Preheat oven to 400°. Line rimmed baking pan with foil; spray with cooking spray and place pork on pan. In small bowl, stir cinnamon and paprika. Brush all sides of pork with 1 tablespoon oil; sprinkle with 1 1⁄2 teaspoons cinnamon mixture, 1⁄2 teaspoon salt and 1⁄4 teaspoon pepper.
In large bowl, toss garlic, apple, squash, onion, cherries, remaining cinnamon mixture and 1 tablespoon oil, and 1⁄4 teaspoon each salt and pepper; spread on pan around pork. Roast 25 minutes or until internal temperature of pork reaches 145° and vegetable mixture is tender. Let pork stand 5 minutes before slicing.