Background/Objectives: Several surgical procedures have been proposed for the treatment of hypospadias, a common and heterogeneous congenital abnormality in males. Most surgeons utilize either a urethral stent or bladder catheter for 2–14 days as a postoperative urine diversion method depending on the severity of each case and the surgeon’s preferences. The aim of the present study was to evaluate the feasibility of anterior and mid-penile hypospadias repair while placing the urethral catheter for only 20 h. Methods: A single-centre retrospective study was conducted, including all patients who underwent anterior or penile hypospadias repair from January 2012 to January 2023. All operations were performed based on the Tubularized Incised Plate (TIP) Urethroplasty. At the end of the operation, a 6 Fr 100% silicon catheter was stabilized. The catheter was removed 20 h postoperatively, and all patients were discharged on the first postoperative day. The primary endpoint of the study was the complication rate. Results: In total, 104 patients were enrolled. Eighty (76.9%) patients presented with distal penile hypospadias, while 24 patients (23.1%) had mid-penile hypospadias. The mean age at the operation was 20.8 ± 12.4 months, while the mean operative time was 114.2 ± 28.7 min. All the operations were successfully completed. During the follow-up period (mean duration 101.1 ± 44.8 months), complications were recorded in 16.3% of the patients. Conclusions: The application of 20-h catheterization seems to be an effective alternative with outcomes comparable to other conventional drainage approaches, as it reduces the discomfort of the patients without increased risk of complications.