That didn’t steer away bettor James Adducci who got his wife to allow him to place an $85,000 wager on Woods to win the 2019 Masters at the William Hill sportsbook with 14/1 odds.

• Some of the most amazing historical sports betting upsets in the past 100 years. Check out the top underdog payouts in US history: http://www.bigonsports.com.
• Sports betting has come a long way – from the days when horse races were reserved for those of an upper social class, to the unending list of online bookies found nowadays. In fact, the first online betting platforms only originated towards the end of the 90s – and look at the many options now! One can only imagine what the world of sports betting has yet to introduce It certainly has.
• Below are the biggest sports betting wins of all time across American football, basketball, soccer, cricket, rugby, and horse racing. Anonymous – $14 million One lucky punter became $14 million richer after placing a successful bet between the L.A Dodgers and the Houston Astros, in the 2017 World Series.

Long-shot wins in sports-betting history

Everyone loves an underdog, especially when that underdog not only defies the longest of odds, but gives a few lucky gamblers the biggest paydays of their lives. Long-shot bets have a magical quality about them. For them to pay off, the team or athlete has to achieve what seems like the impossible and for that miraculous feat, the people who took their chances to wager on them are rewarded handsomely.

With the advent of advanced technologies and less restrictive governments, the global sports-betting market has exploded in recent years, giving rise to more long-shot bettors and a handful of extremely lucky winners. The worldwide betting market was valued around $104 billion in 2017 and is expected to reach $155 billion by 2024, according to Zion Market Research. Growth in this sector is expected to be at 8.83% between 2018 and 2024.

With all this rapid growth, Stacker dug into the past to find the biggest long-shot bets in history, and maybe a few unlucky bettors along the way. Every sport from horse racing and boxing to basketball and golf has their share of come-from-behind victories, crazy parlays, and unfathomable buzzer-beaters. Here is a list of the most unbelievable wagers in sports that are sure to tantalize even the most gun-shy gambler.

You may also like:One trick ponies of the PGA

Golf: Rory McIlroy's father's 500-1 bet his son wins the British Open within 10 years

Talk about confidence in one's own kid. When pro golfer Rory McIlroy was only 15 years old in 2004, his father bet $683 with 500-1 odds that his son would win the British Open before his 26th birthday. Coming in just under the deadline, McIlroy won the 2014 British Open and his father took home $342,000. Rory pocketed a cool $1.6 million for his efforts on the course.

Hockey: U.S. hockey 1,000-1 to win 1980 gold medal

“Do you believe in miracles!?” Legendary sports announcer Al Michaels made his famous call after the 1980 U.S. men's Olympic hockey team defeated the heavily favored Russians. The Russian team had won the previous four Olympic golds in a row—winning five of the past six Olympic golds total—and the U.S. was a 1,000-1 underdog. But sometimes miracles happen, and the U.S. pulled off the upset 4-3, and went on to defeat Finland to win the gold medal.

Soccer: Mick Gibbs 1,666,666-1 on 15 match parlay

In what's considered one of the greatest sports bets of all time with insanely long odds, British gambler Mick Gibbs hit a 15-match parlay. For betting neophytes, a parlay is when a bettor gambles on multiple games at the same time, making the odds of winning harder, but the payout much bigger. Back in 2001, Gibbs bet about 47 cents on a 15-match soccer parlay with 1,666,666-1 odds of winning. Well, he won and took home $784,000.

Soccer: Leicester City 5,000-1 to win 2015 Premier League

The Premier League is the most prestigious league in all of English football and was created in 1992. Since its inception, the league has only seen a handful of winners (the same teams win most of the time), which is why 2015 was such an anomaly. Perennial underdog Leicester City entered the season in 2015 with a 5,000-1 chance of winning the league. Not only did Leicester City win, they cost the English bookmakers the biggest loss on a single sporting market, forcing them to pay out around £25 million.

