The Undertaker's Top 30 Moments

Mark Freitas
BarnBurner Sports Writer


Saturday, November 21, 2020

Growing up, I had a lot of favourite wrestlers. I had lots to choose from, from The Rock, Stone Cold Steve Austin, Triple H, Chris Jericho Kane. But the one who was my number one favourite was The Undertaker. There was something about him that just pulled me in. Coming up on November 22nd tomorrow night. WWE will be having its annual Survivor Series pay-per-view. But this year it will mark the 30th anniversary of the debut of The Undertaker. They will be celebrating his career and The Undertaker will be having his final farewell. So, I figured I would do a top 30 moments/feuds of The Undertaker’s career. Let’s get started.


30. The Undertaker’s debut (1990)


Kicking off, this list at number 30 is The Undertaker’s debut. The Undertaker debuted at the 1990 Survivor Series show on November 22nd, 1990. Being the final member of Ted DiBiase's team. DiBiase introduced The Undertaker to the ring being accompanied by Brother Love. Everyone in the arena had a look of shock on their face because they had never seen anyone like this before in the world of wrestling. Besides his debut, the other highlight of this match was Koko B. Ware becoming the first of many victims to fall to the Tombstone Piledrive. Ever since then The Deadman has buried lots of souls.


 29. Undertaker winning his first WWE Championship (1991)


One year after his debut at the 1991 Survivor Series, The Undertaker faced off against Hulk Hogan for the WWE Championship. Going into this match it was promoted as the gravest challenge for Hulk Hogan. This match escalated The Undertaker in his young career. Regardless of the way he won the match with help of Ric Flair it was still big because at that time Hulk Hogan was the biggest name in professional wrestling and to beat Hogan for the belt after only being there for one year, not many men can say that they have done it.


28. Undertaker vs. Jeff Hardy for the Undisputed Title in a Ladder Match (2002)


On the July 1st, 2002 edition of RAW the main event of the night was Jeff Hardy vs. Undertaker in a ladder match for the Undisputed Title. This match is one of my favourites because both men put on a great match and because of The Undertaker, this match helped Jeff Hardy for his career. It had lots of great spots and even though Taker had never been in a ladder match before he did a great job. I loved the big chokeslam he delivered off the ladder to Hardy and he retained his championship. But the big part of this match was after the bell as Hardy grabbed the mic and told Taker he is still standing and Undertaker went back to the ring, as it looked like he was going to lay another beat down on Hardy he gave him respect and it planned the seed to a face turn.


 27. The Undertaker Crucifies Stone Cold on RAW (1998)


On the December 7th, 1998 edition of Monday Night Raw. The main event of the night was a tag-team match with Stone Cold Steve Austin and Mankind vs. The Rock and The Undertaker. After the match, Austin received chair shots to the head. The Undertaker then carried Stone Cold up the ramp, where his ministry and druids were waiting for him while they brought out his symbol. Taker placed Austin down on top of his symbol the druids then tied Stone Cold to it. The symbol was lifted with Austin on it and The Undertaker doing his signature pose. Leaving an iconic photo that people remember. This segment iconic that even religious were not happy about and it kept the WWE in the headline news for weeks.


26. Undertaker winning the Royal Rumble (2007)


2007, was a big year for The Undertaker as he closed out 2006 with his feud with MR. Kennedy. Going into January of 07 he wasn’t in a feud yet with anybody, so heading into the Royal Rumble it was going to plant seeds. The Great Khail entered the match at number 28 and he began to dominate this match. Khali was eliminating men left, right and center. It looked like he wasn’t going to be stopped, that was until we got the countdown to see who would be number 30. The clock hit zero, the buzzer went off and we heard the famous “gong” go off. The Undertaker entered the ring as the last entry no one at the time entered at number 30 and won the match. Taker brought the fight to Khail, he wasn’t backing down. Taker laid big punches to Khail knocking him back to the ropes and clotheslining him over to eliminate him. Undertaker then wasted no time as he eliminated MVP. It was then down to the final four men Undertaker, Edge, Randy Orton and Shawn Michaels. As Undertaker turned his focus to Edge, MVP came back into the ring with a chair but was stopped by the referee. Randy Orton then grabbed the chair and laid out Undertaker.


Edge and Orton then worked on The Undertaker, hitting him with more chair shots and busting him open.


As he was down, Shawn Michaels saved Taker eliminating both Randy Orton and Edge. It was now down to these two legends Shawn Michaels and The Undertaker winner goes to Wrestlemania. They stared down at each other. Undertaker signalled Michaels to come at him. 


For the six minutes these men had with each other it was a classic. Both men went back and forth. The crowd was going wild, HBK and Taker went to the top rope Shawn won that battle as he followed up with his famous elbow from the top rope. He then went to hit Undertaker with a Sweet Chin Music but got caught into a Chokeslam by The Undertaker. Taker signalled for the Tombstone, but Shawn countered and hit a Sweet Chin Music out of nowhere. Both men got up Taker used the ropes to get up and Michaels looked to take advantage by hitting another superkick on Taker but this time to knock him over the ropes similar to how he eliminated Diesel. As he went for the kick Undertaker caught him and tossed over the ropes. 


The Undertaker won his first Royal Rumble match. This was the start to a great year for The Undertaker as he had memorable storylines with Edge, Batista and Mark Henry.


25. The start of The Streak (1991)


Heading into Wrestlemania 7 at the Joe Louis Arena in Detroit. it would be the Undertaker’s first Wrestlemania match. The Deadman took on “Superfly” Jimmy Snuka. Since this was early in Taker’s career his matches started slowly paced and as Undertaker said in his Last Ride documentary, they would pick up unexpectedly. Taker dominated this match and in the blink of an eye, he hit a big flying clothesline. Snuka tried to get the offence in but it did not work on The Deadman. Snuka hit a headbutt he then tried to follow up with a slingshot only to get caught in midair. After Taker caught Snuka he turned it into a Tombstone Piledriver, and Jimmy Snuka was the first of many men to fall victim to The Undertaker at Wrestlemania.


