When your 10-year-old granddaughter requests pineapple upside-down cupcakes for her luau birthday party, you begin researching. There aren’t a lot of recipes out there for this mini dessert… Although I’ve made pineapple upside-down cakes in the past, I haven’t made a cupcake version.
(We are an Amazon affiliate and may receive a small percentage of any sales through the links in this post at no cost to you. Thanks for supporting our website!)
This recipe makes enough batter for at least six more cupcakes. After filling the 12 cups in the muffin tin, I had 1-1/2 cups left. I pulled out my Wilton mini angel food cake pan and filled it with the remaining batter. It made a little cake about one inch deep.
I used most of a can of pineapple rings, piecing together the last couple with some of the leftover pieces removed from each of the rings. (There aren’t 12 rings in a can.) If you plan on making 6 or more additional cupcakes, you will need two cans of pineapple rings and extra cherries.
Click here to jump to and print the recipe. ◄
Pineapple Upside Down Cupcakes
Makes 12 Cupcakes
Topping Ingredients
- 1/4 cup Butter, melted
- 1/2 cup Brown sugar
- 12 Pineapple rings – canned
- 12 Maraschino cherries – set on a paper towel to drain
Cake Batter Ingredients
- 1 cup sugar
- 1/3 cup butter, softened
- 1-1/3 cup all-purpose Flour
- 2/3 cup milk
- 1/4 cup Vegetable oil
- 1-1/2 teaspoons Baking powder
- 1/2 teaspoon Vanilla extract
- 2 large Eggs
- 1/4 teaspoon salt
Directions:
Preheat oven to 350°
In a small bowl, mix the melted butter and brown sugar.
Divide the mixture evenly between 12 muffin cups. Start with a teaspoon of the butter-sugar mixture in each cup.
Lay the cherries on a folded paper towel to absorb the excess liquid. If you don’t do this, that excess will leak into and discolor the pineapple ring.
I removed about 1-1/2 inches of the pineapple ring so it would fit into the cup better. (When you do this, the hole in the center becomes smaller. Unfortunately, the cherry is not as visible. I’m still pondering this dilemma. Any ideas?)
Set a pineapple ring on top of the butter mixture. Place a cherry in the center of each pineapple ring.
Prepare the Batter


My Conclusion
These cupcakes are very tasty. Dave and the girls really liked them. The girls commented that they were really cute and had never seen the cupcake version of this dessert before.
The cherry didn’t show as much because I cut down the pineapple slices, and the hole wasn’t as large. I’m wondering if I should put the cherry in the center before placing the pineapple slices.🤔
Don’t tell anyone, but I added another cherry to the top of the cupcake in the picture for aesthetic reasons. I guarantee the kids won’t complain.

Pineapple Upside Down Cupcakes
Here's a mini version of the classic pineapple upside-down cake.
Ingredients
Topping Ingredients
- 1/4 cup Butter, melted
- 1/2 cup Brown sugar
- 12 Pineapple rings - canned
- 12 Maraschino cherries - set on a paper towel to drain
Cake Batter
- 1 cup sugar
- 1/3 cup butter, softened
- 1-1/3 cup all-purpose Flour
- 2/3 cup milk
- 1/4 cup Vegetable oil
- 1-1/2 teaspoons Baking powder
- 1/2 teaspoon Vanilla extract
- 2 large Eggs
- 1/4 teaspoon salt
Instructions
Makes 12 Cupcakes
Preheat oven to 350°
In a small bowl, mix the melted butter and brown sugar.
Divide the mixture evenly between 12 muffin cups. Start with a teaspoon of the butter-sugar mixture in each cup.
Lay the cherries on a folded paper towel to absorb the excess liquid. If you don't do this, that excess will leak into and discolor the pineapple ring.
I removed about 1-1/2 inches of the pineapple ring so it would fit into the cup better. (When you do this, the hole in the center becomes smaller. Unfortunately, the cherry is not as visible. I'm still pondering this dilemma. Any ideas?)
Set a pineapple ring on top of the butter mixture. Place a cherry in the center of each pineapple ring.
Prepare the Batter
Beat the butter and sugar until light and creamy.
Beat in one egg at a time. Then, stir in the vanilla extract.
Whisk together flour, baking powder, and salt in a separate bowl.
Slowly mix the dry ingredients and milk into the butter mixture, alternating between the two, beginning and ending with the flour.
Gently fold in the vegetable oil.
Spoon the batter over the pineapple and cherries, filling each cup about 3/4 full. Bake for 20 minutes or until a toothpick inserted in the center comes out clean.
Allow cupcakes to cool in the pan for 5 minutes, then place a wire rack on top of the muffin tin and flip the tin and rack over. Do this while the cupcakes are still warm to ensure the caramelized topping releases cleanly. Carefully, run a knife around the edges to release the cupcake from the pan, if necessary. Let cool before serving.
Be Social!

