Devimon - Devimon is Adult level, Virus attribute, and a Fallen Angel Digimon. His attacks are Death Claw, Razor Wing, and Hell Contract. He belongs to the Nightmare Soldiers. Devimon resided on File Island, in a castle atop Infinity Mountain. He was controlling many other Digimon with Black Gears, but one by one the Chosen Children defeated these Digimon, removing the Black Gears. They also one by one learned how to evolve their Digimon to Adult - except Takeru. The Chosen Children eventually set off to fight Devimon, but they were losing badly. Devimon went for Takeru and Patamon, since legend said the smallest would defeat him, and in that moment, Patamon evolved to Angemon, his Adult. Angemon poured all his energy into one Heaven's Knuckle which deleted Devimon, but he died doing so.
Etemon - Etemon is Perfect level, Virus attribute, and a Puppet Digimon. His attacks are Love Serenade and Dark Spirits. His family is unknown. Etemon was the first evil Digimon the Chosen Children encountered on the continent of Server. He had a large network where he could detect people and objects, and he had a vehicle pulled by Monochromon, and several Gazimon serving under him. During this time, the Chosen Children aquired their Crests, but Taichi forced his to work, and the result was Skull Greymon. Skull Greymon went out of control, but he made Etemon flee. Eventually, Greymon attained his proper evolution, and one Giga Blaster from Metal Greymon defeated him. He later returned as Metal Etemon, but Saber Leomon and Zudomon managed to defeat him.
Vamdemon - Vamdemon is Perfect level, Virus attribute, and an Undead Digimon. His attacks are Bloody Stream, Night Raid, and Cloud Minion. He belongs to the Nightmare Soldiers. Vamdemon was the second evil Digimon the Chosen Children encountered on the continent of Server. Vamdemon had many Adults, Perfects, and Child Digimon under his command, three of which were Tailmon, Wizarmon, and Pico Devimon. Pico Devimon caused much damage to the Chosen, but when Taichi returned from the Real World, most of it was repaired. One by one the Chosen Children's Digimon were able to attain Perfect - except Patamon. The Chosen Children learned Vamdemon intended to go to the Real World, but they were unable to stop him. They re-opened the gate and went through to attempt to repair whatever damage he had done. They defeated many of his army, and learned of his search for the eighth Chosen Child. They found her, Taichi's sister Hikari, and her partner was Tailmon, and her Crest was that of Light. It would not have been possible without Wizarmon, who had only served Vamdemon because of Tailmon. Vademon used Night Raid on Hikari and Tailmon, but Wizarmon jumped in the way and took the full blast, dying in the process. Tailmon evolved to Angewomon and defeated Vamdemon with the help of the other Perfects and Angemon. However, he was later revived as Venom Vamdemon, consuming all his remaining servants in the process - but thanks to a prophecy unearthed by Gennai, Taichi and Yamato were able to Warp Evolve Agumon and Gabumon into War Greymon and Metal Garurumon. With the help of the Crests, Venom Vamdemon was defeated as well.
Metal Seadramon - Metal Seadramon is Ultimate/Final level, Data attribute, and a Cyborg Digimon. His attacks are Ultimate Stream, Hell Squeeze, and Poseidon Divide. He belongs to the Deep Savers. Metal Seadramon was one of the Dark Masters who reformed the Digital World after the Chosen Children left to fight Vamdemon in the Real World. He helped to seal away the Holy Beasts. Metal Seadramon nearly defeated the Chosen Children - he had War Greymon in his teeth. But thanks to a sacrafice by Whamon, War Greymon was able to use his Dramon Killers and rip apart Metal Seadramon, even his Chrome Digizoid armor. His deletion led to one fourth of the Digital World deleting to be later reconfigured.
