It’s still hard to believe we might indeed have witnessed the Undertaker’s last match. The Phenom has been taking souls and digging holes for the better part of three decades. And while he usually has no issue taking down his targets, there have been a few men who stood toe-to-toe with the Deadman over the years.
So, as we celebrate The Dead Man’s remarkable career, let’s take a look back at his greatest rivals, and The Undertaker’s 10 greatest opponents.
10. Randy Orton
Long before he became the Viper, Randy Orton was the “Legend Killer”, and he soon found himself in the crosshairs of the biggest legend of them all — the Undertaker. Orton and Taker fought each other throughout most of 2005, engaged in a heated rivalry. Both men thrived on playing mind games with the other and in many people’s eyes, this is where the maniacal Randy Orton of today originated from. As far as their matches are concerned — whether it was their first clash at WrestleMania 21, their excellent match on SmackDown or their violent Hell In A Cell match, the Undertaker and Orton never failed to steal the show. And this feud helped take Orton’s career to unimaginable heights.
9. CM Punk
CM Punk could have a great rivalry with just about anyone. While he crossed paths with the Phenom in 2009’s controversial Montreal Screwjob 2.0 — which culminated with the Deadman winning his seventh World Championship — it was their 2013 rivalry that immortalized this feud. Punk’s mocking of the Deadman due to the real-life death the late great Paul Bearer led to a clash between the two superstars at WrestleMania 29. And despite being 48 at the time, the Phenom stood toe-to-toe with his younger opponent as the two managed to steal the show in an incredible match. It showed how well they worked together, highlighting all that we weren’t allowed to see in their unfairly short 2009 matches.
From a storyline standpoint, these two always excelled together, but as far as their matches are concerned — WrestleMania 29 is untouchable.
8. Edge
Edge and the Undertaker’s vicious SmackDown rivalry lasted for over a year, beginning in May 2007 and eventually culminating in August 2008. But thanks to the excellent storytelling and incredible matches, it never grew old.
With a year-long build, they finally met at WrestleMania 24 in an amazing main event match. They would go on to co-main event four more PPVs and brought their A-game every time. The Rated R Superstar pushed the Undertaker further than anyone, and this always came across in their matches. Their pure unadulterated hatred for each was felt in every strike, Spear and Tombstone. And the epic Hell In A Cell match was the perfect ending to this heated rivalry. They don’t make feuds like this anymore.
7. Batista
On paper, many believed that this simply wouldn’t work. But when the Undertaker and Batista finally met in the ring for the World Championship at WrestleMania 23, they ended up stealing the show. Their first meeting told an incredible story as Batista desperately threw everything at the Phenom, who would eventually power back and win the title. But they went on to prove that it wasn’t just a fluke — it was followed by four epic rematches throughout 2007, including a Last Man Standing Match, Steel Cage match and Hell In A Cell. Each time these beasts got together in the ring, they told a remarkable story — simply the two biggest dogs in the yard wanted supremacy — and the World Heavyweight Championship. The drama, the emotion and the hard-hitting blows were always there in what was easily 2007’s greatest storyline.
While the two men did engage in a new rivalry in 2009, the storyline and match quality never lived up to their first five incredible outings — all of which did wonders for both of their careers and was a huge part of SmackDown’s success.
6. Brock Lesnar
Whether they were battling in 2002 or 2015, the Deadman and the Beast always found new ways to thrill us with their violent altercations. The feud that brewed for over a decade began with the Big Evil iteration of the Undertaker taking on the young beast Lesnar in vicious Hell In A Cell and Biker Chain matches. But it would be reignited in 2014 when the world watched Lesnar break the Deadman’s undefeated streak. Ironically that match was the pair’s only dud — due to the Undertaker suffering a concussion during the match — but it paved the way for two far superior matches the following year.
The grizzled, angry veteran returned for vengeance — and got it — in a hard-fought brawl at SummerSlam 2015 before the feud finally culminated in a barbaric Hell In A Cell match later that year — the rematch which arguably exceeded the original from 13 years prior.
These two were always happy to destroy each other, and it almost always made for edge-of-seat moments and great matches.
5. Triple H
The “cerebral assassin” has always loved to brawl, and nobody loves a fight better than the Undertaker. These two men battled on and off over the better part of 15 years and always produced high quality matches. Whether Triple H was begging the BikerTaker not to hurt him or promising to be the “one” to defeat the Deadman at WrestleMania, the two legends knew exactly how to keep us invested in their matches.
