The Undertaker is one of the most dominant and feared wrestlers in WWE history. From a booking perspective, he was constantly for three decades one of the most consistently booked wrestlers. He was one of the biggest winners throughout multiple different eras of WWE, and it was rare to ever see him lose at all – let alone cleanly at that.
However, there were times in which The Undertaker lost throughout his career, and it took fans by complete surprise. These losses mentioned are either huge upsets or moments in which fans assumed an Undertaker win was inevitable – even against top names.
10 The Great Khali – Judgment Day 2006
The Undertaker didn’t lose clean all too often in his WWE career, and to see someone with such a reputation of being an unstoppable monster being beaten so decisively was a huge shock.
The Great Khali was new to the scene in 2006, and he found himself going up against The Undertaker in his first major feud. WWE wanted to make Khali the next big monster heel, and to do so they had him destroy The Undertaker here.
9 Kane – Hell In A Cell 2010
The Undertaker losing to Kane isn’t the most shocking result ever, but the context matters. Kane’s heel rise in 2010 saw him attack The Undertaker and rule him out of action for months, eventually leading to his return and look for revenge.
Fans predicted that the story would lead to Undertaker winning the World Heavyweight Championship, especially after Kane beat them in their first match. Their rematch was inside Hell in a Cell, but a Paul Bearer turn led to Kane shockingly picking up a second straight win over his brother.
8 Edge – One Night Stand 2008
The Undertaker’s feud with Edge in 2007 and 2008 was iconic, but the Undertaker got the better of his opponent numerous times. However, at One Night Stand 2008 he suffered a hugely surprising defeat.
This was extra shocking due to the fact The Undertaker’s career was on the line, and given that he was getting on with age and some wrestlers choose to step away at certain points, there was a brief belief that he may be gone for good. Seeing him take a ridiculously huge bump through tables added to the surprising nature of this too.
7 Big Show – No Mercy 2008
WWE had tried periodically to make Big Show a dominant monster heel, and in 2008 it became time for it to happen again. When it comes to the WWE pecking order, Undertaker had been above The Big Show for a long time, so to see such a one-sided assault and victory was a complete shock here.
Big Show got the advantage early on and just took The Deadman apart, winning the match by referee stoppage after two massive punches to the head. To see Undertaker lose so decisively was a surprise, especially in 2008, and especially at the hands of Big Show.
6 Tito Santana – WWF On Telenico 1991
Early into The Undertaker’s career, losses came few and far between. In fact, this match against Tito Santana was his first ever pinfall loss in the company, which makes it among the most surprising of his entire run.
This match came in Spain, leading to there being a thunderous crowd who supported Santana. His win may not have been clean, using the urn to help him score the win, but the result was still a massive shock either way.
5 Shawn Michaels – Bad Blood 1997
Shawn Michaels defeated The Undertaker numerous times, but it was the way he won which made the 1997 Bad Blood win incredibly surprising. In the first ever Hell in a Cell match, Kane made his shocking debut, attacking The Undertaker and leading to Michaels winning.
The way this match went down makes it one of the most surprising results in The Undertaker’s career, even if it wasn’t the most surprising on paper.
4 Edge – SmackDown 2007
Back in 2007, the concept of the Money in the Bank was still a very new one, so to see a cash-in take place was a complete shock. Amidst a match with Batista, Mark Henry arrived to attack The Undertaker, and this led to Edge taking advantage of the situation.
It took fans by surprise and seeing Edge win the World Heavyweight Championship wasn’t something anyone expected to see when the show began.
3 Vladimir Kozlov – SmackDown 2009
A few of the shocking upsets on this list have seen a monster heel somehow manage to topple The Undertaker, and the same happened again at the start of 2009 on an episode of SmackDown when new resident monster Vladimir Kozlov got a clean win.
Kozlov was already cold by this point, which made it even more of a surprise when he scored the victory, putting him in contention to face The Undertaker at WrestleMania for a shot at the illustrious streak.
2 Maven – SmackDown 2002
Maven was one of The Undertaker’s bogey opponents over the course of his career. The Tough Enough upstart would score one of the most shocking eliminations in Royal Rumble history by dumping out The Undertaker, and this was followed up by an upset victory in singles action too.
They would battle over the Hardcore Championship on SmackDown, and even though it wasn’t all clean, seeing Maven get the upper hand again was a surprise for sure.
1 Brock Lesnar – WrestleMania 30
Not only was Brock Lesnar’s WrestleMania 30 victory the most shocking result in The Undertaker’s career, it may very well be the most shocking in all of WWE history.
Lesnar ended Undertaker’s WrestleMania undefeated streak in a moment no one would ever have thought to happen, and once the three count was completed you could hear a pin drop.