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Pineapple Upside Down Cheesecake

Pineapple Upside Down Cheesecake

Pineapple Upside Down Cheesecake is a layer of buttery pineapple upside down cake with a creamy smooth cheesecake.

This is the perfect combination that goes great together.

My son’s birthday is coming up and I decided not to buy anymore cakes, but to make one at home.

Let’s be honest, the only reason why kids want us to buy a cake is to get all that sugar from the frosting and the toy (if any comes with it).

Then it sits in the fridge for weeks and into the garbage it goes.

Just a waste of money.

So since he loves a Cheesecake and also a Pineapple Upside Down cake, I decided, why not put them both together and make the best combination.

Don’t worry, I did ask him if for this birthday, how about we don’t buy a cake but make one instead.

He had a question mark on his face, but then he said okay let’s do it.

Plus, to be honest I wanted to dive into some of my homemade version of The Cheesecake Factory type.

The top view of the Pineapple Upside Down Cheesecake.

The cake batter is not from scratch.

It is made from a cake box mixture.

This makes it easier to make.

Also, I added a package of Vanilla Instant Pudding mix that helps the cake to be much more softer and moist.

However, as for the cheesecake, I made it similar to my Blueberry Cheesecake, except without a crust but with the same water bath method.

I decided to make the Cheesecake a day before, just to make sure it is all set and cool.

Making a Water Bath for the Pineapple Upside Down Cheesecake

I always use a water bath when I am baking a cheesecake, just like my Blueberry Cheesecake Recipe.

This helps add moisture to the oven to prevent any cracks from forming when baking.

If you can use a roasting pan to create a water bath, please do.

If not, then use the deepest baking sheet pan you have.

Fill the roasting pan with hot water to about 3/4 to 1 inch , depending on the depth of the roasting pan.

Wrap the filled spring form pan with aluminum foil paper (double wrapped), put it in the roasting pan and then in the oven.

Or if you can place the roasting pan in the oven, pour the hot water in it first and then put in the filled spring form pan that is double wrapped with aluminum foil paper.

The hot water should be halfway up the spring form baking pan that has the cheesecake batter.

How to make a Pineapple Upside Down Cheesecake

Firstly, mix together the ingredients to make the cheesecake batter and bake it. You can choose to do it in a water bath or do it the regular way. For this recipe, I used a water bath, just make sure the spring form pan is double wrapped to prevent water leaking into the cheesecake while baking. Let it cool and allow to chill in the refrigerator preferably overnight.

Making the cheesecake batter.
Cheesecake batter in a spring form baking pan.

Secondly, in a 9 inch pan put the butter and brown sugar and let the butter melt in the oven while it preheats to 350 degrees Fahrenheit. Add the pineapple slices and cherries. Set aside.

Melted butter and brown sugar.
Adding pineapple slices and cherries.

Thirdly, in a large bowl whisk together the dry ingredients. Add the eggs, oil and pineapple juice. Mix together until smooth. Divide the cake batter into 2 equal amounts: first over the pineapple slices and then in another 9 inch baking pan. Bake and let them cool.

Making the cake batter.

Finally, assemble the cakes. Place the cake without the pineapple toppings on the cake stand first, then the cheesecake and lastly the cake with the pineapple toppings. Slice and serve. Enjoy.

A slice of the Pineapple Upside Down Cheesecake.

Pineapple Upside Down Cheesecake Recipe

Ingredients

The Cake Batter

  • 1 (15.25 oz) Yellow Cake Mix
  • 1 3.4 oz Vanilla Instant Pudding Mix
  • 4 large Eggs
  • 1 cup Pineapple Juice (from the 20 oz can pineapple)
  • 1/2 cup Vegetable Oil

For The Topping

  • 1 20 oz can Pineapple Slices
  • Maraschino Cherries
  • 1/2 cup Brown Sugar
  • 4 Tablespoon Unsalted Butter

For The Cheesecake Filling

  • 3 (8 oz) blocks Cream Cheese, softened
  • 3/4 cup Sour Cream
  • 3 large Eggs
  • 1 1/2 teaspoon Vanilla Extract
  • 3/4 cup Granulated Sugar

