Cookies ‘n Cream Cupcakes

My older son, Jack, is five today! It’s bittersweet — on one hand, I’m so proud of the big boy he’s become and amazed by how much he’s grown in the last five years (and, let’s be honest, I’m also glad that he’s more physically independent now; sippy cups, Pull-Ups, and huge messes at every meal are ancient history at this point). On the other hand, I just want to stop time because I can’t believe that the tiny newborn I held in my arms five years ago today is now bouncing around the house, excitedly shouting out everything he wants to do today. In the fall, he goes to kindergarten, and I know it won’t be long until hanging out with me, Johnny and Derek isn’t his only idea of an awesome time. ::sniff:: Good thing I have Derek to hang on to for a little longer!

But, enough of the mushy stuff. Jack requested an Oreo cake for his special day (like father, like son!), but since I just made one last month, I made him cookies ‘n cream ice cream cupcakes instead. These were so easy and took very little time.

Essentially, I hollowed out chocolate cupcakes, filled them with cookies ‘n cream ice cream, then topped them with homemade Oreo cream cheese frosting (which is really just the filling from this cake). These can be stored in the freezer until you’re ready to serve them. Jack saw me make them and is counting down the hours to dinnertime. I’ve already had one and can say that they’re absolutely delicious!

Cookies ‘n Cream Cupcakes

Makes 24  cupcakes


  • 24 chocolate cupcakes, either store-bought or baked and then cooled
  • 8-oz block of cream cheese (reduced fat is OK), at room temperature
  • 1/2 cup sugar
  • 2 cups Cool Whip, thawed
  • 2 cups of crushed Oreos (if you buy a bag of mini Oreos, then crush them with a rolling pin or wine bottle, you’ll have the perfect amount)
  • Cookies ‘n cream ice cream


Before you begin, put the cupcakes in the freezer for an hour or so. They’re easier to work with when slightly frozen.

When you’re ready to assemble the cupcakes, set the ice cream on the counter so it can soften slightly. Meanwhile, beat the cream cheese and sugar until light and airy.

With a spatula, gently fold in the thawed Cool Whip into the cream cheese mixture. When well-mixed, fold in the crushed Oreos. Set the bowl of frosting aside.

Remove the cupcakes from the freezer, a few at a time. With a serrated knife, hollow out the cupcake.

Take the cupcake interior that you removed, then slice off the very top. This will go back on top of the cupcake after you fill it with ice cream.

Fill the hollowed-out cupcake with ice cream, then gently place the cupcake top above the ice cream.

Slather the whole thing with a generous amount of Oreo cream cheese frosting. Repeat until you’ve assembled all the cupcakes, then place the cupcakes back into the freezer in a covered container until a few minutes before you’re ready to serve them.

Enjoy! And happy birthday, Jack!


About Saucy Mommy

I'm Beverly, a mom of two who loves to cook and write. Check out my blog at for family-friendly (but tasty) meal ideas and pictures of bento box lunches.


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