Surgical treatment of the advanced tumors of the oral cavity determines challenging anatomical and functional defects of the involved districts. The aim of our study was to supply reconstructive guidelines for the surgical treatment of the tumors of the oral cavity. Indications and conclusions were drawn following a retrospective review of data of 76 patients undergone oral and oromandibular reconstruction with either pedicled (17) or free flaps (59). The analysis included for both groups the registration of type of selected flap, success rate, early and late complications rate, functional results at 6 months to 1 year, ie oral feeding recovery and quality of oral feeding. The results obtained point out that the anatomical and functional complexity of the oral cavity needs a wide armamentarium of surgical techniques and skills at prompt disposal of the reconstructive surgeon. Free flaps should be kept in mind as the first choice for middle-sized to wide defects. An extended range of options in this group are available, and the selection should be based on type and extent of the defect following surgical oncologic ablation, but also on the surgeon experience itself. Pedicled flaps should be alternatively selected on case of general, vascular or local contraindications to major free flaps surgery, for the higher complications rate and worse functional outcomes to be faced.