Heat oven to 425°F (220°C). Spray a 17x11-inch roasting pan with cooking spray.
Brush the pork with the oil and sprinkle with the black pepper. Put the pork in the prepared pan.
Put the apples, squash, brown sugar, cinnamon, and only ½ cup of the broth in a large bowl. Toss to coat with the broth mixture. Add the squash mixture to the pan.
Bake for 25 minutes or until the pork is cooked through, stirring the squash mixture once while it’s cooking. Remove the pork from the pan to a cutting board and let it stand for 10 minutes before slicing. Continue to bake the squash mixture for 15 minutes more or until browned. Remove the squash mixture form the pan with a slotted spoon.
Stir the flour into the drippings in the roasting pan. Cook and stir over medium heat for 1 minute then gradually stir in the remaining broth. Cook and stir until the mixture boils and thickens. Thinly slice the pork ad arrange on a serving platter with the vegetables. Pour the sauce into a gravy boat and serve with pork.