Fate/Zero/Tear Jerker

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    • Numerous occasions. Lancer's shock and grief at being betrayed, Berserker's final moments with Saber, Saber herself - there are too many to count.
      • 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, Saber after Kiritsugu forces her to destroy the Grail. She returns to the hill of her scene of death, even more emotionally broken and undergoing a severe Heroic BSOD at the thought of what the rest of her men experienced. She concludes that the fall of her country was all because of her, because she was chosen as the king, and starts crying and and crying and apologizing, over and over again, after deciding that the only way she can repent is to use the grail to erase all her mistakes.
      • Caster's hallucination of Jeanne d'Arc, smiling kindly and holding out a hand for him to take before his death. Even worse, it's implied that he might have been about to make a Heel Face Turn.
    • Kayneth willingly gives up in the Grail war in order to save Sola-Ui, throwing away his pride, magic, and basically everything he worked his entire life for, and choosing to protect the woman he loves instead, even knowing she didn't love him half as much as he did her. Then, they are both shot (with her in his arms) and Sola-Ui dies. Kayneth is left bleeding and nearly dead, but upon seeing Sola IS dead, he then begs for Kiritsugu to kill him, but Kiritsugu reminds him that per their contract... HE couldn't... Saber then walks up and finishes Kayneth off... His blood's stains are ALL over Excalibur. Kayneth may have been a jerk, but this troper wouldn't wish what happened to him to happen to my worst enemy on my worst day...
    • Kiritsugu having to kill his mentor and adoptive mother to prevent a zombie outbreak in his backstory.
      • The episode in question aired on Mother's Day for extra despair.
      • When Kiritsugu is inside the holy grail, he sees visions of the past and is shown just how his wish was going to be granted, but then to rub extra salt in the wound, it implies that what he truly wanted was Iris and Ilya back. How then was the grail going to grant this? By wiping out all the rest of the world. So it forces him to come to a decision... In the grail, he shoots Ilya, and then kills Iris with his bare hands (both were just visions, but still.) The biggest grain of salt about THAT episode, comes from the fact that said episode premiered on Father's Day.
    • Rider's defeat. It doesn't really need much explanation beyond that, but in ALL of the Zero, he was probably the only one who brought genuine light to the story from start to finish. Thus it makes it all the sadder when he charged Gilgamesh... Everyone who knows about the main Fate/Stay Night story knew how it was going to end.
      • For that matter, anyone who knows about Fate/Stay Night's plot and who is in it, knew how Zero was going to end, right off the bat, but to actually see it all play out? THAT was like having tears ripped out, not jerked.
    • Irisviel's secret. Given her origins, it makes full sense that she never truly understood Kiritsugu's wish to save the world. She never understood the true meaning behind it, but at the same time, she believed in him and accepted his wish. Later on however, it's revealed that although she isn't as invested in it for the same reasons as Kiritsugu, she had one reason why she wished for Kiritsugu's wish to be granted when she would become the Holy Grail: If there were true peace on Earth, and an end to all conflict and suffering, that would mean that the 4th Holy Grail war would be the last one, which means that Ilya would have been spared from suffering the same fate as her.
      • To make matters sadder/worse, the evil entity within the Grail takes on her appearance and uses her image to converse with Kiritsugu to grant his wish. He rejects it, and is forced to kill the image of his mistress, his daughter, AND his wife. But it still doesn't stop there, because the Holy Grail continues to use Iris' image to appear to Ilya as well during the 10 year gap between the 4th and 5th Grail wars, all with the intention of turning Ilya against Kiritsugu AND twisting Ilya's mind.
    • 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 for the 10 years between Zero and Fate/Stay Night:
      • 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 5 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 her father having been murdered and her mother brain damaged and living in a mental hospital (signs point to her once beloved Uncle Kariya to have been framed for both of these things), with her parents gone or unfit to raise her, Kirei Kotomine became her legal guardian (yes... the REAL person who was behind destroying her family... became Rin's guardian), and it is pretty evident that while Kirei wasn't openly cruel to her, he was very sadistically manipulating her to cause additional suffering for her, such as giving her a gift of a dagger that her father had given him... The very same dagger that Kirei had used to murder him with. Also, her sister, Sakura was left in the custody of the Matou family, and she would never know the horrors Sakura was going through.
      • Sakura Tohsaka Matou - Rin's biological sister Is left in the custody of the Matou family, and by the end of Zero, she was completely broken and lost all hope of going against Zouken. As evidenced when Kariya finally dies amidst trying one last time to escape with her, she called him a fool for going against "grandpa". For the next 10 years, she would be continuously subjected to the Bug Room on practically a daily basis, but it gets worse, because Shinji had been away during the 4th Grail War, and upon returning to find he had a new sister, he was initially happy and treated her well, until he found out the reason she was there was so SHE could inherit the Matou's magic instead of him. After that, he started treating her like garbage just as bad as the others, and it's even said that he had molested and raped her on a few occasions. A few years before F/SN, Sakura met Shirou and Taiga, which were her first 2 real friends she ever had.
      • Ilyasviel Von Einzbern - Iris and Kiritsugu's biological daughter. The destruction of the Holy Grail at the end of the war, was seen as treason by the rest of the Einzbern family, so they prevented Kiritsugu from ever seeing Ilya ever again. In the meantime, they lied to her by telling her that Kiritsugu had abandoned her and started a new family with a new child in Japan. Additionally, Ilya began getting visions thanks to the spirit of the grail posing as her mother to turn her further against Kiritsugu and twist her mind. On top of all that, Ilya was being subjected to various surgeries and operations on a daily basis to make her stronger and stronger so that by the time of the 5th Holy Grail War, she was the strongest mage ever, with her body being 70% magical circuits.