Never in the manga but in the anime, I came close at Gaara's death and Naruto getting so upset over it. Gaara's a favorite of mine and I was happy to see how far he'd come only to see him die.
Naruto learning Jiraiya died. Man, he was so sad, it was heartbreaking.
Kakashi's death, man! I remembered watching it, and all I could think was "Kakashi really died to save the fat guy..." Lol I almost hated Choji.
Kushina and Minato's goodbye to Naruto, that whole scenario and the music was so sad, I actually teared up then but I can proudly say the manga had never made me shed tears =D