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{Triple Layer} Pineapple Upside-Down Cake

Cakes and Cupcakes

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{Triple Layer} Pineapple Upside-Down Cake: This pineapple upside down cake is three layers of caramelized pineapples, maraschino cherries, and homemade cinnamon whipped cream! This layered twist on the classic pineapple upside-down cake recipe is sure to be a family favorite!

This pineapple upside down cake is three layers of caramelized pineapples, maraschino cherries, and homemade cinnamon whipped cream! This layered twist on the classic pineapple upside-down cake recipe is sure to be a family favorite!

This is our favorite recipe for the Best Pineapple Upside Down Cake! Don’t let the multiple layers and homemade whipped cream fool you — this is an Easy Pineapple Upside Down Cake Recipe!

This pineapple upside down cake is three layers of caramelized pineapples, maraschino cherries, and homemade cinnamon whipped cream! This layered twist on the classic pineapple upside-down cake recipe is sure to be a family favorite!

I’m out of control.

Well, in the cake department, at least.

Coconut Cake.

Chocolate Peanut Butter Oreo Cake.

Lemon Coconut Cake.

Vanilla Cake with Strawberry Buttercream.

Aaaaaand there are two more cupcake recipes in the works.

It’s becoming a problem.

This pineapple upside down cake is three layers of caramelized pineapples, maraschino cherries, and homemade cinnamon whipped cream! This layered twist on the classic pineapple upside-down cake recipe is sure to be a family favorite!

In my defense, this very large, very tasty, monstrosity of a cake was made for my dad for Father’s Day.

Of course, I’m obnoxious and couldn’t leave well enough alone, and decided that three layers were far better than one layer.

Yeah.

Like I said, I’m out of control.

But, triple the layers means triple the fruit, right? Aka triple the nutrients?

I mean, it makes sense. And it totally justifies us being able to have our cake and eat it too!

(Plus, if you’re already making one layer, why not just make three?? It’s easy–I promise!!)

This pineapple upside down cake is three layers of caramelized pineapples, maraschino cherries, and homemade cinnamon whipped cream! This layered twist on the classic pineapple upside-down cake recipe is sure to be a family favorite!

Pineapple Upside Down Cake From Scratch: 

So, let’s get down to the nitty gritty of this tower of a cake.

Preheat the oven to 350. With a mixer, cream together butter and oil. Add in white and brown sugar, mixing until combined. Add in eggs, one at a time, stirring until just combined.

In a separate bowl, sift together, flour, corn starch, baking powder and salt.

This pineapple upside down cake is three layers of caramelized pineapples, maraschino cherries, and homemade cinnamon whipped cream! This layered twist on the classic pineapple upside-down cake recipe is sure to be a family favorite!

In a liquid measuring cup, whisk together milk, pineapple juice, Greek yogurt, and vanilla extract. Alternately add in the dry ingredients and the wet ingredients into the butter batter, beginning and ending with the dry ingredients.

Add melted butter to each cake pan and sprinkle with brown sugar. Place 7 pineapple rings in each cake pan. Cut maraschino cherries in half, and place two, uncut side down, in each pineapple hole. Spread crushed pineapple over the pineapple and cherries, in order to fill all the areas with pineapple.

Divide the batter between the three cake pans, and bake for 30 minutes, or until a cake tester comes out clean.

This pineapple upside down cake is three layers of caramelized pineapples, maraschino cherries, and homemade cinnamon whipped cream! This layered twist on the classic pineapple upside-down cake recipe is sure to be a family favorite!

Homemade Pineapple Upside Down Cake Tips & Tricks:

  • Due to all of the caramelized goodness, pineapple upside down cakes can be slightly fragile. Be extra careful when handling the cakes, because they can crack easily.
  • The corn starch in this recipe makes the cakes extra tender. Cornstarch + all purpose flour = homemade cake flour.
  • I cut the maraschino cherries in half, but you can add them in whole.
  • The cake should be refrigerated until you are ready to serve.
  • The butter and oil combination yields for a super moist cake, and makes, in my opinion, for an award winning Pineapple Upside Down Cake!

This pineapple upside down cake is three layers of caramelized pineapples, maraschino cherries, and homemade cinnamon whipped cream! This layered twist on the classic pineapple upside-down cake recipe is sure to be a family favorite!

Be still my pineapple lovin’ heart.

