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4.5 from 6 votes
Top-down view of my pineapple upside down cake.
Next-Level Pineapple Upside Down Cake
Prep Time
20 mins
Cook Time
35 mins

My version of this iconic pineapple-upside down cake recipe is next-level — but keeps the classic pineapple ring and cherry look you know and love.

Course: Dessert
Cuisine: American
Servings: 12 people
Author: Gemma Stafford
For vthe Caramel:
  • ½ cup (4oz/115g) butter
  • 1 ¼ cups (7½oz/213g) dark brown sugar
  • 1 large can (20oz/567g) sliced pineapple in juice
  • 10-13 maraschino cherries (stems removed)
For the Cake:
  • ½ cup (4oz/115g) butter, softened
  • ½ cup (4oz/115g) granulated sugar
  • cup (2oz/57g) dark brown sugar
  • 2 large eggs
  • ½ cup (4floz/120ml) whole milk
  • ½ cup (4floz/120ml) juice from the tinned pineapple
  • 1 teaspoon almond extract
  • 2 cups (10oz/284g) all-purpose flour
  • 2 teaspoons baking powder
  • ½ teaspoon salt
To Make The Caramel:
  1. Preheat the oven to 350°F (180°C) and generously butter a 9x13-inch (23x33cm) baking pan. Set aside.

  2. In a small saucepan over medium-low heat, combine butter and brown sugar and simmer until the sugar is dissolved in about 2-3 minutes. Pour into the prepared baking pan.

  3. Drain the pineapple rings and reserve ½ cup (4floz/120ml) of juice. Arrange as many rings 4 x 3 or as you can fit in a single layer in the pan on top of the butter and brown sugar mixture.

  4. Place a maraschino cherry in the center of each pineapple ring.

To Make The Cake:
  1. In a large bowl cream together the butter, dark brown sugar and granulated sugar until light and fluffy.

  2. Whisk in the eggs, milk, reserved pineapple and almond extract and stir to combine.

  3. In a medium mixing bowl, combine the flour, baking powder and salt, and then fold this into the wet ingredients until just combined.

  4. Carefully spread the batter over the pineapples and then bake for 35-40 minutes, until a wooden skewer inserted into the center comes out clean.

  5. Let the cake cool for 10 minutes in the pan before inverting onto a serving tray.

  6. This cake is best the day it is made, but you can store leftovers in an airtight container at room temperature for up to 2 days.

Watch the Recipe Video!