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Heat oven to 375°F. Spray a 13x9-inch (3-quart) baking dish with cooking spray.
In 12-inch skillet, cook beef over medium-high heat 5 to 7 minutes, stirring frequently, until beef is brown; drain. Add the pasta sauce and oregano and bring to a boil. Reduce heat to medium-low and simmer, uncovered, for 5 minutes. Add pepperoni slices and olives. Cook for 1 to 2 minutes, until hot. Stir in cheese. Spoon into baking dish.
Unroll dough; press to form 13x9-inch rectangle. Place on beef mixture; cut 4 to 5 vent holes in dough. Brush dough with olive oil. Sprinkle the top with Italian seasoning.
Bake 20 to 25 minutes or until crust is a deep golden brown.