To assess whether the treatment of children with oral midazolam and pediatric hypnosis techniques can improve the compliance in consecutive sessions, a retrospective longitudinal practice-based observational study was designed and carried out. A total of 311 children between 3 and 12 years of age were treated under hypnosis and sedation with midazolam (0.40 mg/kg body weight). Treatments were performed in one to a maximum of three sessions. A total of 183 children received one, 103 received two and 25 children received three treatment sessions. The behavior of the children during the sessions was examined by means of the Venham score. The self-evaluation of the children was based on the Wong–Baker Scale. Child behavior using midazolam and hypnosis techniques showed little difference and good compliance between the sessions. Venham scores did not increase significantly regarding total treatment from the first (0.99 ± 1.41) to the second (1.17 ± 1.39) and to the third session (1.27 ± 1.20) (p > 0.05). However, considering the highest Venham scores that occurred in each case, the behavior of the children worsened significantly (p < 0.01) during the three treatment sessions, from 1.37 ± 1.31 (first) to 1.87 ± 1.74 (second) to 2.32 ± 1.33 (third). In 6.11% of the children, treatment was discontinued in the first session (n = 19), 0.96% in the second (n = 3) and 0% in the third. Treatment with low-dose midazolam, combined with hypnosis techniques, showed to be an effective option for dental treatment in children. Within the limitations of the current study, and with consideration of highest possible compliance, no more than two treatment sessions for pediatric dental treatment should be performed.