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Old Fashioned Pineapple Upside Down Cake

Imagine a cake that is old fashioned and reminiscent of a time when things were simpler. A cake that has a beautiful caramelized top and sweet pineapple flavor.

That’s right, we’re talking about old fashioned pineapple upside down cake.

This vintage treat is still as delicious today as it was decades ago. So if you’re looking for a unique dessert to wow your guests, look no further than this retro classic!

A Classic Dessert

Homemade Pineapple Upside Down Cake is a delicious and refreshing cake.

Pineapple upside down cake is a classic recipe, one of the best out there, and it’s easy to make.

The combination of pineapple, cherries, and a white moist fluffy cake creates an explosion of flavors in your mouth. 

Our old neighbor gave us the top of her pineapple a couple of years ago and we grew a pineapple with it. It was easy and all we had to do was wait about two years. Ha! 

I never knew, before growing this pineapple, that it took so long to grow them. Ours was small but as ripe and sweet as they get. 

As a kid, my husband asked his mom to make homemade pineapple upside down cake quite often, and he always loved it.

So, he asked me to make one with our homegrown pineapple and it turned out amazing.

Growing a pineapple in the backyard was easy.

Here’s the pineapple in the pot. It’s neat the way the pineapple grows out of the top of the leaves. Those are some sharp leaves, too. Might poke your eye out! 

Homemade pineapple upside down cake is a delicious dessert any time of year.

The pineapple didn’t grow too large, but it was as sweet as they get. 



  • Butter, melted
  • Brown sugar
  • Pineapple slices (fresh pineapple or pineapple rings from a can)
  • Pitted cherries


  • Butter, softened
  • Granulated sugar
  • Eggs
  • Vanilla extract
  • All-purpose flour, sifted
  • Baking powder
  • Salt
  • Milk

Full printable recipe with measurements and instructions listed at the bottom of the post in the recipe card.

How To Make Pineapple Upside Down Cake

  1. The the brown sugar and melted butter to the bottom of a baking dish.
  2. Top with slices of pineapple and cherries.
  3. In a large bowl, cream the butter and sugar.
  4. Add the eggs, vanilla extract, flour, baking powder, salt, and milk. Mix together.
  5. Gently pour over the pineapple and brown sugar mixture.
  6. Bake for 40-45 minutes or until cake tester comes out clean.

Step-By-Step Instructions


Brown sugar gives the pineapple upside down cake a deeper sweet taste.

Spray a 8 inch by 8 inch baking dish with nonstick cooking spray.

Add the brown sugar to the greased baking dish. 

The sugar will create a brown sugar glaze on the top of the cake after baking.

Upside down pineapple cake is a wonderful summer cake.

Pour the melted butter over the brown sugar and mix it all together. Spread the butter and sugar mixture over the bottom of the dish. 

Delicious upside down pineapple cake from scratch.

Next, lay the pineapple slices on top of the brown sugar and butter mixture. Place the cherries in the little spaces in between. 

You can add as many cherries as you’d like. Typically, you add more pineapples, but mine was small, so I only had a few slices. 

I used a glass baking dish, but you can also use a heavy skillet, such as a cast-iron skillet for the recipe, as well.


Pineapple upside down cake, from scratch, is an amazing dessert that's easy to make.

Add the softened butter to a large mixing bowl and cream for about one minute. 

Ingredients for pineapple upside down cake include butter, sugar, flour, and eggs.

Add the sugar and cream for about one more minute. 

This is the best pineapple upside down cake recipe. You are going to love the flavors including pineapple, cherries, and a moist white cake.

Plop in the eggs, one at a time, and mix them into the batter. 

Pineapple upside down cake can be baked in a glass dish, or a cast iron skillet.

Add the vanilla extract.

We go through vanilla here like it’s goin’ out of style. It adds a little bit of flavor to what you’re baking. It’s almost like you’re best friend in baking – it’s always there for you. 

Homemade Pineapple Upside Down Cake

Get your baking powder measured out and ready to add to the flour. 

Sifted flour gives pineapple upside down cake a light and fluffy texture.

Add the flour, salt, and baking powder to a sifter. Sift the ingredients into the bowl. 

Sifting the flour will add a light fluffy texture to your cake. 

Cake recipes from scratch taste better than any store bought cake! This pineapple upside down cake is a delectable dessert!

Mix the flour mixture into the batter. 

The flour always looks so pretty when it’s sifted. It looks like snow! This is the only snow I will get down here in Florida. Sigh…

Quick pineapple upside down cake is a fun summer treat.

Pour the milk into the batter and mix together. 

Homemade pineapple upside down cake is a traditional summer cake. Its perfect for birthday parties and potlucks.

Pour the batter on top of the pineapple and spread it out evenly. 

Normally, you’re going to make this in a 9″ x 13″ baking dish, but with such a small amount of pineapple, I baked it in my 8″ x 8″ dish.

It did make it a thicker cake in the smaller dish, which was delish! 

Bake for approximately 40-45 minutes, or until a cake tester comes out clean. 

Homemade pineapple upside down cake is a fun and easy dessert to make. The pineapple bakes up soft and is sweet in flavor.

Allow the cake to cool and invert it onto a plate or cookie sheet.

It helps to scrape the sides with a knife before inverting so the cake doesn’t stick. 

Why Is My Pineapple Upside Down Cake Soggy?

Pineapple slices have a lot of juice, so you need to make sure and dry off the slices before adding them to the baking dish.

