Cancer-associated thrombosis (CT) is a major contributor to morbidity and mortality in patients with malignancy and remains the second leading cause of death after cancer progression itself. Patients with cancer have a markedly increased risk of venous thromboembolism, especially within the first 6 months following diagnosis and during the periods of active treatment. Over the past two decades, anticoagulation strategies for CT have evolved substantially, transitioning from vitamin K antagonists to low molecular weight heparin, and more recently to direct oral anticoagulants. Despite these advances, optimal management remains challenging due to the heterogeneity in cancer types, bleeding risks, comorbidities, and patient preferences. This review summarizes the epidemiology and pathophysiology of CT, appraised current treatment strategies, and contextualized randomized trial findings with preliminary real-world observations from a tertiary hospital in Singapore. These institutional observations are presented to provide clinical context rather than perform comparative effectiveness analyses.