Squamous cell carcinomas are often seen on the sun-exposed areas of the skin and are rarely observed on the digits of the foot. However, there have been incidences of squamous cell carcinoma developing in the presence of chronic wounds with osteomyelitis, thus complicating the treatment. We present a patient with osteomyelitis who developed invasive squamous cell carcinoma of the third digit. We conclude that wounds with osteomyelitis may have underlying pathologic abnormalities that are not obvious on initial presentation.