The Undertaker’s WrestleMania legacy will always be the biggest thing tied to his career. Fans were enthralled by The Undertaker going over two decades without a loss at the biggest show until finally falling to Brock Lesnar in 2014. The long history of names to face Undertaker at WrestleMania have a mixed bag of stories for their careers afterwards.
WWE booked certain wrestlers weak after the loss to Undertaker and they never found greater success in the company. However, others used that to gain the relevant momentum and experience to thrive afterwards. Undertaker sees them all as part of his history, but they have different stories. The following wrestlers either found success or never recovered after losing to Undertaker at WrestleMania.
10. Success: Kane
The most interesting booking decision in the early portion of The Undertaker’s WrestleMania history was his feud with Kane. The Undertaker and Kane having their first match could have gone Kane’s way since he was a new character in need of some wins.
However, the feud itself helped Kane look strong even when taking the loss to Undertaker at WrestleMania 14. WWE continued pushing Kane afterwards and he scored some future wins over Undertaker to benefit more from the feud.
9. Never Recovered: King Kong Bundy
The veteran status of King Kong Bundy earned him a big WrestleMania 11 match representing the Million Dollar Corporation against The Undertaker. Ted DiBiase’s group was feuding with Undertaker and Bundy was the big man selected for the match.
Undertaker and Bundy had a forgettable match that could have been better with a different member. WWE started to lose interest in Bundy shortly afterwards as this ended up being one of the final relevant things he did in wrestling.
8. Success: Edge
There was real doubt for the undefeated streak when The Undertaker faced Edge in the main event of WrestleMania 24. Edge was already a top star, but he was ascending to an even higher level around the time of this program.
Despite rumors of WWE considering having the streak end, Edge revealed in future interviews that he refused to ever end it. Undertaker beating Edge for the World Championship was a great moment and they continued to have a great feud for the rest of 2008.
7. Never Recovered: Big Boss Man
The Undertaker was involved in a personal feud with Vince McMahon heading into WrestleMania 15. McMahon’s henchmen in The Corporation faction represented Vince in various matches against Undertaker in early 1999.
The Big Boss Man was selected from the faction to face Undertaker in a Hell in a Cell match with the streak on the line. Undertaker hanging Boss Man as the cell raised after winning was more memorable. Boss Man continued trending downhill and wasn’t the right person for such big matches.
6. Success: Mark Henry
The WrestleMania 22 casket match between The Undertaker and Mark Henry disappointed many fans upset with the choice. Henry was in the midst of a push after returning from multiple failed stints that sent him to developmental.
Undertaker and Henry had a fun but uneventful match on the overall great card. The loss did help Henry moving forward as this was the first year that he got over in the way WWE wanted. Henry continued the dominant heel character for years and had a Hall of Fame worthy career.
5. Never Recovered: Sycho Sid
The main event run of Sycho Sid in WWE saw him reaching the top of the mountain in late 1996 and early 1997. Sid won the WWE Championship for a second time after Shawn Michaels “lost his smile” and retired to vacate the title.
WWE changed their entire upper card for WrestleMania 13 due to the change by having The Undertaker challenge Sid in the main event. Undertaker getting his big moment winning the WWE Championship closed the show and continued the streak. Sid instantly moved down the card before leaving WWE just months later after main eventing the major event.
4. Success: Batista
The idea of having The Undertaker wrestle another top face created a huge attraction for the World Championship at WrestleMania 23. Undertaker winning an all-time great Royal Rumble led to him challenging Batista for the top prize.
Both men gave their all for an outstanding match worthy of the biggest stage. Batista benefited from facing Undertaker in defeat and continued to have great matches with the legend throughout 2007 to help his legendary career.
3. Never Recovered: A-Train
WWE booked The Undertaker in his strangest WrestleMania match at WrestleMania 19. The streak was established enough to know Undertaker’s opponent was a big deal. WWE went with an originally planned tag match of Undertaker and Nathan Jones vs Big Show and A-Train.
Jones not being ready for the role led to Undertaker going at it alone and winning a handicapped match. A-Train specifically had his biggest match here due to a huge push in 2003. Unfortunately, he never felt like an equal to Undertaker again after losing a handicap match.
2. Success: Randy Orton
The Undertaker getting to face Randy Orton at WrestleMania 21 helped them both find one of the best feuds of their respective careers. Orton was coming off a failed World Championship reign and face run flopping ahead of the match.
WWE even turned Orton heel to make the feud make more sense. Fans bought into the false finishes of Orton coming close to ending the streak, but Undertaker prevailed to keep it going. Orton still came out a winner by having his momentum restart after the disappointment as a face.
1. Never Recovered: Giant Gonzalez
WWE didn’t realize the streak would become a big deal when booking The Undertaker to face Giant Gonzalez at WrestleMania 9. The big man came over from WCW and received a huge push against WWE’s top giant.
A horrible finish saw Undertaker winning by DQ in an all-time bad match. Gonzalez looked ridiculous in a hairy bodysuit trying to make an outlandish gimmick work. The streak continued, but Gonzalez never recovered from an embarrassing night at the office.