Sliced grilled cheese with stringy cheese pulls, next to 3 unsliced sandwiches, sliced tomatoes, and pesto

Grilled Cheese Sandwich with 5 Cheeses, Pesto & Tomato

  • Author: Nicole Cutchall
  • Prep Time: 10 minutes
  • Cook Time: 13 minutes
  • Total Time: 23 minutes
  • Yield: 4 sandwiches 1x


Gooey 5 cheese grilled cheese sandwich slathered with pesto, and sliced tomato.



  • 1 cup grated Dubliner cheese or cheddar cheese
  • 1 cup grated monterey jack cheese
  • ¾ cup grated asiago cheese
  • ⅓ cup feta cheese
  • 4 slices provolone cheese
  • 4 tbsp pesto
  • 2 Roma tomatoes, sliced ¼ inch thick
  • 4 tbsp mayo
  • 1½ tbsp butter, softened
  • 8 ¾ inch thick slices of sourdough bread


  1. Preheat a large saute pan or flat griddle on low heat.
  2. Combine all cheese, except provolone in a medium bowl. Mix to combine.
  3. On one side of each slice of bread, spread ½ tbsp of pesto.
  4. On the other side of each slice of bread, spread ½ tbsp of mayo. *See note*
  5. Melt the butter in the pan or griddle, making sure to spread it evenly.
  6. Add 4 slices of bread to the pan or griddle, mayo side down.
  7. On top of each slice of bread, layer on one slice of provolone, ⅛ of the cheese mixture, 2-3 slices of tomato, and another ⅛ of the cheese mixture.
  8. Take the remaining 4 slices of bread, and put them on top of the 4 slices in the pan or griddle with the mayo side facing up.
  9. Press lightly or place a heavy bottom pan on top of the sandwiches. *See note*
  10. Turn the heat up to medium, and cook for 5-7 minutes.
  11. When the bottom of the grilled cheese is golden brown, flip it over.
  12. Cook for an additional 4-6 minutes. Serve when golden brown.


  • Once you have both sides slathered, I recommend standing the bread on its side. If you bread is thick enough, it should stand upright.
  • Putting a heavy bottomed pan on top of the sandwiches helps to press them down. Be careful not to press too hard, otherwise the filling with come out.
  • Category: Dinner, Lunch
  • Cuisine: American

Keywords: grilled cheese, dubliner cheese, cheddar cheese, feta, provolone, asiago, monterey jack, 5 cheese, gooey, pesto, mayo, roma tomatoes, sandwich