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WrestleMania's Biggest Losers
Originally published March 28, 2011 and updated for 2024

WrestleMania's Biggest Losers

WrestleMania is just around the corner (it's just a figure of speech; don't literally look around the corner for it, dumbass). With that in mind, I thought this would be as good a time as any to look at the many, many losers that have competed in it.


Let's face it: not everyone out there has an Undertaker-like streak going for them (actually.... no one else does). But some have seen more than their fair share of canvas when it comes to The Showcase Of The Immortals, while others have been less than impressive on The Grandest Stage Of Them All.


To wit:

WrestleMania's Biggest Losers

Tito Santana

Tito Santana has really done it all in this business. WWE Hall of Famer. Intercontinental Champion. Tag Team Champion. King Of The Ring.  And let's make no mistake about it: they don't give you a spot on the biggest show of the year on nine separate occasions if you suck.


What I'm calling into question here is Chico's ridiculously poor track record on the biggest show of the year. Sure, he had two wins, but they're not exactly much to brag about: Beating The Executioner (Playboy Buddy Rose under a hood) would only be considered a big deal if your name was Iron Mike Sharpe or Ricky Ataki.


And while Papa Shango was no slouch in the voodoo department.... you have to remember that the only people to even see the match were in the arena that night. Contrast that with seven losses, each one more humiliating than the last. I can kind of understand why Rick Martel turned on Chico when he had the chance.

WrestleMania's Biggest Losers


It's hard to blame Finlay for this one (or any of the other wrestlers listed here, for that matter, as they're pretty much all given instructions on what to do beforehand).


For the most part, he's been stuck in matches that he had no chance of winning. I mean, three Money In The Bank appearances? Really? Buddy probably can't even climb a ladder to fix the roof at his age; never mind to grab a briefcase suspended from a flimsy cable. Same with the dark match battle royal. I'm pretty sure someone flips a coin beforehand to decide who gets the 'honor' of winning what will, at best, be an extra or the Mania DVD a few months later.


But in the one match where The Man They Called Fit probably should have come out on top... he didn't. At WrestleMania 24, Finlay challenged JBL to the dreaded Belfast Brawl. This was Finlay's specialty match -- to him, it was just like the ones they have on the mean streets of Ireland every day!


Did The Belfast Bruiser win his own specialty match? Er... nope. JBL simply beat the crap out of him with a garbage can lid, and then punked out his snot-nosed kid for good measure. Way to shine, Papa Finlay!

WrestleMania's Biggest Losers

Ultimo Dragon

Now.... being 0 and 1 isn't a terrible track record in itself, and you have to consider that he was competing against many other top cruiserweights. And Funaki.


But the reason Ultimo Dragon appears on this list has nothing to do with the match result. It has to do with his botched entrance at WrestleMania XX, where he slipped on the stage of The Grandest Stage Of Them All.

WrestleMania's Biggest Losers

Jeff Hardy

It's one thing to call out a Finlay type for having an 0 and 5 WrestleMania record. It's another entirely when Jeff Hardy -- a four-time former World Champion who routinely steals the show -- fares only slight better.


In some of the crazy tag team matches, it was anyone's guess who would win. Same deal with Money In The Bank at WM23. But to lose to his own brother Matt Hardy at WrestleMania 25 still makes no sense, to this very day! After all, Jeff was clearly the more "over" of the two Hardyz, had been World Champion mere months earlier, AND he was out for revenge against his bro.


Oh, and a fun fact: Hardy was scheduled to be in WrestleMania 24's MITB ladder match -- he even qualified for it by winning a match against Snitsky. It's likely Jeffy would have even won that year, fixing his crappy WM record for good and probably setting up for a title reign. But because Hardy was suspended by WWE for a drug violation, he was forced to not wrestle on the show and watch from the sidelines. Thank goodness he and brother Matt returned to WWE in 2017 for a "Delightful" victory.

WrestleMania's Biggest Losers

Ron Simmons

What does Ron Simmons, a former WCW World Champion and WWE Hall of Famer, have to say about his 1-5 record at The Showcase of the Immortals?

WrestleMania's Biggest Losers

The Big Show

One could argue that at six foot twenty, or whatever WWE was advertising The Big Show's height at, the guy probably doesn't need to do too many jobs. Yet here he is with a 5 and 12 record at WrestleMania.


Some of the losses were unavoidable; it's not like he was going to win a World Title match in the main or semi-main event, and it was quite obvious at WrestleMania 20 that the powers-that-be were about to push John Cena hype into overdrive.


