Background: Managing anxiety and behavior during pediatric dental procedures is challenging. This study examines the effects of combining ibuprofen with midazolam sedation using both behavioral management and clinical hypnosis to improve patient cooperation and reduce post-treatment pain. Methods: A retrospective cohort study of 311 children (mean age 74.2 months, standard deviation (SD) = 24.7) was conducted. Patients received either midazolam with ibuprofen (n = 156) or midazolam only (n = 155). Behavior was assessed using the Venham Behavior Rating Scale and anxiety with the Dental Subscale of Children’s Fear Survey Schedule (CFSS-DS) and the Inventory of Stressful Situations (ISS) questionnaires. Statistical analyses included Mann–Whitney U tests and correlation analyses. Results: Ibuprofen did not significantly improve behavior during procedures (drinking phase 0.61, SD 1.31, p = 0.13; before treatment 0.25, SD 0.93, p = 0.53, anesthesia 1.21, SD 1.55, p = 0.29; after treatment 0.51, SD 1.22, p = 0.68), indicating that pharmacological pain management alone is insufficient to address behavioral challenges. Ibuprofen significantly reduced post-treatment pain, with 7.2% of cases reporting pain in the non-ibuprofen group compared to none in the ibuprofen group (p < 0.05). Conclusions: Ibuprofen had no effect on intraoperative behavior and only a limited effect on post-procedural pain, mainly for more invasive procedures. This study highlights the integration of sedation with behavioral strategies, such as clinical hypnosis, to manage anxiety and improve patient cooperation, aiming to enhance treatment outcomes using this integrative approach to pediatric dentistry. Further research is needed to optimize these strategies and verify them in a prospective setting.