Biggest Sports Parlay Win

Parlays are the ultimate big-win chaser’s dream. The combined bets provide massive potential payouts on nominal wagers, and nearly every online sportsbook offers them. Though the odds are low for a given parlay to hit, the possible winnings are huge, and a handful of lucky bettors have cashed in some gargantuan parlay jackpots at legal sportsbooks worldwide.

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1. With the Lions securing the parlay win with a 24-10 victory over the Giants the bettor walked away with $250,000. This went down as one of the biggest parlays wins in the sports betting space.
2. The former because parlay paydays are so attractive and the latter because parlays are so hard to win. According to data compiled by the UNLV Center For Gaming Research from 1984 to 2019, the win percentage Nevada sportsbooks enjoyed on parlays was over 30%, compared to around 5% for all sports.

A bettor at the William Hill Sportsbook at the Venetian in Las Vegas is walking home a big winner after cashing in on a seven-leg parlay. The ticket was bought for $4,000 and flipped for a total. If your bankroll is limited to just $100, using straight wagers you’d make four separate bets of $25 to win $22.73. If you we’re feeling both lucky and in the mood to gamble, you might instead bet them all together as a four team parlay. Under the parlay option, the stakes would be $100 to win at least $1,000. The $62.5k win for the bettor is a huge sum to win from a $25 wager. However, where does it rank compared to the biggest sports betting wins ever recorded in the US? Well, it’s not a bad payout but.

But before jumping into some of the craziest parlay wins on record, it helps to better understand the betting method, its upsides, and the inherent risk.

How Parlays Work

In simple terms, parlays are “all or nothing” bets. Parlays combine two or more individual bets into a single wager. This ramps up the odds so that a parlay pays much higher than any of the individual bets.

For example, I combined four bets with odds of -110, -110, +150, and +115 today on PointsBet, and the parlay payout came in at +1859. A $20 bet would pay more than $390.

Of course, there’s a catch. For a parlay to win, each individual bet must win. If you combine four bets into a parlay and one of them loses, you lose your bet even if the other three bets won. For that reason, parlays are risky bets, and most experts encourage you to steer clear.

On the other hand, casual bettors might enjoy making a weekly parlay every NFL Sunday or while any other league is in the thick of its season. There’s nothing wrong with making the occasional parlay bet as long as you acknowledge that your odds to win are low, similar to playing a slot machine.

Five Crazy Parlay Wins

Some bettors have beat the odds and been lucky enough to nab astronomical parlay wins in the past. Here’s a round-up of five amazing parlay wins.

The Three Sport Combo

Last year brought a huge windfall to one FanDuel sportsbook bettor who won on a $200 parlay combining 15 NBA, NFL, and NHL bets. The bet hit in November 2019 when all of the bettor’s moneyline wagers won for a payout of $229,276.

The moneyline bets boosted this wager over the edge for a massive win, because moneylines tend to offer longer odds if you pick the underdog. Whether it was sheer luck or educated guessing, this bettor came out on top.

The Charcuterie Parlay

In March 2019, sportsbooks were starting to take off in Mississippi on the heels of an August 2018 launch. March brought one noteworthy parlay win that featured a little bit of everything.

Rather than sticking to one type of bet, this bettor wagered $25 on a 20-leg parlay. The parlay was a veritable smorgasbord of bets and sports, including point spreads, moneylines, and totals. The wager covered a slate of Friday-night games across the NBA and NCAA basketball.

According to ESPN, the customer at BetAmerica sportsbook in Vicksburg, Mississippi’s Riverwalk Casino wagered on 14 favorites, three underdogs, and three “over” totals bets.

After a few close calls, the 20-leg bet won, netting the bettor a $104,412 win.

The Homecoming Special

In September 2020, a BetMGM customer raked in a $152,341 win on a $10 parlay.

The 11-leg bet featured five moneyline bets, five totals, and a single point spread wager (Duke +20.5). The majority of the bets predicted college football match-ups, but a few additional professional games sent the bet over the edge. The Rockets-Lakers under and the Yankees moneyline contributed to the win, resulting in a huge payday for the lucky bettor.

The 15-Leg NFL Slate

Amateur sports bettor Tayla Polia’s parlay success story is featured on countless lists just like this one, and for good reason. In 2015, Polia placed a $5, 15-leg parlay that included 14 point spread bets and one totals wager for the Steelers-Broncos matchup.

To her surprise, Polia’s bet won and paid out 20,000-1 for a cool $105,000. She actually thought the bet had failed initially because the Giants lost their match-up. But Polia had bet on the team to cover, which they did, completing her parlay and netting her a huge win.

Root, Root, Root For The Home Team

In 2015, MLB fans worldwide witnessed history. For the first time since the league’s inception, all 15 home teams won their games on a single day.

One lucky bettor cemented his place in the story by predicting the event with a 15-leg parlay bet. The Ireland bettor had plenty of reason to celebrate proverbial Irish luck when his ~$78 bet, placed at William Hill’s sportsbook, won him $100,810.

Should I Place Parlay Bets?

You may see these wins and instantly open your sportsbook app to start placing a few parlays for yourself. Before you do, it’s important to note that these wins are the exception, not the rule. The sage advice from sports betting experts is to stay away from parlays.

However, it’s okay to place a parlay bet once in a while, especially if you feel confident about a select few match-ups. Parlays can be a fun way to get in on the action and invest yourself in the match-ups of the day. Just play responsibly and keep in mind that your chances of winning any parlay are slim.

Parlay Tips

If you’re planning to place parlay bets, there are a few tips to keep in mind.

Less Is More

Sure, a 15-leg parlay is enticing, especially if the payout has four, five, or even six digits. But the more bets you include, the less likely you are to win. IF you’re interested in placing parlays, keep them simple at first. Combine two or three bets and see how they perform. If you’re lucky, you might win a few hundred dollars.

Favoritism Can Be A Benefit

Underdogs offer better payouts, but that’s only because they are viewed as less likely to win their match-up. If you’re building a parlay of moneyline bets, pay close attention to the odds. If one team is heavily favored to win, that might be the wiser pick.

Carefully Consider Home Team Bets

Unless it’s the mid-90s and you’re placing Chicago Bulls bets every week, try to steer clear of home-team bets when you’re building a parlay. I’ve fallen victim to the trap many times–I place a 5-leg parlay bet that includes my Chicago Bears to win only to find a disappointing 4-1 parlay that loses me my initial bet thanks to a crushing Chicago loss.

If you want to bet on your home team, keep that wager out of your parlays or risk disappointment.

Point Spreads Even Out The Odds

Betting on point spreads gives you smaller individual payouts, but combining them into parlays can produce big potential wins. Point spreads even out the odds of a given match-up, giving the predicted underdog a chance to cover the spread even if they lose the match.

Biggest Parlay Wins

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.

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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.

Biggest Sports Parlay Wins

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.

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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

Biggest Sports Parlay Winning

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

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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.