24. The first-ever Casket Match (1992)


In 1992, the WWE debuted a new match it would be called a “Casket Match”. Going into Summerslam 1992 at Wembley Stadium, The Undertaker took on “The Ugandan Giant” Kamala. The Undertaker entered in style as he came out on the back of a Hurst. What makes it memorable was Undertaker’s entrance and the fact that this was the first-ever Casket Match. 

 Both men battled it out in a short but fun match and in the end, The Undertaker came out on top with the win and putting the final nail in the coffin for Kamala, ending their feud.


23. Undertaker vs. Mankind (1996-1998)


In 1996, Undertaker began a long and historic rivalry with the crazy and deranged Mankind their first match took place at the King of the Ring on June 23, 1996, in Milwaukee Wisconsin. Mankind drew first blood at the start of this amazing rivalry as he picked up the first win. The second match between these two legends was the first-ever Boiler Room Brawl at Summerslam. This match is most famous for Paul Bearer turning heel on The Undertaker by hitting him in the head with the urn and helping Mankind to the victory.


At in Your House: Buried Alive, these men went at it in another first-time match and this match was a Buried Alive Match. In this heavy-hitting match, The Undertaker got the win, but in the end, he was buried alive by Mankind, The Executioner and Paul Bearer with the help of other superstars. This match was memorable for it’s an amazing shot of The Undertaker’s hand coming out of the grave signalling that he is still alive.


The Undertaker did not stay Buried Alive for long, as the fourth match with Mankind took place at Survivor Series. The Undertaker made his entrance by coming down from the rafters looking like a bat and he debuted a new all-black look. Paul Bearer was put in a cage that was lifted above the ring and if Taker won, he would get five minutes alone with Paul Bearer.


Undertaker won the match but did not get the chance to get his hands-on Bearer and The Executioner stepped in.


Mankind and Undertaker’s rivalry cooled off for a bit as Taker had a mini-feud with Executioner. Undertaker then had his eyes set on the WWE Championship, at Wrestlemania 13 he defeated Psycho Sid to win the championship.


Undertaker’s first title defence was against Mankind in match five between the two at In Your House: Revenge of the Taker. Mankind wanted to hurt Undertaker and take away the championship. Leading up to the match Mankind hit Undertaker in the face with a fireball. The Undertaker successfully retained his title at the show after he hit Mankind with the Tombstone and after the match, he lit Paul Bearer’s face on fire planting the seeds for his story with Kane.


After both men went on different things one year later. Their rivalry was ignited again in 1998 after Mankind cost The Undertaker a shot at the WWE Championship. To settle the score it was decided that they would face each other inside a Hell In A Cell. This match was crazy from the start as the match started on top of the cell. The Undertaker threw Mankind off of the cell crashing him through the announce table. Foley was stretchered off, but he came back for more.


They continued to battle and The Undertaker Choke Slammed Mankind through the cell to the ring. This caused Mankind to get his tooth jammed through his nose, as well as getting knocked out during the match. This match had everything. It had storytelling, hardcore wrestling and realism. The Undertaker got the win after Choke Slamming Mankind through thumbtacks and following that with a Tombstone. This was the sixth and final time that these men take on each other in a pay per view match.


This match will go down as one of the greatest Hell in A Cell matches ever and as well as one of the most controversial and brutal matches in the history of wrestling.


After this match, they would have two more singles matches against each other on RAW, but they were noting really as one ended in DQ and the other in a count-out.


To me, this rivalry ended at King of the Ring 98 and it will forever be one of the greatest rivals The Undertaker has ever had.


 22. The Undertaker returns at the Royal Rumble (2006)


The 2006 Royal Rumble show ended with Kurt Angle retaining his World Heavyweight Championship against Mark Henry. But what stood out to fans is what happened after the match.


The Undertaker’s gong went off and the crowd went nuts. The Undertaker came out on a horse and signalled to Kurt Angle that he was going for his World Championship. Taker then raised his hands in the air and brought them down using his “powers” to cause a lightning strike to hit the ring and it collapsed with Kurt inside. This was the first step to their mini-feud.


21. A five-star classic match against Kurt Angle at No Way Out (2006)


After his return at the Royal Rumble Undertaker made it clear he was coming for Kurt Angle’s World Heavyweight Championship. The match was set, Kurt Angle told Undertaker that he would plan on breaking Taker’s ankle peace’s. While Taker planned to make Angle rest in peace.


For the 31:21, that this match was it was amazing. This match should have taken place at Wrestlemania 22. From the start, it was such a fast-paced match and both men put on a fantastic wrestling match. It was back and forth from the get-go. You didn’t know who was going to win this match. This match is just perfect It was the best match of that year in the WWE.


Even though Taker lost this match it was one of his greatest matches ever. It is just a shame that this match did not happen at Wrestlemania, because if it did, it would have been the main event and it could have been the best way to end the streak. Kurt Angle had the right amount of wrestling and credibility to do so at that time. But this match is one of my favourite Undertaker matches.


20. The Undertaker vows to not Rest in Peace (1994)


At the 1994 Royal Rumble, Undertaker took on Yokozuna in a casket match. Yokozuna won the match with the help of a bunch of other wrestlers. As they stuffed Undertaker into the casket and wheeled him away the casket began to smoke and the lights when out and the gong hit.


