Leiomyomas are rare, benign tumors arising from smooth muscle cells. Due to the heterogeneous anatomical locations, as well as clinical and radiological findings, early and correct diagnosis is usually tricky. The clinical symptoms depend on the anatomical structure the tumors are compromising by their growth. We present a case of a 53-year-old male patient who suffered from swelling of the right foot and ankle. Initially, arthritis and deep vein thrombosis were ruled out. As the swelling progressed to the entire leg, CT scan was performed showing a tumor compressing the right femoral vein. However, a magnetic resonance imaging (MRI) and a biopsy did not show any conclusive findings. Tumor excision was planned and immunohistochemical staining confirmed leiomyoma. The authors conclude that unspecific, progressive symptoms should prompt further investigation and whenever planning a biopsy, a possible malignant finding should be considered and excision of the biopsy canal together with the tumor must be assured.