Blake shared the funny story with Access Hollywood prior to Wednesday's CMA Awards.
Blake says that he and Luke were up for Country Song of the Year at the iHeartRadio Music Awards in May. The friends made an agreement that whoever won the prize would have to buy dinner for the loser.
Turns out Blake won and then lost … big time.
"Luke [came] walking in with his wife. That's great. Then, with his entire band, and crew, his management team, some label people," Blake said of the dinner surprise.
"They had to like, find a room to put us all in. It was like a damn $10,000 dinner that I bought him that night. So, it was like, 'Hey, hope you win next time buddy. I hope you win.'"
Well if you were wondering how Luke beat out Blake for the recent CMA Awards Entertainer of the Year category, I guess you now have your answer – Blake jinxed it.