An icon of World Wrestling Entertainment, The Undertaker enjoyed a 30-year-long career with the company, wrestling from 1990 all the way to 2020. A top star and a huge attraction, ‘Taker didn’t lose a whole lot of matches during his later years, as he’d become one of those wrestlers who’d only show up on special occasions like WrestleMania.
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But “The Demon of Death Valley” did lose matches, albeit sporadically over the last 12 years of his career. Without further ado, let’s take a look at the wrestlers who were able to directly defeat The Undertaker, either by winning a singles match or by beating him in multi-man affairs like the Elimination Chamber.
Updated on 27th April 2022 by Andrew Kelly:Up until his official retirement in 2020, in which he went out with a victory at WrestleMania 36, The Undertaker was a part-time performer for the better part of a decade in WWE, making his matches feeling special, and making it even more significant when he would pick up a loss. With him often appearing just for WrestleMania, it was hard to find many opportunities for him to actually lose, but WWE found ways to put some superstars over during the last ten years or so, though it didn’t come around too often. The Undertaker is one of the most protected names of all time, from his dominance to his character, with him only shedding kayfabe since he hung up his boots. Having a match with Taker was a big deal and beating him was even more of a rub. Since late 2008, November to be exact, only a select number of wrestlers have been given the distinction of defeating him, with that number tallying up to 13 lucky individuals who managed to secure a victory in the record books. Some of those came in straight up singles matches, clean as a whistle, some of which involved shenanigans, and some happened within tag team matches or others where Taker may not necessarily have been pinned, but he did officially lose.
12 * Shawn Michaels & Triple H (WWE Crown Jewel, 11/2/2018)
In a match which many want to be wiped from their memories, Shawn Michaels teamed up with Triple H in a DX reunion to battle The Brothers of Destruction at the Crown Jewel 2018 event in Saudi Arabia, which had dollar signs written all over it.
DX picked up the win after a long, uncomfortable slog of a match, which was filled with botches and mistakes, making it an almost laughable match. This wasn’t quite an example of Taker putting over some hot and new stars.
11 * The Shield (WWE Raw, 04/22/2013)
It is easier to lump Dean Ambrose & Seth Rollins within a singular entry, largely due to the fact that it was in the same match. In a rare match on Raw and Smackdown over the course of Undertaker’s part-time stint in WWE, he teamed up with Team Hell No to take on The Shield.
RELATED: The Shield's First 10 WWE Rivalries, Ranked From Worst To BestOn an episode of Raw taking place in London, England shortly after WrestleMania 29, The Shield defeated the face trio, which was yet another huge rub for three young stars on the rise. Taker would later wrestle Dean Ambrose in singles action, but The Deadman would win that match, only to be taken out and put through the announce table by The Shield, allowing them to ultimately stand tall.
10 Triple H (WWE Super Show-Down, 10/6/2018)
Triple H put on three great losing efforts against The Undertaker at WrestleMania 17, 27, and 28, but their last singles encounter would be a No Disqualification match at WWE’s Super Show-Down special in Australia. The bout was not well-received, as it was a slow-paced affair that lasted nearly half an hour, but Triple H would get the win thanks to help from Shawn Michaels and a sledgehammer.
This would lead to a tag team match as Trips and Shawn took on Kane and The Undertaker at Crown Jewel a month later in a famously reviled effort. DX would defeat The Brothers of Destruction at Crown Jewel when Triple H pinned Kane for the win.
9 Roman Reigns (WWE WrestleMania 33, 4/2/2017)
The main event of WrestleMania 33 had Roman Reigns taking on The Undertaker in a No Holds Barred affair that seemed slated to be ‘Taker’s retirement match, but the result ended up becoming one of the more disappointing ‘Mania headliners of recent years. Running over 20 minutes, the match got increasingly sloppy as it went on and the live crowd openly did not enjoy it. However, Reigns got the win here, becoming one of two men to defeat The Undertaker at WrestleMania.
8 Brock Lesnar (WWE WrestleMania 30, 4/6/2014 & WWE Hell In A Cell, 10/25/2015)
The other man to defeat The Undertaker at WrestleMania was Brock Lesnar, who shocked the world by putting away The Dead Man at WrestleMania 30. While some questioned the decision for Brock to be the guy who did it, it felt like a passing of the torch as Lesnar became WWE’s big monster attraction wrestler in the years following the event.
