Preheat oven to 350 degrees and lightly spray 2 mini muffin tins with cooking spray.
Divide the cookie dough evenly between the tins about 1 tablespoon each.
Bake for 10-12 minutes or until middles are done. Cookie cups will continue to set after they bake.
Cool on a wire rack or in the fridge to speed up the process.
With a mixer, beat the pudding mix and eggnog for 2 minutes. Add the cream cheese and beat until combine. Chill in the fridge until set.
Once cookie cups have cooled, fill the cups with the pudding mix. I filled a ziploc bag with the pudding mix and snipped off the corner and piped the filling into the cups.
Top with a dallop of whipped cream. You can use the stuff in the can but that must be used right before serving. If you make homemade whipped cream it lasts longer. Sprinkle with cinnamon or a tiny bit of nutmeg (it's pretty strong). Store in the fridge until serving. I like them best after they have sat out of the fridge for about 5-10 minutes because the cookie gets a little softer.
Cookie cups and filling can be prepared up to 3 days ahead of time (if not longer).