The Undertaker had an iconic career in WWE that spanned 30 years with countless championship reigns. There is no one in the wrestling business that has been more loyal to WWE than Undertaker. During the tough times in the mid-90s, Undertaker could have left WWE to join WCW, but he stayed. Undertaker started his career at Survivor Series 1990 as a heel, but he had his greatest success as a hero in WWE.
Nevertheless, Undertaker has always had the ability to reinvent himself to ensure that he stayed relevant. It certainly worked, and Undertaker carved out a career that only some could dream of. He's feuded with the likes of Shawn Michaels, Triple H, and Kurt Angle, and he had some of his best matches against those legends.
11 Undertaker Vs. Brock Lesnar - No Mercy 2002 (Rating: 9.02)
Brock Lesnar skyrocketed to the WWE Championship within months of his WWE career, and at No Mercy 2002, he put the coveted title on the line against The Undertaker. However, Lesnar had to collide with Undertaker in a Hell in a Cell match which suited The Deadman.
Despite having a broken hand, Undertaker put on a vintage performance, and he and Lesnar tore the house down in one of the best matches that WWE produced in 2002. Cementing his spot as The Next Big Thing, Lesnar delivered a jaw-dropping F5 to beat Undertaker cleanly.
10 Team WWE Vs. Team Alliance - Survivor Series 2001 (Rating: 9.02)
The Invasion storyline came to a halt at Survivor Series 2001 in a Winner Takes All match. Undertaker represented Team WWE alongside Kane, Chris Jericho, Big Show, and The Rock. They went head-to-head with Team Alliance's leader Shane McMahon, Stone Cold Steve Austin, Kurt Angle, Booker T, and Rob Van Dam.
This was one of the best traditional Survivor Series elimination matches in history with everyone except for Shane becoming a World Champion in WWE. Undertaker did not eliminate anyone, but he certainly played a part by delivering a Tombstone to Shane. Team WWE went on to prevail, putting an end to Team Alliance once and for all.
9 Undertaker Vs. CM Punk - WrestleMania 29 (Rating: 9.05)
WrestleMania 29 wasn't the greatest of spectacles, but Undertaker and CM Punk knocked it out of the park in an enticing affair. The Straight Edge Savior was looking to put a dent in Undertaker's sensational 20-0 unbeaten WrestleMania streak.
Before the match even began, Living Color played Punk's theme song "Cult of Personality" to the ring which had Punk pumped up for the match. Punk mixed it up with the very best in his final full year in WWE, and he pushed Undertaker to his limit, but he ended up being the last victim in Undertaker's WrestleMania unbeaten streak.
8 Undertaker Vs. Edge - WrestleMania XXIV (Rating: 9.09)
The Undertaker headlined WrestleMania for the first time in 11 years at WrestleMania XXIV, and he challenged Edge for the World Heavyweight Championship. The Phenom's entrance was first, which was rare even though traditionally the reigning champion usually enters the ring last.
Nonetheless, Undertaker and Edge masterfully told an excellent story, and Edge had a lot of offense in this match which made you think that he could end the streak. The Ultimate Opportunist gave it his best shot, but Undertaker expertly countered Edge's Spear into Hell's Gate to leave the Citrus Bowl as the new World Heavyweight Champion.
7 Undertaker Vs. Mankind - King Of The Ring 1998 (Rating: 9.10)
Undertaker and Mankind reignited their rivalry in 1998 and they took it to new heights (literally) at King of the Ring inside Hell in a Cell. Both men wasted no time by battling at the top of the cell, and Undertaker flung Mankind off the cell, crashing onto the announce table.
Mankind had a high threshold of pain, so it was no surprise that he continued the match. However, he took another brutal bump when he was Chokeslammed through the cell and into the ring. Mankind became a legitimate World Title contender that night, and Undertaker winning was irrelevant.
6 Undertaker Vs. Triple H - WrestleMania XXVIII (Rating: 9.16)
For the second consecutive year, Undertaker and Triple H battled at WrestleMania but this time it was in a Hell in a Cell match. No man has won more Hell in a Cell matches than these two, so it made sense that they collided in the Devil's Favorite Playground.
Shawn Michaels had a history with both men, and he oversaw proceedings as the special guest referee. HBK could not stay impartial throughout as he nailed Undertaker with Sweet Chin Music but Triple H failed to capitalize as Undertaker kicked out of the Pedigree. The Phenom walked away triumphant, but all three legends standing at the top of the ramp afterward was a heartfelt WrestleMania moment.
5 Undertaker Vs. Edge - SummerSlam 2008 (Rating: 9.21)
The Undertaker clashed with Edge in a Hell in a Cell match to bring SummerSlam 2008 to a close. It was the first time that The Rated R Superstar had competed in a Hell in a Cell match, but he looked right at home.
Neither man pulled any punches, and they used the Cell as a weapon to inflict punishment on their opponent. Edge put on a stellar performance for a debutant in a Hell in a Cell match, but he suffered another loss to Undertaker which ended their brilliant feud.
4 Undertaker Vs. Kurt Angle - No Way Out 2006 (Rating: 9.26)
Two of the all-time greats in Kurt Angle and The Undertaker squared off in an exceptional World Heavyweight Championship match at No Way Out 2006. This match was so good that it was arguably the match of the year, and it could have headlined WrestleMania.
This was an instant classic and Angle's title reign was in serious jeopardy. Their efforts certainly took a lot out of each but Angle narrowly escaped with his title intact at the skin of his teeth.
3 Undertaker Vs. Shawn Michaels - WrestleMania XXVI (Rating: 9.53)
The Undertaker and Shawn Michaels' longstanding rivalry had major implications at WrestleMania XXVI. Undertaker's WrestleMania unbeaten streak was at stake and so was Michaels' legendary career.
HBK's stubbornness is the reason why he lasted so long in WWE, and he showed signs of that in this bout with Undertaker as he refused to stay down. They traded blows and kicked out of each other's trademark finishers. Ultimately, HBK's show was stopped as Undertaker delivered a thunderous jumping Tombstone for the win.
2 Undertaker Vs. Shawn Michaels - Badd Blood: In Your House (Rating: 9.54)
The Undertaker and Shawn Michaels had the honor of competing in the inaugural Hell in a Cell match at Badd Blood: In Your House. There was nowhere to run or hide for the reigning European Champion but there was a significant prize at stake for the winner, as either HBK or the Deadman would face the WWE Champion Bret Hart at Survivor Series 1997.
Michaels was locked inside the cell all by his lonesome without the help of Triple H, Rick Rude, and Chyna, but he put on a five-star classic with Undertaker. The Deadman was closing in on the win, but Kane made his long-awaited debut. He ripped off the door, and emphatically Tombstoned Undertaker. The Showstopper prevailed and booked his ticket to Survivor Series.
1 Undertaker Vs. Shawn Michaels - WrestleMania XXV (Rating: 9.65)
The Undertaker and Shawn Michaels had a match for the ages at WrestleMania XXV. They were the rightful main event but failed to close out the show. Nonetheless, fans were mesmerized at what they witnessed. The quality of the wrestling that Undertaker and Michaels displayed was at the highest order.
There were several countless false finishes as expected in a high-caliber match. However, there was a scary moment for Undertaker when he did his trademark dive over the top rope and landed on his head. The Deadman managed to recover, extending his WrestleMania unbeaten streak to 17-0.