Gather all ingredients. Preheat the oven to 425 degrees F (220 degrees C). Line a baking sheet with parchment paper.
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Photographer: Grant Webster / Food Styling: Shannon Goforth / Prop Styling: Gabriel Greco
Slice eggplant lengthwise into four 1/4-inch thick slices. Reserve remaining eggplant for another use.
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Photographer: Grant Webster / Food Styling: Shannon Goforth / Prop Styling: Gabriel Greco
Brush eggplant slices evenly with 1 tablespoon olive oil. Evenly season with 1/4 teaspoon salt and 1/4 teaspoon pepper. Set on the prepared baking sheet.
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Photographer: Grant Webster / Food Styling: Shannon Goforth / Prop Styling: Gabriel Greco
Roast in the preheated oven until tender and lightly browned,20 to 22 minutes.
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Photographer: Grant Webster / Food Styling: Shannon Goforth / Prop Styling: Gabriel Greco
Add flour to a large shallow bowl. Season chicken with 1/4 teaspoon salt and 1/4 teaspoon pepper. Dredge chicken in flour until fully coated.
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Photographer: Grant Webster / Food Styling: Shannon Goforth / Prop Styling: Gabriel Greco
Heat 2 tablespoons oil in a 12-inch oven-proof skillet over medium-high heat. Add chicken breasts to skillet and cook until lightly browned, 3 to 4 minutes. Flip and cook other side until lightly browned, 3 to 4 minutes. Remove chicken from skillet; set aside.
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Photographer: Grant Webster / Food Styling: Shannon Goforth / Prop Styling: Gabriel Greco
Heat remaining 1 tablespoon oil in the skillet. Add onion and cook over medium heat until softened, about 3 minutes. Add garlic and cook until fragrant, about 30 seconds.
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Photographer: Grant Webster / Food Styling: Shannon Goforth / Prop Styling: Gabriel Greco
Pour chicken stock and marsala wine into the skillet. Bring to a boil and cook until liquid is reduced by half, scraping any browned bits from the bottom of the skillet, about 4 minutes.
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Photographer: Grant Webster / Food Styling: Shannon Goforth / Prop Styling: Gabriel Greco
Reduce heat and add crushed tomatoes. Season with remaining 1/4 teaspoon salt and 1/4 teaspoon pepper. Simmer until sauce comes together, about 5 minutes. Reserve 1/4 cup sauce.
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Photographer: Grant Webster / Food Styling: Shannon Goforth / Prop Styling: Gabriel Greco
Return chicken to the skillet. Top each chicken breast with 1 slice prosciutto, 1 slice cooked eggplant (folding to fit, if needed), 1 tablespoon reserved sauce, 2 tablespoons shredded fontina cheese, and 1 tablespoon grated Pecorino Romano.
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Photographer: Grant Webster / Food Styling: Shannon Goforth / Prop Styling: Gabriel Greco
Transfer skillet to the oven and bake until cheese is melted and chicken is cooked through (165 degrees F or 74 degrees C), about 10 minutes.
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Photographer: Grant Webster / Food Styling: Shannon Goforth / Prop Styling: Gabriel Greco
Serve topped with chopped herbs.
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Photographer: Grant Webster / Food Styling: Shannon Goforth / Prop Styling: Gabriel Greco
Recipe developed by Barrett Heald