AIM: This study examined the associations between the position of impacted mandibular third molars and postoperative complications, with a focus on pain, swelling, and their associations with proximity to the mandibular canal. METHODS: A retrospective cohort of 270 patients who underwent surgical extraction of mandibular third molars was analyzed. Preoperative panoramic radiographs were evaluated by three experienced surgeons to classify the tooth position (Winter classification) and proximity to the mandibular canal (Rood and Shehab classification). Postoperative complications (pain, swelling, trismus, paresthesia, hematoma, and hemorrhage) were assessed via standardized questionnaires and clinical records 7 days postoperatively. Data analysis included descriptive statistics and multinomial logistic regression. RESULTS: Mesioangular and horizontal impactions were significantly associated with increased postoperative pain and swelling. Logistic regression indicated that the mesioangular position increased the odds of pain by 95% (odds ratio [OR] = 1.95) and swelling by 85% (OR = 1.85). The horizontal impact increased the odds of pain by 2.8 times (OR = 2.8) and swelling by 5.0 times (OR = 5.0). Tooth position was a significant predictor of postoperative complications ( = 0.007), whereas proximity to the mandibular canal, patient age, and the mandibular side were not. Root darkening emerged as a notable radiographic finding. CONCLUSIONS: The position of impacted mandibular third molars, particularly mesioangular and horizontal angulations, significantly influences postoperative pain and swelling. These findings highlight the importance of considering the tooth position in surgical planning to reduce complications. Although panoramic radiography is useful in resource-limited settings, cone-beam computed tomography is advised for complex cases or when vital structures are at risk.