One of the all-time greats to walk through the doors in WWE is The Undertaker. Undertaker spent three decades in WWE before calling it quits at Survivor Series 2020. Moreover, the WWE Hall of Famer has been involved in some memorable marquee matches, and whilst he has generally won a lot of significant matches, Undertaker has lost some matches in one-on-one action by pinfall on pay-per-view.
It's always a shock when the Phenom is beaten by pinfall, especially when you least expect it. Many legends have managed to cover Undertaker for the win, but whilst, Mankind has two wins over Undertaker on a WWE pay-per-view, he hasn't done it by pinfall. The likes of Edge and Yokozuna have also beaten Undertaker in a singles match on PPV but not via pinfall. Nonetheless, to get a win over Undertaker isn't easy but some of the all-time greats have done it.
15 Hulk Hogan
The Undertaker defeated Hulk Hogan for the WWE Championship at Survivor Series 1991. Just six days later, the Hulkster was looking to reclaim the gold in a rematch at This Tuesday in Texas.
Undertaker was unbeaten in televised one-on-one matches, hoping his WWE Championship reign would continue. However, that failed to materialize with Hogan regaining the gold with a rollup to kickstart another WWE Championship reign.
14 Mabel
The 1995 King of the Ring tournament is arguably the worst in WWE history. Undertaker competed on a King of the Ring event for the first time, and he was up against Mabel in the quarterfinals. This wasn't a good wrestling match with Mabel not on Undertaker's level.
Undertaker had parts of the match under his control, but that changed when Kama Mustafa interfered. Mabel took advantage, and he upset Undertaker en route to winning the King of the Ring tournament. Remarkably, it was Undertaker's first singles loss by pinfall on a PPV in over three years.
13 Vader
The Undertaker had a dismal record at the Royal Rumble, and he was hoping to overturn his bad record at the 1997 Royal Rumble in his one-on-one match with Vader. Unfortunately, this match between the heavy hitters was underwhelming.
Undertaker's former manager Paul Bearer came down to ringside, and he had a closer look at the action. A Vader Bomb from the Mastodon was enough for him to pick up a huge win over Undertaker.
12 Bret Hart
There was a blockbuster main event between The Undertaker and Bret Hart at SummerSlam 1997 with the Deadman's WWE Championship up for grabs. Moreover, Shawn Michaels was the man in the middle as the special guest referee.
The match wasn't the greatest between the pair, but it was still an intriguing match. However, the Hitman wound up Michaels by spitting in his face, and a steel chair shot intended for Hart caught Undertaker in the face instead. Michaels reluctantly counted Undertaker's shoulders down and he handed his bitter rival, his fifth WWE Title reign.
11 Shawn Michaels
The Hell in a Cell match between The Undertaker and Shawn Michaels at Badd Blood: In Your House is a five-star epic. The winner would go on to face Bret Hart for the WWE Championship at Survivor Series 1997.
Michaels shed buckets of blood, and he was a beaten man. That was until Kane made his WWE debut, and he laid out his brother. Ultimately, HBK crawled across Undertaker to become the number one contender for the WWE Championship.
10 Steve Austin
Steve Austin and The Undertaker's matches failed to live up to the hype, but their clash over the WWE Championship at SummerSlam 1998 was their best match. The Texas Rattlesnake sustained a concussion, but that did not stop him from registering a clean win over Undertaker to retain the WWE Championship.
Austin had beaten Undertaker in rematches on pay-per-views down the line but not by pinfall for another three years. That all changed when Austin defeated Undertaker in another WWE Title match at Judgment Day, all thanks to outside interference from Triple H.
9 Kurt Angle
Another man who has registered a couple of wins over The Undertaker by way of pinfall on a WWE pay-per-view is Kurt Angle. At Survivor Series 2000, Kurt's brother Eric traded places with Kurt, which allowed Kurt to get back into the match, and he pulled Undertaker's tights en route to a successful WWE Championship defense.
Their encounter at No Way Out 2006 was one of the best matches that year. The wrestling was out of this world, and it went back and forth but by the skin of his teeth, Angle remained as World Heavyweight Champion.
8 The Rock
Similar to his chemistry with Steve Austin, The Undertaker and The Rock's chemistry was non-existent. Which is disappointing considering the caliber of the two former WWE Champions. They were on a collision course at No Way Out 2002.
The Phenom dropped his Hardcore Championship to Maven because of The Rock. Nonetheless, their match wasn't anything special but Rock earned a huge win over Undertaker.
7 Triple H
Two of the all-time greats in Triple H and The Undertaker were opponents at Insurrextion 2002. This was the final WWE PPV main event under the WWF banner. Their match was competitive, but it was the Cerebral Assassin who came out on top.
The Game had to wait another 16 years to replicate that feat after he sustained losses to The Undertaker in back-to-back WrestleMania encounters. Their final meeting at Super ShowDown 2018 in Australia saw Triple H overcome Undertaker once more.
6 Brock Lesnar
The rivalry between Brock Lesnar and The Undertaker is one of the most physical feuds that WWE has produced. Lesnar retained the WWE Championship against Undertaker at No Mercy 2002 in a brutal Hell in a Cell match. He followed it up with another win at No Mercy for the second year in succession in a Biker Chain match.
Lesnar's most shocking win over Undertaker took place at WrestleMania 30 when Lesnar unexpectedly broke Undertaker's 21-0 WrestleMania unbeaten streak. The final chapter of their rivalry saw Lesnar once again get the better of Undertaker at Hell in a Cell 2015.
5 Randy Orton
Randy Orton was looking to avenge his loss to The Undertaker at WrestleMania 21 in a rematch at SummerSlam 2005. Orton and Undertaker had good chemistry together, and Orton needed to bounce back here.
Undertaker was in control of proceedings, but Orton held his own by working on his knee throughout. Nevertheless, Orton earned a huge win over Undertaker, after his father Cowboy Bob interfered.
4 The Great Khali
WWE pushed The Great Khali in a huge way when he debuted in 2006. At Judgment Day, Khali took on The Undertaker, and the Phenom had faced the likes of Giant Gonzales in the past. However, Khali posed a new threat to Undertaker.
Khali systematically broke Undertaker down in a one-sided affair. It was one of Khali's best performances, and he nailed Undertaker with his patented chop and he finished him off with a big boot.
3 Batista
The feud between Batista and The Undertaker dominated SmackDown in 2007. The Animal was once again the World Heavyweight Champion, and he defended his title against Batista at Cyber Sunday with Steve Austin as the special guest referee.
This is an underrated match, and Batista registered a clean win over Undertaker in a successful title defense. Weeks later, they battled inside Hell in a Cell at Survivor Series, and Batista defeated the Deadman once again with Edge interfering.
2 Kane
Kane and The Undertaker reignited their feud for the final time in 2010, and the World Heavyweight Championship was involved this time around. Surprisingly, Kane had never beaten Undertaker on pay-per-view, but that changed at Night of Champions in their No Holds Barred match.
The brothers were once again on a collision course inside Hell in a Cell. Paul Bearer was in Undertaker's corner to start with but he betrayed Undertaker. The Devil's Favorite Demon chokeslammed his brother to pick up his second straight win over Undertaker to retain the World Heavyweight Championship.
1 Roman Reigns
The Undertaker was up against Roman Reigns at WrestleMania 33, and several wrestling fans disliked Roman Reigns as they felt that he was being shoved down their throats. Unfortunately, Undertaker was far from his best in this bout.
This was an atrocious match, and it was sad to see Undertaker not operating at the peak of his powers. Nevertheless, the Big Dog handed Undertaker just his second defeat on the Grandest Stage of Them All.