As I pulled my first slice of Pineapple Upside-Down Cheesecake Cake from the pan, the golden crust and shimmering pineapple topping glimmered like a sun-kissed treasure. This delightful dessert combines the creamy decadence of cheesecake with the nostalgic charm of a classic pineapple upside-down cake, creating an irresistible treat any home chef would be proud to serve. Not only is it a showstopper for gatherings, but this cake also comes with the bonus of being semi-homemade—perfect for those busy weeknights when you crave something special without the fuss. Plus, it’s a fantastic way to impress your guests and satisfy your sweet tooth all in one bite. Are you ready to dive into this delicious adventure? Let’s get baking!

Why is this cake so special?
Irresistibility comes from its perfect blend: creamy cheesecake, rich yellow cake, and tangy pineapple. Time-saving elements make it easy to whip up, combining homemade flavors with ready-to-use ingredients. Impressive presentation transforms any gathering, leaving guests raving. Versatility shines—serve it warm or chilled, making it suitable for any occasion. Lastly, crowd appeal is guaranteed; who can resist a slice of this scrumptious delight?
Pineapple Upside-Down Cheesecake Cake Ingredients
• Here's everything you need to create this delightful dessert!
For the Pineapple Layer
- ½ cup butter – This adds richness and helps the brown sugar caramelize beautifully.
- 1 cup brown sugar – Provides a deep, molasses-like sweetness that complements the pineapple.
- 1 can (20 oz) pineapple slices, drained – Their tangy flavor shines through the cheesecake, making it the star of the show.
- 12 maraschino cherries – These not only add a pop of color but also a burst of sweetness with each slice.
For the Cheesecake Batter
- 16 oz cream cheese, softened – Ensures a smooth, creamy texture in the cheesecake layer.
- 1 cup granulated sugar – Balances the tang of the cream cheese, creating the perfect sweetness.
- 3 large eggs – Acts as a binder, giving the creamy cheesecake its structure.
- 1 teaspoon vanilla extract – Adds a warm, aromatic depth of flavor.
- ½ cup sour cream – Adds tanginess and moisture, keeping the cheesecake from being too dense.
- 2 tablespoons all-purpose flour – Helps stabilize the batter, ensuring a perfect bake.
For the Cake Layer
- 1 package (15.25 oz) yellow cake mix – Makes this recipe semi-homemade and incredibly easy to prepare.
- 1 cup water – Standard moisture for the cake mix, keeping it fluffy and light.
- ½ cup vegetable oil – Adds moisture to the cake, resulting in a tender crumb.
- 3 large eggs (again) – For the cake mix, ensuring it rises nicely.
With these Pineapple Upside-Down Cheesecake Cake ingredients, you're all set for a baking adventure that combines flavors and textures in every heavenly slice!
Step‑by‑Step Instructions for Pineapple Upside-Down Cheesecake Cake
Step 1: Preheat and Prepare the Pan
Begin by preheating your oven to 325°F (163°C). While that’s warming up, grab a 9-inch springform pan, coat it generously with nonstick spray, and wrap the bottom in aluminum foil to catch any drips during baking. This preparation is crucial for your Pineapple Upside-Down Cheesecake Cake’s successful release without any sticking.
Step 2: Create the Pineapple Layer
In the prepared pan, pour in the melted butter, allowing it to coat the bottom evenly. Next, sprinkle the brown sugar over the butter, creating a sweet base. Now beautifully arrange the pineapple slices atop the brown sugar, ensuring an even layer, and place a maraschino cherry in the center of each pineapple slice for a pop of color and sweetness.
Step 3: Make the Cheesecake Batter
In a medium bowl, use an electric mixer to beat the softened cream cheese until it’s velvety smooth. Gradually mix in the granulated sugar, continuing to beat until fluffy and well combined. Add the eggs one at a time, mixing thoroughly after each addition. Finally, stir in the vanilla extract, sour cream, and flour, taking care to blend until smooth; this mixture will be the creamy centerpiece of your Pineapple Upside-Down Cheesecake Cake.
Step 4: Layer the Cheesecake Mixture
Carefully pour the creamy cheesecake mixture over your pineapple layer in the pan, smoothing the top with a spatula to create a flat surface. Pop the pan into the preheated oven and bake for 40 to 45 minutes. The center should be slightly jiggly yet not liquid, signaling that your cheesecake is perfectly baked and ready for cooling.
Step 5: Cool and Chill the Cheesecake
Once baked, remove the cheesecake from the oven and let it cool completely on a wire rack. This cooling stage is essential for the cake’s structure. After it comes to room temperature, cover it and chill in the refrigerator for at least 4 hours, or preferably overnight, allowing those flavors to meld beautifully.
Step 6: Prepare the Yellow Cake Batter
When you’re ready to complete your Pineapple Upside-Down Cheesecake Cake, prepare the yellow cake batter according to the package instructions. As you do this, preheat your oven to 350°F (175°C) to ensure it’s ready for baking the cake layer immediately after.
Step 7: Invert the Cheesecake
Once the cheesecake has chilled and firmed up, carefully remove it from the springform pan. Gently invert it onto a greased 9-inch round cake pan, ensuring the pineapple layer is facing down. This step is crucial in achieving the stunning presentation of your dessert, highlighting the caramelized pineapples.
Step 8: Add the Cake Batter
Pour the prepared yellow cake batter evenly over the cheesecake layer, being cautious not to disturb the cheesecake. Bake the cake in the oven for 35 to 40 minutes, checking for doneness by inserting a toothpick into the center; it should come out clean, indicating a perfectly baked cake.
Step 9: Cool and Serve the Cake
After baking, allow the cake to cool in the pan for about 15 minutes. Then, carefully invert it onto a serving plate to unveil the gorgeous pineapple topping. Let the entire cake cool completely before slicing, ensuring each piece showcases the beautiful layers of your Pineapple Upside-Down Cheesecake Cake.