 

5 from 2 votes
This pineapple upside down cake is three layers of caramelized pineapples, maraschino cherries, and homemade cinnamon whipped cream! This layered twist on the classic pineapple upside-down cake recipe is sure to be a family favorite!
Print
{Triple Layer} Pineapple Upside-Down Cake
Prep Time
45 mins
Cook Time
30 mins
Total Time
1 hr 15 mins
 
This pineapple upside down cake is three layers of caramelized pineapples, maraschino cherries, and homemade cinnamon whipped cream! This layered twist on the classic pineapple upside-down cake recipe is sure to be a family favorite!
Course: Dessert
Cuisine: American
Keyword: Pineapple Upside-Down Cake
Servings: 12 -14 Slices
Author: Michelle
Ingredients
Pineapple Topping
  • 3 20 oz cans pineapple rings (in pineapple juice or fresh); drained (save 1/4 cup of juice for the cake)
  • 1 20 oz can crushed pineapple (in pineapple juice or fresh); drained
  • 14 maraschino cherries, cut in half
  • 6 Tbsp butter, melted
  • 3/4 cup brown sugar
Cake
  • 1/2 cup butter, softened
  • 1/3 cup vegetable oil
  • 3/4 cup brown sugar
  • 3/4 cup white sugar
  • 4 large eggs
  • 2 2/3 cups all purpose flour
  • 1/3 cup corn starch
  • 2 1/2 tsp baking powder
  • 1/2 tsp salt
  • 3/4 cup milk
  • 1/4 cup pineapple juice, drained from can is fine
  • 3 tsp vanilla extract
  • 1/4 cup Greek Yogurt
Whipped Cream
  • Cinnamon Whipped Cream (recipe linked below)
Instructions
  1. Preheat oven to 350 degrees and grease 3 cake pans ( 9" cake pans) with cooking spray (just to ensure the cakes do not stick).
Pineapple Topping
  1. Place 2 Tbsp of melted butter in each cake pan, and tilt the cake pan around until the better has spread a bit. Sprinkle 1/4 cup brown sugar in each pan.
  2. Arrange pineapple rings in each pan (7 rings should fit nicely in each pan). To fill in any gaps on the outer edge, slice any leftover pineapple rings into cubes and add them between the rings. Place two cherry halves in the center of each pineapple ring, making sure the uncut side is facing downwards (that way the pretty side will show when the cake is out of the pan). Lastly, spread about 1/4 cup of crushed pineapple over the pineapple rings in order to fill in all areas with pineapple. Set aside.
Cake
  1. With a mixer, beat butter until light and fluffy, about 1-2 minutes. Add in oil and mix until combined. Add in both brown sugar and white sugar, beating until well combined (scrape the sides of the bowl with a rubber spatula if needed). Add in the eggs, one at a time, beating until just combined.
  2. In a separate bowl, sift together flour, corn starch, baking powder, and salt.
  3. Whisk together milk, pineapple juice, vanilla extract and Greek yogurt.
  4. Alternately add the dry ingredients and the wet ingredients into the butter mixture, beginning and ending with the dry ingredients. Mix until just combined.
  5. Divide batter evenly between the three cake pans. Bake for 30-35 minutes (mine was done right at 30 minutes), or until a cake tester comes out clean.
  6. Allow cakes to cool completely.
Whipped Cream
  1. Once your cakes have cooled, make the Cinnamon Whipped Cream. Set aside 1/2 cup of whipped cream for decorating.

  2. Place the bottom cake layer on a cake stand and spread about half of the remaining whipped cream over the cake, keeping the whipped cream about 1/2" in from the edge of the cake (as the layers are stacked on top, the whipped cream will spread to the edge). Place the middle layer on top, and spread with remaining whipped cream. Add the top layer, and with a piping bag and star tip, pipe on the whipped cream. Top with a cherry, if desired.
  3. Cake must be kept in the refrigerator until you are ready to eat.
  4. Enjoy!
Recipe Notes

Cinnamon Whipped Cream

 

This pineapple upside down cake is three layers of caramelized pineapples, maraschino cherries, and homemade cinnamon whipped cream! This layered twist on the classic pineapple upside-down cake recipe is sure to be a family favorite!

If you like this recipe, here are some other recipes you might enjoy:

{No Bake} Tropical Cream Pie

{No-Bake} Tropical Cream Pie | A Latte Food

Double Chocolate Cupcakes

Double Chocolate Cupcakes | A Latte Food

Dr. Pepper Cherry Cheesecake Cookie Cups

These double chocolate cookie cups are filled with a no bake Dr. Pepper Cherry® cheesecake filling and topped with homemade whipped cream! | www.alattefood.com

Shared by Michelle

Comments

  1. Michelle @ Blackberry Babe says

    June 22, 2015 at 11:39 am

    This is so gorgeous! Love the layers!

