These Mini Pineapple Upside Down Cheesecakes are a delightful fusion of two classic desserts in one bite-sized treat. Buttery caramelized pineapple and cherries form a golden topping over creamy cheesecake and a sweet graham cracker crust. They’re perfect for parties, holidays, or anytime you want a tropical twist on traditional cheesecake.
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Why You’ll Love This Recipe
Two Desserts in One – Combines pineapple upside down cake and cheesecake.
Perfect Portions – Great for serving at parties or gatherings.
Tropical Flavor – Pineapple and cherry topping adds sweet, fruity goodness.
Make-Ahead Friendly – Chill and serve when ready.
Eye-Catching – A beautiful, glossy finish in every mini bite.
Ingredients You’ll Need
For the Topping:
- ¼ cup unsalted butter, melted
- ½ cup brown sugar
- 12 canned pineapple rings, cut to fit muffin cups
- 12 maraschino cherries
For the Crust:
- 1 cup graham cracker crumbs
- 3 tbsp granulated sugar
- 4 tbsp unsalted butter, melted
For the Cheesecake Filling:
- 16 oz cream cheese, softened
- ½ cup granulated sugar
- 2 large eggs
- 1 tsp vanilla extract
- ¼ cup sour cream
- 1 tbsp all-purpose flour
Tools You’ll Need
- 12-cup muffin pan
- Cupcake liners or nonstick spray
- Electric mixer or hand mixer
- Mixing bowls
- Spatula
- Spoon or cookie scoop
- Wire rack
Step-by-Step Instructions
Step 1: Prep the Muffin Pan
Preheat your oven to 325°F (160°C).
Line a muffin pan with paper liners or grease generously with nonstick spray.
Step 2: Add the Topping
In a small bowl, mix melted butter and brown sugar.
Spoon about 1 tbsp of this mixture into the bottom of each muffin cup.
Place a small piece of pineapple (cut to fit) and one maraschino cherry in each cup, pressing them gently into the sugar mixture.
Step 3: Make the Crust
In a medium bowl, combine graham cracker crumbs, sugar, and melted butter.
Press about 1 to 1½ tbsp of the mixture into each cup over the pineapple layer, pressing firmly to form a crust.
Set aside.
Step 4: Make the Cheesecake Filling
In a large bowl, beat cream cheese until smooth and creamy.
Add sugar and beat until combined.
Mix in eggs one at a time, scraping the bowl as needed.
Add vanilla, sour cream, and flour, and mix until smooth.
Spoon the cheesecake mixture evenly over each crust, filling nearly to the top.
Step 5: Bake the Mini Cheesecakes
Bake for 18–22 minutes, or until centers are set and edges are slightly puffed.
Turn off the oven and let cheesecakes sit inside for 5 minutes with the door ajar.
Remove and cool completely at room temperature, then refrigerate for at least 2 hours (or overnight).
Step 6: Invert and Serve
Once chilled, carefully remove each cheesecake from the pan.
Invert onto a plate or serving platter so the pineapple and cherry are on top.
Serve chilled or at room temperature for best texture.
Tips for the Best Mini Pineapple Upside Down Cheesecakes
Use Canned Pineapple – It’s the perfect texture and sweetness. Cut to fit muffin cups.
Chill Completely – Allows the cheesecakes to set and makes removing easier.
Use Paper Liners – Makes for simpler cleanup and serving.
Wipe Knife Clean – If slicing or trimming, use a clean knife for sharp edges.
Decorate Simply – A dollop of whipped cream or mint leaf adds a nice touch.
Serving Suggestions
Party Platters – Add to dessert trays for showers, brunches, or holidays.
Tropical Dessert Table – Pair with coconut macaroons or mango mousse.
Mini Cheesecake Sampler – Serve alongside chocolate or berry mini cheesecakes.
Light Treat – Enjoy with iced coffee or tea for a summery snack.
How to Store & Reheat
Storing:
- Refrigerate: Store in an airtight container for up to 4–5 days.
- Freeze: Wrap tightly and freeze for up to 1 month. Thaw in the fridge before serving.
Reheating:
- Not needed—best served chilled or at room temperature.
Frequently Asked Questions
1. Can I make this without a muffin pan?
You can use a mini cheesecake pan or ramekins, but muffin tins are easiest for individual servings.
