Spoilers Off applies to all "Moments" pages. Proceed at your own risk.
Examples in Both Versions/Original Examples
Hitomi's backstory and her experiences with babysitting a young Giorno (known as Haruno at the time) on request of his mother Shiori, which is told over the course of several chapters. It's already somber enough that Shiori's neglect and abuse had taken some of its toll with how aloof Giorno is for his age. Then said abuse becomes gradually clearer to Hitomi, from noticing bruises while giving him a bath, learning of his fear of the dark, to seeing it fully come to light that same night when Shiori comes back to pick him up, where she witnesses her abuse firsthand.
After a failed asking of her parents for help, this is what causes her to hatch her plan to take him away and flee to her relatives in Morioh to raise him there...which is Doomed by Canon. It comes to a head when Hitomi decides to back out of the plan after realizing she didn't consider his feelings from seeing Giorno cry from being separated from his mother, making Hitomi realize she was so caught up in her desire to help Giorno and to spite Shiori.
Once Shiori arrives back at her home, Hitomi snaps and attempts a Calling the Old Woman Out, which ends up failing miserably as Shiori proceeds to Break Her By Talking and even Bitch Slap her in retaliation, which ends in Hitomi running out of the Shiobana house and then a Stress Vomit as she breaks down. That night spritually hurt Hitomi so much that it's what lead to her being Delicate and Sickly to the point of near-death at the start of the story. Even after that, she later mentions that she still felt bad about her attemped plan to flee with Giorno.
Jotaro's expanded backstory in chapter 42 of the original version, which talks about Jotaro's life in and outside of high school prior to the story's events, is a pretty sad story.
For one thing, at school he was resented by his classmates just for being better than them, sticking out when Jotaro didn't intend to, and being half-American to the point where they spread nasty rumors about him. A female student he took a blow for from some delinquents even rejected his help because of his heritage. Despite all that, he didn't fight back since he wanted to be the perfect kid for his mother and not worry her. However, even two of his teachers would pick on him, them being Ms. Shiobana, and his Social Studies teacher Mr. Okamoto, who singled Jotaro out and tore off the chain from his uniform the first day he decided to wear it, which was the same day he got pelted with an egg from Tabasaki.
For outside of school, Jotaro ends up finding out that his father Sadao seemingly cancelled some Mother's Day plans with his family because of his band, only for Jotaro to find out that he was seemingly cheating on Holly with Ms. Shiobana instead. Despite that, he doesn't tell Holly about it, but he becomes more distant from his father as a result. Despite his father's explanation that Shiori was just a friend and she tried to make advances on him despite him being married and how he wanted to end their friendship the day Jotaro found him, Jotaro's still upset that he kept her a secret from the family. Later on, Shiori even tries to make an advance on Jotaro, which Jotaro responds with some Tranquil Fury about how she should stay away from his father. Essentially, it's not just Hitomi whose life was negatively affected by Ms. Shiobana.
As time went on, his frustrations from his harassment at school begin to build up, which is when Jotaro starts smoking in secret to relieve stress. Only Holly knows, but continues to dote on him anyway much to his annoyance. Jotaro's frustrations finally boil over when Holly steps in to protect Jotaro from being picked on by Tabasaki and other delinquents, where Tabasaki shares a false rumor about Holly cheating on Sadao and teases about making an advance on Holly. This finally causes Jotaro to snap and he delivers a No-Holds-Barred Beatdown on Tabasaki before Holly stops him. This nearly results in Jotaro's explusion, and it takes Holly begging the headmaster to let him stay (but not without a one week suspension), but this was the event that led to Jotaro losing his status as an honors student. While it's an expansive way to explain why Jotaro is the way he is at the start of the story, it's so sad because of what he strove to be at the start and all the hardships that came with it.
The epilogue takes the cake for how the story has a Bittersweet Ending. It opens with what everyone did after they went home following the events in Cairo, and then the deaths of Avdol, Iggy, and Kakyoin, doubling both as Dies Differently in Adaptation and a harsh subversion of Spared by the Adaptation. How upfront the story is about this can hit pretty hard, especially with how Kakyoin's death hit Hitomi the hardest thanks to the bond they developed over the course of the story. To top that all off, Jotaro and Hitomi ended up growing apart, but it's remedied by the Time Skip showing Hitomi on her way to meet him in Morioh again.
7th Stand User Version Examples
The small scene of Utah challenging Vins at the end of chapter 7 can be a sad sight on its own knowing that he's Doomed by Canon to become a zombie.
Then there's Utah's death. In addition to how he Dies Differently in Adaptation, it's played more tragically than in the game. Once he regains a bit of his sentience, he uses it to commit suicide with his Stand. It's enough for Hitomi to cry his name in anguish and she's reduced to a crying mess once he's gone. Joseph comforts her, understanding her pain, and there's an extra heart tug with how it's implied to be because of his experience with Caesar's death in Battle Tendency.
The deaths of Stroheim and Speedwagon at the ruins of Aswan in chapters 36 and 37. While Stroheim is Killed Offscreen, just hearing Freu mention he killed someone matching his description is enough to make Joseph shake with rage. Then comes his final interaction with Speedwagon after Vins mortally wounds him. While Joseph sheds only Manly Tears this time, his sorrow about the situation is very clear as he makes his last exchange with Speedwagon, followed by his thoughts after the group escapes the Collapsing Lair.
Speedwagon: I still can't believe I discovered oil and then started a vast foundation! Even though I never met you before... You're like a family to me. Joseph: ...We were a family before. You and Granny Erina raised me. Speedwagon: I did...? Then I did a wonderful job.
Rewrite Version Examples
Tina revealing herself to have trained and been infatuated with Polnareff back when he had a flesh bud in him makes for a surprisingly sad twist, as Tina recalls that she admired Polnareff's honor, and it made him the only one of Dio's servants to have treated her as a warrior despite her gender. As a result, she sees his freedom from Dio's control as the death of the man she was in love with. While Polnareff refutes it and finishes her off, their last exchange is pretty sad as Polnareff even feels somber about her death.
Tina: You left me behind...why didn't you bring me along? Tina collapsed on the ground and instantly died. Polnareff kneeled next to her and stared at her, his own heart filled with sympathy for the poor woman. Polnareff: Au revoir...
