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This battle is fought on a looped circuit. Here, Sonic and Shadow must race each other to gain Energy Cores. During the race, Shadow will use his own version of the Boost when Sonic gets ahead of him or activate his own Boost. Should each character collide while boosting, they will ricochet to the left and right. There are certain parts of the arena where Shadow will slow down to collect Rings and maintain his boost, during which the player can hurt him with the Homing Attack or Boost. However, it is not advised to attack Shadow when he and the player are close to the Energy Core, as that may launch Shadow directly at it.
There are certain sections on the circuit that both the player and Shadow can take advantage of; between the straight paths on the circuit, there will be sharp corners where the player will have a hard time collecting the Energy Core if they do not use the Drift or Boost. Also, before the section leading to the starting point of this circuit, there is a wavy plateau that only the player can access by alternate paths, giving them the chance to take the Energy Core without opposition. It should be noted that on the final stretch on this circuit before returning to its starting point, the Energy Core cannot be collected. Instead, it will stop floating and vanish until the player passes the starting point for the circuit again.
During the race, the player can pick up Rings, destroy blue-tinted Meteorites and utilize Trick Jump Panels to keep the Boost Gauge filled. During the course, should Sonic fall too far behind Shadow, Shadow will fire several damage-inducing Chaos Spears directly at him. Once either Sonic or Shadow gain two Energy Cores, they will immediately perform a special attack. If Shadow gains two Energy Cores first, he will launch several Chaos Spears onto the ground that Sonic will have to avoid using Quick Step, before launching a large Chaos Spear at Sonic (while applying Chaos Control) to throw off Sonic's timing. If Sonic gains two Energy Cores first, he will automatically use a powered-up Boost which lets him smash into purple Meteorites that will fly into Shadow, slowing him down. If Sonic can catch up to Shadow, he can ram into Shadow, eating away at his rings. In order to win the battle, the player must attack Shadow this way when he has no Rings.
In Hard Mode, both characters have to get three Energy Cores in order to perform their special attacks. Shadow also seems to be faster and more proficient in pursuing Energy Cores, taking the higher routes more often. The blue meteors and almost all Trick Jump Panels are also absent, making it harder to maintain boost.
In the Nintendo 3DSversion, Shadow has three attacks: Chaos Spear, the Boost and the Homing Attack. Every time Sonic gets ahead of him, Shadow will use his Boost to catch up, which is faster than Sonic's boost and as a result it could end in Shadow running over Sonic. If Shadow is ahead of Sonic, he will start throwing him Chaos Spears and if the hedgehogs are really close to each other, Shadow will try to homing attack Sonic. Sonic can hit Shadow with either the boost, the Slide Attack or the Stomp.
The main stage theme music is a remix of "For True Story" from Sonic Adventure 2. During the stage when using the default music, the music switches to "Live and Learn" if Sonic gains two Energy Cores. If Shadow gains two Energy Cores, the music switches to the Crush 40 version of "All Hail Shadow". After about forty seconds, if neither character has defeated the other at this point, the music returns to "For True Story".
However, there is a minor difference: In the original, the entire side of the moon (that the camera is pointing at) is light, but in Sonic Generations, one half is light, and the other side is dark (this is also the side Shadow is on when he jumps).
This version of the fight takes place on a looping arena with many interactive objects such as grind rails and meteorites, which differs greatly from the original, which took place in a never-ending straight track, with no rails and meteorites as merely destructible objects
Perhaps the largest change in the structure of the course is the fact that the platforms do not disintegrate as Sonic runs on them, as they did in the original.
Although there are rails terminated with green marks in the arena, as can be found in Sonic Adventure 2, the user cannot do a jump trick at the end of the said rails.
When Shadow runs into the trick ramp, he does one Trick Action and a round kick, then falls to the ground.
Before the race, it is shown that Shadow guards the fourth Chaos Emerald. Although this is just due to his position as a boss (both chronologically and in order), this ends up as a coincidental reference to one of Shadow's famous lines from Shadow the Hedgehog, "Where's that DAMN fourth Chaos Emerald?"
The music played in the hub world is a short, instrumental remix of "Throw It All Away", Shadow's main theme in Sonic Adventure 2.
If one manages to leave the area where Shadow unleashes his special move quickly enough, this causes a number of problems that occur for the rest of the fight though these issues are fixed upon restarting or quitting the stage:
Shadow would constantly knock into walls and reach ridiculous speeds that even the Sonic Boost cannot keep up with. If Shadow is attacked, he will constantly be flashing for the rest of the stage and cannot be attacked.
In the console versions, if the player stays at a particular area with the Trick Jump Panel long enough, he will unleash a Chaos Spear that can sometimes mute the sounds of the whole game. (In the Xbox 360 version, the mute is temporary while in the PlayStation 3 version, the mute lasts indefinitely.)
Energy Cores will not appear on the stage, making it impossible to complete the stage.
If the player gets the second Energy Core as they are doing tricks, the models for Shadow and the asteroids will disappear for the rest of the fight.
If Sonic, from the area where Shadow uses his power-up, runs a long distance until the path ends, he will fall into a pit and lose a life.
If Sonic were to run the track backwards while Shadow goes forwards, Shadow will gain energy cores much faster.