Oral leiomyoma are rare neoplasms of the oral cavity. Ossification within leiomyoma is not unusual but is mostly reported in leiomyoma of the deep soft tissue. Ossifying leiomyoma is extremely rare in the head and neck. We identified a total of three cases of extensively ossified leiomyoma in the head and neck in the literature including lesions in the lateral pterygoid muscle and orbit. To the best of our knowledge, only one case of extensively calcified leiomyoma has been reported in the oral cavity. We present two such rare cases of oral leiomyoma with extensive intratumoral calcifications and ossification. Ossified leiomyoma should be considered in the differential diagnosis of calcified or hard/firm soft tissue masses in the oral cavity.