10 Best WWE Matches of The Undertaker

The Undertaker is a once in a lifetime superstar. He is the conscience of WWE, the gatekeeper of WWE and arguably, the greatest of all-time.

The Undertaker has had some of the greatest matches of all time and some of the most legendary feuds in the history with the like of Stone Cold Steve Austin, The Rock, Shawn Michaels, Triple H, Brock Lesnar, Batista and many more. He is without a doubt the greatest character in the history of professional wrestling and living proof of how a performer can stay through to their character.

The Undertaker has been taking souls and digging holes for over 28 years now and with rumors of the Deadman finally calling it a career in 2019, I think it's time we take a look at the top 10 best matches in the career of the phenom.

#10 The Undertaker vs. Kurt Angle - SmackDown September 4, 2003

Taking place on the September fourth episode of SmackDown in 2003, The Undertaker challenged Kurt Angle for the WWE Championship, and it was one hell of a showdown.

This was the best match SmackDown had by this point in 2003 and one of the best matches of the entire year. The Undertaker himself later went onto calling it one of his all-time favourite matches and called Kurt one of the greatest wrestlers he had ever been in the ring with.

The match saw several finishing moves, reversals, fast-paced action, both men pull out everything they have to try and beat each other. The last five minutes or so are epic, with Angle desperately trying to make The Undertaker tap out to the Ankle Lock, and The Undertaker trying his best to survive, and take Angle down. The final moment saw Taker setting up Kurt for another Last Ride before Brock Lesnar ruined the ending by attacking both men.

This was easily the best match The Undertaker had in 2003 and the last and one of the best matches of his American Badass persona.

#9 The Undertaker vs. Jeff Hardy - RAW July 1st, 2002

"Climb the ladder, kid! Make yourself famous!"

The Undertaker in a ladder match. the mere idea of it sounded strange but boy did it blow everyone's expectations.

Going into this one, no one believed Jeff Hardy stood a chance, especially with the match only being made on short notice and having no build up.

Amazingly, there were so many moments during the match where you actually believed Jeff really did stand a chance.

There were so many death-defying spots and Jeff really shined as what may happen if he were to go solo.

The Undertaker played his part very well and helped make Jeff look like a future megastar. Taker would Chokeslam Jeff off the ladder before taking the WWE Championship down.

We then got a truly awesome moment where Jeff took to the mic to proclaim that he was still standing. Taker hit the ring prepared to further beat him down, before raising his arm in respect.

#8 The Undertaker vs. Kurt Angle vs. The Rock - Vengeance 2002

Now, this was a war!

After a mostly dismal 2001, The Undertaker was on top of his game in 2002, and this was one of his shining moments. The Rock was also at the peak of his career, while Kurt Angle was just always this damn good.

The audience was red hot for this, and rightly so. Some crazy cool moments including The Rock hitting The Undertaker with a Chokeslam, Rock uses Angle`s Anklelock until Angle reverses it until Angle hits a Rock Bottom.

Everyone is hitting their own finishers left and right with each man kicking out at every pinfall attempt. Rock pins Angle after a Rock Bottom for the three count and Taker's WWE Championship.

WWE and wrestling as a whole have had so many excellent Triple Threat matches over the years, but this one may just the best of all time.

#7 The Undertaker vs. Brock Lesnar - No Mercy 2002

The Undertaker losing his legendary WrestleMania streak to Brock Lesnar at WrestleMania 30 in 2014 might be what everyone will always remember from the matches and feud of these two, but this Hell in A Cell bloodbath will always be their finest encounter.

Where before Taker took Shawn Michaels, Mankind and Rikishi outside of the Cell for moments that made those matches truly epic, Taker and Brock stayed inside for all near 30 minutes of this often underrated stunner.

The match was just pure violence. Both men were covered in blood long before the match ended, in fact, there was so much blood that even Paul Heyman, who was outside the Cell, bled like a stuffed pig. We have a lot of use from a steel chair, several power moves, and some near fall from the Chokeslam and Last Ride.

Much like Wrestlemania 30, Brock reverses an attempted Tombstone into an F-5 for the win. Brock and Taker would go at it again n another Hell in A Cell match 13 years later in 2015, but as great as that was, it still doesn't hold a candle to this gem.

#6 The Undertaker vs. Triple H - WrestleMania XXVIII

The end of an era.... Well, at the time it was — The end of an era

It was the end of an era! Well, until WWE Super Showdown 6 years later in 2018, but for all these years the Hell in A Cell match between Triple H and The Undertaker had been the original final match ever between them, and at the time it was a hell of a way to go out.

With the dream match of The Rock vs John Cena taking place in the main event, The Undertaker and Triple H went out there to steal the show, and that they did. Shawn Michaels volunteered his services as referee here, only adding to the drama. Everything about this encounter was simply electric.

The two battled it out for just over 30 minutes. They went back and forth, fought all over the Cell, use of the sledgehammer, several finishing moves, several near falls, Shawn Michaels gave Undertaker a Superkick leading to the Triple H Pedigree for another nearfall, which was one of the better nearfalls you will ever see.

When Undertaker kicked out, the arena became unglued. After another nearfall from another Tombstone, Taker beat Triple H senseless with a chair and has Triple H fought back and attempted to use his sledgehammer, Taker took it and hit him in the face with it.

With The Game on his knees, Undertaker picked him up and hit the Tombstone for the win.

