In a mixing bowl, combine diced Roma tomatoes, minced garlic, chopped fresh basil, olive oil, and balsamic vinegar. Season with salt and pepper. Let sit for at least 15 minutes.

Season the chicken breasts with oregano, basil, garlic powder, salt, and pepper. Cook in a skillet over medium-high heat with olive oil for 3-4 minutes on each side until golden brown.

Cook the penne pasta in salted boiling water according to package instructions, typically 8-9 minutes until al dente. Reserve 1/4 cup pasta water before draining.

Add the bruschetta topping to the skillet over medium-low heat and warm it through for 1-2 minutes. Add the drained pasta and reserved pasta water, tossing everything to combine.

Slice the rested chicken and place it on top of the pasta. Sprinkle with grated Parmesan cheese and basil leaves before serving instantly.