This old-fashioned pineapple upside-down cake is everything a classic dessert should be: tender vanilla cake, a buttery brown sugar topping, and juicy pineapple slices baked into a glossy, caramelized crown.
As the cake bakes, the butter and sugar melt into a rich syrup that soaks into the fruit, creating a moist crumb and that iconic golden top once inverted. It is simple, nostalgic, and made entirely from scratch, just the way home baking was meant to be.
Looking for more company-worthy cakes that feature fruits and vegetables in season? Try chocolate beet cake, my Grandma’s pumpkin cake roll recipe, from-scratch strawberry rhubarb dump cake (no Jello or cake mix!), tangerine cake, or this easy blueberry cake.
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Quick Look at This Recipe
- ✅ Recipe Name: Old-Fashioned Pineapple Upside-Down Cake
- 🕒 Ready In: About 1 hour 15 minutes
- 🍞 Method: Oven baked
- 👪 Yield: 8 to 10 servings
- 🍽 Calories: Approximately 350 per slice
- 🥄 Tools: Mixing bowls, hand or stand mixer, 9 inch round or 8 inch square cake pan
- ❄️ Freezer Friendly: Yes, sliced
- 📖 Dietary Info: Vegetarian
- ⭐ Why You’ll Love It: A timeless dessert with caramelized fruit and tender crumb
- 👩🍳 Tip: Chill the topping briefly before adding batter so it stays perfectly layered
What Makes This Recipe Unique
- Old-Fashioned – Classic comfort food that never goes out of style. This recipe uses simple pantry staples with no boxed mix.
- Flavor – Perfect balance of sweet pineapple and buttery vanilla cake.
- Adaptable – Bakes beautifully in either a round or square pan.
- Convenient – A reliable make-ahead dessert that stores and freezes well.
Key Ingredients:
A full ingredients list, including measurements, can be found in the recipe card below.
- Pineapple – Canned or fresh both work well. If using canned pineapple, reserve the juice for the cake batter.
- Brown Sugar – Creates the signature caramelized topping once baked.
- Luxardo Cherries – A naturally colored option that elevates the classic look and taste.
- Cake Flour – Produces a lighter, more tender crumb than all-purpose flour.
Recipe Substitutions and Variations
Check out my full list of ingredient substitutions every home cook should know.
- Flour – Swap cake flour for all-purpose flour by removing 1 tablespoon flour per cup and replacing it with cornstarch.
- Milk – Use coconut milk in place of regular milk for a subtle tropical flavor.
- Cherries – Replace Luxardo cherries with halved fresh cherries or traditional maraschino cherries if preferred.
- Nutmeg – Add a pinch of nutmeg if you want extra warmth alongside the cinnamon and ginger.
Recipe Instructions
Step 1: Preheat the oven to 350°F. Prepare a 9-inch by 2-inch round cake pan or an 8-inch square cake pan. In a small bowl, mix the melted butter, brown sugar, cinnamon, and ginger until well combined.
Step 2: Pour the mixture evenly into the bottom of the cake pan.
Step 3: Blot the pineapple slices to remove excess liquid and arrange them over the sugar mixture. Place a cherry in the center of each pineapple ring. Refrigerate the pan while preparing the cake batter.
Step 4: Cream the butter on high speed for about 1 minute until light. Add the eggs, vanilla, and milk, mixing until combined.
Step 5: Add the dry ingredients and mix on low speed. Slowly pour in the pineapple juice while mixing. Beat just until combined. The batter will be thick.
Step 6: Remove the pan from the refrigerator and carefully spread the batter evenly over the topping.
Step 7: Bake for 40 to 50 minutes. Tent with foil if the top browns too quickly. Test for doneness by inserting a toothpick into the center of the cake. It should come out clean.
Step 8: Cool the cake on a wire rack for 20 minutes, then invert onto a serving platter while still warm. Allow the syrup to drizzle over the sides before cooling completely.