Instructions

Making the Cheesecake

  1. Preheat the oven to 350 degrees Fahrenheit. Grease a 9 inch spring form baking pan with butter or non stick cooking spray. Tightly wrap the outside of the pan with 2 layers of aluminum foil paper, covering the bottom and sides. Set aside.
  2. In a mixing bowl, mix the cream cheese and sugar on medium speed, until smooth.
  3. For the eggs, add them one at a time on low speed. Do not over mix.
  4. Add the sour cream and vanilla extract and continue to mix on low speed.
  5. Pour the filling into the greased spring form baking pan and spread evenly.
  6. Place the spring form pan (that is already wrapped in aluminum foil paper) in a roasting pan, into the oven and pour some boiling water to make a water bath or pour the boiling water in the roasting pan with the cheesecake and then put it in the oven.
  7. Bake the cheese cake for about 60 to 65 minutes or gently shake the cheesecake and if the center jiggles slightly, then it is done.
  8. Turn off the oven and crack the oven open and leave the cheesecake in the oven for about an hour. Then remove from the oven and let it cool on a wire rack.
  9. Once it is cool, remove the outer rim from the spring form and cover with plastic wrap. Allow to chill into the refrigerator preferably overnight or at least for 4 to 5 hours.

To make the Pineapple Upside Down Topping

  1. Preheat the oven to 350 degrees Fahrenheit.
  2. In a regular 9 inch baking pan, melt the butter in the preheated oven. Add the brown sugar to the melted butter. Spread evenly to the edges, to cover the bottom of the baking pan.
  3. Then add enough pineapple slices to the bottom with some cherries inside and between the pineapple slices. Set aside.

To make the Pineapple Upside Down Cake batter

  1. In a mixing bowl, whisk together the cake mix and vanilla instant pudding. Add the oil, eggs and pineapple juice. Mix together with a hand mixer, until smooth.
  2. Pour half of the mixture in a greased 9 inch baking pan and the other over the pineapple slices and cherries with the sugar mixture in the other 9 inch baking pan.
  3. Bake both cakes for about 25 minutes or until a toothpick inserted comes out clean.
  4. Remove them from the oven and allow to cool for assembling.

Assembling the Pineapple Upside Down Cheesecake

  1. Once both the cakes are cool, place the cake without the pineapples and cherries on the cake stand. Level the cake if needed.
  2. Remove the cheesecake from the refrigerator and remove the plastic wrap. Place it on top of the cake. Then place the cake with the pineapple topping on top of the cheesecake.
  3. Level off the sides, if it need any.
  4. Serve and enjoy.

Notes

  • Doing a water bath works for me when I am making a cheesecake. It helps prevent cracks. You can choose to bake the cheesecake the regular way too.
  • Allow the cheesecake to cool first, then chill in the refrigerator preferably overnight or for about 4 to 5 hours.
  • Let both the pineapple cakes cool properly, especially the one with pineapple topping. It makes it easier to remove from the pan when assembling.
Pineapple Upside Down Cheesecake ready to eat.

Please let me know what you think about this Pineapple Upside Down Cheesecake in the comment section below.

Thanks for stopping by and please come back again.

Blessings and Love, as you carry on, on your YouNique Journey!

Pineapple Upside Down Cheesecake

Pineapple Upside Down Cheesecake

Yield: 12 Servings
Prep Time: 15 minutes
Cook Time: 1 hour 30 minutes
Additional Time: 5 hours
Total Time: 6 hours 45 minutes

Pineapple Upside Down Cheesecake is a layer of buttery pineapple upside down cake with a creamy smooth cheesecake.

