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+ servings
two pineapple upside down cupcakes served on white plates with silver forks

Pineapple Upside Down Cupcakes

These are perfect little packages of vanilla cake and caramelized pineapple topped with whipped cream and a cherry.
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Course: Dessert
Cuisine: American, Western
Prep Time: 10 minutes
Cook Time: 20 minutes
Servings: 12
Calories: 509kcal


  • 1 ⅛ cup (255g) butter melted
  • 1 cup (200g) sugar
  • 2 cups (240g) flour
  • 1 tablespoon pineapple juice
  • 4 eggs
  • ¼ cup (50g) brown sugar
  • 12 pineapple rings
  • 2 cups (480ml) heavy whipping cream
  • 2 tablespoons powdered sugar
  • 12 maraschino cherries for garnish


  • Combine a ⅛ cup melted butter with the brown sugar, then add a portion to each of the 12 sections in your cupcake pan, Place one pineapple ring in each cupcake section.
  • In a mixing bowl, whisk together the cup of melted butter with sugar, pineapple juice, and eggs.
  • Stir in the flour, then add to each cupcake section, filling about ¾ from the top.
  • Bake cupcakes at 350F / 180C for 20 minutes, or until a toothpick inserted in the center comes out clean.
  • Remove from oven and allow cupcakes to cool fully before removing from pan.
  • Make whipped cream by beating cream and powdered sugar together until soft peaks form.
  • Transfer whipped cream into a piping bag with and pipe onto the cupcakes with a star attachment. Garnish each cupcake with a cherry.


  • If you have trouble fitting the pineapple into your cupcake pan, you can slice the pineapple rings in half.
  • You can also use a jumbo muffin pan and make 6 large cupcakes instead of 12 smaller ones. 
  • For easy removal, allow the cupcakes to cool for a few minutes then slide a knife around the edges before inverting onto a waxed paper lined tray. 
  • Whenever possible, serve these cupcakes warm and add a scoop of vanilla ice cream on the side. It’s the best way to enjoy them! 
  • Prep - Make the cupcakes a day ahead and store them in the fridge until needed. Allow them to come to room temperature and top them with whipped cream and a cherry before serving. 
  • Store - Place the cupcakes in an airtight container and store them in the fridge for up to 4-5 days.
  • Freeze – Cool the cupcakes completely and set them on a tray in the freezer for one hour. Remove the tray and wrap each cupcake with plastic wrap and foil or seal in a freezer-safe container. Use within 2 to 3 months.  Defrost on the counter and top before serving. 


Calories: 509kcal | Carbohydrates: 49g | Protein: 5g | Fat: 33g | Saturated Fat: 13g | Trans Fat: 1g | Cholesterol: 109mg | Sodium: 239mg | Potassium: 160mg | Fiber: 1g | Sugar: 31g | Vitamin A: 1452IU | Vitamin C: 6mg | Calcium: 57mg | Iron: 1mg