It’s best to make the football cookie part ahead of time so the chocolate and royal icing have time to harden.
Melt wafers according to package instructions. Dip one Milano cookie into the chocolate at a time. Use a fork to remove the cookie from the chocolate, and set it on a silicone lined baking sheet to harden. Dip all the cookies and allow the chocolate to harden.
To make a small batch of royal icing, combine powdered sugar, meringue powder, and water into a small bowl. Use an electric mixer to beat it until it’s combined and smooth - 2 minutes. Transfer the royal icing to a piping bag.
After the chocolate-dipped cookies harden, draw football stitches on each cookie with the royal icing. I find it easiest to draw the center strip on all the cookies first. Let it hardens, then go back and add the stitches to each cookie.
Blend the Oreos in a blender or food processor until you have Oreo crumbs.
Using a chilled bowl, add the heavy cream, powdered sugar, and green food coloring to the bowl, mix with an electric mixer until stiff peaks form, 3-4 minutes.
To assemble the dirt cups, place about an inch in the bottom of each cup. Layer with a few spoonfuls of chocolate pudding. Spoon or pipe on the green whipped cream. Top each cup with a football cookie right before serving. The pudding cups can be made ahead of time and stored in the fridge, but be sure to add the cookie to the top right before serving.