Horse racing: Darren Yates 25,000-1 on 7 race parlay

There are many great feats in horse racing: winning the Kentucky Derby, the Dubai World Cup, or the Royal Ascot in England. In September 1996, jockey Frankie Dettori didn't just win one race, he won all seven races at the Royal Ascot, from which the odds were 25,000-1. Unfortunately for the bookmaker, one lucky bettor named Darren Yates actually wagered on Dettori taking down all seven races and won £550,000 from a £67.58 bet.

Horse racing: Fred Cragg 2,000,000-1 on 8-race parlay

On a lark, Fred Cragg bet 50 pence on an eight-horse parlay in 2008 right before his 60th birthday. The odds of winning were 2,000,000-1 and shockingly, all eight horses won. The bookmaker William Hill paid out £1 million instead of the £1.4 million he should've given Cragg because the fine print said payouts were capped at £1 million. Nonetheless, it remains one of the most lopsided wins in betting history.

Soccer: Inter Milan 999-1 to beat Sampdoria down two goals in 88th minute

It's hard enough to score one goal in soccer, let alone three in the final two minutes of a game. But that's what Inter Milan did in 2005 during an Italian League Serie A match against Sampdoria. One lucky bettor evidently thought Milan had a chance when they were down two goals and placed a £1 wager on them coming through, ultimately winning £1,000 for the lucky guess.

Soccer: Mali 1000-1 to make a four-goal comeback with 11 minutes left

The beauty of betting in Great Britain is that a gambler can wager on the outcome of a game at almost any time during the game itself. One lucky bettor in 2010 saw that Mali was down 4-0 in the African Cup of Nations to Angola with odds of coming back at 1000-1. The bettor threw down £5 and when Mali made one of the greatest comebacks in history, the bettor got £5,000 in return.

Football: St. Louis Rams 300-1 to win Super Bowl

Going into the 1999 NFL season, the St. Louis Rams had 300-1 odds of winning the Super Bowl. That wasn't all that surprising considering they only won four games the year before. But with a change at quarterback to Kurt Warner, the team went 13-3, Warner won the MVP of the regular season and Super Bowl, and the team wound up beating the Tennessee Titans 23-6. One other footnote was that the Rams were actually a seven-point favorite to win over the Titans.

Football: Auburn Tigers 1,000-1 to win 2014 Bowl Championship Series

Hedging one's bet is a strategy that gamblers use to maximize their chances at winning, regardless of the result. There are times when the odds change so dramatically that an early wager and a late wager can result in large wins. Leading into the 2013 college football season, one fan bet $100 for Auburn to win the 2014 Bowl Championship Game at 500-1 (getting in a little late missing out on 1,000-1). Auburn didn't win the game though, and the fan missed out on an enormous hedging opportunity by not betting big on Auburn's opponent Florida State. All he wanted was for Auburn to win, according to an ESPN article.

Soccer: Xabi Alonso 125-1 own end goal

There's a lot of luck in gambling. So, when a football fan dreamt that Xabi Alonso would score a goal from behind the halfway mark, he needed fate to intervene on his behalf. Amazingly, the bet that Adrian Hayward made at 125-1 paid off, and his £200 wager resulted in a £25,000 win when Alonzo scored a lengthy goal for Liverpool in the third round of the FA Cup back in 2006.

Soccer: Greece 150-1 to win 2004 UEFA Euro

The UEFA European Championship is the most prestigious soccer competition on the continent and held once every four years since 1960. Heading into the 2004 Euro, Greece was given 150-1 odds of winning the tournament. To the shock of the world, Greece pulled off a major upset, beating host country Portugal, led by legendary footballer Cristiano Ronaldo, 1-0.

Golf: James Adducci bets $85,000 at 14-1 on Tiger Woods to win The Masters

While most of the world had lost faith in Tiger Woods' ability to win another major championship, one lucky gambler never gave up. Heading into the 2019 Masters, Woods was on a major drought that went back to 2008. James Adducci saw an opening when he found 14-1 odds on Tiger Woods to win the Masters again. Adducci bet $85,000 on Woods, and ultimately won $1.2 million once Woods prevailed at the 2019 Masters Championship.

