It's a very easy battle, and you'll probably S Rank it unless Shadow gets charged up before you do. Run into meteors to send pieces of them at Shadow to slow him down, and then stay on his tail to drain rings from him until he runs out.
Once that happens, you'll be chasing Shadow on a much more flat piece of terrain. To win, you just have to collect two of the energy cores moving around the stage before Shadow gets two of them himself. Mimicking a scene from Sonic Adventure 2 is this fight against Shadow, who debuted in the same game. Sonic Generations | Boss Battles (S Rank) Shadow the Hedgehog The ninja will warn you to keep on your toes. Once you've cleared Seaside Hill Zone, the gang will realize a little bit more of the situation they're in, as well as release Espio from his stone prison.