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5 from 1 vote

Tipsy Philly Cheesesteak Quesadillas

In addition to wine soaked onions, mushrooms and green bell peppers, what makes this quesadilla ultra ooey is the wine soaked cheese. Its edible rind soaked in Palatine Hills Cabernet Merlot, slices of grilled sirloin steak and drunk veggies is what makes these the ultimate dinner dish.
Prep Time15 mins
Cook Time30 mins
Course: Food + Drink, Main
Cuisine: north american
Keyword: gourmet quesadilla, philly cheesesteak recipes, quesadilla recipes
Servings: 8 servings
Author: Chef Sous Chef


  • 200 g wine soaked cheese grated
  • 454 g ribeye or sirloin steak
  • 200 g cremini mushrooms sliced
  • 1 green pepper thinly sliced
  • 1 red pepper thinly sliced
  • 1 red onion thinly sliced
  • 1 tablespoon chili powder
  • 1 tablespoon cumin
  • 1 tablespoon smoked paprika
  • ½ teaspoon cayenne pepper
  • ½ teaspoon salt
  • ½ cup red wine
  • 3 tablespoon olive oil
  • 8 large tortillas
  • ½ cup sour cream or yogurt
  • ½ cup guacamole


  • No. 1 | Pat the beef dry and place in the freezer while you prepare the vegetables. Slice mushrooms, peppers, and onions and place in separate bowls.
  • No. 2 | Preheat a cast iron skillet to medium-high heat with 1 tablespoon of olive oil. Remove the steak from the freezer and slice as thin as possible against the grain. Liberally season the beef with salt and pepper, and place in the skillet one at a time, ensuring to leave space around each piece. Cook until browned, about 1 minute per side, and transfer to a bowl or plate.
  • No. 4 | Return the pan to heat and pour in 1 tablespoon olive oil. In a small bowl, mix together the chili powder, cumin, paprika, cayenne pepper, salt and half the red wine. Pour into the skillet and cook for 30 seconds stirring constantly. Add the mushrooms and cook for 2 minutes, until they start to sweat. Next add the peppers and onions and cook for 3-4 minutes, stirring often. Add the remainder of the red wine and any juices from the resting steak. Cook until the wine is evaporated. Remove from heat and place in a bowl. Wipe the pan with a paper towel.
  • No. 5 | To assemble the quesadillas, spread about 3-4 tablespoon of cheese on half of the tortilla, top with some of the vegetable mixture and a few slices of the steak, then cover with additional cheese. Repeat for each of the quesadillas.
  • No. 6 | Reheat the same skillet you used to cook the vegetables on medium high heat. Add a tablespoon of olive oil and cook 1-2 quesadillas for about 2 minutes or until golden brown. Flip and cook for an additional 2 minutes. Repeat with each quesadilla.
  • No. 7 | Cut the quesadillas into thirds and serve with sour cream and guacamole.


Tip: Topping the quesadillas only on one side then folding it over results in a cleaner flip on the frying pan. Plus, when cut into thirds, it ensures 2 of the 3 pieces have that clean folded over crust perfect for dipping in sour cream or guac.