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The 8 Best And 7 Worst Opponents Of The Undertaker's Career

The Undertaker is arguably one of the most iconic figures in WWE. Throughout his career, he has managed to be compelling and captivating and throughout the decades he has managed to stay relevant, keeping the audiences captivated. The Undertaker has always been a league of his own with his unique entrance, style and technique to give the WWE Universe and the world performances of a lifetime. While The Undertaker is legendary in his own right, perhaps his undefeated WrestleMania streak between 1991-2013 is something that will always remain a distinct point in his legacy because no one has ever gotten close to remaining undefeated for twenty-one WrestleMania before.

Maybe it was the build up or the intensity that The Undertaker was willing to do to unhinge and unnerve his opponents, one thing was for certain, The Undertaker knew how to play mind games to get into his opponent's head in order to get the advantage.  This has led to some unbelievable feuds that have left resounding impressions on the WWE Universe and his opponents. Although the Undertaker isn't just known for his impeccable WrestleMania fights, the Undertaker was also known for breathtaking Hell in A Cell matches that have left people speechless at the lengths that he would go to in order to get the win.

With a career that has spanned decades, he has faced many different opponents from all shapes, sizes and heights, here are eight of The Undertaker's best opponents and seven of his worst.

15 Best: CM Punk 

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CM Punk was the last opponent before Brock Lesnar went to break the streak a year later. The two shared epic verbal assaults back and forth. With CM Punk in possession of Paul Bearer's ashes, the feud between the two hit an intense point, the feud was no longer just about the streak, it was to protect and defend the legacy of The Undertaker's "Father". The Undertaker was furious and had Paul Bearer's ashes returned to him.

For weeks, CM Punk continued to disrespect the urn of Paul Bearer, he dropped it, kicked it around. It wasn't just exciting and emotive exchanges that the two exchanged when the time came at WrestleMania, the two tore each other to shreds, which led it to become one of The Undertaker's longest WrestleMania matches, lasting twenty-two minutes and seven seconds.

14 Worst: Big Boss Man

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The Undertaker faced Big Boss Man at WrestleMania XV in 1999, while this match was arguably iconic since it was a WrestleMania Hell In A Cell match, it didn't match The Undertaker's normally high standard. At the time The Undertaker was feuding with the McMahon Corporation. The Big Boss Man claimed that he was representing the McMahon Corporation, the two failed to have any chemistry.

While The Undertaker was handcuffed to the cage itself, it appeared that it wasn't going to stop The Deadman from winning the match. After the Big Boss Man dealt The Undertaker a particularly hard blow that knocked him to the ground, the handcuff ripped off allowing the Undertaker to successfully gain control and win the match. At some point, The Undertaker ended up hanging the Big Boss Man from the top of the cell and watched as the match ended and the cell rose with the Big Boss Man still attached to it.

13 Best: Randy Orton

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Many would argue that The Undertaker feud was the one that pushed Randy Orton to the next level. Although he had previously won the WWE World Heavyweight title, his title run wasn't as great as one would expect. He lost his momentum shortly after, and he wouldn't gain it back until he began feuding with The Undertaker.

Orton was known as The Legend Killer at the time, as he feuded with various legends from Mick Foley to Shawn Michaels. The Undertaker and Orton faced off at WrestleMania 21, with The Deadman emerging victorious. The feud would continue for months to come as Orton picked up the win at SummerSlam 2005.

12 Worst: Sycho Sid

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At WrestleMania 13, Sycho Sid and The Undertaker faced off for the WWE World Heavyweight championship, the match and feud had all of the potentials in the world to be a great one. However, things didn't go as planned.

Bret Hart interfered in the match helping The Undertaker pick up a win. The match, which closed out WrestleMania, went for twenty-one minutes and nineteen seconds. Critics and fans thought the match was boring, especially after having witnessed a classic between Bret Hart and Stone Cold Steve Austin.

11 Best: Edge

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Edge and the Undertaker had many feuds over the course of their careers, they battled at WrestleMania XXIV and later on at SummerSlam that same year, the two had intense battles. Edge described the matches between the two as "the biggest of my career". The feud involved Edge and the Undertaker trying to outdo each other when it came to mind games and manipulation.

The match were intense as they exchanged spears, tombstones and chokeslams. It is arguably one of The Undertaker's greatest feuds as they had amazing chemistry and the ability to pull off an exciting main event match that was for the World Heavyweight Championship.

10 Worst: Roman Reigns

Roman Reigns always causes some sort of debate, some people love him, some loathe him but nobody can deny that The Undertaker has officially passed the torch to Roman Reigns following their WrestleMania bout. The feud was a battle for dominance with both claiming WWE as their yard.

Everything was laid out on the table, the Undertaker had everything to lose while Roman Reigns had everything to gain. It was Roman Reigns, who ended up coming out on top. Sadly, the build for the feud was underwhelming and the match wasn't exactly a great one. It had several botches and many believe that Roman Reigns shouldn't have been The Deadman's last opponent.

9 Best: Brock Lesnar 

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It came as a shock to everyone when Brock Lesnar defeated The Undertaker, ending his undefeated streak at WrestleMania. But what was more surprising was how long The Undertaker managed to fend and deal with Brock Lesnar's savage assault on The Deadman. Every time Brock Lesnar thought the Undertaker was down and out, he managed to get back up.

