Step 1Heat the oven to 350 degrees. Drain the pineapple, reserving 2 tablespoons of syrup.
Step 2Melt 2 tablespoons of butter in a 6-inch oven-proof skillet. Add the brown sugar and stir until dissolved. Remove from the heat. Place the pineapple slices on top of the sugar mixture. Fill the center of each pineapple with 1 cherry.
Step 3Combine the flour, granulated sugar, baking powder, salt and allspice in a bowl. Blend the orange zest with the milk in a separate bowl. Add the remaining 1 tablespoon soft butter, egg and the reserved 2 tablespoons of syrup. Beat until blended. Add the flour mixture and stir to make a batter.
Step 4Pour the batter over the pineapple in the skillet, being careful not to disturb the slices. Bake until the cake springs back when lightly touched, 45 minutes. Let stand 5 minutes. Loosen the edges from the sides of the pan and invert the cake onto a platter.