Preheat the oven to 425° F.Place the squash in a baking dish and rub with 1 tablespoon of olive oil. Sprinkle with Italian seasoning. Season with salt and pepper.Slice off the top portion of the garlic head to expose some of the cloves. Place the garlic in a piece of foil. Drizzle with olive oil and wrap it up and place on the pan with the squash. Bake 15 minutes. Meanwhile, make the sauce. Heat 3 tablespoons olive oil in skillet over medium-low heat. Add the shallot and sage. Cook until the shallots begin to caramelize, about 5 minutes. Reduce the heat to low, add the tomato paste and red pepper flakes, cook 4-5 minutes, until thickened. Stir in the vodka, cook another 2 minutes. Stir in 1/2 cup water, the pesto, and the cream. Season with salt and pepper. Add the parmesan and basil. Remove the squash from the oven and sprinkle each with mozzarella cheese. Divide the sauce between the squash. Top with the fontina and provolone cheese. Bake the squash and garlic another 15-20 minutes or until the squash is tender and the cheese is golden brown on top.Let the garlic cool, then squeeze the cloves out into a bowl. Add the butter and 1 tablespoon of sage. Mash the cloves into the butter with a fork. Spread the butter over the squash, then use a fork to scrape the squash into strands, mixing the cheese with the squash. Enjoy!