He would have a huge size advantage here because Sugar Ray Robinson was a natural Welterweight and Middleweight. But, great as Calzaghe was, Robinson was the greatest of all time, and I think he'd dominate Joe Calzaghe.
I don't really know how to call this fight, but Calzaghe doesn't even compare to Robinson in my opinion. He was dropped by Bernard Hopkins, who wasn't the hardest hitter, and I think his speed wouldn't bother Sugar Ray at all. Robinson was just as fast, and probably more powerful too. Maybe Calzaghe could do well early on, but I think Robinson wins an easy unanimous decision.
Robinson UD12 or 15.
Sugar Ray Robinson. Nobody beats Sugar Ray Robinson in his prime.
Sugar Ray Robinson would give him a beating.
A natural 147 pounder vs a natural 168-175 pounder? Not a fair fight, Ray Robinson is an all time great fighter, but to put him up against another great fighter who has a 20 pound weight advantage is just a bad idea. Good big-un usually beats a great little-un.
Sugar "Ray" Robinson was light years ahead of Joe..................No comparison. Sorry.