In a medium bowl, whisk together cold milk, sweetened condensed milk, and vanilla pudding mix until the pudding mix is fully dissolved. Set the mixture aside in the fridge to set while you prepare the whipped cream.
In a large mixing bowl, pour in the whipping cream. Using an electric hand mixer with the whisk attachment, whip the cream until stiff peaks form.
Add the chilled pudding mixture to the whipped cream and gently fold them together with a spatula until fully combined and no streaks remain.
Spoon half of this pudding mixture into a 9x13" dish and spread it evenly with a spatula.
Slice the bananas into ¼" thick rounds and arrange about ¾ of them over the pudding layer. Crumble approximately 18 Biscoff cookies and sprinkle them over the bananas.
Add the remaining pudding mixture on top of the banana and cookie layers, spreading it out evenly with a spatula.
Top the pudding with the remaining Biscoff cookies and banana slices as garnish. If you plan to serve the pudding in 1-2 days, slice and add the final banana just before serving to prevent browning.
Cover the dish and chill the Biscoff Banana Pudding in the fridge for at least 2 hours or overnight before serving. You can serve it directly from the dish or divide it into smaller containers if you prefer a mixed presentation.