Philly Cheese Steak Quesadillas

Last modified on May 25th, 2019 at 11:30 am

Philly Cheese Steak Quesadillas with drunken mushrooms, peppers and onions, fresh beef, and melty wine soaked cheese is the ultimate blend of quesadilla meets cheese steak and pulls the highest compliments from each into a melted dish. 

Close up of Philly Cheese Steak Quesadillas Sliced on a Cutting Board

Being the Sous Chef in our house doesn’t mean what it means in a restaurant setting. Here at home, I’m the Chef’s assistant. I stir, I plate, I taste test and outside the kitchen I style and shoot. Unlike the traditional Sous Chef, it’s not often that I step in for the Chef and command the kitchen.

The only time that actually happens is when I slice open a few limes, mix the guac and grab the spatula. Moments like this only mean one thing: it’s time for quesadillas, and today we’re sharing the recipe for our Tipsy Philly Cheese Steak Quesadillas courtesy of me, the Sous Chef.

Various Images of Sliced Red Onions, Sliced Mushrooms, and Grated Cheese


In addition to wine soaked onions, mushrooms and green bell peppers, what makes this quesadilla ultra ooey is the Gunn’s Hill Tipsy 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. But what makes my Philly Cheese Steak Quesadillas different from the rest is all in the assembly and a heavy hand on the skillet.

A crisp ouster layer tortilla with ooey gooey strings of melty Tipsy Cheese, this dish is the ultimate blend of quesadilla meets cheese steak and pulls the highest compliments from each into melted Philly Cheese Steak Quesadillas.

Bon appetit xo

Chef Sous Chef

How to Make Philly Cheesesteak Quesadillas

Ingredients for Philly Cheesesteak Quesadillas

Ribeye or sirloin steak, wine soaked cheese, cremini mushrooms, bell peppers, red onion, chili powder, cumin, smoked paprika, cayenne pepper, red wine, tortillas, salt and pepper. Use sour cream and guacamole for serving.

Prepare the Beef

A traditional Philly Cheesesteak features thinly sliced beef cooked to perfection. To make it easier to slice the beef, pat dry and place in the freezer for 10-15 minutes to slightly firm up. Very thinly slice the beef against the grain and place on a plate. Season liberally with salt and pepper and cook in a cast iron skillet until browned on both sides. Transfer to a bowl until ready to assemble.

Sauté the Vegetables

A key to developing deep flavour for our quesadillas is cooking the spices before sautéing the vegetables. Make a spice paste by mixing the chili powder, cayenne, paprika, and a pinch of salt with 1/4 cup of red wine. Heat the skillet on medium-high with olive oil. Once smoking, pour in the spices and cook for 30 seconds. Add the mushrooms and sauté for a few minutes, then finally add the onions and peppers. Once the veggies have cooked through, add remaining wine, juices from the beef and allow to reduce until absorbed. Transfer to bowl for assembly.

How to Assemble a Quesadilla

To assemble the quesadillas, spread about 3-4 tbsp 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.

Quesadilla Frying in a Blue Cast Iron Skillet

How to Cook a Quesadilla to Perfection

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.

Mystique's Hands Cutting the Quesadillas with a Chef's Knife
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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.

  • Author: Chef Sous Chef
  • Prep Time: 15 minutes
  • Cook Time: 30 minutes
  • Total Time: 45 minutes
  • Yield: 8 servings 1x
  • Category: Food + Drink, Main
  • Method: Stovetop
  • Cuisine: North American
Scale

Ingredients

  • 200g wine soaked cheese, grated
  • 454g ribeye or sirloin steak
  • 200g cremini mushrooms, sliced
  • 1 green pepper thinly sliced
  • 1 red pepper, thinly sliced
  • 1 red onion, thinly sliced
  • 1 tbsp chili powder
  • 1 tbsp cumin
  • 1 tbsp smoked paprika
  • 1/2 tsp cayenne pepper
  • 1/2 tsp salt
  • 1/2 cup red wine
  • 3 tbsp olive oil
  • 8 large tortillas
  • 1/2 cup sour cream or yogurt
  • 1/2 cup guacamole

Instructions

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 tbsp 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 tbsp 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.

Notes

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.

Keywords: quesadilla recipes, gourmet quesadilla, philly cheesesteak recipes

Philly Cheese Steak Quesadilla Image with Title

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7 Comments

  • Reply
    Amanda
    July 21, 2017 at 6:27 pm

    Delish! I love how it’s loaded with veggies and ooey gooey, melty cheese. Your spice mixture sounds like the perfect compliment to the Tipsy cheese! Cheers!

    • Reply
      chefsouschef
      July 22, 2017 at 11:07 am

      Thanks Amanda! All the ingredients worked so well together. The Tipsy cheese was the perfect for quesadillas!

  • Reply
    Isabelle @ Crumb
    July 22, 2017 at 9:15 pm

    What a great way of showing off that beautiful Tipsy cheese. I love the way you’ve added another layer of flavour with the drunken veggies… this is definitely my kind of quesadilla!

    • Reply
      chefsouschef
      July 23, 2017 at 9:11 am

      Thanks so much Isabelle!

  • Reply
    Kacey @ The Cookie Writer
    July 25, 2017 at 10:48 am

    I can see many family members fighting over this one! You guys really know how to show off the star of the show (Tipsy was awesome!!)

    • Reply
      chefsouschef
      July 25, 2017 at 12:31 pm

      LOL! We fight over it too Kacey. The Tipsy was definitely a perfect fit for this recipe.

  • Reply
    Janet
    November 20, 2017 at 11:30 pm

    I love the use of red wine in the onions and peppers. It makes this a more grown up version of quesadillas! Awesome.

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