Background: Osteoradionecrosis significantly reduces quality of life. In this study, we reviewed our experience of surgically managing complicated cases of osteonecrosis and discussed the perioperative problems encountered. Methods: We retrospectively evaluated 15 patients with osteoradionecrosis of the craniofacial or trunk skeleton who underwent flap reconstruction surgery at our institution between January 2002 and December 2021. In all cases, the irradiated tissues were excised, followed by coverage with well-vascularized tissue. Surgical methods and postoperative complications were evaluated as outcomes. Results: The 15 patients included six men and nine women, with a mean age of 67.8 ± 17.0 years (range 20-83 years). The affected bone was the skull in one case, mandible in five cases, clavicle in one case, ribs in five cases, sacrum in two cases, and pubic bone in one case. In seven cases, a postoperative fistula formed in the craniofacial or pelvic region. The fistulas in the craniofacial region were closed by the removal of the infected plate or excision of the sequestrum. Conclusions: Surgical treatment of osteoradionecrosis should include excision of the irradiated tissues followed by coverage with well-vascularized tissue. Well-vascularized transplanted tissues can be effective for wound healing in complicated cases.