Background and Objectives: Minimally invasive surgery (MIS) has recently increased its application in the treatment of gynecological malignancies. Despite technological and surgical advances, urologic complications (UC) are still the main concern in gynecology surgery. Current literature reports a wide range of urinary tract injuries, and consistent scientific evidence is still lacking or dated. This study aims to report a large single-center experience of urinary complications during laparoscopic hysterectomy for gynecologic oncologic disease. Materials and Methods: All patients who underwent laparoscopic hysterectomy for gynecologic malignancy at the Department of Medicine and Surgery of the University Hospital of Parma from 2017 to 2021 were retrospectively included. Women with endometrial cancer, cervical cancer, ovarian cancer, uterine sarcoma, or borderline ovarian tumors were included. Patients undergoing robotic surgery with incomplete anatomopathological data or patients lost during follow-up were excluded from the analysis. Intraoperative and postoperative UC were analyzed and ranked according to the Clavien-Dindo classification. Results: Two hundred-sixty patients were included in the study: 180 endometrial cancer, 18 cervical cancer, nine ovarian cancer, two uterine sarcomas, and 60 borderline ovarian tumors. Nine (3.5%) UCs were reported (five intraoperative and four postoperative complications). No anamnestic variables showed a statistical correlation with the surgical complication in the univariable analyses. C1 radical hysterectomy, a higher FIGO stage, and postoperative adjuvant treatment (p-value = 0.001, p-value = 0.046, and p-value = 0.046, respectively) were independent risk factors associated with the occurrence of UC. Conclusions: The urological complication rates in patients with oncological disease are relatively rare events in the expert hands of dedicated surgeons. Radical hysterectomy, FIGO stage, and adjuvant treatment are independent factors associated with urinary complications.