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He may be a cowered and would likely be frighted by a bunch of Naruto clones but thanks to his level of Regenerationn, and the fact that he can take a hell of a lot of butt kickings so he could outlast Naruto.
Courage should win this fairly easily if not with minor difficulty. And here are my reasons why.
1 - There's no way Naruto can get past Courage's level of Regenerationn.
2 - Courage can disperse any clones Naruto tries to spam with a casual scream
3 - If it were to come to a straight up fist fight beat down, Courage has endurance for days. Based off of watching virtually all episode of both Courage and Naruto, the "Stupid Dog" (who is far from it" can outlast him for sure.