The Undertaker's WWE career has been highly successful which is why he managed to endure three decades in WWE. Undertaker has been involved in a plethora of outstanding wrestling matches with his two WrestleMania epics with Shawn Michaels amongst the highlights of his greatest bouts. Whilst, Undertaker is one of the best big men in WWE history, he isn't exempt from competing in some woeful matches.
Credit has to be given to The Undertaker as he tried his best in poor situations. Sometimes, the opponents he has been up against have not been at his level, which is why the match hasn't clicked, and the quality of the match has been dire and are matches the Deadman would not look back on fondly himself.
10 The Undertaker Vs. Big Boss Man - WrestleMania 15
The Undertaker and Big Boss Man clashed in the first Hell in a Cell match to take place at WrestleMania at WrestleMania 15. It was the penultimate match of the night with Undertaker representing the Ministry of Darkness, and Boss Man was looking to pick up a huge win for the Corporation.
This was a sluggish Hell in a Cell match, both competitors were busted wide open. Undertaker finished off Boss Man with his devastating Tombstone Piledriver to remain unbeaten at WrestleMania. The aftermath is more remembered for the match itself as Undertaker "hung" Boss Man with some assistance from the Brood and Paul Bearer.
9 The Undertaker Vs. The Undertaker - SummerSlam 1994
The Undertaker returned to in-ring action for the first time in seven months at SummerSlam 1994 and he faced off with his doppelganger. The best thing about Undertaker's return was his grand entrance alongside Paul Bearer.
This was one of the worst main events in the history of SummerSlam with Bret Hart and Owen Hart's WWE Championship steel cage match the best match of the night. Nevertheless, the fake Undertaker executed the Tombstone, and Ted DiBiase was raging as he refused to pin Undertaker. Nonetheless, the real Undertaker marked his return with a win after he laid out the Impostor Undertaker with three Tombstones in succession.
8 The Undertaker Vs. Roman Reigns - WrestleMania 33
Fans witnessed an atrocious main event between The Undertaker and Roman Reigns at WrestleMania 33. Undertaker looked sluggish in this bout, and he apologized to Reigns after their match as he was displeased with his performance.
Reigns was shoved down wrestling fans' throats as he was poised to take over as the next major star in WWE. Nonetheless, the Big Dog was victorious handing Undertaker his second WrestleMania loss, and Undertaker teased retirement by leaving his hat and coat in the ring.
7 The Undertaker Vs. Kane - Judgment Day: In Your House, 1998
Steve Austin was the special guest referee in The Undertaker and Kane's battle for the vacant WWE Championship. There was a caveat as Austin would be fired if he failed to crown Undertaker or Kane as the new WWE Champion.
Unfortunately, Undertaker and Kane's match was slow and methodical. However, Paul Bearer interfered and he betrayed his son Kane by reuniting with Undertaker after the Phenom hit Kane with the steel chair. Austin refused to award Kane or Undertaker the WWE Championship by counting both competitors' shoulders' down.
6 The Brothers Of Destruction Vs. KroniK - Unforgiven 2001
KroniK's Bryan Clark and Brian Adams were tasked with bringing the WCW Tag Team Championship back to the Alliance as they challenged the Brothers of Destruction for the titles. Kane and Undertaker dominated parts of the match, but it was a match that went downhill rapidly.
This was never going to be a technical masterclass, and the in-ring action was poor. The battle ensued for 10 minutes, and Undertaker executed the Chokeslam on Clark which was enough to retain the WCW Tag Team Championship.
5 The Brothers Of Destruction Vs. DX - Crown Jewel 2018
A large chunk of wrestling fans was relieving their childhood/adolescent years when they witnessed the Brothers of Destruction squaring off with DX at Crown Jewel 2018. This was Shawn Michaels' first match in eight years, and it was a forgettable outing for all four men.
The match was clunky, and nothing flowed throughout the match. All four competitors were past their prime, and everything that could go wrong went wrong. Ultimately, the night belonged to DX who saw off the Brothers of Destruction.
4 The Undertaker Vs. Hulk Hogan - Judgment Day 2002
Hulk Hogan had one last run as WWE Champion in 2002, and the Hulkster's WWE Championship title defense at Judgment Day was against The Undertaker. Undertaker was hoping that lightning stroke twice as he defeated Hogan for his first WWE Championship reign at Survivor Series 1991.
This was a poor match for their high standards. Hogan was unable to replicate his WrestleMania 18 outing with The Rock which played into Undertaker's hands as he put Hogan out of his misery with one of the worst Chokeslams in his career to become WWE Champion once more.
3 The Undertaker Vs. Giant Gonzalez - WrestleMania 9
The Undertaker had a mixed bag of opponents in the early stages of his WrestleMania career. However, The Undertaker and Giant Gonzalez clashed at WrestleMania 9, and it was one of the worst matches in the history of WrestleMania.
Giant Gonzalez's skillset was limited and his movement around the ring was slow and methodical. The match didn't go on forever and Undertaker won the match by disqualification to remain unbeaten at WrestleMania.
2 The Undertaker Vs. Goldberg - Super ShowDown 2019
The Undertaker and WWE Hall of Famer Goldberg were adversaries in Saudi Arabia and it was a woeful battle. Both men were in their 50s, and there were timing issues when both were trying to hit their respective signature moves.
Undertaker could have sustained a serious injury when Goldberg attempted the Jackhammer and he dropped Undertaker on his head. Nevertheless, the Demon of Death Valley prevailed, and he shook his head after the match to express his displeasure.
1 The Undertaker Vs. Giant Gonzalez - SummerSlam 1993
The Undertaker and Giant Gonzalez's match at WrestleMania 9 was bad but fans were subjected to the rematch between the pair at SummerSlam 1993 in a Rest in Peace match. This was another tough watch for fans in attendance as nothing improved from their WrestleMania 9 encounter.
Paul Bearer wasn't present at the start of the match but he returned midway through to retrieve the urn. Ultimately, this was the worst feud in Undertaker's career but he managed to secure the victory with a flying clothesline from the top rope.