The Biggest Ever Sports Bets to Ever Come in?

Date Created: Sep 25
Written by Jerico

The popularity of sports betting has increased exponentially over the past few years. With gambling being legalized in many parts of the world, more and more people are putting down big money, looking for the chance to bag a massive payday.

But it’s not just sports bettors who are making money, athletes too are making money. From superstar boxer Floyd Mayweather to champion golfer Phil Mickelson and so many more, athletes are just as thrilled to bet on the big games as their fans.

But who has made the most money on a sports bet? And what are the largest bets to ever come in? Let’s try to answer those questions with this list we have made.

1) Floyd Mayweather’s million-dollar bet

Floyd “Money” Mayweather is not just one of the richest athletes in the history of sports, he’s also the granddaddy of all gamblers when it comes to sporting events. The boxing champ consistently places six-figure bets on everything from boxing to football to basketball. However, it’s his whopping £5.9 million bet on Miami Heat to win over the Indiana Pacers that makes him a huge contender on this list. Mayweather’s punt earned him a crazy $6.49 million in cash and clearly shows that he’s a heavyweight gambler in any punter’s books.

2) The Suitcase Man

Way back in 1980, real estate owner William Lee Bergstrom earned himself the reputation of gambling legend as the Texan became known as the “Suitcase Man” after pitching up to a Vegas casino holding two suitcases – one with $777,000 in cash and the other, empty.

The casino had pledged to match any bet as long as it was a visitor’s first – a promise which it soon regretted. Bergstrom placed the entire six-figure sum on a single craps bet and won. He piled the winnings into his empty suitcase and disappeared. Whether he had “baggage” to deal with, nobody would ever know!

3) A whopper of a World Cup wager

During the summer of 2010, the world had World Cup fever and one anonymous punter put down the largest bet in the tournament’s history. The gutsy gambler bet £417,000 on Germany beating Spain in the semi-finals at odds of 10/11. Things were going well for him during the first half when the scoreline remained at 0-0. But when Spain scored a goal in the 73rd minute and the Germans were denied a late penalty, the punter had to say “auf wiedersehen” to £800,000 in potential winnings.

4) The political punter

The year 2014 would go down in history as the year the Scots voted “No” to independence. But it was also the time when one lucky punter made the largest political bet ever. The anonymous punter bet a massive £900,000 on a “No” vote and went home with £193,000 in winnings when the result was declared.

Although he should have quit while he was ahead, the bettor liked his chances on May’s General Election as well. He re-invested his winnings to stake £200,000 on a hung parliament outcome – and went on to lose.

5) The wacky Super Bowl punt

Billy Walters is another legend in the sports gambling world as well as one of the most successful sports bettors ever. He’s claimed millions of dollars from betting big and has been prohibited from a lot of betting establishments for the very same reason.

But it was his whopper of a bet on the 2010 Super Bowl that helped solidify his legendary reputation. Billy bet $3.5 million on the New Orleans Saints beating the Indianapolis Colts. And when the Saints won, his bank account got a cool $3.5 million.

6) Sports better wins on 15-leg parlay on just his second bet

Right before Week 15 of the 2015 season of the National Football League, Tayla Polia had made only one bet in her life. On her second bet, a 15-leg parlay at 20,000-to-1 odds, it managed to return a remarkable $100,005 on a $5 bet. Polia initially believed she had lost the bet.

Tayla Polia’s ridiculous parlay included 14 picks against the spread and one over/under. When she saw the Carolina Panthers had defeated the New York Giants, which she picked, Polia thought her chances at winning had vanished. But because she was picking against the spread, the Giants — who lost by three points as a five-point underdog — actually aided her in getting the massive victory.

7) Rory McIlroy’s father takes advantage of son’s victory

No one was more thrilled than Rory McIlroy when the ace golfer captured his first Open Championship in 2014. However, as it turns out, he wasn’t the only person who won. The golfer’s very own dad joined in on the celebration, cashing in on one of the largest wins in sports betting history.

A decade before his son Rory would claim the Open Championship, Gerry McIlroy had already bet 200 British pounds at 500-1 odds that his then-15-year-old son would claim victory at the Open Championship in the next 10 years. McIlroy’s certainty in his son ended up getting him an estimated $130,000!

8) Tennis fan claims victory even in death

Almost 10 years right before Roger Federer won his seventh Wimbledon win, a gambler named Nicholas Newlife placed a bet that would project Federer’s impressive achievement. But before he ever had a chance to go and gather his winnings, Newlife passed away.

When Nicholas Newlife died in 2009, he left all his belongings to an anti-poverty charity entitled Oxfam. Newlife’s 1,500-pound bet on 66/1 odds eventually hit, allowing the charity to cash in on his winning ticket of more than $155,000. The charity said the money could feed 10,000 West African families for an entire month.

9) Grandfather’s belief in grandson proves lucrative

62-year-old Peter Edwards was so confident that his grandson — who was just a little tyke at the time — would one day play as a professional soccer player. Less than 15 years after Edwards placed his wager of 50 British pounds at 2,500/1 odds, his grandson would suit up for Wales.

Edwards’ grandson, Harry Wilson, thus became a soccer star at the age of just 16. As a matter of fact, Wilson became the youngest player to ever represent Wales. The impressive bet made by Wilson’s grandfather returned 125,000 British pounds (almost $160,000 USD). With the returns of his win, Edwards immediately quit his job and went off to a comfortable retirement.

