Dead Man Feuding.

The Undertaker is a first-ballot Hall of Famer if there ever was one; an icon of the industry and someone who has been counted on time and time again to boost business, main event and sell tickets. Given he's clashed with so many different opponents during his 30-year run in the WWE, it's a valid question to ask which people have brought out the best in the Dead Man.

 

We're basing this on storyline rivalries The Phenom had with wrestlers and non-wrestlers alike, not speculating on what may have happened backstage. 

 

In counting down the Top 50 Undertaker Rivalries, Wrestling Merchandise and Memories looked at the following criteria:

 

  • How prominent was the rivarly?

  • What type of stage(s) did it play out on?

  • How memorable were the matches and/or segments?

  • How much did the rivalry do to advance either person's career?

 

If you'd like to be a part of this conversation, Tweet us at @canadianbulldog using the hashtag #Top50, or leave a comment below.

 

Ready? Here we go!

50.

Superfly Jimmy Snuka

WWE Hall of Famer Superfly Jimmy Snuka was The Undertaker's very first WrestleMania opponent for a streak that would span decades. In addition to their WrestleMania VII match, Snuka and The Dead Man also battled on the house show circuit during 1991.

48.

The Million Dollar Man Ted DiBiase

While WWE Hall of Famer The Million Dollar Man Ted DiBiase never faced The Undertaker in a wrestling match, he did send a variety of people to battle against The Dead Man over the years during his managerial career, including an evil doppleganger. 

46.

John Cena

John Cena faced Undertaker several times in the early heel part of his career, with The Dead Man teaching The Doctor Of Thuganomics some respect. Many years later, Cena challenged Taker to a match at WrestleMania XXXIV, which was brief and fairly unremarkable.

44.

King Kong Bundy

After The Undertaker vanquished IRS, his stablemate King Kong Bundy came to ringside and stole The Dead Man's prized urn, allegedly the source of his power. The theft led to a match at WrestleMania XI, where Taker made quick work of The Walking Condominium.

42.

The Dudley Boyz

In 2004, WWE Hall of Famers The Dudley Boyz abducted Undertaker's long time manager Paul Bearer at the urging of Paul Heyman. This led to Bubba Ray and D-Von Dudley facing The Dead Man in a match where Bearer was buried alive in a concrete crypt.

40.

Rob Van Dam

In late 2001, a newly-turned heel Undertaker targeted Rob Van Dam's Hardcore Championship. The Dead Man captured the gold at the Vengeance PPV. The next year, RVD appeared to have defeated World Champion Undertaker on Raw when the decision was reversed by GM Ric Flair.

38.

AJ Styles

In 2020, AJ Styles had appeared to win the Tuwaiq Trophy gauntlet match when The Undertaker appeared out of nowhere and pinned him. This led to a very personal grudge match at WrestleMania XXXVI in which The Dead Man prevailed in the first-ever Boneyard Match.

36.

Kama

Yes, we realize Kamala and Kama's names seem awfully similar. But in 1995, Kama (a/k/a WWE Hall of Famer The Godafther) stole The Undertaker's urn and turned it into a necklace of sorts. This led to a (yet another) casket match at SummerSlam that year.

34.

John Bradshaw Layfield

The Undertaker attempted to ended John Bradshaw Layfield's reign of terror as World Heavyweight Champion at SummerSlam in 2004. However, Taker accidentally got himself disqualified and later chokeslammed Bradshaw through the roof of his own limousine. This led to a Last Ride Match between the two.

32.

The Great Khali

When The Great Khali debuted in the WWE in 2006, his very first target was none other than The Undertaker. Surprisingly, Khali easily pinned The Phenom during their first match at Judgment Day. They battled on and off until later in the year, when Taker won in a Last Man Standing match.

30.

Muhammad Hassan

In a scene that shouldn't have aired on television in 2005, Muhammad Hassan ordered followers wearing ski masks to attack The Undertaker and then carry him off, making it look like an abduction. Of course, the segment aired the week of the infamous London subway bombings, sealing Hassan's fate in WWE.