Baseball: Blake Snell 300-1 to win 2018 AL Cy Young

Blake Snell wasn't an unknown going into the 2018 Major League Baseball season, but nobody was picking him to win the Cy Young Award (the award given to the best pitcher in each conference). Snell was a 300-1 favorite for the award while turning in one of the most surprising pitching seasons in baseball history. In fact, Snell was so good, that despite having the lowest innings pitched total for any award winner in history, he still won 21 games and had an ERA of 1.89.

Baseball: St. Louis Cardinals 999-1 to win 2011 World Series

In September 2011, the St. Louis Cardinals looked like they were going to miss the playoffs. But one lucky bettor had a hunch, and it paid off, big time. The gambler wagered $250 at 500-1 that the Cardinals would win the National League Pennant. He then bet another $250 at 999-1 that the Cardinals would win the World Series. Both bets came in when St. Louis won it all and the gambler took home $375,000 for taking his chances.

Horse racing: Donerail 91-1 in 1913 Kentucky Derby

The Kentucky Derby has seen its share of betting long shots, but nothing quite like Donerail in 1913. Heading into the race, no one, including the horse's owner, thought Donerail had any shot at winning. And at 91-1 odds, they had good reason. But Donerail's jockey Roscoe Goose convinced the horse's owner to race and they ended up winning the whole thing. Anyone who bet $2 on the horse would've won $184.90—no small change for 1913.

Golf: Ben Curtis 300-1 to win the 2003 British Open Golf Championship

There have been some shocking one-hit-wonders through the PGA Tour's history. There was Danny Willett's unlikely Masters in 2016, Yang Yong-eun's PGA Championship in 2009, and Todd Hamilton's Open Championship in 2004. But then there was Ben Curtis, who was a 300-1 favorite for winning the British Open in 2003. And win it he did. Curtis fended off a leaderboard that consisted of Tiger Woods, Vijay Singh, and Nick Faldo to win by a single stroke. It was the only major of his career and was just one of four tournaments he won in total.

Darts: Robert Thornton 250-1 to win the 2012 U.K. Darts Open

Back in 2012 a relatively unknown darts player overcame pneumonia and the sport's best throwers to take down the U.K. Open championship. As a 250-1 underdog, no one gave Robert Thornton a chance. But after besting everyone from Mark Webster and Gary Anderson to Dave Chisnall and the all-time great Phil Taylor, Thornton walked away with £40,000 and one of the unlikeliest and biggest long-shot wins in the sport's history.

Basketball: #16 UMBC 40-1 to beat #1 Virginia

It had never been done. They said it was impossible. But the University of Maryland, Baltimore County (UMBC) Retrievers had other ideas. Coming into the NCAA Tournament in 2018, UMBC was the 16 seed playing against the #1 seeded Virginia Cavaliers. A 16 seed had never beaten a #1 in tournament history and UMBC's odds were placed at 40-1. The Retrievers did the impossible though and beat the Cavaliers 74-54 and earned one incredibly lucky bettor $16,800 off an $800 bet. Don't feel too bad for Virginia, they won the National Championship in 2019.

Wrestling: Rulon Gardner 2,000-1 to win 2000 gold

The most dominant Greco-Roman wrestler in history was a man dubbed the Siberian Superman. Wrestling for the Soviet Union, Alexander Karelin was basically unbeatable and went 13 straight years of wrestling in international competition without a loss. In the 2000 Olympic Games in Sydney, Australia, he squared off against American Rulon Gardner, who at 2,000-1, had little to no chance of victory. But miracles can happen and Gardner somehow managed to score the one and only point of the match to clinch the gold and beat Karelin.

