- 8 slices bacon, divided
- 1 pound ground beef
- 1/4 cup dry bread crumbs
- 1 egg, beaten
- 1 clove garlic, minced
- 1 teaspoon Worcestershire sauce
- 1 teaspoon salt
- 1 teaspoon ground black pepper
- Stuffing:
- 1 cup shredded Cheddar cheese, or as needed
- Pineapple glaze:
- 1/3 cup ketchup
- 1/4 cup brown sugar
- 1/4 cup crushed pineapple, drained
- 1 teaspoon Worcestershire sauce
- Preheat oven to 350 degrees F (175 degrees C). Chop 4 bacon strips; set remaining 4 bacon strips aside.
- Cook chopped bacon in a large skillet over medium heat, stirring often, until bacon is browned and crisp, 8 to 10 minutes. Set chopped bacon aside.
- Lightly mix ground beef, bread crumbs, beaten egg, garlic, 1 teaspoon Worcestershire sauce, salt, and black pepper together in a bowl until thoroughly combined. Spread meat mixture out on a piece of waxed paper, forming a rectangle about 10 inches square. Spread Cheddar cheese and cooked chopped bacon over the meat, leaving a 1/2-inch edge all around. Carefully lift an edge and roll the meat around the filling. Place into a loaf pan with the seam side down.
- Bake meat loaf in the preheated oven until hot and beginning to brown, about 30 minutes. Mix ketchup, brown sugar, pineapple, and 1 teaspoon Worcestershire sauce together in a bowl, stirring to dissolve brown sugar. Remove meat loaf from oven and place remaining 4 bacon strips onto meat loaf, weaving them together. Spread pineapple mixture over woven bacon and top of loaf.
- Return meat loaf to oven and bake until bacon topping is crisp and pineapple mixture has baked into a glaze, about 20 more minutes. An instant-read meat thermometer inserted into the center of the meat loaf should read 160 degrees F (70 degrees C).