I have loved pineapple upside down cake for as long as I can remember and the pineapple rings are honestly iconic. However, this crushed pineapple upside down cake (in a cute lil loaf shape) has upped the ante because there's pineapple in every single bite! And it's easy to make so let's go ahead and get into it.
And if you enjoy this recipe, you'll also love my pineapple upside down rum cake made in a bundt pan!

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❤️ Why You'll Love this Recipe
Quick & Easy - You don't need any fancy kitchen tools or advance baking techniques for this one. It's beginner friendly and ready in a hurry--because who wants to wait on all that goodness?
Unique Shape - Whoever invented pineapple upside-down cake did their big one. And this loaf shape is the best small batch option that makes for easy slicing, too.
Classic Tropical Taste - The flavor profile is fabulous: caramelized buttery brown sugar, sweet pineapples, and a lil hint of spice. It's low-key a soulful pineapple upside down cake and you could NEVER get this flavor out of a box!
I have a thing for fruity cake recipes and think you should, too: plum upside down cake with bourbon, peach cobbler pound cake, fresh strawberry sheet cake, pineapple pound cake!
What You'll Need for this Recipe

Crushed Pineapple is key to getting sweet pineapple topping across the entire surface of the cake. Make sure to drain it very well.
Brown Sugar not only on top but in the cake batter as well. I love the deeper caramel molasses flavor and beautiful brown color it provides compared to granulated sugar. You can use dark or light brown sugar interchangeably here.
Pineapple Juice goes into the batter, too, to infuse every bite with sweet fruity flavor! You can use the juice strained from the crushed pineapple for ease.
Nutmeg and Ginger add a lil somethin' that nicely complements the pineapple flavor with zing and warmth. Use freshly ground nutmeg if you have it!
Check out the recipe card below for full ingredients list, measurements, nutrition facts, and step-by-step instructions!
Substitutions & Variations
Maraschino Cherries are an traditional part of the pineapple upside down cake presentation but, honestly, optional so if you don't have them, don't sweat it. You can also use brandied or cocktail cherries instead.
Milk of any plant-based or dairy variety will work, including buttermilk!
Vanilla Extract can be substituted with vanilla paste or pure vanilla beans, if needed.
How to Make Crushed Pineapple Upside Down Cake

- Step 1: Melt the butter in the loaf pan then mix in brown sugar and press in crushed pineapple and cherries over top.

- Step 2: Whisk together the flour, baking powder and soda, and spices.
Pro Tip #1
Be sure to press the cherries through the crushed pineapple and all the way to the bottom of the pan so that they will show through once the cake is flipped.

- Step 3: Mix the remaining cake ingredients together then combine with the flour mixture to form cake batter.

- Step 4: Gently pour the batter over the pineapple topping in the loaf pan.

- Step 5: Bake the cake until golden brown and a toothpick inserted into multiple places comes out clean.

- Step 6: Let the cake rest for a few minutes then flip it--see my tips for this below!
Pro Tip #2
Bake this cake on the middle oven rack. You never want to burn the bottom of a cake but especially don't want burned pineapple upside down cake because the bottom is really the top! So don't bake it on the bottom rack.
Tips for Removing Upside Down Cake From Pan
Wondering how to remove this pineapple upside down cake from the pan? Don't be nervous--it's actually quite easy. Here are the steps I follow for a beautiful result every time with no sticking!
- Use a non-stick pan. Pineapple upside down cake is quite buttery so sticking is not typically a problem but you don't want to be disappointed, right?
- Let the cake rest for about 10 minutes before flipping it over.
- Run a butter knife around the edges of the cake to release any sticky bits on the sides.
- Flip the upside down cake over by placing a plate or platter on top then gently inverting the pan onto it.
- Let the pan sit on top of the cake for a couple of minutes so all the buttery, brown sugary, pineapple-y goodness seeps down into it.
- Tap the pan a couple of times then gently pull it straight up off the cake.
Frequently Asked Questions
Yes, you can bake the cake up to three days ahead of time so long as you store it properly.
Store in an airtight container at room temperature for up to two days and in the refrigerator beyond that. Keeps for up to five days.
To freeze, wrap snugly in plastic wrap then again in aluminum foil before placing in the freezer. Cake will keep for up to one month.
More Favorite Fruity Cake Recipes
Want more recipes like this one? Try these:
I hope you'll enjoy a lil slice of pineapple upside down cake with crushed pineapple soon and very soon. And sharing is caring so be sure to pin this recipe on Pinterest. Thanks for reading!

