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The big names in wrestling have gone through hundreds, sometimes thousands, of matches. We mainly remember them for their big, climactic PPV moments or their matches that were so well-performed that they became timeless. But they can’t all be winners, and even the most decorated wrestler has an off day. Maybe it’s their own failings, maybe it’s the opponent they’re stuck with, maybe it’s the storytelling, or maybe it’s just bad luck. Either way, we’re looking back at some of the worst matches by some of the sport’s top stars.
Just some ground rules first. It has to be someone considered consistently entertaining in matches, so no low-hanging fruit names like Hulk Hogan, Kevin Nash, Ultimate Warrior, or latter years Andre the Giant. No matches based around someone enduring a career-ending/threatening injury (e.g. Steve Austin vs. Owen Hart or Bret Hart v. Goldberg). Lastly, no matches with more than four participants. Bringing up a bad battle royal type match just feels like cheating and dilutes the role of the wrestler in question.
Steve Austin and Terrance Taylor vs. Beautiful Bobby and PN News (WCW Great American Bash 1991)
Due to various reasons, Great American Bash 1991 is considered a cursed show, and its opener is part of it. What could have been a solid tag match was dead on arrival thanks to being a team scaffold match. For those unaware, as this is a gimmick match wrestling hasn’t done very often in the last 30 years, a scaffold match has wrestlers fight it out on a thin platform high above the ring. Usually, these kinds of matches end when one guy gets knocked off the platform, Mortal Kombat Pit style. This one was instead a game of “Capture the Flag.” Why? Because nobody involved wanted to take such a stupid bump.
Even though this was Steve Austin near his physical prime, he and the rest of the wrestlers had very little to work with. Just four guys on a wooden bridge, trying to do the most careful brawling necessary because it was so, so easy to accidentally fall and get messed up. The extra-large PN News probably would have died if his footing was off. The ending was a mess as well, as Bobby Eaton got his hands on the flag and started walking it over to his side, winning the match, all while Austin climbed down to get his hands on some hairspray to put in his opponents’ eyes. Then everyone just awkwardly climbed down with Bobby and PN News announced as winners.
Rocky Maivia vs. The Sultan (WWF WrestleMania 13, 1997)
The rise of The Rock was the direct result of the people behind the scenes realizing something wasn’t working with the character and that they needed to pivot. “Blue Chipper” and third-generation sensation Rocky Maivia wasn’t grabbing the attention of the crowd, outside of all the booing and chanting for him to die because he sucked. The low point of the Maivia era came at the tail end of his Intercontinental Championship run and was probably the straw that broke the camel’s back.
Rocky was up against The Sultan, probably Rikishi/Fatu’s worst gimmick, as he didn’t get to show off any charisma or interesting moves. Just Rikishi in a mask, not yet big enough to be booked as a monster. The two had a match that went for far too long, the Honky Tonk man guest commentary didn’t help, and they just had no chemistry. Unlike a few years later, Rikishi just didn’t do it for The Rock.
Ric Flair vs. Hulk Hogan (WCW Uncensored 2000)
We strongly considered Ric Flair’s extremely uncomfortable retirement match in 2022, but at least it was a tag match, and the other three guys involved were good enough to make up for Flair’s age. No, for this one we’re going to the dark era of 2000 WCW. Flair and Hogan were feuding for the umpteenth time, and this time they decided to settle the score in a Strap Match. Not just any Strap Match, but a Yapapi Strap Match! What does that mean? It means that Hogan got to do some hilarious and unhinged promos to build to this PPV main event.
It was a big slog of a match where nobody seemed to know what to do. Lots of run-ins and interference, as well as Flair hiding the fact that he was cheating in a match with no disqualification. The commentators were unsure if this was a match decided by pinfall or touching every corner of the ring, and to be fair, the wrestlers weren’t sure either. Each guy went for pinfalls, and the whole thing came to an end when Hogan hit his leg drop, pinned Flair, THEN touched every corner.
Chris Jericho and Test vs. Scott Steiner and Stacy Kiebler (WWE Raw, 2003)
The storyline going into the match was that Test had become an abusive boyfriend to his manager Stacy Kiebler and Scott Steiner had enough, coming to her rescue. Eric Bischoff decided to make a tag match out of it, throwing the obnoxious Chris Jericho onto Test’s side. So at best, it was a handicap match where the semi-mobile, past-his-prime Steiner never got a chance to rest, and at worst, an avenue for a dude to physically abuse a woman.
We ended up with a gassed Steiner fighting off Jericho and Test for about eight minutes, only for the heel team to get disqualified for shoving the ref. Bischoff restarted the match with a no DQ stipulation, followed immediately by Steiner taking a gnarly chair shot to the head and Test flattening Stacy with a pumphandle slam. Jericho’s been in some awesome matches throughout the decades, but he was wasted here. Luckily, he got to duck out of what became a gradually worse storyline.
Bret Hart vs. Vince McMahon (WWE WrestleMania 26, 2010)
Bret Hart always claimed that his WrestleMania 11 match with Bob Backlund was the worst of his career. It certainly wasn’t good, but at least he could work the match! After getting his bell rung too hard and too many times over at WCW to the point that he suffered a stroke, Bret had to retire. But he returned to the ring 10 years later, but with one major drawback: thanks to the stroke, Bret could not take a single bump, or it could literally kill him.
