Canadian superstar Drake faced a $300,000 loss after Canada’s 2-0 defeat to Argentina in the Copa America semifinal. With total odds of $9.60, Drake stood to win an estimated $2.88 million had Canada emerged victorious against the reigning world champions.

Drake shared his bet slip on Instagram on Tuesday afternoon with a caption that humorously referenced Argentina’s star player, Lionel Messi: “This could get Messi @stake.” This marks the second high-profile bet Drake has lost this year, following a $565,000 wager on Tyson Fury’s unsuccessful bout against Oleksandr Usyk in May.

Goals from Lionel Messi and Manchester City’s Julian Alvarez secured Argentina’s victory at New York’s MetLife Stadium, advancing them to the final. Argentina will now await the winner of the semifinal between Uruguay and Colombia, with the final set to take place at Hard Rock Stadium in Miami Gardens, Florida, on Sunday, July 14. Meanwhile, Canada will contest for third place against the loser of the Uruguay vs. Colombia match.