We report an unusual case of hemangiopericytoma-like dermatofibroma in the right shoulder of an 82-year-old patient with a well-defined nodular growth located in the dermis. Microscopic study revealed a band of haphazardly arranged cells with a vascular component of gaping, simple, endothelial-lined vascular structures with intervening postcapillary venules and capillary-sized slit-like “staghorn” vascular channels filled with erythrocytes; abundant mast cells were also observed. The neoplasm cells were positive for CD68 and Factor XIIIA and negative for CD34. Few data have been published on the presence of abundant mast cells (tryptase and CD117 positive) in these neoplasm. The differential diagnosis of this entity should consider other spindle cell neoplasm, including hemangiopericytoma/solitary fibrous tumor, dermatofibrosarcoma protuberans, myopericytoma, angioleiomyoma, amelanotic melanoma, pecoma, and benign and malignant peripheral nerve tumors. We present an infrequent case of dermatofibroma with a vascular pattern resembling hemangiopericytoma and the presence of abundant mast cells, which may be responsible for this vascular component.