Riley Green has plenty of stories from his years on the road, but one arm-wrestling match at Flora-Bama may be the wildest of them all.

The country star once accepted an unexpected challenge from a fan while performing at the famous Florida-Alabama club. What started as a casual arm-wrestling contest ended with one man being taken to the hospital.

Green recalled the bizarre night during a 2024 interview with Taste of Country.

“I was playing at the Flora-Bama, and I came on the stage, and some guy was like, ‘Let’s arm wrestle.’ I was like, ‘That’s weird,’” Green remembered.

But he accepted the challenge.

According to Green, he quickly defeated the first fan. That only encouraged more people to step up. He said he went on to beat two or three more challengers before the crowd decided to find someone they thought could finally take him down.

“They’re like, ‘We’re gonna go find somebody,’” Green recalled.

They eventually brought over a much bigger man who was ready for the challenge.

But the new challenger still could not beat Green.

Instead, the match ended in a shocking injury.

Video of the incident was later shared by Green on TikTok, showing the moment the man’s arm suddenly gave way during the match.

@rileyduckman Throwback to that one time I broke a guys arm at the #florabama #overthetop #armwrestling #ouch #sports #countrymusic ♬ original sound – Riley Green

Green said the aftermath was chaotic, with an ambulance arriving to take the injured man to the hospital.

“Mayhem,” Green recalled. “He had, like, his arm laid over on the table, and an ambulance came and got him. I felt horrible about it.”

Despite feeling bad about what happened, Green admitted that his friends were celebrating the unexpected victory.

He recalled being carried out of the club by his buddies and joked that he felt like “the coolest guy ever.”

But was the unfortunate challenger actually a fan of Green’s music?

Green had a simple answer when asked.

“I don’t know. Not anymore,” he joked.

Years later, the arm-wrestling story remains one of the most unexpected tales from the country singer’s time performing at Flora-Bama.