Of course Winky would win a couple rounds. I see it 8-4 or 9-3. But Winky wouldn't be able to handle the volume Joe throws at him.
If it was the amatuers Winky would shut him out, as Joe would not land what you would consider an actual scoring punch with the knuckle part of the glove. In the pros it would go something like this https://www.youtube.com/watch?v=iCgjQD1kvrc