- Matthew's death. Though there's plenty of foreshadowing, it's still shocking.
- Also, Gilbert almost dying of typhoid fever in Anne of the Island. Anne's anguish can be palpably felt.
- The death of Joyce, Anne's first child who lived for less than a day.
- To add insult to injury, a few days after Anne gets a telegram from Phillipa Gordon, congratulating her.
- Walter's death in World War I.
- Even more so, his last letter. And before that his anguish over how he was afraid to enlist and thought himself a coward for it. His and Rilla's final conversation before he goes overseas is at once beautiful and tragic.
- Anne's childhood before she came Marilla and Matthew.
- In Anne's House of Dreams, the entire back-story of Leslie Moore, including seeing her brother crushed to death under a wagon, her father's suicide, marrying a horrible man so he wouldn't evict her mother, her mother's subsequent death, etc.
- In Anne of the Island, in which Gilbert professes his love for Anne and asks her to marry him and she tells him she can never love him.
- Anne's childhood friend Ruby Gillis admitting that she is aware of the fact that she is dying, followed by her death in Anne of the Island.
- Little loveable Bruce Meredith drowning his own kitten in hopes it will bring the missing in action Jem back safely. A horrifying moment by anyone's standard, when one considers this is a young child willing to kill his very favourite pet and actually believing it will make Jem return.
Tear Jerker / Anne of Green Gables