Preheat oven to 350°F. Spray two regular sized muffin tins with cooking spray.
Whisk together flour, cocoa powders, baking soda, and salt. Set aside.
Beat butter and sugars on med-high until light and fluffy (approx. 2-3mins). Reduce speed and add eggs one at a time and vanilla. Beat until combined. Add flour mixture and mix until just combined.
Using a large cookie scoop (3 Tbsp) scoop dough into muffin tins, press down to flatten.
Bake for approx. 10-13mins or until mostly set, but still soft in the middle.
Remove from oven and immediately use a small jar or container to press firmly down in the center to create a well. Cool in pans for 10mins, loosen each slightly by twisting it in the pan. Cool for 5 more minutes then remove from pan and cool completely on a wire rack.
Baileys Chocolate Cheesecake Filling:
Whip heavy cream until stiff peaks (ideally with a cold whisk and in a cold bowl).
In a separate bowl, beat cream cheese and sugar until smooth. Add chocolate and Baileys and beat until incorporated.*
Fold cream cheese mixture into whipped cream and pipe into cooled cookie cups. Refrigerate until set (approx. 2 hours).
Sprinkle with chocolate shavings or cocoa powder if desired. Serve chilled and eat within 2-3 days. Or freeze for up to 4 weeks.
* I whipped the cream in my stand mixer, transferred the cream to a bowl, then whipped up the cream cheese using the same bowl and whisk from the whipped cream (without cleaning it- easier this way!)