Preheat the oven to 350°F. Coat a 12-well muffin pan with nonstick cooking spray. Stir together the panko and beef broth in a large bowl and let stand until the breadcrumbs are softened, about 5 minutes. Stir in the ketchup and Worcestershire sauce.
Whisk the eggs and add to the softened panko breadcrumbs mixture. Stir in the Italian seasoning, garlic powder, salt, and pepper. Add the minced onion, ground chuck, and ground pork and mix just until combined.
Divide the meat mixture evenly between the wells in the muffin pan, pressing until they're even with the top of the pan. Place the muffin pan on a rimmed cookie sheet and bake in the preheated oven for 20 minutes.
Meanwhile, make the glaze. Stir together the ketchup, brown sugar, and apple cider vinegar in a small bowl. Remove the meatloaves from the oven and brush with the glaze. Return to the oven and bake for 15 more minutes, or until a meat thermometer inserted in the thickest portion registers 160°F.
Carefully remove the meatloaves from the muffin tin to a plate. Insert a toothpick into each olive and place two toothpicks into each meatloaf to look like eyes.