Pineapple Upside Down Cake

A convenient and delicious dessert to please the family!

Prep time 15 mins
Total time 55 mins
Servings 10
Calories per serving 380

About This Recipe

The pineapple upside down cake has earned its stripes as a classic dessert by reigning over the hearts of Americans for almost a century. The origins of the cake are from the late 1800’s, but you can thank Dole® for catapulting it into the well known dessert it is today! Way back in 1925, Dole® held a recipe contest for the best dishes made with pineapple. The pineapple upside down cake recipe stole the show: it was so ridiculously popular that Dole® had to let the whole country know about it through a huge advertising campaign! This all might be hard to believe, but if you’ve ever had the pleasure of taking a bite of this dessert, you’d understand.

Now, of course, nothing beats the original, old fashioned recipe from Dole®, but this easy pineapple upside down cake sure comes close! Plus, by using a boxed mix instead of baking from scratch, you’ll find this recipe to be a cakewalk. After you layer your butter, sugar, pineapple slices, and cherries, simply pour your batter over and bake. Then, place a plate on top of the skillet or pan, and flip it upside down to reveal a cake that’s presented like a work of art!

Traditionally, the upside down cake is cooked in a cast iron skillet, which is how the captivating flower-like design of caramelized pineapples and cherries comes from. In the 1800’s, when the very first upside down cakes were created, the pans had legs to hold it above an open fire. If you looked at the pan from above, the legs stuck out like little spider legs. This led to the affectionate nickname for the cake: the “Spider Cake”. But you shouldn’t feel confined to a skillet when you make this cake! This recipe is just as delicious and easy to make in a baking pan, as we’ve outlined below.

Everyone loves the pineapple upside down cake, but did you know there’s variations with all kinds of fruits? The first recipes used other fruits like apples, apricots, and even prunes. It wasn’t until Dole® showed the world the best fruit for upside down cakes that pineapples became the most popular topping. It’s no surprise pineapples became known as the best, because the tangy notes balance amazingly with the sweetness of the caramelized sugar and the cake.

This cake is also traditionally created using pineapple slices, but with this recipe, feel free to get creative with other types of pineapple like tidbits, chunks, or even crushed pineapple. Have fun experimenting with different patterns and textures for the top of your cake, and let us know in a review if you found one you really like!

If you’re feeling adventurous, it’s perfectly fine to try substituting the pineapple with other fruits altogether, like our ancestors did when inventing the first “spider” cakes. But we recommend exploring entirely different recipes, like our Mandarin Spice Upside Down Cake or Banana Gingerbread Upside Down Cake recipe. When it comes to using fruit other than pineapple, the best upside down cake recipes will replace pineapple’s tangy bite with a flavor that carries a similar kick, like allspice or clove.

Now that you’ve read all about this unique cake, your mouth is probably watering in anticipation. Don’t keep your taste buds waiting any longer! Grab your ingredients, preheat the oven, and get ready to make a little slice of paradise, just like people did back in the day.


  • 1/4 cup butter or margarine
  • 2/3 cup packed brown sugar
  • 10 maraschino cherries
  • 1 package (2-layer) Pineapple Flavored or Yellow Cake Mix
  • 1 can (15.25oz) Dole® Tropical Gold® Slices


  1. Drain pineapple slices; reserve 3/4 cup syrup.
  2. Stir together melted butter and brown sugar in 12-inch skillet with heat-proof handle. Arrange pineapple slices in sugar mixture. Place cherry in center of each pineapple slice.
  3. Prepare cake mix according to package directions, replacing some of the water with reserved 3/4 cup syrup that is needed to prepare the batter. Pour batter evenly over pineapple.
  4. Bake at 350 Fº, 35 to 40 minutes or until toothpick inserted in center comes out clean.  Cool 5 minutes.  Loosen edges and invert onto serving platter.

Note: Cake can be baked in 13 x 9-inch baking pan instead of skillet. Prepare and assemble cake as above except cut two pineapple slices in half and place whole slices along edges of pan and halved slices in center. Place cherries in center of slices. Bake and cool as above.

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