WWE, for all the ire they draw from the fans, generally gets things right a lot of the time. They know how to surprise a crowd, and they know which outcome will keep a story going or give it a satisfying conclusion. I think that’s why we get so annoyed when they get it wrong – we expect more from them.
But wrestling fans are always as appreciative as they are critical, and I think that’s what I like most about the fan base. If the WWE gets something right, we’re all quick to let them know. But on the other hand, that same passion means when they get something wrong…we never really forget it.
It’s especially hard to forget a booking decision so bad it rocked the careers of the wrestlers involved, making it impossible or very difficult for them to recover. Even if the right person won, sometimes simply the way the match concluded can be a negative. At best, a bad result is a bump people will eventually forget, but at worst it’s a major stain on a career that’ll never quite go away.
The following 15 matches are definitely the latter, with each one of these having utterly baffling outcomes that did no one any favors, let alone the fans who invested their time and money into watching them.
15 AJ Styles vs. John Cena - Money in the Bank 2016
There’s only so many times the WWE can describe things as “dream matches” before you start getting a bit cynical towards the term. But no one was cynical for AJ Styles vs. John Cena. In the one corner, you have Mr. TNA and one of the biggest indie sensations of the past few years, hot off of one of the best NJPW runs in years. In the other corner, the most famous active wrestler in the world, John Cena.
This match met a lot of expectations. AJ looked incredibly strong, with Cena not really knowing how to counter the guy many consider to be the best in the world. Hell, AJ Styles even won, which was a great decision and made the new guy look like a million bucks. Everything about this match was perfect…except the way the ending played out.
14 Sheamus vs. Daniel Bryan - WrestleMania 28
Two years before his big Wrestlemania moment, Daniel Bryan was still insanely over. In the opening match of WM28, he stood in the ring opposite Sheamus as the Wold Heavyweight Champion. 18 seconds later he would no longer be champion, as the Celtic Warrior won after a single brogue kick.
13 Big Show vs. Brock Lesnar - Survivor Series 2002
Brock Lesnar is a huge deal these days after beating The Undertaker’s WrestleMania streak and promptly dismantling anybody he’s put in the ring with. But during his first run in the company, while he was still a beast of a competitor, he wasn’t completely invincible. He had his fair share of losses, though this particular loss was completely and utterly unjustifiable.
Brock was a rising star at this point, a young and powerful champion that the crowd were excited to see climb to the top of the card and dominate. At Survivor Series, he was put in a match against the Big Show, and should have been another crowning achievement during his fantastic career. However, due a confusing betrayal by Paul Heyman after a huge F-5, Brock found himself dropping the belt to Big Show, losing a lot of momentum in the process.
12 Christian vs. Randy Orton - SmackDown, 2011
Christian was a much beloved wrestler after a long stint alongside Edge as a tag team. However, while Edge would go on to become one of the company’s biggest stars, Christian never quite reached that top level.
That all changed at Extreme Rules 2011, when after a long career of fighting and climbing to the top, he ascended a ladder to take the World Heavyweight Championship, celebrating with Edge in the middle of the ring in a heart-warming moment for fans around the world.
11 The Miz vs. John Cena - WrestleMania 27
I love The Miz. I think he’s great on the mic and has shown a vast improvement in his in-ring style over the years. He’s worked hard and has become one of the most endearing heels at the company, and WrestleMania 27 was him at the very top of his career. Headlining WrestleMania against John Cena, it should have been all about The Miz and the journey he’d been on to get there.
Instead, it was about The Rock. The ending of the match saw a double-countout between Cena and Miz, before The Rock came out to cut a promo, using his status as host to restart the match. He then rock bottomed Cena, allowing Miz to get the pin. But his celebration was cut short as The Rock then beat The Miz up, ending WrestleMania in the spotlight.
10 Bret Hart vs. Yokozuna - WrestleMania IX
Hulkamania was waning, and Bret Hart was the obvious replacement. However, after a little while out of the company, Hulk Hogan had returned and the WWE immediately wanted to put the belt on him, but not have their new babyface champion Bret Hart lose to him. So instead, we got the…baffling conclusion we got at WrestleMania IX.
Yokozuna was the heel challenger going into WM9, and managed to beat Bret Hart after his manager threw salt into Bret’s eyes. Hogan then immediately came out and challenged Yokozuna, beating him for the belt and ending WM9 with a Hogan victory.
9 The Rock vs. CM Punk - Royal Rumble 2013
The Rock was preparing for his second match with John Cena, ending a trilogy of WrestleMania confrontations between the two. However, for some bizarre reason, the WWE felt that this second match-up between two of the biggest stars in the wrestling business needed something extra, and decided to make it for the World Heavyweight Championship. The big problem with this though, was that CM Punk was in the middle of his record-breaking reign during a period where he was one of the most over guys in the company.
