Drake made yet another big bet on a sporting event, and this one definitely did not pay off.

On Friday (November 15), the superstar revealed that he had placed a $355K wager on Mike Tyson to beat Jake Paul in their fight that evening.

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“I’m late but I’m here money on the liiiiiiiiine for today and tmrw,” he captioned his Instagram post.

Paul was heavily favored, so Drizzy stood to win over a million dollars if his bet turned out.

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However, that was not to be the case.

Paul defeated Tyson by unanimous decision in the eight-round bout, meaning Drake lost the bet. As yet, he has not commented on his defeat.

In addition to the Tyson/Paul bout, Drake shared that he’d placed an additional six-figure bet on a different fight: the UFC bout between Jon Jones and Stipe Miocic, which takes place on Saturday (November 16). The rapper bet $450K that Jones would win by knockout — a bet that would more than double his money if he wins.

This was not Drizzy’s first time losing money on a Logan Paul fight.

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Back in 2023, he bet money on a Paul fight — and ended up nearly $1 million poorer.

Paul ultimately triumphed over his opponent, Dillon Danis, in Manchester on October 14 of last year. However, the triumph was due to a disqualification, as Danis tried to choke Paul out during the match.

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So even though the 6 God placed his bet (via the online casino Stake) for Paul to be the victor, he predicted the fighter would win by knockout, not disqualification. As a result, the $850,000 bet was a loss.

Had Drake won the bet, however, he would have won $1.3 million.

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He also placed a huge bet on an August 2023 fight between Paul and former UFC contender Nate Diaz.

According to TMZ, the 6 God made a wager to the tune of $250,000, ahead of the 10-round cruiserweight bout (catchweight of 185 pounds), in favor of Diaz. “Jake is a dog but I can never bet against a Diaz brother that’s just how I was raised,” Drizzy told the outlet.

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Drizzy has a long history of betting on the Stake platform, of which he has an ownership slice, per GrandPrix.

In February 2022, it was revealed that the Scorpion rapper has bet almost $1 billion in virtual gambling since 2021, all of it done on the Stake platform.