Gently crumble ground beef into a large bowl. Add ¼ cup of prepared sauce to the bowl, as well as breadcrumbs, milk, Worcestershire, egg, salt, pepper, onion, and pickles. Gently combine all ingredients with your hands until well mixed.
Ladle enough sauce on the bottom of a bread pan to cover.
Place half of meatloaf mixture into the pan and spread out evenly.
Place two layers of cheddar cheese into the middle of the meatloaf, keeping it about an inch from any edge. (Approximately 3 slices of cheese, broken up as needed.)
Add the remaining meatloaf mixture into the bread pan and press firmly to seal the edges around the interior layer of cheese.
Coat the top of the meatloaf with the remaining sauce.
Place the meatloaf in the oven and bake for 80 minutes, or until the internal temperature reaches 160 degrees.
Remove from oven, cover the top of the meatloaf with slices of cheese and place back in the oven until melted, ~3 minutes.
Remove from oven, let rest for five minutes, then serve.