Will he eat more before he goes to bed? He might be going through a growth spurt. When my son goes through his, he is hungry more often.. so he wants to eat more often.. (every 3 hours through the whole night). My solution has been to shorten his naps, and feed him cereal, baby food, and a bottle before he goes to bed. If he wakes up in the middle of the night, leave him in his crib, and feed him a bottle... 99% of the time, he has a few ounces, and rolls on his side and falls asleep... Some other moms in my family have woken their baby up at 11pm to feed them and play.. and then the baby would sleep the rest of the night through.. you have to try different things... I have had to try about 3 different routines to get one that stuck and is finally working.. every baby is different.