Design to Dish: Mini Pineapple Upside-Down Cakes

pineapple cake mini whipped cream cupcakes “Pining for Pineapple” print by Joni Tyrrell; Mini Pineapple Upside-Down Cakes (recipe below)

Pineapples had a very big year in 2014—the tropical fruit popped up on everything from clothing and home décor to party goods and wall art. It felt like not a single day went by without someone blogging about pineapples or sharing a pineapple-themed DIY project. Whether or not this pineapple trend will continue this year is debatable, but regardless, pineapples will always be popular in the kitchen.

Pineapple upside-down cake is an old-school favorite, it’s been a kitchen classic for over 50 years! These mini versions have all of the sweet, brown sugary goodness of the original, packed into a cute, single-serving size. They’d look great on a dessert table and the recipe makes enough to feed a crowd.

mini pineapple upside-down cupcakes

Keep reading for the recipe for these delicious mini cakes!

Mini Pineapple Upside-Down Cakes
Adapted from the America’s Test Kitchen Family Cookbook

4 8-oz cans crushed pineapple
1 1/2 cups (3 sticks) butter, softened
1 1/2 cups brown sugar
3 cups flour
1 tablespoon baking powder
1 teaspoon salt
1 1/2 cups sugar
5 large eggs
2 teaspoons vanilla
2/3 cup whole milk

Pour pineapple into a fine-mesh sieve and allow to drain for 30 minutes; discard liquid. Preheat the oven to 350 degrees F. Spray 24 cupcake tins lightly with nonstick spray. In a small saucepan, melt 1 stick butter. Add brown sugar. Divide mixture evenly among the cupcake tins, then top with drained pineapple. Use a spoon to firmly pack the brown sugar and pineapple into the bottom of each tin, then set aside. In a medium bowl, combine flour, baking powder, and salt. In a large bowl, beat remaining 2 sticks of butter with sugar until light and fluffy, 2-3 minutes. Add eggs one at a time, beating after each addition. Beat in vanilla and scrape down the sides of the bowl with a spatula.  With the mixer on low, add 1/3 of the flour mixture, then half of the milk. Repeat until ingredients have been added. Turn the mixer up to medium briefly to make sure all ingredients are mixed in.  Spoon enough batter into each tin to fill it almost to the top. DO NOT OVERFILL! You will probably have extra batter left over. You can discard it or bake a few plain cupcakes with it. Bake mini cakes 20-25 minutes, until a toothpick inserted in the center of one cake comes out clean. Remove mini cakes from oven, immediately flip them over onto a cookie sheet lined with parchment paper, remove pan, and allow to cool completely. If any pineapple topping sticks to the pan, simply scoop it out with a spoon and put it back on top of the mini cake it belongs to. Serve topped with sweetened whipped cream. Makes 24 mini cakes.

mini pineapple upside down cupcakes

Find more of Melissa on her blog.

  1. How cute are these mini pineapple upside down cakes? Pineapple upside down cake was a childhood favorite of mine. Seeing these brings back memories. Time to get in the kitchen and make these lickety split.

    • Hi Lynn! Pineapple upside down cake was a childhood favorite of mine too! These are so good and so cute!