T.G.
Put him in his own room, then break him of the cup. If you do it the other way around, he'll wake for a cup in his new room because he's scared. His cup will be a comfort to him after that. Also, I would suggest using a no-spill sippie cup. Put it in his crib after he goes to bed (before you go to bed) so that when he wakes up, it will be there. Let him cry until he finds it, then he'll know how to comfort himself. I know it sounds a bit harsh, but really it's not. He needs to know self-comfort measures, otherwise he'll always look to the outside for comfort (i.e. - food, other people, toys, etc).