Oral infections and tissue defects remain significant clinical challenges, often requiring localized, sustained, and multifunctional therapeutic solutions. In this study, baicalein-loaded chitosan films were developed and comprehensively characterized as novel biomaterials for oral and maxillofacial applications. Using a 32 factorial design, nine film formulations were prepared via solvent casting, varying chitosan molecular weight and composition. Physicochemical and structural analyses (microscopy, SEM, FTIR, and XRPD) confirmed uniform drug distribution and matrix compatibility. Mechanical testing and dissolution studies demonstrated zero-order baicalein release kinetics, with controlled, sustained delivery influenced by chitosan content and molecular weight. The optimal formulation (F5: CS MMW 2%, Gel 2%) combined favorable mechanical integrity, drug release, and potent antioxidant and anti-inflammatory activities. Further evaluation on 3D anatomical models simulating bone and soft tissue defects highlighted excellent membrane adaptability, stability, and ease of handling under conditions mimicking clinical surgery. The films acted as effective barriers in guided tissue regeneration and donor site protection, with improved surgical visibility due to their baicalein-induced coloration. Biocompatibility assays confirmed the safety of the materials, while antibacterial testing demonstrated activity against Streptococcus mutans. These results support the potential of baicalein-loaded chitosan films as multifunctional membranes for regenerative dentistry, periodontal therapy, and peri-implant care. The modular formulation design provides a platform for future integration of additional bioactive agents, paving the way for personalized, advanced wound healing solutions. Keywords: baicalein; chitosan films; oral infections; drug delivery; biomaterials; regenerative dentistry; biocompatibility