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Ranking The Wrestling Careers Of The Undertaker's 21 WrestleMania Opponents

The Undertaker is one of the greatest creations in the history of WWE. Aside from having been with the company for over 25 years, there are few talents who are more revered or respected than The Dead Man. In 1991, The Undertaker made his WrestleMania debut, and over 25 years later, the match involving The Undertaker is still one of the featured matches of the Showcase of the Immortals. Just below the world title matches, and the match featuring the big ticket part-timer, is the match where The Undertaker defends his WrestleMania record against yet another challenger.

The Undertaker’s record at WrestleMania is 23-1, and through those 24 matches, The Undertaker has faced 21 different opponents, as some who faced him have done so more than once. Some of those 21 opponents have been among the best wrestlers in the history of the business, while others have been individuals whose careers never amounted to very much. In ranking the careers of The Undertaker's WrestleMania opponents, it is necessary to remember that the rankings cover the entirety of the individuals’ careers, and not just the match against Big Evil. So here now is a look at the careers of the 21 individuals who were fortunate enough to have faced The Undertaker in a match at WrestleMania.

21 Giant Gonzales (IX)

via youtube.com

The debate here was whether or not Giant Gonzalez deserved to be ranked behind or ahead of Shane McMahon. Shane is an executive, who has had a number of matches, but Gonzalez was actually listed as a wrestler, and his career warranted his position on this list. Gonzalez, at nearly eight-feet tall, was the tallest professional wrestler in the history of the business, but unfortunately for him, his talent did not match his massive size. Gonzalez was brought into the WWE to feud with The Undertaker, but after a pair of losses to the Undertaker at WrestleMania and SummerSlam, the feud was essentially over, and Gonzalez’ career in the WWE ended shortly after.

20 Shane McMahon (XXXII)

via mirror.co.uk

Shane McMahon is, to date, the most recent victim of The Undertaker, having lost to him at WrestleMania XXXII. Though the match had a stipulation that was not adhered to by WWE, it was one of the better matches of recent years. Oddly, Shane, who is not an actual wrestler, but is instead an executive, has had a better career than Giant Gonzalez. Aside from the fact that Shane has won some championship gold while in WWE, his matches have been more compelling than Gonzalez’ were, which is why Shane is ranked higher than the Argentine Giant.

19 A-Train (XIX)

via wwe.com

At WrestleMania XIX, in what was his eleventh match, The Undertaker competed in his only Handicap match, against A-Train and the Big Show. The match was supposed to be a tag team match with Nathan Jones as The Undertaker's partner, but Jones suffered a beating and left The Undertaker on his own against two very big and very strong men. With a little help from Jones, The Undertaker pinned A-Train Of the two wrestlers who faced the Undertaker in that match, A-Train is clearly the one who deserved to be ranked lower that the other.

18 King Kong Bundy (XI)

via prowrestling-hirek.blogspot.ca

King Kong Bundy was more of an attraction in the WWE than he was a viable competitor. During his time with the company, he feuded with Hulk Hogan and Andre the Giant, but he was the heel whose job it was to elevate the faces, and he did that job well, losing in decisive fashion when called upon. His match against The Undertaker came about because Bundy was a member of Ted DiBiase’s Corporation faction that was feuding with 'Taker, and Bundy had stolen The Undertaker's urn during Taker’s Royal Rumble match against Irwin R. Shyster. The WrestleMania match was a glorified squash victory for Taker, and was designed to jumpstart the feud between 'Taker and Kama.

17 The Big Bossman (XV) 

via wwe.com

The Big Bossman’s match against The Undertaker at WrestleMania XV represented the first gimmick match in the streak. The match was a Hell in the Cell match, and was more about the feud between Vince McMahon’s “Corporation” and The Undertaker’s “Ministry of Darkness” than it was about the two men. Though the match was the second longest match on a subpar card, the match was the shortest cell match in which The Undertaker has been involved.

16 Mark Henry (XXII)

via blogspot.com

Mark Henry, “The World’s Strongest Man”, is the only man on this list who was actually defeated in a match but was not pinned or forced to submit. Giant Gonzalez was disqualified in his match, but Mark Henry was stuffed into a casket at WrestleMania 14. Mark Henry’s feud with the Undertaker began because Henry interfered in a world title match between The Undertaker and the then-champion Kurt Angle. Strangely, the feud escalated quickly and the first match between the two men was a casket match at WrestleMania. The match was one of the shortest WrestleMania matches that the 'Taker has been involved in, and feud ended the day after WrestleMania after only two matches.

