Crush 9 of the Oreo cookies and evenly distribute the crumbs among seven 8-ounce clear cups.
In a large mixing bowl, beat together the cream cheese, powdered sugar, milk, and vanilla extract until smooth and creamy. Gently fold in only 2 cups of the thawed Cool Whip.
Split the cheesecake mixture evenly into two separate bowls. Color one portion orange using gel food coloring. Keep the other mixture white.
Pipe or spoon 3 Tablespoons of the white cheesecake mixture, over the cookie crumbs in each cup, in a circular motion. Using a spoon, gently press the cheesecake mixture into an even layer.
Crush the remaining 9 Oreo cookies and sprinkle about a 1/4 cup of crumbs evenly over the white cheesecake layer in each cup.
Pipe or spoon 3 Tablespoons of the orange cheesecake mixture on top of the second cookie layer in each cup. Using a spoon, gently press the cheesecake mixture into an even layer. Cover and store the cheesecake cups in the fridge to chill for at least 2 hours before serving. (Can be stored in the fridge for up to 4 days when tightly covered.)
Right before serving, dollop each cup with the remaining Cool Whip, and decorate with more crushed Oreo, Halloween sprinkles, and/or candy as desired. Enjoy!