Background: Mandibular third molar (M3M) removal and the management of postoperative complications represent a common matter of interest in oral and maxillofacial surgery. Pain represents a great symptom for patients affected by pericoronitis and it is the most common indication for third molar removal. The aim of the present article is to search for patterns of pre-operative pain in patients before undergoing third molar surgery and to test for a relation between some patterns of symptoms, such as pain intensity, site of symptomatic tooth, and referred area of pain. Methods: This retrospective observational study enrolled a total of 86 patients, aged (mean ± SD) 34.54 ± 13.62 years (range 17–78 years), scheduled for outpatient third molar extraction at the Oral Surgery School, Department of Medical Biotechnologies, Policlinico “Le Scotte”, University of Siena. Pericoronitis and pain were the symptoms of the patients and the indication of extraction. Inclusion criteria were the presence of partially impacted third molars, confirmed with a preoperative panoramic radiograph, and preoperative pain. Exclusion criteria were known neurological disease (such as previous trigeminal or facial nerve injuries), impaired communicative or cognitive disease, diagnosed diabetes mellitus, and oral surgical intervention within 30 days before data collection. Patients were visited and asked to answer a morphometric analytic questionnaire about their perception of pain referred to the third molar. Analyses were performed on statistical evaluation on age, age ranges, patient gender, prior third molar extraction, site of pericoronitis, pain score (1–10), and pain area. Two-tailedpvalues of less than 0.05 were considered significant if not otherwise specified. Results: No correlations were found between age, gender, previous extraction, tooth site (maxillar on mandible), pain score, and pain area. Patterns of third molar pericoronitis pain among 86 patients were reported. A significant correlation was found between pain score and pain area (p= 0.0111,rs= 0.3131). Conclusions: Pain intensity has indeed some kind of responsibility in determining the orofacial distribution of pain. The pain area referral patterns of the present article could be considered as a pain model resulting from the pericoronitis of maxillar and mandibular third molars.