The Biggest Betting Upsets in Recent History

By in Sports & Betting on
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Trump Coco Gauff Holy Holm

As many regular punters will know, it’s difficult to beat the bookmakers. Sports betting sites set their odds based on statistics, and most of the time, the favorites win.

However, every once in a while, a black swan event will happen. This is an event that’s so improbable that nobody could have seen it coming. In betting, the bookie typically loses lots of money when black swan events occur, and lucky players who took a chance by placing a wager on the event win big.

“The central idea in The Black Swan is that: rare events cannot be estimated from empirical observation since they are rare” – Nassim Nicolas Taleb

In this piece, we’re going to explore some of the rarest events in betting history, true black swan events which broke the bookies and made lots of lucky players a heck of a lot richer than they were the day before.

The Biggest Betting Upsets in Recent History

1.   Leicester City Wins the English Premier League

If you had asked veteran English football fans what the chances were of Leicester City winning the English Premier League at the beginning of the 2015/16 season, they probably would have laughed in your face before saying “impossible.”

The bookies didn’t quite rule it out, but they did put 500/1 (+50,000) odds on it, meaning that it was considered highly improbable, to put it mildly.

Yet, on May 2nd, 2016, Leicester won the EPL when rivals Tottenham blew a 2-0 lead over Chelsea to finish with a 2-2 draw at Stamford Bridge.

This was the team’s 111th season playing in the various English football leagues. If that doesn’t prove that dreams can come true after relentless persistence and despite all the odds being against you, I don’t know what does.

2.   Donald Trump Becomes US President

There are few names in the world of politics that evoke such a broad range of emotions as Donald Trump. Whatever you think of the US President, there’s no doubt that he pulled off one of the biggest political upsets of all time when he defeated Hillary Clinton in 2016.
Donald Trump Podium

Sometimes, I wonder if some gamblers are either crazy or have insider knowledge of something common folk don’t. One such gambler would be the British man who placed a £200,000 wager on Trump to win just a couple of days before the election.

By this stage, the bookmakers had already slashed the odds due to the huge number of longshot bets on Trump. However, the punter still won £500,000 on top of his original stake when Trump shocked the world.

Did he know something we didn’t at the time? Who knows. Either way, his courage to wager on what became one of the biggest betting upsets paid off.

3.   Coco Gauff Defeats Venus Williams at Wimbledon

What are the chances of a 15-year-old beating one of the greatest champions of all time in any sport? Close to zero, right?

That’s what most would have said during Wimbledon in June 2019. Coco was 1500/1 (+150,000) going into the tournament, yet she stunned Williams and the world on this historic day.

I couldn’t find the exact odds for Coco to win the match, given the time that has passed. All I know is that you’d have made a heck of a return if you had wagered on her to win. These longshot bets are always worth a wager of a few bucks.

4.   Holly Holm Destroys Ronda Rousey at UFC 193

In the couple of years running up to 2015, Ronda Rousey looked unstoppable. She dominated opponents, finished them in seconds, and even secured herself a part in the Fast and the Furious movie franchise. She was on top of the world.

That all came crashing down when underdog Holly Holm, who the bookies had as a 7/1 (+700) underdog, defeated her in two rounds ending with a brutal knockout kick.

Holm utterly dismantled Rousey, who didn’t look like she stood a chance from the beginning of the fight, and became queen of the octagon. One lucky guy made $240,000 betting on Holm.

MMA is one of the best sports to bet on if you want to place longshot bets since one significant strike can change everything in an instant. One of the biggest betting upsets of all time could occur spontaneously, so I always drop $10 or $20 on underdogs at major UFC events. In a fight, you just never know what will happen!

Going a Bit Further Back in Time…

I did title this piece the biggest betting upsets in recent history, but recent is all in your perspective, so I decided to go back a little further than just the last 10 years.

5.   Greece Wins Euro 2004

A few big teams dominate European football. Italy, Spain, Portugal, France, England, and Germany are always contenders to win the Euro championship. However, in 2004, Greece stunned the world by winning the tournament.

What were the odds of such an event happening? 150/1 (+15,000) going into the tournament. That made a nice return for those brave enough to bet on it.

This one particularly sticks out in my mind because of opportunity loss. I was only a young punter making my bones at the time, but I had a feeling about Greece for some unknown reason. My gut feeling told me they would win, but my father convinced me not to place the bet. Lesson learned! There is such a thing as a punter’s premonition, and don’t listen to the naysayers who tell you otherwise. The next biggest betting upset could be right around the corner!

6.   Buster Douglas Stuns Mike Tyson in Tokyo

Few fighters of “Iron” Mike Tyson’s caliber have ever or will ever grace the boxing ring. At 20 years old, this kid from Brooklyn was world heavyweight champ and the most feared fighter on the planet.

