Blend the butter, sugar, egg, and cinnamon in a large bowl. Add the flour and blend until just combined.
Scoop the cookie dough into standard muffin tins that have been sprayed liberally with baking spray.
Use a pastry tamper (or fingers) to work the cookie dough into cookie cups and up the sides of each well in the tin. *Note - twisting and lifting the tamper after pressing it into the dough is the best way to release the tool from the sticky dough.
Bake the cookie cups in a preheated 350-F (175 C) oven for 18-20 minutes or until the edges of the cups are lightly golden brown.Remove the cookie cups from the oven and press again with the tamper (if needed) to redefine the cups.
Cool the cookie cups completely on a baking rack.
To make the pumpkin cheesecake filling:
In a large bowl, blend together the softened cream cheese, vanilla, cinnamon, and nutmeg until creamy.Add in the pumpkin purée and Greek yogurt, blending again until completely incorporated.
Spoon the pumpkin cheesecake filling into a large piping bag or large zip-top bag and work the filling into one of the bottom corners.
Snip a small corner off of the bottom of the bag and carefully squeeze the pumpkin cheesecake filling into the baked and cooled cookie cups.
Dust the tops of the pumpkin cheesecake cookie cups with ground cinnamon or freshly grated nutmeg before serving.
Notes
Store leftovers in an airtight container in the refrigerator for up to 5 days.May be frozen. Store in an airtight freezer container. Label and date. Freeze for up to 2 months. Thaw in the refrigerator overnight.