Preheat oven to 350 degrees. Coat a 5x9 pan with cooking spray and set aside. In a large bowl, combine the ground beef, crackers, egg, milk, 1/2 cup Raspberry Chipotle Ketchup, onion, salt and pepper. Mix thoroughly with your hands.
Spread evenly into pan. Place the pan on a baking sheet and bake for 1 and a half hours. In a small bowl, mix 3/4 cup Raspberry Chipotle Ketchup, brown sugar and worcestershire sauce. Spread half of the mixture evenly over the meatloaf halfway through baking. Save the rest for dipping.