Preheat the oven to 375 degrees F and line a baking sheet with parchment paper.
In a mixing bowl, combine the ground chicken, pesto, breadcrumbs, egg, minced garlic, salt, and black pepper until evenly mixed.
Divide the mixture into four equal portions. Flatten each portion slightly, place one piece of provolone in the center, and shape the meat around the cheese to fully enclose it.
Place the formed meatloaves on the prepared baking sheet and brush the tops lightly with olive oil.
Bake for 25 to 30 minutes until the internal temperature reaches 165 degrees F and the cheese inside has melted.
Remove from the oven and let the meatloaves rest for 5 minutes before serving.