Aims: Head and neck cancer predominantly affects adults older than 65 years. The goals of resection and free flap reconstruction are oncological clearance, functional reconstruction and stability for adjuvant treatment. For many elderly patients, recovery of preoperative functional status and maintaining independence are more important than life extension. This study aims to evaluate the relationship between age and postoperative functional status, focusing on care needs and length of hospital stay. Methods: We retrospectively reviewed patients who underwent head and neck cancer resection with free flap reconstruction at the Royal Brisbane and Women’s Hospital between January 2015 and December 2020. Patients were stratified by age (<65, 65–74, ≥75 years). Demographics, surgical characteristics, and changes in functional status from admission to discharge were analysed. Results: Of 200 patients, functional decline—defined as increased care needs at discharge—occurred in 16.5% (n=33), most commonly in those aged ≥75 years (60.61%, n=20). Increasing age was a significant predictor of functional decline, with patients aged 65–74 (OR 5.19, 95% CI 1.32–20.38, p=0.018) and ≥75 (OR 27.17, 95% CI 6.84–107.90, p<0.001) more likely to experience decline than those <65. Surgical factors, including ablative site, flap type, and operative duration, were not associated with functional decline. Functional decline was associated with longer hospital stay (median 19 vs. 14 days, p<0.01). Mucosal ablation and latissimus dorsi flaps increased stay by 7.97 and 8.79 days, respectively (p≤0.001). Conclusion: Increasing age was associated with postoperative functional decline in our cohort, while surgical factors influenced length of hospital stay but not functional status. These findings support the need for comprehensive preoperative counselling and proactive discharge planning to address the priorities and care needs of elderly patients undergoing major head and neck reconstruction.