Preheat the oven to 425 degrees F and line 2 rimmed baking sheets with parchment.
Whisk together the brown sugar, maple syrup, butter, chili powder, cayenne and 2 teaspoons salt in a large bowl to combine.
Cut the squash in half and trim and discard both ends. Using a spoon, remove the seeds and discard. Place the squash cut-side down and slice crosswise into 1/2-inch-thick wedges.
Toss the squash with the maple syrup mixture to coat evenly. Arrange the squash in a single layer on the prepared baking sheets, reserving the excess maple syrup mixture. Roast, flipping the squash and rotating the baking sheets top to bottom halfway through, until golden brown and tender, 24 to 26 minutes. While still hot, loosen the squash with a metal spatula from the baking sheets and flip to avoid sticking. Brush the squash with the reserved maple syrup mixture and transfer to a serving dish. Serve warm or at room temperature.
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