My son is 10 months old and we just introduced him to a sippy cup in the last month. We did go through a few cups to find out which one he liked. But what I did was to give him the cup with milk in it when he was hungry and left the room. He explored the cup himself and figured out how to put it in his mouth. He couldn't drink from it right away but I did praise him to putting it up to his mouth and attempting. At each meal for a week, we gave him the sippy cup and left the room. Eventually, he got the hang of it and drank from it by himself.
Note; we left the room b/c he would cry and attempt to push away the cup and give it back to us. If he didn't see us in the room, he figured that he couldn't give it back to us. He actually prefers to drink from the sippy cup now. I am actually introducing another type of cup tonight to see if he'll figure it out.