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Preheat oven to 400 degrees.
Cut squash in half and then into slices, scooping out seeds (save to roast!). Heat olive oil, butter, brown sugar, and maple syrup over medium-low heat until sugar is dissolved. Brush squash slices with maple and sugar liquid, and place on oiled baking sheet. Sprinkle squash with salt, pepper, and brown sugar and bake until soft and golden brown, about 30-40 minutes.
Remove from oven and plate. Sprinkle with sage leaves and serve.