Oreo-Stuffed Double Chocolate Cookie Cups - The Recipe Rebel (2024)

The Recipe Rebel / Desserts

written by Ashley Fehr

5 from 3 votes

Prep Time 40 minutes mins

Total Time 55 minutes mins

Servings 24 cookie cups

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Last updated on June 9, 2020

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These Oreo-Stuffed Double Chocolate Cookie Cups are crisp on the edges, chewy in the middle and absolutely LOADED with chocolate! Frosted or unfrosted — you decide!

Oreo-Stuffed Double Chocolate Cookie Cups - The Recipe Rebel (2)

This recipe is brought to you by my maternity pants.

Because they are way too stretchy and enable me to create and eat things like this.

In all fairness, I made these to bring to my coworkers at the high school when I went to bring the baby for a visit. So I guess, knowing that I wouldn’t actually be left to eat these by myself, I went a little overboard.

I was trying to think of something to bake to bring to the school, because I have a bit of a reputation.

Now, I’m not saying that I am some sort of baking queen and everything I make is amazing, but I’ve experimented on them quite a bit in the past so they’ve gotten a little used to me bringing goodies.

It’d be a little awkward to go empty-handed.

And plus, I’ll never get out of these darn maternity pants if I don’t share.

Oreo-Stuffed Double Chocolate Cookie Cups - The Recipe Rebel (3)

So I started scanning my Bars, Square and Cookies board on Pinterest, thinking maybe I would try another blogger’s recipe or make something that was already on the blog so that I could just relax and bake, and not worry about the photography and all that jazz.

And I saw some oreo-stuffed chocolate chip cookies, and I thought, “I should make those.”

And then I thought, “more chocolate.”

So obviously, I made some double chocolate cookies and stuffed them with an Oreo. And then I remembered this Oreo filling frosting and thought I had better make some to smother on top. And top that with crushed Oreos.

I know not everyone is into frosting (and to be honest, the older I get, the less I enjoy the overly sweet!), so that part is up to you 😉

Oreo-Stuffed Double Chocolate Cookie Cups - The Recipe Rebel (4)

And, to be honest, they don’t need any frosting. And if you’re someone who doesn’t like things overly sweet, unfrosted is the way to go. But if you’re looking to get a little crazy…. go all out.

Oreo-Stuffed Double Chocolate Cookie Cups - The Recipe Rebel (5)

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Oreo-Stuffed Double Chocolate Cookie Cups

written by Ashley Fehr

5 from 3 votes

These Oreo-Stuffed Double Chocolate Cookie Cups are crisp on the edges, chewy in the middle and absolutely LOADED with chocolate! Frosted or unfrosted — you decide!

Oreo-Stuffed Double Chocolate Cookie Cups - The Recipe Rebel (7)




Prep Time 40 minutes mins

Cook Time 15 minutes mins

Total Time 55 minutes mins

Cuisine American

Course Dessert

Servings 24 cookie cups

Calories 348cal



  • 1 cups butter
  • 2 cups sugar
  • 1 tsp vanilla
  • 2 eggs
  • 2 cups flour I used half whole wheat
  • 1 tsp baking soda
  • 1 tsp salt
  • 2/3 cup cocoa
  • 1 cup mini chocolate chips
  • 24 Oreo cookies


  • 1/2 cup white chocolate chopped
  • 1/4 cup milk
  • 1/2 cup butter
  • 1 tsp vanilla
  • 3 cups powdered icing sugar
  • 3-4 Oreos, crushed



  • Preheat oven to 350 degrees.

  • In the bowl of a stand mixer, beat butter and sugar until light and fluffy. Add vanilla and eggs and beat until smooth.

  • Add flour, baking soda, salt and cocoa and beat until combined. Add chocolate chips and beat on low until combined. If cookie dough is still a bit sticky, refrigerate for 1 hour.

