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The 30 biggest wins in sports betting history

Sports betting has become wildly popular over the years. Legalized gambling is taking the world by storm, and with so much money being put down on big games, athletes are no longer the only people making millions from sports. But it’s not just the big-name sports bettors who are making money—athletes are making money too. From Floyd Mayweather to Phil Mickelson and more, athletes are just as excited to bet on the big games as their fans. But who has made the most money on a sports bet? That question will be answered later on in this story.

Sports betting has become wildly popular over the years. Legalized gambling is taking the world by storm, and with so much money being put down on big games, athletes are no longer the only people making millions from sports. But it’s not just the big-name sports bettors who are making money—athletes are making money too. From Floyd Mayweather to Phil Mickelson and more, athletes are just as excited to bet on the big games as their fans. But who has made the most money on a sports bet? That question will be answered later on in this story.

Second-time sports better wins on 15-leg parlay

Prior to Week 15 of the 2015 NFL season, Tayla Polia had only made one previous bet in her life. Her second bet, a 15-leg parlay at 20,000-to-1 odds, returned an incredible $100,005 on a $5 bet. At first, Polia actually thought she lost the bet.

New York Giants quarterback Eli Manning

(Photo from Flickr/Erik Drost)

Tayla Polia’s insane parlay included 14 picks against the spread and one over/under. When she saw the Carolina Panthers beat the New York Giants, who she picked, Polia thought her chances at winning were long gone. But because she was picking against the spread, the Giants—who lost by three points as a five-point underdog—actually helped her win.

Rory McIlroy’s father cashes in on his son’s win

No one was more excited than Rory McIlroy when the superstar golfer won his first Open Championship in 2014. But as it turns out, he wasn’t the only person celebrating. The golfer’s father joined in on the celebration, cashing in on one of the biggest wins in sports betting history.

Rory McIlroy and his father Gerry McIlroy

(Photo from Flickr/TourProGolfClubs)

10 years before his son Rory would win the Open Championship, Gerry McIlroy bet 200 British pounds at 500-1 odds that his then-15-year-old son would win the Open Championship in the next 10 years. McIlroy’s confidence in his son ended up netting him roughly $130,000—and probably one heck of a celebration!

Tennis fan wins huge from beyond the grave

Nearly a decade before Roger Federer secured his seventh Wimbledon win, an unknown punter (British slang for  “gambler”) named Nicholas Newlife placed a bet that would predict Federer’s impressive feat. But before he ever had a chance to collect his winnings, Newlife passed away. What would happen to his payout?

Roger Federer secures his seventh Wimbledon win

(Photo from Flickr/Robbie Dale)

When Nicholas Newlife passed away in 2009, he left all his belongings to an anti-poverty charity called 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.

Grandfather bets his grandson will play professionally, wins big

Have you ever looked at a toddler and thought he or she could one day be a professional athlete? 62-year-old Peter Edwards was just that confident that his grandson—a toddler at the time—would one day represent Wales as a professional soccer player.

Liverpool wing Harry Wilson

(Photo by Wikimedia Commons/Kaosz113)

Less than 15 years after Edwards placed his bet of 50 British pounds at 2,500/1 odds, his grandson would take the field for Wales. Edwards’ grandson, Harry Wilson, became a soccer star at the age of just 16. In fact, Wilson became the youngest player to ever represent Wales. The ambitious bet made by Wilson’s grandfather yielded 125,000 British pounds (nearly $160,000 USD). With the proceeds of his win, Edwards retired immediately.

Roofer wins giant accumulator bet

Mick Gibbs is a roofer by profession. The British man constructs and repairs roofs all across Staffordshire in England. However, roofing isn’t his only skill. Gibbs also has an incredible ability to win accumulator bets. In 1999, Gibbs would win his first six-figure payout on a crazy accumulator bet.

