- The attack on Ryuudou Temple, where Kuzuki is killed, and Caster is corrupted. Once again, the Princess of Colchis is denied her one shred of happiness, and now she intends to make the world pay for her loss in terrible fashion.
- In Chapter 14, Shirou is visited by the disembodied spirit of Irisviel, who softly asks him to do his best to save Illya.
- Berserker's death in Chapter 22, particularly his regret that he can't protect Illya any longer, and as he passes she - despite being unconscious - seems to feel it, and starts to cry in her sleep.
- Rin going through the Matou household in Chapter 29. Especially the part where she finds evidence of what Shinji did to Sakura.
- Much earlier, when Sakura wakes up from falling unconscious at Tohsaka Manor, with Rin looking after her. Rin offers to form an alliance with her against Shirou and Illya, and Sakura is quite hesitant to accept. As Tohsaka declares she will help her, Sakura is reminded vividly that, no matter where she goes Zouken still controls her, and can barely think of a chance to escape. Even worse than the SICKENING physical abuse she has suffered, is the psychological pain she has endured, having no hope of truly being free or deserving happiness.
- Caster being killed by Dark Sakura. Both of them loved each other (in a platonic sense), but Dark Sakura felt the need to punish her for hurting her sister and Emiya.Sakura: "I supposed I could have tried to do it without destroying her mind, but...well, she did hurt senpai, and even tried to kill nee-san. I loved her, really, but I had to punish her for that. I'm sure she'd understand. And if you think about it, a part of her will exist inside me forever, so it wasn't even that harsh."
- Pretty much everyone who had a role in Chapter 33 needed a hug at one point or another.
Shirou: "You... aren't calling me senpai anymore."
- Rin is obviously guilt ridden over not being able to help Sakura and in a fit of stress and anger takes her frustration out on Ilya. The latter in turn reveals she will not have long to live and wished to spend as mush time with Shirou as possible before dying.
- Seeing what Sakura has become, especially though Shirou's eyes. She seems to have forgotten who she was entirely as well as the ones she loved. Shirou sums it all up in one line.
- Archer... just Archer.
- Avenger summoning corrupted versions of Enkidu, Lancer!Child!Medusa, and Lancelot.
- What EMIYA Alter's very presence and Noble Phantasm do to poor Shirou.
- The corrupted Mordred's final moments, mixed with happiness because Arturia renamed her attack Excalibur Mordred.
- Illya's reaction to Heracles trying to do a Heroic Sacrifice.
- Avenger does not Face Death with Dignity, breaking down and sobbing it only tried to do what it thought humans wanted, it only tried to make pain end, it only tried to help. Its emotional outburst is so raw Shirou briefly, almost feels sorry for it.
- As soon as Avenger is defeated, all the Heroic Spirits Illya and Sakura summoned disappear.
Tear Jerker / Chaos Theory