This is a fight that no one has ever mentioned before. I think….Shadow can win. Now hear me out. Superman may be strong but he’s weak against magic. Chaos is magic. So a couple Chaos Spears and it would be all over. Aside from that Shadow can go Super Saiyan in a way. When he has all of the chaos emeralds he turns gold and gets extreme power. Also Superman has been known to lose to humans sometimes.I thnk Shadow easily wins.