Sportsbook in Las Vegas

(Photo by Flickr/Baishampayan Ghose)

Gibbs wagered just two-and-a-half British pounds, hoping to win a big payout on the accumulator. To win, he would need to correctly predict nine soccer games across Europe. Gibbs won the accumulator and collected 157,000 pounds (nearly $200,000 USD). As impressive as Gibbs’ win is, the next big bet he’d win (later in this story) makes this payout look like chump change.

Fan cashes in on bet he made on 13-year-old Formula One racer

You could say Richard Hopkins has an eye for talent. When the British man took his son Evan go-kart racing, he noticed another go-kart driver by the name of Lewis Hamilton. Impressed with Hamilton’s talent, Hopkins placed multiple bets on Hamilton, hoping he’d eventually become a Formula One champion.

Formula One racer Lewis Hamilton

(Photo by Flickr/Mark McArdle)

About 10 years after Hopkins placed his bets in 1998, 22-year-old Lewis Hamilton won 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. All in all, Hopkins’ day at the go-kart track with his son netted him 165,000 British pounds (more than $200,000 USD).

5-team parlay nets six-figure win for anonymous bettor

An MGM Resorts sports book bettor won big on 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.

Detroit Lions quarterback Matthew Stafford

(Photo from Flickr/Mike Morbeck)

The final leg of the ticket was the Detroit Lions on the money line. This means the Lions, a three-point underdog, had to win their matchup with the New York Giants outright. The Lions rewarded the bettor, dominating throughout the game and earning a 24-10 victory. With $8,500 originally on the line, the unidentified bettor walked away with $250,000.

Anonymous bettor cashes in on Leicester City’s miracle run

5,000/1 underdogs to win the Premier League in 2015, Leicester City’s incredible run to become Premier League champions is a tale that will live on forever. When a massive underdog defies the odds, there’s always a handful of fans who win some money on an absurd bet. But who won the most money on Leicester City?

Leicester City in 2015

(Photo by Flickr/Ian Johnson)

Before Leicester City’s miracle run, one anonymous bettor placed a 100-pound bet on the team winning 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 (more than $250,000 USD).

‘Vegas Dave’ wins huge on Holly Holm fight

Las Vegas gambler Dave Oancea had a month to remember in November 2015, crushing two of the biggest bets in sports gambling history. One of those two bets took place at UFC 193, where Holly Holm faced Ronda Rousey. Oancea put $20,000 on the line at 11-1 odds that Holm would beat the undefeated Rousey.

Las Vegas gambler Dave Oancea

(Photo by Instagram/@itsvegasdave)

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—that’s a pretty good return on investment. But Oancea’s win on the Holm fight pales in comparison with his winnings from earlier that month. (Spoiler alert: you’ll find “Vegas Dave” again later on in the story.)

Las Vegas bettor turns $5 into six-figure payout

An anonymous bettor hit the jackpot at William Hill sports books in 2016, and it took a minor miracle to 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.

Golden State Warriors guard Stephen Curry

(Photo by Wikimedia Commons/Cyrus Saatsaz)

The bettor correctly selected 12 college basketball winners over the course of a weekend. He also picked 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 managed to make an insane comeback. The total value of the bettor’s ticket? $305,375.

Poker player wins huge bet on the golf course

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

Erick Lindgren

(Photo by Wikimedia Commons/flipchip)

There was another catch: Lindgren had to play in the 100+ degree Las Vegas weather, carry his own clubs, and shoot under 100 in each round from the pro tees. Lindgren walked more than 20 miles in the blistering heat, and he won the bet. Lindgren earned a total of $340,000 for his efforts.

Anonymous bettor cashes in twice on Cardinals’ World Series win

Before the 2011 MLB season, an anonymous bettor went to the MGM sports book in Las Vegas and placed two bets that would come back to yield incredibly high rewards. First, he put $250 down in hopes that the St. Louis Cardinals would win the National League pennant. He wagered another $250 on the Cardinals winning the World Series later that year.

