A pineapple upside-down bundt cake topped with pineapple rings and maraschino cherries sits on a white plate over a patterned wooden surface and a pumpkin-printed cloth.

I can’t express to you enough just how delicious vintage recipes are. They are usually pretty simple, but the impact is nothing short of deliciously amazing! THIS is my vintage pineapple upside down cake. The thing about our mothers and grandmothers from the past is they rarely wasted any ingredients. Just like this vintage pineapple upside down cake. The can of pineapples doesn’t JUST give you the pineapple rings, but also the 100% juice it’s packed in you’ll use in place of water when you make the cake batter. THIS is the recipe of all recipes for pineapple upside down cake. Just wait and see. If you love vintage recipes as much as I do, try these vintage recipes: Vintage Mexican Casserole, Vintage Coffee Ice Cream Cake, and Vintage Tuna Casserole.

A pineapple upside-down bundt cake with cherries is on a plate, in a bright kitchen. In the background, theres a checkered vase holding colorful flowers on a wooden table.

A cutting board holds eggs, a measuring cup with water, pineapple slices, cake mix, maraschino cherries, a stick of butter, and other baking supplies, set against a tiled kitchen background.

Box of yellow cake mix, just one can of pineapple slices packed in 100% juice, maraschino cherries, butter, brown sugar, eggs, and the juice from the can!

A box of Betty Crocker Super Moist cake mix, a can of Dole pineapple slices, and a glass measuring cup with pineapple juice on a wooden cutting board in a kitchen.

Here’s the trick of the women from our past. Waste nothing! Instead of buying a can of pineapple juice to replace the water when you’re making the box of cake mix; use the juice from the can of pineapple slices. This can will give you exactly 1 cup. which is what you need.

A bundt pan with pineapple rings and maraschino cherries arranged at the bottom, coated with butter, ready for making a pineapple upside-down cake.

I like to butter my cake pan like my grandmother used to do it, instead of using PAM or a nonstick spray for this recipe. You really got to get in the grooves of the bundt pan and up the sides. That way the cake will just slide right out! The butter also gives you extra flavor. Butter the pan, add the brown sugar and butter mixture, then arrange the pineapple slices. Pop a cherry in each whole!

A bundt cake pan filled with unbaked yellow cake batter sits on a wooden cutting board, ready to go into the oven.

I like to twist the pan with one hand and pour the batter from the bowl with the other. Make it nice and even!

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A golden-brown Bundt cake sits in a black Bundt pan, resting on a checkered wooden cutting board. The cake has a cracked circular ridge around the center hole.

A woman in a red sleeveless top smiles in a kitchen beside a pineapple upside-down cake on a white plate. A bouquet of colorful flowers is on the counter next to her.

A close-up of a sliced pineapple upside-down cake on a white plate, showing caramelized pineapple rings and moist, golden cake with a crumbly texture.

A pineapple upside-down bundt cake topped with pineapple rings and maraschino cherries sits on a white plate in a kitchen setting.

Melissa Jo

Vintage Pineapple Upside Down Cake

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You get box of yellow cake mix, pineapple juice from canned slices, and melted butter in every tasty bite of this Vintage Pineapple Upside Down Cake sweet treat.

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Prep Time 30

Cook Time 43

Course: Dessert

Cuisine: American

Ingredients

1 box of yellow cake mix
Ingredients called for on the back of the box: usually 3 eggs & 1/2 cup of oil, and water (except we will be replacing the water with the juice from the can of pineapple slices.) sometimes the box calls for 1/3 cup of softened butter.
pineapple juice from canned slices instead of the 1 cup of water called for on the back of the box we will replace that with the pineapple juice from the can. The can of pineapple slices I showed in the photos yields exactly 1 cup of pineapple juice. Just tip the can over into a measuring cup and pour it in. Press the pineapples down to squeeze all the juice out, if needed.
1/2 cup of melted butter I used salted butter so, 1 stick of butter
1/2 cup of brown sugar
20 oz. can of pineapple slices packed in 100% juice you will use the pineapple slices & the juice from this can
6-7 marachino cherries
Pam or butter to grease the bundt pan. use A LOT

Method

Preheat your oven to 350°F (180°C).
Prepare the cake batter: In a mixing bowl, prepare the cake mix according to the package directions, substituting the reserved pineapple juice for the equal amount of water listed on the back of the box. (So, instead of using water, you will be using 1 cup of the pineapple juice drained from the can of pineapple slices.) (be sure to buy the pineapple slices packed in 100% juice.)
In a separate bowl, mix the melted butter and brown sugar together.
Pour the butter and brown sugar mixture evenly into the bottom of a greased bundt pan.
Arrange the pineapple slices in a single layer over the butter and brown sugar mixture.
Place one cherry half in the center of each pineapple slice.
Pour the cake batter evenly over the pineapple slices.
Bake for 40-45 minutes, or until a toothpick inserted into the center of the cake comes out clean.
Remove the cake from the oven and let it cool for 5 minutes.
Invert the bundt pan onto a serving platter and let the cake cool completely.
Serve and enjoy!