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Upside Down Pineapple Cupcakes feature
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5 from 2 votes

Pineapple Upside Down Cupcakes

These pineapple upside-down cupcakes take all the flavors of a traditional upside down cake and makes it in the perfect portion size. These light and fluffy cupcakes make the perfect cupcake for an easy weeknight dessert or for a special occasion.
Prep Time15 minutes
Cook Time20 minutes
Total Time35 minutes
Course: Dessert
Cuisine: American
Keyword: pineapple cupcakes
Servings: 24
Calories: 205kcal
Author: Jill



  • Preheat oven to 350 degrees.
  • Spray two 12 count cupcake pans with non-stick cooking spray.
  • Mix cake mix, oil, eggs and pineapple juice on low speed of mixer until combined. Switch to med. Speed and mix for about 2 min.
  • Spoon 1 teaspoon melted butter in bottom of each cupcake cup.
  • Add 2 teaspoons brown sugar to each cup.
  • Place a cherry in the center of the cups.
  • Add 1 Tablespoon of the crushed pineapple to each cup and pack down.
  • Fill the cups with the cake batter to just below the tops of each cup.
  • Bake on center rack of oven for 20 min. or until toothpick inserted in center comes out clean.
  • Only push toothpick part way into the cupcake so you don’t reach it into the pineapple mixture.
  • Allow to cool in pan on baking rack for 5 min., then invert onto another pan or wax paper covered surface. Turn each cupcake right side up.


Serving: 24g | Calories: 205kcal | Carbohydrates: 23g | Protein: 1g | Fat: 13g | Saturated Fat: 6g | Polyunsaturated Fat: 3g | Monounsaturated Fat: 3g | Trans Fat: 0.3g | Cholesterol: 41mg | Sodium: 73mg | Potassium: 91mg | Fiber: 1g | Sugar: 22g | Vitamin A: 289IU | Vitamin C: 5mg | Calcium: 27mg | Iron: 0.4mg