28.

Diesel

At the Royal Rumble in 1996, Disel (a/k/a WWE Hall of Famer Kevin Nash) cost The Undertaker his shot at the WWF World Title. The following month, when Diesel was challenging for the same title, The Dead Man appeared from underneath the ring to cost him the match. They finally settled their score at WrestleMania XII.

26.

Kurt Angle

Shortly after his debut in 2000, WWE Hall of Famer Kurt Angle found himself at odds with The Undertaker after accidentally knocking over his motorcycle. Angle's brother Eric cost Taker their match at Survivor Series that year, and the two also had short-term programs in 2002, 2003 and 2006.

24.

The Big Show

In 1999, The Big Show chokeslammed The Undertaker "to hell" through a hole in the ring. This led to several bouts between the two over the years, including a handicap match at WrestleMania XIX, a Punjabi Prison match at The Great American Bash, and their very own Casket Match at Survivor Series 2008.

22.

Roman Reigns

Roman Reigns is one of the few challenges The Undertaker wasn't able to turn back. Reigns defeated The Dead Man at WrestleMania XXXIII, leading many to think at the time they'd witnessed The Undertaker's final match.

20.

Stephanie McMahon

The Undertaker has had several run-ins with Stephanie McMahon. During The Attitude Era, he abducted her in an attempt to marry the boss' daughter. Speaking of Triple H, there was also the angle before WrestleMania XVII where Stephanie tried to prevent her husband's Mania match with Taker.

18.

Jake The Snake Roberts

At first, The Undertaker was WWE Hall of Famer Jake The Snake Roberts's partner-in-crime for some time as they went after the likes of Randy Savage and Sycho Sid. But when Roberts attempted to blindside Miss Elizabeth with a steel chair, The Undertaker stopped The Snake and turned babyface in the process for the first time.

16.

Edge

By the time WWE Hall of Famer Edge and The Undertaker locked up at WrestleMania XXIV, it was a rivalry almost a year in the making. The Ultimate Opportunist cashed in his Money In The Bank briefcase against a prone Dead Man, and later that year cost Taker a shot at the championship. The two then feuded for months after Mania.

14.

Paul Bearer

While WWE Hall of Famer Paul Bearer is largely remembered for being in the corner of The Undertaker, it wasn't always that way. For example, at the conclusion of the Boiler Room Brawl in 1996, Bearer sided with Mankind instead of Taker. He then tried to rid the WWF of The Dead Man by debuting his brother Kane.

12.

Paul Heyman

In addition to making his life miserable while being SmackDown General Manager, Paul Heyman also had two of his clients go after The Undertaker at consecutive WrestleManias. According to Taker's one-time WCW manager, Heyman sent Brock Lesnar after The Phenom after CM Punk failed in his turn to do so.

10.

Randy Orton

At WrestleMania XXI, Randy Orton attempted to "make an impact" by defeating The Undertaker and like many before him, he was unsuccessful. But The Legend Killer didn't give up - he recruited his father Cowboy Bob Orton, and the two made 2005 a difficult year for Taker, including defeating him in a Casket Match.

8.

Yokozuna

It was during a Casket Match at Royal Rumble 1994 that The Undertaker lost to WWE Hall of Famer Yokozuna and apparently rose up to the heavens. The Dead Man wasn't seen for most of that year, resurfacing at SummerSlam and eventually turning his attention back to Yokozuna in (another) Casket Match at that year's Survivor Series.

6.

Hulk Hogan

In 1991, exactly a year after his WWF debut, The Undertaker defeated WWE Hall of Famer Hulk Hogan at Survivor Series, dropping the belt to The Hulkster days later at This Tuesday In Texas. In 2002, they rekindled their rivalry older and wiser, with Undertaker once again ending Hogan's Undisputed WWF World Title run.

4.

Mankind

Unlike many of this list, Mankind (a/k/a WWE Hall of Famer Mick Foley) was one of the first people to get into The Undertaker's head. It worked for a while, with Mankind scoring victories over The Dead Man in Boiler Room Brawl and Buried Alive matches, but Taker getting the last word during their infamous Hell In a Cell Match.