We then see The Undertaker on the video screen in the arena of Taker inside the casket. He awakes and says, “the spirit of The Undertaker lives within the soul of all mankind the internal flame of life that cannot be extinguished the origin of which cannot be explained the answers lies in the ever-lasting spirit soon all mankind will witness the rebirth of The Undertaker”. Undertaker then says, “I will not rest in peace”. After that, The Undertaker then ascended to the rafters. He would not be seen again until later that year at Summerslam where he took on the fake Undertaker.


19. Undertaker turns heel on RAW in (2001)


On November 26, 2001, episode of RAW Mr. McMahon planned for Stone Cold Steve Austin to kiss his butt, but instead Stone Cold whipped him with his belt. After the show came back from the commercial Jim Ross was laughing at what just happened to Mr. McMahon, Kurt Angle who was out there with him noticed JR was laughing he and Mr. McMahon dragged him over the announce table and threw him in the ring so he can kiss Vince’s butt. Right when JR was about to be forced to kiss Vince’s butt, The Undertaker came out to save him.


Taker then got on the mic and said he has been there for a long time. He mentioned he has seen guys come and go such as Hogan, Bret, Warrior, Piper and Michaels. Undertaker said they all kissed Mr. McMahon’s butt, but the one who did the most was him. Taker asks JR if he was going to do it, JR responded by saying no and unexpectedly Undertaker asked JR if it was because he was better than him? 


The Undertaker then punched JR in the face and forced him to kiss McMahon’s butt. Taker had turned heel unexpectedly. The best part of this segment was seeing the fan's faces in the background when it happened because you can see their Deadman Walking signs being lowered down as they were surprised.


Undertaker would go on to be a heel for one year, he then turned face again in the summer of 2002.



18. Winning the Undisputed Championship against Hulk Hogan at Judgement Day (2002)


After Undertaker turned heel, he became one of the top bad guys in the company from late 2001 to the middle of 2002. Undertaker would on to win the Hardcore Championship from Rob Van Dam at Vengeance 2001.


Going into 2002 The Undertaker feuded for a bit with The Hardy Boyz, he gave the last ride to Jeff Hardy off the stage and even tossed Lita off of the stage as well.


At the 2002 Royal Rumble, The Undertaker made quick work of the Hardy’s as he eliminated them. The next entry was Tough Enough winner Maven. Maven would eliminate Undertaker by dropkicking him over the top rope. What came next was Maven’s funeral as Taker brutally assaulted Maven after that hitting with a chair and tossing him into a popcorn machine.


Maven would beat Undertaker for the Hardcore Championship on an episode of SmackDown with a little help from The Rock.


The Undertaker and The Rock had a small feud. They would have a match at No Way Out where The Rock won the match. 


Taker then feuded with Ric Flair and faced him at Wrestlemania 18. After this Undertaker had his eyes set on becoming Undisputed Champion. He would have a number one contender match against Stone Cold at Backlash. Taker got the win at Backlash. On the same night, Hulk Hogan took on Triple for the Undisputed Championship. Hogan won the belt because of Undertaker coming down and hitting Triple H with a chair. After Hogan won at Backlash the main event was set at Judgement Day Hulk Hogan vs. The Undertaker for the Undisputed Championship.


The buildup to the match was fun as Hogan stole Taker’s bike and Undertaker even hog-tying Hogan to the back of his bike and dragging him around the arena.


The Undertaker would defeat Hogan at Judgement Day after getting some help from Mr. McMahon and capitalizing with a Choke Slam becoming a four-time WWE Champion.


Taker would hold onto the belt until July after he would lose it in a triple threat at Vengeance to The Rock.


17. Choke Slamming Rikishi off of the Hell in a Cell at Armageddon (2000)


At Armageddon 2000 the main event of the night was a six-man Hell in a Cell match between Undertaker, The Rock, Stone Cold Steve Austin, Triple H, Kurt Angle and Rikishi. Long story short during the buildup for this match Mr. McMahon was against it he did everything in his power for it not to happen (storyline-wise).


So, during the match, he brought out a pickup truck with a chain hook to it and was going to tear down the cell. The cell door got removed and as McMahon got ready to do that to the rest of the cage Commissioner Mick Foley came out and got McMahon dragged out by security.


The fight ended up on the outside of the cell and eventually on top. This is where the chaos went crazy as Stone Cold gave a stunner to Triple H on the top of the cage. But the crazy part was when The Undertaker Choke Slammed Rikishi off of the cell and onto the bed of the truck that was left there by Mr. McMahon. Although Taker didn’t win the match, he won the spot of the night. This match has a memorable photo/video of Undertaker laughing and doing his classic eye roll with his lounge sticking out.


16. The first-ever Brothers of Destruction Entrance (1998)


On August 24, 1998, history in the making happened as The Undertaker and Kane walked side by side together down to the ring after months of battling each other.


During this segment, Paul Bearer came down to the ring, as he tried to win Kane back to his side. It did not work as The Undertaker laid a beatdown on Bearer and Kane turned his back as it happened.


Mankind came down to the ring, it looked like he was going to save Paul Bearer, but entered the ring and turned his and accepted a butt-kicking from Kane and The Undertaker. Undertaker and Kane delivered an amazing spike Tombstone to Mankind.


15. Undertaker vs. Stone Cold Steve Austin Summerslam (1998)


In my opinion, this is one of the best Summerslam main events ever. The buildup to this match was great as you didn’t know what to expect. At this pay-per-view Undertaker vs. Stone Cold was promoted as “The Highway to Hell”. 


After re watching this match, it’s got everything wrestling fans like it was a well-paced match and both men got 50/50 offence in. My favourite part from this match was Undertaker’s leg drop from the top rope to the announce table hitting Austin.


