Transvaginal aspiration of ovarian cysts has been advocated as a viable alternative to surgery in patients who are high-risk surgical candidates. We describe a retrospective study evaluating the results of transvaginal aspirations of benign ovarian cysts in patients at increased surgical risk, focusing on long-term follow-up for recurrence of the cyst and/or development of malignancy. Twenty-four women with ovarian cysts underwent 34 transvaginal drainages between October 1998 and December 2004. All patients were referred following diagnosis of a persistent ovarian cyst with a benign appearance on ultrasound. All patients were unsuitable candidates for surgery (history of previous pelvic surgery, n = 21; high risk for anesthesia, n = 1; and unsuitable for laparoscopy due to obesity, n = 2). Patients with a history of pregnancy, acute abdominal symptoms, or previous gynecologic malignancy were excluded. A 20G x 20 cm Chiba needle was used for transvaginal aspiration using an endocavity probe (Acuson XP, Mountain View, CA, USA; Siemens Sololine, Erlangen, Germany) and intravenous sedoanalgesia. Cysts were aspirated to dryness. Long-term follow-up of patients was performed and revealed a recurrence rate of 75%. Eighty-three percent of cysts on the left and 42% of those on the right recurred. Nine of 15 (60%) patients with recurrence required further intervention. Two of 9 underwent surgical intervention only, 4 of 9 had repeat transvaginal aspiration(s) performed, and 3 of 9 had a combination of both transvaginal aspiration and surgery. No patient developed ovarian malignancy. Transvaginal cyst aspiration has many advantages including short hospital stay, rapid recovery, excellent patient tolerance, and a low rate of procedure-related complications. Our study demonstrates that ovarian cyst recurrence following transvaginal drainage is a more significant problem than previously documented, especially if the cyst is on the left side. However, when recurrences do occur, repeat transvaginal aspirations may be considered in the symptomatic patient.