15 Iconic Wrestling Matches That Were Actually Terrible

As fans of pro wrestling we’ve seen both extremes; from the highest of highs and lowest of lows. There truly is nothing worse however, than a profile match not living up to the expectations of fans. What makes this article so unique is that during the climate of the 90s, in-match quality wasn’t really our focus. Instead, the story-of-it-all is what really drew our attention; the match itself became secondary (in most cases) and it generally played that way, with some matches being typical Attitude Era encounters which saw the combatants wrestle a hardcore style, which was really all over the place.

Ironically, today we do not have that problem and matches are generally performed at a higher standard than before. Though, the storytelling-of-it-all has left fans wanting so much more. With a brand split in place, we hope the company can find that happy medium.

For now we document some cases that were rather interesting; the matches were so iconic that we really forgot how bad they truly were because of the outcomes or circumstances. Here is a list of 15 iconic wrestling matches that were actually terrible. Enjoy!


15 WrestleMania I: Hulk Hogan & Mr. T Vs. Roddy Piper & Paul Orndorff

Iconic doesn’t even begin to describe the meaning of this matchup. Vince McMahon and the WWE took a leap of faith on March 31st, 1985, hosting the first ever WrestleMania from Madison Square Garden. The show sold out with a little over 19,000 strong. The goal of this show was simple: make it the premiere night in the world of wrestling. I think we can safely say (decades later) that is exactly what it has become; an even greater night if that’s possible.

It was clear with the booking of the event, the company was opening a new door towards the entertainment aspect. The main event was highlighted by a couple of celebrities, like Mr. T, who was involved in the encounter and the late great Muhammad Ali, who was the special guest enforcer.

The match itself was pretty awful when looking back; it was clear, the WWE was all about pushing the entertainment value and less focused on what went on during the matches. The main event only lasted 13 minutes but hey, the night was so iconic that most fans don’t even remember just how bad it was.

14 WrestleMania 32: Triple H Vs. Roman Reigns

We push the fast forward button from WrestleMania I to the most recent one that took place in front of a record-setting crowd of over 100,000 screaming WWE fans. The show desperately needed to be iconic with such a crowd and ultimately, it just wasn’t that well received (specifically because of the main event).

The ingredients of the matchup indicated that it was a big deal. The WWE labelled the encounter as a 'passing of the torch' type of match and one that was going to pave the way for a new era. Weeks leading up to the match, the plot seemed a little disappointing with promos that seemed to drag on for way too long. Some believed that Shane and The Undertaker were going to main event, but that was not the case.

Instead of making up for the lackluster build-up and going full throttle in the match, it was instead built way too slow and the crowd lost interest rather quickly. The bout was 27 minutes long and was a big snooze fest on a night that demanded so much more.

13 WrestleMania 21: Triple H Vs. Batista

The Roman Reigns encounter with Triple H reminded us a lot of this match, although the build-up to the Triple H and Batista match was one of the greatest storylines of that era in sports and entertainment. The company built the match beautifully, as WrestleMania 21 was an event that showcased the new guards in the co-main events.

A night that was meant for them, was instead focused on two other talents that stole the show in one of the most epic WrestleMania matches ever between HBK and Kurt Angle.

After that, everything just seemed okay (mediocre at best). Cena put on a good display in a quick ten minute bout against JBL, winning the WWE Championship. The stage was set for a second passing of the torch match which was regarded as iconic in so many ways, especially considering that Cena and Batista were chosen to be the new faces of the company. Well, as we know one of them did, while the other clearly didn't and it all started with this match. Batista did not really shine and the match wasn’t good, being booked similar to the Roman/Triple H encounter with a very slow (and at times dull) pace. Batista won the match and it was apparent soon after that he was not 'the guy'.

12 Starrcade 98’: Goldberg Vs. Kevin Nash

Starrcade was regarded as WCW’s WrestleMania; the company put a major emphasis on its high profile main events but year after year, they’d miss the mark with terrible in-ring performances. 98’ was yet another example. Although to be fair, Nash and Goldberg aren’t really the greatest in-ring technicians to begin with.

With Goldberg set to lose his first match, the spectacle needed to be something special; after all, the circumstances were truly iconic. The company oddly chose Kevin Nash to do the job and man, was this ever a mistake. The bout was 11 minutes and all over the place. Ultimately, a stun gun ended Goldberg’s win streak. Ironically, the best match of the night was the very first one featuring three Cruiserweights in Billy Kidman, Rey Mysterio and Juventud Guerrera. The match was the longest of the night and definitely stole the show. Again, WCW had the ingredients, but failed miserably when it mattered most.

