Lloyd Cook, 30, was on Saona Island proudly donning his Leeds United home shirt when a man who spoke "zero English" started shouting the name of the popular former manager at him.
Lloyd, who said he had drunk "a few rums", started a conversation with the man using Google translator on his phone.
The Argentinian fan typed: "Please can I have your shirt, they're so expensive back home.."
"He laughed and his face was a picture", Lloyd told the YEP.
"It was such a small gesture which goes a long way.
"Always be kind."
Lloyd's small act has received praise across Leeds United social media forums.
One said: "What a kind thing to do.
"You will have made his day."
Another added: "Brilliant!
"A great memory for him."