The objective of the study was to compare the rate of complications and the functional outcomes following reconstructive surgery with pedicled and free flaps for recurrences after laryngeal cancer treatment. A retrospective analysis was conducted among the clinical records of the Department of Otolaryngology Head Neck Surgery of the University of Pavia from January 1995 to December 2004. Twenty-three patients were identified as having been reconstructed with pedicled or free flaps for hypopharyngeal recurrences after laryngeal cancer treatment. We observed a higher rate of postoperative complications after pedicled flaps (60%) than free flaps reconstructions (23%). The pedicled flaps group evidenced a longer hospitalization time (35 versus 14 days); a lower rate of patients with pedicled flaps (14% versus 69%) was able to resume a normal feeding 1 year after surgery; no patient achieved an esophageal voice, but the entire free flaps group reached an intelligible voice with the positioning of a voice prosthesis. The possibility to achieve such functional results in this kind of patient justifies the use of a surgical approach that generally requires a longer operation time than pedicled flaps, and the need for a surgical team with special skills in microsurgical techniques.