11. WrestleMania XIXThe Victims: Big Show and A-Train
Why did they fight? For several weeks, the Undertaker got strange gifts from the Big Show. A few days after beating him at No Way Out, he was beaten up by both the Big Show and A-Train until new-comer Nathan Jones showed up to help him.
The Match: This was originally scheduled to be a tag team match with Nathan Jones serving at the Undertaker's tag team partner. However, on Sunday Night Heat that took place right before the show, Nathan was attacked in the locker room by his two opponents and was taken out of this match which now became a 2-on-1 Handicap bout. The Undertaker came out on his motorcycle while Limp Bizkit performed his theme song, Rollin'. Nathan Jones made an appearance during the bout and took the Big Show out of commission. He then kicked A-Train in the face which allowed the Undertaker to hit A-Train with the Tombstone to get the victory.
The Aftermath: The Undertaker would go on to beat A-Train at SummerSlam a few months later. He would then get into a feud with Brock Lesnar which he wound up losing due to the interference of Vince McMahon. That would lead to the two men having a Buried Alive Match at the Survivor Series.
12. WrestleMania XXThe Victim: Kane
Why did they fight? At Survivor Series 2003, Kane interfered in the Buried Alive Match between Vince McMahon and his brother. For several months, the Undertaker would play mind games with his brother but was never seen.
The Match: The Undertaker's return marked the return of both his dead-man gimmick and also saw him reunite with Paul Bearer who had not been seen in years. Just like their match a few years earlier, the Undertaker defeated his brother after hitting him with the Tombstone.
The Aftermath: A few months later, Paul Heyman kidnapped Paul Bearer in an attempt to make the Undertaker do his bidding. The Undertaker refused and wound up burying Paul in a concrete crypt just so he would no longer have any weaknesses anyone could exploit. Since Kane was on RAW and the Undertaker was on SmackDown, the long-running feud became dormant for a while after this bout.
13. WrestleMania 21The Victim: Randy Orton
Why did they fight? Despite being a former World Heavyweight Champion, Randy was very unhappy with the way his career was going. He took the advice of Superstar Billy Graham who encouraged Randy to step up and go where no man has gone before in order to set himself apart. At the time, Randy was looking at a magazine with the Undertaker on it. Randy agreed with Billy Graham's advice and challenged the Undertaker to this match the following week.
The Match: Randy's father, “Cowboy” Bob Orton Jr. was at ringside for this bout. Despite using the cast on his arm to help his son, the Undertaker was able to reverse an attempted tombstone pile driver by Randy into one of his own for the win.
The Aftermath: Since both men were on different brands, the Undertaker got involved in a feud with Muhammad Hassan. Due to UPN banning that character from SmackDown, that feud ended prematurely. At SummerSlam, the feud with Randy resumed and Randy got the win. A few months later, the Orton's beat the Undertaker in a 2-on-1 Handicap Casket Match and then set fire to the casket. The feud ended at Armageddon when the Undertaker beat Randy in a Hell in a Cell Match.
14. WrestleMania 22
The Victim: Mark Henry
Why did they fight? During a bout in February on Friday Night SmackDown between World Heavyweight Champion Kurt Angle and the Undertaker, Mark Henry interfered in the bout and splashed the Undertaker through the announcers table. Mark Henry was managed by Daivari, who was aligned with Muhammad Hassan a year earlier. On an episode of Saturday Night's Main Event a few weeks prior to this show, Daivari was injured by the Undertaker when he was given a tombstone on the lid of a casket.
The Match: This was a Casket Match. The Undertaker was able to give Mark Henry the Tombstone and then rolled him into the casket to get the win.
The Aftermath: There was a rematch between the two men the following week and that match saw the Great Khali come out and destroy the Undertaker. The Great Khali was also managed by Daivari. That feud was supposed to end in a Punjabi Prison Match but the Great Khali was medically cut from the show due to issues with his enzyme levels. The feud wound up ended with the Undertaker beat the Great Khali in a Last Man Standing Match during an edition of Friday Night SmackDown.
15. WrestleMania 23The Victim: Batista
Why did they fight? The Undertaker won the Royal Rumble Match and chose to wrestle Batista for the World Heavyweight Championship.
The Match: Despite hitting the Undertaker with a Batista Bomb, he was unable to end the streak. The Undertaker wound up winning the match and the World heavyweight Championship with the Tombstone. As a result of this victory, the Undertaker became the first man to win both the WWE and the World heavyweight Championship at WrestleMania and his victory over Batista resulted in him beating every member of the once dominant group Evolution at the show.
The Aftermath: Over the next few months, the Undertaker was able to hold onto the title after fighting Batista to a draw in both a Last Man Standing Match and a Steel Cage Match. However, Edge cashed in his Money in the Bank title shot and won the title from the Undertaker after that cage match.
16. WrestleMania XXIVThe Victim: Edge
Why did they fight? At the Survivor Series, Edge pretended to be a cameraman and wound up costing the Undertaker a chance to regain the title from Batista in a Hell in a Cell Match. The following month, Edge regained the title in a triple-threat bout against Batista and the Undertaker due to the help of his Edgeheads. The Undertaker earned a title shot against Edge by winning an Elimination Chamber Match at No Way Out.
