Preheat the oven to 350 degrees.
Place the wontons in a muffin tin. Spray them with cooking spray and bake for 13-15 minutes or until golden brown.
Remove from the oven and allow to cool.
Meanwhile, chop the Romaine lettuce and place in a large bowl. Add in the tomatoes, Parmesan cheese, croutons, and Caesar salad dressing. Toss to combine and add salt and pepper to taste.
Place several tablespoons of salad into each wonton cup and serve immediately.