For the Robot Master from the Mega Man series, see Shadow Man.
Shadow was among the first four of Sonic's friends to be abducted in order to be turned into one of the Roboticized Masters. After being captured by Metal Sonic and Bass along with Tails, Knuckles and Amy, Shadow was transformed into Shadow Man. Together with his new teammates Tails Man, Knuckles Man and Rose Woman, he attacked the Mega City bank, only to be confronted by Proto Man. Shadow Man's comrades quickly overwhelmed the Robot Master, only to be attacked by Mega Man. Shadow Man quickly had his teammates attack the interloper while he transported the grey Chaos Emerald. He was briefly stunned by Mega Man's Mega Buster weapon, but managed to escape through a Warp Ring alongside his teammates and Metal Sonic. On orders from Dr. Eggman and Dr. Wily, he and his teammates split up after entering Green Hill Zone, leaving Metal Sonic to continue antagonizing Mega Man while they made their way to a rendezvous point. Along with Knuckles Man and Rose Woman - Tails Man having stayed behind to observe the ensuing battle between the duped Mega Man and Sonic - Shadow Man returned to the Wily Egg and presented the Chaos Emerald to his masters.
Shadow Man and his remaining teammates - now joined by Silver Man, Blaze Woman, Vector Man, Espio Man, and Charmy Man - were soon dispatched to battle Sonic and Mega Man after the two heroes joined forces. After a brief battle, Shadow Man and most of the Masters were sent to pursue Proto Man deeper into the Skull Egg Zone, leaving the roboticized Chaotix to deal with Sonic, Mega Man, the de-roboticized Tails, and Rush. Following the restoration of the trio, Shadow Man was called away from the search, and the doctors decided to team him up with Wily's Shadow Man to challenge the heroes again. Sonic and Mega man de-roboticized Shadow Man as soon as he warped away with Chaos Control. As soon as he was de-roboticized, Sonic asked for Shadow's help. He refused and warped away.
With his natural ability to manipulate Chaos energy, Shadow Man was believed to be exceptionally powerful. He retained his Chaos Control ability to warp space-time and teleport, and also possessed a powerful energy weapon called the Chaos Cannon which could essentially freeze targets in time.
In order to defeat Shadow Man, Mega Man tricked him using the Chroma Camo ability he took from Espio Man. He then counter-attacked using the Tails Wind weapon and de-roboticized Shadow using his modified Mega Buster.