Irresistible Cherry Pineapple Upside Down Cake Recipe

Are you ready to take your baking skills to the next level? Look no further than Dee’s Cherry Pineapple Upside Down Cake recipe. This dessert is perfect for any special day or occasion, and is sure to impress even the toughest of food critics.

With just a handful of ingredients, this easy pineapple upside down cake can be made using a cake mix to simplify the process. Don’t let the simplicity fool you though; every bite is packed with juicy and sweet flavors that will have you and your guests coming back for more.

But why stick to the standard pineapple rings when you can switch it up by adding cherry pie filling, maraschino cherries, and brown sugar into the mix? This old fashioned skillet pineapple upside down cake recipe using cake mix 1-2-3 will have your taste buds dancing thanks to the delicious blend of flavors that make it truly irresistible.

Whether you’re making this beautiful upside cake as a centerpiece for a party or just as a sweet treat for yourself or your family, one thing is for certain: this Dee Cherry Pineapple Upside Down Cake is guaranteed to be a hit. So get ready to bake up something special and make some memories in the kitchen with this mouthwatering dessert recipe.

Why You’ll Love This Recipe

Dee's  Cherry Pineapple Upside Down Cake
Dee’s Cherry Pineapple Upside Down Cake

Listen up, fellow dessert lovers! I have a recipe that will knock your socks off – Dee’s Cherry Pineapple Upside Down Cake. This delectable cake is the perfect dessert for any occasion, whether it’s a special day or just a casual get-together.

Now let me tell you why this cake is simply irresistible. First of all, it’s easy to make. You don’t need to be a professional baker to whip up this delightful treat. All you need are some basic ingredients like eggs, brown sugar, and cherry pie filling. The best part? You can use a cake mix as the base!

But just because it’s easy doesn’t mean it lacks in flavor. Oh no, quite the opposite actually! The combination of juicy pineapple slices and cherries on top of a moist and buttery cake is pure heaven. And if you’re feeling adventurous, you can even add some almond or rum brandy flavorings for an extra kick.

And here’s the thing: this cake isn’t just for pineapple upside-down cake lovers. Even those who aren’t fans of traditional pineapple upside-down cakes will love this recipe. It’s not too sweet or overwhelming; instead, it strikes the perfect balance between tart and sweet flavors.

So what are you waiting for? Give Dee’s Cherry Pineapple Upside Down Cake a try and get ready to fall in love with this easy-to-make, mouthwatering dessert. Whether you prefer cupcakes, bundt cakes or dump cakes you won’t regret trying out Dee’s recipe with fresh pineapples, chunks or crushed pineapples!

Ingredient List

 Take a big slice of tropical joy with Dee's Cherry Pineapple Upside Down Cake!
Take a big slice of tropical joy with Dee’s Cherry Pineapple Upside Down Cake!

Here are the ingredients that you’ll need to make this marvelous Dee’s Cherry Pineapple Upside Down Cake Recipe:

Dry Ingredients:

  • 1 box yellow cake mix
  • 1/2 cup brown sugar

Wet Ingredients:

  • 1/2 cup unsalted butter, melted
  • 1 (20 oz) can pineapple slices, drained and patted dry
  • 1 (21 oz) can cherry pie filling, divided in half
  • 3 large eggs
  • 1 cup pineapple juice (reserved from the canned pineapple slices)
  • 1/3 cup vegetable oil
  • 1 teaspoon vanilla extract, divided in half
  • 1/4 teaspoon almond flavoring, divided in half


  • Maraschino cherries

Note that you will need to reserve the juice from the canned pineapple slices and set it aside for this recipe. You will also need a 10-inch cast iron skillet or a baking dish of similar size.

The Recipe How-To

 A burst of sweet cherry and tangy pineapple in every bite.
A burst of sweet cherry and tangy pineapple in every bite.

Preheat the oven to 350°F (175°C).
Prepare a 10-inch (25-cm) cast-iron skillet. Melt 1 cup (2 sticks or 226 grams) of butter in the skillet. Add 1 ½ cups (300 grams) of packed brown sugar and stir until dissolved.

Arrange pineapple slices in the melted butter and brown sugar mixture. Add maraschino cherries inside each pineapple ring.

In a separate bowl, mix 1 box of cake mix according to package instructions, but substitute the water required with the juice from the can of pineapple slices. Add 1 teaspoon (5 ml) of almond rum or brandy flavoring divided between the cake batter and reserved juice.

Pour the batter over the pineapple slices, and spread evenly, making sure it reaches every corner.

Bake for 30 to 35 minutes or until a toothpick inserted in the center of the cake comes out clean.

After baking, let it cool for a few minutes before flipping. Flip onto the serving plate, removing skillet from on top.

