In a large bowl, beat whipping cream, granulated sugar and vanilla with an electric mixer until soft peaks form. Remove 3/4 cup of the whipped cream and set aside.
Fold pumpkin into the remaining whipped cream, along with the cinnamon, nutmeg, cloves and powdered sugar.
Spoon or pipe the pumpkin mixture into the fillo shells. Top with a dollop of the reserved whipped cream and sprinkle with graham cracker crumbs, for garnish.
Refrigerate until serving. Best if served within a few hours.