Preheat your oven to 350°F (175°C).
In a large mixing bowl, combine the ground beef, shredded cheddar cheese, breadcrumbs, milk, chopped onion, minced garlic, egg, Worcestershire sauce, Italian seasoning, salt, and black pepper. Mix until all the ingredients are evenly incorporated, being careful not to overmix.
Transfer the meat mixture to a loaf pan and shape it into a loaf. Smooth the top with a spatula.
Spread 1/2 cup of ketchup evenly over the top of the meatloaf for added flavor and moisture.
Place the loaf pan on a baking sheet and bake in the preheated oven for 60 minutes or until the internal temperature reaches 160°F (70°C).
Once cooked, remove the meatloaf from the oven and let it rest for 10 minutes to hold its shape when sliced.
Slice and serve warm, enjoying the cheesy goodness in every bite.