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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

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.

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21 Giant Gonzales (IX)

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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.

Giant Gonzalez holds the distinction of being one of only two of The Undertaker’s opponent to not be pinned or forced to submit. Gonzalez lost his match by disqualification for rendering The Undertaker unconscious with a rag soaked in chloroform. Sadly, this was the highlight of Gonzalez’ career in WWE and solidifies his position on this list.

20 Shane McMahon (XXXII)

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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.

Shane is a former European and Hardcore Champion, and Shane was voted Rookie of the Year by Pro Wrestling Illustrated. Shane has main-evented cards, and has had four-star matches against people like Kurt Angle and other top stars. Shane is not a wrestler, and probably never wanted to be one, but among The Undertaker’s WrestleMania opponents, his career was at least better than Giant Gonzalez’.

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.

Surprisingly, A-Train, or Albert, as he was known then, was able to sneak an IC title reign in between the likes of Chris Jericho, Triple H, Jeff Hardy, and Kane during the Attitude Era. His reign began a period when the title was pushed down the card with people like Lance Storm, William Regal, and Test holding the title after Albert. A-Train didn’t do much else in WWE, as he was constantly enduring gimmick changes, but now, he is the head trainer in NXT.

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.

Bundy, like most giants in the 1980s, never captured any championship gold, or actually made any real impact within the company. Bundy never seriously challenged for the WWF Championship, and his most memorable feud was against Hillbilly Jim, in matches that involved several “midget wrestlers”.

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.

The Big Bossman was more of an '80s “character” in the mold of Doink the Clown and Duke “The Dumpster” Droese than he was a credible wrestler. His career received new life in the Attitude Era, as his character went from prison guard to body guard to member of the Corporation to four-time Hardcore champion. The Hardcore title’s 24/7 rule created title reigns for many wrestlers, but the Bossman holds the record for the longest single reign with the title, and the Bossman is the only multi-time Hardcore champion who does not have a reign that lasted less than two weeks.

16 Mark Henry (XXII)

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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.

In WWE, Henry has been a World Champion, the European Champion, and the ECW Champion. He is also one of the longest tenured talents on the WWE roster, debuting in 1996, after competing in the 1996 Summer Olympics. His actual first appearance was in 1994, when he was interviewed by Jerry Lawler, meaning that he has been involved with WWE for more than 20 years.

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.

Snuka was one of the top baby faces in the company during the Hulkamania era, and by the time that the Undertaker arrived in WWE, Snuka was nearing the end of his career, but he was still a credible opponent for The Dead Man. Snuka never won any titles while in the WWE or WWE, but his feud with the Magnificent Muraco, and his appearance on Piper’s Pit, leading to his feud with Roddy Piper are legendary and they show the greatness of Jimmy “Superfly” Snuka.

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.

During his time in WWE, Sid was mainly a giant who was treated like the many other very large men who worked for the company during that period. The feeling was that, in the suspension of disbelief, if a really large, really strong man was to win the WWE Title, it would not be believable for a smaller man to defeat the larger man for the belt. As such, Sid’s two title reigns lasted less than 100 days combined, and each title loss was due to outside interference. Sid accomplished very little in WWE, but he was involved in the Undertaker’s first WrestleMaina title match and that can never be taken away from him.

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.

Bray Wyatt has not won many titles during his brief time in WWE, only recently, as of this writing, gaining the SmackDown tag titles, his first taste of WWE gold. However, Wyatt’s influence on the business has made him a legitimate star. Currently, Wyatt is arguably the most popular heel character in professional wrestling, as fans around the world light up arenas whenever The Wyatt Family music hits and the lights go out, and no matter how many good guys The Wyatt Family torments, his “fireflies” are always there for him, looking to “follow the buzzards”.

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.

Show has 18 total championships under the WWE banner, including four world titles and eight tag title reigns with four different partners. His 18 titles in WWE puts him ahead of many of the top stars in the company’s history, and in addition to these, he also has two world titles and three tag title reigns from WCW. The only WWE men’s title that he never won was the European title, but he will go down in history as the only wrestler to ever win a WCW World War 3, 60-man battle royal, and an Andre the Giant Battle Royal at WrestleMania.

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.

