Purpose: The purpose of this cross sectional study was to evaluate the health-related quality of life of patients following maxillectomy and to compare obturation and free flap reconstruction. Patients and Methods: At the Regional Maxillofacial Unit in Liverpool, United Kingdom, between 1992 to 1996, 39 patients underwent maxillectomy for malignant pathology. Of these patients, 28 (10 underwent obturation and 18 underwent free tissue reconstruction) completed a postoperative semi-structured interview. Eight questionnaires were used to test aspects of health-related quality of life and function. Results: The main findings were the associations between the size of maxillectomy defect and the University of Washington activity ([minus ]0.53; P = .005) and recreation ([minus ]0.70; P [lt ] .001) domains, and with the physical functioning ([minus ]0.58; P = .001) and quality of life ([minus ]0.51; P = .007) domains of the European Organization for Research and Treatment of Cancer questionnaire. No statistically significant differences were seen between the obturator and free flap groups. Borderline trends were for obturator patients to be more concerned about their appearance, to have more pain and soreness in their mouths, to be more aware of their upper teeth, more self-conscious and less satisfied with their upper dentures, and less satisfied with function. Conclusion: Similar subjective outcomes were found for both groups, and a larger longitudinal study is needed to test these relationships more rigorously.