If you love the tropical sweetness of pineapple upside down cake and the creamy indulgence of cheesecake, these Mini Pineapple Upside Down Cheesecakes bring you the best of both worlds in one perfectly portioned dessert. With buttery caramelized pineapple, sweet maraschino cherries, and a smooth cheesecake filling, they’re fun, festive, and incredibly easy to make.
Want recipes like this delivered straight to your inbox? Subscribe now to get the latest culinary creations you’ll love.
Why You’ll Love This Recipe
Two Desserts in One – A fusion of pineapple upside down cake and cheesecake.
Perfectly Portioned – Great for parties, picnics, or anytime sweet cravings.
Tropical Flavor – Pineapple, cherry, and vanilla all wrapped in creamy goodness.
Make-Ahead Friendly – Chill and serve when ready.
Eye-Catching & Fun – Beautiful presentation that’s sure to impress.
Ingredients You’ll Need
For the Fruit Layer:
- ¼ cup unsalted butter, melted
- ⅓ cup brown sugar, packed
- 12 maraschino cherries
- 1 cup canned pineapple tidbits or crushed pineapple (drained well)
For the Crust:
- ¾ cup graham cracker crumbs
- 2 tbsp granulated sugar
- 3 tbsp unsalted butter, melted
For the Cheesecake Filling:
- 16 oz cream cheese, softened
- ½ cup granulated sugar
- 2 large eggs
- 1 tsp vanilla extract
- 2 tbsp sour cream
- 1 tbsp all-purpose flour (helps stabilize)
Tools You’ll Need
- Standard 12-cup muffin tin
- Cupcake liners
- Mixing bowls
- Electric mixer
- Spoon or scoop
- Cooling rack
Step-by-Step Instructions
Step 1: Prepare the Muffin Tin
- Preheat oven to 325°F (163°C).
- Line each cavity of a 12-cup muffin pan with cupcake liners.
- Spoon about 1 teaspoon of melted butter into each liner, followed by 1 teaspoon of brown sugar.
- Add a cherry in the center and spoon 1 tablespoon of drained pineapple around it. Set aside.
Step 2: Make the Crust
- In a small bowl, combine graham cracker crumbs, sugar, and melted butter.
- Stir until the texture resembles wet sand.
- Press about 1 tablespoon of the crust mixture into each cup over the pineapple layer.
- Press down firmly with a spoon or bottom of a small glass.
Step 3: Make the Cheesecake Filling
- In a large bowl, beat the softened cream cheese until smooth.
- Add granulated sugar and mix until combined and creamy.
- Beat in eggs, one at a time.
- Add vanilla extract, sour cream, and flour. Mix just until smooth and well combined.
Step 4: Fill and Bake
- Spoon the cheesecake filling over the crusts, filling each liner almost to the top.
- Bake for 18–22 minutes, or until the centers are set and no longer jiggle.
- Remove from oven and cool in the pan for 10 minutes.
- Carefully transfer to a wire rack to cool completely, then chill in the fridge for at least 2 hours.
Step 5: Unmold and Serve
- Once chilled, carefully peel back the liners and invert the cheesecakes onto a serving platter.
- The caramelized pineapple and cherry should now be on top—beautiful and glossy.
- Garnish with fresh mint if desired and serve cold.
Tips for Perfect Mini Cheesecakes
Drain the Pineapple Well – Excess juice can make the crust soggy.
Use Room Temperature Cream Cheese – Ensures a smooth, lump-free filling.
Don’t Overbake – The center should just be set to keep them creamy.
Chill Thoroughly – Cold cheesecakes hold their shape better when unmolded.
Gently Invert – Use care when flipping to keep the topping in place.
Serving Suggestions
With Whipped Cream – A light topping to balance the richness.
On a Dessert Platter – Pair with mini tarts, brownies, and cookies for variety.
For Tropical Vibes – Serve with coconut flakes or mango slices.
At Brunch – A sweet option alongside savory items and fresh fruit.
For Holidays or Birthdays – A fun and elegant individual treat.
How to Store & Reheat
Storing:
- Refrigerate: Keep in an airtight container for up to 4 days.
- Freeze: Wrap individually and freeze for up to 1 month. Thaw in the fridge before serving.
Reheating:
- Not needed—these cheesecakes are best served chilled.
Frequently Asked Questions
1. Can I use fresh pineapple?
Yes, just chop finely and drain well before using.
