The Undertaker might be the most respected wrestler in WWE history, but that doesn’t mean he’s had a flawless career. Fans may be surprised to truly look back at Undertaker’s career and witness just how many embarrassing moments he was a part of. Undertaker’s unique character placed him in strange storylines and feuds against unlikely wrestlers.
The recent episode of The Last Ride showed him cringing watching back an embarrassing performance against Roman Reigns. Undertaker’s embarrassing botches made him ashamed to watch back the match. It made him feel like he’d fallen to a low point following the classics against the likes of Shawn Michaels and Triple H. Find out what other incidents would provide the same experience. The following WWE moments would make Undertaker cringe to watch back today.
14 Pointless retirement moment vs Roman
The Undertaker cringed at his botches in the WrestleMania 33 stinker vs Roman Reigns, but the post-match moment of him leaving his gear in the ring could be worse. Fans gave Undertaker a pass for the performance by thanking him for his overall iconic career. The moment of retirement is cringeworthy to watch back today knowing he came back for more matches.
13 Putting over The Great Khali
The Great Khali was viewed as a huge signing by WWE due to his size. Vince McMahon wanted Khali to become a top star and placed him into a singles feud with The Undertaker instantly. Khali squashed Undertaker in attacks and their first match against each other. Undertaker expected Khali to become a star, but he turned into a joke due to his horrible in-ring skills.
12 Match with Goldberg
Saudi Arabia shows have become a staple of The Undertaker’s annual schedule due to the massive payday associated with the dream matches. Undertaker defeated Goldberg in arguably the worst match of their respective careers. The botches and dangerous moments made every wrestling fan watch them with embarrassment. Undertaker admitted to Steve Austin that it was a “bad day at the office.”
11 Sacrificing wrestlers on his symbol
WWE used to love pushing the envelope in the Attitude Era. The Undertaker joined that aspect of the show with his Ministry of Darkness character. Various wrestlers would get sacrificed on his own symbol similar to a cross. The imagery was powerful and intimidating at the time, but it would get him in a lot of trouble today.
10 Abducting Teddy Long
The Undertaker and CM Punk had a horrible feud in 2009 that saw WWE do another scripted rehash of the Montreal Screwjob. Teddy Long instructed the referee to cost Undertaker a match via ringing the bell early. Undertaker got his revenge by abducting Teddy Long on Smackdown as the night saw the segment continue little by little. The hokey moment is one Undertaker would prefer to avoid.
9 Breaking his nose vs Mabel
Injuries are a part of wrestling, but sometimes it’s worse witnessing a wrestler get reckless. Mabel developed a poor reputation for injuring others during his biggest push after winning King of the Ring in 1995. One memorable moment saw him landing on Undertaker’s face and breaking his nose. Undertaker made it work with a cool face mask that added to his character, but the ugly move gone wrong is hard to watch back.
8 Giant Gonzalez WM match
WrestleMania became associated with The Undertaker due to his undefeated streak, but one match almost ended that early. Giant Gonzalez did not tap out or get pinned in his WrestleMania 9 loss to Undertaker. The finish saw Undertaker winning by DQ, but the overall match was a train wreck. WWE trusted Undertaker to face some of the worst wrestlers in company history with mixed results.
7 Maven eliminating him from Royal Rumble
The Undertaker was willing to do his part in helping make stars like Kane, Brock Lesnar and Jeff Hardy. However, there were a couple of misses that wasted his time. WWE booked the shocking moment of Maven eliminating heel Undertaker from the 2002 Royal Rumble match. Undertaker beating Maven senseless afterwards was a lot of fun, but he likely regrets getting eliminated by someone that flopped.
6 Hanging the Big Boss Man in Hell in a Cell
The Ministry of Darkness version of The Undertaker’s character often crossed the line with some of his actions. Vince McMahon handpicked The Big Boss Man to face Undertaker on his behalf at WrestleMania 15. Undertaker easily won the match and hung Boss Man’s neck into a rope noose as the Hell in a Cell structure raised. The symbolism of him hanging Boss Man is not a visual WWE wants to highlight today for obvious reasons.
5 Last feud with Kane
The Undertaker and Kane had a great history together in WWE as both opponents and partners. WWE tried to get one last feud out of them in 2010. Many of the matches were disasters as both men had lost a few steps. Kane didn’t get the credibility as a World Champion during the feud due to the weak results.
4 His ex-wife becoming his manager
WWE showed the ultimate loyalty to The Undertaker by hiring his then-wife Sara in 2001. Sara had no experience in wrestling nor acting, but WWE still brought her in to manage Undertaker for a few months. Diamond Dallas Page debuted by stalking Sara to get in Undertaker’s head. Given the relationship ended poorly, Undertaker likely regrets mixing business with pleasure.
3 Burying Paul Bearer alive
One of the oddest Undertaker storylines saw Paul Heyman threatening him by abducting and threatening Paul Bearer. Undertaker faced the Dudley Boyz in a Concrete Crypt match that would see Heyman burying Bearer alive if Undertaker didn’t follow Heyman’s wishes. The ending saw Undertaker gaining control and making the call to bury his manager. It was meant to showcase Undertaker having no weaknesses, but he just looked like a jerk.
2 The Higher Power reveal
WWE ran a big storyline of a Higher Power figure giving orders to The Undertaker during his time leading the Ministry of Darkness. Undertaker’s actions going after Steve Austin and trying to sacrifice Stephanie McMahon had fans wondering who was behind it. Vince McMahon disappointed everyone by once again turning heel as the Higher Power. Undertaker looked weaker as McMahon’s lackey to ruin the momentum for his new character.
1 Feud with Fake Undertaker
WWE’s most cringeworthy storyline involving The Undertaker saw Ted DiBiase introducing a fake version of the character. DiBiase claimed he had found Undertaker’s price to do his bidding, but fans realized it was a fake. Undertaker returned from an injury to defeat the fake character played by Brian Lee in the Summerslam 1994 main event. The match was viewed as a huge failure and all-time worst WWE main event.