The Best Pineapple Upside Down Cake

a top down image of a sliced pineapple upside down cake

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We think this is THE Best Pineapple Upside Down Cake recipe! This cake is moist, sticky, delicious and full of pineapple flavour! Serve for dessert with a scoop of vanilla ice cream or whipped cream. Yum.


Units Scale

Pineapple Cake:

  • 1/2 cup butter
  • 1 cup white sugar
  • 2 large eggs
  • 1 tsp vanilla extract
  • 1398 mL (14 oz) can crushed pineapple (drained well, set juice aside)
  • 1 1/2 cups all purpose flour
  • 1 tsp baking soda
  • 1/2 tsp salt

Pineapple Sugar Topping:

  • 1/4 cup melted butter
  • 1/2 cup of brown sugar (golden or dark brown sugar both work)
  • 1 (398 mL) can pineapple rings (this size can has 8 rings)
  • 78 maraschino cherries (depends on how many pineapple rings you use)

Pineapple Sugar Glaze:

  • 2 tbsp powdered sugar
  • 4 tbsp pineapple juice


Making the cake:

  1. Preheat your oven to 350 degrees F.
  2. Use a wire mesh strainer to drain the juice from the crushed pineapple. I put the strainer over a small bowl to keep the juice, which you can use later for the glaze. Set everything aside.
  3. Using an stand mixer cream together the butter and sugar.
  4. Add the eggs, one at a time, until the mixture is smooth.
  5. Mix in the vanilla.
  6. Add the drained crushed pineapple and mix well.
  7. In a separate bowl whisk together the flour, baking soda and salt.
  8. Add the flour mix to the pineapple mix, and stir to combine.

Putting it all together:

  1. Now make the ‘Pineapple Sugar Topping’: Melt the butter then pour it in to a pineapple upside down cake pan or a 10-inch round pan. Make sure to tip the pan so some butter gets onto the sides of the pan.
  2. Sprinkle on 1/2 cup brown sugar.
  3. Lay out the pineapple rings in a single layer on the bottom of the pan.
  4. Add a maraschino cherry to the centre of each pineapple ring.
  5. Now add the cake batter, making sure to smooth it out to the edges of the pan.
  6. Bake for 45 minutes. NOTE: At the 30 minute mark check the cake and if the top looks like it’s browning too quickly tent it with a piece of aluminum foil.
  7. The cake is done when it is golden in colour and a toothpick inserted into the centre of the cake comes out clean.
  8. While the cake is baking, you can make the glaze.
  9. Combine 4 tablespoons of pineapple juice with 2 tablespoons of powdered sugar. If you want it thicker just add more powdered sugar.
  10. Once the cake has completed baking, remove it from the oven then let the cake cool in the pan for about 10-15 minutes. After this time turn the cake out onto a plate. To do this I lay a serving plate over the open part of the pan and then turn the cake upside down onto the plate.
  11. If you want to add the extra glaze drizzle it on now.
  12. The cake should cool for at least an hour before serving.
  13. Enjoy!