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Ch'rell was a dangerous Utrom who had many years/centuries/whatever experience as a villain. His time masquerading as Oroku Saki/Shredder and getting even better at fighting made him a force to be reckoned with. No matter how many times they beat him., he always came back. Karai even mentioned this at the end of Turtles Forever.
Doomquest, while only a one-shot villain in the OT, was someone Dregg was genuinely scared of. The Turtles had a slight advantage of becoming supermutants even if, at the time, they were starting to lose their intelligence every time they mutated. But they used the brains over brawn method to finally banish him to the Darkrealm. A future confrontation would've been nice especially during Dregg's Krang and Turtle enhanced period or even in Divide and Conquer. But that was one of the best episodes of Season 9 and that says something about the kind of threat Dregg was at the time.
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