Chekhov wrote four different stories that share the theme of woe and misfortune. Words denoting the theme are present in the titles of these stories, and the plots are built around it. The first story, “Woe”, was written in 1885. The second and third stories, “Other People's Misfortune” and “In Trouble”, were written in 1886. The fourth story, “In Trouble”, was written in 1887. A comparative analysis of these four stories is done for the first time. The relevance of the study lies in the novelty of the study of “trouble” in Chekhov's works. The phenomenon of trouble is widespread in the writer's works, and it has several peculiarities. This article analyses “Chekhovian misfortune” and aims to determine its unique features. The key research method is comparative analysis, which helps indicate the differences and similarities of Chekhov's misfortunes in the four stories, it helps us to better understand Chekhov's philosophy as a writer and as a psychologist. The course of the study is first studying the four stories, then conducting their analysis, and comparing them based on the results of the analysis. This study explores the creation of these stories and compares them to each other. Despite the differences in the plots of these works, common themes and motifs still can be traced. The phenomenon of disaster for Chekhov is a fundamental plot. Chekhov pays great attention to creating a unique, Chekhovian misfortune in the story “In Trouble” in 1887. This story was written after “In Trouble” in 1886, the “trouble” motif of which did not leave the writer satisfied. Chekhov unravels his thoughts of human misfortunes in distinctive context. One of the main features of Chekhovian misfortune is that the writer swiftly gets straight to the point, lets the reader see the character's misfortune and immerse into it. However, the real Chekhovian misfortune is how people treat the ones facing it. It is evident in “Other People's Misfortune”, through which the writer is trying to share his ideas about the fundamental human issues, his outlook on ethics and empathy. These problems are scrutinized in all four of the novels that are being analysed in this work. Combined together they, represent the Chekhovian problem of human relations, which in his writings often leads characters to feeling complete indifference to everything in life. The four different works are united by the moral social problem described in them. The problem consists in the lack of desire for understanding others. Grief or misfortune are not really true misfortunes for Chekhov, especially if they end happily, like in “In Trouble” (1886), but, despite the good ending, the story still has its title. Randomness or inattention to the main or secondary things in life, indifference or aimlessness of the plot gives Chekhov a position of neutrality. Chekhov does not want to evaluate and define trouble (misfortune, woe), since he alone will not be able to persuade the whole humanity of what real trouble is. So, he tried to be as as neutral as possible in relation to his characters, entrusting the reader with the task of evaluating.