Preheat oven to 350 degrees F. Grease and line a 8"x8" baking pan, set aside.
In a large mixing bowl whisk together the oil, sugar, eggs and vanilla extract until smooth. Gently whisk in the milk. Fold in the mashed banana.
Add in the flour, baking powder baking soda, salt, and cinnamon if desired. Mix until smooth. Transfer the batter into the prepared baking pan.
Bake in a preheated oven for 28-30 minutes or until a toothpick inserted comes out clean. Allow to cool completely before frosting.
For the Buttercream:
In the bowl of a stand mixer fitted with the paddle attachment or in a large bowl with a handheld electric mixer, beat the butter until light and fluffy, 4-5 minutes.
Add about half of the powdered sugar, beat on low until fully incorporated. Add in the remaining powdered sugar, and vanilla extract. Beat on low speed again just until the powdered sugar is incorporated.
Add in the heavy cream and mix on low again until smooth. Spread the buttercream over the cooled banana cake.