Top 5 Biggest Boxing Betting Payouts Of All Time

Boxing is a sport of thrilling excitement that can turn on its head in a matter of seconds - so it should come as little surprise that it is one of the most popular betting sports, too. From journeyman underdogs causing incredible upsets, to fighters betting on themselves, there have been some incredible boxing payouts over the years - let's take a look at a few of our favorites...

5. Floyd Mayweather Jr. v Manny Pacquiao (2015) - £225,000 ($287,000)

In the making since 2009, this fight is frequently referred to as the ‘Fight of the Century’, taking place in May, 2015 at MGM Grand Garden Arena in Las Vegas. The bout was between eight-division world champion Manny Pacquiao and undefeated five-division world champion Floyd Mayweather Jr.

The fight went the distance, with Mayweather getting the unanimous decision, which delivered an unforgettable win for one punter. The anonymous Irish bettor, who was in his 80s, placed an eye-watering bet of £150,000 on Mayweather at odds of 1-2, which landed him a handy payout of £225,000.

4. Curtis Woodhouse Betting On Himself To Win (2014) - £250,000

After winning a British welterweight title in 2014, footballer-turned-boxer Curtis Woodhouse refused to rule out the possibility he had bet on himself, stating: "I can neither confirm nor deny these rumors, but the drinks are on me!"

The rumors he was referring to suggested he had placed a £5,000 bet on himself becoming a future boxing champion at eye-catching odds of 50-1. A winning return from such a bet would have pocketed the outspoken former football £250,000.

The bet was thought to have been placed back in 2006, when Woodhouse turned professional. A mere six years and 27 fights later, he achieved his aim when he claimed a split-decision win over Darren Hamilton - taking the title - and potentially a life-changing betting win, too!

3. Floyd Mayweather Jr. v Conor McGregor (2017) - $1 Million

The inaugural 'crossover' fight between Floyd Mayweather and Conor McGregor is still considered one of the biggest events in sporting industry, having grabbed everyone's attention back in August 2017. More than that, it was considered an epic betting event, too, with RJ Bell from the Associated Press quoted as saying it was "the biggest bet fight ever".

An entertaining fight lasted 10 rounds before the far superior Mayweather put a tiring McGregor out of his misery. One lucky punter placed a ridiculous high-stakes bet of $800,000 on the undefeated Mayweather at odds of -550 at the South Point Sportsbook. Returning just $120,000 extra against his original bet, you have to wonder whether this bet was worth the stress!

2. Drake Betting On Gervonta Davis To Beat Ryan Garcia (2023) - $1.38 Million

When Gervonta Davis faced off against Ryan Garcia in April 2023, he wasn't just looking to overcome one of the world's best boxers, but also the 'Drake Curse'! Before the fight, the Canadian rapper had made it known he had placed a sizeable bet on the undefeated Davis, but given his track record of dodgy bets, that 'support' looked unlikely to help.

However, Davis took his record to a perfect 29-0 with a knockout win over Garcia, having floored him in the seventh round with a mean strike to the stomach. With the talented fighter being the overwhelming favorite in the bout, Drake's incredible $1 million bet with his partner company Stake.com only returned a total win of $1.38 million - still... not bad for a single bet, especially when you're meant to be cursed!

1. Buster Douglas v Mike Tyson (1990) - $2.1 Million

February 1990 will always be etched into boxing folk lore, with Buster Douglas causing one of the biggest upsets in the sport's history. Undefeated world champion Mike Tyson was expected to walk through the 42-1 underdog on the way to bigger things, but an incredible 10th-round knockout turned the boxing world on its head.

One anonymous bettor was deliriously happy with this unexpected outcome, having placed a $50,000 wager on Douglas to win at those 42-1 odds. The bet landed as soon as Tyson hit the canvas and he made an incredible return of $2.1 million!