Million Dollar Bets: The Biggest Sports Bets Ever Placed

High StakesWhilst the majority of us are content with a cheeky fiver on the racing, or the occasional Saturday afternoon acca, there are some people out there in the world who are putting down ridiculous amounts of money on a bet.

Of course, these are very wealthy people who can afford to lose that sort of money in the first place, but nevertheless, it must be quite an experience to lay down the sort of money we are talking about here.

In this section we’ve collated the biggest bets that we can find, with a minimum bet size of around $1,000,000 (apart from the odd one or two) this makes them mostly million dollar bets at least.

The bets here are shown regardless of whether they win or lose as we’re more interested in the size of the wager than the payout for this page.

We also track the biggest wins and biggest accas in history as well, if that’s what you’re looking for.

Largest Bets in Sports Betting History

Date Bettor Bet Stake Odds Result Payout
30/10/2019 Jim "Mattress Mack" McIngvale Astros to Win the World Series £10,700,000 Lost -
05/11/2022 Jim "Mattress Mack" McIngvale Several Singles on the Houston Astros to Win the World Series £8,226,900 15/2 Won £61,701,750
13/02/2022 Jim "Mattress Mack" McIngvale Two Singles on the Cincinnati Bengals to Win Super Bowl LVI £7,452,180 17/10 Lost -
04/04/2022 Jim "Mattress Mack" McIngvale Kansas Jayhawks to Win NCAA Men's Competition £7,300,000 15/8 Won £12,500,000
11/01/2022 Jim "Mattress Mack" McIngvale Alabama Crimson to win the College Football Playoff National Championship £5,100,000 Lost -
03/11/2020 Unknown Donald Trump to Win Second Term as President of USA £3,943,705 37/20 Lost -
07/02/2010 Billy Walters New Orleans to Win the Superbowl £2,898,245 4/5 Won £5,212,431
06/10/2007 Harry Findlay New Zealand to Win Rugby World Cup £2,500,000 4/5 Lost -
13/11/2022 Drake Adesanya To Beat Pereira £1,622,680 9/20 Lost -
15/01/2023 Unknown LA Chargers to Beat Jacksonville Jaguars £1,159,816 0.01/1 Lost -
01/01/2007 Billy Walters USC to Beat University of Michigan £1,100,000 5/2 Won £3,850,000
02/05/2005 Fred Done Man Utd to Finish Higher than Chelsea £1,000,000 1/1 Lost -
20/01/2020 Unknown Joe Biden to Become President of the USA £1,000,000 8/15 Won £1,540,000
06/05/2023 Jim "Mattress Mack" McIngvale Angel of Empire to Win Kentucky Derby £952,188 9/2 Lost -
27/01/2023 Drake Kansas Chiefs To Beat Cincinnati Bengals £916,147 13/15 Won £1,713,196
18/12/2022 Drake Argentina to Win the World Cup £811,380 7/4 Lost -
22/04/2023 Drake Gervonta Davis to Beat Ryan Garcia £802,810 4/11 Won £1,107,878
12/02/2023 Drake Kansas City Chiefs to Win the Superbowl £580,000 11/10 Won £1,005,000
15/03/2023 Tony Bloom Energumene to Win Champions Chase at Cheltenham £400,000 7/5 Won £960,000

The People Behind the Bets (AKA The Worlds Biggest Gamblers)

Drake

Drake

Biggest Bet: $2,000,000 (£1,622,680) - Adesanya To Beat Pereira (Lost)

Most people would recognise the name Drake. The Canadian is one of the most successful rappers in the world, amassing huge amounts of money from his musical abilities. He also likes to bet huge amounts of money though, and quite often he does so at very short odds too, taking a lot of risk for not much return.

Well known for losing big money, the 'curse of Drake' became something of an industry joke for a while, and even led to sports teams/people being forbidden from being seen with him before big events in case his curse impacted on the result.

Mattress Mack

Jim "Mattress Mack" McIngvale

Biggest Bet: $13,000,000 (£10,700,000) - Astros to Win the World Series (Lost)

Jim 'Mattress Mack' McIngvale is a furniture business owner in Texas, USA, who was initially known for whacky TV ads and catchphrases, but who is almost as well known as a high stakes sports bettor these days.

