Fresh Pineapple Upside Down Cake

This Fresh Pineapple Upside Down Cake recipe is not overly sweet like the traditional dessert, but it is sweet enough to curb a sweets craving. It is easy to make and uses fresh pineapple in place of canned.

Fresh Pineapple Upside Down Cake


Vintage Dessert

Pineapple Upside Down Cake is a vintage dessert dating back to the early 1900s when it was baked in a cast iron skillet. Back when this dessert was created, the cake was usually baked over an open fire or in a stone oven. This cake became popular in the 1950s and 1960s but it seems to be gaining popularity again.

Many Pineapple Upside Down Cake recipes call for a vanilla or white cake mix. This cake recipe is from scratch. The cake is dense and holds up well with the weight of the syrup and the pineapples.

Nowadays, this dessert is baked in a cake pan, like a square or rectangular pan. It can also be baked in a skillet. This particular recipe calls for a 13″ x 9″ cake pan. I have not tried to bake this recipe in a skillet since I have a different recipe I use for the skillet and bake it on the barbecue.

Fresh or Canned Pineapple

I like to use fresh pineapple, which is what this recipe calls for. But you can use canned, which I have used as a test and the results are similar. The use of canned pineapple makes the cake sweeter. If using canned pineapple, you can reserve the juice from the can to use in the cake batter in place of fresh pineapple juice.

Ingredients Used For This Pineapple Upside Down Cake Recipe

Butter- For me, it has to be real butter, not margarine to make the sauce. You can use margarine, but the flavour won’t be the same. The sauce for the pineapple is what makes this cake stand out so the ingredients really do matter.

Brown Sugar- Light, golden or yellow is the variety I use. (light brown sugar is known by different names in different regions) Dark brown sugar overpowers the taste of fresh pineapples.

Flour- I use all-purpose flour in this recipe and like most of my recipes, the flour is not sifted. I fill and level the measuring cup before adding.

Shortening- I use all vegetable shortening for this cake recipe.

Buttermilk- I like the taste that the buttermilk gives to the cake. I had originally used milk in this cake recipe for years and it can still be used if buttermilk is not available. One day when the kids had drank all the milk and I only had buttermilk or heavy cream in the fridge, I tried the buttermilk and loved the results. I have been using buttermilk since. The buttermilk adds a tangy flavour to the cake which goes well with the sweetness of the pineapples and sauce.

The rest of the ingredients for this cake include eggs, baking powder, sugar, vanilla, pineapple juice, salt, and maraschino cherries.


Yes, the cake is a pineapple cake, but the pineapple can be replaced with other fruits. Oranges are a great alternative. Also, green apple slices are a good choice.

If you don’t have buttermilk, you can easily make substitute buttermilk by adding a tablespoon of lemon juice or vinegar to a cup of regular milk. An equal amount of whole milk or half-and-half cream can also be used.

In place of the traditional maraschino cherries, you can use fresh cherries or candied cherries. Blueberries are also a good choice.

Serving and Storing Fresh Pineapple Upside Down Cake

Plated slice of pineapple upside down cakeThis recipe makes 12 servings that can be served with fresh whipped cream on top. A sprinkle of powdered sugar on top is also a great way to serve this cake. Cinnamon sprinkled on top is also delicious.

In the winter, I like to pour some warm maple syrup over the cake before serving. This is how I remember being served Pineapple Upside Down Cake when I was little. Maple syrup is a staple for Canadians, especially those of us with a French Quebec background.

To store this cake, cover and refrigerate for up to 3 days. The cake can also be cut into squares and stored in airtight containers in the fridge.

The cake can also be cut into squares and frozen for later use. To do this, place the pieces of cake in the freezer for 45 minutes to set the topping. Wrap semi-frozen pieces in plastic wrap, then foil wrap before placing them in freezer bags. Freeze for up to three months.


Fresh Pineapple Upside Down Cake

Fresh Pineapple Upside Down Cake

Prep Time 10 minutes
Cook Time 55 minutes
Resting and Cooling 15 minutes
Course Dessert
Cuisine American
Servings 12 pieces



  • cup butter, melted
  • 1 cup light brown sugar
  • 6-9 fresh pineapple slices
  • 12-16 maraschino cherries


  • 3 cups all purpose flour
  • Tbsp baking powder
  • ½ tsp salt
  • cup all vegetable shortening
  • 1⅓ cup sugar
  • 3 eggs
  • tsp vanilla extract
  • 1⅓ cup buttermilk
  • cup pineapple juice


  • Preheat oven to 350°F
  • Line a 13" x 9" pan with parchment paper
  • In a medium bowl, whisk together flour, baking powder and salt. Set aside.
  • In a large bowl, beat together shortening, sugar and vanilla together, until smooth.
  • Add half of flour mixture and half of buttermilk alternatively, continue to beat.
  • Add remaining flour and beat just to incorporate flour.
  • Beat in remaining buttermilk and pineapple juice, until smooth and creamy.
  • Pour melted butter into prepared pan.
  • Sprinkle brown sugar over melted butter.
  • Line pineapple slices over butter and brown sugar.
  • Place cherries in centre of each pineapple slice and between the slices and the corners of the pan.
  • Pour cake batter evenly over pineapple slices.
  • Bake in preheated oven for 50-55 minutes or until a toothpick inserted in centre comes out clean.
  • Allow cake to cool for 5 minutes in pan.
  • Flip pan over onto a serving plate or tray and allow to rest with pan in place for 10 minutes.
  • Remove pan and carefully peel parchment paper off top of cake.
  • Cut into 12 equal pieces and serve warm.

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