The problem with Punisher trying to calculate against Deadpool is that, honestly, Deadpool probably doesn't even know what he's about to do... he just does things. He's unorthodox and, let's face it, kinda sloppy. It's that sloppiness that gets him in trouble sometimes, like Taskmaster once hinted to.
And for all of his antics, Deadpool is not an idiot, and part of his fighting style is playing mind-games with the opponent; breaking their concentration and irritating them. That kinda tactic may not work well on Punisher though, he's way too focused so I don't think he's get thrown off his game, at least not at first.
As for their fighting skills, I'd give Deadpool the advantage since he can throw down evenly with people like Wolverine and Iron Fist. He also possesses a powerful healing factor whereas Punisher is a normal human. Weapons-wise, until recently their weapons were pretty similar, but now as G-Man pointed out, Punisher has started using some crazy equipment... it's practically a power-up, like Cosmic Spidey or something.
I know that they fought before, and although Punisher gave Deadpool trouble, Deadpool did have the advantage.
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