Make the tomato-arugula salad: in a medium bowl whisk 1 tbsp olive oil and 2 tbsp balsamic vinegar, then add the diced tomatoes, chopped basil and sliced red onion; season with kosher salt and fresh cracked black pepper and toss. Let sit at least 10 minutes to combine.
Preheat the oven to 450°F (230°C) and place a large baking sheet in the oven to heat.
Prepare the breading: combine the whole wheat Italian seasoned breadcrumbs and grated Romano cheese in a shallow bowl.
In another shallow bowl whisk together 1 tbsp olive oil, the juice of 1 lemon, and several grinds of fresh cracked black pepper.
Pound the chicken breasts to an even thickness with a meat mallet or rolling pin until you have six cutlets. Pat dry with paper towels and season both sides lightly with kosher salt and pepper.
Dip each cutlet into the lemon-oil mixture, then press into the breadcrumb-cheese mixture until well coated. Press firmly so crumbs adhere.
Remove the preheated baking sheet from the oven, lightly spray with olive oil spray, and arrange the breaded cutlets on the sheet. Lightly spray the tops of the cutlets with olive oil spray.
Bake the chicken at 450°F for about 15 minutes total, turning once halfway through, until golden brown and cooked through.
Remove the chicken from the oven and top each cutlet with a generous handful of baby arugula and a spoonful of the tomato mixture; serve immediately.