Heat oven to 350°F. Grease a 9x13-inch baking pan with cooking spray and set aside.
In a bowl of a stand mixer fitted with a paddle attachment, mix together all cake ingredients, except eggs, on low to medium speed until smooth. Mix in eggs one at a time until well combined. Pour batter into the prepared baking pan.
Bake for 35 minutes or until a wooden pick inserted in the center comes out clean or with a few dry crumbs. Allow the cake to cool for 10 minutes. Use a skewer to poke holes all throughout the cooled cake.
In a small saucepan over medium to high heat, mix sugar, water and maraschino cherry juice together. Bring the mixture to a soft boil until sugar is completely dissolved. Reduce heat to low and allow the mixture to simmer for 1 minute. Remove the saucepan from heat and transfer the syrup into a shallow bowl. Mix in liqueur. Add more liqueur about 1 tablespoon at a time if a stronger flavor is desired.
Using a pastry brush, dip into the syrup and brush coat the surface of the cake. Reserve the remainder of the liqueur mixture.
In a medium bowl, whisk all filling ingredients together. If desired, mix in 1/4 cup of the remaining cherry syrup. Evenly pour filling onto the cake. Cover the cake with aluminum foil making sure the foil does not touch the cake. Allow the cake to chill in the fridge for 3 hours or until most of the milk mixture is absorbed into the cake.
In a chilled bowl of a stand mixer fitted with the whisk attachment, beat heavy cream, sugar and vanilla on high speed until stiff peaks form. Frost the top of the cake, decorate with chocolate curls and cherries. Slice, serve and enjoy!