Oreo Stuffed Mint Chocolate Chip Cookie Cups

A few weeks ago I made this scrumptious dessert bar made of chocolate chip cookie dough and Oreos soaked in condensed milk overnight and then backed to a gooey perfection. It was about the best dessert I had ever made save for the Gooey Payday Scotcheroo bars I made last week.

There’s this store near-ish to my house that sells chocolate chip cookies stuffed with Oreos. If you like that sort of thing, you can top the cookie with ice cream and chocolate syrup and even some whipped cream. My sister made the comment the other day that the time she tried the cookie she wasn’t overly fond of it because the Oreo was crunchy in the middle of the cookie. And it got me to thinking about the bars I made a few weeks ago and the possibility of turning the bars into a fantastic cookie by soaking the Oreo in condensed milk before baking.

So I set out to perfect the recipe confident I could do it on the first try.


I had every intention of making an Oreo stuffed cookie, not cookie cups. However, the cookies ended up being a flop because they spread out too much. I blame this on the butter. Everyone knows that butter cookies spread out into a thin cookie, right? I mean I know this. It’s basic. Yet I didn’t adjust my recipe in order to yield a thicker cookie by adding more flour. I have no idea what I was thinking, but I watched the first batch of cookies spread into the oven until they turned into gigantic cookies the size of a large pancake with an Oreo “nose” sticking out the approximate middle of the pancake-cookie.

So after the first batch I switched gears and turned these into cookie cups by placing them in extra-large muffin tins. These cookie cups are perfect for cupping a scoop of ice cream and, in that regard, I got a winner.


  • 1 ½ c. butter, softened
  • ½ c. shortening
  • 1 c. sugar
  • 2 c. packed brown sugar
  • 2 eggs, room temperature
  • 1 tsp. salt
  • 2 tsp. baking soda
  • 3 ¾ c. all-purpose flour
  • 1 package mint chocolate chips, plus more for garnish


  1. Cream butters and sugars in the bowl of a stand mixer (if you have one; a hand mixer works just fine as well) on medium high speed until light and fluffy. Add eggs and vanilla and mix until combined on low or medium-low speed. Add dry ingredients and stir until thoroughly combined. Add chips; stir to combine.
  2. Form dough into small hockey pucks that fit into the palm of your hand and place on a parchment paper lined baking sheet.
  3. Spoon a small amount of condensed milk on half of the pucks. Place an Oreo on top of each dot of condensed milk and then spoon an additional amount of condensed milk on top. Cover with another dough puck and seal the edges to form a sealed sandwich so that the condensed milk does not leak out. Repeat until all the dough is used.
  4. Store, covered, overnight in the refrigerator.
  5. The next day, preheat the oven to 375 degrees. Place one cookie sandwich in each cup of an extra large muffin tin and dot with chocolate chips.
  6. Bake for 20 to 22 minutes or until the edges are golden brown. The dough may be a bit undercooked but that’s OK. That’s what makes the cup form. Let cool completely within the muffin tins (if you have enough muffin tins and can do so) and then gently remove using a butter knife to dislodge if necessary.
  7. Top with ice cream or any other filling that you think would go great inside of a cup.

These cookie cups go perfect with Ben and Jerry’s Mint Oreo ice cream. Incidentally, the ice cream is what inspired me to make this cookie turned dessert.

Recipe rating: 


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