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Preheat oven to 425°F. Cook tortellini according to package directions, drain, and spread evenly in a 9×13-inch baking dish.
In a small bowl, mix 1 tbsp olive oil, Italian seasoning, salt, and pepper. Coat chicken cutlets in the mixture.
Grill chicken over high heat (425–450°F) for 7–8 minutes per side, until internal temperature reaches 165°F. Let rest before slicing.
In a saucepan over medium heat, melt butter. Add minced garlic and garlic powder, sauté briefly. Sprinkle in flour and whisk until smooth. Gradually add milk and cream, whisking constantly. Bring to a gentle boil, reduce heat, and simmer 2–3 minutes until thickened. Stir in Parmesan until melted and smooth.
Pour Alfredo sauce over tortellini in the baking dish.
In a small bowl, combine breadcrumbs, Asiago cheese, and remaining 1 tbsp olive oil. Sprinkle over tortellini.
Bake uncovered for 15 minutes, until bubbly and lightly golden.
Slice grilled chicken and place on top of baked tortellini. Garnish with fresh parsley before serving.