He ties his bets in with promotions at his store as a sort of hedge, so even if he loses, his store wins. In 2022, he won a record $75 million payout on the World Series.

Billy Walters Big Bets

Billy Walters

Biggest Bet: $3,500,000 (£2,898,245) - New Orleans to Win the Superbowl (Won)

A gambler for his whole life, Billy Walters was born very poor, earned a fortune selling cars, and lost a fortune in the casinos playing blackjack and roulette. Then he got his head around sports betting, and began wagering on an industrial scale.

The man has enough resources to move the line where he wants it with his own bets, and knows exactly how to take advantage of odds movements when they happen. So feared by the bookies is Billy Walters that he even has to place bets via other people in order to get them placed at all, and this explains why he is so secretive about the bets he makes.

Vegas Dave Oancea

Dave 'Vegas Dave' Oancea

Biggest Bet: $305,000 (£207,400) - Denver Broncos to Win the Super Bowl (Won)

Dave Oancea is not a popular man in the betting community, and many have even called him out for being a liar and a fraudster, but whatever you think of him, he has been proven to have placed some of the biggest sports wagers in history.

He doesn't bet himself anymore, but sells picks for hundreds and thousands of dollars to newbie punters who are all hooked on the idea of making their fortunes with Vegas Dave's help. Whether or not he is a genius sports bettor is up for debate, but the guy certainly has a lot of money, so his marketing skills ae unquestionably sound.

Harry Findlay High Stakes Punter

Harry Findlay

Biggest Bet: £2,500,000 - New Zealand to Win Rugby World Cup (Lost)

A man who divides opinion in betting circles, Harry Findlay is one of the most prolific punters in British sports betting. A Londoner with a big personality and an even bigger appetite for high stakes short odds wagers, Harry has won and lost millions in his lifetime, betting on horse racing, greyhound racing, rugby, football, tennis, and more.

He is a colourful character and no mistake, having lived a life worthy of a film script, including owning Denman, winner of the Gold Cup at Cheltenham, amongst other things. His biggest ever loss was £2.5 million, but Harry estimates he has spent more than £20 million in winnings during his lifetime.

How do High Rollers Place Such Large Bets?

High Stakes Betting SlipIt’s a nice problem to have, but one of the issues the people on this list will all have faced, is finding somewhere to accept their bets in the first place.

All bookmakers know how to balance risk, so while huge bets on a single outcome might be tempting for them, if the bettor wins they are going to be heavily out of pocket; in other words, the bets are so big they unbalance the books to the point that the bookie would struggle to rebalance them.

There is no law stating how much someone can and can’t bet, but there are strict regulations in terms of proving a punter’s affordability or source of wealth.

Even if a bookie is willing to accept such a large bet, the person making that bet would have to satisfy the bookie that they had come by that money legally and could afford to lose it.

There are also maximum payouts to consider, which all bookies have in place to protect themselves. After all, if they accept a huge bet on a market they get very little traffic for, they have no chance of balancing their book and are taking a huge risk, so payout caps are put in place to manage this.

For example, even the biggest UK companies will have a payout cap of £1 or £2 million on top football leagues, and this will drop to a few hundred thousand for less popular sports, so making a bet of millions wouldn’t make a whole lot of sense unless the odds were incredibly short.

Bettors with much larger than average wallets will therefore have to make special arrangements with a bookmaker who will take the bet under slightly different terms. If the individual is known to the company they will often have a direct point if contact as they would be seen as a very high value customer, and can negotiate with them on terms, payout caps, and bet size.

Another option is to spread their bet across multiple different bookmakers, so they turn one huge bet into several medium sized bets.

Mattress Mack is a good example of someone who often does this. He will place several bets with several different bookmakers, and often at different points in a season too, in order to build an overall bet total.

There are also some bookmakers out there who sell themselves as high stakes or no limit bookmakers, but they will still have terms, and are not that common in the UK.

As you can see from the table above, most of the 7 figure bets (and even most of those in the high hundreds of thousands), were placed in America, where bookmakers seem happier to take big risks in order to either make big money or gain publicity.

It’s much harder in the UK unless the bet is a private one between friends of colleagues, such as the £1 million wager between Fred Done and Victor Chandler in 2004.