Introduction: The odontogenic cutaneous sinus tract (OCST), caused by pulp necrosis, creates connections between pathological spaces and anatomical structures. Extraoral manifestations pose diagnostic challenges leading to inappropriate treatments such as multiple surgery and antibiotic therapies. Effective management requires the treatment of dental pathology through endodontic therapy or extraction. This paper presents two cases of OCST and emphasizes the importance of accurate diagnosis and successful non-surgical endodontic treatment. Observations: Case report 1: A 23-year-old male patient referred by his dermatologist with a cutaneous sinus tract on his chin that had appeared five years ago. During this period, he reported spontaneous pain and pus discharge from the chin area. The examination revealed a periapical lesion associated with tooth number 31. Cone beam computed tomography (CBCT) revealed the existence of a localized perforation on the buccal alveolar table and a second root canal of the tooth. After six months of follow-up, the cutaneous sinus tract was significantly improved by the appropriate endodontic treatment. Case report 2: A 36-year-old female patient was referred by her dentist to examine a chin lesion that had appeared a month ago. In clinical examination and radiographic assessment, periapical lesion associated with two mandibular central incisor teeth #41 and #31 was observed. After identifying the source of infection, endodontic treatment was carried out, and a good improvement in fistula was observed after one month. Conclusions: The correct diagnosis and treatment of OCST are important for healing. CBCT aids to identify odontogenic origin of the sinus tract through the detection of apical periodontitis and bone lesion. Root canal therapy is the treatment of choice for these cases and should always be attempted first. Monitoring the patients is necessary until complete healing of the disease.