11 WWE Raw: Mankind Vs. The Rock

On January 4th, 1999, WCW made perhaps the biggest blunder in the company’s history after they announced that Mick Foley was scheduled to win the WWE Championship that night. This tactic worked for a little while, but it finally came back to haunt the company. Millions of fans turned the channel to watch Mankind do the impossible and win the Championship from the Great One, The Rock. This was a major turning point in the Monday Night Wars and turned the rivalry upside down.

The match is certainly historical and iconic, however if you watch the contest it was by no means a classic. In today’s WWE climate, the company loves to have classic Championship matches which are predominantly held in the ring. If you remember correctly, Attitude Era matches were nothing of the sort. Wrestlers were hardcore and over the top; this match signified that and was spent on the outside for most of the time. It wasn’t classic by any means but we'll still remember it forever because of its impact and outcome.

10 WrestleMania XI: Lawrence Taylor Vs. Bam Bam Bigelow

1995 was a dark year for the WWE. The company seemed complacent and things were not going well with WCW continuing to fill up its roster with highly valued and established wrestling stars. The WWE decided to take a risk on April 2nd, giving the main event slot of the biggest show of the year to an NFL player. The goal was simple: get mainstream hype which would add viewers in the long run, a formula that has worked but in a different time.

In front of 16,305 in Hartford, the match was regarded as one of the worst in WrestleMania history. The risk didn’t pay off and actually did more harm than good. Today, this match is iconic for all the wrong reasons, being labelled as one of the worst in WrestleMania history. Thankfully, the match was only a little more than ten minutes, making it one of the shortest main events in history. The bout was just awkward with Bam Bam being surrounded by WWE stars, and Taylor alongside his fellow NFLers. Lawrence picked up the victory and following the event, the WWE struggled to once again find its form for the next couple of years.

9 WrestleMania XV: The Undertaker Vs. Big Bossman (Hell In A Cell)

In an era which was all about run and gun wrestling, the company took a risk and booked the first ever Hell in a Cell match at the WrestleMania event (not in history) between The Undertaker and Big Boss Man. The company had high hopes making such a bold decision, as many thought it would have been a potential show-stealer because of the stipulation.

What was labelled as an iconic match fell flat in terms of the in-ring work from the two. Rare to see Taker in something that failed, but this one certainly did. Taker won the nine minute cell match and brutally hung the Boss Man following the encounter. Ladies and gentleman, that was The Attitude Era. We tend to forget because it was so long ago, but man were some matches so bad (and this was yet another example). Thankfully, Austin and The Rock came out for the main event following the match and put on a tremendous display which paved the way for one of the greatest rivalries in pro wrestling history.


8 Halloween Havoc 98’: Hulk Hogan Vs. The Ultimate Warrior

They built it like a match of the century, although it ended up perhaps ruining the entire company’s image. This match is exactly what we all hated from Bischoff’s promotion; a match we had seen before, just repacked and recycled in a different way.

It worked in one era, but as we’ve seen time and time again, every match has its place and this one clearly did not any longer. The match was an absolute snooze fest filled with errors. Not to mention it was insanely slow. Hogan ended up winning the match and many people saw it as a way for Hogan to pat himself on the back, avenging his loss to the Warrior from their WrestleMania VI encounter.

The match was not only one of the worst in history, but it also lasted way too long, thus making the main event between Goldberg and DDP cut short and fans not being allowed to see the ending of the match. So ironic that the young stars who had a great match that night were overshadowed by a couple of veterans that were way past their prime. WCW didn’t take the hint and continued to run operations that way, which led to their demise.

7 WrestleMania XX: Goldberg Vs. Brock Lesnar

WrestleMania XX was a stacked card from top to bottom and had one of the best shows in recent memory at the time. One of the only matches that did deliver that night was with two wrestlers that were set to leave following the match, in Goldberg and Lesnar.

The match was a recipe for disaster with both Superstars being on their way out. In a desperate attempt to salvage the match the company placed Steve Austin as the special referee, though not even the Texas Rattlesnake could have saved this match.

Thinking about such a match is exciting; two of the most dominant performers in history going toe-to-toe. However, the circumstances made the match fall flat and become iconic for all the wrong reasons. Thankfully, the card was good enough to overcome its shortcomings but man did these two drop the ball on such a massive opportunity.

6 WWE Raw: Booker T Vs. Buff Bagwell

On July 2nd, 2001, the WWE made history on its Monday Night flagship program giving the main event driver’s seat to a pair of WCW wrestlers. It was an iconic night and one that is still being discussed today; though, for all the wrong reasons.

