10 Greatest Sports Betting Wins of All Time

betting for newbies

Whether you are a fervent fan of baseball or soccer, you must admit that wagering money on your favorite team doubles the pleasure. This is maybe the main reason why sports betting is one of the most popular ways you can make money in the gambling world.

While some bettors see wagering on sports as a kind of a fun pastime, others take it seriously, even turning betting on various sports events into their profession. Whichever group you think you belong to when this entertaining and profitable activity is in question, we are sure you would want to hear something more about the most incredible amounts of money won at a sportsbook.

We’ve prepared for you a list of ten greatest sports betting wins. After reading this, we are sure you too will start thinking about placing some money on your favorite team.

This list of ours won’t just contain incredible wins money-wise. We will also honor some betting choices that usually go under the “Believe it or not” section.


This one goes out to the Liverpool fans. What seemed to be an uneventful third round of FA cup game between Luton and Liverpool soon became a dream come true, literally. Xabi Alonso scored a fantastic goal from his part of the field, thus bringing Liverpool a sure win of 5:3. This made it possible for Adrian Hayward to walk into a sportsbook and claim his winnings. As it turns out, Hayward had a dream of the exact situation happening a year before. So he went and placed a 200-pound bet that Xabi would score a goal from his half of the soccer field. The bookies gave him 125:1 odds of winning this kind of bet. After this FA cup game in 2006, Hayward was 25,000 pounds richer.


We all know that betting on horse racing is a synonym for sports betting. So we have to dedicate some space here and describe some of the foolishly brave accumulator wins on horses that came true and brought the bettors small fortune.

Let’s first mention the incredible accumulator bet that Fred Craggs made in 2008 on his 60th birthday. He has chosen eight random horses that raced in a different part of the world and made an accumulator bet that contained eight horses. He invested 50 pence in this bet while the sportsbook gave him an incredible 2 million: 1 odds for it. We can only say that Mr. Craggs became a millionaire that day because all of his horses won. The craziest thing was that he selected the horses whose names he liked.


A similar thing happened across the ocean when two bettors placed 50 cents each on “superfecta” bet. This is a kind of bet where you try to guess the placement of the horses in the race. They correctly predicted the top four horses in the race 7 on the Saratoga horse track. Their bold predicament brought them $76,000 each.


Sports betting isn’t always about being unbelievably lucky. Sometimes, you only have to support your team and believe in them, even when times are rough. Eventually, your fidelity will pay out. An ardent St.Louis Cardinals fan is a hero of this winning story. First, he placed a $500 bet that Cardinals will make it to the World Series. At that moment, his favorite was dragging through the league, but somehow, they succeeded. Then, this man placed another bet saying that Cardinals will win the World Series in baseball. The odds of this happening were the same as for a cold day in hell!

Imagine who had the broadest smile on their face when Cardinals became the baseball champions that year. Their faithful fan collected a hefty sum of $375,000.


Another extraordinary soccer bet follows. The African Cup may not be widely popular soccer competition, but it can bring some bold bettors generous winnings. The year is 2010; Mali is playing against Angola and losing 4:0. Eleven minutes before the end, someone places a 5-pound in-game bet that the game will finish in a tie. Then, an amazing streak of goals for Mali follows, and the bettor who predicted this result ends up with 5000 pounds in his pocket.


The following story is a clear example of parental love and confidence. Rory McIlroy was only 15 and a promising golf player when his father decided to wager an astonishing 200 pounds, betting that his son would win the British Open Championship in the following ten years. When Rory achieved this goal in 2014, the sportsbook had to pay out 100,000 pounds in winnings to his father and an extra 80,000 pounds to their friends who took a ride on Gerry’s wave of confidence.


Another bettor that successfully foresaw the future was Richard Hopkins who placed a 200-pound bet on Lewis Hamilton winning both major competitions in Formula 1. But what is so unusual here, you might ask? After all, we all know that Lewis Hamilton is a great Formula 1 champion. Well, you see, Mr. Hopkins made this bet when Hamilton was only 13 years old.

You can only imagine the odds of this bet. Anyway, the amount of money won for this prediction was 165,000 pounds.


Darren Yates became the hero of the day in 1996 when he managed to win big at the Ascot. This man decided to make a selection of seven Frankie Dettori’s races and make one bet — that Dettori would win them all.

Dettori himself doubted this was possible, even though he was considered a favorite, and he predicted winning only a couple of races before the event started.

Mr. Yates went to play football with his friends after placing this crazy bet, and since his team lost 4 to 0, he returned reluctantly to the tracks, only to find out that he had become richer for over half a million pounds. Frankie Dettori managed to win all seven races.


Mick Gibbs had some experience of winning big on accumulator bets in soccer games all over Europe. The unforgettable win, however, happened in 1999, when Gibbs made a selection of 15 different soccer games all over Europe. He was not surprised to see that 14 games ended the way he predicted. However, the only game left was a Champions League match between Bayern Munich and Valencia. Gibbs needed Bayern to win, which happened after penalties. This amazing outcome made Mick Gibbs richer for half a million pounds.


As we have mentioned at the beginning of this article, many people turned sports betting into their profession. We are going to finish this list by mentioning one of those bettors.

Billy Walters was a poker pro before he decided to apply his poker playing skills to sports betting, which has brought him loads of money. Walters advocates the theory that sports betting isn’t just about luck. He claims that it demands developing certain skills, just like poker playing does. So he always analyzes the information he gets on various sports events before he places his bets. That’s how the successful prediction of the Super Bowl game outcome came to fruition. He calculated the odds, taking all relevant info into consideration, and decided to place an incredible $3.5 million on the team which was seen as the underdog. Needles to say that Billy’s strategy worked — his team won the game, bringing him an unknown amount of money.

Final Thoughts

There you have it. This is a short compilation of the most impressive winnings at sportsbooks. Some of these winners made random choices relying on luck, while others analyzed all the info they’ve gathered on the event in question in great detail. So whatever you may rely on when placing a bet, we wish you the best of luck.

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