Serve hot or cold, with whipped cream or a scoop of vanilla ice cream if desired.

Optional: Cut into squares to make individual servings, or use as topping for cupcakes, bundt, dump cakes or pound cakes. You can also add cherry pie filling and fresh pineapple chunks for a twist on this old-fashioned dessert.

Substitutions and Variations

 Who can resist the classic charm of an upside down cake?
Who can resist the classic charm of an upside down cake?

Now, let’s talk about some ways to customize and play around with this recipe to make it your own.

First off, if you’re not a fan of cherry pie filling, you can easily swap it out for another fruit filling of your choice. Peach or apple pie filling would be great options here. You could also try using fresh pineapple chunks instead of canned.

If you’re looking for a lighter version of this cake, you could use a white cake mix instead of yellow and swap out the pineapple slices in syrup for ones in juice. You may also want to consider using a sugar substitute like Splenda in place of the brown sugar.

For some added crunch and texture, try adding chopped nuts like pecans or almonds to the brown sugar mixture before pouring it into the pan.

If you’re feeling experimental and want to try something new, consider adding 2-3 tablespoons of rum or brandy flavoring to the cake batter. Trust me, the boozy flavors will take this cake to a whole new level.

Lastly, if you’re short on time or just want individual servings, you can make cupcakes instead of a full cake. Simply divide the batter among cupcake liners and top with a pineapple slice and cherry before baking.

As always, feel free to get creative and have fun with this recipe!

Serving and Pairing

 A heavenly caramelized topping with a soft and spongy center makes this cake irresistible.
A heavenly caramelized topping with a soft and spongy center makes this cake irresistible.

If you ask me, there’s nothing better than a warm slice of Dee’s Cherry Pineapple Upside Down Cake fresh out of the oven. Serve it up with a dollop of whipped cream or a scoop of vanilla ice cream, and you’ve got yourself a dessert fit for a king.

But this cake isn’t just limited to after-dinner indulgences. In fact, it’s versatile enough to be served at any time of day. A slice in the morning alongside your cup of coffee is sure to set your day off on the right foot, while some sticky-sweet leftovers can make for a decadent mid-day snack.

If you’re feeling adventurous, try pairing this cake with a glass of fruity red wine like a Pinot Noir or even something sparkling like Moscato d’Asti. The subtle notes of cherry and almond in the cake play perfectly against these light and refreshing wines.

But let’s not forget about our beer lovers! Pairing this cake with a rich stout or porter can create an indulgent flavor experience with the bold and malty notes enhancing the cake’s sweetness.

No matter when or how you choose to serve it up, Dee’s Cherry Pineapple Upside Down Cake is sure to impress.

Make-Ahead, Storing and Reheating

 Every forkful is like a journey to paradise.
Every forkful is like a journey to paradise.

This cake is perfect for making ahead of time, as it only gets better with age. Store the cake in an airtight container at room temperature for up to three days.

If you want to make this cake even further in advance, you can prepare it up until the point where you add the fruit topping. Cover the pan tightly with plastic wrap and refrigerate it for up to 24 hours before baking. When you’re ready to bake, just remove the plastic wrap and let the pan come to room temperature for 30 minutes before proceeding with the recipe.

If you have any leftover cake that you want to store, just cover it tightly with plastic wrap or transfer it to an airtight container and store it in the refrigerator. The flavors will continue to deepen and develop over time.

To reheat individual pieces of cake, just pop them into the microwave for about 10-15 seconds. If you prefer a crispy topping, try reheating the cake slices under the broiler for a minute or so. Be careful not to burn them though!

One word of caution: since this cake contains fresh fruit, it does not freeze well and should not be frozen. It will lose its texture and integrity upon thawing. So enjoy each slice of this delicious cherry pineapple upside-down cake while still fresh!

Tips for Perfect Results

 Turn your frown upside down with a slice of this delicious cake.
Turn your frown upside down with a slice of this delicious cake.

There’s no doubt that making a Dee’s Cherry Pineapple Upside Down Cake can be intimidating. However, with the right tips and techniques, you can create a stunning dessert that everyone will love. Here are my top tips for achieving perfect results every time:

1. Use room temperature ingredients. Be sure to take your eggs and butter out of the fridge at least an hour before you start baking. Cold ingredients can negatively affect the texture of your cake.

2. Grease your pan well. A well-greased pan will ensure that your cake doesn’t stick and that it comes out looking perfect.

3. Dry your pineapple slices. If using canned pineapple slices, be sure to dry them well with paper towels before arranging them in the bottom of your pan. This will prevent excess moisture from making your cake soggy.

4. Don’t overmix your batter. Overmixing can lead to tough, dense cake. Mix just until everything is combined and then stop.

