Philly Cheesesteak Grilled Cheese (Printable Version)

A fusion sandwich featuring juicy steak, sautéed peppers, and melty provolone between golden buttery bread.

# What You’ll Need:

→ Filling

01 - 10 oz ribeye steak, thinly sliced
02 - 1 tablespoon olive oil
03 - 1 small green bell pepper, thinly sliced
04 - 1 small red bell pepper, thinly sliced
05 - 1 medium yellow onion, thinly sliced
06 - 1/2 teaspoon kosher salt
07 - 1/4 teaspoon black pepper

→ Sandwich Assembly

08 - 8 slices sturdy white or sourdough bread
09 - 8 slices provolone cheese
10 - 4 tablespoons unsalted butter, softened

# Step-by-Step Guide:

01 - Heat olive oil in a large skillet over medium-high heat. Add sliced steak, season with salt and pepper, and cook for 2-3 minutes until browned. Remove steak and set aside.
02 - In the same skillet, add bell peppers and onion. Sauté for 4-5 minutes until softened and lightly caramelized. Return steak to the pan, toss to combine, and remove from heat.
03 - Butter one side of each bread slice. Place 4 slices buttered side down on a work surface. Top each with 1 slice of provolone, generous portion of steak and veggie mixture, another slice of provolone, and remaining bread slices buttered side up.
04 - Heat a large non-stick skillet or griddle over medium heat. Place sandwiches in the skillet in batches if necessary. Grill for 3-4 minutes per side, pressing gently, until bread is golden and cheese is melted.
05 - Transfer to a cutting board, let cool for 1 minute, then cut in half and serve immediately.

# Expert Tips:

01 -
  • It turns two comfort food classics into one ridiculously satisfying sandwich that feels like a warm hug.
  • The crispy, buttery crust gives way to tender steak and sweet, caramelized peppers in every bite.
  • You can have it on the table in about half an hour, making it perfect for nights when you want something special without the fuss.
  • It reheats surprisingly well, so leftovers actually feel like a bonus instead of a compromise.
02 -
  • If your skillet is too hot, the bread will burn before the cheese melts, so keep it at medium heat and be patient.
  • Slicing the steak against the grain makes it tender and easy to bite through, which I learned after chewing my way through a too-chewy version once.
  • Don't skip removing the steak before the vegetables, or it will turn tough and rubbery by the time everything else is done.
03 -
  • Use a heavy skillet or press down gently with a second pan while grilling to help the cheese melt faster and the bread crisp evenly.
  • If you want extra cheesy pull, add a thin layer of shredded mozzarella between the provolone slices.
  • Let your butter come to room temperature so it spreads smoothly without tearing the bread, which makes all the difference in getting an even golden crust.
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