📖 Recipe

Crushed Pineapple Upside Down Loaf Cake
Equipment
- 1 loaf pan
- 1 whisk
- 1 silicone spatula or kitchen spoon
Ingredients
Caramelized Pineapple Topping
- ¼ cup butter
- ½ cup brown sugar
- 1 cup crushed pineapple drained
- 8 maraschino cherries
Spiced Pineapple Cake
- 1 ½ cup flour
- ¾ teaspoon baking soda
- ¾ teaspoon baking powder
- ½ teaspoon fine sea salt
- ½ teaspoon ground ginger
- ¼ teaspoon ground nutmeg
- ¾ cup butter melted
- ¾ cup brown sugar
- ¼ cup pineapple juice
- 2 eggs
- 3 tablespoons milk
- 1 ½ teaspoon vanilla extract
Instructions
To Make the Caramelized Pineapple Topping
- Preheat oven to 350 degrees. Place butter into a non-stick or prepared loaf pan and place in oven for about three minutes or until butter is melted.
- Carefully remove loaf pan from oven and mix brown sugar in with melted butter. Spread crushed pineapple into this mixture then arrange cherries on top, gently pushing them through the crushed pineapple so that they touch the bottom of the pan.
To Make the Pineapple Loaf
- Meanwhile, whisk together the flour, baking soda, baking powder, sea salt, ginger, and nutmeg.
- In another bowl, combine the butter, brown sugar, pineapple juice, eggs, milk, and vanilla extract until uniform. Then add wet mixture to dry mixture and stir until just combined and no dry pockets remain.
- Carefully pour cake batter into pan with topping. Transfer pan to the oven and bake on the middle rack for about 40 minutes or until a toothpick inserted into the center of the cake comes out clean.
- Let cake sit for about 10 minutes then run a butter knife around the edges of the cake to release any sticky parts from the pan. Invert cake onto a plate by placing the plate on top of the pan then gently flipping it over.
- Allow cake to cool to at least 20 minutes then serve warm.
Notes
-
- Use a non-stick pan. Pineapple upside down cake is quite buttery so sticking is not typically a problem but you don't want to be disappointed, right?
-
- Let the cake rest for about 10 minutes before flipping it over.
-
- Run a butter knife around the edges of the cake to release any sticky bits on the sides.
-
- Flip the upside down cake over by placing a plate or platter on top then gently inverting the pan onto it.
-
- Let the pan sit on top of the cake for a couple of minutes so all the buttery, brown sugary, pineapple-y goodness seeps down into it.
-
- Tap the pan a couple of times then gently pull it straight up off the cake.










Erin says
This was FANTASTIC!
Jazzmine Woodard says
Hi, Erin! I'm so glad you enjoyed this one. Thanks for your feedback.
Tammy says
I have made this twice. The First cake was a loaf, made per recipe and baked until a clean toothpick the very center of the loaf. When I cut it was just a bit underdone. The cake was a bit bland. The second time, I doubled the ginger and nutmeg, and this was tasty.
The second time, I made it in an 8-inch square glass baking dish with double the pineapple mixture. Bake at 350 preheated. The cake was browning too fast at about 20 minutes into the bake. I turned the heat down to 325 and covered the cake to stop it from over-browning. I checked the cake at 45 minutes. Not even close to done, did not need to put a toothpick in to see that. added 10 minutes, left it covered. Check at 55 minutes, still not quite done. Added 10 more minutes. It was perfect at this point. Let the cake rest and turn it out upside down. It was beautiful, the inside was so moist melted in my mouth. The double-crushed pineapple was perfect. This is not a sweet cake, which I like, so the extra brown sugar on top made it delicious. The bake was perfect. Love this recipe!!
Jazzmine Woodard says
Hi, Tammy! Thank you for your note and your creativity trying this bake different ways. I'm so glad you found a version that works best for you--I don't like super sweet cakes either.
Krys says
Pineapple upside down is my husband's favorite cake! I wanted to try this because it looked so easy. The caramelized pineapple topping was my favorite! I used dark brown sugar and it was perfect. Definitely going to make this again.
Jazzmine Woodard says
Thanks for your note, Krys! I'm glad y'all enjoyed this one.