Background and Objectives: Remimazolam is a recently introduced benzodiazepine that has been increasingly adopted as an alternative to propofol. Although several trials have compared remimazolam with propofol, these studies have primarily focused on induction-related hypotension in non-gynecologic settings. To the best of our knowledge, both intraoperative hypertension and hypotension have not been systematically evaluated throughout the full anesthetic course in the specific physiologic context of robot-assisted laparoscopic gynecologic surgery performed in the steep Trendelenburg position with pneumoperitoneum. Materials and Methods: In this retrospective study, propensity score matching was performed to minimize selection bias. The demographic data of 694 patients, along with the incidence of intraoperative hypertension and hypotension, were collected through a review of medical records. Results: A total of 694 patients met the selection criteria, all of whom underwent total intravenous anesthesia (TIVA) using either remimazolam (n = 321) or propofol (n = 373). After propensity score matching, 317 pairs were analyzed. The incidence of intraoperative hypertension was higher in the remimazolam group (66.2% vs. 52.1%; p < 0.001), whereas hypotension was more frequent in the propofol group (12.0% vs. 5.4%; p = 0.003). Conclusions: TIVA with remimazolam was associated with a higher incidence of intraoperative hypertension compared to propofol, whereas propofol was more likely to cause hypotension in patients undergoing laparoscopic gynecologic surgery.