15 Jimmy “Superfly” Snuka (VII)

via dailywrestlingnews.com

Jimmy Snuka is a wrestler who many other wrestlers were inspired by. Many New York-based wrestlers were in Madison Square Garden when Jimmy Snuka dove off of the top of a steel cage against the Magnificent Muraco. Snuka was the veteran who was given the task of testing out the newcomer when Snuka became the first WrestleMania notch on the belt of The Undertaker. Not only was Snuka the Undertaker’s first opponent, he also holds the distinction of appearing in the shortest WrestleMania match that The Undertaker participated in.

14 Sycho Sid (XIII)

via m.goliath.com

The Undertaker’s match against Sycho Sid at WrestleMania was the first time that the Undertaker would compete at WrestleMania for the WWF Championship. Sid came into the match as champion, and left WrestleMania as another victim of the Undertaker, though Bret Hart interfered in the match and helped Taker to win the title. This match, in 1997, was the first of Taker’s WrestleMaina matches to exceed 20 minutes, though Taker would not reach that plateau again until 2008.

13 Bray Wyatt (XXXI)

via pintrest.com

Bray Wyatt was the first person to face The Undertaker at WrestleMania after The Streak was ended. Bray, referring to himself as “The New Face of Fear,” challenged 'Taker almost immediately after 'Taker was defeated at WrestleMania XXX, feeling that The Dead Man was at his most vulnerable. However, as with others who challenged The Undertaker at WrestleMania, Bray Wyatt would taste defeat. Wyatt’s match would be the first match that finished in less than 20 minutes since The Undertaker's match against Batista at WrestleMania XXIII.

12 Big Show (XIX)

via pwmania.com

Big Show was the other person who faced The Undertaker in the Handicap match at WrestleMania XIX, along with A-Train. The Undertaker pinned A-Train because Nathan Joes interfered in the match and neutralized Show. Oddly, Big Show never got another opportunity to face The Undertaker at WrestleMania, though they have faced numerous times throughout their careers. Aside from this match, Big Show has done everything in WWE that a performer could do, with numerous title reigns to his credit.

11 Jake “The Snake” Roberts (VIII)

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Jake “The Snake” Roberts was able to forge out a Hall of Fame career for himself without ever putting a title belt around his waist in WWE. Jake was considered one of the smartest performers in the business, and many wrestlers, like Dallas Page and Raven, cite Roberts as someone who they were able to learn from, particularly about ring psychology and how to deliver a promo with maximum effectiveness. Jake was The Undertaker’s second WrestleMania opponent, a match which stemmed from Roberts’ feud with Randy Savage. Roberts tried to hit Savage’s manager Elizabeth with a chair, and the Undertaker stopped him, and the two men, who had previously been aligned against Savage, were suddenly at odds with each other, making this match The Undertaker's first babyface WrestleMania match.

10 Diesel (XII)

via wweindonesia.com

Kevin Nash, in the character of Diesel in WWE had begun feuding with The Undertaker as each man pursued then-WWE Champion Bret Hart, with each costing the other victories in the title opportunities. Interestingly, Nash was negotiating with WCW at the same time as he was preparing for this match, as his WWE contract was coming to an end, with Vince McMahon unable to match WCW’s offer. Nash’s match with The Undertaker was Taker’s first WrestleMania match that lasted longer than 10 minutes, as 'Taker was built as a destroyer before he was placed into title contention and his level of competition improved.

9 Kane (XIV/XX)

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Perhaps The Undertaker’s most memorable feud was against his “brother” Kane. Kane and the Undertaker have been both allies and foes throughout their time in WWE. Kane is the first person to face the Undertaker twice in WrestleMania matches, but that also made him the first person to lose twice to the Undertaker in WrestleMania matches. Many fans view Kane’s career as one filled with longevity but not much acclaim, but there has been a lot of success in Kane’s career.

