The Definitive List of Must-Watch Matches from WWE Legend The Undertaker

The Definitive List of Must-Watch Matches from WWE Legend The Undertaker
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110. Survivor Series 1991 vs. Hulk Hogan
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29. Royal Rumble 1994 vs. Yokozuna
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38. No Mercy 2002 vs. Brock Lesnar
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47. WrestleMania XXIX vs. CM Punk
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56, WrestleMania XXVI vs. Shawn Michaels
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65. No Way Out 2006 vs. Kurt Angle
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74. Badd Blood: In Your House 1997 vs. Shawn Michaels
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83. King of the Ring 1998 vs. Mankind
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92. WrestleMania XXVIII vs. Triple H
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101. WrestleMania XXV vs. Shawn Michaels
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The Definitive List of Must-Watch Matches from WWE Legend The Undertaker

Jan 4, 2022

The Definitive List of Must-Watch Matches from WWE Legend The Undertaker

In the larger-than-life world of professional wrestling, few characters have captivated and engrossed fans the way The Undertaker did. 

Straight out of Death Valley, The Deadman stalked toward the ring with haunting purpose, ready to lay waste to his latest opponent. He was a different breed than others, showing total respect to the character by maintaining it and leaving little doubt he was invested in everything he did.

Between the ropes, he was a brawler who could deliver a devastating throat thrust or flatten opponents with a chokeslam. Later in his career, he introduced elements of MMA to ensure he could hang with a new, more athletic crop of talent.

Over the course of his 30 years with WWE, he created magical moments and produced all-time great matches with the likes of Shawn Michaels, Triple H, "Stone Cold" Steve Austin, Kurt Angle, Brock Lesnar and CM Punk.

Which of those contests are considered the definitive, must-watch matches that encompass all that made The Phenom the icon that he is, though? 

10. Survivor Series 1991 vs. Hulk Hogan

They say you never forget your first time for anything, and The Undertaker's first taste of the WWE Championship came at the 1991 Survivor Series.

The Deadman challenged Hulk Hogan in the biggest test of his ability to be a star for Vince McMahon's company to date and passed with flying colors. While the in-ring action was far from stellar, the crowd in Detroit loved the character and a vocal portion of the audience were keen to see him end Hulkamania as WWE knew it.

He may not have ended it, but Undertaker did capture his first world title, thanks in large part to timely interference from Ric Flair.

In hindsight, the bout was less about crowning a new champion and more about setting in motion the events that would lead to the 1992 Royal Rumble match and the vacating of the WWE title.

Still, it was a milestone moment for Undertaker and the first piece of evidence for what McMahon and Co. saw in the character and the performer. 

9. Royal Rumble 1994 vs. Yokozuna

There are few better examples of the mystique and showmanship of The Undertaker than what unfolded in the Casket match for the WWE Championship at the 1994 Royal Rumble.

Yokozuna entered the bout as champion, but his fear of caskets and The Deadman were established in the build to the event. Combating both, he enlisted the services of nine other heels to brutally beat down The Phenom and stuff him in the casket for the win.

Then it happened.

The arena darkened, and the green smoke that had come from the magical urn moments earlier poured from underneath the casket. Suddenly, the image of Undertaker inside the coffin appeared on the video screen. The promo that followed remains one of the best of his career:

"Be not proud. The spirit of the Undertaker lives within the soul of all mankind. The eternal flame of life that can not be extinguished. The origin of which can not be explained. The answer lies within the everlasting spirit. Soon all mankind will witness the rebirth of The Undertaker. I will not rest in peace." 

From there, he ascended out of the video screen and to the heavens, not to be seen for eight months.

The theatricality of the character would be something the company would grow and expand upon over the years but there are few moments that helped fans, especially youngsters, fall in love with the uniqueness of The Undertaker the way his match with Yokozuna and everything that followed it at the 1994 Rumble did.

Some will call it one of the worst matches and angles they have seen. Maybe it is. It's so over over top that it is understandable if it turns some off.

For others, it is childhood nostalgia that helped intensify one's love for the entertainment side of the business and, more importantly, the aura of The Deadman.

