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You are here: Home / Dessert / Cheesecake / Pineapple Upside Down Cheesecake

Pineapple Upside Down Cheesecake

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September 27, 2023 by Hugs & Cookies xoxo 359 Comments

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Pineapple Upside Down Cheesecake

If you love cheesecake and pineapple upside down cake then this is a no brainer! It began with my favorite cheesecake…the one from the famous restaurant Juniors! I let the cheesecake chill completely. I even made it two days before serving because it holds up that well! Then I prepared my pineapple upside down cake. I let it cool at room temp and then transferred it directly on top of the cheesecake! Perfect fit. I chilled that overnight and served straight from the fridge. Perfection. This is such a great dessert because you can prepare it days in advance! Feel free to just use the pineapple upside down cake recipe without the cheesecake too!

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You’ll Need:

HUGE spatula

9 inch springform pan

9 inch x 2 inch cake pan

Cheesecake Moat-LOVE this!!!

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Cheesecake Portion of Recipe

Junior's Cheesecake With Cracker Crust
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Ingredients
  

  • Cheesecake
  • Crust:
  • 1 1 /2 c. graham cracker crumbs
  • 1 T sugar
  • 6 T melted butter
  • Cheesecake:
  • Four 8-ounce packages PHILADELPHIA cream cheese at room temperature
  • 1 ⅔ cups sugar
  • ¼ cup cornstarch
  • 1 tablespoon pure vanilla extract
  • 2 extra-large eggs
  • ¾ cup heavy whipping cream

Instructions
 

  • Crust:
  • Combine all ingredients and press into a 9 inch springform pan.
  • Bake at 350 for 8 minutes. Let cool.
  • Cheesecake:
  • In a large bowl, using an electric mixer fitted with the paddle attachment, beat 1 package of the cream cheese, 1/3 cup of the sugar, and the cornstarch together on low until creamy, about 3 minutes, scraping down the bowl several times.
  • Blend in the remaining cream cheese, one package at a time, beating well and scraping down the bowl after each.
  • Increase the mixer speed to medium and beat in the remaining sugar, then the vanilla.
  • Blend in the eggs, one at a time, beating well after each.
  • Beat in the cream just until completely blended.
  • The filling will look light, creamy, airy, and almost like billowy clouds. Be careful not to overmix! Gently spoon the batter over the crust. Wrap the sides of the pan in aluminum foil.
  • Place the cake pan in a large shallow pan containing hot water that comes halfway (about 1 inch) up the side of the springform. Bake until the edge is light golden brown, the top is light gold, and the center barely jiggles, about 1 1/4 hours. If the cake still feels soft around the edge, let it bake for 10 minutes more (the cooking time will be about the same for both the 8- and 9-inch cheesecakes). Remove the cheesecake from the water bath, transfer to a wire rack, and let cool for 2 hours. Chill until cold.
  • Cheesecake recipe adapted from Junior's

Pineapple Upside Down Cake

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Ingredients
  

Topping

  • ¼ cup butter melted
  • ½ cup packed light brown sugar
  • sliced pineapples 8 canned slices
  • 15-20 maraschino cherries

Cake

  • 1 and 2/3 cups flour
  • ½ teaspoon baking powder
  • ¼ teaspoon baking soda
  • ½ teaspoon salt
  • ½ cup butter melted
  • ¾ cup packed light brown sugar
  • ¼ cup granulated sugar
  • 1 large egg
  • ¾ cup milk
  • ½ cup pineapple juice
  • 1 Tablespoon vanilla

Instructions
 

  • Preheat oven to 350°F
  • Prepare topping first:
  • Place 1/4 cup of melted butter into a 9-inch cake pan
  • Sprinkle the brown sugar on top.
  • Lay pineapple slices on top and add cherries in the spaces!

Cake

  • In a microwave-safe bowl, melt the butter.
  • Whisk in the sugars.
  • Whisk in the egg, milk, pineapple juice, and vanilla.
  • Add dry ingredients and whisk to remove lumps.
  • Pour batter into the pan on top of the pineapples.
  • Bake for at 20 minutes and then loosely tent with foil to prevent browning.
  • Bake an additional 20-25 minutes until a toothpick comes out clean.
  • Cool for 10 minutes and invert onto large plate.
  • Let cool completely and use a HUGE spatula to transfer this on top of your cheesecake.
  • Chill until cold!

Pineapple Upside Down Cake adapted from Sally’s Baking Addiction

Pineapple Upside Down Cheesecake

Pineapple Upside Down Cheesecake pineapple upside down cheesecake baked pineapple upside down cake and cheesecake

Pineapple Upside Down Cheesecake

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Filed Under: Cheesecake, Dessert, Fruit Desserts

This post may contain affiliate links, view my Disclosure Policy. Sharing of this post is both encouraged and appreciated. Copying and/or pasting of full recipes to ANY social media or blogs is strictly prohibited without written consent. Recipes- including exact wording and photographs- are Copyright of hugsandcokiesxoxo.com. Any unauthorized use of content or photos from hugsandcookiesxoxo.com is a violation of my Copyright.

Hi, I'm Danielle!

Welcome! I am married to my Prince Charming and we have 2 beautiful boys. I am also a first grade teacher and I love my students more than chocolate chip cookies!  Hope your day is filled with Hugs & Cookies!  xoxo

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