Pre-heat the oven to 375. Lightly mist 12 cups in a standard mun/cupcake tin with cooking spray and set aside.
Cook the ground beef in a medium skillet at medium heat. Use a wooden spoon to break it up into small pieces as it cooks. When the meat is almost browned, add the onions and the garlic and stir together. Continue to cook for another few minutes until the meat is browned and onions are softened.
Add the kidney beans, diced tomatoes, Carroll Shelby’s Chili Seasoning and cayenne (if you want it spicy) to the meat mixture and stir together until well combined. Reduce the heat to low and simmer, uncovered, for 10 minutes or until thickened.
Push a wonton wrapper into the bottom of each of the sprayed cups in the mun tin.
Using about half of the chili mixture, spoon evenly into the wonton wrappers.
Sprinkle about half of the shredded cheddar evenly over the top of each cup. Press another wonton wrapper on top and repeat the layering steps with the remaining chili mixture and shredded cheddar. You are making “Double Decker” chili cups here.
Bake for 18-20 minutes until the wontons are golden brown and the contents are heated through. Remove the muntin from the oven and allow it to cool for 2-3 minutes before removing it from the tin.
Top with Sour Cream and garnish with Green Onions.