SOLITAYRE'S PROFILE

Quick rundown of their respective abilities

Weaponry

Both characters have preposterously implausible weapons. Cloud's is larger and heavier and thus probably the stronger of the two, but Squall's weapon never misses and can crit 100% of the time if he uses the trigger properly, and his Renzokuken can be used repeatedly if he's at low health. I give advantage to Squall.

Armor

Cloud can equip bangle and accessories to shore up his defenses and protect him from status effects. Squall relies on Guardian Forces for defense, able to junction magic to his defense stat, and can summon GFs to take damage for him. Tough call but I think Squall has a slight advantage here, mostly because letting a GF take damage for him lets him survive even devastating Limit Break Attacks.

Physical Abilities

Augmented by Mako energy, Cloud is one tough son of a bitch. Not only can he swing the Buster Sword around like it's nothing, but we observe him demonstrating superhuman levels of durability. He has survived falls of hundreds of feet without serious injury, survives being totally impaled by Sephiroth, and even survived being fully immersed in the lifestream.

We don't see Squall accomplish anything close to this. As others have observed, Squall's ability to tolerate injury doesn't appear to be any greater than a normal human's, GFs be damned.

Cloud holds a monstrous advantage in this category.

Supernatural Abilities

Cloud can use Materia to cast spells and unlock new abilities. He can equip as many of these as he has slots in his weapons and armor. These materia do have negative effects on his stats, but the benefits generally outweigh the drawbacks.

Squall uses GFs to unlock new abilities, can summon them in battle, and can draw magic with their power. This gives him the ability to cast magic almost infinitely, but his selection is limited by what he can draw from his enemies or environment. Squall can equip as many GFs as he likes. The primary drawback of GFs are memory damage, which are not germane to this battle.

At the start of their adventures, Squall has Shiva and Quetzalcoatl available, and Cloud has the Ice and Bolt materia. If we give them both the fully developed versions of those, Squall holds the advantage here.

Personality

Cloud is a profoundly broken individual, having a hard time understanding who or what he is. He is easily misled or confused. He has few driving forces in his life besides defeating Sephiroth and protecting the planet. Without friends to back him up, Cloud is prone to severe depression and mental breakdowns.

Squall lives his life by a principle of self-reliance. He too is rather broken but not nearly as badly as Cloud. Squall always does his best to accomplish his mission, even if he doesn't agree with it. He eventually comes to trust and rely on his friends but is capable of functioning without them. Squall's main disadvantage is he is terrible at communicating on a personal level and lacks empathy or the ability to understand other people's feelings.

Both pretty much suck at this, but Squall sucks slightly less. However, there's a catch here that will come back to haunt him.

Combat Experience

Cloud's entire life is a lie and he actually has much less combat experience than you might think. He was never actually in SOLDIER. He learned most of his fighting style by stealing it from his friend Zack.

Squall has been training to be a soldier for several years and has participated in multiple drills and actual live combat scenarios. He knows the value of following orders.

Both are thrust into leadership roles they're not comfortable with, but eventually become reasonably good at it. But only Squall gives commands and orders during an actual military confrontation.

Again, Squall holds the advantage here by actually having combat experience.

So who wins?

As we can see, Squall holds a small advantage in many categories, but Cloud has one key advantage in that his Mako augmentation makes him really hard to actually put down. Even Sephiroth couldn't do it. In the end I think Squall puts up a good fight but even with two GFs backing him, Cloud's superior strength and durability are just too much.

There's one category where Squall could win out, and that would be to fight Cloud psychologically and try to trigger a breakdown episode. Unfortunately for Squall, this happens to be one of the things he's the worst at.

I give the fight to Cloud.