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See how to make this easy recipe for Pineapple Upside Down Cupcakes
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5 from 1 vote

Pineapple Upside Down Cupcakes

A delicious homemade dessert featuring pineapple, brown sugar, butter and a cherry on top!
Prep Time15 mins
Cook Time20 mins
Total Time30 mins
Course: Dessert
Cuisine: American
Keyword: pineapple upside down cupcakes
Servings: 6 servings
Calories: 367kcal
Author: Cindy


  • 1/4 cup unsalted butter
  • 2/3 cup brown sugar
  • 14- oz pineapple rings canned or fresh
  • 6 maraschino cherries optional
  • 2 large eggs
  • 2/3 cup sugar
  • 4 tbsp pineapple juice
  • 1 tsp vanilla
  • 2/3 cup flour
  • 1 tsp baking powder
  • 1/4 tsp salt


  • Preheat oven to 350°F. Spray a jumbo size muffin pan thoroughly with nonstick cooking spray.
  • In a small saucepan, melt the butter over medium heat, and whisk in brown sugar until blended.
  • Spoon about 2 tablespoons of topping mixture into each muffin cup, and then place a pineapple ring and cherry on top.
  • In a medium bowl, beat eggs and sugar until smooth. Mix in pineapple juice, vanilla, flour, baking powder and salt.
  • Divide batter evenly across 6 muffin cups and bake for 20-25 min until golden brown. 
  • Remove from oven and cool for 5 min before running a knife around the outside of each cake.
  • Place a cooling rack on top of muffin pan and quickly invert to unmold. Bang on counter to help loosen the cakes. Serve warm.



  • Ahead of Time Note: You can store these cupcakes in an airtight container in the fridge for up to 3 days or in the freezer for up to 2 months.


Calories: 367kcal | Carbohydrates: 67g | Protein: 4g | Fat: 10g | Saturated Fat: 6g | Polyunsaturated Fat: 1g | Monounsaturated Fat: 3g | Cholesterol: 92mg | Sodium: 359mg | Potassium: 195mg | Fiber: 1g | Sugar: 56g | Vitamin A: 350IU | Vitamin C: 9.1mg | Calcium: 120mg | Iron: 1.6mg