Dave Portnoy loses $25k World Cup bet and rages at ‘impossible’ knockout scenario

Jun 29, 2026 - 18:45
Dave Portnoy loses $25k World Cup bet and rages at ‘impossible’ knockout scenario

Dave Portnoy lost an eye-watering amount of money betting on Canada to lose their Round of 32 game at the World Cup.

The co-hosts played South Africa in the first knockout game of this summer’s tournament on Sunday, which featured a dramatic finale in Los Angeles.

Stephen Eustáquio 7 of Canada celebrates with teammates after scoring a goal during the FIFA World Cup 2026 Round Of 32 match between South Africa and Canada at Los Angeles Stadium on June 28, 2026
Canada booked their place in the World Cup Last 16 with a dramatic win over South Africa
Getty

In a goalless game that looked destined for extra time, Stephen Eustaquio stepped up to became an instant hero for Canada by netting a 92nd-minute winner.

The result sent the Canadians through to the Last 16, and cost Barstool Sports founder Portnoy quite the sum of money.

Dave Portnoy lost massive World Cup bet on Canada vs South Africa

Moments before that game kicked off, he revealed to his followers that he put a $25,000 bet on South Africa to advance instead.

“I think I’ve decided to bet and win every knockout round game the rest of the World Cup,” he posted Sunday.

“It starts today with South Africa. I just don’t see Canada advancing in soccer.”

The screenshot of his Draft Kings bet revealed that the $25,000 stake would have returned $83,750 had South Africa beaten Canada.

Instead, Portnoy is $25k down — and it’s fair to say he wasn’t very happy about it.

Speaking in the hours that followed the dramatic game, he shared his shock at Canada being one of the ‘top 16’ soccer teams in the world.

“I can’t believe, and I don’t know if we’re the victim here of the NCAA-iffication of the World Cup in which we had a lot more teams in,” he told Wake Up Barstool.

“But I cannot almost live in a world where Canada… you’re telling me Canada has one of the best 16 soccer teams in the (world)?

Dave Portnoy looks on prior to Game Four of the 2024 NBA Finals between the Dallas Mavericks and the Boston Celtics at American Airlines Center on June 14, 2024
Portnoy lost $25,000 betting against Canada at the World Cup
Getty

“That just seems impossible.

“Who’s playing soccer in Canada? Losers? Canada’s such a hockey (nation).”

Jesse Marsch celebrates ‘heroes’ after World Cup history

While Portnoy was left red-faced and $25k down after Canada’s win, those north of the border are revelling in some soccer history.

Sunday’s game was the first time in World Cup history that a host nation has played outside their own country.

It also marked Canada’s first-ever knockout game at the tournament, and in turn, their first knockout win.

Speaking after the drama, head coach Jesse Marsch heaped praise on his history-making players.

Jesse Marsch, Head Coach of Canada, speaks with his players in a huddle after the team's victory and their side's progression to the Round of 16 after the FIFA World Cup 2026 Round Of 32 match between South Africa and Canada at Los Angeles Stadium on June 28, 2026
Marsch described his team as ‘heroes’ after they made World Cup history
Getty

“Canadian heroes,” he called his team.

“The future of the sport in this country is huge because of you.”

Canada will face a tough challenge against either Morocco or the Netherlands in the Last 16 of the World Cup, in a game set for Saturday, July 4 in Houston.

Regardless of who they face, Marsch’s team will be big underdogs — but Portnoy might be more hesitant to bet against them this time around.

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