Kane came out during the match, but Undertaker told him to go backstage as he wanted the match to be a fair fight and have it only one on one.


Stone Cold won the match by hitting Taker with the Stone-Cold Stunner. After this, their rivalry continued, but out of all of their matches, this one is the best. It will go down as one of the best Undertaker matches in his career.


14. Undertaker vs. AJ Styles Boneyard Match Wrestlemania 36 (2020)


In an interesting year that 2020 has been. Going into Wrestlemania 36 was going to be interesting because we did not know what to expect.


Undertaker’s feud with AJ Styles all began at WWE Super Showdown in February of this year and that feels like ages ago. But this all came to be when AJ Styles declared himself the winner of the Tuwaiq Trophy at Super Showdown when Gallows and Anderson took out his final opponent Rey Mysterio in this gauntlet match. After AJ said that we cut backstage to Gallows and Anderson on the ground and we see somebody walk by and that somebody is The Undertaker.


Taker makes his entrance to the ring. He enters the ring and the ref signals for the bell so this match can start. AJ tried to make a run at Taker, but he got caught and he received a chokeslam Undertaker defeated AJ in 10 seconds he would be the winner of the Tuwaiq Trophy.


We would not see Undertaker for a couple of weeks. AJ Styles would tease Undertaker and the fans during his match with Aleister Black because when he pinned Black, he crossed his arms in the pinfall just like Undertaker.


At the Elimination Chamber pay-per-view AJ Styles took on Alester Black in a No DQ match Gallows and Anderson would get involved. They were setting Black up for the Phenomenal Forearm and when AJ was about to make his jump the lights when out and a gong went off. It was The Undertaker he had Gallows and Anderson by the throats he let them go and caught AJ in midair and gave Styles another chokeslam. Undertaker would cost Styles the match and Black got the win.


The next night on RAW AJ called out Undertaker and challenged him to a match at Wrestlemania. AJ would go on to say that Taker is a broken-down old man and says he longer sees Undertaker as this monster or Phenom anymore all he sees is just Mark Calaway. AJ then talked about Taker’s wife Michelle McCool saying that she is going to run him to the ground and AJ would help her.


The next week on RAW we got a contract signing between the two. Styles did not come down to the ring. But an angry Undertaker did. AJ who was backstage signed the contract and sent Gallows and Anderson to bring to Undertaker and they did. Undertaker beat up both of them and signed the contract.


Two weeks later on RAW AJ announced that their match would be a Boneyard match which is a Buried Alive Match. On the final RAW before Wrestlemania, we got a different type of an Undertaker promo. This wasn’t Undertaker talking it was Mark Calaway I loved this promo because it felt like Big Evil talking with a mix of The Deadman characters. Taker told AJ “try me, I’ll make you famous”. Taker would go to say that he would be bringing an unholy trinity with him to Wrestlemania and that he would make Styles “rest in peace”.


We now head into the match and it was cool because it was shot cinematically, and it felt different. AJ Styles showed up to the Boneyard in a Hurst coming out of a casket with the help of Undertaker’s druids. 


Undertaker made his entrance next riding down the road on his motorcycle with Metallica’s ”Now That We’re Dead” playing in the background. This was awesome Undertaker because Taker was a mix of himself, The Deadman and Big Evil all in one. 


This match was a slugfest and to me, it was fun because it had wrestling, entertainment and enjoyment. Undertaker would win the match after he gave AJ a chokeslam off of the roof of the barn. He then followed it up by kicking Styles in the face into the grave and burying him alive. Undertaker raised his fist in the air with pyro going off and his symbol showing in the background and he would ride off into the night.


If this was his final match it was the perfect way to retire The Undertaker character fittingly.


13. Brothers of Destruction vs. The Wyatt Family Survivor Series (2015)


At Fast Lane 2015, it seemed like The Undertaker was going to return. Taker’s druids came down to the ring, rolling down a casket, the casket opened and inside of it was Bray Wyatt and he called out The Undertaker.

For weeks he was doing this until he got a response from The Deadman on the final RAW before Wrestlemania 31. Undertaker made his return at the show. This match was good for what it was and both men put on an enjoyable match. Taker looked healthy which was the most important part. Undertaker won the match, and we would not see him again until the summer of 2015.


Undertaker faced Brock Lesnar in a Hell in a Cell match at the Hell in a Cell pay-per-view. After losing the match and going to war with Brock, Taker received a standing ovation from the crowd, but it was cut short by The Wyatt Family who came down and beatdown Undertaker. Following the beatdown, they carried him out.


The next night on RAW Kane was scheduled to have a match, but it did not happen as The Wyatt Family came down again and beat-up Kane and carried him to the back as well.


Weeks went on and we did not hear or see anything from the brothers until the November 9th, 2015, episode of RAW from London England. Bray Wyatt cut a promo saying that he had Kane and Undertaker’s powers. Bray said the apocalypse is here, Bray went down on his knees. Thunder, lightning and fire hit the ring and the Undertaker theme song went off. Undertaker and Kane came down to the ringside by side in an amazing moment as the crowd went insane.


The other members of The Wyatt Family appeared, Kane and Undertaker took then out the show ended with Bray Wyatt getting to receive a double choke-slam.


The match was set for Survivor Series it was the 25th Anniversary of The Undertaker. At the show, Undertaker’s entrance was awesome because in the background was a giant casket with a hologram of all the different Undertaker personas.


This match was also good for what it was. It was short, but in the end, Undertaker and Kane came out on top. This was a pretty cool moment as it brought back childhood memories.


 12. Brothers of Destruction reunite at the Royal Rumble (2001)


At the 2001 Royal Rumble, Undertaker entered the Rumble at No. 25, Kane who was already in the match was raising havoc and dominating. When the Undertaker entered the match, no one would stand in their way. 


