Preheat oven to 375 degrees F (190 degrees C). Grease a 9x11-inch baking dish.
Place bacon in a large skillet and cook over medium-high heat until edges just start to curl, 1 to 2 minutes per side. Drain the bacon slices on paper towels. Reserve about 1 tablespoon bacon drippings in the skillet.
Cook and stir onion and garlic in the bacon drippings until onion is softened, 6 to 7 minutes. Remove from heat and cool.
Mix cooled onion and garlic, ground beef, 1/2 cup barbeque sauce, bread crumbs, eggs, Worcestershire sauce, Dijon mustard, oregano, and chili powder together with your hands in a large bowl. Form beef mixture into a log-shaped meatloaf; place in the prepared baking dish.
Wrap partially-cooked bacon slices around the meatloaf, tucking the ends of bacon underneath the loaf.
Bake in the preheated oven for 35 minutes. Brush bacon-wrapped meatloaf with 3 tablespoons barbeque sauce. Continue baking until no longer pink in the center, about 10 more minutes. An instant-read thermometer inserted into the center should read at least 160 degrees F (70 degrees C). Let stand for 10 minutes before serving.