BackgroundFree tissue transfer has fundamentally changed head and neck surgery, enabling reliable reconstruction of large defects with better function and aesthetics. This study assesses two decades of trends in free flap reconstruction, and how disease incidence, survival, surgeon caseload, team approach, and technology have impacted practice.MethodsRetrospective analysis of 1027 head and neck free flaps from 2006 to 2022. Outcomes examined include chronological changes in flap selection, indication, length of stay, incorporation of virtual surgical planning (VSP), annual caseload, survival, and their associations with the single versus multi‐team approach.ResultsThere were 764 soft‐tissue and 263 osseous reconstructions utilizing 21 different flaps. Anterolateral thigh and radial forearm accounted for 76.7% of soft tissue flaps, with recent increase in superficial circumflex iliac perforator flaps in young patients. Osseous flap proportion remained stable, but fibula flaps increased five‐fold with more VSP, dental implants, oral cancer, and multi‐team surgery. Outcomes such as complication rates, length of stay and disease specific/overall survival have improved over time despite increasing complexity (P = 0.001, P = 0.001, P < 0.001, and P < 0.001, respectively). However, there was no significant difference in operative time, complication rate, or disease specific/overall survival between single team or multi‐team approaches (P = 0.45, P = 0.054, P = 0.57, and P = 0.60, respectively).ConclusionSingle and multi‐team approaches may have similar fundamental outcomes, but as caseload, complexity, and life‐expectancy increases, both patients and surgeons benefit from a collaborative multi‐team approach that focuses on improving long‐term functional outcomes.