Boxing: Buster Douglas 42-1 to beat Mike Tyson

It's easily the biggest upset in boxing history; virtually no one thought that Buster Douglas would beat Mike Tyson in Tokyo in 1990 for the heavyweight championship of the world. Douglas was a relative unknown heading into the competition and was a 42-1 underdog to defeat Tyson, who at the time was considered one of the best of all time and had never lost a fight. On the betting side, The Mirage Casino took one bet on Mike Tyson to win for $168,000 (oops). They also took a $1,500 bet on Douglas to win that paid out $57,000.

One of the most exciting aspects of sports betting is that anybody can win big, amateur or pro.

The catch, though, is that you either have to bet long odds or risk lots of money. But some bettors have proven that the risk is worth the reward in either case.

Several sports bettors have gotten rich off one or more successful wagers. Even Drake’s dad recently netted six figures with a huge betting win.

Below, you can see more on Dennis Graham’s story, along with other gamblers who’ve won big with sports gambling.

Dennis Graham

Dennis Graham is known first and foremost as the father of Aubrey Graham (a.k.a. Drake). While his son may be one of the world’s biggest hip-hop icons today, Dennis was the first musician in the family.

Graham started playing drums in 1962. He used a makeshift setup that included round tin tubs that people used to bathe in.

James Brown’s drummer gave Dennis his first reel set of drums. This gift helped pave the way for his eventual career, which included drumming for Jerry Lee Lewis.

What does any of this have to do with sports betting?

Well, Graham recently wagered $100,000 on the Toronto Raptors winning the 2019 NBA championship. The Raptors were underdogs to the two-time defending champs, the Golden State Warriors.

Biggest Sports Betting Wins Ncaa Basketball

However, Dennis wasn’t phased and decided to put a six-figure sum down on Toronto anyway. He was likely inspired to do so by Drake, who’s the global ambassador for his hometown Raptors.

Graham was rewarded handsomely when Toronto pulled off the upset, winning the series four games to two. Drake’s dad, meanwhile, pocketed $300,000 after taking the Raptors at 3-1 odds.

Sir Ride A Lot

The 2017 World Series was one of the best in recent memory. The LA Dodgers and Houston Astros went the full seven games, with the Astros pulling out the victory.

An interesting side story involving an Eastern European gambler developed on the side of the World Series. The anonymous gambler, who became known as “Sir Ride A Lot,” placed enormous wagers on the first six games.

Of course, betting big on baseball’s premiere event isn’t a story in itself. But the fact that this gambler let his winnings ride after every game is.

He accumulated $6 million in profits after five successful bets in five games. The logical thing to do in this situation would’ve been to pocket the multimillion-dollar win, or at least only bet a portion of it.

Sir Ride A Lot had other ideas, though. He wagered all $6 million on the Dodgers (-126) winning Game 6. His hot streak continued as LA won and his winnings soared up to $14 million.

He actually thought about risking the $14 million on Game 7. However, the temptation to keep the eight-figure fortune was too great and he stopped betting.

Haralabos Voulgaris

The first couple of gamblers covered in this post were the beneficiaries of incredible luck. But Haralabos Voulgaris (a.k.a. H-Bob) is a professional bettor who’s earned millions of dollars through skill alone.

Voulgaris’ journey towards success began in the early 2000s, when he discovered that bookmakers were setting inefficient NBA halftime totals.

H-Bob began taking the “over” with second-half totals and making a fortune. He’d collect millions of dollars before bookmakers realized and adjusted their strategies.

Voulgaris wasn’t done yet, though, because he developed a betting algorithm in the mid-2000s. He used this program to continue building on his fortune.

He’s since parlayed his immense knowledge of the NBA into a front-office job with the Dallas Mavericks. He also still has much of the fortune that he made by gambling on basketball.

Billy Walters

Billy Walters is another professional bettor who used his wits to win big. Walters started his professional life as a car salesman in Kentucky.

He quickly proved a success at this job, before deciding to bolt to Las Vegas. Here, Walters partnered with the “Computer Team” to dominate the sports betting world.