Ingredients

FOR THE CAKE BATTER

  • 1 (15.25 oz) Yellow Cake Mix
  • 1 3.4 oz Vanilla Instant Pudding Mix
  • 4 large Eggs
  • 1 cup Pineapple Juice (from the 20 oz can pineapple)
  • 1/2 cup Vegetable Oil

FOR THE TOPPING

  • 1 20 oz can Pineapple Slices
  • Maraschino Cherries
  • 1/2 cup Brown Sugar
  • 4 Tablespoon Unsalted Butter

FOR THE CHEESECAKE FILLING

  • 3 (8 oz) blocks Cream Cheese, softened
  • 3/4 cup Sour Cream
  • 3 large Eggs
  • 1 1/2 teaspoon Vanilla Extract
  • 3/4 cup Granulated Sugar

Instructions

TO MAKE THE CHEESECAKE

  1. Preheat the oven to 350 degrees Fahrenheit. Grease a 9 inch spring form baking pan with butter or non stick cooking spray. Tightly wrap the outside of the pan with 2 layers of aluminum foil paper, covering the bottom and sides. Set aside.
  2. In a mixing bowl, mix the cream cheese and sugar on medium speed, until smooth.
  3. For the eggs, add them one at a time on low speed. Do not over mix.
  4. Add the sour cream and vanilla extract and continue to mix on low speed.
  5. Pour the filling into the greased spring form baking pan and spread evenly.
  6. Place the spring form pan (that is already wrapped in aluminum foil paper) in a roasting pan, into the oven and pour some boiling water to make a water bath or pour the boiling water in the roasting pan with the cheesecake and then put it in the oven.
  7. Bake the cheese cake for about 60 to 65 minutes or gently shake the cheesecake and if the center jiggles slightly, then it is done.
  8. Turn off the oven and crack the oven open and leave the cheesecake in the oven for about an hour. Then remove from the oven and let it cool on a wire rack.
  9. Once it is cool, remove the outer rim from the spring form and cover with plastic wrap. Allow to chill into the refrigerator preferably overnight or at least for 4 to 5 hours.

TO MAKE THE PINEAPPLE UPSIDE DOWN TOPPING

  1. Preheat the oven to 350 degrees Fahrenheit.
  2. In a regular 9 inch baking pan, melt the butter in the preheated oven. Add the brown sugar to the melted butter. Spread evenly to the edges, to cover the bottom of the baking pan.
  3. Then add enough pineapple slices to the bottom with some cherries inside and between the pineapple slices. Set aside.

TO MAKE THE PINEAPPLE UPSIDE DOWN CAKE

  1. In a mixing bowl, whisk together the cake mix and vanilla instant pudding. Add the oil, eggs and pineapple juice. Mix together with a hand mixer, until smooth.
  2. Pour half of the mixture in a greased 9 inch baking pan and the other over the pineapple slices and cherries with the sugar mixture in the other 9 inch baking pan.
  3. Bake both cakes for about 25 minutes or until a toothpick inserted comes out clean.
  4. Remove them from the oven and allow to cool for assembling.

Notes

  • Doing a water bath works for me when I am making a cheesecake. It helps prevent cracks. You can choose to bake the cheesecake the regular way too.
  • Allow the cheesecake to cool first, then chill in the refrigerator preferably overnight or for about 4 to 5 hours.
  • Let both the pineapple cakes cool properly, especially the one with pineapple topping. It makes it easier to remove from the pan when assembling.
Nutrition Information:
Yield: 12 Serving Size: 1
Amount Per Serving: Calories: 688Total Fat: 22gSaturated Fat: 7gTrans Fat: 0gUnsaturated Fat: 13gCholesterol: 130mgSodium: 413mgCarbohydrates: 115gFiber: 6gSugar: 82gProtein: 8g

The nutritional information that is provided, is computer generated and therefore it is an estimate. Please do your own research with the ingredients that are listed here, if you have any concern about any specific diet or your health.

Jackie DeHollander

Tuesday 15th of March 2022

sounds sooo good-could you do pineapple on both cakes

Yanique Vincent

Tuesday 15th of March 2022

Hi Jackie, Putting the pineapple on both cakes is your preference. I have never done it before. So please let me know the outcome when you do it. Thanks in advance.

Elizabeth

Wednesday 19th of August 2020

This recipe looks absolutely incredible. Among my father's favorite desserts are cheesecake and pineapple upside down cake, so I'm certain he'd enjoy a combination of the two. Thanks for sharing the recipe!

Yanique Vincent

Wednesday 19th of August 2020

Thank you so much. If you make it for your father, let me know. You are most welcome...thanks again.

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