The St. Louis Cardinals celebrate their World Series win in 2011

(Photo by Wikimedia Commons/Jleybov)

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

Star golfer makes huge Super Bowl bet

Prior to the 2000 NFL season, professional golfer Phil Mickelson really liked the Baltimore Ravens’ Super Bowl chances. In fact, he liked them so much that he decided to form a betting syndicate, which placed a $20,000 wager on the Ravens to win the Super Bowl—before the season even started.

Phil Mickelson

(Photo by Flickr/minds-eye)

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.

British roofer beats astronomical odds

British roofer Mick Gibbs has already been featured earlier on this list, winning more than 157,000 British pounds (nearly $200,000 USD) on a nine-game accumulator bet. But that wasn’t his only big win. Two years after cashing in his winning ticket, Gibbs wagered 30 pence on a 15-leg accumulator bet. His odds? 1,666,666/1.

Bayern Munich goalkeeper

(Photo by Flickr/Bernd Schrade)

Incredibly, the first 14 games went exactly as Gibbs had predicted. Everything now depended on a Champions League match between Bayern Munich and Valencia. The game ended in penalties, and Bayern Munich’s goalkeeper made a game-winning save that would make Gibbs 500,000 British pounds (more than $633,000 USD) richer.

Bettor wins seven horse races in a single day

In 1996, a bettor named Darren Yates accomplished one of the greatest feats in the history of sports betting. In fact, the accomplishment is well-known in horse racing circles. It’s now referred to as the “magnificent seven.” Yates has since become one of the biggest names in horse racing, and it’s possible his success would have never happened if not for what occurred on this day.

Horse at Ascot Chase

(Photo by Wikimedia Commons/Jamesatkins)

In a life-changing wager, Yates placed 62 British pounds on a bet that jockey Frankie Dettorri would win all seven of his rides that day at Ascot. The bettor’s gutsy wager paid off, as Yates came out with over 550,000 British pounds (nearly $700,000 USD) at the end of the day.

80-pence bet delivers six-figure payout to anonymous bettor

UK bookmakers will forever remember November 2011, a month in which the favorites seemed to win almost every match. The biggest payout of the month went to an anonymous bettor from the island of Malta, who made a bet for just 80 pence (about $1 USD).

Liverpool vs Chelsea

(Photo by Flickr/CFCUnofficial)

The punter’s bet was made on a 19-match accumulator with record odds of 683,738/1. He correctly predicted all 19 matches, which concluded with Liverpool’s victory over Chelsea. The punter, who had never staked more than one euro an any bet he had placed, won more than 585,000 British pounds (more than $740,000 USD) for his efforts.

NBA legend wins big on Super Bowl gamble

NBA Hall of Famer Charles Barkley is known for putting big money down on sports bets. Barkley has won some big bets throughout the years, but one sticks out above the rest. His biggest win came after he bet on one of the most unlikely Super Bowl champions in history: the New England Patriots.

Charles Barkley

(Photo by Gene Bromberg/Flickr)

In 2002, the Patriots were a 14-point underdog against the St. Louis Rams in Super Bowl XXXVI. Barkley liked what he saw, putting $500,000 on New England to pull off the upset. Tom Brady won his first of many Super Bowls, and Barkley walked away with $800,000.

Charles Barkley loses on huge gamble

Despite losing more than $10 million gambling over the years, Charles Barkley still loves to gamble. The NBA legend and TNT analyst has made (and lost) a lot of money in sports betting. Barkley made a lot of money on the Patriots’ first Super Bowl victory, but eventually, he decided to bet against New England (and paid the consequences).

Charles Barkley

(Photo by Flickr/Aaron Frutman)

When the Patriots faced the Atlanta Falcons in Super Bowl LI, Barkley made a big bet on the underdog Falcons. Atlanta took a 28-3 lead after halftime, and the game appeared all but over. But the Patriots made a historic comeback, taking out the Falcons and ruining Barkley’s bet. It was later revealed Barkley lost $100,000 backing the Falcons.

