Being a far darker take on the beloved books, there are bound to be sad moments throughout the stories.
- "Spectre" has the vengeful ghost of Dominic murder Lily’s guard (who was going to be a father) and break the mind of James’ guard by showing him something.
- "Armaments" has James revealing his reasoning on why he’s been a jerk throughout the episode as while pulling a gun back on his old line, he bumped it slightly and since it was loaded, James accidentally killed 43 workmen and caused his girlfriend Amanda to be scrapped. Even Diesel was shocked by this revelation and vows to be more careful in the future.
- Everything about The Stories of War miniseries and the many deaths that occur:
- Evacuation has 84 of Gordon’s passengers die in a bombing of High Bridge.
- Blitz has the death of Colin who had saved numerous lives by moving gunpowder vans away from Knapford. Diesel/Bruce’s reaction does not help.
- Thanks to the events of "Espionage", both Alfred and Mr. Star are killed in an explosion by the BUF.
- Lily sacrificing herself to protect Henry from an explosion in "Atrocity".
- The death of Adam in Diagnosis as he undergoes the final firing and calmly awaits his end. What really twists the knife is that Adam was the only member of his class left making it so the Wellsworth and Suddery are now extinct. At least until Brian returns.
- "Secrets" reveals why Sheffield has acted like a prat towards the other engines. While speeding, he had ran a danger signal causing him to derail. This caused his crew to suffer injures and caused the green engine to crash into a car that had someone in it causing their death. This caused Sheffield to become terrified of going fast and began to do his work at a slower pace. Whenever he’d try to explain his reasoning, the engines and staff would just snap at him. This in turn caused Sheffield to lash out and be sent place to place until he ended up on Sodor.
- The death of Andreas in "Expansion" and the ensuing fallout that follows as the engines are utterly beside themselves especially Duncan who has nothing but guilt since Andreas died saving his life. Making matters worse is that in their grief, the other engines chew Duncan out and for once, he doesn’t retort at all.
- Season 5 in a nutshell.
- Geoffrey’s death in "Vandalism" as he and crew are derailed. Making matters worse is that this was not the work of the vandals but something much more sinister.
- Avery Halifax getting run over by breakaway trucks in "Enthusiasts". Yes, he was a nuisance, but a weirdly likeable one.
- Barry’s situation in "Rescued". Due to BR’s fumbling, Barry was set to rust alongside the numerous other faceless engines for years. It’s a miracle Neil found him.
- Matthew and Neil losing their marbles due to Smokebox Syndrome.
- Basically the entirety of Revenge. To highlight the two most brutal instances:
- Peter, having finally finished serving his fifteen-year sentence in Railgate, is suddenly gunned down by the now-adult son of one of his victims, minutes after pulling his first passenger train and experiencing genuine happiness for the first time in two decades. Made worse by poor Donald having to watch helplessly as his old Middie colleague is murdered mere feet away.
- Nigel Zorro, once Director of the Sodor Middies and briefly the Controller of the entirety of what would one day be known as the NWR, is shot dead outside his own home, by Sean Creedy. Once again, one of the Scottish twins is present nearby, this time Douglas, who hears the assassination take place. Bruce put it best:
Bruce: The man survived the western front, he survived the Blitz, he survived bloody cancer, only to be gunned down by some mongrel!- The flashbacks we get is of the children who would grow up to be Robert and Sean Hall are just as sobering though one in particular stands out. Occurring right after the Flying Kipper Incident, it’s revealed how ruthless Mr. Zorro could be back then as he refuses to give Angela, who is Robert’s mother, any more money after discovering some discrepancies in her husband’s records. This causes their house to foreclose and Angela to kill herself, leaving the children to be adopted by the abusive Gregory Hall.
- The last scene of "Munitions".
- The confirmation in "Fallout" that Thomas died from his injuries.
- Mickey's Heroic Sacrifice to protect Donald from an explosion, eerily mirroring Lily's death.
