The History of The Undertaker at SummerSlam

For so long, the Undertaker was a starring attraction at WrestleMania due to his lengthy winning streak. Only in recent years has he been beaten by the likes of Brock Lesnar and Roman Reigns, two of the few wrestlers modern-day WWE cares about protecting.

WrestleMania was always the Undertaker at his strongest, where you have to be at the top of your game to defeat him. But what is the Undertaker without his mythological plot armor? Sure, he’s a top tier threat, but has SummerSlam given him the same unstoppable mystique? Well…no, not really. SummerSlam honestly hasn’t been all too good for Undertaker all in all.

Undertaker started with the WWF in the end of 1990 and he almost immediately became the company’s top heel. In fact, one segment of Saturday Night’s Main Event had him throw Ultimate Warrior around like a rag doll and then completely no-sell a belt to the face from Hulk Hogan. They were absolutely dead serious about treating him as a big deal. So what did he do at SummerSlam ’91?

Nothing, really.

SummerSlam ’91 was this weird season finale for WWF. A series of happy endings and feud blow-offs where the good guys always came out on top. The company’s three top heels – Jake Roberts, Ric Flair, and Undertaker – were nowhere in sight. The show ended with Randy Savage’s wedding to Elizabeth (well, it technically ended with a prison rape joke at the Mountie’s expense, but we’ll ignore that).

At the PPV itself, the Undertaker didn’t show.

read more: SummerSlam 2019 Matches and Results

But afterwards, they filmed the reception and Savage started opening up gifts. One box had a snake in it, which was Jake Roberts and Undertaker’s cue to come out and wreak havoc until Sid Justice warded them off with a chair. So that was Undertaker’s SummerSlam debut. Sort of.

Undertaker’s actual SummerSlam debut came in 1992, when he was early into his run as an invincible face who was usually too busy to remember that he could easily win the WWF Championship if he wanted to. He took on fellow monster Kamala, which was unfortunate, since Undertaker couldn’t really do any of his few trademark moves against a guy that size. And man, early ’90s Undertaker’s offense was reaaalllly limited.

Luckily, the match ended after a few minutes thanks to a disqualification. Kamala started repeatedly crushing Undertaker with various splash attacks, each from higher up. After Kamala splashed him off the ropes, Paul Bearer merely smacked the mat and Undertaker sat up, scaring the hell out of Kamala, who promptly ran off in terror, guaranteeing another few months of this feud.

read more: The History of John Cena at Summerslam

SummerSlam 1993 was a WrestleMania rematch…of Undertaker’s worst match ever. Undertaker took on Giant Gonzalez in an RIP Match, which they hyped up for weeks without explaining, only to finally say, “Uh, it’s a no DQ match, I guess?” right before the opening bell. It was especially bad, mainly because of Gonzalez, but again, Undertaker was no spring chicken either back in the day. He finally ended their rivalry with a clothesline off the top rope.

The streak of bad matches continued in 1994 with the infamous Undertaker vs. Undertaker match. See, after being murdered by the entire heel locker room at the ’94 Royal Rumble, Undertaker vanished for a while and Ted Dibiase supposedly brought him back. It was really a lookalike with similar abilities who was powered by money instead of Paul Bearer’s urn. The entire thing was ridiculous and involved Leslie Nielsen and Domino’s Pizza getting involved. The real Undertaker, debuting his purple trim attire, appeared to have a match against his evil doppelganger.

read more: Why Summerslam 1991 Was the End of an Era for WWE

I should note that this was the main event while a championship cage match happened in the undercard. Really.

After a boring battle, the good Undertaker won and placed the fake into a casket. Leslie Nielsen and George Kennedy opened it up to find the casket empty and Vince McMahon decided not to continue this failure of a storyline.

Undertaker’s SummerSlam opponents didn’t get much better. In 1995, his lengthy feud with Ted Dibiase’s Million Dollar Corporation came to an end when he took on Kama the Supreme Fighting Machine. Keep in mind, by this point, he had already dealt with an evil Undertaker and King Kong Bundy.

This is like playing through a Teenage Mutant Ninja Turtles video game, getting past Shredder and Krang, then having to defeat Bebop in the final level.

It was a Casket Match and to add some flavor to the battle, Kama had stolen the urn and had it melted down into gold chains. I can’t fault the man for style. Kama (otherwise known as Papa Shango and the Godfather) is one of the worst performers in the company’s history, so this fight was borderline unwatchable.

