In the majority of orthodontic premolar extraction cases, the canine retraction phase is the most laborious procedure. This randomized clinical trial aimed to assess the effect of single versus repeated micro-osteoperforations (MOPs) during orthodontic canine retraction.In this split-mouth study, two equal groups of 18 patients who required maxillary first premolar extractions and fixed orthodontic therapy were randomly assigned (n=9). In Group I, MOPs were only performed once on one site before retraction, whereas in Group II, MOPs were performed on one site repeatedly once a month for four months. In both groups, the contralateral control sites received no MOPs. The canines were retracted using mini-screws and closed-coil nickel-titanium springs. Using the patients' 3D models, the primary outcome measure at four months was the amount of orthodontic canine distal movement. The amount of anchorage loss (AL), degree of molar rotation (MR) and canine rotation (CR), and degree of canine tipping (CT) were measured as the secondary outcomes. The comparison of mean changes in the primary and secondary outcomes between the groups was done using the independent sample t-test (p0.05). Additionally, there were no statistically significant variations in the maxillary first MR and the degree of AL (p>0.05).When maxillary canine retraction was performed with a single and repeated regimen of MOPs, comparable levels of distal CR and tipping were observed, along with an identical minimal degree of MR and AL.