5. Use good quality flavorings. The almond and rum/brandy flavorings in this recipe are what really set it apart from other pineapple upside-down cakes, don’t skimp on them!

6. Let the cake cool in the pan for 10-15 minutes before inverting onto a serving platter so that all topping falls perfectly.

7. Serve the cake warm or at room temperature, as cold will make it hard for you to slice and chew.

8. Store leftovers properly.Cover any remaining cake with aluminum foil or plastic wrap and store it in an airtight container at room temperature for up to 3 days.

By following these tips, you can make sure that this Dee’s Cherry Pineapple Upside Down Cake turns out beautifully every time!


Now, if you’re still feeling uncertain about some aspects of our Dee’s Cherry Pineapple Upside Down Cake Recipe or maybe have a specific question about an ingredient, don’t fret! In this section, we’ve compiled some frequently asked questions that we believe will help you clear up any doubts while preparing this succulent cake. Grab your apron and spatula and let’s dive right in!

Why is my pineapple upside down cake soggy?

One common issue with Pineapple Upside Down Cake is that it can turn out soggy. This might occur due to the excess juice in the pineapple slices. To ensure your cake is not too moist, it is essential to pat dry the pineapple slices with a paper towel before placing them in the baking dish. This will help remove the excess moisture and prevent the cake from turning out too wet.

Does Cherry upside down cake need to be refrigerated?

One helpful tip to keep your cherry cake fresh is to store it in the refrigerator. Simply cover the cake with plastic wrap and it should stay good for up to three days. Additionally, if you find yourself with leftover cake that you want to save for even longer, you can freeze it after allowing the cake to fully cool. Make sure to wrap it well in plastic and place it in a freezer-safe container or bag.

Can I make pineapple upside down cake the night before?

Making a delectable pineapple upside-down cake ahead of time is a great idea, just like with most cakes. You can easily store the cake in the refrigerator or freezer and warm it up slightly before serving to make it taste freshly baked.

Does pineapple upside down cake need to be refrigerated after baking?

It is recommended to refrigerate a pineapple upside down cake due to the presence of perishable ingredients like eggs, cream, and butter. If these ingredients are left at room temperature for more than two hours, there is a risk of spoilage leading to potential illnesses caused by contaminated food.

Bottom Line

In conclusion, Dee’s Cherry Pineapple Upside Down Cake is a recipe that you don’t want to miss out on. With its delicious combination of cherries and pineapple slices on top of a moist and fluffy cake, this will be sure to impress anyone who takes a bite. Not only is it easy to make with common ingredients you may have in your pantry, but the options for substitutions and variations are endless.

So next time you have a special day coming up or just want to treat yourself and your loved ones, give this recipe a try. Whether you prefer it as a cake or pancake, in cupcakes or a bundt pan, with cherry pie filling or fresh pineapple chunks, Dee’s Cherry Pineapple Upside Down Cake will not disappoint.

Trust me, I know a thing or two about baking and this recipe is definitely worth adding to your repertoire. So grab your cast iron skillet, preheat your oven, and get ready to experience the magic of this classic yet unforgettable dessert.

Dee's Cherry Pineapple Upside Down Cake

Dee’s Cherry Pineapple Upside Down Cake Recipe

I made this dump cake up when I had 1 cup of cherry pie filling left over and my SIL likes pineapple upside down cake so I thought why not...
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Course: Dessert
Cuisine: American
Keyword: < 4 Hours, Dessert, Fruit, Pineapple, Tropical
Prep Time: 30 minutes
Cook Time: 35 minutes
Servings: 1 cake
Calories: 428.9kcal


  • 1 cup cherry pie filling
  • 1 teaspoon almond flavoring, divided
  • 1 teaspoon rum flavoring, divided
  • 1 teaspoon brandy flavoring, divided
  • 20 ounces drained pineapple slices
  • 1 cup brown sugar
  • 18 ounces yellow cake mix
  • 1/4 cup oil
  • 3 eggs


  • Mix 1/2 teaspoon of the almond, rum and brandy flavorings into the cherry pie filling.
  • Spread cherry mixture in the bottom of a 9x13 cake pan.
  • Put the pineapple slices on top of cherry pie filling.
  • Put brown sugar on top of pineapple.
  • Mix the cake mix, oil, eggs and balance of the flavorings together.
  • Pour over top of the brown sugar.
  • Bake in a 375 degree Fahrenheit oven for the time recommended on cake box or until browned and toothpick comes out clean.

Your Own Notes


Serving: 173g | Calories: 428.9kcal | Carbohydrates: 74.9g | Protein: 4.5g | Fat: 12.9g | Saturated Fat: 2.1g | Cholesterol: 64.5mg | Sodium: 369.5mg | Fiber: 1.5g | Sugar: 48.6g

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