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Cheesecake Filled Pineapple Upside Down Cake

A delightful twist on a classic, this cheesecake filled pineapple upside down cake combines tangy pineapple and creamy cheesecake in a fluffy, buttery base.
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Prep Time 20 minutes
Cook Time 50 minutes
Total Time 1 hour 10 minutes
Servings: 8 servings
Course: Dessert
Cuisine: American
Calories: 350
Ingredients Method Notes

Ingredients
  

For the Pineapple Topping
  • 1 can (20 oz) sliced pineapple in juice Drain before using
  • 1/2 cup unsalted butter
  • 1 cup packed brown sugar
  • to taste Maraschino cherries For decoration
For the Cheesecake Filling
  • 16 oz cream cheese, softened
  • 2/3 cup granulated sugar
  • 2 large eggs
  • 1 tsp vanilla extract
For the Cake
  • 1 1/2 cups all-purpose flour
  • 1 cup granulated sugar
  • 1/2 cup unsalted butter, softened
  • 2 large eggs
  • 2 tsp baking powder
  • 1/2 tsp salt
  • 1/2 cup milk
  • 1 tsp vanilla extract

Method
 

Preparation
  1. Preheat your oven to 350°F (175°C). Spray a 9-inch round cake pan with non-stick cooking spray.
Make the Pineapple Topping
  1. In a saucepan over medium heat, melt the butter and brown sugar together until it becomes syrup.
  2. Drain the pineapple and add slices to the pan. Let them simmer for about 3-5 minutes.
  3. Pour the mixture evenly into the prepared cake pan and top with maraschino cherries.
Prepare the Cheesecake Filling
  1. In a mixing bowl, beat together the cream cheese and sugar until smooth.
  2. Add the eggs one at a time, followed by the vanilla extract, and mix until combined.
Prepare the Cake Batter
  1. In a large bowl, cream together the butter and sugar.
  2. Add the eggs, milk, and vanilla, mixing until well combined.
  3. Gradually add flour, baking powder, and salt until combined.
Layer It Up
  1. Pour the cheesecake filling over the pineapple in the cake pan, followed by the cake batter.
Bake
  1. Bake in your preheated oven for 45-50 minutes, or until a toothpick inserted in the center comes out clean.
  2. If the top starts browning too much, cover it loosely with tin foil.
Cool and Serve
  1. Once baked, allow the cake to cool in the pan for about 10 minutes.
  2. Carefully flip it onto a serving plate.
  3. Slice and serve. Pairs wonderfully with whipped cream or vanilla ice cream.

Notes

Be sure to cool the cake before flipping. Variations include swapping pineapple for peaches or berries. Store leftovers in the fridge for up to 3 days covered with plastic wrap.