Chondrosarcoma is a malignant neoplasm that results in abnormal bone and cartilage growth. Although Chondrosarcoma is rare, it is the second most common primary bone malignancy. Mesenchymal Chondrosarcoma (MCS) is a rare histological variant of Chondrosarcoma (CS) that accounts for only 1% of all CS and has high predilection for the head and neck region with a peak incidence in 2^nd and 3^rd decade of life. There is comparable male to female ratio with two thirds of the cases arising from bone and one third from soft tissue. The tumor is unique because of its aggressive growth with a high tendency for late recurrence and delayed metastasis. We present a case of this highly malignant lesion arising from the infratemporal fossa and rapidly involving maxillary tuberosity and mandibular ramus.