Preheat oven to 350°F. Line 9×13 baking dish with parchment paper and spray liberally with cooking spray.
Cut off top, bottom, and sides of pineapple skin and core pineapple. Then cut pineapple into six 1/4″ slices (substitute canned pineapple, if preferred).
Place pineapple slices into the bottom of the pan and drizzle with 3 tablespoons of Cheerwine Syrup. Spread chopped pecans evenly over pineapple slices.
Chop remaining pineapple into small pieces and mix with cherry pie filling, cinnamon, nutmeg, and ginger. Pour fruit mixture over pecans and spread evenly.
Mix all cake ingredients together and pour over prepared fruit.
Bake for 35-45 minutes or until cake springs back when touched or toothpick in center comes out clean. Cool completely and flip the pan over on a plate. Drizzle remaining 3 tablespoons of Cheerwine Syrup over cake.