How to Store and Freeze Pineapple Upside-Down Cheesecake Cake
Fridge: Keep any leftovers in an airtight container in the fridge for up to 3 days. This will maintain the cake’s creamy consistency and fresh flavor.
Freezer: For longer storage, wrap the cake tightly in plastic wrap and then in aluminum foil. It can be frozen for up to 2 months. Thaw it overnight in the fridge before serving.
Reheating: When ready to enjoy, you can either slice and enjoy it cold or warm individual pieces in the microwave for about 20 seconds for a cozy treat!
Airtight Guidance: Make sure the cheesecake is completely cool before wrapping to prevent condensation, keeping your Pineapple Upside-Down Cheesecake Cake delicious and fresh!
Expert Tips for Pineapple Upside-Down Cheesecake Cake
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Perfect Butter: Use unsalted butter for the pineapple layer to control the sweetness and flavor balance in your Pineapple Upside-Down Cheesecake Cake.
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Don’t Rush Cooling: Allow the cheesecake to cool fully before chilling. This helps it set properly and prevents a soggy texture.
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Be Gentle: When inverting the cheesecake, be careful! A sudden move can break the cheesecake layer. Take your time for a smooth transition.
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Check Consistency: The cheesecake should be jiggly but firm in the center after baking. Don’t overbake—you want that creamy texture!
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Chill Longer for Flavor: For best results, let the cheesecake chill overnight. The flavors meld beautifully for a more delicious slice.
Pineapple Upside-Down Cheesecake Cake Variations
Feel free to explore these delightful twists that will make your pineapple upside-down cheesecake cake even more exciting!
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Dairy-Free: Substitute cream cheese with vegan cream cheese and use coconut milk in place of sour cream for a dairy-free delight.
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Tropical Twist: Add shredded coconut to the cheesecake batter for a delightful tropical flavor that complements the pineapple beautifully.
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Nutty Crunch: Fold in chopped pecans or walnuts into the cake batter for an added crunch, enhancing the texture with every bite.
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Chocolate Drizzle: Drizzle melted chocolate over the finished cake for a rich and indulgent touch that contrasts wonderfully with fruity flavors.
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Spiced Up: Add a pinch of cinnamon and nutmeg to the cheesecake batter for a warm spice that elevates the flavor profile, perfect for cozy gatherings.
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Coconut Oil: Replace vegetable oil with melted coconut oil in the cake batter for a subtly sweet hint of coconut that pairs well with pineapple.
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Different Fruits: Exchange pineapple for other fruits, like peaches or cherries, for a unique fruit twist that’s equally delicious.
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Extra Sweetness: Add caramel sauce drizzled on top before serving to amplify the sweetness and give the cake an elegant finish that will wow your guests.
Make Ahead Options
These Pineapple Upside-Down Cheesecake Cakes are perfect for busy home cooks looking to save time during the week! You can prepare the cheesecake layer and refrigerate it up to 3 days in advance, allowing the flavors to deepen. After it cools, wrap it tightly in plastic wrap to keep it fresh and moist. You can also make the yellow cake batter ahead of time and store it in the refrigerator for up to 24 hours. When you’re ready to assemble, simply follow the finishing steps of inverting the cheesecake onto the cake layer and bake it straight away. This way, you’ll have an impressive dessert with minimal last-minute effort, just as delicious as if made fresh!
What to Serve with Pineapple Upside-Down Cheesecake Cake
Elevate your dessert experience by pairing this creamy delight with complementary dishes that enhance its flavors and textures.
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Tropical Fruit Salad: A medley of fresh tropical fruits provides a refreshing contrast, balancing the rich cheesecake with vibrant flavors and textures.
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Whipped Cream: Light and airy, a dollop of freshly whipped cream on each slice adds a touch of elegance while emphasizing the cake's sweetness.
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Coconut Flavored Rice: This subtly sweet and fragrant side dish brings a delightful tropical twist that harmonizes with the pineapple topping beautifully.
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Toasty Nuts: Chopped pecans or walnuts can add a crunchy element, enhancing the overall texture and offering a nutty richness that complements the dessert's creaminess.
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Creamy Vanilla Ice Cream: Serve a scoop alongside the cake for a comforting combination that melts into each bite, enriching the flavors of both the cake and ice cream.
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Mint Infused Iced Tea: Refreshing and light, this herbal drink can cleanse the palate between bites, making it the perfect thirst-quencher to enjoy with the cheesecake cake.
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Lemon Sorbet: A tangy and icy treat serves as a bright contrast, cutting through the richness of the cake while providing a palate-cleansing sensation.
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Chocolate Drizzle: A drizzle of dark chocolate sauce on top enhances the dessert's sweetness, creating a delectable contrast that chocolate lovers will adore.

