I think WInky could beat him even now... Roy would is too fast and big for him... Anyways Roy in his prime would hit any version of Winky about 3 times as much as anyone he has ever faced, and though I have no idea if Roy could knock out WInky, if anyone at middleweight could it would be him. I see him winning most arounds, and his footwork, reflexes, power giving Winky fits.