Heat oven to 400 degrees. If convection roast is an option, it is best to use.
Place the quartered tomatoes, cloves of garlic, and quartered white onion into a 9x13 pan. Heavily salt and pepper the vegetables. Pour the oil evenly over the vegetables and place them in the oven.
Bake for 30 min, or until the tomatoes and onions have some dark burning on the tips.
Remove from the oven and place in a medium to large pot. Add in the chicken stock, sugar, and half the basil leaves.
Using your hand blender, blend the soup until smooth. The consistency of the soup will be personal preference, and you can blend more or less. Keep the soup on low heat while you make the sandwich.
Heat the Panini Press or Grill to medium heat.
Spread butter on 1 side of all of the sourdough. Flip to build the sandwich.
Grate the extra old cheddar cheese, followed by the apple. Mix the grated cheese and apple together and set it aside.
Spread brie on the bottom of the sourdough slice, top with 1/2 the grated cheese and apple. Take the arugula leaves and place it on top of the cheeses, topped with the rest of the cheese and apple mixture.
Place the top piece of bread on the finished layers, and place it on the panini grill, and press down. Grill until the bread is browned and the cheese is melty.
Remove the sandwich from the grill and let it sit while the soup is finished for serving.
Remove the soup from the low heat and ladle it into bowls. Julian Basil leaves and sprinkle on top of the soup. Take the Parmigiano Reggiano and grate fresh from the block or sprinkle on top of the basil.
Cut the sandwich in half and serve it with the tomato soup immediately.