Undertaker and Kane cleared house one by one, Scotty 2 Hotty, who came in at No. 26, received a double choke-slam and was eliminated by Undertaker and Kane together.


As we all know Stone Cold Steve Austin would go onto win the Royal Rumble. But we will never forget the Brothers of Destruction’s dominance and reign of terror they did in this match with a combined 14 eliminations.



11. Undertaker vs. Bret Hart Summerslam (1997)


Bret Hart is one of the best wrestlers of all time. Him and The Undertaker always worked great together in the ring.


In this match, Bret worked on Undertaker’s lower body for most of the match so Taker couldn’t hit any of his big moves. Shawn Michaels was the special guest referee for this match, so it kept everyone on their toes to wait and see if something was going to happen.


That something did happen, and Shawn Michaels hit the Undertaker in the head with a chair. This chair shot was supposed to be aimed for Bret after Bret spat in Shawn Michaels face. Bret Hart would end up winning the championship.


Due to Michaels costing the Undertaker the championship. This was the seed that was planted to lead to the first ever Hell in a Cell match between the two.


10. The Debut of the American Badass (2000)


In late 1999, the Undertaker took time off from the company to nurse a groin injury. He was advertised for Armageddon 1999, but he tore his pectoral muscle. Due to this injury Undertaker was out of action for almost eight months.


In the weeks leading up to Judgement Day we got creepy promos of kids talking about someone coming back from the dead, in the promos it said, “Judgement Day is Coming”. Needless to say fans back then figured it out that it would the Undertaker, but what the fans did not know is that it would be a brand new Undertaker.


At Judgement Day, the main event was The Rock vs. Triple H in a 60-minute Iron Man match with Shawn Michaels as the Special Guest Referee. With three minutes left in the match Triple H was up 5-4. Vince, Shane and Stephanie came down to the ring to make sure The Rock couldn’t tie the match. The Rock fought off all three of them and tied it up at 5. It looked like The Rock was about to get lead in the match, but Shane pulled HBK out of the ring. HBK took out Shane and Vince. As that was going on DX interfered and beatdown The Rock, during this attack HBK was knocked off of the apron.


As DX was beating down The Rock, the creepy Judgement Day promo played and the girls in the video said “he’s here” with “Judgement Day is now” appearing on the screen. Kid Rock’s 

 “American Badass” began to play and the Undertaker came down to the ring on a motorcycle. Taker was wearing a leather coat with sunglasses and a bandana. He entered the ring and started whooping butt. Taker punched Vince in the face and delivered chokeslams to X-Pac and other wrestlers. Taker grabbed Stephanie McMahon by the throat ready to chokeslam her, but Triple H made the save by hitting Undertaker in the back with a chair, but it did not affect him as Undertaker delivered a chokeslam to The Game in the closing moments of the match followed by a Tombstone. Unfortunately, Shawn Michaels witnessed Taker put his hands-on Triple H. Due to Undertaker’s involvement this caused The Rock to get disqualified and Triple got the sixth point and got the win. 


Undertaker was not pleased as he stalked Shawn Michaels up with the ramp and rolled his eyes at the camera.


The big talk that came out of this show was Undertaker’s new look gone was The Deadman we all knew and loved. What we got was Mark Callaway updating his character in an attempt to get with the age demographic at the time.


As a kid, this was the Undertaker that I grew up with and I am glad that I did because you got to see a different side of the man who played the character. Undertaker would go on to be this character until Survivor Series 2003.


9. Undertaker vs. Brock Lesnar (2002)


Undertaker and Brock Lesnar’s rivalry is one of my favourites. Their first feud in 2002 stands out to me because they put on one of my favourite Hell in a Cell match ever.


Let’s begin, Undertaker won a No. 1 contender match in a triple threat match on August 29th, 2002 episode of SmackDown the main event was now set for Unforgiven Brock Lesnar vs. Undertaker.


On the September 5th, 2002 episode of SmackDown, SmackDown General Manager Stephanie McMahon arranged a contract signing with Lesnar and Taker. Brock talked about his amateur wrestling career and reminded Taker that became champion in less than a year.


Undertaker puts Brock over by saying his debut months in the WWE have been extremely impressive but Lesnar lax experience. The Undertaker says he has seen it all before and at Unforgiven, The Undertaker will properly test Brock by taking him to places he’s never been Taker says Brock Lesnar has not been beaten up yet in the ring but that will change at the upcoming pay-per-view.


Paul Heyman gets personal with Undertaker by saying he won’t be able to provide for his family after Brock is done with him. Heyman then brings up Undertaker’s unborn child. Taker goes to attack Paul, only to get stopped by Lesnar and the two have an intense staredown.


The next week on SmackDown Undertaker brought his wife to the show and Paul Heyman decided to intimidate her. Taker had a match with Matt Hardy in the main event. Undertaker saw on the titantron what Heyman was doing and Taker then ran back to see if Sarah was ok but instead, he got hit in the head with a steel chair by Brock Lesnar. Lesnar then intimidated Undertaker‘s wife as the show went off the air. On the following week's show before Unforgiven Undertaker called out Brock Lesnar and the two had a scuffle in the ring but Matt hardy was there to help Lesnar. The Undertaker went backstage to after Brock, but Brock got himself put in protective custody and the Undertaker was stopped by the cops.


Undertaker vs. Lesnar at Unforgiven was a good match, but the finish was weak as both men put their hands on the referee because they would not stop brawling. The match was no contest, and the fans were not happy. The show ended big though as Undertaker tossed Brock Lesnar through the Unforgiven sign.


Undertaker and Brock’s battled would be carried over to No Mercy, as they would collide in a Hell in a Cell match. A match that Undertaker made famous.