The match desperately needed to showcase the brand's talents. The company was on the right track using a pair of young stars but the match failed to deliver and the fans were just not into it. The match was so bad that not only did the company never resort to something similar again, but Buff Bagwell was immediately terminated after the match. According to Bagwell, the company blamed his behavior, though many believe the match was so bad that it got him fired. The intent was to make it groundbreaking and iconic, ultimately it was received as such, but for all the wrong reasons. Sounds like WCW.

5 Survivor Series 97’: Shawn Michaels Vs. Bret Hart

From a 60 minute-plus breathtaking wrestling match to a 12 minute encounter which was spent outside more so than anything else, this basically sums up the match these two had from WrestleMania VII to the iconic 97’ Survivor Series. The outcome certainly overshadowed the match, as fans don’t remember anything from the contest and just remember the aftermath of Bret Hart getting screwed out of his job.

The match itself was a glorified Attitude Era match and anything but a classic. The match was spent predominantly outside while Shawn took every opportunity to get some heat from the Montreal crowd, taunting them every two minutes as it seemed. Out of the seven matches on the card, the iconic battle was one of the shortest matches and certainly won’t be remembered for its quality. Such a shame that the last time we got to see these guys compete against one another was under such terrible circumstances.

4 WrestleMania XXVI: Vince McMahon Vs. Bret Hart

The match had iconic written all over it... a decade prior. How many times have we seen the WWE take a really great idea but put it into fruition far too late? The most recent example of this was with Sting; the company didn’t bring him in for years until they finally decided to bring him in. His run was short-lived and he was forced to retire because of an injury. Fans hope Kurt Angle won’t suffer a similar fate, which is why we want to see him sooner rather than later.

Now for this match, once again the company tried to resurrect an old story by adding Bret Hart to the mix. The company billed it as one of the most iconic matches ever but it was anything but that, ultimately because of Bret’s inabilities to perform. The bout basically saw Hart ragdoll Vince in front of 72,000 fans around the arena for 11 minutes. The match was terrible but will still be remembered as iconic because of everything the two had previously gone through. Had this been done ten year earlier, we’d probably being having a different conversation. Yes, I understand it still probably would not be a classic, but the brutality of it all would certainly fit the bill much more.

3 Starrcade 97’: Sting Vs. Hulk Hogan

Thinking of this match still makes my blood boil; it is regarded as iconic but the booking of it all was absolutely mind-blowing. Once again, Hogan found it necessary to show how dominant he was by winning the match initially by performing a random leg drop and getting the 1-2-3 victory. The crowd was so confused by it all.

Things got worse when Bret Hart was apparently given the right to start the match over. At the sound of the bell Sting would go on to win the match and claim the title back to WCW, in one of the worst passing of the torch matches in history of pro wrestling.

We remember it as a triumph event and the changing of the guard, but the 12 minute match was not that at all. This match is literally the poster one for this article and sums up the WCW product. Once again, the match of the night went to the opening Cruiserweight bout between Eddie Guerrero and Dean Malenko. The company had their solution staring them in the face, though a constant reliance on the likes of Hulk Hogan put them in ground.

2 WrestleMania VI: Hulk Hogan Vs. Ultimate Warrior

Not very hard to see why some extremists dislike Hulk Hogan (who once again makes an appearance on this list). In fairness, this match was not all that terrible considering how limited the two really were in the ring.

It was promoted as the two main baby faces of the WWE going head-to-head for ultimate supremacy. A surprise to most, Hogan accepted the fact that he was going to lose, but sneaky Hulk creatively put the attention on himself as the camera followed his every move following the loss as he made his way backstage.

The match to this day is regarded as one of the most iconic in wrestling history but if you watch the 22 minute match again today, you’ll realize that the WWE was certainly in a different climate at the time which catered to storytelling more so than in match quality. It was iconic yes, but not an in-ring classic by any means.

1 WrestleMania XIV: Shawn Michaels Vs. Steve Austin

In terms of historical significance this match is pretty high up on the list. With Shawn Michaels set to leave, the WWE was set to welcome in a new era of sports and entertainment with Stone Cold Steve Austin leading the way for the company. On that night on March 29th, 1998, Steve took the ball and never looked back ushering the way for a new era and eventually slaying the dragon that was WCW.

Ironically, the match itself that put Steve over was anything but a classic, which is mind-blowing then you consider these two phenomenal in-ring performers. The circumstances were not good. At the Royal Rumble that year Shawn took a terrible bump against The Undertaker, leading to a severe back injury which was regarded as career threatening. With this going down, some believed Shawn wouldn’t even have the match, although he put his ego aside and fought through the pain.

It was a typical 20 minute Attitude Era match which was spent all over the place, from in the ring, to the outside to even up the ramp where the combatants used a drum set as a weapon. The outcome and what it did for the business overshadowed what the match was truly like.


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