Of al their classic encounters, three were at WrestleMania — and the amazing thing is that their latter two (in 2011 and 2012) were arguably even better than their meeting a decade prior.
Their hard-hitting styles have always meshed well together, and made for great tension and drama in the ring during their many matches together. And let’s not forget that Triple H had to follow the two five-star classics with Shawn Michaels in the Undertaker’s WrestleMania Streak — and both times he delivered, proving that he wasn’t just a formidable foe, but that he too could take the Deadman’s WrestleMania matches to incredible heights.
4. Stone Cold Steve Austin
The rattlesnake and the Deadman were constant thorns in each other’s sides throughout the Attitude Era. Stone Cold Steve Austin headlined pay per views while the Undertaker was busy doing what he did best throughout the rest of the card. But it wouldn’t be long until the Deadman looked to reclaim his place at the top of the food chain and the animosity was unleashed. And when you put these two in the ring together — with the championship on the line — you were usually guaranteed a showstopper. No matter how many transformations the Phenom underwent between 1996 and 2002, his hatred for Austin always survived. Whether you prefer their epic brawl at SummerSlam in Madison Square Garden, their hellacious Buried Alive match or their underrated No Holds Barred match — an Austin vs. Taker match is guaranteed entertainment. And that’s the bottom line.
3. Mankind
If one superstar in WWE had the Undertaker’s number — it was Mankind. The maniacal superstar debuted by attacking the Deadman and somehow managed to prove he was even more sadistic than Taker himself. But his violent and deranged approach forced the Undertaker to adapt and in many ways, gave us the Deadman we know and love today. Mankind pushed the Phenom to become more aggressive, agile and aerial in the ring. And in doing so, we got countless classics from these two, including their Boiler Room Brawl and Buried Alive matches, and their infamous Hell In A Cell match in 1998 — a match we are destined to talk about forever.
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2. Shawn Michaels
They say your greatest rivals will push you beyond your greatest limits — and that’s exactly what the Heartbreak Kid and the Deadman did for each other. Shawn Michaels and the Undertaker are undoubtedly two of the greatest, so it’s no surprise that these two individuals are single-handedly responsible for five of the greatest matches in WWE history.
When Michaels accidentally struck the Phenom with a steel chair in 1997, he unleashed a feud that would fester for over a decade. The two met in the first ever Hell In A Cell match — a match that has gone down as one of the all-time greats. They would also meet in a singles match and a Casket match before their rivalry finally concluded. However, it was their meetings the following decade that would solidify this feud’s immortal presence.
Michaels and the Undertaker’s match at WrestleMania 25 is considered by many to be the greatest wrestling match of all time. With both of them in their 40s, they should have been well past their primes, but they proved any critic wrong and stole the show from performers half their age. And the best thing about it is that they managed to do it all again the following year. Main-eventing WrestleMania 26, the Undertaker put an end to the rivalry by ending Shawn Michaels’ career and closing this historic chapter of both mens’ legacies. Few opponents ever produced magic with the Undertaker like Michaels did.
1. Kane
Hell hath no fury like the Brothers of Destruction. Kane is easily one of WWE’s greatest creations and could rival The Undertaker at just about everything. The storyline which saw Paul Bearer bring him to WWE, and the subsequent feud he had with the Undertaker is undoubtedly the greatest piece of epic storytelling the company has ever done.
A gigantic mute and masked monster, Kane pushed the Undertaker well past his limits and their first meeting at WrestleMania XIV is the first real standout contest of the Deadman’s Streak. But it was their Inferno match a month later that immortalized the rivalry as one of WWE’s fieriest feuds.
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And while they united many times throughout their careers, they also reignited their feud many times — most notably in 1999, 2000, 2004 and 2010 but none were quite as ferocious as that initial rivalry.
For both men being such a considerable size, they shouldn’t have worked so well together, but they absolutely excelled whenever they were in the ring together. They brought out the best in each other and pushed each other to deliver great matches, while redefining the storytelling process. But more than anything, they added a great deal to each other’s legacies in what was quite possibly the greatest rivalry of all time.
Who do you think are The Undertaker’s greatest opponents of all-time? Let us know in the comment section below!
