The Best Pineapple Upside Down Cake

This post may contain affiliate links. Please read our disclosure policy.

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
4.95 from 34 votes

Pineapple Upside Down Cake

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!
Servings: 9 servings
Prep: 10 minutes
Cook: 50 minutes
Total: 1 hour


  • 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.

Last Step:

Please leave a rating and comment letting us know how you liked this recipe! This helps our business to thrive and continue providing free, high-quality recipes for you.


Serving: 9g | Calories: 342kcal | Carbohydrates: 54g | Protein: 3g | Fat: 13g | Saturated Fat: 8g | Cholesterol: 52mg | Sodium: 256mg | Potassium: 142mg | Fiber: 1g | Sugar: 39g | Vitamin A: 427IU | Calcium: 74mg | Iron: 1mg


Leave a Review!

We LOVE hearing from you! Submit your question or comment here.

Your email address will not be published.

Your email address will not be published. Required fields are marked *

Recipe Rating:

I accept the Privacy Policy

14 comments on “The Best Pineapple Upside Down Cake”

  1. 5 stars
    I decided to try making this yesterday. It was a big hit. Infact I caught my husband sneaking out during the night and sneaking some more. Yum yum

  2. 5 stars
    I made this for my mother-in-law’s birthday and it was a hit! I didn’t have any vanilla but it didn’t take away from the deliciousness!

  3. 5 stars
    I add one small can of crushed pineapple along with the rings Also I put the mirachino cherries in the center rings after it has baked and flipped onto a plate. They’re pretty and bright.
    It’s my go-to easy dessert – and fabulous!

  4. 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 delicious

  5. 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. 

  6. 5 stars
    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.