Background: The desire to ensure prolonged survival for patients with advanced gynaecological cancer is a key concern for every doctor. This study presents an analysis of outcomes from an Estonian regional cancer center, evaluating prognostic factors associated with locally advanced gynecological cancer and the potential for long-term survival following pelvic exenteration. Methods: The study included patients with resistant or recurrent gynecological cancer. The analysis present data on all 34 cases in which pelvic exenteration was performed at the Tartu University Hospital. The majority of patients (88.2%) had tumour recurrence. Thirteen patients (38%) had previously undergone surgery for gynaecological cancer. Results: Of the 34 patients, 21 (62%) underwent total pelvic exenteration and 13 (38%) exenterations with vulvectomy. The median age of the study cohort was 59 years (range, 34–80). The median duration of surgery was 4.4 hours (range, 121–530 minutes). The median blood loss was 707 mL (range 100–2500 mL). The median tumor diameter was 7 cm (range 2–25 cm). The mean follow-up was 52 months. The overall postoperative complication rate was 41%. One patient died postoperatively (2.9%). Median survival for ovarian cancer was 48.3 months, cervical cancer 31.6 months, vaginal or urethral cancer 29.2 months and for endometrial cancer 7.7 months. Overall survival rates were 62% at 1 year, 44% at 3 years, 28% at 5 years, and 15% at 15 years. Multivariable analysis showed that distant metastasis (p = 0.0002), endometrial cancer (p = 0.0096), resection line (p = 0.017) were the most important factors affecting long-term survival. Conclusions: In the present study, we found that patients with relapsed or persistent locally advanced cervical, vaginal, or ovarian cancer who underwent pelvic exenteration demonstrated substantially better survival outcomes than patients with endometrial cancer, particularly those with aggressive histologic subtypes and multiple unfavorable prognostic markers.