Oichi's story mode in Heroes. Starting from witnessing Nagamasa's death, and then being told to do atrocities by her brother Nobunaga, no matter how much she begged that she didn't want to (Nobunaga, you S.O.B), until eventually she fell into madness and became possessed by her own dark powers, killed her brother and his whole army, then regained her self, breaking down in tears...and got crushed by the collapsing temple. All with a heart-wrenching song "Nemure no Hana" by her seiyuu Mamiko Noto to end it.
The third game is filled with these.
Case in point, Ieyasu's first ending. With him sitting next to Mitsunari's corpse, reflecting on their past interactions, and crying tears of genuine grief.
Every time you have to kill Yoshitsugu in the Osaka: Winter campaign.
Yoshitsugu: Is this...the end? Am I to leave him behind?
Mitsunari: NOOOO! YOU CANNOT DIE!
As if she hasn't been through enough, there's Oichi's Eastern Army ending, where she breaks down because she can't remember the precious thing she lost (i.e. Nagamasa). Then she quietly goes to sleep, since that's the only comfort she can find.
Even Oichi's Joke Weapon is a Tear Jerker. The shadow hands wear cute puppets of Nagamasa, with the flavor text, "Don't you remember why you're crying?"
When Sasuke is killed during the Ueda Castle stage, he tells Yukimura to find a replacement, fondly calling him by his old nickname of "danna". Ninja generally aren't worth much, but Yukimura tearfully begs for some time to grieve his friend.
Kasuga's death is equally upsetting, murmuring how she won't be able to return to Kenshin. Keiji's reaction is one of the few times he shows genuine rage, and Kasuga's distraught cry of "Give him back!" if Keiji dies before her isn't much better.
The last stage of Mitsunari's second route, when the time comes for Kojuro's death and his final conversation with Masamune.
Kojuro: After having gone through so much...I suppose it was beginning to get a little tedious.
Masamune: What are you saying? Kojuro, I can't go on without you.
Motonari's blue route ending. Dear God, Motochika's voice actor carried that through well...
Keiji's purple route concludes with him finding out from Ieyasu that Hideyoshi's last thoughts were of Hanbe, and shedding a Single Tear for his dead former friend. Even more heart-wrenching when you realize that Hideyoshi looked back on his past for the first time, despite being someone who believed that only the future was worth thinking of.
And despite its name, UTAGE proves devastatingly depressing at points. No wonder they included so many comedy characters; it was to balance out Hisahide, Sasuke and Kojuro's stories!
For a game that was supposed to be more lighthearted than its predecessor, SB4 has many routes that invoke Tear Jerkers:
Keiji defeating Hideyoshi in his drama route isn't much of a victory at all, as he's forced to come to the realization that he and Hideyoshi have gone down far too different paths for them to ever go back to being friends, no matter what changes. Keiji's tears only make this scene even more heart wrenching.
Mitsunari cradling Hanbe as he succumbs to his wounds in Hanbe's drama route. Mitsunari begins to break down in tears during the battle between each other in the game.
Hideyoshi's monologues during his last stage in his drama route. Before dying from his illness, Hanbe told Hideyoshi he should find another right arm to take his place should he fall in battle - Hideyoshi persists in believing that the only man suitable of being by his side is Hanbe, as he's the only friend he has.
Katsuie and Sakon's anime routes are probably the most upsetting of the game. You really have to see them to cry along with them. Context - Katsuie is finally set free by Nobunaga, which shatters the last of his resolve and leads him to murder both Oichi and Nagamasa, but he eventually decides to let Yoshiteru execute him, as he believes he has nothing left to live for if things can't go back to the way they were. Hideyoshi and Hanbe have been killed by Ieyasu's forces, leaving Mitsunari in an uncontrollable trance of rage and bloodlust. Sakon wants to calm him down and bring him back to reality from the denial that H&H are dead, but Mitsunari believes that Sakon is really a spy of Ieyasu's come to assassinate him, and will not calm down unless the 'spy' dies...which he does, willingly.
Matabe's backstory is possibly this. Matabe used to be a prominent and sane member of the Toyotomi, as well as a good fighter. He was incredibly confident until he suffered his first defeat at the hands of Kenshin - #2 in his revenge book. This is where his mind started to break down. Eventually the Date troops laid siege to Odawara and, working under the Ishida forces, Matabe ignored the orders given to him, went to attack the Date on his own and was defeated. This caused people in the Toyotomi army to laugh at him and deride him, and that's when he snapped. When he fights Kenshin, Kenshin tries to bring him back to his senses but doesn't succeed, and regrets that he wasn't capable of saving him. Soon he's hunting down Masamune, his #1. During the Date stage, he's talking as if he were back in Odawara during his first meeting with Masamune, and as if, should he defeat him this time, then his failure will be reset and he could be recognized again by Hideyoshi and Hanbe as the former's real "Left Arm"...Masamune notices it too and feels pity since he's clearly off his rocker at this point.
When Katsuie kills Nagamasa in Oichi's story. Oichi sees his dead body and goes insane with anger, manifesting an authoritative voice not unlike her husband in a stark contrast to her normal fragile tone. Katsuie's dialogue with Oichi during this is heartbreaking as he begins to realize that Oichi will never be his, dead love rival or not.
Mitsunari's drama ending. After killing Ieyasu for his betrayal, he picks him up and carries him off. Its seems as though Ieyasu wasn't delusional in saying that he and Mitsunari were once friends.
Ieyasu's drama route. Hideyoshi has just defeated Matsunaga and has him right where he wants him - above the ground. Matsunaga retaliates with a suicide nuke from point blank range that turns Hideyoshi into an overcooked corpse. Keiji watched this first hand and is completely distraught with what just happened. Ieyasu is also deeply distressed from what he saw unfold.
If you kill both Hideyoshi and Hisahide before Keiji can arrive in the Toyotomi Reminisce Struggle, Keiji lets out a pretty soul-crushing cry off-screen and says that he couldn't do anything. You don't feel very proud of yourself for doing it afterwards.
Season 2 pretty much made anything and everything involving Keiji a tearjerker:
Keiji ends up fighting Toshiie to prevent the Maeda Clan (who have allied with Toyotomi) from conquering Kenshin's land of Echigo and extending Toyotomi's influence. Keiji wins, but the victory isn't satisfying at all, leaving Toshiie critically injured, Matsu crying and Keiji struggling to hold back his own tears.
Keiji pleading with Hideyoshi in the penultimate episode to stop the war he's waging and turn back to the way he used to be. Hideyoshi not only ignores him, but runs him over with his horses. Keiji lies on the ground for the remainder of the season.
In Hideyoshi's dying moments, he, Keiji and Hanbe (who died earlier) meet up in a sort of Dream Land and enjoy the breeze together. Hideyoshi goes on to explain why he did what he did - Keiji's the only person he knows who can live freely in happiness, and not everyone can live that way. So he believed he had to forsake everything weak in order to find strength - including his feelings and his past. But it turned out he was a bit of a hypocrite - Keiji's charm, which belonged to Nene and went missing a few episodes back, was actually given to Hideyoshi by Yumekichi and he had been holding onto it ever since. Even during his battle with Date. When the cause that he killed Nene for was about to die along with him, he told Keiji that he was no longer worthy of having it and somehow passed it onto him even though they were kilometers apart from each other, believing that his lover's charm was better in Keiji's hands. Keiji sheds a Single Tear as the charm appears in his hand, and calls him a stubborn fool before he finally passes away.