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