WARNING: Spoilers are unmarked.
- The Horseman comforting the wounded Daredevil with what passes for grief on his face.
- The senseless murder of Thomas Killian. He's already had both his parents killed, so Lady Van Tassel's beef with them was settled and came off as wholly unnecessary to kill an innocent child. It's even sadder when you look at it from the Horseman's perspective: he spared the young Lady Van Tassel and her sister despite knowing they could easily give away his position. It must have been painful even for him to be forced to do such an awful thing.
- The scene in which Ichabod confides in Katrina about the murder of his mother at the hands of his father.Ichabod: I was seven... when I lost my faith.
- Dr. Lancaster's death is both somber and tragically sudden. While not an innocent man by any means, his mounting guilt and remorse from seeing all the deaths and suffering wrought by the Horseman eventually leads him to try confessing the truth behind the Horseman's actions and the nefarious conspiracy behind it all, wanting to make things right. Sadly, Rev. Steenwyck kills him before he could truly find redemption.
- Her father and stepmother are both (supposedly) dead, and Katrina just looks so hollow and broken, having seen the former killed in front of her.
- While it in no way excuses or justifies her horrible crimes, Lady Van Tassel's backstory is rather tragic in itself. As a child, she lived with her loving parents and twin sister in a decent and apparently happy home. Then suddenly, her father unexpectedly died, and shortly afterwards, the Archers' landlord Peter Van Garrett, instead of showing compassion and mercy for the family who had served him and his own faithfully for many years in their time of need, heartlessly evicted them from their house and land, which he then gave to his relative Baltus Van Tassel and his family, leaving the Archers homeless and starving. Even worse, due to Lady Van Tassel's mother being suspected of committing witchcraft, no one in town would take the Archers in or help them in any way, and ostracized them to live in the woods. Within a year, Mrs. Archer had died herself, leaving her daughters orphaned, destitute, and fending for themselves in the woods.
- It also shows the tragedy between both Lady Van Tassel and her sister, the crone witch. Lady Van Tassel wanted revenge against Van Garrett and Baltus for stealing her family's home and leaving them to starve during their Darkest Hour and thus ruining their lives further, and sought to get it by not only killing them, but taking ownership of everything they both owned. She possibly tried to include her sister in on the plan, but her sister refused, likely after realizing or discovering that said plan involved killing innocent people who had nothing to do with their family's misfortunes. This disagreement likely led to a long estrangement between the two, which culminated in Lady Van Tassel personally murdering her sister as revenge for going against her and helping Ichabod in his investigation.
- Katrina is especially shocked at the latter, saying "you killed your own sister?" as if she can't conceive of someone being that evil.
- Poor Young Masbath, who already lost his mother before the events of the film, and his father is killed for being witness to the secret marriage. He doesn't appear to have anyone else, and can only offer himself as service to a complete stranger.
- Katrina discovers that Ichabod suspects her beloved father of summoning the Horseman and, not daring to believe he could be responsible, burns the evidence and tells Ichabod how much he has hurt her."You have no heart. And I had a mind once to give you mine. Goodbye, Ichabod Crane. I curse the day you came to Sleepy Hollow."
