When I saw this recipe for the first time, I squealed! Pineapple Upside Down Cake is something I hold dear to my heart, and I could not believe I hadn’t heard about, or thought about, making them in cupcake form. My mom made this cake literally all the time when I was growing up. Then, I started making it because it was easy, and I loved it so much. The love never waned, and I continued making it often and eventually my daughter fell in love with it as well.

When my husband and I first started dating, I was preparing to meet his granny for the first time, and I had been warned that she never liked anyone he brought to meet her. Hmmm… no pressure at all! I decided to bake a Pineapple Upside Down Cake to take to her with nervous hope that it might make a difference. Well, she loved me and my cake so I think of Pineapple Upside Down Cake as a miracle worker! Our daughter had heard this story many times so when she began dating someone seriously, and was about to meet the granny, she made the same cake and won the love of that granny forever!

Enter this recipe and I found out that I love this cupcake version. They are perfect for parties, picnics, or just having individual portions. I usually double the recipe because 12 cupcakes go really fast in our house! They are easy to make, delicious, and look so lovely!


Serving Ideas: Top with whipped cream or serve with vanilla ice cream.

Pineapple Juice: If you forget to save the pineapple juice (which I have done!) a perfect substitute is the same amount of buttermilk. If you don’t have buttermilk, you can combine 1/2 cup milk with 1/2 Tablespoon white vinegar, stir, and let sit for 5 minutes.

Pineapple Choices: I prefer crushed pineapple because of the small area in a muffin cup, but you can use rings or chunks and just play around with positioning pieces in the muffin cups. It will be delicious with whichever style of pineapple you choose!

Cake Mix Version: If you want to use a boxed cake mix, it will turn out great as well. Just replace the water called for in your cake mix with pineapple juice.

Store: Wrap the cupcakes in plastic wrap and place in an airtight container. Keep in the fridge for up to 4 days.

Freeze: Let the cupcakes cool completely. Either wrap each cupcake in plastic wrap and then foil or place in an airtight container. They will be good for up to 3 months.

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  • Author: Olivia



For the Caramelized Topping

1/2 cup butter – melted
3/4 cup packed light brown sugar
1 (20 oz.) can crushed pineapple in pineapple juice – Drain well but Save the Juice!
12 Maraschino cherries (or more if you like extra cherries!)

For the Cupcake Batter

1 1/2 cups all-purpose flour
3/4 cup granulated sugar
1 1/2 tsp. baking powder
1/4 tsp. salt
1/4 cup unsalted butter – softened
1/2 cup pineapple juice (reserved from the canned pineapple)
2 large eggs
1 tsp. vanilla extract


Preheat oven to 350°F

Grease 12 muffin cups with butter or spray with cooking spray

Spoon melted butter into the bottom of each muffin cup – divide the butter equally.

Spoon 1 Tablespoon of brown sugar over the butter in each muffin cup.

Press a Maraschino cherry into the center of the brown sugar in each muffin cup.

Spoon a heaping tablespoon of drained crushed pineapple over the cherry and compact it with the back of a spoon into an even layer.

Set aside while you make the cupcake batter.

For the Cupcakes
In a mixing bowl, beat together the softened butter and sugar until creamy and well-combined.

Add eggs, beating one at a time until combined.

Stir in vanilla extract.

In a separate bowl, whisk together flour, baking powder, and salt.

Using a wooden spoon or spatula, alternate adding the flour mixture and pineapple juice to the butter mixture, starting and ending with the flour mixture and mixing until just combined after each addition. Don’t overmix or the cupcakes will be tough.

Using a spoon, evenly divide the cupcake batter into the prepared muffin cups. The batter will be thick! Spread the batter evenly into each cupcake well using the back of the spoon.

Fill each cupcake well all the way to the top.

Bake for 22-25 minutes or until toothpick inserted into center of cupcake comes out clean.

Remove from oven and allow to cool 5 minutes, then use a toothpick to go around the edges to make sure the sides are loosened.

Using potholders, carefully place a wire cooling rack over top of muffin pan and flip to invert onto wire rack.

Lift the muffin tin carefully and the cupcakes should release easily.

Allow to cool before serving.

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