Roasted Tomato Soup & Grilled Cheese
I spent years making tomato soup the sad way — canned tomatoes straight into a pot, simmer, shrug. Then one night I roasted the tomatoes first because the oven was already on, and I genuinely haven’t gone back since. This is that soup: sweet, smoky at the edges, and thick enough to hold a grilled cheese corner without falling apart.
The whole trick happens on one sheet pan. Tomatoes, a quartered onion, and a fistful of garlic cloves get 35 minutes at high heat until they’re blistered and jammy. Blend that with stock and a splash of cream and you’ve done 90% of the work without stirring anything. The grilled cheese cheat: mayo on the outside of the bread, not butter. It browns more evenly and crisps harder. Trust me, then thank me.
Why you’ll love this one
A few ingredient notes
Roma tomatoes are the move here — meaty, cheap, and they roast down beautifully, though any ripe tomato works in summer. Don’t skip the teaspoon of sugar; it rounds out the acidity. For the sandwich, sharp cheddar brings flavor and a little low-moisture mozzarella brings the pull — all cheddar works fine if that’s what you’ve got.
Roasted Tomato Soup & Grilled Cheese
Ingredients
Instructions
Heat the oven to 425°F. Pile the tomatoes (cut side up), onion quarters, and garlic on a sheet pan, coat with the olive oil, and season with salt and pepper. Roast 35 minutes, until the tomatoes are collapsed and charring at the edges.
Scrape everything on that pan — juices included — into a blender with the stock. Blend until completely smooth, working in batches if needed and venting the lid so hot soup doesn’t redecorate your kitchen.
Pour the soup into a pot over medium-low heat. Stir in the cream and sugar, then taste and season. Tear in the basil and keep it at a bare simmer while you build sandwiches.
Spread mayo on the outside of each bread slice — edge to edge. Pile the cheddar and mozzarella between the un-mayo’d sides.
Cook the sandwiches in a skillet over medium-low heat, about 4 minutes per side, pressing gently. Low and slow is the whole game: the cheese melts fully right as the bread goes deep golden.
Slice each sandwich on the diagonal (mandatory), ladle the soup into bowls, and start dunking.
The one mistake: cranking the sandwich heat — you’ll get burnt bread hugging cold cheese, so stay at medium-low. Soup keeps 4 days in the fridge and freezes beautifully for 3 months; make the sandwiches fresh, always.
Dan started Otoko Cooking in 2019 to prove weeknight food could taste like weekend food. Every recipe is tested at least twice — usually because he ate the first batch. More about Dan →
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