Lightly brush both sides of each wonton wrapper with olive oil.

Press the wrappers into the cups of a standard muffin tin, creating small edible bowls.

Bake until golden brown and crisp, about 8–10 minutes, then transfer to a cooling rack.

Finely chop the romaine lettuce and place it in a large mixing bowl.

Add the diced chicken, Parmesan cheese, croutons, salt, and black pepper.

Pour in the Caesar dressing and gently toss until everything is evenly coated.

Allow the wonton cups to cool completely so they remain crisp.

Spoon the Caesar salad mixture into each baked cup, filling generously.

Top each cup with a cherry tomato half and an extra sprinkle of Parmesan cheese.

Arrange on a serving platter and serve immediately while the cups are crisp and fresh.