Pineapple Upside Down Cheesecake – Cheesecake Factory CopyCat

Pineapple Upside Down Cheesecake, two layers of buttery pineapple upside-down cake stuffed with pineapple cheesecake, just like The Cheesecake Factory… but homemade!

Who knew your two favorite desserts could get any better, pineapple upside down cheesecake for the win.

Pineapple Upside Down Cheesecake

Oooooh boy… you know we love our cheesecakes. I have posted many a cheesecake recipe. But, normally it’s all about what Jeremy likes *eye roll*

…. but yesterday it was my birthday so it has been all about what I likes. So, I wanted a massive dessert for my birthday… is that a crime?!

My favorite cheesecake from The Cheesecake Factory of all time is their Pineapple Upside-Down Cheesecake. It’s a lightly flavored pineapple cheesecake layered between two buttery pineapple upside-down cakes.

It’s Heaven, basically.

So, for my epic birthday cake this year, I made this bad baby! It’s everything I hoped for! And then some. Cheesecake Factory cheesecakes are big… but this… this thing is ginormous!

This recipe, like my last cheesecake cake Strawberry Shortcake Cheesecake, takes a little planning ahead.

I suggest making the cheesecake the day ahead and letting it get nice and cold in the fridge overnight. BUT, the pineapple upside-down cakes should be made the day of for a nice presentation.

You can still eat it for days and days after but that first day it will look the best.

The recipe for the cheesecake is adapted from Allrecipes.com and for the pineapple upside-down cakes from Sally’s Baking Addiction (I’m obsessed with her, I know.)

This recipe contains affiliate links

Tools Needed to make Pineapple Upside Down Cake Cheesecake:

I have to be honest, I always get nervous after typing up a recipe like this. It looks like it’s totally complicated and will take forever but in reality, it’s not that bad.

Sure, this recipe probably isn’t for a complete beginner but just break it down into steps. Just look at the cheesecake recipe, then the topping, then the batter. See, not that bad.

I’m also being sensible with the portion sizes, believe me, a small slice of this goes a long way!!

Yummm, excuse me while I wipe the drool off my keyboard. This is one heck of a cake!!

I truly hope you liked today’s recipe! What is your favorite Cheesecake Factory cheesecake flavor??

How to make Pineapple Upside Down Cheesecake

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Pineapple Upside Down Cheesecake

Pineapple Upside Down Cheesecake, two layers of buttery pineapple upside-down cake stuffed with pineapple cheesecake, just like The Cheesecake Factory… but homemade! 
Prep Time40 mins
Cook Time2 hrs
Total Time2 hrs 40 mins
Course: Dessert
Cuisine: American
Keyword: cheesecake, cheesecake cake, pineapple, pineapple upside down cake, pineapple upside down cheesecake
Servings: 18 servings
Calories: 587kcal
Author: Dana at ThisSillyGirlsLife.com

Ingredients

Pineapple Cheesecake

  • 4 8 oz packages cream cheese room temp
  • 1 1/2 Cups granulated sugar
  • 3/4 Cup milk
  • 4 eggs
  • 1 Cup sour cream
  • 1 Tablespoon vanilla bean paste or extract
  • 1/4 Cup all purpose flour
  • 1/3 Cup pineapple juice

Pineapple Upside-Down Cake Topping

  • 1/2 Cup unsalted butter melted
  • 1 Cup packed light brown sugar
  • 12 slices canned or fresh pineapple rings
  • 12 maraschino cherries

Pineapple Upside-Down Cake Batter

  • 3 1/3 Cup all purpose flour sifted
  • 1 teaspoon baking powder
  • 1/2 teaspoon baking soda
  • 1 teaspoon salt
  • 1 Cup unsalted butter melted
  • 1 1/2 Cup light brown sugar packed
  • 1/2 Cup granulated sugar
  • 2 eggs
  • 1/2 Cup sour cream
  • 1 Cup milk
  • 1/2 Cup pineapple juice
  • 2 Tablespoon vanilla bean paste or extract

Instructions

Pineapple Cheesecake

  • Preheat oven to 350 degrees. Grease a 9-inch springform pan. Cream the cream cheese with the sugar until smooth in a large bowl. Mix in the milk fully then add in one egg at a time and mix. Add in the remaining ingredients and mix until smooth with no lumps.
  • Pour into the pan and bake for 1 hour, the center will be slightly jiggly. Shut off oven and let cool down in the oven for 5 hours. Top with plastic wrap and place in fridge overnight to get cold.

Pineapple Upside-Down Cake

  • Start with the topping by dividing the melted butter equally between two 9 inch cake pans. Sprinkle 1/2 Cup of the brown sugar into each pan. Arrange the pineapple slices and cherries as pictured, set aside.
  • Preparing and cooking the cake: Preheat oven to 350 degrees. In a large bowl, add in the sifted flour, baking powder, baking soda, and salt, whisk to combine.
  • In a medium-sized bowl, add in the 1 Cup melted butter, brown sugar, and granulated sugar. Whisk to combine, getting all the brown sugar lumps broken up. Whisk in the eggs, sour cream, milk, pineapple juice and vanilla until combined.
  • Add the wet mixture to the dry mixtures and mix until combined, with no dry spots or lumps.
  • Evenly divide the batter between the two pans, about 2/3 of the way full, do not overfill!
  • Line oven with foil or two cookie sheets, cakes may bubble over some. Bake for 48-53 minutes, covering loosely with foil at the 20-minute mark to avoid burning. Cakes are down when a toothpick inserted in the middle comes out clean.
  • Place cakes on a wired rack to cool for 10 minutes.

Pineapple Upside-Down Cheesecake Assembly

  • Invert cakes, one onto a flat surface like a cutting board and the other on the plate you will be presenting on.
  • Take out the pineapple cheesecake. Trim top of the cheesecake if it is not even. Take it out of the pan and lift it off the bottom carefully, you may need to use a tool like a frosting spatula to help. Place on top of the first cake layer. Trim the sides of the cheesecake with a knife if necessary. Place the second layer of cake on top. Serve as is or with whipped cream, enjoy!!

Nutrition

Calories: 587kcal | Carbohydrates: 78g | Protein: 6g | Fat: 28g | Saturated Fat: 16g | Cholesterol: 128mg | Sodium: 278mg | Potassium: 209mg | Sugar: 58g | Vitamin A: 19.3% | Vitamin C: 1.6% | Calcium: 12.1% | Iron: 10%
Tried this recipe?Follow me @danadevolk or tag #danadevolk!

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36 Comments at Pineapple Upside Down Cheesecake – Cheesecake Factory CopyCat

  1. I wonder if I messed something up.. I never made a Cheesecake before, and really don’t make cakes for that matter.. I just finished the Cheesecake batter but when I poured it into the 9″ spring form pan its literally all the way to the top of the pan.. So then I thought, maybe cheesecake shrinks because it’s cheese.. Now I’m watching it ooze out of the pan in the oven lol.. Did I mess something up? Or does this make more better than needed?.. My lack of inexperience is showing lol

    1. I honestly don’t know why there would be an issue. Did you happen to add the cheesecake batter on top of one of the pineapple cake batters and baked it that way? Everything should be baked separately.

  2. Nope, I did just the cheesecake. It didn’t actually overflow, just came close. And when I took it out of the oven 5 hours later it did shrink back down a little bit but it’s still a lot thicker than your pictures, so I’m not sure. At least it didn’t overflow though 🙂

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