Iliofemoral venous obstruction may arise from either primary compressive lesions or may be secondary to an episode of deep venous thrombosis. Regardless of aetiology, these lesions, either alone or in association with more distal reflux, may be responsible for lower extremity pain, swelling, and ulceration. Conventional surgical procedures for the treatment of iliofemoral venous obstruction have largely been supplanted by endovascular approaches relying on the deployment of venous stents. Large series have reported good technical and clinical results from venous stenting, particularly for primary lesions. However, early stent occlusions and late re-stenosis do occur. Although most of these appear related to technical factors, there is likely a role for pharmacological adjuncts in maintaining stent patency. The use of anticoagulants and antiplatelet agents is largely based on the underlying pathophysiology and extrapolation from arterial interventions, which likely are significantly different with respect to their pathophysiology and natural history. Although lacking substantial evidence demonstrating efficacy, the use of adjunctive antiplatelet agents in stents placed for primary lesions and consideration of anticoagulation for high-risk post-thrombotic lesions appears to be reasonable.