The two have battled on multiple occasions, even going back to the early 2000s. After the streak came to an end, The Undertaker was looking for redemption and he certainly did so, as he got his revenge on Lesnar.

8 Worst: Giant Gonzales 

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Giant Gonzales and The Undertaker faced each other at WrestleMania IX in 1993. Although he had the height and presence that WWE loves, Giant Gonzales didn't possess the ring ability as he could barely move. When he feuded with The Undertaker, it didn't make sense as to why were feuding.

When the two came to blows at WrestleMania, the match only lasted seven minutes and thirty-three seconds and the match itself ended rather peculiarly, Giant Gonzales got himself disqualified. It is unclear why WWE thought it was a wise idea to put Giant Gonzales against The Undertaker in the first place.

7 Best: Mick Foley 

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Mick Foley is arguably one of the most extreme wrestlers that has ever been in WWE, there was nothing that Mick wouldn't do from Hell In A Cell, to barbed wire spots. Mick put his body on the line for everyone. One of the most iconic moments featured him and The Undertaker in a Hell in a Cell match, with Foley being thrown off the top of the cage.

The famous feud between the two lasted for a considerable amount of time. It's one of the most legendary feuds of all time, and many consider Mick Foley to be The Undertaker's best opponent thanks to the legendary matches that they had. Footage from that rivalry continues to be shown to this day.

6 Worst: Vladimir Kozlov 

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Kozlov feuded with The Undertaker briefly and why we couldn't be too sure. He beat The Undertaker once via disqualification which was due to Jeff Hardy intervening and attacking Kozlov, allowing him to reach a title opportunity to face Triple H at Survivor Series. The feud soon died down and Kozlov went on to face the likes of Jeff Hardy and Triple H.

During his rookie year, Kozlov got a clean victory over The Deadman on SmackDown. He would go on to become a comic act not too long after, doing multiple segments with Santino Marella. Kozlov was another example of WWE giving up on creating a monster after giving him a push.

5 Best: Triple H 

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Triple H and The Undertaker have also feuded numerous times throughout their careers. Triple H was determined to break the streak after his best friend Shawn Michaels failed to do so. The matchup between Triple H and The Undertaker was epic, they had the chemistry and star quality, as the match left people sitting on the edge of their seats.

A year later saw The Undertaker return to face Triple H in a Hell in a Cell match. This time, he was thought to be pitted to lose with Shawn Michaels as the special guest referee. The odds were stacked against him but The Undertaker managed to come out victorious once again.

4 Worst: Heidenreich

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While we aren't quite sure why The Undertaker ended up feuding with Heidenreich, it occurred when Heidenreich interrupted The Undertaker's championship match as he defended the title against John Bradshaw Layfield. Heidenreich was known for crazy behaviour, often becoming spontaneous and an erratic poet.

The feud went on to Survivor Series and then several more matches. Yet there seemed to be no apparent reason as to why the two were feuding. Originally, The Undertaker and Kane were supposed to team up to take on Heidenreich and Snitsky at WrestleMania 21. However, The Undertaker refused which led him to go on and feud with Randy Orton. Heidenreich was one of the many monsters that The Undertaker had to go against, who would end up going nowhere.

3 Best: Shawn Michaels 

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Shawn Michaels and The Undertaker had one of the greatest matches of all time at WrestleMania. Shawn was close to ending the streak at WrestleMania XXV, but as usual, The Undertaker managed to come out on top. The two would face off once again although there was much more on the line.

WrestleMania XXVI had a different tone, The Undertaker refused to give Shawn the right to a rematch. He eventually agreed but it came with a price, Shawn Michaels had to put something up, which was his career. The match was electric and Shawn gave everything he had but it wasn't enough to put The Deadman away and it led to Shawn Michaels retiring from professional Wrestling.

2 Worst: The Great Khali 

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The Great Khali had an impressive stature in height. For some reason, The Great Khali thought it would be wise to attack The Undertaker. The Deadman wasn't one to turn down a challenge and took on The Great Khali. Why? No one can be sure, perhaps WWE thought if they put him against The Undertaker, The Great Khali could perhaps get over.

If someone was going to be pitted against The Undertaker, it could have gone one of two ways, either it was going to heavily impact the Great Khali's career in a positive light or it was going to completely destroy it. While it didn't necessarily destroy The Great Khali's career it definitely did him no favours. The feud, as well as their matches were very sloppy.

1 Best: Kane

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There was always something unique whenever Kane and The Undertaker went to blows and the two did so on several different occasions. When the brothers collided, there were matches like no other, they would go to measures that no other WWE Superstar would dare to go. The feuds were dark and interesting as they feuded several times.

Both Kane and The Undertaker possess a natural ability in and out of the ring. While they were strong as The Brothers of Destruction, they made even better enemies. They would literally bring the house down, creating some truly memorable moments for everyone's entertainment. It's only right for The Undertaker's brother to be his greatest opponent.

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The 8 Best And 7 Worst Opponents Of The Undertaker's Career