does your vet think sullie (cute name BTW

) is at a healthy weight? he may be going through his last growth spurt therefore eating a bit more than usual...if this is the case, he is still a puppy at 10 months and should be able to eat when he is hungry
some dogs can regulate their food intake and only eat when they are hungry...some cannot (my bentley cannot regulate himself so he needs to be schedule fed) and you do need to figure out how much food they need and only give them that...but i would check with your vet first and go from there
but to answer your question, in my uneducated opinion, a cup seems like a lot for a 5 pounder but i could be way off

my kids - the ones who eat kibble - all eat about 1/2 cup (sometimes a little more) per day
hope that helps