Over the course of 32 years, fans of the WWE have seen 316 matches take place at the Showcase of the Immortals, and have witnessed several shocking moments.
From surprise title wins, to underdogs overcoming the odds, to WrestleMania XXVII when the brass just decided to mess with the fans. This list looks at the truly unexpected results that veered away from the presumed booking and expected norms of the WWE.
No telegraphed Mysterio win or Brogue Kicks to Daniel Bryan here, just amazed onlookers.
Honourable Mentions
Hogan vs Andre WrestleMania III
Looking back now, it seems like the only way WrestleMania’s biggest main event could go was for the Hulkster to scoop up the Giant and cement his place in sports entertainment history. Well, the Immortal Hulk Hogan was not always a god amongst men.
In 1987, his biggest friend turned adversary in Andre represented a huge obstacle that had been 15 years undefeated. Even Vince McMahon claims to have been undecided on the winner until the day of the event, and Andre almost unintentionally pinned Hogan early in the match after the first unsuccessful lift attempt
Also read: 5 times the Undertaker’s streak was booked to end and changed
Hogan was able to muster up the strength when it counted, though, and the slam heard around the world still reverberates today.
Fandango vs Chris Jericho WrestleMania XXIX
It’s almost blasphemous to mention this immediately following up an all-time great moment, yet Fandango’s victory on the biggest stage (in his re-debut) against the first undisputed champion is simply unmatched in stupidity.
Y2J has always been an exceptionally generous performer, but even the biggest Fandango fan could tell that he was not destined for Superstardom. No potential storyline, no logical excuse, just an upset so random that no one even remembers it.
#5 Triple H vs Randy Orton WrestleMania XXV
Randy Orton had been pegged by the brass as a future star from the moment that the third-generation talent had stepped into OVW. Triple H himself, along with Evolution, ushered him his first title win, and as a veteran champion opponent when it finally looked like he had hit his stride as a character.
One of, if not the, hottest commodities in the business in 2009, it seemed that destiny had finally arrived and that Randy Orton would get his moment in the main event to overcome an old mentor and show all of his potential.
Even if Orton’s potential is a little romanticised here, it’s still mindboggling how Triple H ended up thoroughly crushing him to close the anniversary show.
Yes, HHH was the face and had the redemption angle behind him with the heated build-up. Yes, it was the closer, which in the WWE, translates to sending the fans home happy. It still did not make sense and capped Orton’s ceiling for the rest of his career.
A number of other factors pile on the shock. The McMahons had all returned and had gotten their hands on Legacy at the go-home show, jumping the gun on the retribution angle. The match itself had no champion’s advantage, playing into Orton’s mind games and providing an easy loophole to get creative.
#4 Rick Rude vs The Ultimate Warrior WrestleMania V
Ravishing Rick Rude was a phenomenal heel in late 1980s WWF. He had the look, he was a terrific technical wrestler, he would showboat and mock the crowd regularly before, during and after his matches.
He was even partnered with Bobby Heenan as if to solidify himself as a main event level star. However, in this time period, Hogan was the king, Savage was the man, and the Ultimate Warrior was a runaway freight train on the way to beating Hogan the following year.
So for Rick Rude to beat Warrior for his Intercontinental championship when Warrior had never been pinned, would count as an upset under any circumstance.
This shock was not a bad one as the previous entry was. In fact, the match at Trump Plaza proved to be a hit on an otherwise underwhelming card. Had Warrior not regained the title in time for WrestleMania VI in Toronto, this may even have lifted the profile of the entire card for the long term.
A little like Rude’s career, though, the undeniable potential of this feud was never fully grasped and made into something special. The clash with Warrior, though, was an intriguing battle of the brawn that Rude soon figured he would not win, and decided instead to outwit his opponent with help from The Weasel.
An assist from the outside helped Rude get the pin before he bolted and left his manager to face the repercussions. This was a classic wrestling tactic that provided a great swerve and ultimately helped both parties involved.
#3 The Rock vs John Cena WrestleMania XXVIII
Even though fans were not foolish enough to believe the tagline ‘Once in a lifetime’, many would have still believed that a rematch, or further activity with The Rock, would have come off as a way of passing the torch to John Cena.
Cena had lost in the main event the year before because of the Rock and had since lost twice to CM Punk (clean!), legitimising the Straight Edge Champion who would go on to outlast Cena’s own championship reign record.
The very same Cena had also swept aside all other challengers for the previous 7 years and was now put up versus The Rock who had received the rub from Hogan at WrestleMania a decade before.
This was the moment where he would pay back and Cena would officially be permitted entry into the big boy table. Oh, how the Cena haters rejoiced.
After an extended back and forth between the gassed out hometown hero and the savvy main event veteran who still shouts out his spots for all the arena to hear, The Rock caught Cena in a final Rock Bottom and the crowd erupted.
It had been a dream for many, and this was an upset that reinvigorated fans in earnest, so even when Cena would come back and avenge his loss, he was relegated to a supporting act in the WrestleManias that followed.
Fans have roared for Bryan and Lesnar, and booed Roman Reigns unlike anyone ever in the main event, largely thanks to what was proven possible in Miami.
#2 Owen vs Bret WrestleMania X
The opening match to kick off the tenth edition of WrestleMania at Madison Square Garden was a clash between brothers. Like most bouts between older and younger siblings, big brother Bret Hart had the experience, as well as the championship resume and was generally accepted the superior worker.
Bret had a strong fan base and a main event slot later on the very same night, in which he would regain his championship crown and get his WrestleMania moment.
Owen Hart, while no slouch in the ring, was the oft-forgotten little brother who had gone through a variety of gimmicks, had been released, resigned, and seemed to just be along for his brother’s ride.
Understandably, Owen was fired up and his personality shone through so much that it clearly overshadowed his brother. Add a Jerry Lawler at the peak of his abrasive colour commentary, and the match exceeded all likely expectations as the opener.
Still, it was just impossible to think that Bret would lose in that situation, with everything coming his way and with Owen having achieved so little before.
An attempted victory roll to close the match was abruptly stopped by Owen, and with Bret stuck underneath, a career highlight for the little brother and one of the biggest upsets in WrestleMania history.
The fallout from this show and the levels of success the brothers achieved over their careers makes it even more bizarre looking back. Just chalk this one up for all the little brothers out there.
#1 Brock Lesnar vs Undertaker WrestleMania XXX
No real surprise here as to the biggest upset in the event’s history. For 21 WrestleManias they had come, and over the course of 23 years did each and every challenger of the Undertaker’s streak fall.
The matches had become a standard for Match of the Night, and for many older fans, represented the true main event each year. However, the nostalgia and emotion may have just peaked and started to slip at the point when the Beast Incarnate and his associate Paul Heyman came to conquer.
After the emotional pinnacle of the ‘End of an Era’ and 5-time World Champion CM Punk being denied the chance to snap it after 20-0, fans may have felt resigned to the fact that the achievement was now too big, and after so many all-time great matches, Undertaker would now no longer be able to produce a match worthy of the feat.
So after 25 minutes of good, but not great action, a third F-5 and a 1-2-3 really felt like we’d all been RKO’d out of nowhere.
A bold and ultimately wise move, Lesnar has the presence and potential to pass on a rub of this size for many years to come. Yet it is still a little hard to accept.
Without question, the Undertaker finally losing was always going to be the biggest upset and one of the most significant moments in WrestleMania history. Sadly, the biggest factor behind it is that it is indeed an upset, rather than a monumental happening as it deserved to be.
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