Top 5 biggest winnings in betting history

If we’re being 100% honest – we all enjoy a punt or two on the odd sports event. Of course, some go a little more extreme than others, and we have a feeling that these sports bets will shock you. At the time of writing, we’ve managed to shortlist some of the largest and most courageous sports bets that have paid out (big time), and some of the stories behind them are almost too good to be true. So without wasting any time, let’s kick things off with one of the most impressive of them all. Before we do that however, we thought we would share some of the best football betting sites in England.

Top 5 biggest winnings in betting history

Tayla Polia – 15-leg NFL Parlay

Parlay betting, or accumulator betting as it is known in various parts of the world, is the riskiest form of betting that currently exists. This is because a parlay bet requires that every single prediction you make needs to come true so that you receive any payout at all. As you can imagine, the more legs you add to a parlay bet, the more unlikely it is to pull through – which is what makes this one so amazing. Just a few years ago, Tayla Polia, on her second-ever sports bets, placed a 15-leg parlay on a series of NFL games. This consisted of six underdogs and nine favourites, resulting in total odds of 20,000-1.

With these kinds of odds, you’d be forgiven for thinking that this is near enough impossible to win the bet. But sure enough, Polia laid down a $5 wager and ultimately received a payout of $105,000! This is one of the biggest parlay returns ever recorded, and it’s pretty sensational that this parlay consisted of 15 legs – since it’s hard enough to win a parlay that has even 3 or 4 different legs! Whether Polia has tried to repeat this feat since is somewhat of a mystery, but we have no doubt that this colossal return was enjoyed to the fullest.

James Adducci – Tiger Woods winning the 2019 Masters

If you follow golf, you will probably be familiar with the name Tiger Woods. Back in his heyday, Woods was an absolute force to be reckoned with, but due to a series of personal and even professional problems – he really fell off the wagon at one point. Anyway, this essentially meant that Woods didn’t have a great shot at taking home a trophy as prestigious as The Masters, but one gutsy punter didn’t shy away from backing the great one. In fact, he went in rather heavy with a stake of $85,000, and this was accepted at odds of 14-1 at William Hill. Of course, not many people have that amount of cash sitting around to back such a risky market, but James Adducci clearly did, and it paid off.

Woods defied the odds and played a stellar tournament to ultimately win the event, and this meant that Adducci received a payout of $1.2 million. And if you thought that the fairytale was over – this was the very first wager that Adducci had ever placed.

Do you believe in beginners' luck? You probably will after this story!

The Top 5 biggest winnings in betting history

Vegas Dave – Kansas City Royals

To state the obvious, Vegas Dave isn’t everyone’s cup of tea. This rather brash and outspoken gambler isn’t shy about his betting activities, and as much as he is a character that is difficult to warm to – we can’t help but respect this bet that he made on the Kansas City Royals. For this story, we need to jump back to 2015, where the Kansas City Royals were listed at 30-1 to win the World Series. These odds were apparently too good for Vegas Dave to pass up, and he wandered around multiple Vegas casinos to lay down a total of $100,000 on this outright market. As they say, the rest is history, and the Kansas City Royals miraculously won the World Series – netting Vegas Dave a total return of $2.5 million.

For us, the best part of the store is that he then had to go and collect his winnings from the 15 different casinos that he had placed the wager at. Hopefully, he had a good security team with him when he was doing so, as he had made it rather public that he had managed to win such an amount.

Charles Barkley – Patriots Super Bowl

Charles Barkley – everyone’s favourite TV host when discussing the NBA and all of its stories. But as much as Barkley is a bit of a character on the TV, it would seem that he likes to place the odd wager or two as well. Sure, he has the money to do it, and in 2002, he backed the New England Patriots to win the Super Bowl, with a total stake of $500,000. That’s a pretty gutsy bet by anyone's standards, and despite the 14 point handicap that most bookmakers were offering, Barkley still went for the Patriots getting the win. His courage was subsequently rewarded, with a profit of $800,000 when the Patriots managed to upset the odds and win their very first Super Bowl crown.

Richard Hopkins – Lewis Hamilton Futures

The final wager we’d like to discuss is arguably the biggest fairytale story of them all. In 1998, as rumour has it, Hopkins took his kid to a local go-kart track where he then discovered a promising young driver by the name of Lewis Hamilton. Upon witnessing Hamilton’s skills, he ran out to the bookmakers to bet that Hamilton would win a Formula 1 Grand Prix event by 23 years of age – at 300/1 odds, which came through. But this wasn’t enough for Hopkins, as he also laid down a bet that Hamilton would actually become World Champion by the same age, for which he received odds of 500/1. Amazingly, both bets paid off, and this netted Hopkins a payout of £165,000 from just a total stake of £200.

If you are looking to bet on the performance of footballers in the Euros, here is an updated list of the Best African X1 Players that you could have a look at.

Gavin is a full-time copywriter based in the UK and has developed in-depth knowledge of the igaming world by working in the betting industry for over five years. During this time, he has written thousands of articles covering various topics, including bookmaker reviews, ‘how to’ guides, bonus comparisons and much more.