Objective. To compare surgical, ultrasound guided drainage, and medical management of tuboovarian abscesses (TOA) and determine if different characteristics in patient presentation influence treatment and outcome. Methods. Retrospective cohort study of 158 patients admitted to Jackson Memorial Hospital between 2007 and 2012 with a TOA. Results. Patients treated with IV antibiotics (IV) alone were hospitalized for 5.59 days (SD 2.52), IV antibiotics and US guided drainage (IV/US) were hospitalized for 9.63 days (SD 7.58), and IV antibiotics and surgery (IV/surgery) were hospitalized for 8.14 days ((SD 3.9), ( < 0.001)). A total of 52 patients were readmitted with TOA; 41.8% were treated with IV; 26.9% were readmitted with IV/US; 7.1% were readmitted with IV/surgery ( < 0.022). Patients with a TOA measuring 0-8 cm were hospitalized for 5.97 days (SD 4.24), while those greater than 8 cm were hospitalized for 7.71 days ((SD 4.69), ( < 0.029)). Patients treated with a triple antibiotic regimen were hospitalized for 8.42 days (SD 5.70) versus 5.8 days (SD 3.24) when receiving an alternative regimen ( < 0.002). Conclusions. Longer hospitalization in patients treated uniformly with either triple antibiotics, ultrasound guided drainage, or surgery represents a delay in optimal treatment. Tailoring treatment plans based on patient presentation may allow for shorter hospital stays and improved morbidity.