Preheat the oven to 250 degrees . Season the pork chops with salt and pepper. In a large, heavy skillet, heat 1 tablespoon olive oil over medium-high heat. Working in 2 batches, add the pork chops and 1 more tablespoon olive oil between batches. Cook until browned, about 5 minutes on each side. Transfer to an ovenproof dish and tent with foil; place in the oven.
Add the remaining 1 tablespoon olive oil to the skillet over medium-high heat. Add the onion and cook for 2 minutes, scraping up any browned bits. Stir in the apple juice, squash, raisins and sage; season with salt and pepper. Cover and cook until the squash is tender, about 10 minutes. Using a slotted spoon, transfer the squash mixture to a bowl. Cook the remaining liquid until syrupy, about 5 minutes. Serve the pork with the squash and pan sauce.