That meant his grudge match with Vince had to be entirely smoke and mirrors. After an overbooked opening that had the entire Hart Family (or anyone willing to take the paycheck to be there) work over Vince, Bret showed up and also brutalized him in a one-sided fight. This would have been fine, but it kept going. And going. And going. It went from, “Stop! He’s already dead!” to “Okay, we get it! Move on!” There’s a reason why WWE’s YouTube only shows the post-match celebration. Bret proceeded to wrestle more matches over the next year where they had to write around his complete inability to endure any physical damage.
Will Ospreay vs. Vader (RevPro Uprising 2016)
Once upon a time, Will Ospreay and Ricochet had a banger match in NJPW, and footage of them in a flippy stalemate at the start of the match went viral. It was divisive footage, as a lot of people—namely older wrestling folk—thought it was an affront to wrestling. There were too many acrobatics and it was unrealistic. Why couldn’t it be more like real wrestling, where voodoo is real, Andre the Giant’s son lives in a magic dungeon, a zombie can control the lights, and a man with orange skin can just decide he wants to become invincible? One of the more outspoken people during this fiasco was Big Van Vader.
Jumping on the controversy, Revolution Pro Wrestling decided to bring in Vader for a match against Ospreay. An interesting novelty, there was little they could really do with it, as Vader was in his 60s, was too hefty to do much moving, and refused to lose, or even bump. That meant it was a whole lot of Ospreay bouncing off him. At least he had the crowd behind him, and they went with a screwy ending where Ospreay lost thanks to the ref getting knocked out and Pete Dunne interfering. Vader offered to make this a trilogy, but Ospreay declined.
Daniel Bryan vs Big Cass (WWE Backlash 2018)
First off, if we’re talking about the worst Bryan Danielson matches, honorable mention goes to a match he had in Pro Wrestling Guerilla with Claudio Castagnoli where Claudio held him in a 15-minute headlock just to see if the crowd would buy into it. Still, it’s somehow not the worst match of Bryan’s career.
Bryan has wrestled several uncoordinated giants over the years, like Great Khali and Satnam Singh. They did the best with what they could, but then there was his match against Big Cass. This was right after Bryan came back from retirement and WWE was intent on making Cass a big deal. Cass looked like he was sleepwalking through the match and the whole thing never seemed to get to second gear. Right as it seemed like it might be ramping up to something, Bryan put Cass in the LeBell Lock and made him tap. On top of that, Bryan could be seen grabbing Cass’ wrist to remind him that he was supposed to try and block the hold.
Shawn Michaels and Triple H vs. Undertaker and Kane (Crown Jewel 2018)
At WrestleMania 26, Shawn Michaels retired in the best way possible. He lost to The Undertaker in what remains one of the greatest matches in WWE history. Michaels was very adamant about committing to his retirement, refusing various opportunities to come back for a one-off. Then the Saudi government backed up the armored truck full of cash, and Michaels decided he could squeeze in one more main event. He and Triple H teamed up against Undertaker and Kane at Crown Jewel, the controversial PPV that made sure not to namedrop where the show was being held.
The match was nearly a half hour of utter garbage. 49-year-old Triple H was the youngest guy in the match and tore his pec almost immediately. Everyone spent the match being tired and uncoordinated, including a bit where Kane’s mask just fell off out of nowhere. Yes, a lot of these Saudi Arabia events are based on ideas that sound cool on paper, but don’t work out when you factor in age. We have another one of those in a little bit.
Kurt Angle vs. Baron Corbin (WrestleMania 35, 2019)
When Kurt Angle returned to WWE, he was certainly a shell of his former self (TNA will do that to you), but he had his moments. After a few years, it was apparent that he didn’t have much gas left in the tank and announced that he would be calling it a day at WrestleMania 35. Surely, there was a great wrestler to complement him in his one last go. Maybe put him up against his old rival Samoa Joe. Perhaps John Cena to bring their relationship full circle. But when Baron Corbin was announced as his rival, people figured it was a red herring to trick us into thinking we were getting the worst possible choice, but nope, it was Corbin!
The two did not mesh well at all. Angle was too broken down and Corbin wasn’t the guy to make it work. The match went for six minutes and felt, at best, like a forgettable Raw match you’d see in the middle of the show. Corbin ended up winning anyway, because WWE was really intent on making him seem like a big deal around that time. It didn’t really last.
Undertaker vs. Goldberg (Super ShowDown 2019)
20 years earlier, this would have been one of the biggest matches possible. Two of the most protected, unbeatable, mythical wrestlers in history taking each other on in an epic clash. It was an absolute dream match. Was. Both wrestlers were very much over the hill by this point. Undertaker was broken down physically, and Goldberg didn’t have much going for him if his matches weren’t based around hitting a Spear or two and winning in under two minutes. This match went for nine.
But it gets worse! It was outdoors in the burning Saudi sun, reducing both men to an exhausted, sweaty mess before the first minute had ended. On top of that, Goldberg accidentally gave himself a concussion during his entrance. Afraid that Undertaker was going to feel left out, the dazed Goldberg ended up dropping the Dead Man on his skull in a failed attempt to do a Jackhammer. Undertaker got him back with a botched Tombstone. By the time Undertaker won with a chokeslam (more of a choke push), Undertaker sat up, openly furious about how bad that went down.
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