Drake has made headlines once more with a massive bet on this weekend’s UFC 305 main event between Dricus Du Plessis and Israel Adesanya.

The rapper, who is estimated to be worth $250 million, has become almost as well-known for his high-stakes gambling as he is for his chart-topping music. But with his latest wager, fans are left wondering: will the infamous ‘Drake Curse’ strike again?

Drake has placed a $450,000 bet on Adesanya to defeat Du Plessis and reclaim his middleweight title in Perth. ‘The Last Stylebender’ hasn’t stepped into the octagon since losing his title to Sean Strickland last year, and this fight is seen as a crucial comeback opportunity.

However, Drake’s track record with betting on high-profile fights is less than stellar. The ‘Drake Curse’—a social media phenomenon—originated after a series of athletes experienced losses or setbacks following their association with the Canadian musician.

One of Drake’s most recent missteps saw him lose a staggering $615,000 when he backed Francis Ngannou to defeat Anthony Joshua in their March bout in Saudi Arabia. Joshua, however, emerged victorious with a sensational win.

If Adesanya triumphs in Perth, Drake stands to win $855,000. But history suggests the rapper might be in for another disappointment.

“Always with Izzy,” wrote Drake.

Earlier this year, Drake lost over half a million pounds when he incorrectly bet on Strickland to defend his UFC middleweight title against Du Plessis at UFC 297.

He also lost £430,000 when Adesanya suffered a shocking defeat to Strickland last year. Despite his confidence in ‘The Last Stylebender,’ the fighter was unable to secure the knockout victory Drake had hoped for.

Drake’s penchant for gambling isn’t limited to UFC bouts. Last year, he placed a significant bet on YouTuber-turned-boxer Logan Paul to knock out Dillon Danis in their Misfits Boxing match. While Paul didn’t secure the knockout, Drake still walked away with over a million dollars after Danis was disqualified in the final round for attempting an illegal chokehold, which triggered a massive brawl in the ring.

The rapper has also tested his luck in football, notably losing a substantial £777,000 ($1 million) bet on Argentina to defeat France in normal time during the 2022 World Cup final. Although Argentina eventually won the match in a penalty shootout, Drake’s bet failed as the game was tied 2-2 at the end of 90 minutes.

As UFC 305 approaches, all eyes are on Adesanya to see if he can break the ‘Drake Curse’ or if the rapper’s betting luck will continue to falter.