Having a little flutter on a sports match can be a fun pastime; however, Drake has ended up getting stung hard after betting the wrong way on a boxing match.
One press conference even descended into a fight of its own as security tussled.
Drake had decided to throw his money behind Nate Diaz. And we're not just talking twenty quid here either, the rapper bet nearly £200,000 on the outcome of the fight.
Unfortunately for Drake, Diaz ended up losing the fight, which cost the rapper some £196,080 on his bet. Ouch.
The fight went for the full ten rounds, with neither fighter achieving a decisive knockout. However, in the end, the decision for the fight was that Jake Paul was the victor.
Paul did manage to knock down Diaz, 38, in the fifth round of the contest. However, Diaz soldiered on to go the full ten rounds against his opponent.
However, the odds would have been quite something, as Drake had bet some $250k on Diaz to win the contest. If he had won then Drake would have walked away with $1 million in prize money.
He shared a photo of a betting slip to his Instagram.
The picture was captioned: "Jake is a dog but I can never bet against a Diaz brother that's just how I was raised."
The Canadian's run of bad luck at the bookies has even led to him being christened with 'The Drake Curse'.
Last year he lost $1 million (£784,320) when he bet on a match between Argentina and France, betting that Argentina would beat France at the World Cup final in normal time.
On another occasion, he lost $684,000 (£537,000) betting Barcelona to beat Real Madrid in El Classico. Prior to that he had lost a whopping $2m (£1.7m) betting on UFC fighter Isreal Adesanya to beat Brazilian fighter Pereira.
At this point it might even be worth watching who he bets on next and betting the opposite way!
It's also not the first time that Drake has lost money on a fight involving Jake Paul, as he previously bet $400,000 (£313,728) on him, only for Paul to lose out to Tommy Fury.
Paul jokingly blamed Drake's loss on him, though he did apologise for costing him the money.
He said: "$400k is nothing to him. He's won a lot more money betting on me before, so he's probably about even now."