Preheat the oven to 375°F (190°C) and prepare a loaf pan or baking sheet by greasing or lining it.
In a large bowl, combine ground beef, breadcrumbs, onion, garlic, eggs, milk, ketchup, Worcestershire sauce, Italian seasoning, salt, and pepper. Mix gently until just combined.
Press half of the meat mixture into a loaf shape on the prepared pan.
Add a layer of shredded cheddar cheese in the center, then cover with the remaining meat mixture and seal the edges.
Form the mixture into a loaf and prepare the glaze by mixing ketchup, brown sugar, and mustard.
Spread half of the glaze over the top of the meatloaf.
Bake for 40 minutes, then remove from the oven and spread the remaining glaze over the meatloaf.
Return the meatloaf to the oven and bake for an additional 10 to 20 minutes until fully cooked and internal temperature reaches 160°F (71°C).
Let the meatloaf rest for 10 minutes before slicing.
Garnish with fresh parsley and serve warm.