Introduction: Bladder cancer is a common and serious disease globally, often requiring radical cystectomy as the preferred treatment. However, this procedure carries substantial risks and complications. To evaluate its success, pentafecta, a five-component measure, was introduced. This study investigates the attainment of pentafecta following radical cystectomy and examines factors that influence its achievement. Methodology: This retrospective, single-group study was conducted at AIIMS Jodhpur. The study population included 42 patients who underwent radical cystectomy for bladder cancer. Various data, including demographic characteristics, clinical features, surgical techniques, and postoperative outcomes, were collected from medical records. The primary outcome measure was the rate of achieving pentafecta, which comprises five parameters. Results: Out of 42 patients, 26 (61.9%) achieved pentafecta. Age, gender, comorbidities and surgical approach did not significantly affect the attainment of pentafecta. Negative surgical margins were achieved in 95.2% of cases, and adequate lymph node dissection (>16 lymph nodes) was performed in 85.7% of cases. The absence of Clavien-Dindo grade 3–5 complications and recurrence was observed in 80.9% and 90.47% of cases, respectively. Uretero-enteric stricture was absent in 95.2% of cases. Conclusion: The study emphasizes the significance of negative surgical margins, thorough lymph node dissection, absence of complications, recurrence, and uretero-enteric strictures in evaluating the success of radical cystectomy as pentafacta outcomes. Patients with higher drain output and wound infections are less likely to achieve pentafacta outcome and indicates poorer outcome. By considering these factors, clinicians can assess patient outcomes and identify areas for improvement.