Objective To investigate the role of port-site bupivacaine hydrochloride injection in laparoendoscopic single-site surgery (LESS) as a means of postoperative umbilical pain alleviation. Methods A total of 200 consecutive patients who underwent LESS from October 2018 to February 2019 were included in this randomized prospective case control study. The patients were alternatively assigned to either the study group (0.25% 10-mL bupivacaine hydrochloride injection at the 1.5-cm umbilical incision site after surgery) or the control group (no injection). All patients underwent surgery at the National Health Insurance Service Ilsan Hospital under the same operational setting by 3 board-certified gynecologists. Postoperative umbilical pain scores assessed using the visual analog scale were compared between the 2 groups as the primary outcome. Student's t-test, χ 2 test, and a linear mixed model were used for the statistical analysis. A P-value of <0.05 was considered to be statistically significant. Results The patients' age, body mass index, and menopausal status; type of surgery performed; and need for additional trocar insertion exhibited a significant difference between the bupivacaine injection and non-injection groups. After adjusting for various confounding variables, the postoperative umbilical pain scores measured at postoperative 2-3 hours, 6-10 hours, 1 day, and 3 days did not exhibit a significant difference between the 2 groups. Conclusion Port-site bupivacaine injection in LESS did not show any additive effect in alleviation of postoperative umbilical pain.