Cerrone turns $10,000 into $45,000 backing Strickland's upset win over Chimaev at UFC 328

Donald ‘Cowboy’ Cerrone turned a $10,000 wager into $45,000 by backing Sean Strickland to defeat Khamzat Chimaev at UFC 328 in Newark, New Jersey earlier this month — one of the most lucrative personal paydays to emerge from one of the biggest upsets in recent UFC title fight history.

Strickland entered the middleweight title bout as a massive +450 underdog, with most analysts expecting Chimaev to impose his grappling-heavy game and retain the belt. Cerrone, a UFC Hall of Famer, was not among the doubters. He confirmed the windfall in an interview with The Schmo and provided a screenshot of the betting slip as proof.

“Yeah, I won $45,000,” Cerrone said. “I put $10,000 on Sean.”

Cerrone was not alone in his conviction. Jorge Masvidal had also publicly stated he would be betting heavily on Strickland ahead of the fight.

The bout itself unfolded in dramatic fashion. Chimaev controlled Strickland on the ground through the first round, appearing to validate the pre-fight consensus. The dynamic shifted in the second, and by the third round Strickland had taken clear command. Chimaev pushed hard in the championship rounds but could not reverse the momentum. The judges awarded Strickland a split decision, handing him the middleweight title at 30-7.

For those who read Strickland’s boxing and ring generalship as a genuine equaliser against Chimaev’s wrestling, the result — and the odds — made for a significant return.