Board Thread:Versus Debates/@comment-1018594-20150608074819/@comment-26127155-20150608085840

Jiraiya
 * Summons include Gamabunta, Gamahiro, Gamaken, Shima and Fukusaku.
 * Sage mode which requires assistance to use.
 * Higher chakra reserves

Kakashi
 * Much more flexible movepool which can handle most occasions.
 * Mangekyo sharingan which assists in genjutsu and he also has Kamui.
 * Tactically more adept than Jiraiya.

The Major hurdle for Kakashi in this match up is the summons that Jiraiya possesses. Gamahiro, Gamaken and Gamabunta are very powerful summons and Kakashi only has a limited amount of ways to handle them.
 * 1) Use Kamui to kill them (one at a time at the max considering their size).
 * 2) Use genjutsu as this could immobilize them (all though, they could be freed by an allies interference).
 * 3) Using shadow clones to distract them while he tries to kill Jiraiya.

Jiraiya's main focus would be to avoid kamui (as his senjutsu's healing abilities wouldn't really matter). I am not sure if Jiraiya canonically knows about kamui, which could be a major deciding factor in the fight. Kakashi's win condition would be to have kamui land on Jiraiya which sounds simple, but he requires a clear line of sight on Jiraiya as well as enough time to execute the technique.

In the end I could see either person winning in this fight but I am leaning more towards Jiraiya since there are several hurdles that Kakashi needs to overcome in order to complete his win condition while Jiraiya 'only' needs to land a direct blow onto Kakashi (which in theory is more easy).