Deep penetrating fibrous histiocytoma (DPFH) is a rare variant of fibrous histiocytoma that can arise in the subcutis and deep soft tissues with different clinical implications from dermatofibromas. Dermatofibromas are mainly cosmetic annoyances and do not require surgical management. However, the DPFH does require that negative surgical margins be achieved because of the possibility of local recurrence and distant metastasis. We describe a case of a 24-year-old man diagnosed with DPFH through histologic examination and immunohistochemistry. The lesion displayed diffuse, strong D2-40 positivity and a minority of cells were highlighted with factor XIIIa. The lesion was negative for CD34. The patient's lesion was incompletely excised and a repeat excision was required.