Pineapple Upside-Down Cupcakes

A fun twist on the classic cake recipe, these Pineapple Upside Down Cupcakes have the perfect hint of pineapple flavor throughout, and are topped with tasty caramelized pineapple and cherry slices.

This delicious dessert is a great addition to any BBQ or get together. If you love the classic Pineapple Upside Down Cake, then these individualized treats are sure to be a hit anywhere you take them.

Pineapple Upside Down Cupcakes with whipped cream

classic cake in cupcake form

Whenever I eat Pineapple Upside Down Cake, it always brings back fond memories of family gatherings. It’s a popular recipe during holidays like Christmas and Easter, but we also love enjoying it during the summer. There’s nothing more refreshing than pineapple flavor!

For a fun twist on the classic cake recipe, I decided to try a cupcake version! I couldn’t be more pleased with how they turned out!! All the amazing tastes of pineapple flavored cake, with caramelized pineapple slices and cherries on top, but in individual serving sizes!

The cupcake version was just as simple—if not simpler—to make, and ended up being a crowd pleaser. Everyone loved them, especially the kids. Plus, are they not adorable?!

pineapple and cherry slices in the bottom of a cupcake tin

tips for making Pineapple Cupcakes

You’ll start by spooning some butter and brown sugar into the wells of two muffin tins, then adding your pineapple rings (cut into fourths to fit) and your maraschino cherry halves.

Then you’ll add your cake batter, filling nearly all the way full (don’t worry – they won’t puff up too much). Bake in the oven at 350° F for 20-25 minutes.

They bake up into lovely golden cupcakes, but of course the most delicious part is underneath!

Once they have cooled, flip the cupcakes so the pineapple/cherries are on top (tips for flipping the cupcakes below). Serve when you’re ready. We love to serve ours with some freshly whipped cream on the side!

Baked pineapple upside down cake cupcakes


Flipping the cupcakes is the hardest part, and even then, it’s not too difficult. Here are some tips to help you flipping the cupcakes.

  • Wait a few minutes for the little cakes to cool a bit.
  • Use a sharp paring knife or a small rubber spatula and slide it around each cake.
  • Flip the cupcake pan onto wax paper.
  • Allow the cupcakes to sit for another few minutes with the pan still covering them.
  • Carefully remove the pan.

Voila – not too hard, right?!

How to store pineapple cupcakes? You can store the cupcakes in the fridge, in an airtight container, for about 3 days.

To store in the freezer, allow the cupcakes to cool and flash freeze by placing them in the freezer for about an hour. Take the cupcakes out, wrap them with plastic wrap, then again with foil. Or place the wrapped cupcakes in a freezer safe container. Label and freeze for 2-3 months. 

Pineapple Upside Down Cupcakes Recipe

For more fruity cupcake recipes, try:

Pineapple Upside Down Cupcakes Recipe

5 from 17 votes
A fun twist on the classic cake recipe, these pineapple upside down cupcakes have the perfect hint of pineapple flavor!
Course Dessert
Cuisine American
Prep Time 10 minutes
Cook Time 20 minutes
Total Time 30 minutes
Servings 24
Calories 192 kcal
Author Lil' Luna


  • 1 (20-ounce) can pineapple rings drained and juice reserved
  • 1 (15.25-ounce) box yellow cake mix
  • ½ cup vegetable oil
  • 3 eggs
  • cup butter melted
  • cup brown sugar packed
  • 12 maraschino cherries cut in half


  • Preheat the oven to 350°F. Prepare 24 wells of a muffin tin by spraying with cooking spray.
  • In a large bowl, mix together the pineapple juice, yellow cake mix, oil, and eggs until well blended.
  • Cut each of the pineapple rings into four equal-sized pieces. Mix together the butter and brown sugar, and add about 1 teaspoon of the butter mixture to each well of the muffin tin. Add two pieces of pineapple and a maraschino cherry half, cut side up.
  • Pour the cake batter into the muffin tins, filling to about ¼ inch from the top. Bake 20-25 minutes or until golden brown. Remove from oven and let cool 15 minutes, then loosen the cupcakes from the sides of the muffin tin with a knife and invert onto a cooling rack.
  • Serve warm with freshly whipped cream, if desired.


adapted from Betty Crocker

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About Alicia

Hi! I’m Alicia and I blog at The Baker Upstairs. I am in love with all things food! I love to bake bread, cupcakes, cookies… you name it! When I’m not baking, I am running after my two adorable little girls, working as an RN, knitting, reading, and trying to squeeze in time with my husband every day.

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  1. These look absolutely fantastic. I made similar cupcakes for a church function last year and they went over very well. I used some crushed pineapple and some which had been cut into quarters (two to a muffin cup). 1/4 tsp butter, one tsp crushed pineapple, 1/2 cherry then fill each cup to about 1/4 inch from top.

      1. Must have been. I’ve been volunteered to make more this year (+ 3 additional cakes) for their bake sale

  2. 5 stars
    My husband can eat a whole upside down cake by himself. Excited to try these individual servings. Same great taSte.

  3. 5 stars
    Pineapple upside down cake made in a dutch oven is my moms favorite camping treat. With your delicious recipe and instructions im able to have it at home!

  4. 5 stars
    My hubby loves these! I am more of the chocolate fan & him the fruity, but I really do like these! They are soft & full of flavor! I love pineapple, so if I can’t have chocolate, this is the next best!

  5. 5 stars
    Okay I am terrified of cake, it always ends up horrible even from box mixes, but this recipe was so easy and ended up so delicious and tender!! The flipped out clean, they’re moist and sweet and have that perfect pineapple summer Tang. My family is anti MARACHINO cherry SO we threw a pecan in the middle and iT was amazing. Definitely going to be making these over and over this summer. Thank you!!

    1. This makes me so happy to hear! Thank you so much for letting me know 🙂 Adding a pecan would be perfect!

  6. 5 stars
    A very tasty treat that everyone enjoyed more than a whole cake. They already gone before I remembered to take a picture. Lol