The biggest bet in sports betting history

In 2017, one big-time bettor in Las Vegas reportedly made a bet on the winning team of the World Series game—just one of five consecutive World Series games he had bet on. And after each win, he has bet the winnings on the next game. The man is reportedly an Eastern European who at the time was under the age of 30, and he has earned the nickname of the “Let It Ride” gambler.

2017 World Series between the Los Angeles Dodgers and Houston Astros

(Photo by Wikimedia Commons/John Bowles)

When the Dodgers faced the Astros in Game 6 of the 2017 World Series, the bettor put $8 million on the Dodgers to win. Los Angeles ended up winning, which made his ticket worth $14 million. If reports of the bet are true, this would likely be the largest return in sports betting history.

Fan puts $85,000 on Tiger Woods and wins

Tiger Woods’ historic 2019 Masters victory will live on in sports history forever—but for more than one reason. Woods’ comeback—his first major championship victory in 11 years—was insane. But deciding to bet $85,000 on a golfer who hadn’t won a championship in more than a decade? Now that sounds really insane.

Tiger Woods

(Photo by Flickr/Keith Allison)

39-year-old James Adducci claims the first sports bet he’s made in his life was the bet just described: an $85,000 wager on Tiger Woods to win the Masters. Of course, Woods went on to claim his victory, and Adducci won $1.2 milion. Adducci’s bet broke the record for the largest individual payout on a futures bet in the history of William Hill.

Horse owner cashes in massive ticket on his own horse

A widely recognized international gambler, Mike Futter owns bingo halls in Ireland and likes to bet on horse races. In 2003, Futter made a bet most people don’t have the luxury of making: he gambled on his own horse. Futter’s horse, named Monty’s Pass, ran hard and ended up winning the race. So how much did Futter win?

Horse racing

(Photo by Flickr/Paul)

As the owner of Monty’s Pass, Fetter was awarded with 348,000 British pounds for the victory. But because he bet on his horse steadily at all rates, from 40/1 down to 16/1 odds, Futter won around 800,000 pounds (more than $1 million USD).

Fertilizer salesman turns pocket change into seven-figure prize

There isn’t a better rags-to-riches story than that of 60-year-old fertilizer salesman Fred Craggs. The native of Yorkshire in the United Kingdom made one of the most famous wagers in sports betting history by placing 50 pence (less than $1 USD) on an eight-fold accumulator that would go on to return a seven-figure prize.

Horse racing

(Photo by Flickr/Paul)

Craggs placed an eight-fold accumulator bet with selections from horse races around the world. Interestingly, the 60-year-old didn’t even realize he won until he visited his bookmaker to make another bet. Had Craggs made a no-limit bet, his ticket would have been worth about 1.4 million British pounds. But his ticket capped at 1,000,000 pounds (about $1.26 million USD).

Heating engineer hits the Jackpot

One day in 2011, Steve Whiteley took the bus to the races, used a free ticket to get in and placed a bet for two British pounds. Later that day, he left as a millionaire. Whiteley, a 61-year-old heating engineer, accomplished a feat no other punter in the U.K. could achieve.

Horse racing

(Photo by Flickr/Paul)

Gamblers filled the crowd at the race, trying to win the Jackpot: a Tote bet (like a lottery) which had been rolling over for more than a week. Whiteley picked all six winners at the event, including a horse that had been beaten in each of its 28 previous races over hurdles. The prize for Whiteley’s two-pound bet? 1.5 million pounds (about $1.9 million USD).

“Vegas Dave” makes history

One week into the 2015 MLB season, gambler Dave Oancea decided to bet on the Kansas City Royals to win the World Series. Vegas had them at 30/1 odds, even after Kansas City won their first seven games. But because the Royals were hot, it was difficult for “Vegas Dave” to make his bet.

Vegas Dave at the Royals World Series

(Photo by Instagram/@itsvegasdave)

Oancea had to spread his $140,000 bet across 15 different casinos, because they didn’t want to take on his liability. But Oancea’s payout was well worth the hard work it took. After the Kansas City Royals defeated the New York Mets to win the World Series, “Vegas Dave” cashed in his ticket for $2.5 million.

