This recipe for vintage pineapple upside down cake is a true classic, featuring a light, airy butter cake topped with a sweet caramel sauce, pineapples, and maraschino cherries.
This recipe for pineapple upside down cake shares the vintage recipe for a popular 1950s dessert. The cake’s light sponge, adorned with a caramelized layer of pineapple and maraschino cherries, is a perfect balance of sweet and fruity flavors that will leave you craving more.
If you love pineapple desserts, then you’re in for a treat. My cherry pineapple dump cake is an easy and tasty alternative. And if you’re in the mood for something chilled, try my Watergate salad and frozen fruit salad, both using canned pineapple, which are sure to hit the spot.
The recipe was found in a vintage Dole pineapple cookbook. With the handwritten notes, I knew this recipe had been enjoyed before. That’s typically a clue that a recipe is a good one to test out for you! Check out that specialized cake pan.
Table of Contents
Why I Love This Recipe
- Showstopper: The stunning presentation of this cake, with its caramelized pineapple and cherry topping, makes it a showstopper on any dessert table.
- Vintage: If you’ve always wanted to try a classic, old-fashioned recipe, then this is perfect for you. It’s not a new recipe I’ve created, but a vintage cake recipe that has been loved and enjoyed for decades.
- Time-Tested: This is a tried and true recipe that has stood the test of time, thanks to its irresistible flavor and simplicity.
- Crowd Pleaser: Whether it’s a potluck, family gathering, or a simple dinner at home, this cake is always a hit. Its beautiful presentation and delicious flavor make it a surefire crowd-pleaser.
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- Butter: This ingredient, being the fat in our easy pineapple upside-down cake with cake mix recipe, imparts a rich, buttery flavor to the dessert.
- Brown Sugar: Brown sugar will provide a deep, caramel-like sweetness to the cake, enhancing the overall flavor.
- Sliced Pineapple: The star of our classic pineapple upside-down cake, these pineapple slices will be arranged on the bottom of the pan to create the iconic pineapple ring pattern when the cake is flipped.
- Maraschino Cherries: These will add a pop of color and a hint of tartness to balance the sweetness of the pineapple rings and the cake batter.
- Yellow Cake Mix: This is the base of our cake batter, providing a moist and fluffy texture to our pineapple upside-down cake.
- Vegetable Oil: This will be used in the cake batter to ensure a moist and tender crumb in our old fashioned pineapple upside down cake.
- Eggs: These are crucial for the structure of the cake. Make sure they are at room temperature so they incorporate more easily into the batter.
- Water: This will be used to prepare the cake mix, ensuring the right consistency for the best pineapple upside down cake.
- Deep Dish Pie Plate – This is essential for the classic pineapple upside-down cake as it allows the butter and brown sugar to melt together, creating a delicious caramelized base for the pineapple slices and cherries. The deepness of the dish allows for the cake to rise. A regular-sized pie plate will not work with this recipe.
- Large Bowl – You’ll need this to prepare the cake batter. It provides ample space to mix the yellow cake mix, vegetable oil, eggs, and water.
- Hand Mixer – This tool is crucial for achieving a smooth and well-blended cake batter. It ensures that all the ingredients are evenly mixed for the best pineapple upside down cake.
- Serving Platter – After baking, you’ll need to let the cake cool and then invert it onto a serving platter. This not only makes serving easier but also beautifully showcases the upside-down pineapple cake.
How to Make Vintage Pineapple Upside Down Cake
To start, preheat your oven to 350˚ F and gather all your ingredients. Make sure you have a deep dish pie plate and a serving platter ready.
Step 1 – Prepare the Pineapple and Cherry Base
First, melt the butter in your deep dish pie plate using the microwave. Once it’s melted, add in the brown sugar and 2 tablespoons of pineapple juice. It’ll give a caramel-like sweetness to the cake. Stir until well combined.
Step 2 – Arrange Pineapples and Cherries
Now, arrange the pineapple rings and cherries in this sweet mixture, creating a flavorful base for your upside-down pineapple cake.
Step 3 – Prepare and Pour the Cake Batter
Next, prepare the cake batter according to the directions on the box. Once it’s ready, slowly pour the batter over the arranged pineapples and cherries. Make sure to cover them evenly with the batter.
Step 4 – Bake the Cake
Place your pie plate in the preheated oven and bake for 40-50 minutes. You’ll know your classic pineapple upside-down cake is done when a toothpick inserted in the middle comes out clean.
Step 5 – Cool and Invert the Cake
After baking, let your cake cool for about 5 minutes. Then, carefully invert it onto your serving platter. Allow it to sit for another 3 minutes before removing the pie plate. This will ensure your pineapple slices and cherries stay intact, giving you the best pineapple upside down cake. It’s now ready to be served!
