Itachi would lose against Jiraiya.

[LuckyMan]

Manga fact. Even with Kisames combined power the best they could do is stalemate him, Itachi's own words. That was base Jiraiya Itachi was referring to though. SM Jiraiya stomps them at the same time low difficulty.

Frog Call paralizes them both then Sage Ultra Rasengan kills them. GG. Woot!

 

[Draphsin]

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Replace sasuke with jiraiya & that's how the fight would go.

 

[yamato san]

You are right but sasuke and itachi hardcore fans wont accept this.

 

[I'm stupid real stupid]

Fight would be a draw
SM Rivals MS and Databook ranks them 35.5

 

[Gerkak]

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Replace sasuke with jiraiya & that's how the fight would go.

This^^^^^^^^^

Tsukuyomi ends the fight

 

[LuckyMan]

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Replace sasuke with jiraiya & that's how the fight would go.

Until Itachi realize it was a clone...

 

[LuckyMan]

Hmmmmmmmmmmmm