Preheat oven to 350. Chop tomatoes & pepper. Place on baking sheet & drizzle with oil. Roast for 40 minutes.
Add to a large pot with garlic, puree, stock, & sugar. Set to low/medium heat and bring to a low boil for 10 minutes.
Spread butter on one side. Top with pimento cheese then top with other slide of buttered bread. Cook on med/high heat.
Cook 3 minutes, flip, then cook 3 more minutes until the middle is melted. Serve with the tomato soup.