To report outcomes of percutaneous ureteroplasty and stenting of anastomotic ureteral strictures which occurred within 1 year of urinary diversion (ureteroenteric anastomosis -UEA) or renal transplantation (ureterovesical anastomosis-UVA). We retrospectively identified patients who underwent ureteroplasty with percutaneous nephroureteral (PCNU) or double pigtail ureteral stent placement (stent) for benign anastomotic strictures occurring within one year of urinary diversion or renal transplantation from March 2004 to July 2016 (N = 54). 31 patients had UEA strictures (25 men and 6 women; mean age 65, 19 ileal conduits and 12 continent diversions) and 23 renal transplant patients had UVA strictures (15 men and 8 women; mean age 53). Mean follow-up was 31 months (range, 1.107 months). Primary endpoint was freedom from ureteral stent or nephrostomy without the need for surgical revision (i.e., tube free). Mean balloon diameter used for ureteroplasty in the urinary diversion and renal transplant cohorts was 7.7 mm and 6 mm, respectively (p < 0.01). Mean French size of PCNU or stent placed after ureteroplasty was 10 French. In the UEA group, 8/31 (25%) patients underwent surgical revision and 18/31 (58%) required chronic ureteral stents after failed ureteroplasty. Only 5/31(16%) were tube free without surgery. In the UVA cohort, 2/23 (8%) patients underwent surgical revision and 9/23 (39%) required chronic indwelling ureteral stents after failed ureteroplasty. 12/23 (52%) renal transplant patients were tube free without surgery. By Kaplan Meier analysis, the actuarial mean time to PCNU or stent removal was 81 ± 10 months and 41 ± 11 months for UEA and UVA respectively (p = 0.01). Ureteroplasty had greater success in achieving the primary endpoint of freedom from PCNU or ureteral stent in patients after renal transplantation as compared with patients after urinary diversion.