Hemosiderotic Fibrolipomatous Tumor (HFLT) and pleomorphic hyalinizing angiectatic tumor of soft parts (PHAT) are rare, locally aggressive neoplasms with overlapping morphological and immunohistochemical features. HFLT is a recently described neoplasm whose cytological features have not been widely described in the literature. We present the cytological and histopathological features of this case because of its rarity and the intermediate features exhibited in this tumor, suggesting a continuous spectrum of tumors of uncertain differentiation, which includes both HFLT and PHAT. A 29 year old female presented with a painful swelling over the dorsum of foot for 1½ months. FNA of the swelling showed features of a spindle cell neoplasm with marked pleomorphism, cytoplasmic pigment, intranuclear and intracytoplasmic inclusions. A possibility of a sarcoma was given. Histopathological examination of the excised specimen showed features in favor of a soft tissue tumor of intermediate malignancy of uncertain type. Immunohistochemistry showed immunoreactivity for CD34 and negativity for CD31, S-100, HMB-45, Melan-A and pancytokeratin. These findings favoured the possibility of a HFLT. An early PHAT was also considered owing to considerable overlap seen in these two tumors.