Pineapple Upside-Down Cheesecake Cake Recipe FAQs
How do I know if my pineapple is ripe?
Absolutely! When selecting fresh pineapple, look for one that has a sweet aroma at the base. It should be slightly soft to the touch, and the skin should be golden and free of dark spots. A bright, healthy color indicates ripeness, ready for your delightful cake!
What’s the best way to store leftovers?
Very! After indulging in your Pineapple Upside-Down Cheesecake Cake, store any leftovers in an airtight container in the fridge for up to 3 days. This will help preserve its creamy texture and fresh flavors. If you’re not planning on finishing it within that timeframe, consider freezing it for later enjoyment!
Can I freeze the Pineapple Upside-Down Cheesecake Cake?
Absolutely! To freeze, wrap the cooled cake tightly in plastic wrap, and then wrap it in aluminum foil for added protection. It will stay fresh for up to 2 months in the freezer. When you're ready to enjoy it, simply thaw it in the refrigerator overnight for the best results.
What if my cheesecake cracks during baking?
If you find that your cheesecake has cracked, don't worry—it happens to the best of us! To avoid this in the future, make sure not to overmix the batter and bake at a low temperature to ensure even cooking. A simple fix is to cover the cracks with whipped cream or fresh fruit when serving, adding both flavor and visual appeal.
Is this cake suitable for those with allergies?
When it comes to dietary considerations, this Pineapple Upside-Down Cheesecake Cake contains dairy and eggs, so it’s not suitable for vegans or those with dairy allergies. If you have guests with allergies, substitute the cream cheese with a dairy-free alternative and use egg replacers to ensure everyone can enjoy this delightful dessert!

Irresistibly Creamy Pineapple Upside-Down Cheesecake Cake
Ingredients
Equipment
Method
- Preheat the oven to 325°F (163°C) and prepare a 9-inch springform pan with nonstick spray and aluminum foil.
- Pour melted butter into the prepared pan, sprinkle brown sugar on top, arrange pineapple slices, and place cherries in the center.
- Beat softened cream cheese until smooth, gradually mix in granulated sugar, then add eggs, vanilla, sour cream, and flour.
- Pour cheesecake mixture over the pineapple layer and bake for 40 to 45 minutes.
- Let cool completely and chill in the refrigerator for at least 4 hours.
- Prepare the yellow cake batter according to package instructions and preheat oven to 350°F (175°C).
- Carefully invert the chilled cheesecake onto a greased round cake pan.
- Pour yellow cake batter over the cheesecake and bake for 35 to 40 minutes.
- Allow the cake to cool for 15 minutes, then invert onto a serving plate.





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