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).
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