Double Pineapple Upside Down Cake Recipe! Double, We Say!

Double Pineapple Upside-Down Cake Recipe

April 20th is National Pineapple Upside Down Cake Day. They should really find a way to shorten that one. Anyway, the Pineapple Upside Down Cake became popular in the 1940’s with the help of the Dole company making it a classic American dessert. This type of cake is usually made with the pineapple topping at the bottom of the cake and the cake batter pour over the top. After baking, the cake is then flipped over showing the colorful pineapples and cherries. And since things are usually upside-down in our kitchen anyway, we were all set to double the Pineapple Upside Down Cake goodness with this recipe for Double Pineapple Upside-down Cake…  [photo via flickr]

  • 1 box of Pineapple Supreme Cake Mix
  • 1 large can sliced pineapples, drained
  • 1 large jar Maraschino Cherries
  • 1/3 cup vegetable oil
  • 1-1/3 cups pineapple juice
  • 4-5 eggs
  • 1 cup butter
  • 2 cups firmly packed brown sugar
  • 1 small can crushed pineapples, drained
  • 1 (8oz) can vanilla frosting


  • Place pineapple slices at the bottom of two round, well oiled baking pans.
  • Place whole cherries in the center of each pineapple and between each of the slices.
  • In a medium sauce pan, melt butter.  Add brown sugar and cook until bubbling.
  • Pour the brown sugar mix over the cherries and pineapple in each of the pan up to two inches deep.


  • Blend together cake mix, eggs, pineapple juice and vegetable oil until smooth. Pour equal amounts of the batter over the pineapple mixture and brown sugar in each of the pan.
  • Bake for 30 minutes in a 350 degree oven or until the center of the cake is done (insert a toothpick in the center and if it comes out clean, then the cake is done).
  • The cake should allowed to be cooled for 15 minutes. Remove from pans and allow for them to cool on a plate for two hours.


  • Drain the can of pineapples until there is no liquid left. Mix together the frosting and pineapples.
  • After the cakes have cooled for the minimum of two hours, place one of the cakes on top of the other, pineapple side up. Frost the sides of the cake.
  • Leave the top and center of the cakes unfrosted and place the cakes in the refrigerator until ready to serve.

And a tip when creating this classic dessert: Using fresh pineapples and cherries will make the cake more delectable and sweet. Also, make sure that a non-stick pan is used so that the cake does not stick to the pan when flipping it out.