Place spelt in a large saucepan. Cover with water to 2 inches above spelt; bring to a boil. Reduce heat, and simmer 20 minutes or until tender. Drain; set aside.
Heat oil in a Dutch oven over medium-high heat. Add onion, carrot, celery, pancetta, and garlic; sauté 8 minutes or until mixture is very fragrant and beginning to brown. Stir in broth and wine, scraping pan to loosen browned bits. Add chestnuts, squash, Brussels sprouts, and pepper; bring to a boil. Reduce heat, and simmer, uncovered, 10 minutes. Stir in spelt and tomatoes; cover and cook 10 minutes. Ladle about 1 cup soup into each of 6 bowls; sprinkle evenly with cheese.