1.Preheat the oven to 350 degrees. Place 9 cupcake liners in a muffin pan.
2.Place the cream cheese and sugar into a standing mixer with paddle attachment and beat until light and fluffy. Add the sour cream, pumpkin, nutmeg, cinnamon, and flour and beat until creamy. Add the egg and 1/2 teaspoon vanilla and beat until mixed in.
3.Place half of an Oreo, frosting side up, in the bottom of 9 cupcake liners and spoon the batter into the liners. Place the other half of an Oreo into the top of the batter, frosting side down. Bake for 24 minutes.
4.Cool in pan for 15 minutes before removing and placing on a wire rack to finish cooling. Keep refrigerated for at least 4 hours prior to serving.
5.Prior to serving, add heavy cream, powdered sugar, and 1/4 teaspoon vanilla to a standing mixer with whisk attachment. Whip until soft peaks. Crush remaining cookie. Top the cheesecakes with whipped cream and cookie crumbs.