The classic American pairing of grilled cheese and tomato soup – what could be more simple and comforting?!  For the soup, I’ve adapted chef Barbara Lynch’s tomato soup recipe from her cookbook Stir. It’s intensely tomatoey with a spicy kick.  For the grilled cheese I went for high flavor, using grated sharp cheddar, grated onion, dijon mustard and a bit of mayo for texture.


The soup is super easy, especially if you can puree it right in the pot with an immersion blender.


Open-faced grilled cheese sandwiches are my preference because I like a higher cheese-to-bread ratio without upping the amount of cheese. For similar reasons I prefer thin crust pizza to thick and I usually hollow out my bagel before toasting it and topping it.  It’s not that I’m so calorie-conscious but more that I don’t like to dilute the delicious flavors of sandwich and pizza toppings with too much dough or bread.


The other benefit of the open-faced grilled cheese is that you don’t have to stand over a frying pan and you can cook six sandwiches at once in just a few minutes in a pre-heated oven.


My inspiration for this tasty version of grilled cheese comes from a vintage recipe my mother used to make when she entertained.  She called it “cheese grille.”  It was a sinfully scrumtious appetizer consisting of equal parts grated parmesan, grated onion, and mayonnaise, mixed together and mounded onto small triangles of white bread, and broiled.



Don’t worry!  I’ve lightened it up quite a bit.  And it’s still sublime – especially when paired with spicy tomato soup.



Recipe type: lunch or dinner
Cuisine: American
Prep time:
Cook time:
Total time:
Serves: 6
The ultimate comfort food pairing - grilled cheese with tomato soup. Here's an extra special version.
  • Tomato Soup
  • 2 tablespoons olive oil
  • 1 teaspoon crushed red pepper flakes
  • 1 cup chopped yellow onion (1 medium onion)
  • 2 28-ounce cans Italian plum tomatoes (San Marzano or Muir Glen Organic is best)
  • 1½ cups water
  • ½ teaspoon salt
  • fresh ground pepper, to taste
  • Garnish
  • 18-24 fresh basil leaves, slivered
  • Plain yogurt, sour cream, or creme fraiche
  • Grilled Cheese
  • 6 slices of sour dough bread cut in half (or your favorite sandwich bread)
  • 6 ounces grated extra sharp cheddar cheese (I used Cracker Barrel Extra Sharp)
  • ¾ cup very finely chopped or grated yellow onion (you can use a food processor)
  • 2 tablespoons mayonnaise (I recommend Hellman's)
  • 1 tablespoon dijon mustard (I recommend Grey Poupon)
  1. Preheat oven to broil. For soup, in a large pot or Dutch oven, heat oil over medium heat. Add chopped onion and red pepper flakes. Sauté for 8-10 minutes until onion is softened and just starting to brown. Add tomatoes and their juice, water and salt. Bring to a boil. Reduce heat to a simmer and cook for 30 minutes.
  2. Meanwhile for the grilled cheese put bread onto a jellyroll or sheet pan. Toast lightly in the hot oven with the door slightly ajar for 2-3 minutes, watching carefully to avoid burning. Remove pan and set aside to cool. (Keep the oven on)
  3. In a medium sized bowl, stir grated cheese, onion, mayonnaise and mustard to combine. Flip bread over so the toasted side is facing down. Divide the cheese mixture evenly onto the bread, using a fork to press it down and spread it out to the edges. Set aside.
  4. Allow soup to cool for 5 minutes. Puree to your desired consistency using an immersion blender, blender or food processor. Season with salt and pepper, to taste.
  5. Right before serving, broil the sandwiches in the center of the preheated oven for 3 minutes. Continue cooking for 1-2 minutes longer with oven door slightly open, watching the sandwiches as they start to get brown and bubbly. When you see brown spots covering about ⅓ of each sandwich, remove them from the oven and tent with foil while you divide the soup among 6 bowls. Top soup with a dollop of yogurt or sour cream and some slivered basil. Serve with sandwiches alongside. Enjoy!
  6. Note: Both the soup and the cheese mixture can be made up to 2 days ahead, each stored in an airtight container in the fridge.

Related products that are available in my Amazon Store:  cheese grater, immersion blender, food processor

Disclaimer:  On occasion I provide links in my posts to cookbooks or other products, available for purchase on Amazon. If you purchase a product through these links, I receive a small commission with no extra cost to you.


  1. Hill says

    For guys who may be a little cooking-challenged like me, this is a good one to make you a hero in this cold weather. Enjoy.

  2. says

    Hi, Lisa! It is my first time here. Thanks a lot for visiting me.
    What a perfect meal to enjoy on these cold winter days…I am a fan of both tomato soup and grilled cheese. I am looking forward to try your recipe with the red pepper flakes. I love some heat! wishing you an awesome weekend!

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