Line a baking sheet with parchment paper and preheat oven to 400 degrees F.
Place raw shrimp onto the prepared baking sheet. Add 1 tablespoon olive oil, salt and pepper, to taste, and gently toss to combine. Place in oven and cook until they are pink and cooked through, about 5-8 minutes depending on size of shrimp. Remove from oven and let the shrimp cool before cutting into large bite-size pieces.
Reduce oven temperature to 350 degrees F. Lightly grease a 9x13 baking pan.
Heat remaining 1 tablespoon olive oil in a large skillet. Add red pepper and onion. Cook until peppers are tender and onions become translucent, about 5 minutes. Stir in oregano and cayenne pepper. Add shrimp and gently toss to combine. Remove from heat.
Take one corn tortilla and dip one side of the tortilla in the sauce, lay tortilla on a flat surface sauce side up and spoon 1/4 cup of the shrimp mixture in the center; sprinkle with cheese. Roll the tortilla and place seam side down onto prepared baking dish. Repeat with remaining tortillas.
Pour half of the poblano cream sauce evenly over the top. Cover and bake until lightly golden and bubbly, about 20 minutes
Serve immediately with remaining sauce, garnished with cilantro and fresh tomatoes.