Preheat oven to 350 degrees F (175 degrees C). Spray a miniature muffin pan with cooking spray.
Insert wonton wrappers into the muffin pan so as to form small cups. Bake 5 minutes in the preheated oven. Allow the baked wrappers to cool. Remove from the pan.
In a medium bowl, mix the sausage, Monterey Jack, Cheddar, black olives and Ranch-style dressing. Fill the baked wonton wrapper cups with the mixture.
Bake the filled wonton wrappers 10 to 15 minutes, until the sausage mixture is bubbly and slightly brown. Watch closely so the wonton wrappers do not burn.
