Pre-operative computer-aided design and manufacturing (CAD/CAM) revolutionized head and neck reconstruction after extirpative surgery. However, studies performing head-to-head comparison to the conventional technique have limited long-term follow-up. We aimed to compare short and long-term outcomes between conventional and CAD/CAM approaches for mandibular reconstruction with free fibula flaps. Patients undergoing free flap reconstruction from 2012 to 2021 were included. Data regarding patient demographics, past medical history, surgical details, complications, and reconstructive outcomes were collected. Patients who had CAD/CAM were compared with the patients who underwent reconstruction with the conventional technique. The cumulative incidence of hardware maintenance was displayed using the Kaplan-Meier method. A total of 215 patients (n=79 conventional, n=136 CAD/CAM) were included. Both cohorts had similar demographics except the CAD/CAM cohort was younger (p=0.043). The mean operative duration was 54 minutes shorter with the use of CAD/CAM (p=0.014). Total and partial flap loss rates were similar. Patients with CAD/CAM had significantly lower rates of early wound dehiscence (p=0.037). Median [interquartile range] follow-up duration was similar (931 [1854] days in conventional vs 728 [841] days in CAD/CAM, p=0.084). After excluding patients with major surgical complications in the first 30-days, CAD/CAM cohort had a lower hardware removal rate (28.8% vs 13.9%, p=0.011). The significance persisted after including only the patients with more than 2 years of follow-up. The use of preoperative CAD/CAM may reduce operative duration, while allowing for longer maintenance of hardware with reduced removal rates due to complications.