Mini Pineapple Upside Down Cakes & a little history


Pineapples have been around forever, right? Yes! Well, almost. In reality, canned pineapples that we use in our beloved upside down cakes were not available until 1903 when Jim Dole of the Hawaiian Pineapple Company (now Dole Pineapple) perfected a way to tin them.

So where did people get the idea of putting fruit at the bottom of a cake pan?

Well, this technique has been around since the Middle Ages. Traditionally made with apples, cherries and other seasonal fruit upside down cakes were often made in cast-iron skillets on top of the stove. The use of pineapple (and an oven) was just the newest most novel twist, an ode to twentieth century technologies and notions of convenience. Indeed it did not take long for the recipe to work its way into the American housewife’s repertoire.

By 1925 the Hawaiian Pineapple Company was receiving 2500 recipes for Pineapple Upside Down Cake when it asked people to submit creative ways to prepare pineapples. Only 2 decades after the introduction of the canned pineapple the Pineapple Upside Down Cake had become a pop icon!


While rooting around in old women’s magazines I found a Gold Medal Flour ad with a full-page, four-color picture of Pineapple Upside-Down Cake–a round cake with six slices of pineapple, candied red cherries, and a brown sugar glaze. The date: November 1925.” —American Century Cookbook: The Most Popular Recipes of the 20th Century, Jean Anderson.


The next year (1926) the Hawaiian Pineapple company capitalized on the popularity of the Pineapple Upside Down Cake by running a national ad campaign featuring the recipe. Further solidifying its place in culinary history.

pineapple-upside-down-muffins copy.jpgHere’s a new twist to our adored, heirloom favorite. Minis!  I love this recipe not only because I love pineapple upside down cake, but because they provide one individual serving. The perfect anytime treat without tainting the entire gorgeous cake. This is a time to play with your food.

This recipe is for a muffin-like cupcake and are amazing. However, I like to pretty them up right before serving by placing them in cupcake papers, adding a swirl of butter cream frosting or whipped cream in the center and if you insist,  another cherry on top 🙂



  • 4 tablespoons butter
  • 1⁄2 cup brown sugar
  • 1 teaspoon cinnamon
  • 1 (8 ounce) can pineapple slices, preferably in heavy syrup. Chunks in a round work great too!
  • 12 maraschino cherries


  • 1 1⁄2 cups unbleached all-purpose flour
  • 2 teaspoons baking powder
  • 6 tablespoons butter, softened
  • 1 cup sugar
  • 2 teaspoons vanilla
  • pinch of nutmeg
  • 2 large eggs
  • 1⁄2 cup pineapple juice (reserved from can)
  • 1⁄2 cup milk

mini pineapple upside down cakes jumbo batter.JPG


  • In a small pan melt 4 tablespoons of butter over medium heat. Add brown sugar and cinnamon, stir until sugar has melted. Remove from heat. Grease muffin tin (do not use liners).
  • Break pineapple slices in half and arrange in muffin tin. The broken halves should over-lap each other within one muffin round. Place cherries in the center hole and sprinkle about a tablespoon of brown sugar mix over each pineapple and cherry.
  • Preheat oven to 350°


  • In a large bowl, sift flour and baking powder; set aside. In a medium bowl beat softened butter and sugar until light and fluffy. Stir vanilla and nutmeg into butter/sugar mix add eggs and beat well. In a small bowl, combine pineapple juice and milk. Fold wet mixes into the dry in alternating fashion (between the butter/sugar mix and juice/milk mix).
  • Stir until it’s just combined — don’t over mix. Pour batter into muffin tin over topping.
  • Bake for 20 minute or until cupcake is spongy to the touch. Let cool for 5 minute and run the edges of cupcakes with butter knife and carefully lift out and transfer to plate. Or carefully cover top of cupcakes with a large cookie/baking sheet and flip/invert.

Makes 12

26 Comments Add yours

  1. These are so cute 🙂

    Liked by 1 person

    1. Thanks, Lynne! Almost guiltless since they are so small! Let’s have 2 shall we?? xoxo

      Liked by 1 person

      1. Oh for sure 🙂 xxx

        Liked by 1 person

  2. Antonia says:

    These look delicious Lana and I Iove the idea of adding whipped cream! I enjoyed reading your post….just fascinating 😀

    Liked by 1 person

    1. Thanks, Antonia! Oh yes! The whipped cream is almost a must 🙂

      Liked by 1 person

  3. Such lovely mini cakes!
    Thanks also for all the historical info. Always a pleasure to read. 🙂

    Liked by 1 person

    1. Thank you, Ronit! I’m so happy you enjoy the history too!

      Liked by 1 person

  4. Love the history! I remember my mom making this cake, I have to tell her about this idea.

    Liked by 1 person

    1. Thanks so much! They stay so moist this way…unless we plan to eat the entire cake in one sitting 🙂

      Liked by 1 person

  5. I tired to make these once and I failed completely! The cupcake pan I was using was not big enough for everything to fit haha Your’s look great!

    Liked by 1 person

    1. Aww! haha, Sweetie! Cupcake overflow! I can see it lol! Thanks a bunch!

      Liked by 1 person

    1. Thanks, Lynn! This way everyone can say “I ate the whole cake!” haha! ♥

      Liked by 1 person

  6. They are so cute and perfect little morsels of sweetness 🙂

    Liked by 1 person

    1. Aww, Thanks Sweet Marisa! You say the most beautiful things! ♥

      Liked by 1 person

  7. Ohhh love these mini pineapple upside down cake, they look so cute Lana 🙂 great read about the history as well!

    Liked by 1 person

    1. Thank you, Freda my friend! They’re quite impressive when served on a pretty platter. I’m so happy you enjoyed this!! ♥

      Liked by 1 person

  8. cynthiamvoss says:

    These look so cute and delicious! It’s like somehow you knew that I’ve been taking about making pineapple upside down cake for weeks 🙂 Now I have no excuse not to!

    Liked by 1 person

    1. Thank you, Cynthia! That’s right–no excuses lol! 🙂 They’re even more simple to prepare than the big cake.

      Liked by 1 person

      1. cynthiamvoss says:

        Looks so good. I’m thinking maybe for Mother’s Day.

        Liked by 1 person

      2. This would be perfect! Thanks again, Cynthia!

        Liked by 1 person

  9. Wow, this is an awesome idea, love it Lana!

    Liked by 1 person

    1. Thanks, Kathryn! We love them!

      Liked by 1 person

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