2. Do I have to use cupcake liners?
Highly recommended for easy removal. If not using liners, grease the muffin tin very well and use a knife to loosen edges.
3. Can I make this in a mini muffin pan?
Yes, reduce baking time to 10–12 minutes. Watch closely for doneness.
4. Can I use a different crust?
Sure! Crushed vanilla wafers or shortbread cookies make great alternatives.
5. Are they gluten-free?
Use gluten-free graham crackers and ensure all other ingredients are labeled gluten-free.
Final Thoughts
Mini Pineapple Upside Down Cheesecakes are a fun and delicious twist on two classic desserts. With their tropical flavor, creamy texture, and eye-catching presentation, they’re sure to become a favorite for any occasion. Whether you’re hosting a party or treating yourself to something special, these minis are a guaranteed hit.
Try it out and let me know what you think! Don’t forget to leave a review below and share your photos on Pinterest! I can’t wait to see how your cheesecakes turn out.
Preparation Time: 20 minutes
Cooking Time: 20 minutes
Chilling Time: 2 hours
Cuisine: American
Nutritional Information (Per Serving):
Calories: 270 | Protein: 4g | Carbohydrates: 24g | Fat: 18g | Fiber: 1g | Sodium: 140mg

Mini Pineapple Upside Down Cheesecakes
- Total Time: 40 minutes
Description
If you love the tropical sweetness of pineapple upside down cake and the creamy indulgence of cheesecake, these Mini Pineapple Upside Down Cheesecakes bring you the best of both worlds in one perfectly portioned dessert. With buttery caramelized pineapple, sweet maraschino cherries, and a smooth cheesecake filling, they’re fun, festive, and incredibly easy to make.
Want recipes like this delivered straight to your inbox? Subscribe now to get the latest culinary creations you’ll love.
Ingredients
For the Fruit Layer:
-
¼ cup unsalted butter, melted
-
⅓ cup brown sugar, packed
-
12 maraschino cherries
-
1 cup canned pineapple tidbits or crushed pineapple (drained well)
For the Crust:
-
¾ cup graham cracker crumbs
-
2 tbsp granulated sugar
-
3 tbsp unsalted butter, melted
For the Cheesecake Filling:
-
16 oz cream cheese, softened
-
½ cup granulated sugar
-
2 large eggs
-
1 tsp vanilla extract
-
2 tbsp sour cream
-
1 tbsp all-purpose flour (helps stabilize)
Instructions
Step 1: Prepare the Muffin Tin
-
Preheat oven to 325°F (163°C).
-
Line each cavity of a 12-cup muffin pan with cupcake liners.
-
Spoon about 1 teaspoon of melted butter into each liner, followed by 1 teaspoon of brown sugar.
-
Add a cherry in the center and spoon 1 tablespoon of drained pineapple around it. Set aside.
Step 2: Make the Crust
-
In a small bowl, combine graham cracker crumbs, sugar, and melted butter.
-
Stir until the texture resembles wet sand.
-
Press about 1 tablespoon of the crust mixture into each cup over the pineapple layer.
-
Press down firmly with a spoon or bottom of a small glass.
Step 3: Make the Cheesecake Filling
-
In a large bowl, beat the softened cream cheese until smooth.
-
Add granulated sugar and mix until combined and creamy.
-
Beat in eggs, one at a time.
-
Add vanilla extract, sour cream, and flour. Mix just until smooth and well combined.
Step 4: Fill and Bake
-
Spoon the cheesecake filling over the crusts, filling each liner almost to the top.
-
Bake for 18–22 minutes, or until the centers are set and no longer jiggle.
-
Remove from oven and cool in the pan for 10 minutes.
-
Carefully transfer to a wire rack to cool completely, then chill in the fridge for at least 2 hours.
Step 5: Unmold and Serve
-
Once chilled, carefully peel back the liners and invert the cheesecakes onto a serving platter.
-
The caramelized pineapple and cherry should now be on top—beautiful and glossy.
-
Garnish with fresh mint if desired and serve cold.
Notes
Drain the Pineapple Well – Excess juice can make the crust soggy.
Use Room Temperature Cream Cheese – Ensures a smooth, lump-free filling.
Don’t Overbake – The center should just be set to keep them creamy.
Chill Thoroughly – Cold cheesecakes hold their shape better when unmolded.
Gently Invert – Use care when flipping to keep the topping in place.
- Prep Time: 20 minutes
- Cook Time: 20 minutes
- Cuisine: American