Although the most common cause of the intermittently suppurating cutaneous sinus tract in the face and neck area is chronic dental infection, chronic draining sinus tracts of the face and neck continue to be a diagnostic challenge. The attending clinician must look carefully for a potential odontogenic infection; chronicity, lasting for weeks, months, and even years and the recognition of the lesion as a sinus tract are keys to making the correct diagnosis. Diagnostic errors can result in multiple surgical excisions and biopsies, long-term antibiotic therapy, and even radiation therapy or electrodesiccation. A review of 137 cases of cutaneous draining sinus tracts from the literature is presented, and four cases are reported. Conservative, nonsurgical root canal therapy is recommended as the first choice of treatment.