Preheat your oven to 350°F (175°C) and prepare two regular-sized muffin tins by spraying them lightly with cooking spray.

In a medium bowl, whisk together the all-purpose flour, Dutch-processed cocoa, black cocoa, baking soda, and salt until well combined.

In a separate large bowl, beat the room temperature butter along with granulated and brown sugars using an electric mixer until light and fluffy. Add in the eggs and vanilla extract, mixing well, then slowly incorporate the dry ingredients until just combined.

Scoop the cookie dough into the prepared muffin tins, pressing down gently to flatten each scoop into a cup shape. Bake in the preheated oven for 10 to 13 minutes, until the edges are set but the centers are still soft.

Allow the cookie cups to cool in the muffin tins for about 10 minutes. Once cool enough to handle, gently remove them from the tins and transfer them to a wire rack to cool completely.

In a chilled bowl, whip the heavy cream using an electric mixer until stiff peaks form. In a separate bowl, beat the cream cheese with granulated sugar until smooth and creamy. Gradually fold in the Oreo cookie crumbs, then gently incorporate the whipped cream until just combined.

Once the cookie cups are completely cool, pipe or spoon the cheesecake filling into each well until it’s generously heaped.

After assembling, refrigerate them for 1 to 2 hours, allowing the filling to set.

Serve your Oreo Cheesecake Cookie Cups chilled at parties or gatherings.