Grab a paper towel and pat dry the slices to help dry them off a little.

Does Upside Down Pineapple Cake Need To Be Refrigerated?

Yes, you will need to refrigerate the cake.

Can You Freeze An Upside Down Pineapple Cake?

Yes, you can freeze an upside down pineapple cake. Be sure to allow the cake to cool to room temperature and wrap it up in plastic wrap and keep in an airtight container.

The cake can be frozen for up to three months. When you’re ready to serve it, place it in the refrigerator to thaw overnight.

How Was Pineapple Upside Down Cake Invented?

Most likely the cake was invented in the early part of the 1900s. The Dole Pineapple Company ran a contest and received a lot of recipes with upside down cake and it took off!

Can Pineapple Upside Down Cake Be Frozen?

Yes, you can freeze pineapple upside down cake. Be sure to let it cool before storing it in the freezer. Keep the cake in an airtight container in the freezer for up to two months. You can leave it in the refrigerator for about 24 hours when you’re ready to let it thaw.

More Delicious Pineapple Recipes

Pineapple upside down cake from scratch is an easy and delightful dessert.

Pineapple upside down cake is definitely a classic dessert that always impresses guests.

It’s easy to make, so you can knock this one out of the park even if you’re not an experienced baker.

Be sure to get the single layer cake recipe, add a scoop of vanilla ice cream on the side, and give it a try! It might just become your favorite cake.

Homemade Pineapple Upside Down Cake is a delicious and easy recipe.

Homemade Pineapple Upside Down Cake

Yield: 12 pieces
Prep Time: 20 minutes
Cook Time: 40 minutes
Total Time: 1 hour

Who doesn’t love an old fashioned pineapple upside down cake? It is such a classic dessert that always seems to hit the spot. Plus, it is really easy to make – you just need a few simple ingredients that you probably already have in your kitchen. So why not give it a try today? You won’t be disappointed!



  • 1/4 cup butter, melted
  • 1/2 cup brown sugar
  • 20 ounce can pineapple slices (or fresh pineapple)
  • Handful of pitted maraschino cherries


  • 1/2 cup butter, softened
  • 3/4 cup sugar
  • 2 eggs
  • 1 teaspoon vanilla extract
  • 1-1/2 cups all-purpose flour, sifted
  • 1-1/2 teaspoons baking powder
  • 1/4 teaspoon salt
  • 1/2 cup milk


Preheat oven to 350-degrees.

Grease a 8-inch x 8-inch baking dish.


  1. Add the brown sugar to the bottom of the pan.
  2. Melt butter, pour over the top of the brown sugar, mix together, and spread over the entire dish.
  3. Place the pineapples and cherries on top of the brown sugar. (I like to place cherry in the center of each pineapple slice).


  1. Start by adding the butter to a large bowl and cream for one minute.
  2. Add the sugar and cream again for one more minute.
  3. Add the eggs, one at a time, and mix together.
  4. Add the vanilla and mix together.
  5. Combine flour, salt, and baking powder. Sift into the bowl and mix.
  6. Add the milk, mix together, and gently pour cake batter over pineapple.
  7. Bake for 40-45 minutes or until a cake tester comes out clean.
  8. Let cake cool to room temperature and turn cake upside down onto a cake plate.


I used an 8-inch by 8-inch baking dish for the recipe because my pineapple was small. If you use more pineapple, you can use a larger cake pan. However, your cake will not be as thick.

If you used canned pineapple, be sure to drain pineapple juice before removing the pineapple slices.

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Nutrition Information:
Yield: 16 Serving Size: 1
Amount Per Serving: Calories: 356Total Fat: 10gSaturated Fat: 6gTrans Fat: 0gUnsaturated Fat: 3gCholesterol: 47mgSodium: 184mgCarbohydrates: 67gFiber: 5gSugar: 45gProtein: 4g

Nutrition is approximate.

Did you make this recipe?

Please leave a comment on the blog or share a photo on Pinterest

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Leanne H

Friday 6th of January 2023

I've made this cake 5 times now and it's always delicious. Pineapples were on sale and this recipe compliments fresh pinnapple perfectly.

Julie Pollitt

Saturday 7th of January 2023

I love to hear that! It's wonderful when they are on sale.

April Walker

Friday 23rd of December 2022

I double recipe for a 9x13. I also add crushed pineapple to the batter as well as some of the juice, in addition to the milk. Comes out perfectly every time! My family loves it and it's also one of my go tos for work potlucks!


Friday 15th of July 2022

I made this recipe and it came out moist and delicious. Will definitely make again.

Julie Pollitt

Saturday 16th of July 2022

That's great to hear! Thanks for sharing!


Sunday 29th of May 2022

Great recipe, thank you. I've doubled the recipe for a 9x13" glass dish and added ~0.5 cup of crushed pineapple to the batter. The cake raised well and was light and moist. Definitely a keeper :)


Monday 17th of October 2022

@Amanda, I always use the saved juice to add in place of half of the milk.. Crushed pineapple sounds even better!!!! 👍


Friday 9th of September 2022


Thank for the tip! I can't wait to make this recipe tonight.

Thanks Julie

Julie Pollitt

Sunday 29th of May 2022

Hi Irina,

You're welcome and that's great to hear! Thanks for stopping by and sharing!


Monday 2nd of May 2022

My cake came out dry. Would have liked a moister cake.

Julie Pollitt

Monday 2nd of May 2022

Hi SMT, I am sorry to hear that.

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