Pineapple Upside Down Cupcakes Recipe

Pineapple Upside Down Cupcakes Recipe

How To Make Pineapple Upside Down Cupcakes

Whip up an adorably delicious fruit dessert with these pineapple upside down cupcakes topped with whipped cream and maraschino cherry.

Preparation: 25 minutes
Cooking: 25 minutes
Total: 50 minutes



  • 28ozpineapple chunks,in pineapple juice, divided
  • cuplight brown sugar,packed
  • cupunsalted butter,plus ¼ cup, softened
  • 1cupall-purpose flour
  • ¾cupgranulated sugar
  • ½tspbaking powder
  • ¼tspsalt
  • ½cuppineapple juice,from pineapple chunk can
  • 1large egg
  • ½tspvanilla extract

For Topping:

  • ¾cupheavy cream
  • 2tbspgranulated sugar
  • 12maraschino cherries


  1. Preheat the oven to 350 degrees F. Spray 12 muffin cups well with non-stick cooking spray.

  2. Drain both cans of the pineapple chunks while reserving ½ cup of the juice.

  3. Place the pineapple over several layers of paper towels to drain well.

  4. Melt ⅓ cup of butter in a microwave-safe bowl, then stir in the brown sugar into the melted butter.

  5. Divide the mixture among the muffin wells, adding about 2 teaspoons to each.

  6. Arrange the pineapple chunks on top of the sugar mixture, about 5 in each. Set aside.

  7. In the bowl of an electric stand mixer, whisk together the flour, granulated sugar, baking powder, and salt.

  8. Set the mixer with a paddle attachment, add ¼ cup of softened butter and pineapple juice, then mix for about 1 to 2 minutes until batter is smooth. Occasionally stop the mixer and scrape down the sides and bottom of the bowl throughout the mixing process.

  9. Mix in the egg and vanilla extract until well combined.

  10. Divide the batter evenly among the muffin cups, layering the batter over the pineapple layer.

  11. Bake in the oven for 23 to 26 minutes, until a toothpick inserted into the center of the cupcake comes out clean.

  12. Remove from the oven, then allow to cool for 5 minutes.

  13. Run a sharp knife around edges of the tins to loosen the cupcakes.

Sweetened Whipped Cream:

  1. In a mixing bowl using an electric hand mixer, whip the cream on high speed until soft peaks form.

  2. Add the sugar, then whip until stiff peaks form. Set aside.

To Assemble:

  1. Place a wire cooling rack over top of the muffin pan, then flip to invert onto the wire rack.

  2. Let cool completely, then pipe the sweetened whipped cream over the cupcakes.

  3. Top each cupcake with a maraschino cherry.

  4. Serve, and enjoy!


  • Calories: 259.59kcal
  • Fat: 11.22g
  • Saturated Fat: 6.82g
  • Trans Fat: 0.21g
  • Monounsaturated Fat: 3.09g
  • Polyunsaturated Fat: 0.55g
  • Carbohydrates: 39.12g
  • Fiber: 1.39g
  • Sugar: 28.44g
  • Protein: 2.37g
  • Cholesterol: 49.44mg
  • Sodium: 78.41mg
  • Calcium: 45.38mg
  • Potassium: 122.19mg
  • Iron: 0.87mg
  • Vitamin A: 113.02µg
  • Vitamin C: 32.75mg
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