Undertaker’s Greatest Matches: Not many people in wrestling history are as respected or mysterious as The Undertaker, and few have lasted as long. Since he showed up at Survivor Series in 1990, The Deadman has been a part of WWE through many changes, really becoming what the company is all about.
Over an amazing 30 years, Undertaker wrestled almost every top star WWE had. He created moments that made it hard to tell what was real and what was just for show. His WrestleMania streak might be what he’s known for most, but Undertaker had great matches that weren’t at WrestleMania. These matches really show what makes him WWE’s most loved icon. Let’s take a look on Undertaker’s Greatest Matches of his legendary WWE career
Undertaker’s Greatest Matches of WWE
Table of Contents
- 10. Undertaker vs. Undertaker – SummerSlam 1994
- 9. Undertaker vs. Kane – Unforgiven 1998
- 8. Undertaker vs. Batista – WrestleMania 23
- 7. Undertaker vs. Kane – WrestleMania 20
- 6. Undertaker vs. Brock Lesnar – Hell in a Cell 2015
- 5. Undertaker vs. Edge – SummerSlam 2008
- 4. Undertaker vs. Triple H – WrestleMania 27
- 3. Undertaker vs. Bret Hart – SummerSlam 1997
- 2. Undertaker vs. Kurt Angle – No Way Out 2006
- 1. Undertaker vs. Shawn Michaels – Streak vs. Career (WrestleMania 26)
10. Undertaker vs. Undertaker – SummerSlam 1994
The SummerSlam 1994 match between the true Undertaker & his “imposter” remains one of WWE’s most surreal events based purely on its story rather than the quality of the wrestling. Ted DiBiase (the manager/representative of the fake Undertaker) had manipulated the fake Undertaker for weeks and had a build up to the match that was very intriguing.
When the true Deadman finally returned, it was one of the most chilling moments in WWE history. The image of two identical men colliding in the ring will always stand out and the decisive finish (three Tombstone piledrivers followed by a coffin sendoff) established the real Undertaker’s legitimacy in WWE.
9. Undertaker vs. Kane – Unforgiven 1998
The epic feud of the Undertaker versus Kane was taken to another level at Unforgiven 1998 when WWE held its first-ever Inferno Match. Flames engulfed the ring, making the fight both more dangerous and more of a mind game between the hellish brothers. The match was more of a show than a technical wrestling match, but the vibe was incomparable.
By killing the match with fire, hence, a very fittingly dark Undertaker’s win he actually set fire to Kane’s arm helped add one more eerie chapter to the storied WWE feud and was the very first time a stipulation of this kind was used which would still be felt for years to come.
8. Undertaker vs. Batista – WrestleMania 23
WrestleMania 23 is the start of Undertaker’s historic performance at WrestleMania when he stole the show. After winning the Royal Rumble, The Deadman went head-to-head against World Heavyweight Champ Batista in a match that was heavy on power, yet still went above and beyond expectations.
While both wrestlers were predominantly known for their power, they displayed an unexpected level of quickness, countering expertise, and common matches of near fall situations throughout the match.
The Undertaker won his first World Heavyweight Championship with his Tombstone Piledriver; and the energy from the audience at Detroit made this match one of the greatest heavyweight matches in the history of WrestleMania.
7. Undertaker vs. Kane – WrestleMania 20
WrestleMania 20 is unforgettable because it was the night The Undertaker came back. After being the American Badass for years, Undertaker showed up again as his original supernatural character, and the crowd went absolutely wild – it was one of the loudest reactions ever in WWE history.
When Paul Bearer walked out and the classic gong rang, everyone knew a legend was back. The match itself wasn’t anything too special, but the moment meant so much to everyone. Undertaker beat Kane pretty easily with a Chokeslam and Tombstone, which showed that his most powerful version was back.
6. Undertaker vs. Brock Lesnar – Hell in a Cell 2015
After the Streak was surprisingly ended at WrestleMania 30, Undertaker went on a one-man war against Brock Lesnar. The 2015 Hell in a Cell fight between them was, in a way, a cruel yet beautiful testament of how the Undertaker could still endure even in the last days of his career.
The bout became notable as one of the most brutal WWE PG Era Hell in a Cell matches. Although it was Lesnar’s last F-5 that made the final, it was, however, the resistance of the Undertaker that most notably, once again, reminded him to be of the greatest and toughest ones.
5. Undertaker vs. Edge – SummerSlam 2008
At SummerSlam 2008, Undertaker and Edge put on a clinic on how to tell a story in a Hell in a Cell Match. This match had drama, creativity and intensity, despite the restrictions imposed by being in the PG Era.
The forces of Edge’s desperation and Undertaker’s insatiable thirst for vengeance made for an electrifying ending to the match when Undertaker chokeslammed Edge off a ladder through the ring creating a lasting image that will never be forgotten as one of the greatest visual moments in WWE’s history and also will ensure that this match is remembered as a defining moment in both men’s careers.
4. Undertaker vs. Triple H – WrestleMania 27
The Undertaker versus Triple H at WrestleMania 27 really showed how tired wrestlers can get. They called it “End of an Era” because both guys went all out. Triple H beat on Undertaker pretty hard with chairs and got super close to winning a bunch of times.
Undertaker won with Hell’s Gate, but the image of Triple H standing while Undertaker got taken away on a stretcher was intense. It’s one of the most memorable and unsettling fights WrestleMania ever had.
3. Undertaker vs. Bret Hart – SummerSlam 1997
One of the most technically brilliant matches that ever existed was the one between the Undertaker and Bret “Hitman” Hart at SummerSlam 1997. Hart carefully broke down the Undertaker’s legs, thus preventing him from using his power, and the presence of Shawn Michaels as a special guest referee was adding to the tension.
A chair shot that was supposed to hit Hart but hit the Undertaker instead, giving the victory to Hart. More importantly, the match directly set the stage for the iconic Hell in a Cell bout between Undertaker and Michaels, cementing its historical significance.
2. Undertaker vs. Kurt Angle – No Way Out 2006
Described by many as the most underrated masterpiece of The Undertaker’s career, the match that took place between The Undertaker and Kurt Angle at No Way Out in 2006 was of WrestleMania quality months before WrestleMania.
The way Kurt Angle’s technique based wrestling blended with the striking and submission style of The Undertaker was a perfect combination to create an exciting fast-paced, reversal-based match. Even though The Undertaker lost the match, it is a perfect example of how he could adapt to wrestlers who are viewed as the best technical wrestlers in the business.
1. Undertaker vs. Shawn Michaels – Streak vs. Career (WrestleMania 26)
WrestleMania 26 is definitely a high point in The Undertaker’s career. Shawn Michaels risked it all, putting his own career on the line for one last try to break The Streak, so the pressure was intense. Every near miss and close call felt huge.
In the end, Undertaker’s Tombstone Piledriver finished Michaels and made The Streak WWE’s biggest symbol of power. It’s still seen as not just Undertaker’s best match, but one of wrestling’s all-time greats.
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