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Preheat your oven to 350°F (175°C). Lightly grease a loaf pan.
Combine the meatloaf mixture: In a large bowl, mix together the ground beef, crumbled bacon, cheddar cheese, bread crumbs, ketchup, mustard, Worcestershire sauce, onion, garlic, eggs, salt, and pepper until well combined.
Form the meatloaf: Transfer the mixture to the prepared loaf pan, shaping it to fit.
Prepare the topping: In a small bowl, mix together the ketchup, mustard, and brown sugar. Spread this mixture over the top of the meatloaf.
Bake: Place the meatloaf in the oven and bake for 1 hour, or until the meatloaf is cooked through and the topping is caramelized.
Serve: Let the meatloaf rest for 10 minutes before slicing.
Serve warm for a hearty and satisfying meal.