    Reply
  2. Kate @ Diethood says

    June 22, 2015 at 11:45 am

    3 layers of one of the best cakes ever?!? Oh my! YEAH! And it’s gorgeous!

    Reply
  3. Stephanie says

    June 22, 2015 at 12:24 pm

    Yes, yes! 3 layers are better than one for sure! What a beauty of a cake!

    Reply
  4. Medha @ Whisk & Shout says

    June 22, 2015 at 12:40 pm

    This is over the top delicious! So yum 🙂

    Reply
  5. [email protected] The Well Floured Kitchen says

    June 22, 2015 at 2:58 pm

    I’ve never seen a layered upside down cake – but I love it!! It definitely looks like triple the yum 🙂

    Reply
  6. June @ How to Philosophize with Cake says

    June 22, 2015 at 5:15 pm

    What a creative cake! Usually you see upside down cakes as single layers but obviously layer cakes are three times more awesome 😀

    Reply
  7. Courtney @ Neighborfood says

    June 22, 2015 at 7:59 pm

    Whoa! I love that this is layered! What a great twist on the original.

    Reply
  8. Dolores says

    June 23, 2015 at 9:59 am

    You are going to send me to the moon with that cake.
    Yummy !!!!!

    Reply
  9. Mary Frances says

    June 23, 2015 at 6:48 pm

    Why yes, three is always better than one. It’s like the golden rule of cake making. And wow, hello gorgeous! This cake is one stunner, especially with those pineapple slices. Well done!

    Reply
  10. Ashlyn @ Belle of the Kitchen says

    June 23, 2015 at 11:51 pm

    WOW WOW WOW! Girl, three layers is always better than one. I think you made a great choice, there! I bet your dad enjoyed every bite of this gorgeous cake! 🙂

    Reply
  11. Gayle @ Pumpkin 'N Spice says

    June 24, 2015 at 4:22 am

    This cake looks absolutely gorgeous, Michelle! I’ve never made a pineapple upside down cake before, so I’m loving this! Sounds like the perfect summer dessert!

    Reply
  12. Kim (Feed Me, Seymour) says

    June 24, 2015 at 4:31 am

    I can’t remember the last time I had a pineapple upside down cake. But making it triple layer?! Well that is just genius!

    Reply
  13. Meg @ The Housewife in Training Files says

    June 25, 2015 at 6:09 pm

    I am totally jealous of your caking baking ability! This is gorgeous and totally swooning over the pineapple!

    Reply
  14. Georgia says

    January 15, 2016 at 1:15 pm

    I got so excited when I found this recipe! My boyfriend loves pineapple but has never had pineapple upside down cake, so I knew I had to find the perfect recipe for his birthday cake. I baked the cakes a day ahead and assembled them a couple of hours before serving. I did modify the cinnamon whip cream recipe a bit with some cream cheese because I was afraid it would squish out the sides. The cake turned out beautiful and was a huge hit! Not too sweet, very dense like a bundt cake but this could be because I measured my flour before sifting, not after. Everyone was super impressed, thanks for the recipe!

    Reply
  15. ALSTON says

    September 12, 2017 at 8:38 am

    MENTIONED IN RECIPE 1/4 GREEK YOGURT. HOW MUCH 1/4 CUP??

    Reply
    • Michelle says

      September 12, 2017 at 3:18 pm

      Hi Alston! Yep, 1/4 cup. Just a typo–all fixed. Thanks for letting me know!

      Reply
  16. Victoria says

    May 3, 2018 at 7:22 pm

    5 stars
    Can I make this cake the day before and refrigerate it until we serve it the next day? Or is the consistency better if made day of?

    Reply
  17. Randi says

    July 15, 2021 at 7:40 am

    5 stars
    Made this cake for friends bday turned out absolutely beautiful. Thank you for the recipe. LOVE it!

    Reply

Trackbacks

  1. Pineapple Upside Down Cake - Chocolate Dessert Recipes - OMG Chocolate Desserts says:
    March 27, 2016 at 1:02 pm

    […] I saw this cake at A Latte Food  I became  totally obsessed with it. It took the finest part of the entire Pineapple Upside Down […]

    Reply
  2. Pineapple Upside Down Cake - OMG Chocolate Desserts says:
    June 12, 2018 at 1:48 am

    […] I saw this cake at A Latte Food  I became  totally obsessed with it. It took the finest part of the entire Pineapple Upside Down […]

    Reply

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I'm Michelle and this is where you'll witness my baking addiction. I bleed coffee and breathe sugar. Come join me as I journey through life one recipe at a time! READ MORE
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