Pineapple Upside Down Cake

Pineapple Upside Down Cake Recipe is always a favorite with guests.


Pineapple Upside Down Cake Recipe is a simple pineapple cake recipe topped with pineapple slices, maraschino cherries and brown sugar to form a caramel glaze.

This recipe was popular in the 1960's when I acquired it and is still a favorite cake of many people.

Serve this scrumptious classic cake warm, at room temperature or chilled.


Then freeze leftovers to reheat or eat cold, quickly. Great to pull out of the freezer when guests drop in.

Wrap cold slices in plastic wrap and pack in a lunch box for a welcomed dessert for that special person.

The second Pineapple Upside Down Cake recipe (in the picture above) is the one I use when I want more pineapple slices.


It's slightly sweeter and excellent served cold.


Pineapple Upside Down Cake


  • 1 stick butter, divided

  • 1/2 cup light brown sugar

  • 4 slices pineapple

  • Maraschino Cherries

Melt 1/2 stick butter in 8 inch iron skillet.


Stir in brown sugar until mixed well.

Remove from heat and top with pineapple slices.


Strategically place cherries on top to decorate.

Set aside, then mix the cake

  • l/2 stick butter (from divided butter above)

  • 3/4 cups white sugar

  • 1 egg

  • 1 teaspoon vanilla flavoring

  • 1 1/3 cups sifted cake flour

  • 2 teaspoons baking powder

  • 1/4 teaspoon salt

  • 1/2 cup milk

  • Homemade Whipped Cream (optional)

In a mixing bowl, cream remaining butter and white sugar together.

Add egg and cream until light and fluffy.

Stir in vanilla.


Sift together flour, baking powder, and salt.

Add flour and milk to batter and beat on medium speed of mixer for 1 minute.

Pour batter over mixture in skillet and bake in a preheated oven 350 F. until light brown and done in center when probed with a knife.

Remove from oven, let set 5 minutes.


Loosen around edges, invert pan and let cake slide out.

Serve topped with whipped cream if preferred.

It is very pretty decorated with additional whole, halved, or chopped maraschino cherries.

I like to sprinkle the whipped cream with a few chopped cherries and a tiny amount of maraschino cherry juice.

This classic cake is awesome served with a scoop of ice cream.

Pineapple Upside Down Cake Recipe No. 2


  • 1/4 cup butter (1/2 stick butter)

  • 1 cup brown sugar

  • 6 slices pineapple (need 15.5 oz. can pineapple slices packed in natural juice. (Reserve juice)

  • 6 Maraschino cherries

Melt butter in bottom of 9" round or 9" square baking pan. (I use a 9 1/2" spring form Pan).

Sprinkle on brown sugar.


Arrange pineapple slices over brown sugar.

Place one cherry in center of each pineapple slice.

Set aside. Prepare batter.

  • 1 stick butter (1/2 cup)

  • 1 cup sugar

  • 2 eggs

  • 1 teaspoon vanilla extract

  • 2 cups sifted cake flour

  • 1 tablespoon baking powder

  • 1/2 teaspoon salt

  • 3/4 cup pineapple juice

Cream butter on high speed.


Gradually, add sugar and continue creaming until light and fluffy.

Add eggs beating well after each addition.


Stir in vanilla.

Sift together cake flour, baking powder and salt.

By hand fold into batter alternately with pineapple juice until all is incorporated.

Beat batter on medium speed for 30 seconds.


Scrape down sides and beat another 30 seconds.

Pour batter over pineapple in pan and spread evenly.

Bake in preheated oven 350F. 50-55 minutes or until cake test done in center with a toothpick.

Remove from oven and let sit 10 minutes in pan.

Invert and turn cake out upside down onto cake plate.

This cake is excellent served warm or cold with vanilla ice cream.

Pineapple Upside Down Cake Tips


If baking in a spring form cake pan, check it for leakage before using.

Lock the bottom of pan in and fill it with water.

If it leaks, line the bottom and sides with parchment paper before melting the butter.

You will probably have rough edges around the finished cake if you line it with the paper.

Spread sides with whipped cream to hide the rough edges, if you prefer.


A visitor to this website informed me she used the No. 2 recipe above, to make individual Pineapple Upside Cake in jumbo muffin tins and served them at a function at the White House.


I have no further information on how many mini cakes she made nor if she decorated the sides with whipped cream for a lovely presentation.


She said they were perfect and the recipients loved them.


History Of
Pineapple Upside Down Cake Recipe


The Pineapple Upside Cake has been around since the 1920s.


However, there are no records on the exact date or who invented it.


In 1925, Dole's Hawaiian Pineapple Company ran a recipe contest in several ladies magazines requesting a created, original Pineapple Upside Cake Recipe.


According to legend, there were 2,500 recipes submitted.


Upside down cakes were popular in those days.


Most of those recipes were made with Pineapple.

However, there were recipes for other fruit upside down cakes, including , banana, orange, peach, and even Chocolate Upside Down Cake in my 1942 Burnt Toast Cook Book.


Some cook books called for nuts to be added to the topping.


Upside Down Cakes were popular back in those days and most were instructing the cook to cook it an iron skillet on top of the stove.


The Upside Down Pineapple Cake was called by other names, too.


That included skillet cakes because most recipes called for cooking in an iron skillet on top of the stove.


Back in those days there were few stoves with an oven.

I remember Mama cooking her cakes in an iron skillet on top of the stove up until she got her first stove with an oven from Sears and Roebuck Company in 1945.


Incidentally, according to my research, Sears and Roebuck published a Pineapple Upside Down cake in it's catalog in 1936.


The Pineapple Upside Down Cake has stood the test of time for good reasons... it is deliciously attractive, quick and easy to make with it's own topping, and downright delicious!


Enjoy and share the recipe!


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