Background: Virtual surgical planning has become a well-established practice in head and neck surgery. In oncological surgery, it permits the achievement of safe margins resections and ensures functional reconstructions and optimal esthetic outcomes. This study aimed to evaluate the long-term outcomes after virtually planned mandibular microvascular reconstruction, focusing on functional and esthetic results, as well as health-related quality of life. Methods: A long-term retrospective evaluation of 17 patients with oral cavity malignancy who underwent computer-assisted mandibular resection and reconstruction was performed. Functional and esthetic outcomes were analyzed using the EORTC, QLQ-C30, H&N35, and FACE-Q questionnaires. Results: Time since reconstruction ranged from 7 to 14 years. Patients reported high functional levels on the QLQ-C30 functional scales but lower scores on H&N35. On FACE-Q, patients demonstrated higher appraisal and satisfaction with their smiles compared to their overall facial appearance. Conclusions: In this retrospective case series, patients undergoing computer-assisted mandibular reconstruction for oral malignancies achieved good long-term functional and esthetic outcomes. Although limited by the small sample size, these results support the enduring benefits of virtual planning for mandibular reconstruction. To minimize declines in function and appearance, considerations should include immediate dental implants, enhanced reconstruction of the temporomandibular joint, newer methods of radiotherapy to minimize xerostomia, and oral exercises to prevent trismus.