SummerSlam 1996 brought the end of the streak. Not only in the sense that we got a decent enough Undertaker match, but also that he lost. Undertaker had been the target of Mankind, the psychotic self-mutilator who was constantly capable of bringing Undertaker to his knees. They were put into a rather bizarre Boiler Room Brawl, where they would fight it out in a boiler room, then make their way to the ring in order to grab the urn from Paul Bearer.

It wasn’t great for the fans in attendance, since they could only watch monitors of most of the action, but in terms of early hardcore brawls, it was a pretty good time. Although Undertaker bested Mankind in the boiler room, victory wasn’t his, considering Paul Bearer turned on him, smashed him with the urn, and handed it over to Mankind instead.

Better luck next year, I suppose.

Or maybe not. At WrestleMania 13, Undertaker won the WWF Championship from Sycho Sid. He would defend the belt against US-hating Bret Hart at SummerSlam 1997 with Bret’s eternal rival Shawn Michaels as the referee. If Bret lost, he would never wrestle in the United States again and if Michaels didn’t call it down the line, he’d be fired.

Being a Bret Hart match, it was easily Undertaker’s best match so far. Not just in terms of SummerSlam, but his 7 years in the company. Unfortunately for Undertaker, he lost his title thanks to Bret’s trickery. Behind Michaels’ back, Bret hit Undertaker with a chair. Michaels had no proof, but confronted Bret anyway and got a big loogie of spit splattered into his face. Losing his temper, Michaels swung the chair at Bret, missed, and smashed it into Undertaker’s skull. Bret made the cover and Michaels made the most reluctant 3-count you’ve ever seen.

Coincidentally, that spot was really important to the history of the company. Not only did it build up Bret’s America-hating heel run, but the Undertaker vs. Michaels feud that followed gave us fuel for D-Generation X to become huge, the very first Hell in a Cell, and the first appearance of Kane.

By SummerSlam 1998, Steve Austin was champ and Undertaker was named his opponent as the company’s biggest money match. It wasn’t nearly as good as Undertaker vs. Bret Hart, but it was notably the Undertaker’s only SummerSlam loss that didn’t involve shenanigans. Austin simply got the better of him and laid him out with a Stunner. That’s three losses in a row for those keeping score.

The good news is that he won in 1999. The bad news is that it was a lame match. It was Undertaker teaming up with Big Show to face Kane and X-Pac. This was during the tail end of Undertaker’s Satanic days when he hung around with Big Show and cut hilariously dumb promos about riding motorcycles in the desert and leaving Show to die.

Anyway, while Kane was big enough to match either opponent, X-Pac wasn’t and succumbed to a Tombstone in the end.

A year later, Undertaker would face Kane once more, mainly because neither had anything better to do (and original opponent Big Show pissed off the brass enough to be sent to developmental). By now, Undertaker had left and returned as a biker who no longer had special powers. Like all Undertaker/Kane matches, it looked fun on paper, but the two never had the chemistry to make it work. It ended in a no-contest as Undertaker kept tearing at Kane’s mask. With Kane maskless and distracted, Undertaker kept attacking him as they made their way to the back.

Good job by the camera guys for somehow never giving us a clear shot of Kane’s face, though. I’m not being sarcastic, that’s some skill in there.

In 2001, the two would be working together as the Brothers of Destruction in a cage match against Diamond Dallas Page and Chris Kanyon. It was sadly the poster match of everything wrong with the WWF vs. WCW feud going on at the time. Despite DDP being a really big deal in WCW, he was turned into a cowardly stalker wimp who spent every segment being beaten relentlessly by the Undertaker. This was no different as he and Kanyon were made to look like incompetent jokes and got torn to pieces inside that cage.

At SummerSlam 2002, Undertaker stopped doing Kane-related matches and instead slummed it in the midcard by taking on Test. It’s a pretty decent match, all things considered, and the only bad thing I can really say about it is that it’s probably the worst match of the night in a show that’s amazing from top to bottom. Despite getting a little botchy, Undertaker won via a Last Ride.

read more: Summerslam, No Holds Barred, and Zeus’ 0-5 Record

Undertaker’s 2003 wasn’t too different. This time he was up against A-Train (fittingly, Test’s former tag partner) in what was probably the closest we’d ever see to A-Train being considered a major threat. Of all of Undertaker’s SummerSlam matches, it was probably the most forgettable. Undertaker won, natch, but then it devolved into a Stephanie McMahon/Sable catfight.

