Preheat oven to 350°F and prepare a jelly roll pan lined with parchment paper and lightly greased.
Lay a clean kitchen towel flat and dust generously with powdered sugar; set aside.
In a medium bowl, whisk flour, cocoa powder, baking powder, and salt together.
In a large bowl, beat eggs and granulated sugar on high speed for 4 to 5 minutes until thick and pale.
Add vegetable oil, vanilla extract, and milk to the eggs and mix gently until combined.
Fold dry ingredients into the wet mixture carefully until no streaks remain.
Pour batter into the prepared pan and smooth the top evenly.
Bake for 10 to 12 minutes, or until the cake springs back when lightly touched.
Invert the hot cake onto the sugared towel, peel off parchment, and roll the cake with the towel inside; let cool completely.
Beat peanut butter and powdered sugar until smooth, then add heavy cream and vanilla extract; beat until light and spreadable.
Fold chopped peanut butter cups into the filling gently.
Unroll the cooled cake and spread the peanut butter filling evenly, leaving a border around the edges.
Re-roll the cake tightly without the towel and place seam-side down on a serving platter.
Heat heavy cream until steaming and pour over chocolate chips; let sit for 2 minutes, then stir until smooth to make ganache.
Drizzle or spread the ganache over the cake and allow to set before slicing and serving.