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Preheat oven to 400ºF. Line a large rimmed baking sheet with foil.
Combine onions, pepper, ketchup, mustard, breadcrumbs, eggs, Worcestershire, oregano, and thyme in a bowl. Season with salt and pepper.
Gently mix in beef with your hands, being careful not to overmix. (It should be soft but hold its shape.)
Transfer meat to prepared baking sheet and shape into a 10-by-5-inch loaf.
Combine ketchup, Worcestershire, and brown sugar in a bowl. Brush meatloaf with 3 tablespoons topping.
Place bacon crosswise over top of meatloaf and cover with remaining glaze.
Bake 15 minutes. Reduce oven temperature to 350°F and bake until an instant-read thermometer reaches 160°F, 35 to 40 minutes.
Let rest 15 minutes before serving.