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Preheat oven to 400º. On a work surface, cut a pocket into thickest side of chicken breast, being sure not to cut all the way through. Stuff each with spinach, tomatoes and their oil, and mozzarella. Season chicken all over with Italian seasoning, salt, and pepper. Secure with toothpicks.
In a large heatproof skillet over medium-high heat, heat reserved tomato oil. Sear chicken until golden brown, about 3 minutes per side.
Transfer skillet to oven and bake until no longer pink and an instant-read thermometer inserted into thickest part registers 165°, about 15 minutes.
Remove toothpicks. Arrange chicken on a platter. Pour pan juices over.