Pour chocolate sauce into a bowl and rim the top of each glass. Crumble 1 cookie into a bowl. Dip the glass into the cookie crumbles. Set aside.
Add ice cream, 1 cookie and coffee into a blender. Blend until smooth. Pour into prepared glass. Garnish with whipped cream and 1 crumbled chocolate chip cookie.
Cut a small triangle out of the last two cookies. Place on the rim of each glass for garnish and serve.