Step 1: Preheat oven to 375 degrees.
Step 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 over the phyllo; top with another phyllo sheet.
Step 3: Combine tomatoes and the next 5 ingredients (through fontina cheese) in a bowl. Arrange about 1/3 cup tomato mixture along the short side of the phyllo. Roll up phyllo, jelly roll fashion, starting with short side. Lightly brush the outside of the roll with oil. Cut into thirds. Place on a baking sheet coated with cooking spray.
Step 4: Repeat procedure with the next 6 sheets of phyllo, pepper mixture, oil, and tomato mixture.
Step 5: Bake at 375 degrees for 10 minutes or until phyllo is golden. Serve warm or at room temperature.
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