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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. It’s such a happy cake!

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. It 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. Add the brown sugar and melted butter to the bottom of a baking dish. Heat oven to 350 degrees and grease a square 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 the cake tester comes out clean.

Step-By-Step Instructions


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

Spray an 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. 

The yellow pineapple slices and the red maraschino cherries add such a nice pop of color.

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.

You will love how the top comes out with caramelized pineapple slices.


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. 

If the cake is not done, extend the baking time for a few minutes at a time.

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 to 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, wrap it up in plastic wrap, and keep it 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!

We’re so glad because we love the classic pineapple upside down cake. The easy recipe is the kind of cake that is perfect for a party or gathering.

Upside down cakes make a beautiful cake when you invert them, and they are a lot of fun, too!

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

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.

Tips For A Moist And Flavorful Pineapple Upside Down Cake

Although you only need a few basic ingredients for this retro cake, here are a few tips that will make things perfect.

  • Make sure you don’t over-mix the batter; otherwise, it might turn out dry and dense. You want it to be a moist cake.
  • If you don’t have fresh pineapple to slice and top the cake, use canned. It works perfectly; just make sure you drain the juice from the can first. Don’t worry if you don’t have perfect whole rings; the from-scratch cake tastes amazing.
  • If you want to add a little extra flavor, add a sprinkle of ground cinnamon or nutmeg on the pineapple rings before you pour in the batter.
  • Make sure you grease the pan well before adding the pineapple and cherries; otherwise, the cake might stick to the pan and not come out easily.
  • Try some peaches instead of cherries the next time you make the cake. Or, add some bananas to the middle of the pineapple rings for a fun twist and a change from the classic pineapple upside-down cake.

Ways To Add Some Variety to the Cake

  1. Sour Cream for Moisture: Adding some sour cream to your batter can add moisture and richness to your cake. It helps balance the sweetness and gives a creamy texture.
  2. Yellow Cake Mix as a Base: Using a yellow cake mix such as Betty Crocker can help you make the recipe faster.
  3. Choice of Pan: While a round or square cake pan is traditional, using a cast iron skillet can add a rustic charm and help in caramelizing the sugar and pineapples perfectly. A springform pan or a Bundt cake pan can also be used for the recipe.
  4. Use Dark Brown Sugar: dark brown sugar will give the cake a little bit more of a deeper flavor.

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.

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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Wednesday 23rd of August 2023

In your tips,,,it said to make sure you grease your pan. The #2 step with the brown sugar and butter say mix together in bottom of pan? Whyyyy do we need to geease the pan if we are mixing the brown sugar mixture in bottom??

Julie Pollitt

Thursday 24th of August 2023

Great question! I don't like anything sticking to my pans, because it makes clean up easier. You might be able to get away with not greasing the pan, but the brown sugar will stick to the pan easily. If you don't do it on the bottom, I would definitely do it on the sides.


Thursday 20th of July 2023

I would like to double this cake for a thick 9×13. I have made it in a 8×8 pan and it turned out perfectly.

How long would it take to bake at 350° if I were to double the recipe?

Julie Pollitt

Friday 21st of July 2023

I haven't doubled the recipe, so I am not sure. But, I would check it at the 45 minute mark and use a cake tester or toothpick and if it comes out with batter still on it, you might need to cook 10 more minutes. Keep checking after 5 to 10 minute increments. Hope that helps! Let us know what the final time is.


Sunday 23rd of April 2023

Can you use lactose free milk??

Julie Pollitt

Monday 24th of April 2023

Hi Roe,

I am not sure. I haven't used it before with this recipe.


Wednesday 19th of April 2023

I made this and followed the recipe exactly and it came out perfectly. It was the most delicious cake I have ever baked! My husband loved it too.

Julie Pollitt

Thursday 20th of April 2023

That's awesome! I am so glad to hear that. Thank you for sharing!


Tuesday 11th of April 2023

I had heart bypass surgery about 2 months ago, so have to lower my salt and saturated fat. I used unsalted butter in the topping. I made several substitutions in the batter. I used brown sugar for more richness. I used sodium free baking powder. Left the salt out. Replaced the milk with pineapple juice. Used slightly less avocado oil in place of the butter. I also had no cherries or Pineapple slices so I used the well drained crushed pineapple and walnut pieces and slivered almonds instead.

Julie Pollitt

Tuesday 11th of April 2023

Sounds like a great alternative! And delicious! Thank you for sharing that and hope you're on the mend. :)

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