For the second year in a row, the country superstar lived out his gridiron fantasies by practicing with the New Orleans Saints in Jackson, Miss., according to the Associated Press.
Donning a white Saints game jersey with his name sewn on the back, Chesney, who is pals with the team's coach, Sean Payton, ran plays with the team and caught a long pass from quarterback Drew Brees.
But Chesney's grip faltered during a couple crucial moments.
At the practice, which was open to the public, Payton told players they would get Sunday off if Chesney – who was a receiver on his Tennessee high school football team – caught a punt in two tries.
"On the first one, I totally blew it," Chesney told the AP. "On the second one, not only were they offside, but they interfered with me."
Luckily for the players, Chesney got a third try at redemption. As the ball landed in his hands, he juggled it – but refused to let it hit the ground.
Jubilant players whooped it up, including Reggie Bush – Kim Kardashian's boyfriend – who winged a water bottle across the field in celebration.
Rogelio V. Solis / AP
Payton declared Chesney "part of our team" – an honor the sports loving singer embraced.
"I quit growing too young to ever think about getting to have a shot at playing in college," said Chesney, "so this is about as much fun I can have."
See how the country superstar made headlines on multiple PEOPLE covers.