Preheat an oven to 350 degrees F (175 degrees C). Stir ketchup, brown sugar, bacon bits, pineapple, and 1 dash Worcestershire sauce together in a small bowl; reserve.
Combine the ground beef, bread crumbs, saltines, egg, garlic, onion, and 2 dashes of Worcestershire sauce in a large bowl; mix well. Pat meat mixture into a 9x5 inch loaf pan.
Bake meatloaf in the preheated oven for 30 minutes. Remove from oven; pour reserved pineapple mixture over loaf. Return to the oven; bake until no longer pink in the center, about an additional 20 minutes. An instant-read thermometer inserted into the center should read at least 160 degrees F (70 degrees C).