8 Batista (XXIII)

via wwe.com

Batista walked into WrestleMania XXIII as World Heavyweight Champion, prepared to face the 2007 Royal Rumble winner, The Undertaker. The Rumble victory was The Undertaker's only victory in the Rumble match, and the victory over Batista made 'Taker the first wrestler to win both the WWE Championship and the World Heavyweight Championship at WrestleMania. This match is arguably the point where WWE began to realize that the streak existed, because it was after this match that the company created the DVD that detailed The Undertaker's undefeated record at WrestleMania.

7 CM Punk (XXIX)

via nexterawrestling.ne

Seemingly, CM Punk earned his match against The Undertaker by complaining to management about how he was being used despite the fact that he was, at times, the WWE Champion and supposedly the top man in the company. Punk had a sound argument because in the short time that he was with the company, he amassed quite a few championships, had risen to the top of the company, and was deserving of true main event status. Punk achieved the WWE Triple Crown in 197 days, 30 days faster than previous record holder Kevin Nash. His achievement broke a record that had stood for 15 years.

6 Brock Lesnar (XXX)

via Sportskeeda.com

“The Beast” Brock Lesnar is the only man who faced The Undertaker at WrestleMania and walked out victorious. Brock Lesnar shocked the wrestling world by defeating the unbeatable Undertaker at the show where The Dead Man has never lost, but this was just another fight for the man considered the greatest combat athlete on the planet. Brock is the only athlete in the history of combat sports to win an NCAA Division-1 wrestling championship, a UFC title and a WWE World Championship.

5 Randy Orton (XXI)

via prowrestling-hirek.blogspot.ca

Randy Orton’s match against The Undertaker came during Orton’s “Legend Killer” phase when Orton, on the advice of “Superstar” Billy Graham, was attempting to “go where no other wrestler had gone before”. The advice gave Orton the notion to attempt to end Taker’s WrestleMania undefeated streak. The match was the beginning of a nine-month feud between Orton and The Undertaker.

4 Edge (XXIV)

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Edge is one of the most highly decorated wrestlers in the history of the business, and in addition to all of the accolades that he achieved; he is also one of the select few men who were given the honor of facing The Undertaker at WrestleMania. WWE began to realize that 'Taker was undefeated at WrestleMania once the streak reached double figures, and the company made a DVD about The Streak when it reached 15 wins. Edge was chosen to be in the first match after the creation of that DVD.

3 Triple H (XVII/XXVII/XXVIII)

via WWE.com

Triple H first fought The Undertaker years before the first time that HBK faced “he Dead Man but Triple H came back to avenge HBK’s losses by facing 'Taker again. Triple H holds the distinction of being the only competitor to face The Undertaker three times at WrestleMania, but it has amounted to three losses, and makes tRIPLE h one of the two men to lose by submission. Hunter is also on record as participating in the longest of The Undertaker's WrestleMania matches, and at WM XXVII, though Triple H lost by submission; he was able to walk out of the ring while Taker had to be helped to the back.

2 Shawn Michaels (XXV/XXVI)

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“The Heartbreak Kid” Shawn Michaels is arguably the greatest perform in WWE and WrestleMania history, but he too fell victim to The Undertaker. Michaels was the second performer to face 'Taker twice, and was the first to face him in WrestleMania matches in consecutive years. Even though the second match cost Shawn Michaels his career, the two losses to the Undertaker do not diminish the Hall of Fame resume of HBK.

1 Ric Flair (XVIII)

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This one is a no-brainer. Ric Flair is arguably the greatest professional wrestler in the history of the business. Ric Flair is listed as a 16-time World Heavyweight Champion, but some lists have him winning as many as 25 World titles. Flair has also won 15 Wrestler of the Year awards between Pro Wrestling Illustrated and the Wrestling Observer Newsletter. Ric Flair won his first world title in 1981, and won his last world title in the year 2000, nineteen years later.

Ric Flair wrestled The Undertaker at WrestleMania X8 in what was The Undertaker’s 10th match. The match was a no disqualification match, and despite interference from Arn Anderson, 'Taker was able to emerge victorious. Flair was 53 years old at this point in time, and was two years removed from his last world title, but he was still able to go out and have a stellar match. Ric Flair is one of the most decorated wrestlers in the history of the business, and this is why he is the first; and so far only two-time WWE Hall of Fame inductee.

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Ranking The Wrestling Careers Of The Undertaker's 21 WrestleMania Opponents