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Double-Decker Pineapple Upside-Down Cake – Recipe

Upside-down cakes always intrigued me, since the beauty of the cake is at the bottom of the pan rather than at the top, and revealed after it is fully baked and inverted. Fancy that?

Pineapple upside-down cakes are so colorful; bejeweled by maraschino cherries.

I call it a “double-decker” pineapple cake, because two upside-down cakes are stacked up to create the finished product.

Cream cheese frosting, and cake crumbs, were used as finishing touches to complete this cake’s decor.

I was inspired by Paula Deen’s recipe, but made several modifications to satisfy my own taste, thus creating a similar, yet different cake.

Double-Decker Pineapple Upside-Down Cake – Recipe

Double-Decker Pineapple Upside-Down Cake – Recipe


  • 1 cup unsalted butter, room temperature
  • 1 1/3 cup granulated sugar
  • 5 large eggs
  • 2 tsp. vanilla extract
  • 3 cups cake flour (I used Softasilk by Pillsbury)
  • 2 tsp. baking soda
  • 1 tsp. baking powder
  • 1/8 tsp kosher salt
  • 1 1/4 cup low fat buttermilk
  • 14 slices of pineapple (2 -20 oz cans- there will be left overs)
  • 14 maraschino cherries (about 1/2 of a 10 oz jar)
  • 1 cup light brown sugar
  • 1 cup unsalted butter,melted
  • Cooking spray (I used Baker's Joy which has flour incorporated in it)
  • Cream Cheese frosting
  • 8 oz. Philadelphia cream cheese (not Fat Free or even 1/3 less fat - this will make the frosting too thin)
  • 4 Tbs unsalted butter, room temperature
  • 1 tsp. vanilla extract
  • 1 tsp. pineapple juice (left over from the canned fruit)
  • 1 cup confectioners sugar


  1. Place butter and sugar in a large mixing bowl, and beat until light and fluffy.
  2. Add the eggs, one at a time, beating well after each.
  3. Mix in vanilla extract, and set aside.
  4. Use a medium bowl to mix flour, salt, baking soda and baking powder ( I use a whisk)
  5. Mix in some of the buttermilk into the egg mixture, then mix in some flour, then buttermilk again and end with flour.
  6. Mix all for a minute longer and set aside.
  7. Preheat the oven to 350 degrees F, and place one oven rack in the middle of the oven, and the second rack just below it.
  8. Place foil paper on the middle rack, where you will rest the cake pans to prevent any overflow dripping down to the bottom of your oven.
  9. Spray bottom and sides of two 9 inch round cake pans with cooking spray, and flour  them, or use the Baker's Joy spray with flour, as I did.
  10. Sprinkle 1/2 cup of  brown sugar over the bottom of each cake pan.
  11. Drizzle each with 1/2 cup of melted butter.
  12. Arrange 7 slices of pineapple over the sugar-butter mixture to cover the bottom of each pan.
  13. Place a maraschino cherry in the middle of each pineapple slice.
  14. Pour 1/2 half of the cake batter over the pineapple in one pan, and spread the remaining half of the batter in the second pan.
  15. Place cake pans over foil on the middle oven rack, and bake for 45 minutes, or until the toothpick test comes out clean.
  16. Remove from the oven, and cool for 1o minutes in pan, on a cooling rack.
  17. Invert cakes onto a cooling rack, and let them cool completely.
  18. Once cooled, I inverted them again, and trimmed off the top of each cake, to make it flat for easier stacking.
  19. Place one of the cakes, with pineapple on the top, onto a cake platter, and stack the other cake on top of the first one, also with pineapple on the top, since this will be the final top of the finished cake.
  20. Prepare Cream Cheese frosting, and frost the sides of the cake.
  21. Keep refrigerated until ready to serve.
  22. Cream Cheese Frosting
  23. Place the cream cheese and butter in a medium mixing bowl, and mix until well incorporated and creamy.
  24. Beat in vanilla extract and pineapple juice.
  25. Add confectioners sugar and mix well until smooth and creamy.


I placed two pieces of wax paper over the cake platter, slightly overlapping at the center, before placing the cake on it for frosting, to prevent the icing from getting on the platter. Once I completed frosting the cake, I gently pulled out each piece of wax paper from under the cake, and discarded it.

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