2.

Triple H

WWE Hall of Famer Triple H is the only person to face The Undertaker at three different WrestleManias - XVII, XXVII and XXVIII, including their brutal Hell In A Cell "End of an era" match. The Game also waged war with the Dead Man over the Undisputed WWF World Title in 2002.

49

Bray Wyatt

Following The Undertaker's unexpected loss to Brock Lesnar, Bray Wyatt coaxed The Dead Man back to the ring, implying that Undertaker was afraid to still compete. The two met in a match at WrestleMania XXXI, with The Phenom proving to Wyatt he wasn't "dead yet."

47.

Goldust

The Undertaker likes to play mind games with his opponents, but Goldust turned the tables when he tried to hit on The Dead Man in the mid-1990s. An alliance between Goldust and Mankind was soon formed, leading to a casket match at In Your House: Beware Of Dog, where Goldust actually defeated The Undertaker!

45

Irwin R. Shyster

The only things that are certain in life are death and taxes, making The Undertaker versus Irwin R. Shyster an interesting matchup. IRS repossessed some of The Dead Man's tombstones and burial plots because of an outstanding tax bill, leading to a match at the 1995 Royal Rumble.

43.

Maven

At the Royal Rumble in 2002, Tough Enough winner Maven surprisingly eliminated The Undertaker from the match. And while Maven paid dearly for his upset move that night, it was enough to ignite a brief rivarly between the two.

41.

King Mabel

In 1995, King Mabel interfered in a match between The Undertaker and Yokozuna and (legitimately) fractured The Dead Man's orbital bone after an errant legdrop to the face. When he returmed, The Dead Man battled The King in a casket match on pay-per-view.

39.

Booker T

WWE Hall of Famer Booker T swore he wasn't afraid of The Undertaker when the two feuded in 2004. This prompted Booker to visit the graveyard, practice voodoo and find out ways to topple The Dead Man before their Judgment Day match, a clash which The Undertaker won handily. 

37.

Kamala

In 1992, Kamala and The Undertaker battled at SummerSlam. Just as Taker was about to tombstone his foe, handler Kimchee interfered and the two laid a savage beating on The Dead Man. This led to to a casket match between the two at the Survivor Series.

35

Shane McMahon

Throughout The Attitude Era, The Undertaker and Shane McMahon alternately were rivals and allies, depending on the situation. Years later, Shane O'Mac returned to WWE and battled The Phenom in a Hell In A Cell match at WrestleMania XXXII.

33.

Giant Gonzales

At the 1993 Royal Rumble, Giant Gonzales (formerly El Gigante in WCW) appeared out of seemingly nowhere and eliminated Undertaker from the Rumble match. This led to an inconclusive match at WrestleMania IX and a Rest In Peace match at SummerSlam where Taker was able to slay the giant.

31.

The Rock

At first blush, it may appear as though The Undertaker and The Rock merely co-existed as top stars during The Attitude Era. However, The Dead Man and The Great One did battle on numerous pay-per-views, including Survivor Series 1998, King of the Ring 1999, Unforgiven 2000 and Vengeance 2002.

29.

Mark Henry

The Undertaker's rivalry with WWE Hall of Famer Mark Henry began in 2006, when The World's Strongest Man interfered in Undertaker's match, leading to (yet another) Casket Match, this one at WrestleMania XXII. A year later, Henry returned to WWE and attacked Taker once again.

27.

Jeff Hardy

In 2002, The Undertaker defended his World Championship against Jeff Hardy and was dismissive of the challenge at first. But by the time they faced off in a Ladder Match on Raw, The Dead Man showed respect for Hardy, turning The Phenom babyface and giving Hardy quite the endorsement.

25.

Diamond Dallas Page

In 2001, an unknown stalker showed disturbing videos, creeping around The Undertaker's home with footage of his wife. The stalker was revealed to be WWE Hall of Famer Diamond Dallas Page, who wanted to become "famous" at the hands of The Dead Man. And if by "famous," he meant "losing repeatedly," DDP accomplished that.

