With the growing popularity of the use of free flaps, surgeons may frequently encounter situations necessitating the performance of multiple free flap surgeries in a single day. Given its prolonged duration and technical complexity, concerns remain regarding their safety. This study investigated whether a single surgeon conducting multiple free flap surgeries in a day heightens the risk of complications. Patients who underwent free flap-based reconstruction from March 2002 to May 2023 were reviewed and categorized into 3 groups: one flap per day (Group 1), multiple flaps per day on the same patient (Group 2), and multiple flaps per day on different patients (Group 3). Outcomes, particularly perfusion-related complications (PRCs), were compared. In total, 1910 cases were analyzed: 1570 in Group 1, 126 in Group 2, and 214 in Group 3. Over time, the proportion of cases in Group 3 increased. Group 3 had fewer breast reconstruction cases but more lower extremity reconstructions, with a higher prevalence of chronic wounds. Although the rates of PRCs varied among groups, multivariable analysis exhibited no association of performing multiple flaps in a day with their occurrence, regardless of breast or nonbreast reconstruction. The rate of arterial insufficiency was significantly higher in group 3 compared with group 1 after adjusting for other variables. Performing multiple free flaps in a single day may not significantly increase the risks of overall PRCs. However, there appears to be a higher incidence of arterial insufficiency, emphasizing the need for careful planning and precise execution of procedures.