Aims: The reconstruction of maxillofacial defects is inherently complex, affecting key functions such as breathing, mastication, swallowing, and speech. Virtual surgical planning (VSP) has been shown to improve surgical efficiency and reconstruction accuracy; limited research has examined its impact on health-related quality of life (HRQOL) or orofacial function. This study aimed to compare HRQOL and functional outcomes in patients with maxillofacial defects treated using VSP technology versus conventional or freehand techniques. Methodology: This retrospective comparative cohort study included 61 patients who had undergone bony free-flap reconstruction of a maxillofacial defect at two sites: Royal Brisbane and Women’s Hospital and Gold Coast University Hospital. Patients were assessed at least 12 months postoperatively using the Performance Status Scale for Head and Neck Cancer (PSS-HN) and the University of Washington Quality of Life Questionnaire (UW-QOL). Baseline patient characteristics and details regarding their dental rehabilitation were also collected for analysis. Results: VSP was not associated with improved HRQOL or better functional outcomes in domains including diet, eating, or appearance (p > 0.05). Conversely, dental rehabilitation, independent of VSP, was associated with significantly higher scores for public eating (p=0.01) and overall PSS-HN score (p=0.01), as well as chewing (p=0.03), taste (p=0.04), and saliva (p<0.01) on the UW-QOL. Conclusion: As VSP is increasingly utilised in the reconstruction of maxillofacial defects, it is imperative that we continue to consider the potential costs and limitations of this technology. Although VSP has clear utility in optimising reconstructive accuracy for complex defects, the results of this study suggest that well-planned and delivered dental rehabilitation (facilitated by endosseous dental implants) is likely to provide greater benefit to patient function and overall HRQOL.