Pineapple Upside Down Cupcakes are the perfect miniature version of the classic cake with buttery yellow cake, pineapple chunks, and cherries.
This amazing miniature Cake Recipe is the perfect cupcake version of Pineapple Upside Down Cake. If you love this adaptation, you should also try my sweet Strawberry Upside Down Cake!

Sabrina’s Pineapple Upside Down Cupcakes
This recipe takes an iconic dessert and makes them into adorable cupcakes that are the perfect addition to any celebration. Bright red and yellow colors from the fruit make the cakes look amazing, and are sure to bring a smile to everyone’s face. Making them into cupcakes makes this classic pineapple dessert easy to serve to a crowd without worrying about slicing the cake into pieces.


Ingredients
Topping Ingredients (Go into the muffin tin first)
- 3 tablespoons unsalted butter , melted
- 1/2 cup brown sugar , packed
- 20 ounces pineapple chunks in juice , drained (reserve ¼ cup of juice for cake)
- 12 maraschino cherries , stems removed
Cake Batter Ingredients
- 1 1/3 cups flour
- 1 teaspoon baking powder
- 1/2 teaspoon kosher salt
- 1/4 cup unsalted butter , softened
- 1/2 cup sugar
- 1/4 cup brown sugar , packed
- 1 large egg
- 1 teaspoon vanilla extract
- 1/4 cup sour cream
Instructions
- Preheat the oven to 350 degrees.
- Spray a 12 cup muffin tin with baking spray.
- Melt the butter and brown sugar in a microwave-safe bowl then mix together and pour into the muffin tins.
- Add pineapple chunks to the bottom of muffin tins then place cherries in the middle of the circles.
- To your stand mixer add butter, sugar, and brown sugar on medium speed until light and fluffy, for 1-2 minutes.
- Add in the egg, vanilla extract, sour cream, and pineapple juice at low speed until combined.
- Sift together flour, baking powder and salt then add it into the stand mixer on low speed until just combined.
- Spoon batter carefully into muffin tin until ¾ full.
- Bake for 20-22 minutes or until a toothpick comes out clean.
- Let cool for 10 minutes.
- Place baking sheet upside down on muffin tin and flip over quickly while still warm.
Nutrition
Table of contents
About this Recipe
Just like the classic cake, these cupcakes have a pineapple cherry layer that’s baked on the bottom but served on top. To make a mini version, you simply add the fruity, caramel topping to the bottom of muffin cups, then scoop the cake batter over top. And just like the regular cake, once it’s all baked you flip the pan. Instead of one whole cake you have a dozen cute pineapple and cherry topped treats! These tropical cupcakes are the perfect way to end a summer BBQ or pool party. I like to serve them with a swirl of whipped cream and an extra cherry as an easy decoration.
Key Ingredients
- Pineapple: The cans of pineapple from the store are sweetened which add to the sugary caramel topping! If your pineapple is not cut into chunks, you’ll need to cut them up so they fit around the bottom of the muffin cup.
- Cherry: The sweet and slightly tartness of maraschino cherries add a pop of color and are a classic part of this iconic cake.
- Cake Batter: I upgraded my regular homemade yellow cake mixture with sour cream which gives it an extra richness and makes the cake practically melt in your mouth!
How to Make
Time needed: 40 minutes
- Prep time
Preheat the oven to 350 degrees. Then spray a 12-cup muffin tin with nonstick cooking spray. You want to use nonstick spray instead of paper liners so that the cupcakes will easily come out with the pineapple topping.
- Topping
Melt the butter and brown sugar in a microwave-safe bowl. Mix the ingredients together and divide it evenly into the muffin cups. Add the pineapple pieces on top, then place cherries in the middle of the pineapples.
- Cake batter
Add the butter, granulated sugar, and brown sugar to your electric stand mixer. Mix for 1-2 minutes until light and fluffy. Then add in the egg, vanilla extract, sour cream, and pineapple juice. Turn the electric mixer to low speed until combined. Then sift in the flour, baking powder, and salt. Mix at low speed again until just combined.
- Baking time
Spoon the batter from the bowl into the muffin cups over the sliced pineapple. Pop the pan in the preheated oven to bake for 20-22 minutes. Keep the cupcakes in the oven until a toothpick inserted in the center of one comes out clean.
- Cool and Flip
Let the cupcakes cool down for 10 minutes while still in the tin. After 10 minutes run a knife around the edge of each cake to loosen them up. Then put a baking sheet on top of the muffin tin, and flip it over so the cupcakes come out with the pineapple slices on top.
Can this be made ahead of time?
Yes, absolutely! This is a great treat to make ahead of time. Simply bake it according to the instructions below and store it in an airtight container in the fridge for up to 3 days before you want to serve them. Technically they will say good for 5 days but they taste freshest they first few days.
How to Store
- Serve: You don’t want to leave these cupcakes at room temperature for more than 2 hours.
- Store: Cover the cupcakes or put them in an airtight container to store in the fridge for up to 5 days.
- Freeze: You can also freeze the pineapple cakes for up to 1 month. Take them out of the freezer and let them thaw in the fridge for a few hours before dessert time.
Frequently Asked Questions
Traditional cakes are baked and then the topping is added on after it has finished baking. With upside down cakes, the topping is baked into the cake by being placed first in the baking dish and the batter cooking on top of it. When it’s finished baking, it’s flipped upside down so that it’s ready to serve!
Yes, you can. Be aware that fresh pineapple will not have the extra sweetness that canned pineapple does because it won’t have the syrup. Be sure to cut the pineapple up into chunks about an inch thick.
Simply place a baking sheet upside down onto the muffin tin. While the cupcakes are still warm, hold both sheet and tin together and quickly flip it with caution. With the baking sheet flat on the table or counter, lift the muffin tin up. The cupcakes should just fall right out. If not, then you can coax them with a little pressure from a fork or your hand.
Variations
- Yellow cake mix: Instead of fully making a cake from scratch, you can save time by using a boxed cake mix. To make the boxed cake mix extra moist, add one extra egg to what the back of the box said. You should also exchange the water with milk and the oil with melted butter.
- Coconut: Coconut and pineapple make a wonderful tropical flavor combo. Sprinkle coconut flakes into the pineapple topping and add some coconut extract to the cake batter.
- Different Berries: For some variations in the fruit topping, you can try using different kinds of berries like blueberries, strawberries, or raspberries.
More Delicious Pineapple Desserts

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