Get ready to fall in love with the Pineapple Upside-Down Cheesecake Cake—a showstopping dessert that marries the sweet nostalgia of pineapple upside-down cake with the creamy indulgence of classic cheesecake. Layers of caramelized pineapple and cherries, creamy vanilla cheesecake, and moist yellow cake come together in a dessert that’s as beautiful as it is delicious. Whether you’re baking for a celebration or just craving something extraordinary, this unique twist on a retro favorite will make everyone swoon.

Ingredients You’ll Need
This Pineapple Upside-Down Cheesecake Cake is pure magic, yet the list of ingredients is refreshingly simple. Each component plays a vital role, from the butter-laced pineapple topping to the creamy cheesecake layer and fluffy cake base—all coming together for amazing flavor, gorgeous color, and the perfect texture contrast.
- Pineapple rings (canned or fresh): Juicy rings add fruity sweetness and a pop of sunshine right on top—use canned for ease or fresh for a touch of tartness.
- Maraschino cherries: These cheery red jewels make the cake irresistible and add a burst of color in every slice.
- Unsalted butter (melted): The base for that golden, caramelized layer that seeps into the fruit.
- Packed light brown sugar: Gives the topping its signature glossy, gooey texture and sweet molasses flavor.
- Cream cheese (softened): The foundation of the cheesecake layer—room temperature for ultimate smoothness.
- Granulated sugar: Balances the tanginess of the cream cheese in the cheesecake layer.
- Large eggs: Essential for both structure and richness in the cheesecake and cake layers.
- Sour cream: Adds a velvety, tangy creaminess to the cheesecake.
- Vanilla extract: Enriches every bite with classic flavor.
- Yellow cake mix: Your trusty shortcut for a fluffy cake layer that always bakes up perfectly.
- Vegetable oil: Keeps the cake ultra-moist and tender.
- Pineapple juice: Infuses the cake with real pineapple flavor—bonus if it’s from your pineapple can!
How to Make Pineapple Upside-Down Cheesecake Cake
Step 1: Prep the Pan and Topping
Start off by lining and greasing a 9-inch springform pan—this helps guarantee easy release and keeps your layers intact. Drizzle the melted butter across the bottom, then scatter the brown sugar over the top for that irresistible caramel effect. Carefully arrange pineapple rings in a single layer and nestle a maraschino cherry snugly in each center. This becomes the star-studded crown of your Pineapple Upside-Down Cheesecake Cake once it’s inverted!
Step 2: Make the Cheesecake Layer
Grab your mixer and beat the softened cream cheese until it’s gloriously smooth and lump-free. Add in the sugar, eggs, sour cream, and vanilla, mixing until creamy and dreamy. Pour this silky-smooth cheesecake batter gently over the arranged pineapple and cherries. Smooth the top with a spatula to create an even layer—this ensures every slice is sheer perfection.
Step 3: Bake and Chill the Cheesecake
Bake your cheesecake layer at 325°F (163°C) for 40 to 45 minutes. You’ll know it’s done when the edges look set but the center still has a light jiggle. Let it cool to room temperature before popping it in the fridge for at least 2 hours (overnight is best if you have the patience!). This crucial step helps the cheesecake set firm enough to layer.
Step 4: Prepare the Cake Batter
Mix up the yellow cake layer while the cheesecake chills. In a large bowl, combine the cake mix, eggs, vegetable oil, and pineapple juice until the batter is velvety and no lumps remain. The pineapple juice infuses subtle tropical flavor, making every bite sing.
Step 5: Layer and Bake the Cake
Once your cheesecake layer is fully chilled and firm, gently remove it from the springform pan and place it in a greased 9-inch round cake pan. Carefully pour the cake batter over the cheesecake layer, smoothing the top. Bake at 350°F (177°C) for 35 to 40 minutes, until a toothpick inserted into the cake layer comes out clean. Allow the cake to cool in the pan for 15 minutes.
Step 6: Invert, Chill, and Serve
Now comes the magic moment! Quickly invert the cake onto a serving platter while it’s still slightly warm—this reveals the golden pineapple and cherry topping. Pop the cake in the fridge to chill for about an hour before slicing. Your Pineapple Upside-Down Cheesecake Cake is ready to dazzle!
How to Serve Pineapple Upside-Down Cheesecake Cake

Garnishes
A dollop of freshly whipped cream and a sprinkling of toasted coconut take this cake to delicious new heights. If you’re feeling fancy, garnish with a fresh pineapple wedge or extra maraschino cherries for a celebratory finish—no one can resist that tropical flair!
Side Dishes
For a dessert spread, balance the sweetness of your Pineapple Upside-Down Cheesecake Cake with simple sides like fresh berries or a tart lemon sorbet. A scoop of vanilla ice cream also complements the warm, buttery flavors beautifully, making dessert hour unforgettable.
