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A baking pan with Chicken Pizzaiola with Pepperoni. As well as one plated with a side of Caesar salad.

Chicken Pizzaiola with Pepperoni (Stuffed Recipe)

Inspired by traditional Italian Chicken Pizzaiola, this recipe transforms a classic dish into a uniquely indulgent experience. Tender chicken breasts are butterflied and stuffed with gooey mozzarella and a savoury vegetable-pepperoni mixture, then topped with a rich tomato sauce, extra cheese, and more pepperoni for a delightful crunch. The result is a hearty, comforting, and delicious meal that's perfect for busy weeknights or special occasions.
5 from 1 vote
Prep Time 20 minutes
Cook Time 35 minutes
Total Time 55 minutes
Course Dinner, Entree, Main Course
Cuisine Italian, Italian-American
Servings 4

Ingredients
  

  • 2 teaspoons avocado oil or extra virgin olive oil
  • 1 small onion diced
  • 1 large red bell pepper diced
  • 1 jalapeño diced, seeds and membrane optional
  • 2 teaspoons dried oregano divided
  • 64 slices approx. 100g Grimm’s Dry Pepperoni Toppers (divided- 28 whole for topping, roughly chop the remaining 36)
  • 4 fresh garlic cloves minced
  • 1 bottle of passata
  • 3 tablespoons tomato paste
  • 4 skinless chicken breasts about 6 ounces each
  • 1 teaspoon freshly ground black pepper
  • 2 cups mozzarella cheese grated and divided
  • ¼ cup grated Parmesan cheese or Grana Padano
  • 2 tablespoons fresh basil leaves sliced into thin ribbons

Instructions
 

Prepare the Vegetable Mixture & Sauce

  • Heat 2 tablespoons of the olive oil in a medium skillet over medium heat. Add the diced onion, red bell pepper, and 1 teaspoon of oregano. Sauté for 5–7 minutes until soft.
  • Add the roughly chopped pepperoni and cook for 2 minutes. Stir in the minced garlic and cook for another 2 minutes until the garlic turns lightly golden. Transfer the mixture to a plate.
  • In the same skillet, combine the passata, tomato paste, and remaining oregano. Heat over medium-low for 1–2 minutes while stirring, then remove from the heat and set aside.

Prepare the Chicken

  • Preheat your oven to 375°F and lightly grease a 9” x 11” baking dish.
  • Place chicken breasts on a cutting board. Using a sharp knife, carefully slice along the side of each breast to butterfly it (open it like a book).
  • Fill the opening of each breast with ¼ cup of mozzarella, then add about ¼ cup of the vegetable-pepperoni mixture on top of the cheese.
  • Gently fold each breast closed, ensuring the stuffing is securely enclosed.

Assemble and Bake

  • Pour a thin layer of the tomato sauce into the baking dish. Arrange the stuffed chicken breasts on top and season with freshly ground pepper.
  • Pour the remaining sauce over the tops of the chicken. Sprinkle each breast with the reserved Parmesan and mozzarella cheeses.
  • Top each breast with 7 whole pepperoni slices.
  • Bake uncovered for 30–40 minutes, or until the chicken reaches an internal temperature of 165°F.

Serve and Enjoy

  • Remove from the oven and spoon sauce on the plate. Place the chicken over the sauce and sprinkle with fresh basil ribbons. Serve with a crisp Caesar salad and enjoy!

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Notes

Chef Tips:
  • Prep in Advance: You can prepare this chicken recipe ahead of time! Assemble the stuffed chicken breasts and store them, covered, in the refrigerator for up to 24 hours. When you're ready to cook, let the chicken sit at room temperature for about 15 minutes before baking. You can also make the sauce in advance and gently reheat it before assembly. This make-ahead approach helps streamline your final cooking process, making a delicious dinner stress-free and quick.
  • For even cooking: Make sure to butterfly the chicken breasts evenly so that the stuffing is well distributed.
  • Extra Cheesy: If you want extra gooeyness, feel free to add a little more mozzarella to the stuffing.
  • Adjust the Heat: Adjust the jalapeño amount based on your family’s heat preference.
What to Serve with Chicken Pizzaiola (Pollo alla Pizzaiola)
  • Serve with a crisp Caesar salad or a simple green salad.
  • If you like spice, serve with red pepper flakes on the side. 
  • Pair with garlic bread, crusty bread or pasta to soak up the sauce.
  • A glass of your favourite red wine (or a chilled rosé) can nicely complement this chicken dish.
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