In a mixing bowl, combine the drained whole tomatoes, olive oil, light brown sugar, carrots and shallots, and toss to coat. Season the vegetables with salt and pepper. Place the vegetables on a silicone or parchment-lined baking sheet and roast until caramelized, about 30 minutes.
Heat a soup pot over medium heat. Add the butter and cook until foaming. Add the crushed red pepper and garlic and saute for 1 minute. Add the tomato paste and cook for 1 to 2 minutes. Then add the sherry. Cook until all the liquid has evaporated and the alcohol has cooked off, 1 to 2 minutes. Add the roasted vegetables, crushed tomatoes and 1 cup chicken stock. Season with salt and pepper and bring to a simmer. Let simmer for 15 minutes.
Add the heavy cream and, using an immersion blender, puree the soup until uniform in texture. Add more chicken stock to adjust the consistency to how you like it.