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Add the diced butternut squash, chopped onion, whole garlic cloves, olive oil, salt, and pepper to a baking sheet, tossing until fully coated. Bake until the squash is golden brown and tender, about 30 minutes. While the squash is in the oven, make the dough. When the squash is finished cooking, add it to the food processor along with the brown sugar and Parmesan cheese. Rinse the bowl of the food processor.

To the bowl of a food processor, add the flour, eggs, and olive oil, and pulse until the dough comes together into a large ball and swirls around the processor. Remove the dough, wrap in plastic wrap, and rest it the refrigerator for 30 minutes. Lay a sheet over an empty ice cube tray, and press the dough down gently into each of the holes. Fill each hole with a tablespoon of the butternut squash filling. Place a second sheet on top of the ice cube tray. Press down on all the sides of the raviolis.