Preheat oven to 350 degrees. Place 18 cupcake liners in muffin pan(s).
OREO COOKIE CRUST: Use a food processor to crush the Oreo cookies into fine crumbs. Add melted butter, pulse to combine. Add 1 packed tablespoon of crumb mixture to each cupcake liner. Use the back of the tablespoon to firmly press in place.
PUMPKIN CREAM CHEESE FILLING: Beat the cream cheese and sugar until light and fluffy. Add the eggs one at a time, beating after each addition. Add the pumpkin, sour cream, vanilla, pumpkin pie spice and cinnamon; beat until creamy and smooth. Spoon filling over each Oreo crust, dividing evenly, about 3/4 full.
Bake for 20 minutes. Cool in pan for 15-20 minutes before removing and placing on a wire rack to finish cooling. Keep refrigerated until ready to serve.
Before serving, top with whipped cream and crushed Oreos.