Sorry Pitch, I'm a much bigger fan of Jack than I am of you (and considering how big a fan I am of you, that's saying something.) No one can win against Jack Skellington. He will eternally rule the realm of fear
Pitch would have a better chance to win because he has the ability to use his shadows and his dream dust while Jack Skellington is unable to use anything from along those lines. But since Pitch thrives off of fear, and Jack wouldn't really be scared of him, that would even the odds a bit.
Depends on the nature of the battle. Neither of them are generals, but Pitch has a meanness that Jack really doesn't; Jack always means well, and seeks to inspire others and create grand things. Pitch, on the other hand, lusts primarily for control. In a hand-to-hand battle, I believe Pitch would win. However, on a grander scale, I'd go with Jack, as Jack is the better leader.
*uhm.....first General Kosmitiz Pitchiner (before he became Pitch) second when he became Pitch Black he lead the Dream Pirates on the Nightmare Galeon (a twisted black ship that sailed through space ).
Well; technically Pitch should probably be put against Oogie Boogie too (and on scariness Oogie would probably win- since Oogie actually wanted to cook and eat Santa Clause stew) On this- um- I'm not sure at all I like them both- no actually- what would win would be them teaming up together and having some "fun".