Objective: This study aims to evaluate the management and outcomes over 14 years at a tertiary maxillofacial surgery unit. Methods: Retrospective cohort study of patients from a Portuguese tertiary center of maxillofacial surgery with histopathologically confirmed diagnoses of chronic osteomyelitis of the jaws between January 2010 and December 2023. Demographic and clinical characteristics, treatment, and progression of the disease were evaluated. Results: Fifty-three patients were included—28 women (52.8%), mean age 55 (95% CI 5–90) years. The mandible was affected in 84.9% (
n = 45) of cases. Secondary chronic osteomyelitis was diagnosed in 88.7% (
n = 47), with medication-related osteonecrosis of the jaw (MRONJ) being the most common etiology (38.3%). Bacteriological samples were contributory in 52% (
n = 13) and 46.1% (
n = 6) were resistant to amoxicillin. All received antibiotics for a median time of 27.3 days. Surgical treatment included sequestrectomy (
n = 40, 75.5%), marginal (
n = 5, 9.4%), and segmental mandibulectomy (
n = 8, 15.1%). Clinical remission was achieved in 77.4% (
n = 41) of cases with higher success in MRONJ (
n = 15, 83.3%) than ORN (
n = 4, 57.1%). Conclusions: Almost half of the isolates were amoxicillin-resistant, reinforcing the need for susceptibility testing. Surgical management guided by etiology and disease stage remains essential, with more extensive resection needed in MRONJ and ORN.
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