Arguably one of the most popular wrestlers in WWE history is The Undertaker. The Deadman is a one-of-a-kind athlete who captivated audiences for many years. Even casual fans who didn't follow wrestling religiously still tuned in for WrestleMania to watch Undertaker's matches. However, Undertaker's matches for the first five years in his WWE career weren't always the best to watch as his bouts were slow and methodical.

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Inevitably, Undertaker is a big man and it was natural that he feuded with several big guys. The majority of the big guys, Undertaker has engaged in a rivalry with has shown that the matches were extremely underwhelming. Despite all of the brilliance that Undertaker has shown in his career, there have been a few duds.

10 The Undertaker Vs. A-Train & Big Show - WrestleMania XIX (Rating: 3.24)

The Undertaker was due to team up with Nathan Jones at WrestleMania XIX but he collided against A-Train and Big Show on his lonesome in a handicap match. Jones wasn't quite ready for a match of this magnitude which is why he no longer featured in the bout.

Nevertheless, Undertaker certainly deserved a better marquee match at WrestleMania as this match completely missed the mark. It was the worst match on the card but Undertaker single-handedly dispatched the behemoths to go 11-0 at The Showcase of the Immortals.

9 Gauntlet Match - Super ShowDown 2020 (Rating: 3.13)

Super ShowDown 2020 remains to be WWE's latest show in Saudi Arabia and they have not returned yet due to the coronavirus pandemic. However, there was a Gauntlet match to crown the winner of the Tuwaiq Mountain Trophy.

The likes of AJ Styles, R-Truth, Andrade, Bobby Lashley, and Erick Rowan were featured. Nonetheless, Styles thought that he had won the trophy but Undertaker made an unexpected appearance. The Phenom was wearing his trademark trench coat and hat, and he didn't even remove them as he had a brief stand-off with Styles and prevailed with a Tombstone Piledriver to win the trophy.

8 The Undertaker Vs. Kane - SummerSlam 2000 (Rating: 2.67)

The rivalry between The Undertaker and Kane became tedious by the time 2000 rolled around. The brothers battled in a hard-hitting No Disqualification match at SummerSlam with The Big Red Machine turning heel once again in the lead up to this bout.

This was one of their weaker matches which is often forgotten about despite it taking place at SummerSlam. Moreover, Undertaker had an obsession with trying to remove Kane's mask which would unveil his disfigured face. The Deadman was successful but Kane retreated to the back with the match ruled as a no contest.

7 The Undertaker Vs. "The Undertaker" - SummerSlam 1994 (Rating: 2.20)

The Undertaker returned to action after a seven-month absence to face off with the fake "Undertaker" in the main event of SummerSlam 1994. This was not worthy of main eventing SummerSlam but it was done for Undertaker's big grand return.

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The Phenom traded his iconic grey for purple which was one of the first major instances of a revamp in Undertaker's character. The match was extremely slow and methodical with Undertaker picking up the win with three successive Tombstones, and he rolled his doppelganger into the casket.

6 The Undertaker Vs. Big Boss Man - WrestleMania XV (Rating: 1.85)

The rivalry between The Ministry of Darkness and The Corporation reached its fever pitch at WrestleMania XV. The Deadman collided with The Corporation's Head of Security The Big Boss Man in the first Hell in a Cell match to take place at WrestleMania.

Despite Undertaker being a specialist of some sorts in Hell in a Cell matches, this was one of the worst iterations of the match. Both men wore the proverbial crimson mask but the match was extremely boring and since both were heels, no one cheered for either man. Undertaker prevailed with a Tombstone Piledriver but the aftermath was remembered with Undertaker "hanging" Boss Man.

5 The Undertaker Vs. King Kong Bundy - WrestleMania XI (Rating: 1.67)

Undertaker missed WrestleMania for the first time at WrestleMania X, and a year later he was looking to make amends at WrestleMania XI. The Deadman had been feuding with The Million Dollar Corporation for the majority of 1995, and King Kong Bundy was his latest opponent on The Grandest Stage of Them All.

This was the fourth WrestleMania appearance for both participants as mentioned by Jerry "The King" Lawler on commentary. Bundy was way past his prime, and he was not able to keep up with Undertaker. This was another prime example of Undertaker working with a big guy and a poor match coming out of it. Nevertheless, Undertaker ensured that he remained unbeaten at WrestleMania.

4 The Undertaker Vs. The Dudley Boyz - The Great American Bash 2004 (Rating: 1.43)

The whole rivalry between The Undertaker, The Dudley Boyz, and Paul Heyman made little sense in 2004. Undertaker found himself competing against the reigning WWE Tag Team Champions The Dudley Boyz in a handicap Concrete Crypt match at The Great American Bash.

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This was an underwhelming handicap match that shouldn't have gone on last. However, Undertaker dismantled The Dudleys with ease and he was given an ultimatum by Paul Heyman to save Paul Bearer who was in the crypt with cement by pulling the lever down or not, and he chose not to save Bearer.

3 The Undertaker Vs. The Giant Gonzalez - WrestleMania IX (Rating: 0.93)

The Giant Gonzalez made his WWE debut at the 1993 Royal Rumble, and he set his eyes on The Undertaker by removing him from the Rumble match. The two finally collided at WrestleMania IX in unquestionably the worst WrestleMania match in Undertaker's illustrious career.

Gonzalez's height certainly hampered him in matches as his movement was non-existent and he looked clumsy in the ring. Undertaker won by disqualification and Gonzalez temporarily knocked Undertaker out with chloroform.

2 The Brothers Of Destruction Vs. DX - Crown Jewel 2018 (Rating: 0.76)

The Undertaker and Kane reunited The Brothers of Destruction and they went head-to-head with fellow veterans in the shape of a reunited DX in Shawn Michaels and Triple H at Crown Jewel 2018. It was a mouthwatering prospect on paper but the match was catastrophic.

All four were not capable of putting on 30-minute classics anymore which this match somehow lasted. Kane's mask was removed, Triple H's involvement was limited as he tore his pec, Michaels botched a moonsault, and Undertaker was far from his best. It wasn't a great night for the legends with Michaels better off staying retired than coming out of retirement for this big-money match.

1 The Undertaker Vs. Goldberg - Super ShowDown 2019 (Rating: 0.48)

Fans in Saudi Arabia were treated to seeing Undertaker in action at Super ShowDown 2019 but the problem he encountered was Goldberg. This would have been a dream match had it happened years prior when both were in the prime of their careers but their paths never crossed.

There was a catalog of botches with Goldberg failing to execute Undertaker's Tombstone Piledriver with both falling to the mat. Goldberg sustained a concussion but Undertaker prevailed in arguably the worst match of his career with a terrible-looking Chokeslam. Undertaker's reaction after the match told you everything you needed to know about the match's quality.

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