Pineapple Upside Down Cheesecake Cake

Name: Pineapple Upside Down Cheesecake Cake
Prep time: 30 min
Cook time: 1 h 15 min
Total time: 2 h 30 min
Cuisine: American
Ingredients: 1 1/2 cups graham cracker crumbs; 1 Tablespoon sugar; 6 Tablespoons melted butter; 4 (8-ounce) packages cream cheese, room temperature; 1 2/3 cups sugar; 1/4 cup cornstarch; 1 Tablespoon vanilla extract; 2 extra large eggs; 3/4 cup heavy cream; 1 can (20 ounces) pineapple slices in juice, drained; 1/2 cup brown sugar; 4 Tablespoons salted butter; Maraschino cherries (about 7); 5 Tablespoons salted butter (additional for cake); 2/3 cup sugar; 2 large eggs; 1/2 cup buttermilk; 1 teaspoon baking powder; 1 teaspoon vanilla extract; 1/4 teaspoon salt; 1/4 teaspoon baking soda; 1 1/4 cups all-purpose flour

By:

Lena Carter

March 1, 2026

Delicious Pineapple Upside Down Cheesecake with pineapple and cherry topping

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Pineapple Upside Down Cheesecake Cake Recipe

Pineapple upside-down cake is a nostalgic dessert that bursts with tropical flavors and a sweetness that ignites fond memories of birthdays and summer gatherings. But imagine combining that classic with a luscious cheesecake—a dreamy creation that’s as visually stunning as it is delicious! This recipe is perfect for celebrations, family dinners, or simply satisfying your dessert cravings, making it a delightful centerpiece at any gathering.

Why You’ll Love This Dish

This Pineapple Upside Down Cheesecake Cake isn’t just about looks—it offers a delightful blend of textures and flavors that will impress your guests and delight your taste buds.

Unique Dessert Experience: The creamy cheesecake layers harmoniously mix with the sweet, caramelized pineapple, creating a symphony of flavors in every bite.
Versatile for Occasions: Whether you’re hosting a festive holiday dinner or celebrating a special anniversary, this cake is sure to steal the spotlight.
Kid-Approved: Kids love both cheesecake and cake, making it a fantastic treat that appeals to all ages.

“This is the ultimate dessert! The cheesecake is rich and creamy, and the pineapple adds a fun twist. Everyone in the family loved it!” – A happy baker’s review.

How to Make Pineapple Upside Down Cheesecake Cake

Creating this show-stopping dessert requires a bit of time, but the steps are straightforward. Here’s what to expect:

Prepare a cheesecak
Assemble the cake layer with pineapple and cherries.
Bake, cool, and combine the layers.

Now let’s break it down!

What You’ll Need

Gathering your ingredients ahead of time will make the process smoother. Here’s what you’ll need:

For the Cheesecake Layer:
- 1 1/2 cups graham cracker crumbs
- 1 Tablespoon sugar
- 6 Tablespoons melted butter (salted or unsalted)
- Four 8-ounce packages of cream cheese (preferably Philadelphia), room temperature
- 1 2/3 cup sugar
- 1/4 cup cornstarch
- 1 Tablespoon vanilla extract
- 2 extra large eggs
- 3/4 cup heavy cream
For the Cake Layer:
- 1 can (20 ounces) pineapple slices in juice, drained
- 1/2 cup brown sugar
- 4 Tablespoons salted butter
- Maraschino cherries (about 7, depending on design)
- 5 Tablespoons salted butter (additional for cake)
- 2/3 cup sugar
- 2 large or extra large eggs
- 1/2 cup buttermilk
- 1 teaspoon baking powder
- 1 teaspoon vanilla extract
- 1/4 teaspoon salt
- 1/4 teaspoon baking soda
- 1 1/4 cups all-purpose flour
- Optional: Extra cherries and warmed caramel sauce for serving

Feel free to substitute fresh fruit or gluten-free cake mix depending on your preferences.

