May‑Thurner Syndrome is a rare vascular disease in which the right common iliac artery compresses the left common iliac vein. It oc curs 5 times more often in women than in men, usually in their 20s and 40s. Patients suffer from deep vein thrombosis, post‑thrombotic syndrome, and pulmonary embolism. They usually present with swelling of the left leg, chronic leg pain, skin colour changes, tingling and/or numbness of the affected limb, varicosities, phlebitis, and venous stasis ulcers. Available diagnostic tests include venous duplex ultrasound, computed tomography, magnetic resonance imaging, venography, and intravascular ultrasound. Endovascular therapy, in cluding angioplasty, stenting, and catheter‑directed thrombolysis is the current mainstay of treatment. Long‑term anticoagulation and elastic compression stockings are used to prevent recurrent blood clot formation and decrease the risk of post‑thrombotic syndrome. Thrombophilia screening is essential, as it would aid in the decision‑making process regarding continuation of anticoagulant therapy. We present the case of a 38‑year‑old woman in her fourth pregnancy, presenting with persistent left leg oedema and recurrent deep vein thrombosis, eventually diagnosed with May‑Thurner Syndrome. JRCD 2018; 4 (1): 22–25