Grease a 9X13-inch pan and preheat oven to 350 degrees.
Prepare cake mix according to package directions, using the 1 cup of Cheerwine instead of water and stirring in chopped cherries.
Pour batter into prepared pan and bake for recommended time on cake box. Cool 15 minutes.
In a small saucepan, bring 1 1/2 cups Cheerwine to a boil. Remove pan from heat and stir in gelatin until dissolved.
Use a straw or handle of a wooden spoon to poke holes in cake about every 2 inches.
Pour gelatin mixture evenly over cake.
Cover and refrigerate for at least 4 hours.
Using an electric mixer, beat heavy cream, confectioners' sugar and cherry juice until stiff peaks form. Spread whipped cream on top of cake and garnish with cherries. Keep leftovers refrigerated.