"Tears" (涙, Namida) is chapter 403 of the original Naruto manga.
Naruto thinks about his last encounter with Itachi, where he told Itachi that he was more of a brother to Sasuke than Itachi was. Itachi asked, if this were true, what he would do if Sasuke attacked Konoha. Naruto responded that he would defend the village and stop Sasuke without killing him. Pleased, Itachi gave him some of his power, hoping Naruto would not need it. He then left. Sasuke, elsewhere, also thinks about Itachi; the night he killed the Uchiha clan. At the point Sasuke had thought he had passed out that night, Sasuke had followed Itachi and attacked him. Itachi was not harmed, but he looked upon Sasuke with tears in his eyes. Sasuke concludes that he cannot do as Itachi wanted him to.