Old Fashioned Pineapple Upside Down Cake Recipe

This old fashioned pineapple upside down cake is the perfect antidote to the winter blues.

A Short History of this Old Fashioned Pineapple Upside Down Cake Recipe

“Upside down” cakes as a genre seem to have appeared in the late 19th century. They are called “upside down” because typically fruit of some kind is placed at the bottom of the pan or bottom of the skillet, with a buttery cake batter on top. After baking, the cake is flipped upside down and the fruit decorates the top of the cake. Up until the late 19th century, while they may have existed, upside down cakes weren’t being written about.

The invention of technology to can pineapple in the early 20th century made the fruit, for the first time, accessible to many Americans. To stimulate demand for this new product, the Dole Pineapple Company sponsored a recipe contest in 1925. They received over 60,000 entries, of which 2,500 were recipes for a version of a pineapple upside down cake, indicating that the recipe had already attained a certain level of popularity. 100 recipes were selected and included in a printed recipe book.

A Note About Fresh Pineapple

We have made this recipe with fresh pineapple and it works equally well (should you want to make it in a season when it’s readily available). In that case, replace the pineapple juice called for in the recipe with 1/2 cup of milk.

Tropical Antidotes to the Winter Blues

Does all that grey have you down? Us to! Here are some our favorite sunny desserts to help us through the long winter months.

Useful Tools for Making this Old-Fashioned Pineapple Upside Down Cake Recipe

Old Fashioned Upside Down Pineapple Cake Recipe

Old Fashioned Pineapple Upside Down Cake Recipe

This old fashioned pineapple upside down cake is the perfect antidote to the winter blues.
5 from 1 vote
Prep Time 20 minutes
Cook Time 1 hour
Course Dessert
Cuisine American
Servings 8 servings


  • 9-inch cake pan
  • parchment paper


  • 1/4 cup unsalted butter melted (1/2 stick)
  • 3/4 cup packed light brown sugar
  • 2 canned pineapple rings in juice
  • 8 to 12 maraschino cherries
  • 1 3/4 cup all-purpose flour
  • 1 1/2 tsp baking powder
  • 1/2 tsp salt
  • 1/2 tsp ground cinnamon
  • 1/4 tsp nutmeg
  • 1 tsp cardamom
  • 1 tsp ginger
  • 1/2 cup softened butter
  • 3/4 cup granulated sugar
  • 2 large eggs at room temperature
  • 1 1/2 tsp vanilla extract


Prepare the pans:

  • Preheat oven to 350 F.
  • Grease and line a 9 inch round cake pan with parchment paper.
  • Melt the 1/4 cup butter in the microwave or in a small saucepan over low heat. Stir the sugar into the melted butter.
  • Spread the brown sugar mixture in the bottom of the cake pan.
  • Remove the slices of pineapple from the can, reserving a half cup juice — you will need it later in the recipe.
  • Arrange one pineapple slice in the center of the pan and then add pineapple slices in a circle pan around it. You can cut slices to fill in gaps as you meet the edge of the pan. Bonus points for lining the sides of the pan with pineapple chunks.
  • Cut each maraschino cherry in half. Place cherry half inside the center of each pineapple ring on the cake and at the center of a cupcake, and in between rings. If there is additional pineapple tidbits left over, you can chop it finely and squeeze it in any gaps.

Make the Cake Batter:

  • Sift together the flour, baking powder, salt, and spices into a small bowl.
  • In the bowl of a stand mixer using the paddle attachment, beat the stick of butter slowly on low speed until smooth, about 2 minutes.
  • Turn the mixer up to medium speed and gradually add in the sugar, beating until light and fluffy, about 4 minutes.
  • Add in eggs one at a time, beating well after each addition and scraping bowl, and vanilla.
  • Add the flour mixture, alternating with the juice, beginning and ending with the dry ingredients. You can do this in 2 or 3 additions. Then, continue to beat until creamy, about 1 minute, scraping down the sides of the bowl.

Bake and Serve:

  • Pour batter over the pineapples in the cake pan or prepared muffin cup.
  • Next, bake in a preheated oven until the cake (or cupcakes) springs back when lightly touched and the sides of the cake begin to pull away from the pan, 45-55 minutes for the cake, or 20-30 minutes for the cupcakes.
  • Cool cake on wire rack for 10 minutes, then run a knife around the edge and invert onto a serving plate and lift off the pan.
  • Serve slightly warm or at room temperature. Some vanilla ice cream on the side is quite nice.
  • Wrap in plastic wrap and store at room temperature for up to 2 days.
Keyword cake, pineapple
Tried this recipe?Let us know how it was!

Affiliate Disclosure: As Amazon Associates, we earn a small commission from qualifying purchases when you click on links embedded in this post.