Pineapple Upside Down Cake

This homemade Pineapple Upside Down Cake made with an easy buttery and moist vanilla cake and topped with delicious caramelized pineapple topping and even a cherry on top. The perfect spring and summer dessert!
Author: Jennifer Fishkind
Prep Time: 10 minutes
Cook Time: 40 minutes
Total Time: 50 minutes
Course: Dessert
Cuisine: American
Servings: 8 slices
Pineapple upside down cake square
4.45 from 9 votes


Pineapple Glaze:

  • ¼ cup Butter
  • ½ cup Brown Sugar
  • ½ tsp Cinnamon
  • 24 oz. can Pineapple Rings
  • Maraschino Cherries

Cake Batter:

  • 6 tbsp Butter (softened)
  • ¾ cup Granulated Sugar
  • cup Cream Cheese (softened)
  • 2 Eggs
  • 1 tsp Vanilla
  • ¾ cup Crushed Pineapple (in Juice)
  • 1 ¼ cup All Purpose Flour
  • ½ tsp Baking Powder
  • ½ tsp salt


  1. Pre-heat oven to 350 degrees. Line a 9 or10 inch cake pan with parchment paper or spray with non-stick cooking spray. Be sure to cover the sides thoroughly to prevent sticking.
  2. Add the pineapple glaze ingredients to a saucepan and melt for 5 minutes. Pour the glaze into the cake pan and spread around the pan.
  3. Arrange pineapple slices over the glaze and place a cherry in each ring. Set aside.
  4. Cream Butter, Sugar and Cream Cheese in a stand mixer or using a hand mixer until light and fluffy.
  5. In a medium bowl combine dry ingredients.

  6. With the mixer on low-speed beat in eggs one at a time, followed by vanilla and crushed pineapple until combined.
  7. Slowly add dry ingredients until combined. Do not over mix!
  8. Carefully spoon batter over pineapples in the pan.
  9. Bake for 30-40 minutes. Let cool for 5 minutes. Invert onto serving platter. (see tips for removing cake from the pan in the post above.)

Recipe Video

Nutrition per serving

Calories: 456kcal
Fat: 19g
Saturated fat: 11g
Cholesterol: 89mg
Sodium: 324mg
Potassium: 270mg
Carbohydrates: 69g
Fiber: 2g
Sugar: 52g
Protein: 4g
Vitamin A: 700%
Vitamin C: 13%
Calcium: 71%
Iron: 1.6%
Keyword: cake, pineapple
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