Tyson’s storied history is well-known, but despite the drugs, parties, womanizing, and all that went with being so incredibly rich and famous at such a young age, few gave any of his opponents a chance. He was just too powerful and too aggressive…until Buster Douglas came along.

The two squared off in 1990 in Tokyo, Japan. Tyson was undefeated in 37 fights, and the bookmakers gave Douglas odds of 42/1 (+4,200) of beating Tyson. In the 10th round, the unthinkable happened when Douglas knocked Iron Mike out cold with a vicious flurry followed by a straight left.

It just goes to show you that fights are some of the best opportunities for longshot bets.

7.   Leon Spinks Knocks out “the Greatest”

When I said that few fighters of Tyson’s caliber have ever graced the boxing ring, one of the exceptions I had in mind was Muhammad Ali. Largely considered the greatest of all time, Ali probably saw Leon Spinks as just another young wannabe trying to take down the champ.

Yet, he did take him down. Spinks shocked the 2 billion viewers of the fight when he won by split decision. The bookmakers had given him odds of 10/1 (+1,000) going into the fight, which was only his eighth pro bout.

Ali did win his belts back in the rematch, but that’s not to take away from Spinx’s historic victory.

8.   The US Hockey Team Defeats the Soviet Union

Of all of the events listed in this article, this is probably the greatest upset of them all. This was deemed borderline impossible by bookmakers who set the odds of an American victory at 1,000/1 (+100,000) odds. For those of you who don’t know, that means they figured the probability of the USA winning was 0.1%.

It was 1980, and the Soviet Union’s dominance of hockey in this era was a well-known thing. They had won the gold medal in five out of the previous six Winter Olympic Games. Hockey fans gave the young American team consisting of little more than a few college players and some amateurs no chance of beating the mighty Soviets, but the history books will forever show that they did. This game is known as the “Miracle on Ice.”

Sports Illustrated named this event the top sporting moment of the 20th century. That’s a heck of an achievement and is further proof that improbable bets are always worth a shot.

Five Sports Betting Tips to Help You Win More Often

I did make money from a couple of the events on this list, but the truth is that longshot bets rarely pay. I’ve decided to finish this piece by giving you some top sports betting tips.

1.   Learn to Hedge Your Bets

If you’re going to place a larger wager on the favorite to win a match, fight, or event, it’s always a good idea to hedge with a smaller bet on the underdog. This is particularly true when the odds of the underdog winning are 10/1 (+1,000) or greater. This way, you have a good chance of making back your money, or even winning money should the improbable happen.

2.   Only Place Educated Wagers

It’s a bad idea to bet on sports you don’t have the first clue about. For example, I don’t bet on winter sports or motor racing because I don’t follow them closely. I bet on soccer and fights because I follow them religiously. However, betting on what you know and understand is just the first step. The second phase is to make use of the various betting stats centers which the top online betting sites offer. You’ll find evidence of historical performances and much more, which can help you make educated bets.

3.   Take Advantage of Free Bet Offers

Lots of online sports betting sites offer free bets to new players. Even if you already have a favorite online bookie, you should use the free bets at other sites regardless. I always take free bets with fair terms and use them to hedge my bets. For example, I claimed one such offer and bet on Conor McGregor to beat Floyd Mayweather while I made a bigger bet elsewhere that Floyd would win. Since it was a free bet, I lose nothing when the inevitable happened, and I’ve gone on to use that betting site a few times since.

4.   Think Outside the Box

The vast majority of sports bettors will place outright bets, trying to predict who will ultimately win the event. There’s nothing wrong with that, but you should be aware that you have many more options these days. You can place accumulator bets which can pay tens of thousands for bets worth a few bucks, or live/in-play bets on in-game events such as penalty kicks. Feel free to think outside the box and place exotic wagers.

5.   Manage Your Bankroll Effectively

Most punters are amateurs, and that’s why most don’t make money consistently. You should treat your bankroll like capital in a business and manage it as such.

Let’s say that you start with a bankroll of $1,000. It’s a smart betting strategy to never risk more than 1% of your capital on a bet. In this case, that would be $10. You can scale up or down depending on how much you plan to bet, and as you win and lose.

It’s also worth remembering that you can lose the majority of your longshot bets and still make money. If you start with a $100 bankroll and lose 9x $10 bets (-$90), but win $120 on the final $10 bet at odds of 12/1 (+1,200), you’ll be up $20 from where you started.

Now, you’ve been inspired by some of the biggest betting upsets which paid, and you have these top betting tips to help you succeed. The only question left is, what will you bet on today?

Oliver Hughes

Based out of London, I began freelance writing for the UK section of GamblingSites.org in October of 2019. Having worked in the gambling industry for over 10 years, I now have the pleasure of adding this site to my list of accomplishments as a casino writer. ...

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