Back in 2013, Digital Spy did a piece where they named the Undertaker the greatest wrestler in WWE history. Anyone who has followed his journey since his debut will agree with that statement. He has achieved a lot throughout his career and to this day he is still giving fans matches that they will always remember.
Like any wrestler though, The Undertaker has had some matches that have put a damper in his legacy. For example, his loss to Roman Reigns, his absurd match with Shane McMahon, that horrible match he had with Goldberg, and of course, his matches with Brock Lesnar.
At the end of the day though, he could wrestler in a wheelchair, and fans would still cheer for him. Here are 15 of the most iconic moments in The Undertaker’s career.
15 His WWF Debut During Survivor Series In 1990
We are all wondering when The Undertaker will retire, but does anyone remember when he debuted at the 1990 Survivor Series PPV as the mystery man for Ted DiBiase’s Million Dollar team? Right off the bat, he got everyone’s attention and after dishing out a Tombstone Piledriver, and then eliminating Dusty Rhodes, he proved he was there to invoke misery in everyone and could care less about the titles and such.
14 Winning His First-Ever WrestleMania Match Against Jimmy “Supafly” Snuka At Wrestlemania 7 In 1991
The Undertaker has a lot of great moments throughout his career, but his top must be his match with Jimmy ‘Supafly’ Snuka at WrestleMania 7. The Undertaker was still a rookie at that time and had only been working for the company for a few months. His win over Snuka is what began “The Streak,” which ended with him winning 21 victories in a row.
13 Winning His First-Ever WWF Championship Against Hulk Hogan At The 1991 Survivor Series
Another top moment in Undertaker’s career is when he won his first WWF Championship at a Survivor Series PPV back in 1991. As stated above, The Undertaker wasn’t much for titles, which is why he hasn’t won many during his career. After beating Hulk Hogan though, he not only won his first-ever title but became the then-youngest WWF Champion.
12 When Paul Bearer Left Him To Join Mankind, Causing Him To Lose At SummerSlam In 1996
Like any big-time wrestler, The Undertaker had some help to boost his success every now and again. One of his biggest helpers was the late Paul Bearer, who played a major part in his gimmick early on. At one point though in 1996, Paul turned on the Undertaker and joined Mankind instead, causing Undertaker to lose at the first-ever Boiler Room match at SummerSlam.
11 Going Face-To-Face With Kane For The First Time During Badd Blood: In Your House In 1997
Not only do a lot of fans think that this was the best Hell in a Cell match ever, but the thrill of seeing watch The Undertaker practically demolish Shawn Michael doesn’t even compare to when Kane made his appearance. Kane’s distraction gave Shawn enough time to gather what little strength he had and pick up the win against Undertaker.
10 When He Threw Mankind Off Of Hell In A Cell During King Of The Ring In 1998
This is not only one of the greatest matches of Undertaker’s career, but also one of Mankind’s. During the match, these two phenomenal superstars found their way fighting on top of the cage. What ended the match though is when Undertaker grabbed Mankind by the shirt and tights and literally threw him off the top without hesitation and down on the announcer tables below.
9 The Ladder Match For The Undisputed Championship With Jeff Hardy That Took Him To His Limit On Monday Night Raw In 2002
This ladder match between Jeff Hardy and The Undertaker might have premiered on Monday Night Raw, but it was a match fit for a PPV such as WrestleMania. Jeff truly brought Undertaker to his limit and beyond in this match. In the end, Undertaker retained his WWE Undisputed Championship and even raised Jeff’s hand in respect for his courage and how hard he fought.
8 Winning His First Royal Rumble In 2007
The Undertaker won his first-ever WrestleMania match a few months after he debuted and went on to win 20 more in a row. When it comes to the Royal Rumble though, he was not as lucky. In fact, he didn’t win his first match until 2007 when he entered at the number 30 spot. Eliminating three people, he went on to WrestleMania to win his first World Heavyweight Championship against Batista.
7 Defeating Shawn Michaels For The First Time At WrestleMania 25 In 2009
When Undertaker faced Shawn Michaels for the first time at WrestleMania, he had been already been on a 17-win streak. Many fans held their breath as these two iconic superstars battled it out, not knowing who would come out victorious. In the end, though, Undertaker added another notch to his WrestleMania streak.
6 ….Then Going On To Retire Shawn Michaels At WrestleMania 26 In 2010
After his loss to The Undertaker at WrestleMania 25, Shawn Michaels bet his entire career that he could end the streak at WrestleMania 26. It was an epic match between two superstars and in the end, The Undertaker would keep his streak alive and end up retiring Shawn for eight long years. Shawn would later team up with Triple H to face Kane and The Undertaker during the Saudi Arabia PPV in 2018.
5 Defeating Triple H In A Hell In A Cell Match To End An Era At WrestleMania 28 In 2012
After Shawn Michaels failed to end the Undertaker’s streak, Triple H decided to step up to the plate. First facing him at WrestleMania 27 in a No Holds Barred match, the two went on to face off again at WrestleMania 28 in 2012, this time with Shawn Michaels as a Special Guest Referee though. In the end, it was a memorable match that ended with The Undertaker winning and a hug between greats.
4 Paying His Respects To The Late Paul Bearer During The WWE Hall Of Fame In 2013
Paul Bearer was an icon who helped legends such as The Undertaker, Kane and Mankind become such a terrifying force in the WWE. Many believe that he deserved to be inducted into the WWE Hall of Fame while he was still alive. Sadly, WWE didn’t do this until after his passing in 2013, which also means he didn’t get to see the heartfelt tribute that The Undertaker did for him on Monday Night Raw.
3 Winning His Match Against CM Punk, Which Ended Up Being His Last Winning Streak Match, At WrestleMania 29 In 2013
There have been a few WrestleMania matches throughout The Undertaker’s career that fans weren’t sure would either add to his streak or finally end it. His match with CM Punk at WrestleMania 29 was one of those matches. For years, these two were at each other’s throats and their hatred only intensified for their WrestleMania match. Luckily though, Undertaker pulled through for yet another win though.
2 Defeating John Cena At WrestleMania 34 In 2018
During the road to WrestleMania 34 though, John Cena spent weeks trying to goad him into another match. Finally, when it looked like Cena would be spending WrestleMania as part of the audience, The Undertaker returned and in a matter of minutes, proved to everyone that he was alive and not ready to hang it up just yet.
1 Burying AJ Styles Alive During A Boneyard Match At WrestleMania 36 In 2020
WrestleMania 36 wasn’t a WrestleMania that we are used to. Thanks to the pandemic due to the Covid-19 virus, this WrestleMania took place in an empty arena. With or without a crowd though, The Undertaker once again proved why he is the King of WrestleMania by proving to everyone he may be old and a bit slower, but he still can kick some butt. The match ended with Styles being buried alive.