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Tomato Soup and Waffle Iron Grilled Cheese

Tomato soup and grilled cheese is a crave-worthy combination. In this version, the soup gets its richness from olive oil instead of cream and the sandwiches are done panini-style in an old-fashioned waffle iron. The duo is bound to win over kids and grown ups alike. 

Course Main Course, Soup
Prep Time 5 minutes
Cook Time 20 minutes
Total Time 25 minutes
Servings 4 cups of soup and 4 sandwiches
Calories 450 kcal
Author Katie Morford


Tomato Soup

  • 4 tablespoons extra-virgin olive oil, divided
  • 1 large yellow onion, roughly chopped
  • 1 large clove garlic, smashed and peeled
  • 1/2 teaspoon ground fennel
  • 1/2 teaspoon dried oregano
  • Pinch red pepper flakes
  • One 28- ounce can diced unsalted tomatoes
  • 1 to 1 1/2 cups water
  • 1 1/4 teaspoon kosher salt
  • Black pepper
  • One 3/4- inch thick slice crusty French or Italian bread that's about 4 inches long (stale is fine)

Grilled Cheese Sandwich

  • 8 slices whole-grain sandwich bread
  • 6 ounces grated sharp Cheddar cheese (or other favorite cheese)
  • Olive oil for brushing the waffle iron


For the soup

  1. Heat 1 tablespoon of olive oil in a medium pot over medium heat. Add the onion, garlic, fennel, oregano, and red pepper flakes and saute until the onion is tender, about 8 minutes.
  2. Add the tomatoes, 1 cup water, salt, several generous grinds of black pepper. Tear the bread into pieces and add it to the soup.Turn up the heat and bring the soup to a boil. Drop the heat until the soup simmers and cook for 9 minutes.

  3. Use an immersion blender or transfer soup to a conventional blender. Add the remaining olive oil and puree until smooth. Taste and add more red pepper flakes, salt, and/or black pepper if desired. If the soup seems too thick, add  more water and blend again.

For the sandwiches

  1. Preheat a waffle iron. 

  2. While the waffle iron is heating, assemble the sandwiches: Lay 4 slices of bread on your work surface and cover each one with cheese, dividing it evenly. Top the sandwiches with the remaining bread slices. 

  3. Use a pastry brush to lightly coat the inside of the waffle iron with olive oil. Set one sandwich into the waffle iron and bring the top down firmly (it may not close completely). Cook until the bread is browned and the cheese melted. Remove from the waffle iron and repeat with the remaining 3 sandwiches, lightly brushing the waffle iron with olive oil before each one. 

  4. Cut the sandwiches in half and serve with warm cups of soup.