Preheat oven to 400F. Line a rimmed baking sheet with parchment paper.

Heat the olive oil over medium heat. Add onion and cook until translucent, stirring occasionally. Once softened, add garlic and cook for another 30 seconds, just until fragrant. Remove from heat and scrape the mixture into a large mixing bowl. Let cool slightly.

To the bowl, add ground beef, bread crumbs, milk, 2 tablespoons ketchup, worcestershire sauce, egg, salt and pepper, and cheddar cubes. Mix until just combined, being careful not to overmix.

Shape the mixture into a loaf on the prepared baking sheet. Spread remaining 2 tablespoons of ketchup on top.

Bake 40 - 45 minutes or until the inside reaches 160F. Let cool for 5 minutes before slicing and serving.