The Biggest Upsets in Online Gambling History



Gambling is full of upsets and non-obvious outcomes, whether you’re playing at Kansino Casino or betting on sports. While the house usually wins in the long run, there have been some truly monumental moments where the players managed to beat the odds and walk away as unlikely victors.

In this post, we’ll take a look at some of the most earth-shattering, odds-defying upsets in the history of internet gaming and sports betting. From single bets that won millions to underdogs smashing expectations, these are the moments that proved anything can happen with a little bit of luck.

The Unsinkable Titanic Ticket

In what is likely one of the most famous bets of all time, a bold British woman named Jess Willard managed to turn tiny odds into an enormous windfall with a prop bet on the Titanic. The year was 1912, and the brand-new RMS Titanic was prepping for her maiden voyage.

Hype around the massive ocean liner was through the roof, with papers calling her “unsinkable.” When Willard heard about the Titanic mania, an idea struck – she decided to place a bet that the ship would sink on its first journey across the Atlantic. The odds were a staggering 50 to 1, so she put a modest £100 on the bet.

As we all know, the Titanic infamously struck an iceberg and sank four days into her first voyage, killing over 1,500 people. It was a tragedy of epic proportions, but for Willard, it meant winning £5,000 – the equivalent of over £500,000 today! Her long-shot bet earned her a fortune and cemented the Titanic’s place in gambling history.

The Rise of the Underdogs

While individual bets like Willard’s demonstrate how upsets can happen, some of the biggest shocks in online gambling have come in team sports when perennial underdogs somehow manage to defy expectations. The many upsets in sports like football and basketball have proven that anything can happen when the underdog gets motivated.


In the world of American sports, the ultimate underdog story has to be the 1980 U.S. Olympic hockey team. Dubbed the “Miracle on Ice,” this young amateur squad managed to defeat the mighty Soviet team, who had won gold medals in 6 out of the last 7 Olympics. The U.S. team was given only a 2% chance to win, making their victory all the more miraculous.

More recently, we saw the ultimate underdog tale in the NFL when the St. Louis Rams won their first Super Bowl in 2000. The Rams were heavy underdogs against the Tennessee Titans, who were favored by 7 points. But with MVP Kurt Warner leading the way, the Rams shocked the football world by winning 23-16 for one of the biggest Super Bowl upsets ever.

Mega Moolah’s Millionaire Maker

The online Theoverviewscasino Mega Moolah has created some of the internet’s biggest gambling winners thanks to its ever-increasing progressive jackpot. The jackpot starts at $1 million and keeps rising with each bet until somebody finally triggers the bonus round and wins the massive prize.

In 2018, Mega Moolah entered the record books when it awarded the largest online slot jackpot ever to a player named Jon Heywood. The British soldier decided to play the Arabian-themed slot before going to bed and incredibly managed to hit the jackpot, winning an astounding £13.2 million!

With such an astronomical prize, Heywood understandably thought it was too good to be true. But after checking with customer support, he realized he had just won over $17 million on a single slot spin. Mega Moolah has produced many millionaires, but none quite as shockingly lucky as Heywood.

When the House Loses Big

While players cashing in big is always exciting, some of the most satisfying upsets happen when the gambling providers themselves lose huge sums. These epic losses remind us that even the casinos and bookmakers are vulnerable to getting it wrong sometimes.

One of the most famous of these losses came in 1990 at the Caesars Palace Casino in Las Vegas. A high roller named Archie Karas arrived with just $50 in his pocket but proceeded to embark on an incredible winning streak at the baccarat table. Karas managed to turn his tiny bankroll into over $40 million in winnings – the biggest loss ever for a Vegas casino at the time!

Even more recently, some betting companies lost millions in the 2018 FIFA World Cup when they failed to predict just how far Croatia would go. The bookies thought Croatia had no chance in the semis against England. But led by Luka Modrić, the Croatians shocked England 2-1 in extra time before eventually falling to France in the final. Sportsbooks worldwide took a bath on the Croatia payouts.

When Lightning Strikes Twice

Of course, the rarest of upsets are those when a person manages to beat the odds not just once, but two times in a row. These back-to-back shockers are almost unheard of, which makes them legendary when they do occasionally happen.


One of the best examples came back in 2003 when an insanely lucky Australian man named Peter won the lottery twice in the same raffle. The odds of winning any lottery are usually well over 1 in a million. So, what are Peter’s odds of winning twice in a row? Roughly 1 in 10 to the power of 21! Yet somehow, fate smiled on him, and he nabbed two top prizes in the same drawing.

Similarly, a British woman named Violet Large scored not one but two massive online slot jackpots within the span of a single month. Large first won close to £500,000 while playing the Beach Life slot. Then, just weeks later, she spun the slots again and triggered another half-million-pound windfall. Talk about luck!

The Thrill of the Upset

While the house usually has the edge, these crazy stories show how unpredictable internet gambling can be. You just never know when a perfect storm of luck and skill will lead to someone walking away with a massive, life-changing score against all odds. That unpredictability is part of what makes gambling so thrilling.

So next time you log in to play the slots, bet on your favorite team, or join the baccarat table, remember – you could be moments away from making history with the next big upset! The underdog might just have its day if lady luck is on your side.



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