In a 12-inch nonstick skillet, heat the oil on medium-high. Season the pork chops with salt and pepper. Add to skillet and cook 3 min. per side, until browned. Transfer to a plate.
Meanwhile, to a microwave-safe bowl, add the butternut squash, butter, ½ tsp pumpkin pie spice, and 2 tbsp water. Season with salt and pepper. Cover with vented plastic and microwave 4–5 min., until tender. Stir to combine.
While pork and squash cook, thinly slice the apple.
Add the apple and 2 tbsp water to empty skillet. Season with salt. Cover and cook 2 min., stirring once.
In a small bowl, stir the maple syrup and remaining 1 tsp pumpkin pie spice together and add to skillet. Add pork chops and spoon apples on top. Cook 1–2 min., until pork chops are cooked through and register 145°F on a meat thermometer . Serve pork chops and apples with butternut squash.
Garnish with parsley for a pop of fresh herb flavor.