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Preheat oven to 400 degrees. In a large skillet, heat oil over medium-high. Coat pork with garlic and fennel seed, then season with salt and pepper. Cook until browned on all sides, 4 minutes total. Transfer to a rimmed baking sheet (reserve skillet) and roast, turning occasionally, until cooked through, 15 minutes. Transfer to a cutting board, tent with foil, and let rest 10 minutes.
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On a baking sheet, brush tops of pitas with oil and season with salt and pepper. Bake until edges are golden, 8 minutes. Cut into wedges.
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Divide arugula, parsley, and carrots among four plates. Slice pork into rounds and add to salad. Remove any dark garlic bits from skillet, add vinegar and any accumulated juices from board, and swirl to combine. Drizzle sauce on pork and serve with pitas.