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Preheat oven to 400°F. Coat four 8- to 12-ounce small baking dishes, such as mini loaf pans, with cooking spray and place on a rimmed baking sheet. (Alternatively, make freeform meatloaves and bake directly on the baking sheet.)
Combine beef, onion, breadcrumbs, egg, 2 tablespoons ketchup, chili powder, cumin, salt and pepper in a bowl; mix well. Divide the mixture into 4 even portions and place in the prepared baking dishes. Make a 1 1/2-inch-deep indentation with your finger down the length of each meatloaf. Stuff each with 2 tablespoons cheese and pinch the edges closed to seal.
Combine the remaining 4 tablespoons ketchup and chipotle in a bowl; spread over each loaf.
Transfer the baking sheet to the oven. Bake until an instant-read thermometer inserted in the center of a loaf registers 165°F, 20 to 30 minutes.