The primary aim of this report was to compare urethroplasty complications for primary distal and proximal repairs with those after 1, 2, 3, and 4 or more re-operations. Prospectively collected data on consecutive hypospadias repairs (tubularized incised plate (TIP), inlay, two-stage graft) from 2000 to 2015 were reviewed. Isolated fistula closures were excluded. Extracted information included patient age, meatal location, repair type, primary vs. re-operative surgery, number of prior operations, any testosterone use, glans width, and urethroplasty complications. Pre-operative testosterone stimulation was used during the study period until 2012. Initially, it was given for a subjectively small-appearing glans, but from 2008 to 2012 use was determined by glans width <14mm. Patients initially managed elsewhere were queried for any testosterone treatment. The number of prior operations was determined by patient history and confirmed by review of records. Calibrations, dilations, cystoscopies, and/or isolated skin revisions were not considered as prior urethroplasty operations. Multiple logistic regression was performed for all patients, and for the subset of patients undergoing re-operation, using stepwise regression for the following potential risk factors: meatal location (distal vs. midshaft/proximal), number of prior surgeries (0, 1, 2, 3, ≥4), pre-operative testosterone use (yes/no), small glans (<14 vs. ≥14), surgery type (TIP, inlay and two-stage graft), and age (continuous in months), with P-values <0.05 considered statistically significant. In contrast to the 135/1085 (12%) complication rate in patients undergoing primary distal and proximal TIP repair, re-operative urethroplasty complications occurred in 61/191 (32%) TIP, 16/46 (35%) inlay, and 49/124 (40%) two-stage repairs, P<0.0001. Data regarding testosterone use was available for 1490 (96%) patients. A total of 139 received therapy, of which 65 (46%) had urethroplasty complications vs. 229 of 1351 (16%) without treatment, P=0.0001. Logistic regression in 1536 patients demonstrated that each prior surgery increased the odds of subsequent urethroplasty complications 1.5-fold (OR 1.51, 95% CI 1.25-1.83), along with small glans <14mm (OR 2.40, 95% CI 1.48-3.87), mid/proximal meatal location (OR 2.54, 95% CI 1.65-3.92), and use of pre-operative testosterone (OR 2.57, 95% CI 1.53-4.31); age and surgery type did not increase odds (AUC=0.739). Urethroplasty complications doubled in people undergoing a second hypospadias urethroplasty compared with those undergoing primary repair. This risk increased to 40% with three or more re-operations. Logistic regression demonstrates that each surgery increases the odds for additional complications 1.5-fold. Mid/proximal meatal location, small glans <14mm, and use of pre-operative testosterone also significantly increase odds for complications. These observations support the theory that previously operated tissues have less robust vascularity than assumed in a primary repair, and suggest additional adjunctive therapies are needed to improve wound healing in re-operations. The finding that even a single re-operative urethroplasty has twice the risk for additional complications vs. a primary repair emphasizes the need for hypospadias surgeons to 'get it right the first time'. The fact that 40% of the re-operative urethroplasties in this series followed distal repairs emphasizes that there is no 'minor' hypospadias. A single re-operative hypospadias urethroplasty has twice the risk for additional complications vs. the primary repair, which increases to 40% with three or more re-operations. These results support a theory that vascularity of penile tissues decreases with successive operations, and suggest the need for treatments to improve vascularity. The higher risk for complications during re-operative urethroplasties also emphasizes the need to get the initial repair correct.