Lightly coat the grids of a waffle baker with cooking spray. Preheat waffle baker according to manufacturers directions.
Meanwhile, in a medium bowl combine flour, sugar, baking powder, salt, and cinnamon. Make a well in the center of the flour mixture.
In another medium bowl combine egg, milk, mashed banana, and oil. Add egg mixture to flour mixture all at once. Stir just until moistened (batter should be slightly lumpy).
Pour about 2 tablespoons of the batter onto each quarter of the preheated waffle baker. Close lid quickly; do not open until done. Bake according to manufacturer's directions. When done, use a fork to lift waffle off grid. Repeat with remaining batter.
For each serving, stack 3 of the mini-waffles onto a plate. Immediately top each with banana slices, dessert topping, and maraschino cherry. Serve warm.