Pineapple Upside Down Cheesecake

Pineapple Upside Down Cheesecake

 Kristina Vanni

Prep: 30 mins
Cook: 90 mins
Chill Time: 3 hrs
Total: 5 hrs
Servings: 16 servings
Nutrition Facts (per serving)
331 Calories
19g Fat
34g Carbs
7g Protein
Show Full Nutrition Label Hide Full Nutrition Label
Nutrition Facts
Servings: 16
Amount per serving
Calories 331
% Daily Value*
Total Fat 19g 25%
Saturated Fat 11g 54%
Cholesterol 108mg 36%
Sodium 200mg 9%
Total Carbohydrate 34g 12%
Dietary Fiber 1g 2%
Total Sugars 28g
Protein 7g
Vitamin C 5mg 23%
Calcium 64mg 5%
Iron 1mg 4%
Potassium 148mg 3%
*The % Daily Value (DV) tells you how much a nutrient in a food serving contributes to a daily diet. 2,000 calories a day is used for general nutrition advice.
(Nutrition information is calculated using an ingredient database and should be considered an estimate.)

This recipe has everything you love about a classic pineapple upside down cake in the rich, creamy form of a decadent cheesecake!

The cheesecake starts with a traditional graham cracker crust that is filled with a cream cheese batter. When it comes out of the oven, that's when things get really exciting. A can of pineapple slices in heavy syrup is drained and used to create a topping for the cheesecake. Then the pineapple rings are arranged like a typical upside down cake, with maraschino cherries inside each ring. The result is a stunning dessert that looks like it came from a restaurant or bakery.


For the Cheesecake:

  • 1 1/3 cups graham cracker crumbs

  • 1 1/2 cups sugar

  • 1/4 cup butter, melted

  • 3 (8-ounce) packages cream cheese, at room temperature

  • 2 tablespoons all-purpose flour

  • 3 large eggs

  • 1 large egg yolk

  • 2 teaspoons pure vanilla extract

  • 3 tablespoons heavy cream

For the Topping:

  • 1 (20-ounce) can pineapple slices in heavy syrup

  • 1 (1-ounce) packet unflavored gelatin

  • 2 tablespoons orange juice, or water

  • 8 maraschino cherries

Steps to Make It

  1. Gather the ingredients.

    Pineapple Upside Down Cheesecake
     Kristina Vanni
  2. Make the crust. Combine the graham cracker crumbs, 1/4 cup of the sugar, and melted butter.

    Pineapple Upside Down Cheesecake
     Kristina Vanni
  3. Press the mixture evenly on the bottom and halfway up the side of a lightly buttered 9-inch springform pan. Chill while preparing the next steps.

    Pineapple Upside Down Cheesecake
     Kristina Vanni


    When making cheesecakes, line the springform pan with foil to prevent leaks.

  4. Make the cheesecake filling. Beat the cream cheese in a large bowl until smooth; blend in 1 1/4 cups of the remaining sugar, and the flour. Beat with an electric mixer until light and fluffy. 

    Pineapple Upside Down Cheesecake
     Kristina Vanni
  5. Add the eggs and egg yolk, 1 at a time, beating well after each addition. Stir in the vanilla and cream.

    Pineapple Upside Down Cheesecake
     Kristina Vanni
  6. Pour into the prepared crust and smooth the top. Bake in a 450 F oven for 10 minutes. Lower temperature to 250 F and bake 1 hour and 20 minutes longer. 

    Pineapple Upside Down Cheesecake
     Kristina Vanni
  7. Remove cake from the oven and cool completely on a wire rack. 

    Pineapple Upside Down Cheesecake
     Kristina Vanni
  8. Make the topping. Drain the juice from the can of pineapple slices into a small bowl. Set aside pineapple slices. 

    Pineapple Upside Down Cheesecake
     Kristina Vanni
  9. In a small saucepan, combine the reserved syrup from the can of pineapples with the orange juice or water. Sprinkle gelatin over the juices to soften, about 5 minutes. Heat over very low heat, stirring often, until gelatin clears and dissolves. Chill until syrupy but not set.

    Pineapple Upside Down Cheesecake
     Kristina Vanni
  10. Cut 4 of the reserved pineapple slices in half and arrange around the edge on top of cake. Place one whole pineapple ring in the center. (Reserve remaining pineapple slices for another use.)

    Pineapple Upside Down Cheesecake
     Kristina Vanni
  11. Spoon the chilled pineapple topping over to cover the center of the cake. Place maraschino cherries in the center of each pineapple ring. 

    Pineapple Upside Down Cheesecake
     Kristina Vanni
  12. Chill for at least three hours or until topping is set. Remove the side of the springform pan before slicing and serving.

    Pineapple Upside Down Cheesecake
     Kristina Vanni
  13. Enjoy!