Place a rack in the upper and lower thirds of the oven and preheat the oven to 400 degrees F. Line two rimmed baking sheets with aluminum foil and lightly coat with cooking spray.
Halve, seed, and slice the squash into 1-inch thick crescent slices, then arrange in a single layer on the prepared baking sheets.
In a small bowl, stir together the olive oil and maple syrup and then brush the squash slices with half of the olive oil/maple syrup mixture.
Add the brown sugar and pecans to a food processor fitted with a steel blade and process until the pecans are finely ground. Add the salt, black pepper, and cayenne pepper and pulse to combine. Sprinkle half of the brown sugar mixture over the top of the brushed squash slices, reserving the other half.
Place the squash in the oven and roast for 5 minutes, until the brown sugar begins to melt. Remove from the oven and, using tongs, a fork, or very quick fingers, flip over each slice. Brush with the remaining olive oil/maple syrup mixture and sprinkle them with the remaining brown sugar mixture. Return the baking sheets to the oven and continue roasting until the squash slices are fork-tender, about 20 additional minutes. Serve warm or at room temperature.
TOSTORE: Leftover roasted squash slices may be stored, covered, in the fridge for up to 3 days.
TO REHEAT: Warm in a 350 degree F oven, on a parchment-lined baking sheet, or in the microwave until steaming.
TO MAKE-AHEAD: The brown sugar topping can be prepped up to 2 days in advance. Store in an airtight container at room temperature. The squash can be sliced up to 1 day in advance. Store in an airtight container or ziptop bag in the refrigerator. Brush and sprinkle the squash slices just before baking.