, who has reigned supreme at the sport’s marquee event for more than twenty years.

The Undertaker WrestleMania history isn’t just a record of wins and losses; it’s a collection of epic stories, each chapter representing a year in the life of what many consider the greatest WWE performer of all time.

Early Career and Debut at Wrestlemania

His early WWE tenure set the stage for what would become one of the most iconic Undertaker WrestleMania history moments.

Wrestlemania VII Debut

In 1991, the Undertaker made an unforgettable entrance into the WrestleMania arena. At WrestleMania VII, he faced “Superfly” Jimmy Snuka and secured his first victory on the grand stage. This win was more than just a match; it marked the beginning of a legendary series of triumphs that would elevate the Undertaker to an all-time great status in WWE history.

The Undertaker first Wrestlemania Match
by Pinterest

Undertaker WrestleMania History of his Initial Streak Build

Following his debut, the Undertaker embarked on a series of victories that would form the foundation of his unprecedented WrestleMania winning streak. His dominance at the event grew with each passing year, gripping the attention of fans and intimidating opponents alike as the count climbed.

Streak Ascendancy and Marquee Matches

Diving into the Undertaker WrestleMania history, you’ll marvel at the sheer dominance of ‘The Streak’. Iconic clashes that stand out transforming WrestleMania into the Undertaker’s personal stage of supremacy.

Encounters with Kane

WrestleMania XIV & XX

  • 1998: The Undertaker’s first confrontation with his storyline brother, Kane, which he won, despite Kane’s colossal strength.
  • 2004: A resurrected Undertaker, with a new Deadman persona, triumphed over Kane once again.
    Key Match Element: The emotional turmoil of a sibling rivalry played out on the grandest stage, adding layers to The Streak’s narrative.
The Undertaker vs Kane
by Pinterest

Battles against Triple H and Shawn Michaels

WrestleMania X-Seven, XXVII, XXVIII

  • 2001 Triple H: The Undertaker endured a grueling battle, culminating in a victory that solidified his reign as the unyielding force at WrestleMania.
The Undertaker vs Thriple H
by Pinterest
  • 2011 & 2012 Triple H: Back-to-back matches, including a brutal ‘Hell in a Cell’ with Shawn Michaels as special guest referee, which tested the limits of all competitors involved.
The Undertaker vs Thriple H and Shawn Michaels
by Pinterest

WrestleMania XXV & XXVI

  • 2009 Shawn Michaels: A match widely regarded as one of the greatest in WrestleMania history, marked by high stakes and near falls.
The Undertaker vs Shawn Michaels
by Pinterest
  • 2010 Shawn Michaels: A career-threatening rematch where The Undertaker’s win resulted in the retirement of Shawn Michaels.
The Undertaker wins against Shawn Michaels
by Pinterest

The Streak’s Climax and The Legendary 21-0

As you dive into the Undertaker WrestleMania history, you’ll find the narrative eventually crescendos with ‘The Streak’—a testament to endurance and performance, marking an unparalleled 21 wins without a single loss at WWE’s flagship event.

WrestleMania XXIX Against CM Punk

In what would become the 21st jewel in the streak’s crown, the Undertaker faced off against CM Punk at WrestleMania XXIX. This match wasn’t just about keeping the streak alive; it was steeped in raw emotion, elevated by the passing of Paul Bearer, Undertaker’s long-time manager, just weeks before the event. ‘The Phenom’ battled with his usual blend of stoicism and supernatural flair to secure a gripping victory.

The Undertaker vs CM Punk
by Pinterest

The Pinnacle

Reaching 21-0 at WrestleMania was more than just a number; it forever immortalized the Undertaker’s name in WWE lore. The Streak’s pinnacle cannot be understated— a physical and theatrical display that fans looked forward to annually. Each match, each year, each victory added to an ever-growing saga that would stand as one of the most impressive accomplishments in professional wrestling history.

The Undertaker Reaching 21 wins at Wrestlemania
by Pinterest

End of the Streak and Legacy

Exploring the latter part of the Undertaker WrestleMania history, you’ll uncover the moment that left fans in disbelief.

The Shocking Loss at WrestleMania XXX

At WrestleMania XXX, a phenomenon that had seemed eternal was shattered. The Undertaker’s undefeated streak at WrestleMania met its end. Brock Lesnar, the man responsible for the upset, broke the streak in what would be remembered as one of the most startling moments in Wrestlemania history.

The Undertakers lose against Brock Lesnar
by Pinterest

Subsequent WrestleMania Appearances

Despite the end of the streak, The Undertaker continued to grace the WrestleMania stage with his ominous presence. Notably, he suffered his second WrestleMania loss to Roman Reigns at WrestleMania 33, which was initially speculated to be his retirement match.

The Undertaker lose his second match
by Pinterest

However, he returned triumphantly at WrestleMania 34, defeating John Cena in a showdown that proved his enduring appeal and prowess in the ring are as strong as ever.

The Undertake vs John Cena
by Pinterest

Cultural Impact

The Undertaker’s streak was not just a tally of victories; it grew to represent an unparalleled legacy within professional wrestling. It showed that a well-crafted narrative could evoke deep emotional reactions and conversations among audiences worldwide. The streak will forever be etched in the memories of fans.

Retirement and Post-Wrestlemania Career

You’ve witnessed the Undertaker’s formidable presence at WrestleMania, looming large over the event’s history. Now, let’s explore how he hung up his hat and what he’s been up to since stepping out of the ring.

The Final Matches

He returned for a few more bouts, with his final match being the memorable Boneyard Match against AJ Styles at WrestleMania 36.

The Undertake final match vs AJ Styles
by Pinterest

Post-Retirement Appearances

Even after retiring, the Undertaker has remained an influential figure in the wrestling world. He was inducted into the WWE Hall of Fame in 2022, an honor reflecting his incredible impact on the sport.


How many times has Undertaker been to WrestleMania?

The Phenom competed in a record 27 WrestleMania matches

Did John Cena ever wrestle Undertaker at WrestleMania?

Yes, Cena wrestled Undertaker at WrestleMania 34

What was Undertaker’s last match?

The Undertaker’s final WrestleMania match was also his last match in the WWE. The Phenom squared off against AJ Styles in a Boneyard Match

I hope you liked this Post about Undertaker WrestleMania History. Let us know what you think about it in the comments ⬇️

Avatar photo
Dominik Weiss
Articles: 109

Leave a Reply

Your email address will not be published. Required fields are marked *