Preheat your oven to 350°F (175°C).
In a large mixing bowl, combine the ground beef, breadcrumbs, milk, ¼ cup of ketchup, shredded cheddar cheese, chopped onion, chopped cooked bacon, egg, garlic powder, Worcestershire sauce, salt, and pepper. Mix until just combined, being careful not to overmix.
Transfer the meat mixture into a loaf pan, shaping it into a loaf shape. Smooth the top with a spatula.
Spread the remaining ¼ cup of ketchup on top of the meatloaf.
Lay the additional strips of bacon on top of the ketchup-covered meatloaf, overlapping slightly.
Place the loaf pan on a baking sheet to catch any drippings, and bake in the preheated oven for 1 hour or until the internal temperature reaches 160°F (70°C).
Once cooked, let the meatloaf rest for about 10 minutes before slicing. Serve warm.