Preheat oven to 450°.
Cut fennel bulb in half lengthwise; discard core. Chop the fennel into bite-sized pieces. Combine fennel, olives, rosemary, oregano, and tomatoes in a 13 x 9-inch baking dish. Sprinkle fennel mixture with pepper; drizzle with olive oil. Toss well to coat. Bake fennel mixture at 450° for 30 minutes or until fennel is tender, stirring once.
Prepare pasta according to package directions, omitting salt and fat. Drain; place in a large bowl. Add fennel mixture and salt, and stir to combine. Add cheese; toss to combine.