Make this pineapple upside-down cupcake recipe in 5 easy steps

Pineapple upside-down cupcake recipe from Click Americana

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Pineapple upside-down cupcake recipe: A mini classic

The old-fashioned pineapple upside-down cake, with its caramelized topping and bright pineapple rings, holds a cherished spot in the vintage baking tradition. It’s a cake that has seen countless occasions, gracing the tables of mid-century potlucks and modern-day gatherings alike.

But let’s not overlook its charming little sibling: pineapple upside-down cupcakes. These miniatures honor their classic counterpart, delivering the same upside-down delight in a size that’s perfect for a single serving. A wonderful blend of retro appeal and modern convenience, they’re a testament to the enduring allure of this timeless dessert tradition.

Retro-style pineapple upside down cupcakes

Ready to give it a whirl? Let’s get baking with our kitchen-tested vintage pineapple upside-down cupcake recipe.

How to make pineapple upside-down cupcakes

And now, without further ado, let’s pivot to the centerpiece of our vintage dessert showcase — the recipe!

It’s all about the thrill of transformation here, as we turn simple, everyday ingredients into a scrumptious, single-serving take on a classic treat. Here’s the step-by-step rundown:

Pineapple upside-down cupcake recipe ingredients

Clockwise from the top: Eggs, brown sugar, cake mix, butter, maraschino cherries, and canned pineapple rings


Step 1: Prep cake batter

Set your oven to 350 F and give a liberal coating of cooking spray to 24 muffin tin wells. 

At center stage, have a large bowl at the ready. Into this goes your yellow cake mix, the pineapple juice you drain from the can of rings, oil, and eggs. Using a hand mixer, beat until you have a smooth batter.

Step 2: Prep brown sugar-pineapple topping

Grab another bowl and mix together your melted butter and brown sugar. Once combined, spoon about a teaspoon of the sugar mixture into the bottom of each sprayed muffin well.

Step 3: Fill the muffin cups

Time for some pineapple ring acrobatics. Divide each ring into four roughly equal segments.

Then, place two pineapple pieces in each well (you might want to break them into smaller chunks) followed by a bright red cherry in the center.

ALSO SEE: Weird retro ways to serve pineapple (and a few good ideas, too)


Step 4: Spoon batter & bake

Now comes the final act! Spoon the batter into the prepared muffin tin wells. Be mindful to stop when you’re about a quarter inch from the top. Then, place in the oven for a 20-25 minute bake, or until they’re golden brown.


Step 5: Cool & serve

Finally, let the cupcakes cool for 15 minutes without removing from the tins. Once cooled, gently circle a knife around the edges of each well to loosen the cupcakes, then stage a well-orchestrated flip onto a cooling rack (or, as we prefer, a wax paper-lined baking sheet — it’s messy!).

And there you have it — a parade of adorable pineapple upside-down cupcakes ready to steal the show at your next gathering!




Pineapple upside-down cupcake recipe

Yield: 24 cupcakes
Prep Time: 20 minutes
Cook Time: 25 minutes
Additional Time: 15 minutes
Total Time: 1 hour


  • 1-20 ounce can pineapple rings drained and juice reserved
  • 1 box yellow cake mix
  • 1/2 cup vegetable oil
  • 3 eggs
  • 1/3 cup melted butter
  • 2/3 cup packed brown sugar
  • 12 maraschino cherries cut in half


  1. Preheat oven to 350 F. Generously spray 24 muffin tin wells with cooking spray.
  2. Take a large bowl and blend the yellow cake mix, pineapple juice (from the can), oil, and eggs into a smooth batter.
  3. Next, divide each pineapple ring into four equal segments.
  4. In another bowl, blend butter and brown sugar.
  5. Spoon approximately 1 teaspoon of the brown sugar mixture into each prepared muffin tin well.
  6. Carefully place two pineapple segments and a maraschino cherry half into each well.
  7. Spoon batter evenly into the muffin tins. Stop when you're about 1/4 inch from the top.
  8. Bake for 20-25 minutes. Cupcakes should be golden brown.
  9. Once baked, allow the cupcakes to cool for 15 minutes in the tins.
  10. To remove cupcakes from the tins, gently slide a knife around the edges of each well to loosen them, then flip the tin onto a baking sheet lined with wax or parchment paper.
  11. Voilà! Your pineapple upside-down cupcakes are ready to charm!
Nutrition Information:
Yield: 24 Serving Size: 1
Amount Per Serving: Calories: 194Total Fat: 8gSaturated Fat: 2gTrans Fat: 0gUnsaturated Fat: 5gCholesterol: 30mgSodium: 196mgCarbohydrates: 28gFiber: 1gSugar: 19gProtein: 2g

Click Americana offers approximate nutrition information as a general reference only, and we make no warranties regarding its accuracy. Please make any necessary calculations based on the actual ingredients used in your recipe, and consult with a qualified healthcare professional if you have dietary concerns.

ALSO TRY: Dole’s crushed pineapple upside-down bundt cake recipe (1970)

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