But that doesn't explain losses to both a boxer and a sumo wrestler! They even turned his losing ways into a storyline during his feud with Cody Rhodes. Which, fine, he won, but at that point.... whatevs.


Perhaps the most disappointing loss took place at WrestleMania XXX, when he was more than expected to win the match named after his "father", during the first Andre The Giant Memorial Battle Royal.


Sure, he won on his second attempt, but buddy was involved in the match for four straight years - odds were he was going to eventually be put over. But being eliminated three-quarters of those matches didn't make much sense...

WrestleMania's Biggest Losers

The Dudley Boyz

How come The Dudley Boyz -- the most decorated tag team in history and WWE Hall of Famers -- never got a single 'W' in the history of WrestleMania?


Maybe it was because Vince kept sticking them in friggin' three- and four-team matches! Nothing against the tag team dynasties that were Billy & Chuck or Garrison Cade & Mark Jindrak, but they probably could have taken the respective nights off and no one would have blinked.


Or, here's a brilliant idea: You have four teams? Book TWO tag team matches! Or eight singles matches! Or..... none at all, for that matter -- it wouldn't have made much difference in the grand scheme of things.


Any way you slice it, D-Von and Bubba Ray certainly have the single worst WrestleMania of any tag team in history.



WrestleMania's Biggest Losers

Vince McMahon

Look, no one ever suggested that Vince McMahon was this unstoppable legend, capable of ending The Undertaker's streak or anything. But still - 1 and 4 in a collection of street fights and "No Holds Barred" matches?


You'd figure that someone who always works No Holds Barred (and produced the atrocity of a movie by the same name) would know how to compete in one!


What's more, three quarters of Vinnie Mac's opponents weren't exactly top guys -- at least, at that point in their careers. Shane O' Mac was an executive that liked to take crazy leaps off the furniture; The Hulkster had already had 34 or his 68 back surgeries before squaring off against The Boss; and no offense, but The Hitman was recovering from a friggin' stroke.

Mr. McMahon finally got his first "W" at a WrestleMania, ordering an impromptu match against Pat McAfee, after McAfee had already competed against Austin Theory. While it was impressive that the octogenarian McMahon could still physically climb into the ring, the sub-four minute spectacle wasn't exactly a Match Of The Year candidate.

WrestleMania's Biggest Losers

Shawn Michaels

Everyone calls Shawn Michaels "Mr. WrestleMania," but I have to respectfully disagree.


Sure, he's had the best matches almost every time he's been out there, and with 17 matches to his credit... there are few people who have even come close to the number of appearances he's had (with the exception of The Undertaker, and we all know what his track record is like). HBK even won the WWF World Championship in the lengthiest Mania match on record - no small task.


"If that's true, why are you calling the guy a... loser!?!" is what you must be asking yourselves, assuming you have a habit of talking to wrestling columns.


Look, I get that this is a controversial pick... but hear me out. Going 6 and 11 is, relatively speaking, hardly anything one should be bragging about. If WWE superstars were NFL franchises, The Heartbreak Kid would be the Cleveland Browns.


Sure, if you play the percentages, Michaels had a better day at the office than Tito Santana, Finlay or Big Show. But who would compare Mr. Sweet Chin Music to those guys? I'd be more inclined to put him in the same category as certified WWE Legends such as Macho Man Randy Savage (7 wins, 4 losses), Stone Cold Steve Austin (5 wins, 2 losses), Bret Hart (7 and 7) or The Rock (6 and 5).

WrestleMania's Biggest Losers

Triple H

This one is going to be a controversial pick;  I realize that.


Triple H has been a part of WrestleMania since 1996, missing only two events in that time (2007's WrestleMania 23, due to injury, and 2020's WrestleMania 36).


During that time, particularly since WrestleMania 2000, Triple H has been in a featured match, if not the main event itself. Hell, in nine of those matches he's been defending or competing for some form of World Championship, and of those matches... The Game closed the show six times (WrestleManias 16, 18, 20, 21, 25 and 32, to be exact). On top of that, The King of Kings holds Mania victories over some of the biggest names in the business, including Brock Lesnar, Chris Jericho, Booker T, Randy Orton and Sting.


So what's our freaking problem with Triple H, exactly?


It's the fact that you have match his very-impressive ten career wins against 13 losses -- which statistically makes The Cerebral Assassin the single-biggest loser in WrestleMania history.


A string of bad luck? Probably not. After all, he's given the rub to some of the company's biggest stars, including John Cena, Batista, Daniel Bryan, Roman Reigns and Seth Rollins, which one has to believe is by design. No one appears to be better than Triple H at laying down when it matters most -- despite the rep he's always had for holding talent down.

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