For Topping: Combine cookie crumbs and sugar in airtight container. Set aside until ready to use.
For Funnel Cake Batter: Combine dry ingredients in large bowl. Whisk milk and eggs in second large bowl. Add dry ingredients to egg mixture; mix well.
Heat a pot of oil on medium-high heat to 375ºF. Place #1 piping tip into a funnel, then fill with 1/4 cup batter. Holding funnel close to the surface of the oil, swirl batter into oil. Fry until golden brown on both sides, turning once. Drain. While still hot, coat Funnel Cake with Topping mixture. Repeat with remaining batter.
For each serving: Combine 6 oz. ice cream, 2 oz. strawberries and 1.5 oz. cookie pieces, being careful not to break up the cookie pieces. Spoon into small serving glass. Top with 1 Funnel Cake.