Preheat oven to 190ºC (375ºF). In a small bowl, stir together brown sugar, chili powder, cumin, pepper and salt; set aside.
Cut acorn squash in half along ridges. With large spoon, scrape out and discard pulp and seeds. Cut each half into five wedges. Place wedges in a large bowl. Toss with oil and half the brown sugar mixture.
Cut bacon slices in half. Wrap each piece around the middle of a squash wedge. Place on parchment-lined baking sheet, with ends of bacon slices on underside of squash wedges. Sprinkle with remaining brown sugar mixture.
Bake 25 to 35 min., turning over halfway, until squash is tender and starts to caramelize and bacon is golden. If bacon browns before squash is tender, tent baking sheet with foil and continue baking.
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