5 Shocking Undertaker Matches You Definitely Don’t Remember Happening

Hamish Woodward

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The Undertaker has been wrestling since the 1980s, and there are very few wrestlers that he’s never crossed paths with in the ring. However, there are a few wrestlers from his storied past that you may be surprised to have wrestled with the legendary Phenom.

This list looks at all of the wrestlers to have wrestled the Undertaker that may not remember, or may never have known they did. The Deadman wrestled a legendary near 40 year career and thus has many matches and opponents that may have slipped through the cracks .

While he has had huge main event matches with stars like The Rock, Stone Cold Steve Austin, Hulk Hogan and Brock Lesnar, The Undertaker was never shy in facing off with some of the lower-card wrestlers too. He was very giving in the ring, and always made the less-popular stars look better than they did before he beat them.

5. Jon Moxley


In a long forgotten match, AEW star Jon Moxley took on The Undertaker in singles competition on an episode of Smackdown in 2013. Then known as Dean Ambrose and part of The Shield, Moxley took on the Undertaker in a singles match that proved to be his last ever televised match in WWE.

The Undertaker had been a part time wrestler for a number of years at this point. He wrestled sporadically, mainly only at Wrestlemania and other incredibly select pay per views. However, he wrestled Dean Ambrose on Smackdown in 2013, just a few weeks after he teamed with Kane and Daniel Bryan to face the Shield on Monday Night Raw.

Whilst The Undertaker vs Jon Moxley technically never happened, The Undertaker vs Dean Ambrose was a key match in WWE in 2013 and Moxley should be remembered as the last ever TV opponent of the Undertaker in WWE.

4. Festus

Despite becoming a star in NJPW as part of the Bullet Club as Doc Gallows, former WWE star Luke Gallows was known under a different name.

Before being “saved” by CM Punk as part of his Straight-Edged Society, Gallows was known as the mentally disabled partner of Jesse, known as Festus.

Festus would come to the ring in an almost trance-like state, not responding to anything or anyone, acting as if brain dead. However, as soon as the bell would ring he would transform into a monster and trample anyone in his path.

Undertaker wrestled Festus on a 2008 episode of Smackdown, with The Undertaker winning with a triangle choke move he called the “Hell’s Gate”. It was a surprisingly good, if not short, match that showed that Festus could have been than he was.

3. Bob Orton

Whilst it was not in the latter’s prime years, The Undertaker did take on “Cowboy” Bob Orton in a singles match on Smackdown. The match took place on 30th September 2005, and was part of the feud between The Undertaker and Randy Orton, the son of Cowboy Bob.

The match of course was mainly just Randy Orton running in to attack Undertaker, due to the age and physical condition. Nevertheless, the match is in the history books as one of the Undertaker’s matches you would not have expected to ever happen.

Despite Randy Orton being The Legend Killer, it was The Deadman who battled against the WWE Hall of Famer, in one of the most shocking matches of The Undertaker’s career so far.

2. Bruiser Brody

Despite his tragic murder in 1988 in Puerto Rico, the legendary Bruiser Brody did share the ring with the Undertaker. In a strange turn of events, The Undertaker vs Bruiser Brody was the very first match in the legendary career of The Phenom!.

Then known as Texas Red, The Undertaker took on Brody in his debut match on June 26, 1987. The pairs clash was for World Class Championship wrestling, which Bruiser Brody ran out the winner against the rookie Undertaker.

The Undertaker later revealed that he was too physical with his opponent due to his inexperience, and it took a stern kick to the jaw to teach him to be less aggressive with his opponents.

“The temperature in the room changed a little bit at that moment. So we tie up again, I’m about to shoot him across the ring.

I’m yelling, I’m gonna hit him with a clothesline. So as I [throw Bruiser Brody] I’m like, ‘Clothesline!’ He comes off the ropes like a bullet, like a six-foot-five, 300-pound bullet, and he kicks me square in my f***ing jaw.”

The Undertaker on his debut match against Bruiser Brody

1. Sting

Yes, that’s right. Despite topping every single list of matches that never happened, Sting vs The Undertaker is a match that did take place.

Well, sort of. Whilst the men playing the characters (Steve Borden and Mark Calaway) did face off with each other inside the ring, it was not as the characters that fans would have expected, and have asked for for 21 years since WCW closed.

In WCW in 1990, the man known as Sting took on a tall, ginger man by the name of “Mean” Mark Callous. This was before he went to the WWF and became the legendary Undertaker, and the match was little more than a “Monster of the Week” deal for then-NWA Heavyweight Champion Sting.

Sting was not the Sting we know today, either. Back then he had bleached blonde hair and colourful face paint, and was colloquially known as Surfer Sting. Whilst we never got The Undertaker vs the Sting Crow gimmick, these two did wrestle before, albeit years, or decades, before either mans peak.

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