Type 2 diabetes mellitus is a major concern globally and well known for increasing risk of complications. However, diabetes complications often remain undiagnosed and untreated in a large number of high-risk patients. In this study based on claims data collected in South Korea, we aimed to explore the diagnostic progression and sex- and age-related differences among patients with type 2 diabetes using time-considered patterns of the incidence of comorbidities that evolved after a diagnosis of type 2 diabetes. This study compared 164,593 patients who met the full criteria for type 2 diabetes with age group-, sex-, encounter type-, and diagnosis date-matched controls who had not been diagnosed with type 2 diabetes. We identified 76,423 significant trajectories of four diagnoses from the dataset. The top 30 trajectories with the highest average relative risks comprised microvascular, macrovascular, and miscellaneous complications. Compared with the trajectories of male groups, those of female groups included relatively fewer second-order nodes and contained hubs. Moreover, the trajectories of male groups contained diagnoses belonging to various categories. Our trajectories provide additional information about sex- and age-related differences in the risks of complications and identifying sequential relationships between type 2 diabetes and potentially complications.