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A rivalry between the two would play out in 2015, with Undertaker winning their rematch at SummerSlam only to ultimately lose their rubber match at Hell in a Cell -- in the Cell, to boot.
7 Kane (WWE Night of Champions, 9/19/2010, WWE Hell in a Cell, 10/3/2010 & WWE Bragging Rights, 10/24/2010)
In 2010, The Undertaker went through his last major feud as an active competitor before becoming a special attraction in 2011, and it was appropriately against his kayfabe brother Kane. The Undertaker would challenge Kane for the World Heavyweight Title on three occasions in September and October of 2010, and Kane ended up winning every single time in a different stipulation match: first No Holds Barred, then Hell in a Cell, and finally a Buried Alive match. That last one at Bragging Rights would be ‘Taker’s last match before returning to the ring at WrestleMania 27 the following year.
6 Chris Jericho (WWE SmackDown, 2/12/2010 & WWE Elimination Chamber, 2/21/2010)
The Undertaker was set to defend his World Heavyweight Championship inside the Elimination Chamber in February 2010 and took on Chamber participant Chris Jericho in a non-title No DQ match over a week before the PPV, with Jericho scoring a surprising win. ‘Taker and Jericho would end up becoming the last two men in the chamber, but interference from Shawn Michaels would result in Jericho coming out of the Chamber with the World Title. Undertaker would then take on Shawn Michaels in their classic Streak vs. Career match at WrestleMania XXVI.
5 Randy Orton (WWE Monday Night Raw, 12/14/2009)
A mid-December 2009 Raw brought a “Superstar of the Year” tournament, wherein four wrestlers -- CM Punk, Randy Orton, The Undertaker, and John Cena -- all competed for the chance to win the 2009 Superstar of the Year Slammy Award rather than holding a vote. It was a weird tournament amounting to three short matches, including Randy Orton beating The Undertaker by countout in four minutes. The finals would come down to Orton vs. John Cena, with an ending most fans could guess in their sleep. In other words, Cena won.
4 CM Punk (WWE Breaking Point, 9/13/2009 & WWE SmackDown, 9/25/2009)
While CM Punk famously fell victim to The Streak at WrestleMania 29 in 2013, he did manage to score a huge win over The Undertaker back in 2009. It was in the main event of 2009’s Breaking Point that Punk defended his World Heavyweight Championship against ‘Taker in a submission match, which ended with yet another Montreal Screwjob riff as the bell suddenly rang while The Undertaker was stuck in the Anaconda Vise.
The two would clash in another match over a week later on SmackDown, this time with Punk winning via countout.
3 The Big Show (WWE SmackDown, 4/24/2009)
The Big Show spent so much of his recent WWE years as a guy who loses matches, making it surprising to find out that he actually has a win over The Undertaker. It was on an April episode of SmackDown in 2009 that Big Show took on Undertaker just before Show’s jump over to Raw. What resulted was a surprisingly substantial 14-minute singles match where Big Show came out on top in the end after punching ‘Taker so hard that it drew a ref stoppage.
2 Vladimir Kozlov (WWE SmackDown, 2/27/2009)
Likely the most surprising name to show up on this list, Vladimir Kozlov’s WWE run isn’t exactly well-regarded -- he had a great look but never really put on a great match -- but he does somehow have a win over The Undertaker.
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It happened on a late February 2009 SmackDown, days after both took part in the Elimination Chamber at No Way Out. There wasn’t even any cheating either, as Kozlov managed to score a surprise Powerslam for a three-count.
1 Jeff Hardy (SmackDown, 11/14/2008)
In the main event of this mid-November 2008 episode of SmackDown, Jeff Hardy and The Undertaker clashed in an Extreme Rules match. Late in their near-16-minute effort, The Big Show would interfere in the match, distracting The Undertaker’s attention enough for Hardy to take advantage, utilizing chair and ladder-based maneuvers to win the bout. This incident would result in ‘Taker putting away Big Show in a Casket Match at Survivor Series later that month.
