Pineapple Upside-Down Cake from Scratch


This is an old-fashioned upside-down cake recipe from my German grandmother from scratch. She used this same cake batter for many different fruits as an alternative to pineapple. She often used fresh Italian prunes or pitted fresh cherries. My grandparents owned a bakery and this cake was very popular in the 1950s and 1960s. Serve warm or at room temperature with whipped cream.

Prep Time:
15 mins
Cook Time:
40 mins
Additional Time:
15 mins
Total Time:
1 hr 10 mins
1 9-inch cake


  • ½ cup brown sugar

  • ¼ cup unsalted butter, melted

  • 3 (1/2 inch thick) slices fresh pineapple, quartered

  • 12 frozen cranberries

  • cup white sugar

  • ½ cup unsalted butter, softened

  • 2 large eggs

  • 1 ½ teaspoons baking powder

  • 1 teaspoon vanilla extract

  • ½ teaspoon almond extract

  • ½ teaspoon ground cinnamon

  • ¼ teaspoon salt

  • 1 ½ cups unbleached all-purpose flour

  • ¾ cup milk


  1. Preheat the oven to 350 degrees F (175 degrees C). Grease a 9-inch diameter, 2 1/2-inch tall round cake pan.

  2. Stir brown sugar and melted butter together in a bowl. Spread evenly over the bottom of the prepared cake pan. Place pieces of pineapple on top of brown sugar mixture and around the outer edge of the pan, all facing the same way. Place 2 pieces in the center. Place a cranberry between each pineapple piece.

  3. Beat white sugar and softened butter together using an electric mixer in a bowl until light and fluffy. Add eggs, one at a time, beating well and scraping the sides of the bowl after each addition. Pour in baking powder, vanilla extract, almond extract, cinnamon, and salt. Mix well.

  4. Add 1/2 cup flour and 1/4 cup milk to batter at a time, mixing well after each batch until thoroughly blended.

  5. Pour batter over pineapple slices, making sure batter gets between them. Spread and smooth batter using an offset spatula.

  6. Bake in the preheated oven until a toothpick inserted into the center comes out clean, 40 to 45 minutes.

  7. Remove cake from the oven and let cool on a wire rack for 15 to 20 minutes. Run a knife around the edges of the cake to loosen. Place a plate over the cake pan and quickly invert, waiting a few seconds for it to fall if it doesn't immediately separate from the pan.

Cook's Notes:

This is a very easy cake to make. A young person could make it with some parental guidance with the pineapple cutting and handling of the hot pan.

This cake is not as sickeningly sweet as some pineapple upside-down cakes and not as greasy because less butter and brown sugar are used to prepare the pan.

I use frozen cranberries or frozen pitted cherries instead of maraschino cherries, because I don't like the taste or artificial coloring of the maraschino cherries. But something red on the cake makes this one still look traditional.

You can use canned sliced pineapple instead of fresh, and vanilla bean paste instead of vanilla extract.

Nutrition Facts (per serving)

319 Calories
15g Fat
42g Carbs
4g Protein
Nutrition Facts
Servings Per Recipe 10
Calories 319
% Daily Value *
Total Fat 15g 20%
Saturated Fat 9g 47%
Cholesterol 75mg 25%
Sodium 158mg 7%
Total Carbohydrate 42g 15%
Dietary Fiber 1g 3%
Total Sugars 27g
Protein 4g
Vitamin C 8mg 42%
Calcium 87mg 7%
Iron 1mg 7%
Potassium 102mg 2%

* Percent Daily Values are based on a 2,000 calorie diet. Your daily values may be higher or lower depending on your calorie needs.

** Nutrient information is not available for all ingredients. Amount is based on available nutrient data.

(-) Information is not currently available for this nutrient. If you are following a medically restrictive diet, please consult your doctor or registered dietitian before preparing this recipe for personal consumption.

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