Pineapple Upside-Down Cheesecake

Posted on January 1, 2026

Modified: January 1, 2026

By Antonio
A delicious slice of Pineapple Upside-Down Cheesecake with a graham cracker crust, creamy filling, pineapple, cherries, and whipped cream.

Oh, this Pineapple Upside-Down Cheesecake! The caramelized pineapple, the tangy cream cheese filling, and that buttery graham cracker crust… it’s a symphony of flavors that just sings to my soul. I love creating new versions of classic desserts, just like my No-Bake Orange Creamsicle Cheesecake, and this recipe is no exception.

I remember when my grandma used to make pineapple upside-down cake for every family gathering. The sweet, comforting aroma would fill the whole house. This recipe is a tribute to those cherished memories.

This Pineapple Upside-Down Cheesecake is both decadent and surprisingly easy to make. Plus, it’s a guaranteed crowd-pleaser! My secret is the touch of sour cream in the cheesecake filling, which adds a delightful tang.

What You Need to Make This Recipe

This Pineapple Upside-Down Cheesecake brings together the best of both worlds: the familiar sweetness of pineapple upside-down cake with the creamy richness of cheesecake. The buttery brown sugar caramel, the juicy pineapple slices, and the creamy cheesecake filling create a truly irresistible dessert. You’ll find the full list of ingredients and measurements in the recipe card below. And if you like to experiment with your desserts, you can find inspiration in this Funfetti Angel Food Cake!

pineapple upside down cheesecake recipe
Pineapple Upside-Down Cheesecake 5

How to Make Pineapple Upside-Down Cheesecake

Making this Pineapple Upside-Down Cheesecake is easier than you might think! It starts with a buttery caramel base topped with pineapple slices and cherries, followed by a creamy cheesecake filling, and finally baked to golden perfection. The result is a stunning dessert that’s sure to impress. If you want the perfect texture, just think about this Fluffy Pink Angel Food Cake while you are mixing the ingredients.

Pro Tips for Making This Pineapple Upside-Down Cheesecake

To ensure your Pineapple Upside-Down Cheesecake turns out perfectly every time, here are a few of my go-to tips:

  • Don’t skip the graham cracker crust: It adds a lovely textural contrast to the creamy filling and provides a sturdy base.

  • Use room-temperature ingredients: This will help the cheesecake filling come together smoothly and prevent lumps.

  • Bake in a water bath: This helps to keep the cheesecake moist and prevents cracking.

For Extra Flavor

  • Add a pinch of cinnamon or nutmeg to the graham cracker crust for a warm, spicy note.
  • Use dark brown sugar instead of light brown sugar for a richer caramel flavor.

Avoiding Common Mistakes

  • Don’t overbake the cheesecake: It should still have a slight jiggle in the center when you remove it from the oven.
  • Let the cheesecake cool completely before refrigerating: This will prevent condensation from forming on the surface.

My Secret Trick: I always place a layer of parchment paper between the pineapple and the cheesecake filling. This prevents the pineapple from becoming soggy and keeps the cheesecake nice and firm.

pineapple upside down cheesecake pinterest
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Fun Variations for Pineapple Upside-Down Cheesecake

Want to put your own spin on this Pineapple Upside-Down Cheesecake? Here are a few fun and easy variations:

  • Coconut Dream: Add shredded coconut to the graham cracker crust and the cheesecake filling for a tropical twist.
  • Berry Bliss: Use mixed berries instead of pineapple for a colorful and flavorful variation.
  • Chocolate Lover’s Delight: Swirl melted chocolate into the cheesecake filling for a decadent treat.
  • Caramel Swirl: Add a ribbon of caramel sauce to the filling before baking to enhance the rich flavors.

How to Store Pineapple Upside-Down Cheesecake

To keep your Pineapple Upside-Down Cheesecake fresh and delicious, store it in the refrigerator, covered tightly, for up to 3-4 days. You can also freeze it for longer storage; wrap it tightly in plastic wrap and then in foil, and it will keep for up to 2 months. When ready to enjoy, thaw it overnight in the refrigerator. Reheating gently can bring back the flavors, but I usually enjoy it cold!