There was a big variable going into this match though and that was the cast that the Undertaker wore on his hand and forearm on the October 3rd, 2002 episode of SmackDown the Undertaker lost a falls count anywhere against Matt Hardy due to the help of Lesnar and after the match, Lesnar broke the Undertaker’s hand with a propane tank. There was some report out there regarding the Undertaker’s broken hand that some people seem to think he did work the match with a broken hand but there isn’t enough evidence to say if he did or didn’t. 


Paul Heyman and Brock Lesnar tried to get the cast officially removed from the match, complaining that It gave the Undertaker an advantage, but Undertaker was allowed to keep the cast on during the match. Things got ridiculous in the weeks leading up to No Mercy when Paul Heyman and Brock Lesnar introduced a woman named Tracy. Tracy said she had an affair with the Undertaker. To me, this shouldn’t have been a part of the storyline, because it was ridiculous thankfully it was dropped quickly, and Tracy admitted that there was no affair between her and Undertaker.


We now head into the main event at No Mercy. As a kid, I used to love Hell in a Cell match because they used to mean a lot. There was a time where you can see the look on the wrestler's faces that they were intimidated by the structure. Brock Lesnar played the part well. Brock soon realized that he didn’t want to be inside the cell with the Undertaker, but he was forced to fight. After a brutal showdown, Lesnar was able to win the match after reversing a Tombstone into the F5.


This was one of the bloodiest Hell in a Cell match ever and it is one of the best. It is something both of these men should be proud of.


8. The end of The Streak


Leading up to Wrestlemania 30, Brock Lesnar had no challengers for Wrestlemania 30. Weeks went by and no one accepted the challenge. But that all changed on the February 24, 2014, episode of Monday Night Raw, the closing segment was a contract signing for Brock Lesnar and for whoever he faces. Time went by and as Heyman and Lesnar were about to leave Undertaker’s gong and music hit, this would Undertaker’s first appearance in quite some time. Taker had a new look where he grew back his goatee and I got Ministry of Darkness Undertaker vibes.


Brock signed the contract, he then slammed on the table for Taker to sign. Taker then stabbed Brock in the hand with the pen and choke-slammed him through the table. Also, keep in mind that Undertaker didn’t sign the contract. Nonetheless, the match was set for Wrestlemania 30.


The buildup to this match was ok for me, it was nothing special. Both men sent messages to each other during the weeks that followed.


We all know how this match went down with Taker getting seriously hurt in the early going of this match. Brock broke the streak by hitting three F5’s. I’ll never forget how shocked and upset I was when this happened, I always think they could have done it differently.


I think they should have used the finish from their match at Summerslam 2015 at Wrestlemania because I think it would have given a better surprise and their feud in 2015 could have meant more than it did. But I still enjoyed the direction they went.


7. Undertaker vs. Batista (2007)


Let me just say this, the matches these two men had with each other were incredible and entertaining as hell.


We all know the Undertaker won the Royal Rumble in 2007. In the weeks that came Undertaker sent messages to WWE Champion John Cena, ECW Champion Bobby Lashley and World Heavyweight Champion Batista.


On the February 5th, 2007 episode of RAW Undertaker kicked off the show to choose his Wrestlemania 23 opponent Cena, Lashley and Batista made their way to the ring. Undertaker stared down all three men. Undertaker then looked at Batista and gave him the throat slash signalling Batista that Taker has chosen him for Wrestlemania. Undertaker would then send the first message as he chokeslams Batista.


Batista would get revenge on Taker at the No Way Out pay-per-view. In the main event, it was Batista and Undertaker taking on Shawn Michaels and John Cena. When it looked like Batista and Taker were going to roll to a victory. Batista grabbed The Deadman and delivered a spine buster costing them the match. When it was all set and done Batista stood over Taker raising the championship.


On the final SmackDown before Wrestlemania on March 30th, 2007 both men brawled in the ring while security tried to break them up. It was a crazy finish to this episode of SmackDown I remember it like it was yesterday.


We go into the match at Wrestlemania 23, Batista hit a spear on The Undertaker right when the bell rang. You knew right there that this match was going worth it. Undertaker hit one of his best dives over the top rope.


I could go on all day about this match it was truly one of Undertaker's best matches in this rivalry. The Deadman would hit the Tombstone on Batista to win his first World Heavyweight Championship in four years.


Their next match would take place at Backlash on April 29th, 2007 in a Last Man Standing Match this match was just as good it was back and forth. The finish of the match was crazy both men ended up near the stage as it looked like Undertaker was going to Tombstone Batista, Batista countered it and speared Taker off of the stage. Everything collapsed and both men stayed down for the count. This match ended in a draw.


The third match with these men would take place on May 11th, 2007 on SmackDown in a cage match. This was a very good match and we got it for free on TV. It was a hard-fought battle. Both men climbed the cage to escape. They both landed on the floor at the same time and the match ended in a draw this meant that Undertaker retained his title. After the match, Mark Henry brutally attacked Undertaker this would cause Edge to come out and take advantage of a beaten-down Undertaker and successfully cash in his Money in the Bank briefcase. This happened Undertaker was injured, and they needed to write him off. Taker would not be seen again until Unforgiven in September.


 Undertaker took on Mark Henry at Unforgiven after Henry took him out months prior Taker would win the match by hitting the Last Ride after the match, Taker signalled that he was coming for the World Heavyweight Championship.


On Cyber Sunday, Batista and The Deadman continued their unfinished business. This time the fans got to choose who would be the special guest referee and they picked Stone Cold Steve Austin. Batista would go on to retain the championship with a clean victory.


Undertaker and Batista would end their feud at Survivor Series the only way possible and that would be inside a Hell in a Cell.


