The Article is a part of a broad historical and literary problem of ‟Chekhov and his literary environment”. The paper under discussion is devoted to a comparative study of dramaturgical methods used by playwrights of the turn of the XIX‒XX centuries and the determination of the vector of the writers’ artistic search. The research subject is the system of structural and typological features such an element of dramaturgical methods as plot in the plays ‟The Cherry Orchard” by A. P. Chekhov, ‟Redemption” by I. N. Potapenko, “The Work of Life” by N. I. Timkovsky and ‟The Question” by A. S. Suvorin, the methods affiliation with a certain type of dramaturgical system (classical and ‟new drama”). The aim of the investigation is analysis of the features of the structure of the plot in selected plays, comparing them with the principles of classical drama and ‟new drama”, and comparing the findings among themselves. The main method used in the paper is the method of structural and typological comparison. The ideological and thematic unity of the plays, the interconnection of some motives, plot elements are revealed. It is proved that of all the plays considered, only the plot of Suvorin’s play ‟The Question” corresponds to the principles of classical drama, while elements of decentralization are already observed in it due to a certain independence of the secondary plot lines. The plot models of the plays ‟The Atonement” by Potapenko and ‟The Work of Life” by Timkovsky occupy an intermediate position between the classical and the ‟new drama”. In both plays, an ‟inner plot” appears. Unlike the aforementioned playwrights, Chekhov's plot model is fundamentally different from classical drama. The main principle of the organization of the plot of ‟The Cherry Orchard” is the decentralization of plot lines. The most important is the internal plot: a person in the flow of time. In addition, all the plays are united by an invariant plot reflecting the Russian reality of that time, connected with the fate of the noble estate mortgaged for debts.