Doctor Doom's force fields, sorcery, and superior firepower overwhelm Deadpool despite the healing factor.
Deadpool's healing factor makes him virtually impossible to kill, but Doctor Doom has countless ways to incapacitate without killing. Magical containment, force field imprisonment, molecular manipulation, or simply teleporting Deadpool to another dimension are all within Doom's capabilities.
Doom's force fields prevent Deadpool's weapons from ever reaching him. Guns, swords, and explosives bounce off shields that withstand attacks from Marvel's heavy hitters. Meanwhile, Doom's energy blasts and mystical attacks can damage Deadpool faster than his healing factor can regenerate.
Deadpool's unpredictability and fourth-wall awareness are amusing but practically useless against someone of Doom's power level. Victor Von Doom has fought the Fantastic Four, Avengers, and cosmic entities โ a mercenary with swords and jokes is not tactically challenging.
Deadpool's healing factor makes him impossible to permanently defeat, and his unpredictable fighting style has thrown off opponents far more powerful than him. His arsenal is diverse and he never stops coming.
Doom's force fields block all of Deadpool's weapons, his sorcery can trap or contain Deadpool without needing to kill him, and his power level makes Deadpool's entire arsenal irrelevant.
Doom wins by containing or incapacitating Deadpool rather than trying to kill him. The healing factor prevents a permanent defeat, but Doom has too many ways to end the fight without needing to overcome regeneration.
Deadpool also fights
Doctor Doom also fights