Creative Ways to Present
Turn your cake into a special occasion centerpiece! Bake mini versions for individual pineapple upside-down cheesecakes, or slice and serve on platter tiers with fresh fruit in between. For a party, try cutting into bars for a handheld treat—guaranteed crowd-pleasers every time.
Make Ahead and Storage
Storing Leftovers
Leftover Pineapple Upside-Down Cheesecake Cake stores wonderfully in the refrigerator for up to four days. Simply wrap the cake tightly with plastic wrap or pop it into an airtight container to keep it moist and flavorful. The topping gets even gooier and more delicious as it rests!
Freezing
Yes, you can freeze this cake! Slice it into portions, wrap each slice in plastic wrap, and then in foil before placing them in a freezer bag. The Pineapple Upside-Down Cheesecake Cake stays delicious in the freezer for up to two months. Thaw overnight in the fridge before serving.
Reheating
If you like your cake slightly warm, gently reheat slices in the microwave for about 15 seconds. This revives the buttery caramel topping and softens the textures—just enough to make every bite taste freshly baked! Avoid overheating to protect the cheesecake’s creamy consistency.
FAQs
Can I make the Pineapple Upside-Down Cheesecake Cake a day ahead?
Absolutely! In fact, making it a day ahead can improve both flavor and texture. The layers have time to meld and the topping becomes extra luscious. Just keep it chilled until ready to serve for best results.
Can I use fresh pineapple instead of canned?
Yes, you can use fresh pineapple for a more tangy, juicy kick. Slice the pineapple into rings about 1/2 inch thick for consistent baking. Just make sure to pat them dry with paper towels to avoid excess moisture in the topping.
What if I don’t have a springform pan?
While a springform pan makes removing the cheesecake layer a breeze, you can use a regular 9-inch round cake pan lined with parchment. Run a knife around the edge before releasing, and invert carefully to keep the layers intact.
Can I use a homemade cake batter instead of a box mix?
Definitely! If you prefer baking cake from scratch, swap in your favorite yellow cake recipe. Just keep the ingredient ratios similar—you want a batter that’s sturdy enough to support the cheesecake but soft and fluffy.
Why does the cheesecake need to chill before adding the cake layer?
Chilling the cheesecake ensures it’s firm and set, which prevents the cake batter from mixing into it when layered. This step is crucial for creating those distinct, gorgeous layers in your Pineapple Upside-Down Cheesecake Cake.
Final Thoughts
If you’re looking to wow your friends and family, nothing compares to the flavor and flair of this Pineapple Upside-Down Cheesecake Cake. Trust me, every luscious bite is worth the little bit of effort—so go ahead and try it. You’ll never look at pineapple upside-down cake the same way again!
Print
Pineapple Upside-Down Cheesecake Cake Recipe
- Prep Time: 45 minutes
- Cook Time: 1 hour 20 minutes
- Total Time: 2 hours 5 minutes (plus chilling time)
- Yield: 12 servings
- Category: Dessert
- Method: Baking
- Cuisine: American
- Diet: Vegetarian
Description
Indulge in the decadent fusion of pineapple upside-down cake and creamy cheesecake with this Pineapple Upside-Down Cheesecake Cake. Layers of sweet pineapple, rich cheesecake, and moist yellow cake come together for a show-stopping dessert that’s perfect for any occasion.
Ingredients
Pineapple Topping:
- 1/4 cup unsalted butter, melted
- 1/2 cup packed light brown sugar
- 6–8 pineapple rings (canned or fresh)
- 6–8 maraschino cherries
Cheesecake Layer:
- 2 (8 oz) blocks cream cheese, softened
- 1/2 cup granulated sugar
- 2 large eggs
- 1/4 cup sour cream
- 1 teaspoon vanilla extract
Cake Layer:
- 1 box yellow cake mix
- 3 large eggs
- 1/2 cup vegetable oil
- 1 cup pineapple juice (from canned pineapple or fresh)
Instructions
- Prepare Pineapple Topping: Preheat oven to 325°F (163°C). Grease and line a 9-inch springform pan. Pour melted butter in the pan, sprinkle brown sugar, arrange pineapple rings, and place cherries on top.
- Make Cheesecake Layer: Beat cream cheese until smooth, add sugar, eggs, sour cream, and vanilla. Pour over pineapple layer and bake.
- Prepare Cake Layer: Combine cake mix, eggs, oil, and pineapple juice. Pour over chilled cheesecake layer and bake.
- Chill and Serve: Cool, invert onto a platter, and chill before serving.
Notes
- Use canned pineapple rings for consistent size
- Chill cheesecake before adding cake batter
- Store leftovers in the fridge for up to 4 days
Nutrition
- Serving Size: 1 slice
- Calories: 520
- Sugar: 42g
- Sodium: 410mg
- Fat: 27g
- Saturated Fat: 14g
- Unsaturated Fat: 10g
- Trans Fat: 0.5g
- Carbohydrates: 64g
- Fiber: 1g
- Protein: 6g
- Cholesterol: 105mg