Heat olive oil in a large skillet over medium-high heat.
Add diced onion to the skillet and sauté for 3-4 minutes until softened.
Add minced garlic and cook for 30 seconds until fragrant.
Add ground beef to the skillet and cook, breaking it apart with a spatula, until browned and cooked through, about 6-8 minutes.
Drain excess fat from the skillet if necessary.
Stir in diced tomato, ketchup, yellow mustard, Worcestershire sauce, salt, black pepper, and smoked paprika.
Cook the mixture for another 3-4 minutes, stirring occasionally, until heated through and combined.
Sprinkle shredded cheddar cheese evenly over the beef mixture and cover the skillet with a lid.
Allow the cheese to melt for 2-3 minutes.
While the cheese melts, toast the hamburger buns in a separate pan or toaster until golden brown.
Serve the cheeseburger skillet hot with toasted buns on the side.