2 amazing retro pineapple upside-down cake recipes

Old-fashioned Pineapple Upside Down Cake

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If you love the tangy taste of pineapple, and have been hoping to find some delicious old-fashioned pineapple upside-down cake recipes, you just need to look back a few decades!

We have two tasty classic tropical dessert recipes here for you from the olden days.

Homemade double pineapple upside-down cake


#1. From the 70s: Vintage pineapple upside-down cake recipe (1975)

ALSO TRY: Dole’s crushed pineapple upside-down bundt cake recipe (1970)

Old-fashioned Pineapple Upside Down Cake

Old-fashioned pineapple upside down cake (1975)

Yield: 8
Prep Time: 20 minutes
Cook Time: 50 minutes
Additional Time: 10 minutes
Total Time: 1 hour 20 minutes

Ingredients

  • 1 cup sugar
  • 3 tablespoons cornstarch
  • 1 can crushed pineapple (16 to 17 ounces/2 cups)
  • 2 tablespoons melted butter
  • 1/2 cup maraschino cherries
  • 1-2/3 cup all purpose flour
  • 1/2 teaspoon salt
  • 2-1/4 teaspoons baking powder
  • 1/3 shortening
  • 2 eggs, beaten
  • 1/2 teaspoon vanilla
  • 1/2 cup milk

Instructions

  1. Mix 1/3 cup of the sugar with the corn starch, add juice drained from the pineapple.
  2. Cook in heavy 10-inch skillet over direct heat stirring constantly until sauce boils and becomes clear.
  3. Add drained pineapple and butter.
  4. Drain cherries thoroughly and arrange in a pattern in the pineapple mixture.
  5. Sift flour; measure and re-sift 3 times with salt and baking powder.
  6. Cream the 1/3 cup shortening until soft.
  7. Add the remaining 2/3 cups sugar and the eggs.
  8. Beat vigorously until smooth and fluffy.
  9. Stir in vanilla.
  10. Add flour mixture and milk alternately, beginning and ending with flour and beating well after each addition.
  11. Turn batter into skillet over pineapple.
  12. Bake in moderate oven at 350 (F) for 35 to 40 minutes or until center of cake is springy when lightly pressed with fingertips.
  13. Cool in pan or rack for about 10 minutes; then turn out on serving plate.
  14. Serve warm with or without whipped cream.

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Nutrition Information:
Yield: 8 Serving Size: 1
Amount Per Serving: Calories: 534Total Fat: 6gSaturated Fat: 3gTrans Fat: 0gUnsaturated Fat: 2gCholesterol: 56mgSodium: 427mgCarbohydrates: 108gFiber: 3gSugar: 32gProtein: 12g

Click Americana offers approximate nutrition information as a general reference only, and we make no warranties regarding its accuracy. Please make any necessary calculations based on the actual ingredients used in your recipe, and consult with a qualified healthcare professional if you have dietary concerns.


#2. From the 70s: Waikiki pineapple upside-down cake (1975)

SEE MORE: Hawaii travel in the ’70s: Look back at Honolulu & Waikiki

Pineapple Upside Down Cake and cup of coffee on white wooden tab
Photo by Mark_KA/Deposit Photos

Pineapple Upside Down Cake and cup of coffee on white wooden tab

Piña colada pineapple upside-down cake (1975)

Yield: 8
Prep Time: 20 minutes
Cook Time: 35 minutes
Total Time: 55 minutes

Ingredients

  • 2 tablespoons butter or margarine
  • 1/4 cup brown sugar (packed)
  • 8-1/2 ounces sliced pineapple, drained
  • 1-1/2 cups buttermilk baking mix
  • 1/2 cup granulated sugar
  • 1 egg
  • 1/2 cup coconut milk
  • 2 tablespoons shortening
  • 1 teaspoon vanilla
  • 3/4 cup coconut, separated

Instructions

  1. Melt butter in oven in square pan (8- by 8- by 2-inches) or round layer pan (9-1/2- by 1-1/2-inches).
  2. Sprinkle with brown sugar and 1/4 cup shredded coconut, then arrange pineapple slices over the brown sugar.
  3. Blend baking mix, sugar, egg, coconut milk, shortening and vanilla.
  4. Add 1/2 cup shredded coconut.
  5. Mix on low speed for about 1/2 minute.
  6. Scrape bowl frequently.
  7. Beat for 4 minutes at medium speed.
  8. Pour batter over butter mixture and pineapple slices.
  9. Bake for 30 to 35 minutes or until wooden pick inserted in center comes out clean.
  10. Invert to heat-proof plate. Serve warm.

Recommended Products

As an Amazon Associate and member of other affiliate programs, qualifying purchases made via our links earns us a small commission at no additional cost to you.

Nutrition Information:
Yield: 8 Serving Size: 1
Amount Per Serving: Calories: 263Total Fat: 11gSaturated Fat: 6gTrans Fat: 0gUnsaturated Fat: 5gCholesterol: 37mgSodium: 378mgCarbohydrates: 36gFiber: 1gSugar: 26gProtein: 5g

Click Americana offers approximate nutrition information as a general reference only, and we make no warranties regarding its accuracy. Please make any necessary calculations based on the actual ingredients used in your recipe, and consult with a qualified healthcare professional if you have dietary concerns.

NOW SEE THIS: Weird retro ways to serve pineapple (and a few good ideas, too)

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