There are few meals more comforting than a nice warm bowl of tomato soup with a grilled cheese sandwich. This version takes that classic combo and gives it a little extra love, with sweet roasted tomatoes, carmelized onion, and an entire head of roasted garlic.
Roasting the vegetables brings out their natural sweetness and gives this soup a rich, deep flavor that you just can’t get from canned tomato soup. Add to that a crispy sourdough grilled cheese filled with sharp cheddar and creamy Gouda and it makes this a meal that feels a little more special while still being simple to make.
It’s cozy, flavorful and just about perfect for a chilly fall afternoon.
I SHOW YOU HOW TO MAKE THIS ROASTED ROMA TOMATO SOUP WITH SOURDOUGH GRILLED CHEESEÂ BELOW! For more video recipes, subscribe to my YouTube channel: Mr. B Cooks.

Roasted Roma Tomato Soup
Ingredients
Method
- Preheat and Prep: Preheat your oven to 400°F (205°C). Slice the 15 Roma tomatoes in half lengthwise and place them cut-side down on a large baking sheet along with the onion wedges. Cutting them this way helps them caramelize beautifully.
- Prep the Garlic: Slice the very top off the head of garlic to expose the cloves. Drizzle it with a little olive oil and wrap it tightly in aluminum foil. Place it on the baking sheet alongside the veggies.
- Season and Roast: Drizzle everything generously with olive oil. Season with a heavy pinch of salt and black pepper. Roast in the oven for 40 to 45 minutes until the tomatoes are shriveled and show some charred, dark edges.
- Combine and Simmer: Let the garlic cool for a few minutes, then squeeze the roasted cloves out of their skins straight into a large soup pot or Dutch oven. Transfer all the roasted tomatoes, onions, and any pan juices into the pot. Pour in the 2 cups of broth. Bring to a boil over medium-high heat, then reduce to low and simmer for 10 minutes.
- Blend: Stir in the fresh basil leaves. Use an immersion blender directly in the pot to blend the soup until completely smooth. (If using a countertop blender, let it cool slightly and blend in batches with the lid cap cracked open to vent steam).
- Finish and Season: Stir in the 1/2 cup of heavy cream. Taste the soup and adjust the seasoning with more salt, pepper, or red pepper flakes. If it tastes too acidic, stir in 1 teaspoon of sugar to balance the flavors. Simmer for 2 more minutes, then serve hot.
Video
Notes
Ingredients
Method
- Prep the Bread: Lay both slices of sourdough flat on a clean cutting board. Spread a thin, layer of mayonnaise over the top side of each slice. These mayo-coated sides will make direct contact with the pan.
- Layer the Cheeses: Invert the bread slices so the mayonnaise sides face down. On one slice, build your cheese profile by laying down the extra-sharp cheddar first, followed immediately by the Gouda. Top with the second slice of sourdough, ensuring the mayonnaise-coated side faces outward.
- Heat the Skillet: Place a seasoned cast-iron or heavy non-stick skillet over medium low heat. Add 1 tablespoon of your unsalted butter, swirling it across the skillet until fully melted.
- Toast Low and Slow: Carefully transfer the sandwich into the pool of melted butter. Cook undisturbed for 4 to 5 minutes. Maintain a low temperature to give the sourdough time to crisp, while allowing the interior cheeses to completely melt.
- Flip and Finish: Once the underside reaches a deep golden color, carefully slip the sandwich over. Introduce the remaining butter to the skillet if the surface seems dry. Toast for an additional 3-4 minutes until both sides are crisp and the cheese core is completely melted and gooey.
- Serve: Remove from heat, slice in half, and serve immediately alongside hot, roasted tomato soup.

