Tomato Soup and Grilled Cheese (The Perfect Pairing)

What Makes This Recipe Work

Cooking the soup on high heat for a short time keeps the tomato flavor bright, and a cream finish rounds the acidity without muting it. Grilling the sandwiches on medium-low lets the cheese fully melt before the bread burns.

Ingredients for Tomato Soup and Grilled Cheese (The Perfect Pairing)

• 2 tbsp (28 g) unsalted butter, divided
• 1 small shallot or yellow onion, finely chopped
• 2 cloves garlic, minced
• 1 (28 oz / 794 g) can crushed tomatoes
• 1 1/2 cups (360 ml) chicken or vegetable broth
• 1 tsp sugar
• 1/2 tsp salt and 1/4 tsp black pepper, plus more to taste
• 1/4 cup (60 ml) heavy cream or whole milk, optional
• 8 slices sturdy sandwich bread
• 4 tbsp (55 g) softened butter or mayonnaise, for the bread
• 1 1/2 cups (170 g) shredded cheese blend (sharp cheddar and gruyere or fontina)
• 6 fresh basil leaves, torn, plus more for serving

How to Make Tomato Soup and Grilled Cheese (The Perfect Pairing)

1. Melt 1 tablespoon of the butter in a medium saucepan over medium heat. Add the shallot and cook until softened, about 3 minutes, then stir in the garlic for 30 seconds.
2. Add the crushed tomatoes, broth, sugar, salt, and pepper. Bring to a boil, then simmer at a lively bubble for 15 minutes, stirring occasionally.
3. Blend the soup with an immersion blender until smooth, then stir in the cream if using and the torn basil. Keep warm over low heat.
4. While the soup simmers, spread the softened butter or mayonnaise evenly on one side of each bread slice. Divide the shredded cheese evenly over 4 slices, then close each sandwich with the second slice, buttered side facing out.
5. Heat a large skillet or griddle over medium-low. Cook the sandwiches for 3 to 4 minutes per side, pressing gently with a spatula, until the bread is deep golden and the cheese is fully melted.
6. Rest the sandwiches for 1 minute so the melted cheese sets slightly, then cut in half on the diagonal.
7. Ladle the soup into bowls, finish with basil and black pepper, and serve the sandwiches alongside for dipping.

Tips for the Best Tomato Soup and Grilled Cheese (The Perfect Pairing)

• Mayonnaise on the outside browns more evenly than butter and gives a crispier crust; either works.
• Shred the cheese from a block; pre-shredded cheese melts more slowly and can leave the center cold.
• Keep the heat at medium-low so the cheese has time to melt before the bread over-browns.
• A pinch of sugar tames canned tomato acidity without making the soup taste sweet.

Variations and Substitutions

• For peak tomato season, swap the canned base for the roasted Fresh Tomato Soup and keep the same sandwich method.
• For the full standalone pot with more depth, make the pantry Tomato Soup and pair it with this grilled cheese.
• Add a thin layer of pesto inside the sandwich for a basil-forward twist that echoes the soup.
• Use sourdough or rye for a tangier bread that stands up to the rich tomato base, or blend cheddar with provolone for a milder melt.

How to Store and Reheat

• Refrigerate leftover soup and sandwiches separately for up to 3 days; store the soup in a sealed container and reheat on the stove.
• Re-crisp grilled cheese in a dry skillet over medium-low heat for 2 minutes per side, or in a 350F (175C) oven for 8 minutes.

Tomato Soup and Grilled Cheese (The Perfect Pairing) FAQ