Dave Portnoy lost an eye-watering amount of money when betting on Canada to lose their FIFA World Cup 2026 round of 32 match with South Africa.
Canada progressed out of Group B with four points after drawing with Bosnia and Herzegovina and beating Qatar.
That teed up a round of 32 meeting with South Africa, who surprisingly emerged from Group A behind co-hosts Mexico ahead of South Korea.
Jesse Marsch’s team then made history in Los Angeles as Canada beat South Africa 1-0 thanks to a late goal from Stephen Eustaquio.
It is fair to say that Portnoy, the founder and owner of the popular Barstool Sports, did not see that coming.
Portnoy loses huge bet on Canada
Ahead of the game, the 49-year-old took to social media platform X to write: “I think I’ve decided to bet and win every knockout round game the rest of the World Cup. It starts today with South Africa. I just don’t see Canada advancing in soccer.”
He posted an image of his bet, with a whopping $25,000 placed on South Africa to progress at Canadian expense. That would have seen him rake in a huge $83,750.
However, the fact that Canada won clearly means the bet was lost, with that late goal from Eustaquio proving very expensive for Portnoy.
Marsch hailed his players as “Canadian Heroes” after their victory.
Never before had Canada even won a game at a World Cup but now they are just one game away from the quarter-finals.
Still, a difficult task lies in wait in Houston next time up. The co-hosts will play the winners of Netherlands vs Morocco.
Yet, with so much attention paid to the USMNT’s surprisingly good campaign so far, as well as the joy Mexico have found when playing at home, it is no doubt good to see Canada making significant progress.
Arguably the most overlooked of the three host nations, they are going about their business somewhat under the radar as they eye yet more history.
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