They were named the Computer Team because they were among the rare gamblers using PCs in the 1980s. Their early knowledge of computers paid off, as they were able to calculate advanced metrics.

Walters continued winning big bets long after bookmakers caught up to the Computer Team’s ways. His crowning achievement is when he won $3.5 million on Super Bowl 44.

He had a good feeling about the New Orleans Saints toppling the favored Indianapolis Colts. His intuition paid off when the Saints won 31-17.

Walters admits that he used bad bankroll management in this case. But few can argue with the result. Unfortunately, Billy was convicted in an insider-trading scandal involving Dean Foods. He’s now serving a stint in federal prison.

Gerry McIlroy

Rory McIlroy is one of the most successful golfers of all time. He has four Major titles and 14 overall PGA tournament wins.

It appears that McIlroy was always destined to be a success. However, this wasn’t entirely the case when he was growing up in Northern Ireland.

Nevertheless, his father, Gerry, placed a bet on his teenage son winning the British Open within 10 years. The proud dad bet £200 at 500 to 1 odds that Rory would soon be a British Open champ.

Biggest Sports Betting Wins Reddit

Rory was 15 when the bet was made and went on to win the Open at age 24. His father pocketed £100,000 as a result.

50 Cent

Curtis Jackson (a.k.a. 50 Cent) is a New York native who loves the Giants. That said, he was looking to bet big when the G-Men made Super Bowl 46.

50 first caught betting hysteria when New York played the San Francisco 49ers in the 2011 NFC Championship. He won a $500,000 wager when the Giants pulled out a 20-17 overtime victory.

Next up was an even tougher task, the undefeated New England Patriots. Jackson bet $1 million on the underdog Giants and was successful again when they won 21-17.

An interesting side story here is that fellow rapper Birdman wanted to bet $5 million against Jackson. 50 declined the $5 million amount, but was willing to wager $1 million against Birdman.

The latter thought the stakes were too low and turned Jackson down. However, 50 did find a sportsbook that took the bet.

Mick Gibbs

Mick Gibbs was just a simple roofer from Staffordshire, UK, when he decided to make a life-changing bet. He wagered 30 pence on a 15-team soccer accumulator.

The odds of him winning were just 1.67 million to 1. He was on his way to defying the odds, though, when the first 14 teams won.

The final game involved Bayern Munich and Valencia. Gibbs had Bayern winning this Champions League final.

The match provided extra suspense by going to penalty kicks. Bayern Munich emerged victorious, giving Gibbs a £500,000 payout on his tiny original bet.

Fred Craggs

Fred Craggs is similar to Mick Gibbs in that he was just a simple man before sports betting changed his life. The fertilizer salesman decided to make an eight-horse parlay wager on his 60^th birthday.

He risked 50 pence on the bet and didn’t take much time looking over the selections. His odds of winning were 2 million to 1.

Craggs walked into a William Hill betting shop later on to make more bets. He didn’t realize, though, that his parlay had been successful.

He should’ve actually won £1.4 million on the wager. But William Hill’s terms capped his parlay win at £1 million.

Regardless, he was still extremely happy about the win. Craggs was able to retire earlier than expected afterward.

Sports Betting Odds

Conclusion

You can see that people from all walks of life are capable of winning big in sports gambling. Some are skilled pros who develop a great strategy, while others are amateurs who’ve defied the odds.

Drake’s dad is the latest remarkable story from the sports betting world. He risked quite a bit ($100k) on the Raptors winning, but was well rewarded with a $300,000 payout.

Biggest Sports Betting Wins College Football

Sir Ride A Lot brings another impressive tale. He let his winnings ride on six straight World Series games, earning a combined $14 million as a result.

Haralabos Voulgaris and Billy Walters both relied on strategy rather than luck to win big. Both have made millions from sports gambling over their careers.

50 Cent, Gerry McIlroy, Fred Craggs, and Mick Gibbs are a few more cases of being lucky, rather than great bettors. Nevertheless, they all profited big from sports wagering as well.