#5 The Undertaker vs. Shawn Michaels - WrestleMania XXVI

An incredible end to an incredible career, at the time at least

Shawn Michaels, arguably the best in-ring performer in the history of professional wrestling would step in the ring to compete for what would be his last ever time... until WWE Crown Jewel 8 years later in 2018.

Just like the previous year, HBK and The Undertaker danced at WrestleMania in one of the best matches you will ever see and the best ever retirement match a wrestler has ever had. They really pulled out all the stops, and though their chemistry has always been phenomenal, the drama was incredible.

The Undertaker did a great job in looking like he believed he couldn't put the resilient showstopper away. The match featured Sweet Chin Music after Sweet Chin Music, dives, fantastic exchanges and much more. The Prince of Darkness delivered possibly his biggest and best Tombstone ever to put away the Heartbreak Kid.

#4 The Undertaker vs. Kurt Angle - No Way Out 2006

Then WWE World Heavyweight Champion Kurt Angle and The Undertaker had an instant classic in the main event of No Way Out 2006, easily the best match of the year and one of the best match of either man's careers.

Almost every time Kurt and The Undertaker got in the ring together, they created magic, so it was no surprise that this match was yet another instant classic. One thing that was really great about this match was that despite a size difference and Taker being very dominant in recent years, Kurt was treated as Taker's equal, and the two had a show-stopping affair where at no point did Kurt look like he would go down easy.

The two went back and forth, several reversals, Kurt hit the Angle Slam and Ankle Lock to no avail, Taker hit the Chokeslam and other vintage Deadman moves but failed to win. At one point it looked like Kurt would take in a countout victory over the Deadman after an Angle Slam through the announcer's table, but stops the referee from doing so.

The end of the match came when Kurt countered the Triangle Choke into a bridge pin for the victory. We had a cool respect moment from Taker after the match as he handed Kurt the World title.

#3 The Undertaker vs. Shawn Michaels - Badd Blood 1997

WWE WrestleMania 25 in 2009 wasn't the first time that Shawn Michaels and The Undertaker had a 10/10 epic encounter.

They feuded in 1997 through early 1998 with many good matches, but the one that stands out the most is their clash at Badd Blood 1997, which also happened to be the first ever Hell in A Cell match. It was half an hour of a flat-out action-packed bloodbath.

Everything here was just so perfect. While Michaels did get a lot of offence and moves in, he also took one of the biggest beatings in history, probably only being beaten by The Undertaker's destruction on Mankind the following year in the same match. Shawn looked like he had walked out of heel when all was said and done, he was covered in that much blood.

We have some very violent chair shots that you would never see in today's world, as well as Michaels hitting Taker with a piledriver onto the steel steps. They make it outside the Cell and to the top where we have some scary moments that eventually lead to Taker stamping Michaels off the top to the table below.

As Michaels is lying helpless, looking like he is already dead, Taker signals for the Tombstone before his 'brother' Kane makes his historic debut and hits Taker with a Tombstone of his own, allowing Shawn to make the cover for the win. An absolutely excellent match.

#2 The Undertaker vs. Mankind - King of The Ring 1998

Perhaps one of the most, if not the most famous match in the history of WWE and all of wrestling, The Undertaker and Mick Foley went to hell and back at the King of The Ring event in 1998.

The second ever Hell in A Cell match on pay-per-view, this one just outperforms The Undertaker and Shawn Michaels from Badd Blood, just for the sheer violence upgrade. The two start things off at the very top of the cell. As they trade blows, the cage roof starts to give way as they battle over to the side. Then, to the amazement and horror to everyone watching, both at home and in the Igloo in Pittsburgh, Pennsylvania, Taker hurls Mankind off the top of the cell, and he falls 20 ft through the Spanish announcer's table below.

The thud of Mankind's landing is sickening. Although the bell didn't ring, Jim Ross says the match will be coming to an end as Foley is being stretchered away, but instead, he hops off and climbs back up on top of the cell, only to be met with a Chokeslam from The Undertaker, as Foley drops another near 20 ft, this time through the Cell roof to the ring below.

Amazingly, Mankind continues the match. The battle goes on for another near 15 minutes, where Foley amazingly got some offence in and even managed to make Taker bleed thanks to help from the cell. The sick carnage wasn't over yet however as Mankind retrieves a bag of thumbtacks from under the ring. He empties them in a quarter of the ring and tries to knock Undertaker into them. After nearly hitting each other into them, Taker backdrops him onto the tacks, and then delivers a Chokeslam, again on the tacks, followed by a Tombstone for The Undertaker to take it on home.

Easily the most violent match in WWE history.

#1 The Undertaker Shawn Michaels - WrestleMania XXV

This match might just be the best wrestling match we will ever see. Having put on a 5-star classic once before, back in the first ever Hell in A Cell match at Bad Blood 1997, Shawn Michaels and The Undertaker managed to have an even better, more incredible match at WrestleMania 25.

Everyone knew Shawn was going to lose, especially since the match had a build up of only about two weeks, but during the match itself, you really believed it was possible Michaels could pull off a win. They kicked out of each other's finishing moves more than once, with perfect exchanges and reversals everywhere, an incredible dive from the ring by Taker and even some of the best frustrated facial expressions you will ever see in a match.

This match rightfully won several Match of The Year awards and even spawned a sequel, to be Shawn Michaels' final WWE match (for 8 years) the following year.

There was no doubt in anyone's mind that after this match, no one else could go out in a 5-star match with Shawn Michaels other than The Undertaker. The WrestleMania 26 match between them was excellent, but this match at WrestleMania 25 was just perfect.