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Pineapple Upside Down Yogurt Cake Recipe

This post is sponsored by STAR FINE FOODS, maker of awesome Olive Oils, Vinegars, glazes, capers, anchovies, onions, and the list goes ON and ON! Thank YOU, friends, for supporting the brands that make Diethood possible!

Pineapple Upside Down Yogurt Cake is an easy dessert recipe for super moist homemade pineapple upside-down cake. This cake is made with olive oil and yogurt, and has a buttery-sweet brown sugar topping!

If you like this cake recipe you should also try my classic Pineapple Upside Down Cake Recipe or this Bananas Foster Upside Down Cake.

A whole Pineapple Upside Down Cake with cherries and pineapple on top of a wire rack

This Pineapple Upside Down Cake Is Perfect For Special Occasions 

Celebrating Leap Day with cake! Yeah!

Hi-ya! Happy Leap Day, Happy Monday! To all the babies that were born on this day, please do tell on what day will you celebrate your birthday next year, when the 29th ain’t around?! Will it be on the 1st of March, or on the 28th of February? Is that how it works? I really, really do want to know. 

Second discussion on the agenda; talking about 2 sweet treats within 4 days… It’s like someone else took over my blog AND kitchen. But that Lemon Bread? Ugh. It was so dang good.

A close up top view of a Pineapple Upside Down Cake

While I do have a sweet tooth, I try to calm down that beast by not making a whole lot of desserts. I mean, when I look at the sugar content in what is about to go into my belleh, I make myself all kinds of promises. Things like, I’ll eat spinach salads for days. Or, let me have this cake and I’ll run on the treadmill for days. All lies, but still. I’ll believe anything for a slice of cake, know whadda mean?

You’ll Love This Healthier Version Of Classic Pineapple Upside Down Cake

Having said that, this is a good one, I swear. It’s a bit different than your classic Pineapple Upside Down Cake recipe, but I think that it’s still just as decadent.

STAR Butter Olive Oil container

There’s at least 1 cup of butter, if not more, in a classic Pineapple Upside Down Cake, but I lightened it up a bit with the help of my trusted nonfat yogurt and STAR’s Butter Flavored Olive Oil, which is a healthier alternative to butter in baked goods. If interested in how to use this olive oil in other baked goods, be sure to check out STAR’s conversion chart for butter to olive oil.

Butter to Olive Oil Conversion Chart

But, the only thing I didn’t mess with in this classic cake is the buttery brown sugar topping. I mean, come on. Who would do that?! We have to live a little.

Pineapple rings and cherries laid out on a baking sheet

Is This Pineapple Upside Down Cake Easy To Make?

Also? I call this the very easy cake because we’re just mixing it all in a bowl, or two, with a spoon, and layering it on top of pineapples and sweet, tart Maraschino Cherries by STAR Fine Foods. STAR Maraschino Cherries are premium grade cherries, but more importantly, they are the prettiest darn garnish for cocktails and desserts. 

Pineapple Upside Down Cake topped with a cherry and pineapple on a wire rack

I should add that I’m also VERY thankful for one layer cakes because I don’t have the skills to make a layer cake with pretty frosting and ribbons. I’m more of a bake-a-cake-with-fruit-underneath-it-and-flip-it-over type of girl. Example 1: Peach Upside-Down Ricotta Cake. Example 2: Bananas Foster Upside Down Cake.

Pineapple Upside Down Cake topped with whipped cream and a cherry on a white plate with a fork

I am nuts over this one, though. It’s that good. And with that whole brown sugar topping stuff? AND some whipped cream? I just can’t. I have zero patience to frost a cake so THIS? It just… it works. 

For more information on STAR Fine Foods Products, please check them out on Facebook, Twitter, and Pinterest.

STAR Butter Flavored Olive Oil is available at select Savemart, Raley’s, Stater Bros. and Food Maxx stores and ONLINE.



A whole Pineapple Upside Down Cake with cherries and pineapple on top of a wire rack

Pineapple Upside Down Yogurt Cake Recipe

Katerina | Diethood
Pineapple Upside Down Yogurt Cake is an easy dessert recipe for super moist homemade pineapple upside-down cake. This cake is made with olive oil and yogurt, and has a buttery-sweet brown sugar topping!
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Servings : 10
Prep Time 20 minutes
Cook Time 1 hour
Total Time 1 hour 20 minutes


  • 6 to 8 pineapple rings (fresh or canned)
  • 6 to 8 STAR Maraschino Cherries
  • 1-1/2 cups all-purpose flour
  • 1-1/2 teaspoons baking powder
  • 1/2 teaspoon baking soda
  • 1/2 teaspoon salt
  • 3/4- cup nonfat yogurt (I always use Dannon)
  • 2 large eggs
  • 1 teaspoon pure vanilla extract
  • 1/3- cup STAR Butter Flavored Olive Oil
  • 3/4- cup light brown sugar
  • 4 tablespoons unsalted butter
  • 3/4- cup light brown sugar
  • 1 tablespoon bourbon


  • Preheat oven to 350F.
  • Grease an 11x7 baking pan with cooking spray or you can also use an 8-inch cake pan or an 8x8 brownie pan.
  • Arrange the pineapples on the bottom of the prepared pan and add a maraschino cherry in each pineapple hole; set aside.
  • In a medium bowl, whisk together flour, baking powder, baking soda, and salt; set aside.
  • In a large bowl, whisk together yogurt, eggs, vanilla, olive oil, and 3/4 cup light brown sugar.
  • Add flour mixture to the yogurt mixture and mix just until combined and no lumps appear. Set aside.
  • In a nonstick skillet, melt 4 tablespoons butter over medium-high heat; add the brown sugar and bourbon and stir and cook until sugar is dissolved.
  • Pour the buttery mixture over the pineapples.
  • Pour the previously prepared batter over pineapples.
  • Tap the pan on the counter to settle the batter, and smooth top with an offset spatula.
  • Bake for 40 to 50 minutes, or until a toothpick inserted in the center comes out clean.
  • Let stand for 30 minutes in the pan; invert onto a serving platter.
  • Cut and serve.


Calories: 305 kcal | Carbohydrates: 45 g | Protein: 3 g | Fat: 12 g | Saturated Fat: 4 g | Cholesterol: 45 mg | Sodium: 208 mg | Potassium: 172 mg | Fiber: 0 g | Sugar: 39 g | Vitamin A: 205 IU | Vitamin C: 3.4 mg | Calcium: 86 mg | Iron: 0.8 mg

Nutritional info is an estimate and provided as courtesy. Values may vary according to the ingredients and tools used. Please use your preferred nutritional calculator for more detailed info.

Course: Dessert
Cuisine: American
Keyword: best pineapple upside down cake, easy pineapple upside down cake, from scratch pineapple upside down cake, pineapple upside down cake recipe, yogurt cake, yogurt in cake
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