Combine pumpkin, ice cream, milk, sugar, vanilla extract, cinnamon, cloves, and nutmeg in a blender; blend until smooth. Add ice; blend until smooth.
Place 1/3 of the graham cracker crumbs in the bottom of 2 small glasses. Fill glasses halfway with blended pumpkin mixture. Top with another 1/3 of the graham cracker crumbs. Pour in remaining pumpkin mixture. Top each glass with 1 tablespoon whipped cream and remaining graham cracker crumbs.