Undertaker finally returned to the title picture in 2004 against WWE Champion JBL. It was a very good match outside of the bullshit ending. After surviving two Clotheslines from Hell and being able to ward off JBL’s sidekick Orlando Jordan several times over, Undertaker lost his patience and smashed JBL in the face with the title belt in front of the referee. Undertaker was disqualified and took out his aggression in a badass spot where he chokeslammed JBL through the roof of his limousine.

Fun fact: Undertaker wanted to lose that match cleanly, but JBL figured he’d be better off as a champ unable to fight his own battles.

He’d lose yet again at SummerSlam 2005 in a WrestleMania rematch with “Legend Killer” Randy Orton. Towards the end of a competitive match between the two, Undertaker had it won. Then a fan ran to the ring to distract him and Undertaker fell prey to an RKO. Orton got the pin and the “fan” turned out to be none other than Bob Orton Jr. That feud continued for another few months, ending when Undertaker destroyed Randy Orton in Hell in a Cell.

In 2006, Undertaker fought, well…nobody. Even though he was healthy, on the active roster, and was feuding with the Great Khali, Undertaker was missing from SummerSlam 2006. He challenged Khali to a Last Man Standing match and it was done on SmackDown instead. No idea why they would cut such a big deal from such a big show, but that happened. Probably because they were afraid of having Khali perform live and figured a taped match could be covered up with editing if need be.

Undertaker missed out on SummerSlam 2007 too, but that was because he was injured. As part of the angle that sent him off TV, Edge cashed in his Money in the Bank briefcase against a barely-breathing Undertaker and won. This would feed into a lengthy feud between the two that would finally reach its climax at SummerSlam 2008.

Throughout the list, there have been nothing but matches that aren’t worthy of a talent like the Undertaker. He lost a bunch of matches. He was in a lot of outright terrible matches. He was dropped down on the card, far below where he deserved to be. But at SummerSlam 2008 we finally got an Undertaker match that felt right.

Undertaker took on Edge in the main event in Hell in a Cell. It was one of the all-time best Hell in a Cell matches and is a must-watch if you have the WWE Network. Not only did Undertaker win, but after winning, he decided to chokeslam Edge through the ring itself from off a ladder, and flames burned out from that hole in the mat, suggesting that Edge was thrown straight into Hell. Awesome.

That would be the Undertaker’s final SummerSlam match for a long time, but he did make a few surprise appearances.

He popped in at the very end of SummerSlam 2009. CM Punk had just defeated Jeff Hardy for the World Heavyweight Championship in a TLC Match and during the post-match celebration, Undertaker teleported into the ring to chokeslam him.

SummerSlam 2010 was Undertaker’s final appearance for years, as he showed up as part of the Rey Mysterio/Kane match for the World Heavyweight Championship. Having returned from a near-death coma, Undertaker appeared sickly and confronted the man behind it all, Kane. Undertaker was too weak and ended up being destroyed by his brother. The feud was shockingly one-sided with Kane winning again and again for months until Undertaker stopped being a regular competitor and would only show up once or twice a year.

In his absence, there was a new face of fear and dominance. Brock Lesnar returned to WWE and made Triple H tap out in the main event of SummerSlam 2012. A year later, he defeated CM Punk. A year after that, he suplexed John Cena into mush and won the WWE World Heavyweight Championship. Brock Lesnar has been at five SummerSlams so far and only lost once. He arguably has the same sense of mythological edge that Undertaker once had at WrestleMania.

In the middle of that, Brock was able to pin Undertaker at WrestleMania XXX, becoming the man to end the streak. Even though Brock lived up to making that win mean something by being WWE’s unbeatable final boss, Paul Heyman made sure not to let up on reminding everyone that his client was the man who made Undertaker mortal. He laid into this for so long that Undertaker finally did something about it. Namely, he teleported into the ring and kicked Brock in the junk.

That set the stage for the main event of SummerSlam 2015. On one hand, it was the Undertaker’s only win against Brock and a way better match than at WrestleMania. On the other hand, it ended in such a dumb way that it hurt the show. Brock made Undertaker tap to the Kimura Lock, but Undertaker tapped in a way that the referee couldn’t see. The timekeeper did see it, so he rang the bell. While the ref yelled at the timekeeper, Undertaker punched Brock in the crotch and locked him in the Hell’s Gate. Brock flipped him off and passed out.

And so, the Undertaker’s final SummerSlam ended with people scratching their heads in confusion. Ah, well. At least he came out of it a winner.

Gavin Jasper writes for Den of Geek and will never get tired of talking about Undertaker vs. Undertaker. It’s so silly. Read more of his articles here and follow him on Twitter @Gavin4L

Read and download the Den of Geek SDCC 2019 Special Edition Magazine right here!