In terms of battle, Squall would win b/c he is overall a bit weaker than cloud, yet much faster. Cloud wouldn't be able to hit him and Squall would quickly gain an upper hand as cloud tires from lifting a three-hundred lb swd. Ok it's not really that heavy, but you get my point. Oh, and Squall can also :shoot: Cloud's balls off
In terms of coolness, Squall would win again b/c, first of all, VIII was better than VII and the storyline had way more character development in Squall than Cloud. And is Cloud like, (SPOILER)the ONLY main char guy in a FF that didn't die instead of his girlfriend? Weakness :twak: