The Undertaker's Biggest Losses

The Undertaker is unquestionably one of the greatest wrestlers of all time. Undertaker's WWE career spanned three decades, and his longevity in the company was unrivaled. Undertaker had a legendary career that saw him win seven WWE World Championships and he boasted a 21-0 unbeaten streak at WrestleMania that lasted for 23 years.

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The Undertaker had many legendary opponents throughout his career, but fans missed out on these potential amazing showdowns.

The Phenom was largely protected throughout his WWE career, but he wasn't immune from losing wrestling matches. Some of his losses in his career were huge, whether it be a championship match or a grudge match. Registering a win over the Deadman is a fantastic achievement and not a lot of wrestlers can say that they have beaten The Undertaker.

10 Hulk Hogan Ended The Undertaker's Maiden WWE Championship Reign

The Undertaker's First WWE Championship Reign Lasted Just Six Days

Event	This Tuesday in Texas 1991
Match Length	13:09
Match Type	WWE Championship match
Finish	Hulk Hogan defeated The Undertaker via pinfall to win the WWE Championship

The Undertaker defeated Hulk Hogan at Survivor Series 1991 to become the youngest WWE Champion in history at 26. It was a shocking moment, but six days later, Undertaker defended his newly won WWE Championship against Hulk Hogan in a rematch at This Tuesday in Texas.

Undertaker and the Hulkster had an average match, but just like their Survivor Series encounter there was repeated outside interference. Undertaker and Paul Bearer's plan backfired, and Hogan reclaimed the WWE Championship with Undertaker's reign lasting just six days and he wouldn't hold the WWE Title again for five-and-a-half years.

9 Edge Sends The Undertaker Packing For A Short While

The Deadman Is Banished From WWE

Event	One Night Stand 2008
Match Length	23:50
Match Type	TLC match for the vacant World Heavyweight Championship
Finish	Edge defeated The Undertaker by retrieving the World Heavyweight Championship

The rivalry between Edge and The Undertaker was a solid feud that was on and off in 2007 and 2008. Their encounter at One Night Stand 2008 had a lot riding on it as Undertaker would be banished from WWE if he failed to beat Edge in a TLC match for the vacant World Heavyweight Championship.

This was Undertaker's first TLC match in the Rated-R Superstar's specialty. Undertaker had some bright spells in the match, but La Familia was a distraction, Edge recovered after he was put through the tables, and pushed the Deadman off the ladder to clinch the World Heavyweight Championship with Undertaker banished from WWE until Vickie Guerrero halted it and he returned to face Edge at SummerSlam 2008.

8 The Undertaker Loses Another Casket Match At The Royal Rumble

Kane Costs The Undertaker The WWE Championship

Event	Royal Rumble 1998
Match Length	20:37
Match Type	Casket match for the WWE Championship
Finish	Shawn Michaels defeated The Undertaker to retain the WWE Championship

The 1998 Royal Rumble featured the only one-on-one World Championship match between The Undertaker and Shawn Michaels. It was a casket match for the Heartbreak Kid's WWE Championship, and Undertaker was seeking his third WWE Championship reign.

This match is notable for Michaels sustaining a near career-ending back injury after his back caught the edge of the casket. They had arguably the greatest casket match in WWE history, and it was a missed opportunity for Undertaker to walk into WrestleMania 14 as the reigning WWE Champion. His brother Kane interfered and he cleaned out the house, but it was a ruse as he attacked Undertaker with Michaels and DX taking advantage of the situation with the Heartbreak Kid retaining the WWE Championship.

7 Kurt Angle Narrowly Sees Off The Undertaker In An Epic

The Olympic Gold Medalist And The Deadman Had A WrestleMania-Worthy Match

Event	No Way Out 2006
Match Length	29:38
Match Type	World Heavyweight Championship match
Finish	Kurt Angle defeated The Undertaker via pinfall to retain the World Heavyweight Championship

The World Heavyweight Championship match between Kurt Angle and The Undertaker was one of the greatest World Title matches in WWE history. Fans were mesmerized by what they were witnessing and this match easily could have headlined WrestleMania 22.

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While he never strayed from his singlet, Kurt Angle's look is still legendary and provided fans with plenty of memorable attires!

The pendulum swung back and forth in a match that fans could not call. It was a war of attrition of pure drama and the in-ring action on show was out of this world. Undertaker was close to capturing the World Heavyweight Championship but Angle escaped with his title by the skin of his teeth.

6 Brock Lesnar Cements His Dominance As The Next Big Thing

Lesnar Beats Undertaker Cleanly Inside Hell In A Cell

Event	No Mercy 2002
Match Length	27:18
Match Type	Hell in a Cell match for the WWE Championship
Finish	Brock Lesnar defeated The Undertaker via pinfall to retain the WWE Championship

Brock Lesnar had a huge test in the early stages of his maiden WWE Championship reign as he defended his title against The Undertaker inside Hell in a Cell at No Mercy 2002. Lesnar and Undertaker knocked it out of the park in one heck of a bout.

