Drake lost £401,000 [$500K] backing Israel Adesanya at UFC 293.
Just hours before 'Stylebender' was due to defend his middleweight title against Sean Strickland, the rapper revealed the massive amount of money he'd placed on the fight.
Drake has often gambled big on combat sports, including the UFC, and has earned a reputation for being 'cursed' due to his bad luck with betting.
At odds of 1.84, he was hoping to see £738,000 [$920K] enter his bank account after Adesanya delivered on his favourite tag, but things didn't go his way in Sydney, Australia on Sunday morning.
Strickland scored a heavy knockdown in round one before avoiding Adesanya's power shots for the next four frames to cost Drake big time.
The 32-year-old was ultimately crowned the new champion after all three cageside judges scored the fight 49-46 in his favour.
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Despite his reputation as a jinx, the Hotline Bling singer does have sporadic success with gambling and earlier this year he landed a whopping £2.2 million at UFC 287 for a succession of bets that came in.
Adesanya was the man he was backing, and on that occasion, he managed to KO Alex Pereira to regain his UFC middleweight belt.
However, with every high comes a low and the Canadian rapper has also experienced some damaging losses.
Drake splashed £200,000 [$250K] on Nate Diaz to beat Jake Paul in August, only for the YouTube star to claim victory via unanimous decision.
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He also bet a million dollars that Argentina would beat France in the World Cup final - in normal time - a match that Lionel Messi and co. would win on penalties.
Drake also reckoned Paul would knock Tommy Fury out in their bout earlier this year, only for TNT to win via unanimous decision.
This is not the first time Adesanya has let down the 36-year-old.
Drake went bet a £1.7 million [$2M] on the New Zealander to beat Pereira at UFC 281, only for him to suffer a fifth-round stoppage loss.
It'll be interesting to see if he backs Adesanya in his comeback bout.
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