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a from scratch pineapple upside down cake with pineapple and cherries
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5 from 5 votes

Pineapple Upside Down Cake

Pineapple Upside Down Cake is an old-fashioned recipe that is absolutely delicious with a buttery, moist crumb and sweetly caramelized fruit on top that makes for a beautiful presentation without a need for additional decoration! Serve it warm or room temperature with whipped cream or a small scoop of vanilla ice cream for a special treat!
Prep Time15 mins
Cook Time30 mins
Total Time45 mins
Course: Cake
Cuisine: American
Servings: 8 servings
Calories: 460kcal
Author: Amy Nash



  • ½ cup brown sugar
  • ¼ cup melted butter
  • 20 ounces sliced pineapple rings, drained, reserving juice
  • 20 maraschino cherries without stems


  • ½ cup salted butter softened
  • ½ cup granulated sugar
  • ¼ cup brown sugar packed
  • 1 large egg
  • ¼ cup sour cream room temperature
  • ¼ cup milk
  • ¼ cup pineapple juice
  • 1 teaspoon vanilla extract
  • 1 ½ cups cake flour
  • 1 ½ teaspoons baking powder
  • ½ teaspoon salt


  • Preheat oven to 350 degrees F. Spray a 9-inch cake pan with baking spray. Drain the pineapple (reserving ¼ cup of the juice) and pat the pineapple rings and maraschino cherries dry on paper towels.
  • Combine the brown sugar and melted butter in a small bowl, then spread into the bottom of the prepared pan. Arrange seven of the pineapple slices in the bottom of the pan, then cut the others in half and place them along the sides of the pan, filling in holes with the maraschino cherries.
  • In a large bowl, beat the butter, granulated sugar, and brown sugar until creamy and light. Add the egg, sour cream, milk, pineapple juice, and vanilla and mix again, scraping down the sides of the bowl. The batter may start looking curdled, but that's okay.
  • Add the flour, baking powder, and salt, then mix until combined. The batter will be fairly thick. Spoon the batter over the fruit and spread it into an even layer.
  • Bake for 40-45 minutes, just until a toothpick inserted into the center of the cake comes out clean and the cake is golden brown on top. Let cool for 5-10 minutes before turning out onto a serving plate. Loosen the sides of the cake from the pan first by running a thin, sharp knife around the edges. Then place your serving plate upside down on top of the cake pan before flipping both over. The cake will drop right out of the pan, although you may have a piece of fruit or two that likes to stick. If so, just lift it out and place it back on top of the cake.
  • Serve warm or at room temperature.


  • Store any uneaten cake in an airtight container on the counter or in the fridge for 2-3 days. To reheat, you can warm individual slices in the microwave for a few seconds or cover with foil and warm in a 350 degree F oven for 5-10 minutes.
  • Freezing: You can freeze this cake for up to 2 months. Let it cool completely, then wrap in plastic wrap before freezing. Thaw on the counter before rewarming in a 350 degree F oven for 5-10 minutes before serving.
  • I don't recommend using fresh pineapple for this cake as it releases more liquid than canned pineapple, which can make for a soggy cake. If you only have pineapple chunks or tidbits on hand, you can use those instead of rings. You need about 1 ½ cups of fruit.


Calories: 460kcal | Carbohydrates: 68g | Protein: 5g | Fat: 20g | Saturated Fat: 12g | Polyunsaturated Fat: 1g | Monounsaturated Fat: 5g | Trans Fat: 1g | Cholesterol: 74mg | Sodium: 402mg | Potassium: 186mg | Fiber: 2g | Sugar: 49g | Vitamin A: 665IU | Vitamin C: 7mg | Calcium: 109mg | Iron: 1mg