5 'lasts' of The Undertaker's WWE career

Over the last two months, the WWE Universe has had unprecedented access to the life of the man known as Mark Calaway through the five-part docuseries 'Undertaker: The Last Ride'. The Undertaker was seen in a new avatar throughout this WWE Network special, chronicling the events of his career in the company.

Throughout the series though, The Phenom's retirement was a central agenda, which led to speculation that he could indeed call it quits soon. And after spending 30 years in WWE, The Undertaker finally did hang up his boots in the final chapter of The Last Ride with these words:

"At this point in my life, and in my career, I have no desire to get back in the ring. This time the cowboy really rides away."

The Undertaker indeed has nothing more left to achieve. He's accomplished various milestones while in the WWE and vowed millions worldwide. Taking the theme of his last few years in the company forward, let's take a look at a few of the 'lasts' from The Deadman's iconic career.

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#5 The Undertaker's last pay-per-view appearance in front of a live audience

The last time fans saw The Undertaker inside a WWE ring

The world as we know it has changed in 2020. Mass gatherings are a strict no-no and thus, we've been seeing WWE programming without fans in attendance since March this year.

Given that The Undertaker has had such an impact on fans worldwide, it's imperative to talk about the last time a live audience was able to witness the toll of the bell as The Phenom walked down the entrance ramp. It was at Super ShowDown 2020 in Saudi Arabia, where The Undertaker made his presence felt.

The Tuwaiq Trophy Gauntlet Match was on, and AJ Styles had just eliminated R-Truth with Rey Mysterio being the last entrant in the match. However, he was attacked by Karl Anderson & Luke Gallows. The Phenomenal One asked the ref to declare him the winner by forfeit but it was then that lightning struck.

The Undertaker attacked The OC backstage before making it out to the ring outside. He chokeslammed a flabbergasted Styles and pinned him to eventually win the Tuwaiq Trophy.

#4 The Undertaker's last title reign

The Undertaker's seventh world title

Such has been the stature of The Undertaker in WWE that he immediately becomes the USP of any show or pay-per-view that he's a part of. He has not needed to chase gold in the company to stay relevant and nothing highlights this more than the fact that his last title reign came more than a decade ago.

Back in 2009, a few months after having probably the best WrestleMania match in his career against Shawn Michaels, The Undertaker attacked CM Punk – who was the then World Heavyweight Champion – at SummerSlam.

This immediately set up a feud between the two and after a few controversial finishes, the duo faced off at Hell in a Cell in a titular match. The Phenom was able to get the better of Punk there and won the World Heavyweight Championship for the third time in his career.

The Phenom had successful title defenses against the likes of Punk, Batista, and Rey Mysterio on separate occasions but eventually dropped the title at Elimination Chamber 2010 to Chris Jericho after Shawn Michaels' interference. This, of course, led to the famous 'Streak vs Career' match at WrestleMania 26 which 'Taker won.

The Undertaker challenged for the title again that year when Kane was the champion but failed to re-capture the same.

#3 The Undertaker's last loss (singles and tag team)

Iconic!

The Undertaker has been taking it easy in recent years, wrestling only on limited occasions. He stepped foot inside a WWE ring the most times in the last five years in 2018. The Phenom was a part of five matches in total, including the special show at Madison Square Garden. However, it was also the year in which he suffered two consecutive losses, the final ones of his career.

The Undertaker squared off with Triple H in a no-disqualification match at WWE Super ShowDown in Melbourne, Australia. The fight was billed as "Last Time Ever" and also featured Kane and Shawn Michaels standing in the corners of the two men, respectively.

The encounter was nothing to write home about as The Game picked up the win. However, after the match, under the pretense of showing respect, the Brothers of Destruction attacked Triple H and HBK. This eventually resulted in a showdown between D-Generation X and the Brothers of Destruction at Crown Jewel with Michaels making his in-ring return after nine years.

The match was another letdown with all Superstars visibly suffering from ring rust but DX won the match by recreating an iconic moment. HBK delivered the Sweet Chin Music on Kane as he dallied into a Pedigree by The Game. Triple H then pinned The Big Red Machine as an exasperated Undertaker failed to interfere and the saga was brought to a close.

#2 The Undertaker's last Hell in a Cell match

One last time in his own backyard

The Undertaker has been a part of many stipulation matches throughout his long tenure in WWE. However, the one stipulation that has time and again added gleam to 'Taker's career and has also been referred to as The Deadman's own backyard is Hell in a Cell.

The Undertaker has had some of the most iconic moments of his WWE career during Hell in a Cell matches. Be it the time he threw Mankind off the roof of the cage into the announce table or his 'End of an Era' match against Triple H at WrestleMania 28, we've always seen The Phenom deliver inside the vicious steel structure.

The Undertaker's last outing inside Hell in a Cell saw him face off with Shane McMahon in what was the latter's first match in almost seven years. A returning Shane O'Mac wanted control of RAW but Vince McMahon said that he'll have to wrestle one person at one place with one stipulation for that.

The person turned out to be The Undertaker with the place being WrestleMania 32. And the stipulation was obviously Hell in a Cell. While the match wasn't one of 'Taker's greatest bouts ever, it did have one spot which was talked about for days.

Shane McMahon jumped off the roof of Hell in a Cell and while his intention was to hit The Deadman, the latter moved away and Shane exploded through the announce table. The Undertaker then carried Shane O'Mac to the ring, delivered a Tombstone Piledriver, and picked up the win.

#1 The Undertaker's last WrestleMania match

The last ride?

Of course this list had to come to an end with this. If you think about The Undertaker, you automatically think about 'The Streak' and all the fine matches that he's had at WrestleMania. This year though, the game changed. The stipulation of The Phenom's final match at the Grandest Stage of Them All was an unfamiliar one.

AJ Styles challenged The Undertaker to a Boneyard Match at WrestleMania 36 after weeks of directing personal barbs at him. He mentioned 'Taker's wife Michelle McCool and even referred to him by his real name.

The Undertaker still had his doubters following the trainwreck of a match against Goldberg, but once again, The Deadman rose from the ashes to prove to the world once again why he had survived in the company for three decades.

In a brilliant cinematic affair, The Phenom buried The Phenomenal One six feet deep to bring curtains to his last feud in the WWE and his last match at WrestleMania. The encounter had everything you could ask for. We saw 'Taker bring back the American Badass and Big Evil gimmicks, there was a lot of crude trash-talking, and then there were the masked druids as well.

The Undertaker enthralled fans once again, as he took care of business and rode away into the night on his bike one last time on WWE programming.