This post may contain affiliate links, please see the privacy policy for details.
This pineapple upside down cheesecake is the ultimate dessert mashup, combining the tropical sweetness of pineapple upside-down cake with the rich, creamy decadence of cheesecake. Juicy caramelized pineapple, a hint of brown sugar, and a velvety cheesecake filling come together in perfect harmony. It’s a show-stopping treat that’s surprisingly simple to make and just like you can get at the Cheesecake Factory. Whether it’s for a celebration or a cozy family dessert, this recipe will have everyone asking for seconds—and the recipe!
Indulge in a delicious pineapple upside down cheesecake that’s perfect for pretty much any occasion. It’s creamy, moist, sweet and fruity – a wonderful choice.
A versatile dessert: Whether you’re planning a party, looking for new recipes to serve up after dinner or you just love cheesecake, this is a versatile dessert that’s great for any occasion. So delicious: The fruity flavors of pineapple and cherry pair with a creamy cheesecake filling and soft, fluffy cake for a really flavor-packed dessert. Not hard to make: It’s a little time-consuming to make, as you prepare the cheesecake filling, the cake and the other components separately and then you have hours of setting time, but the recipe itself is pretty simple.
Pineapple Upside Down Cheesecake Ingredients
A complete list of ingredients and amounts can be found in the recipe card below.
Canned pineapple: Fresh pineapple can be used instead if you prefer. Ensure that you slice it evenly and that the pineapple is ripe for the best flavor. Cream cheese: For the cheesecake filling. Full fat cream cheese is the most flavorful. Maraschino cherry juice: From the jar of maraschino cherries. Vanilla extract: To flavor the cake layers. Sugar: For sweetness, of course. Baking powder and baking soda: To achieve a light, fluffy cake. Sour cream and heavy cream: These make the cheesecake layer creamy.
How to Make Pineapple Cheesecake
For more detailed instructions with weights and measurements, jump to the printable recipe card.
Prepare the cheesecake: Beat the cream cheese and granulated sugar, and then add the eggs one by one. Next add sour cream, heavy cream and pineapple juice and mix until you achieve a smooth batter. Pour this cheesecake batter into a greased, parchment paper lined springform pan. Pour the cherry juice on top and swirl it into the cream cheese mixture. Bake the cheesecake: Put a roasting pan low in the oven and fill it with warm water. Put the springform pan with the cheesecake on the rack above the roasting pan and bake until set. Let it cool for an hour, then take the collar off the pan and freeze the cheesecake for a few hours. Make the cake batter: Grease and flour 2 cake pans. Combine the flour, baking powder, baking soda, and salt. Beat the butter and sugar in a large bowl and then mix in the egg, vanilla, pineapple juice, and half the flour mixture. Mix well and then add the milk and remaining flour mixture. Prepare the cake pans: Soak fabric cake slings (like these) in water and then squeeze out most of the water. Fit them around your cake pans. Assemble the cakes: Divide the melted butter between a pair of cake pans. Combine the brown sugar and cinnamon and sprinkle this over the melted butter. Add chopped pineapple rings and cherries to each one, then divide the cake batter between the cake pans. Bake the cakes: Bake the cakes until done and let them cool completely. Assemble the pineapple upside down cheesecake: Put the cheesecake on top of one layer of cake on a cake stand or large serving plate. Top with the second layer of cake. Chill until you’re ready to slice and serve, adding whipped cream or powdered sugar just before serving.
Substitutions and Variations
Gluten-free option: If you want a gluten-free version, use gluten-free flour and gluten-free baking powder. Baking soda is naturally gluten-free. Pineapple juice: Use the pineapple juice from the canned pineapple. If you don’t have enough, make up the remainder with water. Vanilla extract: Try a different extract if you prefer. Ground cinnamon: Substitute ground nutmeg or ginger.
Store: Refrigerate any leftovers in an airtight container or wrapped tightly with plastic wrap. Freeze: You can freeze it in an airtight container for up to 3 months. Thaw: Defrost it in the refrigerator overnight.
Top Tips
Don’t let the layers sink or shift: Ensure all layers are fully cooled or chilled before assembling. Cutting neat slices: Cut slowly with a back and forth motion to prevent the middle layer squishing out. Great garnishes: Fresh whipped cream with a cherry on top or maybe dusting with some powdered sugar are both good garnish options.
Copycat Pineapple Upside Down Cheesecake FAQs
Can I make this recipe ahead of time?
Yes, the cake and cheesecake layers can be made a day or 2 in advance and assembled closer to serving time. Keep the assembled cake refrigerated.
Is this best served chilled or at room temperature?
This layer cake tastes best when served chilled.
