Kitchen Fun With My 3 Sons

The Best Pineapple Upside Down Cake

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This Pineapple upside down cake is seriously the BEST! Topped with a delicious caramelized pineapples and cherries. This classic dessert is super soft and moist, filled with the perfect amount of pineapple flavor!

We love making delicious pineapple desserts like our pineapple upside-down monkey bread, no-bake pineapple dream dessert, pineapple poke cake, and pineapple whipped pie. You will definitely want to check those out as well!

Pineapple Upside Down Cake Recipe

How to make Pineapple Upside Down Cake

We have tried a LOT of pineapple upside-down cakes and this is our favorite. This cake is completely from scratch, but it’s super easy to make! In fact, it takes only 10-15 minutes to prepare.

Topping – Mix your butter and sugar mixture and pour it into a 9 inch square pan. Place the drained pineapple rings and cherries in the pan, and set aside.

Cake Batter – Mix the dry ingredients and wet ingredients separately and then combine. While you’re still mixing, add milk, pineapple juice, and vanilla extract. Spread batter over the pineapple rings in the 9 inch square pan.

Bake –  Bake at 350 for 45-50 minutes, or until a toothpick comes out clean in the center.

Pineapple Upside-Down Cake

How do I flip an Upside-Down Cake?

  1. Make sure your cake is fully baked before you flip. You can loosen the edges using a knife to make sure nothing is sticking on the sides.
  2. You will want to add a heat-proof dish, pan or platter on top of the cake pan. For this cake, you will want to flip with the dish attached right out of the oven. Otherwise the pineapples might stick to the pan if you let it sit to too long.
  3. Once you flip, leave the pan on the cake/dish for a few minutes to allow the topping to ooze around the edges of the cake.
  4. Now you can remove the pan and serve the warm cake!

How do I freeze Pineapple Upside-Down Cake

Allow the cake to completely cool and place it in the freezer for 1 hour or so until firm. Then wrap with plastic wrap to store. This can be frozen for up to 3 months.

More Delicious Cake Recipes

Banana Pudding Cake

Strawberry Bundt Cake

Orange Crush Cake

Milk and Cookies Cake

Lemon Ricotta Pound Cake

Margarita Cake

Pineapple Upside Down Cake Recipe

Pineapple Upside Down Cake

Published By Jill
This Pineapple upside down cake is seriously the BEST! Topped with a delicious caramelized pineapples and cherries. This classic dessert is super soft and moist, filled with the perfect amount of pineapple flavor!
5 from 23 votes
Prep Time 10 mins
Cook Time 50 mins
Total Time 1 hr
Course Cake
Servings 9
Calories 342 kcal


  • 1/4 cup butter
  • 2/3 cup packed brown sugar
  • 1 20-oz can 9 pineapple slices in juice, drained (reserve juice)
  • 9 10 maraschino cherries
  • 1 1/3 cups all-purpose flour
  • 1 cup granulated sugar
  • 1/3 cup butter (softened)
  • 1 1/2 teaspoons baking powder
  • 1/2 teaspoon salt
  • 3/4 cup milk
  • 1/4 cup reserved pineapple juice
  • 1 egg
  • 1 teaspoon vanilla extract


  • Heat oven to 350°F. Melt butter in the microwave. Pour the melted butter in a 9 inch square pan and then evenly sprinkle with the brown sugar. Arrange pineapple slices over the brown sugar. Place a cherry in center of each pineapple slice.

  • In medium bowl, beat remaining ingredients with electric mixer on low speed 40 seconds, then beat on high speed 3 minutes, until well blended. Pour the cake batter over the pineapples.

  • Bake 45 to 50 minutes or until toothpick inserted in center comes out clean. Immediately top the pan with a plate, pan or serving dish, then flip the cake/dish over. Let the cake sit for a few minutes then remove the pan. This will allow the topping to drizzle over the cake.

  • Serve warm and this is also good topped with whipped cream or ice cream. Cover and store the cake at room temperature or in the fridge.


Serving: 9gCalories: 342kcalCarbohydrates: 54gProtein: 3gFat: 13gSaturated Fat: 8gCholesterol: 52mgSodium: 256mgPotassium: 142mgFiber: 1gSugar: 39gVitamin A: 427IUCalcium: 74mgIron: 1mg
Tried this recipe?Mention @kitchenfunwithmy3sons or tag #kitchenfunwithmy3sons!

about me


I am a mom of 3 awesome boys that love to get crafty with me in the kitchen. Our blog is full of all sorts creative food ideas for the Holidays, Party Ideas, Free Printables, Featured DIY Ideas, Recipes, & Kids Craft Ideas! Read more...

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Whipped this recipe up this evening with dinner…OMG! It was so delicious! My husband requested a pineapple upside down cake for tonight, I had never made such a cake! So I was a little nervous, but this recipe was super easy and quick. 5 stars

This was seriously the easiest and most delicious pineapple upside down cake I’ve ever made. My husband fell in love with it. My kids stood at the stove and ate it straight out of the pan. The cake was super fluffy and the pineapple and ‘glaze’ were spot on. I’ll never use another recipe. 5 stars

Oops I’m using a 9×13 rectangular pan, do I still cook it for 45min? Or less now? Thanks!

Made this today. My husband loved it. Thank you so much for the yummy  recipe.5 stars

This was such and easy recipe everyone loved it but I used a 9×13 pan by mistake came out a lil thin but still delicious5 stars



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