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Preheat oven to 375 degrees.
Toss squash, sage leaves, garlic, oil, sea salt, and pepper together on baking sheet. Roast 20 minutes.
While squash is roasting, melt butter with sugar in small saucepan over medium heat until butter is melted.
Remove squash from oven, drizzle with butter mixture, and carefully toss to coat squash. Roast 20 to 25 minutes or until squash is tender and caramelized. Squeeze cloves from garlic bulb halves to serve with squash, discarding papery outside.