Old fashioned pineapple upside down cake with crushed pineapple

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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

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.

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! 

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

Ingredients

Topping

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

Cake

• 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

Topping

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.

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. 

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.

Cake

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

Add the sugar and cream for about one more minute. 

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

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. 

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

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. 

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…

Pour the milk into the batter and mix together. 

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. 

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.

More Delicious Pineapple Recipes

• How to grill pineapple
• Easy no-bake pineapple lush
• No bake pineapple pie

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.

Ingredients

Topping

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

Cake

• 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

Instructions

Preheat oven to 350-degrees.

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

Topping

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).

Cake

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.

Notes

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.

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