23.

CM Punk

CM Punk first feuded with The Undertaker in 2009, with a couple of brutal encounters at the Breaking Point and Hell In A Cell pay-per-views. A few years later, Punk challenged The Dead Man to a match at WrestleMania XXIX, with Punk and manager Paul Heyman mocking the recent death of manager Paul Bearer.

21.

Sycho Sid

Sycho Sid presented an interesting challenge for The Undertaker at WrestleMania XIII - here was someone with roughly the same size and strength as The Dead Man, and he was going into the event as WWF Champion. However, Undertaker managed to end the event with his streak and the belt intact.

19.

Ric Flair

WWE Hall of Famer Ric Flair began his rivalry with The Undertaker while General Manager of Raw. A personal feud developed, with The Phenom attacking Flair's son David and best friend Arn Anderson ahead of their brutal clash at WrestleMania XVIII.

17.

Batista

When The Undertaker won the Royal Rumble in 2007, he received an automatic title shot at the champion of his choosing. He selected World Champion Batista and defeated The Animal at WrestleMania XXIII. The match was close, though, and led to Steel Cage and Last Man Standing matches that year.

15.

Evil Undertaker

What could be possibly be more personal than someone stealing your identity? After The Undertaker disappeared in early 1994, Ted DiBiase claimed to have signed him to a contract. It turned out to be Evil Undertaker, with the two clashing at that year's SummerSlam.

13.

Vince McMahon

The Undertaker and Vince McMahon have been at odds numerous times, beginning in 1998 and carrying on when Mr. McMahon's Corporation waged war with Undertaker's Ministry. Years later, The Chairman managed to defeat The Dead Man in a Buried Alive match at Survivor Series.

11.

Bret Hart

WWE Hall of Famer Bret Hart and The Undertaker had several matches over the years; they were on opposing teams in Taker's very first match. Perhaps the most definitive was their SummerSlam match in 1997 with The Phenom's WWF World Title on the line. The Hit Man won the Championship due to special referee Shawn Michaels.

9.

The Ultimate Warrior

The Undertaker's very first major rivalry was with WWE Hall of Famer The Ultimate Warrior, which began at a television taping the day after WrestleMania VII. Warrior was locked in an "airtight" casket by The Dead Man leading to a feud that was played out in months of live events, including the rarely seen Body Bag matches.

7.

Stone Cold Steve Austin

WWE Hall of Famer Stone Cold Steve Austin and The Undertaker often found themselves on the opposite side of the fence during their respective runs including a match at the Cold Day In Hell PPV in 1997 and a fan favorite vs. fan favorite match at SummerSlam in 1998, which Austin won via a relatively clean pinfall victory.

5.

Brock Lesnar

The Undertaker and Brock Lesnar had two major rivalries, with about a decade's time in between. The first time was in 2002, with Lesnar holding a victory over Taker in a Hell In A Cell match. And of course, at WrestleMania XXX, The Beast Incarnate was able to end Undertaker's 21-0 winning streak with a pinfall loss.

3.

Shawn Michaels

The Undertaker and WWE Hall of Famer Shawn Michaels have never seen eye to eye, beginning with the very first Hell In A Cell Match, which Michaels managed to win due to outside interference. The two also engaged in back-to-back classics at WrestleManias 25 and 26, including Michaels's final match as an active wrestler.

1.

Kane

Who else has caused The Undertaker more sleepless nights than his own flesh and blood Kane? After attacking him in his 1997 debut, Kane haunted The Dead Man for some time, and the pair had two different WrestleMania encounters! Although they've teamed up as The Brothers of Destruction, The Big Red Machine upset The Phenom in a World Title match as recently as 2010 after leaving him lying in a "vegetative state." Sounds like more than a typical sibling rivalry to us...

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Wrestling Merchandise and Memories podca
Wrestling Historian Mike Rickard