Pineapple Upside-Down Cheesecake

Total Time

Prep: 25 min. Bake: 35 min. + chilling


4 servings

Updated: Feb. 10, 2022
My mom often made pineapple upside down cake, but I prefer something creamier. This recipe looks just like her cake, but gets even tastier as pineapple upside down cheesecake. —Marilyn McGinnis, Citrus Heights, California
Pineapple Upside-Down Cheesecake Recipe photo by Taste of Home


  • 3/4 cup packed brown sugar
  • 4 slices canned pineapple (one 8-oz. can)
  • 4 maraschino cherries
  • 1 package (8 ounces) cream cheese, softened
  • 1/2 cup confectioners' sugar
  • 2 teaspoons all-purpose flour
  • 1 teaspoon vanilla extract
  • 1 large egg, room temperature, lightly beaten
  • 1/4 cup crushed pineapple, well drained
  • CRUST:
  • 1 tablespoon butter
  • 1/3 cup graham cracker crumbs
  • 1/4 teaspoon ground cinnamon


  1. Preheat oven to 325°. Sprinkle brown sugar into an 8-in. ovenproof skillet. Arrange pineapple in a single layer over brown sugar; place a cherry in the center of each pineapple slice.
  2. For filling, in a large bowl, beat cream cheese and confectioners' sugar until smooth. Beat in flour and vanilla. Add egg; beat on low speed just until blended. Fold in crushed pineapple. Spoon over fruit.
  3. Bake 35-40 minutes or until center is almost set. Cool on a wire rack 10 minutes. Loosen sides from pan with a knife. Cool 1 hour longer. Refrigerate overnight, covering when completely cooled.
  4. For crust, in a small skillet, melt butter over medium-low heat. Add cracker crumbs and cinnamon; cook and stir 4-6 minutes or until toasted. Cool. Just before serving, top cheesecake with toasted crumbs, pressing to adhere. Invert cheesecake onto a serving plate.

Nutrition Facts

1 piece: 549 calories, 24g fat (13g saturated fat), 117mg cholesterol, 298mg sodium, 79g carbohydrate (72g sugars, 1g fiber), 6g protein.