1. Preheat oven to 375°.
2. Place 1 phyllo sheet on a work surface (cover remaining phyllo to prevent drying); lightly brush phyllo sheet with 1 1/2 teaspoons oil. Combine Parmigiano-Reggiano cheese and pepper, stirring well. Sprinkle about 1 teaspoon pepper mixture evenly over phyllo; top with another phyllo sheet. Combine tomatoes and next 5 ingredients (through fontina cheese) in a bowl. Arrange about 1/3 cup tomato mixture along short side of phyllo; roll up phyllo, jelly-roll fashion, starting with short side. Lightly brush outside of roll with oil. Cut into thirds. Place on a baking sheet coated with cooking spray. Repeat procedure with remaining 6 phyllo sheets, pepper mixture, oil, and tomato mixture.
3. Bake at 375° for 10 minutes or until phyllo is golden. Serve warm or at room temperature.