Doctor Eggman (both fights)
King Boom Boo (first fight)
In the first battle, the player must look for Shadow's moves. As when he is near, he will do a surprising Homing Attack at the player, so must evade being near. There are two ways to hurt Shadow, one to watch when he is on the ground, and launch a Spin Dash at him at fast rate, or waiting for him when he stops and sit still. The player must hit him three times to defeat.
In this battle, Shadow in now more fearsome than in the previous battle. The player must now race Shadow along an infinite line of platforms that fall into a bottomless pit one after another behind Sonic.
At the beginning, the player must launch a Homing Attack or Spin Dash at Shadow to hurt him. If the player takes the lead in this race though, Shadow will teleport up in front using Chaos Control or launch a Homing Attack at Sonic to hurt him and take the lead. To avoid the latter, the player simply has to use to Spin Jump. After the player has hit Shadow three times, Shadow will complicate his moves and attacks. The player must now get behind him and wait until he stops to launch his Chaos Spear. Before he can launch it though, move in on him, even after he uses the Chaos Spear, to attack Shadow. His Chaos Spears can be avoided by Spin Dashing, changing directions, or Somersaulting. Continue this pattern until Shadow is defeated. Sometimes, even the Light Speed Dash can hurt Shadow should he teleport into a trail of Rings.
- The second battle against Shadow is revisited in Sonic Generations as one of the three rival battles.
- If noticed during the first battle, Big the Cat can be seen below a vent.
- If ten minutes has elapsed in the second battle, the road ahead will collapse with further sections falling down just as they appear. While Shadow stays safe thanks to Chaos Control, the player will eventually die after hitting the death line.