Batista and The Deadman had a brutal Hell in a Cell match. As it looked like Taker was about to win the championship Edge made his return as a cameraman and attacked Undertaker, which would cost him the title. This would be the end of Undertaker vs. Batista as this feud lasted almost an entire year and it was incredible that is for sure, these guys put their bodies on the line in these brutal matches just to entertain us and they worked amazing together. 


6. Undertaker vs. Randy Orton (2005)


In 2005, Randy Orton was the next hottest superstar to be climbing the ranks in the WWE. On February 28th, 2005 during an episode of Monday Night Raw. WWE Hall of Famer “Superstar” Billy Graham is backstage talking to Randy Orton, he tells Orton that he has to go places where no other wrestler has gone before. Graham then adds that Orton needs to be unique, different and special. After Graham leaves the room Orton looks at the magazine in his hands and says “that’s exactly what I was thinking”. Orton put the magazine on the table and on the cover of that magazine was The Undertaker.


The interesting thing about this rivalry was it was the first Undertaker storyline where the streak would be the main focus. Everyone knew Taker was undefeated at Wrestlemania, but it was never pointed out until Wrestlemania 21. 


Leading up to this match Randy rko’d Jake The Snake Roberts and on an episode of SmackDown Taker and Orton had a contract signing. Orton tells Taker he has nothing but respect for him and his legacy, but at Wrestlemania, you will be 12-1. After Orton and Undertaker signed the contract, Orton would slap Undertaker in the face. Undertaker starts smiling and Randy leaves the ring. As Randy is up at the stage the lights go out and put his hands in the air and lightning strikes down near Orton. 


 To make sure nothing distracted Orton from his preparation for his match with Undertaker at Wrestlemania. Orton brought out his on-screen girlfriend Stacy Keebler, they’re standing in the middle of the ring and Orton wants to show the world how dedicated he is for this match so Randy kisses her and then just rko’s Stacey in the middle of the ring. This showed that Randy Orton was focused, and nothing was going to distract him from this opportunity.


As the weeks went on Undertaker played mind games with Randy Orton. Even Randy Orton’s father Cowboy Bob Orton got involved in the buildup.


We finally get to Wrestlemania, this match was up there as the match of the night. It went both ways and both men put on an amazing match. Orton got two close calls on almost beating the streak, one was when the referee got knocked out and Cowboy Bob Orton hit the Undertaker in the head with his cast and the other was when Orton reversed a chokeslam into a rko. In the end, Orton tried to tombstone the Undertaker, but Taker countered and hit his tombstone and getting the victory.


This rivalry got even better when Orton was drafted to SmackDown. These two men would battle each other again at Summerslam where Orton would get the win with the help of his father dressed up as a fan.


In the fall of 2005 these men had a match on SmackDown, it was a very good match as it was similar to the one at Wrestlemania. Taker and Orton battled back-and-forth during the match the Undertaker was going to put Randy Orton in a casket that the Orton brought outside during the match but inside the casket was a Manikin of the Undertaker this was set up to for them to have a match at No Mercy in a Casket Match. Undertaker would get the win going up 2-1 in this storyline.


At No Mercy 2005, Randy and Cowboy Bob Orton would take on Undertaker in a two on one handicap Casket Match. This match was good, but it wasn’t the best in their series. Once again it was back-and-forth and the Orton’s got the win after Undertaker went to chokeslam Randy in the casket, but cowboy Bob Orton pulled Undertaker‘s hair and Randy pulled out a chair and cracked the Undertaker in the head after the match Randy Orton set the casket on fire with the Undertaker inside. This was similar to what Kane did at the 1998 Royal Rumble. Randy did Undertaker’s signature throat slash telling him to Rest in Peace.


The Undertaker was not seen for weeks. Since he was gone Orton went on to join Team SmackDown at Survivor Series. Orton would win the match for his team. But after the match, while the SmackDown locker room came out to congratulate Orton, Undertaker’s gong went off and his druids came out carrying a casket. The casket was hit with a lightning bolt and it got set on fire. As the casket was burning Orton’s face was in shock. The casket lid got pushed open and Undertaker came out of the casket wearing a new attire and growing out his beard. Taker entered the ring and took out everyone, but Randy and his father as they escaped the ring. Taker signalled to Orton that he was next.


On a special Tuesday night episode of SmackDown on November 29th, 2005, Randy Orton blindsided the Undertaker by hitting him with a rko. Undertaker would sit up and go after Orton, but the numbers game caught up to Undertaker and Randy knocked out Taker with a tire iron shot to the back of the head. Undertaker’s body was inside the lowrider where Orton got the tire iron. Orton would then drive the lowrider into the SmackDown stage causing a big explosion. 


In the weeks that followed Randy thought he killed the Undertaker again, but he did not as the Undertaker started to play mind games with Randy. Undertaker told Randy that they would go one on one at Armageddon in a Hell in a Cell match. 


This was also one of my favourite Hell in a Cell match ever. As it was brutal, and it was a perfect way to end this feud. Undertaker would get the win by hitting a tombstone pile driver on Randy Orton and Randy sold it perfectly.


Undertaker made Randy into a legit contender with this storyline.

5. The Undertaker pays tribute to Paul Bearer (2013)


In 2013, Undertaker’s long-time manager and friend Paul Bearer passed away. On the March 11th, 2013 episode of Monday Night Raw. The Undertaker kicked off the show by paying tribute to Paul Bearer. As well as at the end of the show when he and his brother Kane paid tribute together.


It was a touching scene by both men as Paul Bearer played big roles in their career. Paul Bearer would be inducted into the Hall of Fame in 2014.


