Usopp vs Naruto

[Lone Wolf]

Usopp from OP vs Naruto. Naruto can't use Boss summons, he starts in base form, can go SM during the fight.

[Space Cowboy Sasori]

Base Naruto isn't fast enough to dodge Usopp's projectiles, it takes time for Naruto to become SM so during that time Usopp can nail him with projectiles.

If Naruto goes SM, I'm not sure who wins but I believe Naruto would with FRS behind him.

[Vivi]

Usopp from OP vs Naruto. Naruto can't use Boss summons, he starts in base form, can go SM during the fight.

Usopp wins.

He's much faster than Base Naruto hence he got away from Kiss Arlongs fastest Runner.

SM needs time to gather all the Energy enough for Usopp to strike.

His Projectiles are hypersonic.
Base Naruto is Supersonic only.

So one shot and its over and Usopp is a master marksman.

Heck he went toe-to-toe with Luffy and lost to plot.

[Miles Edgeworth]

Usopp wins.

He's much faster than Base Naruto hence he got away from Kiss Arlongs fastest Runner.

SM needs time to gather all the Energy enough for Usopp to strike.

His Projectiles are hypersonic.
Base Naruto is Supersonic only.

So one shot and its over and Usopp is a master marksman.

Heck he went toe-to-toe with Luffy and lost to plot.

Actually it's SM Naruto who's supersonic, Base Naruto is subsonic.

Anyway I say that Usopp stomps Base Naruto, I think SM Naruto might win against Usopp by a slight margin due to his durability and FRS. Unfortunately in this match he won't get time to use SM.