Layer the bottom of the pan with a single layer of chessmen cookies, you should be able to fit about 20. Then layer with the sliced bananas.
In a bowl, combine the milk and pudding mix using a hand mixer. Mix until smooth then allow to set.
In a separate bowl using a hand mixer beat the cream cheese with condensed milk (1 minute). With a spatula, scrape down the sides and bottom of the bowl and mix again for 30 seconds.
Fold in the whipped topping into the cream cheese mixture.
Add the cream cheese mixture to the pudding mixture and stir until well combined.
Spread/pour the mixture over the cookies and fresh banana layer in the pan.
Top with the remaining Chessmen cookies, cover with plastic wrap and chill in the fridge overnight (or at least 4 hours).