  • Prepare 24 muffin cups: use a regular muffin pan, well-greased or use silicone muffin cups ungreased (a dark pan will result in crispier edges, a silicone pan will result in softer edges)

  • Drop a rounded teaspoon of cookie dough in each muffin cup. Press down with your fingers and work dough up the edges just slightly. Place one Oreo in the middle, pressing down gently. Scoop another rounded teaspoon of dough and flatten it into a circle the size of the muffin cup. Place on top of each Oreo and press down the sides gently to surround the Oreo.

  • Bake for 12-14 minutes until centers appear set. Set aside to cool.

Frosting (optional)

  • In a small bowl, melt white chocolate and milk in the microwave in 30 second intervals, stirring in between. Set aside to cool slightly (15-20 minutes)

  • With an electric mixer, beat butter until smooth. Add cooled chocolate mixture and vanilla and beat until combined.

  • Add powdered sugar, one cup at a time, beating until combined after each addition. Beat on high 2-3 minutes until light and fluffy.

  • Frost cooled cookie cups and garnish as desired.

Nutrition Information

Calories: 348cal | Carbohydrates: 50g | Protein: 3g | Fat: 15g | Saturated Fat: 9g | Cholesterol: 42mg | Sodium: 276mg | Potassium: 88mg | Fiber: 1g | Sugar: 37g | Vitamin A: 355IU | Vitamin C: 0.1mg | Calcium: 27mg | Iron: 2mg

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Oreo-Stuffed Double Chocolate Cookie Cups - The Recipe Rebel (8)

Meet Ashley

My name is Ashley Fehr and I love creating easy meals my family loves. I also like to do things my way, which means improvising and breaking the rules when necessary. Here you will find creative twists on old favorites and some of my favorite family recipes, passed down from generations!

Read More

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Reader Interactions


  1. Joseph says

    Hi Ashley, I’m making these a head of time, tonight For an event tomorrow. Should I refrigerate or freeze these overnight?

    Love this recipe and I cannot wait to make it


    • Ashley Fehr says

      Thanks! No need to refrigerate or freeze unless they are frosted, they should be great!


  2. Susan says


    These look very delicious! Plan on making these in the next couple of months.

    I do have a question. What type of flour should be used? All Purpose? It would be nice, if recipes had the type of flour that the recipes require, along with the Brands which people used to make them.

    My son had just gotten his own place & he likes Oreo’s. I’m going to send him the link to your website & recipe.

    Thanks for the Chocolate Recipes!


    • Ashley Fehr says

      Hi Susan! You’re right, that would be helpful! Unless otherwise stated, I always use all-purpose flour. I hope he enjoys them!


  3. Mary says

    I’m not sure if I hit send so I am asking Again! Can you freeze this Oreo cookie cup
    and if so how do they hold up?


    • Ashley Fehr says

      Yes they hold up perfectly in the freezer!


  4. Rachel Conners says

    These cookie cups look amazing! I love anything with Oreos…too good, and I would totally devour too many of them. Pinned!


    • Ashley says

      Thanks Rachel! LOVE Oreos too!


  5. Jess @ Flying on Jess Fuel says

    These look so awesome!! I love that you added MORE CHOCOLATE! LOL, you can never have too much chocolate! Perfect little bite sized treats!


    • Ashley says

      Lol. That’s what I thought! Thanks Jess 🙂


  6. Stacey @ Bake.Eat.Repeat. says

    Wow! Just, wow. Those look like the perfect cookie. More chocolate was the right call! Let’s be honest, more chocolate is always the right call! Love these! Pinned!


    • Ashley says

      Haha, glad we’re on the same page Stacey!


  7. Kelley says

    These are like little clouds of heaven! They look amazing.. and the frosting..mmm. I need to make these soon!


    • Ashley says

      Thanks Kelley!


  8. Sarah@Whole and Heavenly Oven says

    Oh my gosh, WOW! How awesome do these look? Seriously this is my kinda cookie-cup heaven right here! Love the whole double-cookie/double choc action going on. Perfection. 😀


    • Ashley says

      Haha, thanks Sarah! I’m glad you’re on the same page!


  9. Meg @ The Housewife in Training Files says

    Oh the frosting is totatly needed!


    • Ashley says

      I agree!


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