Preheat oven to 350°.
Coat a 15 x 10-inch jelly-roll pan with cooking spray; line bottom of pan with wax paper. Coat wax paper with cooking spray; set aside.
Place sugar and butter in a large bowl; beat with a mixer at medium speed 5 minutes or until well blended. Add eggs, 1 at a time, beating well after each addition.
Lightly spoon flour into dry measuring cups; level with a knife. Combine flour, baking powder, baking soda, and salt, stirring well with a whisk. Add flour mixture and buttermilk alternately to sugar mixture, beginning and ending with flour mixture; mix after each addition. Beat in extracts. Pour batter into prepared pan. Sharply tap pan once on counter to remove air bubbles. Bake at 350° for 20 minutes or until a wooden pick inserted in center comes out clean. Cool in pan 10 minutes on a wire rack; remove from pan. Carefully peel off wax paper; cool completely on wire rack. Place cake on a large platter or cutting board; refrigerate until cold (about 2 hours).
Spread ice cream evenly over top of cake; cover with plastic wrap. Freeze until firm (6 hours to overnight).
Uncover cake. Cut cake with a 2-inch round cutter into 24 cake rounds. Discard scraps. Working quickly, place one cake round, ice cream side up, in a paper muffin cup liner; top with another cake round, ice cream side down. Repeat procedure with remaining cake rounds to form 12 filled ice-cream cakes.
Combine whipped topping and cherry juice, if desired. Top each cake with 2 tablespoons whipped topping; arrange 1 maraschino cherry on each cake. Freeze until ready to serve. Let ice-cream cakes stand at room temperature 5 minutes before serving.