Place an oven rack in the center of the oven. Preheat the oven to 400 degrees F. Line a baking sheet with a silpat or parchment paper sprayed with vegetable cooking spray.
Unroll the pie crust out on a work surface. Using a 3-inch round cookie cutter, cut out 8 disks of pastry. Arrange the pastry disks on the prepared baking sheet. Using the tines of a fork, prick the pastry all over. Bake until brown and crispy, 8 to 10 minutes. Remove to a wire rack to cool completely, about 10 minutes.
Slice the bottom of the apples to create an even surface for cutting. Slice each apple into 6 (1/2-inch) slices. Cut each apple slice in half and remove any seeds or pieces of core. In a medium bowl, mix together the sugar and 1 tablespoon cinnamon. Add the apple slices and toss until coated. Shake off any excess mixture. Arrange the apple slices on the same baking sheet in a single layer. Bake until dark brown, about 12 to 15 minutes. Remove from the oven and let cool for 15 minutes.
In a medium bowl, using an electric hand mixer, beat the cream until thick, about 1 minute. Add the powdered sugar and continue to beat until the cream is very thick.
To assemble the pies: Place the pastry disks on a work surface. Divide the cooked apple slices among 4 of the disks. Dollop about 2 tablespoons of the cream on top of the apples and cover with the remaining disks.
Transfer the apple pies to dessert plates, dust with cinnamon and serve immediately.