4. Undertaker vs. Triple H End of an Era Wrestlemania 28 (2012)


On January 30th, 2012, Monday Night Raw the Undertaker made his return since Wrestlemania 27 to confront Triple H. Taker came down and looked at the Wrestlemania sign, Triple H did as well and then he gave a pat on Undertaker’s shoulder and left the ring.


Weeks went on until Undertaker would get an answer from Triple H as he kept saying no to another match. It got to a point what the Undertaker shaved his head until Hunter said yes.


On February 28th, Undertaker finally got a yes from Triple H after Taker said that Shawn Michaels was always better them. After Triple H accepted, he added on that the only way everything will end is inside a Hell in a Cell


Shawn Michaels would be the special guest referee for this match. I enjoyed this match as it told an amazing story between the three men in the ring that night. I loved the close call where Shawn superkicks Taker and then Triple H hits a pedigree because it honestly felt like the streak was about to end. But as we all know Taker went on to be 20-0 at Wrestlemania.


This match was a classic for some fans as after the match we got an amazing moment where Undertaker, Shawn and Triple H walked up the stage together and embraced in a big hug.


3. Two Wrestlemania Classic matches with Shawn Michaels (2009-2010)


Wrestlemania 25, Mr. Wrestlemania Shawn Michaels took on the Undertaker. I love this match so much. To me was amazing because I honestly felt like Michaels was going to win and maybe beat the streak. it was an incredible match, and the buildup was fantastic. This match is one of the best matches ever it is up there as one the best Wrestlemania matches ever, and it stole the show it was too bad that it did not close it out as fans would’ve gone home in shock.


 In December of 2009 at the Slammy Awards, Shawn Michaels and the Undertaker won the match of the year. Shawn Michaels throughout the challenge again saying he wanted a rematch against the Undertaker as weeks and months went on Undertaker said no. So Shawn Michaels cost the Undertaker the World Heavyweight Championship at the elimination chamber pay-per-view the next night on raw undertaker agreed to the match vs. Michaels but only if Michaels put his career on the line and he agreed and this match was another instant classic as it brought out the best in both men. To me, the match at 26 is better because it meant so much more. After all, the stakes were raised.


Both of these matches are instant classics.


2. Undertaker vs Kane Wrestlemania 14 (1998)


In 1997, Paul Bearer mentioned that the Undertaker’s brother Kane was still alive. In the first-ever Hell in a Cell match against Shawn Michaels, It looked like The Undertaker was going to curse to a victory, but the lights when off and an explosion hit. Paul Bearer came down to the ring with Kane. Vince McMahon gave us the famous line of “That’s gotta be Kane”. Kane ripped the cell door open and tossed the referee, Kane entered the ring and lifted his hands and brought them down causing fire to appear on the ring posts. Kane would tombstone the Undertaker and cost him the WWE Championship.


The next night on Raw Kane destroyed the Hardy Boyz, and Paul Bearer welcomed Undertaker to his “worst nightmare”


Kane would challenge his brother to a match as the months went on, but Undertaker kept refusing. As it looks like Kane and the Undertaker we’re going to join as a team Kane turned on his brother at the Royal Rumble in 1998. Kane choke slammed the Undertaker into a casket and locked it. Kane would then light the casket on fire with Undertaker inside.


Undertaker would return on an episode of Raw after Kane thought he killed him. Undertaker would say “I will walk through the fires of hell to face you, Kane”. The match was set for Wrestlemania 14.


The battle was coming to a head, I re-watched this match recently and it still holds up today. Kane dominated the majority of this match and he was the first person to kick out of the tombstone. Undertaker would win the match after hitting three tombstones on his brother.


As we all know this was supposed to be a one-off, but Vince McMahon loved the Kane character so much that they continued this feud for a bit. Kane and Undertaker would go on to have the first-ever inferno match, but to me, that match was never as good as their Wrestlemania 14 match.




The return of The Deadman at Wrestlemania 20 (2004) 

On November 16th, 2003 The Undertaker took on Mr. McMahon in a buried alive match. It wasn’t really a wrestling match as it was just Undertaker beating the hell out of McMahon. Mr. McMahon was such an amazing heel at this time as you could not stand the things he was doing.


The Undertaker wasted no time at all as he busted Vince open early with a punch to the face. From here the undertaker destroys McMahon with anything he can find at ringside. To gain the upper hand Vince throws dirt in the Undertakers eyes and he then takes a blow to the head with a shovel, but Vince isn’t able to capitalize long enough and eventually the chairman is dragged into the grave Taker jumps into a dump truck that set on the side of the grave, but a huge explosion occurs, and Kane shows up. Kane then puts the Undertaker into the grave for allowing Vince McMahon to score the win.


On the following SmackDown Kane arrived to give a eulogy for his brother and calling him a fraud. Kane would go onto say that his brother is dead.


Two months later at the Royal Rumble match, Kane was dominating the match. The countdown for the next entry came up and when the clock hit zero the buzzer went off and we got two gongs. This was the first message sent by Undertaker since getting buried alive.


As weeks went on leading up to Wrestlemania Undertaker left messages for Kane saying that “The Dead will Rise”. I remember being a kid and getting a little spooked out by these video packages.


At Wrestlemania 20, everything came full circle as The Undertaker returned as the deadman going back to his original roots and not only did we get the return of The Undertaker, but we also got the return of Paul Bearer. The Undertaker would go on to defeat his brother once again at Wrestlemania and go 12-0. In my opinion, this is the best moment in his career as I remember hearing the crowd go insane and begin to chant “Undertaker”.


The Undertaker has left us with so many memories and this Sunday he will give us one more memory when he bids his final farewell in an amazing 30-year career. It has been an amazing ride of being a fan of his for all these years.



Photo Credits: WWE Instagram