The biggest and boldest sports bets of all time

Let’s look at some of the craziest record-breaking sports bets ever made.

The Biggest Horse Racing Collect of All Time

In 2015, a syndicate of betting professionals won over R182 million in one day at the Melbourne Cup horse race in Australia. They accurately predicted the winner of the first five races at the event, cashing in on a series of bets with Ladbrokes and William Hill. They reinvested their winnings into the next race with each correct pick, culminating in a massive pay-out.

Ladbrokes alone paid out R121 million to the syndicate, marking the betting agency’s largest racing loss ever.

This monumental win shattered the previous record for the biggest multi-race payout of R16 million won by a British bettor in 1996.

R250 Million Scored Betting on Tiger’s Masters Comeback

In 2018, an unknown punter bet R25 million at 14.0 odds that Tiger Woods would win the Masters Tournament. At the time, Woods was over a decade removed from his last major golf title and had recently ranked outside the top 1000 players. But the mystery bettor had faith in Tiger’s chances.

Woods secured his fifth green jacket and first major win in 11 years at Augusta National, triggering a payout of over R250 million. The bettor took home one of the biggest payouts in sports betting history by trusting in the comeback capacity of one of golf’s greatest champions.

“Mattress Mack” Uses World Series Bet as Marketing Ploy

James “Mattress Mack” McIngvale, owner of Gallery Furniture in Houston, Texas, is known for large wagers on his beloved Astros. But his biggest bet came in 2019, before the World Series. He placed R58 million on the Astros to win at 2.20 odds.

He offered a store promotion to hedge against a loss to refund any mattress purchases over R3,000 if the Astros won the Series. Houston ultimately prevailed, saving Mack from eating the considerable loss and instead giving his business a marketing boost. With clever hedging, Mack transformed sports betting into a business opportunity.

Mayweather’s Big Fight Sets Betting Record

In August 2017, Conor McGregor crossed from UFC to boxing to take on undefeated champion Floyd Mayweather Jr. While McGregor was an underdog, one anonymous bettor staked R91 million on Mayweather to win the bout. With Mayweather victorious by 10th round TKO, the bet paid over R100 million at 1.12 odds.

This wager set records for the largest bet on a boxing match from a single, confirmed source. Most reports estimate it as one of the biggest bets ever on a sporting event. The fact that the mystery bettor risked over R91 million showcases the massive money exchanged during premium matchups.

100-1 Underdog Horse Delivers R50K Score

While big bets on favourites make headlines, underdogs occasionally defy the odds. In Australia’s 2015 Preston Bend Mile horse race, galloper Bellmare Princess scored an upset at 101.0 odds. One lucky punter bet R500 on the horse pre-race, cashing out a ticket worth R50,000 when Bellmare Princess crossed the line first.

This regular bettor broke betting records by owning the only winning ticket on the longshot winner. His modest wager demonstrates that anyone can land a life-changing score, even when betting on the extreme underdog.

Placing Massive Sports Bets Can Lead to Huge Payouts

As these stories prove, any sports bettor can land a huge win with some luck. For those looking to get in on the action, legal sports betting sites like Easybet makes it simple to place bets online for almost any sports event on their betting app.

Please note: Only gamble what you can afford to lose. Gambling involves risk.

(USD/ZAR converted at 18.70 for the purposes of this article).