Grease and lightly sprinkle with flour a 9-x-13 inch cake pan.
Prepare cake mix according to box instructions. Once the batter is ready, stir in 10 crushed Oreo cookies.
Pour batter into the prepared pan and bake for about 25-30 minutes, or until a toothpick inserted into the center comes out clean. Let cool for 10 minutes and using the bottom of a wooden spoon, poke holes all over the cake.
While the cake is cooling, mix condensed milk and chocolate chips in a medium bowl, microwave for 1 minute, and stir until fully melted and smooth.
Pour the mixture evenly over the cake surface.
In another bowl, combine pudding mix with whole milk and stir just until it thickens. Immediately pour the mixture on top of the cake and spread it evenly.
Top it with 10 crushed Oreo cookies, distributing them evenly.
Let cake fully cool to room temperature.
Oreo Whipped Cream:
Add all the ingredients, except Oreos, to a large bowl, beat until stiff peaks form.
Stir in crushed Oreos.
Scoop the whipped cream all over the cake and spread it with a spatula in an even layer. Smooth the top with a spatula.
Sprinkle mini chocolate chips all over the surface. Sprinkle crushed Oreo cookies and add the whole Oreos in the center of the cake.
Refrigerate the cake overnight or for at least 8 hours before serving.