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Top 10 Biggest & Most Craziest Parlay Bets Ever Won

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Feb 15, 2022 05:02Andrej Trajkovski

Some experienced punters say that if a parlay doesn’t promise a payout worth two times the bet, then it’s not worth playing. Most people agree with this statement, but some bettors are taking this to another level and placing crazy parlay bets hoping to become rich overnight. Well, guess what? Some of these people made it!

We are not sure whether a betting strategy like this makes sense, but one thing is for sure – the big parlay wins that we are about to present in this article are life-changing events. To be honest, some bettors have placed relatively significant amounts of money to get these crazy payouts. Still, others invested just a few bucks and went from rags to riches.

Another thing that you should know is that some of these punters have used popular betting systems while others have created their own. So, if you think that there’s a magic formula that can help you, you are wrong. In most cases, it’s all about following your instinct and, of course – having fun! Anyway, let’s check some of the biggest parlays ever won so you can get a better idea of what we are talking about here.

1. $25 bet for a $104,000 win – Vicksburg, Mississippi (2019)

Now, this is what we call making a profit. A player who visited the Riverwalk Casino in Vicksburg, Mississippi, decided to place a very long 20-leg parlay. He has selected NBA and NCAA basketball matches. Interestingly, he covered several betting options, including money lines, over/under, and point spreads. The good news is that all his predictions were correct.

Another thing that’s fun is that he diversified his slip by throwing some underdogs to the mix too. As a result, he multiplied his initial investment by 4160 times. In other words, he turned his $25 into a $104,000 win. Sometimes it’s difficult to guess the outcome of two matches, but this guy made it with twenty!


2. $604 bet for a $998,000 win – King of Prussia, Pennsylvania (2021)

There are situations when you have to play big to win big. In 2021, the Valley Forge Casino Resort saw the biggest parlay ever won on their ground. This time we have a betting slip with 15 teams. Once again, we are looking at basketball teams from the NBA and NCAA.

Also, some of them are point spreads, while others are money lines. Imagine the amount of luck you need to see all these matches come through. Some people say that this is one of the craziest parlay bets they’ve seen, given the amount of money placed. Why $604? Why not $600? We are not sure, but we are confident that the punter who did it is happy.


3. $3 bet for a $2 million win – Exeter, UK (2011)

We thought these things could happen only in movies, but we were wrong. Unlike many other successful bettors, the person with the biggest parlay win (at least in the UK) decided to share his identity. Steve Whiteley took a day off, hopped on a bus, and went to Exeter, where he used just $3 to place a bet on the six daily races. He guessed all the winners even though most of them were underdogs (including a horse who lost its last 26 races). This parlay helped him win the jackpot, turning his $3 into a stunning $2 million. He may not be one of the richest gamblers of all time but we hope he used his new wealth to upgrade his life forever.


4. $500 bet for a $115,000 win – Somewhere in the US (2015)

Who says that big parley wins are possible only when you bet on basketball or football? An anonymous punter won a huge prize worth $115,000 thanks to his bold $500 bet back in 2015. He used the nearest Willian Hill betting shop to cover eight MLB matches. As you can see, MLB can be pretty profitable if you know how to play on these teams. In addition to clubs, this bettor played on duels between specific players. Not all the matches went smoothly, but in the end, he made the correct predictions and walked away with a prize worth 232 times his initial bet.


5. $100 bet for a $41,000 win – Somewhere in the US (2020)

Now here’s an example of an NFL fan with excellent prediction skills. He was either an Eagles or a Packers fan because his parlay included bets focused on this duel only. So, there were no other sports involved or even other teams from this American football competition. Maybe the player wanted to know the outcome right away because placing bets on different matches can postpone the final result for hours or even days in some cases. This interesting 7-leg parlay included a spread bet, scorers, passing yards, receiving yards, and rushing yards bets.


6. $68 bet for a $101,000 win – Peterborough, UK (2008)

This has to be one of the craziest parlay bets we’ve seen. When the famous Formula 1 driver Lewis Hamilton was 13 years old, he was a successful go-kart driver. That’s when Richard Hopkins decided to place a bet involving this world-renowned driver. Namely, this parlay predicted that Hamilton will win his first race before he turns 23, and he will become an F1 champion before 25. How crazy is that? Well, it’s not crazy because Hopkins turned his $68 bet into a $101,000 prize. We should mention that this bettor was a go-kart driver, too, and it seems that he noticed Lewis’ talents on time. Interestingly, he’s still a passionate bettor and works as a freelance journalist.


7. $84 bet for a $750,000 win – Morecambe, UK (1996)

This one is an oldie but a goldie. In 1996, Frankie Dettori was a successful horse jockey, but even Frankie didn’t think he could win all seven races at Ascot in one day. The only one who thought that something like that was possible was Darren Yates, a man who admitted that he was a compulsive gambler after winning this incredible parlay and striking one of the biggest parlays ever won. The odds were just above 25,000 to 1, but Yates still did it. Unlike many other bettors, he decided to use this small fortune to create a property and development business. In the end, Darren made it and sold the company for over 27 million dollars! This is a piece of good advice for those wondering what to do with their big wins.


8. $0.5 bet for a $130,000 win – Somewhere in Pennsylvania, US (2022)

Truth be told, this is not the biggest parlay win we’ve seen, but it’s one of the craziest. First of all, who places a $0.5 bet? Some bookies will not accept a stake that’s so low. Fortunately, this bet was accepted, and the lucky punter won a prize that’s worth over 260,000 times his original bet. Imagine what would happen if he placed a $2 stake? In addition, we should mention that three people placed the same bet, so the bookie had to pay $130,000 three times that day. This was a 6-leg parlay with first basket bets. It had 6 names on it, including some that were not really favorites for the first basket. Judging by the size of the stake, we would say that these guys were just testing their luck (and the test was positive!).


9. $15 bet for a $1,400,270 win – Somewhere in the UK (2019)

Online betting makes it even easier for players to come up with innovative bets. Sometimes these bets include several sports like in this case. The creative punter used Betfair to place a parlay with four golf players and two soccer teams. Picking a gold tournament winner is often like picking a horse racing winner – it’s not easy. So, how lucky does one have to be to pick four golf tournament winners at once and put two soccer match-winners on top? Since his parlay was diverse, the player had to wait for a few days to discover that he had become a millionaire. It was worth it!


10. $5 bet for a $100,000 win – Las Vegas, US (2015)

Betting is fun, and that’s why we have so many casual bettors. When Tayla Polia placed a 15-leg NFL parlay in 2015, she was not very careful because she didn’t understand some of her picks. She later claimed that the spread she chose for the Giants (+5) was a wrong choice because the Carolina Panthers won by three. Obviously, she didn’t know that it was alright even if the Panthers won by four. So, it turned out that this was the right pick, just like the other 14 on the list leading her to one of the biggest parlay wins. Another thing that we should mention here is that the odds were 20,000 to 1, but these are just numbers that don’t mean much when you feel lucky!

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Andrej Trajkovski
Lady Liberty
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As a gambling editor, Andrej aims to provide readers with everything new from the world of gambling. Since he is our columnist, his topics are often a bit more extensive and fun. Whether it’s analysis on the reunification of Ireland, Spotify gambling playlists, or history posts, he gets the job done.
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