I think it would be a draw if they fought in a one versus one battle. There are lots of factors that can edge either Cloud or Squall. On one side, we have Cloud with his Ultima Weapon, which grants bonus attack when Cloud's HP is full (Attack bonus decreases when Cloud's HP falls.) On the other hand, we have Squall with his Lion Heart which does not have that same restriction. For their limit breaks, it seems as if Cloud will be able to out damage Squall due to Omnislash's property to auto-critical hit each attack. Then again, Squall can use the junction mechanic from Final Fantasy VIII to immensely improve his defense statistics from physical attacks. At the end of the day, it's impossible to draw a fair conclusion since both of these warriors have different skill sets, different strengths, and weaknesses, and most of all, they live in two separate worlds.