Professional sports bettor racks up millions

Billy Walters is widely considered one of the most successful sports gamblers in Las Vegas, with a winning streak that extended for more than 30 years. He’s made countless big bets, including a $2.2 million bet on USC beating the University of Michigan in January 2007 (which they did). But that win wasn’t even Walters’ biggest victory.

Saints Super Bowl parade

(Photo by Flickr/Tulane Public Relations)

Entering Super Bowl XLIV, the New Orleans Saints were underdogs against the Indianapolis Colts. Walters made a bold decision, putting a huge bet on New Orleans. And when the Saints beat the Colts outright, Walters won $3.5 million. In 2011, Walters claimed he could make $50–60 million on a good year. But as Walters continued to win, trouble followed.

The consequences of winning big

Billy Walters became an accomplished gambler, but trouble loomed for the multimillionaire. To date, Walters has been indicted by the Nevada Attorney General’s office four times, though the charges were dropped each time. Later on, the law finally caught up.

U.S. Prison

(Photo by Wikimedia Commons/Federal Bureau of Prisons)

In 2017, Billy Walters was convicted of making $43 million on private information of dairy-processing company Dean Foods. Phil Mickelson was also mentioned during the trial as someone who had traded in the company’s shares. He’s also said to have owed nearly $2 million in gambling debts to Walters. Walters was forced to pay a $10 million fine, and he was sentenced to five years in prison.

Floyd Mayweather’s betting habit

Floyd Mayweather Jr. is one of the richest, most successful and most controversial figures to ever grace the sport of boxing. He’s a multimillionaire, a champion, and an Olympic medalist, but Mayweather Jr. may be best known for his legendary sports bets.

Floyd Mayweather Jr

(Photo by Flickr/DEWALT POWER TOOLS FIGHT NIGHT CLUB 2010)

Mayweather has an outrageous personality. He calls $50,000 and $100,000 per-game bets “normal.” One of Mayweather’s biggest wins came in 2014, when he bet $720,000 on the Indianapolis Colts to cover a seven-point spread against the Jacksonville Jaguars. The Colts covered, giving the boxer an opportunity to walk home with $1.4 million. But that wasn’t close to Mayweather’s biggest win…

Mayweather’s massive payout

There are multiple reports of the boxer laying down bets of more than a million dollars on a single game. The first came in 2012, when Mayweather supposedly bet $1.8 million on the L.A. Clippers to beat the Memphis Grizzlies. In that game, the Clippers overcame a 24-point deficit to come out on top.

Floyd Mayweather Jr. gambling

(Photo by Instagram/@floydmayweather)

But Mayweather’s largest reported bet came in June of 2013, when he is said to have bet $5.9 million on Game 7 of the series between the Miami Heat and the Indiana Pacers. He’s said to have bet on the Heat to cover the seven-point spread. The Heat won by 23 points, leaving fans to wonder how much Mayweather’s ticket would’ve been worth if the reports are true.

Anonymous punter wins giant accumulator bet

Behind each massive betting win is a bookmaker that wishes it could go back in time and change the odds. The victim in this story is Coral, who had to pay out the largest bet it has ever paid to an anonymous punter that made a 19-pound (about $24 USD) accumulator bet.

Las Vegas sportsbook

(Photo by Flickr/Tomás Del Coro)

The lucky winner resided in the county of Leicestershire in the United Kingdom. There were high odds on the five-fold accumulator bet, but the individual’s larger bet stake made the reward even sweeter. After wagering just 19 British pounds, the anonymous punter walked away with 823,000 pounds (about $1.04 million USD).

Connor Howe has been working in the sports industry for more than a half-decade, having spent time on the writing side as well as the marketing side of professional sports. He's spent time with the San Diego Chargers, Bleacher Report, and SB Nation, among others, and is excited to bring his knowledge and experience to Tiebreaker.

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