The Match: Despite the interference of the Edgeheads, the Undertaker was able to win this match via submission when Edge tapped out to the Hell's Gate (which was unnamed at that point). Following the bout, there was a pyro accident that injured a few fans at the Citrus Bowl.
The Aftermath: A few days after beating Edge at Backlash with the same move, SmackDown General Manager Vickie Guerrero stripped the Undertaker of the title because she deemed the move to be illegal. The Undertaker beat Edge via count out at Judgment Day but Vickie ruled that the title was still vacant due to the match not ending by pin fall or submission. Edge beat the Undertaker at One Night Stand in a TLC Match and due to pre-match stipulations, he was banned from the WWE. After Edge cheated on Vickie Guerrero with their wedding planner, Vickie reinstated the Undertaker and he beat Edge in a Hell in a Cell Match at SummerSlam.
17. 25th Anniversary of WrestleManiaThe Victim: Shawn Michaels
Why did they fight? Shawn Michaels defeated both JBL and then Vladimir Kozlov to earn the right to challenge the Undertaker at WrestleMania.
The Match: I have referred to this bout as the best non-title/non-stipulation match I have ever seen. This incredible bout ended when Shawn attempted a moonsault but was caught by the Undertaker who gave him the Tombstone to get the win.
The Aftermath: Because Shawn was on RAW and the Undertaker was on SmackDown, they did not get to interact with one another. However, at the Slammy Awards later in the year, Shawn made it known that he wanted another chance to end the streak.
18. WrestleMania XXVIThe Victim: Shawn Michaels
Why did they fight? The Undertaker refused Shawn's request for a rematch. Shawn knew that as long as the Undertaker was the World Heavyweight Champion then he would not be able to fight him. Shawn interfered in an Elimination Chamber Match and cost the Undertaker the title. This enraged the Undertaker who accepted Shawn's challenge only with the stipulation that Shawn retires if he loses.
The Match: Despite the lofty expectations that were set from their match a year earlier, this match was even better. After kicking out of two Tombstone pile drivers, the Undertaker was giving his throat slash gesture for a third when he stopped an yelled at Shawn to stay down. However, Shawn struggled to his knees, did the throat gesture himself and slapped the Undertaker. The Undertaker hit the third Tombstone to end the career of Shawn Michaels.
The Aftermath: This bout marked the end of the career of Shawn Michaels. The Undertaker wound up missing several months of action when he was put into a vegetative state by his brother. The reason Kane attacked his brother was because he saw the Undertaker's actions at the end of this bout as a sign of weakness that he could exploit. That feud ended with the Undertaker losing a Buried Alive Match to his brother.
19. WrestleMania XXVII
The Victim: Triple H
Why did they fight? The Undertaker returned to RAW on 2/21/11 after weeks of spooky videos signifying that date. Before the Undertaker could address the crowd following his hiatus, Triple H, who also had been gone for several months, made his way to the ring. Using only their body language and using no words, the match was set. The Undertaker later requested that this be a No Holds Barred Match.
The Match: The Undertaker forced Triple H to submit to the Hells Gate but not after being put through his most physical battle at WrestleMania. He survived three Pedigrees, a Tombstone, multiple chair shots, and being put through both a table and the Cole Mine.
The Aftermath: The Undertaker was taken out of the stadium by the medical staff via a motorized cart. He wasn't seen again for almost a year.
20. WrestleMania XXVIII
The Victim: Triple H
Why did they fight? Even though he won the match, the Undertaker felt like he lost since he couldn't leave the stadium under his own power. After initially not wanting to fight again because he knew he had to end the Undertaker if they fought again and it would be bad for business, Triple H finally relented. However, this time they would fight inside of the Hell in a Cell and Shawn Michaels would be the referee.
The Match: This was the most brutal of all the matches he has fought at this event. During the bout, Triple H hit him with over a dozen chair shots to the back and the Undertaker's back looked horrible by the time the match was over. Despite getting hit by the chair, ring steps, and the sledgehammer, the Undertaker was able to win via pin fall with the Tombstone.
The Aftermath: In a show of respect, the Undertaker and Shawn Michaels helped Triple H to the back of the stadium.
21. WrestleMania XXIX
Victim: CM Punk
Why did they fight? CM Punk earned the right to try and break the streak by defeating Sheamus, Randy Orton and Big Show in a Fatal 4Way Match. Things then got very personal following the death of Paul Bearer. CM Punk stole the urn that contained his remains and would later dump the ashes onto Undertaker.
The Match: CM Punk felt his bets chance to win the match would be by either disqualification or count out. His disrespectful antics caused the referee to warn Undertaker several times and he came close to winning via count out when he hit the dead man with a Macho Man elbow on the Spanish announcers table. However, Undertaker prevailed with the Tombstone.
The Aftermath: After the match, Undertaker regained possession of the urn that was stolen from him.