Retrocaval ureter is a rare congenital vascular anomaly described as the passage of the ureter behind the inferior vena cava (IVC) and then turning around the IVC to attain the final lateral position. The condition is usually associated with obstruction in the ipsilateral kidney, causing different degrees of hydronephrosis and complications associated with urinary stasis, such as stone formation. Imaging has a crucial role in the diagnosis and management of retrocaval ureter. CT urography may be the procedure of choice to confirm the diagnosis and avoid retrograde ureteropyelography. Indications for treatment include flank pain, recurrent infection, hydronephrosis, and stone formation due to obstruction. Surgical management is standard and can be done through either an open, laparoscopic, or robotic approach. In this case series, we are going to see two cases of retrocaval ureter in a 56-year-old male and a 14-year-old male child who presented with a right flank of less than a couple of months duration. The first case has an associated horseshoe kidney and a solitary secondary stone. Both cases were surgically managed with open ureteral division, relocation, and ureteroureterostomy. Both have uneventful post-operative follow-ups.