Objectives The aim of this study was to identify patient- and treatment-specific independent risk factors for the recurrence of proximal fibular tumors and complications of their surgical management. Methods Patients who underwent surgical treatment of proximal fibular tumors at our institution from 2004 to 2015 were retrospectively reviewed. All patients had a pathologically confirmed diagnosis and were followed up for at least 12 months for recurrence and complications. All patients were evaluated with respect to seven patient-, disease-, and treatment-specific variables. Results In the univariate analysis, peroneal nerve palsy at presentation and malignancy were associated with an increased risk of recurrence, iatrogenic peroneal nerve injury, and wound healing problems. The multivariate analysis showed that peroneal nerve palsy at presentation was an independent risk factor for recurrence and iatrogenic peroneal nerve injury and that malignancy was an independent risk factor for wound healing problems. Conclusions Peroneal nerve palsy and malignant potential are independent risk factors for complications of surgical treatment of proximal fibular tumors. The recognition of these factors may contribute to proper management and help to prevent recurrence and postoperative complications.