Preheat your oven to 350°F (175°C) and prepare cake pans.
In a large mixing bowl, combine the flour, sugar, cocoa powder, baking powder, baking soda, and salt.
Add the eggs, milk, oil, and vanilla to the dry ingredients and blend until combined.
Fold in the crushed Oreo cookies gently to your batter.
Divide the batter evenly between your prepared cake pans and bake for 30–35 minutes.
Once baked, allow the cakes to cool in the pans for 10 minutes before transferring to a wire rack.
While the cakes cool, prepare the frosting by whipping the heavy cream with powdered sugar until stiff peaks form.
Once cakes are completely cool, place one layer on a serving platter and spread a layer of frosting on top.
Stack the second layer on top and frost the top and sides of the entire cake.
Top the entire cake with crushed Oreo cookies for decoration and serve.