Roberts worked for several years in the wrestling business without winning titles, but his specialty was in creating intrigue in his story lines with his promo ability. It was this ability, along with his stellar ring work that earned him a spot in the WWE Hall of Fame.

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.

While Nash achieved most of his acclaim in WCW, he was able to capture a fair amount of championship gold in the WWF. In April of 1994, he won the Intercontinental title, and in August of the same year, he won the tag titles with Shawn Michaels. In November of 1994, Diesel defeated Bob Backlund in eight seconds to become the WWF World Champion, making him the third ever WWE Triple Crown Champion, as well as the fastest man to ever achieve the feat, with only 227 days between the first title and the last, a record that would stand until CM Punk achieved it faster. Nash has achieved many firsts in professional wrestling, including, at the time, taking carrying the Undertaker in a match at WrestleMania longer than 'Taker had gone prior.

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.

Kane was the third ever Grand Slam Champion in WWE history, with two World Championships, two Intercontinental Championship, one reign each as ECW and Hardcore Champion, and 12 tag title reigns with seven different partners. Kane also won the 2010 Money in the Bank Ladder match, and has appeared in 19 Royal Rumbles. Kane has 18 titles during his WWE tenure. By comparison, The Rock has 17 championships, Steve Austin has 13, and Shawn Michaels, considered one of the greatest performers in WWE history, has 14, which says a lot about 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.

Batista came from the legendary training class that featured Brock Lesnar, John Cena, Randy Orton and Shelton Benjamin. He was a six-time World Champion and a four-time Tag Team Champion, and is one of only six men who have won the Royal Rumble twice. Unfortunately for Batista, he will be remembered by new fans as the guy who returned to WWE as a supposed babyface and won the 2014 Royal Rumble, only to be loudly booed because Daniel Bryan was not entered into the match, and thus did not win the coveted title match 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.

Punk was a five-time World Champion, and also won the ECW Championship, the tag titles and the Intercontinental title. Punk is also the only wrestler who ever won the Money in the Bank Ladder match twice, winning twice in his four attempts in the match. If Punk had remained in WWE, his career might have been placed higher on this list, as he would have continued to amass championships and accolades.

6 Brock Lesnar (XXX)

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“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.

Brock has only won four WWE World Championship, but his title wins came at the expense of The Rock, Kurt Angle twice, and John Cena, three of the best performers in the history of the business. Brock has been in the ring with many of the all-time greats, and he has emerged victorious more often than not. Being the one man who was able to defeat The Undertaker at WrestleMania makes Brock a major part of wrestling history and that accomplishment can never be taken away from him.

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.

Unlike many other top stars in WWE, Orton, though he is a 12-time World Champion, has not won many other titles other than World titles during his time in WWE. Orton has one reign as Intercontinental Champion, and has had two reigns as a tag champ; one in 2004 as a member or Rated RKO with Edge, and another eleven years later with Bray Wyatt and the Wyatt Family. However, his IC Title reign is one of the longest since the turn of the century, which shows that Orton is truly one of the top stars in WWE.

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.

Edge ended his WWE career as an 11-time World Champion, a 14-time tag champion, a five-time Intercontinental Champion, and as the first man to successfully cash-in two Money in the Bank contracts, though he won the second one from Mr. Kennedy. Edge is also the first man to win the Money in the Bank match and the Royal Rumble, though he was unsuccessful title match after winning the Rumble. Edge’s 31 total titles in WWE are the most of any competitor in WWE history, which places his career ahead of the all-time greats in the history of the company.

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.

Triple H is one of the most decorated performers in WWE, having won 24 championships, including 14 World Titles. Triple H was also named as the Wrestler of the Decade by Pro Wrestling Illustrated for the period between 2000 and 2009. Without the two guys ranked ahead of him, Hunter would be at or near the top of nearly every list that ranks the top wrestlers in a given category.

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.

Apart from all of the championships that Michaels has won, he is the first ever WWE Grand Slam Champion, and has won Pro Wrestling Illustrated’s Match of the Year eleven times. Nine of those eleven matches were WrestleMania matches, including his two matches against the 'Taker at the tail end of a seven year streak of winning the award. Shawn Michaels was called “Mr. WrestleMania”, and that title is much deserved, but against the Undertaker, he was just another victim.

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