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Pineapple Upside Down Cupcakes
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5 from 4 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 mins
Cook Time20 mins
Total Time35 mins
Course: Dessert
Cuisine: American
Keyword: pineapple cupcakes
Servings: 24
Author: Jill


  • Pineapple Cake Mix can use yellow
  • 3 eggs
  • ½ c. vegetable oil
  • 1 c. pineapple juice
  • ½ c. melted butter
  • 1-1/2 c. brown sugar
  • 4 c. crushed pineapple drained
  • 24 maraschino cherries patted dry


  • 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 t. melted butter in bottom of each cupcake cup.
  • Add 2 t. brown sugar to each cup.
  • Place a cherry in the center of the cups.
  • Add 1 T. 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.