It was a bloodbath, and Undertaker masterfully sold his broken hand. Both men were determined to leave the event as the WWE Champion, and Lesnar defeated Undertaker cleanly to remain as WWE Champion which was Undertaker's second loss in a one-on-one Hell in a Cell match.

5 "That's Gotta Be Kane!"

Undertaker Misses Out The Chance To Become The Number One Contender For The WWE Championship

Event	Badd Blood: In Your House 1997
Match Length	30:00
Match Type	Hell in a Cell match to determine the Number one contender for the WWE Championship
Finish	Shawn Michaels defeated The Undertaker via pinfall

Arguably, the greatest Hell in a Cell match in WWE history was Shawn Michaels and The Undertaker's battle with the winner becoming the number one contender for Bret Hart's WWE Championship at Survivor Series 1997. They had a five-star instant classic with Michaels and Undertaker battering each other from pillar to post.

The Heartbreak Kid crashed and burned through the broadcast table and he wore the proverbial crimson mask. Undertaker nailed HBK with an earth-shattering chair shot, and he was closing in on victory but he was face-to-face with Kane who made his WWE debut. Kane executed the Tombstone on Undertaker, and Michaels prevailed with Undertaker unable to edge one step closer to the title he was screwed out of.

4 The Undertaker Suffers Another Devasting Loss Inside Hell In A Cell

Edge Returned And Disguised As A Cameraman

Event	Survivor Series 2007
Match Length	21:24
Match Type	Hell in a Cell match for the World Heavyweight Championship
Finish	Batista defeated The Undertaker via pinfall to retain the World Heavyweight Championship

The Undertaker and Batista were inseparable in 2007 as they collided in some epic World Heavyweight Championship matches. Their clash at Survivor Series inside Hell in a Cell was the decider to determine the outright winner in their exceptional feud.

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There have been several World Heavyweight Championship matches at WWE Survivor Series, but they have ranged in quality!

Batista and Undertaker stole the show in an outstanding Hell in a Cell match with the Animal bleeding profusely. Undertaker almost recaptured the World Heavyweight Championship but Edge returned in disguise as a cameraman and he assaulted Undertaker with Batista taking advantage and he retained the World Heavyweight Championship in a devastating defeat for the Deadman.

3 Bret Hart Receives An Unlikely Assist To Win The WWE Championship

The Heartbreak Kid Accidentally Hits Undertaker With A Steel Chair

Event	SummerSlam 1997
Match Length	28:09
Match Type	WWE Championship match with Shawn Michaels as the special guest referee
Finish	Bret Hart defeated The Undertaker via pinfall to win the WWE Championship

One of the biggest main events in the history of SummerSlam featured The Undertaker and Bret Hart slugging it out over the WWE Championship. There was a caveat as Shawn Michaels oversaw proceedings as the special guest referee.

This match didn't live up to the hype as parts of the action were slow and methodical. Nevertheless, the drama intensified when Bret Hart provoked Michaels by spitting in his face and Michaels took exception to that and he swang for Hart but he accidentally caught Undertaker. The Deadman's second WWE Championship reign was over when HBK reluctantly counted his shoulders down.

2 The Undertaker And Steve Austin Battle On The Highway To Hell

The Deadman Was Unable To Win Back The WWE Championship

Event	SummerSlam 1998
Match Length	20:52
Match Type	WWE Championship match
Finish	Steve Austin defeated The Undertaker via pinfall to retain the WWE Championship

12 months after dropping the WWE Championship to Bret Hart, The Undertaker was once again involved in a WWE Championship match in the main event of SummerSlam. Austin and Undertaker were two of the all-time greats in the Attitude Era, and this was arguably their best match against each other.

The Deadman had a good outing here, and he pushed the reigning WWE Champion to his limit. Kane interfered but Undertaker instructed him to head back to the locker room. There was a table bump with Austin knocked out, but he beat Undertaker cleanly with a Stunner to continue his WWE Championship reign.

1 Brock Lesnar Shocks The World By Ending The Undertaker's WrestleMania Streak

The Undertaker's 21-0 WrestleMania Unbeaten Streak Is Over

Event	WrestleMania 30
Match Length	25:12
Match Type	Singles match
Finish	Brock Lesnar defeated The Undertaker via pinfall

The Undertaker's WrestleMania streak garnered a lot of interest and it was as big as some World Championship matches at WrestleMania - that's how important the streak was. Undertaker squared off with Brock Lesnar at WrestleMania 30 and it was a foregone conclusion to many that Undertaker would prevail.

Lesnar and Undertaker wrestled several times in the past, but no one was prepared for what happened when Lesnar hit Undertaker with the F-5. Undertaker was defeated handing him his first WrestleMania loss in the process with Undertaker going from 21-0 at WrestleMania to 21-1 with the crowd in a hushed silence and disbelief.