Preheat the oven to 375 degrees. Line a baking sheet with foil for easier cleanup.
In a mixing bowl, combine the ground beef, breadcrumbs, egg, milk, onion, garlic powder, salt, and pepper. Mix until just blended.
Shape the mixture into a loaf about 8 inches long and place it on the prepared baking sheet.
Lay the bacon slices across the top of the loaf, tucking the ends underneath so the bacon stays in place.
Bake for 30 minutes.
While the meatloaf bakes, stir together the brown sugar, ketchup, apple cider vinegar, and Worcestershire sauce in a small bowl.
Remove the meatloaf from the oven and spread the glaze evenly over the top and sides.
Return to the oven and bake for 20 to 25 more minutes, until the internal temperature reaches 160 degrees and the bacon is crisp.
Let the meatloaf rest for 10 minutes before slicing.