Drake was confident that Jake Paul could pull off an upset victory over Anthony Joshua in their heavyweight boxing match on Friday night.

The Jake Paul-Anthony Joshua bout Friday night has the boxing world enamored on social media ahead of the biggest fight of ...

Drake’s reputation as a terrible sports bettor remained intact Friday after he showed his personal pick for the Jake ...

Drake loses $200,000 betting on Jake Paul as infamous betting curse strikes again, leaving fans stunned online.

The Drake curse could be on full display again. The famed rapper, who tends to gamble — and often lose — a lot of money on ...

Jake Paul fans might need to close their eyes after rapper Drake, who is known for losing big bets, backed the fighter.

Canadian rapper Drake has reportedly lost about ₦300 million ($200,000) bet after backing Jake Paul to defeat Anthony Joshua ...

In Paul’s highly controversial fight against Mike Tyson last November, Drake wagered a huge $355,000 bet on Tyson to beat the ...

Drake has lost of $500,000 betting on Jake Paul. Paul's latest match was against former heavyweight champion Anthony Joshua.

On Saturday night (August 5) in Dallas, actor-influencer turned quasi-pro boxer Jake Paul fought Nate Diaz, one of the most notable names in mixed martial arts in the last decade. Although no ...

Drake apparently is trying to avoid making the same mistake in two straight Jake Paul fights. The rapper didn’t cash in on a $400,0000 wager on Paul to knock out Tommy Fury in February, as Fury ended ...

Drake would be willing to settle his legendary rap feud with Kendrick Lamar in the boxing ring, but doesn’t want it broadcast. The two music moguls have had one of the defining beefs of this ...