- After spending most of an episode talking to Sieg and telling him all the wonderful things he will experience, Jeanne sends him away to the village where he will live. Her internal narration then reveals that she knows that he will fight in the war, with the visuals implying that this will end badly for him.
- Berserker of Black's death. She's the second Servant to fall despite the bond that she had with Caules setting her up as one of the most sympathetic Servant/Master pairing. Caules himself feels that he's failed her as a Master and he could have done more for her.
- Mordred's past is filled with this. Even with her mother manipulating her, Mordred was very devoted to her king. However when Morgan revealed that Arthur was her father, Mordred had this child like innocence. Things took a turn for the worse when her father basically just ignored her causing Mordred to be enraged leading that fateful battle where she perished. Eversince then, Mordred awaited to be part of the Holy Grail War in hopes that it could win the approval of Artoria.
- Lancer of Black trying and failing to hold on to his sense of self when Darnic forces him to turn into a vampire.
- Roche begging and pleading with Caster of Black to not turn him into Adam's core and demanding to know why the man he came to respect so much would do this. Even worse is how utterly calm Avicebron is being in return.
- Reika sacrificing herself to save Jack from being shot by Atalanta. The horrified Jack stays by her mother's side even as Reika uses her last Command Seals and Jack herself gets hit next by Atlanta's arrows. It's heartbreaking enough that Atalanta herself was disgusted for what she did. And in hindsight, this turns out to be Atalanta's very own Tragic Mistake, since this action is the start of the majority of her misery and downfall.
- Episode 18 was both this and nightmare fuel.
- Sieg finally comes to see the ugly side of the world as he views Jack's memories of many children being killed for no reason and thrown away. He's on the verge of a breakdown before he meets Jeanne again.
- Jeanne refusing to help the children that make up Jack the Ripper, as they are already part of her legend and can't be saved anymore. She puts them down but it's obvious that she's not happy about doing it at all.
- Atalanta does break down after Jeanne kills Jack, since that was reliving her pain of being abandoned by her parents when she was a baby. It's not a pretty sight.
- In Episode 19, Achilles looks so ashamed of himself when he can't think of anything to cheer Atalanta up after what happened to Jack the Ripper.
- In Episode 21, Chiron dies after having fought with his all against Achilles.
- In Episode 22, Achilles made up his shame at 19 by attacking the now mad Atalanta. They ended up killing each other, Atalanta recovered... and she started to cry, knowing that deep down she knew Jeanne was right, but she couldn't bring herself to deny that, not when her dream of a world where children were loved was on the line... It was one of the few moments that the old self of Atalanta was known to genuinely cry, which would be her last.
- Karna's death ends up being both this and a Heartwarming Moment at the same time, as Sieg is astonished that he treated him as a fellow human being as a matter of course. Karna goes on to say that for Heroic Spirits like himself, every living person in the present is a treasure that they fought for the sake of in the distant past, so of course the same would go for Sieg.
- Kairi and Mordred dying together in the Hanging Gardens' throne room, sharing One Last Smoke and talking about how it was fun.
- A bit sadder, given that Mordred comes to an understanding about her issues with her father and being king at the end. Given that this is a parallel universe to Fate/Stay Night, she may never see her father to hash out their issues.
- Jeanne being Mind Raped by Shakespeare's Noble Phantasm with various scenarios of Sieg dying, because of her growing feelings of love for him. She's also reunited with her old friend Gilles de Rais, and is forced to see him as the Serial Killer he became in his later years.
- When Jeanne recovered next episode, Gilles went on a rant that he wouldn't end up being saved, crying his eyes out. It's surprising that for someone who would end up being a gleeful Serial Killer, he's aware of what he has done and is desperately craving for forgiveness and salvation.
Tearjerker / Fate/Apocrypha