Cheesecake Factory Copycat Pineapple Upside Down Cheesecake Recipe
Preheat the oven to 325°F and put a large roasting pan in the lower ⅓ of the oven. Fill the pan with a gallon of warm or hot water.
Put the second oven rack in the middle of the oven.
Grease with shortening or spray a 9-inch springform pan well with nonstick spray and line the bottom with parchment paper.
In a large mixing bowl of a stand mixer, combine the cream cheese and sugar fitted with the paddle/roller attachment until smooth, scraping down the sides as necessary.
Add the eggs one at a time, blending each into the cream cheese.
Add the sour cream, heavy cream and pineapple juice. Mix until smooth and combined.
Pour the cheesecake batter into the prepared springform pan.
Pour the maraschino cherry juice into a circle in the center of the batter and swirl using the dull end of a butter knife.
Put the springform pan on the oven rack above the water-filled large roasting pan.
Bake the Cheesecake Layer:
Bake for 55 to 60 minutes or until the cheesecake is set to the touch and not jiggling.
Remove it from the oven and cool it for 1 hour.
Remove the collar from the springform pan and put the cheesecake in the freezer for at least 3 hours while you make the cake.
Make the Cake Layers:
Turn up the oven to 350°F.
Grease and flour a pair of 9-inch cake pans and set aside. Use bake even fabric wrap strips around the cakes to ensure even, flat baking – soak them in a bowl of warm water while you prepare the cake batter.
In a mixing bowl, mix the flour, baking powder, baking soda, and salt together.
In a large mixing bowl, add the butter and sugar and with a handheld electric mixer beat on a high speed until the texture is sandy and color is pale yellow.
Add the egg and blend to combine.
Add the vanilla and pineapple juice and mix until combined.
Add half the flour mixture to the egg mixture and mix on low until combined.
Add all the milk and mix again.
Finally, add the rest of the flour mixture and mix until combined.
Set the cake batter aside while you prepare the cake pans.
Prepare the Cake Pans:
Remove the fabric cake slings from the water, gently wringing out some water (not all of it).
Fit them around the prepared cake pans and set aside.
In a small bowl, mix the brown sugar and cinnamon together.
Divide the melted butter between the bottom of 2 x 9-inch round cake pans, then divide the brown sugar cinnamon mixture into each pan on top of the melted butter.
Arrange the slices of pineapple in each cake pan and add a cherry in the center of each pineapple slice.
Divide the batter evenly between the 2 pans and smooth out the top.
Bake the Cake Layers:
Bake on the center rack for 28 to 30 minutes, until a toothpick inserted in the center comes out clean.
Remove the cakes from the oven and let them cool for 10 minutes.
Invert the first cake onto a plate or cake stand with the pineapple/cherry topping facing up.
Invert the second cake onto parchment paper on a baking tray.
Allow to cool at room temperature, then wrap and refrigerate until cold. Note: It’s possible 1 or 2 pineapple slices will not release when inverted out of the cake pan – this happens. But it's easily placed back to its space while warm as the brown sugar will provide caramelization to hold the toppings while it cools.
Assemble the Cake:
Remove the cheesecake from the springform pan plate and put it on top of the cake on the cake stand.
Carefully top the cheesecake with the second cake, with the pineapple/cherry design facing up. Tip: Now that the second pineapple cake is cooled, use parchment paper to flip the cake over onto a board which then allows it to be flipped onto the cheesecake layer.
Refrigerate until you are ready to serve.
Garnish with homemade whipped cream or dust with powdered sugar, then slice and serve.
Notes
Don’t let the layers sink or shift: Ensure all layers are fully cooled or chilled before assembling. Cutting neat slices: Cut slowly with a back and forth motion to prevent the middle layer squishing out. Great garnishes: Fresh whipped cream with a cherry on top or maybe dusting with some powdered sugar are both good garnish options.
Whip up this delicious pineapple upside down cheesecake and you might well find it becomes your new favorite cheesecake recipe! It’s one of my favorite desserts. Instead of a graham cracker crust, the cheesecake filling nestles between two cake layers, so you get two desserts in one. It has all the flavor of pineapple upside down cake but with a cheesecake layer for added yumminess!
Bella Bucchiotti is a Canadian-based syndicated food, travel, and lifestyle writer, photographer, and creator at xoxoBella. She founded xoxoBella in 2015, where she shares her love for food, dogs, sustainability, fitness, crafts, outdoor adventures, travel, and philanthropy to encourage others to run the extra mile, try new recipes, visit unfamiliar places, and stand for a cause. Bella creates stress-free and family-friendly recipes for weeknight dinners and festive feasts.
This was a total hit! The best of both worlds in one dessert.
This was such a hit! The flavors blended perfectly, and it was so easy to make.
Wow, this dessert was divine! The caramelized pineapple was a total game-changer.