May-Thurner syndrome (MTS) is an underdiagnosed cause of lower limb deep vein thrombosis (DVT). The clinical prevalence of MTS-related DVT is likely underestimated, particularly in patients with other more recognisable risk factors. MTS is classically described in females between the age group of 20-50 years. In patients with acute iliofemoral thrombosis, medical treatment with anticoagulation alone has been associated with higher risk of postthrombotic syndrome (PTS) and lower iliofemoral patency rates, as compared to endovascular correction. We describe a case of MTS-related extensive iliofemoral DVT occurring in a middle age male who presented with acute onset of left lower limb swelling and pain, complicated by pulmonary embolism. Doppler compression ultrasonography of the left lower limb showed partial DVT extending from the left external iliac to the popliteal veins, and contrasted computed tomography (CT) of the thorax abdomen and pelvis established features of MTS, together with right pulmonary embolism. He was started on low molecular weight heparin (LMWH) and then underwent left lower limb AngioJet pharmacomechanical thrombolysis/thrombectomy, iliac vein stenting, and temporary inferior vena cava (IVC) filter insertion. After the procedure, the patient recovered and improved symptomatically with rapid resolution of this left lower limb swelling and pain. He was switched to an oral Factor Xa inhibitor and was subsequently discharged. After 1-month follow-up, he remained well with stent patency visualised on repeat ultrasound and underwent an uneventful elective IVC filter retrieval with subsequent plans for a 1-year follow-up.