Preheat the oven to 350°F (175°C) and prepare the cupcake pan.
In a large mixing bowl, cream together the softened butter, granulated sugar, and brown sugar until light and fluffy.
Add the eggs, one at a time, mixing well after each addition.
Stir in the mashed bananas and vanilla extract until well combined.
In a separate bowl, whisk together the flour, baking powder, baking soda, salt, and cinnamon.
Gradually add the dry mixture to the wet ingredients, mixing until just combined.
Divide the batter evenly among the cupcake liners, filling them about two-thirds full.
Bake for 18–20 minutes or until a toothpick inserted in the center comes out clean.
Allow the cupcakes to cool in the pan for five minutes, then transfer them to a wire rack to cool completely.
While the cupcakes cool, prepare the cinnamon cream cheese frosting.
In a mixing bowl, beat together the softened cream cheese and butter until creamy and well blended.
Gradually add the powdered sugar, mixing on low speed until incorporated, then beat on high until fluffy.
Add cinnamon and milk, adjusting the consistency to your preference.
Once the cupcakes are completely cooled, frost them with the cinnamon cream cheese frosting using a piping bag or a spatula.
