Prep the Oven and Mushroom: Preheat your oven to 375°F / 190°C. Lightly oil a small baking dish. To prepare the portobello, gently wipe it clean with a damp paper towel. Twist off the stem and, using a spoon, gently scrape out the black gills from the underside of the cap.
Mix the Filling: In a medium bowl, combine the cooked orzo, tomato sauce, shredded mozzarella, chopped tomato, and dried oregano.
Season generously with salt and freshly ground black pepper and mix until everything is well incorporated.
Stuff and Bake: Brush the entire portobello mushroom—cap and underside—with olive oil and place it gill-side-up in your prepared baking dish. Mound the orzo mixture generously into the mushroom cap.
Bake to Perfection: Transfer the baking dish to the preheated oven and bake for 25 to 30 minutes. The mushroom is ready when it's tender and the cheese on top is melted, bubbly, and slightly golden.
Serve immediately.