Preheat the oven to 300 degrees F (150 degrees C). Place pumpkin in a shallow baking pan and lightly coat with olive oil.
Bake in the preheated oven until tender when poked using a fork, 55 to 65 minutes. Remove pumpkin from oven and allow to cool 30 minutes. Increase oven temperature to 375 degrees F (190 degrees C). Line 2 pie plates with the pie crusts.
Cut the tops off of the persimmons and scoop pulp out into a bowl. Mash slightly and transfer to a food processor. Add roasted pumpkin, brown sugar, milk, cream, mascarpone cheese, apricot preserves, cornstarch, cinnamon, nutmeg, ginger, and salt and blend well. Pour mixture into a large bowl and add eggs; blend using a whisk. Pour the filling equally into the 2 pie crusts. Sprinkle additional cinnamon on top.
Bake in the preheated oven for 35 minutes. If crust is overcooking, wrap edges with aluminum foil. Continue baking until set, about 10 minutes more.
Remove pies from oven and let cool before serving. Top with confectioners' sugar and additional nutmeg.
