Assemble, prepare, and measure ingredients. Core and cut apples into eighths but don’t peel them. Pound pork cutlets to 1/2-inch/1 cm thickness using a meat tenderizer. Peel and smash garlic.
In a large skillet over medium-high heat, melt butter. Add apples, season with a pinch of cinnamon and salt and pepper, and cook for 12–15 minutes, turning every so often, until apples have softened but not turned into applesauce. Transfer apples and their cooking juices to a bowl.
In the same skillet, cook 11/2 tablespoons of olive oil with 3 garlic cloves, 2 anchovies, 6 sage leaves, and a liberal grinding of black pepper for about 30 seconds. Add half the cutlets and cook for 2 minutes per side, until deep brown in places. Transfer cooked cutlets to a platter and keep warm. Repeat with remaining olive oil, garlic, anchovies, sage leaves, and cutlets.
Return the same skillet to medium heat, add vinegar, and stir for about 2 minutes to pick up any brown bits from bottom of pan and reduce liquid slightly, just until starting to thicken. Gently stir this mixture into the apples.
To serve, arrange pork cutlets on a serving platter. Carefully place apples on top and drizzle cooking juices over everything.