I'm a little curious about this so about two well known horror masters and what would happen if they would fight each other. Who would win a fight between Freddy Krueger and Pinhead?

Pinhead doesnt sleep.

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What about if in New Nightmare, instead of Nancy having to go after Freddy, Pinhead did? [Sure, it deviates from the whole plotline of the flik, but meh]

The dude asked a hypothetical question which carries some weight in the Bad Guy Vs. Bad Guy field.

Personally, I reckon Pinhead would win because he's just total carnage, Freddy would just spend too much time making puns about his face. But then again, Freddy is hard to kill. I have only seen the first 2 Hellraiser flix [Hellraiser was a brilliant flik but the second left a lot to be desired, so I kinda stopped there] and I grew out of Freddy when my brothers stopped making me watch 'em, so I'm probably not an authoritative source. But, yeah, Pinhead in my books.

Pinhead!

pinhead would definately win kuz he also has his own world and he has disiples hes brutal as fuck!

Freddy can get only get to through your dreams, but pinhead he needs someone to play with the cube then he can come out with his little hell pals and evil looking pets :)
So umm yeah Pinhead would win

Pinhead's a bitch.
Freddy would totally win.