Preheat oven to 425°F. Cook beef, onion, bell pepper, and garlic in a large skillet over medium heat until beef is browned and crumbly; drain and return to skillet. Stir in Italian seasoning, salt, and pepper.
Unroll dough on a large greased rimmed baking sheet, and press into a large rectangle. Sprinkle with 1 cup cheese. Top with beef mixture, leaving a 1-inch border on all sides. Sprinkle with 1 cup cheese; drizzle with ¼ cup dressing.
Starting at one long side, roll up dough, pinching ends to seal. Arrange, seam side down, on baking sheet; cut slits in dough at 1-inch intervals.
Bake 20 to 25 minutes or until deep golden brown. Let stand 10 minutes before slicing. Serve with remaining dressing for dipping.