Nutritional Benefits

While Pineapple Upside-Down Cheesecake is definitely a treat, it does offer some nutritional benefits. Pineapple is a good source of vitamin C and bromelain, an enzyme with anti-inflammatory properties. Plus, the dairy ingredients provide calcium and protein, making it a slightly less guilty pleasure for the whole family.

FAQs

Can I use canned pineapple instead of fresh?

Yes, you can use canned pineapple slices for this Pineapple Upside-Down Cheesecake. Just make sure to drain them well before using to prevent the cheesecake from becoming soggy. I recommend using pineapple slices in juice rather than syrup for a less sugary result.

Can I make this cheesecake ahead of time?

Absolutely! This Pineapple Upside-Down Cheesecake is a great make-ahead dessert. In fact, I often find that the flavors meld together even better after it has been refrigerated overnight. Just be sure to store it properly to maintain its freshness.

What is a water bath and why is it important?

A water bath involves placing the cheesecake pan in a larger pan filled with hot water during baking. This creates a humid environment that helps the cheesecake bake evenly and prevents it from cracking. For a Pineapple Upside-Down Cheesecake, it ensures a smooth and creamy texture.

Can I freeze this Pineapple Upside-Down Cheesecake?

Yes, you can freeze this Pineapple Upside-Down Cheesecake. Wrap it tightly in plastic wrap and then in foil, and it will keep for up to 2 months. Thaw it overnight in the refrigerator before serving.

A delicious slice of Pineapple Upside-Down Cheesecake with a graham cracker crust, creamy filling, pineapple, cherries, and whipped cream.
ec1e86bc8055c952d4763129110a16bb02d1976091eb51bb2a4cc20c42d4dbfa?s=30&d=https%3A%2F%2Fyummyget.com%2Fwp content%2Fuploads%2F2024%2F11%2Fcropped FOOD Website 2 iconAntonio

Pineapple Upside-Down Cheesecake

A delightful twist on a classic! This Pineapple Upside-Down Cheesecake combines the tangy sweetness of pineapple with the creamy richness of cheesecake for an unforgettable dessert.
Prep Time 45 minutes
Cook Time 1 hour 15 minutes
Total Time 2 hours
Servings: 12 servings
Course: Dessert
Cuisine: American
Calories: 450

Ingredients
  

  • 1/2 cup Unsalted Butter melted
  • 3/4 cup Light Brown Sugar packed
  • 20 oz Pineapple Slices drained
  • 1/4 cup Maraschino Cherries halved
  • 1 1/2 cups Graham Cracker Crumbs
  • 1/4 cup Granulated Sugar
  • 6 tbsp Unsalted Butter melted
  • 32 oz Cream Cheese room temperature
  • 1 1/4 cups Granulated Sugar
  • 1/4 cup Sour Cream room temperature
  • 2 tsp Vanilla Extract
  • 4 Large Eggs room temperature
  • 2 tbsp All-Purpose Flour

Equipment

  • 9-inch springform pan
  • Mixer
  • Mixing Bowls
  • Spatula

Method
 

  • Preheat oven and prepare pan.
  • Arrange fruit attractively.
  • Prepare crust.
  • Make cheesecake filling.
  • Continue filling.
  • Assemble and bake.
  • Cool gradually.
  • Chill.
  • Invert.
  • Enjoy!

Notes

For best results, use room temperature ingredients. To prevent cracking, bake in a water bath. Leftovers can be stored in the refrigerator for up to 3 days.

Conclusion

This Pineapple Upside-Down Cheesecake is a delightful twist on a classic dessert, perfect for any occasion. With its layers of caramelized pineapple, creamy cheesecake, and buttery graham cracker crust, it’s a guaranteed crowd-pleaser. So gather your ingredients, preheat your oven, and get ready to create a sweet masterpiece that will bring joy to your family and friends. I encourage you to try this Raspberry Coconut Snowball Cake as well!

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