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    Home » Comfort

    Philly Cheesesteak Quesadillas

    Published: Jul 21, 2017 · Modified: Jul 7, 2021 by Philip + Mystique · This post may contain affiliate links

    Jump to Recipe Print Recipe

    Philly Cheesesteak Quesadillas with drunken mushrooms, peppers and onions, fresh beef, and melty wine soaked cheese is the ultimate blend of quesadilla meets cheesesteak 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 Cheesesteak 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 Cheesesteak 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 cheesesteak 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 ¼ 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 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.

    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

    Tipsy Philly Cheesesteak Quesadillas

    Chef Sous Chef
    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.
    5 from 1 vote
    Print Recipe Pin Recipe
    Prep Time 15 mins
    Cook Time 30 mins
    Course Food + Drink, Main
    Cuisine north american
    Servings 8 servings

    Ingredients
      

    • 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

    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 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.

    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.
    Keyword gourmet quesadilla, philly cheesesteak recipes, quesadilla recipes
    Have you tried this recipe?Tag us on Instagram @chef.souschef or use the hashtag #chefsouschef and let us know how it was!
    Philly Cheesesteak Quesadillas on a plate with guacamole and text overlay

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    Reader Interactions

    Comments

    1. Amanda says

      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 says

        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
    2. Isabelle @ Crumb says

      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 says

        July 23, 2017 at 9:11 am

        Thanks so much Isabelle!

        Reply
    3. Kacey @ The Cookie Writer says

      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 says

        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
    4. Janet says

      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.5 stars

      Reply

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