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Despite the advent of robotics and the decreasing rate of complications after radical cystectomy, several factors are renowned to impair the early outcomes of this procedure. The aim of this paper is to provide a multivariate analysis (MVA) of patient and surgical procedure-related variables likely to affect postoperative course and 30-day complication rate. Fifty-five robotic-assisted radical cystectomies (RARCs) performed at a single center from July 2021 to March 2023 were enrolled. Baseline demographics, comorbidities, and intraoperative and postoperative data were collected. Uni- and multivariate analyses were performed to evaluate the relationship with Clavien ≥ II complications arising within 30 days of surgery. A postoperative Clavien ≥ II complication was evident in 15 patients (28%), whereas Clavien ≥ III occurred only in 5 (9%). At MVA, the only independent predictor of Clavien ≥ II complications was a prior neoadjuvant chemotherapy (OR 5.6; 95% CI 1.22-25.3, p = 0.026). Recognized the small sample size, patients who received a prior NAC should deserve special care within the postoperative course.