Pineapple Upside Down Cupcakes

Published March 14, 2018. Updated May 22, 2024

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I’m definitely adding these delicious Pineapple Upside Down Cupcakes to my list of favorite cupcakes! They’re just as delicious as a standard size pineapple upside down cake but they’re cuter, funner and less messy in these smaller individual servings.

Pineapple Upside Down Cupcakes With Cherry and Whipped Cream

Pineapple Upside Down Cupcakes

I love these so much because they are just one of those good old fashioned recipes like your mom or grandma used to make, but rather they’re made into cupcakes!

I could eat three of them in one sitting no problem, which is why I’m making them again tomorrow for the second time this week!

I’m having family over for a ham and potato dinner (my mom makes the best ham gravy) and I thought these would be the perfect finish for that meal. Pineapple and ham it just goes together, right?

How To Make Pineapple Upside Down Cupcakes



Mini Pineapple Upside Down Cakes on Cooling Rack

Easy to Make Pineapple Upside Down Cupcakes

These are actually really easy to make, they require a few steps but it goes pretty fast.  It’s worth the extra steps, I promise.

Whatever you do though, don’t leave off the maraschino cherries. It’s just wouldn’t be the same without them.

You can usually find the cherries either by the canned fruit at the grocery store or buy the ice cream cones.

My kids go crazy for the things (oh, and me too). I have to hide them when I buy them or it’s like the first thing they ask for every day.

Smart kids, I mean how could your day go wrong when you start it out with a maraschino cherry? The finer things in life.

Scroll below the recipe to see the steps for making these cupcakes!


Individual Pineapple Upside Down Cakes on Plate

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4.86 from 14 votes

Pineapple Upside Down Cupcakes

These delicious Pineapple Upside Down Cupcakes are the perfect party dessert.
Servings: 12 servings
Prep25 minutes
Cook25 minutes
Ready in: 50 minutes


  • 1 (20 oz) can pineapple chunks in pineapple juice
  • 1 (8 oz) can pineapple chunks in pineapple juice
  • 1/3 cup (2.7 oz) packed light brown sugar
  • 1/3 cup (2.6 oz) unsalted butter
  • 1 cup (5 oz) all-purpose flour
  • 3/4 cup (5.6 oz) granulated sugar
  • 1/2 tsp baking powder
  • 1/4 tsp salt
  • 1/4 cup (2 oz) unsalted butter, softened
  • 1/2 cup (4 oz) pineapple juice (from pineapple chunk can)
  • 1 large egg
  • 1/2 tsp vanilla extract



  • Preheat oven to 350 degrees. Spray 12 muffin cups well with non-stick cooking spray.
  • Drain both cans of the pineapple chunks while reserving 1/2 cup of the juice for batter. Place pineapple over several layers of paper towels to drain well. Melt 1/3 cup butter in a microwave safe bowl then stir brown sugar into melted butter.
  • Divide mixture among muffin wells, adding about 2 tsp to each. Arrange pineapple chunks on top of the sugar mixture, about 5 in each (you may not use all of them but I found one 20 oz can wasn't quite enough so I ended up opening 2 cans. The pineapple may be too long to make a flower shape but try to squeeze in 5 of them unless they are large chunks). Set aside.
  • In the bowl of an electric stand mixer whisk together flour, 3/4 cup sugar, baking powder and salt.
  • Set mixer with a paddle attachment, add 1/4 cup softened butter and pineapple juice then mix until batter is smooth, about 1 - 2 minutes (if using a paddle attachment that doesn't constantly scrape bowl, then occasionally stop mixer and scrape down sides and bottom of bowl throughout mixing process).
  • Mix in egg and vanilla extract until well combined. Divide batter evenly among muffin cups, layering batter over pineapple layer.
  • Bake in preheated oven until toothpick inserted into into center of cupcake comes out clean, about 23 - 26 minutes. Remove from oven and allow to cool 5 minutes, then run a sharp knife around edges to loosen.
  • Place a wire cooling rack over top of muffin pan and flip to invert onto wire rack. Let cool completely then pipe sweetened whipped cream over cupcakes just before serving and top with a maraschino cherry.
  • For the sweetened whipped cream:
  • In a mixing bowl using an electric hand mixer (or in a clean stand mixing bowl set with whisk attachment), whip cream on high speed until soft peaks form. Add sugar then whip until stiff peaks form.
  • Recipe source: adapted from Bake Create Love
Nutrition Facts
Pineapple Upside Down Cupcakes
Amount Per Serving
Calories 313 Calories from Fat 126
% Daily Value*
Fat 14g22%
Saturated Fat 9g56%
Cholesterol 57mg19%
Sodium 63mg3%
Potassium 152mg4%
Carbohydrates 44g15%
Fiber 1g4%
Sugar 33g37%
Protein 2g4%
Vitamin A 540IU11%
Vitamin C 7.3mg9%
Calcium 45mg5%
Iron 0.9mg5%
* Percent Daily Values are based on a 2000 calorie diet.
Nutrition values are estimates only. See full disclaimer here.