Sports betting is a very popular pastime for people all around the globe. And while the phrase “the house always wins” is true for the vast majority of the time, there have been some notable exceptions.
In this article, we took a look at some of the biggest sports betting wins in history. Well, the verifiable ones.
Biggest Sports Betting Wins
1. Jim “Mattress Mack” McIngvale won $75 million
Game: MLB World Series
Bet: $10,000,000
We are gonna start our list with what might be the biggest bet ever won.
Introducing Jim McIngvale, better known as “Mattress Mack.” Good old Mattress Mack is a furniture magnate, famous in the Houston area for his… Well, let's call them unique commercials.
In 2022, Mattress Mack placed a ten-million-dollar bet that the Houston Astros would win the world series. And, well, the furniture kingpin was right. The odds were 7.5 to 1, with the Astros playing their sixth game against the Philadelphia Phillies, winning 4-1.
2. Floyd Mayweather won $6.5 million
Game: NBA
Bet: $5.9 million
There can't be a list of the craziest bets ever won without including Floyd Mayweather. Placing six-figure bets is a common pastime for the “Money,” but one of the biggest was the $5.9 million he put on Miami Heat beating the Indiana Pacers back in 2013.
Being one of the highest-paying athletes ever, hence the nickname “Money,” means these kinds of bets aren't that big of a deal for him. Still, the $600,000 he won from the game certainly put a smile on his face.
3. Fred Craggs won $1.4 million
Game: Horse Racing
Bet: $0.4
Fred Craggs deserves his own place in sports betting history thanks to the ridiculous 2,800,000 to 1 bet he made on an eight-leg parlay. With a bet that is, essentially, money he could have found on the floor, Craggs becomes a millionaire overnight.
The funniest thing in the story is that the man wasn't even aware he had won the bet. He actually went to his bookie, placed another, completely unrelated wager, and only then was informed that his life had changed forever.
4. James Adducci won $1.2 million
Game: Golf
Bet: $85,000
And while we're on the topic of golf betting, let's talk about James Adduci.
Now, 2019 was a different time. Then, betting on Tiger Woods was far from a sure win. The odds of Woods winning The Masters were 14 to 1. Adduci, however, liked those odds.
The man recognized something in Woods and believed who could go the distance. He placed $85,000 on Woods and, sure enough, brought home more than one million dollars.
5. Mike Futter won $1.1 million
Game: Horse Racing
Bet: N/A
We believe horse racing deserves a spot on our list. For that reason, we are going to talk a bit about Mike Futter.
Futter put all his trust in his horse, the eclectically named Monty’s Pass. As the proud owner, Futter got roughly $600,000 on his bet and another $500,000 because, well, it was his horse that won.
6. Charles Barkley won $800,000
Game: NFL
Bet: $300,000
Usually, it's Barkley who helps people earn some extra cash from the NFL. This time, he was on the other side, becoming one of the biggest football bet winners in 2002.
During 2002’s Super Bowl, he put $300,000 on the New England Patriots beating the Pittsburgh Steelers.
What also makes this one stand out is that this was Tom Brady’s first big win (even though he was injured and was replaced by Drew Bledsoe).
7. Phil Mickelson won $560,000
Game: NFL
Bet: $20,000
The professional golfer saw something in the Baltimore Ravens way back before they made it big. This kind of trust turned out pretty good for him in the early Aughts.
With one of the biggest sports bets ever put on the Baltimore Ravens, Phil Mickelson took home a substantial half a mil.
8. Erick Lindgren won $340,000
Game: Golf
Bet: N/A
You'd expect a professional poker player to stick to poker. But betting is in Erick Lindgren’s blood, and he famously won over a third of a million over a game of golf.
Back in 2007, Lindgren’s winning sports bet started with a couple of friends challenging him to an intense four straight lines of golf under the blazing Las Vegas summer Sun, carrying his own clubs and shooting below 100! Honestly, this was more a game of endurance than just simple skill and luck.
Lindgren, however, obliged, proved his friends wrong, and took home $340,000.
9. Dave Oancea won $200,000
Game: UFC
Bet: Roughly $165
You know you deserve a place on a list like this when people start calling you Vegas Dave.
In 2015 put an 11 to 1 wager that Holly Holm would beat Ronda Rousey in the big 2015 UFC women’s match.
What makes this especially impressive is that Ronda Rousey was an overwhelming favorite and a media darling at the time. Still, Dave trusted his gut and made a nice bit of cash from the UFC.
10. Peter Edwardson won $150,000
Game: Football
Bet: $60
Another wholesome story revolving around the biggest sports betting wins, this one is about a Welsh grandfather’s faith in his grandson.
When little Harry Wilson was just one year old, Edwardson placed fifty pounds on the boy not only becoming a professional football player but also representing Wales.
Now, whether it was a shared love of football or Edwardson being really into betting and putting some pressure on the boy, we will never know. What we can say is that Harry Wilson became a professional player at the age of 16 and made a lot of people happy that day.
11. Nicholas Newlife won $122,000
Game: Tennis
Bet: $280
Nicholas’s story is kind of tragic, honestly. Way back in 2003, the man was spellbound by Fedarers skills, as many were (just ask David Foster Wallace). The man placed a bet that Federer would win 14 Grand Slams by 2020.
Not only did Federer do that, but he also achieved this by the middle of 2009. Sadly, Newlfie had died just before this win and never got to collect his winnings.
On the brighter side, according to Newlife's will, his winnings were directed to Oxfam International.
12. Tayla Polia won $100,000
Game: NFL
Bet: $5
Now, Tayla’s prize is not as high as most of the wins on this list. However, she deserves a special mention since her winning bet was a measly five bucks. You can barely buy a cup of coffee and a bear claw at Starbucks with that.
With those five dollars, Tayle took on a 15-leg NFL parlay, betting on nine favorites and five underdogs, and a points total. More of a statistical mental exercise than an actual bet — the odds of her winning were 2,000 to 1.
Well, she won. For the price of a Big Mac, Tayla Polia got enough money to send her kids to college and pretty much made US sports betting history.
13. Adrian Hayward won $30,000
Game: Football
Bet: $240
Now, let's talk about some really out-there bets. In 2006, Liverpool's Xabi Alonso made Hayward one happy winner for the sports bet he placed on the Spanish midfielder.
In 2005 Hayward placed a $240 dollar bet (or 200 British pounds) that Alonso, who had been struggling a bit that year, would score from his own half. The odds? A hefty 125 to 1.
Even the best online betting sites will tell you that it’s a gutsy bet. Well, Hayward had guts, and so did Alonso, and in 2006 during the FA Cup’s third round, Xabi scored from his own half and helped the lucky Brit earn a cool twenty-five thousand pounds.
Bonus: Jim “Mattress Mack” McIngvale lost $9.5 million
Game: Superbowl
Bet: $9.5 million
Ok, we know this is an article on the biggest betting wins, but we still believe a loss of this magnitude needs to be reported on. And what makes it even better is that the largest bet ever placed that didn't pan out was made by none other than good old Mattress Mack.
He bet $9 million dollars that the Cincinnati Bengals would win Super Bowl LVI, and, well, they didn't. However, Mattress Mack, known for his eccentricities, set up a huge promotion tied to the game.
Namely, if the Bengals won, he would refund every single one of his furniture customers who bought a mattress or recliner that's worth $3,000 before kick-off. In the end, he made a cool one million off the entire event at least.
Cash in Your Chips
Well, that concludes our article on the biggest sports betting winners. Just remember that not most people don't get so lucky. Betting is exciting, but always remember - everything in moderation.
