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Heat oven to 400°F (204°C). Lightly oil a rimmed baking sheet or 9-inch by 13-inch baking pan lined with aluminum foil.
Heat oil in a large skillet over medium-low heat. Add the onion and cook, stirring occasionally, until softened; about 5 minutes. Add the garlic and cook until fragrant, about 1 minute. Stir in the mushrooms, a ½-teaspoon of salt, and a ¼-teaspoon of pepper. Cook until the mushrooms give off their liquid and it boils away; about 10 minutes.
Transfer the onions and mushrooms to a large bowl, and then stir in the Worcestershire sauce and three tablespoons of the ketchup. Set aside to cool for 5 minutes.
Meanwhile, combine the breadcrumbs and milk in a small bowl. Stir the breadcrumb mixture and the eggs into the mushrooms and onions. Using a fork or your hands, gently mix in the turkey, a ¼-teaspoon of salt, and a ¼ teaspoon of pepper. The mixture will be very wet.
Form the meatloaf into a 9-inch by 5-inch oval in the middle of the prepared baking sheet. Spread the remaining four tablespoons of ketchup on top.
Bake the meatloaf until an instant-read thermometer inserted into the thickest part of the meatloaf registers 170°F, about 50 minutes. Let rest 10 minutes before slicing.