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Biggest Betting Upsets! Top WWE Fights that beat the Odds!

Since the 16th Century when betting on horses first became commonplace, there has been good money to be made in sports betting. Even though Vince McMahon disavowed Wrestling as a sport, some bookmakers still allow you to place money on the biggest wrestling events. Betting on WWE has become a ritual for some every Wrestlemania. For some it has become a painful reminder of the losses that some can occur.

Betting should always be something to be taken with a pinch of salt. While betting companies will want you to see all the victories and big money prizes, that is not always the case. Gambling expert like Casinomech team recommend, always bet responsibly, and only bet what you can afford to lose. WWE betting is risky and despite it’s pre-determined nature, always has the chance of losing you money.

Here is the biggest betting upsets in WWE history, where the smart money wasn’t always right. With a company a servant to the whims of Vince McMahon, it’s shocking that huge upsets were not more an occurrence of the company’s 60+ year history.

5. Brock Lesnar (9-2) over Roman Reigns (Wrestlemania 34)

The first match on the list is one match where no-one saw the winner coming. Roman Reigns had been the poster boy of WWE since the Shield’s break up in 2014. He had waited for his star making moment for years.

He was supposed to be coronated at Wrestlemania in 2015, but Seth Rollins cashed in his Money in the Bank contract to steal the title and rob Reigns of his destiny.

The fans couldn’t have been more uninterested in the match. The WWE betting odds showed Reigns as the huge favourite. However, the fans booed both men and chanted for the match to end.

Brock Lensar won the match with a succession of F5’s to the Samoan, who would win the title off of Lesnar a few months later.

It was one of the worst main events in Wrestlemania history. However, it was brilliant for those who followed the money and bet big on Lesnar.

4. Cesaro (7-1) over Andre the Giant Memorial Battle Royal (Wrestlemania XXX)

Very few would have bet on Cesaro to win the Andre the Giant Memorial Battle Royale – Because he wasn’t meant to be in it!

The Swiss Superman competed on the pre-show that year, losing a tag team title match with his partner Jack Swagger.

Cesaro then entered the inaugural Battle Royale as a secret number 31 entrant, and survived all the way to end. He had some memorable moment, such as throwing Kofi over the turnbuckle for the New Day member’s signature Battle Royale save, and body slammed The Big Show over the top rope to win the match.

With odds of 7-1, a £50 bet would have netted you £350. This was some great odds for a match where the winner could have been anyone.

3. Michael Cole (8-1) over Jerry Lawler (Wrestlemania 27)

Voted as one of the worst matches in Wrestlemania history by wrestling fans, Michael Cole beating Jerry Lawler at Wrestlemania 27 is also one of the biggest upsets.

Michael Cole had been annoying fans over the previous year, turning heel on commentary and isolation himself in a giant glass box called “The Cole Mine”. He became insufferable on commentary, calling people “nerds” and generally annoying everyone who watched the show.

Their match was billed as Jerry Lawler’s first ever Wrestlemania match. Just months after he competed for the WWE Championship against The Miz. Cole, being a non-wrestler, had no hope of winning the bought, or so the bookies thought.

Cole defeated his commentary partner in a match that went over 20 minutes. It was the longest match on the show that year and provided great returns for anyone backing the insufferable commentator.

2. Brock Lesnar (10-1) over The Undertaker (Wrestlemania 30)

Second on the list is of the most obvious ones, with one of the most shocking losses.

The Undertaker, the legendary wrestler who’s career spanned over 30 years, was undefeated at Wrestlemania. The biggest show in WWE history is where he made his name. The Undertaker went 23 years without defeat and overcoming all he encountered.

This seemed to be another paint-by-the-numbers victory for the Deadman. Brock Lesnar was his opponent at Wrestlemania 30, and was announced to very little fan fair. Having just come off victories over The Big Show and Mark Henry, Lesnar’s 2013 had been a lacklustre year, with only a Summerslam match against CM Punk a bright spark to show.

The build up was short. Brock Lesnar was given an open contract by the Authority, in response to being refused a WWE Championship match at Wrestlemania. Whilst his manager Paul Heyman aired his complaints in the ring, the Undertaker interrupted the pair, and the match was set for Wrestlemania.

In shocking fashion, Brock Lesnar would defeat the Undertaker to beat the odds and end the streak. It was one of the biggest upsets in wrestling history. One fan was so sure the Deadman would win that he bet his entire life savings on the match! He lost £35,000 and learned a valuable lesson!

1. Zack Ryder (33-1) over The Intercontinal Championship Ladder Match (Wrestlemania 32)

When he was announced into the match at Wrestlemania 32, nobody believed Zack Ryder would walk out as champion.

Especially not the bookies, who placed 33-1 odds on “Long Island Iced Z” to walk away with “Bad-news” Barrett’s Intercontinental Championship.

The match was chopped and changed in the weeks before the show, with original winner Neville injuring himself on Raw ruining the plans for the match.

The wrestlers in the match were asked to decide who should win the match, and they all decided that due to the years of dedication in the ring, Zack Ryder would win the match. If they’d have put a bet on, they’d have won a pretty penny themselves! With 33-1 odds, a £50 would have netted Ryder fans over £1500 in winnings!

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Mark Perry
Mark, a stalwart in the pro wrestling journalism industry, is the editor, writer, and owner of Pro Wrestling News Hub brand. With an experience spanning over two decades, he has left an indelible mark on the wrestling media landscape. Mark started his journey by covering WWE, meticulously chronicling the ever-changing narratives, players, and game-changing moments in the industry. His knack for in-depth analysis, coupled with a passionate flair for storytelling, made his work stand out, transforming him into a go-to source for dedicated WWE fans. He created one of the first pro wrestling podcasts. Always one to stay ahead of the curve, Mark was there when All Elite Wrestling (AEW) and Impact Wrestling were mere fledglings in the pro wrestling scene. He recognised their potential early on and has been instrumental in bringing their stories, matches, and wrestlers into the limelight. His coverage has been pivotal in fostering the growth and popularity of both promotions. But Mark's journey in the wrestling journalism realm extends beyond writing. He has proved his business acumen and foresight by successfully owning and operating multiple wrestling websites. His entrepreneurial ventures include ImpactWrestling.com and AllWrestling.com, both of which he skillfully developed into thriving platforms before selling them. Mark's blend of journalistic prowess and business savvy is a testament to his multifaceted approach towards pro wrestling coverage. His commitment to delivering quality content, his ability to spot trends and opportunities, and his unwavering passion for the industry set him apart in the wrestling media landscape. Through Pro Wrestling News Hub, Mark continues to be a reliable and influential voice in the wrestling community, delivering insightful content to readers and setting the bar high for wrestling journalism. The passion and commitment he brings to his work continue to inspire wrestling fans and aspiring journalists alike.
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