Background: The prediction of antibiotic treatment failure is helpful to identify patients with a high likelihood of needing surgical treatment early in patients diagnosed with tubo-ovarian abscess (TOA). The aim of this study was to compare the clinical characteristics of patients with TOA) who responded to medical treatment and those who underwent surgical intervention due to medical treatment failure. Material and Methods: Electronic medical records were evaluated retrospectively to identify patients who were diagnosed with TOA and hospitalized in our obstetrics and gynecology department between March 2014 and June 2019. Demographic, clinical, and laboratory data including white blood cell (WBC) count, erythrocyte sedimentation rate (ESR), and C-reactive protein (CRP) were compared between the medical treatment group and the surgical intervention group. Logistic regression was used to determine the independent predictors of treatment failure. Results: Patient age, TOA diameter, WBC count, CRP, and ESR were significantly different between the groups. On multiple regression analysis, significant correlations were identified between age ( p = 0.001), ESR ( p = 0.045), and failure of medical treatment. TOA diameter ( p = 0.065) showed a borderline association with surgical intervention. The risk group was defined as the combination of factors producing a risk score > 2. The area under the curve (AUC) for the risk group (age >34.3 years, ESR > 45 mm/h, and TOA size > 5.9 cm) was 0.844. The sensitivity, specificity, accuracy, PPV, and NPV were 93.8%, 75%, 83.3%, 75%, and 93.8%, respectively. Conclusions: The risk of needing surgical intervention in TOA patients can be predicted using ESR in addition to age and TOA size as risk factors.