Preheat your oven to 350°F (175°C) and lightly grease a loaf pan.

In a large bowl, combine the ground beef, bread crumbs, milk, egg, chopped onion, 0.25 cup ketchup, Worcestershire sauce, salt, and black pepper, mixing until just combined.

Press half of the meat mixture into the bottom of the prepared loaf pan, forming the first layer.

Evenly spread the shredded cheddar cheese and crumbled bacon over the first meat layer to create the middle layer.

Carefully top with the remaining meat mixture, gently pressing it down to secure the layers.

In a small bowl, whisk together the brown sugar, the remaining 0.25 cup ketchup, and Dijon mustard for the glaze, then spread this mixture evenly over the top of the meatloaf.

Bake for 50-60 minutes, or until the internal temperature reaches 160°F (71°C), then let the meatloaf rest for 10 minutes before slicing and serving.