Cut each squash in half crosswise; remove and discard seeds. Place squash halves, cut side down, in a 15- x 10- x 1-inch jellyroll pan lightly coated with cooking spray. Bake, uncovered, at 350° for 35 minutes.
Combine pineapple, orange, and brown sugar; spoon evenly into squash halves. Sprinkle with cinnamon. Bake, uncovered, an additional 10 to 15 minutes or until fruit mixture is thoroughly heated. If desired, garnish with orange rind curls and cinnamon sticks.