8 John Cena vs. Brock Lesnar - Extreme Rules 2012
When Brock Lesnar returned in 2012, John Laurinaitis said it was to bring legitimacy back to the WWE. Ultimately, it did, as after a stint in UFC, Lesnar was seen as an actual killing machine capable of dismantling anyone he was put in the ring with. Except, apparently, John Cena.
In Lesnar’s very first match back, he was put against John Cena at Extreme Rules, and while Lesnar did dominate the match, Cena ended up coming out victorious. But not only did he come out victorious, he then celebrated emphatically before delivering a promo saying how much he loved performing in Chicago.
7 Triple H vs. Randy Orton - WrestleMania 25
While Randy Orton had already been a WWE Champion by this point, and had a great run as both a beloved babyface and despicable heel, this match really could have been his crowning moment. Going against his former mentor in Triple H, it would have been great to see Randy Orton stand victorious after a brutal and bloody affair.
Instead, we got a slow technical wrestling match that ended with Triple H winning, only for Orton to win the title a month later at Backlash in a bizarre tag-team match. While Orton was playing heel during this feud, and typically heels don’t win at WrestleMania, this moment should have solidified Orton as the one of the best heels of all time, rather than another stepping-stone for Triple H.
6 John Cena vs. Bray Wyatt - WrestleMania XXX
Out of everyone in WWE, Bray Wyatt is the person who has been hurt the most by bad booking. The guy is inherently engrossing, able to cut a superb promo and has some of the best in-ring psychology on the roster, and yet his story-lines before 2016 never strayed much outside the territory of “he is evil” and he very rarely won a feud.
At WM30 there was an opportunity for this to change, as he went one-on-one with John Cena. There were two great ways for this match to end – either with Cena falling to the dark-side like Bray wanting and cheating to win, or by Wyatt himself overcoming the biggest face in the company.
5 Team Cena vs. The Nexus - SummerSlam 2010
There were a lot of opportunities for this feud to go right, and Wade Barrett should have really held the WWE Championship during the Nexus storyline. But out of all the matches he should have won, this is the one that rubs a lot of fans the wrong way.
4 Triple H vs. Sting - WrestleMania 31
This was Sting’s first ever match for WWE, and it took place on the grandest stage of them all, WrestleMania. But what should have been a great moment for fans of wrestling worldwide turned into bitter disappointment as Triple H stood victorious at the end.
The warning signs were all there. The moment they started to build the match as a WCW vs WWE event it should have been obvious that this was how it was going to end. While the spectacle of seeing Sting in a WWE ring, alongside run-ins from DX and the nWo, was simply magical, it can’t erase the sour feeling that Sting really should have captured a victory here.
3 Triple H vs. Brock Lesnar - WrestleMania 29
Another Triple H match in this list, and unsurprisingly not the last one. The guy just loves to use his backstage sway to win, doesn't he?
Let’s simply look at who needed the win more here. Brock Lesnar had returned a year prior, but only had two matches under his belt, and only one of them was a win for the beast incarnate. For someone who was brought in to bring legitimacy back to the WWE, he had an awful track record at this point. In the other corner, was part-timer and mostly-retired Triple H, coming back to seek revenge on Brock after losing to him at the previous SummerSlam.
2 Triple H vs. Booker T - WrestleMania XIX
Remember when Triple H, a very very white man, stood in the ring with Booker T, a very not white man, on Monday Night Raw and said “People like you don’t deserve to be champion,” before asking him to do a little dance?
The segment was incredibly uncomfortable to watch then, and is still uncomfortable to watch now. Using racist undertones in a story is a very cheap way to build heat, especially when Triple H’s heel character was already despicable, but at least it should lead to a satisfying end. Except it didn’t.
1 Macho Man Randy Savage vs. Hulk Hogan - WrestleMania V
You may have noticed a lot of this list is comprised of Triple H and John Cena matches. They have a history of going over opponents that should have won, but Hulk Hogan was the founding father when it came to winning every match he was put in.
The Mega Powers was a tag-team of Randy Savage and Hulk Hogan, the two biggest babyfaces in the company. However, after some miscommunication and a friendship breakdown, the two became bitter rivals. Hogan thought Randy was overly paranoid about his girlfriend, Miss Elizabeth, and couldn’t handle the pressure of being champion. Randy thought that Hogan was a glory-seeker and a promise-breaker, someone who was always looking to steal the spotlight for himself.
In the end, Hogan got the win, capturing the WWE Championship and proving he was better than Randy Savage. In reality, this should have been a crowning moment showing that Savage was just as good as Hogan, but after Hogan no-sold an elbow drop, it was obvious this was simply another match where Hogan would inexplicably win.
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