Buying a new pan is always a good excuse to bake cake. The very moment I set eyes on this lovely cast-iron cake pan in Winners, I knew I was going to eat pineapple upside down cake pretty soon. After browsing through dozens of recipes, I was strongly attracted by the one from The History Kitchen due to the delightful, mouth-watering food photography. While my cake was nowhere close to that sensational beauty, it did give me the satisfaction of holding the ‘inaugural ceremony’ of my newly acquired bake ware. I felt that the batter was a tad stiff; maybe I should have gone for milk instead of pineapple juice. The caramelized fruit fortunately did not stick to my pan and I did not have to struggle at all to get the cake out in a single piece. Most of the syrup, however, was immediately absorbed by the cake itself so I had none to drizzle on the top and sides. It was an overall modest attempt of what I think might become a regular teatime treat and is best served warm from the oven.



1/4 cup unsalted butter, melted

3/4 cup packed light brown sugar

7 pineapple slices, drained

7 maraschino cherries

1 3/4 cups all-purpose flour, sifted

1 1/2 teaspoons baking powder

1/2 cup unsalted butter, softened

3/4 cup granulated sugar

2 large eggs, room temperature

1 1/2 teaspoons vanilla extract

1/2 cup pineapple juice


  • Position a rack in the lower third of the oven. Preheat the oven to 350°F (325°F for a convection oven).

  • Use a 9 to 10-inch ovenproof skillet or 10-inch round baking pan or 9-inch square baking pan for this cake.

  • Beat butter and sugar together and spread evenly over pan. Arrange pineapple slices and cherries over base.

  • Sift together flour and baking powder. In a large bowl, beat butter on low speed until smooth, about 2 minutes.

  • Increase the speed to medium, gradually add the sugar, and beat until light and fluffy, about 4 minutes.

  • Beat in eggs, one at a time. Add vanilla. Add flour mixture alternately with the juice and beat until creamy.

  • Pour batter over pineapples. Bake until a tester inserted in the center comes out clean for 45 to 55 minutes.

  • Let the cake cool in the pan set on a wire rack for about 10 minutes, then run a knife around the edge.

  • Invert onto a serving plate, and lift off the pan. Serve the cake slightly warm or at room temperature.

  • Wrap in plastic wrap and store at room temperature for up to 2 days or in the freezer for up to 2 months.

Pineapple Upside Down Cake