Preheat oven to 350°F and adjust rack to lower-middle position.

Core and hollow out tomatoes using a melon baller or teaspoon.

Place tomatoes upside down on paper towels to drain.

Combine feta cheese, roasted peppers, pickled banana peppers, minced garlic, dried oregano, and crushed red pepper in a medium bowl.

Season with black pepper and gently stir to combine.

Fill each tomato with the feta mixture.

Nestle the stuffed tomatoes together, right side up, in an 8x8 inch baking dish.

Drizzle with olive oil.

Bake until tomatoes are tender and slightly wrinkled and the filling is warm, about 25 minutes.

Serve warm.