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Pineapple Upside-Down Cheesecake Recipe

5 Stars 4 Stars 3 Stars 2 Stars 1 Star 4.6 from 11 reviews
  • Author: Taylor
  • Prep Time: 20 minutes
  • Cook Time: 1 hour 35 minutes
  • Total Time: 7 hours 40 minutes
  • Yield: 12 servings
  • Category: Dessert
  • Method: Baking
  • Cuisine: American
  • Diet: Vegetarian

Description

This Copycat Pineapple Upside Down Cheesecake recipe combines the tropical flavors of pineapple and cherries with a rich, creamy cheesecake layered between two moist pineapple upside-down cake layers. Perfect for a special dessert, it features a buttery brown sugar topping and a velvety cheesecake center, baked with care for an elegant presentation and delicious taste.


Ingredients

Scale

Pineapple Cheesecake

  • 16 ounces cream cheese room temp
  • 1/2 cup granulated sugar
  • 2 large eggs
  • 1/2 cup sour cream
  • 2 tablespoons pineapple juice
  • 1 teaspoon vanilla extract

Pineapple Upside-Down Cake Topping

  • 1/2 cup unsalted butter melted
  • 1 cup packed light brown sugar
  • 14 slices canned or fresh pineapple rings
  • 14 maraschino cherries

Pineapple Upside-Down Cake Batter

  • 1 1/2 cup + 3 tablespoons all-purpose flour sifted
  • 1/2 teaspoon baking powder
  • 1/4 teaspoon baking soda
  • 1/2 teaspoon salt
  • 1/2 cup unsalted butter melted
  • 3/4 cup light brown sugar packed
  • 1/4 cup granulated sugar
  • 1 large egg
  • 1/4 cup sour cream
  • 1/2 cup milk
  • 1/4 cup pineapple juice
  • 1 tablespoon vanilla extract


Instructions

  1. Prepare the cheesecake: Preheat the oven to 325°F. Grease a 9-inch springform pan, wrap it in heavy-duty foil to prevent water from seeping in, and set aside.
  2. Mix cream cheese and sugar: In a large bowl, whip the cream cheese with 1/2 cup granulated sugar until smooth using an electric hand mixer for a creamy base.
  3. Add eggs: Mix in the eggs one at a time, ensuring each is fully incorporated. Scrape down the sides of the bowl as needed to maintain an even mixture.
  4. Add sour cream and flavorings: Stir in the sour cream, pineapple juice, and vanilla extract until the mixture is completely smooth and creamy.
  5. Pour and prepare water bath: Pour the cheesecake batter into the prepared pan and place it inside a large roasting dish. Reduce the oven temperature to 300°F.
  6. Add water bath: Carefully fill the roasting pan with hot water halfway up the sides of the cheesecake pan to help the cheesecake cook evenly and prevent cracks.
  7. Bake cheesecake: Bake for 45 minutes, then turn off the oven heat and leave the cheesecake inside for an additional 20 minutes to set gently.
  8. Cool cheesecake: Remove cheesecake from the oven and the water bath. Allow it to cool to room temperature on the counter, then cover with plastic wrap and refrigerate for at least 8 hours or overnight for best results.
  9. Prepare cake topping: Divide the melted butter equally between two 9-inch cake pans. Sprinkle 1/2 cup of brown sugar evenly into each pan.
  10. Add fruit topping: Arrange the pineapple slices and maraschino cherries over the sugar and butter mixture in each pan as shown for the classic pineapple upside-down look. Set aside.
  11. Make cake batter: Preheat oven to 350°F. In a large bowl, whisk together the sifted all-purpose flour, baking powder, baking soda, and salt to combine.
  12. Mix wet ingredients for cake: In a separate medium bowl, whisk melted butter, brown sugar, and granulated sugar until smooth. Add egg, sour cream, milk, pineapple juice, and vanilla extract. Mix until combined.
  13. Combine cake batter: Add the wet ingredients to the dry ingredients and stir until no lumps remain and mixture is smooth.
  14. Fill pans and bake cake layers: Evenly divide the batter between the two prepared pans on top of the pineapple and cherry topping, smoothing the tops carefully. Bake for 30 minutes or until a toothpick inserted in the center comes out clean and the tops are golden brown.
  15. Cool cake layers: Let the cakes cool in their pans on wire racks for 10 minutes.
  16. Assemble the cake: Invert one cake onto a flat surface like a cutting board and the other onto the serving plate. Carefully remove the cheesecake from its pan and place it on top of the first inverted cake layer.
  17. Top and serve: Place the second cake layer on top of the cheesecake. Serve immediately or chill in the refrigerator until ready. Optionally garnish with whipped cream before serving.

Notes

  • Room Temperature Ingredients: Use cream cheese, eggs, and sour cream at room temperature for a smooth cheesecake batter.
  • Water Bath: Baking the cheesecake in a water bath helps prevent cracks and keeps the texture creamy.
  • Proper Mixing: Mix cheesecake filling on low speed to avoid incorporating excess air that can cause cracks.
  • Cool Completely: Allow the cheesecake to cool fully at room temperature before refrigerating to help it set perfectly.
  • Invert Carefully: When turning the pineapple upside-down cakes out of the pans, do so gently to keep fruit topping intact.
  • Chill Time: Refrigerate the assembled dessert for several hours for best flavor and texture before serving.

Nutrition

  • Serving Size: 1 slice
  • Calories: 450 kcal
  • Sugar: 38 g
  • Sodium: 220 mg
  • Fat: 25 g
  • Saturated Fat: 15 g
  • Unsaturated Fat: 8 g
  • Trans Fat: 0 g
  • Carbohydrates: 45 g
  • Fiber: 1 g
  • Protein: 6 g
  • Cholesterol: 110 mg