Oreo-Stuffed Double Chocolate Cookie Cups

Prep Time 40 minutes
Total Time 55 minutes
Servings 24 cookie cups

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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 cookie cups stacked with top cookies cut in half to reveal oreo inside

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 chocolate cookie cups in bowl with some whole and some halved to reveal oreo inside

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 šŸ˜‰

frosted oreo cookie cups on marble with piece of oreo cookie on top

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.

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Oreo-Stuffed Double Chocolate Cookie Cups

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!
Prep Time 40 minutes
Cook Time 15 minutes
Total Time 55 minutes
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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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!

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Reader Interactions


  1. Isadora @ she likes food says

    Hahaha! I think I need a pair of maternity pants and not because I’m expecting a baby! For some reason I don’t really like oreos by themselves but cookies and cream is one of my favorite ice creams and I want to eat all of these cookie cups!

  2. Tina @ Tina's Chic Corner says

    First, you had me at the title (before even seeing the gorgeous pics). Second, I’m cracking up over your first line.
    I’m guessing that I won’t be able to stop at just having one of these! Yummers.

  3. Kristine @ Kristine's Kitchen says

    I am living in my maternity leggings and loving it. I was just telling my husband yesterday, that I need to buy a pair of non-maternity leggings because they are just too comfortable and I want to be able to wear them even once the maternity pants are no longer acceptable to wear. šŸ™‚ I’m also enjoying the excuse to eat whatever I want right now – and these Oreo cookie cups look like the perfect way to satisfy my chocolate cravings! Pinned!

    • Ashley says

      Lol, I JUST started working out today. I LOVE leggings, and I actually bought a bunch more leggings and yoga pants knowing that I was going to be on maternity leave. That being said, occasionally I need to leave the house so I try not to eat all the chocolate I want… šŸ™‚

  4. marcie says

    There’s only one packaged cookie that I love, and that’s Oreos — there’s just nothing like them. I love cookies & cream themed desserts, and these cookie cups look amazing, Ashley! And I do my best over the top stuff when I know I’m taking the bulk of it elsewhere because yeah…the pants won’t fit if I keep them. haha Your co-workers must have loved these!

    • Ashley says

      It works perfectly! That way there’s no temptation, otherwise I would definitely eat them all! Lol. Luckily now that I’m at home the hubs is working in town and I can just send the leftovers with him back to HIS coworkers. Lol

  5. Nora @ Savory Nothings says

    My baby girl is five months now and I’m still in maternity pants. Not because my normal pants don’t fit but this stretchy band is just so amazingly comfortable and I can move in every direction without anything pinching me! Slightly embarrassing but oh well šŸ™‚
    I should definitely not be all over these wonders of oreo and chocolate you produced here – or else maternity pants will definitely be my only option in the pants department!

    • Ashley says

      I think it’ll be a little while longer before the pants fit, but I DID start working out today, so it’s a step. Lol. And then I made 2 batches of cookies, because, you know, this food blog thing. šŸ™‚

  6. Jocelyn (Grandbaby cakes) says

    I’m too in love with these. I think I would eat that entire plate. The oreo inside is fantastic!

5 from 3 votes (1 rating without comment)

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