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Preheat oven to 425°F (220°C).
Add tomatoes, onion & garlic to a baking sheet. Drizzle with olive oil and season with salt, black pepper, red pepper flakes & oregano.
Roast for 35–45 mins until the tomatoes are very soft and caramelized around the edges.
Let cool slightly before blending.
Squeeze the roasted garlic from its skin and add the roasted tomatoes, onion & garlic to a blender along with the broth, heavy cream, fresh basil & balsamic vinegar.
Blend until completely smooth.
Taste and adjust with salt, pepper, balsamic or a little honey/sugar if the tomatoes need more balance.
Mix softened butter with Parmesan, garlic powder & black pepper.
Spread evenly over the outside of both sourdough slices.
Add sharp cheddar & Gruyère between the slices of bread.
Place the sandwich in a cold pan, then turn the heat to medium-low.
Cook for 3–4 mins until deeply golden and crispy.
Flip and cook another 3–4 mins.
Cover the pan for 30–60 seconds to help the cheese fully melt, then uncover and crisp for another 30 seconds.
Remove from the pan and let rest for about 1 min before slicing diagonally.
Pour the tomato soup into a bowl and garnish with a drizzle of heavy cream, olive oil, fresh basil, Parmesan & cracked black pepper.
Serve with the crispy grilled cheese, dunk generously & enjoy!!