But luck isn't usually on the rapper's side. This weekend, he has lost a staggering $430,000 (£363,000) on UFC bets.
Drake had £169,000 ($200,000) on Kamaru Usman to defeat British fighter Leon Edwards, with the Brit eventually coming out on top.
This comes after earlier in the night, the hip-hop star had also bet on Jose Aldo to beat Merab Dvalishvili, however, that also went against him.
That stake was worth more than the Kamaru fight at £194,000 ($230,000).
Drake had split the Kamaru, Edwards fight into two separate wagers, both of which he lost.
The Canadian originally placed a £125,000 ($149,000) bet on the Nigerian Kamaru to win the fight by KO. He then spent a further £44,000 ($49,000) on Kamaru to win in the fourth round.
The rapper has been constantly accused of cursing fighters as he often ends up placing bets on the eventual loser.
Drake's first public bet came back in March where he staked an incredible £232,000 ($275,000) on Jorge Masvidal to beat Colby Covington, but Covington resoundingly beat his competitor.
Two months later, the rapper elected to bet on an outsider, putting down £338,000 ($400,000) on Justin Gaethje beating Charles Oliveira at UFC 274. Gaethje eventually lost the fight in the first round.
However, it is not all bad luck for Drake when it comes to betting on the UFC.
The rapper eventually turned things around with a bet on on Israel Adesanya successfully defending his belt against Jarod Cannonier.
The long-awaited good luck for Drake bagged him around £850,000 ($1 million).
You might have thought that luck was changing, as recently he backed British pair Paddy Pimblett and Molly McCann in a double bet which saw him pocket a cool £3 million ($3.5 million). Sadly, his winning streak quickly ended.
Drake's unfortunate betting luck is not just associated with UFC.
He made a £186,000 ($220,00) bet on Charles Leclerc to win the Spanish Grand Prix in Formula 1, only for the driver to retire from the race due to an engine failure after starting on pole.
Prior to this, just spending time with Drake appeared to be enough to lead to a catastrophic sporting loss.
Footballers such as Sergio Aguero, Pierre Emerick Aubameyang and Jadon Sancho have all gone on to lose matches shortly after being photographed with the musician.
Meanwhile, other sports stars like Serena Williams and Anthony Joshua have also been hit by the Drake 'curse'