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an image of 4 white dessert bowls with a Mini Pineapple Upside Down Cake with a pineapple ring and cherry on the top

Mini Pineapple Upside Down Cakes

  • Author: EsmeSalon
  • Prep Time: 20 minutes
  • Cook Time: 35 minutes
  • Total Time: 55 minutes
  • Yield: 12 servings 1x
  • Category: Dessert
  • Method: Moderate


Mini Pineapple Upside-Down Cakes are just like the classic dessert but in the mini single-serving form! Perfect for any time of year!


Units Scale

For the topping:

  • 1 can pineapple rings (or you can use fresh pineapple)
  • 1 teaspoon whiskey
  • 6 maraschino cherries
  • 1/4 cup butter
  • 1/2 cup brown sugar

For the batter:

  • 1 1/2 cups flour
  • 2 teaspoons baking powder
  • 1/4 teaspoon salt
  • 1/4 teaspoon cinnamon
  • 1/2 cup softened butter
  • 1 cup of sugar
  • 2 eggs
  • 1 tablespoon whiskey
  • 1/2 teaspoon vanilla extract
  • 1/2 cup pineapple juice


  1. In a small pot over medium heat stir together 1/4 cup butter, Β½ cup brown sugar, and a teaspoon of whiskey.
  2. Once the mixture starts to bubble, let it cook for another minute or two.
  3. It should thicken a little.
  4. Remove from heat and spoon into a buttered cupcake pan.
  5. Now lay in the pineapple slices and cherry halves.
  6. I found that my pineapple slices were a bit too big for standard-size baking cups.
  7. To remedy this, I sliced out a bit of the pineapple.
  8. For the batter first whisk together the flour, baking powder, salt, and cinnamon.
  9. Now cream together the softened butter and sugar.
  10. Stir in the eggs, whiskey, and vanilla extract.
  11. Now add half the flour mixture, and stir.
  12. Then pour in the reserved 1/2 cup pineapple juice, stir, then the remaining flour mixture.
  13. Spoon the mixture over the prepared pineapple-filled pans.
  14. Don’t overfill the cups, but they will be slightly full than standard cupcake recipes.
  15. One heaping spoonful per cup should do it.
  16. Bake at 350Β°F for 25-28 minutes until golden brown and a toothpick inserted in the center comes out clean.
  17. Allow cooling for a few minutes.
  18. While they cooled, I laid a cutting board over the cakes to help create a flatter bottom for them to sit on.
  19. Invert the pan over a cutting board or large plate to turn the mini cakes upside down (which of these is right-side up).
  20. If any pineapple pieces fall off, put them back in place.
  21. These are absolutely delicious and served right out of the oven, but they can also sit in the refrigerator overnight in an airtight container.
  22. Somehow the pineapple top helps to keep them moist if you want to make them the night before an event.


Prepared, tried, and tested by Hilda’s DIL from The Recipe Hunter: Tried Β and Tested Recipes from Home Chefs


  • Serving Size: 1 cake
  • Calories: 300
  • Sugar: 31.1 g
  • Sodium: 66.7 mg
  • Fat: 12.5 g
  • Carbohydrates: 44.5 g
  • Fiber: 0.8 g
  • Protein: 3 g
  • Cholesterol: 61.5 mg

Keywords: pineapple, Upside Down

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