Fate/Zero/Tear Jerker


 * Numerous occasions.
 * Kariya Matou's farewell to Sakura after having just been infested by Zouken's insects in an effort to prevent Sakura from having to take part in the Fifth War. "It seems I've already lost [a bit] to the bugs inside me. I guess I'm not as strong as you..."
 * Being The Stoic, distant, cruelly practical Magus that he is, you wouldn't think Kiritsugu would be able to inspire this with one sentence. However, his realization that "Ilya weighs less than that Walther" (the Walther being his sniper rifle) and his reaction to this simply convey despair and depression and hopelessness far better than anything else ever could.
 * His breakdown in front of Irisviel in the second book is another one.
 * The prologue itself, too. Kiritsugu saying "Then, what about her? I... am not fit to hold that child", and crying at the realization that he's going to eventually have to choose between his beloved wife and daughter, and his ideals and his dream, fearing the time that he'll have to sacrifice what he wanted to protect.
 * Rider's incredibly blunt and harsh speech to Saber in episode 11, as he systematically tries to break down her ideals, ending with calling her a little girl. Saber's shaken reaction and her flashbacks to the battlefield, where we see her broken and severely wounded, is definitely a tearjerker.
 * On the same topic,
 * Caster's hallucination of Jeanne d'Arc, smiling kindly and holding out a hand for him to take Even worse, it's implied that he might have been about to make a Heel Face Turn.
 * What.....have I...
 * Kiritsugu having to kill to prevent a zombie outbreak in his backstory.
 * A great deal happens during the events of Fate/Zero, to be certain, but one of the most heart-wrenching tear jerking things of the entire series is what becomes of the 4 main children following the events of Zero. It's actually VERY difficult to determine who has it the worst of the 4:
 * Shirou Emiya - A young boy who would later become the main character of the events of Fate/Stay Night. He only shows up at the very end of Zero, but when he DOES appear, it's because the fire following the destruction of the holy grail had burned a huge portion of the city. It leaves him deeply traumatized, but it also took away all that he was prior to the fire, his old life, his old home, and his old family. He lost everything that day. Sure, Kiritsugu saved his life and adopted him, but he passed away 3 or 4 years prior to F/SN's beginning, leaving Shirou alone once more.
 * Rin Tohsaka - A child prodigy seeking to become a great mage to carry on her family legacy. The events of Zero end with.
 * Sakura Matou -  Is left in the custody of the Matou family, and by the end of Zero, she was.
 * Ilyasviel Von Einzbern - Iris and Kiritsugu's biological daughter..
 * Rin Tohsaka - A child prodigy seeking to become a great mage to carry on her family legacy. The events of Zero end with.
 * Sakura Matou -  Is left in the custody of the Matou family, and by the end of Zero, she was.
 * Ilyasviel Von Einzbern - Iris and Kiritsugu's biological daughter..