Mesenchymal chondrosarcoma (MC) is an uncommon tumor with an aggressive behaviour. We present two cases of MC. The first one is a unique case of MC of the maxilla metastasized from the clavicle. The second describes MC in the mandible with extensive involvement of the condyle. A 31-year-old male and a 22-year-old male presented to Saveetha Dental College, with a 2-month history of progressive mass in left posterior maxilla and a firm swelling in the right mandibular region, respectively. Incisional biopsy of both the cases revealed characteristic bimorphic pattern composed of sheets of undifferentiated round and spindle cells along with areas of chondroid matrix of variable cellularity. Histopathological features were suggestive of MC. These type of neoplams show local aggressive behaviour with high metastatic and recurrence potential due to which the prognosis of MC is poor.