Preheat the oven to 400°F. Use non-stick spray to spray the sides and bottom of your 9.5 x 5” loaf pan. I also like to put a piece of parchment paper in so it’s easier to remove from the pan.
Heat olive oil in a medium skillet over medium-high heat. Begin to sauté the diced green peppers, onions and mushrooms. Cook until the peppers are tender and mushrooms slightly brown, approximately 2 to 3 minutes. When done, set aside to cool.
Place ground beef in a large bowl. Add garlic powder, salt, pepper, Italian seasoning, tomato paste and Worcestershire sauce. Mix thoroughly using either a wooden spoon or clean hands.
Next add in the remaining ingredients; milk, egg, breadcrumbs, as well as the sautéed mushrooms, onions and peppers.
Take half of the provolone and cut them into squares. Mix well into the meatloaf, separating the cheese slices if they stick together so it is well incorporated throughout the meatloaf.
Press philly cheesesteak meatloaf into the prepared loaf pan. Bake uncovered in the oven for approximately 40 to 45 minutes or until the internal temperature is 160°F.
Remove the meatloaf from the oven. Cut the provolone slices in half and layer the slices over the meatloaf. Bake until the cheese melts, and starts to bubble, approximately 5 minutes.
Remove from the oven, let cool for 10 minutes to allow the meatloaf to set and be easier to remove from the pan. Slice and enjoy.