Pound chicken breasts with a meat mallet to 1/2-in. thickness. Brush with oil and sprinkle with salt and pepper. Place chicken on a lightly oiled grill rack. Grill, covered, over medium heat until a thermometer reads 165°, 4-5 minutes on each side.
Meanwhile, cook tortelloni according to package directions. Preheat broiler. Drain tortelloni and toss with warmed Alfredo sauce. Transfer to a greased broiler-safe 9-in. square baking dish; sprinkle with Asiago. Broil 3-4 inches from heat until top is golden brown, 2-3 minutes.
To serve, slice chicken and place on top of tortelloni. Sprinkle with additional Asiago if desired.
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