This pineapple upside down cake is three layers of caramelized pineapples, maraschino cherries, and homemade cinnamon whipped cream! This layered twist on the classic pineapple upside-down cake recipe is sure to be a family favorite!
{Triple Layer} Pineapple Upside-Down Cake
Prep Time
45 mins
Cook Time
30 mins
Total Time
1 hr 15 mins
 
This pineapple upside down cake is three layers of caramelized pineapples, maraschino cherries, and homemade cinnamon whipped cream! This layered twist on the classic pineapple upside-down cake recipe is sure to be a family favorite!
Course: Dessert
Cuisine: American
Keyword: Pineapple Upside-Down Cake
Servings: 12 -14 Slices
Author: Michelle
Ingredients
Pineapple Topping
  • 3 20 oz cans pineapple rings (in pineapple juice or fresh); drained (save 1/4 cup of juice for the cake)
  • 1 20 oz can crushed pineapple (in pineapple juice or fresh); drained
  • 14 maraschino cherries, cut in half
  • 6 Tbsp butter, melted
  • 3/4 cup brown sugar
Cake
  • 1/2 cup butter, softened
  • 1/3 cup vegetable oil
  • 3/4 cup brown sugar
  • 3/4 cup white sugar
  • 4 large eggs
  • 2 2/3 cups all purpose flour
  • 1/3 cup corn starch
  • 2 1/2 tsp baking powder
  • 1/2 tsp salt
  • 3/4 cup milk
  • 1/4 cup pineapple juice, drained from can is fine
  • 3 tsp vanilla extract
  • 1/4 cup Greek Yogurt
Whipped Cream
  • Cinnamon Whipped Cream (recipe linked below)
Instructions
  1. Preheat oven to 350 degrees and grease 3 cake pans ( 9" cake pans) with cooking spray (just to ensure the cakes do not stick).
Pineapple Topping
  1. Place 2 Tbsp of melted butter in each cake pan, and tilt the cake pan around until the better has spread a bit. Sprinkle 1/4 cup brown sugar in each pan.
  2. Arrange pineapple rings in each pan (7 rings should fit nicely in each pan). To fill in any gaps on the outer edge, slice any leftover pineapple rings into cubes and add them between the rings. Place two cherry halves in the center of each pineapple ring, making sure the uncut side is facing downwards (that way the pretty side will show when the cake is out of the pan). Lastly, spread about 1/4 cup of crushed pineapple over the pineapple rings in order to fill in all areas with pineapple. Set aside.
Cake
  1. With a mixer, beat butter until light and fluffy, about 1-2 minutes. Add in oil and mix until combined. Add in both brown sugar and white sugar, beating until well combined (scrape the sides of the bowl with a rubber spatula if needed). Add in the eggs, one at a time, beating until just combined.
  2. In a separate bowl, sift together flour, corn starch, baking powder, and salt.
  3. Whisk together milk, pineapple juice, vanilla extract and Greek yogurt.
  4. Alternately add the dry ingredients and the wet ingredients into the butter mixture, beginning and ending with the dry ingredients. Mix until just combined.
  5. Divide batter evenly between the three cake pans. Bake for 30-35 minutes (mine was done right at 30 minutes), or until a cake tester comes out clean.
  6. Allow cakes to cool completely.
Whipped Cream
  1. Once your cakes have cooled, make the Cinnamon Whipped Cream. Set aside 1/2 cup of whipped cream for decorating.

  2. Place the bottom cake layer on a cake stand and spread about half of the remaining whipped cream over the cake, keeping the whipped cream about 1/2" in from the edge of the cake (as the layers are stacked on top, the whipped cream will spread to the edge). Place the middle layer on top, and spread with remaining whipped cream. Add the top layer, and with a piping bag and star tip, pipe on the whipped cream. Top with a cherry, if desired.
  3. Cake must be kept in the refrigerator until you are ready to eat.
  4. Enjoy!
Recipe Notes

Cinnamon Whipped Cream