Residual urethra is a common site of recurrence in patients undergoing radical cystectomy with urinary diversion for bladder cancer. Urethral recurrence (UR) clinically manifests as a penile mass or a bloody or purulent penile discharge at a median of 13 months after surgery. And on imaging studies, it characteristically appears as a focal intraluminal mass, urethral wall thickening, or an infiltrating mass arising from the urethra. We, herein, present an unusual case of UR manifesting as a large cyst in the penile root 4 years after radical cystectomy with urinary diversion for muscle-invasive bladder cancer. Further, a complex cystic mass developed in the same location 2 years after the excision of the cystic UR. This case shows that the imaging spectrum of UR after radical cystectomy may be wider and may include cystic and complex patterns.