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The notion of Bill Cipher ever beating Pennywise was debunked hard a while back.

And Madness isn't its main form of hax at all. It has actual psychic powers that should be far superior to anything Bill has experienced before, and as far as IC behavior goes, it regularly abused these powers throughout the novel.
 
Paulo.junior.969 said:
Why is the loss against Bill still on IT's page? Heck, it was even removed from Bill's page.
Because Pennywise's page is locked, and because nobody ever bothers with fixing the Dark Tower pages when I'm not around.
 
Ugh I don't want to talk about anything now with all of these problems but I will just say a much weaker bill has defeated pennywise before so know that he is stronger he will do it even easier than before
 
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