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Preheat the oven to 375°F.
Peel squash and cut in half lengthwise. Scoop out seeds from the center and discard. Cut squash into large chunks. Coat with 2 tablespoons of the olive oil. Season with 1/2 teaspoon salt and 1/4 teaspoon pepper and arrange on a parchment-lined baking sheet. Bake for about 10 minutes.
Meanwhile, peel onions and cut into large chunks. Coat with remaining 2 tablespoons olive oil. Season with the remaining 1/2 teaspoon salt and 1/4 teaspoon pepper.
Use a spatula to move the butternut squash to one half of the baking sheet. Spread the onions on the second half and bake until the squash and onions are well caramelized, about 20 minutes. When squash and onions are done, toss with sage and cranberries. Serve immediately.