About how big is he?
He reminds me of a toy set I had when I was small that was a parent plush dog with two puppies. There were some spaces in the box they came in as if there were more puppies that had been ripped out and stolen, so I have no idea what they looked like or how they were posed. While my toys were not dalmatians but something more along the lines or terriers or boxers, they do look very similar to the eyes, smile, and general style of your little Poochie. I'm thinking that if he's about 2-3 inches, he could be one of the puppies, but that's only if they're the same line.
If he DOES come from the line that I just described, I would pinpoint the date around 1994. I was in kindergarten when I was rewarded some kind of good behavior or good grade coupon and got to pick out a toy at this old department store back in the day called Hills. Mom tried to get me to pick something else that wasn't half-stolen, but when you're five and you neeeeeed a toy, then that's the one you're going to have. I remember the "daddy" was named Charlie and the pups were Squishy and Squashy, and they were a step family to those Puppy Surprise fakies by Dandee. I actually did an MS Paint doodle a while ago about the way I used to play with them, so if I find it, I'll post it and see if that jogs a memory.