Make Pineapple Upside Down Cupcakes for a fun and delicious twist on the traditional pineapple upside down cake. These individual servings are perfect for parties, potlucks and more.

I’m so excited to share this easy recipe for upside down pineapple cupcakes. This dessert is full of pineapple flavor and so moist and delicious. Cupcake Recipes are always a hit, and this one is sure to impress.
Not only are they so yummy but they look gorgeous. If you enjoyed our Pineapple Upside Down Cake, this is another must try recipe. These cupcakes are made with simple ingredients and the perfect size. You might also like Hummingbird Bread and Pineapple Cookies.
Table of contents
What are Pineapple Upside Down Cupcakes?
If you love the classic pineapple upside down cake, then you must make these cupcakes. They are the mini version of the classic cake and they are the perfect size for your next BBQ.
Ingredients

- Canned Pineapple Slices. The rings are easier to work with because you can cut them into pieces. You can use diced but sometimes those are thicker, and I just find the rings easier.
- Yellow Cake Mix. This variety will give the cupcakes the same taste as the traditional cake recipe.
- Brown Sugar. Try making The Best Brown Sugar Substitutes.
Scroll to the bottom of the page for the complete ingredient list.
Variations
- Pineapple – We used pineapple rings in this recipe, but you can use crushed pineapple. Pineapple tidbits will also work in this recipe.
- Cake Mix – Feel free to use other types of cake mix in this recipe. White cake mix or a pineapple cake mix are great options.
- Chopped Nuts – If you love chopped nuts, then you can add some to the top prior to baking.
How to Make Pineapple Upside Down Cupcakes
- Step 1 – Prepare Oven – Preheat the oven to 350 degrees.

Step 2. Cut the pineapple rings into quarters.

Step 3. Now, combine the cake mix with the oil, eggs and pineapple juice. Mix until everything is blended.

Step 4. Mix the butter and brown sugar together.

Step 5. Place about 2 teaspoons of the butter mixture into the bottom of each cupcake tin sprayed with cooking spray. Place the pineapple pieces in a circle around the bottom and one maraschino cherry in the center.

Step 6. Finally, put the cake batter on top of each muffin tin.

Step 7. Bake for about 25 minutes until a toothpick inserted into the center comes out clean.

Step 8. Let the cupcakes cool in the muffin pan for a few minutes then remove. Then move to a cooling rack.

Step 9. To make removing each one easier, I suggest running a butter knife around the edges of each cup. Serve with Homemade Whipped Cream Recipe or No Churn Vanilla Ice Cream if desired.
Pro Tips
- Cooking Cupcakes – You will know the cupcakes are done when the toothpick inserted comes out clean.
- Removing Cupcakes – We recommend using a sharp knife to go around the edges of the cupcake. Flip cupcake pan onto wax paper then after a few minutes cupcakes will release from pan.
- Cooling Cupcakes – After removing the cupcakes, allow them to cool on wax paper.
Frequently Asked Questions
To prevent the cupcakes from sticking to the pan, only allow the cupcakes to cool for a few minutes. If they cool to long in the cupcake pan, then the sugary bottom will begin to stick.
For best results, you can place a piece of parchment paper in the muffin tin.
Store you leftover Pineapple Upside Down Cupcakes in an air tight container. Place in the fridge and they will last about 3 days.
These cupcakes can be placed in the freezer. We recommend flash freezing the cupcakes by placing the cupcakes on a baking sheet and freezing for an hour.
Then store them in a freezer container for about 2 months. This way you can take out as many as needed without thawing a large amount.
When ready to serve, allow the cupcakes to thaw in the fridge overnight.
More Easy Pineapple Desserts
- Pineapple Poke Cake Recipe
- Cherry Pineapple Dump Cake Recipe
- Baked Pineapple Dessert
- 2 Ingredient Pineapple Angel Food Cake Recipe
- Pineapple Bread Pudding
- See more Easy Pineapple Dessert Recipes
Try making Pineapple Upside Down Cupcakes recipe today. Then leave a comment and star recipe rating.
Pineapple Upside Down Cupcakes
Ingredients
- 20 oz canned Pineapples
- 1 box Yellow Cake Mix
- 1/2 cup Vegetable Oil
- 3 Eggs
- 1/3 cup melted Butter
- 2/3 cup Brown Sugar
- 24 maraschino cherries
Instructions
- Preheat oven to 350.
- Cut pineapple rings into quarters.
- Spray muffin pan with non stick spray.
- Combine cake mix, oil, eggs and pineapple juice in a bowl and beat on low until incorporated.
- In another bowl combine melted butter and brown sugar and stir until blended.
- Spoon 2 teaspoons of butter mixture into each cup.
- Place pineapple pieces in a circle around bottom with cherry in center.
- Fill each cup 2/3 full with batter.
- Bake 20-25 minutes or until toothpick inserted in center comes out clean.
- Allow to cool in pan for 5 minutes.
- Run a butter knife around edges of each cup and invert onto baking sheet to remove cupcakes.