Mugen Dramon - Mugen Dramon is Ultimate/Final level, Virus attribute, and a Machine Digimon. His attacks are Mugen Cannon, Booster Claw, and Catastrophe. He belongs to the Metal Empire. Mugen Dramon was one of the four Dark Masters who reformed the Digital World after the Chosen Children left to fight Vamdemon in the Real World. He helped to seal away the Holy Beasts. Mugen Dramon had made a massive city for himself, and he had metal oriented servants. He was able to locate the Chosen Children every time Koushirou plugged his computer into to the city, and there were many fights as a result. Mugen Dramon blew the Chosen Children into the lower depths of the city, where they came upon enslaved Numemon who were being forced by Waru Monzaemon, who served Mugen Dramon, to produce electricity for the city above. The Chosen Children freed them, and Waru Monzaemon was killed by Mugen Dramon for his incompetence. The Chosen Children then met Andromon, who was forming an underground resistance force, and he joined them. War Greymon ripped through Mugen Dramon with his Dramon Killers. Another fourth of the Digital World deleted to be reconfigured later...however, Mugen Dramon survived, barely alive, and jogressed with Chimeramon, resulting in Millenniumon.
Pinocchimon - Pinocchimon is Ultimate/Final level, Virus attribute, and a Puppet Digimon. His attacks are Bullet Hammer and Lie. He belongs to the Wind Guardians. Pinocchimon was one of the four Dark Masters who reformed the Digital World after the Chosen Children left to fight Vamdemon in the Real World. He helped to seal away the Holy Beasts. He made Takeru play with him - with real guns. The other Chosen Children arrived, but Pinocchimon could control War Greymon, and he made his house attack the rest. Metal Garurumon leaped out of the forest and killed him. Another fourth of the Digital World deleted to be reconfigured later.
Piemon - Piemon is Ultimate/Final level, Virus attribute, and a Demon Man Digimon. His attacks are Trump Sword and Clown Trick. He belongs to the Nightmare Soldiers. Piemon is the leader of the four Dark Masters who reformed the Digital World after the Chosen Children left to fight Vamdemon in the Real World. He helped to seal away the Holy Beasts. Piemon watched the Chosen Children delete the other Dark Masters from his observatory on the top of Spiral Mountain. He sent Lady Devimon to fight them when they came near his base, and she was defeated after a long fight between Angewomon and herself. Once all the Chosen except Mimi were assembled, they began fighting Piemon, but were turned into keychains. Takeru, Hikari, and Angemon attempted to escape, being the last, but Piemon cut the rope and then Angemon evolved for the first time to Holy Angemon. He smacked Piemon around and took the keychains back, restoring them with his holy power. Piemon retaliated with an army of Vilemon, but then Mimi arrived with a small army of the Chosen Children's surviving friends. Holy Angemon sucked all the injured Vilemon through his Heaven's Gate, but Piemon laughed, because it could not put him in. Metal Garurumon and War Greymon reminded him of their presence by attacking and knocking him into the gate, which closed. The last pof the Digital World deleted.
Apocalymon - Apocalymon is Ultimate/Final level, unknown attribute, and unknown type. His attacks are Death Evolution, Darkness Zone, and Grand Death Big Bang. He belongs to the Dark Area. He passed from the World of Darkness to through the Wall of Fire into the Digital World with the help of a time-traveling Millenniumon. He presence caused a warp in time which made time run faster in the Digital World than on Earth, and the Dark Masters were created. Apocalymon sat back and waited, and the Chosen Children came to fight him. He used Bloody Stream and Mugen Cannon on the Chosen, then Death Evolution, which devolved their Digimon. He used Darkness Claw to destroy the Crests, then he deleted the Chosen and their Digimon. They ended up in a sort of Digital Limbo, where they realized their Crests were truely inside of them. All their Digimon evolved to their highest forms, and they wished themselves back to life, to Apocalymon's shock. The Perfects took out Apocalymon's giant claws, and Metal Garurumon and War Greymon deleted his body...but then, he used Grand Death Big Bang which would delete the Real and Digital Worlds! Thankfully, the Chosen's Digivices contained the attack, and the Digital World was recreated.