Both singers were up for Country Song of the Year at the iHeartRadio Music Awards in May (14), and the close friends made a pact that whoever won the prize would have to buy dinner for the loser.
Shelton was the victor for his track Boys 'Round Here, but he tells Access Hollywood that the bet ultimately backfired on him, saying, "Luke comes walking in with his wife, then with his entire band and crew, his management team, some label people - they had to find a room to put us all in! It was like a damn $10,000 dinner I bought him that night. So it was like, 'Hey, I hope you win next time!'"
When asked if he would make the bet again, Shelton added, "I'm not real sure those awards are worth 10 grand! I need to find out exactly how much they're worth before I do that again."
If they had decided to make the bet again for Wednesday night's (05Nov14) 2014 CMA Awards, it would have been a win-win - Shelton beat out Bryan for the Male Vocalist of the Year award, while Bryan took home the coveted Entertainer of the Year trophy over his friend.