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Preheat the oven to 400°F.
Slice the squash in half and remove the seeds with a spoon. Cut each half crosswise into long wedges, about 1/2-inch thick. Toss the wedges with the olive oil until coated, and spread on a baking sheet. Season with salt and pepper.
Slice the top off the garlic head so the tops of the cloves are exposed. Drizzle on a bit of olive oil, sprinkle with salt and pepper, and wrap in aluminum foil. Place on the edge of the baking sheet with the squash.
Bake the squash and garlic for about 30 minutes, turning the squash once, until both are soft and slightly caramelized. (Depending on how big the head of garlic is, it may take longer. Leave it in the oven while you peel and chop the squash.)
Allow the squash to cool slightly. Then, peel each wedge of squash and cut into large chunks.
Bring a pot of water to boil to cook the pasta. In a large, wide saucepan (you'll add the pasta to this pan at the end) sauté the pancetta until most of the fat is rendered and the meat is crispy, about 15 minutes. About halfway through, cook the pasta, making sure to salt the water.
When the pancetta is finished cooking, remove with a slotted spoon and set aside. Deglaze the pan with the broth, scraping up any brown bits on the bottom. Stir in the rosemary and about four cloves of the roasted garlic, mashing them up in the liquid with the back of a spoon or spatula.
Add the chunks of squash and pancetta to the pan. Drain the pasta, reserving about 1/2 cup of the cooking water, and add the pasta to the squash/pancetta mixture. Toss everything to coat, then stir in the Parmesan. Add a bit of the pasta water if the mixture seems too dry.