Donald W. Winnicott has considerably referred to adolescence in his work, which involves very rich theoretical hypotheses. However, it won't be wrong to say that the writer has collected his writings on adolescence in two of his papers. The first one of these papers, “Adolescence: Struggling through the doldrums” was given as a conference in 1961. Winnicott's second speech on adolescence was in 1968. This speech was published with two separate titles: “Contemporary concepts on adolescent development” and “Adolescent immaturity”. In both of these papers, important and problematic aspects of adolescence are discussed comprehensively. Here in this paper, we'll discuss Winnicott's views on adolescence based on these two major papers.