To compare self-reported pain levels across various treatment phases using passive self-ligating (Damon) and conventional (Victory) standardized fixed appliance systems. Adolescents (12-17 years old) with crowding and displaced teeth, planned for non-extraction treatment, were recruited from four orthodontic clinics. They were randomized into stratified blocks (1:1 ratio) using concealed allocation to receive Damon Q™ (34 boys, 28 girls) or Victory™ (39 boys, 31 girls). Pain and analgesic intake were assessed on seven different occasions with validated self-report questionnaires using a 10-grade scale. Of the 132 patients included, six were lost to follow up. Clinically relevant mean pain scores (≥4) were registered in both groups after bonding upper and lower arches and after insertion of 0.019 × 0.025 stainless steel archwire. The highest mean scores were reported on day two after bonding the upper arch (Damon 5.96, Victory 7.18, P = .011). In both groups, at least 40% reported taking analgesics during various treatment phases. The Damon group reported a lower intake of analgesics on days one and two (P = .042 and .037) after treatment initiation. In the entire sample, boys reported significantly higher mean pain scores than girls on the second and third days after bonding (P = .008 and .026, respectively). Lower pain levels were reported from the Damon group after bonding. In general, boys reported higher pain than girls did. Clinicians and adolescents need to be aware that clinically relevant pain levels can be expected not only after bonding but also in later phases.