Preheat the oven to 350°F (175°C). Gently coat a muffin tin with a light mist of olive oil spray to ensure easy removal of the muffins after baking.

Make the wonton cups: Press each wonton wrapper into the prepared muffin tin, molding them to form small cups. Lightly spray the tops of the wrappers with olive oil spray and bake for 8-10 minutes, or until they turn golden brown and crispy. Remove and set aside to cool.

Cook the bacon: In a small skillet, cook the diced bacon over medium heat until crispy.

Prepare the croutons: In the same skillet, lightly toast the diced bread in the bacon fat, adding a sprinkle of salt if needed. Toast until golden and crispy. Set aside.

Make the Caesar dressing: In a bowl, whisk together the minced garlic, mashed anchovy fillets, lemon juice, Dijon mustard, and Worcestershire sauce. Stir in the mayonnaise and freshly grated parmesan cheese. Incorporate a splash of milk to achieve your desired consistency, then season with salt and freshly cracked black pepper to enhance the flavor to your preference.

Assemble the salad: In a large bowl, toss the shredded romaine lettuce, diced chicken, crispy bacon, and croutons together. Add a generous amount of Caesar dressing and toss until everything is well coated.

Fill the wonton cups: Spoon the Caesar salad mixture into the cooled wonton cups. Sprinkle with freshly grated parmesan cheese and parsley for garnish, if desired.

Serve immediately and enjoy your delicious Caesar Salad Wonton Cups!