I got some great recommendations to the same question the other day: http://www.mumsnet.com/Talk/behaviour_development/1662509-Looking-for-a-non-leak-spill-cup-for-nighttime-use
Been using the Tommee Tippee Explora Active for the past week or so and it's working great for us. I did give DS milk in it during the day the first day, so he could learn how to sip from it effectively. Then in the night he got a bit upset when he didn't get his bottle, but when he realised it was this or nothing he drank from it.
DD managed to make the Tommee Tippee one leak. I have no idea how, but I had to throw it away as when I turned it upside down it literally poured out.
She has made four different types of "non-spill" cups spill like fountains. It's a talent....
Her favourite game is to pour her water all over the floor, usually down herself as well, and then play in it. So making her cups leak is a life goal.
The only one she hasn't managed to ruin the reputation of is the Nuby No Spill Super Straw Link. She has thrown it literally everywhere, pulled on it, bashed it against things, stretched the straw, chewed it etc and it still will not leak. I now have four and dry floors .
You might be as well off putting it in his bed with him to start with, unless he is happy sitting up to find it outside his bed. DD has been in a bed for 8 months now, and still won't reach out of bed unless we're in the room with her. Even if she falls out, she waits until she sees one of us at the door to climb back in
DS has just turned 2, he still wakes at night for a drink of milk which at moment he has in a bottle. We have just transferred him into a bed and I am hoping that we can put a cup of milk on his bedside table and he can help himself rather than waking us up in the night.
Is there a good sippy cup that wouldn't spill milk from if he didn't put it back on the bedside table? I imagine that he will fall asleep while drinking it