The Oreo Anniversary Series – Crushing Oreos to Bake Inside Out Oreo Stuffed Chocolate Chip Cookies!


Happy Passover and Easter, everyone!  I hope everyone has a little room left in their bellies for my cookie treat because I KNOW you guys will absolutely love and foam at the mouth over this one!  First off, how do you all like to eat your Oreo cookies?  Twisting them?  Dunking them in milk?  Shoving them in your mouth and closing your eyes as you float through cookie heaven?  Or do you prefer to have a dessert within a dessert, with your Oreos in a cupcake or cheesecake or cake?  How about a cookie…within a cookie?!  Introducing my beloved inside out Oreo stuffed chocolate chip cookies!!  *Cue harps and angels singing* 

With all the crazy Oreo birthday madness going around and my constant cookie recipe brainstorming, I thought to myself, “how awesome would it be to have an Oreo stuffed cookie full of crushed Oreos!”  And so the crushed Oreo chocolate chip studded cookie was born.  I used crushed golden Oreos since that’s what I had on hand in my pantry, but think of all the delicious possibilities!  You could crush chocolate fudge ones, chocolate mint ones, and – wait for this – the brand spankin’ new birthday cake Oreos!  I tested this out with the cookie recipe base that I had been using for the last several recipes I posted on Ate by Ate (just substituting and switching around “add-on” ingredients” each time”) and I loved them!  My mum lifts the lid of our cookie box every day just to get a whiff of them and my dad said that after eating one, he wants a gazillion more because they’re delicious! 

Two facets of the food industry I really enjoy having fun with are the collectibles and hunting down fun flavours of things.  I am crazy about collectibles and special edition things, even though being Canadian sometimes has me stymied when it comes to special flavours that aren’t available on my side of the pond.  Lip glosses, Hello Kitty items, and food-related memorabilia rank at the top of my list of fun things to collect and I have cargo ship sized collections of all three to prove it!  My favourite sweets and snacks to chase down are M&M tins and collectibles, M&M flavours, flavoured Kit Kats (not regular ones, just flavoured ones), and of course, Oreo cookies! 

Which leads me to another one of my more recent happy moments: getting my hands on Oreo’s 100th birthday cake cookies!  Do you know what I did when my mum brought home a beautiful, shiny new bag of special 100th birthday and anniversary Oreos from the supermarket?  I grabbed it and I hugged it.  The same way Winnie the Pooh hugs his pot of honey.   

Recipe for Inside Out Oreo Stuffed Chocolate Chip Cookies (yields 4-5 dozen small cookies)


  • 2 cups all-purpose flour
  • 1 cup quick-cooking or old-fashioned rolled oats
  • 1 teaspoon baking powder
  • 1 teaspoon baking soda
  • 1 teaspoon kosher salt
  • 2½ sticks unsalted butter (10 ounces), at room temperature (make sure the butter is super soft and squishy!)
  • 1 cup brown sugar
  • 1/2 cup granulated sugar
  • 1 large egg, at room temperature
  • 1 large egg yolk, at room temperature
  • 1 tablespoon pure vanilla extract
  • 20 crushed Oreo cookies (I just crushed them with my hands but you could also crush them with a mallet) 
  • 1 ½ cups of semisweet chocolate chips
  • 1 ½ cups of white chocolate chips


  • Preheat the oven to 325°F.  Line 2 baking sheets with parchment paper (*Deb’s Note: Depending on how big you make your cookie dough balls, you’ll need to reuse your cookie sheets a few times.  My oven runs hot, so I actually don’t bother putting anything on the bottom rack and only use the top rack, placing 2 baking sheets vertically side by side).
  • In a medium bowl, mix the flour with the oats, baking powder, baking soda, and salt (*Deb’s Note: I didn’t use the mixer for this step, I just used a large spoon to mix everything together).
  • Beat the butter and both sugars at medium speed until creamy.  Add the egg followed by egg yolk and vanilla, beating well between additions and scraping down the side of the bowl as necessary (*Deb’s Note: I don’t have a standing mixer so I used a handheld).
  • Beat in the dry ingredients, then add the crushed Oreo cookies, followed by the semisweet chocolate chips and white chocolate chips.  Using a large spoon or your clean hands, fold in until evenly distributed. 
  • Grab fistfuls of cookie dough and shape into golf ball sized balls.  Place cookie dough balls onto the baking sheets, 2 inches apart.  Flatten them slightly with either the bottom of a spatula or the palm of your hand.  Bake 11-13 minutes, until the cookies begin to brown at the edges.  Let the cookies cool on the baking sheets, then transfer them to a rack to cool completely (*Deb’s Note: I placed 15 dough balls on each baking sheet and took them out after 11 minutes for super soft cookies.  If you prefer crispier cookies, leave them in for 12 or 13 minutes).


Recipe inspired by Food & Wine magazine.  Sampson, Sally.  “How Baking Can Change the World.” Food & Wine November 2011: 130.

5 thoughts on “The Oreo Anniversary Series – Crushing Oreos to Bake Inside Out Oreo Stuffed Chocolate Chip Cookies!

    • Thanks, Breige!! 😀 I wish there was a way to incorporate Oreos into everything, but I don’t think that would fly with more savoury items, haha. I’d love to see someone do it though, kind of like an Iron Chef challenge! Aside from the birthday cake Oreos, I SO want to get my hands on different kinds (like the mint and fugde and all that) but here in Canada (at least where I live) it’s slim pickins’ :\

  1. Omg, I am drooling just reading this post. I need to find these Birthday Cake Oreos. Thanks for the share! 🙂

    • Thank you, Julia, and thanks so much for visiting and leaving me a message! If you do end up trying the recipes and cookies, I hope you enjoy them as much as my family and I did! My dad was totally over the moon with these cookies – he had to stop himself and step away before he ate the whole cookie box, haha! I hope you come by again, Julia, and I hope you enjoy the blog!

  2. Pingback: Yellow Cream Filling, Flowers & Bunnies – Springtime Oreos & the Oreo Anniversary Series, One Year Later!! | Ate by Ate

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