Throughout history, we’ve witnessed some of the craziest outcomes for some of the most unexpected bets ever made. In fact, some bets could’ve earned you a fortune worth retiring with if you happened to make them in time. In this article, we’ll be reviewing some of the most famous bets that you could’ve made and earned you a fortune if you made them in time!


Keep in mind that, in some cases, you might still be able to make some of these bets as the bookmakers are offering similar odds for some of these events happening again. There’s a good reason why, though: it’s very unlikely for any of this happening once more except, perhaps, Federer winning once more!

Leicester City Winning the Premier League

Anyone who was mad enough to place a bet on Leicester City to win the Premier League in the 2015-2016 was lucky enough to win a massive sum of money. The outcome of such a bet was so unlikely that some bookmakers offered as much as 5000-1 odds on it happening. Even our guide to bet on football wouldn’t have helped much in this case!

As the season went on, some bookmakers offered payouts worth 2500-1 to encourage people to cash out while they were on top, as it was becoming far more likely that Leicester clearly had a chance to take the glorious prize of a PL title as the season ended.

When it happened, reports from all over the world started showing how some lucky people who wagered small sums of cash managed to multiply it. There was a British man who trusted Leicester so much that he placed a €100 bet on them winning the league that season, which turned into a €500,000 profit after it actually happened!

This still remains as one of the largest sporting upsets of all time and the most glorious Premier League run in the history of English football. Will it happen again and will you be able to predict when to place a large enough bet to make a profit on it?

Tiger Woods to Win the 2019 Masters

This bet might’ve not been a huge-paying one to make if the tournament had happened 10 years before, but in 2019, Tiger seemed like a shadow of his former self. Some sportsbooks like William Hill were paying out as much as 14/1 for Tiger to win the competition, which meant that a bet of €1000 would’ve gotten you back as much as €14,000 worth of rewards!

There was someone, in fact, that placed an €85,000 bet on Woods to win the tournament, which also happened to be the first-ever sportsbook bet that the man had ever placed. It made him a millionaire as well, as he came back home with a fortune of €1.2 million after Woods shook the world to win yet again at a professional sports tournament.

Real Madrid Winning Three Back-to-Back Champions League Titles

Even though Real Madrid did have a good enough squad to win Champions League titles in a row, no one expected them to actually go ahead and win two CL titles back to back, let alone a third one, when two in a row hadn’t been achieved by then yet. When Zidane took charge of the Merengues and lead them to three CL titles in a row, almost no bookmakers were paying less than 200-1 for that to happen.

The odds of something like that happening again are very low as winning the competition requires a ton of consistency as well as an unmeasurable amount of luck, but should any team happen to do it again, it could earn some lucky bettors quite a large fortune.

This is one of those bets that you might want to place if you truly feel lucky and you want to bet a small amount of cash in an unlikely outcome. Just be sure that the casino or sportsbook in which you’re going to bet offers good odds, as this is one of those bets that you’ll most likely end up losing unless something really crazy happens!

An 8-Horse Parlay Bet

Placing an 8-horse parlay bet is one of the most insane things that you can do as a gambler, especially because of how darn unlikely it is for something like this to actually happen.

There was a case of someone in Britain, though, who happened to place a cheeky small bet on an 8-horse parlay, expecting nothing in return, but doing it only for the sake of fun as it was the guy’s birthday.

Little did he know that his small bet would net him a fortune of €1 million, which he was paid through the William Hill offices in England. In fact, his parlay bet would’ve been worth a staggering €1.4 million, but William Hill has capped player wins at a million on these types of bets. An insane amount of money, nonetheless!


Crazy Playoff Parlays Throughout History

Guessing the outcome of a playoff is crazy – regardless of the sport upon which you’re looking to place your bets on. There are just too many factors that come into play at the finals of any competition and some of them could completely change the way you look at the sport for good.

That’s why Playoff parlays tend to give you some of the best payouts in the industry. Guessing the outcome of some of these bets will completely change the way you perceive sports and could give you massive sums of money in return.

Let’s take a look at the New York Giants run in the NFL back in 2007. The Patriots were unbeaten and they even managed to beat the Giants in the regular season, but Eli Manning had other plans for the New Yorkers as they headed into the Super Bowl and pulled one of the craziest upsets in the history of the sport.

The event didn’t only go down in history but it also filled the pockets of some very lucky gamblers all over the planet!

Betting on Federer to Win – Back in 2003!

Sure, if you’re telling us now that betting on Roger Federer would be a semi-safe bet (let’s take Djokovic into account for a second, too), we would tell you that you’re right. However, back when Federer hadn’t made his way into the global tennis scene, it was highly unlikely for someone to place a bet on him winning anything.

In fact, back in that Grand Slam that he won in 2003, some houses were paying 60-1 for him to win it. No one really expected this newcomer to pull any surprises, but he did – and some people actually placed bets on it to happen.

Had you happened to place a cheeky €10 on Federer winning that competition back in the day, you would’ve walked away with €600 worth of winning money. An insane outcome indeed, but not one that many predicted.

Rory McIlroy Winning the Green Jacket in his First 10 Years as a Pro

Bets like this one are not likely to be made, but there was a man who trusted McIlroy so much that he actually placed a bet on him winning a tournament in his first 10 years as a pro – and that was his own father. The man had so much trust in his son that he placed the bet that earned him quite a significant sum of money back in the day!

The thing is, to place bets like this one, you would need to speak to bookies so they can give you the odds for something like this to happen. Not many sportsbooks have these bets available, so you would have to directly talk to them to give you the odds on a rookie producing such a feat!

Where to Place These Bets? – The Best Sportsbooks

Now that you’ve seen what sportsbooks are capable of producing, chances are that you’re keen to dive straight into the action to claim the most lucrative of rewards out there.

We know how keen you are to place your wagers, but hold onto your hats: we’re also going to tell you all about the best online casinos that have sportsbooks so you can place the best bets out there and win a fortune on these unprobeable outcomes.

Betsson Casino

When it comes to world-class, complete online casinos, you will hardly come across anything better than the majestic Betsson website. Here, you will find an amazing sportsbook and some of the best features that any online casino could give you, alongside casino bonuses that fill your account with free bonus cash that you can use to spend on the best games on the planet.

You will also be able to claim free bonus money that you can spend on the site’s sportsbook. Who knows? You might place a lucky bet with the free bonus cash that you’re given and walk away with a large profit without putting much of your own cash on the line – if any at all!

Play at Betsson Casino


William Hill Casino

The William Hill Casino is another fantastic website that will put you on a roll towards adventure if you’re looking for a unique experience in an online casino wit ha quality sportsbook. William Hill is known to offer some of the craziest outcomes out there, along with Paddy Power, so this is the site that you’ll want to visit if you’re looking to make one of the crazy bets that we talked about in this article!

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