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and if in character ash uses his entire arsenal of pokemon thrs to many variables for me to consider, so good luck guys.
I don't recall Ash ever releasing the entirety of his Pokemon in his usual fights.

This fight begins as a one on one, Ash usually starts with Pikachu or releases another Pokemon.

While Sage Mode Naruto spawns two or three clones.
 
He had information on Pain and needed the backup because he knew Pain outnumbered him (The Six Paths + the numerous Summons)
Oh yeah he did know pain had multiple bodies, but wouldn't that encourage him from summoning here? cause ash summons pokemon so he might use it if he sees ash throw out a pokemon, but then again maybe not cause its only one whereas pain had 6 bodies and summonings, still a possibility tho
 
Greninja is FTL... Would ash's pokemon be equalized? And Pikachu has stat amps. I'm unsure if Naruto can win, Tho naruto's combat unpredictability is good so he has advantages with that.

 
I am voluntarily voting Naruto For Reasons Above. I swear this is my own doing.
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