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Voiced by: Bob Papenbrook
- Super Mode: As Super Ultimate in the climax of Dawn of Chaos.
BlackGuilmon and Co.
BlackGuilmon/ChaosGallantmon/Destructor Mode/Hazard Mode
- I am the last reminder of the monster you were before you and that Tamer removed me after you Biomerged for the first time! I intend to destroy you both and absorb you! Then, the circle will become complete!
Voiced by: Steve BlumThe evil 'twin brother' of Guilmon who is spawned from the essence of Megidramon.
- Black Knight
- Evil Twin: To Guilmon.
- The Rival: To Guilmon as well.
- The Sociopath
- Super Mode: As Destructor Mode and Hazard Mode in the climax of Dawn of Chaos.
- Villainous Breakdown: In Chapter 60 of Dawn of Chaos when near defeat.
Yamidramon & Atolmdramon/Doomsdramon (OC)
Yamidramon & Atolmdramon voiced by: Chris Sabat
The main antagonists of the Digidestined's side in Season 3 entitled, Dawn of Chaos.
Madoudramon/MahouGarurumon /Titan Mode (OC)note
Voiced by: Geoff Dolan
- Big Bad: To the Digi-Destined.
- Black Knight
- The Dragon: To Valmarmon.
- Expy: Of Koragg the Knight Wolf/Dark Magic Knight Wolzard from Power Rangers Mystic Force/Mahou Sentai Magiranger. His Titan Mode is the Centaurus Wolf Megazord/Wolkaiser.
- HeelFace Turn: The memories of his former self seem to help in Chapter 59.
- Off with His Head!: In Chapter 59 by Madoudramon (after recovering his memories of his goodness) nonetheless.