Cake,  Mini Desserts,  Single Layer Cake

Pineapple Upside Down Cake

I’m not a huge pineapple fan. It’s okay, but definitely not my favorite. Pineapple Upside Down Cake, though, is another story.

Pineapple upside down cake reminds me of my Grandma (my mom’s mom), since it was a favorite of hers. My mom always made pineapple upside down cake for her on Mother’s Day and on her birthday. Because of that, pineapple upside down cake has nostalgic properties for me. One bite and I’m transported to my Grandma’s kitchen.

I love the textures of pineapple upside down cake. The cake absorbs some of the butter and juice from the pineapple that are in the bottom of the pan, but aaaaall that brown sugar crisps up and gives you a little crunch.ย The flavor of the baked, caramelized pineapple is much more appealing to me than when it’s raw. Then again, I might eat anything baked in a bath of butter and brown sugar.

This cake is extremely simple to make. All the ingredients mix up in one bowl, it bakes up in one pan, and there are no additional steps after baking. You don’t need to frost or decorate or finish the cake in any way. You just invert it and you’re done!

I did try something a little different with this recipe, too. Of course. It’s not like me to leave “old fashioned” alone. I wanted to see if I could make mini pineapple upside down cakes. You know me and mini desserts. (If you don’t, see a few links below).

I baked up individual pineapple upside down cakes in a jumbo muffin pan (like this one here), each complete with its very own slice of pineapple and halved maraschino cherry. I really liked how they turned out. My kids thought having their own little cake to themselves was cool, too. Check out the notes at the end of the recipe for how to make baby ones. ๐Ÿ™‚

I had never made a homemade pineapple upside down cake before this. Honestly, the only reason that I did was because I had maraschino cherries and pineapple leftover in the fridge from other recipes. I had forgotten about pineapple upside down cake, and I definitely hadn’t had a slice since before my grandmother passed away almost four years ago. My tastebuds jogged my memory as soon as I tasted it. I love, love, love that about food.

Other posts you may like:

Hummingbird Cake

Coconut Pineapple Tart

Orange Upside Down Cake

Pineapple Upside Down Cake

Pineapple Upside Down Cake

Buttery cake with caramelized pineapple, maraschino cherries, and loads of brown sugar. You know the one. ๐Ÿ™‚
Recipe adapted from Martha Stewart (link here).
Prep Time 15 mins
Cook Time 40 mins
Total Time 55 mins
Servings 8 slices


  • 1 1/3 cups flour
  • 3/4 cup sugar
  • 2 tsp baking powder
  • 1/4 tsp salt
  • 1/4 cup vegetable oil
  • 3/4 cup milk
  • 1 tsp vanilla extract
  • 1 egg
  • 1 1/2 tsp lemon juice
  • 1/4 cup unsalted butter, melted
  • 1/2 cup brown sugar, packed
  • 1 pineapple (or one 20 oz. can pineapple slices)
  • maraschino cherries


  • Preheat oven to 350F.
  • Combine dry ingredients (flour, sugar, baking powder, and salt) in a large bowl. Add oil and milk, and whisk to combine.
  • Add vanilla, egg, and lemon juice. Whisk to combine.
  • Add dry ingredients. Whisk until just incorporated and batter is smooth.
  • Pout melted butter into a 9" cake pan (see notes). Sprinkle brown sugar evenly in the pan. 
  • Arrange Pineapple slices and maraschino cherries in the pan. Pour batter over top.
  • Bake 40 minutes, or until cake is golden and a toothpick inserted in the center of the cake comes out clean. Cool in pan 5 minutes. If the cake domed during baking, level cake, then invert cake onto a platter.


Note on cake pan: I used a 9" cake pan with a dark finish, because I wanted the brown sugar to get crunchy. If you use an 8" pan and/or one that is light in color, it will likely take a few extra minutes for your cake to bake through.
Note on making mini cakes: Prepare batter as directed. Recipe will make 10-12 mini pineapple upside down cakes, depending on the size of the jumbo muffin pan used (like this one here).
In each pan cup, pour about 1/2 tablespoon melted butter and top with about 1 tablespoon brown sugar. Place one ring fresh pineapple and one half maraschino cherry in each cup (I placed the cherries cut-side up so that the round edge of the cherry would show after the cakes were inverted). Divide batter evenly between pan cups, filling each about 2/3 full.
Bake 20 minutes, or until lightly golden and a toothpick inserted in the center comes out clean. Let cool in pan 5 minutes. If the cakes domed during baking, level the cakes before inverting.

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