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Old Fashioned Pineapple Upside-Down Cake

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  • Author: Amy
  • Prep Time: 15 minutes
  • Cook Time: 40–45 minutes
  • Total Time: 1 hour
  • Yield: 8 servings
  • Category: Dessert, Cake
  • Method: Baking
  • Cuisine: American
  • Diet: Vegetarian

Description

This Old Fashioned Pineapple Upside-Down Cake is a classic American dessert featuring a rich, buttery cake topped with sweet caramelized pineapple rings and vibrant maraschino cherries. It’s a retro recipe that’s as beautiful as it is delicious, with a golden glaze and a perfectly tender crumb. This easy, crowd-pleasing treat is ideal for holidays, potlucks, or anytime you’re craving a nostalgic homemade dessert.


Ingredients

  • 1/4 cup unsalted butter, melted
  • 3/4 cup packed brown sugar
  • 1 can (20 oz) sliced pineapple, drained (reserve juice)
  • 9 maraschino cherries
  • 1 1/2 cups all-purpose flour
  • 1 cup granulated sugar
  • 1/2 cup unsalted butter, softened
  • 2 large eggs
  • 1 teaspoon vanilla extract
  • 1/2 cup milk (or reserved pineapple juice)
  • 2 teaspoons baking powder
  • 1/4 teaspoon salt

Instructions

  • Preheat oven to 350°F (175°C). Grease a 9-inch round cake pan.
  • Pour melted butter into the pan and evenly sprinkle brown sugar over it.
  • Arrange pineapple slices on top of the sugar and place a cherry in each ring’s center.
  • In a large bowl, cream softened butter and granulated sugar until light and fluffy.
  • Beat in eggs one at a time, then stir in vanilla extract.
  • In another bowl, whisk flour, baking powder, and salt.
  • Alternate adding the dry mixture and milk (or pineapple juice) into the creamed mixture, starting and ending with the dry ingredients. Mix just until combined.
  • Gently pour batter over the arranged fruit and smooth the top.
  • Bake for 40–45 minutes, or until a toothpick comes out clean.
  • Cool for 5 minutes, run a knife along the edges, then invert the cake onto a serving plate. Let it cool before slicing.

Notes

  • Use fresh pineapple slices for a more natural taste.
  • Add cinnamon or nutmeg for extra warmth.
  • Substitute dairy-free butter and milk for a vegan-friendly version.
  • Sprinkle shredded coconut for a tropical twist.
  • Store leftovers at room temperature for 3 days or refrigerate for up to 1 week. Freeze for up to 2 months.