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.

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Recipe Summary

prep:
15 mins
cook:
40 mins
additional:
15 mins
total:
1 hr 10 mins
Servings:
10
Yield:
1 9-inch cake
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Ingredients

10
Original recipe yields 10 servings
The ingredient list now reflects the servings specified
Ingredient Checklist

Directions

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

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  • 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.

  • 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.

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

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

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

  • 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

319 calories; protein 4.1g; carbohydrates 42.2g; fat 15.4g; cholesterol 75.3mg; sodium 158.4mg. Full Nutrition
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Reviews (4)

Read More Reviews

Most helpful positive review

Rating: 4 stars
05/16/2020
Not too shabby! I did add more brown sugar and butter to the topping, one of my favorite parts of pineapple upside down cakes. Not a fan of the cinnamon in the cake, so will omit next time I make this. I was a little concerned about the amount of batter when I was filling the pan, but I like the shorter cake, really balanced this recipe. Read More
4 Ratings
  • 5 star values: 2
  • 4 star values: 1
  • 3 star values: 1
  • 2 star values: 0
  • 1 star values: 0
Rating: 5 stars
08/18/2020
My first try at a Pineapple Upside-Down Cake. This was an easy recipe to use, I did use bleached all-purpose flour because it was what I had. Also lined my pan with parchment paper to make removal trouble free, this is a personal weakness, I can make things stick. The topping was delicious and as I had hoped, the cake was light and delicious. Excellent classic recipe. Very tasty and the wife, plate and fork in hand, is looking at me as if I just turned into Mr. Wizard. Read More
Rating: 5 stars
04/29/2020
This cake was yummy! I made some substitutions because of what I had on hand - vanilla bean paste, maraschino cherries and drained crushed pineapple - and it was still very good and easy to pull together. Read More
Rating: 4 stars
05/16/2020
Not too shabby! I did add more brown sugar and butter to the topping, one of my favorite parts of pineapple upside down cakes. Not a fan of the cinnamon in the cake, so will omit next time I make this. I was a little concerned about the amount of batter when I was filling the pan, but I like the shorter cake, really balanced this recipe. Read More
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Rating: 3 stars
02/25/2021
Not my favorite I did leave out the cinnamon and almond extract. my problem was the sweetness of the cake itself, or I guess lack of. My daughter remarked that it tasted like corn bread. Read More
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