the undertaker randy orton

The Undertaker’s Greatest WWE Feuds

The Undertaker is one of the most legendary stars in WWE history. Throughout his 30-year career, “The Phenom” stacked up numerous accolades, as he won seven world titles. But beyond championships, his true legacy is his character and the memorable stories he was part of. “The Deadman” was involved in some all-time classic feuds that will go down in WWE history.

Here are The Undertaker’s five greatest feuds and opponents:

Undertaker Kane WWE
Image Credit: WWE


The Undertaker’s storyline with Kane is not only one of the defining parts of his career; it is one of the most renowned programs in WWE history. Kane debuted at In Your House: Bad Blood in 1997, where he cost Undertaker his Hell in a Cell match with Shawn Michaels. They eventually clashed at WrestleMania XIV, and they waged war in the first-ever Inferno Match.

The duo eventually joined forces to form the Brothers of Destruction, but “The Deadman” later turned on Kane. The brothers eventually teamed up again and dominated the tag team division. They renewed their rivalry in 2003, as Kane cost Undertaker his Buried Alive match aganst Mr. McMahon. Undertaker beat Kane in a WrestleMania rematch in 2004 before they reformed the Brothers of Destruction in 2006.

Kane ad The Undertaker reignited their feud in 2010, as Kane was revealed as the attacker that put Undertaker in a vegetative state. They battled on a number of occasions, including a Hell in a Cell match where Paul Bearer turned on Undertaker and helped Kane win. Kane also beat Undertaker in a Buried Alive match, which marked their final singles encounter. They continued to team up occasionally over the years until Undertaker retired in 2020.

Factor in all of the mythos, which centered around Undertaker burning his parents’ funeral home and scarring a young Kane, and you have the recipe for a rivalry that will likely never be topped.

Image Credit: WWE

Shawn Michaels

The Undertaker’s rivalry with Michaels was unique in that there are two distinct parts, and both of them are legendary. In 1997, Michaels and The Undertaker were two of WWE’s top stars. Michaels cost “The Deadman” his match with Bret Hart at SummerSlam 1997, which set the stage for their buzzworthy clash at In Your House: Ground Zero.

That bout ended in a no contest. The rivals met again in the first Hell in a Cell match at Bad Blood 1997. The arrival of Kane helped Michaels score the win. Michaels later defeated Undertaker in a Casket Match at Royal Rumble 1998, bringing the first version of their feud to an end.

Over a decade later, Michaels and Undertaker renewed their rivalry. Now of the most respected veterans in the business, they faced off at WrestleMania 25 and delivered one of the best matches of all time. The Undertaker won, and they ran it back a year later in the high-stakes Streak vs. Career match. “The Phenom” won that one and sent Michaels into retirement. Their two WrestleMania matches remain among the best bouts in WWE history.

Image Credit: WWE

Mankind (Mick Foley)

Mankind (Mick Foley) and The Undertaker will always be linked together. That’s the clearest sign of a truly iconic rivalry. Mankind started feuding with Undertaker upon his WWE debut in 1996. They made history on multiple occasions, as the duo competed in the first-ever Boiler Room Brawl Match and the first Buried Alive Match. They later clashed for the WWF Championship, but the high point of this story came in 1998.

In one of the most legendary matches in WWE history, Mankind and The Undertaker clashed in a Hell in a Cell match at King of the Ring 1998. The battle remains one of the most brutal bouts WWE fans have ever seen, as “The Phenom” threw Foley off the top of the cell and down through a broadcast table below. Jim Ross delivered the classic lines “Good God almighty! They’ve killed him!” and “As God as my witness, he is broken in half!”, which turned the moment into an all-timer.

The Undertaker also chokeslammed Foley through the ceiling of the cell and sent him crashing to the mat. “The Phenom” won, but Foley’s incredible toughness turned him into an absolute legend. The match is even more special with the knowledge that The Undertaker was working with a fractured ankle, which highlights his own dedication to the business.

Undertaker Edge WWE
Image Credit: WWE


Other feuds may spring to mind faster, but The Undertaker’s rivalry with Edge was a fun ride that spanned the better part of a year. “The Rated-R Superstar” unforgettably attacked The Undertaker during his Hell in a Cell match against Batista at WWE Survivor Series 2007. Edge later beat both men to win the gold, but the legend would earn a rematch at WrestleMania 24. There, The Undertaker scored the win and took the title back.

“The Phenom” then beat Edge at WWE Backlash and Judgment Day before “The Rated-R Superstar” defeated him in a Tables, Ladders, and Chairs match at One Night Stand. After some time away, The Undertaker came back in pursuit of revenge. The blowoff match came at WWE SummerSlam, where The Undertaker sent Edge to hell by slamming him through the ring, at which point the collapsed part of the canvas burst into flames. Talk about a cinematic ending!

Years later, it was revealed that Edge was at least considered to be the one who broke The Undertaker’s WrestleMania streak. In hindsight, that would made this rivalry even more remarkable. Regardless, the two stars carried SmackDown’s main event scene for months and kept it engaging the entire time. The feud also helped cement Edge’s status as a genuine main-eventer near the end of his first WWE run.

Undertaker Randy Orton WWE
Image Credit: WWE

Randy Orton

Perhaps more so than any other feud on this list, this rivalry was a clash of generations. In 2005, The Undertaker was still somewhat in his prime, at least comparatively speaking. However, he had already been established for a top guy for well over a decade. Meanwhile, Orton was still new to the main-event level, and his first world title run fizzled out.

However, his “Legend Killer” gimmick gave him a boost, and The Undertaker was the perfect adversary. Orton took out Jake “The Snake’ Roberts” as he continued his path towards “The Phenom.” The storyline continued to heat up as The Undertaker amped up his supernatural antics, and “Cowboy” Bob Orton, Randy’s father, got involved.

Undertaker ultimately won the WrestleMania match and continued his streak. That being said, Orton was a made man after he worked with the veteran and held his own with him. The WrestleMania bout was also one of the legend’s strongest outings, compared to some of his other contests at “The Showcase of the Immortals.”