Preheat oven to 325ºF.
Place a cooling rack over a baking sheet. Arrange tomatoes on the rack then drizzle with a touch of EVOO and season the tomato slices with salt and pepper. Roast tomatoes 45 minutes.
When the tomatoes are about ready, place a large skillet over medium-high heat with 2 turns of the pan of EVOO, about 2 tablespoons. While the pan is heating up combine the sirloin with some salt and pepper and form into 4 patties, thicker at edges and thinner in the center for even cooking and to insure you end up with a flat burger as the burger bulges up during cooking. Cook patties 10 minutes for medium-rare patties turning once. Cook 12 minutes for pink centers and 14 minutes for well-done.