Classic Pineapple Upside Down Cake

A few years ago, while visiting a friend in Montreal, she pulled out a pineapple upside down cake that she had made the day before. Not one for “fruit” cakes, I was hesitant to try it. It turned out to be the moistest, delicious cake ever. I sheepishly asked for the recipe!

Classic Pineapple Upside Down Cake

I’m not one to ask for a recipe and add it to a pile and never make it. If I ask for a recipe, it’s usually because I want to make it the following weekend! However, this one got away from me! It’s been in my recipe book staring at me.

Classic Pineapple Upside Down Cake

At work, a few of the ladies bake cakes for the others when it’s their birthday. There is a colleague having a milestone birthday this weekend and is leaving on a secret excursion that her husband put together. Some of the girls at work, including myself, knew this was happening as the husband contacted the boss to request that his wife have a few days off. That’s when we put into motion setting up a birthday lunch before she left. 🙂

Classic Pineapple Upside Down Cake

When asked what kind of cake she wanted, she couldn’t chose! She owns a cookbook dedicated to cakes that she was going to tab for me and I was going to pick one at random, but given our busy schedules and another surprise birthday party (where she was told about the secret excursion) it got forgotten about. So last week, I suggest this one as a possibility. I think we’re all happy that she said yes, as it was gone in record timing!

Classic Pineapple Upside Down Cake

From my research, Pineapple upside down cake is from the 1920’s and hasn’t changed much since. Today, another colleague said she adds rum to the cake when it’s pulled out of the oven to soak in before flipping over. I think this would be a grand idea for next time!

Classic Pineapple Upside Down Cake

I could just eat the cake by itself without the upside down part, but it does make it special, and extra tasty! Perfect with coffee or tea!

Classic Pineapple Upside Down Cake

Turning it over always stops your heart as it’s the moment of truth! Beautiful little jewels. My friend in Montreal cuts the pineapple into quarters, as this helps slicing the cake. It’s not always easy, or nice looking, to try and cut through the pineapple in the end.

Classic Pineapple Upside Down Cake

I found that cutting them into quarters was perfect for serving sizes! This cake made about 25 little slices. Or 12 medium slices 🙂

Classic Pineapple Upside Down Cake

You can also use a round cake tin, and you will not have the half slices on the side.

Classic Pineapple Upside Down Cake

Classic Pineapple Upside Down Cake

Prep time: 20 minutes Cook time: 40-45 minutes Cool time: 5 minutes


1 8oz can pineapple slices, juice retained
4 maraschino cherries, halved
1/2 cup unsalted butter, melted
3/4 cup packed brown sugar

1 1/2 cup flour
2 tsp baking powder
1/4 tsp salt
1/2 tsp cinnamon
3/4 cup packed brown sugar
1/2 cup unsalted butter
1 tsp vanilla
2 large eggs


Preheat oven to 350 degrees F.

Drain pineapple and retain juice. Adding enough water to the juice to measure 3/4 cup and set aside.

Pat dry pineapple slices and slice in half or quarters.

In a small bowl, melt butter and mix in brown sugar.

In a greased 9 inch square pan, spread the butter/sugar mixture into the bottom and arrange pineapple slices and cherries. Set aside.

Sift together flour, baking powder, salt and cinnamon. Set aside.

Using a stand mixer cream together butter and sugar and until light and fluffy.

Add vanilla and eggs beating well after each addition.

Add flour to creamed mixture, alternating with pineapple juice, beating well after each addition.

Carefully pour batter into pan.

Bake for 40-45 minutes or until tester comes out clean.

Cool 5 minutes, then invert onto a serving plate.

Serve warm with ice cream






3 thoughts on “Classic Pineapple Upside Down Cake

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s