Eli is a bit younger than 5 months but he wakes about 2-3 times generally. We are putting him down around 9pm and he wakes anywhere between 12-2 for another feed, then sometime around 6-7. Lately he's been going through both a growth spurt and teething so I'm not trying to enforce anything rigid about scheduling, he gets a feed when he wants one and sometimes I give him Calpol in the night if he's in pain.
Usually he goes down for sleeping peacefully, then will wake about 15 minutes later and sometimes we'll have to give him a dummy, once he's asleep we take it away. There have been a few times where we've put him down sleepy but awake and he's settled himself, we're moving in that direction but he's only young so we're not expecting that every time, just trying to set him on the right path. Hopefully once this growth spurt is done he'll go more than 4-5 hours without waking. The good thing about breastfeeding is that I can at least doze a bit while he's feeding.