The Undertaker’s undefeated WrestleMania streak became the top-selling point for WWE in the 2000s when the run reached new levels of success. WWE realized the fans cared a lot about Undertaker’s attachment to the event. The undefeated streak was an accident of the ‘90s that started to become more intentional in the 2000s.
WWE booked some of the top names in the company to face off with Undertaker on the biggest stage by selling the streak as an attraction. Undertaker missed WrestleMania 2000 to start the decade, but he had noteworthy matches on every other show in the decade. Find out which matches found success and which ones missed the mark, with each 2000s WM match ranked from worst to best.
9 The Undertaker vs Big Show & A-Train (WrestleMania XIX)
WWE missed the boat with their Undertaker match at WrestleMania 19. The scheduled match was to be The Undertaker teaming up with his protégé Nathan Jones to face the heel team of Big Show and A-Train.
Jones clearly wasn’t ready for such a spotlight and was pulled at the last minute. Undertaker won the lackluster handicap match that felt like a waste of time for his streak. Big Show and A-Train tried to pose a threat, but fans just weren’t buying it.
8 The Undertaker vs Kane (WrestleMania XX)
The story for the WrestleMania 20 match between The Undertaker and Kane was bigger than the match itself. Kane was coming off his unmasking in 2003 when burying Undertaker alive to end the American Badass chapter of his career.
Undertaker returned as the Deadman to get revenge against Kane at WrestleMania 20 as one of the top matches on the card. Fans were happy to see the old gimmick back, but the match was forgettable with little action in between the memorable entrance and post-match celebration.
7 The Undertaker vs Mark Henry (WrestleMania 22)
WrestleMania 22 featured WWE taking a chance on Mark Henry as a credible opponent for The Undertaker on the biggest stage. Undertaker was coming off a classic title match with Kurt Angle on the prior PPV that had fans disappointed in this being his big WM program.
Henry was gaining momentum at the time when feuding with Undertaker and the match was passable. The disappointment came from fans just wanting to have the legend in a more important match. Undertaker added another victory to The Streak by defeating Henry in a Casket match.
6 The Undertaker vs Ric Flair (WrestleMania X8)
The Undertaker wanted to work with Ric Flair when Vince McMahon discussed potential WrestleMania 18 opponents with him. Flair was struggling with his confidence at the time, but Undertaker felt it was an ideal WM program.
The build saw Undertaker targeting Flair and even attacking his son David. Ric tried his best to have a great match, but it was just fine. Both guys did enough to have a good match without reaching the next level.
5 The Undertaker vs Randy Orton (WrestleMania 21)
Randy Orton’s rise as The Legend Killer from 2003 to 2005 saw him becoming the ideal person to threaten The Undertaker’s undefeated streak at WrestleMania 21. WWE ended a failed face run for Orton and turned him heel heading into the match.
Undertaker delivered a classic match that was arguably his best WM match at that point with Orton stepping up as well. Fans believed Orton had a chance to add to the importance of the false finishes. Undertaker pulled out the victory in a streak defining match.
4 The Undertaker vs Triple H (WrestleMania X-Seven)
Triple H and The Undertaker received the semi-main event position at WrestleMania 17 which was arguably the biggest show in wrestling history. The heel antics of Triple H attacking Undertaker in the weeks leading up to the event added another main event caliber match.
Undertaker was in the American Badass stage of his career and this was the match most associated with it. Triple H had a few close calls that fans believed would end the streak, but Undertaker prevailed at the historic event.
3 The Undertaker vs Edge (WrestleMania 24)
Edge was the only wrestler to build up a somewhat relevant undefeated streak at WrestleMania leading to a showdown with The Undertaker. WWE wanted to make the most of this when putting the two in a World Heavyweight Championship program at WrestleMania 24.
Fans loved the match between the two since Edge was the top heel in the company at the time. Undertaker overcame the interference of some of Edge’s entourage to pull out the victory in the main event of another great show.
2 The Undertaker vs Batista (WrestleMania 23)
Batista was a top face in 2007 when The Undertaker won the Royal Rumble match to challenge him for the World Heavyweight Championship at WrestleMania 23. Fans were forced to choose between the two faces in a hot feud and clearly preferred Undertaker based on his legacy.
The match was a classic with Batista playing into the heat of fans wanting him to lose. There were a few moments where The Streak felt to be in jeopardy in a way it never felt before. Undertaker scored the win over Batista in an instant classic to win the World Championship and extend the streak.
1 The Undertaker vs Shawn Michaels (WrestleMania 25)
WrestleMania 25 created the perfect stage for The Undertaker’s undefeated WrestleMania streak to peak in the best way possible. Shawn Michaels wanted a shot at cracking the streak since he was viewed as “Mr. WrestleMania” for his show-stealing classics.
In 2009, the two most important wrestlers in WrestleMania history had a match on the biggest stage for the first time. Michaels delivered an iconic performance, making the audience believe he was going to end the streak. Undertaker defeating Michaels gave us a match that is still considered the best of all time by many fans and wrestlers.