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I adore pineapple upside-down cake. It’s just one of those classics that I return to over and over again. I’ve even asked for one several times instead of a birthday cake. This is a relatively easy recipe that makes a substantial 9 x 13 cake. I used a glass pyrex pan which worked nicely here. The topping stayed put and gave me no trouble at all. My son watched in awe as I flipped the cake over to reveal the pineapple top. (I love that he thinks I am some kind of master baker. He is five years old and I will enjoy it while it lasts.) I like that this is a dense coffee cake. It makes for just the right amount of cake to pineapple topping. Don’t forget the cherry on top to make it extra special!
Pineapple Upside-Down Coffee Cake
Source: Adapted from Better Homes and Gardens, April 2011
1/2 cup (1 stick) butter
1 cup packed brown sugar
12 canned pineapple rings in juice (You will need one 20 oz. can plus one 8 oz. can of pineapple slices for 12 rings. Save the extra for snacking!)
2 cups all-purpose flour
2 teaspoons baking powder
1/2 teaspoon salt
1/2 teaspoon ground nutmeg
1/2 cup (1 stick) butter, softened
1/2 cup granulated sugar
1/2 cup packed brown sugar
2 eggs
1/2 cup milk
1 teaspoon vanilla
Sweetened whipped cream and 12 maraschino cherries (optional)
Heat oven to 350 degrees F. Butter the bottom and sides of a 13 x 9 x 2 inch baking pan. Line the bottom of pan with parchment paper; set pan aside.
For pineapple topping, melt 1/2 cup butter in a medium saucepan over low heat. Stir in 1 cup brown sugar. Bring to boiling over medium heat, stirring frequently. Pour into prepared pan. Drain pineapple rings, reserving 1/2 cup juice. Fit 12 rings into bottom of pan.
In a medium bowl whisk together flour, baking powder, salt and nutmeg.
In a large mixing bowl beat softened butter, granulated sugar, and 1/2 cup brown sugar with electric mixer on medium speed for 2 minutes, scraping the sides of the bowl occasionally. Add eggs; beat until combined. On low speed, beat in half the flour mixture. Pour in reserved 1/2 cup pineapple juice and the milk; beat until combined. Beat in remaining flour mixture and vanilla.
Spread batter carefully over pineapple slices in pan. Bake for 35-40 minutes or until toothpick inserted near center comes out clean. Cool in pan on wire rack for 10 minutes.
Place a serving tray or baking sheet over coffee cake; carefully invert. Peel off the parchment paper. If any pineapple sticks to the pan, gently replace on cake top.
Top with whipped cream and maraschino cherries. Yum!

My kids tell me all the time that I should have a restaurant. This, of course, is only true if you are 9 and 11 and biologically connected to me
It’s a feel good compliment, though. Love pineapple upside down cake. Yours is awfully pretty! Maybe he was right to be amazed!
Thanks! It does feel great to have your kids think you are wonderful at something! I’m sure mine will change their minds as they get older.
Looks so good!!!
It’s years since I had pineapple upside-down cake, and it’s high time I had it again. Thanks for the reminder!
I strongly recommend it! Simple but so good!
Reblogged this on UNIQUE GREETING CAKES.
That’s so funny! I recently re-discovered pineapple upside down cake at a pot luck. I didn’t track down the person who made it and I wish I had. I made a square one the other day too! But I wasn’t that happy with the results. My hubby liked it but I felt it could have been better. I’ll have to try yours because it’s different from the one I made. Maybe this is the one I’m searching for!
Sounds yummy! I will have to try it. I’ve made pineapple upside down cakes before, but amazingly never from scratch.
You have a way of making me hungry….
Looks great!
Do you have a favorite pineapple upside down cake recipe? My dad requested one for his birthday this year (in about a month), and I’ve never made one before!
Thanks!
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I actually don’t have a favorite. This one is more of a coffee cake than a birthday cake. They are not difficult and I’m sure you’ll have no trouble finding a great tasting recipe. (I’ll admit that I have often made a box mix from the grocery store. Still yummy to me!)
Umm yum! I need to try this
First cake that I’ve ever baked was a Pineapple Upside Down cake for Home Economics class, no less. I was caught snacking on the cherry halves that were meant to put in the middle of the pineapples and it caused me some points in my grade. Fond memories.