Heat the oven to 400 degrees and line a sheet pan with parchment paper or foil.
In a mixing bowl, combine the ground beef, chopped mushrooms, 1 cup of the Swiss cheese, breadcrumbs, egg, diced onion, minced garlic, Worcestershire sauce, and a pinch of salt and pepper. Mix gently until just combined.
Divide the mixture into four equal portions and shape each into a small loaf. Place the loaves on the prepared sheet pan.
In the same bowl, toss the asparagus spears with the olive oil and a sprinkle of salt and pepper. Arrange the spears around the meatloaves on the sheet pan.
Top each meatloaf with the remaining 1/2 cup of shredded Swiss cheese.
Bake for 25 to 30 minutes until the meatloaves reach an internal temperature of 160 degrees and the cheese is melted and lightly browned.