Directions to Follow

Preparing the Cheesecake

Prepare the Cheesecake: The day before serving, preheat your oven to 350°F (175°C). Wrap the bottom and sides of a 9-inch springform pan with heavy aluminum foil to prevent leaks.
Make the Crust: In a mixing bowl, combine graham cracker crumbs, sugar, and melted butter. Press the mixture into the bottom and slightly up the sides of the pan. Bake for 8 minutes and let it cool.
Make the Filling: In a large bowl, beat one package of cream cheese with 1/3 cup sugar and cornstarch on low speed for 3 minutes until creamy. Add remaining cream cheese packages one at a time, mixing well after each.
Mix: Increase the speed to medium, and mix in the rest of the sugar and vanilla. Blend in the eggs, one at a time, then add the cream, mixing until just combined.
Bake: Place the cheesecake pan in a large, shallow baking dish. Pour hot water into the dish until it reaches halfway up the side of the cheesecake. Bake for about 1 hour and 15 minutes until it’s lightly golden. Remove from the water bath and cool for 2 hours, then refrigerate overnight.

Making the Cake

Prepare for the Cake Layer: The next day, preheat your oven to 350°F (175°C) and spray a 9-inch cake pan with cooking spray.
Caramelize the Pineapple: Melt the brown sugar and 4 tablespoons of butter in a saucepan, mixing until combined. Pour this into the prepared cake pan. Arrange the pineapple slices and cherries on top.
Prepare the Cake Batter: Melt the remaining butter in a microwave-safe bowl, combine with sugar and eggs, and then whisk in buttermilk and the rest of the ingredients. Stir in the flour until just combined.
Combine the Layers: Pour the cake batter over the pineapples and bake for about 30 minutes or until a toothpick comes out clean. Cool for 1 minute; then invert onto a flat surface.

Assemble

Final Assembly: Remove the sides of the springform pan from the chilled cheesecake. Place the cake on a serving plate, then carefully slide the pineapple layer on top. Serve with warmed caramel sauce and additional cherries if desired.

Best Ways to Enjoy It

While this cheesecake cake is delicious on its own, there are plenty of ways to elevate your serving experience:

Pair with a dollop of whipped cream as a delightful garnish.
Serve alongside a scoop of vanilla or coconut ice cream for an indulgent experience.
Drizzle with caramel sauce or melted chocolate to add an extra touch of sweetness.

Storage and Reheating Tips

To ensure your leftovers stay fresh, follow these guidelines:

Refrigerate: Store any uneaten cake in the refrigerator for up to 4 days.
Freezing: Wrap each slice in plastic wrap and store in an airtight container before freezing. It can last up to 3 months. Thaw overnight in the refrigerator before serving.
Food Safety: Always ensure to handle your ingredients safely, especially when working with dairy and eggs.

Helpful Cooking Tips

Room Temperature Ingredients: Allow cream cheese and eggs to reach room temperature for a smoother batter.
Don’t Overmix: Carefully beat the batter after adding eggs and cream to avoid a dense cheesecake.
Water Bath Precautions: Ensure no water seeps into the cheesecake during baking to maintain its texture.

Creative Twists

Feeling adventurous? Consider these variations:

Fruit Variations: Swap the pineapple for peaches or strawberries for a different fruity flair.
Flavored Cheesecake: Add lemon zest or coconut extract to the cheesecake filling for a tropical vibe.
Gluten-Free Option: Replace regular graham cracker crumbs with gluten-free options or almond flour for a gluten-free version.

Frequently Asked Questions

How long does prep and bake time take?

Typically, expect about 30 minutes for prep and 2 hours of total baking time, plus overnight chilling for the cheesecake.

Can I substitute fresh pineapple?

Absolutely! Fresh pineapple will work well—just ensure it’s ripe for the best flavor.

How can I store the leftovers securely?

Wrap the cake slices in plastic wrap or store them in an airtight container in the fridge. Be sure to consume them within 4 days for optimal taste.

This Pineapple Upside Down Cheesecake Cake is not just a dessert; it’s a conversation starter infused with nostalgia, flavors, and an air of culinary creativity. Enjoy every bite!