To evaluate and compare the outcomes and complications of three different surgical techniques for treating primary proximal hypospadias with ventral curvature (VC) ≥30°, we retrospectively reviewed the medical records of patients who underwent primary repair of proximal hypospadias with VC ≥30° after degloving at Beijing Children's Hospital Affiliated to Capital Medical University (Beijing, China) from January 2019 to January 2021. A total of 152 patients were divided into three groups: transverse preputial island flap (TPIF) combined with Duplay, modified Koyanagi, and staged TPIF, which were performed on 55, 16, and 81 patients, respectively. A total of 39 (25.7%) patients had complications. Complications rates were similar for the TPIF combined with the Duplay group (40.0%) and modified Koyanagi group (50.0%) but lower for the staged TPIF group (11.1%; P < 0.01). The incidence of urethrocutaneous fistulas was significantly higher in TPIF combined with Duplay group (21.8%) compared to staged TPIF group (4.9%; P = 0.01). In univariate analysis, the length of the urethral defect was the single factor that could predict complications; the cutoff was 4.55 cm. More patients in the long urethral defect group than in the short one had complications (34.1% vs 15.7%, P = 0.01). These results indicate that staged TPIF produced a better outcome, whereas more patients in the TPIF combined with Duplay group presented with two or more complications.