10) Roofer wins huge accumulator bet

Mick Gibbs is a roofer and is tasked with constructing and repairing roofs all across Staffordshire in England. However, roofing isn’t his only talent. Gibbs also has an astonishing ability to win accumulator bets. In 1999, Gibbs would win his first six-figure payout on a crazy accumulator bet.

Gibbs staked just two-and-a-half British pounds, looking to win a big payout on the accumulator. To get the win, he would need to accurately predict nine soccer games across Europe. Gibbs won the accumulator and came away with 157,000 pounds (almost $200,000 USD).

11) Fan wins on a bet he made on 13-year-old Formula One racer

Richard Hopkins’ eye for talent paid off in a huge way. When the British man brought his son Evan to go-kart racing, he took notice of another go-kart driver by the name of Lewis Hamilton. Impressed with Hamilton’s genius on the track, Hopkins placed a number of bets on Hamilton, hoping he’d later become a Formula One champion.

About a decade after Hopkins placed his bets back in 1998, 22-year-old Lewis Hamilton captured the Brazilian Grand Prix. Hopkins won several bets, including a bet of 200 British pounds with 200/1 odds and a 50-pound bet with 1,500/1 odds. Overall, that fateful day at the race track with his son allowed Hopkins to win165,000 British pounds (over $200,000 USD).

12) 5-team parlay nets six-figure win for an unidentified bettor

A sportsbook bettor at the MGM Resort won in a huge way during an NFL weekend slate in 2017, hitting on five legs of an $8,500 parlay. The bettor hit on the first four legs of the parlay on Sunday, as the Ravens, Patriots, Chiefs, and Raiders all covered as favorites.

The final leg of the ticket listed the Detroit Lions on the money line. This meant that the Lions, a three-point underdog, had to claim a victory in their matchup with the New York Giants outright. The Lions rewarded the bettor, dominating throughout the game to win, 24-10. With $8,500 initially on the line, the unidentified bettor went home with a cool $250,000.

13) Anonymous bettor wins on Leicester City’s miracle run

A longshot — 5,000/1 underdogs — to win the Premier League in 2015, Leicester City’s Cinderella run to become Premier League champions is a sports story that would be remembered for a very long time. When a massive underdog defies the odds, there’s always a handful of fans who would manage to win some money on such an incredulous bet. So, who won the most money on Leicester City?

Before Leicester City’s miracle run, an anonymous bettor placed a 100-pound bet on the team hoisting the Premier League title. Back in October, when the bet was made, Leicester City was a 2,000/1 underdog. The punter won 200,000 British pounds on the wager (over $250,000 USD).

14) Holly Holm rewards “Vegas Dave” in win

Renowned Las Vegas gambler Dave Oancea would never forget November 2015, as it was this time when he crushed two of the biggest bets in sports gambling history. One of those two bets happened at UFC 193, where Holly Holm faced off against heavy favorite Ronda Rousey. Oancea put $20,000 on the line at 11-1 odds that Holm would beat the undefeated Rousey.

The gamble paid off big for “Vegas Dave,” who claimed he would bet against Rousey until she lost. Oancea turned his $20,000 into $200,000 with the bet —a pretty good return on investment if you ask us.

15) Las Vegas bettor turns $5 into a six-figure payout

An anonymous bettor hit paydirt at the William Hill sportsbooks in 2016, and it took a minor miracle to make it happen. The Las Vegas resident went 15-for-15 picking straight-up basketball winners on a progressive parlay card. William Hill charges a $5 weekly entry fee to participate.

The bettor accurately picked 12 college basketball winners over the course of a weekend. He also chose two NBA winners: the Detroit Pistons and the Golden State Warriors. Golden State trailed by four points with only 14 seconds left in regulation but still was able to make a remarkable comeback. The total value of the bettor’s ticket? Just a cool $305,375.

16) Poker player wins massive bet on the golf course

Professional poker player Erick Lindgren has won millions of dollars at the poker table. But his win on this bet may have been the toughest money he’s ever earned! One day, a few pro players — this included the legendary Phil Ivey and Gavin Smith — bet Lindgren that he couldn’t play four straight rounds of golf in a day.

And there was more to the bet as well: Lindgren had to play in the 100+ degree Las Vegas weather, hold his own clubs, and shoot under 100 in each round from the pro tees. Lindgren walked more than 20 miles in the searing heat, and he won the bet. Lindgren went home with a total of $340,000 for his efforts.

17) Anonymous bettor cashes in on Cardinals’ World Series win

Right before the start of the 2011 MLB season, an anonymous bettor went to the MGM sportsbook in Las Vegas and placed two bets that would come back to yield extraordinarily high returns. First, he bet $250 in hopes that the St. Louis Cardinals would capture the National League pennant. He also staked another $250 on the Cardinals winning the World Series later that year.

With $500 laid on the line in the far cry that St. Louis would win the World Series, the unnamed bettor was blessed with victory, twice. After the victory, the anonymous bettor was able to cash in his two winning tickets for $375,000.

18) Star golfer makes huge Super Bowl bet

Before the 2000 NFL season, professional golfer Phil Mickelson was confident in the chances of the Baltimore Ravens winning the Super Bowl. So much so, that he decided to make a betting syndicate, which placed a $20,000 wager on the Ravens to win the Super Bowl — before the season had even begun.

Mickelson noted that Baltimore had finished off the previous season with a 6-2 record and made some great off-season player acquisitions. Mickelson’s bet, made at 22/1 odds, paid out a reported $560,000. He also reportedly won big later that same year, betting on the Arizona Diamondbacks to win the World Series.