Chondroblastoma is a benign bone neoplasm, which usually presents in the epiphysis of long bones, but can occur in unusual locations. This report describes the clinical, radiologic, and cytologic features on FNA of two chondroblastomas of the temporomandibular region that were only recognized by histopathologic study. This emphasizes the diagnostic pitfalls of this entity and expands the cytologic differential diagnosis of tumors of the parotid region.