8. No Mercy 2002 vs. Brock Lesnar

One cannot overstate what working with The Undertaker, then having him put you over, means to the career of a young star.

We saw it to a degree early in 2002, when Jeff Hardy challenged him for the WWE Championship in a ladder match. While The Charismatic Enigma did not dethrone him, the show of respect from The Deadman after the match helped elevate Hardy in the eyes of the fans.

Fast-forward a few months and you had young Brock Lesnar, early in his run as world champion, defending against The Phenom inside Hell in a Cell.

The physical, bloody match saw The Next Big Thing overcome an early ass-whooping to down the challenger with an F-5 for the win, but what Lesnar received from the contest was something no manufactured victory could replace: credibility.

Lesnar was a made man. He just went to war with Undertaker inside Hell in a Cell and didn't win; he survived. He retained his title by the thinnest of margins, but he did it fairly and in the center of the ring, proving to be The American Badass' superior on that night.

It was a milestone victory for Lesnar and a prime example of Undertaker doing what was best for business by putting over the star tapped by management to be the face of the company moving forward.

7. WrestleMania XXIX vs. CM Punk

The 2013 war between Undertaker and CM Punk should have headlined WrestleMania XXIX.

The storyline was better than what John Cena vs. The Rock had to offer. Punk was in the middle of the hottest run of his WWE career and Undertaker was on a streak of extraordinary WrestleMania wins.

The pieces were there for a Match of the Year main event, but WWE opted for the predictable route with a rematch of the previous year's show that no one asked for.

Perhaps driven by the frustration caused by the company's decision, Punk and Undertaker proceeded to steal the show with one of the best matches of either man's career. A crowd of 80,000-plus in MetLife Stadium hung on every spot of the match, which saw Punk shrug off a painful leg injury following a top rope elbow through the announce table and maintain control of the bout.

In the end, though, it was his hubris that got the best of him.

So sure was he that he was The Best in the World and destined to beat Undertaker, he let his guard down and paid for it as The Deadman picked up the win to advance his unbeaten streak at WrestleMania to 21-0.

6, WrestleMania XXVI vs. Shawn Michaels

After an all-timer the year before, it made sense that WWE would want to capitalize on the buzz and run Undertaker vs. Michaels back again in Phoenix at WrestleMania XXVI. Desperate to prove he could beat his foe, HBK put his career on the line in an attempt to do so.

The emotions surrounding the stipulation and excitement for the match itself helped make the main event of the 2010 Show of Shows one of the most anticipated ever. And the combatants did not disappoint.

In another work of art, The Phenom and Michaels tore the house down with an epic clash that blew away everything else on the card. 

Sensing his career was coming to a close, a defiant HBK slapped Undertaker across the face, encouraging him to do what was necessary to put him out to pasture, just as he had done to Ric Flair two years earlier.

The Deadman did just that, ending Michaels' career with a Tombstone. It was the post-match show of respect by Undertaker for a guy with whom he had many wars that enhanced the overall impact of the bout. 

5. No Way Out 2006 vs. Kurt Angle

Undertaker's match with Kurt Angle for the World Heavyweight Championship at the 2006 No Way Out pay-per-view served as a turning point in his career.

Prior to the contest, there was no denying he was among the greatest and most iconic Superstars in WWE already. But there were questions about his in-ring legacy. He had long been a character performer, who focused on the intricacies of his on-screen persona, and was never really confused with the elite wrestlers of his era. 

The match with Angle changed that. The Olympic gold medalist helped introduce the mat and MMA-based style Undertaker would favor later in his career. He inspired counters and reversals out of The Phenom, almost single-handedly igniting a desire to change with the times.

Not only was the contest a Match of the Year candidate and one of the best of his entire career, but it also set the stage for The Deadman to go on the run of phenomenal in-ring performances that would enhance his legacy and ensure he was not remembered solely for rolling his eyes into the back of his head and saying "Rest in peace."

There are several matches on this list more memorable than his war with Angle, but few meant so much to his legacy between the ropes. 

4. Badd Blood: In Your House 1997 vs. Shawn Michaels

Badd Blood: In Your House introduced fans to Hell in a Cell, a match-type Undertaker would become synonymous with over the years.