Recipe Tips
- Blotting the pineapple prevents excess liquid from thinning the topping.
- Do not overmix the batter or the cake will be dense instead of tender.
- Invert the cake while warm so the topping releases cleanly.
- Use a rimmed platter to catch the caramelized juices.
Storage Instructions
Cover and store leftovers in the refrigerator for up to 3 days. For longer storage, slice the cake and freeze for up to 3 months. Do not freeze the cake whole, as the topping does not thaw evenly. Thaw slices at room temperature before serving.
Plated By Season Magazine
Want More From-Scratch Recipes Like This?
This old-fashioned pineapple upside-down cake recipe is featured in the March 2026 edition of Plated By Season, our seasonal print magazine designed to help you get real food on the table without stress or complicated planning.
Each issue walks you through from-scratch, seasonal meals that come together in about 30 minutes or less, using ingredients you can grow, preserve, or keep stocked in your pantry. No rigid meal plans. No spreadsheets. Just practical, flexible recipes that actually work in real life.
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Did you make this old-fashioned pineapple upside-down cake? If so, please leave a star ⭐ rating in the recipe card below (this really helps me out)… then, snap a photo and tag me on social media @melissaknorris so I can see! I love getting a glimpse of what you all make in your kitchens.
Old-Fashioned Pineapple Upside Down Cake
Equipment
- Mixing Bowls
- mixer
- cake pan 9" round or 8" square
Ingredients
Topping
- 1/4 cup unsalted butter melted
- 1/2 cup brown sugar packed
- 8 slices pineapple fresh or canned
- 20 whole cherries Luxardo or maraschino
- 1/4 teaspoon cinnamon
- 1/4 teaspoon ginger ground
Cake
- 1/2 cup cake flour
- 1 teaspoon baking powder
- 3/4 cup sugar
- 1/2 teaspoon salt I love Redmond Real Salt. Use code “Pioneering” for 15% off.
- 1/2 cup butter room-temperature
- 2 large eggs
- 2 teaspoons vanilla I love this homemade vanilla extract recipe.
- 1/2 cup milk
- 1/4 cup pineapple juice If using canned pineapple, reserve the liquid.
Instructions
- Preheat the oven to 350°F. Bake in a 9" x 2" round cake pan or an 8" square cake pan.
- Mix the melted butter, brown sugar, cinnamon and ginger together in a small bowl. Put the topping mixture into the bottom of the cake pan.
- Blot the pineapple slices to remove excess liquid then layer on top of the liquid mixture, place a cherry in the center of each pineapple ring. Place the pan in the refrigerator to allow the topping to solidify a bit while you prepare the cake batter.
- Cream the butter on high, about 1 minute. Add the eggs, vanilla and milk and beat until combined. Add the dry cake mix to the wet ingredients and mix on low. While it is mixing slowly add the pineapple juice.
- Continue beating until all of the ingredients are just combined. Don't over mix because that will result in a tougher cake. The batter will be on the thicker side.
- Take the topping out of the fridge and spread the cake batter over top evenly.
- Bake for 40-50 minutes. To prevent the top from over browning before the cake is fully baked, tent the top with foil. To test for doneness, insert a toothpick in the center of the cake. If it comes out clean, the cake is done.
- When done, remove from the oven and place on a wire rack. Allow to cool for 20 minutes. After the cooling time (it'll still be warm), invert the cake onto a platter or cake stand. Allow the juices from the topping to run over the sides.
- Allow the cake to cool at room temperature before slicing and serving. You can slice and serve while it's warm but the slices will be messy.
Notes
- Blotting the pineapple prevents excess liquid from thinning the topping.
- Do not overmix the batter or the cake will be dense instead of tender.
- Invert the cake while warm so the topping releases cleanly.
- Use a rimmed platter to catch the caramelized juices.
This old-fashioned pineapple upside-down cake turned out perfectly moist with the most delicious caramelized topping, and my family said it tasted even better than Grandma’s!