For the crust: Pulse the flour, granulated sugar and salt together in a food processor to combine. Add the 5 ounces Cheddar and pulse, then add the butter and pulse until it creates a coarse meal with some larger butter lumps. Add water a tablespoon at a time (no more than 1/2 cup) while processing just until the dough comes together. Turn out onto a piece of plastic wrap and form into a disc. Refrigerate while making the filling.
For the filling: Preheat the oven to 450 degrees F.
Stir together the apples, brown sugar, flour, butter, bourbon, maple syrup, lemon juice, cinnamon, pepper, salt, cloves and nutmeg in a large bowl.
Roll out the dough, using additional flour as needed, into a circle large enough to drape into a 10-inch pie plate or cast-iron skillet. Cover with the filling. Bake for 10 to 15 minutes, then lower oven to 350 degrees F and bake for 30 minutes more. Sprinkle on the remaining 6 ounces Cheddar to the top of the pie and bake until browned and melted, 15 minutes. Let cool until cheese hardens.
For the whipped cream: Beat together the cream, syrup and granulated sugar until firm.
Serve the pie with the whipped cream.
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