The Undertakers Best Matches

In the world of professional wrestling you can never take a star’s word when they retire. Ric Flair, Shawn Michaels, Mick Foley and Terry Funk are all names that supposedly hung up their boots just to put them back on again.

One man who seems to be retiring for the last decade is the Undertaker. Every year seems to be his last year. Then Wrestlemania comes around and the dead man shows up again. You’ll never hear me complain he is a childhood hero of mine. Plus, the man that got me into wrestling in the first place.

He seemed to bow out at Wrestlemania 33. After losing to Roman Reigns he symbolically left his hat, jacket and gloves in the ring. He even broke character and went to embrace his wife in the crowd. In that moment we didn’t see the Undertaker. We saw Mark Calaway the man behind the character.

It seemed perfect. Wrestlemania is where Undertaker made his name with his legendary undefeated streak. In front of over 75,000 adoring fans is where he will say goodbye.

Of course, he just kept coming back and back and back.

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Most of the returns were sad to watch for fans. With Undertakers body understandably just not what it once was. Father time waits for no man not even a dead one.

They weren’t all stinkers thankfully. He had a great showing in a tag team match with Roman Reigns at Extreme Rules in 2019. Along with a brilliant cinematic Boneyard Match against AJ Styles at this years Wrestlemania.

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Its now believed that match will be his last. WWE began to air a fantastic documentary series on the Undertaker called The Last Ride. It’s a fascinating look at the man himself and a joy for any fan. However, in the last episode Undertaker revealed he had “no desire to return to the ring.”

This seemed to be confirmed by WWE. They recently dedicated an episode of Smackdown as a tribute show to the Undertaker. With the announce team even saying multiple times on the show that his match against AJ Styles at Wrestlemania 36 was his last.

Already people are asking for one more match. Honestly, I would be happy to see such an icon walk away on his own terms. In the wrestling business its just hard to tell if someone will return or not. Especially when talking about the Undertaker who puts butts in seats with his name value.

Undertaker has been with the company since 1990. He has nothing else to prove. He has recently signed a 15-year contract with WWE. So, he will have fruitful comfortable employment for as long as he wants. Well deserved after all his years of loyal service to Vince McMahon.

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With all that been said now is a perfect time to look back. The Undertaker has had many classic matches over his 30-year WWE career. Which one is his best?

That’s what we will be talking about today. As we count down the best five matches of Undertakers WWE career.

Honourable Mentions – Randy Orton at Wrestlemania 21, CM Punk at Wrestlemania 29, Brock Lesnar at No Mercy 2002, Batista at Wrestlemania 23, Kurt Angle at No Way Out 2006, Triple H at Wrestlemania 27 & 28, Edge at Summerslam 2008, Kane at Wrestlemania 14 and Jeff Hardy at RAW 2002.

5. Undertaker vs Mankind (King of the Ring 1998)

This one isn’t here for the match quality but the legacy of the match. Undertaker and Mankind always fit perfectly when feuding against each other. This match showed the world how mad Mick Foley really is.

The Hell in a Cell match only debuted the year before, so the match was still fresh and new. Stunt wise this match set the bar and still hasn’t been beaten. Its still the most infamous match in the cell.

The biggest highlight been when Undertaker threw Mankind off the top of the structure and through an announcer desk. Followed by the amazing JR call “Good God almighty! Good God almighty! That killed him!”

The two mad men would find themselves back on top of the cell. Mankind would then take a chokeslam through the cage. Which wasn’t meant to happen. Mankind hit the ring hard below legitimately knocking himself out. Undertaker would even say years later he taught he was dead.

Then came a camera shot we will never forget. Mankind gets up smiling with one of his teeth lodged in his nose.

Thankfully, Undertaker would soon win the match. Bringing an end to the madness. Not the most technical match but a pure legendary spectacle. Once again proving how tough professional wrestlers really are. Still fake and phony is it?

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4. Undertaker vs Edge (Wrestlemania 24 2008)

Genuinely one of the most underrated Wrestlemania matches of all time. It won’t be in most peoples top five but I love this match. Edge put his World Heavyweight Championship on the line for this one.

As you can see by the honourable mentions Undertaker was on a Wrestlemania hot streak at this point. Edge was really proving himself as the top main event heel in WWE.

It was a classic Undertaker Wrestlemania match. With a slow start building into an epic battle. With both men busting out their big moves and big reversals.

Edge seemed to have an answer for everything. He hit a spear surely retaining his title and breaking Undertakers Wrestlemania undefeated streak. Undertaker locked in his Hells Gate submission from nowhere. We had a new World Heavyweight Champion. Undertaker went 16-0 at Wrestlemania.

An instant classic. Plus, a worthy main event to any Wrestlemania.

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3. Undertaker vs Shawn Michaels (Wrestlemania 26 2010)

When Undertaker showed up to Wrestlemania you knew to expect a stellar match.

This was a rematch from their match the year before. Spoiler alert we might see that one in a few minutes.

Shawn Michaels was desperate for one more crack at the dead man. So desperate he even put his career on the line. In what was an excellent build up. This one was billed as Career vs Streak.

This turned out to be one of the best Wrestlemania matches of all time. Certainly, the best retirement match in WWE history. These two always had unbelievable in ring chemistry together. Which you will come to find out.

This match featured multiple finishing move kick outs. With both men facial selling the disbelief perfectly each time.

Undertaker pulled out one of his best Tombstone Piledrivers of all time. Winning the match in the process. Michaels in ring career was over and Undertaker was still undefeated at Wrestlemania.

Now lets all forget about HBK returning at Crown Jewel in 2018.

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2. Undertaker vs Shawn Michaels (Badd Blood 1997)

Told you these two had amazing chemistry. Wrestlemania isn’t the only place you can find a classic between these two.

This was also the first ever Hell in a Cell match. While it wasn’t as chaotic as the previous one on our list. It was much better. It was 30 minutes of non-stop action. Giving everyone a feel for the dangerous nature of the demonic structure.

It was also during a time when both men were at their physical best. It really shows during this match.

HBK got battered in the cell. Showing that this really was Undertakers playground. With Shawn been covered in blood by the end. We see weapon shot after weapon shot.

Michaels even got stamped while dangling off the top of the cell. Sending him crashing through the announcer table below.

Just as Undertaker went for the win the lights go out. Out comes a debuting Kane. He rips the cell door off with his bare hands. Gives Undertaker a Tombstone Piledriver. Then drags a lifeless HBK on to Undertaker for the win.

An excellent match. Which gave us one of the best wrestling debuts of all time.

Classic Match: Undertaker vs. Shawn Michaels, Badd Blood: In Your ...

1. Undertaker vs Shawn Michaels (Wrestlemania 25 2009)

The HBK hattrick. Just something about these two that always produced magic. Let me tell you this one was magic.

It was the first time these two met at Wrestlemania. Both men could be known as Mr. Wrestlemania. With Michaels always delivering at the show of shows and Undertaker with his famous streak.

It was so good nobody remembers the very short two week build up to the match. When looking you would forget both men were in their 40s during this match. Along with the follow up next year.

Both men kicked out of finishing moves several times. Perfect exchanges and seamless reversals. Big move after big move for the occasion. With Undertaker eventually picking up the win.

Words will never do this one justice just go watch it if you haven’t. It rightfully won loads of Match of the Year awards. Even gave us the sequel we previously mentioned. Nothing was ever going to top this ever. It was simply perfect.

Not only is this the best Undertaker match ever. It’s the best Wrestlemania match ever. Plus, the best WWE match ever.

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