Philly Cheesesteak Grilled Cheese (Printable)

Steak and provolone with sautéed peppers and onions grilled between buttery bread. A hearty fusion sandwich ready in 35 minutes.

# What You 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

# Directions:

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, a generous portion of steak and veggie mixture, another slice of provolone, and then the 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 Hints:

01 -
  • It takes two comfort food legends and smashes them into one glorious, drippy sandwich you can hold with both hands.
  • The steak cooks fast, the cheese melts slow, and the peppers add just enough sweetness to keep you reaching for another bite.
  • You get crispy edges, gooey insides, and that satisfying heft of a sandwich that actually fills you up.
  • It uses one skillet for the filling and one for grilling, so cleanup is faster than you think.
02 -
  • If your steak slices are too thick, they wont cook through before the bread burns, ask your butcher to slice them thin or freeze the steak for twenty minutes and slice it yourself with a sharp knife.
  • Dont skip the resting step after grilling, cutting too soon turns the sandwich into a cheese waterfall and you lose half the filling on the plate.
  • Medium heat is your friend here, high heat will char the bread before the cheese melts and youll end up with a crunchy shell and cold middle.
03 -
  • Press the sandwich gently with your spatula while it grills, this helps the cheese melt faster and glues the layers together so nothing slides out when you bite.
  • Use a cast iron skillet if you have one, it holds heat evenly and gives you the crispiest, most evenly browned crust without hot spots.
  • If youre making multiple sandwiches, keep the finished ones warm in a low oven while you grill the rest so everyone eats at the same time.
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