Preheat oven to 350°F. Grease or line a 9x5 inch loaf pan with parchment paper. Set aside.
In a large bowl, mix together the stuffing, milk, onion and garlic. Let sit for 5 minutes.
In the meantime, mix together the sweet tomato glaze ingredients. Set aside.
To the bowl with the stuffing, mix in the eggs, Worcestershire, ketchup, salt and pepper, then mix in the beef until just combined. Transfer to the prepared loaf pan.
Evenly spread half of the sweet tomato glaze over the meatloaf, and bake uncovered for 45 minutes.
Remove from the oven and top with the remaining sweet tomato glaze. Bake another 25 minutes.
Let the meatloaf rest for 10 minutes, then slice and serve!