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Preheat the oven to 400°F. Place onions, fennel, garlic, salt and pepper in a glass baking dish, toss with olive oil. Roast until the they begin to soften, about 25 minutes, stirring once halfway through. Stir in tomatoes, oregano, chile flakes, wine and vinegar. Roast until the sauce has thickened and reduced slightly, about 30 minutes.
Meanwhile, bring a large pot of salted water to a boil over high heat. Add pasta and cook until al dente, about 8 minutes. Drain well. Serve vegetable mixture over pasta and topped with cheese, if using.