These Mini Pineapple Upside-Down Cakes are just like the classic dessert, but in mini form! Perfect for any time of year!

Three mini pineapple upside down cakes on a white dessert plate. A fork rests in the background.

How was your weekend?! I spent the last few days at a food blogging conference in Salt Lake City, Utah and it was so amazing. I had such a fun time getting to meet other food bloggers and bloggers I’ve been talking to for a couple years now. I’m also a little jealous of those of you who live in Salt Lake City. It is absolutely beautiful there and I was a little sad to have to leave on Sunday.

Also, flying alone made me a little nervous. I mean, I’ve flown before and out of the country a few times. But flying alone? It was a little weird, but thankfully all of my flights were on time and everything went smoothly.

Another thing that was great? These Mini Pineapple Upside-Down Cakes. They’re even cuter because they’re in mini form. Right??

This Caramel Apple Upside-Down Cake has been pretty popular on the blog and lately, all I’ve had on my mind was making a Pineapple Upside-Down version. Because I love mini desserts, I decided to go with a smaller version instead.

I played around with my caramel apple upside-down cake recipe because the batter in that recipe was a bit too much and would’ve made more than 12 pineapple upside down cake cupcakes. I also figured most people don’t want to break out another muffin pan just to bake 2-3 more little cakes, so I tweaked the recipe to make exactly 12! Yeah!

Four pineapple upside down cake cupcakes, surrounded by maraschino cherries, on a piece of parchment paper.

Ingredients for This Recipe 

These individual pineapple upside down cakes are made using the same ingredients you’d need to make the classic cake. Here’s what goes into them: 

  • Butter: Always use unsalted butter when baking. If using salted butter, omit the additional salt called for in the recipe. 
  • Sugar: I used a blend of both brown and granulated sugar to make the cake batter. The topping is made with just brown sugar, which caramelizes beautifully while the mini cakes bake. 
  • Canned crushed pineapple: I bought a 20-ounce can and used most of it, but still had a little bit left over.
  • Maraschino cherries: A must when making homemade pineapple upside down cake, mini or otherwise! 
  • All-purpose flour: Spoon and level the flour when measuring it rather than scooping it out of the bag with the measuring cup. This will ensure you don’t measure out too much by mistake. 
  • Baking soda & salt: Helps the cakes rise and balances out the sweetness of the batter. 
  • Egg: Must be room temperature before being whisked into the cake batter. 
  • Vanilla extract: Pure vanilla is preferred. 
  • Whole milk: You can use 2% milk as well, but whole milk is best. It contains the most fat, which results in a moist cake. 

How to Make Mini Pineapple Upside-Down Cakes

First, you’ll make the topping. Add the butter and brown sugar to a saucepan and melt over medium heat until the mixture is smooth. Once smooth, divide the mixture between 12 standard size muffin cups. Place a maraschino cherry in the center of each muffin cup, then spoon crushed pineapple over top. 

Then, it’s time to make the cake batter. Mix the dry ingredients together in one bowl. In another bowl, beat together the butter and sugars. Slowly add in the egg and vanilla extract. 

To the wet ingredients, add the dry ingredients and the milk. You’ll want to alternate between the two to avoid over mixing the batter. 

Distribute the cake batter between the 12 muffin cups. Bake the pineapple upside down cake cupcakes until a toothpick inserted in the center comes out clean. 

You’ll need to let the cakes cool in the muffin tin for about 10 minutes before inverting onto a wire rack. They’ll need to cool completely before you can eat them. 

Three individual pineapple upside down cakes on a white plate with a fork. One mini cake has a bite missing.

Can I Make This Recipe as a Regular Cake? 

If you want to make this recipe in a cake tin, I recommend using my classic pineapple upside-down cake recipe instead. That way, there’s no guesswork on your part! 

Baking Tips 

  • For the topping, I used crushed pineapple. I did test the recipe with some sliced pineapple, but an entire ring will not fit very well in the muffin pan. You can use sliced pineapple, you’ll just need to cut them into smaller pieces and arrange a few pieces at the bottom.
  • You could also use pineapple tidbits, but the crushed pineapple was just much easier to spoon into the muffin pan and took less time. It also stays on top of the cakes just a little bit better too when you cut into them.

More Pineapple Desserts to Try! 

Mini Pineapple Upside-Down Cakes

4.86 from 7 ratings
Prep Time: 25 minutes
Cook Time: 25 minutes
Total Time: 50 minutes
These Mini Pineapple Upside-Down Cakes are just like the classic dessert, but in mini form! Perfect for any time of year!


Servings: 12 mini cakes

For the topping:

  • 1/4 cup (60 grams) unsalted butter
  • 1/2 cup (100 grams) brown sugar
  • 1 (20-ounce can) crushed pineapple (drained)
  • 12 maraschino cherries

For the cake:

  • 1 cup (125 grams) all-purpose flour (spooned & leveled)
  • 3/4 teaspoon baking powder
  • 1/4 teaspoon salt
  • 1/4 cup (60 grams) unsalted butter (softened)
  • 1/3 cup (65 grams) brown sugar
  • 1/3 cup (65 grams) granulated sugar
  • 1 large egg (room temperature)
  • 1 teaspoon vanilla extract
  • 1/2 cup (120 ml) whole milk


To make the topping:

  • Preheat the oven to 350°F. Spray a standard 12-count muffin pan well with non-stick cooking spray and set aside.
  • Add the butter and brown sugar to a small saucepan over medium heat. Mix until the butter is melted and the mixture is completely smooth. Remove from the heat and evenly distribute between all 12 muffin cavities.
  • Place 1 maraschino cherry in the middle of each muffin cavity. Spoon the crushed pineapple evenly between all 12 muffin cavities (you'll probably have some left over). Set aside.

To make the cake:

  • In a large mixing bowl, mix together the flour, baking powder, and salt. Set aside.
  • In the bowl of a stand mixer fitted with the paddle attachment, or in a large mixing bowl using a hand-held mixer, beat the butter, brown sugar, and granulated sugar until light and fluffy. Add in the egg and vanilla extract, making sure to mix well after each ingredient.
  • Add the dry ingredients in three additions alternating with the milk, starting with the dry ingredients and ending with the dry ingredients, mixing each time until just combined. Evenly distribute the cake batter between all 12 muffin cavities.
  • Bake at 350°F for 20-25 minutes or until a toothpick inserted into the center of the cakes comes out clean.
  • Remove from the oven and allow to cool in the pan for 5-10 minutes. Slide a knife around the outside of each cake (to loosen them from the pan), place a wire rack on top of the muffin pan. Very carefully (the pan will be hot!) flip the wire rack over with the muffin pan on top. Gently remove the muffin pan to release the upside-down cakes. Allow to cool, then serve and enjoy!
Cuisine: American
Course: Dessert
Author: Danielle
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