Leiomyosarcoma is characterized by its aggressive behavior, poor prognosis, resistance to chemotherapeutic drugs, and high recurrence rate. This study aimed to identify prognostic factors affecting the effectiveness of cytoreductive surgery (CRS) on overall survival (OS) in patients with recurrent leiomyosarcoma (LMS). A retrospective analysis was conducted at Başkent University Ankara Hospital from 2007 to 2016, involving 59 patients with uterine LMS who underwent surgery. We assessed demographic and clinical variables, disease recurrence intervals, and treatment outcomes. The median age of the patients was 50.0 (23-78) years, and the median follow-up time was 25.0 (2-87) months. Median disease-free survival (DFS) and OS were 15.0 and 37.0 months, respectively. Disease recurrence occurred in 44 patients (74.6%). After recurrence, 34 (77.3%) patients underwent CRS and chemotherapy (CT), while 10 (22.7%) patients received only CT. The median OS was 19.0 months for patients who underwent CRS and received CT and 15.0 months for those who received only CT (p = 0.132). Notably, OS was significantly longer for patients whose recurrence occurred after 6 months compared to those with early recurrence (19 versus 8 months, p = 0.049). CRS provided a modest survival benefit for patients with recurrent LMS, although statistical significance was not achieved. The results of this study indicate that the timing of recurrence plays a crucial role in survival.