1. WrestleMania VII
Why did they fight? There were no major incidents that led up to this fight between the newcomer to the company and the grizzled veteran.
The Match: The Undertaker, a heel at the time, dispatched of the future Hall of Famer in less than five minutes. The end came when Jimmy Snuka attempted a springboard off the top rope and was caught by the Undertaker and given the Tombstone Piledriver.
The Aftermath: With this victory, the Undertaker moved up the ranks in the company and would go on to win his first WWE Championship from Hulk Hogan at the Survivor Series which marked the one-year anniversary of his debut with the company.
2. WrestleMania VIIIThe Victim: Jake “The Snake” Roberts
Why did they fight? Jake and the Undertaker became allies when they lured the Ultimate Warrior into a room full of snakes. After the Ultimate Warrior left the company, Jake set his sites on Randy Savage and Elizabeth. Jake was about to clock Miss Elizabeth with a chair when the Undertaker grabbed it from him. A few weeks later, Jake Roberts got his revenge on The Funeral Parlor by locking the Undertaker's hand in a casket, giving Paul Bearer a DDT, and then whacking the Undertaker with a steel chair several times.
The Match: The Undertaker survived two DDT's and came back to life when Jake was about to attack Paul Bearer outside of the ring. The Undertaker gave Jake a tombstone outside of the ring and rolled him back into the ring to get the win.
The Aftermath: This was Jake's final appearance in World Wrestling Entertainment for almost four years. After vanquishing the evil snake man, the Undertaker became one of the most popular stars in the company. He would go on to have a feud with Kamala,who was managed by Harvey Wippleman, and introduced the coffin match to the WWE during that feud.
3. WrestleMania IX
The Victim: Giant Gonzalez
Why did they fight? After defeating Kamala, his manager brought in a new man to finish off the dead man. Giant Gonzalez debuted at the Royal Rumble and his interference in the bout caused the Undertaker to be eliminated.
The Match: This is the only bout in his WrestleMania tenure where the Undertaker did not gain a conclusive victory. This bout ended by disqualification when Harry Wippleman gave Gonzalez a chloroform soaked rag which was then used on the Undertaker. The Undertaker was able to recover from this chemical attack and magically reawakened after being taken out of the arena on a stretcher. This bout marked the first time the Undertaker had a fancy entrance at the show as he entered on a chariot with a vulture.
The Aftermath: This feud was settled at SummerSlam when the Undertaker defeated Giant Gonzalez.
4. WrestleMania XI
The Victim: King Kong Bundy
Why did they fight? The Undertaker missed the prior WrestleMania when he went missing following a bizarre incident at the 1994 Royal Rumble. Ted DiBiase then brought a fake Undertaker into the company which the real Undertaker defeated. That didn't stop Ted DiBasie and his Million Dollar Corporation from trying to destroy the Undertaker. At the 1995 Royal Rumble, King Kong Bundy attacked the Undertaker following a match he had with IRS and helped the Corporation steal the Undertaker's urn.
The Match: The referee for this bout, which took place while baseball was still dealing with their work stoppage, was American League Umpire Larry Young. The most interesting parts of this match took place outside of the ring. During the bout, the Undertaker took the urn back from Ted DiBiase. However, the urn was stolen by Kama later on in the match. After surviving the Avalanche, the Undertaker was able to win the bout after hitting Bundy with a body slam and then a clothesline.
The Aftermath: The Undertaker would regain control of the urn, which had been melted into a gold chain, when he beat Kama in a Casket Match at SummerSlam. That marked the end of his feud with the Million Dollar Corporation.
5. WrestleMania XII
The Victim: Diesel
Why did they fight? When the Undertaker was about to win the WWE Championship from Bret Hart at the 1996 Royal Rumble, Diesel ran to ring side and pulled the referee out of the ring which caused the match to end in a disqualification. The following month at In Your House 6, the Undertaker got his revenge when he pulled Diesel down through the floor of the ring during his steel cage championship bout against Bret Hart.
The Match: Two jackknife power bombs were not enough to put the Undertaker away. The Undertaker hit the choke slam and followed that with the Tombstone to get the win in his first bout at WrestleMania to go over 10 minutes.
The Aftermath: Diesel left the company a few months later and along with Scott Hall and Hulk Hogan formed the new World order. A few months later, the Undertaker began feuding with Mankind and was betrayed by his long-time manager, Paul Bearer.
6. WrestleMania 13
The Victim: Sid
Why did they fight? The WWE Championship scene was in turmoil following Shawn Michaels' vacating the title. The Undertaker was the number one contender to the title based upon being the runner-up in the Final Four match a few months before this event. Bret Hart won that match but lost the title to Sid the following night due to the interference of Steve Austin. A steel cage match was held between Bret and Sid with it already being known that the Undertaker was going to fight Sid and Bret was going to fight Austin at WrestleMania. Because Sid wound up winning that match, this WrestleMania bout was for the WWE Championship.
The Match: Shawn Michaels provided color commentary for this bout and that caused Bret to come out and insult all three men. Bret also made an appearance at the end of the bout when Sid was about to give the Undertaker the power bomb. Sid went over to attack Bret but was given a hot shot in the ropes by the former champion, That move stunned Sid enough to allow the Undertaker to hit the Tombstone and win the WWE Championship. This marked the start of the Undertaker's second WWE Championship reign.
