Biggest Long Shot Sports Betting Lines Of All-Time

Sometimes, an underdog no one expects to win takes the game — and sportsbook operators' money. So, what are some of the biggest 'longshot' betting lines in history, that ended up winning? Here's my top 5.


Winning one big bet that delivers a life-changing amount of money is something millions of sports betting fans can only dream of. There’s a reason the phrase “against the odds” truly means an outcome is unlikely to ever happen. But that doesn’t mean shock sporting results are beyond the reach of normal punters.

In a digital age where you can bet on sports from around the world with just the tap of a screen or click of a button, the opportunity to place ‘longshot’ bets and chase big rewards has never been greater.

And as history shows us, some punters have benefitted from the basic principle of sport that anyone can beat anyone on their day. Here, we’ve looked at five of the biggest longshot sports betting lines in history, and how they came about…

Biggest Ever Longshot Sports Bets

The drama, the narrative, the against-the-odds heroism. Here are our top five longshot winning sports bets:

1. Horse Racing

  • Donerail wins the 1913 Kentucky Derby | +9100 winner

The Kentucky Derby forms part of American racing’s Triple Crown and decades after Donerail won the 1913 race bettors still dreamed of backing such an outsider to glory. Racing betting records show there was a $2 bet placed on Donerail before the Kentucky Derby that year and that the lucky punter walked away with $182 profit, meaning a bet at +9100 had been placed.

Donerail not only beat his closest rival Ten Point by half a length but also ran the fastest Derby time ever recorded by that date – 2:04:80. That record stood for just one year before Old Rosebud shaved over a second off the time, but it was Donerail’s name that survives in Kentucky Derby folklore as the first big upset against the odds.

2. Soccer

  • Leicester City win the 2016 Premier League | +50000 winner

Leicester’s shock charge to the English Premier League championship in 2016 fundamentally changed soccer betting odds and the wider world of sports betting as a whole. The Foxes had started the league season as one of the favorites for relegation under Italian manager Claudio Ranieri, whose band of players was largely made up of the squad that two years previous had been competing in the second tier of English football.

manchester vs leicester 2016 game

Manchester vs. Leicester, 2016.

But Ranieri’s side found a remarkable knack of sucker-punching traditionally bigger teams and was soon vying for the top four in the league. Victories over Liverpool and Manchester City within four days in February suddenly catapulted Leicester into the title race for real. They held off the challenge of Tottenham and Arsenal to win the league by 10 points and force bookmakers into serious payouts. Some hopeful fans had stuck £10 on Leicester at odds of +50000 and made a fortune. Bookies lost an estimated $15m and since then sports odds never go as high as +50000.

3. Boxing

  • Buster Douglas beats Mike Tyson in 1990 | +4200 winner

The mark of a champion is one who takes their chance when it’s within their grasp – and Buster Douglas certainly did this. Mike Tyson was the undisputed, undefeated heavyweight champion when he went up against Douglas in Tokyo for what was expected to be a routine win. Tyson had KOed Carl Willians within 93 seconds of his previous fight and was odds-on to win here in Las Vegas’ boxing betting markets.

black and white photo of boxer getting hit by punch

Nobody thought Douglas had what it took — how wrong they were.

But Douglas was on a roll of six straight wins and believed he had earned his shot at Tyson. He came at Tyson from the first bell and wasn’t cowed by the stinging hands of Iron Mike. Indeed, Tyson began to tire as the fight wore on, even though he did manage to floor Douglas in the eighth round. Douglas recovered, got back to his corner, and two rounds later delivered a fierce uppercut that sent Tyson to the canvass for the first time in his career.

Vegas had taken scores of bets in the lead-up to the fight, most of which were on which round Tyson would win. Jimmy Vaccaro, bookmaker at the Mirage at the time, claimed one bettor placed $168,000 on Tyson to win, for a payout of just $4,000.

4. Tennis

  • Sergiy Stakhovsky beats Roger Federer at Wimbledon in 2013 | +4500

Roger Federer was still at the peak of his powers when he entered Wimbledon as defending champion in 2013. The Swiss maestro had 17 Grand Slams in his locker, had beaten Andy Murray in the Wimbledon final the year before, and came into the 2013 Slam as the favorite in the tennis betting markets, having won the Halle title on grass two weeks previous.

But Federer suffered arguably the biggest shock defeat of his career when he went four sets against World No.116 Sergiy Stakhovsky. Federer won the first set on a tie break but Russian Stakhovsky rallied back with three straight sets – two of which went to tie breaks. Despite his prowess and technical mastery on grass, Federer just couldn’t force Stakhovsky into submission.

The match ended with Federer backhanding a routine shot down the line, with the ball sailing out. Stakhovsky fell on his back as the Centre Court crowd roared in delight. The champion was defeated and Stakhovsky earned some punters a smooth $450 off a tennis $1 bet.

5. NFL

  • St Louis Rams win the 1999 Super Bowl |+15000 in pre-season

No one expected the Rams to do much in the 1999 NFL season as head coach Dick Vermeil sought to pick the team up from back-to-back fifth-place finishes in the NFC West. St Louis were a joke team, having strung together four successive losing seasons. The NFL betting odds paid them no attention.

kurt warner at super bowl xxxiv press conference for st louis rams 1999

Kurt Warner at a press conference post-1999 Super Bowl.

But things changed at the start of the ’99 season when Trent Green’s injury means reserve QB Kurt Warner was suddenly the main man. Aided by an offensive arsenal that included Marshall Faulk, Torry Holt, Isaac Bruce, Ricky Proehl, and Az-Zahir Hakim, Warner spearheaded a Rams revival that led them to the top of the conference and into the playoffs.

Even at that stage, the Rams weren’t expected to go all the way but they demolished Minnesota 49-37 before edging a tight game with Tampa Bay 11-6. By that point, fans who had bet on St Louis at +15000 in pre-season were cashing out early. But those who stayed loyal to the team watched them cruise past Tennessee 23-16 in the Georgia Dome, with Warner throwing TDs for Holt and Bruce.

Cliff Spiller

Cliff Spiller is a veteran casino writer with decades of experience writing online casino reviews and game guides. His betting strategy articles, and gambling news updates have been a fixture in the industry since 2004.

Back To Top
Back To Top