Remove Phyllo cups from freezer and let sit on counter while preparing filling
Cut bacon into 1-inch pieces. Cook in skillet until crispy. Remove from pan and drain on paper towels. Dice bacon into smaller pieces. Set aside. Remove any additional grease in skillet. Cook ground beef on medium heat until no longer pink. Add ketchup, Worchestershire sauce, salt, pepper and ½ of bacon. Stir to incorporate all ingredients.
Place Phyllo cups on a baking sheet. Fill each cup with a heaping spoonful of cheeseburger mixture. Place in oven and bake for 8 minutes or until cups are crispy. Remove from oven. Top with grated cheese and remaining bacon. Serve immediately.