Peel and core apple. Cut into eight wedges. Halve fingerling potatoes lengthwise. Zest lemon, halve, and juice. Mince chives. Core Roma tomato and cut into 1/4" dice. Rinse chicken breasts, pat dry, and season both sides with 1/2 tsp. salt and 1/4 tsp. pepper.

Place potatoes on prepared baking sheet. Drizzle with 1 Tbsp. olive oil, 1/2 tsp. salt, and 1/4 tsp. pepper. Toss to coat, then spread into a single layer. Roast 20-23 minutes, until browned and fork-tender. While potatoes roast, cook chicken.

Place a medium oven-safe pan over medium-high heat. Add 2 tsp. olive oil and chicken to hot pan. Sear undisturbed until well-browned, 3-4 minutes. Flip onto second side and place pan in oven. Roast until chicken reaches a minimum internal temperature of 165 degrees, 5-7 minutes. Remove chicken from pan, cover loosely with foil, and rest 3-5 minutes. Reserve pan for making sauce; no need to wipe clean.

Carefully wrap a dry dish towel around handle of pan used to cook chicken and place over medium-high heat. Add 1 tsp. olive oil and apples to hot pan. Cook until fragrant, 1 minute. Add white cooking wine, bring to a boil, and reduce by half. Add cream, bring to a simmer, and cook 1 minute until slightly thickened. Season with 1/4 tsp. salt and remove from heat.

Toss together arugula, tomatoes, Parmesan, 1 tsp. lemon zest, 1 Tbsp. lemon juice, 1.5 Tbsp. olive oil, 1/4 tsp. salt, and 1/4 tsp. pepper in a medium mixing bowl.

Place fingerling potatoes on plate. Spoon sauce and apples on plate and top with chicken. Garnish with chives. Serve salad on side.