Preheat oven to 350ºF. Line cupcake pans with liners and set aside
Whisk together cake mix, Cheerwine and cherry flavor until combined. Pour into prepared pans about ⅔ or ¾ full and bake according to package instructions, about 18-20 minutes or until a toothpick inserted in center comes out clean. Cool completely.
Meanwhile, in a saucepan, boil down the Cheerwine until it has reduced to ½ cup. Cool completely.
In a stand mixer, cream butter and 2 cups of powdered sugar on medium speed. Slow speed to low and incorporate Cheerwine reduction. Increase speed to high and beat until light and fluffy, adding additional sugar if needed to achieve desired consistency.
Pipe onto cupcakes and top each one with a maraschino cherry.