Chronic Urinary Retention (CUR) can be either asymptomatic or associated with lower urinary tract symptoms. There has been no report of case of CUR presented with unilateral scrotal swelling. In the present report, a 69-year-old man came with an abdominal distension and left scrotal swelling. He was initially diagnosed with ascites secondary to a possible malignancy. A diagnosis was established after a computed tomography (CT) scan was done that revealed a giant bladder distension with volume of 10.1 litres. The left scrotal swelling was resolved after catheterization was carried out. There was a possibility that the patient had inferior vena cava obstruction secondary to the huge bladder.