Background and Objectives Undifferentiated pleomorphic sarcoma (UPS) is an aggressive type of soft tissue sarcoma (STS) with high rates of metastatic disease and local recurrence. We sought to identify risk factors for local recurrence, metastasis, and overall death, and assess their impact on overall survival (OS), local recurrence‐free survival (LRFS), and metastasis‐free survival (MFS). Methods A total of 386 cases of UPS treated at our institution from 1980 to 2020 were included. Cox proportional hazards regression was used to identifying risk factors for death, local recurrence, and/or metastasis. Using the Kaplan–Meier method, we assessed OS, LRFS, and MFS. Results Sixty‐six (17%) and 121 (30%) patients with UPS developed local recurrence or metastasis, respectively. Lymph node (LN) involvement was present in 13.5% of patients. The most affected organ in patients with metastatic disease was the lungs (76.9%). Age ≥ 60 (hazard ratio [HR] = 2.42) and size ≥7 cm (HR = 1.52) were some of the significant risk factors for overall death. LN involvement was an important risk factor for both LR (HR = 2.79) and distant metastasis (HR = 5.73). Conclusions UPS displays high rates of metastatic disease and local recurrence. Using a tumor size cutoff value of 7 cm yields superior prognostic value than the standard STS T‐score thresholds. Lymphovascular invasion is an important risk factor for the development of metastasis.