2. Can I use fresh pineapple?
Yes, but it should be thinly sliced and slightly cooked or caramelized before using to avoid excess moisture.
3. Can I make them gluten-free?
Absolutely—use gluten-free graham crackers for the crust.
4. How do I prevent cracks in cheesecake?
Avoid overmixing and do not overbake. Let them cool gradually.
5. Can I make these ahead of time?
Yes! These are ideal for making 1–2 days ahead and storing in the fridge until ready to serve.
Final Thoughts
Mini Pineapple Upside Down Cheesecakes are the perfect combination of creamy, fruity, and indulgent. These bite-sized beauties are guaranteed to steal the show at any gathering and are easy enough to whip up whenever you need a sweet tropical escape.
Make them once and they’ll be requested again and again! Share your mini masterpieces online and let me know how they turned out!
Preparation Time: 20 minutes
Baking Time: 20 minutes
Chill Time: 2+ hours
Cuisine: American
Nutritional Information (Per Cheesecake):
Calories: 260 | Protein: 4g | Carbohydrates: 24g | Fat: 17g | Fiber: 1g | Sugar: 16g | Sodium: 150mg

Mini Pineapple Upside Down Cheesecakes
- Total Time: 20 minutes
Description
These Mini Pineapple Upside Down Cheesecakes are a delightful fusion of two classic desserts in one bite-sized treat. Buttery caramelized pineapple and cherries form a golden topping over creamy cheesecake and a sweet graham cracker crust. They’re perfect for parties, holidays, or anytime you want a tropical twist on traditional cheesecake.
Want recipes like this delivered straight to your inbox? Subscribe now to get the latest culinary creations you’ll love.
Ingredients
For the Topping:
-
¼ cup unsalted butter, melted
-
½ cup brown sugar
-
12 canned pineapple rings, cut to fit muffin cups
-
12 maraschino cherries
For the Crust:
-
1 cup graham cracker crumbs
-
3 tbsp granulated sugar
-
4 tbsp unsalted butter, melted
For the Cheesecake Filling:
-
16 oz cream cheese, softened
-
½ cup granulated sugar
-
2 large eggs
-
1 tsp vanilla extract
-
¼ cup sour cream
-
1 tbsp all-purpose flour
Instructions
Step 1: Prep the Muffin Pan
Preheat your oven to 325°F (160°C).
Line a muffin pan with paper liners or grease generously with nonstick spray.
Step 2: Add the Topping
In a small bowl, mix melted butter and brown sugar.
Spoon about 1 tbsp of this mixture into the bottom of each muffin cup.
Place a small piece of pineapple (cut to fit) and one maraschino cherry in each cup, pressing them gently into the sugar mixture.
Step 3: Make the Crust
In a medium bowl, combine graham cracker crumbs, sugar, and melted butter.
Press about 1 to 1½ tbsp of the mixture into each cup over the pineapple layer, pressing firmly to form a crust.
Set aside.
Step 4: Make the Cheesecake Filling
In a large bowl, beat cream cheese until smooth and creamy.
Add sugar and beat until combined.
Mix in eggs one at a time, scraping the bowl as needed.
Add vanilla, sour cream, and flour, and mix until smooth.
Spoon the cheesecake mixture evenly over each crust, filling nearly to the top.
Step 5: Bake the Mini Cheesecakes
Bake for 18–22 minutes, or until centers are set and edges are slightly puffed.
Turn off the oven and let cheesecakes sit inside for 5 minutes with the door ajar.
Remove and cool completely at room temperature, then refrigerate for at least 2 hours (or overnight).
Step 6: Invert and Serve
Once chilled, carefully remove each cheesecake from the pan.
Invert onto a plate or serving platter so the pineapple and cherry are on top.
Serve chilled or at room temperature for best texture.
Notes
Use Canned Pineapple – It’s the perfect texture and sweetness. Cut to fit muffin cups.
Chill Completely – Allows the cheesecakes to set and makes removing easier.
Use Paper Liners – Makes for simpler cleanup and serving.
Wipe Knife Clean – If slicing or trimming, use a clean knife for sharp edges.
Decorate Simply – A dollop of whipped cream or mint leaf adds a nice touch.
- Prep Time: 20 minutes
- Cuisine: American