Background: Orofacial pain is defined as pain felt in the soft or hard tissues of the head, face, mouth, and neck. Chronic orofacial pain is often challenging to diagnose and difficult to treat. Due to the lack of available information about the prevalence and clinical form of orofacial pain, this study aimed to evaluate the characteristics of chronic orofacial pain in patients presenting at the Department of Oral Medicine of Shahid Beheshti Dental School between 2012 and 2022. Methods: In this retrospective study, we evaluated the files of 121 patients at the Department of Oral and Maxillofacial Diseases of Shahid Beheshti Dental School, which were completed during 2012–2022. We extracted the required information from these files. Results: In total, 121 files were included in the study (30 male, 91 female). The mean age of the patients was 43.68 ± 16.79 years. The most common diagnosis in patients with chronic orofacial pain was temporomandibular disorders (TMD) (55.3%). Among pain-related factors, psychological factors showed the highest frequency (30.5%).Opening and closing (43.8%) had the highest frequency among factors that increased pain, and the rest (6.6%) had the highest frequency among the factors that reduced pain. Most patients experienced unilateral pain over the masseter area. Most patients reported their pain intensity to be greater than 7 in the verbal analog scale (VAS). The most common symptom associated with pain was joint noise (37.1%). Conclusion A ten-year retrospective evaluation of patient files showed that more than half of the patients with chronic orofacial pain had TMD.