At the PPV, The Phenom battled Shawn Michaels in the culmination of their months-long feud that began with HBK blasting him in the head with a steel chair at SummerSlam the previous August and costing him the WWE Championship.

Michaels became a more obnoxious villain after the incident, and the result was a clear desire to see him get his ass kicked by the man whose career he stunted with his errant chair shot. And fans got what they wanted.

In a brilliant match, Undertaker whooped up on Michaels for nearly 30 minutes. Just when it appeared as though The Deadman would put away HBK and move on to challenge for the WWE title, the arena darkened and out came his brother, Kane.

The Big Red Monster laying out his sibling was the first chapter in one of the greatest storylines told by WWE. Undertaker would lose the match but the quality of it, coupled with the epic first encounter with his brother, helped make it almost impossible to top.

3. King of the Ring 1998 vs. Mankind

There isn't much to say about the Hell in a Cell match from King of the Ring 1998 that hasn't already been said.

Despite having a broken foot, Undertaker threw Mankind off the top of the steel structure. He then chokeslammed his barely conscious opponent onto thumbtacks and put him down for the count with a Tombstone.

The sheer brutality of the bout captivated Attitude Era fans and made a bigger star out of Mick Foley than he was entering the match.

It is a contest that is still talked about nearly a quarter of a century later and one that will forever define the Superstars involved.

Whether you believe it to be a masterpiece or an overrated stunt show is irrelevant. What is not is the fact that you cannot tell the story of either man's career without mentioning this match.

For that reason, it absolutely earns a spot on this list.

2. WrestleMania XXVIII vs. Triple H

Undertaker retired Shawn Michaels at WrestleMania XXVI and narrowly defeated Triple H the following year in Atlanta.

Those two matches set up a masterpiece of professional wrestling in 2012 at WrestleMania XXVIII in Miami, where The Deadman battled The Game inside Hell in a Cell, with HBK as the special referee. 

Michaels was reluctant to get involved, promising to remain impartial in a bout with enormous stakes. Dubbed "The End of an Era," it would be the presumptive final chapter in a story that had stretched years and delivered some of the best matches in WWE history. 

He did, until he uncorked Sweet Chin Music, blasting Undertaker right into a Pedigree from Triple H. The drama that ensued on the count was extraordinary and had everyone in attendance and watching at home thinking they may have witnessed the conclusion of The Phenom's unbeaten streak.

It was not. Undertaker, as he had done countless times to that point, absorbed everything thrown at him in the violent, unforgiving match and advanced. Eventually, he did as he had done the previous year and hoisted a defiant member of D-Generation X on his shoulder and drove him into the mat with a Tombstone for the win.

The three icons of sports entertainment standing at the top of the entrance ramp, embracing and acknowledging the roar of the crowd was a special moment that only enhanced the contest.

1. WrestleMania XXV vs. Shawn Michaels

Undertaker and Shawn Michaels wrestled what is, arguably, the greatest match of all time at WrestleMania XXV.

Some will point to the Ric Flair-Ricky Steamboat series in 1989 or Bret Hart's classic with "Stone Cold" Steve Austin at WrestleMania 13 in March 1997 as the pinnacle of pro wrestling, but The Phenom and HBK tore the house down on The Grandest Stage of Them All with a masterclass in drama.

For nearly 30 minutes, fans in Houston hung on every spot, every move and every near-fall as they waited to see if Michaels could do what no other could by beating Undertaker at The Show of Shows. He could not.

Michaels launched himself off the top rope with a moonsault, right into the waiting arms of his opponent. The Deadman drove him into the mat with a Tombstone, finally putting him down and securing the win.

Few remembered the outcome in the moments after the match, though. Instead, they relived the emotions they felt as the performers took them on a roller-coaster ride that culminated with the right guy going over and two of the last gunslingers of a bygone era creating magic on wrestling's most prestigious night.

        

The Definitive List... is an ongoing series detailing the 10 greatest matches in the careers of wrestling's greatest Superstars. Catch up now with these previous installments: "Macho Man" Randy Savage, The Attitude Era, Scott Hall, Mick Foley, Kurt AngleTrish Stratus and Shawn Michaels.

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