Pineapple Cheesecake-Topped Cake

Total Time

Prep: 30 min. Bake: 1 hour + chilling


16 servings

Updated: Jun. 27, 2023
My brother-in-law asked me to make a cheesecake version of pineapple upside down cake, and after many attempts, I created one. It’s a yummy twist on a classic.—Rebecca Everett, Kansas City, Missouri
Pineapple Cheesecake-Topped Cake Recipe photo by Taste of Home


  • 1/4 cup butter, melted
  • 1/3 cup packed brown sugar
  • 8 canned unsweetened pineapple slices
  • 4 maraschino cherries, halved
  • 3 packages (8 ounces each) cream cheese, softened
  • 1 cup sugar
  • 2 tablespoons all-purpose flour
  • 1 teaspoon vanilla extract
  • 3 eggs, lightly beaten
  • CAKE:
  • 1/2 cup butter, softened
  • 1 cup sugar
  • 2 large eggs
  • 1 teaspoon vanilla extract
  • 1-1/2 cups all-purpose flour
  • 1-1/2 teaspoons baking powder
  • 1/4 teaspoon salt
  • 1/2 cup 2% milk


  1. Preheat oven to 325°. Place a greased 10-in. springform pan on a double thickness of heavy-duty foil (about 18 in. square). Wrap foil securely around pan. Place on a baking sheet.
  2. Pour butter into prepared pan; sprinkle with brown sugar. Arrange pineapple in a single layer over brown sugar; place a cherry half in the center of each pineapple slice.
  3. For cheesecake, in a large bowl, beat cream cheese and sugar until smooth. Beat in flour and vanilla. Add eggs; beat on low speed just until blended. Spoon over fruit.
  4. For cake, in another bowl, cream butter and sugar until light and fluffy. Add eggs, one at a time, beating well after each addition. Beat in vanilla. In a small bowl, whisk flour, baking powder and salt; add to creamed mixture alternately with milk, beating well after each addition. Spoon over cheesecake. Bake 60-70 minutes or until golden brown and a toothpick inserted in cake portion comes out clean.
  5. Cool on a wire rack 20 minutes. Remove foil. Loosen sides of cake with a knife; remove rim from pan. Invert cake onto a serving plate; remove bottom of pan. Cool 1 hour longer. Refrigerate overnight, covering when completely cooled.

Nutrition Facts

1 slice: 490 calories, 29g fat (18g saturated fat), 155mg cholesterol, 333mg sodium, 52g carbohydrate (39g sugars, 1g fiber), 8g protein.