Every once in a while I make this. My Mother made this when I was a child, although I believe the cake part was more of a shortcake rather than a raised cake.

Since we have fresh pineapple in the house fairly often (I like pineapple), I make this with fresh rather than canned bits. I use more maraschino cherries than it calls for but thats a “ymmv” call. The option to make the topping in the microwave is the one I use and, if possible, I use fresh orange juice.

I’ll try to get my Mothers recipe and compare the two.

Pineapple Upside Down Cake

8 servings


1/4 cup butter

1/2 cup brown sugar

8 canned pineapple, spears drained well

5 maraschino cherries, halves


1 1/4 cups all-purpose flour

1 1/2 teaspoons baking powder

1/4 teaspoon salt

1/3 cup shortening or butter

2/3 cup sugar

1 egg

1 teaspoon vanilla essence

1/2 cup orange juice


Melt butter in a small skillet on direct heat. Add brown sugar and stir until well blended and bubbly. Pour into a 9″ square baking dish, spreading to cover the bottom. (Alternately, microwave butter and brown sugar in a 9″ square glass baking dish till well blended and bubbly).

Arrange pineapple spears on top of the brown sugar in a sun-burst pattern. Chill in refrigerator while preparing batter.



Sift together flour, salt and baking powder. Cream shortening/butter and sugar in a mixing bowl until light and fluffy. Add egg and vanilla and beat until smooth.

At low speed, and in alternate additions, add in the flour and orange juice, beginning and ending with the flour mixture. Beat only until smooth.

Remove cake pan from the refrigerator and spread batter over topping. Bake at 325 degrees for 40 minutes. Remove from oven, let stand for 5-10 minutes and Invert on a plate. Serve warm.