Re: When did Naruto surpass Jiraiya ?
I don't believe it to be the moment he mastered sage mode... People, underrate Jiraiya in my eyes.
I would say it depends, purely because i doubt that Naruto would be able to use summons, considering that they've know jiraiya allot longer so it's unlikely they will even enter the fight, which is a disadvantage to Naruto. Then again, Jiraiya can't enter sage mode without Maa & Paa, so i guess if they were on his side, then i believe jiraiya would have a good chance.
Jiraiya may not have mastered Sage mode the the same degree as Naruto, however, Jiraiya has a vast amount of experience and jutsu, not to mention he knows how Naruto think's and operates, he was his trainer after all.
Naruto had time to prepare for the battle, by having sage mode clones stand by which was a massive advantage for him, since he at the time was only able to go in to sage mode for 5 mintues...
It's impossible to say because there are allot of conditions that you would have to take in to account, such as does maa & Paa help him go into sage mode, would they use genjutsu...
This is them 1 on 1, however... Overall i believe he surpassed him when he learned Kyubbi mode, however... At this point in moment i believe he would beat him while in Sage mode because he's got experience and has learned how to use sage mode more sufficiently, although i doubt he surpassed him the moment he learned sage mode.