To ensure the best pineapple upside down cake, keep a close eye on the cake after the 25-minute mark. If it starts to brown too much on top, add a layer of foil sprayed with cooking spray to prevent overbrowning. This will help maintain the perfect color and texture of your dessert. The cake will rise quite a bit but that’s ok, use a toothpick in the middle to see when it’s done.
- Larger Cake: For a larger, 11x5x2 cake, increase the butter to ½ cup + 2 tablespoons, use 1 ¼ cup brown sugar, and double the pineapple to 40 oz of slices. This will give you a bigger, bolder version of the classic pineapple upside-down cake.
- Crushed Pineapple: For a different texture and flavor, try using crushed pineapples instead of the pineapple slices. This variation gives the cake a more integrated pineapple flavor and a unique twist on the old fashioned pineapple upside down cake recipe.
What to Serve With
- To take this vintage pineapple cake to the next level, top with some whipped cream before serving. Everyone will love this classic combination.
- Looking for a dessert pairing? Try serving this old fashioned pineapple upside down cake with a scoop of vanilla ice cream. The cool, creamy ice cream is the perfect contrast to the warm, caramelized pineapple slices.
- For a coffee break, pair this upside-down pineapple cake with a cup of strong black coffee. The bitterness of the coffee will balance out the sweetness of the cake, making for a satisfying mid-afternoon treat.
For the best pineapple upside down cake, arrange the pineapple rings at the bottom of the pie plate starting with one ring in the center and then placing the other rings around it as space allows. Place a maraschino cherry in the center of each pineapple ring. The cherries not only add to the flavor but also make the dessert visually appealing when you flip it onto the serving platter.
The classic pineapple upside-down cake is done when a toothpick inserted into the middle of the cake comes out clean. This means the cake batter is fully baked. It usually takes about 40-50 minutes in a preheated 350˚ F oven.
Letting the cake cool for a few minutes allows for the baked cake to naturally pull away from the sides of the pie plate to help it hold its shape when you invert it. However, don’t let it cool completely in the pan or the caramelized sugar might stick to the pan, making it difficult to remove.
Yes, you can. While this classic recipe calls for a yellow cake mix, you can experiment with other flavors to change the overall flavor of the dessert. Just remember to follow the directions on the box when preparing the cake batter.
Storing and Reheating
- Refrigerate: After you’ve enjoyed serving your classic pineapple upside-down cake, any leftovers should be stored in the refrigerator. Make sure your cake is cool, then place it in an airtightly sealed container. It can be kept in the fridge for up to 3 days, maintaining its delicious flavor and moist cake batter.
- Freeze: Unfortunately, this old fashioned pineapple upside down cake does not freeze well. The texture of the pineapple slices and the moistness of the cake batter don’t hold up to freezing and thaw, which can affect the overall quality and flavor of the dessert.
- Reheat Instructions: When you’re ready to enjoy another slice of the best pineapple upside down cake, simply let it come to room temperature on your serving platter. If you prefer it warm, you can also gently reheat it in the oven at a low temperature.
More Vintage Cake Recipes You’ll Enjoy
- What to Expect: This classic pineapple upside-down cake recipe makes one delicious dessert that’s enough for 8 servings.
- How to Scale: If you want to make more than one cake, you can easily double the recipe and follow the rest of the instructions as is. Alternatively, you can make a larger cake by increasing the butter to ½ cup + 2 tablespoons, using 1 ¼ cup brown sugar, and doubling the pineapple to 40 oz of slices. You’ll need an 11x5x2 cake pan for the larger cake.
Pineapple Upside Down Cake
- 1 Deep Dish Pie Plate
- ¼ Cup butter
- ½ Cup brown sugar
- 20 oz can of sliced pineapple rings
- 7 maraschino cherries
- 13.25 oz yellow cake mix
- 1/3 Cup vegetable oil may be different, follow box directions
- 3 large eggs may be different, follow box directions
- 1 Cup water may be different, follow box directions
- Preheat oven to 350˚ F.
- Melt the butter. Pour into a deep dish pie plate. Add brown sugar and 2 Tablespoons of pineapple juice. Whisk together.
- Arrange the pineapples and cherries in the pie plate on top of the butter mixture.
- Prepare the batter for the cake based on the directions on the box. Slowly pour over the pineapples and cherries.
- Bake in a preheated 350˚ F oven for 40-50 minutes or until the cake tests are done by inserting a toothpick in the middle.
- Let stand for 5 minutes. Invert onto a serving plate. Wait 3 minutes before lifting the pie plate off the cake. Serve warm.