Preheat a baking sheet in the oven to 475º. Toss the potatoes in 1/2 of the olive oil, a pinch of salt and a grind or two of black pepper. Spread the potatoes out on the hot baking sheet and roast for 25 minutes, flipping over at about the halfway mark.
Make several shallow cuts in the fat along the side of the pork chop which will stop it curling in the pan. Season with half of the oregano, salt and pepper. Heat remaining olive oil in a skillet over medium heat. Add the pork and cook for about 2-3 minutes per side. Set aside on a plate.
Add the tomatoes, garlic and remaining oregano to the skillet. Cook, stirring gently for a couple of minutes until the tomatoes have softened. Add the wine and cook for a further 2-3 minutes, until the wine has almost disappeared. Deglaze with a couple of tablespoons of water, crushing the tomatoes until slightly thickened. Stir in the olives, sugar and any pork juices on the pork plate. Season with salt and pepper.
When the potatoes are cooked, sprinkle with the feta cheese and set aside for a minute or two to allow the feta to soften. Sprinkle with the dill. place the potatoes and pork chop on a plate and top with the tomato mixture. Drizzle with a little olive oil.