Samurai Jack has taken on many machines in the past, but he’s never fought a powerful ninja like Naruto before. Naruto doesn’t need to face Samurai Jack directly, as he can just blow up the country that Samurai Jack is in. Naruto can use his speed to evade Samurai Jack’s attacks and launch his counters with ease. Samurai Jack just won’t be able to stop Naruto. Naruto wins.