Background: The study evaluated how often pharmacological therapies were started, modified, or discontinued after a consultation in a sample of orofacial pain patients and identified potential factors associated with treatment choices in the pharmacological management of orofacial pain. Methods: For this study, patient files (N = 208) originating from the daily routine of the Orofacial Pain Unit, University of Zurich (January 2017–December 2022) were analysed. Demographics, lifestyle, pain characteristics, diagnosis, and pharmacological therapy pre- and post- consultation with an orofacial pain specialist were recorded. Changes in pharmacotherapy, pain perception, and therapeutic success were assessed. Descriptive statistics, paired McNemar and chi-square tests were conducted. Results: A total of 208 patients were included in the study (64.4% females, mean age 45.9 years). The mean pain intensity was 6.93 for maximum pain and 4.62 for average pain. The most common pain locations were the face (64.3%), followed by the head (33.3%). At the initial consultation, 51.4% of patients were already using pharmacological therapy. The most common pre-diagnosis medications were non-steroidal anti-inflammatory drugs (NSAIDs) (44.9%), antidepressants with pain-modulating properties (9.3%), and magnesium (7.5%). After consultation, myofascial orofacial pain was the most common diagnosis (50.5%). The prescription of medications increased significantly to 74.5%(p < 0.001). Topical NSAIDs (64.0%) and magnesium supplements (40.0%) were the most prescribed. A significant relationship between therapy changes and diagnosis was observed, particularly for myofascial pain (p = 0.024) and temporomandibular joint disorders (p < 0.001). Therapy outcomes were positive for 67.0% of the observed patients. Conclusions: Age, psychological distress, and pain location significantly influenced pharmacological management of orofacial pain. Pharmacological therapy differed between before and after consultation at the Orofacial Pain Unit. Accurate diagnosis and a multidisciplinary approach to treatment can significantly improve therapy success.