With a WWE career that lasted exactly thirty years, there is a dearth of matches to talk about when it comes to discussing The Undertaker. He’s been in all kinds of matches over his decades long career and faced all sorts of competitors. It’s easy to forget some of The Undertaker’s matches, both regular and gimmick.
That’s not to say these matches are the worst (although some of them you’ll certainly need to tape your eyeballs open for), but when some of these matches only happened once, whether it be the gimmick or the opponent, it’s easy to forget them.
10 Rest In Peace Match
Vince McMahon, no matter how much he doesn’t want to admit it, always has a bit of that old school carnival barker mentality to hire all sorts of performers. All sorts of sizes too, hence why Giant Gonzalez, the former El Gigante, was able to get a run in WWE. Unfortunately, he was paired up with The Undertaker, leaving The Phenom with the arduous task of trying to get a few matches out of him. The two met at SummerSlam 1993 in a Rest In Peace match, which was essentially a No Holds Barred match. The stipulation didn’t do much to help the match; Gonzalez just wasn’t that good.
9 Body Bag Match
Fun fact: Paul Bearer in real life was actually a funeral director. That meant he had access to purchase body bags. During the early part of The Undertaker’s career, he’d put his victims into a body bag before carrying their defeated carcass to the back.
The practice eventually led to Body Bag matches where you’d have to get your opponent into one in order to win. The Phenom took on The Ultimate Warrior in this contest at house shows and somehow was on the losing end of them.
8 Armageddon Rules
There are a lot of old school wrestlers and old school wrestling fans who have a deep respect for Terry Gordy. The former Freebird was one of the few who got the business so fast at such a young age. Once Michael Hayes was into the WWE brass deep enough, he made a play to bring his friend in for a few paydays. But thanks to ODing mid-flight on an airplane, he was a shell of himself both personally and professionally. The Undertaker was also one of the people with an adoration for Gordy and was happy to work with him. Gordy debuted as The Executioner and the two collided at In Your House in an Armageddon Rules match, which Gordy lost when he couldn’t answer the 10 count.
7 Casket Match Vs. Rusev
It wasn’t a lot of times that Chris Jericho and The Undertaker collided. But they were all set to in a Casket Match at the Greatest Royal Rumble. But Y2J appearing in New Japan is supposedly what squashed this dream match. Rusev was called on instead to deal with The Deadman in his specialty match. With little effort, Taker was able to put both Rusev and his cornerman, Aiden English into the box.
6 Punjabi Prison Match Vs. The Big Show
He might be a Hall of Famer and even might have a fan or two (billion) across the globe, but The Punjabi Playboy, The Great Khali wasn’t much of a good wrestler. But The Undertaker was still set to carry The Punjabi Nightmare through a match that was designed for him. He was set to take on The Undertaker in first ever Punjabi Prison match at The Great American Bash 2006. Elevated enzymes took Khali out and Big Show was put into the strange match where The Deadman was able to eke out the victory.
5 Buried Alive
Several times in WWE history, the company dug a massive grave near the entrance ramp and had a match where the goal was put your opponent in the grave and bury him alive.
Naturally the match was set up for The Undertaker who competed in every single one of them, including one against Vince McMahon. The match featured interference by Kane and the final appearance of The American Badass before he would return months later at WrestleMania 20 as the original Deadman.
4 The Final Curtain Match
One of The Undertaker’s unique overlooked rivalries was with Goldust. The two feuded briefly in 1996 and met up in a Final Curtain match at In Your House: Mind Games, which was essentially a sanctioned version of a Lights Out match. The only way to win was by pinfall, otherwise all rules were out the window.
3 Last Ride Match
Despite going back to The Deadman gimmick, The Undertaker embraced his Big Evil persona for a Last Ride Match. Essentially, an Ambulance match, the goal was beat the heck out of your opponent so badly that you can shove them into the back of a hearse to win. The Undertaker took on JBL at No Mercy 2004 in the first match of this kind, and Mr. Kennedy at Armageddon 2006 for the second, and last match with this gimmick. The Phenom got cheated thanks to Heidenreich against JBL, but against Kennedy, he destroyed the poor soul.
2 Biker Chain Match
When The Undertaker became The American Bad Ass, plenty of gimmick matches centered around the macabre had to go away for a little while. In their stead was a Biker Chain match, which actually was one of the many wars Big Evil had with a young Brock Lesnar.
Without Vince Russo in sight, at Unforgiven 2003 the chain was suspended on a pole, ready for either man to snatch it and use it. After interference from the FBI, Lesnar was able to grab the chain and deck The Deadman to retain the WWE title.
1 Pick Your Poison Match Vs. Edge Raw May 17, 2010
Randy Orton and Edge had broken up Rated RKO and were gearing up for their match at Over the Limit. They had agreed to a Pick Your Poison match on Raw where each man got to pick their opponents’ opponent for the night. After Edge said a few choice words about Orton, Christian’s music blared out and the former partners and best friends collided in a back and forth contest befitting the pair of lifelong friends. But Randy Orton outsmarted Edge when he came onto the TitanTron and declared that he had no idea why Christian was out there and summoned The Undertaker as Edge’s true opponent. Despite intentionally getting counted out, Christian tossed him back in for The Deadman to quickly decimated his former rival.