Why? Your first thread has no replies, this one has two. It'd be better to keep the thread up which somebody has posted in already, and have the other one closed instead. Even if this is the newer one. ...Er, if you ask me.
Ash's Squirtle will win. Why?
The writers don't want to imagine what would happen if they had May's Squirtle win the battle. ...I guess it would be something involving hydrogen bombs and bazookas *shrug* I don't care that much about her Squirtle , but I assume that's what would happen
Seriously, we have seen how agile and strong SquadSquirtle has gotten in the Johto League. I'm pretty sure it gets lots more training with the Squirtle Squad than May's. I can't think of a believable way to make May's Squirtle tougher than Ash's. Just think of what stunts it could pull off (shooting off an attack although the opponent got the command first, hitting Water Gun at the exact same spot over and over again, etc.). Sure, they were uber-izing it a bit at that point to show how much it has improved under Jenny's control, but strength is strength.