The Aftermath: The Undertaker held the title until SummerSlam when Bret Hart beat him in a match where Shawn Michaels served as the special guest referee. In addition to defending the title, the Undertaker had to deal with a much more sinister plot that was in the works. Paul Bearer threatened to reveal a dark secret from the Undertaker's past. Over the course of the next few months, we found out that the Undertaker had a brother.
7. WrestleMania XIVThe Victim: Kane
Why did they fight? The Undertaker's brother, Kane, entered the company by interfering in a Hell in a Cell Match the Undertaker was having with Shawn Michaels. Despite costing him this bout, the Undertaker refused to fight his brother. Eventually, the brothers appeared to mend their issues but that was all a ruse. Kane cost his brother a chance at the WWE Championship when he interfered in a Casket Match the Undertaker was having with Shawn Michaels. Following the bout, Kane set the casket on fire while his brother was still inside of it.
The Match: Prior to the start of the bout, Pete Rose mocked the fans in Boston and received a Tombstone at the hands of Kane. The Undertaker would go on to win this bout after hitting his brother with three Tombstones and a few other moves in between those pile drivers. Despite winning the bout, Kane was able to get up from the punishment his brother gave him and delivered a Tombstone of his own, only his was onto a steel chair.
The Aftermath: The saga between the Brothers of Destruction has played out like a soap opera for over a decade. The men have feuded countless times with each other only to makeup for a period of time before one of them attacks the other and starts the cycle all over again.
8. WrestleMania XVThe Victim: The Big Boss Man
Why did they fight? For the first time since his debut match at WrestleMania, the Undertaker was hated by the fans. However, he was fighting a man just as hated as he was. At the time, the Undertaker was a leader of a group called the Ministry of Darkness. They were involved in a feud with another group the fans hated, the Corporation. For several weeks, the Undertaker had been stalking the family of Vince McMahon. The Big Boss Man was one of the enforcers of Vince McMahon's group.
The Match: For the first time since WrestleMania XII, Paul Bearer was at ringside with the Undertaker. This was a Hell in a Cell match and was notable for what happened after the Undertaker beat the Big Boss Man with the Tombstone. The Brood descended from the rafters and cut a hole in the cage. They then proceeded to put a noose around the Big Boss Man's neck and tied it to the roof of the cage. When the cage was lifted up, the Boss Man was hanged.
The Aftermath: Amazingly, the Big Boss Man missed no time despite suffering from an act that would have killed a normal man. Even more shocking, the feud between the Ministry and the Corporation was all a ruse to lure Steve Austin into trusting Vince McMahon. It turned out that Vince McMahon was the higher power that the Undertaker was answering to. Later in the year, the Undertaker would suffer a torn pectoral muscle and a groin injury which would lead to him missing WrestleMania 2000.
9. WrestleMania X-SevenThe Victim: Triple H
Why did they fight? The problems began when Triple H bragged that he had beaten everyone there is to beat. Unfortunately, he forgot that he never beat the Undertaker who took exception to those comments. After making life miserable for him, Triple H thought he outsmarted the Undertaker by placing an order of protection for Stephanie McMahon on him. However, Kane kidnapped Stephanie and threatened to throw her off a balcony until William Regal made this match.
The Match: Motörhead performed The Game for Triple H's entrance. The Undertaker came out on his motorcycle. This bout featured one of the longest referee bumps in history. He was unconscious when the Undertaker hit Triple H with a Tombstone. When he set up Triple H for the Last Ride, Triple H grabbed his sledge hammer and whacked the Undertaker in the head with it and busted him wide open. Triple H cornered the Undertaker and stood on the ropes while punching him in the head. This was the perfect position for the Undertaker to give Triple H the Last Ride to get the win.
The Aftermath: Triple H and Steve Austin would join forces as the Two Man Power Trip and feud with the Brothers of Destruction. However, the feud ended a few months later when Triple H injured his leg. The Undertaker then moved on to feud with Dallas Page who was stalking his wife, Sara, during the WCW Invasion angle.
10. WrestleMania X-8The Victim: Ric Flair
Why did they fight? At the time, Ric Flair was the co-owner of the company along with Vince McMahon. Flair did not like the way the Undertaker was behaving at this time. At No Way Out, the Undertaker was going to use a lead pipe against the Rock but Ric Flair not only stopped him but also hit the Undertaker with it. This led the Undertaker to challenge Ric Flair. When Flair refused, the Undertaker went on to attack Ric's friend Arn Anderson and his son, David Flair. These attacks forced Flair to change his mind and in the process, Flair accidentally hit a fan and was arrested. Fuel was further added to this fire by Vince McMahon as he hoped to get Flair fired from his position. Vince McMahon was temporarily given full power of the WWE by the Board of Directors and he immediately made this a No Disqualification Match.
The Match: For the second year in a row, the Undertaker came to the ring on his motorcycle. During the bout, Arn Anderson came out to help his friend and get some revenge on the Undertaker. Despite his interference, the Undertaker was able to hit the Tombstone and bring the streak to 10.
The Aftermath: Because of this bout being caused by the friction between Vince McMahon and Ric Flair as co-owners, the WWE Board of Directors decided to split the company into two brands with Ric Flair being in charge of RAW and Vince McMahon in charge of SmackDown. Despite his disdain for the Undertaker, Ric Flair drafted him to RAW as his number one pick. Flair would go on to lose his power to Vince McMahon a few months later.