The Undertaker: The 10 Classic Matches You May Have Forgotten

Undertaker has had an incredible amount of iconic matches. But we wanted to look at 10 of the best hidden gems from his career.

It’s #Undertakeover Weekend here at Hooked On Wrestling and as part of the celebration of all things Deadman, we wanted to make a suggestion for some additional viewing if you’re in a black and purple mood.

Everyone knows about the absolute classics The Undertaker has had at WrestleMania and elsewhere. He has been responsible for some of the most iconic matches in WWE history.

What many don’t realise, however, is just how deep his body of work is. So with that in mind, how about checking out this list of minor classics that you might have forgotten or never seen. All certainly worth revisiting.

vs. Rob Van Dam – Vengeance, December 2001

Photo Credit: WWE

Right after Team WWF conquered The Alliance at The Survivor Series, The Undertaker marked a fantastic heel turn by laying waste to Jim Ross and launching his Big Evil persona.

His first PPV match under this guise was something of an oddity for him as it involved him contending for the Hardcore Title. The champion was the super-over former ECW stalwart Rob Van Dam who was himself just starting his post-Alliance face run in earnest.

These two opposites really did attract, putting on a compelling brawl all over the arena with RVD throwing everything he could at ‘Taker before being methodically dismantled by the newly ruthless Undertaker who walked out with the broken up belt hung around his neck. A fantastic 11 minute match that many forget about.


Royal Rumble Match, January 2007

Photo Credit: WWE

Whilst it would usually be impossible to single out a Royal Rumble as a marquee match for an individual, there are exceptions. Ric Flair in 1992 springs to mind. 2007 wasn’t really just about one man, it was about two. Taker and Shawn Michaels.

‘Taker entered the match at Number 30 and after a very fun Rumble, the two living legends were the last two men standing. Rather than the traditional last-two segment we usually get in a Rumble, the two embarked on a near 10-minute mini-match that was wonderful in its own right.

It was made all the more special as it was the first time the two had locked horns in a decade. Eventually Undertaker prevailed to win his first Royal Rumble.


vs. John Cena – Smackdown, June 2004

Photo Credit: WWE

Most people are under the assumption that Undertaker and John Cena did not have a match between their PPV match in 2003 and their truncated encounter at WrestleMania 34. Not so.

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They actually encountered each other twice on SmackDown in the interim. One was a draw in 2006 but there was also a match in June 2004 that was the pick of the bunch. No build-up, no huge expectations, just two guys going at it in a splendid TV match. Have you seen it? Do you remember it? I didn’t. But I’m very glad I revisited it and you will be too.


vs. Vince McMahon, Survivor Series, November 2003

Photo Credit: WWE

Vinnie Mac doesn’t tend to do bad matches does he? And this wild brawl of a Buried Alive match with Undertaker in 2003 fits that rule. Often overshadowed by the finish which saw Kane emerge to bury his brother and ultimately give new life to The Deadman, this match marked the end of The American Badass and it went out with a bang. Blood, physicality and an Undertaker intent on beating respect into his prey. Wonderful.


vs. Steve Austin – Judgment Day, May 2001

Photo Credit: WWE

It’s hard to imagine a match between these two icons being a hidden gem but there you are. Whilst their most famous bout at SummerSlam 1998 saw Austin at the peak of his popularity and ‘Taker as the face on the verge of a heel turn, this was the exact opposite.

Sandwiched in that odd hinterland between the amazing WrestleMania X-7 and the start of The Invasion, this May 2001 bout saw the sadistic heel Austin against American Badass Undertaker in a No Holds Barred match.

It was as hard-hitting and as awesome as you might imagine. It was the culmination of the feud between The Brothers Of Destruction and The Two Man Power Trip (Austin and Triple H). Taker took the loss before moving on to a feud with his ‘mystery stalker’ Diamond Dallas Page. Hmmm…


vs. Bret Hart – One Night Only, September 1997

Photo Credit: WWE

The Undertaker had an utterly wonderful 1997. He had high-profile opponents during the year as varied as Shawn Michaels, Bret Hart, Mankind, Vader and Sycho Sid. He was able to put on some absolute classics with all but the latter.

This particular match may well have been the best of them not to be inside Hell In A Cell. Taking place in September at the first UK exclusive PPV, ‘One Night Only’ in Birmingham, the match was for Hart’s WWF Title that he had won from ‘Taker the month before at SummerSlam.

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What a treat these two veterans put together in their final match together. Worth watching for that bit of history alone.


vs. Shawn Michaels – Ground Zero, September 1997

Photo Credit: WWE

The month before their all-time classic Hell In A Cell encounter (and less than two weeks before the One Night Only match above), this match between ‘Taker and HBK saw the two battle to a heated, personal draw which ended with a whole heap of the roster coming to the ring to separate the two icons before ‘Taker performed his iconic over the top rope dive for the first time. Interestingly, the last PPV match before Michaels officially launched D-Generation X.


w/ Team Hell No vs. The Shield – Raw, April 2013

Photo Credit: WWE

This one took place on a Monday Night Raw taping in London in April 2013 and marked ‘Taker’s first match since he defeated CM Punk at WrestleMania 29. As with most six-man tag matches with The Shield in that era, it was a fantastic match that put the absolute shine on apparent ‘weak link’ Daniel Bryan in front of a rabid O2 crowd.


vs. Kurt Angle – Survivor Series, November 2000

Photo Credit: WWE

Annoyingly, this match is probably overshadowed by The Undertaker’s choice of attire. Apparently losing his luggage, he wrestled the match in a pair of shiny, gold, leopard print trousers. Yes, it was as odd as it sounds.

Go beyond that though and you have a wonderful match. Not as acclaimed as his future singles and triple threat matches with Kurt Angle, this match played brilliantly into Angle’s character at the time.

He had just won his first WWF Title from The Rock and he was portrayed as a fluky champion who had to use all his sneaky smarts and guile to keep his title while matched against far superior opponents. As you can imagine, both guys nailed it.


vs. Vader – Royal Rumble, January 1997

Photo Credit: WWE

These two beasts clashed later in the year at In Your House: Canadian Stampede in what, in all honesty, was probably a better match than this. But that match is so often called underrated that it is no nothing of the sort and certainly not a hidden gem. This is. If you want to see the two best big men of all time beat the snot out of each other, this is the match for you.

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