Preheat the oven to 375°F and line a baking sheet with parchment paper.
In a large bowl, combine the ground pork, diced apple, chopped sage, breadcrumbs, egg, onion, garlic, salt, and black pepper. Mix with your hands until the ingredients are evenly distributed but not overworked.
Shape the mixture into a loaf about 8 inches long and place it on the prepared baking sheet. Lay the bacon slices over the top and sides of the loaf, overlapping slightly so the meat is fully covered.
Toss the Brussels sprouts with the olive oil, salt, and black pepper in a separate bowl. Spread them around the meatloaf on the baking sheet.
Bake for 45 to 50 minutes until the internal temperature of the meatloaf reaches 160°F and the bacon looks crisp. Let the meatloaf rest for 5 minutes before slicing. Serve the Brussels sprouts on the side.