Preheat the oven to 350°F. Grease a 12-cup muffin pan.
In a large skillet, heat 1 tablespoon olive oil over medium heat. Add 1 cup finely chopped onion and cook about 5 minutes, stirring occasionally, until softened. Add 2 cloves minced garlic and cook about 30 seconds, until fragrant. Remove from heat and let the onion and garlic cool slightly.
In a large bowl, combine 1 1/2 pounds ground beef, the cooked onion and garlic, 1/2 cup breadcrumbs, 1/2 cup ketchup, 1 tablespoon Worcestershire sauce, 1 lightly beaten large egg, 1 teaspoon dried oregano, 1/2 teaspoon salt, and 1/4 teaspoon black pepper. Mix until just combined — avoid overworking the meat.
Divide the meat mixture evenly among the 12 muffin cups, pressing gently to form compact muffins but not packing them too tightly.
Spoon the remaining ketchup (about 1/2 cup total) evenly over the tops of the 12 meatloaf muffins (about 2 teaspoons per muffin).
Bake in the preheated oven for 25 minutes, or until an instant-read thermometer inserted into the center of a muffin reads 160°F.
Let the meatloaf muffins rest in the pan for about 5 minutes, then remove from the pan and serve.