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A Friendship in Flames

I figure Dave wins here. While John is super elusive and can go intanglible he will eventually tire out and make a mistake. Dave can also try the fight as many times as needed. He would waste a crap load of time clones but theoretically he could fight John an infinite number of times until he wins. Also when it's two Homestuck characters you kind of have to look at their classes and aspects since some are more geared towards fighting than others. For instance, Dave is a Knight of Time, literally someone whose sole purpose in the universe is to fight people using time magic as a weapon.
In character, they would need a very good reason to fight, but Dave takes it due to having more battle experience, as well as reasons listed above (time cloning, although he doesn't like using it) but then he also has the ability to freeze John in time, or just freeze him altogether, allowing him to land several critical blows, before John has time to turn to wind to avoid more effectively. But, on the other hand, John has dealt damage to Bec Noir, whereas Dave got his ass handed to him. Twice. Dave still takes, but not by much.