Preheat the oven to 350 degrees F and butter a 3-quart oval baking dish.
Put the doughnuts and bread into a very large bowl and mix to combine.
In a separate bowl, add the cream, milk, sugar, cinnamon, vanilla and eggs and mix until well combined. Slowly pour the egg mixture over the doughnuts. Mix well and slightly press into the prepared baking dish. Bake until golden brown with a firm consistency, 45 to 50 minutes.
Meanwhile, grease a baking sheet with the oil and lay out the slices of bacon on top, making sure they don't overlap. Bake on another rack in the oven until crispy, about 20 minutes. Allow to cool slightly, then dice into small pieces.
Cut the bread pudding into small rounds using a 3-inch round cutter. Place on round plates, topping each with the crispy bacon and a dollop of whipped cream.
Reserve any remaining bread pudding for another use or just eat the scraps!