A 33 year old man presented to Accident and Emergency with haematuria and intermittent left loin pain radiating to the groin. On examination he had evidence of lower limb chronic venous insufficiency. Plain abdominal radiograph was unremarkable however computed tomography (CT) urogram and subsequent CT of thorax/abdomen/pelvis with contrast demonstrated azygous replacement of the inferior vena cava with an enlarged azygous vein and multiple enlarged veins in the abdomen and pelvis. A 5.7 cm by 4.2 cm low density lesion with surrounding inflammatory change was also visualised in the left para-aortic region. Ultrasound and magnetic resonance imaging confirmed this as a thrombosed collateral of the aberrant venous web drainage. Lifelong anti-coagulation was commenced with symptomatic relief.